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class="vector-toc-link" href="#Adverse_effects"> <div class="vector-toc-text"> 3 Adverse effects </div> </a> <button aria-controls="toc-Adverse_effects-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> Toggle Adverse effects subsection </button> <ul id="toc-Adverse_effects-sublist" class="vector-toc-list"> <li id="toc-Short-term" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Short-term"> <div class="vector-toc-text"> 3.1 Short-term </div> </a> <ul id="toc-Short-term-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Long-term" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Long-term"> <div class="vector-toc-text"> 3.2 Long-term </div> </a> <ul id="toc-Long-term-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Reinforcement_disorders" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Reinforcement_disorders"> <div class="vector-toc-text"> 3.3 Reinforcement disorders </div> </a> <ul id="toc-Reinforcement_disorders-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-During_pregnancy" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#During_pregnancy"> <div class="vector-toc-text"> 3.4 During pregnancy </div> </a> <ul id="toc-During_pregnancy-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Overdose" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Overdose"> <div class="vector-toc-text"> 4 Overdose </div> </a> <ul id="toc-Overdose-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Interactions" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Interactions"> <div class="vector-toc-text"> 5 Interactions </div> </a> <ul id="toc-Interactions-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Pharmacology" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Pharmacology"> <div class="vector-toc-text"> 6 Pharmacology </div> </a> <button aria-controls="toc-Pharmacology-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> Toggle Pharmacology subsection </button> <ul id="toc-Pharmacology-sublist" class="vector-toc-list"> <li id="toc-Pharmacodynamics" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Pharmacodynamics"> <div class="vector-toc-text"> 6.1 Pharmacodynamics </div> </a> <ul id="toc-Pharmacodynamics-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Pharmacokinetics" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Pharmacokinetics"> <div class="vector-toc-text"> 6.2 Pharmacokinetics </div> </a> <ul id="toc-Pharmacokinetics-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Chemistry" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Chemistry"> <div class="vector-toc-text"> 7 Chemistry </div> </a> <button aria-controls="toc-Chemistry-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> Toggle Chemistry subsection </button> <ul id="toc-Chemistry-sublist" class="vector-toc-list"> <li id="toc-Synthesis" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Synthesis"> <div class="vector-toc-text"> 7.1 Synthesis </div> </a> <ul id="toc-Synthesis-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Detection_in_body_fluids" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Detection_in_body_fluids"> <div class="vector-toc-text"> 7.2 Detection in body fluids </div> </a> <ul id="toc-Detection_in_body_fluids-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-History" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#History"> <div class="vector-toc-text"> 8 History </div> </a> <button aria-controls="toc-History-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> Toggle History subsection </button> <ul id="toc-History-sublist" class="vector-toc-list"> <li id="toc-Early_research_and_use" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Early_research_and_use"> <div class="vector-toc-text"> 8.1 Early research and use </div> </a> <ul id="toc-Early_research_and_use-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Shulgin's_research" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Shulgin's_research"> <div class="vector-toc-text"> 8.2 Shulgin's research </div> </a> <ul id="toc-Shulgin's_research-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Rising_recreational_use" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Rising_recreational_use"> <div class="vector-toc-text"> 8.3 Rising recreational use </div> </a> <ul id="toc-Rising_recreational_use-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Media_attention_and_scheduling" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Media_attention_and_scheduling"> <div class="vector-toc-text"> 8.4 Media attention and scheduling </div> </a> <ul id="toc-Media_attention_and_scheduling-sublist" class="vector-toc-list"> <li id="toc-United_States" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#United_States"> <div class="vector-toc-text"> 8.4.1 United States </div> </a> <ul id="toc-United_States-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-United_Nations" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#United_Nations"> <div class="vector-toc-text"> 8.4.2 United Nations </div> </a> <ul id="toc-United_Nations-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Post-scheduling" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Post-scheduling"> <div class="vector-toc-text"> 8.5 Post-scheduling </div> </a> <ul id="toc-Post-scheduling-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Society_and_culture" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Society_and_culture"> <div class="vector-toc-text"> 9 Society and culture </div> </a> <button aria-controls="toc-Society_and_culture-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> Toggle Society and culture subsection </button> <ul id="toc-Society_and_culture-sublist" class="vector-toc-list"> <li id="toc-Legal_status" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Legal_status"> <div class="vector-toc-text"> 9.1 Legal status </div> </a> <ul id="toc-Legal_status-sublist" class="vector-toc-list"> <li id="toc-Australia" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Australia"> <div class="vector-toc-text"> 9.1.1 Australia </div> </a> <ul id="toc-Australia-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-United_Kingdom" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#United_Kingdom"> <div class="vector-toc-text"> 9.1.2 United Kingdom </div> </a> <ul id="toc-United_Kingdom-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-United_States_2" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#United_States_2"> <div class="vector-toc-text"> 9.1.3 United States </div> </a> <ul id="toc-United_States_2-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Netherlands" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Netherlands"> <div class="vector-toc-text"> 9.1.4 Netherlands </div> </a> <ul id="toc-Netherlands-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Canada" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Canada"> <div class="vector-toc-text"> 9.1.5 Canada </div> </a> <ul id="toc-Canada-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Demographics" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Demographics"> <div class="vector-toc-text"> 9.2 Demographics </div> </a> <ul id="toc-Demographics-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Economics" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Economics"> <div class="vector-toc-text"> 9.3 Economics </div> </a> <ul id="toc-Economics-sublist" class="vector-toc-list"> <li id="toc-Europe" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Europe"> <div class="vector-toc-text"> 9.3.1 Europe </div> </a> <ul id="toc-Europe-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-North_America" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#North_America"> <div class="vector-toc-text"> 9.3.2 North America </div> </a> <ul id="toc-North_America-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Australia_2" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Australia_2"> <div class="vector-toc-text"> 9.3.3 Australia </div> </a> <ul id="toc-Australia_2-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Corporate_logos_on_pills" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Corporate_logos_on_pills"> <div class="vector-toc-text"> 9.3.4 Corporate logos on pills </div> </a> <ul id="toc-Corporate_logos_on_pills-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> </ul> </li> <li id="toc-Research_directions" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Research_directions"> <div class="vector-toc-text"> 10 Research directions </div> </a> <ul id="toc-Research_directions-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-See_also" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#See_also"> <div class="vector-toc-text"> 11 See also </div> </a> <ul id="toc-See_also-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-References" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#References"> <div class="vector-toc-text"> 12 References </div> </a> <ul id="toc-References-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-External_links" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#External_links"> <div class="vector-toc-text"> 13 External links </div> </a> <ul id="toc-External_links-sublist" class="vector-toc-list"> </ul> </li> </ul> </div> </div> </nav> </div> </div> <div class="mw-content-container"> <main id="content" class="mw-body"> <header class="mw-body-header vector-page-titlebar"> <nav aria-label="Contents" class="vector-toc-landmark"> <div id="vector-page-titlebar-toc" class="vector-dropdown vector-page-titlebar-toc vector-button-flush-left" title="Table of Contents" > <input type="checkbox" id="vector-page-titlebar-toc-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-vector-page-titlebar-toc" class="vector-dropdown-checkbox " aria-label="Toggle the table of contents" > <label id="vector-page-titlebar-toc-label" for="vector-page-titlebar-toc-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--icon-only " aria-hidden="true" > Toggle the table of contents </label> <div class="vector-dropdown-content"> <div id="vector-page-titlebar-toc-unpinned-container" class="vector-unpinned-container"> </div> </div> </div> </nav> <h1 id="firstHeading" class="firstHeading mw-first-heading">MDMA</h1> <div id="p-lang-btn" class="vector-dropdown mw-portlet mw-portlet-lang" > <input type="checkbox" id="p-lang-btn-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-p-lang-btn" class="vector-dropdown-checkbox mw-interlanguage-selector" aria-label="Go to an article in another language. Available in 64 languages" > <label id="p-lang-btn-label" for="p-lang-btn-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--action-progressive mw-portlet-lang-heading-64" aria-hidden="true" > 64 languages </label> <div class="vector-dropdown-content"> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li class="interlanguage-link interwiki-ar mw-list-item"><a href="https://ar.wikipedia.org/wiki/MDMA" title="MDMA – Arabic" lang="ar" hreflang="ar" data-title="MDMA" data-language-autonym="العربية" data-language-local-name="Arabic" class="interlanguage-link-target">العربية</a></li><li class="interlanguage-link interwiki-ast badge-Q17437798 badge-goodarticle mw-list-item" title="good article badge"><a href="https://ast.wikipedia.org/wiki/MDMA" title="MDMA – Asturian" lang="ast" hreflang="ast" data-title="MDMA" data-language-autonym="Asturianu" data-language-local-name="Asturian" class="interlanguage-link-target">Asturianu</a></li><li class="interlanguage-link interwiki-az mw-list-item"><a href="https://az.wikipedia.org/wiki/MDMA" title="MDMA – Azerbaijani" lang="az" hreflang="az" data-title="MDMA" data-language-autonym="Azərbaycanca" data-language-local-name="Azerbaijani" class="interlanguage-link-target">Azərbaycanca</a></li><li class="interlanguage-link interwiki-azb mw-list-item"><a href="https://azb.wikipedia.org/wiki/%D8%A7%DA%A9%D8%B3%D8%AA%D8%A7%D8%B2%DB%8C" title="اکستازی – South Azerbaijani" lang="azb" hreflang="azb" data-title="اکستازی" data-language-autonym="تۆرکجه" data-language-local-name="South Azerbaijani" class="interlanguage-link-target">تۆرکجه</a></li><li class="interlanguage-link interwiki-bg mw-list-item"><a href="https://bg.wikipedia.org/wiki/MDMA" title="MDMA – Bulgarian" lang="bg" hreflang="bg" data-title="MDMA" data-language-autonym="Български" data-language-local-name="Bulgarian" class="interlanguage-link-target">Български</a></li><li class="interlanguage-link interwiki-bar badge-Q17437796 badge-featuredarticle mw-list-item" title="featured article badge"><a href="https://bar.wikipedia.org/wiki/Ecstasy" title="Ecstasy – Bavarian" lang="bar" hreflang="bar" data-title="Ecstasy" data-language-autonym="Boarisch" data-language-local-name="Bavarian" class="interlanguage-link-target">Boarisch</a></li><li class="interlanguage-link interwiki-ca mw-list-item"><a href="https://ca.wikipedia.org/wiki/MDMA" title="MDMA – Catalan" lang="ca" hreflang="ca" data-title="MDMA" data-language-autonym="Català" data-language-local-name="Catalan" class="interlanguage-link-target">Català</a></li><li class="interlanguage-link interwiki-cs mw-list-item"><a href="https://cs.wikipedia.org/wiki/Ext%C3%A1ze_(droga)" title="Extáze (droga) – Czech" lang="cs" hreflang="cs" data-title="Extáze (droga)" data-language-autonym="Čeština" data-language-local-name="Czech" class="interlanguage-link-target">Čeština</a></li><li class="interlanguage-link interwiki-cy mw-list-item"><a href="https://cy.wikipedia.org/wiki/MDMA" title="MDMA – Welsh" lang="cy" hreflang="cy" data-title="MDMA" data-language-autonym="Cymraeg" data-language-local-name="Welsh" class="interlanguage-link-target">Cymraeg</a></li><li class="interlanguage-link interwiki-da mw-list-item"><a href="https://da.wikipedia.org/wiki/MDMA" title="MDMA – Danish" lang="da" hreflang="da" data-title="MDMA" data-language-autonym="Dansk" data-language-local-name="Danish" class="interlanguage-link-target">Dansk</a></li><li class="interlanguage-link interwiki-de mw-list-item"><a href="https://de.wikipedia.org/wiki/MDMA" title="MDMA – German" lang="de" hreflang="de" data-title="MDMA" data-language-autonym="Deutsch" data-language-local-name="German" class="interlanguage-link-target">Deutsch</a></li><li class="interlanguage-link interwiki-et mw-list-item"><a href="https://et.wikipedia.org/wiki/MDMA" title="MDMA – Estonian" lang="et" hreflang="et" data-title="MDMA" data-language-autonym="Eesti" data-language-local-name="Estonian" class="interlanguage-link-target">Eesti</a></li><li class="interlanguage-link interwiki-el mw-list-item"><a href="https://el.wikipedia.org/wiki/MDMA" title="MDMA – Greek" lang="el" hreflang="el" data-title="MDMA" data-language-autonym="Ελληνικά" data-language-local-name="Greek" class="interlanguage-link-target">Ελληνικά</a></li><li class="interlanguage-link interwiki-es badge-Q17437798 badge-goodarticle mw-list-item" title="good article badge"><a href="https://es.wikipedia.org/wiki/MDMA" title="MDMA – Spanish" lang="es" hreflang="es" data-title="MDMA" data-language-autonym="Español" data-language-local-name="Spanish" class="interlanguage-link-target">Español</a></li><li class="interlanguage-link interwiki-eo mw-list-item"><a href="https://eo.wikipedia.org/wiki/Ekstazilo" title="Ekstazilo – Esperanto" lang="eo" hreflang="eo" data-title="Ekstazilo" data-language-autonym="Esperanto" data-language-local-name="Esperanto" class="interlanguage-link-target">Esperanto</a></li><li class="interlanguage-link interwiki-eu mw-list-item"><a href="https://eu.wikipedia.org/wiki/MDMA" title="MDMA – Basque" lang="eu" hreflang="eu" data-title="MDMA" data-language-autonym="Euskara" data-language-local-name="Basque" class="interlanguage-link-target">Euskara</a></li><li class="interlanguage-link interwiki-fa mw-list-item"><a href="https://fa.wikipedia.org/wiki/%D8%A7%DA%A9%D8%B3%D8%AA%D8%A7%D8%B2%DB%8C" title="اکستازی – Persian" lang="fa" hreflang="fa" data-title="اکستازی" data-language-autonym="فارسی" data-language-local-name="Persian" class="interlanguage-link-target">فارسی</a></li><li class="interlanguage-link interwiki-fo mw-list-item"><a href="https://fo.wikipedia.org/wiki/Ecstasy" title="Ecstasy – Faroese" lang="fo" hreflang="fo" data-title="Ecstasy" data-language-autonym="Føroyskt" data-language-local-name="Faroese" class="interlanguage-link-target">Føroyskt</a></li><li class="interlanguage-link interwiki-fr mw-list-item"><a href="https://fr.wikipedia.org/wiki/MDMA" title="MDMA – French" lang="fr" hreflang="fr" data-title="MDMA" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target">Français</a></li><li class="interlanguage-link interwiki-fy mw-list-item"><a href="https://fy.wikipedia.org/wiki/MDMA" title="MDMA – Western Frisian" lang="fy" hreflang="fy" data-title="MDMA" data-language-autonym="Frysk" data-language-local-name="Western Frisian" class="interlanguage-link-target">Frysk</a></li><li class="interlanguage-link interwiki-ga mw-list-item"><a href="https://ga.wikipedia.org/wiki/MDMA" title="MDMA – Irish" lang="ga" hreflang="ga" data-title="MDMA" data-language-autonym="Gaeilge" data-language-local-name="Irish" class="interlanguage-link-target">Gaeilge</a></li><li class="interlanguage-link interwiki-gl mw-list-item"><a href="https://gl.wikipedia.org/wiki/MDMA" title="MDMA – Galician" lang="gl" hreflang="gl" data-title="MDMA" data-language-autonym="Galego" data-language-local-name="Galician" class="interlanguage-link-target">Galego</a></li><li class="interlanguage-link interwiki-ko mw-list-item"><a href="https://ko.wikipedia.org/wiki/%EB%A9%94%ED%8B%B8%EB%A0%8C%EB%94%94%EC%98%A5%EC%8B%9C%EB%A9%94%EC%8A%A4%EC%95%94%ED%8E%98%ED%83%80%EB%AF%BC" title="메틸렌디옥시메스암페타민 – Korean" lang="ko" hreflang="ko" data-title="메틸렌디옥시메스암페타민" data-language-autonym="한국어" data-language-local-name="Korean" class="interlanguage-link-target">한국어</a></li><li class="interlanguage-link interwiki-hi mw-list-item"><a href="https://hi.wikipedia.org/wiki/%E0%A4%8F%E0%A4%AE%E0%A4%A1%E0%A5%80%E0%A4%8F%E0%A4%AE%E0%A4%8F" title="एमडीएमए – Hindi" lang="hi" hreflang="hi" data-title="एमडीएमए" data-language-autonym="हिन्दी" data-language-local-name="Hindi" class="interlanguage-link-target">हिन्दी</a></li><li class="interlanguage-link interwiki-hr mw-list-item"><a href="https://hr.wikipedia.org/wiki/MDMA" title="MDMA – Croatian" lang="hr" hreflang="hr" data-title="MDMA" data-language-autonym="Hrvatski" data-language-local-name="Croatian" class="interlanguage-link-target">Hrvatski</a></li><li class="interlanguage-link interwiki-id mw-list-item"><a href="https://id.wikipedia.org/wiki/Metilendioksimetamfetamina" title="Metilendioksimetamfetamina – Indonesian" lang="id" hreflang="id" data-title="Metilendioksimetamfetamina" data-language-autonym="Bahasa Indonesia" data-language-local-name="Indonesian" class="interlanguage-link-target">Bahasa Indonesia</a></li><li class="interlanguage-link interwiki-is mw-list-item"><a href="https://is.wikipedia.org/wiki/MDMA" title="MDMA – Icelandic" lang="is" hreflang="is" data-title="MDMA" data-language-autonym="Íslenska" data-language-local-name="Icelandic" class="interlanguage-link-target">Íslenska</a></li><li class="interlanguage-link interwiki-it mw-list-item"><a href="https://it.wikipedia.org/wiki/MDMA" title="MDMA – Italian" lang="it" hreflang="it" data-title="MDMA" data-language-autonym="Italiano" data-language-local-name="Italian" class="interlanguage-link-target">Italiano</a></li><li class="interlanguage-link interwiki-he mw-list-item"><a href="https://he.wikipedia.org/wiki/MDMA" title="MDMA – Hebrew" lang="he" hreflang="he" data-title="MDMA" data-language-autonym="עברית" data-language-local-name="Hebrew" class="interlanguage-link-target">עברית</a></li><li class="interlanguage-link interwiki-ks mw-list-item"><a href="https://ks.wikipedia.org/wiki/%D8%A7%DB%8C%D9%85_%DA%88%DB%8C_%D8%A7%DB%8C%D9%85_%D8%A7%DB%92" title="ایم ڈی ایم اے – Kashmiri" lang="ks" hreflang="ks" data-title="ایم ڈی ایم اے" data-language-autonym="कॉशुर / کٲشُر" data-language-local-name="Kashmiri" class="interlanguage-link-target">कॉशुर / کٲشُر</a></li><li class="interlanguage-link interwiki-sw mw-list-item"><a href="https://sw.wikipedia.org/wiki/MDMA" title="MDMA – Swahili" lang="sw" hreflang="sw" data-title="MDMA" data-language-autonym="Kiswahili" data-language-local-name="Swahili" class="interlanguage-link-target">Kiswahili</a></li><li class="interlanguage-link interwiki-la mw-list-item"><a href="https://la.wikipedia.org/wiki/MDMA" title="MDMA – Latin" lang="la" hreflang="la" data-title="MDMA" data-language-autonym="Latina" data-language-local-name="Latin" class="interlanguage-link-target">Latina</a></li><li class="interlanguage-link interwiki-lv mw-list-item"><a href="https://lv.wikipedia.org/wiki/MDMA" title="MDMA – Latvian" lang="lv" hreflang="lv" data-title="MDMA" data-language-autonym="Latviešu" data-language-local-name="Latvian" class="interlanguage-link-target">Latviešu</a></li><li class="interlanguage-link interwiki-lt mw-list-item"><a href="https://lt.wikipedia.org/wiki/MDMA" title="MDMA – Lithuanian" lang="lt" hreflang="lt" data-title="MDMA" data-language-autonym="Lietuvių" data-language-local-name="Lithuanian" class="interlanguage-link-target">Lietuvių</a></li><li class="interlanguage-link interwiki-li mw-list-item"><a href="https://li.wikipedia.org/wiki/Xtc" title="Xtc – Limburgish" lang="li" hreflang="li" data-title="Xtc" data-language-autonym="Limburgs" data-language-local-name="Limburgish" class="interlanguage-link-target">Limburgs</a></li><li class="interlanguage-link interwiki-hu mw-list-item"><a href="https://hu.wikipedia.org/wiki/Metil%C3%A9ndioxi-metamfetamin" title="Metiléndioxi-metamfetamin – Hungarian" lang="hu" hreflang="hu" data-title="Metiléndioxi-metamfetamin" data-language-autonym="Magyar" data-language-local-name="Hungarian" class="interlanguage-link-target">Magyar</a></li><li class="interlanguage-link interwiki-ml mw-list-item"><a href="https://ml.wikipedia.org/wiki/%E0%B4%AE%E0%B5%86%E0%B4%A4%E0%B5%8D%E0%B4%A4%E0%B4%B2%E0%B5%80%E0%B5%BB_%E0%B4%A1%E0%B4%AF%E0%B5%8B%E0%B4%95%E0%B5%8D%E0%B4%B8%E0%B4%BF_%E0%B4%AE%E0%B5%86%E0%B4%A4%E0%B5%8D_%E0%B4%86%E0%B4%82%E0%B4%AB%E0%B5%8D%E0%B4%B1%E0%B5%8D%E0%B4%B1%E0%B4%AE%E0%B5%88%E0%B5%BB" title="മെത്തലീൻ ഡയോക്സി മെത് ആംഫ്റ്റമൈൻ – Malayalam" lang="ml" hreflang="ml" data-title="മെത്തലീൻ ഡയോക്സി മെത് ആംഫ്റ്റമൈൻ" data-language-autonym="മലയാളം" data-language-local-name="Malayalam" class="interlanguage-link-target">മലയാളം</a></li><li class="interlanguage-link interwiki-arz mw-list-item"><a href="https://arz.wikipedia.org/wiki/%D8%A7%D9%83%D8%B3%D8%AA%D8%A7%D8%B3%D9%89" title="اكستاسى – Egyptian Arabic" lang="arz" hreflang="arz" data-title="اكستاسى" data-language-autonym="مصرى" data-language-local-name="Egyptian Arabic" class="interlanguage-link-target">مصرى</a></li><li class="interlanguage-link interwiki-ms mw-list-item"><a href="https://ms.wikipedia.org/wiki/MDMA" title="MDMA – Malay" lang="ms" hreflang="ms" data-title="MDMA" data-language-autonym="Bahasa Melayu" data-language-local-name="Malay" class="interlanguage-link-target">Bahasa Melayu</a></li><li class="interlanguage-link interwiki-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/MDMA" title="MDMA – Dutch" lang="nl" hreflang="nl" data-title="MDMA" data-language-autonym="Nederlands" data-language-local-name="Dutch" class="interlanguage-link-target">Nederlands</a></li><li class="interlanguage-link interwiki-ja mw-list-item"><a href="https://ja.wikipedia.org/wiki/%E3%83%A1%E3%83%81%E3%83%AC%E3%83%B3%E3%82%B8%E3%82%AA%E3%82%AD%E3%82%B7%E3%83%A1%E3%82%BF%E3%83%B3%E3%83%95%E3%82%A7%E3%82%BF%E3%83%9F%E3%83%B3" title="メチレンジオキシメタンフェタミン – Japanese" lang="ja" hreflang="ja" data-title="メチレンジオキシメタンフェタミン" data-language-autonym="日本語" data-language-local-name="Japanese" class="interlanguage-link-target">日本語</a></li><li class="interlanguage-link interwiki-no mw-list-item"><a href="https://no.wikipedia.org/wiki/MDMA" title="MDMA – Norwegian Bokmål" lang="nb" hreflang="nb" data-title="MDMA" data-language-autonym="Norsk bokmål" data-language-local-name="Norwegian Bokmål" class="interlanguage-link-target">Norsk bokmål</a></li><li class="interlanguage-link interwiki-nn mw-list-item"><a href="https://nn.wikipedia.org/wiki/MDMA" title="MDMA – Norwegian Nynorsk" lang="nn" hreflang="nn" data-title="MDMA" data-language-autonym="Norsk nynorsk" data-language-local-name="Norwegian Nynorsk" class="interlanguage-link-target">Norsk nynorsk</a></li><li class="interlanguage-link interwiki-or mw-list-item"><a href="https://or.wikipedia.org/wiki/%E0%AC%8F%E0%AC%AE%E0%AD%8D%E2%80%8C%E0%AC%A1%E0%AC%BF%E0%AC%8F%E0%AC%AE%E0%AD%8D%E2%80%8C%E0%AC%8F" title="ଏମ୍‌ଡିଏମ୍‌ଏ – Odia" lang="or" hreflang="or" data-title="ଏମ୍‌ଡିଏମ୍‌ଏ" data-language-autonym="ଓଡ଼ିଆ" data-language-local-name="Odia" class="interlanguage-link-target">ଓଡ଼ିଆ</a></li><li class="interlanguage-link interwiki-pl mw-list-item"><a href="https://pl.wikipedia.org/wiki/3,4-Metylenodioksymetamfetamina" title="3,4-Metylenodioksymetamfetamina – Polish" lang="pl" hreflang="pl" data-title="3,4-Metylenodioksymetamfetamina" data-language-autonym="Polski" data-language-local-name="Polish" class="interlanguage-link-target">Polski</a></li><li class="interlanguage-link interwiki-pt mw-list-item"><a href="https://pt.wikipedia.org/wiki/MDMA" title="MDMA – Portuguese" lang="pt" hreflang="pt" data-title="MDMA" data-language-autonym="Português" data-language-local-name="Portuguese" class="interlanguage-link-target">Português</a></li><li class="interlanguage-link interwiki-ro mw-list-item"><a href="https://ro.wikipedia.org/wiki/MDMA" title="MDMA – Romanian" lang="ro" hreflang="ro" data-title="MDMA" data-language-autonym="Română" data-language-local-name="Romanian" class="interlanguage-link-target">Română</a></li><li class="interlanguage-link interwiki-ru badge-Q17437796 badge-featuredarticle mw-list-item" title="featured article badge"><a href="https://ru.wikipedia.org/wiki/MDMA" title="MDMA – Russian" lang="ru" hreflang="ru" data-title="MDMA" data-language-autonym="Русский" data-language-local-name="Russian" class="interlanguage-link-target">Русский</a></li><li class="interlanguage-link interwiki-sco mw-list-item"><a href="https://sco.wikipedia.org/wiki/MDMA" title="MDMA – Scots" lang="sco" hreflang="sco" data-title="MDMA" data-language-autonym="Scots" data-language-local-name="Scots" class="interlanguage-link-target">Scots</a></li><li class="interlanguage-link interwiki-simple mw-list-item"><a href="https://simple.wikipedia.org/wiki/MDMA" title="MDMA – Simple English" lang="en-simple" hreflang="en-simple" data-title="MDMA" data-language-autonym="Simple English" data-language-local-name="Simple English" class="interlanguage-link-target">Simple English</a></li><li class="interlanguage-link interwiki-sk mw-list-item"><a href="https://sk.wikipedia.org/wiki/Ext%C3%A1za_(droga)" title="Extáza (droga) – Slovak" lang="sk" hreflang="sk" data-title="Extáza (droga)" data-language-autonym="Slovenčina" data-language-local-name="Slovak" class="interlanguage-link-target">Slovenčina</a></li><li class="interlanguage-link interwiki-sl mw-list-item"><a href="https://sl.wikipedia.org/wiki/Ekstazi" title="Ekstazi – Slovenian" lang="sl" hreflang="sl" data-title="Ekstazi" data-language-autonym="Slovenščina" data-language-local-name="Slovenian" class="interlanguage-link-target">Slovenščina</a></li><li class="interlanguage-link interwiki-ckb mw-list-item"><a href="https://ckb.wikipedia.org/wiki/%D8%A6%DB%8E%DA%A9%D8%B3%D8%AA%D8%B3%DB%8C" title="ئێکستسی – Central Kurdish" lang="ckb" hreflang="ckb" data-title="ئێکستسی" data-language-autonym="کوردی" data-language-local-name="Central Kurdish" class="interlanguage-link-target">کوردی</a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/%D0%9C%D0%94%D0%9C%D0%90" title="МДМА – Serbian" lang="sr" hreflang="sr" data-title="МДМА" data-language-autonym="Српски / srpski" data-language-local-name="Serbian" class="interlanguage-link-target">Српски / srpski</a></li><li class="interlanguage-link interwiki-sh mw-list-item"><a href="https://sh.wikipedia.org/wiki/Metilendioksimetamfetamin" title="Metilendioksimetamfetamin – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Metilendioksimetamfetamin" data-language-autonym="Srpskohrvatski / српскохрватски" data-language-local-name="Serbo-Croatian" class="interlanguage-link-target">Srpskohrvatski / српскохрватски</a></li><li class="interlanguage-link interwiki-fi badge-Q17437798 badge-goodarticle mw-list-item" title="good article badge"><a href="https://fi.wikipedia.org/wiki/MDMA" title="MDMA – Finnish" lang="fi" hreflang="fi" data-title="MDMA" data-language-autonym="Suomi" data-language-local-name="Finnish" class="interlanguage-link-target">Suomi</a></li><li class="interlanguage-link interwiki-sv mw-list-item"><a href="https://sv.wikipedia.org/wiki/MDMA" title="MDMA – Swedish" lang="sv" hreflang="sv" data-title="MDMA" data-language-autonym="Svenska" data-language-local-name="Swedish" class="interlanguage-link-target">Svenska</a></li><li class="interlanguage-link interwiki-tr mw-list-item"><a href="https://tr.wikipedia.org/wiki/Ekstazi" title="Ekstazi – Turkish" lang="tr" hreflang="tr" data-title="Ekstazi" data-language-autonym="Türkçe" data-language-local-name="Turkish" class="interlanguage-link-target">Türkçe</a></li><li class="interlanguage-link interwiki-uk mw-list-item"><a href="https://uk.wikipedia.org/wiki/MDMA" title="MDMA – Ukrainian" lang="uk" hreflang="uk" data-title="MDMA" data-language-autonym="Українська" data-language-local-name="Ukrainian" class="interlanguage-link-target">Українська</a></li><li class="interlanguage-link interwiki-ur mw-list-item"><a href="https://ur.wikipedia.org/wiki/%D8%A7%DB%8C%D9%85_%DA%88%DB%8C_%D8%A7%DB%8C%D9%85_%D8%A7%DB%92" title="ایم ڈی ایم اے – Urdu" lang="ur" hreflang="ur" data-title="ایم ڈی ایم اے" data-language-autonym="اردو" data-language-local-name="Urdu" class="interlanguage-link-target">اردو</a></li><li class="interlanguage-link interwiki-vi mw-list-item"><a href="https://vi.wikipedia.org/wiki/Thu%E1%BB%91c_l%E1%BA%AFc" title="Thuốc lắc – Vietnamese" lang="vi" hreflang="vi" data-title="Thuốc lắc" data-language-autonym="Tiếng Việt" data-language-local-name="Vietnamese" class="interlanguage-link-target">Tiếng Việt</a></li><li class="interlanguage-link interwiki-wuu mw-list-item"><a href="https://wuu.wikipedia.org/wiki/MDMA" title="MDMA – Wu" lang="wuu" hreflang="wuu" data-title="MDMA" data-language-autonym="吴语" data-language-local-name="Wu" class="interlanguage-link-target">吴语</a></li><li class="interlanguage-link interwiki-zh-yue mw-list-item"><a href="https://zh-yue.wikipedia.org/wiki/%E7%8B%82%E5%96%9C" title="狂喜 – Cantonese" lang="yue" hreflang="yue" data-title="狂喜" data-language-autonym="粵語" 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class="mw-content-ltr mw-parser-output" lang="en" dir="ltr"><div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Psychoactive drug, often called ecstasy</div> <style data-mw-deduplicate="TemplateStyles:r1236090951">.mw-parser-output .hatnote{font-style:italic}.mw-parser-output div.hatnote{padding-left:1.6em;margin-bottom:0.5em}.mw-parser-output .hatnote i{font-style:normal}.mw-parser-output .hatnote+link+.hatnote{margin-top:-0.5em}@media print{body.ns-0 .mw-parser-output .hatnote{display:none!important}}</style><div role="note" class="hatnote navigation-not-searchable">For other uses, see <a href="/wiki/MDMA_(disambiguation)" class="mw-disambig" title="MDMA (disambiguation)">MDMA (disambiguation)</a>. Not to be confused with <a href="/wiki/MDA_(drug)" class="mw-redirect" title="MDA (drug)">MDA (drug)</a>; <a href="/wiki/EDMA" title="EDMA">EDMA</a>; <a href="/wiki/NMDA" class="mw-redirect" title="NMDA">NMDA</a>; or <a href="/wiki/2,3-MDMA" class="mw-redirect" title="2,3-MDMA">2,3-MDMA</a>.</div> <div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Pharmaceutical compound</div> <style data-mw-deduplicate="TemplateStyles:r1269284339">@media screen{html.skin-theme-clientpref-night .mw-parser-output .dark_mode_safe img{background-color:var(--background-color-inverted,#f8f9fa)}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .dark_mode_safe img{background-color:var(--background-color-inverted,#f8f9fa)}}</style> <style data-mw-deduplicate="TemplateStyles:r1257001546">.mw-parser-output .infobox-subbox{padding:0;border:none;margin:-3px;width:auto;min-width:100%;font-size:100%;clear:none;float:none;background-color:transparent}.mw-parser-output .infobox-3cols-child{margin:auto}.mw-parser-output .infobox .navbar{font-size:100%}@media screen{html.skin-theme-clientpref-night .mw-parser-output .infobox-full-data:not(.notheme)>div:not(.notheme)[style]{background:#1f1f23!important;color:#f8f9fa}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .infobox-full-data:not(.notheme) div:not(.notheme){background:#1f1f23!important;color:#f8f9fa}}@media(min-width:640px){body.skin--responsive .mw-parser-output .infobox-table{display:table!important}body.skin--responsive .mw-parser-output .infobox-table>caption{display:table-caption!important}body.skin--responsive .mw-parser-output .infobox-table>tbody{display:table-row-group}body.skin--responsive .mw-parser-output .infobox-table tr{display:table-row!important}body.skin--responsive .mw-parser-output .infobox-table th,body.skin--responsive .mw-parser-output .infobox-table td{padding-left:inherit;padding-right:inherit}}</style><table class="infobox" style="border-spacing:2px;"><caption class="infobox-title">MDMA <abbr title="International nonproprietary name">INN</abbr>: Midomafetamine<a href="#cite_note-INN-1">[1]</a></caption><tbody><tr><td colspan="2" class="infobox-image"><a href="/wiki/File:MDMA_(simple).svg" class="mw-file-description"><img alt="MDMA structure" src="//upload.wikimedia.org/wikipedia/commons/thumb/2/21/MDMA_%28simple%29.svg/250px-MDMA_%28simple%29.svg.png" decoding="async" width="250" height="110" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/2/21/MDMA_%28simple%29.svg/375px-MDMA_%28simple%29.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/2/21/MDMA_%28simple%29.svg/500px-MDMA_%28simple%29.svg.png 2x" data-file-width="256" data-file-height="113" /></a></td></tr><tr><td colspan="2" class="infobox-image"><a href="/wiki/File:MDMA_molecule_from_xtal_ball.png" class="mw-file-description"><img alt="Ball-and-stick model of an MDMA molecule" src="//upload.wikimedia.org/wikipedia/commons/thumb/b/b0/MDMA_molecule_from_xtal_ball.png/250px-MDMA_molecule_from_xtal_ball.png" decoding="async" width="250" height="229" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/b/b0/MDMA_molecule_from_xtal_ball.png/375px-MDMA_molecule_from_xtal_ball.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/b/b0/MDMA_molecule_from_xtal_ball.png/500px-MDMA_molecule_from_xtal_ball.png 2x" data-file-width="3000" data-file-height="2750" /></a></td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd;color:inherit;">Clinical data</th></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;">Pronunciation</th><td class="infobox-data">methylenedioxymethamphetamine: <a href="/wiki/Help:IPA/English" title="Help:IPA/English">/ˌmɛθɪliːndaɪˈɒksi/</a> <a href="/wiki/Help:IPA/English" title="Help:IPA/English">/ˌmɛθæmˈfɛtəmiːn/</a> </td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;">Other names</th><td class="infobox-data"><abbr title="3,4-Methylenedioxymethamphetamine">3,4-MDMA</abbr>; Ecstasy (E, X, XTC); Midomafetamine; Molly; Mandy;<a href="#cite_note-nature.com-2">[2]</a><a href="#cite_note-DrugFacts-3">[3]</a> Pingers/Pingas<a href="#cite_note-4">[4]</a></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/American_Society_of_Health-System_Pharmacists" title="American Society of Health-System Pharmacists">AHFS</a>/<a href="/wiki/Drugs.com" title="Drugs.com">Drugs.com</a></th><td class="infobox-data"><a rel="nofollow" class="external text" href="https://www.drugs.com/MDMA.html">MDMA</a></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Substance_dependence" title="Substance dependence">Dependence liability</a></th><td class="infobox-data"><a href="/wiki/Physical_dependence" title="Physical dependence">Physical</a>: Not typical<a href="#cite_note-palmer-5">[5]</a> <a href="/wiki/Psychological_dependence" title="Psychological dependence">Psychological</a>: Moderate<a href="#cite_note-6">[6]</a></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Addiction" title="Addiction">Addiction liability</a></th><td class="infobox-data">Low–moderate<a href="#cite_note-NHM-MDMA-7">[7]</a><a href="#cite_note-Betzler2017-8">[8]</a><a href="#cite_note-Substance_abuse-9">[9]</a></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Route_of_administration" title="Route of administration">Routes of administration</a></th><td class="infobox-data">Common: <a href="/wiki/Oral_route" class="mw-redirect" title="Oral route">By mouth</a><a href="#cite_note-EU2015-10">[10]</a> Uncommon: <a href="/wiki/Insufflation" title="Insufflation">Insufflation</a>,<a href="#cite_note-EU2015-10">[10]</a> <a href="/wiki/Inhalation" title="Inhalation">inhalation</a>,<a href="#cite_note-EU2015-10">[10]</a> <a href="/wiki/Injection_(medicine)" title="Injection (medicine)">injection</a>,<a href="#cite_note-EU2015-10">[10]</a><a href="#cite_note-11">[11]</a> <a href="/wiki/Rectal_(medicine)" class="mw-redirect" title="Rectal (medicine)">rectal</a></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Drug_class" title="Drug class">Drug class</a></th><td class="infobox-data"><a href="/wiki/Entactogen" class="mw-redirect" title="Entactogen">Entactogen</a>; <a href="/wiki/Stimulant" title="Stimulant">Stimulant</a>; <a href="/wiki/Serotonergic_psychedelic" class="mw-redirect" title="Serotonergic psychedelic">Psychedelic</a>; <a href="/wiki/Serotonin%E2%80%93norepinephrine%E2%80%93dopamine_releasing_agent" title="Serotonin–norepinephrine–dopamine releasing agent">Serotonin–norepinephrine–dopamine releasing agent</a>; <a href="/wiki/Serotonin" title="Serotonin">Serotonin</a> <a href="/wiki/5-HT2_receptor" title="5-HT2 receptor">5-HT2 receptor</a> <a href="/wiki/Agonist" title="Agonist">agonist</a></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Anatomical_Therapeutic_Chemical_Classification_System" title="Anatomical Therapeutic Chemical Classification System">ATC code</a></th><td class="infobox-data"><style data-mw-deduplicate="TemplateStyles:r1126788409">.mw-parser-output .plainlist ol,.mw-parser-output .plainlist ul{line-height:inherit;list-style:none;margin:0;padding:0}.mw-parser-output .plainlist ol li,.mw-parser-output .plainlist ul li{margin-bottom:0}</style><div class="plainlist"><ul><li>None</li></ul></div></td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd;color:inherit;">Legal status</th></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Regulation_of_therapeutic_goods" title="Regulation of therapeutic goods">Legal status</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"> <ul><li><abbr class="country-name" title="Australia">AU</abbr>: <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li>S8 (PTSD)</li><li>S9 (all other uses)</li></ul></div></li> <li><abbr class="country-name" title="Brazil">BR</abbr>: <a href="/wiki/Brazilian_Controlled_Drugs_and_Substances_Act#Class_F2" title="Brazilian Controlled Drugs and Substances Act">Class F2</a> (Prohibited psychotropics)<a href="#cite_note-12">[12]</a></li> <li><abbr class="country-name" title="Canada">CA</abbr>: <a href="/wiki/Controlled_Drugs_and_Substances_Act#Schedule_I" title="Controlled Drugs and Substances Act">Schedule I</a></li> <li><abbr class="country-name" title="Germany">DE</abbr>: <a href="/wiki/Drugs_controlled_by_the_German_Narcotic_Drugs_Act#Anlage_I" title="Drugs controlled by the German Narcotic Drugs Act">Anlage I</a> (Authorized scientific use only)</li> <li><abbr class="country-name" title="New Zealand">NZ</abbr>: <a href="/wiki/Misuse_of_Drugs_Act_1975#Class_B" title="Misuse of Drugs Act 1975">Class B</a></li> <li><abbr class="country-name" title="United Kingdom">UK</abbr>: <a href="/wiki/Drugs_controlled_by_the_UK_Misuse_of_Drugs_Act#Class_A_drugs" class="mw-redirect" title="Drugs controlled by the UK Misuse of Drugs Act">Class A</a></li> <li><abbr class="country-name" title="United States">US</abbr>: <a href="/wiki/Controlled_Substances_Act#Schedule_I_drugs" title="Controlled Substances Act">Schedule I</a></li> <li><abbr class="country-name" title="United Nations">UN</abbr>: <a href="/wiki/Convention_on_Psychotropic_Substances#Schedule_I" title="Convention on Psychotropic Substances">Psychotropic Schedule I</a></li></ul></div> </td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd;color:inherit;"><a href="/wiki/Pharmacokinetics" title="Pharmacokinetics">Pharmacokinetic</a> data</th></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Bioavailability" title="Bioavailability">Bioavailability</a></th><td class="infobox-data"><a href="/wiki/Oral_administration" title="Oral administration">Oral</a>: Unknown<a href="#cite_note-Freye2009-13">[13]</a></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Plasma_protein_binding" title="Plasma protein binding">Protein binding</a></th><td class="infobox-data">Unknown<a href="#cite_note-DrugBank-14">[14]</a></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Drug_metabolism" title="Drug metabolism">Metabolism</a></th><td class="infobox-data"><a href="/wiki/Liver" title="Liver">Liver</a>, <a href="/wiki/Cytochrome_P450_oxidase" class="mw-redirect" title="Cytochrome P450 oxidase">CYP450</a> extensively involved, including <a href="/wiki/CYP2D6" title="CYP2D6">CYP2D6</a></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Metabolite" title="Metabolite">Metabolites</a></th><td class="infobox-data"><a href="/wiki/3,4-methylenedioxyamphetamine" class="mw-redirect" title="3,4-methylenedioxyamphetamine">MDA</a>, <a href="/wiki/4-Hydroxy-3-methoxymethamphetamine" title="4-Hydroxy-3-methoxymethamphetamine">HMMA</a>, <a href="/wiki/4-Hydroxy-3-methoxyamphetamine" title="4-Hydroxy-3-methoxyamphetamine">HMA</a>, <a href="/wiki/3,4-Dihydroxymethamphetamine" title="3,4-Dihydroxymethamphetamine">HHMA</a>, <a href="/wiki/Alpha-Methyldopamine" class="mw-redirect" title="Alpha-Methyldopamine">HHA</a>, <a href="/wiki/2,4,5-Trihydroxymethamphetamine" title="2,4,5-Trihydroxymethamphetamine">THMA</a>, <a href="/wiki/2,4,5-Trihydroxyamphetamine" title="2,4,5-Trihydroxyamphetamine">THA</a>, <a href="/wiki/MDP2P" class="mw-redirect" title="MDP2P">MDP2P</a>, <a href="/wiki/Methylenedioxyhydroxyamphetamine" class="mw-redirect" title="Methylenedioxyhydroxyamphetamine">MDOH</a><a href="#cite_note-pmid22392347-15">[15]</a></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Onset_of_action" title="Onset of action">Onset of action</a></th><td class="infobox-data"><a href="/wiki/Oral_administration" title="Oral administration">Oral</a>: 30–45 min<a href="#cite_note-Freye2009-13">[13]</a></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Biological_half-life" title="Biological half-life">Elimination half-life</a></th><td class="infobox-data"><div><ul><li>MDMA: 8.7 (range 4.6–16) hours<a href="#cite_note-StraumannAvedisianKlaiber2024-16">[16]</a><a href="#cite_note-DunlapAndrewsOlson2018-17">[17]</a></li><li>(S)-MDMA: 5.1 (range 3.5–7.4) hours<a href="#cite_note-StraumannAvedisianKlaiber2024-16">[16]</a></li><li><a href="/wiki/(R)-MDMA" title="(R)-MDMA">(R)-MDMA</a>: 11 (range 5.1–24) hours<a href="#cite_note-StraumannAvedisianKlaiber2024-16">[16]</a></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Pharmacodynamics#Duration_of_action" title="Pharmacodynamics">Duration of action</a></th><td class="infobox-data">3–6 hours<a href="#cite_note-Oeri2021-18">[18]</a><a href="#cite_note-Betzler2017-8">[8]</a><a href="#cite_note-Freye2009-13">[13]</a></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Excretion" title="Excretion">Excretion</a></th><td class="infobox-data"><a href="/wiki/Kidney" title="Kidney">Kidney</a></td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd;color:inherit;">Identifiers</th></tr><tr><td colspan="2" class="infobox-full-data"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold;"><div><a href="/wiki/IUPAC_nomenclature_of_chemistry" title="IUPAC nomenclature of chemistry">IUPAC name</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all; text-align:left; padding-left:1.5em; text-indent:-1.5em;"><li style="line-height: inherit; margin: 0"><div style="font-size: 97%;">(RS)-1-(1,3-Benzodioxol-5-yl)-N-methylpropan-2-amine</div></li></ul> </div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/CAS_Registry_Number" title="CAS Registry Number">CAS Number</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=42542-10-9">42542-10-9</a> <img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" />Y[<a href="/wiki/Wikipedia:WikiProject_Chemicals/Chembox_validation" title="Wikipedia:WikiProject Chemicals/Chembox validation">TOXNET</a>]</li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/PubChem#CID" title="PubChem">PubChem</a> <abbr title="Compound ID">CID</abbr></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/1615">1615</a></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Guide_to_Pharmacology" title="Guide to Pharmacology">IUPHAR/BPS</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><a rel="nofollow" class="external text" href="https://www.guidetopharmacology.org/GRAC/LigandDisplayForward?ligandId=4574">4574</a></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/DrugBank" title="DrugBank">DrugBank</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><a rel="nofollow" class="external text" href="https://www.drugbank.ca/drugs/DB01454">DB01454</a> <img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" />Y</li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/ChemSpider" title="ChemSpider">ChemSpider</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><a rel="nofollow" class="external text" href="https://www.chemspider.com/Chemical-Structure.1556.html">1556</a> <img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" />Y</li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Unique_Ingredient_Identifier" title="Unique Ingredient Identifier">UNII</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><a rel="nofollow" class="external text" href="https://precision.fda.gov/uniisearch/srs/unii/KE1SEN21RM">KE1SEN21RM</a></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/KEGG" title="KEGG">KEGG</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><a rel="nofollow" class="external text" href="https://www.kegg.jp/entry/D11172">D11172</a> <img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" />Y</li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/ChEBI" title="ChEBI">ChEBI</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:1391">CHEBI:1391</a> <img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" />Y</li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/ChEMBL" title="ChEMBL">ChEMBL</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chembl/explore/compound/ChEMBL43048">ChEMBL43048</a> <img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" />Y</li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Protein_Data_Bank" title="Protein Data Bank">PDB ligand</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li>B41 (<a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/pdbe-srv/PDBeXplore/ligand/?ligand=B41">PDBe</a>, <a rel="nofollow" class="external text" href="https://www.rcsb.org/ligand/B41">RCSB PDB</a>)</li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/CompTox_Chemicals_Dashboard" title="CompTox Chemicals Dashboard">CompTox Dashboard</a> (<abbr title="U.S. Environmental Protection Agency">EPA</abbr>)</th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><a rel="nofollow" class="external text" href="https://comptox.epa.gov/dashboard/chemical/details/DTXSID90860791">DTXSID90860791</a> <a href="https://www.wikidata.org/wiki/Q69488#P3117" title="Edit this at Wikidata"><img alt="Edit this at Wikidata" src="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/10px-OOjs_UI_icon_edit-ltr-progressive.svg.png" decoding="async" width="10" height="10" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/15px-OOjs_UI_icon_edit-ltr-progressive.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/20px-OOjs_UI_icon_edit-ltr-progressive.svg.png 2x" data-file-width="20" data-file-height="20" /></a></li></ul></div></td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd;color:inherit;">Chemical and physical data</th></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Chemical_formula" title="Chemical formula">Formula</a></th><td class="infobox-data">C11H15NO2</td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Molar_mass" title="Molar mass">Molar mass</a></th><td class="infobox-data">193.246 g·mol−1</td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;">3D model (<a href="/wiki/JSmol" class="mw-redirect" title="JSmol">JSmol</a>)</th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><a rel="nofollow" class="external text" href="https://chemapps.stolaf.edu/jmol/jmol.php?model=CC%28NC%29CC1%3DCC%3DC%28OCO2%29C2%3DC1">Interactive image</a></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Chirality_(chemistry)" title="Chirality (chemistry)">Chirality</a></th><td class="infobox-data"><a href="/wiki/Racemic_mixture" title="Racemic mixture">Racemic mixture</a></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Density" title="Density">Density</a></th><td class="infobox-data">1.1 g/cm3</td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Boiling_point" title="Boiling point">Boiling point</a></th><td class="infobox-data">105 °C (221 °F) at 0.4 mmHg (experimental)</td></tr><tr><td colspan="2" class="infobox-full-data"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold;"><div><a href="/wiki/Simplified_molecular-input_line-entry_system" class="mw-redirect" title="Simplified molecular-input line-entry system">SMILES</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="word-wrap:break-word; text-indent:-1.5em; text-align:left; padding-left:1.5em; font-size:97%; line-height:120%;">CC(NC)CC1=CC=C(OCO2)C2=C1</div></li></ul> </div></td></tr><tr><td colspan="2" class="infobox-full-data"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold;"><div><a href="/wiki/International_Chemical_Identifier" title="International Chemical Identifier">InChI</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="word-wrap:break-word; text-indent:-1.5em; text-align:left; padding-left:1.5em; font-size:97%; line-height:120%;">InChI=1S/C11H15NO2/c1-8(12-2)5-9-3-4-10-11(6-9)14-7-13-10/h3-4,6,8,12H,5,7H2,1-2H3 <img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" />Y</div></li><li style="line-height: inherit; margin: 0"><div style="word-wrap:break-word; text-indent:-1.5em; text-align:left; padding-left:1.5em; font-size:97%; line-height:120%;">Key:SHXWCVYOXRDMCX-UHFFFAOYSA-N <img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" />Y</div></li></ul> </div></td></tr><tr><td colspan="2" class="infobox-below"><style data-mw-deduplicate="TemplateStyles:r886047488">.mw-parser-output .nobold{font-weight:normal}</style>  <a class="external text" href="https://en.wikipedia.org/w/index.php?title=Special:ComparePages&rev1=632164040&page2=MDMA">(verify)</a></td></tr></tbody></table> 3,4-Methylenedioxymethamphetamine (MDMA), commonly known as ecstasy (tablet form), and molly (crystal form),<a href="#cite_note-19">[19]</a><a href="#cite_note-20">[20]</a> is an <a href="/wiki/Empathogen%E2%80%93entactogen" class="mw-redirect" title="Empathogen–entactogen">empathogen–entactogenic</a> drug with <a href="/wiki/Stimulant" title="Stimulant">stimulant</a> and minor <a href="/wiki/Psychedelic_drug" title="Psychedelic drug">psychedelic</a> properties.<a href="#cite_note-DunlapAndrewsOlson2018-17">[17]</a><a href="#cite_note-GreenMechanElliott2003-21">[21]</a><a href="#cite_note-Current2013-22">[22]</a> In studies, it has been used alongside <a href="/wiki/Psychotherapy" title="Psychotherapy">psychotherapy</a> in the treatment of <a href="/wiki/Post-traumatic_stress_disorder" title="Post-traumatic stress disorder">post-traumatic stress disorder</a> (PTSD) and <a href="/wiki/Social_anxiety" title="Social anxiety">social anxiety</a> in <a href="/wiki/Autism" title="Autism">autism spectrum disorder</a>.<a href="#cite_note-23">[23]</a><a href="#cite_note-:1-24">[24]</a><a href="#cite_note-:2-25">[25]</a> The purported pharmacological effects that may be <a href="/wiki/Prosocial_behavior" title="Prosocial behavior">prosocial</a> include altered sensations, increased energy, empathy, and pleasure.<a href="#cite_note-Current2013-22">[22]</a><a href="#cite_note-Drugs2014-26">[26]</a> When taken by mouth, effects begin in 30 to 45 minutes and last three to six hours.<a href="#cite_note-Freye2009-13">[13]</a><a href="#cite_note-NIH2016-27">[27]</a> MDMA was first synthesized in 1912 by <a href="/wiki/Merck_Group" title="Merck Group">Merck</a> chemist <a href="/wiki/Anton_K%C3%B6llisch" title="Anton Köllisch">Anton Köllisch</a>.<a href="#cite_note-Merck-28">[28]</a> It was used to enhance psychotherapy beginning in the 1970s and became popular as a street drug in the 1980s.<a href="#cite_note-Drugs2014-26">[26]</a><a href="#cite_note-NIH2016-27">[27]</a> MDMA is commonly associated with <a href="/wiki/Dance_party" title="Dance party">dance parties</a>, <a href="/wiki/Rave" title="Rave">raves</a>, and <a href="/wiki/Electronic_dance_music" title="Electronic dance music">electronic dance music</a>.<a href="#cite_note-WHO2004-29">[29]</a> Tablets sold as ecstasy may be <a href="/wiki/Cutting_agent" class="mw-redirect" title="Cutting agent">mixed</a> with other substances such as <a href="/wiki/Ephedrine" title="Ephedrine">ephedrine</a>, <a href="/wiki/Amphetamine" title="Amphetamine">amphetamine</a>, and <a href="/wiki/Methamphetamine" title="Methamphetamine">methamphetamine</a>.<a href="#cite_note-Drugs2014-26">[26]</a> In 2016, about 21 million people between the ages of 15 and 64 used ecstasy (0.3% of the world population).<a href="#cite_note-UN2018-30">[30]</a> This was broadly similar to the percentage of people who use <a href="/wiki/Cocaine" title="Cocaine">cocaine</a> or <a href="/wiki/Substituted_amphetamine" title="Substituted amphetamine">amphetamines</a>, but lower than for <a href="/wiki/Cannabis_(drug)" title="Cannabis (drug)">cannabis</a> or <a href="/wiki/Opioid" title="Opioid">opioids</a>.<a href="#cite_note-UN2018-30">[30]</a> In the United States, as of 2017, about 7% of people have used MDMA at some point in their lives and 0.9% have used it in the last year.<a href="#cite_note-31">[31]</a> The lethal risk from one dose of MDMA is estimated to be from 1 death in 20,000 instances to 1 death in 50,000 instances.<a href="#cite_note-32">[32]</a> Short-term adverse effects include <a href="/wiki/Bruxism" title="Bruxism">grinding of the teeth</a>, <a href="/wiki/Blurred_vision" title="Blurred vision">blurred vision</a>, <a href="/wiki/Sweating" class="mw-redirect" title="Sweating">sweating</a>, and a <a href="/wiki/Tachycardia" title="Tachycardia">rapid heartbeat</a>,<a href="#cite_note-Drugs2014-26">[26]</a> and extended use can also lead to addiction, <a href="/wiki/Amnesia" title="Amnesia">memory problems</a>, <a href="/wiki/Paranoia" title="Paranoia">paranoia</a>, and <a href="/wiki/Insomnia" title="Insomnia">difficulty sleeping</a>. Deaths have been reported due to increased body temperature and dehydration. Following use, people often feel <a href="/wiki/Depression_(mood)" title="Depression (mood)">depressed</a> and tired, although this effect does not appear in clinical use, suggesting that it is not a direct result of MDMA administration.<a href="#cite_note-Drugs2014-26">[26]</a><a href="#cite_note-33">[33]</a> MDMA acts primarily by increasing the release of the <a href="/wiki/Neurotransmitters" class="mw-redirect" title="Neurotransmitters">neurotransmitters</a> <a href="/wiki/Serotonin" title="Serotonin">serotonin</a>, <a href="/wiki/Dopamine" title="Dopamine">dopamine</a>, and <a href="/wiki/Norepinephrine" title="Norepinephrine">norepinephrine</a> in parts of the brain.<a href="#cite_note-Drugs2014-26">[26]</a><a href="#cite_note-NIH2016-27">[27]</a> It belongs to the <a href="/wiki/Substituted_amphetamine" title="Substituted amphetamine">substituted amphetamine</a> <a href="/wiki/Chemical_classification" class="mw-redirect" title="Chemical classification">classes of drugs</a>.<a href="#cite_note-EU2015-10">[10]</a><a href="#cite_note-34">[34]</a> MDMA is structurally similar to <a href="/wiki/Mescaline" title="Mescaline">mescaline</a> (a psychedelic), methamphetamine (a stimulant), as well as <a href="/wiki/Endogeny_(biology)" title="Endogeny (biology)">endogenous</a> <a href="/wiki/Monoamine_neurotransmitter" title="Monoamine neurotransmitter">monoamine neurotransmitters</a> such as serotonin, norepinephrine, and dopamine.<a href="#cite_note-35">[35]</a> MDMA has limited approved medical uses in a small number of countries,<a href="#cite_note-36">[36]</a> but is illegal in most jurisdictions.<a href="#cite_note-37">[37]</a> In the United States, the <a href="/wiki/Food_and_Drug_Administration" title="Food and Drug Administration">Food and Drug Administration</a> (FDA) is evaluating the drug for clinical use as of 2021<a class="external text" href="https://en.wikipedia.org/w/index.php?title=MDMA&action=edit">[update]</a>.<a href="#cite_note-38">[38]</a> Canada has allowed limited distribution of MDMA upon application to and approval by <a href="/wiki/Health_Canada" title="Health Canada">Health Canada</a>.<a href="#cite_note-39">[39]</a><a href="#cite_note-40">[40]</a> In Australia, it may be prescribed in the treatment of PTSD by specifically authorised psychiatrists.<a href="#cite_note-41">[41]</a> <style data-mw-deduplicate="TemplateStyles:r886046785">.mw-parser-output .toclimit-2 .toclevel-1 ul,.mw-parser-output .toclimit-3 .toclevel-2 ul,.mw-parser-output .toclimit-4 .toclevel-3 ul,.mw-parser-output .toclimit-5 .toclevel-4 ul,.mw-parser-output .toclimit-6 .toclevel-5 ul,.mw-parser-output .toclimit-7 .toclevel-6 ul{display:none}</style><div class="toclimit-3"><meta property="mw:PageProp/toc" /></div> <div class="mw-heading mw-heading2"><h2 id="Effects">Effects</h2></div> In general, MDMA users report feeling the onset of subjective effects within 30 to 60 minutes of oral consumption and reaching peak effect at 75 to 120 minutes, which then plateaus for about 3.5 hours.<a href="#cite_note-mcn-42">[42]</a> The desired short-term psychoactive effects of MDMA have been reported to include: <ul><li><a href="/wiki/Euphoria" title="Euphoria">Euphoria</a> – a sense of general <a href="/wiki/Well-being" title="Well-being">well-being</a> and happiness<a href="#cite_note-Current2013-22">[22]</a><a href="#cite_note-Acute_amph_toxicity-43">[43]</a></li> <li>Increased self-confidence, sociability, and perception of facilitated communication<a href="#cite_note-Betzler2017-8">[8]</a><a href="#cite_note-Current2013-22">[22]</a><a href="#cite_note-Acute_amph_toxicity-43">[43]</a></li> <li><a href="/wiki/Entactogen" class="mw-redirect" title="Entactogen">Entactogenic</a> effects—increased <a href="/wiki/Empathy" title="Empathy">empathy</a> or feelings of closeness with others<a href="#cite_note-Current2013-22">[22]</a><a href="#cite_note-Acute_amph_toxicity-43">[43]</a> and oneself<a href="#cite_note-Betzler2017-8">[8]</a></li> <li><a href="/wiki/Mydriasis" title="Mydriasis">Dilated pupils</a><a href="#cite_note-Betzler2017-8">[8]</a></li> <li>Relaxation and reduced anxiety<a href="#cite_note-Betzler2017-8">[8]</a></li> <li>Increased emotionality<a href="#cite_note-Betzler2017-8">[8]</a></li> <li>A sense of inner peace<a href="#cite_note-Acute_amph_toxicity-43">[43]</a></li> <li>Mild hallucination<a href="#cite_note-Acute_amph_toxicity-43">[43]</a></li> <li>Enhanced sensation, perception, or sexuality<a href="#cite_note-Betzler2017-8">[8]</a><a href="#cite_note-Current2013-22">[22]</a><a href="#cite_note-Acute_amph_toxicity-43">[43]</a></li> <li>Altered sense of time<a href="#cite_note-NIH2016-27">[27]</a></li></ul> The experience elicited by MDMA depends on the dose, setting, and user.<a href="#cite_note-Betzler2017-8">[8]</a> The variability of the induced altered state is lower compared to other psychedelics. For example, MDMA used at parties is associated with high motor activity, reduced sense of identity, and poor awareness of surroundings. Use of MDMA individually or in small groups in a quiet environment and when concentrating, is associated with increased lucidity, concentration, sensitivity to aesthetic aspects of the environment, enhanced awareness of emotions, and improved capability of communication.<a href="#cite_note-pmid22392347-15">[15]</a><a href="#cite_note-Landriscina-44">[44]</a> In psychotherapeutic settings, MDMA effects have been characterized by infantile ideas, mood lability, and memories and moods connected with childhood experiences.<a href="#cite_note-Landriscina-44">[44]</a><a href="#cite_note-Baggott-45">[45]</a> MDMA has been described as an "empathogenic" drug because of its empathy-producing effects.<a href="#cite_note-Schmid-46">[46]</a><a href="#cite_note-Wardle-47">[47]</a> Results of several studies show the effects of increased empathy with others.<a href="#cite_note-Schmid-46">[46]</a> When testing MDMA for medium and high doses, it showed increased hedonic and arousal continuum.<a href="#cite_note-Bravo-48">[48]</a><a href="#cite_note-Metzner-49">[49]</a> The effect of MDMA increasing sociability is consistent, while its effects on empathy have been more mixed.<a href="#cite_note-50">[50]</a> <div class="mw-heading mw-heading2"><h2 id="Uses">Uses</h2></div> <div class="mw-heading mw-heading3"><h3 id="Recreational">Recreational</h3></div> MDMA is often considered the drug of choice within the <a href="/wiki/Rave" title="Rave">rave</a> culture and is also used at clubs, festivals, and <a href="/wiki/House_party" title="House party">house parties</a>.<a href="#cite_note-pmid22392347-15">[15]</a> In the rave environment, the sensory effects of music and lighting are often highly <a href="/wiki/Synergy" title="Synergy">synergistic</a> with the drug. The psychedelic <a href="/wiki/Amphetamine" title="Amphetamine">amphetamine</a> quality of MDMA offers multiple appealing aspects to users in the rave setting. Some users enjoy the feeling of mass communion from the inhibition-reducing effects of the drug, while others use it as party fuel because of the drug's stimulatory effects.<a href="#cite_note-51">[51]</a> MDMA is used less often than other stimulants, typically less than once per week.<a href="#cite_note-Epstein2013-52">[52]</a> MDMA is sometimes taken in conjunction with other psychoactive drugs such as <a href="/wiki/LSD" title="LSD">LSD</a>,<a href="#cite_note-:0-53">[53]</a> <a href="/wiki/Psilocybin_mushroom" title="Psilocybin mushroom">psilocybin mushrooms</a>, <a href="/wiki/2C-B" title="2C-B">2C-B</a>, and <a href="/wiki/Ketamine" title="Ketamine">ketamine</a>. The combination with LSD is called "candy-flipping".<a href="#cite_note-:0-53">[53]</a> The combination with 2C-B is called "nexus flipping". For this combination, most people take the MDMA first, wait until the peak is over, and then take the 2C-B.<a href="#cite_note-54">[54]</a> MDMA is often co-administered with <a href="/wiki/Alcohol_(drug)" title="Alcohol (drug)">alcohol</a>, <a href="/wiki/Methamphetamine" title="Methamphetamine">methamphetamine</a>, and prescription drugs such as <a href="/wiki/Selective_serotonin_reuptake_inhibitor" title="Selective serotonin reuptake inhibitor">SSRIs</a> with which MDMA has several drug-drug interactions.<a href="#cite_note-HysekSimmlerNicola2012-55">[55]</a><a href="#cite_note-56">[56]</a><a href="#cite_note-57">[57]</a> Three life-threatening reports of MDMA co-administration with <a href="/wiki/Ritonavir" title="Ritonavir">ritonavir</a> have been reported;<a href="#cite_note-58">[58]</a> with ritonavir having severe and dangerous drug-drug interactions with a wide range of both psychoactive, anti-psychotic, and non-psychoactive drugs.<a href="#cite_note-pmid31038898-59">[59]</a> <div class="mw-heading mw-heading3"><h3 id="Medical">Medical</h3></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951" /><div role="note" class="hatnote navigation-not-searchable">See also: <a class="mw-selflink-fragment" href="#Research_directions">MDMA § Research directions</a>, and <a href="/wiki/MDMA-assisted_psychotherapy" title="MDMA-assisted psychotherapy">MDMA-assisted psychotherapy</a></div> As of 2023, MDMA therapies have only been approved for research purposes, with no widely accepted <a href="/wiki/Medical_indication" class="mw-redirect" title="Medical indication">medical indications</a>,<a href="#cite_note-EU2015-10">[10]</a><a href="#cite_note-60">[60]</a><a href="#cite_note-61">[61]</a> although this varies by jurisdiction. Before it was widely banned, it saw limited use in psychotherapy.<a href="#cite_note-Betzler2017-8">[8]</a><a href="#cite_note-EU2015-10">[10]</a><a href="#cite_note-62">[62]</a> In 2017 the <a href="/wiki/United_States_Food_and_Drug_Administration" class="mw-redirect" title="United States Food and Drug Administration">United States Food and Drug Administration</a> (FDA) granted breakthrough therapy designation for MDMA-assisted psychotherapy for <a href="/wiki/Post-traumatic_stress_disorder" title="Post-traumatic stress disorder">post-traumatic stress disorder</a> (PTSD),<a href="#cite_note-63">[63]</a><a href="#cite_note-64">[64]</a> with some preliminary evidence that MDMA may facilitate psychotherapy efficacy for PTSD.<a href="#cite_note-Zarembo-65">[65]</a><a href="#cite_note-66">[66]</a> Pilot studies indicate that <a href="/wiki/MDMA-assisted_psychotherapy" title="MDMA-assisted psychotherapy">MDMA-assisted psychotherapy</a> may be beneficial in treating <a href="/wiki/Social_anxiety" title="Social anxiety">social anxiety</a> in <a href="/wiki/Autism" title="Autism">autistic adults</a>.<a href="#cite_note-:1-24">[24]</a><a href="#cite_note-:2-25">[25]</a> In these pilot studies, the vast majority of participants reported increased feelings of empathy that persisted after the therapy sessions.<a href="#cite_note-67">[67]</a> Some have proposed that psychedelics in general may act as <a href="/wiki/Active_placebo" title="Active placebo">active</a> "super <a href="/wiki/Placebo" title="Placebo">placebos</a>" used for therapeutic purposes.<a href="#cite_note-DupuisVeissière2022-68">[68]</a><a href="#cite_note-vanElkYaden2022-69">[69]</a> <div class="mw-heading mw-heading3"><h3 id="Other">Other</h3></div> Small doses of MDMA are used by some religious practitioners as an <a href="/wiki/Entheogen" title="Entheogen">entheogen</a> to enhance prayer or meditation.<a href="#cite_note-MDMA_and_Religion-70">[70]</a> MDMA has been used as an adjunct to <a href="/wiki/New_Age" title="New Age">New Age</a> spiritual practices.<a href="#cite_note-Watson_&_Beck-71">[71]</a> <div class="mw-heading mw-heading3"><h3 id="Forms">Forms</h3></div> MDMA has become widely known as ecstasy (shortened "E", "X", or "XTC"), usually referring to its tablet form, although this term may also include the presence of possible <a href="/wiki/Adulterant" title="Adulterant">adulterants</a> or diluents. The UK term "mandy" and the US term "molly" colloquially refer to MDMA in a crystalline powder form that is thought to be free of adulterants.<a href="#cite_note-nature.com-2">[2]</a><a href="#cite_note-DrugFacts-3">[3]</a><a href="#cite_note-DEA_2015_assessment-72">[72]</a> MDMA is also sold in the form of the hydrochloride salt, either as loose crystals or in <a href="/wiki/Capsule_(pharmacy)" title="Capsule (pharmacy)">gelcaps</a>.<a href="#cite_note-Molly_S05E07-73">[73]</a><a href="#cite_note-Molly_S06E05-74">[74]</a> MDMA tablets can sometimes be found in a shaped form that may depict characters from <a href="/wiki/Popular_culture" title="Popular culture">popular culture</a>. These are sometimes collectively referred to as "fun tablets".<a href="#cite_note-75">[75]</a><a href="#cite_note-76">[76]</a> Partly due to the global supply shortage of <a href="/wiki/Sassafras_oil" class="mw-redirect" title="Sassafras oil">sassafras oil</a>—a problem largely assuaged by use of improved or alternative modern methods of synthesis—the purity of substances sold as molly have been found to vary widely. Some of these substances contain <a href="/wiki/Methylone" title="Methylone">methylone</a>, <a href="/wiki/Ethylone" title="Ethylone">ethylone</a>, <a href="/wiki/MDPV" class="mw-redirect" title="MDPV">MDPV</a>, <a href="/wiki/Mephedrone" title="Mephedrone">mephedrone</a>, or any other of the group of compounds commonly known as <a href="/wiki/Bath_salts_(drug)" title="Bath salts (drug)">bath salts</a>, in addition to, or in place of, MDMA.<a href="#cite_note-DrugFacts-3">[3]</a><a href="#cite_note-DEA_2015_assessment-72">[72]</a><a href="#cite_note-Molly_S05E07-73">[73]</a><a href="#cite_note-Molly_S06E05-74">[74]</a> Powdered MDMA ranges from pure MDMA to crushed tablets with 30–40% purity.<a href="#cite_note-EU2015-10">[10]</a> MDMA tablets typically have low purity due to bulking agents that are added to dilute the drug and increase profits (notably lactose) and binding agents.<a href="#cite_note-EU2015-10">[10]</a> Tablets sold as ecstasy sometimes contain <a href="/wiki/3,4-methylenedioxyamphetamine" class="mw-redirect" title="3,4-methylenedioxyamphetamine">3,4-methylenedioxyamphetamine</a> (MDA), <a href="/wiki/3,4-methylenedioxyethylamphetamine" class="mw-redirect" title="3,4-methylenedioxyethylamphetamine">3,4-methylenedioxyethylamphetamine</a> (MDEA), other amphetamine derivatives, caffeine, opiates, or painkillers.<a href="#cite_note-Betzler2017-8">[8]</a> Some tablets contain little or no MDMA.<a href="#cite_note-Betzler2017-8">[8]</a><a href="#cite_note-EU2015-10">[10]</a><a href="#cite_note-Toxnet_MDMA_after-effects-77">[77]</a> The proportion of seized ecstasy tablets with MDMA-like impurities has varied annually and by country.<a href="#cite_note-EU2015-10">[10]</a> The average content of MDMA in a preparation is 70 to 120 mg with the purity having increased since the 1990s.<a href="#cite_note-Betzler2017-8">[8]</a> MDMA is usually consumed by mouth. It is also sometimes <a href="/wiki/Insufflation_(medicine)" title="Insufflation (medicine)">snorted</a>.<a href="#cite_note-Drugs2014-26">[26]</a> <style data-mw-deduplicate="TemplateStyles:r1273380762/mw-parser-output/.tmulti">.mw-parser-output .tmulti .multiimageinner{display:flex;flex-direction:column}.mw-parser-output .tmulti .trow{display:flex;flex-direction:row;clear:left;flex-wrap:wrap;width:100%;box-sizing:border-box}.mw-parser-output .tmulti .tsingle{margin:1px;float:left}.mw-parser-output .tmulti .theader{clear:both;font-weight:bold;text-align:center;align-self:center;background-color:transparent;width:100%}.mw-parser-output .tmulti .thumbcaption{background-color:transparent}.mw-parser-output .tmulti .text-align-left{text-align:left}.mw-parser-output .tmulti .text-align-right{text-align:right}.mw-parser-output .tmulti .text-align-center{text-align:center}@media all and (max-width:720px){.mw-parser-output .tmulti .thumbinner{width:100%!important;box-sizing:border-box;max-width:none!important;align-items:center}.mw-parser-output .tmulti .trow{justify-content:center}.mw-parser-output .tmulti .tsingle{float:none!important;max-width:100%!important;box-sizing:border-box;text-align:center}.mw-parser-output .tmulti .tsingle .thumbcaption{text-align:left}.mw-parser-output .tmulti .trow>.thumbcaption{text-align:center}}@media screen{html.skin-theme-clientpref-night .mw-parser-output .tmulti .multiimageinner span:not(.skin-invert-image):not(.skin-invert):not(.bg-transparent) img{background-color:white}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .tmulti .multiimageinner span:not(.skin-invert-image):not(.skin-invert):not(.bg-transparent) img{background-color:white}}</style><div class="thumb tmulti tnone center"><div class="thumbinner multiimageinner" style="width:593px;max-width:593px"><div class="trow"><div class="tsingle" style="width:163px;max-width:163px"><div class="thumbimage" style="height:157px;overflow:hidden"><a href="/wiki/File:Ecstasy_monogram.jpg" class="mw-file-description"><img alt="Image of Ecstasy tablets" src="//upload.wikimedia.org/wikipedia/commons/thumb/7/7e/Ecstasy_monogram.jpg/161px-Ecstasy_monogram.jpg" decoding="async" width="161" height="157" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/7/7e/Ecstasy_monogram.jpg/242px-Ecstasy_monogram.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/7/7e/Ecstasy_monogram.jpg/322px-Ecstasy_monogram.jpg 2x" data-file-width="434" data-file-height="424" /></a></div><div class="thumbcaption">Ecstasy tablets which may contain MDMA</div></div><div class="tsingle" style="width:212px;max-width:212px"><div class="thumbimage" style="height:157px;overflow:hidden"><a href="/wiki/File:Tan_MDMA_Crystals.jpg" class="mw-file-description"><img alt="Image of a chunk of impure MDMA" src="//upload.wikimedia.org/wikipedia/commons/thumb/4/46/Tan_MDMA_Crystals.jpg/210px-Tan_MDMA_Crystals.jpg" decoding="async" width="210" height="158" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/4/46/Tan_MDMA_Crystals.jpg/315px-Tan_MDMA_Crystals.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/4/46/Tan_MDMA_Crystals.jpg/420px-Tan_MDMA_Crystals.jpg 2x" data-file-width="4032" data-file-height="3024" /></a></div><div class="thumbcaption">A salt of MDMA (typically white) with impurities, resulting in a tan discoloration</div></div><div class="tsingle" style="width:212px;max-width:212px"><div class="thumbimage" style="height:157px;overflow:hidden"><a href="/wiki/File:Crushed_MDMA_crystals.jpg" class="mw-file-description"><img alt="1 gram crushed MDMA crystals" src="//upload.wikimedia.org/wikipedia/commons/thumb/9/9b/Crushed_MDMA_crystals.jpg/210px-Crushed_MDMA_crystals.jpg" decoding="async" width="210" height="157" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/9/9b/Crushed_MDMA_crystals.jpg/315px-Crushed_MDMA_crystals.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/9/9b/Crushed_MDMA_crystals.jpg/420px-Crushed_MDMA_crystals.jpg 2x" data-file-width="640" data-file-height="478" /></a></div><div class="thumbcaption">Crushed MDMA (1 gram) crystals</div></div></div></div></div> <div class="mw-heading mw-heading2"><h2 id="Adverse_effects">Adverse effects</h2></div> <div class="mw-heading mw-heading3"><h3 id="Short-term">Short-term</h3></div> Acute adverse effects are usually the result of high or multiple doses, although single dose toxicity can occur in susceptible individuals.<a href="#cite_note-Current2013-22">[22]</a> The most serious short-term physical health risks of MDMA are <a href="/wiki/Hyperthermia" title="Hyperthermia">hyperthermia</a> and <a href="/wiki/Dehydration" title="Dehydration">dehydration</a>.<a href="#cite_note-Acute_amph_toxicity-43">[43]</a><a href="#cite_note-Hyponatremia-78">[78]</a> Cases of life-threatening or fatal <a href="/wiki/Hyponatremia" title="Hyponatremia">hyponatremia</a> (excessively low sodium concentration in the blood) have developed in MDMA users attempting to prevent dehydration by <a href="/wiki/Water_intoxication" title="Water intoxication">consuming excessive amounts of water</a> without replenishing <a href="/wiki/Electrolytes" class="mw-redirect" title="Electrolytes">electrolytes</a>.<a href="#cite_note-Acute_amph_toxicity-43">[43]</a><a href="#cite_note-Hyponatremia-78">[78]</a><a href="#cite_note-hyperpyrexia-79">[79]</a> The immediate adverse effects of MDMA use can include: <style data-mw-deduplicate="TemplateStyles:r1184024115">.mw-parser-output .div-col{margin-top:0.3em;column-width:30em}.mw-parser-output .div-col-small{font-size:90%}.mw-parser-output .div-col-rules{column-rule:1px solid #aaa}.mw-parser-output .div-col dl,.mw-parser-output .div-col ol,.mw-parser-output .div-col ul{margin-top:0}.mw-parser-output .div-col li,.mw-parser-output .div-col dd{page-break-inside:avoid;break-inside:avoid-column}</style><div class="div-col" style="column-width: 27em;"> <ul><li><a href="/wiki/Bruxism" title="Bruxism">Bruxism</a> (grinding and clenching of the teeth)<a href="#cite_note-Betzler2017-8">[8]</a><a href="#cite_note-pmid22392347-15">[15]</a><a href="#cite_note-Current2013-22">[22]</a></li> <li><a href="/wiki/Dehydration" title="Dehydration">Dehydration</a><a href="#cite_note-pmid22392347-15">[15]</a><a href="#cite_note-Acute_amph_toxicity-43">[43]</a><a href="#cite_note-Hyponatremia-78">[78]</a></li> <li><a href="/wiki/Diarrhea" title="Diarrhea">Diarrhea</a><a href="#cite_note-Acute_amph_toxicity-43">[43]</a></li> <li><a href="/wiki/Erectile_dysfunction" title="Erectile dysfunction">Erectile dysfunction</a><a href="#cite_note-Betzler2017-8">[8]</a><a href="#cite_note-80">[80]</a></li> <li><a href="/wiki/Hyperthermia" title="Hyperthermia">Hyperthermia</a><a href="#cite_note-Betzler2017-8">[8]</a><a href="#cite_note-pmid22392347-15">[15]</a><a href="#cite_note-Hyponatremia-78">[78]</a></li> <li>Increased wakefulness or <a href="/wiki/Insomnia" title="Insomnia">insomnia</a><a href="#cite_note-Betzler2017-8">[8]</a><a href="#cite_note-Acute_amph_toxicity-43">[43]</a></li> <li>Increased perspiration and sweating<a href="#cite_note-Acute_amph_toxicity-43">[43]</a><a href="#cite_note-Hyponatremia-78">[78]</a></li> <li>Increased <a href="/wiki/Heart_rate" title="Heart rate">heart rate</a> and <a href="/wiki/Blood_pressure" title="Blood pressure">blood pressure</a><a href="#cite_note-Betzler2017-8">[8]</a><a href="#cite_note-pmid22392347-15">[15]</a><a href="#cite_note-Hyponatremia-78">[78]</a></li> <li>Increased <a href="/wiki/Psychomotor_agitation" title="Psychomotor agitation">psychomotor</a> activity<a href="#cite_note-Betzler2017-8">[8]</a></li> <li>Loss of <a href="/wiki/Appetite" title="Appetite">appetite</a><a href="#cite_note-Betzler2017-8">[8]</a><a href="#cite_note-Toxnet_MDMA_after-effects-77">[77]</a></li> <li>Nausea and vomiting<a href="#cite_note-Current2013-22">[22]</a></li> <li>Visual and auditory hallucinations (rarely)<a href="#cite_note-Betzler2017-8">[8]</a></li></ul> </div> Other adverse effects that may occur or persist for up to a week following cessation of moderate MDMA use include:<a href="#cite_note-Toxnet_MDMA_after-effects-77">[77]</a><a href="#cite_note-Current2013-22">[22]</a> <dl><dt>Physiological</dt></dl> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1184024115" /><div class="div-col" style="column-width: 18em;"> <ul><li>Insomnia<a href="#cite_note-Toxnet_MDMA_after-effects-77">[77]</a></li> <li>Loss of appetite<a href="#cite_note-Toxnet_MDMA_after-effects-77">[77]</a></li> <li>Tiredness or lethargy<a href="#cite_note-81">[81]</a><a href="#cite_note-82">[82]</a></li> <li><a href="/wiki/Trismus" title="Trismus">Trismus</a> (lockjaw)<a href="#cite_note-Current2013-22">[22]</a></li></ul> </div> <dl><dt>Psychological</dt></dl> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1184024115" /><div class="div-col" style="column-width: 18em;"> <ul><li><a href="/wiki/Anhedonia" title="Anhedonia">Anhedonia</a><a href="#cite_note-Toxnet_MDMA_after-effects-77">[77]</a></li> <li>Anxiety or paranoia<a href="#cite_note-Toxnet_MDMA_after-effects-77">[77]</a></li> <li>Depression<a href="#cite_note-Toxnet_MDMA_after-effects-77">[77]</a><a href="#cite_note-Current2013-22">[22]</a></li> <li>Impulsiveness<a href="#cite_note-Toxnet_MDMA_after-effects-77">[77]</a></li> <li>Irritability<a href="#cite_note-Toxnet_MDMA_after-effects-77">[77]</a></li> <li>Memory impairment<a href="#cite_note-Current2013-22">[22]</a></li> <li>Restlessness<a href="#cite_note-Toxnet_MDMA_after-effects-77">[77]</a></li></ul> </div> Administration of MDMA to mice causes <a href="/wiki/DNA_damage_(naturally_occurring)" title="DNA damage (naturally occurring)">DNA damage</a> in their brain,<a href="#cite_note-83">[83]</a> especially when the mice are sleep deprived.<a href="#cite_note-84">[84]</a> Even at the very low doses that are comparable to those self-administered by humans, MDMA causes <a href="/wiki/Oxidative_stress" title="Oxidative stress">oxidative stress</a> and both <a href="/wiki/DNA_damage_(naturally_occurring)" title="DNA damage (naturally occurring)">single and double-strand breaks in the DNA</a> of the <a href="/wiki/Hippocampus" title="Hippocampus">hippocampus</a> region of the mouse brain.<a href="#cite_note-85">[85]</a> <div class="mw-heading mw-heading3"><h3 id="Long-term">Long-term</h3></div> As of 2015<a class="external text" href="https://en.wikipedia.org/w/index.php?title=MDMA&action=edit">[update]</a>, the long-term effects of MDMA on human brain structure and function have not been fully determined.<a href="#cite_note-Abstinent_MDMA_fMRI_review-86">[86]</a> However, there is consistent evidence of structural and functional deficits in MDMA users with high lifetime exposure.<a href="#cite_note-Abstinent_MDMA_fMRI_review-86">[86]</a> These structural or functional changes appear to be dose dependent and may be less prominent in MDMA users with only a moderate (typically <50 doses used and <100 tablets consumed) lifetime exposure. Nonetheless, moderate MDMA use may still be <a href="/wiki/Neurotoxicity" title="Neurotoxicity">neurotoxic</a> and what constitutes moderate use is not clearly established.<a href="#cite_note-mueller2015-87">[87]</a> Furthermore, it is not clear yet whether "typical" recreational users of MDMA (1 to 2 pills of 75 to 125 mg MDMA or analogue every 1 to 4 weeks) will develop neurotoxic brain lesions.<a href="#cite_note-88">[88]</a> Long-term exposure to MDMA in humans has been shown to produce marked <a href="/wiki/Neurodegeneration" class="mw-redirect" title="Neurodegeneration">neurodegeneration</a> in <a href="/wiki/Striatal" class="mw-redirect" title="Striatal">striatal</a>, <a href="/wiki/Hippocampal" class="mw-redirect" title="Hippocampal">hippocampal</a>, <a href="/wiki/Prefrontal_cortex" title="Prefrontal cortex">prefrontal</a>, and <a href="/wiki/Occipital_cortex" class="mw-redirect" title="Occipital cortex">occipital</a> serotonergic <a href="/wiki/Axon_terminal" title="Axon terminal">axon terminals</a>.<a href="#cite_note-Abstinent_MDMA_fMRI_review-86">[86]</a><a href="#cite_note-Meth_MDMA_NTox-89">[89]</a> Neurotoxic damage to serotonergic axon terminals has been shown to persist for more than two years.<a href="#cite_note-Meth_MDMA_NTox-89">[89]</a> Elevations in brain temperature from MDMA use are positively correlated with MDMA-induced neurotoxicity.<a href="#cite_note-pmid22392347-15">[15]</a><a href="#cite_note-Abstinent_MDMA_fMRI_review-86">[86]</a><a href="#cite_note-mueller2015-87">[87]</a> However, most studies on MDMA and serotonergic neurotoxicity in humans focus more on heavy users who consume as much as seven times or more the amount that most users report taking. The evidence for the presence of serotonergic neurotoxicity in casual users who take lower doses less frequently is not conclusive.<a href="#cite_note-90">[90]</a> However, adverse <a href="/wiki/Neuroplastic" class="mw-redirect" title="Neuroplastic">neuroplastic</a> changes to brain <a href="/wiki/Microvasculature" class="mw-redirect" title="Microvasculature">microvasculature</a> and <a href="/wiki/White_matter" title="White matter">white matter</a> have been observed to occur in humans using low doses of MDMA.<a href="#cite_note-pmid22392347-15">[15]</a><a href="#cite_note-Abstinent_MDMA_fMRI_review-86">[86]</a> Reduced <a href="/wiki/Gray_matter" class="mw-redirect" title="Gray matter">gray matter</a> density in certain brain structures has also been noted in human MDMA users.<a href="#cite_note-pmid22392347-15">[15]</a><a href="#cite_note-Abstinent_MDMA_fMRI_review-86">[86]</a> Global reductions in gray matter volume, thinning of the parietal and orbitofrontal cortices, and decreased hippocampal activity have been observed in long term users.<a href="#cite_note-Betzler2017-8">[8]</a> The effects established so far for recreational use of ecstasy lie in the range of moderate to severe effects for <a href="/wiki/Serotonin_transporter" title="Serotonin transporter">serotonin transporter</a> reduction.<a href="#cite_note-91">[91]</a> Impairments in multiple aspects of cognition, including attention, learning, memory, <a href="/wiki/Role_of_serotonin_in_visual_orientation_processing#MDMA_and_Visual_Orientation_Processing" title="Role of serotonin in visual orientation processing">visual processing</a>, and sleep, have been found in regular MDMA users.<a href="#cite_note-Betzler2017-8">[8]</a><a href="#cite_note-Current2013-22">[22]</a><a href="#cite_note-Pharm2014-92">[92]</a><a href="#cite_note-Abstinent_MDMA_fMRI_review-86">[86]</a> The magnitude of these impairments is correlated with lifetime MDMA usage<a href="#cite_note-Current2013-22">[22]</a><a href="#cite_note-Pharm2014-92">[92]</a><a href="#cite_note-Abstinent_MDMA_fMRI_review-86">[86]</a> and are partially reversible with abstinence.<a href="#cite_note-Betzler2017-8">[8]</a> Several forms of memory are impaired by chronic ecstasy use;<a href="#cite_note-Current2013-22">[22]</a><a href="#cite_note-Pharm2014-92">[92]</a> however, the effects for memory impairments in ecstasy users are generally small overall.<a href="#cite_note-93">[93]</a><a href="#cite_note-Meta_analysis_-_MDMA_memory_impairment-94">[94]</a> MDMA use is also associated with increased impulsivity and depression.<a href="#cite_note-Betzler2017-8">[8]</a> Serotonin depletion following MDMA use can cause depression in subsequent days. In some cases, depressive symptoms persist for longer periods.<a href="#cite_note-Betzler2017-8">[8]</a> Some studies indicate repeated recreational use of ecstasy is associated with depression and anxiety, even after quitting the drug.<a href="#cite_note-95">[95]</a> Depression is one of the main reasons for cessation of use.<a href="#cite_note-Betzler2017-8">[8]</a> At high doses, MDMA induces a <a href="/wiki/Neuroimmune_system" title="Neuroimmune system">neuroimmune response</a> that, through several mechanisms, increases the permeability of the <a href="/wiki/Blood%E2%80%93brain_barrier" title="Blood–brain barrier">blood–brain barrier</a>, thereby making the brain more susceptible to environmental toxins and <a href="/wiki/Pathogen" title="Pathogen">pathogens</a>.<a href="#cite_note-MDMA_BBB-96">[96]</a><a href="#cite_note-97">[97]</a>[<a href="/wiki/Wikipedia:Citing_sources" title="Wikipedia:Citing sources">page needed</a>] In addition, MDMA has <a href="/wiki/Immunosuppressive" class="mw-redirect" title="Immunosuppressive">immunosuppressive</a> effects in the <a href="/wiki/Peripheral_nervous_system" title="Peripheral nervous system">peripheral nervous system</a> and pro-inflammatory effects in the <a href="/wiki/Central_nervous_system" title="Central nervous system">central nervous system</a>.<a href="#cite_note-98">[98]</a> MDMA may increase the risk of <a href="/wiki/Cardiac_valvulopathy" class="mw-redirect" title="Cardiac valvulopathy">cardiac valvulopathy</a> in heavy or long-term users due to activation of serotonin <a href="/wiki/5-HT2B_receptor" title="5-HT2B receptor">5-HT2B receptors</a>.<a href="#cite_note-pmid24361689-99">[99]</a><a href="#cite_note-pmid28676029-100">[100]</a> MDMA induces cardiac <a href="/wiki/Epigenetics" title="Epigenetics">epigenetic changes</a> in <a href="/wiki/DNA_methylation" title="DNA methylation">DNA methylation</a>, particularly hypermethylation changes.<a href="#cite_note-101">[101]</a> <div class="mw-heading mw-heading3"><h3 id="Reinforcement_disorders">Reinforcement disorders</h3></div> Approximately 60% of MDMA users experience <a href="/wiki/Drug_withdrawal" title="Drug withdrawal">withdrawal</a> symptoms when they stop taking MDMA.<a href="#cite_note-Toxnet_MDMA_after-effects-77">[77]</a> Some of these symptoms include fatigue, loss of appetite, depression, and trouble concentrating.<a href="#cite_note-Toxnet_MDMA_after-effects-77">[77]</a> <a href="/wiki/Drug_tolerance" title="Drug tolerance">Tolerance</a> to some of the desired and adverse effects of MDMA is expected to occur with consistent MDMA use.<a href="#cite_note-Toxnet_MDMA_after-effects-77">[77]</a> A 2007 <a href="/wiki/Delphi_method" title="Delphi method">delphic analysis</a> of a panel of experts in pharmacology, psychiatry, law, policing and others estimated MDMA to have a psychological dependence and physical dependence potential roughly three-fourths to four-fifths that of cannabis.<a href="#cite_note-pmid17382831-102">[102]</a> MDMA has been shown to induce <a href="/wiki/%CE%94FosB" class="mw-redirect" title="ΔFosB">ΔFosB</a> in the <a href="/wiki/Nucleus_accumbens" title="Nucleus accumbens">nucleus accumbens</a>.<a href="#cite_note-MDMA_ΔFosB-103">[103]</a> Because MDMA releases dopamine in the <a href="/wiki/Striatum" title="Striatum">striatum</a>, the mechanisms by which it induces ΔFosB in the nucleus accumbens are analogous to other dopaminergic psychostimulants.<a href="#cite_note-MDMA_ΔFosB-103">[103]</a><a href="#cite_note-Nestler-104">[104]</a> Therefore, chronic use of MDMA at high doses can result in <a href="/wiki/Neuroplasticity" title="Neuroplasticity">altered brain structure</a> and <a href="/wiki/Drug_addiction" class="mw-redirect" title="Drug addiction">drug addiction</a> that occur as a consequence of ΔFosB overexpression in the nucleus accumbens.<a href="#cite_note-Nestler-104">[104]</a> MDMA is less addictive than other stimulants such as methamphetamine and cocaine.<a href="#cite_note-105">[105]</a><a href="#cite_note-106">[106]</a> Compared with amphetamine, MDMA and its metabolite MDA are less reinforcing.<a href="#cite_note-107">[107]</a> One study found approximately 15% of chronic MDMA users met the <a href="/wiki/DSM-IV" class="mw-redirect" title="DSM-IV">DSM-IV</a> diagnostic criteria for <a href="/wiki/Substance_dependence" title="Substance dependence">substance dependence</a>.<a href="#cite_note-Steinkellner2011-108">[108]</a> However, there is little evidence for a specific diagnosable MDMA dependence syndrome because MDMA is typically used relatively infrequently.<a href="#cite_note-Epstein2013-52">[52]</a> There are currently no medications to treat MDMA addiction.<a href="#cite_note-109">[109]</a> <div class="mw-heading mw-heading3"><h3 id="During_pregnancy">During pregnancy</h3></div> MDMA is a moderately <a href="/wiki/Teratogenic_drug" class="mw-redirect" title="Teratogenic drug">teratogenic drug</a> (i.e., it is toxic to the fetus).<a href="#cite_note-vorhees-110">[110]</a><a href="#cite_note-meamar-111">[111]</a> <a href="/wiki/Uterus" title="Uterus">In utero</a> exposure to MDMA is associated with a <a href="/wiki/Neurotoxicity" title="Neurotoxicity">neuro</a>- and <a href="/wiki/Cardiotoxicity" title="Cardiotoxicity">cardiotoxicity</a><a href="#cite_note-meamar-111">[111]</a> and impaired motor functioning. Motor delays may be temporary during infancy or long-term. The severity of these developmental delays increases with heavier MDMA use.<a href="#cite_note-Pharm2014-92">[92]</a><a href="#cite_note-singer-112">[112]</a> MDMA has been shown to promote the survival of fetal dopaminergic neurons in culture.<a href="#cite_note-113">[113]</a> <div class="mw-heading mw-heading2"><h2 id="Overdose">Overdose</h2></div> MDMA overdose symptoms vary widely due to the involvement of multiple organ systems. Some of the more overt overdose symptoms are listed in the table below. The number of instances of fatal MDMA intoxication is low relative to its usage rates. In most fatalities, MDMA was not the only drug involved. Acute toxicity is mainly caused by <a href="/wiki/Serotonin_syndrome" title="Serotonin syndrome">serotonin syndrome</a> and <a href="/wiki/Sympathomimetic" class="mw-redirect" title="Sympathomimetic">sympathomimetic</a> effects.<a href="#cite_note-Steinkellner2011-108">[108]</a> Sympathomimetic side effects can be managed with <a href="/wiki/Carvedilol" title="Carvedilol">carvedilol</a>.<a href="#cite_note-RichardsAlbertsonDerlet2015-114">[114]</a><a href="#cite_note-HysekSchmidRickli2012-115">[115]</a> MDMA's toxicity in overdose may be exacerbated by caffeine, with which it is frequently cut in order to increase volume.<a href="#cite_note-116">[116]</a> A scheme for management of acute MDMA toxicity has been published focusing on treatment of hyperthermia, hyponatraemia, serotonin syndrome, and multiple organ failure.<a href="#cite_note-117">[117]</a> <table class="wikitable unsortable" style="margin: 1em auto;"> <caption>Symptoms of overdose </caption> <tbody><tr> <th scope="col" style="text-align:center">System </th> <th scope="col">Minor or moderate overdose<a href="#cite_note-delaTorreFarréRoset2004-118">[118]</a></th> <th>Severe overdose<a href="#cite_note-delaTorreFarréRoset2004-118">[118]</a> </th></tr> <tr> <th scope="row"><a href="/wiki/Cardiovascular_system" class="mw-redirect" title="Cardiovascular system">Cardiovascular</a> </th> <td> </td> <td> <ul><li><a href="/wiki/Disseminated_intravascular_coagulation" title="Disseminated intravascular coagulation">Disseminated intravascular coagulation</a><a href="#cite_note-Acute_amph_toxicity-43">[43]</a></li> <li><a href="/wiki/Intracranial_hemorrhage" title="Intracranial hemorrhage">Intracranial hemorrhage</a><a href="#cite_note-Acute_amph_toxicity-43">[43]</a></li> <li>Severe <a href="/wiki/Hypertension" title="Hypertension">hypertension</a><a href="#cite_note-Acute_amph_toxicity-43">[43]</a><a href="#cite_note-oxford-119">[119]</a> or <a href="/wiki/Hypotension" title="Hypotension">hypotension</a><a href="#cite_note-Acute_amph_toxicity-43">[43]</a></li> <li>Hypotensive bleeding<a href="#cite_note-Betzler2017-8">[8]</a></li></ul> </td></tr> <tr> <th scope="row"><a href="/wiki/Central_nervous_system" title="Central nervous system">Central nervous system</a> </th> <td> <ul><li><a href="/wiki/Hyperreflexia" title="Hyperreflexia">Hyperreflexia</a><a href="#cite_note-delaTorreFarréRoset2004-118">[118]</a></li> <li><a href="/wiki/Psychomotor_agitation" title="Psychomotor agitation">Agitation</a><a href="#cite_note-Acute_amph_toxicity-43">[43]</a><a href="#cite_note-oxford-119">[119]</a></li> <li><a href="/wiki/Mental_confusion" class="mw-redirect" title="Mental confusion">Mental confusion</a><a href="#cite_note-Acute_amph_toxicity-43">[43]</a></li> <li><a href="/wiki/Paranoia" title="Paranoia">Paranoia</a><a href="#cite_note-Acute_amph_toxicity-43">[43]</a><a href="#cite_note-oxford-119">[119]</a></li> <li><a href="/wiki/Stimulant_psychosis" title="Stimulant psychosis">Stimulant psychosis</a><a href="#cite_note-Betzler2017-8">[8]</a><a href="#cite_note-pmid22392347-15">[15]</a></li></ul> </td> <td> <ul><li><a href="/wiki/Cognitive_deficit" class="mw-redirect" title="Cognitive deficit">Cognitive and memory impairment</a><a href="#cite_note-Acute_amph_toxicity-43">[43]</a> potentially to the point of <a href="/wiki/Retrograde_amnesia" title="Retrograde amnesia">retrograde</a> or <a href="/wiki/Anterograde_amnesia" title="Anterograde amnesia">anterograde amnesia</a><a href="#cite_note-120">[120]</a></li> <li>Coma<a href="#cite_note-pmid22392347-15">[15]</a><a href="#cite_note-oxford-119">[119]</a></li> <li><a href="/wiki/Convulsion" title="Convulsion">Convulsions</a><a href="#cite_note-Acute_amph_toxicity-43">[43]</a><a href="#cite_note-oxford-119">[119]</a></li> <li><a href="/wiki/Hallucination" title="Hallucination">Hallucinations</a><a href="#cite_note-Acute_amph_toxicity-43">[43]</a><a href="#cite_note-oxford-119">[119]</a></li> <li><a href="/wiki/Loss_of_consciousness" class="mw-redirect" title="Loss of consciousness">Loss of consciousness</a><a href="#cite_note-pmid22392347-15">[15]</a></li> <li><a href="/wiki/Serotonin_syndrome" title="Serotonin syndrome">Serotonin syndrome</a><a href="#cite_note-pmid22392347-15">[15]</a><a href="#cite_note-Acute_amph_toxicity-43">[43]</a><a href="#cite_note-hyperpyrexia-79">[79]</a></li></ul> </td></tr> <tr> <th scope="row"><a href="/wiki/Musculoskeletal_system" class="mw-redirect" title="Musculoskeletal system">Musculoskeletal</a> </th> <td> </td> <td> <ul><li><a href="/wiki/Hypertonia" title="Hypertonia">Muscle rigidity</a><a href="#cite_note-Acute_amph_toxicity-43">[43]</a></li> <li><a href="/wiki/Rhabdomyolysis" title="Rhabdomyolysis">Rhabdomyolysis</a> (i.e., rapid muscle breakdown)<a href="#cite_note-Acute_amph_toxicity-43">[43]</a><a href="#cite_note-hyperpyrexia-79">[79]</a></li></ul> </td></tr> <tr> <th scope="row"><a href="/wiki/Respiratory_system" title="Respiratory system">Respiratory</a> </th> <td> </td> <td> <ul><li><a href="/wiki/Acute_respiratory_distress_syndrome" title="Acute respiratory distress syndrome">Acute respiratory distress syndrome</a><a href="#cite_note-Acute_amph_toxicity-43">[43]</a></li></ul> </td></tr> <tr> <th scope="row"><a href="/wiki/Urogenital_system" class="mw-redirect" title="Urogenital system">Urinary</a> </th> <td> </td> <td> <ul><li><a href="/wiki/Acute_kidney_injury" title="Acute kidney injury">Acute kidney injury</a><a href="#cite_note-Acute_amph_toxicity-43">[43]</a><a href="#cite_note-121">[121]</a></li></ul> </td></tr> <tr> <th scope="row">Other </th> <td> </td> <td> <ul><li><a href="/wiki/Cerebral_edema" title="Cerebral edema">Cerebral edema</a><a href="#cite_note-pmid22392347-15">[15]</a></li> <li><a href="/wiki/Hepatitis" title="Hepatitis">Hepatitis</a><a href="#cite_note-Acute_amph_toxicity-43">[43]</a><a href="#cite_note-hyperpyrexia-79">[79]</a></li> <li><a href="/wiki/Hyperpyrexia" class="mw-redirect" title="Hyperpyrexia">Hyperpyrexia</a> (a life-threatening elevation of body temperature greater than or equal to 40.0 or 41.5 °C (104.0 or 106.7 °F))<a href="#cite_note-Acute_amph_toxicity-43">[43]</a><a href="#cite_note-hyperpyrexia-79">[79]</a></li> <li><a href="/wiki/Hyponatremia" title="Hyponatremia">Hyponatremia</a> (<a href="/wiki/Syndrome_of_inappropriate_antidiuretic_hormone" class="mw-redirect" title="Syndrome of inappropriate antidiuretic hormone">syndrome of inappropriate antidiuretic hormone</a>)<a href="#cite_note-Acute_amph_toxicity-43">[43]</a><a href="#cite_note-Hyponatremia-78">[78]</a><a href="#cite_note-hyperpyrexia-79">[79]</a></li></ul> </td></tr></tbody></table> <div class="mw-heading mw-heading2"><h2 id="Interactions">Interactions</h2></div> A number of <a href="/wiki/Drug_interactions" class="mw-redirect" title="Drug interactions">drug interactions</a> can occur between MDMA and other drugs, including <a href="/wiki/Serotonin" title="Serotonin">serotonergic</a> drugs.<a href="#cite_note-Toxnet_MDMA_after-effects-77">[77]</a><a href="#cite_note-122">[122]</a> MDMA also interacts with drugs which inhibit <a href="/wiki/CYP450" class="mw-redirect" title="CYP450">CYP450</a> enzymes, like <a href="/wiki/Ritonavir" title="Ritonavir">ritonavir</a> (Norvir), particularly <a href="/wiki/CYP2D6" title="CYP2D6">CYP2D6</a> inhibitors.<a href="#cite_note-Toxnet_MDMA_after-effects-77">[77]</a> Life-threatening reactions and death have occurred in people who took MDMA while on ritonavir.<a href="#cite_note-pmid32228243-123">[123]</a> <a href="/wiki/Bupropion" title="Bupropion">Bupropion</a>, a strong CYP2D6 inhibitor, has been found to increase MDMA exposure with administration of MDMA.<a href="#cite_note-FonsecaFibeiroTapadas2021-124">[124]</a><a href="#cite_note-SchmidRickliSchaffner2015-125">[125]</a> Concurrent use of MDMA high dosages with another serotonergic drug can result in a life-threatening condition called <a href="/wiki/Serotonin_syndrome" title="Serotonin syndrome">serotonin syndrome</a>.<a href="#cite_note-Betzler2017-8">[8]</a><a href="#cite_note-Toxnet_MDMA_after-effects-77">[77]</a> Severe overdose resulting in death has also been reported in people who took MDMA in combination with certain <a href="/wiki/Monoamine_oxidase_inhibitor" title="Monoamine oxidase inhibitor">monoamine oxidase inhibitors</a> (MAOIs),<a href="#cite_note-Betzler2017-8">[8]</a><a href="#cite_note-Toxnet_MDMA_after-effects-77">[77]</a> such as <a href="/wiki/Phenelzine" title="Phenelzine">phenelzine</a> (Nardil), <a href="/wiki/Tranylcypromine" title="Tranylcypromine">tranylcypromine</a> (Parnate), or <a href="/wiki/Moclobemide" title="Moclobemide">moclobemide</a> (Aurorix, Manerix).<a href="#cite_note-126">[126]</a> <a href="/wiki/Serotonin_reuptake_inhibitor" title="Serotonin reuptake inhibitor">Serotonin reuptake inhibitors</a> (SRIs) such as <a href="/wiki/Citalopram" title="Citalopram">citalopram</a> (Celexa), <a href="/wiki/Duloxetine" title="Duloxetine">duloxetine</a> (Cymbalta), <a href="/wiki/Fluoxetine" title="Fluoxetine">fluoxetine</a> (Prozac), and <a href="/wiki/Paroxetine" title="Paroxetine">paroxetine</a> (Paxil) have been shown to block most of the subjective effects of MDMA.<a href="#cite_note-HalberstadtNichols2020-127">[127]</a> <a href="/wiki/Norepinephrine_reuptake_inhibitor" title="Norepinephrine reuptake inhibitor">Norepinephrine reuptake inhibitors</a> (NRIs) such as <a href="/wiki/Reboxetine" title="Reboxetine">reboxetine</a> (Edronax) have been found to reduce <a href="/wiki/Emotional_excitation" class="mw-redirect" title="Emotional excitation">emotional excitation</a> and feelings of <a href="/wiki/Psychostimulant" class="mw-redirect" title="Psychostimulant">stimulation</a> with MDMA but do not appear to influence its <a href="/wiki/Entactogen" class="mw-redirect" title="Entactogen">entactogenic</a> or <a href="/wiki/Euphoriant" class="mw-redirect" title="Euphoriant">mood-elevating</a> effects.<a href="#cite_note-HalberstadtNichols2020-127">[127]</a> MDMA <a href="/wiki/Monoamine_releasing_agent" title="Monoamine releasing agent">induces the release of monoamine neurotransmitters</a> and thereby acts as an indirectly acting <a href="/wiki/Sympathomimetic" class="mw-redirect" title="Sympathomimetic">sympathomimetic</a> and produces a variety of <a href="/wiki/Cardiostimulant" class="mw-redirect" title="Cardiostimulant">cardiostimulant</a> effects.<a href="#cite_note-FonsecaFibeiroTapadas2021-124">[124]</a> It <a href="/wiki/Dose_dependence" class="mw-redirect" title="Dose dependence">dose-dependently</a> increases <a href="/wiki/Heart_rate" title="Heart rate">heart rate</a>, <a href="/wiki/Blood_pressure" title="Blood pressure">blood pressure</a>, and <a href="/wiki/Cardiac_output" title="Cardiac output">cardiac output</a>.<a href="#cite_note-FonsecaFibeiroTapadas2021-124">[124]</a><a href="#cite_note-MendelsonBaggottLi2012-128">[128]</a> SRIs like citalopram and <a href="/wiki/Paroxetine" title="Paroxetine">paroxetine</a>, as well as the <a href="/wiki/Serotonin" title="Serotonin">serotonin</a> <a href="/wiki/5-HT2A_receptor" title="5-HT2A receptor">5-HT2A receptor</a> <a href="/wiki/Receptor_antagonist" title="Receptor antagonist">antagonist</a> <a href="/wiki/Ketanserin" title="Ketanserin">ketanserin</a>, have been found to partially block the increases in heart rate and blood pressure with MDMA.<a href="#cite_note-FonsecaFibeiroTapadas2021-124">[124]</a><a href="#cite_note-LiechtiSaurGamma2000-129">[129]</a> It is notable in this regard that <a href="/wiki/Serotonergic_psychedelic" class="mw-redirect" title="Serotonergic psychedelic">serotonergic psychedelics</a> such as <a href="/wiki/Psilocybin" title="Psilocybin">psilocybin</a>, which act as serotonin 5-HT2A receptor agonists, likewise have sympathomimetic effects.<a href="#cite_note-Wsół2023-130">[130]</a><a href="#cite_note-NeumannDheinKirchhefer2024-131">[131]</a><a href="#cite_note-LeyHolzeArikci2023-132">[132]</a> The NRI <a href="/wiki/Reboxetine" title="Reboxetine">reboxetine</a> and the <a href="/wiki/Serotonin%E2%80%93norepinephrine_reuptake_inhibitor" title="Serotonin–norepinephrine reuptake inhibitor">serotonin–norepinephrine reuptake inhibitor</a> (SNRI) duloxetine block MDMA-induced increases in heart rate and blood pressure.<a href="#cite_note-FonsecaFibeiroTapadas2021-124">[124]</a> Conversely, bupropion, a <a href="/wiki/Norepinephrine%E2%80%93dopamine_reuptake_inhibitor" title="Norepinephrine–dopamine reuptake inhibitor">norepinephrine–dopamine reuptake inhibitor</a> (NDRI) with only weak <a href="/wiki/Dopaminergic" title="Dopaminergic">dopaminergic</a> activity,<a href="#cite_note-HartSpangemacherDefert2024-133">[133]</a><a href="#cite_note-EapGründerBaumann2021-134">[134]</a> reduced MDMA-induced heart rate and circulating <a href="/wiki/Norepinephrine" title="Norepinephrine">norepinephrine</a> increases but did not affect MDMA-induced blood pressure increases.<a href="#cite_note-FonsecaFibeiroTapadas2021-124">[124]</a><a href="#cite_note-SchmidRickliSchaffner2015-125">[125]</a> On the other hand, the robust NDRI <a href="/wiki/Methylphenidate" title="Methylphenidate">methylphenidate</a>, which has sympathomimetic effects of its own, has been found to augment the cardiovascular effects and increases in circulating norepinephrine and <a href="/wiki/Epinephrine" class="mw-redirect" title="Epinephrine">epinephrine</a> levels induced by MDMA.<a href="#cite_note-FonsecaFibeiroTapadas2021-124">[124]</a><a href="#cite_note-HysekSimmlerSchillinger2014-135">[135]</a> The <a href="/wiki/Binding_selectivity" title="Binding selectivity">non-selective</a> <a href="/wiki/Beta_blocker" title="Beta blocker">beta blocker</a> <a href="/wiki/Pindolol" title="Pindolol">pindolol</a> blocked MDMA-induced increases in heart rate but not blood pressure.<a href="#cite_note-FonsecaFibeiroTapadas2021-124">[124]</a><a href="#cite_note-RichardsAlbertsonDerlet2015-114">[114]</a><a href="#cite_note-HysekVollenweiderLiechti2010-136">[136]</a> The <a href="/wiki/%CE%912-adrenergic_receptor" class="mw-redirect" title="Α2-adrenergic receptor">α2-adrenergic receptor</a> <a href="/wiki/Agonist" title="Agonist">agonist</a> <a href="/wiki/Clonidine" title="Clonidine">clonidine</a> did not affect the cardiovascular effects of MDMA, though it reduced blood pressure.<a href="#cite_note-FonsecaFibeiroTapadas2021-124">[124]</a><a href="#cite_note-RichardsAlbertsonDerlet2015-114">[114]</a><a href="#cite_note-HysekBruggerSimmler2012-137">[137]</a> The <a href="/wiki/%CE%911-adrenergic_receptor" class="mw-redirect" title="Α1-adrenergic receptor">α1-adrenergic receptor</a> antagonists <a href="/wiki/Doxazosin" title="Doxazosin">doxazosin</a> and <a href="/wiki/Prazosin" title="Prazosin">prazosin</a> blocked or reduced MDMA-induced blood pressure increases but augmented MDMA-induced heart rate and cardiac output increases.<a href="#cite_note-FonsecaFibeiroTapadas2021-124">[124]</a><a href="#cite_note-RichardsAlbertsonDerlet2015-114">[114]</a><a href="#cite_note-HysekFinkSimmler2013-138">[138]</a><a href="#cite_note-MendelsonBaggottLi2012-128">[128]</a> The dual α1- and <a href="/wiki/%CE%92-adrenergic_receptor" class="mw-redirect" title="Β-adrenergic receptor">β-adrenergic receptor</a> blocker <a href="/wiki/Carvedilol" title="Carvedilol">carvedilol</a> reduced MDMA-induced heart rate and blood pressure increases.<a href="#cite_note-FonsecaFibeiroTapadas2021-124">[124]</a><a href="#cite_note-RichardsAlbertsonDerlet2015-114">[114]</a><a href="#cite_note-HysekSchmidRickli2012-115">[115]</a> In contrast to the cases of serotonergic and noradrenergic agents, the <a href="/wiki/Dopamine" title="Dopamine">dopamine</a> <a href="/wiki/D2_receptor" class="mw-redirect" title="D2 receptor">D2 receptor</a> antagonist <a href="/wiki/Haloperidol" title="Haloperidol">haloperidol</a> did not affect the cardiovascular responses to MDMA.<a href="#cite_note-FonsecaFibeiroTapadas2021-124">[124]</a><a href="#cite_note-LiechtiVollenweider2000-139">[139]</a> Due to the theoretical risk of "unopposed α-stimulation" and possible consequences like <a href="/wiki/Coronary_vasospasm" title="Coronary vasospasm">coronary vasospasm</a>, it has been suggested that dual α1- and β-adrenergic receptor antagonists like carvedilol and <a href="/wiki/Labetalol" title="Labetalol">labetalol</a>, rather than selective beta blockers, should be used in the management of stimulant-induced <a href="/wiki/Sympathomimetic" class="mw-redirect" title="Sympathomimetic">sympathomimetic</a> <a href="/wiki/Toxicity" title="Toxicity">toxicity</a>, for instance in the context of <a href="/wiki/Overdose" class="mw-redirect" title="Overdose">overdose</a>.<a href="#cite_note-RichardsAlbertsonDerlet2015-114">[114]</a><a href="#cite_note-RichardsHollanderRamoska2017-140">[140]</a> <div class="mw-heading mw-heading2"><h2 id="Pharmacology">Pharmacology</h2></div> <div class="mw-heading mw-heading3"><h3 id="Pharmacodynamics">Pharmacodynamics</h3></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951" /><div role="note" class="hatnote navigation-not-searchable">See also: <a href="/wiki/Empathogen#Mechanism_of_action" title="Empathogen">Empathogen § Mechanism of action</a>, <a href="/wiki/Serotonin_releasing_agent#Effects_and_comparisons" title="Serotonin releasing agent">Serotonin releasing agent § Effects and comparisons</a>, and <a href="/wiki/Monoamine_releasing_agent#Mechanism_of_action" title="Monoamine releasing agent">Monoamine releasing agent § Mechanism of action</a></div> <table class="wikitable floatright" style="font-size:small;"> <caption>Activities of MDMA<a href="#cite_note-DunlapAndrewsOlson2018-17">[17]</a> </caption> <tbody><tr> <th><a href="/wiki/Biological_target" title="Biological target">Target</a></th> <th><a href="/wiki/Affinity_(pharmacology)" class="mw-redirect" title="Affinity (pharmacology)">Affinity</a> (Ki, nM) </th></tr> <tr> <td><a href="/wiki/Serotonin_transporter" title="Serotonin transporter"><abbr title="Serotonin transporter">SERT</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Serotonin transporter</td> <td>0.73–13,300 (Ki) 380–2,500 (<a href="/wiki/Half-maximal_inhibitory_concentration" class="mw-redirect" title="Half-maximal inhibitory concentration"><abbr title="half-maximal inhibitory concentration">IC50</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip half-maximal inhibitory concentration) 50–72 (<a href="/wiki/Half-maximal_effective_concentration" class="mw-redirect" title="Half-maximal effective concentration"><abbr title="Half-maximal effective concentration">EC50</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Half-maximal effective concentration) (rat) </td></tr> <tr> <td><a href="/wiki/Norepinephrine_transporter" title="Norepinephrine transporter"><abbr title="Norepinephrine transporter">NET</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Norepinephrine transporter</td> <td>27,000–30,500 (Ki) 360–405 (<abbr title="half-maximal inhibitory concentration">IC50</abbr>) 54–110 (<abbr title="Half-maximal effective concentration">EC50</abbr>) (rat) </td></tr> <tr> <td><a href="/wiki/Dopamine_transporter" title="Dopamine transporter"><abbr title="Dopamine transporter">DAT</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Dopamine transporter</td> <td>6,500–>10,000 (Ki) 1,440–21,000 (<abbr title="half-maximal inhibitory concentration">IC50</abbr>) 51–278 (<abbr title="Half-maximal effective concentration">EC50</abbr>) (rat) </td></tr> <tr> <td><a href="/wiki/5-HT1A_receptor" title="5-HT1A receptor">5-HT1A</a></td> <td>6,300–12,200 (Ki) 36,000 nM (<abbr title="Half-maximal effective concentration">EC50</abbr>) 64% (<a href="/wiki/Maximal_efficacy" class="mw-redirect" title="Maximal efficacy"><abbr title="maximal efficacy">Emax</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip maximal efficacy) </td></tr> <tr> <td><a href="/wiki/5-HT1B_receptor" title="5-HT1B receptor">5-HT1B</a></td> <td>>10,000 </td></tr> <tr> <td><a href="/wiki/5-HT1D_receptor" title="5-HT1D receptor">5-HT1D</a></td> <td>>10,000 </td></tr> <tr> <td><a href="/wiki/5-HT1E_receptor" title="5-HT1E receptor">5-HT1E</a></td> <td>>10,000 </td></tr> <tr> <td><a href="/wiki/5-HT1F_receptor" title="5-HT1F receptor">5-HT1F</a></td> <td><abbr title="No data">ND</abbr> </td></tr> <tr> <td><a href="/wiki/5-HT2A_receptor" title="5-HT2A receptor">5-HT2A</a></td> <td>4,600–>10,000 (Ki) 6,100–12,484 (<abbr title="half-maximal effective concentration">EC50</abbr>) 40–55% (<abbr title="maximal efficacy">Emax</abbr>) </td></tr> <tr> <td><a href="/wiki/5-HT2B_receptor" title="5-HT2B receptor">5-HT2B</a></td> <td>500–2,000 (Ki) 2,000–>20,000 (<abbr title="half-maximal effective concentration">EC50</abbr>) 32% (<abbr title="maximal efficacy">Emax</abbr>) </td></tr> <tr> <td><a href="/wiki/5-HT2C_receptor" title="5-HT2C receptor">5-HT2C</a></td> <td>4,400–>13,000 (Ki) 831–9,100 (<abbr title="half-maximal effective concentration">EC50</abbr>) 92% (<abbr title="maximal efficacy">Emax</abbr>) </td></tr> <tr> <td><a href="/wiki/5-HT3_receptor" title="5-HT3 receptor">5-HT3</a></td> <td>>10,000 </td></tr> <tr> <td><a href="/wiki/5-HT4_receptor" title="5-HT4 receptor">5-HT4</a></td> <td><abbr title="No data">ND</abbr> </td></tr> <tr> <td><a href="/wiki/5-HT5A_receptor" title="5-HT5A receptor">5-HT5A</a></td> <td>>10,000 </td></tr> <tr> <td><a href="/wiki/5-HT6_receptor" title="5-HT6 receptor">5-HT6</a></td> <td>>10,000 </td></tr> <tr> <td><a href="/wiki/5-HT7_receptor" title="5-HT7 receptor">5-HT7</a></td> <td>>10,000 </td></tr> <tr> <td><a href="/wiki/Alpha-1A_adrenergic_receptor" title="Alpha-1A adrenergic receptor">α1A</a></td> <td>6,900–>10,000 </td></tr> <tr> <td><a href="/wiki/Alpha-1B_adrenergic_receptor" title="Alpha-1B adrenergic receptor">α1B</a></td> <td>>10,000 </td></tr> <tr> <td><a href="/wiki/Alpha-1D_adrenergic_receptor" title="Alpha-1D adrenergic receptor">α1D</a></td> <td><abbr title="No data">ND</abbr> </td></tr> <tr> <td><a href="/wiki/Alpha-2A_adrenergic_receptor" title="Alpha-2A adrenergic receptor">α2A</a></td> <td>2,532–15,000 </td></tr> <tr> <td><a href="/wiki/Alpha-2B_adrenergic_receptor" title="Alpha-2B adrenergic receptor">α2B</a></td> <td>1,785 </td></tr> <tr> <td><a href="/wiki/Alpha-2C_adrenergic_receptor" title="Alpha-2C adrenergic receptor">α2C</a></td> <td>1,123–1,346 </td></tr> <tr> <td><a href="/wiki/Beta-1_adrenergic_receptor" title="Beta-1 adrenergic receptor">β1</a>, <a href="/wiki/Beta-2_adrenergic_receptor" title="Beta-2 adrenergic receptor">β2</a></td> <td>>10,000 </td></tr> <tr> <td><a href="/wiki/D1_receptor" class="mw-redirect" title="D1 receptor">D1</a></td> <td>>13,600 </td></tr> <tr> <td><a href="/wiki/D2_receptor" class="mw-redirect" title="D2 receptor">D2</a></td> <td>25,200 </td></tr> <tr> <td><a href="/wiki/D3_receptor" class="mw-redirect" title="D3 receptor">D3</a></td> <td>>17,700 </td></tr> <tr> <td><a href="/wiki/D4_receptor" class="mw-redirect" title="D4 receptor">D4</a></td> <td>>10,000 </td></tr> <tr> <td><a href="/wiki/D5_receptor" class="mw-redirect" title="D5 receptor">D5</a></td> <td>>10,000 </td></tr> <tr> <td><a href="/wiki/H1_receptor" class="mw-redirect" title="H1 receptor">H1</a></td> <td>2,138–>14,400 </td></tr> <tr> <td><a href="/wiki/H2_receptor" class="mw-redirect" title="H2 receptor">H2</a></td> <td>>10,000 </td></tr> <tr> <td><a href="/wiki/H3_receptor" class="mw-redirect" title="H3 receptor">H3</a>, <a href="/wiki/H4_receptor" class="mw-redirect" title="H4 receptor">H4</a></td> <td><abbr title="No data">ND</abbr> </td></tr> <tr> <td><a href="/wiki/Muscarinic_acetylcholine_M1_receptor" class="mw-redirect" title="Muscarinic acetylcholine M1 receptor">M1</a></td> <td>>10,000 </td></tr> <tr> <td><a href="/wiki/Muscarinic_acetylcholine_M2_receptor" class="mw-redirect" title="Muscarinic acetylcholine M2 receptor">M2</a></td> <td>>10,000 </td></tr> <tr> <td><a href="/wiki/Muscarinic_acetylcholine_M3_receptor" class="mw-redirect" title="Muscarinic acetylcholine M3 receptor">M3</a></td> <td>1,850–>10,000 </td></tr> <tr> <td><a href="/wiki/Muscarinic_acetylcholine_M4_receptor" class="mw-redirect" title="Muscarinic acetylcholine M4 receptor">M4</a></td> <td>8,250–>10,000 </td></tr> <tr> <td><a href="/wiki/Muscarinic_acetylcholine_M5_receptor" class="mw-redirect" title="Muscarinic acetylcholine M5 receptor">M5</a></td> <td>6,340–>10,000 </td></tr> <tr> <td><a href="/wiki/Nicotinic_acetylcholine_receptor" title="Nicotinic acetylcholine receptor">nACh</a></td> <td>>10,000 </td></tr> <tr> <td><a href="/wiki/Trace_amine-associated_receptor_1" class="mw-redirect" title="Trace amine-associated receptor 1">TAAR1</a></td> <td>250–370 (Ki) (rat) 1,000–1,700 (<abbr title="half-maximal effective concentration">EC50</abbr>) (rat) 56% (<abbr title="maximal efficacy">Emax</abbr>) (rat) 2,400–3,100 (Ki) (mouse) 4,000 (<abbr title="half-maximal effective concentration">EC50</abbr>) (mouse) 71% (<abbr title="maximal efficacy">Emax</abbr>) (mouse) 35,000 (<abbr title="half-maximal effective concentration">EC50</abbr>) (human) 26% (<abbr title="maximal efficacy">Emax</abbr>) (human) </td></tr> <tr> <td><a href="/wiki/I1_receptor" class="mw-redirect" title="I1 receptor">I1</a></td> <td>220 </td></tr> <tr> <td><a href="/wiki/Sigma-1_receptor" title="Sigma-1 receptor">σ1</a>, <a href="/wiki/Sigma-2_receptor" title="Sigma-2 receptor">σ2</a></td> <td><abbr title="No data">ND</abbr> </td></tr> <tr class="sortbottom"> <td colspan="2" style="width: 1px; background-color:#eaecf0; text-align: center;">Notes: The smaller the value, the more avidly the drug binds to the site. Proteins are human unless otherwise specified. Refs: <a href="#cite_note-PDSPKiDatabase-141">[141]</a><a href="#cite_note-BindingDB-142">[142]</a><a href="#cite_note-DunlapAndrewsOlson2018-17">[17]</a><a href="#cite_note-Ray2010-143">[143]</a><a href="#cite_note-SimmlerBuserDonzelli2013-144">[144]</a><a href="#cite_note-SimmlerRickliHoener2014-145">[145]</a> <a href="#cite_note-RickliKopfHoener2015-146">[146]</a><a href="#cite_note-LuethiKolaczynskaWalter2019-147">[147]</a><a href="#cite_note-EshlemanForsterWolfrum2014-148">[148]</a><a href="#cite_note-GainetdinovHoenerBerry2018-149">[149]</a><a href="#cite_note-SimmlerBuchyChaboz2016-150">[150]</a><a href="#cite_note-SotnikovaCaronGainetdinov2009-151">[151]</a> </td></tr></tbody></table> MDMA is an <a href="/wiki/Entactogen" class="mw-redirect" title="Entactogen">entactogen</a> or <a href="/wiki/Empathogen" title="Empathogen">empathogen</a>, as well as a <a href="/wiki/Stimulant" title="Stimulant">stimulant</a>, <a href="/wiki/Euphoriant" class="mw-redirect" title="Euphoriant">euphoriant</a>, and weak <a href="/wiki/Psychedelic_drug" title="Psychedelic drug">psychedelic</a>.<a href="#cite_note-DunlapAndrewsOlson2018-17">[17]</a><a href="#cite_note-Nichols2022-152">[152]</a> It is a <a href="/wiki/Substrate_(biochemistry)" class="mw-redirect" title="Substrate (biochemistry)">substrate</a> of the <a href="/wiki/Monoamine_transporter" title="Monoamine transporter">monoamine transporters</a> (MATs) and acts as a <a href="/wiki/Monoamine_releasing_agent" title="Monoamine releasing agent">monoamine releasing agent</a> (MRA).<a href="#cite_note-DunlapAndrewsOlson2018-17">[17]</a><a href="#cite_note-DochertyAlsufyani2021-153">[153]</a><a href="#cite_note-RothmanBaumann2003-154">[154]</a><a href="#cite_note-RothmanBaumann2006-155">[155]</a> The drug is specifically a well-balanced <a href="/wiki/Serotonin%E2%80%93norepinephrine%E2%80%93dopamine_releasing_agent" title="Serotonin–norepinephrine–dopamine releasing agent">serotonin–norepinephrine–dopamine releasing agent</a> (SNDRA).<a href="#cite_note-DunlapAndrewsOlson2018-17">[17]</a><a href="#cite_note-DochertyAlsufyani2021-153">[153]</a><a href="#cite_note-RothmanBaumann2003-154">[154]</a><a href="#cite_note-RothmanBaumann2006-155">[155]</a> To a lesser extent, MDMA also acts as a <a href="/wiki/Serotonin%E2%80%93norepinephrine%E2%80%93dopamine_reuptake_inhibitor" title="Serotonin–norepinephrine–dopamine reuptake inhibitor">serotonin–norepinephrine–dopamine reuptake inhibitor</a> (SNDRI).<a href="#cite_note-DunlapAndrewsOlson2018-17">[17]</a><a href="#cite_note-DochertyAlsufyani2021-153">[153]</a><a href="#cite_note-RothmanBaumann2003-154">[154]</a> MDMA enters <a href="/wiki/Monoaminergic" title="Monoaminergic">monoaminergic</a> <a href="/wiki/Neuron" title="Neuron">neurons</a> via the MATs and then, via poorly understood <a href="/wiki/Mechanism_of_action" title="Mechanism of action">mechanisms</a>, reverses the direction of these transporters to produce <a href="/wiki/Efflux_pump" title="Efflux pump">efflux</a> of the <a href="/wiki/Monoamine_neurotransmitter" title="Monoamine neurotransmitter">monoamine neurotransmitters</a> rather than the usual <a href="/wiki/Reuptake" title="Reuptake">reuptake</a>.<a href="#cite_note-DunlapAndrewsOlson2018-17">[17]</a><a href="#cite_note-SulzerSondersPoulsen2005-156">[156]</a><a href="#cite_note-ReithGnegy2020-157">[157]</a><a href="#cite_note-VaughanHenryFoster2024-158">[158]</a> Induction of monoamine efflux by <a href="/wiki/Amphetamine-type_stimulant" class="mw-redirect" title="Amphetamine-type stimulant">amphetamines</a> in general may involve <a href="/wiki/Intracellular" class="mw-redirect" title="Intracellular">intracellular</a> <a href="/wiki/Sodium_ion" class="mw-redirect" title="Sodium ion">Na+</a> and <a href="/wiki/Calcium_ion" class="mw-redirect" title="Calcium ion">Ca2+</a> elevation and <a href="/wiki/Protein_kinase_C" title="Protein kinase C">PKC</a> and <a href="/wiki/CaMKII%CE%B1" class="mw-redirect" title="CaMKIIα">CaMKIIα</a> activation.<a href="#cite_note-SulzerSondersPoulsen2005-156">[156]</a><a href="#cite_note-ReithGnegy2020-157">[157]</a><a href="#cite_note-VaughanHenryFoster2024-158">[158]</a> MDMA also acts on the <a href="/wiki/Vesicular_monoamine_transporter_2" title="Vesicular monoamine transporter 2">vesicular monoamine transporter 2</a> (VMAT2) on <a href="/wiki/Synaptic_vesicle" title="Synaptic vesicle">synaptic vesicles</a> to increase the <a href="/wiki/Cytosol" title="Cytosol">cytosolic</a> concentrations of the monoamine neurotransmitters available for efflux.<a href="#cite_note-DunlapAndrewsOlson2018-17">[17]</a><a href="#cite_note-DochertyAlsufyani2021-153">[153]</a> By inducing release and reuptake inhibition of <a href="/wiki/Serotonin" title="Serotonin">serotonin</a>, <a href="/wiki/Norepinephrine" title="Norepinephrine">norepinephrine</a>, and <a href="/wiki/Dopamine" title="Dopamine">dopamine</a>, MDMA increases levels of these neurotransmitters in the <a href="/wiki/Brain" title="Brain">brain</a> and <a href="/wiki/Peripheral_nervous_system" title="Peripheral nervous system">periphery</a>.<a href="#cite_note-DunlapAndrewsOlson2018-17">[17]</a><a href="#cite_note-DochertyAlsufyani2021-153">[153]</a> In addition to its actions as an SNDRA, MDMA directly but more modestly interacts with a number of <a href="/wiki/Monoamine_receptor" title="Monoamine receptor">monoamine</a> and other <a href="/wiki/Receptor_(biochemistry)" title="Receptor (biochemistry)">receptors</a>.<a href="#cite_note-DunlapAndrewsOlson2018-17">[17]</a><a href="#cite_note-PDSPKiDatabase-141">[141]</a><a href="#cite_note-BindingDB-142">[142]</a><a href="#cite_note-Ray2010-143">[143]</a> It is a low-<a href="/wiki/Potency_(pharmacology)" title="Potency (pharmacology)">potency</a> <a href="/wiki/Partial_agonist" title="Partial agonist">partial agonist</a> of the serotonin <a href="/wiki/5-HT2_receptor" title="5-HT2 receptor">5-HT2 receptors</a>, including of the serotonin <a href="/wiki/5-HT2A_receptor" title="5-HT2A receptor">5-HT2A</a>, <a href="/wiki/5-HT2B_receptor" title="5-HT2B receptor">5-HT2B</a>, and <a href="/wiki/5-HT2C_receptor" title="5-HT2C receptor">5-HT2C receptors</a>.<a href="#cite_note-DunlapAndrewsOlson2018-17">[17]</a><a href="#cite_note-PittsCurryHampshire2018-159">[159]</a><a href="#cite_note-SetolaHufeisenGrande-Allen2003-160">[160]</a><a href="#cite_note-NashRothBrodkin1994-161">[161]</a> The drug also interacts with <a href="/wiki/Alpha-2_adrenergic_receptor" title="Alpha-2 adrenergic receptor">α2-adrenergic receptors</a>, with the <a href="/wiki/Sigma_receptor" title="Sigma receptor">sigma</a> <a href="/wiki/Sigma-1_receptor" title="Sigma-1 receptor">σ1</a> and <a href="/wiki/Sigma-2_receptor" title="Sigma-2 receptor">σ2 receptors</a>, and with the <a href="/wiki/Imidazoline_receptor" title="Imidazoline receptor">imidazoline</a> <a href="/wiki/I1_receptor" class="mw-redirect" title="I1 receptor">I1 receptor</a>.<a href="#cite_note-DunlapAndrewsOlson2018-17">[17]</a><a href="#cite_note-PDSPKiDatabase-141">[141]</a><a href="#cite_note-BindingDB-142">[142]</a><a href="#cite_note-Ray2010-143">[143]</a> It is thought that agonism of the serotonin 5-HT2A receptor by MDMA may mediate the weak psychedelic effects of the drug in humans.<a href="#cite_note-SimmlerLiechti2018-162">[162]</a><a href="#cite_note-Meyer2013-163">[163]</a><a href="#cite_note-StraumannAvedisianKlaiber2024-16">[16]</a> However, findings in this area appear to be conflicting.<a href="#cite_note-Meyer2013-163">[163]</a><a href="#cite_note-Bedi2024-164">[164]</a><a href="#cite_note-StraumannAvedisianKlaiber2024-16">[16]</a> Likewise, findings on MDMA and induction of the <a href="/wiki/Head-twitch_response" title="Head-twitch response">head-twitch response</a> (HTR), a behavioral proxy of psychedelic-like effects, are contradictory in animals.<a href="#cite_note-HalberstadtGeyer2018-165">[165]</a><a href="#cite_note-Dunlap2022-166">[166]</a> Along with the preceding receptor interactions, MDMA is a potent partial agonist of the rodent <a href="/wiki/Trace_amine-associated_receptor_1" class="mw-redirect" title="Trace amine-associated receptor 1">trace amine-associated receptor 1</a> (TAAR1).<a href="#cite_note-GainetdinovHoenerBerry2018-149">[149]</a><a href="#cite_note-SimmlerBuchyChaboz2016-150">[150]</a> Conversely however, it is far weaker in terms of potency as an agonist of the human TAAR1.<a href="#cite_note-DunlapAndrewsOlson2018-17">[17]</a><a href="#cite_note-GainetdinovHoenerBerry2018-149">[149]</a><a href="#cite_note-SimmlerBuchyChaboz2016-150">[150]</a><a href="#cite_note-LewinMillerGilmour2011-167">[167]</a> Moreover, MDMA acts as a weak partial agonist or <a href="/wiki/Receptor_antagonist" title="Receptor antagonist">antagonist</a> of the human TAAR1 rather than as an <a href="/wiki/Intrinsic_activity" title="Intrinsic activity">efficacious</a> agonist.<a href="#cite_note-GainetdinovHoenerBerry2018-149">[149]</a><a href="#cite_note-SimmlerBuchyChaboz2016-150">[150]</a> In relation to the preceding, MDMA has been said to be inactive as a human TAAR1 agonist.<a href="#cite_note-DunlapAndrewsOlson2018-17">[17]</a> TAAR1 activation is thought to auto-inhibit and constrain the effects of amphetamines that possess TAAR1 agonism, for instance MDMA in rodents.<a href="#cite_note-DochertyAlsufyani2021-153">[153]</a><a href="#cite_note-EspinozaGainetdinov2014-168">[168]</a><a href="#cite_note-KuropkaZawadzkiSzpot2023-169">[169]</a><a href="#cite_note-SimmlerBuserDonzelli2013-144">[144]</a><a href="#cite_note-DiCaraMaggioAloisi2011-170">[170]</a> Elevation of serotonin, norepinephrine, and dopamine levels by MDMA is believed to mediate most of the drug's effects, including its entactogenic, stimulant, euphoriant, <a href="/wiki/Hyperthermia" title="Hyperthermia">hyperthermic</a>, and <a href="/wiki/Sympathomimetic" class="mw-redirect" title="Sympathomimetic">sympathomimetic</a> effects.<a href="#cite_note-DunlapAndrewsOlson2018-17">[17]</a><a href="#cite_note-DochertyAlsufyani2021-153">[153]</a><a href="#cite_note-ReinRaymondBoustani2024-171">[171]</a><a href="#cite_note-Kamilar-BrittBedi2015-172">[172]</a> The entactogenic effects of MDMA, including increased <a href="/wiki/Sociability" class="mw-redirect" title="Sociability">sociability</a>, <a href="/wiki/Empathy" title="Empathy">empathy</a>, <a href="/wiki/Emotional_intimacy" title="Emotional intimacy">feelings of closeness</a>, and <a href="/wiki/Antiaggressive" class="mw-redirect" title="Antiaggressive">reduced aggression</a>, are thought to be mainly due to induction of serotonin release.<a href="#cite_note-Kamilar-BrittBedi2015-172">[172]</a><a href="#cite_note-HalberstadtNichols2020-127">[127]</a><a href="#cite_note-Oeri2021-18">[18]</a> The exact <a href="/wiki/Serotonin_receptor" class="mw-redirect" title="Serotonin receptor">serotonin receptors</a> responsible for these effects are unclear, but may include the serotonin <a href="/wiki/5-HT1A_receptor" title="5-HT1A receptor">5-HT1A receptor</a>,<a href="#cite_note-EsakiSasakiNishitani2023-173">[173]</a> <a href="/wiki/5-HT1B_receptor" title="5-HT1B receptor">5-HT1B receptor</a>,<a href="#cite_note-HeifetsSalgadoTaylor2019-174">[174]</a> and 5-HT2A receptor,<a href="#cite_note-PittsMinervaChandler2017-175">[175]</a> as well as 5-HT1A receptor-mediated <a href="/wiki/Oxytocin" title="Oxytocin">oxytocin</a> release and consequent activation of the <a href="/wiki/Oxytocin_receptor" title="Oxytocin receptor">oxytocin receptor</a>.<a href="#cite_note-DunlapAndrewsOlson2018-17">[17]</a><a href="#cite_note-Kamilar-BrittBedi2015-172">[172]</a><a href="#cite_note-Blanco-GandíaMateos-GarcíaGarcía-Pardo2015-176">[176]</a><a href="#cite_note-HeifetsOlson2024-177">[177]</a><a href="#cite_note-Nichols2022-152">[152]</a> Induction of dopamine release is thought to be importantly involved in the stimulant and euphoriant effects of MDMA,<a href="#cite_note-DunlapAndrewsOlson2018-17">[17]</a><a href="#cite_note-PittsCurryHampshire2018-159">[159]</a><a href="#cite_note-KaurKarabulutGauld2023-178">[178]</a> while induction of norepinephrine release and serotonin 5-HT2A receptor stimulation are believed to mediate its sympathomimetic effects.<a href="#cite_note-FonsecaFibeiroTapadas2021-124">[124]</a><a href="#cite_note-DochertyAlsufyani2021-153">[153]</a> MDMA has been associated with a unique subjective "magic" or <a href="/wiki/Euphoria" title="Euphoria">euphoria</a> that few or no other known entactogens are said to fully reproduce.<a href="#cite_note-Baggott2023-179">[179]</a><a href="#cite_note-Baggott2024-180">[180]</a> The mechanisms underlying this property of MDMA are unknown, but it has been theorized to be due to a very specific mixture and balance of pharmacological activities, including combined serotonin, norepinephrine, and dopamine release and direct serotonin receptor agonism.<a href="#cite_note-RothmanBaumann2002-181">[181]</a><a href="#cite_note-Baggott2023-179">[179]</a><a href="#cite_note-Baggott2024-180">[180]</a> Repeated activation of serotonin 5-HT2B receptors by MDMA is thought to result in risk of <a href="/wiki/Valvular_heart_disease" title="Valvular heart disease">valvular heart disease</a> (VHD) and <a href="/wiki/Primary_pulmonary_hypertension" class="mw-redirect" title="Primary pulmonary hypertension">primary pulmonary hypertension</a> (PPH).<a href="#cite_note-McIntyre2023-182">[182]</a><a href="#cite_note-TagenMantuanivanHeerden2023-183">[183]</a><a href="#cite_note-Wsół2023-130">[130]</a><a href="#cite_note-RothmanBaumann2009-184">[184]</a><a href="#cite_note-RothmanBaumann2002-181">[181]</a><a href="#cite_note-RothmanBaumann2002b-185">[185]</a> MDMA has been associated with <a href="/wiki/Serotonergic_neurotoxicity" class="mw-redirect" title="Serotonergic neurotoxicity">serotonergic neurotoxicity</a>.<a href="#cite_note-CostaGołembiowska2022-186">[186]</a><a href="#cite_note-Oeri2021-18">[18]</a><a href="#cite_note-SpragueEvermanNichols1998-187">[187]</a> This may be due to formation of toxic MDMA <a href="/wiki/Metabolite" title="Metabolite">metabolites</a> and/or induction of <a href="/wiki/Serotonin%E2%80%93norepinephrine%E2%80%93dopamine_releasing_agent" title="Serotonin–norepinephrine–dopamine releasing agent">simultaneous serotonin and dopamine release</a>, with consequent uptake of dopamine into serotonergic neurons and breakdown into <a href="/wiki/Reactive_oxygen_species" title="Reactive oxygen species">toxic species</a>.<a href="#cite_note-CostaGołembiowska2022-186">[186]</a><a href="#cite_note-Oeri2021-18">[18]</a><a href="#cite_note-SpragueEvermanNichols1998-187">[187]</a> MDMA is a <a href="/wiki/Racemic_mixture" title="Racemic mixture">racemic mixture</a> of two <a href="/wiki/Enantiomers" class="mw-redirect" title="Enantiomers">enantiomers</a>, (S)-MDMA and <a href="/wiki/(R)-MDMA" title="(R)-MDMA">(R)-MDMA</a>.<a href="#cite_note-PittsCurryHampshire2018-159">[159]</a><a href="#cite_note-StraumannAvedisianKlaiber2024-16">[16]</a> (S)-MDMA is much more potent as an SNDRA <a href="/wiki/In_vitro" title="In vitro">in vitro</a> and in producing MDMA-like subjective effects in humans than (R)-MDMA.<a href="#cite_note-PittsCurryHampshire2018-159">[159]</a><a href="#cite_note-RothmanBaumann2006-155">[155]</a><a href="#cite_note-StraumannAvedisianKlaiber2024-16">[16]</a><a href="#cite_note-AndersonBraunBraun1978-188">[188]</a> By contrast, (R)-MDMA acts as a lower-potency <a href="/wiki/Serotonin%E2%80%93norepinephrine_releasing_agent" title="Serotonin–norepinephrine releasing agent">serotonin–norepinephrine releasing agent</a> (SNRA) with weak or negligible effects on dopamine.<a href="#cite_note-PittsCurryHampshire2018-159">[159]</a><a href="#cite_note-RothmanBaumann2006-155">[155]</a><a href="#cite_note-AcquasPisanuSpiga2007-189">[189]</a> Relatedly, (R)-MDMA shows weak or negligible stimulant-like and <a href="/wiki/Reward_system" title="Reward system">rewarding</a> effects in animals.<a href="#cite_note-PittsCurryHampshire2018-159">[159]</a><a href="#cite_note-CurryYoungTran2018-190">[190]</a> Both (S)-MDMA and (R)-MDMA produce entactogen-type effects in animals and humans.<a href="#cite_note-PittsCurryHampshire2018-159">[159]</a><a href="#cite_note-StraumannAvedisianKlaiber2024-16">[16]</a> In addition, both (S)-MDMA and (R)-MDMA are weak agonists of the serotonin 5-HT2 receptors.<a href="#cite_note-PittsCurryHampshire2018-159">[159]</a><a href="#cite_note-KaurKarabulutGauld2023-178">[178]</a><a href="#cite_note-StraumannAvedisianKlaiber2024-16">[16]</a><a href="#cite_note-SetolaHufeisenGrande-Allen2003-160">[160]</a><a href="#cite_note-NashRothBrodkin1994-161">[161]</a> (R)-MDMA is more potent and efficacious as a serotonin 5-HT2A and 5-HT2B receptor agonist than (S)-MDMA, whereas (S)-MDMA is somewhat more potent as an agonist of the serotonin 5-HT2C receptor.<a href="#cite_note-PittsCurryHampshire2018-159">[159]</a><a href="#cite_note-KaurKarabulutGauld2023-178">[178]</a><a href="#cite_note-StraumannAvedisianKlaiber2024-16">[16]</a> Despite its greater serotonin 5-HT2A receptor agonism however, (R)-MDMA did not produce more psychedelic-like effects than (S)-MDMA in humans.<a href="#cite_note-Bedi2024-164">[164]</a><a href="#cite_note-StraumannAvedisianKlaiber2024-16">[16]</a> MDMA produces <a href="/wiki/3,4-methylenedioxyamphetamine" class="mw-redirect" title="3,4-methylenedioxyamphetamine">3,4-methylenedioxyamphetamine</a> (MDA) as a minor <a href="/wiki/Active_metabolite" title="Active metabolite">active metabolite</a>.<a href="#cite_note-delaTorreFarréRoset2004-118">[118]</a> <a href="/wiki/Cmax_(pharmacology)" title="Cmax (pharmacology)">Peak levels</a> of MDA are about 5 to 10% of those of MDMA and <a href="/wiki/Area-under-the-curve_(pharmacokinetics)" class="mw-redirect" title="Area-under-the-curve (pharmacokinetics)">total exposure</a> to MDA is almost 10% of that of MDMA with <a href="/wiki/Oral_administration" title="Oral administration">oral</a> MDMA administration.<a href="#cite_note-delaTorreFarréRoset2004-118">[118]</a><a href="#cite_note-TagenMantuanivanHeerden2023-183">[183]</a> As a result, MDA may contribute to some extent to the effects of MDMA.<a href="#cite_note-delaTorreFarréRoset2004-118">[118]</a><a href="#cite_note-SimmlerLiechti2018-162">[162]</a> MDA is an entactogen, stimulant, and weak psychedelic similarly to MDMA.<a href="#cite_note-Oeri2021-18">[18]</a> Like MDMA, it acts as a potent and well-balanced SNDRA and as a weak serotonin 5-HT2 receptor agonist.<a href="#cite_note-RothmanBaumann2006-155">[155]</a><a href="#cite_note-SetolaHufeisenGrande-Allen2003-160">[160]</a><a href="#cite_note-NashRothBrodkin1994-161">[161]</a> However, MDA shows much more potent and efficacious serotonin 5-HT2A, 5-HT2B, and 5-HT2C receptor agonism than MDMA.<a href="#cite_note-KaurKarabulutGauld2023-178">[178]</a><a href="#cite_note-SimmlerLiechti2018-162">[162]</a><a href="#cite_note-NashRothBrodkin1994-161">[161]</a><a href="#cite_note-SetolaHufeisenGrande-Allen2003-160">[160]</a> Accordingly, MDA produces greater psychedelic effects than MDMA in humans<a href="#cite_note-Oeri2021-18">[18]</a> and might particularly contribute to the mild psychedelic-like effects of MDMA.<a href="#cite_note-SimmlerLiechti2018-162">[162]</a> On the other hand, MDA may also be importantly involved in <a href="/wiki/Toxicity" title="Toxicity">toxicity</a> of MDMA, such as <a href="/wiki/Cardiac_valvulopathy" class="mw-redirect" title="Cardiac valvulopathy">cardiac valvulopathy</a>.<a href="#cite_note-LuethiLiechti2021-191">[191]</a><a href="#cite_note-TagenMantuanivanHeerden2023-183">[183]</a><a href="#cite_note-SetolaHufeisenGrande-Allen2003-160">[160]</a> The <a href="/wiki/Duration_of_action" class="mw-redirect" title="Duration of action">duration of action</a> of MDMA (3–6 hours) is much shorter than its <a href="/wiki/Elimination_half-life" class="mw-redirect" title="Elimination half-life">elimination half-life</a> (8–9 hours) would imply.<a href="#cite_note-MeadParrott2020-192">[192]</a> In relation to this, MDMA's duration and the offset of its effects appear to be determined more by <a href="/wiki/Tachyphylaxis" title="Tachyphylaxis">rapid acute tolerance</a> rather than by circulating drug concentrations.<a href="#cite_note-HysekSimmlerNicola2012-55">[55]</a> Similar findings have been made for <a href="/wiki/Amphetamine" title="Amphetamine">amphetamine</a> and <a href="/wiki/Methamphetamine" title="Methamphetamine">methamphetamine</a>.<a href="#cite_note-ErmerPennickFrick2016-193">[193]</a><a href="#cite_note-CruickshankDyer2009-194">[194]</a><a href="#cite_note-AbbasBarnhardtNash2024-195">[195]</a><a href="#cite_note-vanGaalenSchlumbohmFolgering2019-196">[196]</a> One mechanism by which <a href="/wiki/Drug_tolerance" title="Drug tolerance">tolerance</a> to MDMA may occur is <a href="/wiki/Endocytosis" title="Endocytosis">internalization</a> of the <a href="/wiki/Serotonin_transporter" title="Serotonin transporter">serotonin transporter</a> (SERT).<a href="#cite_note-BisagnoCadet2021-197">[197]</a><a href="#cite_note-KivellDayBosch2010-198">[198]</a><a href="#cite_note-HolleySimonsonKivell2013-199">[199]</a><a href="#cite_note-UnderhillAmara2020-200">[200]</a><a href="#cite_note-UnderhillAmara2022-201">[201]</a> Although MDMA and serotonin are not significant TAAR1 agonists in humans, TAAR1 activation by MDMA may result in SERT internalization.<a href="#cite_note-UnderhillAmara2020-200">[200]</a><a href="#cite_note-UnderhillAmara2022-201">[201]</a><a href="#cite_note-KittlerLauSchloss2010-202">[202]</a><a href="#cite_note-GainetdinovHoenerBerry2018-149">[149]</a> <table class="wikitable" style="font-size:small;"> <caption><a href="/wiki/Monoamine_releasing_agent" title="Monoamine releasing agent">Monoamine release</a> by MDMA and related agents (<a href="/wiki/Half-maximal_effective_concentration" class="mw-redirect" title="Half-maximal effective concentration"><abbr title="half-maximal effective concentration">EC50</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip half-maximal effective concentration, nM) </caption> <tbody><tr> <th>Compound</th> <th><a href="/wiki/Serotonin_releasing_agent" title="Serotonin releasing agent">Serotonin</a></th> <th><a href="/wiki/Norepinephrine_releasing_agent" title="Norepinephrine releasing agent">Norepinephrine</a></th> <th><a href="/wiki/Dopamine_releasing_agent" title="Dopamine releasing agent">Dopamine</a> </th></tr> <tr> <td><a href="/wiki/Amphetamine" title="Amphetamine">Amphetamine</a></td> <td><abbr title="No data">ND</abbr></td> <td><abbr title="No data">ND</abbr></td> <td><abbr title="No data">ND</abbr> </td></tr> <tr> <td>  <a href="/wiki/Dextroamphetamine" title="Dextroamphetamine">(S)-Amphetamine</a> (d)</td> <td>698–1,765</td> <td>6.6–7.2</td> <td>5.8–24.8 </td></tr> <tr> <td>  <a href="/wiki/Levoamphetamine" title="Levoamphetamine">(R)-Amphetamine</a> (l)</td> <td><abbr title="No data">ND</abbr></td> <td>9.5</td> <td>27.7 </td></tr> <tr> <td><a href="/wiki/Methamphetamine" title="Methamphetamine">Methamphetamine</a></td> <td><abbr title="No data">ND</abbr></td> <td><abbr title="No data">ND</abbr></td> <td><abbr title="No data">ND</abbr> </td></tr> <tr> <td>  <a href="/wiki/Dextromethamphetamine" class="mw-redirect" title="Dextromethamphetamine">(S)-Methamphetamine</a> (d)</td> <td>736–1,292</td> <td>12.3–13.8</td> <td>8.5–24.5 </td></tr> <tr> <td>  <a href="/wiki/Levomethamphetamine" class="mw-redirect" title="Levomethamphetamine">(R)-Methamphetamine</a> (l)</td> <td>4,640</td> <td>28.5</td> <td>416 </td></tr> <tr> <td><a href="/wiki/Methylenedioxyamphetamine" class="mw-redirect" title="Methylenedioxyamphetamine">MDA</a></td> <td>160</td> <td>108</td> <td>190 </td></tr> <tr> <td>MDMA</td> <td>49.6–72</td> <td>54.1–110</td> <td>51.2–278 </td></tr> <tr> <td>  (S)-MDMA (d)</td> <td>74</td> <td>136</td> <td>142 </td></tr> <tr> <td>  <a href="/wiki/(R)-MDMA" title="(R)-MDMA">(R)-MDMA</a> (l)</td> <td>340</td> <td>560</td> <td>3,700 </td></tr> <tr> <td><a href="/wiki/Methylenedioxyethylamphetamine" class="mw-redirect" title="Methylenedioxyethylamphetamine">MDEA</a></td> <td>47</td> <td>2,608</td> <td>622 </td></tr> <tr> <td><a href="/wiki/Methylbenzodioxolylbutanamine" class="mw-redirect" title="Methylbenzodioxolylbutanamine">MBDB</a></td> <td>540</td> <td>3,300</td> <td>>100,000 </td></tr> <tr> <td><a href="/wiki/5,6-Methylenedioxy-2-aminoindane" class="mw-redirect" title="5,6-Methylenedioxy-2-aminoindane">MDAI</a></td> <td>114</td> <td>117</td> <td>1,334 </td></tr> <tr class="sortbottom"> <td colspan="4" style="width: 1px; background-color:#eaecf0; text-align: center;">Notes: The smaller the value, the more strongly the drug releases the neurotransmitter. The <a href="/wiki/Bioassay" title="Bioassay">assays</a> were done in rat brain <a href="/wiki/Synaptosome" title="Synaptosome">synaptosomes</a> and human <a href="/wiki/Potency_(pharmacology)" title="Potency (pharmacology)">potencies</a> may be different. See also <a href="/wiki/Monoamine_releasing_agent#Activity_profiles" title="Monoamine releasing agent">Monoamine releasing agent § Activity profiles</a> for a larger table with more compounds. Refs: <a href="#cite_note-RothmanBaumann2006-155">[155]</a><a href="#cite_note-SetolaHufeisenGrande-Allen2003-160">[160]</a><a href="#cite_note-RothmanBaumannDersch2001-203">[203]</a><a href="#cite_note-RothmanPartillaBaumann2012-204">[204]</a><a href="#cite_note-MarusichAntonazzoBlough2016-205">[205]</a><a href="#cite_note-NagaiNonakaKamimura2007-206">[206]</a><a href="#cite_note-HalberstadtBrandtWalther2019-207">[207]</a><a href="#cite_note-Blough2008-208">[208]</a><a href="#cite_note-DunlapAndrewsOlson2018-17">[17]</a> </td></tr></tbody></table> <div class="mw-heading mw-heading3"><h3 id="Pharmacokinetics">Pharmacokinetics</h3></div> <figure class="mw-halign-left skin-invert-image" typeof="mw:File/Thumb"><a href="/wiki/File:Main_metabolic_pathways_of_MDMA_in_humans.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/7/7c/Main_metabolic_pathways_of_MDMA_in_humans.svg/300px-Main_metabolic_pathways_of_MDMA_in_humans.svg.png" decoding="async" width="300" height="202" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/7/7c/Main_metabolic_pathways_of_MDMA_in_humans.svg/450px-Main_metabolic_pathways_of_MDMA_in_humans.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/7/7c/Main_metabolic_pathways_of_MDMA_in_humans.svg/600px-Main_metabolic_pathways_of_MDMA_in_humans.svg.png 2x" data-file-width="830" data-file-height="560" /></a><figcaption>Main metabolic pathways of MDMA in humans.</figcaption></figure> The MDMA <a href="/wiki/Concentration" title="Concentration">concentration</a> in the <a href="/wiki/Blood_stream" class="mw-redirect" title="Blood stream">blood stream</a> starts to rise after about 30 minutes,<a href="#cite_note-209">[209]</a> and reaches its maximal <a href="/wiki/Concentration" title="Concentration">concentration</a> in the blood stream between 1.5 and 3 hours after <a href="/wiki/Ingestion" title="Ingestion">ingestion</a>.<a href="#cite_note-TORRE1-210">[210]</a> It is then slowly <a href="/wiki/Metabolism" title="Metabolism">metabolized</a> and <a href="/wiki/Excretion" title="Excretion">excreted</a>, with levels of MDMA and its metabolites decreasing to half their peak concentration over the next several hours.<a href="#cite_note-TORRE2-211">[211]</a> The <a href="/wiki/Duration_of_action" class="mw-redirect" title="Duration of action">duration of action</a> of MDMA is about 3 to 6 hours.<a href="#cite_note-Oeri2021-18">[18]</a> Brain serotonin levels are depleted after MDMA administration but serotonin levels typically return to normal within 24 to 48 hours.<a href="#cite_note-Betzler2017-8">[8]</a> <a href="/wiki/Metabolite" title="Metabolite">Metabolites</a> of MDMA that have been identified in humans include <a href="/wiki/3,4-Methylenedioxyamphetamine" title="3,4-Methylenedioxyamphetamine">3,4-methylenedioxyamphetamine</a> (MDA), <a href="/wiki/4-hydroxy-3-methoxymethamphetamine" class="mw-redirect" title="4-hydroxy-3-methoxymethamphetamine">4-hydroxy-3-methoxymethamphetamine</a> (HMMA), 4-hydroxy-3-methoxyamphetamine (HMA), <a href="/wiki/Alpha-Methyldopamine" class="mw-redirect" title="Alpha-Methyldopamine">3,4-dihydroxyamphetamine</a> (DHA) (also called alpha-methyldopamine (α-Me-DA)), <a href="/wiki/MDP2P" class="mw-redirect" title="MDP2P">3,4-methylenedioxyphenylacetone</a> (MDP2P), and <a href="/wiki/Methylenedioxyhydroxyamphetamine" class="mw-redirect" title="Methylenedioxyhydroxyamphetamine">3,4-methylenedioxy-N-hydroxyamphetamine</a> (MDOH). The contributions of these metabolites to the psychoactive and <a href="/wiki/Toxic" class="mw-redirect" title="Toxic">toxic</a> effects of MDMA are an area of active research. 80% of MDMA is metabolised in the liver, and about 20% is excreted unchanged in the <a href="/wiki/Urine" title="Urine">urine</a>.<a href="#cite_note-pmid22392347-15">[15]</a> MDMA is known to be metabolized by two main <a href="/wiki/Metabolic_pathway" title="Metabolic pathway">metabolic pathways</a>: (1) O-demethylenation followed by <a href="/wiki/Catechol-O-methyl_transferase" class="mw-redirect" title="Catechol-O-methyl transferase">catechol-O-methyltransferase</a> (COMT)-catalyzed methylation or glucuronide/sulfate conjugation; and (2) N-dealkylation, deamination, and oxidation to the corresponding <a href="/wiki/Benzoic_acid" title="Benzoic acid">benzoic acid</a> derivatives conjugated with <a href="/wiki/Glycine" title="Glycine">glycine</a>.<a href="#cite_note-delaTorreFarréRoset2004-118">[118]</a> The metabolism may be primarily by <a href="/wiki/Cytochrome_P450_oxidase" class="mw-redirect" title="Cytochrome P450 oxidase">cytochrome P450</a> (CYP450) <a href="/wiki/Enzyme" title="Enzyme">enzymes</a> <a href="/wiki/CYP2D6" title="CYP2D6">CYP2D6</a> and <a href="/wiki/CYP3A4" title="CYP3A4">CYP3A4</a> and COMT. Complex, nonlinear <a href="/wiki/Pharmacokinetics" title="Pharmacokinetics">pharmacokinetics</a> arise via autoinhibition of <a href="/wiki/CYP2D6" title="CYP2D6">CYP2D6</a> and CYP2D8, resulting in <a href="/wiki/Rate_equation" title="Rate equation">zeroth order kinetics</a> at higher doses. It is thought that this can result in sustained and higher <a href="/wiki/Concentration" title="Concentration">concentrations</a> of MDMA if the user takes consecutive doses of the drug.<a href="#cite_note-Kolbrich_2008-212">[212]</a>[<a href="/wiki/Wikipedia:No_original_research#Primary,_secondary_and_tertiary_sources" title="Wikipedia:No original research">non-primary source needed</a>] MDMA and metabolites are primarily excreted as conjugates, such as sulfates and glucuronides.<a href="#cite_note-pmid17643356-213">[213]</a> MDMA is a <a href="/wiki/Chirality_(chemistry)" title="Chirality (chemistry)">chiral</a> compound and has been almost exclusively administered as a <a href="/wiki/Racemic" class="mw-redirect" title="Racemic">racemate</a>. However, the two enantiomers have been shown to exhibit different kinetics. The disposition of MDMA may also be stereoselective, with the S-enantiomer having a shorter elimination half-life and greater excretion than the R-enantiomer. Evidence suggests<a href="#cite_note-fallon-214">[214]</a> that the area under the <a href="/wiki/Blood_plasma" title="Blood plasma">blood plasma</a> concentration versus time curve (AUC) was two to four times higher for the (R)-enantiomer than the (S)-enantiomer after a 40 mg oral dose in human volunteers. Likewise, the plasma half-life of <a href="/wiki/(R)-MDMA" title="(R)-MDMA">(R)-MDMA</a> was significantly longer than that of the (S)-enantiomer (5.8 ± 2.2 hours vs 3.6 ± 0.9 hours).<a href="#cite_note-Toxnet_MDMA_after-effects-77">[77]</a> However, because MDMA excretion and metabolism have nonlinear kinetics,<a href="#cite_note-mueller-215">[215]</a> the half-lives would be higher at more typical doses (100 mg is sometimes considered a typical dose).<a href="#cite_note-TORRE1-210">[210]</a> <div class="mw-heading mw-heading2"><h2 id="Chemistry">Chemistry</h2></div> <table style="float:right"> <tbody><tr> <td><div class="skin-invert-image"> <table role="presentation" cellpadding="0" style="border-spacing:0; clear:right; float:right;"> <tbody><tr> <td><div class="thumb tright"> <div class="thumbinner" style="width:202px;"> <div class="{{{class}}}" style="position:relative; width:200px; height:195px; overflow:hidden; border:solid #ccc 1px; background-color:white;"> <div style="left:0px; top:0px; width:200px; position:absolute"> <a href="https://commons.wikimedia.org/wiki/File:(%C2%B1)-MDMA-Formel_Structural_Formulae.svg" title="commons:File:(±)-MDMA-Formel Structural Formulae.svg"><img alt="Racemic MDMA structure diagram" src="//upload.wikimedia.org/wikipedia/commons/thumb/4/46/%28%C2%B1%29-MDMA-Formel_Structural_Formulae.svg/200px-%28%C2%B1%29-MDMA-Formel_Structural_Formulae.svg.png" decoding="async" width="200" height="182" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/4/46/%28%C2%B1%29-MDMA-Formel_Structural_Formulae.svg/300px-%28%C2%B1%29-MDMA-Formel_Structural_Formulae.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/4/46/%28%C2%B1%29-MDMA-Formel_Structural_Formulae.svg/400px-%28%C2%B1%29-MDMA-Formel_Structural_Formulae.svg.png 2x" data-file-width="430" data-file-height="391" /></a> </div> <div style="text-align:center; font-size:16px; line-height:110%"> <div style="background-color:transparent; color:black"><div id="annotation_60x70" style="position:absolute; left:60px; top:70px; line-height:110%;">(R)-MDMA</div> <div id="annotation_60x175" style="position:absolute; left:60px; top:175px; line-height:110%;">(S)-MDMA</div></div> </div> </div> <div class="thumbcaption" style="clear:left">MDMA is a <a href="/wiki/Racemic_mixture" title="Racemic mixture">racemic mixture</a> and exists as two <a href="/wiki/Enantiomers" class="mw-redirect" title="Enantiomers">enantiomers</a>: <a href="/wiki/(R)-MDMA" title="(R)-MDMA">(R)-MDMA</a> and (S)-MDMA.</div> </div> </div> </td></tr></tbody></table></div> </td></tr> <tr> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1273380762/mw-parser-output/.tmulti" /><div class="thumb tmulti tright"><div class="thumbinner multiimageinner" style="width:204px;max-width:204px"><div class="trow"><div class="tsingle" style="width:202px;max-width:202px"><div class="thumbimage"><a href="/wiki/File:White_MDMA_salt_in_a_bag.jpg" class="mw-file-description"><img alt="A powdered salt of MDMA" src="//upload.wikimedia.org/wikipedia/commons/thumb/f/fe/White_MDMA_salt_in_a_bag.jpg/200px-White_MDMA_salt_in_a_bag.jpg" decoding="async" width="200" height="170" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/f/fe/White_MDMA_salt_in_a_bag.jpg/300px-White_MDMA_salt_in_a_bag.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/f/fe/White_MDMA_salt_in_a_bag.jpg/400px-White_MDMA_salt_in_a_bag.jpg 2x" data-file-width="2264" data-file-height="1920" /></a></div><div class="thumbcaption">A powdered salt of MDMA</div></div></div><div class="trow"><div class="tsingle" style="width:202px;max-width:202px"><div class="thumbimage"><a href="/wiki/File:MDMAjakarta.jpg" class="mw-file-description"><img alt="Reactors used in synthesis" src="//upload.wikimedia.org/wikipedia/commons/thumb/e/e4/MDMAjakarta.jpg/200px-MDMAjakarta.jpg" decoding="async" width="200" height="179" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/e/e4/MDMAjakarta.jpg 1.5x" data-file-width="250" data-file-height="224" /></a></div><div class="thumbcaption">Reactors used to synthesize MDMA on an industrial scale in a <a href="/wiki/Clandestine_chemistry" title="Clandestine chemistry">clandestine chemical factory</a> in Cikande, <a href="/wiki/Indonesia" title="Indonesia">Indonesia</a></div></div></div></div></div> </td></tr></tbody></table> MDMA is in the <a href="/wiki/Substituted_methylenedioxyphenethylamine" title="Substituted methylenedioxyphenethylamine">substituted methylenedioxyphenethylamine</a> and <a href="/wiki/Substituted_amphetamine" title="Substituted amphetamine">substituted amphetamine</a> <a href="/wiki/Chemical_classification" class="mw-redirect" title="Chemical classification">classes of chemicals</a>. As a <a href="/wiki/Free_base" title="Free base">free base</a>, MDMA is a colorless oil insoluble in water.<a href="#cite_note-EU2015-10">[10]</a> The most common salt of MDMA is the hydrochloride salt;<a href="#cite_note-EU2015-10">[10]</a> pure MDMA hydrochloride is water-soluble and appears as a white or off-white powder or crystal.<a href="#cite_note-EU2015-10">[10]</a> <div class="mw-heading mw-heading3"><h3 id="Synthesis">Synthesis</h3></div> There are numerous methods available to synthesize MDMA via different intermediates.<a href="#cite_note-216">[216]</a><a href="#cite_note-217">[217]</a><a href="#cite_note-218">[218]</a><a href="#cite_note-219">[219]</a> The original MDMA synthesis described in Merck's patent involves brominating <a href="/wiki/Safrole" title="Safrole">safrole</a> to 1-(3,4-methylenedioxyphenyl)-2-bromopropane and then reacting this adduct with methylamine.<a href="#cite_note-220">[220]</a><a href="#cite_note-221">[221]</a> Most illicit MDMA is synthesized using <a href="/wiki/MDP2P" class="mw-redirect" title="MDP2P">MDP2P</a> (3,4-methylenedioxyphenyl-2-propanone) as a precursor. MDP2P in turn is generally synthesized from <a href="/wiki/Piperonal" title="Piperonal">piperonal</a>, <a href="/wiki/Safrole" title="Safrole">safrole</a> or <a href="/wiki/Isosafrole" title="Isosafrole">isosafrole</a>.<a href="#cite_note-World_Drug_Report_2014-222">[222]</a> One method is to <a href="/wiki/Isomerization" title="Isomerization">isomerize</a> safrole to isosafrole in the presence of a strong base, and then oxidize <a href="/wiki/Isosafrole" title="Isosafrole">isosafrole</a> to MDP2P. Another method uses the <a href="/wiki/Wacker_process" title="Wacker process">Wacker process</a> to oxidize safrole directly to the MDP2P intermediate with a <a href="/wiki/Palladium" title="Palladium">palladium</a> catalyst. Once the MDP2P intermediate has been prepared, a <a href="/wiki/Reductive_amination" title="Reductive amination">reductive amination</a> leads to <a href="/wiki/Racemic" class="mw-redirect" title="Racemic">racemic</a> MDMA (an equal parts mixture of <a href="/wiki/(R)-MDMA" title="(R)-MDMA">(R)-MDMA</a> and (S)-MDMA).[<a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed">citation needed</a>] Relatively small quantities of essential oil are required to make large amounts of MDMA. The essential oil of <a href="/wiki/Ocotea_cymbarum" title="Ocotea cymbarum">Ocotea cymbarum</a>, for example, typically contains between 80 and 94% safrole. This allows 500 mL of the oil to produce between 150 and 340 grams of MDMA.<a href="#cite_note-223">[223]</a> <div class="skin-invert-image"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1273380762/mw-parser-output/.tmulti" /><div class="thumb tmulti tleft"><div class="thumbinner multiimageinner" style="width:604px;max-width:604px"><div class="trow"><div class="tsingle" style="width:602px;max-width:602px"><div class="thumbimage"><a href="/wiki/File:MDMA_Synthesis_1.svg" class="mw-file-description"><img alt="Synthesis of MDMA from piperonal" src="//upload.wikimedia.org/wikipedia/commons/thumb/c/cf/MDMA_Synthesis_1.svg/600px-MDMA_Synthesis_1.svg.png" decoding="async" width="600" height="56" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/c/cf/MDMA_Synthesis_1.svg/900px-MDMA_Synthesis_1.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/c/cf/MDMA_Synthesis_1.svg/1200px-MDMA_Synthesis_1.svg.png 2x" data-file-width="1559" data-file-height="146" /></a></div></div></div><div class="trow"><div class="tsingle" style="width:402px;max-width:402px"><div class="thumbimage"><a href="/wiki/File:MDMA_Synthese_2.svg" class="mw-file-description"><img alt="Synthesis of MDMA from piperonal" src="//upload.wikimedia.org/wikipedia/commons/thumb/2/27/MDMA_Synthese_2.svg/400px-MDMA_Synthese_2.svg.png" decoding="async" width="400" height="40" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/2/27/MDMA_Synthese_2.svg/600px-MDMA_Synthese_2.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/2/27/MDMA_Synthese_2.svg/800px-MDMA_Synthese_2.svg.png 2x" data-file-width="1026" data-file-height="102" /></a></div><div class="thumbcaption">Synthesis of MDMA from piperonal</div></div></div><div class="trow"><div class="tsingle" style="width:402px;max-width:402px"><div class="thumbimage"><a href="/wiki/File:MDA_from_safrole_en.png" class="mw-file-description"><img alt="Synthesis of MDMA and related analogs from safrole" src="//upload.wikimedia.org/wikipedia/commons/thumb/7/78/MDA_from_safrole_en.png/400px-MDA_from_safrole_en.png" decoding="async" width="400" height="51" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/7/78/MDA_from_safrole_en.png/600px-MDA_from_safrole_en.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/7/78/MDA_from_safrole_en.png/800px-MDA_from_safrole_en.png 2x" data-file-width="1000" data-file-height="127" /></a></div><div class="thumbcaption">Synthesis of MDMA and related analogs from safrole</div></div></div></div></div></div> <div style="clear:left;" class=""></div> <div class="mw-heading mw-heading3"><h3 id="Detection_in_body_fluids">Detection in body fluids</h3></div> MDMA and MDA may be quantitated in blood, plasma or urine to monitor for use, confirm a diagnosis of poisoning or assist in the forensic investigation of a traffic or other criminal violation or a sudden death. Some drug abuse screening programs rely on hair, saliva, or sweat as specimens. Most commercial amphetamine immunoassay screening tests cross-react significantly with MDMA or its major metabolites, but chromatographic techniques can easily distinguish and separately measure each of these substances. The concentrations of MDA in the blood or urine of a person who has taken only MDMA are, in general, less than 10% those of the parent drug.<a href="#cite_note-Kolbrich_2008-212">[212]</a><a href="#cite_note-224">[224]</a><a href="#cite_note-225">[225]</a> <div style="clear:both;" class=""></div> <div class="mw-heading mw-heading2"><h2 id="History">History</h2></div> <div class="mw-heading mw-heading3"><h3 id="Early_research_and_use">Early research and use</h3></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1273380762/mw-parser-output/.tmulti" /><div class="thumb tmulti tright"><div class="thumbinner multiimageinner" style="width:292px;max-width:292px"><div class="trow"><div class="tsingle" style="width:144px;max-width:144px"><div class="thumbimage" style="height:201px;overflow:hidden"><a href="/wiki/File:Merck_MDMA_Synthesis_Patent.pdf" class="mw-file-description"><img alt="Merck MDMA synthesis patent" src="//upload.wikimedia.org/wikipedia/commons/thumb/1/12/Merck_MDMA_Synthesis_Patent.pdf/page1-142px-Merck_MDMA_Synthesis_Patent.pdf.jpg" decoding="async" width="142" height="201" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/1/12/Merck_MDMA_Synthesis_Patent.pdf/page1-213px-Merck_MDMA_Synthesis_Patent.pdf.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/1/12/Merck_MDMA_Synthesis_Patent.pdf/page1-284px-Merck_MDMA_Synthesis_Patent.pdf.jpg 2x" data-file-width="1239" data-file-height="1754" /></a></div></div><div class="tsingle" style="width:144px;max-width:144px"><div class="thumbimage" style="height:201px;overflow:hidden"><a href="/wiki/File:Merck_patent_for_synthesizing_methylhydrastinine_from_MDMA.pdf" class="mw-file-description"><img alt="Merck patent for synthesizing methylhydrastinine from MDMA" src="//upload.wikimedia.org/wikipedia/commons/thumb/7/74/Merck_patent_for_synthesizing_methylhydrastinine_from_MDMA.pdf/page1-142px-Merck_patent_for_synthesizing_methylhydrastinine_from_MDMA.pdf.jpg" decoding="async" width="142" height="201" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/7/74/Merck_patent_for_synthesizing_methylhydrastinine_from_MDMA.pdf/page1-213px-Merck_patent_for_synthesizing_methylhydrastinine_from_MDMA.pdf.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/7/74/Merck_patent_for_synthesizing_methylhydrastinine_from_MDMA.pdf/page1-284px-Merck_patent_for_synthesizing_methylhydrastinine_from_MDMA.pdf.jpg 2x" data-file-width="1239" data-file-height="1754" /></a></div></div></div><div class="trow" style="display:flex"><div class="thumbcaption">German patents for MDMA synthesis and the subsequent methylhydrastinine synthesis filed by Merck on 24 December 1912 and issued in 1914</div></div></div></div> MDMA was first <a href="/wiki/Chemical_synthesis" title="Chemical synthesis">synthesized</a> and <a href="/wiki/Patent" title="Patent">patented</a> in 1912 by <a href="/wiki/Merck_KGaA" class="mw-redirect" title="Merck KGaA">Merck</a> chemist <a href="/wiki/Anton_K%C3%B6llisch" title="Anton Köllisch">Anton Köllisch</a>.<a href="#cite_note-Passie2023-226">[226]</a><a href="#cite_note-Bernschneider-ReifOxlerFreudenmann2006-227">[227]</a> At the time, Merck was interested in developing substances that stopped abnormal bleeding. Merck wanted to avoid an existing patent held by <a href="/wiki/Bayer" title="Bayer">Bayer</a> for one such compound: <a href="/wiki/Hydrastinine" title="Hydrastinine">hydrastinine</a>. Köllisch developed a preparation of a hydrastinine <a href="/wiki/Chemical_analogue" class="mw-redirect" title="Chemical analogue">analogue</a>, methylhydrastinine, at the request of fellow lab members, Walther Beckh and Otto Wolfes. MDMA (called methylsafrylamin, safrylmethylamin or N-Methyl-a-Methylhomopiperonylamin in Merck laboratory reports) was an <a href="/wiki/Reaction_intermediate" title="Reaction intermediate">intermediate compound</a> in the synthesis of methylhydrastinine. Merck was not interested in MDMA itself at the time.<a href="#cite_note-pmid17152992-228">[228]</a> On 24 December 1912, Merck filed two patent applications that described the synthesis and some chemical properties of MDMA<a href="#cite_note-DE274350-229">[229]</a> and its subsequent conversion to methylhydrastinine.<a href="#cite_note-DE279194-230">[230]</a> Merck records indicate its researchers returned to the compound sporadically. A 1920 Merck patent describes a chemical modification to MDMA.<a href="#cite_note-Passie2023-226">[226]</a><a href="#cite_note-Shulgin1990-231">[231]</a> MDMA's <a href="/wiki/Structural_analog" title="Structural analog">analogue</a> <a href="/wiki/3,4-methylenedioxyamphetamine" class="mw-redirect" title="3,4-methylenedioxyamphetamine">3,4-methylenedioxyamphetamine</a> (MDA) was first synthesized in 1910 as a <a href="/wiki/Chemical_derivative" class="mw-redirect" title="Chemical derivative">derivative</a> of <a href="/wiki/Adrenaline" title="Adrenaline">adrenaline</a>.<a href="#cite_note-Passie2023-226">[226]</a> <a href="/wiki/Gordon_A._Alles" class="mw-redirect" title="Gordon A. Alles">Gordon A. Alles</a>, the discoverer of the <a href="/wiki/Psychoactive_drug" title="Psychoactive drug">psychoactive</a> effects of <a href="/wiki/Amphetamine" title="Amphetamine">amphetamine</a>, also discovered the psychoactive effects of MDA in 1930 in a <a href="/wiki/Self-experiment" class="mw-redirect" title="Self-experiment">self-experiment</a> in which he administered a high dose (126 mg) to himself.<a href="#cite_note-Passie2023-226">[226]</a><a href="#cite_note-Alles1959-232">[232]</a> MDA was later tested as an <a href="/wiki/Appetite_suppressant" class="mw-redirect" title="Appetite suppressant">appetite suppressant</a> by <a href="/wiki/Smith,_Kline_%26_French" title="Smith, Kline & French">Smith, Kline & French</a> and for other uses by other groups in the 1950s.<a href="#cite_note-Passie2023-226">[226]</a> In relation to this, the psychoactive effects of MDA were discovered well before those of MDMA.<a href="#cite_note-Passie2023-226">[226]</a> In 1927, Max Oberlin studied the pharmacology of MDMA while searching for substances with effects similar to <a href="/wiki/Adrenaline" title="Adrenaline">adrenaline</a> or <a href="/wiki/Ephedrine" title="Ephedrine">ephedrine</a>, the latter being structurally similar to MDMA. Compared to ephedrine, Oberlin observed that it had similar effects on <a href="/wiki/Vascular_smooth_muscle" title="Vascular smooth muscle">vascular smooth muscle</a> tissue, stronger effects at the uterus, and no "local effect at the eye". MDMA was also found to have effects on <a href="/wiki/Blood_sugar" class="mw-redirect" title="Blood sugar">blood sugar</a> levels comparable to high doses of ephedrine. Oberlin concluded that the effects of MDMA were not limited to the <a href="/wiki/Sympathetic_nervous_system" title="Sympathetic nervous system">sympathetic nervous system</a>. Research was stopped "particularly due to a strong price increase of safrylmethylamine", which was still used as an intermediate in methylhydrastinine synthesis. Albert van Schoor performed simple toxicological tests with the drug in 1952, most likely while researching new stimulants or circulatory medications. After pharmacological studies, research on MDMA was not continued. In 1959, Wolfgang Fruhstorfer synthesized MDMA for pharmacological testing while researching stimulants. It is unclear if Fruhstorfer investigated the effects of MDMA in humans.<a href="#cite_note-pmid17152992-228">[228]</a> Outside of Merck, other researchers began to investigate MDMA. In 1953 and 1954, the <a href="/wiki/United_States_Army" title="United States Army">United States Army</a> commissioned a study of <a href="/wiki/Toxicity" title="Toxicity">toxicity</a> and behavioral effects in animals injected with <a href="/wiki/Mescaline" title="Mescaline">mescaline</a> and several analogues, including MDMA. Conducted at the <a href="/wiki/University_of_Michigan" title="University of Michigan">University of Michigan</a> in <a href="/wiki/Ann_Arbor" class="mw-redirect" title="Ann Arbor">Ann Arbor</a>, these investigations were declassified in October 1969 and published in 1973.<a href="#cite_note-pmid4197635-233">[233]</a><a href="#cite_note-Shulgin-234">[234]</a> A 1960 Polish paper by Biniecki and Krajewski describing the synthesis of MDMA as an intermediate was the first published scientific paper on the substance.<a href="#cite_note-pmid17152992-228">[228]</a><a href="#cite_note-Shulgin-234">[234]</a><a href="#cite_note-235">[235]</a> MDA appeared as a <a href="/wiki/Recreational_drug" class="mw-redirect" title="Recreational drug">recreational drug</a> in the mid-1960s.<a href="#cite_note-Passie2023-226">[226]</a> MDMA may have been in non-medical use in the western United States in 1968.<a href="#cite_note-Passie2023-226">[226]</a><a href="#cite_note-Siegel_1986-236">[236]</a> An August 1970 report at a meeting of crime laboratory chemists indicates MDMA was being used recreationally in the Chicago area by 1970.<a href="#cite_note-Shulgin-234">[234]</a><a href="#cite_note-237">[237]</a> MDMA likely emerged as a substitute for MDA,<a href="#cite_note-Foderaro_1988-238">[238]</a> a drug at the time popular among users of psychedelics<a href="#cite_note-Professor_X-239">[239]</a> which was made a <a href="/wiki/List_of_Schedule_I_controlled_substances_(U.S.)" title="List of Schedule I controlled substances (U.S.)">Schedule 1 controlled substance</a> in the United States in 1970.<a href="#cite_note-Beck_1987-240">[240]</a><a href="#cite_note-exploration-241">[241]</a> <div class="mw-heading mw-heading3"><h3 id="Shulgin's_research">Shulgin's research</h3></div> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:Shulgin_sasha_2011_hanna_jon.jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/e/e0/Shulgin_sasha_2011_hanna_jon.jpg/220px-Shulgin_sasha_2011_hanna_jon.jpg" decoding="async" width="220" height="220" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/e0/Shulgin_sasha_2011_hanna_jon.jpg/330px-Shulgin_sasha_2011_hanna_jon.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/e/e0/Shulgin_sasha_2011_hanna_jon.jpg/440px-Shulgin_sasha_2011_hanna_jon.jpg 2x" data-file-width="3714" data-file-height="3714" /></a><figcaption>Alexander and Ann Shulgin in December 2011</figcaption></figure> American chemist and <a href="/wiki/Psychopharmacologist" class="mw-redirect" title="Psychopharmacologist">psychopharmacologist</a> <a href="/wiki/Alexander_Shulgin" title="Alexander Shulgin">Alexander Shulgin</a> reported he synthesized MDMA in 1965 while researching methylenedioxy compounds at <a href="/wiki/Dow_Chemical_Company" title="Dow Chemical Company">Dow Chemical Company</a>, but did not test the psychoactivity of the compound at this time. Around 1970, Shulgin sent instructions for N-methylated MDA (MDMA) synthesis to the founder of a Los Angeles chemical company who had requested them. This individual later provided these instructions to a client in the Midwest. Shulgin may have suspected he played a role in the emergence of MDMA in Chicago.<a href="#cite_note-Shulgin-234">[234]</a> Shulgin first heard of the psychoactive effects of N-methylated MDA around 1975 from a young student who reported "amphetamine-like content".<a href="#cite_note-Shulgin-234">[234]</a> Around 30 May 1976, Shulgin again heard about the effects of N-methylated MDA,<a href="#cite_note-Shulgin-234">[234]</a> this time from a graduate student in a medicinal chemistry group he advised at <a href="/wiki/San_Francisco_State_University" title="San Francisco State University">San Francisco State University</a><a href="#cite_note-Professor_X-239">[239]</a><a href="#cite_note-242">[242]</a> who directed him to the University of Michigan study.<a href="#cite_note-PiHKAL-243">[243]</a> She and two close friends had consumed 100 mg of MDMA and reported positive emotional experiences.<a href="#cite_note-Shulgin-234">[234]</a> Following the self-trials of a colleague at the <a href="/wiki/University_of_San_Francisco" title="University of San Francisco">University of San Francisco</a>, Shulgin synthesized MDMA and tried it himself in September and October 1976.<a href="#cite_note-Shulgin-234">[234]</a><a href="#cite_note-Professor_X-239">[239]</a> Shulgin first reported on MDMA in a presentation at a conference in Bethesda, Maryland in December 1976.<a href="#cite_note-Shulgin-234">[234]</a> In 1978, he and <a href="/wiki/David_E._Nichols" title="David E. Nichols">David E. Nichols</a> published a report on the drug's psychoactive effect in humans.<a href="#cite_note-Passie2023-226">[226]</a> They described MDMA as inducing "an easily controlled altered state of consciousness with emotional and sensual overtones" comparable "to marijuana, to <a href="/wiki/Psilocybin" title="Psilocybin">psilocybin</a> devoid of the hallucinatory component, or to low levels of MDA".<a href="#cite_note-isbn0-08-021938-1-244">[244]</a> While not finding his own experiences with MDMA particularly powerful,<a href="#cite_note-PiHKAL-243">[243]</a><a href="#cite_note-Dr._Ecstasy-245">[245]</a> Shulgin was impressed with the drug's disinhibiting effects and thought it could be useful in therapy.<a href="#cite_note-Dr._Ecstasy-245">[245]</a> Believing MDMA allowed users to strip away habits and perceive the world clearly, Shulgin called the drug window.<a href="#cite_note-PiHKAL-243">[243]</a><a href="#cite_note-rising-246">[246]</a> Shulgin occasionally used MDMA for relaxation, referring to it as "my low-calorie martini", and gave the drug to friends, researchers, and others who he thought could benefit from it.<a href="#cite_note-PiHKAL-243">[243]</a> One such person was <a href="/wiki/Leo_Zeff" title="Leo Zeff">Leo Zeff</a>, a psychotherapist who had been known to use psychedelic substances in his practice. When he tried the drug in 1977, Zeff was impressed with the effects of MDMA and came out of his semi-retirement to promote its use in therapy. Over the following years, Zeff traveled around the United States and occasionally to Europe, eventually training an estimated four thousand psychotherapists in the therapeutic use of MDMA.<a href="#cite_note-Dr._Ecstasy-245">[245]</a><a href="#cite_note-247">[247]</a> Zeff named the drug Adam, believing it put users in a state of primordial innocence.<a href="#cite_note-Professor_X-239">[239]</a> Psychotherapists who used MDMA believed the drug eliminated the typical fear response and increased communication. Sessions were usually held in the home of the patient or the therapist. The role of the therapist was minimized in favor of patient self-discovery accompanied by MDMA induced feelings of empathy. Depression, substance use disorders, relationship problems, premenstrual syndrome, and autism were among several psychiatric disorders MDMA assisted therapy was reported to treat.<a href="#cite_note-exploration-241">[241]</a> According to psychiatrist George Greer, therapists who used MDMA in their practice were impressed by the results. Anecdotally, MDMA was said to greatly accelerate therapy.<a href="#cite_note-Dr._Ecstasy-245">[245]</a> According to <a href="/wiki/David_Nutt" title="David Nutt">David Nutt</a>, MDMA was widely used in the western US in couples counseling, and was called empathy. Only later was the term ecstasy used for it, coinciding with rising opposition to its use.<a href="#cite_note-Nutt-248">[248]</a><a href="#cite_note-pmid10450215-249">[249]</a> <div class="mw-heading mw-heading3"><h3 id="Rising_recreational_use">Rising recreational use</h3></div> In the late 1970s and early 1980s, "Adam" spread through personal networks of psychotherapists, psychiatrists, users of psychedelics, and <a href="/wiki/Yuppies" class="mw-redirect" title="Yuppies">yuppies</a>. Hoping MDMA could avoid criminalization like LSD and mescaline, psychotherapists and experimenters attempted to limit the spread of MDMA and information about it while conducting informal research.<a href="#cite_note-exploration-241">[241]</a><a href="#cite_note-Eisner-250">[250]</a> Early MDMA distributors were deterred from large scale operations by the threat of possible legislation.<a href="#cite_note-Beck_&_Rosenbaum-251">[251]</a> Between the 1970s and the mid-1980s, this network of MDMA users consumed an estimated 500,000 doses.<a href="#cite_note-Current2013-22">[22]</a><a href="#cite_note-isbn0803936788-252">[252]</a> A small recreational market for MDMA developed by the late 1970s,<a href="#cite_note-isbn9781847656414-253">[253]</a> consuming perhaps 10,000 doses in 1976.<a href="#cite_note-Beck_1987-240">[240]</a> By the early 1980s MDMA was being used in Boston and New York City nightclubs such as <a href="/wiki/Studio_54" title="Studio 54">Studio 54</a> and <a href="/wiki/Paradise_Garage" title="Paradise Garage">Paradise Garage</a>.<a href="#cite_note-254">[254]</a><a href="#cite_note-255">[255]</a> Into the early 1980s, as the recreational market slowly expanded, production of MDMA was dominated by a small group of therapeutically minded <a href="/wiki/Boston" title="Boston">Boston</a> chemists. Having commenced production in 1976, this "Boston Group" did not keep up with growing demand and shortages frequently occurred.<a href="#cite_note-Beck_&_Rosenbaum-251">[251]</a> Perceiving a business opportunity, Michael Clegg, the Southwest distributor for the Boston Group, started his own "Texas Group" backed financially by Texas friends.<a href="#cite_note-Beck_&_Rosenbaum-251">[251]</a><a href="#cite_note-256">[256]</a> In 1981,<a href="#cite_note-Beck_&_Rosenbaum-251">[251]</a> Clegg had coined "Ecstasy" as a slang term for MDMA to increase its marketability.<a href="#cite_note-rising-246">[246]</a><a href="#cite_note-Eisner-250">[250]</a> Starting in 1983,<a href="#cite_note-Beck_&_Rosenbaum-251">[251]</a> the Texas Group mass-produced MDMA in a Texas lab<a href="#cite_note-Eisner-250">[250]</a> or imported it from California<a href="#cite_note-rising-246">[246]</a> and marketed tablets using pyramid sales structures and toll-free numbers.<a href="#cite_note-isbn0803936788-252">[252]</a> MDMA could be purchased via credit card and taxes were paid on sales.<a href="#cite_note-Beck_&_Rosenbaum-251">[251]</a> Under the brand name "Sassyfras", MDMA tablets were sold in brown bottles.<a href="#cite_note-Eisner-250">[250]</a> The Texas Group advertised "Ecstasy parties" at bars and discos, describing MDMA as a "fun drug" and "good to dance to".<a href="#cite_note-Beck_&_Rosenbaum-251">[251]</a> MDMA was openly distributed in <a href="/wiki/Austin,_Texas" title="Austin, Texas">Austin</a> and <a href="/wiki/Dallas%E2%80%93Fort_Worth" class="mw-redirect" title="Dallas–Fort Worth">Dallas–Fort Worth</a> area bars and nightclubs, becoming popular with yuppies, college students, and gays.<a href="#cite_note-Foderaro_1988-238">[238]</a><a href="#cite_note-Beck_&_Rosenbaum-251">[251]</a><a href="#cite_note-isbn0803936788-252">[252]</a> Recreational use also increased after several cocaine dealers switched to distributing MDMA following experiences with the drug.<a href="#cite_note-isbn0803936788-252">[252]</a> A California laboratory that analyzed confidentially submitted drug samples first detected MDMA in 1975. Over the following years the number of MDMA samples increased, eventually exceeding the number of MDA samples in the early 1980s.<a href="#cite_note-257">[257]</a><a href="#cite_note-258">[258]</a> By the mid-1980s, MDMA use had spread to colleges around the United States.<a href="#cite_note-Beck_&_Rosenbaum-251">[251]</a>: 33  <div class="mw-heading mw-heading3"><h3 id="Media_attention_and_scheduling">Media attention and scheduling</h3></div> <div class="mw-heading mw-heading4"><h4 id="United_States">United States</h4></div> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:Federal_Register_notice_of_planned_MDMA_scheduling.pdf" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/7/7b/Federal_Register_notice_of_planned_MDMA_scheduling.pdf/page1-220px-Federal_Register_notice_of_planned_MDMA_scheduling.pdf.jpg" decoding="async" width="220" height="285" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/7/7b/Federal_Register_notice_of_planned_MDMA_scheduling.pdf/page1-330px-Federal_Register_notice_of_planned_MDMA_scheduling.pdf.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/7/7b/Federal_Register_notice_of_planned_MDMA_scheduling.pdf/page1-440px-Federal_Register_notice_of_planned_MDMA_scheduling.pdf.jpg 2x" data-file-width="1275" data-file-height="1650" /></a><figcaption>27 July 1984 Federal Register notice of the proposed MDMA scheduling</figcaption></figure> In an early media report on MDMA published in 1982, a <a href="/wiki/Drug_Enforcement_Administration" title="Drug Enforcement Administration">Drug Enforcement Administration</a> (DEA) spokesman stated the agency would ban the drug if enough evidence for abuse could be found.<a href="#cite_note-Beck_&_Rosenbaum-251">[251]</a> By mid-1984, MDMA use was becoming more noticed. Bill Mandel reported on "Adam" in a 10 June <a href="/wiki/San_Francisco_Chronicle" title="San Francisco Chronicle">San Francisco Chronicle</a> article, but misidentified the drug as <a href="/wiki/MMDA_(drug)" title="MMDA (drug)">methyloxymethylenedioxyamphetamine</a> (MMDA). In the next month, the World Health Organization identified MDMA as the only substance out of twenty phenethylamines to be seized a significant number of times.<a href="#cite_note-Eisner-250">[250]</a> After a year of planning and data collection, MDMA was proposed for <a href="/wiki/Controlled_Substances_Act" title="Controlled Substances Act">scheduling</a> by the DEA on 27 July 1984, with a request for comments and objections.<a href="#cite_note-Eisner-250">[250]</a><a href="#cite_note-259">[259]</a> The DEA was surprised when a number of psychiatrists, psychotherapists, and researchers objected to the proposed scheduling and requested a hearing.<a href="#cite_note-exploration-241">[241]</a> In a <a href="/wiki/Newsweek" title="Newsweek">Newsweek</a> article published the next year, a DEA pharmacologist stated that the agency had been unaware of its use among psychiatrists.<a href="#cite_note-260">[260]</a> An initial hearing was held on 1 February 1985 at the DEA offices in Washington, D.C., with administrative law judge Francis L. Young presiding.<a href="#cite_note-Eisner-250">[250]</a> It was decided there to hold three more hearings that year: Los Angeles on 10 June, Kansas City, Missouri on 10–11 July, and Washington, D.C., on 8–11 October.<a href="#cite_note-exploration-241">[241]</a><a href="#cite_note-Eisner-250">[250]</a> Sensational media attention was given to the proposed criminalization and the reaction of MDMA proponents, effectively advertising the drug.<a href="#cite_note-exploration-241">[241]</a> In response to the proposed scheduling, the Texas Group increased production from 1985 estimates of 30,000 tablets a month to as many as 8,000 per day, potentially making two million ecstasy tablets in the months before MDMA was made illegal.<a href="#cite_note-comprehensive-261">[261]</a> By some estimates the Texas Group distributed 500,000 tablets per month in Dallas alone.<a href="#cite_note-rising-246">[246]</a> According to one participant in an <a href="/wiki/Ethnographic" class="mw-redirect" title="Ethnographic">ethnographic</a> study, the Texas Group produced more MDMA in eighteen months than all other distribution networks combined across their entire histories.<a href="#cite_note-Beck_&_Rosenbaum-251">[251]</a> By May 1985, MDMA use was widespread in California, Texas, southern Florida, and the northeastern United States.<a href="#cite_note-Siegel_1986-236">[236]</a><a href="#cite_note-New_York_Times-262">[262]</a> According to the DEA there was evidence of use in twenty-eight states<a href="#cite_note-263">[263]</a> and Canada.<a href="#cite_note-Siegel_1986-236">[236]</a> Urged by Senator <a href="/wiki/Lloyd_Bentsen" title="Lloyd Bentsen">Lloyd Bentsen</a>, the DEA announced an <a href="/wiki/Comprehensive_Crime_Control_Act_of_1984" title="Comprehensive Crime Control Act of 1984">emergency Schedule I classification</a> of MDMA on 31 May 1985. The agency cited increased distribution in Texas, escalating street use, and new evidence of MDA (an analog of MDMA) neurotoxicity as reasons for the emergency measure.<a href="#cite_note-New_York_Times-262">[262]</a><a href="#cite_note-264">[264]</a><a href="#cite_note-265">[265]</a> The ban took effect one month later on 1 July 1985<a href="#cite_note-comprehensive-261">[261]</a> in the midst of <a href="/wiki/Nancy_Reagan" title="Nancy Reagan">Nancy Reagan</a>'s "<a href="/wiki/Just_Say_No" title="Just Say No">Just Say No</a>" campaign.<a href="#cite_note-266">[266]</a><a href="#cite_note-267">[267]</a> As a result of several expert witnesses testifying that MDMA had an accepted medical usage, the administrative law judge presiding over the hearings recommended that MDMA be classified as a <a href="/wiki/Controlled_Substances_Act#Schedule_III_controlled_substances" title="Controlled Substances Act">Schedule III</a> substance. Despite this, DEA administrator <a href="/wiki/John_C._Lawn" title="John C. Lawn">John C. Lawn</a> overruled and classified the drug as Schedule I.<a href="#cite_note-exploration-241">[241]</a><a href="#cite_note-Harpers-268">[268]</a> Harvard psychiatrist <a href="/wiki/Lester_Grinspoon" title="Lester Grinspoon">Lester Grinspoon</a> then sued the DEA, claiming that the DEA had ignored the medical uses of MDMA, and the federal court sided with Grinspoon, calling Lawn's argument "strained" and "unpersuasive", and vacated MDMA's Schedule I status.<a href="#cite_note-269">[269]</a> Despite this, less than a month later Lawn reviewed the evidence and reclassified MDMA as Schedule I again, claiming that the expert testimony of several psychiatrists claiming over 200 cases where MDMA had been used in a therapeutic context with positive results could be dismissed because they were not published in medical journals.<a href="#cite_note-exploration-241">[241]</a> In 2017, the FDA <a href="#Research">granted</a> <a href="/wiki/Breakthrough_therapy" title="Breakthrough therapy">breakthrough therapy</a> designation for its use with psychotherapy for PTSD. However, this designation has been questioned and problematized.<a href="#cite_note-Halvorsen_1689–1690-270">[270]</a> <div class="mw-heading mw-heading4"><h4 id="United_Nations">United Nations</h4></div> While engaged in scheduling debates in the United States, the DEA also pushed for international scheduling.<a href="#cite_note-comprehensive-261">[261]</a> In 1985, the <a href="/wiki/World_Health_Organization" title="World Health Organization">World Health Organization</a>'s Expert Committee on Drug Dependence recommended that MDMA be placed in Schedule I of the 1971 United Nations <a href="/wiki/Convention_on_Psychotropic_Substances" title="Convention on Psychotropic Substances">Convention on Psychotropic Substances</a>. The committee made this recommendation on the basis of the pharmacological similarity of MDMA to previously scheduled drugs, reports of illicit trafficking in Canada, drug seizures in the United States, and lack of well-defined therapeutic use. While intrigued by reports of psychotherapeutic uses for the drug, the committee viewed the studies as lacking appropriate methodological design and encouraged further research. Committee chairman <a href="/wiki/Paul_Grof" title="Paul Grof">Paul Grof</a> dissented, believing international control was not warranted at the time and a recommendation should await further therapeutic data.<a href="#cite_note-271">[271]</a> The <a href="/wiki/Commission_on_Narcotic_Drugs" class="mw-redirect" title="Commission on Narcotic Drugs">Commission on Narcotic Drugs</a> added MDMA to Schedule I of the convention on 11 February 1986.<a href="#cite_note-272">[272]</a> <div class="mw-heading mw-heading3"><h3 id="Post-scheduling">Post-scheduling</h3></div> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:1995-04-08_Vibe_Tribe_09_(10937582).jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/1/18/1995-04-08_Vibe_Tribe_09_%2810937582%29.jpg/220px-1995-04-08_Vibe_Tribe_09_%2810937582%29.jpg" decoding="async" width="220" height="139" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/1/18/1995-04-08_Vibe_Tribe_09_%2810937582%29.jpg/330px-1995-04-08_Vibe_Tribe_09_%2810937582%29.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/1/18/1995-04-08_Vibe_Tribe_09_%2810937582%29.jpg/440px-1995-04-08_Vibe_Tribe_09_%2810937582%29.jpg 2x" data-file-width="1761" data-file-height="1109" /></a><figcaption>A 1995 Vibe Tribe rave in <a href="/wiki/Erskineville,_New_South_Wales" class="mw-redirect" title="Erskineville, New South Wales">Erskineville, New South Wales</a>, Australia being broken up by police. MDMA use spread globally along with rave culture.</figcaption></figure> <figure class="mw-default-size" typeof="mw:File/Thumb"><video id="mwe_player_0" poster="//upload.wikimedia.org/wikipedia/commons/thumb/c/cb/Ecstasy_-_Is_it_Really_the_Dream_Drug.ogv/220px--Ecstasy_-_Is_it_Really_the_Dream_Drug.ogv.jpg" controls="" preload="none" data-mw-tmh="" class="mw-file-element" width="220" height="165" data-durationhint="595" data-mwtitle="Ecstasy_-_Is_it_Really_the_Dream_Drug.ogv" data-mwprovider="wikimediacommons" resource="/wiki/File:Ecstasy_-_Is_it_Really_the_Dream_Drug.ogv"><source src="//upload.wikimedia.org/wikipedia/commons/c/cb/Ecstasy_-_Is_it_Really_the_Dream_Drug.ogv" type="video/ogg; codecs="theora, vorbis"" data-width="400" data-height="300" /><source src="//upload.wikimedia.org/wikipedia/commons/transcoded/c/cb/Ecstasy_-_Is_it_Really_the_Dream_Drug.ogv/Ecstasy_-_Is_it_Really_the_Dream_Drug.ogv.360p.webm" type="video/webm; codecs="vp8, vorbis"" data-transcodekey="360p.webm" data-width="400" data-height="300" /><source src="//upload.wikimedia.org/wikipedia/commons/transcoded/c/cb/Ecstasy_-_Is_it_Really_the_Dream_Drug.ogv/Ecstasy_-_Is_it_Really_the_Dream_Drug.ogv.144p.mjpeg.mov" type="video/quicktime" data-transcodekey="144p.mjpeg.mov" data-width="192" data-height="144" /><source src="//upload.wikimedia.org/wikipedia/commons/transcoded/c/cb/Ecstasy_-_Is_it_Really_the_Dream_Drug.ogv/Ecstasy_-_Is_it_Really_the_Dream_Drug.ogv.240p.vp9.webm" type="video/webm; codecs="vp9, opus"" data-transcodekey="240p.vp9.webm" data-width="320" data-height="240" /><track src="https://commons.wikimedia.org/w/api.php?action=timedtext&title=File%3AEcstasy_-_Is_it_Really_the_Dream_Drug.ogv&lang=en&trackformat=vtt&origin=%2A" kind="subtitles" type="text/vtt" srclang="en" label="English ‪(en)‬" data-dir="ltr" /></video><figcaption>A 2000 <a href="/wiki/United_States_Air_Force" title="United States Air Force">United States Air Force</a> video dramatizing the dangers of MDMA misuse</figcaption></figure> The use of MDMA in Texas clubs declined rapidly after criminalization, but by 1991, the drug became popular among young middle-class whites and in nightclubs.<a href="#cite_note-Beck_&_Rosenbaum-251">[251]</a> In 1985, MDMA use became associated with <a href="/wiki/Acid_house" title="Acid house">acid house</a> on the Spanish island of <a href="/wiki/Ibiza" title="Ibiza">Ibiza</a>.<a href="#cite_note-Beck_&_Rosenbaum-251">[251]</a>: 50 <a href="#cite_note-273">[273]</a> Thereafter, in the late 1980s, the drug spread alongside <a href="/wiki/Rave_culture" class="mw-redirect" title="Rave culture">rave culture</a> to the UK and then to other European and American cities.<a href="#cite_note-Beck_&_Rosenbaum-251">[251]</a>: 50  Illicit MDMA use became increasingly widespread among young adults in universities and later, in high schools. Since the mid-1990s, MDMA has become the most widely used amphetamine-type drug by college students and teenagers.<a href="#cite_note-Goldfrank_2011-274">[274]</a>: 1080  MDMA became one of the four most widely used illicit drugs in the US, along with <a href="/wiki/Cocaine" title="Cocaine">cocaine</a>, <a href="/wiki/Heroin" title="Heroin">heroin</a>, and <a href="/wiki/Cannabis_(drug)" title="Cannabis (drug)">cannabis</a>.<a href="#cite_note-rising-246">[246]</a> According to some estimates as of 2004, only marijuana attracts more first time users in the US.<a href="#cite_note-rising-246">[246]</a> After MDMA was criminalized, most medical use stopped, although some therapists continued to prescribe the drug illegally. Later,[<a href="/wiki/Wikipedia:Manual_of_Style/Dates_and_numbers#Chronological_items" title="Wikipedia:Manual of Style/Dates and numbers">when?</a>] Charles Grob initiated an ascending-dose safety study in healthy volunteers. Subsequent FDA-approved MDMA studies in humans have taken place in the United States in Detroit (<a href="/wiki/Wayne_State_University" title="Wayne State University">Wayne State University</a>), Chicago (<a href="/wiki/University_of_Chicago" title="University of Chicago">University of Chicago</a>), San Francisco (UCSF and <a href="/wiki/California_Pacific_Medical_Center" title="California Pacific Medical Center">California Pacific Medical Center</a>), <a href="/wiki/Baltimore" title="Baltimore">Baltimore</a> (<a href="/wiki/National_Institute_on_Drug_Abuse" title="National Institute on Drug Abuse">NIDA</a>–<a href="/wiki/NIH" class="mw-redirect" title="NIH">NIH</a> Intramural Program), and <a href="/wiki/South_Carolina" title="South Carolina">South Carolina</a>. Studies have also been conducted in Switzerland (University Hospital of Psychiatry, <a href="/wiki/Z%C3%BCrich" class="mw-redirect" title="Zürich">Zürich</a>), the Netherlands (<a href="/wiki/Maastricht_University" title="Maastricht University">Maastricht University</a>), and Spain (<a href="/wiki/Universitat_Aut%C3%B2noma_de_Barcelona" class="mw-redirect" title="Universitat Autònoma de Barcelona">Universitat Autònoma de Barcelona</a>).<a href="#cite_note-275">[275]</a> "Molly", short for 'molecule', was recognized as a slang term for crystalline or powder MDMA in the 2000s.<a href="#cite_note-276">[276]</a><a href="#cite_note-277">[277]</a> In 2010, the BBC reported that use of MDMA had decreased in the UK in previous years. This may be due to increased seizures during use and decreased production of the precursor chemicals used to manufacture MDMA. Unwitting substitution with other drugs, such as <a href="/wiki/Mephedrone" title="Mephedrone">mephedrone</a> and <a href="/wiki/Methamphetamine" title="Methamphetamine">methamphetamine</a>,<a href="#cite_note-278">[278]</a> as well as legal alternatives to MDMA, such as <a href="/wiki/Benzylpiperazine" title="Benzylpiperazine">BZP</a>, <a href="/wiki/Methylenedioxypyrovalerone" title="Methylenedioxypyrovalerone">MDPV</a>, and <a href="/wiki/Methylone" title="Methylone">methylone</a>, are also thought to have contributed to its decrease in popularity.<a href="#cite_note-279">[279]</a> In 2017, it was found that some pills being sold as MDMA contained <a href="/wiki/Pentylone" title="Pentylone">pentylone</a>, which can cause very unpleasant agitation and paranoia.<a href="#cite_note-280">[280]</a> According to <a href="/wiki/David_Nutt" title="David Nutt">David Nutt</a>, when <a href="/wiki/Safrole" title="Safrole">safrole</a> was restricted by the United Nations in order to reduce the supply of MDMA, producers in China began using <a href="/wiki/Anethole" title="Anethole">anethole</a> instead, but this gives <a href="/wiki/Para-methoxyamphetamine" class="mw-redirect" title="Para-methoxyamphetamine">para-methoxyamphetamine</a> (PMA, also known as "Dr Death"), which is much more toxic than MDMA and can cause overheating, muscle spasms, seizures, unconsciousness, and death. People wanting MDMA are sometimes sold PMA instead.<a href="#cite_note-Nutt-248">[248]</a> <div class="mw-heading mw-heading2"><h2 id="Society_and_culture">Society and culture</h2></div> <table class="wikitable sortable floatright" style="text-align:center;"> <caption>Global estimates of drug users in 2016 (in millions of users)<a href="#cite_note-281">[281]</a> </caption> <tbody><tr> <th>Substance</th> <th>Best estimate</th> <th>Low estimate</th> <th>High estimate </th></tr> <tr> <td><a href="/wiki/Amphetamine-type_stimulants#Schedules_of_Controlled_Substances" class="mw-redirect" title="Amphetamine-type stimulants">Amphetamine- type stimulants</a></td> <td>34.16</td> <td>13.42</td> <td>55.24 </td></tr> <tr> <td><a href="/wiki/Cannabis_(drug)" title="Cannabis (drug)">Cannabis</a></td> <td>192.15</td> <td>165.76</td> <td>234.06 </td></tr> <tr> <td><a href="/wiki/Cocaine" title="Cocaine">Cocaine</a></td> <td>18.20</td> <td>13.87</td> <td>22.85 </td></tr> <tr> <td><a class="mw-selflink selflink">Ecstasy</a></td> <td>20.57</td> <td>8.99</td> <td>32.34 </td></tr> <tr> <td><a href="/wiki/Opiate" title="Opiate">Opiates</a></td> <td>19.38</td> <td>13.80</td> <td>26.15 </td></tr> <tr> <td><a href="/wiki/Opioid" title="Opioid">Opioids</a></td> <td>34.26</td> <td>27.01</td> <td>44.54 </td></tr> </tbody></table> <div class="mw-heading mw-heading3"><h3 id="Legal_status">Legal status</h3></div> MDMA is legally controlled in most of the world under the UN <a href="/wiki/Convention_on_Psychotropic_Substances" title="Convention on Psychotropic Substances">Convention on Psychotropic Substances</a> and other international agreements, although exceptions exist for research and limited medical use. In general, the unlicensed use, sale or manufacture of MDMA are all criminal offences. <div class="mw-heading mw-heading4"><h4 id="Australia">Australia</h4></div> In Australia, MDMA was rescheduled on 1 July 2023 as a schedule 8 substance (available on prescription) when used in the treatment of PTSD, while remaining a schedule 9 substance (prohibited) for all other uses. For the treatment of PTSD, MDMA can only be prescribed by psychiatrists with specific training and authorisation.<a href="#cite_note-282">[282]</a> In 1986, MDMA was declared an illegal substance because of its allegedly harmful effects and potential for misuse.<a href="#cite_note-283">[283]</a> Any non-authorised sale, use or manufacture is strictly prohibited by law. Permits for research uses on humans must be approved by a recognized <a href="/wiki/National_Health_and_Medical_Research_Council" title="National Health and Medical Research Council">ethics committee</a> on human research. In <a href="/wiki/Western_Australia" title="Western Australia">Western Australia</a> under the Misuse of Drugs Act 1981 4.0g of MDMA is the amount required determining a court of trial, 2.0g is considered a presumption with intent to sell or supply and 28.0g is considered trafficking under Australian law.<a href="#cite_note-284">[284]</a> The Australian Capital Territory passed legislation to decriminalise the possession of small amounts of MDMA, which took effect in October 2023.<a href="#cite_note-285">[285]</a><a href="#cite_note-Roy_2023-286">[286]</a> <div class="mw-heading mw-heading4"><h4 id="United_Kingdom">United Kingdom</h4></div> In the United Kingdom, MDMA was made illegal in 1977 by a modification order to the existing <a href="/wiki/Misuse_of_Drugs_Act_1971" title="Misuse of Drugs Act 1971">Misuse of Drugs Act 1971</a>. Although MDMA was not named explicitly in this legislation, the order extended the definition of Class A drugs to include various ring-substituted phenethylamines.<a href="#cite_note-Drugs_2.0-287">[287]</a><a href="#cite_note-UK_legality-288">[288]</a> The drug is therefore illegal to sell, buy, or possess without a licence in the UK. Penalties include a maximum of seven years and/or unlimited fine for possession; life and/or unlimited fine for production or trafficking. Some researchers such as <a href="/wiki/David_Nutt" title="David Nutt">David Nutt</a> have criticized the scheduling of MDMA, which he determined to be a relatively harmless drug.<a href="#cite_note-289">[289]</a><a href="#cite_note-290">[290]</a> An editorial he wrote in the <a href="/wiki/Journal_of_Psychopharmacology" title="Journal of Psychopharmacology">Journal of Psychopharmacology</a>, where he compared the risk of harm for <a href="/wiki/Horse_Riding" class="mw-redirect" title="Horse Riding">horse riding</a> (1 adverse event in 350) to that of ecstasy (1 in 10,000) resulted in his dismissal as well as the resignation of his colleagues from the <a href="/wiki/Advisory_Council_on_the_Misuse_of_Drugs" title="Advisory Council on the Misuse of Drugs">ACMD</a>.<a href="#cite_note-johnson-291">[291]</a> <div class="mw-heading mw-heading4"><h4 id="United_States_2">United States</h4></div> In the United States, MDMA is listed in <a href="/wiki/Controlled_Substances_Act#Schedule_I_controlled_substances" title="Controlled Substances Act">Schedule I</a> of the <a href="/wiki/Controlled_Substances_Act" title="Controlled Substances Act">Controlled Substances Act</a>.<a href="#cite_note-292">[292]</a> In a 2011 federal court hearing, the <a href="/wiki/American_Civil_Liberties_Union" title="American Civil Liberties Union">American Civil Liberties Union</a> successfully argued that the sentencing guideline for MDMA/ecstasy is based on outdated science, leading to excessive prison sentences.<a href="#cite_note-293">[293]</a> Other courts have upheld the sentencing guidelines. The <a href="/wiki/United_States_District_Court_for_the_Eastern_District_of_Tennessee" title="United States District Court for the Eastern District of Tennessee">United States District Court for the Eastern District of Tennessee</a> explained its ruling by noting that "an individual federal district court judge simply cannot marshal resources akin to those available to the Commission for tackling the manifold issues involved with determining a proper drug equivalency."<a href="#cite_note-papers.ssrn.com-294">[294]</a> <div class="mw-heading mw-heading4"><h4 id="Netherlands">Netherlands</h4></div> In the Netherlands, the Expert Committee on the List (Expertcommissie Lijstensystematiek Opiumwet) issued a report in June 2011 which discussed the evidence for harm and the legal status of MDMA, arguing in favor of maintaining it on List I.<a href="#cite_note-papers.ssrn.com-294">[294]</a><a href="#cite_note-295">[295]</a><a href="#cite_note-296">[296]</a> <div class="mw-heading mw-heading4"><h4 id="Canada">Canada</h4></div> In Canada, MDMA is listed as a <a href="/wiki/Controlled_Drugs_and_Substances_Act#Schedule_I" title="Controlled Drugs and Substances Act">Schedule 1</a><a href="#cite_note-CDSA_Schedule_I:_Amphetamines-297">[297]</a> as it is an analogue of amphetamine.<a href="#cite_note-Definitions_and_Interpretations-298">[298]</a> The <a href="/wiki/Controlled_Drugs_and_Substances_Act" title="Controlled Drugs and Substances Act">Controlled Drugs and Substances Act</a> was updated as a result of the <a href="/wiki/Safe_Streets_and_Communities_Act" title="Safe Streets and Communities Act">Safe Streets and Communities Act</a> changing amphetamines from <a href="/wiki/Controlled_Drugs_and_Substances_Act#Schedule_III" title="Controlled Drugs and Substances Act">Schedule III</a> to Schedule I in March 2012. In 2022, the federal government granted <a href="/wiki/British_Columbia" title="British Columbia">British Columbia</a> a 3-year exemption, legalizing the possession of up to 2.5 grams (0.088 oz) of MDMA in the province from February 2023 until February 2026.<a href="#cite_note-299">[299]</a><a href="#cite_note-300">[300]</a> <div class="mw-heading mw-heading3"><h3 id="Demographics">Demographics</h3></div> <figure class="mw-default-size skin-invert-image" typeof="mw:File/Thumb"><a href="/wiki/File:UNODC_2016_World_Drug_Report_use_of_ecstasy_in_2014_(page_1_crop).jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/9/9a/UNODC_2016_World_Drug_Report_use_of_ecstasy_in_2014_%28page_1_crop%29.jpg/330px-UNODC_2016_World_Drug_Report_use_of_ecstasy_in_2014_%28page_1_crop%29.jpg" decoding="async" width="330" height="192" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/9/9a/UNODC_2016_World_Drug_Report_use_of_ecstasy_in_2014_%28page_1_crop%29.jpg/495px-UNODC_2016_World_Drug_Report_use_of_ecstasy_in_2014_%28page_1_crop%29.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/9/9a/UNODC_2016_World_Drug_Report_use_of_ecstasy_in_2014_%28page_1_crop%29.jpg/660px-UNODC_2016_World_Drug_Report_use_of_ecstasy_in_2014_%28page_1_crop%29.jpg 2x" data-file-width="3375" data-file-height="1964" /></a><figcaption>UNODC map showing the use of ecstasy by country in 2014 for the global population aged 15–64</figcaption></figure> In 2014, 3.5% of 18 to 25 year-olds had used MDMA in the United States.<a href="#cite_note-Betzler2017-8">[8]</a> In the European Union as of 2018, 4.1% of adults (15–64 years old) have used MDMA at least once in their life, and 0.8% had used it in the last year.<a href="#cite_note-European_Monitoring_Centre_for_Drugs_and_Drug_Addiction_(EMCDDA)-301">[301]</a> Among young adults, 1.8% had used MDMA in the last year.<a href="#cite_note-European_Monitoring_Centre_for_Drugs_and_Drug_Addiction_(EMCDDA)-301">[301]</a> In Europe, an estimated 37% of regular club-goers aged 14 to 35 used MDMA in the past year according to the 2015 European Drug report.<a href="#cite_note-Betzler2017-8">[8]</a> The highest one-year prevalence of MDMA use in Germany in 2012 was 1.7% among people aged 25 to 29 compared with a population average of 0.4%.<a href="#cite_note-Betzler2017-8">[8]</a> Among adolescent users in the United States between 1999 and 2008, girls were more likely to use MDMA than boys.<a href="#cite_note-302">[302]</a> <div class="mw-heading mw-heading3"><h3 id="Economics">Economics</h3></div> <div class="mw-heading mw-heading4"><h4 id="Europe">Europe</h4></div> In 2008 the <a href="/wiki/European_Monitoring_Centre_for_Drugs_and_Drug_Addiction" class="mw-redirect" title="European Monitoring Centre for Drugs and Drug Addiction">European Monitoring Centre for Drugs and Drug Addiction</a> noted that although there were some reports of tablets being sold for as little as €1, most countries in Europe then reported typical retail prices in the range of €3 to €9 per tablet, typically containing 25–65 mg of MDMA.<a href="#cite_note-303">[303]</a> By 2014 the EMCDDA reported that the range was more usually between €5 and €10 per tablet, typically containing 57–102 mg of MDMA, although MDMA in powder form was becoming more common.<a href="#cite_note-304">[304]</a> <div class="mw-heading mw-heading4"><h4 id="North_America">North America</h4></div> The <a href="/wiki/United_Nations_Office_on_Drugs_and_Crime" title="United Nations Office on Drugs and Crime">United Nations Office on Drugs and Crime</a> stated in its 2014 World Drug Report that US ecstasy retail prices range from US$1 to $70 per pill, or from $15,000 to $32,000 per kilogram.<a href="#cite_note-305">[305]</a> A new research area named Drug Intelligence aims to automatically monitor distribution networks based on image processing and machine learning techniques, in which an Ecstasy pill picture is analyzed to detect correlations among different production batches.<a href="#cite_note-306">[306]</a> These novel techniques allow police scientists to facilitate the monitoring of illicit distribution networks. As of October 2015<a class="external text" href="https://en.wikipedia.org/w/index.php?title=MDMA&action=edit">[update]</a>, most of the MDMA in the United States is produced in British Columbia, Canada and imported by Canada-based Asian <a href="/wiki/Transnational_organized_crime" title="Transnational organized crime">transnational criminal organizations</a>.<a href="#cite_note-DEA_2015_assessment-72">[72]</a> The market for MDMA in the United States is relatively small compared to <a href="/wiki/Methamphetamine" title="Methamphetamine">methamphetamine</a>, <a href="/wiki/Cocaine" title="Cocaine">cocaine</a>, and <a href="/wiki/Heroin" title="Heroin">heroin</a>.<a href="#cite_note-DEA_2015_assessment-72">[72]</a> In the United States, about 0.9 million people used ecstasy in 2010.<a href="#cite_note-Drugs2014-26">[26]</a> <div class="mw-heading mw-heading4"><h4 id="Australia_2">Australia</h4></div> MDMA is particularly expensive in Australia, costing <a href="/wiki/Australian_dollar" title="Australian dollar">A$</a>15–A$30 per tablet. In terms of purity data for Australian MDMA, the average is around 34%, ranging from less than 1% to about 85%. The majority of tablets contain 70–85 mg of MDMA. Most MDMA enters Australia from the Netherlands, the UK, Asia, and the US.<a href="#cite_note-307">[307]</a> <div class="mw-heading mw-heading4"><h4 id="Corporate_logos_on_pills">Corporate logos on pills</h4></div> A number of ecstasy manufacturers brand their pills with a logo, often being the <a href="/wiki/Corporate_logo" class="mw-redirect" title="Corporate logo">logo of an unrelated corporation</a>.<a href="#cite_note-308">[308]</a> Some pills depict logos of products or media popular with children, such as <a href="/wiki/Shaun_the_Sheep" title="Shaun the Sheep">Shaun the Sheep</a>.<a href="#cite_note-309">[309]</a> <div class="mw-heading mw-heading2"><h2 id="Research_directions">Research directions</h2></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951" /><div role="note" class="hatnote navigation-not-searchable">See also: <a href="/wiki/List_of_investigational_anxiolytics" title="List of investigational anxiolytics">List of investigational anxiolytics</a> and <a href="/wiki/Psychedelic_therapy" title="Psychedelic therapy">Psychedelic therapy</a></div> A 2014 review of the safety and efficacy of MDMA as a treatment for various disorders, particularly <a href="/wiki/Post-traumatic_stress_disorder" title="Post-traumatic stress disorder">post-traumatic stress disorder</a> (PTSD), indicated that MDMA has therapeutic efficacy in some patients.<a href="#cite_note-Pharm2014-92">[92]</a> Four clinical trials provide moderate evidence in support of this treatment.<a href="#cite_note-310">[310]</a> Some authors have concluded that because of MDMA's potential to cause lasting harm in humans (e.g., <a href="/wiki/Serotonin_syndrome" title="Serotonin syndrome">serotonergic neurotoxicity</a> and persistent memory impairment), "considerably more research must be performed" on its efficacy in PTSD treatment to determine if the potential treatment benefits outweigh its potential to harm a patient.<a href="#cite_note-Current2013-22">[22]</a><a href="#cite_note-Pharm2014-92">[92]</a> Other authors have argued that the neurotoxic effects of MDMA are dose-dependent,<a href="#cite_note-311">[311]</a> with lower doses exhibiting lower neurotoxicity or even neuroprotection,<a href="#cite_note-312">[312]</a> and that MDMA assisted psychotherapy is considerably safer than current treatments.<a href="#cite_note-313">[313]</a><div style="clear:both;" class=""></div> Animal models suggest that postnatal exposure may ameliorate social impairments in autism.<a href="#cite_note-314">[314]</a> Recent evidence suggests the safe and potentially effective use of MDMA to treat the negative symptoms of schizophrenia.<a href="#cite_note-315">[315]</a> Unlike other treatments for mental illness, MDMA would be intended to be used infrequently and alongside psychotherapy in treatment. <div class="mw-heading mw-heading2"><h2 id="See_also">See also</h2></div> <ul><li><a href="/wiki/Multidisciplinary_Association_for_Psychedelic_Studies" title="Multidisciplinary Association for Psychedelic Studies">Multidisciplinary Association for Psychedelic Studies</a> (MAPS)</li> <li><a href="/wiki/Lykos_Therapeutics" title="Lykos Therapeutics">Lykos Therapeutics</a></li> <li><a href="/wiki/I_Feel_Love:_MDMA_and_the_Quest_for_Connection_in_a_Fractured_World" class="mw-redirect" title="I Feel Love: MDMA and the Quest for Connection in a Fractured World">I Feel Love: MDMA and the Quest for Connection in a Fractured World</a></li></ul> <div class="mw-heading mw-heading2"><h2 id="References">References</h2></div> <style data-mw-deduplicate="TemplateStyles:r1239543626">.mw-parser-output .reflist{margin-bottom:0.5em;list-style-type:decimal}@media screen{.mw-parser-output .reflist{font-size:90%}}.mw-parser-output .reflist .references{font-size:100%;margin-bottom:0;list-style-type:inherit}.mw-parser-output .reflist-columns-2{column-width:30em}.mw-parser-output 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Retrieved 30 March 2016.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=National+Institute+on+Drug+Abuse&rft.atitle=DrugFacts%3A+MDMA+%28Ecstasy%2FMolly%29&rft.date=2016-02&rft_id=https%3A%2F%2Fwww.drugabuse.gov%2Fpublications%2Fdrugfacts%2Fmdma-ecstasymolly&rfr_id=info%3Asid%2Fen.wikipedia.org%3AMDMA" class="Z3988"> </li> <li id="cite_note-Merck-28"><a href="#cite_ref-Merck_28-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFFreudenmannÖxlerBernschneider-Reif2006" class="citation journal cs1">Freudenmann RW, Öxler F, Bernschneider-Reif S (August 2006). <a rel="nofollow" class="external text" href="http://www.thedea.org/docs/2006_Freudenmann_22846_1.pdf">"The origin of MDMA (ecstasy) revisited: the true story reconstructed from the original documents"</a> (PDF). Addiction. 101 (9): 1241–1245. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1111%2Fj.1360-0443.2006.01511.x">10.1111/j.1360-0443.2006.01511.x</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/16911722">16911722</a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20200922140222/http://www.thedea.org/docs/2006_Freudenmann_22846_1.pdf">Archived</a> (PDF) from the original on 22 September 2020. Retrieved 23 May 2019. <q>Although MDMA was, in fact, first synthesized at Merck in 1912, it was not tested pharmacologically because it was only an unimportant precursor in a new synthesis for haemostatic substances.</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Addiction&rft.atitle=The+origin+of+MDMA+%28ecstasy%29+revisited%3A+the+true+story+reconstructed+from+the+original+documents&rft.volume=101&rft.issue=9&rft.pages=%3Cspan+class%3D%22nowrap%22%3E1241-%3C%2Fspan%3E1245&rft.date=2006-08&rft_id=info%3Adoi%2F10.1111%2Fj.1360-0443.2006.01511.x&rft_id=info%3Apmid%2F16911722&rft.aulast=Freudenmann&rft.aufirst=RW&rft.au=%C3%96xler%2C+F&rft.au=Bernschneider-Reif%2C+S&rft_id=http%3A%2F%2Fwww.thedea.org%2Fdocs%2F2006_Freudenmann_22846_1.pdf&rfr_id=info%3Asid%2Fen.wikipedia.org%3AMDMA" class="Z3988"> </li> <li id="cite_note-WHO2004-29"><a href="#cite_ref-WHO2004_29-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFWorld_Health_Organization2004" class="citation book cs1">World Health Organization (2004). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=G9OhG-dZdAwC&pg=PA97">Neuroscience of Psychoactive Substance Use and Dependence</a>. World Health Organization. pp. 97–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-92-4-156235-5" title="Special:BookSources/978-92-4-156235-5"><bdi>978-92-4-156235-5</bdi></a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20160428231233/https://books.google.com/books?id=G9OhG-dZdAwC&pg=PA97">Archived</a> from the original on 28 April 2016.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Neuroscience+of+Psychoactive+Substance+Use+and+Dependence&rft.pages=97-&rft.pub=World+Health+Organization&rft.date=2004&rft.isbn=978-92-4-156235-5&rft.au=World+Health+Organization&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DG9OhG-dZdAwC%26pg%3DPA97&rfr_id=info%3Asid%2Fen.wikipedia.org%3AMDMA" class="Z3988"> </li> <li id="cite_note-UN2018-30">^ <a href="#cite_ref-UN2018_30-0">a</a> <a href="#cite_ref-UN2018_30-1">b</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite class="citation book cs1"><a rel="nofollow" class="external text" href="https://www.unodc.org/wdr2018/prelaunch/WDR18_Booklet_1_EXSUM.pdf">World Drug Report 2018</a> (PDF). United Nations. June 2018. p. 7. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-92-1-148304-8" title="Special:BookSources/978-92-1-148304-8"><bdi>978-92-1-148304-8</bdi></a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20180727030037/http://www.unodc.org/wdr2018/prelaunch/WDR18_Booklet_1_EXSUM.pdf">Archived</a> (PDF) from the original on 27 July 2018. 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Springer Science & Business Media. p. 147. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-90-481-2448-0" title="Special:BookSources/978-90-481-2448-0"><bdi>978-90-481-2448-0</bdi></a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20230113000534/https://books.google.com/books?id=OTAlolM3XlwC&pg=PA147">Archived</a> from the original on 13 January 2023. 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Life Sciences. 97 (1): 37–44. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2Fj.lfs.2013.07.014">10.1016/j.lfs.2013.07.014</a>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3870191">3870191</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/23892199">23892199</a>. <q>In contrast, MDMA produces damage to serotonergic, but not dopaminergic axon terminals in the striatum, hippocampus, and prefrontal cortex (Battaglia et al., 1987, O'Hearn et al., 1988). The damage associated with Meth and MDMA has been shown to persist for at least 2 years in rodents, non-human primates and humans (Seiden et al., 1988, Woolverton et al., 1989, McCann et al., 1998, Volkow et al., 2001a, McCann et al., 2005)</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Life+Sciences&rft.atitle=Neurotoxicity+of+methamphetamine+and+3%2C4-methylenedioxymethamphetamine&rft.volume=97&rft.issue=1&rft.pages=%3Cspan+class%3D%22nowrap%22%3E37-%3C%2Fspan%3E44&rft.date=2014-02&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC3870191%23id-name%3DPMC&rft_id=info%3Apmid%2F23892199&rft_id=info%3Adoi%2F10.1016%2Fj.lfs.2013.07.014&rft.aulast=Halpin&rft.aufirst=LE&rft.au=Collins%2C+SA&rft.au=Yamamoto%2C+BK&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC3870191&rfr_id=info%3Asid%2Fen.wikipedia.org%3AMDMA" class="Z3988"> </li> <li id="cite_note-90"><a href="#cite_ref-90">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFSzigetiWinstockErritzoeMaier2018" class="citation journal cs1">Szigeti B, Winstock AR, Erritzoe D, Maier LJ (July 2018). 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"Development of a rational scale to assess the harm of drugs of potential misuse". Lancet. 369 (9566): 1047–1053. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2FS0140-6736%2807%2960464-4">10.1016/S0140-6736(07)60464-4</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/17382831">17382831</a>. <a href="/wiki/S2CID_(identifier)" class="mw-redirect" title="S2CID (identifier)">S2CID</a> <a rel="nofollow" class="external text" href="https://api.semanticscholar.org/CorpusID:5903121">5903121</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Lancet&rft.atitle=Development+of+a+rational+scale+to+assess+the+harm+of+drugs+of+potential+misuse&rft.volume=369&rft.issue=9566&rft.pages=%3Cspan+class%3D%22nowrap%22%3E1047-%3C%2Fspan%3E1053&rft.date=2007-03&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A5903121%23id-name%3DS2CID&rft_id=info%3Apmid%2F17382831&rft_id=info%3Adoi%2F10.1016%2FS0140-6736%2807%2960464-4&rft.aulast=Nutt&rft.aufirst=D&rft.au=King%2C+LA&rft.au=Saulsbury%2C+W&rft.au=Blakemore%2C+C&rfr_id=info%3Asid%2Fen.wikipedia.org%3AMDMA" class="Z3988"> Lay summary: <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite class="citation web cs1"><a rel="nofollow" class="external text" href="http://news.bbc.co.uk/2/hi/health/6474053.stm">"Scientists want new drug rankings"</a>. BBC News. 23 March 2007. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20071202233524/http://news.bbc.co.uk/2/hi/health/6474053.stm">Archived</a> from the original on 2 December 2007. Retrieved 4 April 2008.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=BBC+News&rft.atitle=Scientists+want+new+drug+rankings&rft.date=2007-03-23&rft_id=http%3A%2F%2Fnews.bbc.co.uk%2F2%2Fhi%2Fhealth%2F6474053.stm&rfr_id=info%3Asid%2Fen.wikipedia.org%3AMDMA" class="Z3988"> </li> <li id="cite_note-MDMA_ΔFosB-103">^ <a href="#cite_ref-MDMA_ΔFosB_103-0">a</a> <a href="#cite_ref-MDMA_ΔFosB_103-1">b</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFOlaussonJentschTronsonNeve2006" class="citation journal cs1">Olausson P, Jentsch JD, Tronson N, Neve RL, Nestler EJ, Taylor JR (September 2006). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6674495">"DeltaFosB in the nucleus accumbens regulates food-reinforced instrumental behavior and motivation"</a>. The Journal of Neuroscience. 26 (36): 9196–204. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1523%2FJNEUROSCI.1124-06.2006">10.1523/JNEUROSCI.1124-06.2006</a>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6674495">6674495</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/16957076">16957076</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=The+Journal+of+Neuroscience&rft.atitle=DeltaFosB+in+the+nucleus+accumbens+regulates+food-reinforced+instrumental+behavior+and+motivation&rft.volume=26&rft.issue=36&rft.pages=%3Cspan+class%3D%22nowrap%22%3E9196-%3C%2Fspan%3E204&rft.date=2006-09&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC6674495%23id-name%3DPMC&rft_id=info%3Apmid%2F16957076&rft_id=info%3Adoi%2F10.1523%2FJNEUROSCI.1124-06.2006&rft.aulast=Olausson&rft.aufirst=P&rft.au=Jentsch%2C+JD&rft.au=Tronson%2C+N&rft.au=Neve%2C+RL&rft.au=Nestler%2C+EJ&rft.au=Taylor%2C+JR&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC6674495&rfr_id=info%3Asid%2Fen.wikipedia.org%3AMDMA" class="Z3988"> </li> <li id="cite_note-Nestler-104">^ <a href="#cite_ref-Nestler_104-0">a</a> <a href="#cite_ref-Nestler_104-1">b</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFRobisonNestler2011" class="citation journal cs1">Robison AJ, Nestler EJ (October 2011). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3272277">"Transcriptional and epigenetic mechanisms of addiction"</a>. Nature Reviews. Neuroscience. 12 (11): 623–37. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1038%2Fnrn3111">10.1038/nrn3111</a>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3272277">3272277</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/21989194">21989194</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Nature+Reviews.+Neuroscience&rft.atitle=Transcriptional+and+epigenetic+mechanisms+of+addiction&rft.volume=12&rft.issue=11&rft.pages=%3Cspan+class%3D%22nowrap%22%3E623-%3C%2Fspan%3E37&rft.date=2011-10&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC3272277%23id-name%3DPMC&rft_id=info%3Apmid%2F21989194&rft_id=info%3Adoi%2F10.1038%2Fnrn3111&rft.aulast=Robison&rft.aufirst=AJ&rft.au=Nestler%2C+EJ&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC3272277&rfr_id=info%3Asid%2Fen.wikipedia.org%3AMDMA" class="Z3988"> </li> <li id="cite_note-105"><a href="#cite_ref-105">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFMackBradyMillerFrances2016" class="citation book cs1">Mack AH, Brady KT, Miller SI, Frances RJ (12 May 2016). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=88W_CwAAQBAJ&pg=PA171">Clinical Textbook of Addictive Disorders</a>. Guilford Publications. p. 169. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1-4625-2169-2" title="Special:BookSources/978-1-4625-2169-2"><bdi>978-1-4625-2169-2</bdi></a>. <q>MDMA's addictive liability appears to be lower than that of other drugs of abuse....</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Clinical+Textbook+of+Addictive+Disorders&rft.pages=169&rft.pub=Guilford+Publications&rft.date=2016-05-12&rft.isbn=978-1-4625-2169-2&rft.aulast=Mack&rft.aufirst=AH&rft.au=Brady%2C+KT&rft.au=Miller%2C+SI&rft.au=Frances%2C+RJ&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3D88W_CwAAQBAJ%26pg%3DPA171&rfr_id=info%3Asid%2Fen.wikipedia.org%3AMDMA" class="Z3988"> </li> <li id="cite_note-106"><a href="#cite_ref-106">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFFavrod-CouneBroers2010" class="citation journal cs1">Favrod-Coune T, Broers B (July 2010). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4036656">"The Health Effect of Psychostimulants: A Literature Review"</a>. Pharmaceuticals. 3 (7): 2333–2361. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.3390%2Fph3072333">10.3390/ph3072333</a>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4036656">4036656</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/27713356">27713356</a>. <q>It seems to present a smaller addiction potential than cocaine or methamphetamine.</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Pharmaceuticals&rft.atitle=The+Health+Effect+of+Psychostimulants%3A+A+Literature+Review&rft.volume=3&rft.issue=7&rft.pages=%3Cspan+class%3D%22nowrap%22%3E2333-%3C%2Fspan%3E2361&rft.date=2010-07&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC4036656%23id-name%3DPMC&rft_id=info%3Apmid%2F27713356&rft_id=info%3Adoi%2F10.3390%2Fph3072333&rft.aulast=Favrod-Coune&rft.aufirst=T&rft.au=Broers%2C+B&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC4036656&rfr_id=info%3Asid%2Fen.wikipedia.org%3AMDMA" class="Z3988"> </li> <li id="cite_note-107"><a href="#cite_ref-107">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFRiesMillerFiellin2009" class="citation book cs1">Ries R, Miller SC, Fiellin DA (2009). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=j6GGBud8DXcC&pg=PA226">Principles of addiction medicine</a> (4th ed.). Philadelphia: Wolters Kluwer/Lippincott Williams & Wilkins. p. 226. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-7817-7477-2" title="Special:BookSources/978-0-7817-7477-2"><bdi>978-0-7817-7477-2</bdi></a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20230113000536/https://books.google.com/books?id=j6GGBud8DXcC&pg=PA226">Archived</a> from the original on 13 January 2023. Retrieved 11 January 2017. <q>MDA and MDMA are less reinforcing than amphetamine...</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Principles+of+addiction+medicine.&rft.place=Philadelphia&rft.pages=226&rft.edition=4th&rft.pub=Wolters+Kluwer%2FLippincott+Williams+%26+Wilkins&rft.date=2009&rft.isbn=978-0-7817-7477-2&rft.aulast=Ries&rft.aufirst=R&rft.au=Miller%2C+SC&rft.au=Fiellin%2C+DA&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3Dj6GGBud8DXcC%26pg%3DPA226&rfr_id=info%3Asid%2Fen.wikipedia.org%3AMDMA" class="Z3988"> </li> <li id="cite_note-Steinkellner2011-108">^ <a href="#cite_ref-Steinkellner2011_108-0">a</a> <a href="#cite_ref-Steinkellner2011_108-1">b</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFSteinkellnerFreissmuthSitteMontgomery2011" class="citation journal cs1">Steinkellner T, Freissmuth M, Sitte HH, Montgomery T (January 2011). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4497800">"The ugly side of amphetamines: short- and long-term toxicity of 3,4-methylenedioxymethamphetamine (MDMA, 'Ecstasy'), methamphetamine and D-amphetamine"</a>. Biological Chemistry. 392 (1–2): 103–15. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1515%2FBC.2011.016">10.1515/BC.2011.016</a>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4497800">4497800</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/21194370">21194370</a>. <q>...approximately 15% of routine MDMA users recently fit the diagnostic criteria for MDMA dependence according to the Diagnostic and Statistical Manual, fourth edition/DSMIV.</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Biological+Chemistry&rft.atitle=The+ugly+side+of+amphetamines%3A+short-+and+long-term+toxicity+of+3%2C4-methylenedioxymethamphetamine+%28MDMA%2C+%27Ecstasy%27%29%2C+methamphetamine+and+D-amphetamine&rft.volume=392&rft.issue=%3Cspan+class%3D%22nowrap%22%3E1%E2%80%93%3C%2Fspan%3E2&rft.pages=%3Cspan+class%3D%22nowrap%22%3E103-%3C%2Fspan%3E15&rft.date=2011-01&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC4497800%23id-name%3DPMC&rft_id=info%3Apmid%2F21194370&rft_id=info%3Adoi%2F10.1515%2FBC.2011.016&rft.aulast=Steinkellner&rft.aufirst=T&rft.au=Freissmuth%2C+M&rft.au=Sitte%2C+HH&rft.au=Montgomery%2C+T&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC4497800&rfr_id=info%3Asid%2Fen.wikipedia.org%3AMDMA" class="Z3988"> </li> <li id="cite_note-109"><a href="#cite_ref-109">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFMackBradyMillerFrances2016" class="citation book cs1">Mack AH, Brady KT, Miller SI, Frances RJ (12 May 2016). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=88W_CwAAQBAJ&q=mdma+addiction&pg=PA171">Clinical Textbook of Addictive Disorders</a>. Guilford Publications. p. 171. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1-4625-2169-2" title="Special:BookSources/978-1-4625-2169-2"><bdi>978-1-4625-2169-2</bdi></a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20230119130056/https://books.google.com/books?id=88W_CwAAQBAJ&q=mdma+addiction&pg=PA171">Archived</a> from the original on 19 January 2023. Retrieved 13 October 2020. <q>There are no known pharmacological treatments for MDMA addiction.</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Clinical+Textbook+of+Addictive+Disorders&rft.pages=171&rft.pub=Guilford+Publications&rft.date=2016-05-12&rft.isbn=978-1-4625-2169-2&rft.aulast=Mack&rft.aufirst=AH&rft.au=Brady%2C+KT&rft.au=Miller%2C+SI&rft.au=Frances%2C+RJ&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3D88W_CwAAQBAJ%26q%3Dmdma%2Baddiction%26pg%3DPA171&rfr_id=info%3Asid%2Fen.wikipedia.org%3AMDMA" class="Z3988"> </li> <li id="cite_note-vorhees-110"><a href="#cite_ref-vorhees_110-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFVorhees1997" class="citation journal cs1">Vorhees CV (November 1997). "Methods for detecting long-term CNS dysfunction after prenatal exposure to neurotoxins". 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MDMA increased systolic and diastolic blood pressure (SBP, DBP) by 26 mmHg (p<0.001 each); prazosin attenuated MDMA effects on DBP by 9.3 mmHg (p<001) but did not alter SBP. [...] MDMA increases HR, producing elevations in CO. 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Neurosci Lett. 177 (1–2): 111–115. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2F0304-3940%2894%2990057-4">10.1016/0304-3940(94)90057-4</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/7824160">7824160</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Neurosci+Lett&rft.atitle=Effect+of+the+R%28-%29+and+S%28%2B%29+isomers+of+MDA+and+MDMA+on+phosphatidyl+inositol+turnover+in+cultured+cells+expressing+5-HT2A+or+5-HT2C+receptors&rft.volume=177&rft.issue=%3Cspan+class%3D%22nowrap%22%3E1%E2%80%93%3C%2Fspan%3E2&rft.pages=%3Cspan+class%3D%22nowrap%22%3E111-%3C%2Fspan%3E115&rft.date=1994-08&rft_id=info%3Adoi%2F10.1016%2F0304-3940%2894%2990057-4&rft_id=info%3Apmid%2F7824160&rft.aulast=Nash&rft.aufirst=JF&rft.au=Roth%2C+BL&rft.au=Brodkin%2C+JD&rft.au=Nichols%2C+DE&rft.au=Gudelsky%2C+GA&rfr_id=info%3Asid%2Fen.wikipedia.org%3AMDMA" class="Z3988"> </li> <li id="cite_note-SimmlerLiechti2018-162">^ <a href="#cite_ref-SimmlerLiechti2018_162-0">a</a> <a href="#cite_ref-SimmlerLiechti2018_162-1">b</a> <a href="#cite_ref-SimmlerLiechti2018_162-2">c</a> <a href="#cite_ref-SimmlerLiechti2018_162-3">d</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFSimmlerLiechti2018" class="citation journal cs1">Simmler LD, Liechti ME (2018). "Pharmacology of MDMA- and Amphetamine-Like New Psychoactive Substances". Handb Exp Pharmacol. Handbook of Experimental Pharmacology. 252: 143–164. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1007%2F164_2018_113">10.1007/164_2018_113</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-3-030-10560-0" title="Special:BookSources/978-3-030-10560-0"><bdi>978-3-030-10560-0</bdi></a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/29633178">29633178</a>. <q>MDMA is also a low-potency partial agonist of the 5-HT2A receptor. Although not frequent, mild hallucinogen-like effects of MDMA have been reported, which may be attributable to 5-HT2A agonism (Nichols 2004; Liechti et al. 2000). MDA, the active metabolite of MDMA (Hysek et al. 2011), shows a tenfold higher potency for 5-HT2A agonism than MDMA (Rickli et al. 2015c). 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Neuropsychopharmacology. 50 (2): 360–361. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1038%2Fs41386-024-02009-8">10.1038/s41386-024-02009-8</a>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11631934">11631934</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/39448866">39448866</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Neuropsychopharmacology&rft.atitle=Is+the+stereoisomer+R-MDMA+a+safer+version+of+MDMA%3F&rft.volume=50&rft.issue=2&rft.pages=%3Cspan+class%3D%22nowrap%22%3E360-%3C%2Fspan%3E361&rft.date=2024-10&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC11631934%23id-name%3DPMC&rft_id=info%3Apmid%2F39448866&rft_id=info%3Adoi%2F10.1038%2Fs41386-024-02009-8&rft.aulast=Bedi&rft.aufirst=G&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC11631934&rfr_id=info%3Asid%2Fen.wikipedia.org%3AMDMA" class="Z3988"> </li> <li id="cite_note-HalberstadtGeyer2018-165"><a href="#cite_ref-HalberstadtGeyer2018_165-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFHalberstadtGeyer2018" class="citation book cs1">Halberstadt AL, Geyer MA (2018). "Effect of Hallucinogens on Unconditioned Behavior". Behavioral Neurobiology of Psychedelic Drugs. Current Topics in Behavioral Neurosciences. Vol. 36. pp. 159–199. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1007%2F7854_2016_466">10.1007/7854_2016_466</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-3-662-55878-2" title="Special:BookSources/978-3-662-55878-2"><bdi>978-3-662-55878-2</bdi></a>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5787039">5787039</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/28224459">28224459</a>. <q>[MDxx] have been assessed in head twitch studies. Racemic [MDA] and S-(+)-MDA reportedly induce WDS in monkeys and rats, respectively (Schlemmer and Davis 1986; Hiramatsu et al. 1989). Although [MDMA] does not induce the HTR in mice, both of the stereoisomers of MDMA have been shown to elicit the response (Fantegrossi et al. 2004, 2005b). 5-HT depletion inhibits the response to S-(+)-MDMA but does not alter the response to R-(−)-MDMA, suggesting the isomers act through different mechanisms (Fantegrossi et al. 2005b). This suggestion is consistent with the fact that S-(+)- and R-(−)-MDMA exhibit qualitatively distinct pharmacological profiles, with the S-(+)isomer working primarily as a monoamine releaser (Johnson et al. 1986; Baumann et al. 2008; Murnane et al. 2010) and the R-(−)-enantiomer acting directly through 5-HT2A receptors (Lyon et al. 1986; Nash et al. 1994). In contrast to their effects in mice, Hiramatsu reported that S-(+)- and R-(−)-MDMA fail to produce WDS in rats (Hiramatsu et al. 1989). The discrepant findings with MDMA in mice and rats may reflect species differences in sensitivity to the HTR (see below for further discussion).</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Effect+of+Hallucinogens+on+Unconditioned+Behavior&rft.btitle=Behavioral+Neurobiology+of+Psychedelic+Drugs&rft.series=Current+Topics+in+Behavioral+Neurosciences&rft.pages=%3Cspan+class%3D%22nowrap%22%3E159-%3C%2Fspan%3E199&rft.date=2018&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC5787039%23id-name%3DPMC&rft_id=info%3Apmid%2F28224459&rft_id=info%3Adoi%2F10.1007%2F7854_2016_466&rft.isbn=978-3-662-55878-2&rft.aulast=Halberstadt&rft.aufirst=AL&rft.au=Geyer%2C+MA&rfr_id=info%3Asid%2Fen.wikipedia.org%3AMDMA" class="Z3988"> </li> <li id="cite_note-Dunlap2022-166"><a href="#cite_ref-Dunlap2022_166-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFDunlap2022" class="citation thesis cs1">Dunlap LE (2022). <a rel="nofollow" class="external text" href="https://escholarship.org/uc/item/5qr3w0gm">Development of Non-Hallucinogenic Psychoplastogens</a> (Thesis). University of California, Davis. Retrieved 18 November 2024. <q>Finally, since R-MDMA is known to partially substitute for LSD in animal models we decided to test both compounds in the head twitch response assay (HTR) (FIG 3.3C).3 The HTR is a well-validated mouse model for predicting the hallucinogenic potential of test drugs. Serotonergic psychedelics will cause a rapid back and forth head movement in mice. The potency measured in the HTR assay has been shown to correlate very well with the human potencies of psychedelics.18 Neither R-MDMA or LED produced any head twitches at all doses tested, suggesting that neither has high hallucinogenic potential.</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Adissertation&rft.title=Development+of+Non-Hallucinogenic+Psychoplastogens&rft.inst=University+of+California%2C+Davis&rft.date=2022&rft.aulast=Dunlap&rft.aufirst=LE&rft_id=https%3A%2F%2Fescholarship.org%2Fuc%2Fitem%2F5qr3w0gm&rfr_id=info%3Asid%2Fen.wikipedia.org%3AMDMA" class="Z3988"> </li> <li id="cite_note-LewinMillerGilmour2011-167"><a href="#cite_ref-LewinMillerGilmour2011_167-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFLewinMillerGilmour2011" class="citation journal cs1">Lewin AH, Miller GM, Gilmour B (December 2011). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3236098">"Trace amine-associated receptor 1 is a stereoselective binding site for compounds in the amphetamine class"</a>. Bioorganic & Medicinal Chemistry. 19 (23): 7044–7048. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2Fj.bmc.2011.10.007">10.1016/j.bmc.2011.10.007</a>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3236098">3236098</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/22037049">22037049</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Bioorganic+%26+Medicinal+Chemistry&rft.atitle=Trace+amine-associated+receptor+1+is+a+stereoselective+binding+site+for+compounds+in+the+amphetamine+class&rft.volume=19&rft.issue=23&rft.pages=%3Cspan+class%3D%22nowrap%22%3E7044-%3C%2Fspan%3E7048&rft.date=2011-12&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC3236098%23id-name%3DPMC&rft_id=info%3Apmid%2F22037049&rft_id=info%3Adoi%2F10.1016%2Fj.bmc.2011.10.007&rft.aulast=Lewin&rft.aufirst=AH&rft.au=Miller%2C+GM&rft.au=Gilmour%2C+B&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC3236098&rfr_id=info%3Asid%2Fen.wikipedia.org%3AMDMA" class="Z3988"> </li> <li id="cite_note-EspinozaGainetdinov2014-168"><a href="#cite_ref-EspinozaGainetdinov2014_168-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFEspinozaGainetdinov2014" class="citation book cs1">Espinoza S, Gainetdinov RR (2014). "Neuronal Functions and Emerging Pharmacology of TAAR1". Taste and Smell. Topics in Medicinal Chemistry. Vol. 23. Cham: Springer International Publishing. pp. 175–194. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1007%2F7355_2014_78">10.1007/7355_2014_78</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-3-319-48925-4" title="Special:BookSources/978-3-319-48925-4"><bdi>978-3-319-48925-4</bdi></a>. <q>Interestingly, the concentrations of amphetamine found to be necessary to activate TAAR1 are in line with what was found in drug abusers [3, 51, 52]. Thus, it is likely that some of the effects produced by amphetamines could be mediated by TAAR1. Indeed, in a study in mice, MDMA effects were found to be mediated in part by TAAR1, in a sense that MDMA auto-inhibits its neurochemical and functional actions [46]. Based on this and other studies (see other section), it has been suggested that TAAR1 could play a role in reward mechanisms and that amphetamine activity on TAAR1 counteracts their known behavioral and neurochemical effects mediated via dopamine neurotransmission.</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Neuronal+Functions+and+Emerging+Pharmacology+of+TAAR1&rft.btitle=Taste+and+Smell&rft.place=Cham&rft.series=Topics+in+Medicinal+Chemistry&rft.pages=%3Cspan+class%3D%22nowrap%22%3E175-%3C%2Fspan%3E194&rft.pub=Springer+International+Publishing&rft.date=2014&rft_id=info%3Adoi%2F10.1007%2F7355_2014_78&rft.isbn=978-3-319-48925-4&rft.aulast=Espinoza&rft.aufirst=S&rft.au=Gainetdinov%2C+RR&rfr_id=info%3Asid%2Fen.wikipedia.org%3AMDMA" class="Z3988"> </li> <li id="cite_note-KuropkaZawadzkiSzpot2023-169"><a href="#cite_ref-KuropkaZawadzkiSzpot2023_169-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFKuropkaZawadzkiSzpot2023" class="citation journal cs1">Kuropka P, Zawadzki M, Szpot P (May 2023). "A narrative review of the neuropharmacology of synthetic cathinones-Popular alternatives to classical drugs of abuse". Hum Psychopharmacol. 38 (3): e2866. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2Fhup.2866">10.1002/hup.2866</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/36866677">36866677</a>. <q>Another feature that distinguishes [synthetic cathinones (SCs)] from amphetamines is their negligible interaction with the trace amine associated receptor 1 (TAAR1). Activation of this receptor reduces the activity of dopaminergic neurones, thereby reducing psychostimulatory effects and addictive potential (Miller, 2011; Simmler et al., 2016). Amphetamines are potent agonists of this receptor, making them likely to self‐inhibit their stimulating effects. In contrast, SCs show negligible activity towards TAAR1 (Kolaczynska et al., 2021; Rickli et al., 2015; Simmler et al., 2014, 2016). [...] It is worth noting, however, that for TAAR1 there is considerable species variability in its interaction with ligands, and it is possible that the in vitro activity of [rodent TAAR1 agonists] may not translate into activity in the human body (Simmler et al., 2016). The lack of self‐regulation by TAAR1 may partly explain the higher addictive potential of SCs compared to amphetamines (Miller, 2011; Simmler et al., 2013).</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Hum+Psychopharmacol&rft.atitle=A+narrative+review+of+the+neuropharmacology+of+synthetic+cathinones-Popular+alternatives+to+classical+drugs+of+abuse&rft.volume=38&rft.issue=3&rft.pages=e2866&rft.date=2023-05&rft_id=info%3Adoi%2F10.1002%2Fhup.2866&rft_id=info%3Apmid%2F36866677&rft.aulast=Kuropka&rft.aufirst=P&rft.au=Zawadzki%2C+M&rft.au=Szpot%2C+P&rfr_id=info%3Asid%2Fen.wikipedia.org%3AMDMA" class="Z3988"> </li> <li id="cite_note-DiCaraMaggioAloisi2011-170"><a href="#cite_ref-DiCaraMaggioAloisi2011_170-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFDi_CaraMaggioAloisiRivet2011" class="citation journal cs1">Di Cara B, Maggio R, Aloisi G, Rivet JM, Lundius EG, Yoshitake T, et al. (November 2011). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6623861">"Genetic deletion of trace amine 1 receptors reveals their role in auto-inhibiting the actions of ecstasy (MDMA)"</a>. J Neurosci. 31 (47): 16928–16940. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1523%2FJNEUROSCI.2502-11.2011">10.1523/JNEUROSCI.2502-11.2011</a>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6623861">6623861</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/22114263">22114263</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=J+Neurosci&rft.atitle=Genetic+deletion+of+trace+amine+1+receptors+reveals+their+role+in+auto-inhibiting+the+actions+of+ecstasy+%28MDMA%29&rft.volume=31&rft.issue=47&rft.pages=%3Cspan+class%3D%22nowrap%22%3E16928-%3C%2Fspan%3E16940&rft.date=2011-11&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC6623861%23id-name%3DPMC&rft_id=info%3Apmid%2F22114263&rft_id=info%3Adoi%2F10.1523%2FJNEUROSCI.2502-11.2011&rft.aulast=Di+Cara&rft.aufirst=B&rft.au=Maggio%2C+R&rft.au=Aloisi%2C+G&rft.au=Rivet%2C+JM&rft.au=Lundius%2C+EG&rft.au=Yoshitake%2C+T&rft.au=Svenningsson%2C+P&rft.au=Brocco%2C+M&rft.au=Gobert%2C+A&rft.au=De+Groote%2C+L&rft.au=Cistarelli%2C+L&rft.au=Veiga%2C+S&rft.au=De+Montrion%2C+C&rft.au=Rodriguez%2C+M&rft.au=Galizzi%2C+JP&rft.au=Lockhart%2C+BP&rft.au=Cog%C3%A9%2C+F&rft.au=Boutin%2C+JA&rft.au=Vayer%2C+P&rft.au=Verdouw%2C+PM&rft.au=Groenink%2C+L&rft.au=Millan%2C+MJ&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC6623861&rfr_id=info%3Asid%2Fen.wikipedia.org%3AMDMA" class="Z3988"> </li> <li id="cite_note-ReinRaymondBoustani2024-171"><a href="#cite_ref-ReinRaymondBoustani2024_171-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFReinRaymondBoustaniTuy2024" class="citation journal cs1">Rein B, Raymond K, Boustani C, Tuy S, Zhang J, St Laurent R, et al. (April 2024). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11042730">"MDMA enhances empathy-like behaviors in mice via 5-HT release in the nucleus accumbens"</a>. Sci Adv. 10 (17): eadl6554. <a href="/wiki/Bibcode_(identifier)" class="mw-redirect" title="Bibcode (identifier)">Bibcode</a>:<a rel="nofollow" class="external text" href="https://ui.adsabs.harvard.edu/abs/2024SciA...10L6554R">2024SciA...10L6554R</a>. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1126%2Fsciadv.adl6554">10.1126/sciadv.adl6554</a>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11042730">11042730</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/38657057">38657057</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Sci+Adv&rft.atitle=MDMA+enhances+empathy-like+behaviors+in+mice+via+5-HT+release+in+the+nucleus+accumbens&rft.volume=10&rft.issue=17&rft.pages=eadl6554&rft.date=2024-04&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC11042730%23id-name%3DPMC&rft_id=info%3Apmid%2F38657057&rft_id=info%3Adoi%2F10.1126%2Fsciadv.adl6554&rft_id=info%3Abibcode%2F2024SciA...10L6554R&rft.aulast=Rein&rft.aufirst=B&rft.au=Raymond%2C+K&rft.au=Boustani%2C+C&rft.au=Tuy%2C+S&rft.au=Zhang%2C+J&rft.au=St+Laurent%2C+R&rft.au=Pomrenze%2C+MB&rft.au=Boroon%2C+P&rft.au=Heifets%2C+B&rft.au=Smith%2C+M&rft.au=Malenka%2C+RC&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC11042730&rfr_id=info%3Asid%2Fen.wikipedia.org%3AMDMA" class="Z3988"> </li> <li id="cite_note-Kamilar-BrittBedi2015-172">^ <a href="#cite_ref-Kamilar-BrittBedi2015_172-0">a</a> <a href="#cite_ref-Kamilar-BrittBedi2015_172-1">b</a> <a href="#cite_ref-Kamilar-BrittBedi2015_172-2">c</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFKamilar-BrittBedi2015" class="citation journal cs1">Kamilar-Britt P, Bedi G (October 2015). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4678620">"The prosocial effects of 3,4-methylenedioxymethamphetamine (MDMA): Controlled studies in humans and laboratory animals"</a>. Neurosci Biobehav Rev. 57: 433–446. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2Fj.neubiorev.2015.08.016">10.1016/j.neubiorev.2015.08.016</a>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4678620">4678620</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/26408071">26408071</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Neurosci+Biobehav+Rev&rft.atitle=The+prosocial+effects+of+3%2C4-methylenedioxymethamphetamine+%28MDMA%29%3A+Controlled+studies+in+humans+and+laboratory+animals&rft.volume=57&rft.pages=%3Cspan+class%3D%22nowrap%22%3E433-%3C%2Fspan%3E446&rft.date=2015-10&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC4678620%23id-name%3DPMC&rft_id=info%3Apmid%2F26408071&rft_id=info%3Adoi%2F10.1016%2Fj.neubiorev.2015.08.016&rft.aulast=Kamilar-Britt&rft.aufirst=P&rft.au=Bedi%2C+G&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC4678620&rfr_id=info%3Asid%2Fen.wikipedia.org%3AMDMA" class="Z3988"> </li> <li id="cite_note-EsakiSasakiNishitani2023-173"><a href="#cite_ref-EsakiSasakiNishitani2023_173-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFEsakiSasakiNishitaniKamada2023" class="citation journal cs1">Esaki H, Sasaki Y, Nishitani N, Kamada H, Mukai S, Ohshima Y, et al. 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However, it is unclear whether MDMA binds here directly or whether one of its active metabolites (for example, MDA exhibits a 5-HT2A affinity almost 10-fold better than MDMA) is responsible.70,80,81 In addition, R-MDMA more potently activates 5-HT2A second messenger signaling, with S-MDMA having a minimal effect and racemic MDMA acting as a weak partial agonist.</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Psychedelic+Medicine&rft.atitle=Balancing+Therapeutic+Efficacy+and+Safety+of+MDMA+and+Novel+MDXX+Analogues+as+Novel+Treatments+for+Autism+Spectrum+Disorder&rft.volume=1&rft.issue=3&rft.pages=%3Cspan+class%3D%22nowrap%22%3E166-%3C%2Fspan%3E185&rft.date=2023&rft_id=info%3Adoi%2F10.1089%2Fpsymed.2023.0023&rft.aulast=Kaur&rft.aufirst=H&rft.au=Karabulut%2C+S&rft.au=Gauld%2C+JW&rft.au=Fagot%2C+SA&rft.au=Holloway%2C+KN&rft.au=Shaw%2C+HE&rft.au=Fantegrossi%2C+WE&rfr_id=info%3Asid%2Fen.wikipedia.org%3AMDMA" class="Z3988"> </li> <li id="cite_note-Baggott2023-179">^ <a href="#cite_ref-Baggott2023_179-0">a</a> <a href="#cite_ref-Baggott2023_179-1">b</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFBaggott2023" class="citation conference cs1">Baggott M (23 June 2023). <a rel="nofollow" class="external text" href="https://2023.psychedelicscience.org/sessions/beyond-ecstasy-progress-in-developing-and-understanding-a-novel-class-of-therapeutic-medicine/">Beyond Ecstasy: Progress in Developing and Understanding a Novel Class of Therapeutic Medicine</a>. 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Journal of Neurochemistry. 102 (1): 121–132. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1111%2Fj.1471-4159.2007.04451.x">10.1111/j.1471-4159.2007.04451.x</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/17564678">17564678</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Journal+of+Neurochemistry&rft.atitle=Differential+effects+of+intravenous+R%2CS-%28%2B%2F-%29-3%2C4-methylenedioxymethamphetamine+%28MDMA%2C+Ecstasy%29+and+its+S%28%2B%29-+and+R%28-%29-enantiomers+on+dopamine+transmission+and+extracellular+signal+regulated+kinase+phosphorylation+%28pERK%29+in+the+rat+nucleus+accumbens+shell+and+core&rft.volume=102&rft.issue=1&rft.pages=%3Cspan+class%3D%22nowrap%22%3E121-%3C%2Fspan%3E132&rft.date=2007-07&rft_id=info%3Adoi%2F10.1111%2Fj.1471-4159.2007.04451.x&rft_id=info%3Apmid%2F17564678&rft.aulast=Acquas&rft.aufirst=E&rft.au=Pisanu%2C+A&rft.au=Spiga%2C+S&rft.au=Plumitallo%2C+A&rft.au=Zernig%2C+G&rft.au=Di+Chiara%2C+G&rfr_id=info%3Asid%2Fen.wikipedia.org%3AMDMA" class="Z3988"> </li> <li id="cite_note-CurryYoungTran2018-190"><a href="#cite_ref-CurryYoungTran2018_190-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFCurryYoungTranDaoud2018" class="citation journal cs1">Curry DW, Young MB, Tran AN, Daoud GE, Howell LL (January 2018). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5714650">"Separating the agony from ecstasy: R(-)-3,4-methylenedioxymethamphetamine has prosocial and therapeutic-like effects without signs of neurotoxicity in mice"</a>. Neuropharmacology. 128: 196–206. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2Fj.neuropharm.2017.10.003">10.1016/j.neuropharm.2017.10.003</a>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5714650">5714650</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/28993129">28993129</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Neuropharmacology&rft.atitle=Separating+the+agony+from+ecstasy%3A+R%28-%29-3%2C4-methylenedioxymethamphetamine+has+prosocial+and+therapeutic-like+effects+without+signs+of+neurotoxicity+in+mice&rft.volume=128&rft.pages=%3Cspan+class%3D%22nowrap%22%3E196-%3C%2Fspan%3E206&rft.date=2018-01&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC5714650%23id-name%3DPMC&rft_id=info%3Apmid%2F28993129&rft_id=info%3Adoi%2F10.1016%2Fj.neuropharm.2017.10.003&rft.aulast=Curry&rft.aufirst=DW&rft.au=Young%2C+MB&rft.au=Tran%2C+AN&rft.au=Daoud%2C+GE&rft.au=Howell%2C+LL&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC5714650&rfr_id=info%3Asid%2Fen.wikipedia.org%3AMDMA" class="Z3988"> </li> <li id="cite_note-LuethiLiechti2021-191"><a href="#cite_ref-LuethiLiechti2021_191-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFLuethiLiechti2021" class="citation book cs1">Luethi D, Liechti ME (2021). "Drugs of Abuse Affecting 5-HT2B Receptors". 5-HT2B Receptors. The Receptors. Vol. 35. Cham: Springer International Publishing. pp. 277–289. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1007%2F978-3-030-55920-5_16">10.1007/978-3-030-55920-5_16</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-3-030-55919-9" title="Special:BookSources/978-3-030-55919-9"><bdi>978-3-030-55919-9</bdi></a>. <q>Notably, in a study by Rickli and colleagues, MDMA did not activate the 5-HT2B receptor in the functional assay at investigated concentrations (EC50 > 20 μM); however, [MDA], the main psychoactive N-demethylated phase I metabolite of MDMA, potently activated the receptor at submicromolar concentrations [14]. This suggests that the metabolite MDA rather than MDMA itself may lead to valvulopathy and that there could be a signifcant metabolic contribution to MDMA-induced effects and adverse effect.</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Drugs+of+Abuse+Affecting+5-HT2B+Receptors&rft.btitle=5-HT2B+Receptors&rft.place=Cham&rft.series=The+Receptors&rft.pages=%3Cspan+class%3D%22nowrap%22%3E277-%3C%2Fspan%3E289&rft.pub=Springer+International+Publishing&rft.date=2021&rft_id=info%3Adoi%2F10.1007%2F978-3-030-55920-5_16&rft.isbn=978-3-030-55919-9&rft.aulast=Luethi&rft.aufirst=D&rft.au=Liechti%2C+ME&rfr_id=info%3Asid%2Fen.wikipedia.org%3AMDMA" class="Z3988"> </li> <li id="cite_note-MeadParrott2020-192"><a href="#cite_ref-MeadParrott2020_192-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFMeadParrott2020" class="citation journal cs1">Mead J, Parrott A (May 2020). 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A dose of 100 mg has a half-life of 8–9h(De la Torre et al., 2004), although as mentioned above, users are unaware of the dose they ingest.</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Brain+Res&rft.atitle=Mephedrone+and+MDMA%3A+A+comparative+review&rft.volume=1735&rft.pages=146740&rft.date=2020-05&rft_id=info%3Adoi%2F10.1016%2Fj.brainres.2020.146740&rft_id=info%3Apmid%2F32087112&rft.aulast=Mead&rft.aufirst=J&rft.au=Parrott%2C+A&rfr_id=info%3Asid%2Fen.wikipedia.org%3AMDMA" class="Z3988"> </li> <li id="cite_note-ErmerPennickFrick2016-193"><a href="#cite_ref-ErmerPennickFrick2016_193-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFErmerPennickFrick2016" class="citation journal cs1">Ermer JC, Pennick M, Frick G (May 2016). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4823324">"Lisdexamfetamine Dimesylate: Prodrug Delivery, Amphetamine Exposure and Duration of Efficacy"</a>. Clinical Drug Investigation. 36 (5): 341–356. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1007%2Fs40261-015-0354-y">10.1007/s40261-015-0354-y</a>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4823324">4823324</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/27021968">27021968</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Clinical+Drug+Investigation&rft.atitle=Lisdexamfetamine+Dimesylate%3A+Prodrug+Delivery%2C+Amphetamine+Exposure+and+Duration+of+Efficacy&rft.volume=36&rft.issue=5&rft.pages=%3Cspan+class%3D%22nowrap%22%3E341-%3C%2Fspan%3E356&rft.date=2016-05&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC4823324%23id-name%3DPMC&rft_id=info%3Apmid%2F27021968&rft_id=info%3Adoi%2F10.1007%2Fs40261-015-0354-y&rft.aulast=Ermer&rft.aufirst=JC&rft.au=Pennick%2C+M&rft.au=Frick%2C+G&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC4823324&rfr_id=info%3Asid%2Fen.wikipedia.org%3AMDMA" class="Z3988"> </li> <li id="cite_note-CruickshankDyer2009-194"><a href="#cite_ref-CruickshankDyer2009_194-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFCruickshankDyer2009" class="citation journal cs1">Cruickshank CC, Dyer KR (July 2009). "A review of the clinical pharmacology of methamphetamine". Addiction. 104 (7): 1085–1099. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1111%2Fj.1360-0443.2009.02564.x">10.1111/j.1360-0443.2009.02564.x</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/19426289">19426289</a>. <q>Metabolism does not appear to be altered by chronic exposure, thus dose escalation appears to arise from pharmacodynamic rather than pharmacokinetic tolerance [24]. [...] The terminal plasma half-life of methamphetamine of approximately 10 hours is similar across administration routes, but with substantial inter-individual variability. Acute effects persist for up to 8 hours following a single moderate dose of 30 mg [30]. [...] peak plasma methamphetamine concentration occurs after 4 hours [35]. Nevertheless, peak cardiovascular and subjective effects occur rapidly (within 5–15 minutes). The dissociation between peak plasma concentration and clinical effects indicates acute tolerance, which may reflect rapid molecular processes such as redistribution of vesicular monoamines and internalization of monoamine receptors and transporters [6,36]. Acute subjective effects diminish over 4 hours, while cardiovascular effects tend to remain elevated. This is important, as the marked acute tachyphylaxis to subjective effects may drive repeated use within intervals of 4 hours, while cardiovascular risks may increase [11,35].</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Addiction&rft.atitle=A+review+of+the+clinical+pharmacology+of+methamphetamine&rft.volume=104&rft.issue=7&rft.pages=%3Cspan+class%3D%22nowrap%22%3E1085-%3C%2Fspan%3E1099&rft.date=2009-07&rft_id=info%3Adoi%2F10.1111%2Fj.1360-0443.2009.02564.x&rft_id=info%3Apmid%2F19426289&rft.aulast=Cruickshank&rft.aufirst=CC&rft.au=Dyer%2C+KR&rfr_id=info%3Asid%2Fen.wikipedia.org%3AMDMA" class="Z3988"> </li> <li id="cite_note-AbbasBarnhardtNash2024-195"><a href="#cite_ref-AbbasBarnhardtNash2024_195-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFAbbasBarnhardtNashStreng2024" class="citation journal cs1">Abbas K, Barnhardt EW, Nash PL, Streng M, Coury DL (April 2024). <a rel="nofollow" class="external text" href="https://doi.org/10.1080%2F14737175.2024.2321921">"A review of amphetamine extended release once-daily options for the management of attention-deficit hyperactivity disorder"</a>. Expert Review of Neurotherapeutics. 24 (4): 421–432. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1080%2F14737175.2024.2321921">10.1080/14737175.2024.2321921</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/38391788">38391788</a>. <q>For several decades, clinical benefits of amphetamines have been limited by the pharmacologic half-life of around 4 hours. Although higher doses can produce higher maximum concentrations, they do not affect the half-life of the dose. Therefore, to achieve longer durations of effect, stimulants had to be dosed at least twice daily. Further, these immediate-release doses were found to have their greatest effect shortly after administration, with a rapid decline in effect after reaching peak blood concentrations. The clinical correlation of this was found in comparing math problems attempted and solved between a mixed amphetamine salts preparation (MAS) 10 mg once at 8 am vs 8 am followed by 12 pm [14]. The study also demonstrated the phenomenon of acute tolerance, where even if blood concentrations were maintained over the course of the day, clinical efficacy in the form of math problems attempted and solved would diminish over the course of the day. These findings eventually led to the development of a once daily preparation (MAS XR) [15], which is a composition of 50% immediate-release beads and 50% delayed release beads intended to mimic this twice-daily dosing with only a single administration.</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Expert+Review+of+Neurotherapeutics&rft.atitle=A+review+of+amphetamine+extended+release+once-daily+options+for+the+management+of+attention-deficit+hyperactivity+disorder&rft.volume=24&rft.issue=4&rft.pages=%3Cspan+class%3D%22nowrap%22%3E421-%3C%2Fspan%3E432&rft.date=2024-04&rft_id=info%3Adoi%2F10.1080%2F14737175.2024.2321921&rft_id=info%3Apmid%2F38391788&rft.aulast=Abbas&rft.aufirst=K&rft.au=Barnhardt%2C+EW&rft.au=Nash%2C+PL&rft.au=Streng%2C+M&rft.au=Coury%2C+DL&rft_id=https%3A%2F%2Fdoi.org%2F10.1080%252F14737175.2024.2321921&rfr_id=info%3Asid%2Fen.wikipedia.org%3AMDMA" class="Z3988"> </li> <li id="cite_note-vanGaalenSchlumbohmFolgering2019-196"><a href="#cite_ref-vanGaalenSchlumbohmFolgering2019_196-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFvan_GaalenSchlumbohmFolgeringAdhikari2019" class="citation journal cs1">van Gaalen MM, Schlumbohm C, Folgering JH, Adhikari S, Bhattacharya C, Steinbach D, et al. (April 2019). <a rel="nofollow" class="external text" href="https://doi.org/10.1124%2Fjpet.118.254508">"Development of a Semimechanistic Pharmacokinetic-Pharmacodynamic Model Describing Dextroamphetamine Exposure and Striatal Dopamine Response in Rats and Nonhuman Primates following a Single Dose of Dextroamphetamine"</a>. The Journal of Pharmacology and Experimental Therapeutics. 369 (1): 107–120. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1124%2Fjpet.118.254508">10.1124/jpet.118.254508</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/30733244">30733244</a>. <q>Acute tolerance has been demonstrated for methamphetamine in rats (Segal and Kuczenski, 2006), and for D-amphetamine in rats (Lewander, 1971), [non-human primates (NHPs)] (Jedema et al., 2014) and humans (Angrist et al., 1987; Brauer et al., 1996; Dolder et al., 2017). In vivo measurement of dopamine by microdialysis was used in rats and NHPs to evaluate these time-dependent effects. In humans, various subjective measures of mood related to the drug's euphoric effects were observed to decline more rapidly than plasma concentrations following D-amphetamine oral doses ranging from 20 to 40 mg (Angrist et al., 1987; Brauer et al., 1996; Dolder et al., 2017). Whereas peak plasma concentrations and subjective effects occurred between 2 and 4 hours following administration, drug effect measures had largely returned to baseline values by 8 hours despite continued exposure to the drug (mean half-life = 8 hours following a 40 mg dose (Dolder et al., 2017)).</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=The+Journal+of+Pharmacology+and+Experimental+Therapeutics&rft.atitle=Development+of+a+Semimechanistic+Pharmacokinetic-Pharmacodynamic+Model+Describing+Dextroamphetamine+Exposure+and+Striatal+Dopamine+Response+in+Rats+and+Nonhuman+Primates+following+a+Single+Dose+of+Dextroamphetamine&rft.volume=369&rft.issue=1&rft.pages=%3Cspan+class%3D%22nowrap%22%3E107-%3C%2Fspan%3E120&rft.date=2019-04&rft_id=info%3Adoi%2F10.1124%2Fjpet.118.254508&rft_id=info%3Apmid%2F30733244&rft.aulast=van+Gaalen&rft.aufirst=MM&rft.au=Schlumbohm%2C+C&rft.au=Folgering%2C+JH&rft.au=Adhikari%2C+S&rft.au=Bhattacharya%2C+C&rft.au=Steinbach%2C+D&rft.au=Stratford%2C+RE&rft_id=https%3A%2F%2Fdoi.org%2F10.1124%252Fjpet.118.254508&rfr_id=info%3Asid%2Fen.wikipedia.org%3AMDMA" class="Z3988"> </li> <li id="cite_note-BisagnoCadet2021-197"><a href="#cite_ref-BisagnoCadet2021_197-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFBisagnoCadet2021" class="citation book cs1">Bisagno V, Cadet JL (2021). "Methamphetamine and MDMA Neurotoxicity: Biochemical and Molecular Mechanisms". Handbook of Neurotoxicity. Cham: Springer International Publishing. pp. 1–24. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1007%2F978-3-030-71519-9_80-1">10.1007/978-3-030-71519-9_80-1</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-3-030-71519-9" title="Special:BookSources/978-3-030-71519-9"><bdi>978-3-030-71519-9</bdi></a>. <q>Injections of large doses of MDMA cause massive release of 5-HT from presynaptic vesicles, followed by a rapid decrease in 5-HT and 5-hydroxyindoleacetic acid (5-HIAA) levels and decreased TPH activity (Górska et al., 2018; Lyles & Cadet, 2003). There do not appear to be losses of 5-HT uptake sites at early time points after MDMA administration (Lyles & Cadet, 2003). [...] MDMA also perturbs the function of SERT (Green et al., 2003), a marker of the integrity of serotonin neurons (Blakely et al., 1994). By virtue of its moderating synaptic 5-HT levels, SERT is crucial for the process of 5-HT neurotransmission (Green et al., 2003). MDMA downregulates SERT function without altering SERT mRNA or protein expression, and this rapid downregulation is sustained for at least 90 min and is dose-dependent (Kivell et al., 2010).</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Methamphetamine+and+MDMA+Neurotoxicity%3A+Biochemical+and+Molecular+Mechanisms&rft.btitle=Handbook+of+Neurotoxicity&rft.place=Cham&rft.pages=%3Cspan+class%3D%22nowrap%22%3E1-%3C%2Fspan%3E24&rft.pub=Springer+International+Publishing&rft.date=2021&rft_id=info%3Adoi%2F10.1007%2F978-3-030-71519-9_80-1&rft.isbn=978-3-030-71519-9&rft.aulast=Bisagno&rft.aufirst=V&rft.au=Cadet%2C+JL&rfr_id=info%3Asid%2Fen.wikipedia.org%3AMDMA" class="Z3988"> </li> <li id="cite_note-KivellDayBosch2010-198"><a href="#cite_ref-KivellDayBosch2010_198-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFKivellDayBoschSchenk2010" class="citation journal cs1">Kivell B, Day D, Bosch P, Schenk S, Miller J (June 2010). "MDMA causes a redistribution of serotonin transporter from the cell surface to the intracellular compartment by a mechanism independent of phospho-p38-mitogen activated protein kinase activation". Neuroscience. 168 (1): 82–95. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2Fj.neuroscience.2010.03.018">10.1016/j.neuroscience.2010.03.018</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/20298763">20298763</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Neuroscience&rft.atitle=MDMA+causes+a+redistribution+of+serotonin+transporter+from+the+cell+surface+to+the+intracellular+compartment+by+a+mechanism+independent+of+phospho-p38-mitogen+activated+protein+kinase+activation&rft.volume=168&rft.issue=1&rft.pages=%3Cspan+class%3D%22nowrap%22%3E82-%3C%2Fspan%3E95&rft.date=2010-06&rft_id=info%3Adoi%2F10.1016%2Fj.neuroscience.2010.03.018&rft_id=info%3Apmid%2F20298763&rft.aulast=Kivell&rft.aufirst=B&rft.au=Day%2C+D&rft.au=Bosch%2C+P&rft.au=Schenk%2C+S&rft.au=Miller%2C+J&rfr_id=info%3Asid%2Fen.wikipedia.org%3AMDMA" class="Z3988"> </li> <li id="cite_note-HolleySimonsonKivell2013-199"><a href="#cite_ref-HolleySimonsonKivell2013_199-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFHolleySimonsonKivell2013" class="citation journal cs1">Holley A, Simonson B, Kivell BM (April 2013). <a rel="nofollow" class="external text" href="https://www.researchgate.net/publication/256328051">"MDMA regulates serotonin transporter function via a Protein kinase C dependent mechanism"</a>. Journal of Addiction & Prevention. 1 (1): 5. <a href="/wiki/ISSN_(identifier)" class="mw-redirect" title="ISSN (identifier)">ISSN</a> <a rel="nofollow" class="external text" href="https://search.worldcat.org/issn/2330-2178">2330-2178</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Journal+of+Addiction+%26+Prevention&rft.atitle=MDMA+regulates+serotonin+transporter+function+via+a+Protein+kinase+C+dependent+mechanism&rft.volume=1&rft.issue=1&rft.pages=5&rft.date=2013-04&rft.issn=2330-2178&rft.aulast=Holley&rft.aufirst=A&rft.au=Simonson%2C+B&rft.au=Kivell%2C+BM&rft_id=https%3A%2F%2Fwww.researchgate.net%2Fpublication%2F256328051&rfr_id=info%3Asid%2Fen.wikipedia.org%3AMDMA" class="Z3988"> </li> <li id="cite_note-UnderhillAmara2020-200">^ <a href="#cite_ref-UnderhillAmara2020_200-0">a</a> <a href="#cite_ref-UnderhillAmara2020_200-1">b</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFUnderhillAmara2020" class="citation journal cs1">Underhill S, Amara S (2020). <a rel="nofollow" class="external text" href="https://doi.org/10.1096%2Ffasebj.2020.34.s1.05856">"MDMA and TAAR1-mediated RhoA Activation in Serotonin Neurons"</a>. The FASEB Journal. 34 (S1): 1. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1096%2Ffasebj.2020.34.s1.05856">10.1096/fasebj.2020.34.s1.05856</a>. <a href="/wiki/ISSN_(identifier)" class="mw-redirect" title="ISSN (identifier)">ISSN</a> <a rel="nofollow" class="external text" href="https://search.worldcat.org/issn/0892-6638">0892-6638</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=The+FASEB+Journal&rft.atitle=MDMA+and+TAAR1-mediated+RhoA+Activation+in+Serotonin+Neurons&rft.volume=34&rft.issue=S1&rft.pages=1&rft.date=2020&rft_id=info%3Adoi%2F10.1096%2Ffasebj.2020.34.s1.05856&rft.issn=0892-6638&rft.aulast=Underhill&rft.aufirst=S&rft.au=Amara%2C+S&rft_id=https%3A%2F%2Fdoi.org%2F10.1096%252Ffasebj.2020.34.s1.05856&rfr_id=info%3Asid%2Fen.wikipedia.org%3AMDMA" class="Z3988"> </li> <li id="cite_note-UnderhillAmara2022-201">^ <a href="#cite_ref-UnderhillAmara2022_201-0">a</a> <a href="#cite_ref-UnderhillAmara2022_201-1">b</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFUnderhillAmara2022" class="citation journal cs1">Underhill S, Amara S (2022). <a rel="nofollow" class="external text" href="https://doi.org/10.1096%2Ffasebj.2022.36.S1.R5394">"3,4-methylenedioxymethamphetamine (MDMA) stimulates activation of TAAR1 and subsequent neurotransmitter transporter internalization in serotonin neurons"</a>. The FASEB Journal. 36 (S1). <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1096%2Ffasebj.2022.36.S1.R5394">10.1096/fasebj.2022.36.S1.R5394</a>. <a href="/wiki/ISSN_(identifier)" class="mw-redirect" title="ISSN (identifier)">ISSN</a> <a rel="nofollow" class="external text" href="https://search.worldcat.org/issn/0892-6638">0892-6638</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=The+FASEB+Journal&rft.atitle=3%2C4-methylenedioxymethamphetamine+%28MDMA%29+stimulates+activation+of+TAAR1+and+subsequent+neurotransmitter+transporter+internalization+in+serotonin+neurons&rft.volume=36&rft.issue=S1&rft.date=2022&rft_id=info%3Adoi%2F10.1096%2Ffasebj.2022.36.S1.R5394&rft.issn=0892-6638&rft.aulast=Underhill&rft.aufirst=S&rft.au=Amara%2C+S&rft_id=https%3A%2F%2Fdoi.org%2F10.1096%252Ffasebj.2022.36.S1.R5394&rfr_id=info%3Asid%2Fen.wikipedia.org%3AMDMA" class="Z3988"> </li> <li id="cite_note-KittlerLauSchloss2010-202"><a href="#cite_ref-KittlerLauSchloss2010_202-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFKittlerLauSchloss2010" class="citation journal cs1">Kittler K, Lau T, Schloss P (March 2010). "Antagonists and substrates differentially regulate serotonin transporter cell surface expression in serotonergic neurons". Eur J Pharmacol. 629 (1–3): 63–67. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2Fj.ejphar.2009.12.010">10.1016/j.ejphar.2009.12.010</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/20006597">20006597</a>. <q>Our results show that exposure to the SSRIs citalopram, fluoxetine, sertraline and paroxetine all induced SERT internalization, but with different efficacies. The substrates 5-HT and MDMA also induced SERT internalization, while cocaine elevated SERT cell surface expression.</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Eur+J+Pharmacol&rft.atitle=Antagonists+and+substrates+differentially+regulate+serotonin+transporter+cell+surface+expression+in+serotonergic+neurons&rft.volume=629&rft.issue=%3Cspan+class%3D%22nowrap%22%3E1%E2%80%93%3C%2Fspan%3E3&rft.pages=%3Cspan+class%3D%22nowrap%22%3E63-%3C%2Fspan%3E67&rft.date=2010-03&rft_id=info%3Adoi%2F10.1016%2Fj.ejphar.2009.12.010&rft_id=info%3Apmid%2F20006597&rft.aulast=Kittler&rft.aufirst=K&rft.au=Lau%2C+T&rft.au=Schloss%2C+P&rfr_id=info%3Asid%2Fen.wikipedia.org%3AMDMA" class="Z3988"> </li> <li id="cite_note-RothmanBaumannDersch2001-203"><a href="#cite_ref-RothmanBaumannDersch2001_203-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFRothmanBaumannDerschRomero2001" class="citation journal cs1">Rothman RB, Baumann MH, Dersch CM, Romero DV, Rice KC, Carroll FI, et al. 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Nonmedical use and intoxication"</a> (PDF). Journal of Psychoactive Drugs. 18 (4): 349–54. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1080%2F02791072.1986.10472368">10.1080/02791072.1986.10472368</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/2880950">2880950</a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20160304090940/http://www.maps.org/images/pdf/1986_siegel_1.pdf">Archived</a> (PDF) from the original on 4 March 2016. Retrieved 11 August 2015.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Journal+of+Psychoactive+Drugs&rft.atitle=MDMA.+Nonmedical+use+and+intoxication&rft.volume=18&rft.issue=4&rft.pages=%3Cspan+class%3D%22nowrap%22%3E349-%3C%2Fspan%3E54&rft.date=1986-10&rft_id=info%3Adoi%2F10.1080%2F02791072.1986.10472368&rft_id=info%3Apmid%2F2880950&rft.aulast=Siegel&rft.aufirst=RK&rft_id=http%3A%2F%2Fwww.maps.org%2Fimages%2Fpdf%2F1986_siegel_1.pdf&rfr_id=info%3Asid%2Fen.wikipedia.org%3AMDMA" class="Z3988"> </li> <li id="cite_note-237"><a href="#cite_ref-237">^</a> The first confirmed sample was seized and identified by Chicago Police in 1970, see <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFSreenivasan1972" class="citation journal cs1">Sreenivasan VR (1972). <a rel="nofollow" class="external text" href="http://www.erowid.org/references/refs_view.php?A=ShowDoc1&ID=1149">"Problems in Identification of Methylenedioxy and Methoxy Amphetamines"</a>. 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Journal of Psychoactive Drugs. 33 (3): 213–21. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1080%2F02791072.2001.10400568">10.1080/02791072.2001.10400568</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/11718314">11718314</a>. <a href="/wiki/S2CID_(identifier)" class="mw-redirect" title="S2CID (identifier)">S2CID</a> <a rel="nofollow" class="external text" href="https://api.semanticscholar.org/CorpusID:31142434">31142434</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Journal+of+Psychoactive+Drugs&rft.atitle=An+exploration+of+the+history+and+controversies+surrounding+MDMA+and+MDA&rft.volume=33&rft.issue=3&rft.pages=%3Cspan+class%3D%22nowrap%22%3E213-%3C%2Fspan%3E21&rft.date=2001&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A31142434%23id-name%3DS2CID&rft_id=info%3Apmid%2F11718314&rft_id=info%3Adoi%2F10.1080%2F02791072.2001.10400568&rft.aulast=Pentney&rft.aufirst=AR&rfr_id=info%3Asid%2Fen.wikipedia.org%3AMDMA" class="Z3988"> </li> <li id="cite_note-242"><a href="#cite_ref-242">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://web.archive.org/web/20141220131529/http://www.shulginresearch.org/home/about/alexander-sasha-shulgin/">"Alexander 'Sasha' Shulgin"</a>. <a href="/wiki/Alexander_Shulgin_Research_Institute" title="Alexander Shulgin Research Institute">Alexander Shulgin Research Institute</a>. 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Retrieved 9 May 2022.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Nature+Medicine&rft.atitle=Challenges+with+benchmarking+of+MDMA-assisted+psychotherapy&rft.volume=27&rft.issue=10&rft.pages=%3Cspan+class%3D%22nowrap%22%3E1689-%3C%2Fspan%3E1690&rft.date=2021-10&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A238636360%23id-name%3DS2CID&rft_id=info%3Apmid%2F34635857&rft_id=info%3Adoi%2F10.1038%2Fs41591-021-01525-0&rft.aulast=Halvorsen&rft.aufirst=J%C3%98&rft.au=Naudet%2C+F&rft.au=Cristea%2C+IA&rft_id=https%3A%2F%2Fhal.archives-ouvertes.fr%2Fhal-03414583%2Ffile%2FHalvorsen%2520et%2520al%2520-%25202021%2520-%2520Challenges%2520with%2520benchmarking%2520of%2520MDMA-assisted%2520psychotherapy.pdf&rfr_id=info%3Asid%2Fen.wikipedia.org%3AMDMA" class="Z3988"> </li> <li id="cite_note-271"><a href="#cite_ref-271">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite class="citation book cs1"><a rel="nofollow" class="external text" href="https://web.archive.org/web/20141019192225/http://whqlibdoc.who.int/trs/WHO_TRS_729.pdf">WHO Expert Committee on Drug Dependence: Twenty-second Report</a> (PDF). Geneva: World Health Organization. 1985. pp. 24–25. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-9241207294" title="Special:BookSources/978-9241207294"><bdi>978-9241207294</bdi></a>. Archived from <a rel="nofollow" class="external text" href="http://whqlibdoc.who.int/trs/WHO_TRS_729.pdf">the original</a> (PDF) on 19 October 2014. Retrieved 29 August 2012.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=WHO+Expert+Committee+on+Drug+Dependence%3A+Twenty-second+Report.&rft.place=Geneva&rft.pages=%3Cspan+class%3D%22nowrap%22%3E24-%3C%2Fspan%3E25&rft.pub=World+Health+Organization&rft.date=1985&rft.isbn=978-9241207294&rft_id=http%3A%2F%2Fwhqlibdoc.who.int%2Ftrs%2FWHO_TRS_729.pdf&rfr_id=info%3Asid%2Fen.wikipedia.org%3AMDMA" class="Z3988"> </li> <li id="cite_note-272"><a href="#cite_ref-272">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite class="citation web cs1"><a rel="nofollow" class="external text" href="http://www.unodc.org/documents/commissions/CND/Drug_Resolutions/1980-1989/1986/CND_Decision-1986-07_S-IX.pdf">"Decision to place MDMA into Schedule I"</a> (PDF). UNODC. 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Retrieved 9 May 2015.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=UNODC&rft.atitle=Decision+to+place+MDMA+into+Schedule+I&rft.date=1986-02-11&rft_id=http%3A%2F%2Fwww.unodc.org%2Fdocuments%2Fcommissions%2FCND%2FDrug_Resolutions%2F1980-1989%2F1986%2FCND_Decision-1986-07_S-IX.pdf&rfr_id=info%3Asid%2Fen.wikipedia.org%3AMDMA" class="Z3988"> </li> <li id="cite_note-273"><a href="#cite_ref-273">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFMcKinley2013" class="citation news cs1">McKinley JC (12 September 2013). <a rel="nofollow" class="external text" href="http://artsbeat.blogs.nytimes.com/2013/09/12/overdoses-of-molly-led-to-electric-zoo-deaths/?_r=0">"Overdoses of 'Molly' Led to Electric Zoo Deaths"</a>. 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Retrieved 9 December 2013.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=The+New+York+Times&rft.atitle=Overdoses+of+%27Molly%27+Led+to+Electric+Zoo+Deaths&rft.date=2013-09-12&rft.aulast=McKinley&rft.aufirst=JC&rft_id=http%3A%2F%2Fartsbeat.blogs.nytimes.com%2F2013%2F09%2F12%2Foverdoses-of-molly-led-to-electric-zoo-deaths%2F%3F_r%3D0&rfr_id=info%3Asid%2Fen.wikipedia.org%3AMDMA" class="Z3988"> </li> <li id="cite_note-Goldfrank_2011-274"><a href="#cite_ref-Goldfrank_2011_274-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFNelsonLewinHowlandHoffman2011" class="citation book cs1">Nelson LS, Lewin NA, Howland MA, Hoffman RS, Goldfrank LR, Flomenbaum NE (2011). Goldfrank's toxicologic emergencies (9th ed.). 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Multidisciplinary Association for Psychedelic Studies (MAPS). Santa Cruz, CA. Archived from <a rel="nofollow" class="external text" href="http://www.maps.org/research/">the original</a> on 3 December 2013.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=Multidisciplinary+Association+for+Psychedelic+Studies+%28MAPS%29&rft.atitle=Bibliography+of+Psychedelic+Research+Studies.&rft_id=http%3A%2F%2Fwww.maps.org%2Fresearch%2F&rfr_id=info%3Asid%2Fen.wikipedia.org%3AMDMA" class="Z3988"> </li> <li id="cite_note-276"><a href="#cite_ref-276">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFJames2015" class="citation web cs1">James SD (23 February 2015). <a rel="nofollow" class="external text" href="https://www.nbcnews.com/health/health-news/what-molly-why-it-dangerous-n311291">"What Is Molly and Why Is It Dangerous?"</a>. 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Frontiers in Psychiatry. 10: 650. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.3389%2Ffpsyt.2019.00650">10.3389/fpsyt.2019.00650</a>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6751381">6751381</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/31572236">31572236</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Frontiers+in+Psychiatry&rft.atitle=Breakthrough+for+Trauma+Treatment%3A+Safety+and+Efficacy+of+MDMA-Assisted+Psychotherapy+Compared+to+Paroxetine+and+Sertraline&rft.volume=10&rft.pages=650&rft.date=2019-09-12&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC6751381%23id-name%3DPMC&rft_id=info%3Apmid%2F31572236&rft_id=info%3Adoi%2F10.3389%2Ffpsyt.2019.00650&rft.aulast=Feduccia&rft.aufirst=AA&rft.au=Jerome%2C+L&rft.au=Yazar-Klosinski%2C+B&rft.au=Emerson%2C+A&rft.au=Mithoefer%2C+MC&rft.au=Doblin%2C+R&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC6751381&rfr_id=info%3Asid%2Fen.wikipedia.org%3AMDMA" class="Z3988"> </li> <li id="cite_note-314"><a href="#cite_ref-314">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFChalihaMamoAlbrechtLam2021" class="citation journal cs1">Chaliha D, Mamo JC, Albrecht M, Lam V, Takechi R, Vaccarezza M (1 July 2021). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8686313">"A Systematic Review of the MDMA Model to Address Social Impairment in Autism"</a>. Current Neuropharmacology. 19 (7): 1101–1154. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.2174%2F1570159X19666210101130258">10.2174/1570159X19666210101130258</a>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8686313">8686313</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/33388021">33388021</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Current+Neuropharmacology&rft.atitle=A+Systematic+Review+of+the+MDMA+Model+to+Address+Social+Impairment+in+Autism&rft.volume=19&rft.issue=7&rft.pages=%3Cspan+class%3D%22nowrap%22%3E1101-%3C%2Fspan%3E1154&rft.date=2021-07-01&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC8686313%23id-name%3DPMC&rft_id=info%3Apmid%2F33388021&rft_id=info%3Adoi%2F10.2174%2F1570159X19666210101130258&rft.aulast=Chaliha&rft.aufirst=D&rft.au=Mamo%2C+JC&rft.au=Albrecht%2C+M&rft.au=Lam%2C+V&rft.au=Takechi%2C+R&rft.au=Vaccarezza%2C+M&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC8686313&rfr_id=info%3Asid%2Fen.wikipedia.org%3AMDMA" class="Z3988"> </li> <li id="cite_note-315"><a href="#cite_ref-315">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFArnovitzSpitzbergDavaniVadhan2022" class="citation journal cs1">Arnovitz MD, Spitzberg AJ, Davani AJ, Vadhan NP, Holland J, Kane JM, et al. 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Journal of Clinical Medicine. 11 (12): 3255. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.3390%2Fjcm11123255">10.3390/jcm11123255</a>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9225098">9225098</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/35743326">35743326</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Journal+of+Clinical+Medicine&rft.atitle=MDMA+for+the+Treatment+of+Negative+Symptoms+in+Schizophrenia&rft.volume=11&rft.issue=12&rft.pages=3255&rft.date=2022-06&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC9225098%23id-name%3DPMC&rft_id=info%3Apmid%2F35743326&rft_id=info%3Adoi%2F10.3390%2Fjcm11123255&rft.aulast=Arnovitz&rft.aufirst=MD&rft.au=Spitzberg%2C+AJ&rft.au=Davani%2C+AJ&rft.au=Vadhan%2C+NP&rft.au=Holland%2C+J&rft.au=Kane%2C+JM&rft.au=Michaels%2C+TI&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC9225098&rfr_id=info%3Asid%2Fen.wikipedia.org%3AMDMA" class="Z3988"> </li> </ol></div></div> <div class="mw-heading mw-heading2"><h2 id="External_links">External links</h2></div> <ul><li><a rel="nofollow" class="external text" href="https://maps.org/mdma/ptsd/mapp2/">A Multi-Site Phase 3 Study of MDMA-Assisted Therapy for PTSD (MAPP2)</a></li></ul> <style data-mw-deduplicate="TemplateStyles:r1235681985">.mw-parser-output .side-box{margin:4px 0;box-sizing:border-box;border:1px solid #aaa;font-size:88%;line-height:1.25em;background-color:var(--background-color-interactive-subtle,#f8f9fa);display:flow-root}.mw-parser-output .side-box-abovebelow,.mw-parser-output .side-box-text{padding:0.25em 0.9em}.mw-parser-output .side-box-image{padding:2px 0 2px 0.9em;text-align:center}.mw-parser-output .side-box-imageright{padding:2px 0.9em 2px 0;text-align:center}@media(min-width:500px){.mw-parser-output .side-box-flex{display:flex;align-items:center}.mw-parser-output .side-box-text{flex:1;min-width:0}}@media(min-width:720px){.mw-parser-output .side-box{width:238px}.mw-parser-output .side-box-right{clear:right;float:right;margin-left:1em}.mw-parser-output .side-box-left{margin-right:1em}}</style><style data-mw-deduplicate="TemplateStyles:r1250146164">.mw-parser-output .sister-box .side-box-abovebelow{padding:0.75em 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sistersitebox plainlinks"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /> <div class="side-box-abovebelow"> MDMA at Wikipedia's <a href="/wiki/Wikipedia:Wikimedia_sister_projects" title="Wikipedia:Wikimedia sister projects">sister projects</a></div> <div class="side-box-flex"> <div class="side-box-text plainlist"><ul><li><img alt="" src="//upload.wikimedia.org/wikipedia/en/thumb/0/06/Wiktionary-logo-v2.svg/27px-Wiktionary-logo-v2.svg.png" decoding="async" width="27" height="27" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/0/06/Wiktionary-logo-v2.svg/41px-Wiktionary-logo-v2.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/0/06/Wiktionary-logo-v2.svg/54px-Wiktionary-logo-v2.svg.png 2x" data-file-width="391" data-file-height="391" /><a href="https://en.wiktionary.org/wiki/MDMA" class="extiw" title="wikt:MDMA">Definitions</a> from Wiktionary</li><li><img alt="" src="//upload.wikimedia.org/wikipedia/en/thumb/4/4a/Commons-logo.svg/20px-Commons-logo.svg.png" decoding="async" width="20" height="27" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/4/4a/Commons-logo.svg/30px-Commons-logo.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/4/4a/Commons-logo.svg/40px-Commons-logo.svg.png 2x" data-file-width="1024" data-file-height="1376" /><a href="https://commons.wikimedia.org/wiki/Category:MDMA" class="extiw" title="c:Category:MDMA">Media</a> from Commons</li><li><img alt="" src="//upload.wikimedia.org/wikipedia/commons/thumb/2/24/Wikinews-logo.svg/27px-Wikinews-logo.svg.png" decoding="async" width="27" height="15" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/2/24/Wikinews-logo.svg/41px-Wikinews-logo.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/2/24/Wikinews-logo.svg/54px-Wikinews-logo.svg.png 2x" data-file-width="759" data-file-height="415" /><a href="https://en.wikinews.org/wiki/MDMA" class="extiw" title="n:MDMA">News</a> from Wikinews</li><li><img alt="" src="//upload.wikimedia.org/wikipedia/commons/thumb/f/fa/Wikiquote-logo.svg/23px-Wikiquote-logo.svg.png" decoding="async" width="23" height="27" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/f/fa/Wikiquote-logo.svg/35px-Wikiquote-logo.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/f/fa/Wikiquote-logo.svg/46px-Wikiquote-logo.svg.png 2x" data-file-width="300" data-file-height="355" /><a href="https://en.wikiquote.org/wiki/Drugs#MDMA" class="extiw" title="q:Drugs">Quotations</a> from Wikiquote</li><li><img alt="" src="//upload.wikimedia.org/wikipedia/commons/thumb/f/ff/Wikidata-logo.svg/27px-Wikidata-logo.svg.png" decoding="async" width="27" height="15" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/f/ff/Wikidata-logo.svg/41px-Wikidata-logo.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/f/ff/Wikidata-logo.svg/54px-Wikidata-logo.svg.png 2x" data-file-width="1050" data-file-height="590" /><a href="https://www.wikidata.org/wiki/Q69488" class="extiw" title="d:Q69488">Data</a> from Wikidata</li></ul></div></div> </div> <ul><li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://www.drugabuse.gov/publications/drugfacts/mdma-ecstasymolly">"MDMA Facts and Statistics"</a>. National Institute on Drug Abuse. 15 June 2020.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=National+Institute+on+Drug+Abuse&rft.atitle=MDMA+Facts+and+Statistics&rft.date=2020-06-15&rft_id=https%3A%2F%2Fwww.drugabuse.gov%2Fpublications%2Fdrugfacts%2Fmdma-ecstasymolly&rfr_id=info%3Asid%2Fen.wikipedia.org%3AMDMA" class="Z3988"></li> <li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite class="citation web cs1"><a rel="nofollow" class="external text" href="http://www.emcdda.europa.eu/publications/drug-profiles/mdma">"Methylenedioxymethamphetamine (MDMA or 'Ecstasy') drug profile"</a>. European Monitoring Centre for Drugs and Drug Addiction.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=European+Monitoring+Centre+for+Drugs+and+Drug+Addiction&rft.atitle=Methylenedioxymethamphetamine+%28MDMA+or+%27Ecstasy%27%29+drug+profile&rft_id=http%3A%2F%2Fwww.emcdda.europa.eu%2Fpublications%2Fdrug-profiles%2Fmdma&rfr_id=info%3Asid%2Fen.wikipedia.org%3AMDMA" class="Z3988"></li> <li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite class="citation web cs1"><a rel="nofollow" class="external text" href="http://www.maps.org/research/mdma">"MDMA-Assisted Psychotherapy"</a>. Multidisciplinary Association for Psychedelic Studies.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=Multidisciplinary+Association+for+Psychedelic+Studies&rft.atitle=MDMA-Assisted+Psychotherapy&rft_id=http%3A%2F%2Fwww.maps.org%2Fresearch%2Fmdma&rfr_id=info%3Asid%2Fen.wikipedia.org%3AMDMA" class="Z3988"></li></ul> <div class="navbox-styles"><style data-mw-deduplicate="TemplateStyles:r1236075235">.mw-parser-output .navbox{box-sizing:border-box;border:1px solid #a2a9b1;width:100%;clear:both;font-size:88%;text-align:center;padding:1px;margin:1em auto 0}.mw-parser-output .navbox .navbox{margin-top:0}.mw-parser-output .navbox+.navbox,.mw-parser-output .navbox+.navbox-styles+.navbox{margin-top:-1px}.mw-parser-output .navbox-inner,.mw-parser-output .navbox-subgroup{width:100%}.mw-parser-output .navbox-group,.mw-parser-output .navbox-title,.mw-parser-output .navbox-abovebelow{padding:0.25em 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href="/wiki/Recreational_drug_use" title="Recreational drug use">Recreational drug use</a></div></th></tr><tr><td colspan="2" class="navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks mw-collapsible mw-collapsed navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="col" class="navbox-title" colspan="2" style="text-align:center;"><div id="Major_recreational_drugs90" style="font-size:114%;margin:0 4em">Major recreational drugs</div></th></tr><tr><td colspan="2" class="navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Depressant" title="Depressant">Depressants</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Barbiturate" title="Barbiturate">Barbiturates</a></li> <li><a href="/wiki/Benzodiazepine" title="Benzodiazepine">Benzodiazepines</a></li> <li><a href="/wiki/Carbamate" title="Carbamate">Carbamates</a></li> <li><a href="/wiki/Alcohol_(drug)" title="Alcohol (drug)">Ethanol (alcohol)</a> <ul><li><a href="/wiki/Alcoholic_beverage" title="Alcoholic beverage">Alcoholic beverage</a></li> <li><a href="/wiki/Beer" title="Beer">Beer</a></li> <li><a href="/wiki/Wine" title="Wine">Wine</a></li></ul></li> <li><a href="/wiki/Gabapentinoid" title="Gabapentinoid">Gabapentinoids</a></li> <li><a href="/wiki/Gamma-Hydroxybutyric_acid" class="mw-redirect" title="Gamma-Hydroxybutyric acid">GHB</a></li> <li><a href="/wiki/Inhalant" title="Inhalant">Inhalants</a> <ul><li>Medical <ul><li><a href="/wiki/Nitrous_oxide" title="Nitrous oxide">Nitrous oxide</a> (<a href="/wiki/Recreational_use_of_nitrous_oxide" title="Recreational use of nitrous oxide">recreational use</a>)</li></ul></li> <li>Hazardous <a href="/wiki/Solvent" title="Solvent">solvents</a> <ul><li><a href="/wiki/Adhesive#Contact" title="Adhesive">contact adhesives</a></li> <li><a href="/wiki/Gasoline" title="Gasoline">Gasoline</a></li> <li><a href="/wiki/Nail_polish#Nail_polish_remover" title="Nail polish">nail polish remover</a></li> <li><a href="/wiki/Paint_thinner" title="Paint thinner">Paint thinner</a></li></ul></li> <li>Other <ul><li><a href="/wiki/Freon" title="Freon">Freon</a></li></ul></li></ul></li> <li><a href="/wiki/Kava" title="Kava">Kava</a></li> <li><a href="/wiki/Nonbenzodiazepine" title="Nonbenzodiazepine">Nonbenzodiazepines</a></li> <li><a href="/wiki/Quinazolinone" title="Quinazolinone">Quinazolinones</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Opioid" title="Opioid">Opioids</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Buprenorphine" title="Buprenorphine">Buprenorphine</a> <ul><li>Suboxone</li> <li>Subutex</li></ul></li> <li><a href="/wiki/Codeine" title="Codeine">Codeine</a> <ul><li><a href="/wiki/Lean_(drug)" title="Lean (drug)">Lean</a></li></ul></li> <li><a href="/wiki/Desomorphine" title="Desomorphine">Desomorphine</a> <ul><li>Krokodil</li></ul></li> <li><a href="/wiki/Dextropropoxyphene" title="Dextropropoxyphene">Dextropropoxyphene</a> <ul><li>Darvocet</li> <li>Darvon</li></ul></li> <li><a href="/wiki/Fentanyl" title="Fentanyl">Fentanyl</a></li> <li><a href="/wiki/Heroin" title="Heroin">Diamorphine</a> <ul><li>Heroin</li></ul></li> <li><a href="/wiki/Hydrocodone" title="Hydrocodone">Hydrocodone</a></li> <li><a href="/wiki/Hydromorphone" title="Hydromorphone">Hydromorphone</a> <ul><li>Dilaudid</li></ul></li> <li><a href="/wiki/Methadone" title="Methadone">Methadone</a></li> <li><a href="/wiki/Mitragyna_speciosa" title="Mitragyna speciosa">Mitragyna speciosa</a> <ul><li><a href="/wiki/Kratom" class="mw-redirect" title="Kratom">Kratom</a></li></ul></li> <li><a href="/wiki/Morphine" title="Morphine">Morphine</a> <ul><li><a href="/wiki/Opium" title="Opium">Opium</a></li></ul></li> <li><a href="/wiki/Oxycodone" title="Oxycodone">Oxycodone</a> <ul><li><a href="/wiki/Oxycodone/paracetamol" title="Oxycodone/paracetamol">/paracetamol</a></li></ul></li> <li><a href="/wiki/Tramadol" title="Tramadol">Tramadol</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Stimulant" title="Stimulant">Stimulants</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Amphetamine" title="Amphetamine">Amphetamine</a></li> <li><a href="/wiki/Arecoline" title="Arecoline">Arecoline</a> <ul><li><a href="/wiki/Areca" title="Areca">Areca</a></li></ul></li> <li><a href="/wiki/Paan" class="mw-redirect" title="Paan">Betel</a></li> <li><a href="/wiki/Caffeine" title="Caffeine">Caffeine</a> <ul><li><a href="/wiki/Coffee" title="Coffee">Coffee</a></li> <li><a href="/wiki/Energy_drink" title="Energy drink">Energy drinks</a></li> <li><a href="/wiki/Tea" title="Tea">Tea</a></li></ul></li> <li><a href="/wiki/Cathinone" title="Cathinone">Cathinone</a> <ul><li><a href="/wiki/Khat" title="Khat">Khat</a></li></ul></li> <li><a href="/wiki/Cocaine" title="Cocaine">Cocaine</a> <ul><li><a href="/wiki/Coca" title="Coca">Coca</a></li> <li><a href="/wiki/Crack_cocaine" title="Crack cocaine">Crack</a></li></ul></li> <li><a href="/wiki/Ephedrine" title="Ephedrine">Ephedrine</a> <ul><li><a href="/wiki/Ephedra_(medicine)" title="Ephedra (medicine)">Ephedra</a></li></ul></li> <li><a href="/wiki/Methylenedioxypyrovalerone" title="Methylenedioxypyrovalerone">MDPV</a></li> <li><a href="/wiki/Mephedrone" title="Mephedrone">Mephedrone</a></li> <li><a href="/wiki/Methamphetamine" title="Methamphetamine">Methamphetamine</a></li> <li><a href="/wiki/Methylone" title="Methylone">Methylone</a></li> <li><a href="/wiki/Methylphenidate" title="Methylphenidate">Methylphenidate</a></li> <li><a href="/wiki/Modafinil" title="Modafinil">Modafinil</a></li> <li><a href="/wiki/Nicotine" title="Nicotine">Nicotine</a> <ul><li><a href="/wiki/Nicotine_polacrilex" title="Nicotine polacrilex">Polacrilex</a></li> <li><a href="/wiki/Nicotine_salt" title="Nicotine salt">Salt</a></li> <li><a href="/wiki/Tobacco" title="Tobacco">Tobacco</a></li></ul></li> <li><a href="/wiki/Theobromine" title="Theobromine">Theobromine</a> <ul><li><a href="/wiki/Cocoa_bean" title="Cocoa bean">Cocoa</a></li> <li><a href="/wiki/Chocolate" title="Chocolate">Chocolate</a></li></ul></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Empathogen%E2%80%93entactogen" class="mw-redirect" title="Empathogen–entactogen">Entactogens</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/2C_(psychedelics)" title="2C (psychedelics)">2C series</a></li> <li><a href="/wiki/6-APB" title="6-APB">6-APB</a> <ul><li>Benzofury</li></ul></li> <li><a href="/wiki/Alpha-Methyltryptamine" class="mw-redirect" title="Alpha-Methyltryptamine">AMT</a></li> <li><a href="/wiki/3,4-Methylenedioxyamphetamine" title="3,4-Methylenedioxyamphetamine">MDA</a></li> <li><a class="mw-selflink selflink">MDMA</a> <ul><li><a class="mw-selflink-fragment" href="#Forms">Ecstasy</a></li> <li><a class="mw-selflink-fragment" href="#Forms">Molly</a></li></ul></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Hallucinogen" title="Hallucinogen">Hallucinogens</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Psychedelic_drug" title="Psychedelic drug">Psychedelics</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Bufotenin" title="Bufotenin">Bufotenin</a> <ul><li><a href="/wiki/Colorado_River_toad" title="Colorado River toad">Psychoactive toads</a></li> <li><a href="/wiki/Anadenanthera_colubrina" title="Anadenanthera colubrina">Vilca</a></li> <li><a href="/wiki/Anadenanthera_peregrina" title="Anadenanthera peregrina">Yopo</a></li></ul></li> <li><a href="/wiki/N,N-Dimethyltryptamine" title="N,N-Dimethyltryptamine">DMT</a> <ul><li><a href="/wiki/Ayahuasca" title="Ayahuasca">Ayahuasca</a></li></ul></li> <li><a href="/wiki/Ergine" title="Ergine">LSA</a></li> <li><a href="/wiki/LSD" title="LSD">LSD-25</a></li> <li><a href="/wiki/Mescaline" title="Mescaline">Mescaline</a> <ul><li><a href="/wiki/Echinopsis_peruviana" class="mw-redirect" title="Echinopsis peruviana">Peruvian torch</a></li> <li><a href="/wiki/Peyote" title="Peyote">Peyote</a></li> <li><a href="/wiki/Echinopsis_pachanoi" class="mw-redirect" title="Echinopsis pachanoi">San Pedro</a></li></ul></li> <li><a href="/wiki/Psilocybin" title="Psilocybin">Psilocybin</a> / <a href="/wiki/Psilocin" title="Psilocin">Psilocin</a> <ul><li><a href="/wiki/Psilocybin_mushroom" title="Psilocybin mushroom">Psilocybin mushrooms</a></li></ul></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Dissociative" title="Dissociative">Dissociatives</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Dextromethorphan" title="Dextromethorphan">DXM</a> (<a href="/wiki/Recreational_use_of_dextromethorphan" title="Recreational use of dextromethorphan">recreational use</a>)</li> <li><a href="/wiki/Glaucine" title="Glaucine">Glaucine</a></li> <li><a href="/wiki/Inhalant" title="Inhalant">Inhalants</a> <ul><li><a href="/wiki/Nitrous_oxide" title="Nitrous oxide">Nitrous oxide</a> (<a href="/wiki/Recreational_use_of_nitrous_oxide" title="Recreational use of nitrous oxide">recreational use</a>)</li> <li><a href="/wiki/Alkyl_nitrites" class="mw-redirect" title="Alkyl nitrites">alkyl nitrites</a></li> <li><a href="/wiki/Poppers" title="Poppers">poppers</a></li> <li><a href="/wiki/Amyl_nitrite" title="Amyl nitrite">amyl nitrite</a></li></ul></li> <li><a href="/wiki/Ketamine" title="Ketamine">Ketamine</a></li> <li><a href="/wiki/Methoxetamine" title="Methoxetamine">MXE</a></li> <li><a href="/wiki/Muscimol" title="Muscimol">Muscimol</a> <ul><li><a href="/wiki/Amanita_muscaria" title="Amanita muscaria">Amanita muscaria</a></li></ul></li> <li><a href="/wiki/Phencyclidine" title="Phencyclidine">PCP</a></li> <li><a href="/wiki/Salvinorin_A" title="Salvinorin A">Salvinorin A</a> <ul><li><a href="/wiki/Salvia_divinorum" title="Salvia divinorum">Salvia divinorum</a></li></ul></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Deliriant" title="Deliriant">Deliriants</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Atropine" title="Atropine">Atropine</a> and <a href="/wiki/Scopolamine" title="Scopolamine">Scopolamine</a> <ul><li><a href="/wiki/Atropa_belladonna" class="mw-redirect" title="Atropa belladonna">Atropa belladonna</a></li> <li><a href="/wiki/Datura" title="Datura">Datura</a></li> <li><a href="/wiki/Hyoscyamus_niger" title="Hyoscyamus niger">Hyoscyamus niger</a></li> <li><a href="/wiki/Mandragora_officinarum" title="Mandragora officinarum">Mandragora officinarum</a></li></ul></li> <li><a href="/wiki/Dimenhydrinate" title="Dimenhydrinate">Dimenhydrinate</a></li> <li><a href="/wiki/Diphenhydramine" title="Diphenhydramine">Diphenhydramine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Cannabinoid" title="Cannabinoid">Cannabinoids</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Tetrahydrocannabinol" title="Tetrahydrocannabinol">THC</a> <ul><li><a href="/wiki/Cannabis_(drug)" title="Cannabis (drug)">Cannabis (Marijuana)</a></li> <li><a href="/wiki/Hashish" title="Hashish">Hashish</a></li> <li><a href="/wiki/Hash_oil" title="Hash oil">Hash oil</a></li></ul></li> <li><a href="/wiki/Neocannabinoid" class="mw-redirect" title="Neocannabinoid">Neocannabinoid / synthetic cannabinoids</a> <ul><li><a href="/wiki/JWH-018" title="JWH-018">JWH-018</a></li> <li><a href="/wiki/APICA_(synthetic_cannabinoid_drug)" title="APICA (synthetic cannabinoid drug)">APICA</a></li> <li><a href="/wiki/APINACA" title="APINACA">APINACA</a></li> <li><a href="/wiki/Spice_(drug)" class="mw-redirect" title="Spice (drug)">Spice</a></li></ul></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Oneirogen" title="Oneirogen">Oneirogens</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Calea_ternifolia" title="Calea ternifolia">Calea zacatechichi</a></li> <li><a href="/wiki/Silene_undulata" title="Silene undulata">Silene capensis</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Club_drug" title="Club drug">Club drugs</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Cocaine" title="Cocaine">Cocaine</a></li> <li><a href="/wiki/Methaqualone" title="Methaqualone">Quaaludes</a></li> <li><a class="mw-selflink selflink">MDMA</a> <ul><li><a class="mw-selflink-fragment" href="#Forms">Ecstasy</a></li> <li><a class="mw-selflink-fragment" href="#Forms">Molly</a></li></ul></li> <li><a href="/wiki/Nitrous_oxide" title="Nitrous oxide">Nitrous oxide</a> (<a href="/wiki/Recreational_use_of_nitrous_oxide" title="Recreational use of nitrous oxide">recreational use</a>)</li> <li><a href="/wiki/Poppers" title="Poppers">Poppers</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr></tbody></table><div></div></td></tr><tr><td colspan="2" class="navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks mw-collapsible mw-collapsed navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="col" class="navbox-title" colspan="2" style="text-align:center;"><div id="Drug_culture90" style="font-size:114%;margin:0 4em"><a href="/wiki/Drug_culture" title="Drug culture">Drug culture</a></div></th></tr><tr><td colspan="2" class="navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Cannabis_culture" title="Cannabis culture">Cannabis culture</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/420_(cannabis_culture)" title="420 (cannabis culture)">420</a></li> <li><a href="/wiki/Cannabis_consumption" title="Cannabis consumption">Cannabis consumption</a></li> <li><a href="/wiki/Cannabis_cultivation" title="Cannabis cultivation">Cannabis cultivation</a></li> <li><a href="/wiki/Cannabis_edible" title="Cannabis edible">Cannabis edible</a></li> <li><a href="/wiki/Cannabis_rights" title="Cannabis rights">Cannabis rights</a></li> <li><a href="/wiki/List_of_cannabis_rights_leaders" title="List of cannabis rights leaders">Cannabis rights leaders</a></li> <li><a href="/wiki/List_of_cannabis_rights_organizations" title="List of cannabis rights organizations">List of cannabis rights organizations</a></li> <li><a href="/wiki/Cannabis_smoking" title="Cannabis smoking">Cannabis smoking</a></li> <li><a href="/wiki/Cannabis_Social_Club" title="Cannabis Social Club">Cannabis Social Club</a></li> <li><a href="/wiki/Cannabis_tea" title="Cannabis tea">Cannabis tea</a></li> <li><a href="/wiki/Vaporizer_(inhalation_device)#Cannabis_vaporizers" title="Vaporizer (inhalation device)">Cannabis vaping</a></li> <li><a href="/wiki/Head_shop" title="Head shop">Head shop</a></li> <li><a href="/wiki/Legal_history_of_cannabis_in_the_United_States" title="Legal history of cannabis in the United States">Legal history of cannabis in the United States</a></li> <li><a href="/wiki/Legality_of_cannabis" title="Legality of cannabis">Legality of cannabis</a></li> <li><a href="/wiki/Marijuana_Policy_Project" title="Marijuana Policy Project">Marijuana Policy Project</a></li> <li><a href="/wiki/Medical_cannabis" title="Medical cannabis">Medical cannabis</a></li> <li><a href="/wiki/National_Organization_for_the_Reform_of_Marijuana_Laws" title="National Organization for the Reform of Marijuana Laws">NORML</a></li> <li><a href="/wiki/Cannabis_and_religion" title="Cannabis and religion">Cannabis and religion</a></li> <li><a href="/wiki/Stoner_film" title="Stoner film">Stoner film</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Coffee_culture" title="Coffee culture">Coffee culture</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Break_(work)#Coffee_break" title="Break (work)">Coffee break</a></li> <li><a href="/wiki/Coffeehouse" title="Coffeehouse">Coffeehouse</a></li> <li><a href="/wiki/Latte_art" title="Latte art">Latte art</a></li> <li><a href="/wiki/Teahouse" title="Teahouse">Teahouse</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Drinking_culture" title="Drinking culture">Drinking culture</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Bartender" title="Bartender">Bartending</a></li> <li><a href="/wiki/Beer#Beer_and_society" title="Beer">Beer culture</a></li> <li><a href="/wiki/Beer_festival" title="Beer festival">Beer festival</a></li> <li><a href="/wiki/Binge_drinking" title="Binge drinking">Binge drinking</a></li> <li><a href="/wiki/Diethyl_ether#Recreational_use" title="Diethyl ether">Diethyl ether</a></li> <li><a href="/wiki/Drinking_game" title="Drinking game">Drinking games</a></li> <li><a href="/wiki/Drinking_song" title="Drinking song">Drinking song</a></li> <li><a href="/wiki/Happy_hour" title="Happy hour">Happy hour</a></li> <li><a href="/wiki/Hip_flask" title="Hip flask">Hip flask</a></li> <li><a href="/wiki/Nightclub" title="Nightclub">Nightclub</a></li> <li><a href="/wiki/Oktoberfest" title="Oktoberfest">Oktoberfest</a></li> <li><a href="/wiki/Pub" title="Pub">Pub</a></li> <li><a href="/wiki/Pub_crawl" title="Pub crawl">Pub crawl</a></li> <li><a href="/wiki/Sommelier" title="Sommelier">Sommelier</a></li> <li><a href="/wiki/Bar_(establishment)" title="Bar (establishment)">Sports bar</a></li> <li><a href="/wiki/Tailgate_party" title="Tailgate party">Tailgate party</a></li> <li><a href="/wiki/Wine_bar" title="Wine bar">Wine bar</a></li> <li><a href="/wiki/Wine_tasting" title="Wine tasting">Wine tasting</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Psychedelia" title="Psychedelia">Psychedelia</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Psychonautics" title="Psychonautics">Psychonautics</a></li> <li><a href="/wiki/Psychedelic_art" title="Psychedelic art">Art</a></li> <li><a href="/wiki/Psychedelic_drug" title="Psychedelic drug">Drug</a></li> <li><a href="/wiki/Psychedelic_era" title="Psychedelic era">Era</a></li> <li><a href="/wiki/Psychedelic_experience" title="Psychedelic experience">Experience</a></li> <li><a href="/wiki/Psychedelic_literature" class="mw-redirect" title="Psychedelic literature">Literature</a></li> <li><a href="/wiki/Psychedelic_music" title="Psychedelic music">Music</a></li> <li><a href="/wiki/Psychedelic_microdosing" title="Psychedelic microdosing">Microdosing</a></li> <li><a href="/wiki/Smart_shop" title="Smart shop">Smart shop</a></li> <li><a href="/wiki/Psychedelic_therapy" title="Psychedelic therapy">Therapy</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Smoking#Society_and_culture" title="Smoking">Smoking culture</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Cigarette_card" title="Cigarette card">Cigarette card</a></li> <li><a href="/wiki/Fashion_cigarettes" title="Fashion cigarettes">Fashion cigarettes</a></li> <li><a href="/wiki/Cloud-chasing" title="Cloud-chasing">Cloud-chasing</a></li> <li><a href="/wiki/Loosie" title="Loosie">Loosie</a></li> <li><a href="/wiki/Smokeasy" title="Smokeasy">Smokeasy</a></li> <li><a href="/wiki/Smoking_fetishism" title="Smoking fetishism">Smoking fetishism</a></li> <li><a href="/wiki/Tobacco_smoking" title="Tobacco smoking">Tobacco smoking</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Other</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Chasing_the_dragon" title="Chasing the dragon">Chasing the dragon</a></li> <li><a href="/wiki/Club_drug" title="Club drug">Club drug</a></li> <li><a href="/wiki/Counterculture_of_the_1960s" title="Counterculture of the 1960s">Counterculture of the 1960s</a></li> <li><a href="/wiki/Dance_party" title="Dance party">Dance party</a></li> <li><a href="/wiki/Drug_paraphernalia" title="Drug paraphernalia">Drug paraphernalia</a></li> <li><a href="/wiki/Recreational_drug_tourism" title="Recreational drug tourism">Drug tourism</a></li> <li><a href="/wiki/Entheogen" title="Entheogen">Entheogen</a></li> <li><a href="/wiki/Hippie" title="Hippie">Hippie</a></li> <li><a href="/wiki/Needle_sharing" title="Needle sharing">Needle sharing</a></li> <li><a href="/wiki/Nootropic" title="Nootropic">Nootropic</a></li> <li><a href="/wiki/Party_and_play" title="Party and play">Party and play</a></li> <li><a href="/wiki/Poly_drug_use" class="mw-redirect" title="Poly drug use">Poly drug use</a></li> <li><a href="/wiki/Rave" title="Rave">Rave</a></li> <li><a href="/wiki/Religion_and_drugs" title="Religion and drugs">Religion and drugs</a></li> <li><a href="/wiki/Self-medication" title="Self-medication">Self-medication</a></li> <li><a href="/wiki/Sex_and_drugs" title="Sex and drugs">Sex and drugs</a></li> <li><a href="/wiki/Urban_legends_about_drugs" title="Urban legends about drugs">Urban legends about drugs</a></li> <li><a href="/wiki/Whoonga" title="Whoonga">Whoonga</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr></tbody></table><div></div></td></tr><tr><td colspan="2" class="navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks mw-collapsible mw-collapsed navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="col" class="navbox-title" colspan="2" style="text-align:center;"><div id="Legality_of_drug_use90" style="font-size:114%;margin:0 4em">Legality of drug use</div></th></tr><tr><td colspan="2" class="navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%">International</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/United_Nations_drug_control_conventions" class="mw-redirect" title="United Nations drug control conventions">International drug control conventions</a> <ul><li><a href="/wiki/Single_Convention_on_Narcotic_Drugs" title="Single Convention on Narcotic Drugs">1961 Narcotic Drugs</a></li> <li><a href="/wiki/Convention_on_Psychotropic_Substances" title="Convention on Psychotropic Substances">1971 Psychotropic Substances</a></li> <li><a href="/wiki/United_Nations_Convention_Against_Illicit_Traffic_in_Narcotic_Drugs_and_Psychotropic_Substances" title="United Nations Convention Against Illicit Traffic in Narcotic Drugs and Psychotropic Substances">1988 Drug Trafficking</a></li></ul></li> <li>Other treaties addressing drugs <ul><li><a href="/wiki/United_Nations_Convention_on_the_Law_of_the_Sea" title="United Nations Convention on the Law of the Sea">Law of the Sea Convention</a></li> <li><a href="/wiki/International_Convention_Against_Doping_in_Sport" title="International Convention Against Doping in Sport">Convention Against Doping</a></li> <li><a href="/wiki/Council_of_the_European_Union_decisions_on_designer_drugs" title="Council of the European Union decisions on designer drugs">Council of the European Union decisions on designer drugs</a></li></ul></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">State level</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Drug_policy" title="Drug policy">Drug policy</a> <ul><li><a href="/wiki/Decriminalization" title="Decriminalization">Decriminalization</a></li> <li><a href="/wiki/Legalization" title="Legalization">Legalization</a></li> <li><a href="/wiki/Prohibition_of_drugs" class="mw-redirect" title="Prohibition of drugs">Prohibition</a></li> <li><a href="/wiki/Regulation" title="Regulation">Regulation</a></li> <li><a href="/wiki/Supply_reduction" title="Supply reduction">Supply reduction</a></li></ul></li> <li><a href="/wiki/Drug_policy_reform" class="mw-redirect" title="Drug policy reform">Policy reform</a> <ul><li><a href="/wiki/Demand_reduction" title="Demand reduction">Demand reduction</a></li> <li><a href="/wiki/Drug_Policy_Alliance" title="Drug Policy Alliance">Drug Policy Alliance</a></li> <li><a href="/wiki/Harm_reduction" title="Harm reduction">Harm reduction</a></li> <li><a href="/wiki/Law_Enforcement_Action_Partnership" title="Law Enforcement Action Partnership">Law Enforcement Action Partnership</a></li> <li><a href="/wiki/Drug_liberalization" title="Drug liberalization">Liberalization</a> <ul><li><a href="/wiki/Latin_American_drug_legalization" title="Latin American drug legalization">Latin America</a></li></ul></li> <li><a href="/wiki/Students_for_Sensible_Drug_Policy" title="Students for Sensible Drug Policy">Students for Sensible Drug Policy</a></li> <li><a href="/wiki/Transform_Drug_Policy_Foundation" title="Transform Drug Policy Foundation">Transform Drug Policy Foundation</a></li></ul></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Drug policy by country</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Drug_policy#Australia" title="Drug policy">Australia</a></li> <li><a href="/wiki/Drug_policy_of_Canada" title="Drug policy of Canada">Canada</a></li> <li><a href="/wiki/Drug_policy_of_China" title="Drug policy of China">China</a></li> <li><a href="/wiki/Drug_policy_of_the_Czech_Republic" class="mw-redirect" title="Drug policy of the Czech Republic">Czech Republic</a></li> <li><a href="/wiki/Drug_policy#Germany" title="Drug policy">Germany</a></li> <li><a href="/wiki/Drug_policy_of_India" title="Drug policy of India">India</a></li> <li><a href="/wiki/Drug_policy_of_Laos" title="Drug policy of Laos">Laos</a></li> <li><a href="/wiki/Drug_policy_of_the_Netherlands" title="Drug policy of the Netherlands">Netherlands</a></li> <li><a href="/wiki/Drug_policy_of_the_Philippines" title="Drug policy of the Philippines">Philippines</a></li> <li><a href="/wiki/Drug_policy_of_Poland" title="Drug policy of Poland">Poland</a></li> <li><a href="/wiki/Drug_policy_of_Portugal" title="Drug policy of Portugal">Portugal</a></li> <li><a href="/wiki/Drug_policy_of_Romania" title="Drug policy of Romania">Romania</a></li> <li><a href="/wiki/Drug_policy_of_Slovakia" title="Drug policy of Slovakia">Slovakia</a></li> <li><a href="/wiki/Drug_policy_of_South_Korea" title="Drug policy of South Korea">South Korea</a></li> <li><a href="/wiki/Drug_policy_of_the_Soviet_Union" title="Drug policy of the Soviet Union">Soviet Union</a></li> <li><a href="/wiki/Drug_policy_of_Sweden" title="Drug policy of Sweden">Sweden</a></li> <li><a href="/wiki/Drug_policy#Switzerland" title="Drug policy">Switzerland</a></li> <li><a href="/wiki/Federal_drug_policy_of_the_United_States" title="Federal drug policy of the United States">United States</a> <ul><li><a href="/wiki/Just_Say_No" title="Just Say No">Just Say No</a></li> <li><a href="/wiki/Office_of_National_Drug_Control_Policy" title="Office of National Drug Control Policy">Office of National Drug Control Policy</a></li> <li><a href="/wiki/School_district_drug_policies" title="School district drug policies">School district drug policies</a></li> <li><a href="/wiki/Drug_policy_of_California" title="Drug policy of California">California</a></li> <li><a href="/wiki/Cannabis_in_Colorado" title="Cannabis in Colorado">Colorado</a></li> <li><a href="/wiki/Drug_policy_of_Maryland" title="Drug policy of Maryland">Maryland</a></li> <li><a href="/wiki/Drug_policy_of_Oregon" title="Drug policy of Oregon">Oregon</a></li> <li><a href="/wiki/Drug_policy_of_Virginia" title="Drug policy of Virginia">Virginia</a></li></ul></li> <li><a href="/wiki/Drug_policy_of_the_United_Kingdom" title="Drug policy of the United Kingdom">United Kingdom</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Drug legality</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Alcohol_law" title="Alcohol law">Alcohol legality</a></li> <li><a href="/wiki/Anabolic_steroid#Legal_status" title="Anabolic steroid">Anabolic steroid legality</a></li> <li><a href="/wiki/Legality_of_cannabis" title="Legality of cannabis">Cannabis legality</a></li> <li><a href="/wiki/Legal_status_of_cocaine" title="Legal status of cocaine">Cocaine legality</a></li> <li><a href="/wiki/Legal_status_of_methamphetamine" title="Legal status of methamphetamine">Methamphetamine legality</a></li> <li><a href="/wiki/Psilocybin_decriminalization_in_the_United_States" title="Psilocybin decriminalization in the United States">Psilocybin decriminalization in the U.S.</a></li> <li><a href="/wiki/Legal_status_of_psilocybin_mushrooms" title="Legal status of psilocybin mushrooms">Psilocybin mushrooms legality</a></li> <li><a href="/wiki/Legal_status_of_Salvia_divinorum" title="Legal status of Salvia divinorum">Salvia legality</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Other</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Arguments_for_and_against_drug_prohibition" title="Arguments for and against drug prohibition">Arguments for and against drug prohibition</a></li> <li><a href="/wiki/Cannabis_rights" title="Cannabis rights">Cannabis rights</a></li> <li><a href="/wiki/Capital_punishment_for_drug_trafficking" title="Capital punishment for drug trafficking">Capital punishment for drug trafficking</a></li> <li><a href="/wiki/Cognitive_liberty" title="Cognitive liberty">Cognitive liberty</a></li> <li><a href="/wiki/Designer_drug" title="Designer drug">Designer drug</a></li> <li><a href="/wiki/Drug_court" title="Drug court">Drug court</a></li> <li><a href="/wiki/Drug_possession" class="mw-redirect" title="Drug possession">Drug possession</a></li> <li><a href="/wiki/Drug_test" title="Drug test">Drug test</a></li> <li><a href="/wiki/Informant" title="Informant">Narc</a></li> <li><a href="/wiki/Politics_of_drug_abuse" title="Politics of drug abuse">Politics of drug abuse</a></li> <li><a href="/wiki/War_on_drugs" title="War on drugs">War on drugs</a> <ul><li><a href="/wiki/Mexican_drug_war" title="Mexican drug war">Mexican drug war</a></li> <li><a href="/wiki/Plan_Colombia" title="Plan Colombia">Plan Colombia</a></li> <li><a href="/wiki/Philippine_drug_war" title="Philippine drug war">Philippine drug war</a></li></ul></li> <li><a href="/wiki/Zero_tolerance" title="Zero tolerance">Zero tolerance</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr></tbody></table><div></div></td></tr><tr><td colspan="2" class="navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks mw-collapsible mw-collapsed navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="col" class="navbox-title" colspan="2" style="text-align:center;"><div id="Other90" style="font-size:114%;margin:0 4em">Other</div></th></tr><tr><td colspan="2" class="navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%">Drug production and trade</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;">Drug production</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Coca_production_in_Colombia" title="Coca production in Colombia">Coca production in Colombia</a></li> <li><a href="/wiki/Precursor_chemicals" title="Precursor chemicals">Drug precursors</a></li> <li><a href="/wiki/Opium_production_in_Afghanistan" title="Opium production in Afghanistan">Opium production in Afghanistan</a></li> <li><a href="/wiki/Rolling_meth_lab" title="Rolling meth lab">Rolling meth lab</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;">Drug trade</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Illegal_drug_trade" title="Illegal drug trade">Illegal drug trade</a> <ul><li><a href="/wiki/Illegal_drug_trade_in_Afghanistan" class="mw-redirect" title="Illegal drug trade in Afghanistan">Afghanistan</a></li> <li><a href="/wiki/Illegal_drug_trade_in_Aruba" title="Illegal drug trade in Aruba">Aruba</a></li> <li><a href="/wiki/Illegal_drug_trade_in_Australia" class="mw-redirect" title="Illegal drug trade in Australia">Australia</a></li> <li><a href="/wiki/Illegal_drug_trade_in_Bangladesh" class="mw-redirect" title="Illegal drug trade in Bangladesh">Bangladesh</a></li> <li><a href="/wiki/Illegal_drug_trade_in_Belize" class="mw-redirect" title="Illegal drug trade in Belize">Belize</a></li> <li><a href="/wiki/Illegal_drug_trade_in_Benin" class="mw-redirect" title="Illegal drug trade in Benin">Benin</a></li> <li><a href="/wiki/Illegal_drug_trade_in_Bhutan" class="mw-redirect" title="Illegal drug trade in Bhutan">Bhutan</a></li> <li><a href="/wiki/Illegal_drug_trade_in_Bolivia" class="mw-redirect" title="Illegal drug trade in Bolivia">Bolivia</a></li> <li><a href="/wiki/Illegal_drug_trade_in_Brazil" class="mw-redirect" title="Illegal drug trade in Brazil">Brazil</a></li> <li><a href="/wiki/Illegal_drug_trade_in_Burma" class="mw-redirect" title="Illegal drug trade in Burma">Burma</a></li> <li><a href="/wiki/Drugs_in_Cambodia" title="Drugs in Cambodia">Cambodia</a></li> <li><a href="/wiki/Illegal_drug_trade_in_Chile" class="mw-redirect" title="Illegal drug trade in Chile">Chile</a></li> <li><a href="/wiki/Illegal_drug_trade_in_China" title="Illegal drug trade in China">China</a></li> <li><a href="/wiki/Illegal_drug_trade_in_Colombia" title="Illegal drug trade in Colombia">Colombia</a></li> <li><a href="/wiki/Illegal_drug_trade_in_Costa_Rica" class="mw-redirect" title="Illegal drug trade in Costa Rica">Costa Rica</a></li> <li><a href="/wiki/Illegal_drug_trade_in_Cuba" class="mw-redirect" title="Illegal drug trade in Cuba">Cuba</a></li> <li><a href="/wiki/Illegal_drug_trade_in_Cyprus" class="mw-redirect" title="Illegal drug trade in Cyprus">Cyprus</a></li> <li><a href="/wiki/Illegal_drug_trade_in_the_Dominican_Republic" class="mw-redirect" title="Illegal drug trade in the Dominican Republic">Dominican Republic</a></li> <li><a href="/wiki/Illegal_drug_trade_in_El_Salvador" title="Illegal drug trade in El Salvador">El Salvador</a></li> <li><a href="/wiki/Illegal_drug_trade_in_Estonia" class="mw-redirect" title="Illegal drug trade in Estonia">Estonia</a></li> <li><a href="/wiki/Illegal_drug_trade_in_Finland" class="mw-redirect" title="Illegal drug trade in Finland">Finland</a></li> <li><a href="/wiki/Illegal_drug_trade_in_Germany" class="mw-redirect" title="Illegal drug trade in Germany">Germany</a></li> <li><a href="/wiki/Illegal_drug_trade_in_Haiti" title="Illegal drug trade in Haiti">Haiti</a></li> <li><a href="/wiki/Illegal_drug_trade_in_Honduras" class="mw-redirect" title="Illegal drug trade in Honduras">Honduras</a></li> <li><a href="/wiki/Illegal_drug_trade_in_India" class="mw-redirect" title="Illegal drug trade in India">India</a></li> <li><a href="/wiki/Illegal_drug_trade_in_the_Indian_Ocean_region" title="Illegal drug trade in the Indian Ocean region">Indian Ocean region</a></li> <li><a href="/wiki/Illegal_drug_trade_in_Iran" class="mw-redirect" title="Illegal drug trade in Iran">Iran</a></li> <li><a href="/wiki/Illegal_drug_trade_in_Italy" class="mw-redirect" title="Illegal drug trade in Italy">Italy</a></li> <li><a href="/wiki/Illegal_drug_trade_in_Japan" title="Illegal drug trade in Japan">Japan</a></li> <li><a href="/wiki/Illegal_drug_trade_in_Kenya" class="mw-redirect" title="Illegal drug trade in Kenya">Kenya</a></li> <li><a href="/wiki/Illegal_drug_trade_in_Kosovo" class="mw-redirect" title="Illegal drug trade in Kosovo">Kosovo</a></li> <li><a href="/wiki/Illegal_drug_trade_in_Kyrgyzstan" class="mw-redirect" title="Illegal drug trade in Kyrgyzstan">Kyrgyzstan</a></li> <li><a href="/wiki/Illegal_drug_trade_in_Laos" class="mw-redirect" title="Illegal drug trade in Laos">Laos</a></li> <li><a href="/wiki/Illegal_drug_trade_in_Latin_America" title="Illegal drug trade in Latin America">Latin America</a></li> <li><a href="/wiki/Illegal_drug_trade_in_Latvia" class="mw-redirect" title="Illegal drug trade in Latvia">Latvia</a></li> <li><a href="/wiki/Illegal_drug_trade_in_Malaysia" class="mw-redirect" title="Illegal drug trade in Malaysia">Malaysia</a></li> <li><a href="/wiki/Drug_trafficking_in_Mauritius" title="Drug trafficking in Mauritius">Mauritius</a></li> <li><a href="/wiki/Illegal_drug_trade_in_Moldova" class="mw-redirect" title="Illegal drug trade in Moldova">Moldova</a></li> <li><a href="/wiki/Illegal_drug_trade_in_Nigeria" class="mw-redirect" title="Illegal drug trade in Nigeria">Nigeria</a></li> <li><a href="/wiki/Illegal_drug_trade_in_Norway" class="mw-redirect" title="Illegal drug trade in Norway">Norway</a></li> <li><a href="/wiki/Illegal_drug_trade_in_Oman" class="mw-redirect" title="Illegal drug trade in Oman">Oman</a></li> <li><a href="/wiki/Illegal_drug_trade_in_Panama" title="Illegal drug trade in Panama">Panama</a></li> <li><a href="/wiki/Illegal_drug_trade_in_Papua_New_Guinea" class="mw-redirect" title="Illegal drug trade in Papua New Guinea">Papua New Guinea</a></li> <li><a href="/wiki/Illegal_drug_trade_in_Paraguay" title="Illegal drug trade in Paraguay">Paraguay</a></li> <li><a href="/wiki/Illegal_drug_trade_in_the_Philippines" title="Illegal drug trade in the Philippines">Philippines</a></li> <li><a href="/wiki/Illegal_drug_trade_in_Poland" class="mw-redirect" title="Illegal drug trade in Poland">Poland</a></li> <li><a href="/wiki/Illegal_drug_trade_in_Portugal" class="mw-redirect" title="Illegal drug trade in Portugal">Portugal</a></li> <li><a href="/wiki/Illegal_drug_trade_in_Puerto_Rico" title="Illegal drug trade in Puerto Rico">Puerto Rico</a></li> <li><a href="/wiki/Illegal_drug_trade_in_Russia" class="mw-redirect" title="Illegal drug trade in Russia">Russia</a></li> <li><a href="/wiki/Illegal_drug_trade_in_Saint_Kitts_and_Nevis" class="mw-redirect" title="Illegal drug trade in Saint Kitts and Nevis">Saint Kitts and Nevis</a></li> <li><a href="/wiki/Illegal_drug_trade_in_Seychelles" title="Illegal drug trade in Seychelles">Seychelles</a></li> <li><a href="/wiki/Illegal_drug_trade_in_Slovakia" class="mw-redirect" title="Illegal drug trade in Slovakia">Slovakia</a></li> <li><a href="/wiki/Illegal_drug_trade_in_South_Africa" class="mw-redirect" title="Illegal drug trade in South Africa">South Africa</a></li> <li><a href="/wiki/Illegal_drug_trade_in_South_Korea" class="mw-redirect" title="Illegal drug trade in South Korea">South Korea</a></li> <li><a href="/wiki/Illegal_drug_trade_in_Spain" class="mw-redirect" title="Illegal drug trade in Spain">Spain</a></li> <li><a href="/wiki/Illegal_drug_trade_in_Suriname" class="mw-redirect" title="Illegal drug trade in Suriname">Suriname</a></li> <li><a href="/wiki/Illegal_drug_trade_in_Switzerland" class="mw-redirect" title="Illegal drug trade in Switzerland">Switzerland</a></li> <li><a href="/wiki/Illegal_drug_trade_in_Taiwan" class="mw-redirect" title="Illegal drug trade in Taiwan">Taiwan</a></li> <li><a href="/wiki/Illegal_drug_trade_in_Thailand" class="mw-redirect" title="Illegal drug trade in Thailand">Thailand</a></li> <li><a href="/wiki/Illegal_drug_trade_in_Turkey" title="Illegal drug trade in Turkey">Turkey</a></li> <li><a href="/wiki/Illegal_drug_trade_in_the_Turks_and_Caicos_Islands" title="Illegal drug trade in the Turks and Caicos Islands">Turks and Caicos Islands</a></li> <li><a href="/wiki/Illegal_drug_trade_in_the_United_Arab_Emirates" class="mw-redirect" title="Illegal drug trade in the United Arab Emirates">United Arab Emirates</a></li> <li><a href="/wiki/Illegal_drug_trade_in_the_United_States" title="Illegal drug trade in the United States">United States</a></li> <li><a href="/wiki/Illegal_drug_trade_in_Venezuela" title="Illegal drug trade in Venezuela">Venezuela</a></li></ul></li> <li><a href="/wiki/Darknet_market" title="Darknet market">Darknet market</a></li> <li><a href="/wiki/Pharmaceutical_distribution" title="Pharmaceutical distribution">Pharmaceutical distribution</a> <ul><li><a href="/wiki/Beer_shop" class="mw-redirect" title="Beer shop">Beer shop</a></li> <li><a href="/wiki/Cannabis_shop" class="mw-redirect" title="Cannabis shop">Cannabis shop</a></li> <li><a href="/wiki/Liquor_store" title="Liquor store">Liquor store</a></li> <li><a href="/wiki/Liquor_license" title="Liquor license">Liquor license</a></li></ul></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Issues with drug use</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Substance_abuse" title="Substance abuse">Abuse</a></li> <li><a href="/wiki/Addiction" title="Addiction">Addiction</a></li> <li><a href="/wiki/Date_rape_drug" title="Date rape drug">Date rape drug</a></li> <li><a href="/wiki/Substance_dependence" title="Substance dependence">Dependence</a></li> <li><a href="/wiki/Driving_under_the_influence" title="Driving under the influence">Driving impaired</a></li> <li><a href="/wiki/Drug_harmfulness" class="mw-redirect" title="Drug harmfulness">Drug harmfulness</a> <ul><li><a href="/wiki/Effects_of_cannabis" title="Effects of cannabis">Effects of cannabis</a></li></ul></li> <li><a href="/wiki/Drug-related_crime" title="Drug-related crime">Drug-related crime</a></li> <li><a href="/wiki/Fetal_alcohol_spectrum_disorder" title="Fetal alcohol spectrum disorder">Fetal alcohol spectrum disorder</a></li> <li><a href="/wiki/Long-term_effects_of_cannabis" title="Long-term effects of cannabis">Long-term effects of cannabis</a></li> <li><a href="/wiki/Neurotoxicity" title="Neurotoxicity">Neurotoxicity</a></li> <li><a href="/wiki/Drug_overdose" title="Drug overdose">Overdose</a></li> <li><a href="/wiki/Passive_smoking" title="Passive smoking">Passive smoking</a> <ul><li>of tobacco or other substances</li></ul></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Harm reduction</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Drug_checking" title="Drug checking">Drug checking</a></li> <li><a href="/wiki/Drug_legalization" class="mw-redirect" title="Drug legalization">Drug legalization</a></li> <li><a href="/wiki/Drug_rehabilitation" title="Drug rehabilitation">Drug rehabilitation</a></li> <li><a href="/wiki/Needle_and_syringe_programmes" title="Needle and syringe programmes">Needle and syringe programmes</a></li> <li><a href="/wiki/Opioid_replacement_therapy" class="mw-redirect" title="Opioid replacement therapy">Opioid replacement therapy</a></li> <li><a href="/wiki/Pharmacovigilance" title="Pharmacovigilance">Pharmacovigilance</a></li> <li><a href="/wiki/Reagent_testing" title="Reagent testing">Reagent testing</a></li> <li><a href="/wiki/Regulation_of_therapeutic_goods" title="Regulation of therapeutic goods">Regulation of therapeutic goods</a></li> <li><a href="/wiki/Responsible_drug_use" title="Responsible drug use">Responsible drug use</a></li> <li><a href="/wiki/Substance_abuse_prevention" title="Substance abuse prevention">Substance abuse prevention</a></li> <li><a href="/wiki/Supervised_injection_site" title="Supervised injection site">Supervised injection site</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Countries by drug use</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/List_of_countries_by_alcohol_consumption_per_capita" title="List of countries by alcohol consumption per capita">Alcohol consumption</a></li> <li><a href="/wiki/List_of_countries_by_prevalence_of_cocaine_use" title="List of countries by prevalence of cocaine use">Cocaine use</a></li> <li>Cannabis <ul><li><a href="/wiki/Annual_cannabis_use_by_country" class="mw-redirect" title="Annual cannabis use by country">Annual use</a></li> <li><a href="/wiki/Adult_lifetime_cannabis_use_by_country" title="Adult lifetime cannabis use by country">Lifetime use</a></li></ul></li> <li><a href="/wiki/List_of_countries_by_prevalence_of_opiates_use" title="List of countries by prevalence of opiates use">Opiates use</a></li> <li><a href="/wiki/List_of_countries_by_tobacco_consumption" class="mw-redirect" title="List of countries by tobacco consumption">Tobacco consumption</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr></tbody></table><div></div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374" /><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235" /></div><div role="navigation" class="navbox" aria-labelledby="Empathogens/entactogens340" style="padding:3px"><table class="nowraplinks mw-collapsible mw-collapsed navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374" /><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231" /><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Entactogens" title="Template:Entactogens"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Entactogens" title="Template talk:Entactogens"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Entactogens" title="Special:EditPage/Template:Entactogens"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Empathogens/entactogens340" style="font-size:114%;margin:0 4em"><a href="/wiki/Empathogen-entactogen" class="mw-redirect" title="Empathogen-entactogen">Empathogens/entactogens</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Substituted_phenethylamine" title="Substituted phenethylamine">Phenylalkyl- amines</a> (other than cathinones)</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li>Unfused benzene ring: <a href="/wiki/3-Chloromethamphetamine" title="3-Chloromethamphetamine">3-CMA</a></li> <li><a href="/wiki/4-Chlorophenylisobutylamine" title="4-Chlorophenylisobutylamine">4-CAB</a></li> <li><a href="/wiki/4-Fluoroamphetamine" title="4-Fluoroamphetamine">4-FA</a></li> <li><a href="/wiki/4-methylamphetamine" class="mw-redirect" title="4-methylamphetamine">4-MA</a></li> <li><a href="/wiki/4-Methylmethamphetamine" title="4-Methylmethamphetamine">4-MMA</a></li> <li><a href="/wiki/4-Fluoromethamphetamine" title="4-Fluoromethamphetamine">4-FMA</a></li> <li><a href="/wiki/4-Methylthioamphetamine" title="4-Methylthioamphetamine">4-MTA</a></li> <li><a href="/wiki/4,4%27-Dimethylaminorex" title="4,4'-Dimethylaminorex">4,4'-DMAR</a></li> <li><a href="/wiki/Ariadne_(psychedelic)" class="mw-redirect" title="Ariadne (psychedelic)">Ariadne</a></li> <li><a href="/wiki/Metaescaline" title="Metaescaline">Metaescaline</a></li> <li><a href="/wiki/3-Methoxy-4-methylamphetamine" title="3-Methoxy-4-methylamphetamine">MMA</a></li> <li><a href="/wiki/Para-Methoxyamphetamine" title="Para-Methoxyamphetamine">PMA</a></li> <li><a href="/wiki/Para-Methoxy-N-ethylamphetamine" title="Para-Methoxy-N-ethylamphetamine">PMEA</a></li> <li><a href="/wiki/Para-Methoxy-N-methylamphetamine" class="mw-redirect" title="Para-Methoxy-N-methylamphetamine">PMMA</a></li> <li><a href="/wiki/3-Methoxy-N-methylamphetamine" class="mw-redirect" title="3-Methoxy-N-methylamphetamine">mMMA</a> Benzodioxine: <a href="/wiki/EDMA" title="EDMA">EDMA</a> Benzodioxoles: Phenethylamine: { <a href="/wiki/Lophophine" title="Lophophine">Lophophine</a> }</li> <li>Amphetamines: { <a href="/wiki/2-Methyl-MDA" title="2-Methyl-MDA">2-Methyl-MDA</a></li> <li><a href="/wiki/2,3-Methylenedioxyamphetamine" title="2,3-Methylenedioxyamphetamine">2,3-MDA</a></li> <li><a href="/wiki/3,4-Methylenedioxyamphetamine" title="3,4-Methylenedioxyamphetamine">3,4-MDA (tenamfetamine)</a></li> <li><a href="/wiki/5-Methyl-MDA" title="5-Methyl-MDA">5-Methyl-MDA</a></li> <li><a href="/wiki/6-Methyl-MDA" title="6-Methyl-MDA">6-Methyl-MDA</a></li> <li><a href="/wiki/DFMDA" title="DFMDA">DFMDA</a></li> <li><a href="/wiki/DMMDA" title="DMMDA">DMMDA</a></li> <li><a href="/wiki/DMMDA-2" title="DMMDA-2">DMMDA-2</a></li> <li><a href="/wiki/3,4-Ethylidenedioxyamphetamine" title="3,4-Ethylidenedioxyamphetamine">EIDA</a></li> <li><a href="/wiki/Lys-MDA" title="Lys-MDA">Lys-MDA</a></li> <li><a href="/wiki/3,4-Methylenedioxy-N-ethylamphetamine" title="3,4-Methylenedioxy-N-ethylamphetamine">MDEA</a></li> <li><a class="mw-selflink selflink">MDMA (midomafetamine)</a> <ul><li><a href="/wiki/(R)-MDMA" title="(R)-MDMA">(R)-MDMA</a></li></ul></li> <li><a href="/wiki/3,4-Methylenedioxy-N-hydroxy-N-methylamphetamine" title="3,4-Methylenedioxy-N-hydroxy-N-methylamphetamine">MDMOH</a></li> <li><a href="/wiki/3,4-Methylenedioxy-N-hydroxyamphetamine" title="3,4-Methylenedioxy-N-hydroxyamphetamine">MDOH</a></li> <li><a href="/wiki/MMDA_(drug)" title="MMDA (drug)">MMDA</a></li> <li><a href="/wiki/MMDA-2" title="MMDA-2">MMDA-2</a></li> <li><a href="/wiki/MMDMA" title="MMDMA">MMDMA</a></li> <li><a href="/wiki/N-t-BOC-MDMA" title="N-t-BOC-MDMA">N-t-BOC-MDMA</a> }</li> <li>1-Phenylbutan-2-amines: { <a href="/wiki/1,3-Benzodioxolylbutanamine" title="1,3-Benzodioxolylbutanamine">BDB</a></li> <li><a href="/wiki/1,3-Benzodioxolyl-N-ethylbutanamine" title="1,3-Benzodioxolyl-N-ethylbutanamine">EBDB</a></li> <li><a href="/wiki/MBDB" title="MBDB">MBDB</a> }</li> <li>Phentermines: { <a href="/wiki/3,4-Methylenedioxy-N-methylphentermine" title="3,4-Methylenedioxy-N-methylphentermine">MDMP</a></li> <li><a href="/wiki/3,4-Methylenedioxyphentermine" title="3,4-Methylenedioxyphentermine">MDPH</a> } Benzofurans, dihydrobenzofurans and benzothiophenes: <a href="/wiki/2-MAPB" title="2-MAPB">2-MAPB</a></li> <li><a href="/wiki/5-APB" title="5-APB">5-APB</a></li> <li><a href="/wiki/5-APDB" title="5-APDB">5-APDB</a></li> <li><a href="/wiki/5-EAPB" title="5-EAPB">5-EAPB</a></li> <li><a href="/wiki/5-MAPB" title="5-MAPB">5-MAPB</a></li> <li><a href="/wiki/5-MAPDB" title="5-MAPDB">5-MAPDB</a></li> <li><a href="/wiki/5-MAPBT" title="5-MAPBT">5-MAPBT</a></li> <li><a href="/wiki/5-MBPB" title="5-MBPB">5-MBPB (5-MABB)</a></li> <li><a href="/wiki/6-APB" title="6-APB">6-APB</a></li> <li><a href="/wiki/6-APDB" title="6-APDB">6-APDB</a></li> <li><a href="/wiki/6-EAPB" title="6-EAPB">6-EAPB</a></li> <li><a href="/wiki/6-MAPB" title="6-MAPB">6-MAPB</a></li> <li><a href="/wiki/6-MAPDB" title="6-MAPDB">6-MAPDB</a></li> <li><a href="/wiki/6-MBPB" title="6-MBPB">6-MBPB (6-MABB)</a></li> <li><a href="/wiki/IBF5MAP" title="IBF5MAP">IBF5MAP</a> Indanes: <a href="/wiki/5-APDI" title="5-APDI">5-APDI</a></li> <li><a href="/wiki/5-MAPDI" title="5-MAPDI">5-MAPDI</a> Indoles: <a href="/wiki/5-IT" class="mw-redirect" title="5-IT">5-IT</a></li> <li><a href="/wiki/6-(2-Aminopropyl)indole" title="6-(2-Aminopropyl)indole">6-API</a> Naphthalenes: <a href="/wiki/Methamnetamine" title="Methamnetamine">Methamnetamine</a></li> <li><a href="/wiki/Naphthylaminopropane" title="Naphthylaminopropane">Naphthylaminopropane</a> Tetralin: <a href="/wiki/6-APT" title="6-APT">6-APT</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Cyclic_compound" title="Cyclic compound">Cyclized</a> <a href="/wiki/Substituted_phenethylamine" title="Substituted phenethylamine">phenyl- alkylamines</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li>Aminoindanes: <a href="/wiki/5-IAI" title="5-IAI">5-IAI</a></li> <li><a href="/wiki/1-Aminomethyl-5-methoxyindane" title="1-Aminomethyl-5-methoxyindane">AMMI</a></li> <li><a href="/wiki/BFAI" title="BFAI">BFAI</a></li> <li><a href="/wiki/Ethyltrifluoromethylaminoindane" title="Ethyltrifluoromethylaminoindane">ETAI</a></li> <li><a href="/wiki/MDAI" title="MDAI">MDAI</a></li> <li><a href="/wiki/MDMAI" title="MDMAI">MDMAI</a></li> <li><a href="/wiki/MMAI" title="MMAI">MMAI</a></li> <li><a href="/wiki/MEAI" title="MEAI">MEAI</a></li> <li><a href="/wiki/NM-2-AI" title="NM-2-AI">NM-2-AI</a></li> <li><a href="/wiki/Trifluoromethylaminoindane" title="Trifluoromethylaminoindane">TAI</a> Aminotetralins: <a href="/wiki/6-CAT" title="6-CAT">6-CAT</a></li> <li><a href="/wiki/MDAT" title="MDAT">MDAT</a></li> <li><a href="/wiki/MDMAT" title="MDMAT">MDMAT</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Substituted_cathinone" title="Substituted cathinone">Cathinones</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/3-Chloromethcathinone" title="3-Chloromethcathinone">3-CMC</a></li> <li><a href="/wiki/3-Methylmethcathinone" title="3-Methylmethcathinone">3-MMC</a></li> <li><a href="/wiki/4-Ethylmethcathinone" title="4-Ethylmethcathinone">4-EMC</a></li> <li><a href="/wiki/BK-5-MAPB" title="BK-5-MAPB">BK-5-MAPB</a></li> <li><a href="/wiki/4-Bromomethcathinone" title="4-Bromomethcathinone">Brephedrone</a></li> <li><a href="/wiki/Butylone" title="Butylone">Butylone</a></li> <li><a href="/wiki/Dimethylone" title="Dimethylone">Dimethylone</a></li> <li><a href="/wiki/Ethylone" title="Ethylone">Ethylone</a></li> <li><a href="/wiki/Eutylone" title="Eutylone">Eutylone</a></li> <li><a href="/wiki/Flephedrone" title="Flephedrone">Flephedrone</a></li> <li><a href="/wiki/Mephedrone" title="Mephedrone">Mephedrone</a></li> <li><a href="/wiki/Methedrone" title="Methedrone">Methedrone</a></li> <li><a href="/wiki/Methylone" title="Methylone">Methylone</a></li> <li><a href="/wiki/TH-PVP" title="TH-PVP">TH-PVP</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Substituted_tryptamine" title="Substituted tryptamine">Tryptamines</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/4-Methyl-%CE%B1-ethyltryptamine" title="4-Methyl-α-ethyltryptamine">4-Methyl-αET</a></li> <li><a href="/wiki/Alpha-Ethyltryptamine" class="mw-redirect" title="Alpha-Ethyltryptamine">αET</a></li> <li><a href="/wiki/Alpha-Methyltryptamine" class="mw-redirect" title="Alpha-Methyltryptamine">αMT</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Chemical_classification" class="mw-redirect" title="Chemical classification">Chemical classes</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Substituted_amphetamine" title="Substituted amphetamine">Substituted amphetamine</a></li> <li><a href="/wiki/Substituted_benzofuran" title="Substituted benzofuran">Sub. benzofuran</a></li> <li><a href="/wiki/Substituted_cathinone" title="Substituted cathinone">Sub. cathinone</a></li> <li><a href="/wiki/Substituted_methylenedioxyphenethylamine" title="Substituted methylenedioxyphenethylamine">Sub. MDPEA</a></li> <li><a href="/wiki/Substituted_phenethylamine" title="Substituted phenethylamine">Sub. PEA</a></li> <li><a href="/wiki/Substituted_tryptamine" title="Substituted tryptamine">Sub. tryptamine</a></li></ul> </div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374" /><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235" /></div><div role="navigation" class="navbox" aria-labelledby="Drugs_which_induce_euphoria105" style="padding:3px"><table class="nowraplinks hlist mw-collapsible autocollapse navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374" /><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231" /><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Euphoriants" title="Template:Euphoriants"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Euphoriants" title="Template talk:Euphoriants"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Euphoriants" title="Special:EditPage/Template:Euphoriants"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Drugs_which_induce_euphoria105" style="font-size:114%;margin:0 4em">Drugs which induce <a href="/wiki/Euphoriant" class="mw-redirect" title="Euphoriant">euphoria</a></div></th></tr><tr><td colspan="2" class="navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/%CE%9C-Opioid_receptor" class="mw-redirect" title="Μ-Opioid receptor">μ-Opioid receptor</a> <a href="/wiki/Agonist" title="Agonist">agonists</a> (<a href="/wiki/Opioid" title="Opioid">opioids</a>) (e.g., <a href="/wiki/Morphine" title="Morphine">morphine</a>, <a href="/wiki/Heroin" title="Heroin">heroin</a>, <a href="/wiki/Hydrocodone" title="Hydrocodone">hydrocodone</a>, <a href="/wiki/Oxycodone" title="Oxycodone">oxycodone</a>, <a href="/wiki/Opium" title="Opium">opium</a>, <a href="/wiki/Kratom" class="mw-redirect" title="Kratom">kratom</a>)</li> <li><a href="/wiki/Voltage-dependent_calcium_channel#.CE.B12.CE.B4_Subunit" class="mw-redirect" title="Voltage-dependent calcium channel">α2δ subunit</a>-containing <a href="/wiki/Voltage-dependent_calcium_channel" class="mw-redirect" title="Voltage-dependent calcium channel">voltage-dependent calcium channels</a> <a href="/wiki/Calcium_channel_blocker" title="Calcium channel blocker">blockers</a> (<a href="/wiki/Gabapentinoid" title="Gabapentinoid">gabapentinoids</a>) (e.g., <a href="/wiki/Gabapentin" title="Gabapentin">gabapentin</a>, <a href="/wiki/Pregabalin" title="Pregabalin">pregabalin</a>, <a href="/wiki/Phenibut" title="Phenibut">phenibut</a>)</li> <li><a href="/wiki/AMPA_receptor" title="AMPA receptor">AMPA receptor</a> <a href="/wiki/Receptor_antagonist" title="Receptor antagonist">antagonists</a> (e.g., <a href="/wiki/Perampanel" title="Perampanel">perampanel</a>)</li> <li><a href="/wiki/CB1_receptor" class="mw-redirect" title="CB1 receptor">CB1 receptor</a> <a href="/wiki/Agonist" title="Agonist">agonists</a> (<a href="/wiki/Cannabinoid" title="Cannabinoid">cannabinoids</a>) (e.g., <a href="/wiki/Tetrahydrocannabinol" title="Tetrahydrocannabinol">THC</a>, <a href="/wiki/Cannabis_(drug)" title="Cannabis (drug)">cannabis</a>)</li> <li><a href="/wiki/Dopamine_agonist" title="Dopamine agonist">Dopamine receptor agonists</a> (e.g., <a href="/wiki/Levodopa" title="Levodopa">levodopa</a>)</li> <li><a href="/wiki/Dopamine_releasing_agent" title="Dopamine releasing agent">Dopamine releasing agents</a> (e.g., <a href="/wiki/Amphetamine" title="Amphetamine">amphetamine</a>, <a href="/wiki/Methamphetamine" title="Methamphetamine">methamphetamine</a>, <a class="mw-selflink selflink">MDMA</a>, <a href="/wiki/Mephedrone" title="Mephedrone">mephedrone</a>)</li> <li><a href="/wiki/Dopamine_reuptake_inhibitor" title="Dopamine reuptake inhibitor">Dopamine reuptake inhibitors</a> (e.g., <a href="/wiki/Cocaine" title="Cocaine">cocaine</a>, <a href="/wiki/Methylphenidate" title="Methylphenidate">methylphenidate</a>)</li> <li><a href="/wiki/GABAA_receptor" title="GABAA receptor">GABAA receptor</a> <a href="/wiki/Positive_allosteric_modulator" class="mw-redirect" title="Positive allosteric modulator">positive allosteric modulators</a> (e.g., <a href="/wiki/Barbiturate" title="Barbiturate">barbiturates</a>, <a href="/wiki/Benzodiazepine" title="Benzodiazepine">benzodiazepines</a>, <a href="/wiki/Carbamate" title="Carbamate">carbamates</a>, <a href="/wiki/Alcohol_(drug)" title="Alcohol (drug)">ethanol (alcohol)</a> (<a href="/wiki/Alcoholic_drink" class="mw-redirect" title="Alcoholic drink">alcoholic drink</a>), <a href="/wiki/Inhalant" title="Inhalant">inhalants</a>, <a href="/wiki/Nonbenzodiazepine" title="Nonbenzodiazepine">nonbenzodiazepines</a>, <a href="/wiki/Quinazolinone" title="Quinazolinone">quinazolinones</a>)</li> <li><a href="/wiki/Gamma-Hydroxybutyric_acid" class="mw-redirect" title="Gamma-Hydroxybutyric acid">GHB</a> (<a href="/wiki/Sodium_oxybate" title="Sodium oxybate">sodium oxybate</a>) and <a href="/wiki/Structural_analog" title="Structural analog">analogues</a></li> <li><a href="/wiki/Glucocorticoid" title="Glucocorticoid">Glucocorticoids (corticosteroids)</a> (e.g., <a href="/wiki/Dexamethasone" title="Dexamethasone">dexamethasone</a>, <a href="/wiki/Prednisone" title="Prednisone">prednisone</a>)</li> <li><a href="/wiki/Nicotinic_agonist" title="Nicotinic agonist">nACh receptor agonists</a> (e.g., <a href="/wiki/Nicotine" title="Nicotine">nicotine</a>, <a href="/wiki/Tobacco" title="Tobacco">tobacco</a>, <a href="/wiki/Arecoline" title="Arecoline">arecoline</a>, <a href="/wiki/Areca_nut" title="Areca nut">areca nut</a>)</li> <li><a href="/wiki/Nitric_oxide_donor" class="mw-redirect" title="Nitric oxide donor">Nitric oxide prodrugs</a> (e.g., <a href="/wiki/Alkyl_nitrite" title="Alkyl nitrite">alkyl nitrites</a> (<a href="/wiki/Poppers" title="Poppers">poppers</a>))</li> <li><a href="/wiki/NMDA_receptor_antagonist" title="NMDA receptor antagonist">NMDA receptor antagonists</a> (e.g., <a href="/wiki/Dextromethorphan" title="Dextromethorphan">DXM</a>, <a href="/wiki/Ketamine" title="Ketamine">ketamine</a>, <a href="/wiki/Methoxetamine" title="Methoxetamine">methoxetamine</a>, <a href="/wiki/Nitrous_oxide" title="Nitrous oxide">nitrous oxide</a>, <a href="/wiki/Phencyclidine" title="Phencyclidine">phencyclidine</a>, <a href="/wiki/Inhalant" title="Inhalant">inhalants</a>)</li> <li><a href="/wiki/Orexin_antagonist" title="Orexin antagonist">Orexin receptor antagonists</a> (e.g., <a href="/wiki/Suvorexant" title="Suvorexant">suvorexant</a>)</li></ul> </div></td></tr><tr><td class="navbox-abovebelow" colspan="2"><div>See also: <a href="/wiki/Template:Drug_use" title="Template:Drug use">Recreational drug use</a></div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374" /><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235" /></div><div role="navigation" class="navbox" aria-labelledby="Hallucinogens356" style="padding:3px"><table class="nowraplinks mw-collapsible mw-collapsed navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374" /><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231" /><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Hallucinogens" title="Template:Hallucinogens"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Hallucinogens" title="Template talk:Hallucinogens"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Hallucinogens" title="Special:EditPage/Template:Hallucinogens"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Hallucinogens356" style="font-size:114%;margin:0 4em"><a href="/wiki/Hallucinogen" title="Hallucinogen">Hallucinogens</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Psychedelic_drug" title="Psychedelic drug">Psychedelics</a> (<a href="/wiki/5-HT2A_receptor" title="5-HT2A receptor">5-HT2A</a> agonists)</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Substituted_benzofuran" title="Substituted benzofuran">Benzofurans</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/2C-B-FLY" title="2C-B-FLY">2C-B-FLY</a></li> <li><a href="/wiki/2CBFly-NBOMe" title="2CBFly-NBOMe">2CBFly-NBOMe</a></li> <li><a href="/wiki/5-MeO-BFE" class="mw-redirect" title="5-MeO-BFE">5-MeO-BFE</a></li> <li><a href="/wiki/5-MeO-DiBF" title="5-MeO-DiBF">5-MeO-DiBF</a></li> <li><a href="/wiki/Bromo-DragonFLY" title="Bromo-DragonFLY">Bromo-DragonFLY</a></li> <li><a href="/wiki/F-2_(drug)" title="F-2 (drug)">F-2</a></li> <li><a href="/wiki/F-22_(psychedelic)" title="F-22 (psychedelic)">F-22</a></li> <li><a href="/wiki/TFMFly" title="TFMFly">TFMFly</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Lysergamides" title="Lysergamides">Lyserg‐ amides</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/1B-LSD" title="1B-LSD">1B-LSD</a></li> <li><a href="/wiki/1cP-LSD" title="1cP-LSD">1cP-LSD</a></li> <li><a href="/wiki/1P-ETH-LAD" title="1P-ETH-LAD">1P-ETH-LAD</a></li> <li><a href="/wiki/1P-LSD" title="1P-LSD">1P-LSD</a></li> <li><a href="/wiki/1cP-AL-LAD" title="1cP-AL-LAD">1cP-AL-LAD</a></li> <li><a href="/w/index.php?title=1cP-MiPLA&action=edit&redlink=1" class="new" title="1cP-MiPLA (page does not exist)">1cP-MiPLA</a></li> <li><a href="/wiki/1V-LSD" title="1V-LSD">1V-LSD</a></li> <li><a href="/wiki/Lysergic_acid_2-butyl_amide" title="Lysergic acid 2-butyl amide">2-Butyllysergamide</a></li> <li><a href="/wiki/Lysergic_acid_3-pentyl_amide" title="Lysergic acid 3-pentyl amide">3-Pentyllysergamide</a></li> <li><a href="/wiki/AL-LAD" title="AL-LAD">AL-LAD</a></li> <li><a href="/wiki/ALD-52" title="ALD-52">ALD-52</a></li> <li><a href="/wiki/BU-LAD" title="BU-LAD">BU-LAD</a></li> <li><a href="/wiki/Diallyllysergamide" title="Diallyllysergamide">Diallyllysergamide</a></li> <li><a href="/wiki/Dimethyllysergamide" title="Dimethyllysergamide">Dimethyllysergamide</a></li> <li><a href="/wiki/ECPLA" title="ECPLA">ECPLA</a></li> <li><a href="/wiki/Ergometrine" class="mw-redirect" title="Ergometrine">Ergometrine</a></li> <li><a href="/wiki/ETH-LAD" title="ETH-LAD">ETH-LAD</a></li> <li><a href="/wiki/IP-LAD" class="mw-redirect" title="IP-LAD">IP-LAD</a></li> <li><a href="/wiki/LAE-32" title="LAE-32">LAE-32</a></li> <li><a href="/wiki/LAMPA" title="LAMPA">LAMPA</a></li> <li><a href="/wiki/LPD-824" title="LPD-824">LPD-824</a></li> <li><a href="/wiki/Ergine" title="Ergine">LSA</a></li> <li><a href="/wiki/LSD" title="LSD">LSD</a></li> <li><a href="/wiki/LSD-Pip" title="LSD-Pip">LSD-Pip</a></li> <li><a href="/wiki/Lysergic_acid_hydroxyethylamide" title="Lysergic acid hydroxyethylamide">LSH</a></li> <li><a href="/wiki/LSM-775" title="LSM-775">LSM-775</a></li> <li><a href="/wiki/Lysergic_acid_2,4-dimethylazetidide" title="Lysergic acid 2,4-dimethylazetidide">LSZ</a></li> <li><a href="/wiki/Methylergometrine" title="Methylergometrine">Methylergometrine</a></li> <li><a href="/wiki/Methylisopropyllysergamide" title="Methylisopropyllysergamide">MIPLA</a></li> <li><a href="/wiki/Methysergide" title="Methysergide">Methysergide</a></li> <li><a href="/wiki/N1-Methyl-lysergic_acid_diethylamide" title="N1-Methyl-lysergic acid diethylamide">MLD-41</a></li> <li><a href="/wiki/PARGY-LAD" title="PARGY-LAD">PARGY-LAD</a></li> <li><a href="/wiki/PRO-LAD" title="PRO-LAD">PRO-LAD</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Substituted_phenethylamine" title="Substituted phenethylamine">Phenethyl‐ amines</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th id="2C-x182" scope="row" class="navbox-group" style="width:1%"><a href="/wiki/2C_(psychedelics)" title="2C (psychedelics)">2C-x</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/2C-B" title="2C-B">2C-B</a></li> <li><a href="/w/index.php?title=2C-B-AN&action=edit&redlink=1" class="new" title="2C-B-AN (page does not exist)">2C-B-AN</a></li> <li><a href="/w/index.php?title=2C-Bn&action=edit&redlink=1" class="new" title="2C-Bn (page does not exist)">2C-Bn</a></li> <li><a href="/w/index.php?title=2C-Bu&action=edit&redlink=1" class="new" title="2C-Bu (page does not exist)">2C-Bu</a></li> <li><a href="/wiki/2C-C" title="2C-C">2C-C</a></li> <li><a href="/w/index.php?title=2C-CN&action=edit&redlink=1" class="new" title="2C-CN (page does not exist)">2C-CN</a></li> <li><a href="/wiki/2C-CP" title="2C-CP">2C-CP</a></li> <li><a href="/wiki/2C-D" title="2C-D">2C-D</a></li> <li><a href="/wiki/2C-E" title="2C-E">2C-E</a></li> <li><a href="/wiki/2C-EF" title="2C-EF">2C-EF</a></li> <li><a href="/wiki/2C-F" title="2C-F">2C-F</a></li> <li><a href="/wiki/2C-G" title="2C-G">2C-G</a></li> <li><a href="/wiki/2C-G-1" class="mw-redirect" title="2C-G-1">2C-G-1</a></li> <li><a href="/wiki/2C-G-2" class="mw-redirect" title="2C-G-2">2C-G-2</a></li> <li><a href="/wiki/2C-G-3" class="mw-redirect" title="2C-G-3">2C-G-3</a></li> <li><a href="/wiki/2C-G-4" class="mw-redirect" title="2C-G-4">2C-G-4</a></li> <li><a href="/wiki/2C-G-5" class="mw-redirect" title="2C-G-5">2C-G-5</a></li> <li><a href="/wiki/2C-G-6" class="mw-redirect" title="2C-G-6">2C-G-6</a></li> <li><a href="/wiki/2C-G-N" class="mw-redirect" title="2C-G-N">2C-G-N</a></li> <li><a href="/wiki/2C-H" title="2C-H">2C-H</a></li> <li><a href="/wiki/2C-I" title="2C-I">2C-I</a></li> <li><a href="/wiki/2C-iP" title="2C-iP">2C-iP</a></li> <li><a href="/wiki/2C-N" title="2C-N">2C-N</a></li> <li><a href="/w/index.php?title=2C-NH2&action=edit&redlink=1" class="new" title="2C-NH2 (page does not exist)">2C-NH2</a></li> <li><a href="/wiki/2C-O" class="mw-redirect" title="2C-O">2C-O</a></li> <li><a href="/wiki/2C-O-4" title="2C-O-4">2C-O-4</a></li> <li><a href="/wiki/2C-P" title="2C-P">2C-P</a></li> <li><a href="/w/index.php?title=2C-Ph&action=edit&redlink=1" class="new" title="2C-Ph (page does not exist)">2C-Ph</a></li> <li><a href="/wiki/2C-SE" class="mw-redirect" title="2C-SE">2C-SE</a></li> <li><a href="/wiki/2C-T" title="2C-T">2C-T</a></li> <li><a href="/wiki/2C-T-2" title="2C-T-2">2C-T-2</a></li> <li><a href="/wiki/2C-T-3" title="2C-T-3">2C-T-3</a></li> <li><a href="/wiki/2C-T-4" title="2C-T-4">2C-T-4</a></li> <li><a href="/w/index.php?title=2C-T-5&action=edit&redlink=1" class="new" title="2C-T-5 (page does not exist)">2C-T-5</a></li> <li><a href="/w/index.php?title=2C-T-6&action=edit&redlink=1" class="new" title="2C-T-6 (page does not exist)">2C-T-6</a></li> <li><a href="/wiki/2C-T-7" title="2C-T-7">2C-T-7</a></li> <li><a href="/wiki/2C-T-8" title="2C-T-8">2C-T-8</a></li> <li><a href="/wiki/2C-T-9" class="mw-redirect" title="2C-T-9">2C-T-9</a></li> <li><a href="/w/index.php?title=2C-T-10&action=edit&redlink=1" class="new" title="2C-T-10 (page does not exist)">2C-T-10</a></li> <li><a href="/w/index.php?title=2C-T-11&action=edit&redlink=1" class="new" title="2C-T-11 (page does not exist)">2C-T-11</a></li> <li><a href="/w/index.php?title=2C-T-12&action=edit&redlink=1" class="new" title="2C-T-12 (page does not exist)">2C-T-12</a></li> <li><a href="/wiki/2C-T-13" title="2C-T-13">2C-T-13</a></li> <li><a href="/w/index.php?title=2C-T-14&action=edit&redlink=1" class="new" title="2C-T-14 (page does not exist)">2C-T-14</a></li> <li><a href="/wiki/2C-T-15" title="2C-T-15">2C-T-15</a></li> <li><a href="/wiki/2C-T-16" title="2C-T-16">2C-T-16</a></li> <li><a href="/wiki/2C-T-17" title="2C-T-17">2C-T-17</a></li> <li><a href="/w/index.php?title=2C-T-18&action=edit&redlink=1" class="new" title="2C-T-18 (page does not exist)">2C-T-18</a></li> <li><a href="/wiki/2C-T-19" title="2C-T-19">2C-T-19</a></li> <li><a href="/w/index.php?title=2C-T-20&action=edit&redlink=1" class="new" title="2C-T-20 (page does not exist)">2C-T-20</a></li> <li><a href="/wiki/2C-T-21" title="2C-T-21">2C-T-21</a></li> <li><a href="/w/index.php?title=2C-T-22&action=edit&redlink=1" class="new" title="2C-T-22 (page does not exist)">2C-T-22</a></li> <li><a href="/w/index.php?title=2C-T-22.5&action=edit&redlink=1" class="new" title="2C-T-22.5 (page does not exist)">2C-T-22.5</a></li> <li><a href="/w/index.php?title=2C-T-23&action=edit&redlink=1" class="new" title="2C-T-23 (page does not exist)">2C-T-23</a></li> <li><a href="/w/index.php?title=2C-T-24&action=edit&redlink=1" class="new" title="2C-T-24 (page does not exist)">2C-T-24</a></li> <li><a href="/w/index.php?title=2C-T-25&action=edit&redlink=1" class="new" title="2C-T-25 (page does not exist)">2C-T-25</a></li> <li><a href="/wiki/2C-T-27" title="2C-T-27">2C-T-27</a></li> <li><a href="/wiki/2C-T-28" title="2C-T-28">2C-T-28</a></li> <li><a href="/w/index.php?title=2C-T-30&action=edit&redlink=1" class="new" title="2C-T-30 (page does not exist)">2C-T-30</a></li> <li><a href="/w/index.php?title=2C-T-31&action=edit&redlink=1" class="new" title="2C-T-31 (page does not exist)">2C-T-31</a></li> <li><a href="/w/index.php?title=2C-T-32&action=edit&redlink=1" class="new" title="2C-T-32 (page does not exist)">2C-T-32</a></li> <li><a href="/wiki/2C-T-33" title="2C-T-33">2C-T-33</a></li> <li><a href="/wiki/2C-TFE" title="2C-TFE">2C-TFE</a></li> <li><a href="/wiki/2C-TFM" title="2C-TFM">2C-TFM</a></li> <li><a href="/wiki/2C-YN" title="2C-YN">2C-YN</a></li> <li><a href="/wiki/2C-V" title="2C-V">2C-V</a></li></ul> </div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/25-NB" title="25-NB">25x-NBx</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%">25x-<abbr title="NB: N-benzyl">NB</abbr></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/25B-NB" class="mw-redirect" title="25B-NB">25B-NB</a></li> <li><a href="/w/index.php?title=25C-NB&action=edit&redlink=1" class="new" title="25C-NB (page does not exist)">25C-NB</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">25x-<abbr title="NB: N-benzyl; 3OMe: 3-methoxy">NB3OMe</abbr></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/w/index.php?title=25B-NB3OMe&action=edit&redlink=1" class="new" title="25B-NB3OMe (page does not exist)">25B-NB3OMe</a></li> <li><a href="/wiki/25C-NB3OMe" title="25C-NB3OMe">25C-NB3OMe</a></li> <li><a href="/w/index.php?title=25D-NB3OMe&action=edit&redlink=1" class="new" title="25D-NB3OMe (page does not exist)">25D-NB3OMe</a></li> <li><a href="/w/index.php?title=25E-NB3OMe&action=edit&redlink=1" class="new" title="25E-NB3OMe (page does not exist)">25E-NB3OMe</a></li> <li><a href="/w/index.php?title=25H-NB3OMe&action=edit&redlink=1" class="new" title="25H-NB3OMe (page does not exist)">25H-NB3OMe</a></li> <li><a href="/wiki/25I-NB3OMe" title="25I-NB3OMe">25I-NB3OMe</a></li> <li><a href="/w/index.php?title=25N-NB3OMe&action=edit&redlink=1" class="new" title="25N-NB3OMe (page does not exist)">25N-NB3OMe</a></li> <li><a href="/w/index.php?title=25P-NB3OMe&action=edit&redlink=1" class="new" title="25P-NB3OMe (page does not exist)">25P-NB3OMe</a></li> <li><a href="/w/index.php?title=25T2-NB3OMe&action=edit&redlink=1" class="new" title="25T2-NB3OMe (page does not exist)">25T2-NB3OMe</a></li> <li><a href="/w/index.php?title=25T4-NB3OMe&action=edit&redlink=1" class="new" title="25T4-NB3OMe (page does not exist)">25T4-NB3OMe</a></li> <li><a href="/w/index.php?title=25T7-NB3OMe&action=edit&redlink=1" class="new" title="25T7-NB3OMe (page does not exist)">25T7-NB3OMe</a></li> <li><a href="/w/index.php?title=25TFM-NB3OMe&action=edit&redlink=1" class="new" title="25TFM-NB3OMe (page does not exist)">25TFM-NB3OMe</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">25x-<abbr title="NB: N-benzyl; 4OMe: 4-methoxy">NB4OMe</abbr></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/w/index.php?title=25B-NB4OMe&action=edit&redlink=1" class="new" title="25B-NB4OMe (page does not exist)">25B-NB4OMe</a></li> <li><a href="/wiki/25C-NB4OMe" title="25C-NB4OMe">25C-NB4OMe</a></li> <li><a href="/w/index.php?title=25D-NB4OMe&action=edit&redlink=1" class="new" title="25D-NB4OMe (page does not exist)">25D-NB4OMe</a></li> <li><a href="/w/index.php?title=25E-NB4OMe&action=edit&redlink=1" class="new" title="25E-NB4OMe (page does not exist)">25E-NB4OMe</a></li> <li><a href="/w/index.php?title=25H-NB4OMe&action=edit&redlink=1" class="new" title="25H-NB4OMe (page does not exist)">25H-NB4OMe</a></li> <li><a href="/wiki/25I-NB4OMe" title="25I-NB4OMe">25I-NB4OMe</a></li> <li><a href="/w/index.php?title=25N-NB4OMe&action=edit&redlink=1" class="new" title="25N-NB4OMe (page does not exist)">25N-NB4OMe</a></li> <li><a href="/w/index.php?title=25P-NB4OMe&action=edit&redlink=1" class="new" title="25P-NB4OMe (page does not exist)">25P-NB4OMe</a></li> <li><a href="/w/index.php?title=25T2-NB4OMe&action=edit&redlink=1" class="new" title="25T2-NB4OMe (page does not exist)">25T2-NB4OMe</a></li> <li><a href="/w/index.php?title=25T4-NB4OMe&action=edit&redlink=1" class="new" title="25T4-NB4OMe (page does not exist)">25T4-NB4OMe</a></li> <li><a href="/w/index.php?title=25T7-NB4OMe&action=edit&redlink=1" class="new" title="25T7-NB4OMe (page does not exist)">25T7-NB4OMe</a></li> <li><a href="/w/index.php?title=25TFM-NB4OMe&action=edit&redlink=1" class="new" title="25TFM-NB4OMe (page does not exist)">25TFM-NB4OMe</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">25x-<abbr title="NB: N-benzyl; F: fluoro">NBF</abbr></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/25B-NBF" title="25B-NBF">25B-NBF</a></li> <li><a href="/wiki/25C-NBF" title="25C-NBF">25C-NBF</a></li> <li><a href="/w/index.php?title=25D-NBF&action=edit&redlink=1" class="new" title="25D-NBF (page does not exist)">25D-NBF</a></li> <li><a href="/w/index.php?title=25E-NBF&action=edit&redlink=1" class="new" title="25E-NBF (page does not exist)">25E-NBF</a></li> <li><a href="/w/index.php?title=25H-NBF&action=edit&redlink=1" class="new" title="25H-NBF (page does not exist)">25H-NBF</a></li> <li><a href="/wiki/25I-NBF" title="25I-NBF">25I-NBF</a></li> <li><a href="/w/index.php?title=25P-NBF&action=edit&redlink=1" class="new" title="25P-NBF (page does not exist)">25P-NBF</a></li> <li><a href="/w/index.php?title=25T2-NBF&action=edit&redlink=1" class="new" title="25T2-NBF (page does not exist)">25T2-NBF</a></li> <li><a href="/w/index.php?title=25T7-NBF&action=edit&redlink=1" class="new" title="25T7-NBF (page does not exist)">25T7-NBF</a></li> <li><a href="/w/index.php?title=25TFM-NBF&action=edit&redlink=1" class="new" title="25TFM-NBF (page does not exist)">25TFM-NBF</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">25x-<abbr title="NB: N-benzyl; MD: methylenedioxy">NBMD</abbr></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/w/index.php?title=25B-NBMD&action=edit&redlink=1" class="new" title="25B-NBMD (page does not exist)">25B-NBMD</a></li> <li><a href="/w/index.php?title=25C-NBMD&action=edit&redlink=1" class="new" title="25C-NBMD (page does not exist)">25C-NBMD</a></li> <li><a href="/w/index.php?title=25D-NBMD&action=edit&redlink=1" class="new" title="25D-NBMD (page does not exist)">25D-NBMD</a></li> <li><a href="/w/index.php?title=25E-NBMD&action=edit&redlink=1" class="new" title="25E-NBMD (page does not exist)">25E-NBMD</a></li> <li><a href="/w/index.php?title=25F-NBMD&action=edit&redlink=1" class="new" title="25F-NBMD (page does not exist)">25F-NBMD</a></li> <li><a href="/w/index.php?title=25H-NBMD&action=edit&redlink=1" class="new" title="25H-NBMD (page does not exist)">25H-NBMD</a></li> <li><a href="/wiki/25I-NBMD" title="25I-NBMD">25I-NBMD</a></li> <li><a href="/w/index.php?title=25P-NBMD&action=edit&redlink=1" class="new" title="25P-NBMD (page does not exist)">25P-NBMD</a></li> <li><a href="/w/index.php?title=25T2-NBMD&action=edit&redlink=1" class="new" title="25T2-NBMD (page does not exist)">25T2-NBMD</a></li> <li><a href="/w/index.php?title=25T7-NBMD&action=edit&redlink=1" class="new" title="25T7-NBMD (page does not exist)">25T7-NBMD</a></li> <li><a href="/w/index.php?title=25TFM-NBMD&action=edit&redlink=1" class="new" title="25TFM-NBMD (page does not exist)">25TFM-NBMD</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">25x-<abbr title="NB: N-benzyl; OH: hydroxy">NBOH</abbr></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/25B-NBOH" title="25B-NBOH">25B-NBOH</a></li> <li><a href="/wiki/25C-NBOH" title="25C-NBOH">25C-NBOH</a></li> <li><a href="/wiki/25CN-NBOH" title="25CN-NBOH">25CN-NBOH</a></li> <li><a href="/w/index.php?title=25D-NBOH&action=edit&redlink=1" class="new" title="25D-NBOH (page does not exist)">25D-NBOH</a></li> <li><a href="/wiki/25E-NBOH" title="25E-NBOH">25E-NBOH</a></li> <li><a href="/w/index.php?title=25F-NBOH&action=edit&redlink=1" class="new" title="25F-NBOH (page does not exist)">25F-NBOH</a></li> <li><a href="/w/index.php?title=25H-NBOH&action=edit&redlink=1" class="new" title="25H-NBOH (page does not exist)">25H-NBOH</a></li> <li><a href="/wiki/25I-NBOH" title="25I-NBOH">25I-NBOH</a></li> <li><a href="/w/index.php?title=25P-NBOH&action=edit&redlink=1" class="new" title="25P-NBOH (page does not exist)">25P-NBOH</a></li> <li><a href="/w/index.php?title=25T2-NBOH&action=edit&redlink=1" class="new" title="25T2-NBOH (page does not exist)">25T2-NBOH</a></li> <li><a href="/w/index.php?title=25T7-NBOH&action=edit&redlink=1" class="new" title="25T7-NBOH (page does not exist)">25T7-NBOH</a></li> <li><a href="/w/index.php?title=25TFM-NBOH&action=edit&redlink=1" class="new" title="25TFM-NBOH (page does not exist)">25TFM-NBOH</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">25x-<abbr title="NB: N-benzyl; OMe: methoxy">NBOMe</abbr></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/25B-NBOMe" title="25B-NBOMe">25B-NBOMe</a></li> <li><a href="/wiki/25C-NBOMe" title="25C-NBOMe">25C-NBOMe</a></li> <li><a href="/wiki/25CN-NBOMe" title="25CN-NBOMe">25CN-NBOMe</a></li> <li><a href="/wiki/25D-NBOMe" title="25D-NBOMe">25D-NBOMe</a></li> <li><a href="/wiki/25E-NBOMe" title="25E-NBOMe">25E-NBOMe</a></li> <li><a href="/w/index.php?title=25F-NBOMe&action=edit&redlink=1" class="new" title="25F-NBOMe (page does not exist)">25F-NBOMe</a></li> <li><a href="/wiki/25G-NBOMe" title="25G-NBOMe">25G-NBOMe</a></li> <li><a href="/wiki/25H-NBOMe" title="25H-NBOMe">25H-NBOMe</a></li> <li><a href="/wiki/25I-NBOMe" title="25I-NBOMe">25I-NBOMe</a></li> <li><a href="/wiki/25iP-NBOMe" title="25iP-NBOMe">25iP-NBOMe</a></li> <li><a href="/wiki/25N-NBOMe" title="25N-NBOMe">25N-NBOMe</a></li> <li><a href="/wiki/25P-NBOMe" title="25P-NBOMe">25P-NBOMe</a></li> <li><a href="/w/index.php?title=25T-NBOMe&action=edit&redlink=1" class="new" title="25T-NBOMe (page does not exist)">25T-NBOMe</a></li> <li><a href="/w/index.php?title=25T2-NBOMe&action=edit&redlink=1" class="new" title="25T2-NBOMe (page does not exist)">25T2-NBOMe</a></li> <li><a href="/w/index.php?title=25T4-NBOMe&action=edit&redlink=1" class="new" title="25T4-NBOMe (page does not exist)">25T4-NBOMe</a></li> <li><a href="/wiki/25T7-NBOMe" title="25T7-NBOMe">25T7-NBOMe</a></li> <li><a href="/wiki/25TFM-NBOMe" title="25TFM-NBOMe">25TFM-NBOMe</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Atypical structures</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/w/index.php?title=25B-N1POMe&action=edit&redlink=1" class="new" title="25B-N1POMe (page does not exist)">25B-N1POMe</a></li> <li><a href="/w/index.php?title=25B-NAcPip&action=edit&redlink=1" class="new" title="25B-NAcPip (page does not exist)">25B-NAcPip</a></li> <li><a href="/w/index.php?title=25B-NB23DM&action=edit&redlink=1" class="new" title="25B-NB23DM (page does not exist)">25B-NB23DM</a></li> <li><a href="/w/index.php?title=25B-NB25DM&action=edit&redlink=1" class="new" title="25B-NB25DM (page does not exist)">25B-NB25DM</a></li> <li><a href="/w/index.php?title=25C-NBCl&action=edit&redlink=1" class="new" title="25C-NBCl (page does not exist)">25C-NBCl</a></li> <li><a href="/w/index.php?title=25C-NBOEt&action=edit&redlink=1" class="new" title="25C-NBOEt (page does not exist)">25C-NBOEt</a></li> <li><a href="/w/index.php?title=25C-NBOiPr&action=edit&redlink=1" class="new" title="25C-NBOiPr (page does not exist)">25C-NBOiPr</a></li> <li><a href="/w/index.php?title=25I-N2Nap1OH&action=edit&redlink=1" class="new" title="25I-N2Nap1OH (page does not exist)">25I-N2Nap1OH</a></li> <li><a href="/w/index.php?title=25I-N3MT2M&action=edit&redlink=1" class="new" title="25I-N3MT2M (page does not exist)">25I-N3MT2M</a></li> <li><a href="/w/index.php?title=25I-N4MT3M&action=edit&redlink=1" class="new" title="25I-N4MT3M (page does not exist)">25I-N4MT3M</a></li> <li><a href="/wiki/25I-NB34MD" title="25I-NB34MD">25I-NB34MD</a></li> <li><a href="/w/index.php?title=25I-NBAm&action=edit&redlink=1" class="new" title="25I-NBAm (page does not exist)">25I-NBAm</a></li> <li><a href="/w/index.php?title=25I-NBBr&action=edit&redlink=1" class="new" title="25I-NBBr (page does not exist)">25I-NBBr</a></li> <li><a href="/w/index.php?title=25I-NBMeOH&action=edit&redlink=1" class="new" title="25I-NBMeOH (page does not exist)">25I-NBMeOH</a></li> <li><a href="/w/index.php?title=25I-NBTFM&action=edit&redlink=1" class="new" title="25I-NBTFM (page does not exist)">25I-NBTFM</a></li> <li><a href="/wiki/2CBCB-NBOMe" title="2CBCB-NBOMe">2CBCB-NBOMe</a></li> <li><a href="/wiki/2CBFly-NBOMe" title="2CBFly-NBOMe">2CBFly-NBOMe</a></li> <li><a href="/wiki/4-EA-NBOMe" title="4-EA-NBOMe">4-EA-NBOMe</a></li> <li><a href="/w/index.php?title=5-APB-NBOMe&action=edit&redlink=1" class="new" title="5-APB-NBOMe (page does not exist)">5-APB-NBOMe</a></li> <li><a href="/w/index.php?title=5MT-NBOMe&action=edit&redlink=1" class="new" title="5MT-NBOMe (page does not exist)">5MT-NBOMe</a></li> <li><a href="/w/index.php?title=C30-NBOMe&action=edit&redlink=1" class="new" title="C30-NBOMe (page does not exist)">C30-NBOMe</a></li> <li><a href="/w/index.php?title=DOB-NBOMe&action=edit&redlink=1" class="new" title="DOB-NBOMe (page does not exist)">DOB-NBOMe</a></li> <li><a href="/w/index.php?title=DOI-NBOMe&action=edit&redlink=1" class="new" title="DOI-NBOMe (page does not exist)">DOI-NBOMe</a></li> <li><a href="/w/index.php?title=FECIMBI-36&action=edit&redlink=1" class="new" title="FECIMBI-36 (page does not exist)">FECIMBI-36</a></li> <li><a href="/w/index.php?title=MDPEA-NBOMe&action=edit&redlink=1" class="new" title="MDPEA-NBOMe (page does not exist)">MDPEA-NBOMe</a></li> <li><a href="/wiki/N-Ethyl-2C-B" title="N-Ethyl-2C-B">N-Ethyl-2C-B</a></li> <li><a href="/w/index.php?title=NBOMe-escaline&action=edit&redlink=1" class="new" title="NBOMe-escaline (page does not exist)">NBOMe-escaline</a></li> <li><a href="/wiki/NBOMe-mescaline" title="NBOMe-mescaline">NBOMe-mescaline</a></li> <li><a href="/wiki/ZDCM-04" title="ZDCM-04">ZDCM-04</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">25x-NMx</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/w/index.php?title=25B-NMe7BF&action=edit&redlink=1" class="new" title="25B-NMe7BF (page does not exist)">25B-NMe7BF</a></li> <li><a href="/w/index.php?title=25B-NMe7BT&action=edit&redlink=1" class="new" title="25B-NMe7BT (page does not exist)">25B-NMe7BT</a></li> <li><a href="/w/index.php?title=25B-NMe7Bim&action=edit&redlink=1" class="new" title="25B-NMe7Bim (page does not exist)">25B-NMe7Bim</a></li> <li><a href="/w/index.php?title=25B-NMe7Box&action=edit&redlink=1" class="new" title="25B-NMe7Box (page does not exist)">25B-NMe7Box</a></li> <li><a href="/w/index.php?title=25B-NMe7DHBF&action=edit&redlink=1" class="new" title="25B-NMe7DHBF (page does not exist)">25B-NMe7DHBF</a></li> <li><a href="/w/index.php?title=25B-NMe7Ind&action=edit&redlink=1" class="new" title="25B-NMe7Ind (page does not exist)">25B-NMe7Ind</a></li> <li><a href="/w/index.php?title=25B-NMe7Indz&action=edit&redlink=1" class="new" title="25B-NMe7Indz (page does not exist)">25B-NMe7Indz</a></li> <li><a href="/w/index.php?title=25B-NMePyr&action=edit&redlink=1" class="new" title="25B-NMePyr (page does not exist)">25B-NMePyr</a></li> <li><a href="/w/index.php?title=25I-NMe7DHBF&action=edit&redlink=1" class="new" title="25I-NMe7DHBF (page does not exist)">25I-NMe7DHBF</a></li> <li><a href="/w/index.php?title=25I-NMeFur&action=edit&redlink=1" class="new" title="25I-NMeFur (page does not exist)">25I-NMeFur</a></li> <li><a href="/w/index.php?title=25I-NMeTHF&action=edit&redlink=1" class="new" title="25I-NMeTHF (page does not exist)">25I-NMeTHF</a></li> <li><a href="/w/index.php?title=25I-NMeTh&action=edit&redlink=1" class="new" title="25I-NMeTh (page does not exist)">25I-NMeTh</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/N-(2C)-fentanyl" class="mw-redirect" title="N-(2C)-fentanyl">N-(2C)-fentanyl</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/w/index.php?title=N-(2C-B)_fentanyl&action=edit&redlink=1" class="new" title="N-(2C-B) fentanyl (page does not exist)">N-(2C-B) fentanyl</a></li> <li><a href="/w/index.php?title=N-(2C-C)_fentanyl&action=edit&redlink=1" class="new" title="N-(2C-C) fentanyl (page does not exist)">N-(2C-C) fentanyl</a></li> <li><a href="/w/index.php?title=N-(2C-D)_fentanyl&action=edit&redlink=1" class="new" title="N-(2C-D) fentanyl (page does not exist)">N-(2C-D) fentanyl</a></li> <li><a href="/w/index.php?title=N-(2C-E)_fentanyl&action=edit&redlink=1" class="new" title="N-(2C-E) fentanyl (page does not exist)">N-(2C-E) fentanyl</a></li> <li><a href="/w/index.php?title=N-(2C-G)_fentanyl&action=edit&redlink=1" class="new" title="N-(2C-G) fentanyl (page does not exist)">N-(2C-G) fentanyl</a></li> <li><a href="/w/index.php?title=N-(2C-H)_fentanyl&action=edit&redlink=1" class="new" title="N-(2C-H) fentanyl (page does not exist)">N-(2C-H) fentanyl</a></li> <li><a href="/w/index.php?title=N-(2C-I)_fentanyl&action=edit&redlink=1" class="new" title="N-(2C-I) fentanyl (page does not exist)">N-(2C-I) fentanyl</a></li> <li><a href="/w/index.php?title=N-(2C-IP)_fentanyl&action=edit&redlink=1" class="new" title="N-(2C-IP) fentanyl (page does not exist)">N-(2C-IP) fentanyl</a></li> <li><a href="/w/index.php?title=N-(2C-N)_fentanyl&action=edit&redlink=1" class="new" title="N-(2C-N) fentanyl (page does not exist)">N-(2C-N) fentanyl</a></li> <li><a href="/w/index.php?title=N-(2C-P)_fentanyl&action=edit&redlink=1" class="new" title="N-(2C-P) fentanyl (page does not exist)">N-(2C-P) fentanyl</a></li> <li><a href="/w/index.php?title=N-(2C-T)_fentanyl&action=edit&redlink=1" class="new" title="N-(2C-T) fentanyl (page does not exist)">N-(2C-T) fentanyl</a></li> <li><a href="/w/index.php?title=N-(2C-T-2)_fentanyl&action=edit&redlink=1" class="new" title="N-(2C-T-2) fentanyl (page does not exist)">N-(2C-T-2) fentanyl</a></li> <li><a href="/w/index.php?title=N-(2C-T-4)_fentanyl&action=edit&redlink=1" class="new" title="N-(2C-T-4) fentanyl (page does not exist)">N-(2C-T-4) fentanyl</a></li> <li><a href="/w/index.php?title=N-(2C-T-7)_fentanyl&action=edit&redlink=1" class="new" title="N-(2C-T-7) fentanyl (page does not exist)">N-(2C-T-7) fentanyl</a></li> <li><a href="/w/index.php?title=N-(2C-TFM)_fentanyl&action=edit&redlink=1" class="new" title="N-(2C-TFM) fentanyl (page does not exist)">N-(2C-TFM) fentanyl</a></li></ul> </div></td></tr></tbody></table><div> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">3C-x</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/3C-AL" title="3C-AL">3C-AL</a></li> <li><a href="/wiki/3C-BZ" title="3C-BZ">3C-BZ</a></li> <li><a href="/wiki/3C-DFE" title="3C-DFE">3C-DFE</a></li> <li><a href="/wiki/3C-E" title="3C-E">3C-E</a></li> <li><a href="/wiki/3C-MAL" title="3C-MAL">3C-MAL</a></li> <li><a href="/wiki/3C-P" title="3C-P">3C-P</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">4C-x</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/4C-B" title="4C-B">4C-B</a></li> <li><a href="/w/index.php?title=4C-C&action=edit&redlink=1" class="new" title="4C-C (page does not exist)">4C-C</a></li> <li><a href="/wiki/4C-D" class="mw-redirect" title="4C-D">4C-D</a></li> <li><a href="/w/index.php?title=4C-E&action=edit&redlink=1" class="new" title="4C-E (page does not exist)">4C-E</a></li> <li><a href="/w/index.php?title=4C-I&action=edit&redlink=1" class="new" title="4C-I (page does not exist)">4C-I</a></li> <li><a href="/w/index.php?title=4C-N&action=edit&redlink=1" class="new" title="4C-N (page does not exist)">4C-N</a></li> <li><a href="/w/index.php?title=4C-P&action=edit&redlink=1" class="new" title="4C-P (page does not exist)">4C-P</a></li> <li><a href="/wiki/4C-T-2" title="4C-T-2">4C-T-2</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/DOx" title="DOx">DOx</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Aleph_(psychedelic)" title="Aleph (psychedelic)">DOT</a></li> <li><a href="/wiki/2,5-Dimethoxy-4-bromoamphetamine" title="2,5-Dimethoxy-4-bromoamphetamine">DOB</a></li> <li><a href="/wiki/2,5-Dimethoxy-4-chloroamphetamine" title="2,5-Dimethoxy-4-chloroamphetamine">DOC</a></li> <li><a href="/wiki/2,5-Dimethoxy-4-(2-fluoroethyl)amphetamine" title="2,5-Dimethoxy-4-(2-fluoroethyl)amphetamine">DOEF</a></li> <li><a href="/wiki/2,5-Dimethoxy-4-ethylamphetamine" title="2,5-Dimethoxy-4-ethylamphetamine">DOET</a></li> <li><a href="/wiki/2,5-Dimethoxy-4-fluoroamphetamine" title="2,5-Dimethoxy-4-fluoroamphetamine">DOF</a></li> <li><a href="/wiki/2,5-Dimethoxy-4-iodoamphetamine" title="2,5-Dimethoxy-4-iodoamphetamine">DOI</a></li> <li><a href="/wiki/2,5-Dimethoxy-4-isopropylamphetamine" title="2,5-Dimethoxy-4-isopropylamphetamine">DOiPR</a></li> <li><a href="/wiki/2,5-Dimethoxy-4-methylamphetamine" title="2,5-Dimethoxy-4-methylamphetamine">DOM</a></li> <li><a href="/wiki/2,5-Dimethoxy-4-nitroamphetamine" title="2,5-Dimethoxy-4-nitroamphetamine">DON</a></li> <li><a href="/wiki/2,5-Dimethoxy-4-propylamphetamine" title="2,5-Dimethoxy-4-propylamphetamine">DOPR</a></li> <li><a href="/wiki/2,5-Dimethoxy-4-trifluoromethylamphetamine" title="2,5-Dimethoxy-4-trifluoromethylamphetamine">DOTFM</a></li> <li><a href="/wiki/2,5-Dimethoxy-4-ethoxyamphetamine" title="2,5-Dimethoxy-4-ethoxyamphetamine">MEM</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">HOT-x</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/HOT-2" title="HOT-2">HOT-2</a></li> <li><a href="/wiki/HOT-7" title="HOT-7">HOT-7</a></li> <li><a href="/wiki/HOT-17" title="HOT-17">HOT-17</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Substituted_methylenedioxyphenethylamine" title="Substituted methylenedioxyphenethylamine">MDxx</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/DMMDA" title="DMMDA">DMMDA</a></li> <li><a href="/wiki/2,3-Dimethoxy-4,5-methylenedioxyamphetamine" class="mw-redirect" title="2,3-Dimethoxy-4,5-methylenedioxyamphetamine">DMMDA-2</a></li> <li><a href="/wiki/Lophophine" title="Lophophine">Lophophine</a></li> <li><a href="/wiki/3,4-Methylenedioxyamphetamine" title="3,4-Methylenedioxyamphetamine">MDA</a></li> <li><a href="/wiki/MDAI" title="MDAI">MDAI</a></li> <li><a href="/wiki/MDBZ" class="mw-redirect" title="MDBZ">MDBZ</a></li> <li><a class="mw-selflink selflink">MDMA</a></li> <li><a href="/wiki/MMDA_(drug)" title="MMDA (drug)">MMDA</a></li> <li><a href="/wiki/MMDA-2" title="MMDA-2">MMDA-2</a></li> <li><a href="/wiki/MMDA-3a" class="mw-redirect" title="MMDA-3a">MMDA-3a</a></li> <li><a href="/wiki/MMDMA" title="MMDMA">MMDMA</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Mescaline (subst.)</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/2-Bromomescaline" title="2-Bromomescaline">2-Bromomescaline</a></li> <li><a href="/wiki/Thioescaline" title="Thioescaline">3-TE</a></li> <li><a href="/wiki/Thioescaline" title="Thioescaline">4-TE</a></li> <li><a href="/wiki/Thiomescaline" title="Thiomescaline">3-TM</a></li> <li><a href="/wiki/Thiomescaline" title="Thiomescaline">4-TM</a></li> <li><a href="/wiki/Allylescaline" title="Allylescaline">Allylescaline</a></li> <li><a href="/wiki/Asymbescaline" title="Asymbescaline">Asymbescaline</a></li> <li><a href="/wiki/Buscaline" title="Buscaline">Buscaline</a></li> <li><a href="/wiki/Cyclopropylmescaline" title="Cyclopropylmescaline">Cyclopropylmescaline</a></li> <li><a href="/w/index.php?title=Difluoromescaline&action=edit&redlink=1" class="new" title="Difluoromescaline (page does not exist)">Difluoromescaline</a></li> <li><a href="/w/index.php?title=Difluoroescaline&action=edit&redlink=1" class="new" title="Difluoroescaline (page does not exist)">Difluoroescaline</a></li> <li><a href="/wiki/Escaline" title="Escaline">Escaline</a></li> <li><a href="/w/index.php?title=Fluoroproscaline&action=edit&redlink=1" class="new" title="Fluoroproscaline (page does not exist)">Fluoroproscaline</a></li> <li><a href="/w/index.php?title=Isobuscaline&action=edit&redlink=1" class="new" title="Isobuscaline (page does not exist)">Isobuscaline</a></li> <li><a href="/wiki/Isoproscaline" title="Isoproscaline">Isoproscaline</a></li> <li><a href="/wiki/Jimscaline" title="Jimscaline">Jimscaline</a></li> <li><a href="/wiki/Mescaline" title="Mescaline">Mescaline</a></li> <li><a href="/wiki/Metaescaline" title="Metaescaline">Metaescaline</a></li> <li><a href="/wiki/Methallylescaline" title="Methallylescaline">Methallylescaline</a></li> <li><a href="/wiki/Proscaline" title="Proscaline">Proscaline</a></li> <li><a href="/wiki/Thioproscaline" title="Thioproscaline">Thioproscaline</a></li> <li><a href="/w/index.php?title=Trifluoroescaline&action=edit&redlink=1" class="new" title="Trifluoroescaline (page does not exist)">Trifluoroescaline</a></li> <li><a href="/wiki/Trifluoromescaline" title="Trifluoromescaline">Trifluoromescaline</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Trimethoxyamphetamine" class="mw-redirect" title="Trimethoxyamphetamine">TMAs</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li>TMA</li> <li>TMA-2</li> <li>TMA-3</li> <li>TMA-4</li> <li>TMA-5</li> <li>TMA-6</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Others</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/2C-B-BUTTERFLY" title="2C-B-BUTTERFLY">2C-B-BUTTERFLY</a></li> <li><a href="/w/index.php?title=2C-B-DragonFLY&action=edit&redlink=1" class="new" title="2C-B-DragonFLY (page does not exist)">2C-B-DragonFLY</a></li> <li><a href="/w/index.php?title=2C-B-DragonFLY-NBOH&action=edit&redlink=1" class="new" title="2C-B-DragonFLY-NBOH (page does not exist)">2C-B-DragonFLY-NBOH</a></li> <li><a href="/w/index.php?title=2C-B-FLY-NB2EtO5Cl&action=edit&redlink=1" class="new" title="2C-B-FLY-NB2EtO5Cl (page does not exist)">2C-B-FLY-NB2EtO5Cl</a></li> <li><a href="/w/index.php?title=2CB-5-hemifly&action=edit&redlink=1" class="new" title="2CB-5-hemifly (page does not exist)">2CB-5-hemifly</a></li> <li><a href="/wiki/2CB-Ind" title="2CB-Ind">2CB-Ind</a></li> <li><a href="/wiki/2CD-5EtO" title="2CD-5EtO">2CD-5EtO</a></li> <li><a href="/wiki/TOET_(psychedelic)#2-TOET" title="TOET (psychedelic)">2-TOET</a></li> <li><a href="/wiki/TOET_(psychedelic)#5-TOET" title="TOET (psychedelic)">5-TOET</a></li> <li><a href="/wiki/TOM_(psychedelic)" title="TOM (psychedelic)">2-TOM</a></li> <li><a href="/wiki/TOM_(psychedelic)" title="TOM (psychedelic)">5-TOM</a></li> <li><a href="/wiki/BOB_(psychedelic)" title="BOB (psychedelic)">BOB</a></li> <li><a href="/wiki/BOD_(psychedelic)" title="BOD (psychedelic)">BOD</a></li> <li><a href="/wiki/%CE%92k-2C-B" title="Βk-2C-B">βk-2C-B</a></li> <li><a href="/w/index.php?title=%CE%92k-2C-I&action=edit&redlink=1" class="new" title="Βk-2C-I (page does not exist)">βk-2C-I</a></li> <li><a href="/wiki/DESOXY" title="DESOXY">DESOXY</a></li> <li><a href="/wiki/2,5-Dimethoxy-4-methylphenylcyclopropylamine" title="2,5-Dimethoxy-4-methylphenylcyclopropylamine">DMCPA</a></li> <li><a href="/wiki/DMBMPP" title="DMBMPP">DMBMPP</a></li> <li><a href="/wiki/DOB-FLY" title="DOB-FLY">DOB-FLY</a></li> <li><a href="/wiki/Fenfluramine" title="Fenfluramine">Fenfluramine</a></li> <li><a href="/wiki/Ganesha_(psychedelic)" title="Ganesha (psychedelic)">Ganesha</a></li> <li><a href="/wiki/Macromerine" title="Macromerine">Macromerine</a></li> <li><a href="/wiki/3-Methoxy-4-methylamphetamine" title="3-Methoxy-4-methylamphetamine">MMA</a></li> <li><a href="/wiki/TCB-2" title="TCB-2">TCB-2</a></li> <li><a href="/wiki/TOMSO" title="TOMSO">TOMSO</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Substituted_piperazine" title="Substituted piperazine">Piperazines</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/2C-B-PP" title="2C-B-PP">2C-B-PP</a></li> <li><a href="/wiki/Benzylpiperazine" title="Benzylpiperazine">BZP</a></li> <li><a href="/wiki/Para-Fluorophenylpiperazine" title="Para-Fluorophenylpiperazine">pFPP</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Substituted_tryptamine" title="Substituted tryptamine">Tryptamines</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Substituted_alpha-alkyltryptamine" class="mw-redirect" title="Substituted alpha-alkyltryptamine">alpha-alkyltryptamines</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/AL-37350A" title="AL-37350A">4,5-DHP-α-MT</a></li> <li><a href="/wiki/5-MeO-AET" title="5-MeO-AET">5-MeO-α-ET</a></li> <li><a href="/wiki/5-MeO-aMT" class="mw-redirect" title="5-MeO-aMT">5-MeO-α-MT</a></li> <li><a href="/wiki/Alpha-Ethyltryptamine" class="mw-redirect" title="Alpha-Ethyltryptamine">α-ET</a></li> <li><a href="/wiki/Alpha-Methyltryptamine" class="mw-redirect" title="Alpha-Methyltryptamine">α-MT</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">x-<abbr title="N,N-Diallyltryptamine">DALT</abbr></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/w/index.php?title=4-HO-DALT&action=edit&redlink=1" class="new" title="4-HO-DALT (page does not exist)">(Daltocin) 4-HO-DALT</a></li> <li><a href="/wiki/4-AcO-DALT" title="4-AcO-DALT">(Daltacetin) 4-AcO-DALT</a></li> <li><a href="/wiki/5-MeO-DALT" title="5-MeO-DALT">5-MeO-DALT</a></li> <li><a href="/wiki/DALT" title="DALT">DALT</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">x-<abbr title="N,N-Diethyltryptamine">DET</abbr></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/4-Acetoxy-DET" class="mw-redirect" title="4-Acetoxy-DET">(Ethacetin) 4-AcO-DET</a></li> <li><a href="/wiki/4-HO-DET" title="4-HO-DET">(Ethocin) 4-HO-DET</a></li> <li><a href="/wiki/5-MeO-DET" title="5-MeO-DET">5-MeO-DET</a></li> <li><a href="/wiki/Diethyltryptamine" title="Diethyltryptamine">(T-9) DET</a></li> <li><a href="/wiki/Ethocybin" title="Ethocybin">(Ethocybin) 4-PO-DET</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">x-<abbr title="N,N-Diisopropyltryptamine">DiPT</abbr></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/4-Acetoxy-DiPT" title="4-Acetoxy-DiPT">(Ipracetin) 4-AcO-DiPT</a></li> <li><a href="/wiki/4-HO-DiPT" title="4-HO-DiPT">(Iprocin) 4-HO-DiPT</a></li> <li><a href="/wiki/5-Methoxy-N,N-diisopropyltryptamine" class="mw-redirect" title="5-Methoxy-N,N-diisopropyltryptamine">5-MeO-DiPT</a></li> <li><a href="/wiki/Diisopropyltryptamine" class="mw-redirect" title="Diisopropyltryptamine">DiPT</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">x-<abbr title="N,N-Dimethyltryptamine">DMT</abbr></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/1-(2-Dimethylaminoethyl)dihydropyrano(3,2-e)indole" class="mw-redirect" title="1-(2-Dimethylaminoethyl)dihydropyrano(3,2-e)indole">4,5-DHP-DMT</a></li> <li><a href="/wiki/2,N,N-TMT" title="2,N,N-TMT">2,N,N-TMT</a></li> <li><a href="/wiki/O-Acetylpsilocin" class="mw-redirect" title="O-Acetylpsilocin">4-AcO-DMT</a></li> <li><a href="/wiki/4-Hydroxy-5-methoxydimethyltryptamine" class="mw-redirect" title="4-Hydroxy-5-methoxydimethyltryptamine">4-HO-5-MeO-DMT</a></li> <li><a href="/w/index.php?title=4,N,N-TMT&action=edit&redlink=1" class="new" title="4,N,N-TMT (page does not exist)">4,N,N-TMT</a></li> <li><a href="/wiki/4-Propionyloxy-DMT" class="mw-redirect" title="4-Propionyloxy-DMT">4-Propionyloxy-DMT</a></li> <li><a href="/w/index.php?title=5,6-diBr-DMT&action=edit&redlink=1" class="new" title="5,6-diBr-DMT (page does not exist)">5,6-diBr-DMT</a></li> <li><a href="/wiki/5-AcO-DMT" class="mw-redirect" title="5-AcO-DMT">5-AcO-DMT</a></li> <li><a href="/wiki/5-Bromo-DMT" title="5-Bromo-DMT">5-Bromo-DMT</a></li> <li><a href="/w/index.php?title=(Indapex)_5-MeO-2-TMT&action=edit&redlink=1" class="new" title="(Indapex) 5-MeO-2-TMT (page does not exist)">5-MeO-2,N,N-TMT</a></li> <li><a href="/w/index.php?title=5-MeO-4,N,N-TMT&action=edit&redlink=1" class="new" title="5-MeO-4,N,N-TMT (page does not exist)">5-MeO-4,N,N-TMT</a></li> <li><a href="/wiki/5-MeO-%CE%B1,N,N-TMT" class="mw-redirect" title="5-MeO-α,N,N-TMT">5-MeO-α,N,N-TMT</a></li> <li><a href="/wiki/5-MeO-DMT" title="5-MeO-DMT">5-MeO-DMT</a></li> <li><a href="/wiki/5,N,N-TMT" title="5,N,N-TMT">5-N,N-TMT</a></li> <li><a href="/wiki/7,N,N-TMT" title="7,N,N-TMT">7,N,N-TMT</a></li> <li><a href="/wiki/Alpha-N,N-Trimethyltryptamine" class="mw-redirect" title="Alpha-N,N-Trimethyltryptamine">α,N,N-TMT</a></li> <li><a href="/wiki/Bufotenin" title="Bufotenin">(Bufotenin) 5-HO-DMT</a></li> <li><a href="/wiki/N,N-Dimethyltryptamine" title="N,N-Dimethyltryptamine">DMT</a></li> <li><a href="/wiki/Norbaeocystin" title="Norbaeocystin">Norbaeocystin</a></li> <li><a href="/wiki/Psilocin" title="Psilocin">(Psilocin) 4-HO-DMT</a></li> <li><a href="/wiki/Psilocybin" title="Psilocybin">(Psilocybin) 4-PO-DMT</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">x-<abbr title="N,N-Dipropyltryptamine">DPT</abbr></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/w/index.php?title=4-Acetoxy-DPT&action=edit&redlink=1" class="new" title="4-Acetoxy-DPT (page does not exist)">(Depracetin) 4-AcO-DPT</a></li> <li><a href="/wiki/4-HO-DPT" title="4-HO-DPT">(Deprocin) 4-HO-DPT</a></li> <li><a href="/wiki/5-MeO-DPT" title="5-MeO-DPT">5-MeO-DPT</a></li> <li><a href="/wiki/Dipropyltryptamine" title="Dipropyltryptamine">(The Light) DPT</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Ibogaine-related</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/18-Methylaminocoronaridine" title="18-Methylaminocoronaridine">18-MAC</a></li> <li><a href="/wiki/18-Methoxycoronaridine" title="18-Methoxycoronaridine">18-MC</a></li> <li><a href="/wiki/Coronaridine" title="Coronaridine">Coronaridine</a></li> <li><a href="/wiki/Ibogaine" title="Ibogaine">Ibogaine</a></li> <li><a href="/wiki/Ibogamine" title="Ibogamine">Ibogamine</a></li> <li><a href="/wiki/2-Methoxyethyl-18-methoxycoronaridinate" title="2-Methoxyethyl-18-methoxycoronaridinate">ME-18-MC</a></li> <li><a href="/wiki/Noribogaine" title="Noribogaine">Noribogaine</a></li> <li><a href="/wiki/Tabernanthine" title="Tabernanthine">Tabernanthine</a></li> <li><a href="/wiki/Voacangine" title="Voacangine">Voacangine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">x-<abbr title="N-Methyl-N-ethyltryptamine">MET</abbr></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/4-HO-MET" title="4-HO-MET">(Metocin) 4-HO-MET</a></li> <li><a href="/wiki/4-AcO-MET" title="4-AcO-MET">(Metocetin) 4-AcO-MET</a></li> <li><a href="/wiki/5-MeO-MET" title="5-MeO-MET">5-MeO-MET</a></li> <li><a href="/wiki/N-Methyl-N-ethyltryptamine" title="N-Methyl-N-ethyltryptamine">MET</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">x-<abbr title="N-Methyl-N-isopropyltryptamine">MiPT</abbr></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/4-Acetoxy-MiPT" class="mw-redirect" title="4-Acetoxy-MiPT">(Mipracetin) 4-AcO-MiPT</a></li> <li><a href="/wiki/4-HO-MiPT" title="4-HO-MiPT">(Miprocin) 4-HO-MiPT</a></li> <li><a href="/wiki/5,N-Dimethyl-N-isopropyltryptamine" class="mw-redirect" title="5,N-Dimethyl-N-isopropyltryptamine">5-Me-MiPT</a></li> <li><a href="/wiki/5-MeO-MiPT" title="5-MeO-MiPT">(Moxy) 5-MeO-MiPT</a></li> <li><a href="/wiki/Methylisopropyltryptamine" class="mw-redirect" title="Methylisopropyltryptamine">MiPT</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Others</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/4-HO-DBT" title="4-HO-DBT">4-HO-DBT</a></li> <li><a href="/wiki/4-HO-EPT" title="4-HO-EPT">4-HO-EPT</a></li> <li><a href="/wiki/4-HO-McPT" title="4-HO-McPT">4-HO-McPT</a></li> <li><a href="/wiki/4-HO-MPMI" title="4-HO-MPMI">(Lucigenol) 4-HO-MPMI</a></li> <li><a href="/wiki/4-HO-MPT" title="4-HO-MPT">(Meprocin) 4-HO-MPT</a></li> <li><a href="/wiki/5-MeO-EiPT" title="5-MeO-EiPT">5-MeO-EiPT</a></li> <li><a href="/wiki/5-MeO-MALT" title="5-MeO-MALT">5-MeO-MALT</a></li> <li><a href="/wiki/5-MeO-MPMI" title="5-MeO-MPMI">5-MeO-MPMI</a></li> <li><a href="/wiki/Aeruginascin" title="Aeruginascin">Aeruginascin</a></li> <li><a href="/wiki/Baeocystin" title="Baeocystin">Baeocystin</a></li> <li><a href="/wiki/Dibutyltryptamine" title="Dibutyltryptamine">DBT</a></li> <li><a href="/w/index.php?title=Dicyclopropyltryptamine&action=edit&redlink=1" class="new" title="Dicyclopropyltryptamine (page does not exist)">DCPT</a></li> <li><a href="/wiki/Ethylisopropyltryptamine" title="Ethylisopropyltryptamine">EiPT</a></li> <li><a href="/wiki/Ethylpropyltryptamine" title="Ethylpropyltryptamine">EPT</a></li> <li><a href="/wiki/Methylpropyltryptamine" title="Methylpropyltryptamine">MPT</a></li> <li><a href="/wiki/Propylisopropyltryptamine" title="Propylisopropyltryptamine">PiPT</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Others</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/AL-38022A" title="AL-38022A">AL-38022A</a></li> <li><a href="/wiki/ALPHA_(psychedelic)" title="ALPHA (psychedelic)">ALPHA</a></li> <li><a href="/wiki/Dimemebfe" title="Dimemebfe">Dimemebfe</a></li> <li><a href="/wiki/Efavirenz" title="Efavirenz">Efavirenz</a></li> <li><a href="/wiki/Glaucine" title="Glaucine">Glaucine</a></li> <li><a href="/wiki/Lorcaserin" title="Lorcaserin">Lorcaserin</a></li> <li><a href="/wiki/M-ALPHA" class="mw-redirect" title="M-ALPHA">M-ALPHA</a></li> <li><a href="/wiki/RH-34" title="RH-34">RH-34</a> Also <a href="/wiki/Empathogen-entactogen" class="mw-redirect" title="Empathogen-entactogen">empathogens</a> in general (e. g.: <a href="/wiki/5-APB" title="5-APB">5-APB</a>, <a href="/wiki/5-MAPB" title="5-MAPB">5-MAPB</a>, <a href="/wiki/6-APB" title="6-APB">6-APB</a> and other <a href="/wiki/Substituted_benzofuran" title="Substituted benzofuran">substituted benzofurans</a>).</li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Dissociative" title="Dissociative">Dissociatives</a> (<a href="/wiki/NMDA_receptor" title="NMDA receptor">NMDAR</a> <a href="/wiki/NMDA_receptor_antagonist" title="NMDA receptor antagonist">antagonists</a>)</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Arylcyclohexylamine" title="Arylcyclohexylamine">Arylcyclo‐ hexylamines</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%">Ketamine-related</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/2-Fluorodeschloroketamine" title="2-Fluorodeschloroketamine">2-Fluorodeschloroketamine</a></li> <li><a href="/wiki/Arketamine" title="Arketamine">Arketamine</a> ((R)-ketamine)</li> <li><a href="/wiki/Deschloroketamine" title="Deschloroketamine">Deschloroketamine</a></li> <li><a href="/wiki/Ethketamine" class="mw-redirect" title="Ethketamine">Ethketamine</a> (N-Ethylnorketamine)</li> <li><a href="/wiki/Esketamine" title="Esketamine">Esketamine</a> ((S)-ketamine)</li> <li><a href="/wiki/Ketamine" title="Ketamine">Ketamine</a></li> <li><a href="/wiki/Methoxetamine" title="Methoxetamine">Methoxetamine</a></li> <li><a href="/wiki/Methoxmetamine" title="Methoxmetamine">Methoxmetamine</a></li> <li><a href="/wiki/Methoxyketamine" title="Methoxyketamine">Methoxyketamine</a></li> <li><a href="/wiki/MXiPr" class="mw-redirect" title="MXiPr">MXiPr</a></li> <li><a href="/wiki/Norketamine" title="Norketamine">Norketamine</a></li> <li><a href="/wiki/Tiletamine" title="Tiletamine">Tiletamine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">PCP-related</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/2%27-Oxo-PCE" class="mw-redirect" title="2'-Oxo-PCE">2'-Oxo-PCE</a></li> <li><a href="/w/index.php?title=3-HO-PCE&action=edit&redlink=1" class="new" title="3-HO-PCE (page does not exist)">3-HO-PCE</a></li> <li><a href="/wiki/3-HO-PCP" title="3-HO-PCP">3-HO-PCP</a></li> <li><a href="/wiki/3-MeO-PCE" title="3-MeO-PCE">3-MeO-PCE</a></li> <li><a href="/wiki/3-MeO-PCMo" title="3-MeO-PCMo">3-MeO-PCMo</a></li> <li><a href="/wiki/3-MeO-PCP" title="3-MeO-PCP">3-MeO-PCP</a></li> <li><a href="/w/index.php?title=3-MeO-PCPr&action=edit&redlink=1" class="new" title="3-MeO-PCPr (page does not exist)">3-MeO-PCPr</a></li> <li><a href="/w/index.php?title=3-MeO-PCPy&action=edit&redlink=1" class="new" title="3-MeO-PCPy (page does not exist)">3-MeO-PCPy</a></li> <li><a href="/wiki/4-MeO-PCP" title="4-MeO-PCP">4-MeO-PCP</a></li> <li><a href="/wiki/BDPC" title="BDPC">BDPC</a></li> <li><a href="/wiki/Dieticyclidine" title="Dieticyclidine">Dieticyclidine</a> (PCDE)</li> <li><a href="/wiki/Eticyclidine" title="Eticyclidine">Eticyclidine</a> (PCE)</li> <li><a href="/wiki/PCPr" title="PCPr">PCPr</a></li> <li><a href="/wiki/Phencyclidine" title="Phencyclidine">Phencyclidine</a> (PCP)</li> <li><a href="/wiki/Rolicyclidine" title="Rolicyclidine">Rolicyclidine</a> (PCPy)</li> <li><a href="/wiki/Tenocyclidine" title="Tenocyclidine">Tenocyclidine</a> (TCP)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Others</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/BTCP" class="mw-redirect" title="BTCP">BTCP</a></li> <li><a href="/wiki/Gacyclidine" title="Gacyclidine">Gacyclidine</a></li> <li><a href="/wiki/PRE-084" title="PRE-084">PRE-084</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Adamantane" title="Adamantane">Adamantanes</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Amantadine" title="Amantadine">Amantadine</a></li> <li><a href="/wiki/Memantine" title="Memantine">Memantine</a></li> <li><a href="/wiki/Rimantadine" title="Rimantadine">Rimantadine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Diarylethylamines</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Diphenidine" title="Diphenidine">Diphenidine</a></li> <li><a href="/wiki/Ephenidine" title="Ephenidine">Ephenidine</a></li> <li><a href="/wiki/Fluorolintane" title="Fluorolintane">Fluorolintane</a></li> <li><a href="/wiki/Methoxphenidine" title="Methoxphenidine">Methoxphenidine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Morphinan" title="Morphinan">Morphinans</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Dextrallorphan" title="Dextrallorphan">Dextrallorphan</a></li> <li><a href="/wiki/Dextromethorphan" title="Dextromethorphan">Dextromethorphan</a></li> <li><a href="/wiki/Dextrorphan" title="Dextrorphan">Dextrorphan</a></li> <li><a href="/wiki/Racemethorphan" class="mw-redirect" title="Racemethorphan">Racemethorphan</a></li> <li><a href="/wiki/Racemorphan" title="Racemorphan">Racemorphan</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Others</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/2-EMSB" class="mw-redirect" title="2-EMSB">2-EMSB</a></li> <li><a href="/wiki/2-MDP" title="2-MDP">2-MDP</a></li> <li><a href="/wiki/8A-PDHQ" title="8A-PDHQ">8A-PDHQ</a></li> <li><a href="/wiki/Aptiganel" title="Aptiganel">Aptiganel</a></li> <li><a href="/wiki/Budipine" title="Budipine">Budipine</a></li> <li><a href="/wiki/Delucemine" title="Delucemine">Delucemine</a></li> <li><a href="/wiki/Dexoxadrol" title="Dexoxadrol">Dexoxadrol</a></li> <li><a href="/wiki/Dizocilpine" title="Dizocilpine">Dizocilpine</a></li> <li><a href="/wiki/Etoxadrol" title="Etoxadrol">Etoxadrol</a></li> <li><a href="/wiki/Herkinorin" title="Herkinorin">Herkinorin</a></li> <li><a href="/wiki/Ibogaine" title="Ibogaine">Ibogaine</a></li> <li><a href="/wiki/Midafotel" title="Midafotel">Midafotel</a></li> <li><a href="/wiki/NEFA_(drug)" title="NEFA (drug)">NEFA</a></li> <li><a href="/wiki/Neramexane" title="Neramexane">Neramexane</a></li> <li><a href="/wiki/Nitrous_oxide" title="Nitrous oxide">Nitrous oxide</a></li> <li><a href="/wiki/Noribogaine" title="Noribogaine">Noribogaine</a></li> <li><a href="/wiki/Perzinfotel" title="Perzinfotel">Perzinfotel</a></li> <li><a href="/wiki/RB-64" title="RB-64">RB-64</a></li> <li><a href="/wiki/Remacemide" title="Remacemide">Remacemide</a></li> <li><a href="/wiki/Selfotel" title="Selfotel">Selfotel</a></li> <li><a href="/wiki/Xenon" title="Xenon">Xenon</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Deliriant" title="Deliriant">Deliriants</a> (<a href="/wiki/Muscarinic_acetylcholine_receptor" title="Muscarinic acetylcholine receptor">mAChR</a> <a href="/wiki/Anticholinergic" title="Anticholinergic">antagonists</a>)</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Atropine" title="Atropine">Atropine</a></li> <li><a href="/wiki/Benactyzine" title="Benactyzine">Benactyzine</a></li> <li><a href="/wiki/Benzatropine" title="Benzatropine">Benzatropine</a></li> <li><a href="/wiki/Benzydamine" title="Benzydamine">Benzydamine</a></li> <li><a href="/wiki/Biperiden" title="Biperiden">Biperiden</a></li> <li><a href="/w/index.php?title=BRN-1484501&action=edit&redlink=1" class="new" title="BRN-1484501 (page does not exist)">BRN-1484501</a></li> <li><a href="/wiki/Brompheniramine" title="Brompheniramine">Brompheniramine</a></li> <li><a href="/wiki/3-Quinuclidinyl_benzilate" title="3-Quinuclidinyl benzilate">BZ</a></li> <li><a href="/wiki/CAR-226,086" title="CAR-226,086">CAR-226,086</a></li> <li><a href="/wiki/CAR-301,060" title="CAR-301,060">CAR-301,060</a></li> <li><a href="/wiki/CAR-302,196" title="CAR-302,196">CAR-302,196</a></li> <li><a href="/wiki/CAR-302,282" title="CAR-302,282">CAR-302,282</a></li> <li><a href="/w/index.php?title=CAR-302,368&action=edit&redlink=1" class="new" title="CAR-302,368 (page does not exist)">CAR-302,368</a></li> <li><a href="/w/index.php?title=CAR-302,537&action=edit&redlink=1" class="new" title="CAR-302,537 (page does not exist)">CAR-302,537</a></li> <li><a href="/wiki/CAR-302,668" title="CAR-302,668">CAR-302,668</a></li> <li><a href="/wiki/Chloropyramine" title="Chloropyramine">Chloropyramine</a></li> <li><a href="/wiki/Chlorphenamine" title="Chlorphenamine">Chlorphenamine</a></li> <li><a href="/wiki/Clemastine" title="Clemastine">Clemastine</a></li> <li><a href="/wiki/CS-27349" title="CS-27349">CS-27349</a></li> <li><a href="/wiki/Cyclizine" title="Cyclizine">Cyclizine</a></li> <li><a href="/wiki/Cyproheptadine" title="Cyproheptadine">Cyproheptadine</a></li> <li><a href="/wiki/Dicycloverine" title="Dicycloverine">Dicycloverine</a></li> <li><a href="/wiki/Dimenhydrinate" title="Dimenhydrinate">Dimenhydrinate</a></li> <li><a href="/wiki/Diphenhydramine" title="Diphenhydramine">Diphenhydramine</a></li> <li><a href="/wiki/Ditran" title="Ditran">Ditran</a></li> <li><a href="/wiki/Doxylamine" title="Doxylamine">Doxylamine</a></li> <li><a href="/wiki/EA-3167" title="EA-3167">EA-3167</a></li> <li><a href="/wiki/EA-3443" title="EA-3443">EA-3443</a></li> <li><a href="/wiki/EA-3580" title="EA-3580">EA-3580</a></li> <li><a href="/wiki/EA-3834" title="EA-3834">EA-3834</a></li> <li><a href="/wiki/Flavoxate" title="Flavoxate">Flavoxate</a></li> <li><a href="/wiki/Hyoscyamine" title="Hyoscyamine">Hyoscyamine</a></li> <li><a href="/wiki/N-Ethyl-3-piperidyl_benzilate" title="N-Ethyl-3-piperidyl benzilate">JB-318</a></li> <li><a href="/wiki/N-Methyl-3-piperidyl_benzilate" title="N-Methyl-3-piperidyl benzilate">JB-336</a></li> <li><a href="/wiki/Meclozine" class="mw-redirect" title="Meclozine">Meclozine</a></li> <li><a href="/wiki/Mepyramine" title="Mepyramine">Mepyramine</a></li> <li><a href="/wiki/Orphenadrine" title="Orphenadrine">Orphenadrine</a></li> <li><a href="/wiki/Oxybutynin" title="Oxybutynin">Oxybutynin</a></li> <li><a href="/wiki/Pheniramine" title="Pheniramine">Pheniramine</a></li> <li><a href="/wiki/Phenyltoloxamine" title="Phenyltoloxamine">Phenyltoloxamine</a></li> <li><a href="/wiki/Procyclidine" title="Procyclidine">Procyclidine</a></li> <li><a href="/wiki/Promethazine" title="Promethazine">Promethazine</a></li> <li><a href="/wiki/Scopolamine" title="Scopolamine">Scopolamine</a></li> <li><a href="/wiki/Tolterodine" title="Tolterodine">Tolterodine</a></li> <li><a href="/wiki/Trihexyphenidyl" title="Trihexyphenidyl">Trihexyphenidyl</a></li> <li><a href="/wiki/Tripelennamine" title="Tripelennamine">Tripelennamine</a></li> <li><a href="/wiki/Triprolidine" title="Triprolidine">Triprolidine</a></li> <li><a href="/wiki/WIN-2299" title="WIN-2299">WIN-2299</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Others</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Cannabinoid" title="Cannabinoid">Cannabinoids</a> (<a href="/wiki/Cannabinoid_receptor_type_1" class="mw-redirect" title="Cannabinoid receptor type 1">CB1</a> agonists)</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Phytocannabinoids" class="mw-redirect" title="Phytocannabinoids">Natural</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Salvinorin_A" title="Salvinorin A">Salvinorin A</a></li> <li><a href="/wiki/Tetrahydrocannabinol" title="Tetrahydrocannabinol">THC (Dronabinol)</a></li> <li><a href="/wiki/THCV" class="mw-redirect" title="THCV">THCV</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Synthetic_cannabinoids" title="Synthetic cannabinoids">Synthetic</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/List_of_AM_cannabinoids" title="List of AM cannabinoids">AM-x</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/AM-087" title="AM-087">AM-087</a></li> <li><a href="/wiki/AM251" class="mw-redirect" title="AM251">AM-251</a></li> <li><a href="/w/index.php?title=AM-279_(disambiguation)&action=edit&redlink=1" class="new" title="AM-279 (disambiguation) (page does not exist)">AM-279</a></li> <li><a href="/w/index.php?title=AM-281_(disambiguation)&action=edit&redlink=1" class="new" title="AM-281 (disambiguation) (page does not exist)">AM-281</a></li> <li><a href="/w/index.php?title=AM-356_(disambiguation)&action=edit&redlink=1" class="new" title="AM-356 (disambiguation) (page does not exist)">AM-356</a></li> <li><a href="/w/index.php?title=AM-374_(disambiguation)&action=edit&redlink=1" class="new" title="AM-374 (disambiguation) (page does not exist)">AM-374</a></li> <li><a href="/w/index.php?title=AM-381_(disambiguation)&action=edit&redlink=1" class="new" title="AM-381 (disambiguation) (page does not exist)">AM-381</a></li> <li><a href="/wiki/AM-404" class="mw-redirect" title="AM-404">AM-404</a></li> <li><a href="/wiki/AM-411" title="AM-411">AM-411</a></li> <li><a href="/wiki/AM-630" title="AM-630">AM-630</a></li> <li><a href="/w/index.php?title=AM-661&action=edit&redlink=1" class="new" title="AM-661 (page does not exist)">AM-661</a></li> <li><a href="/wiki/AM-678" class="mw-redirect" title="AM-678">AM-678</a></li> <li><a href="/wiki/AM-679_(cannabinoid)" title="AM-679 (cannabinoid)">AM-679</a></li> <li><a href="/wiki/AM-694" title="AM-694">AM-694</a></li> <li><a href="/w/index.php?title=AM-735&action=edit&redlink=1" class="new" title="AM-735 (page does not exist)">AM-735</a></li> <li><a href="/wiki/AM-855" title="AM-855">AM-855</a></li> <li><a href="/w/index.php?title=AM-881&action=edit&redlink=1" class="new" title="AM-881 (page does not exist)">AM-881</a></li> <li><a href="/wiki/AM-883" class="mw-redirect" title="AM-883">AM-883</a></li> <li><a href="/wiki/AM-905" title="AM-905">AM-905</a></li> <li><a href="/wiki/AM-906" title="AM-906">AM-906</a></li> <li><a href="/wiki/AM-919" title="AM-919">AM-919</a></li> <li><a href="/wiki/AM-926" class="mw-redirect" title="AM-926">AM-926</a></li> <li><a href="/wiki/AM-938" title="AM-938">AM-938</a></li> <li><a href="/w/index.php?title=AM-1116&action=edit&redlink=1" class="new" title="AM-1116 (page does not exist)">AM-1116</a></li> <li><a href="/w/index.php?title=AM-1172&action=edit&redlink=1" class="new" title="AM-1172 (page does not exist)">AM-1172</a></li> <li><a href="/wiki/AM-1220" title="AM-1220">AM-1220</a></li> <li><a href="/wiki/AM-1221" title="AM-1221">AM-1221</a></li> <li><a href="/wiki/AM-1235" title="AM-1235">AM-1235</a></li> <li><a href="/wiki/AM-1241" title="AM-1241">AM-1241</a></li> <li><a href="/wiki/AM-1248" title="AM-1248">AM-1248</a></li> <li><a href="/w/index.php?title=AM-1710&action=edit&redlink=1" class="new" title="AM-1710 (page does not exist)">AM-1710</a></li> <li><a href="/wiki/AM-1714" title="AM-1714">AM-1714</a></li> <li><a href="/w/index.php?title=AM-1902&action=edit&redlink=1" class="new" title="AM-1902 (page does not exist)">AM-1902</a></li> <li><a href="/wiki/AM-2201" title="AM-2201">AM-2201</a></li> <li><a href="/w/index.php?title=AM-2212&action=edit&redlink=1" class="new" title="AM-2212 (page does not exist)">AM-2212</a></li> <li><a href="/w/index.php?title=AM-2213&action=edit&redlink=1" class="new" title="AM-2213 (page does not exist)">AM-2213</a></li> <li><a href="/wiki/AM-2232" title="AM-2232">AM-2232</a></li> <li><a href="/wiki/AM-2233" title="AM-2233">AM-2233</a></li> <li><a href="/wiki/AM-2389" title="AM-2389">AM-2389</a></li> <li><a href="/w/index.php?title=AM-3102&action=edit&redlink=1" class="new" title="AM-3102 (page does not exist)">AM-3102</a></li> <li><a href="/wiki/AM-4030" title="AM-4030">AM-4030</a></li> <li><a href="/w/index.php?title=AM-4054&action=edit&redlink=1" class="new" title="AM-4054 (page does not exist)">AM-4054</a></li> <li><a href="/wiki/AM-4056" class="mw-redirect" title="AM-4056">AM-4056</a></li> <li><a href="/wiki/AM-4113" class="mw-redirect" title="AM-4113">AM-4113</a></li> <li><a href="/wiki/AM-6545" title="AM-6545">AM-6545</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/List_of_CP_cannabinoids" title="List of CP cannabinoids">CP x</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/CP_47,497" title="CP 47,497">CP 47,497</a></li> <li><a href="/wiki/CP_55,244" title="CP 55,244">CP 55,244</a></li> <li><a href="/wiki/CP_55,940" title="CP 55,940">CP 55,940</a></li> <li><a href="/w/index.php?title=(%C2%B1)-CP_55,940&action=edit&redlink=1" class="new" title="(±)-CP 55,940 (page does not exist)">(±)-CP 55,940</a></li> <li><a href="/w/index.php?title=(%2B)-CP_55,940&action=edit&redlink=1" class="new" title="(+)-CP 55,940 (page does not exist)">(+)-CP 55,940</a></li> <li><a href="/w/index.php?title=(-)-CP_55,940&action=edit&redlink=1" class="new" title="(-)-CP 55,940 (page does not exist)">(-)-CP 55,940</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/List_of_HU_cannabinoids" title="List of HU cannabinoids">HU-x</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/HU-210" title="HU-210">HU-210</a></li> <li><a href="/wiki/HU-211" class="mw-redirect" title="HU-211">HU-211</a></li> <li><a href="/wiki/HU-239" class="mw-redirect" title="HU-239">HU-239</a></li> <li><a href="/wiki/HU-243" title="HU-243">HU-243</a></li> <li><a href="/wiki/HU-308" class="mw-redirect" title="HU-308">HU-308</a></li> <li><a href="/wiki/HU-320" title="HU-320">HU-320</a></li> <li><a href="/wiki/HU-331" title="HU-331">HU-331</a></li> <li><a href="/wiki/HU-336" title="HU-336">HU-336</a></li> <li><a href="/wiki/HU-345" title="HU-345">HU-345</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/List_of_JWH_cannabinoids" title="List of JWH cannabinoids">JWH-x</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/JWH-007" title="JWH-007">JWH-007</a></li> <li><a href="/wiki/JWH-015" title="JWH-015">JWH-015</a></li> <li><a href="/wiki/JWH-018" title="JWH-018">JWH-018</a></li> <li><a href="/wiki/JWH-019" title="JWH-019">JWH-019</a></li> <li><a href="/wiki/JWH-030" title="JWH-030">JWH-030</a></li> <li><a href="/wiki/JWH-047" title="JWH-047">JWH-047</a></li> <li><a href="/wiki/JWH-048" title="JWH-048">JWH-048</a></li> <li><a href="/wiki/JWH-051" title="JWH-051">JWH-051</a></li> <li><a href="/wiki/JWH-057" title="JWH-057">JWH-057</a></li> <li><a href="/wiki/JWH-073" title="JWH-073">JWH-073</a></li> <li><a href="/wiki/JWH-081" title="JWH-081">JWH-081</a></li> <li><a href="/wiki/JWH-098" title="JWH-098">JWH-098</a></li> <li><a href="/wiki/JWH-116" title="JWH-116">JWH-116</a></li> <li><a href="/wiki/JWH-120" title="JWH-120">JWH-120</a></li> <li><a href="/wiki/JWH-122" title="JWH-122">JWH-122</a></li> <li><a href="/wiki/JWH-133" title="JWH-133">JWH-133</a></li> <li><a href="/w/index.php?title=JWH-139&action=edit&redlink=1" class="new" title="JWH-139 (page does not exist)">JWH-139</a></li> <li><a href="/wiki/JWH-147" title="JWH-147">JWH-147</a></li> <li><a href="/wiki/JWH-148" title="JWH-148">JWH-148</a></li> <li><a href="/wiki/JWH-149" title="JWH-149">JWH-149</a></li> <li><a href="/wiki/JWH-149" title="JWH-149">JWH-149</a></li> <li><a href="/wiki/JWH-161" title="JWH-161">JWH-161</a></li> <li><a href="/wiki/JWH-164" title="JWH-164">JWH-164</a></li> <li><a href="/w/index.php?title=JWH-166&action=edit&redlink=1" class="new" title="JWH-166 (page does not exist)">JWH-166</a></li> <li><a href="/wiki/JWH-167" title="JWH-167">JWH-167</a></li> <li><a href="/wiki/JWH-171" class="mw-redirect" title="JWH-171">JWH-171</a></li> <li><a href="/wiki/JWH-175" title="JWH-175">JWH-175</a></li> <li><a href="/wiki/JWH-176" title="JWH-176">JWH-176</a></li> <li><a href="/w/index.php?title=JWH-181&action=edit&redlink=1" class="new" title="JWH-181 (page does not exist)">JWH-181</a></li> <li><a href="/wiki/JWH-182" class="mw-redirect" title="JWH-182">JWH-182</a></li> <li><a href="/wiki/JWH-184" title="JWH-184">JWH-184</a></li> <li><a href="/wiki/JWH-185" title="JWH-185">JWH-185</a></li> <li><a href="/w/index.php?title=JWH-192&action=edit&redlink=1" class="new" title="JWH-192 (page does not exist)">JWH-192</a></li> <li><a href="/wiki/JWH-193" title="JWH-193">JWH-193</a></li> <li><a href="/w/index.php?title=JWH-194&action=edit&redlink=1" class="new" title="JWH-194 (page does not exist)">JWH-194</a></li> <li><a href="/w/index.php?title=JWH-195&action=edit&redlink=1" class="new" title="JWH-195 (page does not exist)">JWH-195</a></li> <li><a href="/wiki/JWH-196" title="JWH-196">JWH-196</a></li> <li><a href="/w/index.php?title=JWH-197&action=edit&redlink=1" class="new" title="JWH-197 (page does not exist)">JWH-197</a></li> <li><a href="/wiki/JWH-198" title="JWH-198">JWH-198</a></li> <li><a href="/w/index.php?title=JWH-199&action=edit&redlink=1" class="new" title="JWH-199 (page does not exist)">JWH-199</a></li> <li><a href="/wiki/JWH-200" title="JWH-200">JWH-200</a></li> <li><a href="/wiki/JWH-203" title="JWH-203">JWH-203</a></li> <li><a href="/w/index.php?title=JWH-205&action=edit&redlink=1" class="new" title="JWH-205 (page does not exist)">JWH-205</a></li> <li><a href="/wiki/JWH-210" title="JWH-210">JWH-210</a></li> <li><a href="/wiki/JWH-210" title="JWH-210">JWH-210</a></li> <li><a href="/w/index.php?title=JWH-213&action=edit&redlink=1" class="new" title="JWH-213 (page does not exist)">JWH-213</a></li> <li><a href="/w/index.php?title=JWH-220&action=edit&redlink=1" class="new" title="JWH-220 (page does not exist)">JWH-220</a></li> <li><a href="/w/index.php?title=JWH-229&action=edit&redlink=1" class="new" title="JWH-229 (page does not exist)">JWH-229</a></li> <li><a href="/w/index.php?title=JWH-234&action=edit&redlink=1" class="new" title="JWH-234 (page does not exist)">JWH-234</a></li> <li><a href="/wiki/JWH-249" title="JWH-249">JWH-249</a></li> <li><a href="/wiki/JWH-250" title="JWH-250">JWH-250</a></li> <li><a href="/wiki/JWH-251" title="JWH-251">JWH-251</a></li> <li><a href="/w/index.php?title=JWH-253&action=edit&redlink=1" class="new" title="JWH-253 (page does not exist)">JWH-253</a></li> <li><a href="/w/index.php?title=JWH-258&action=edit&redlink=1" class="new" title="JWH-258 (page does not exist)">JWH-258</a></li> <li><a href="/w/index.php?title=JWH-300&action=edit&redlink=1" class="new" title="JWH-300 (page does not exist)">JWH-300</a></li> <li><a href="/wiki/JWH-302" title="JWH-302">JWH-302</a></li> <li><a href="/wiki/JWH-307" title="JWH-307">JWH-307</a></li> <li><a href="/w/index.php?title=JWH-336&action=edit&redlink=1" class="new" title="JWH-336 (page does not exist)">JWH-336</a></li> <li><a href="/w/index.php?title=JWH-350&action=edit&redlink=1" class="new" title="JWH-350 (page does not exist)">JWH-350</a></li> <li><a href="/wiki/JWH-359" title="JWH-359">JWH-359</a></li> <li><a href="/w/index.php?title=JWH-387&action=edit&redlink=1" class="new" title="JWH-387 (page does not exist)">JWH-387</a></li> <li><a href="/wiki/JWH-398" title="JWH-398">JWH-398</a></li> <li><a href="/wiki/JWH-424" title="JWH-424">JWH-424</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/List_of_miscellaneous_designer_cannabinoids" title="List of miscellaneous designer cannabinoids">Misc. designer cannabinoids</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/4-HTMPIPO" title="4-HTMPIPO">4-HTMPIPO</a></li> <li><a href="/wiki/5F-AB-FUPPYCA" title="5F-AB-FUPPYCA">5F-AB-FUPPYCA</a></li> <li><a href="/wiki/5F-AB-PINACA" title="5F-AB-PINACA">5F-AB-PINACA</a></li> <li><a href="/wiki/5F-ADB" title="5F-ADB">5F-ADB</a></li> <li><a href="/wiki/5F-ADB-PINACA" title="5F-ADB-PINACA">5F-ADB-PINACA</a></li> <li><a href="/wiki/5F-ADBICA" title="5F-ADBICA">5F-ADBICA</a></li> <li><a href="/wiki/5F-AMB" title="5F-AMB">5F-AMB</a></li> <li><a href="/wiki/5F-APINACA" title="5F-APINACA">5F-APINACA</a></li> <li><a href="/wiki/5F-CUMYL-PINACA" title="5F-CUMYL-PINACA">5F-CUMYL-PINACA</a></li> <li><a href="/wiki/5F-NNE1" title="5F-NNE1">5F-NNE1</a></li> <li><a href="/wiki/5F-PB-22" title="5F-PB-22">5F-PB-22</a></li> <li><a href="/wiki/5F-SDB-006" title="5F-SDB-006">5F-SDB-006</a></li> <li><a href="/wiki/A-796,260" title="A-796,260">A-796,260</a></li> <li><a href="/wiki/A-836,339" title="A-836,339">A-836,339</a></li> <li><a href="/wiki/AB-001" title="AB-001">AB-001</a></li> <li><a href="/wiki/AB-005" title="AB-005">AB-005</a></li> <li><a href="/wiki/AB-CHFUPYCA" title="AB-CHFUPYCA">AB-CHFUPYCA</a></li> <li><a href="/wiki/AB-CHMINACA" title="AB-CHMINACA">AB-CHMINACA</a></li> <li><a href="/wiki/AB-FUBINACA" title="AB-FUBINACA">AB-FUBINACA</a></li> <li><a href="/wiki/AB-PINACA" title="AB-PINACA">AB-PINACA</a></li> <li><a href="/wiki/ADAMANTYL-THPINACA" class="mw-redirect" title="ADAMANTYL-THPINACA">ADAMANTYL-THPINACA</a></li> <li><a href="/wiki/ADB-CHMINACA" title="ADB-CHMINACA">ADB-CHMINACA</a></li> <li><a href="/wiki/ADB-FUBINACA" title="ADB-FUBINACA">ADB-FUBINACA</a></li> <li><a href="/wiki/ADB-PINACA" title="ADB-PINACA">ADB-PINACA</a></li> <li><a href="/wiki/ADBICA" title="ADBICA">ADBICA</a></li> <li><a href="/wiki/ADSB-FUB-187" title="ADSB-FUB-187">ADSB-FUB-187</a></li> <li><a href="/wiki/AMB-FUBINACA" title="AMB-FUBINACA">AMB-FUBINACA</a></li> <li><a href="/wiki/APICA_(synthetic_cannabinoid_drug)" title="APICA (synthetic cannabinoid drug)">APICA</a></li> <li><a href="/wiki/APINACA" title="APINACA">APINACA</a></li> <li><a href="/wiki/APP-FUBINACA" title="APP-FUBINACA">APP-FUBINACA</a></li> <li><a href="/wiki/CB-13" title="CB-13">CB-13</a></li> <li><a href="/wiki/CUMYL-PICA" title="CUMYL-PICA">CUMYL-PICA</a></li> <li><a href="/wiki/CUMYL-PINACA" title="CUMYL-PINACA">CUMYL-PINACA</a></li> <li><a href="/wiki/CUMYL-THPINACA" title="CUMYL-THPINACA">CUMYL-THPINACA</a></li> <li><a href="/wiki/Dimethylheptylpyran" title="Dimethylheptylpyran">DMHP</a></li> <li><a href="/wiki/EAM-2201" title="EAM-2201">EAM-2201</a></li> <li><a href="/wiki/FAB-144" title="FAB-144">FAB-144</a></li> <li><a href="/wiki/FDU-PB-22" title="FDU-PB-22">FDU-PB-22</a></li> <li><a href="/wiki/FUB-144" title="FUB-144">FUB-144</a></li> <li><a href="/wiki/FUB-APINACA" title="FUB-APINACA">FUB-APINACA</a></li> <li><a href="/wiki/FUB-JWH-018" title="FUB-JWH-018">FUB-JWH-018</a></li> <li><a href="/wiki/FUB-PB-22" title="FUB-PB-22">FUB-PB-22</a></li> <li><a href="/wiki/FUBIMINA" title="FUBIMINA">FUBIMINA</a></li> <li><a href="/wiki/JTE_7-31" title="JTE 7-31">JTE 7-31</a></li> <li><a href="/wiki/JTE-907" title="JTE-907">JTE-907</a></li> <li><a href="/wiki/Levonantradol" title="Levonantradol">Levonantradol</a></li> <li><a href="/wiki/MDMB-CHMICA" title="MDMB-CHMICA">MDMB-CHMICA</a></li> <li><a href="/wiki/MDMB-CHMINACA" title="MDMB-CHMINACA">MDMB-CHMINACA</a></li> <li><a href="/wiki/MDMB-FUBINACA" title="MDMB-FUBINACA">MDMB-FUBINACA</a></li> <li><a href="/wiki/MEPIRAPIM" class="mw-redirect" title="MEPIRAPIM">MEPIRAPIM</a></li> <li><a href="/wiki/MAM-2201" title="MAM-2201">MAM-2201</a></li> <li><a href="/wiki/MDA-19" title="MDA-19">MDA-19</a></li> <li><a href="/wiki/MN-18" title="MN-18">MN-18</a></li> <li><a href="/wiki/MN-25" title="MN-25">MN-25</a></li> <li><a href="/wiki/NESS-0327" title="NESS-0327">NESS-0327</a></li> <li><a href="/wiki/NESS-040C5" title="NESS-040C5">NESS-040C5</a></li> <li><a href="/wiki/Nabilone" title="Nabilone">Nabilone</a></li> <li><a href="/wiki/Nabitan" title="Nabitan">Nabitan</a></li> <li><a href="/wiki/NM-2201" title="NM-2201">NM-2201</a></li> <li><a href="/wiki/NNE1" title="NNE1">NNE1</a></li> <li><a href="/wiki/Org_28611" title="Org 28611">Org 28611</a></li> <li><a href="/wiki/Parahexyl" title="Parahexyl">Parahexyl</a></li> <li><a href="/wiki/PTI-1" title="PTI-1">PTI-1</a></li> <li><a href="/wiki/PTI-2" title="PTI-2">PTI-2</a></li> <li><a href="/wiki/PX-1" title="PX-1">PX-1</a></li> <li><a href="/wiki/PX-2" title="PX-2">PX-2</a></li> <li><a href="/wiki/PX-3" title="PX-3">PX-3</a></li> <li><a href="/wiki/QUCHIC" title="QUCHIC">QUCHIC</a></li> <li><a href="/wiki/QUPIC" class="mw-redirect" title="QUPIC">QUPIC</a></li> <li><a href="/wiki/RCS-4" title="RCS-4">RCS-4</a></li> <li><a href="/wiki/RCS-8" title="RCS-8">RCS-8</a></li> <li><a href="/wiki/SDB-005" title="SDB-005">SDB-005</a></li> <li><a href="/wiki/SDB-006" title="SDB-006">SDB-006</a></li> <li><a href="/wiki/STS-135_(drug)" title="STS-135 (drug)">STS-135</a></li> <li><a href="/wiki/THC-O-acetate" title="THC-O-acetate">THC-O-acetate</a></li> <li><a href="/wiki/THC-O-phosphate" title="THC-O-phosphate">THC-O-phosphate</a></li> <li><a href="/wiki/THJ-018" title="THJ-018">THJ-018</a></li> <li><a href="/wiki/THJ-2201" title="THJ-2201">THJ-2201</a></li> <li><a href="/wiki/UR-144" title="UR-144">UR-144</a></li> <li><a href="/wiki/WIN_55,212-2" title="WIN 55,212-2">WIN 55,212-2</a></li> <li><a href="/wiki/XLR-11" title="XLR-11">XLR-11</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Dopamine_receptor_D2" title="Dopamine receptor D2">D2</a> <a href="/wiki/Dopamine_agonist" title="Dopamine agonist">agonists</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Apomorphine" title="Apomorphine">Apomorphine</a></li> <li><a href="/wiki/Aporphine" title="Aporphine">Aporphine</a></li> <li><a href="/wiki/Bromocriptine" title="Bromocriptine">Bromocriptine</a></li> <li><a href="/wiki/Cabergoline" title="Cabergoline">Cabergoline</a></li> <li><a href="/wiki/Lisuride" title="Lisuride">Lisuride</a></li> <li><a href="/wiki/LSD" title="LSD">LSD</a></li> <li><a href="/wiki/Memantine" title="Memantine">Memantine</a></li> <li><a href="/wiki/Nuciferine" title="Nuciferine">Nuciferine</a></li> <li><a href="/wiki/Pergolide" title="Pergolide">Pergolide</a></li> <li><a href="/wiki/Phenethylamine" title="Phenethylamine">Phenethylamine</a></li> <li><a href="/wiki/Piribedil" title="Piribedil">Piribedil</a></li> <li><a href="/wiki/Pramipexole" title="Pramipexole">Pramipexole</a></li> <li><a href="/wiki/Ropinirole" title="Ropinirole">Ropinirole</a></li> <li><a href="/wiki/Rotigotine" title="Rotigotine">Rotigotine</a></li> <li><a href="/wiki/Salvinorin_A" title="Salvinorin A">Salvinorin A</a> Also indirect D2 agonists, such as <a href="/wiki/Dopamine_reuptake_inhibitor" title="Dopamine reuptake inhibitor">dopamine reuptake inhibitors</a> (<a href="/wiki/Cocaine" title="Cocaine">cocaine</a>, <a href="/wiki/Methylphenidate" title="Methylphenidate">methylphenidate</a>), <a href="/wiki/Releasing_agent" class="mw-redirect" title="Releasing agent">releasing agents</a> (<a href="/wiki/Amphetamine" title="Amphetamine">amphetamine</a>, <a href="/wiki/Methamphetamine" title="Methamphetamine">methamphetamine</a>), and <a href="/wiki/Precursor_(chemistry)" title="Precursor (chemistry)">precursors</a> (<a href="/wiki/L-DOPA" title="L-DOPA">levodopa</a>).</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/GABAA_receptor" title="GABAA receptor">GABAA</a> enhancers</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/CI-966" title="CI-966">CI-966</a></li> <li><a href="/wiki/Eszopiclone" title="Eszopiclone">Eszopiclone</a></li> <li><a href="/wiki/Ibotenic_acid" title="Ibotenic acid">Ibotenic acid</a></li> <li><a href="/wiki/Muscimol" title="Muscimol">Muscimol</a> (<a href="/wiki/Amanita_muscaria" title="Amanita muscaria">Amanita muscaria</a>)</li> <li><a href="/wiki/Zaleplon" title="Zaleplon">Zaleplon</a></li> <li><a href="/wiki/Zolpidem" title="Zolpidem">Zolpidem</a></li> <li><a href="/wiki/Zopiclone" title="Zopiclone">Zopiclone</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Inhalant" title="Inhalant">Inhalants</a> (Mixed <a href="/wiki/Mechanism_of_action" title="Mechanism of action">MOA</a>)</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Aliphatic_hydrocarbons" class="mw-redirect" title="Aliphatic hydrocarbons">Aliphatic hydrocarbons</a> <ul><li><a href="/wiki/Butane" title="Butane">Butane</a></li> <li><a href="/wiki/Gasoline" title="Gasoline">Gasoline</a></li> <li><a href="/wiki/Kerosene" title="Kerosene">Kerosene</a></li> <li><a href="/wiki/Propane" title="Propane">Propane</a></li></ul></li> <li><a href="/wiki/Aromatic_hydrocarbon" class="mw-redirect" title="Aromatic hydrocarbon">Aromatic hydrocarbons</a> <ul><li><a href="/wiki/Toluene" title="Toluene">Toluene</a></li></ul></li> <li><a href="/wiki/Ether" title="Ether">Ethers</a> <ul><li><a href="/wiki/Diethyl_ether" title="Diethyl ether">Diethyl ether</a></li> <li><a href="/wiki/Enflurane" title="Enflurane">Enflurane</a></li></ul></li> <li><a href="/wiki/Haloalkane" title="Haloalkane">Haloalkanes</a> <ul><li><a href="/wiki/Chlorofluorocarbon" title="Chlorofluorocarbon">Chlorofluorocarbons</a></li> <li><a href="/wiki/Chloroform" title="Chloroform">Chloroform</a></li></ul></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/%CE%9A-opioid_receptor" title="Κ-opioid receptor">κOR</a> <a href="/wiki/Opioid" title="Opioid">agonists</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Salvinorin_B_ethoxymethyl_ether" class="mw-redirect" title="Salvinorin B ethoxymethyl ether">2-EMSB</a></li> <li><a href="/wiki/Alazocine" title="Alazocine">Alazocine</a></li> <li><a href="/wiki/Bremazocine" title="Bremazocine">Bremazocine</a></li> <li><a href="/wiki/Butorphan" class="mw-redirect" title="Butorphan">Butorphan</a></li> <li><a href="/wiki/Butorphanol" title="Butorphanol">Butorphanol</a></li> <li><a href="/wiki/Cyclazocine" title="Cyclazocine">Cyclazocine</a></li> <li><a href="/wiki/Cyclorphan" title="Cyclorphan">Cyclorphan</a></li> <li><a href="/wiki/Cyprenorphine" title="Cyprenorphine">Cyprenorphine</a></li> <li><a href="/wiki/Diprenorphine" title="Diprenorphine">Diprenorphine</a></li> <li><a href="/wiki/Enadoline" title="Enadoline">Enadoline</a></li> <li><a href="/wiki/Herkinorin" title="Herkinorin">Herkinorin</a></li> <li><a href="/wiki/Heroin" title="Heroin">Heroin</a></li> <li><a href="/wiki/HZ-2" title="HZ-2">HZ-2</a></li> <li><a href="/wiki/Ibogaine" title="Ibogaine">Ibogaine</a></li> <li><a href="/wiki/Ketazocine" title="Ketazocine">Ketazocine</a></li> <li><a href="/wiki/Levallorphan" title="Levallorphan">Levallorphan</a></li> <li><a href="/wiki/Levomethorphan" title="Levomethorphan">Levomethorphan</a></li> <li><a href="/wiki/Levorphanol" title="Levorphanol">Levorphanol</a></li> <li><a href="/wiki/LPK-26" title="LPK-26">LPK-26</a></li> <li><a href="/wiki/Metazocine" title="Metazocine">Metazocine</a></li> <li><a href="/wiki/Morphine" title="Morphine">Morphine</a></li> <li><a href="/wiki/Nalbuphine" title="Nalbuphine">Nalbuphine</a></li> <li><a href="/wiki/Nalmefene" title="Nalmefene">Nalmefene</a></li> <li><a href="/wiki/Nalorphine" title="Nalorphine">Nalorphine</a></li> <li><a href="/wiki/Noribogaine" title="Noribogaine">Noribogaine</a></li> <li><a href="/wiki/Oxilorphan" title="Oxilorphan">Oxilorphan</a></li> <li><a href="/wiki/Pentazocine" title="Pentazocine">Pentazocine</a></li> <li><a href="/wiki/Phenazocine" title="Phenazocine">Phenazocine</a></li> <li><a href="/wiki/Proxorphan" title="Proxorphan">Proxorphan</a></li> <li><a href="/wiki/Racemethorphan" class="mw-redirect" title="Racemethorphan">Racemethorphan</a></li> <li><a href="/wiki/Racemorphan" title="Racemorphan">Racemorphan</a></li> <li><a href="/wiki/Salvinorin_A" title="Salvinorin A">Salvinorin A</a></li> <li><a href="/wiki/Spiradoline" title="Spiradoline">Spiradoline</a></li> <li><a href="/wiki/Tifluadom" title="Tifluadom">Tifluadom</a></li> <li><a href="/wiki/U-50488" title="U-50488">U-50488</a></li> <li><a href="/wiki/U-69,593" title="U-69,593">U-69,593</a></li> <li><a href="/wiki/Xorphanol" title="Xorphanol">Xorphanol</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Oneirogen" title="Oneirogen">Oneirogens</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Calea_ternifolia" title="Calea ternifolia">Calea zacatechichi</a></li> <li><a href="/wiki/Silene_undulata" title="Silene undulata">Silene capensis</a></li> <li><a href="/wiki/Galantamine" title="Galantamine">Galantamine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Others</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Glaucine" title="Glaucine">Glaucine</a></li> <li><a href="/wiki/Isoaminile" title="Isoaminile">Isoaminile</a></li> <li><a href="/wiki/Noscapine" title="Noscapine">Noscapine</a></li> <li><a href="/wiki/Prenoxdiazine" title="Prenoxdiazine">Prenoxdiazine</a></li> <li><a href="/wiki/Pukateine" title="Pukateine">Pukateine</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374" /><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235" /></div><div role="navigation" class="navbox" aria-labelledby="Stimulants535" style="padding:3px"><table class="nowraplinks mw-collapsible mw-collapsed navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374" /><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231" /><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Stimulants" title="Template:Stimulants"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Stimulants" title="Template talk:Stimulants"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Stimulants" title="Special:EditPage/Template:Stimulants"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Stimulants535" style="font-size:114%;margin:0 4em"><a href="/wiki/Stimulant" title="Stimulant">Stimulants</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Adamantane" title="Adamantane">Adamantanes</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Adapromine" title="Adapromine">Adapromine</a></li> <li><a href="/wiki/Amantadine" title="Amantadine">Amantadine</a></li> <li><a href="/wiki/Bromantane" title="Bromantane">Bromantane</a></li> <li><a href="/wiki/Memantine" title="Memantine">Memantine</a></li> <li><a href="/wiki/Rimantadine" title="Rimantadine">Rimantadine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Adenosine_receptor" title="Adenosine receptor">Adenosine antagonists</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/8-Chlorotheophylline" title="8-Chlorotheophylline">8-Chlorotheophylline</a></li> <li><a href="/wiki/8-Cyclopentyl-1,3-dimethylxanthine" title="8-Cyclopentyl-1,3-dimethylxanthine">8-Cyclopentyltheophylline</a></li> <li><a href="/wiki/8-Phenyltheophylline" title="8-Phenyltheophylline">8-Phenyltheophylline</a></li> <li><a href="/wiki/Aminophylline" title="Aminophylline">Aminophylline</a></li> <li><a href="/wiki/Caffeine" title="Caffeine">Caffeine</a></li> <li><a href="/wiki/CGS-15943" title="CGS-15943">CGS-15943</a></li> <li><a href="/wiki/Dimethazan" title="Dimethazan">Dimethazan</a></li> <li><a href="/wiki/Istradefylline" title="Istradefylline">Istradefylline</a></li> <li><a href="/wiki/Paraxanthine" title="Paraxanthine">Paraxanthine</a></li> <li><a href="/wiki/SCH-58261" title="SCH-58261">SCH-58261</a></li> <li><a href="/wiki/Theobromine" title="Theobromine">Theobromine</a></li> <li><a href="/wiki/Theophylline" title="Theophylline">Theophylline</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Psychotropic_alkylamines" title="Psychotropic alkylamines">Alkylamines</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Cyclopentamine" title="Cyclopentamine">Cyclopentamine</a></li> <li><a href="/wiki/Cypenamine" title="Cypenamine">Cypenamine</a></li> <li><a href="/wiki/Cyprodenate" title="Cyprodenate">Cyprodenate</a></li> <li><a href="/wiki/Heptaminol" title="Heptaminol">Heptaminol</a></li> <li><a href="/wiki/Isometheptene" title="Isometheptene">Isometheptene</a></li> <li><a href="/wiki/Methylhexanamine" title="Methylhexanamine">Methylhexaneamine</a></li> <li><a href="/wiki/Octodrine" title="Octodrine">Octodrine</a></li> <li><a href="/wiki/Propylhexedrine" title="Propylhexedrine">Propylhexedrine</a></li> <li><a href="/wiki/Tuaminoheptane" title="Tuaminoheptane">Tuaminoheptane</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Ampakine" title="Ampakine">Ampakines</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/CX-516" title="CX-516">CX-516</a></li> <li><a href="/wiki/CX-546" title="CX-546">CX-546</a></li> <li><a href="/wiki/CX-614" class="mw-redirect" title="CX-614">CX-614</a></li> <li><a href="/wiki/Farampator" title="Farampator">CX-691</a></li> <li><a href="/wiki/CX717" title="CX717">CX-717</a></li> <li><a href="/wiki/IDRA-21" title="IDRA-21">IDRA-21</a></li> <li><a href="/wiki/LY-404,187" class="mw-redirect" title="LY-404,187">LY-404,187</a></li> <li><a href="/wiki/LY-503,430" class="mw-redirect" title="LY-503,430">LY-503,430</a></li> <li><a href="/wiki/Nooglutyl" title="Nooglutyl">Nooglutyl</a></li> <li><a href="/wiki/Org_26576" class="mw-redirect" title="Org 26576">Org 26576</a></li> <li><a href="/wiki/PEPA_(drug)" title="PEPA (drug)">PEPA</a></li> <li><a href="/wiki/S-18986" title="S-18986">S-18986</a></li> <li><a href="/wiki/Sunifiram" title="Sunifiram">Sunifiram</a></li> <li><a href="/wiki/Unifiram" title="Unifiram">Unifiram</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Arylcyclohexylamine" title="Arylcyclohexylamine">Arylcyclohexylamines</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Benocyclidine" title="Benocyclidine">Benocyclidine</a></li> <li><a href="/wiki/Dieticyclidine" title="Dieticyclidine">Dieticyclidine</a></li> <li><a href="/wiki/Esketamine" title="Esketamine">Esketamine</a></li> <li><a href="/wiki/Eticyclidine" title="Eticyclidine">Eticyclidine</a></li> <li><a href="/wiki/Gacyclidine" title="Gacyclidine">Gacyclidine</a></li> <li><a href="/wiki/Ketamine" title="Ketamine">Ketamine</a></li> <li><a href="/wiki/Phencyclamine" class="mw-redirect" title="Phencyclamine">Phencyclamine</a></li> <li><a href="/wiki/Phencyclidine" title="Phencyclidine">Phencyclidine</a></li> <li><a href="/wiki/Rolicyclidine" title="Rolicyclidine">Rolicyclidine</a></li> <li><a href="/wiki/Tenocyclidine" title="Tenocyclidine">Tenocyclidine</a></li> <li><a href="/wiki/Tiletamine" title="Tiletamine">Tiletamine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Benzazepine" title="Benzazepine">Benzazepines</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/6-Br-APB" title="6-Br-APB">6-Br-APB</a></li> <li><a href="/wiki/SKF-77434" class="mw-redirect" title="SKF-77434">SKF-77434</a></li> <li><a href="/wiki/SKF-81297" class="mw-redirect" title="SKF-81297">SKF-81297</a></li> <li><a href="/wiki/SKF-82958" class="mw-redirect" title="SKF-82958">SKF-82958</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Substituted_cathinone" title="Substituted cathinone">Cathinones</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/3-FMC" class="mw-redirect" title="3-FMC">3-FMC</a></li> <li><a href="/wiki/3-MMC" class="mw-redirect" title="3-MMC">3-MMC</a></li> <li><a href="/wiki/3,4-Dimethylmethcathinone" title="3,4-Dimethylmethcathinone">3,4-DMMC</a></li> <li><a href="/wiki/4-Bromomethcathinone" title="4-Bromomethcathinone">4-BMC</a></li> <li><a href="/wiki/4-Chloromethcathinone" title="4-Chloromethcathinone">4-CMC</a></li> <li><a href="/wiki/4-Methylbuphedrone" title="4-Methylbuphedrone">4-Methylbuphedrone</a></li> <li><a href="/wiki/4-Methylcathinone" title="4-Methylcathinone">4-Methylcathinone</a></li> <li><a href="/wiki/4-Methyl-%CE%B1-ethylaminopentiophenone" title="4-Methyl-α-ethylaminopentiophenone">4-MEAP</a></li> <li><a href="/wiki/4-Methylpentedrone" title="4-Methylpentedrone">4-Methylpentedrone</a></li> <li><a href="/wiki/Amfepramone" title="Amfepramone">Amfepramone</a></li> <li><a href="/wiki/Benzedrone" title="Benzedrone">Benzedrone</a></li> <li><a href="/wiki/Buphedrone" title="Buphedrone">Buphedrone</a></li> <li><a href="/wiki/Bupropion" title="Bupropion">Bupropion</a></li> <li><a href="/wiki/Butylone" title="Butylone">Butylone</a></li> <li><a href="/wiki/Cathinone" title="Cathinone">Cathinone</a></li> <li><a href="/wiki/Dimethylcathinone" class="mw-redirect" title="Dimethylcathinone">Dimethylcathinone</a></li> <li><a href="/wiki/Ethcathinone" title="Ethcathinone">Ethcathinone</a></li> <li><a href="/wiki/Ethylone" title="Ethylone">Ethylone</a></li> <li><a href="/wiki/Flephedrone" title="Flephedrone">Flephedrone</a></li> <li><a href="/wiki/Hexedrone" title="Hexedrone">Hexedrone</a></li> <li><a href="/wiki/Isoethcathinone" title="Isoethcathinone">Isoethcathinone</a></li> <li><a href="/wiki/Mephedrone" title="Mephedrone">Mephedrone</a></li> <li><a href="/wiki/Methcathinone" title="Methcathinone">Methcathinone</a></li> <li><a href="/wiki/Methedrone" title="Methedrone">Methedrone</a></li> <li><a href="/wiki/Methylenedioxycathinone" title="Methylenedioxycathinone">Methylenedioxycathinone</a></li> <li><a href="/wiki/Methylone" title="Methylone">Methylone</a></li> <li><a href="/wiki/Mexedrone" title="Mexedrone">Mexedrone</a></li> <li><a href="/wiki/N-Ethylbuphedrone" title="N-Ethylbuphedrone">N-Ethylbuphedrone</a></li> <li><a href="/wiki/N-Ethylhexedrone" title="N-Ethylhexedrone">N-Ethylhexedrone</a></li> <li><a href="/wiki/Pentedrone" title="Pentedrone">Pentedrone</a></li> <li><a href="/wiki/Pentylone" title="Pentylone">Pentylone</a></li> <li><a href="/wiki/Phthalimidopropiophenone" title="Phthalimidopropiophenone">Phthalimidopropiophenone</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Acetylcholine" title="Acetylcholine">Cholinergics</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/A-84,543" title="A-84,543">A-84,543</a></li> <li><a href="/wiki/A-366,833" title="A-366,833">A-366,833</a></li> <li><a href="/wiki/ABT-202" title="ABT-202">ABT-202</a></li> <li><a href="/wiki/ABT-418" title="ABT-418">ABT-418</a></li> <li><a href="/wiki/AR-R17779" title="AR-R17779">AR-R17779</a></li> <li><a href="/wiki/Altinicline" title="Altinicline">Altinicline</a></li> <li><a href="/wiki/Anabasine" title="Anabasine">Anabasine</a></li> <li><a href="/wiki/Arecoline" title="Arecoline">Arecoline</a></li> <li><a href="/wiki/Bradanicline" title="Bradanicline">Bradanicline</a></li> <li><a href="/wiki/Cotinine" title="Cotinine">Cotinine</a></li> <li><a href="/wiki/Cytisine" title="Cytisine">Cytisine</a></li> <li><a href="/wiki/Dianicline" title="Dianicline">Dianicline</a></li> <li><a href="/wiki/Epibatidine" title="Epibatidine">Epibatidine</a></li> <li><a href="/wiki/Epiboxidine" title="Epiboxidine">Epiboxidine</a></li> <li><a href="/wiki/GTS-21" title="GTS-21">GTS-21</a></li> <li><a href="/wiki/Ispronicline" title="Ispronicline">Ispronicline</a></li> <li><a href="/wiki/Nicotine" title="Nicotine">Nicotine</a></li> <li><a href="/wiki/PHA-543,613" title="PHA-543,613">PHA-543,613</a></li> <li><a href="/wiki/PNU-120,596" title="PNU-120,596">PNU-120,596</a></li> <li><a href="/wiki/PNU-282,987" title="PNU-282,987">PNU-282,987</a></li> <li><a href="/wiki/Pozanicline" title="Pozanicline">Pozanicline</a></li> <li><a href="/wiki/Rivanicline" title="Rivanicline">Rivanicline</a></li> <li><a href="/wiki/Sazetidine_A" title="Sazetidine A">Sazetidine A</a></li> <li><a href="/wiki/SIB-1553A" title="SIB-1553A">SIB-1553A</a></li> <li><a href="/wiki/SSR-180,711" title="SSR-180,711">SSR-180,711</a></li> <li><a href="/wiki/TC-1698" title="TC-1698">TC-1698</a></li> <li><a href="/wiki/TC-1827" title="TC-1827">TC-1827</a></li> <li><a href="/wiki/TC-2216" title="TC-2216">TC-2216</a></li> <li><a href="/wiki/Tebanicline" title="Tebanicline">Tebanicline</a></li> <li><a href="/wiki/UB-165" title="UB-165">UB-165</a></li> <li><a href="/wiki/Varenicline" title="Varenicline">Varenicline</a></li> <li><a href="/wiki/WAY-317,538" class="mw-redirect" title="WAY-317,538">WAY-317,538</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Convulsion" title="Convulsion">Convulsants</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Anatoxin-a" title="Anatoxin-a">Anatoxin-a</a></li> <li><a href="/wiki/Bicuculline" title="Bicuculline">Bicuculline</a></li> <li><a href="/wiki/DMCM" title="DMCM">DMCM</a></li> <li><a href="/wiki/Flurothyl" title="Flurothyl">Flurothyl</a></li> <li><a href="/wiki/Gabazine" title="Gabazine">Gabazine</a></li> <li><a href="/wiki/Pentylenetetrazol" title="Pentylenetetrazol">Pentetrazol</a></li> <li><a href="/wiki/Picrotoxin" title="Picrotoxin">Picrotoxin</a></li> <li><a href="/wiki/Strychnine" title="Strychnine">Strychnine</a></li> <li><a href="/wiki/Thujone" title="Thujone">Thujone</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Eugeroic" title="Eugeroic">Eugeroics</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Adrafinil" title="Adrafinil">Adrafinil</a></li> <li><a href="/wiki/Armodafinil" title="Armodafinil">Armodafinil</a></li> <li><a href="/wiki/CRL-40,940" class="mw-redirect" title="CRL-40,940">CRL-40,940</a></li> <li><a href="/wiki/CRL-40,941" class="mw-redirect" title="CRL-40,941">CRL-40,941</a></li> <li><a href="/wiki/Fluorenol" title="Fluorenol">Fluorenol</a></li> <li><a href="/wiki/Modafinil" title="Modafinil">Modafinil</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Oxazoline" title="Oxazoline">Oxazolines</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/4-Methylaminorex" title="4-Methylaminorex">4-Methylaminorex</a></li> <li><a href="/wiki/Aminorex" title="Aminorex">Aminorex</a></li> <li><a href="/wiki/Clominorex" title="Clominorex">Clominorex</a></li> <li><a href="/wiki/Cyclazodone" title="Cyclazodone">Cyclazodone</a></li> <li><a href="/wiki/Fenozolone" title="Fenozolone">Fenozolone</a></li> <li><a href="/wiki/Fluminorex" title="Fluminorex">Fluminorex</a></li> <li><a href="/wiki/Pemoline" title="Pemoline">Pemoline</a></li> <li><a href="/wiki/Thozalinone" title="Thozalinone">Thozalinone</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Substituted_phenethylamine" title="Substituted phenethylamine">Phenethylamines</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/4-Methylphenylisobutylamine" title="4-Methylphenylisobutylamine">1-(4-Methylphenyl)-2-aminobutane</a></li> <li><a href="/wiki/1-Methylamino-1-(3,4-methylenedioxyphenyl)propane" title="1-Methylamino-1-(3,4-methylenedioxyphenyl)propane">1-Methylamino-1-(3,4-methylenedioxyphenyl)propane</a></li> <li><a href="/wiki/2-Fluoroamphetamine" title="2-Fluoroamphetamine">2-Fluoroamphetamine</a></li> <li><a href="/wiki/2-FMA" class="mw-redirect" title="2-FMA">2-Fluoromethamphetamine</a></li> <li><a href="/wiki/2-Hydroxyphenethylamine" class="mw-redirect" title="2-Hydroxyphenethylamine">2-OH-PEA</a></li> <li><a href="/wiki/2-Phenyl-3-aminobutane" title="2-Phenyl-3-aminobutane">2-Phenyl-3-aminobutane</a></li> <li><a href="/wiki/2,3-Methylenedioxyamphetamine" title="2,3-Methylenedioxyamphetamine">2,3-MDA</a></li> <li><a href="/wiki/3-FA" class="mw-redirect" title="3-FA">3-Fluoroamphetamine</a></li> <li><a href="/wiki/3-Fluoroethamphetamine" title="3-Fluoroethamphetamine">3-Fluoroethamphetamine</a></li> <li><a href="/wiki/3-Methoxyamphetamine" title="3-Methoxyamphetamine">3-Methoxyamphetamine</a></li> <li><a href="/wiki/3-Methylamphetamine" title="3-Methylamphetamine">3-Methylamphetamine</a></li> <li><a href="/wiki/4-FA" class="mw-redirect" title="4-FA">4-Fluoroamphetamine</a></li> <li><a href="/wiki/4-FMA" class="mw-redirect" title="4-FMA">4-Fluoromethamphetamine</a></li> <li><a href="/wiki/4-Methylamphetamine" title="4-Methylamphetamine">4-MA</a></li> <li><a href="/wiki/4-Methylmethamphetamine" title="4-Methylmethamphetamine">4-MMA</a></li> <li><a href="/wiki/4-Methylthioamphetamine" title="4-Methylthioamphetamine">4-MTA</a></li> <li><a href="/wiki/6-Fluoronorepinephrine" title="6-Fluoronorepinephrine">6-FNE</a></li> <li><a href="/wiki/AL-1095" title="AL-1095">AL-1095</a></li> <li><a href="/wiki/Alfetamine" title="Alfetamine">Alfetamine</a></li> <li><a href="/wiki/Alpha-Ethylphenethylamine" class="mw-redirect" title="Alpha-Ethylphenethylamine">a-Ethylphenethylamine</a></li> <li><a href="/wiki/Amfecloral" title="Amfecloral">Amfecloral</a></li> <li><a href="/wiki/Amfepentorex" title="Amfepentorex">Amfepentorex</a></li> <li><a href="/wiki/Amidephrine" title="Amidephrine">Amidephrine</a></li> <li><a href="/wiki/2-Amino-1,2-dihydronaphthalene" title="2-Amino-1,2-dihydronaphthalene">2-Amino-1,2-dihydronaphthalene</a></li> <li><a href="/wiki/2-Aminoindane" title="2-Aminoindane">2-Aminoindane</a></li> <li><a href="/wiki/5-(2-Aminopropyl)indole" title="5-(2-Aminopropyl)indole">5-(2-Aminopropyl)indole</a></li> <li><a href="/wiki/2-Aminotetralin" title="2-Aminotetralin">2-Aminotetralin</a></li> <li><a href="/wiki/Acridorex" title="Acridorex">Acridorex</a></li> <li><a href="/wiki/Amphetamine" title="Amphetamine">Amphetamine</a> (<a href="/wiki/Dextroamphetamine" title="Dextroamphetamine">Dextroamphetamine</a>, <a href="/wiki/Levoamphetamine" title="Levoamphetamine">Levoamphetamine</a>)</li> <li><a href="/wiki/Amphetaminil" class="mw-redirect" title="Amphetaminil">Amphetaminil</a></li> <li><a href="/wiki/Arbutamine" title="Arbutamine">Arbutamine</a></li> <li><a href="/wiki/%CE%92-Methylphenethylamine" title="Β-Methylphenethylamine">β-Methylphenethylamine</a></li> <li><a href="/wiki/%CE%92-Phenylmethamphetamine" title="Β-Phenylmethamphetamine">β-Phenylmethamphetamine</a></li> <li><a href="/wiki/Benfluorex" title="Benfluorex">Benfluorex</a></li> <li><a href="/wiki/Benzphetamine" title="Benzphetamine">Benzphetamine</a></li> <li><a href="/wiki/Benzodioxolylbutanamine" class="mw-redirect" title="Benzodioxolylbutanamine">BDB</a></li> <li><a href="/wiki/BOH_(drug)" title="BOH (drug)">BOH</a></li> <li><a href="/wiki/3-Benzhydrylmorpholine" title="3-Benzhydrylmorpholine">3-Benzhydrylmorpholine</a></li> <li><a href="/wiki/Benzofuranylpropylaminopentane" title="Benzofuranylpropylaminopentane">BPAP</a></li> <li><a href="/wiki/Camfetamine" title="Camfetamine">Camfetamine</a></li> <li><a href="/wiki/Cathine" title="Cathine">Cathine</a></li> <li><a href="/wiki/Chlorphentermine" title="Chlorphentermine">Chlorphentermine</a></li> <li><a href="/wiki/Cilobamine" title="Cilobamine">Cilobamine</a></li> <li><a href="/wiki/Cinnamedrine" title="Cinnamedrine">Cinnamedrine</a></li> <li><a href="/wiki/Clenbuterol" title="Clenbuterol">Clenbuterol</a></li> <li><a href="/wiki/Clobenzorex" title="Clobenzorex">Clobenzorex</a></li> <li><a href="/wiki/Cloforex" title="Cloforex">Cloforex</a></li> <li><a href="/wiki/Clortermine" title="Clortermine">Clortermine</a></li> <li><a href="/wiki/Cypenamine" title="Cypenamine">Cypenamine</a></li> <li><a href="/wiki/D-Deprenyl" title="D-Deprenyl">D-Deprenyl</a></li> <li><a href="/wiki/Denopamine" title="Denopamine">Denopamine</a></li> <li><a href="/wiki/Dimethoxyamphetamine" title="Dimethoxyamphetamine">Dimethoxyamphetamine</a></li> <li><a href="/wiki/Dimethylamphetamine" title="Dimethylamphetamine">Dimethylamphetamine</a></li> <li><a href="/wiki/Dobutamine" title="Dobutamine">Dobutamine</a></li> <li><a href="/wiki/L-DOPA" title="L-DOPA">DOPA</a> (<a href="/wiki/D-DOPA" title="D-DOPA">Dextrodopa</a>, <a href="/wiki/L-DOPA" title="L-DOPA">Levodopa</a>)</li> <li><a href="/wiki/Dopamine" title="Dopamine">Dopamine</a></li> <li><a href="/wiki/Dopexamine" title="Dopexamine">Dopexamine</a></li> <li><a href="/wiki/L-DOPS" class="mw-redirect" title="L-DOPS">Droxidopa</a></li> <li><a href="/wiki/Ethylbenzodioxolylbutanamine" class="mw-redirect" title="Ethylbenzodioxolylbutanamine">EBDB</a></li> <li><a href="/wiki/Ephedrine" title="Ephedrine">Ephedrine</a></li> <li><a href="/wiki/Epinephrine" class="mw-redirect" title="Epinephrine">Epinephrine</a></li> <li><a href="/wiki/Epinine" class="mw-redirect" title="Epinine">Epinine</a></li> <li><a href="/wiki/Etafedrine" title="Etafedrine">Etafedrine</a></li> <li><a href="/wiki/Ethylnorepinephrine" title="Ethylnorepinephrine">Ethylnorepinephrine</a></li> <li><a href="/wiki/Etilamfetamine" title="Etilamfetamine">Etilamfetamine</a></li> <li><a href="/wiki/Etilefrine" title="Etilefrine">Etilefrine</a></li> <li><a href="/wiki/Famprofazone" title="Famprofazone">Famprofazone</a></li> <li><a href="/wiki/Fencamfamin" title="Fencamfamin">Fencamfamin</a></li> <li><a href="/wiki/Fencamine" title="Fencamine">Fencamine</a></li> <li><a href="/wiki/Fenethylline" title="Fenethylline">Fenethylline</a></li> <li><a href="/wiki/Fenfluramine" title="Fenfluramine">Fenfluramine</a> (<a href="/wiki/Dexfenfluramine" title="Dexfenfluramine">Dexfenfluramine</a>, <a href="/wiki/Levofenfluramine" title="Levofenfluramine">Levofenfluramine</a>)</li> <li><a href="/wiki/Fenproporex" title="Fenproporex">Fenproporex</a></li> <li><a href="/wiki/Feprosidnine" title="Feprosidnine">Feprosidnine</a></li> <li><a href="/wiki/Fludorex" title="Fludorex">Fludorex</a></li> <li><a href="/wiki/Formetorex" title="Formetorex">Formetorex</a></li> <li><a href="/wiki/Furfenorex" title="Furfenorex">Furfenorex</a></li> <li><a href="/wiki/Gepefrine" title="Gepefrine">Gepefrine</a></li> <li><a href="/wiki/Hexapradol" title="Hexapradol">Hexapradol</a></li> <li><a href="/wiki/4-Hydroxy-3-methoxymethamphetamine" title="4-Hydroxy-3-methoxymethamphetamine">HMMA</a></li> <li><a href="/wiki/Hordenine" title="Hordenine">Hordenine</a></li> <li><a href="/wiki/4-Hydroxyamphetamine" title="4-Hydroxyamphetamine">4-Hydroxyamphetamine</a></li> <li><a href="/wiki/5-IAI" title="5-IAI">5-Iodo-2-aminoindane</a></li> <li><a href="/wiki/Ibopamine" title="Ibopamine">Ibopamine</a></li> <li><a href="/wiki/Indanylaminopropane" class="mw-redirect" title="Indanylaminopropane">Indanylamphetamine</a></li> <li><a href="/wiki/Iofetamine" class="mw-redirect" title="Iofetamine">Iofetamine</a></li> <li><a href="/wiki/Isoetarine" title="Isoetarine">Isoetarine</a></li> <li><a href="/wiki/Isoprenaline" title="Isoprenaline">Isoprenaline</a></li> <li><a href="/wiki/Selegiline" title="Selegiline">L-Deprenyl</a> (Selegiline)</li> <li><a href="/wiki/Lefetamine" title="Lefetamine">Lefetamine</a></li> <li><a href="/wiki/Lisdexamfetamine" title="Lisdexamfetamine">Lisdexamfetamine</a></li> <li><a href="/wiki/Lophophine" title="Lophophine">Lophophine</a></li> <li><a href="/wiki/Methylbenzodioxolylbutanamine" class="mw-redirect" title="Methylbenzodioxolylbutanamine">MBDB</a></li> <li><a href="/wiki/3,4-Methylenedioxyamphetamine" title="3,4-Methylenedioxyamphetamine">MDA (tenamfetamine)</a></li> <li><a href="/wiki/Methylenedioxybutylamphetamine" title="Methylenedioxybutylamphetamine">MDBU</a></li> <li><a href="/wiki/Methylenedioxyethylamphetamine" class="mw-redirect" title="Methylenedioxyethylamphetamine">MDEA</a></li> <li><a class="mw-selflink selflink">MDMA (midomafetamine)</a></li> <li><a href="/wiki/Methylenedioxymethylphenethylamine" class="mw-redirect" title="Methylenedioxymethylphenethylamine">MDMPEA</a></li> <li><a href="/wiki/Methylenedioxyhydroxyamphetamine" class="mw-redirect" title="Methylenedioxyhydroxyamphetamine">MDOH</a></li> <li><a href="/wiki/Methylenedioxypropylamphetamine" class="mw-redirect" title="Methylenedioxypropylamphetamine">MDPR</a></li> <li><a href="/wiki/Methylenedioxyphenethylamine" class="mw-redirect" title="Methylenedioxyphenethylamine">MDPEA</a></li> <li><a href="/wiki/Mefenorex" title="Mefenorex">Mefenorex</a></li> <li><a href="/wiki/Mephentermine" title="Mephentermine">Mephentermine</a></li> <li><a href="/wiki/Metanephrine" title="Metanephrine">Metanephrine</a></li> <li><a href="/wiki/Metaraminol" title="Metaraminol">Metaraminol</a></li> <li><a href="/wiki/Mesocarb" title="Mesocarb">Mesocarb</a></li> <li><a href="/wiki/Methamphetamine" title="Methamphetamine">Methamphetamine</a> (<a href="/wiki/Methamphetamine" title="Methamphetamine">Dextromethamphetamine</a>, <a href="/wiki/Levomethamphetamine" class="mw-redirect" title="Levomethamphetamine">Levomethamphetamine</a>)</li> <li><a href="/wiki/Methoxamine" title="Methoxamine">Methoxamine</a></li> <li><a href="/wiki/Methoxyphenamine" title="Methoxyphenamine">Methoxyphenamine</a></li> <li><a href="/wiki/3-Methoxy-4-methylamphetamine" title="3-Methoxy-4-methylamphetamine">MMA</a></li> <li><a href="/wiki/Methoxyphenamine" title="Methoxyphenamine">Methoxyphenamine</a></li> <li><a href="/wiki/MMDA_(drug)" title="MMDA (drug)">MMDA</a></li> <li><a href="/wiki/MMDMA" title="MMDMA">MMDMA</a></li> <li><a href="/wiki/3-Methoxymethamphetamine" title="3-Methoxymethamphetamine">MMMA</a></li> <li><a href="/wiki/Morforex" title="Morforex">Morforex</a></li> <li><a href="/wiki/N,alpha-Diethylphenylethylamine" class="mw-redirect" title="N,alpha-Diethylphenylethylamine">N,alpha-Diethylphenylethylamine</a></li> <li><a href="/wiki/N,N-Dimethylphenethylamine" title="N,N-Dimethylphenethylamine">N,N-Dimethylphenethylamine</a></li> <li><a href="/wiki/Naphthylaminopropane" title="Naphthylaminopropane">Naphthylamphetamine</a></li> <li><a href="/wiki/Nisoxetine" title="Nisoxetine">Nisoxetine</a></li> <li><a href="/wiki/Norepinephrine" title="Norepinephrine">Norepinephrine</a></li> <li><a href="/wiki/Norfenefrine" title="Norfenefrine">Norfenefrine</a></li> <li><a href="/wiki/Norfenfluramine" title="Norfenfluramine">Norfenfluramine</a></li> <li><a href="/wiki/Normetanephrine" title="Normetanephrine">Normetanephrine</a></li> <li><a href="/wiki/L-Norpseudoephedrine" title="L-Norpseudoephedrine">L-Norpseudoephedrine</a></li> <li><a href="/wiki/Octopamine" title="Octopamine">Octopamine</a></li> <li><a href="/wiki/Orciprenaline" title="Orciprenaline">Orciprenaline</a></li> <li><a href="/wiki/Ortetamine" title="Ortetamine">Ortetamine</a></li> <li><a href="/wiki/Oxifentorex" title="Oxifentorex">Oxifentorex</a></li> <li><a href="/wiki/Oxilofrine" title="Oxilofrine">Oxilofrine</a></li> <li><a href="/wiki/Para-Bromoamphetamine" title="Para-Bromoamphetamine">PBA</a></li> <li><a href="/wiki/Para-Chloroamphetamine" title="Para-Chloroamphetamine">PCA</a></li> <li><a href="/wiki/Para-Chloromethamphetamine" title="Para-Chloromethamphetamine">PCMA</a></li> <li><a href="/wiki/Norpholedrine" class="mw-redirect" title="Norpholedrine">PHA</a></li> <li><a href="/wiki/Pentorex" title="Pentorex">Pentorex</a></li> <li><a href="/wiki/Phenatine" title="Phenatine">Phenatine</a></li> <li><a href="/wiki/Phenpromethamine" title="Phenpromethamine">Phenpromethamine</a></li> <li><a href="/wiki/Phentermine" title="Phentermine">Phentermine</a></li> <li><a href="/wiki/Phenylalanine" title="Phenylalanine">Phenylalanine</a></li> <li><a href="/wiki/Phenylephrine" title="Phenylephrine">Phenylephrine</a></li> <li><a href="/wiki/Phenylpropanolamine" title="Phenylpropanolamine">Phenylpropanolamine</a></li> <li><a href="/wiki/Pholedrine" title="Pholedrine">Pholedrine</a></li> <li><a href="/wiki/Para-Iodoamphetamine" title="Para-Iodoamphetamine">PIA</a></li> <li><a href="/wiki/Para-Methoxyamphetamine" title="Para-Methoxyamphetamine">PMA</a></li> <li><a href="/wiki/Para-Methoxyethylamphetamine" class="mw-redirect" title="Para-Methoxyethylamphetamine">PMEA</a></li> <li><a href="/wiki/Para-Methoxymethamphetamine" title="Para-Methoxymethamphetamine">PMMA</a></li> <li><a href="/wiki/Phenylpropylaminopentane" title="Phenylpropylaminopentane">PPAP</a></li> <li><a href="/wiki/Prenylamine" title="Prenylamine">Prenylamine</a></li> <li><a href="/wiki/Propylamphetamine" title="Propylamphetamine">Propylamphetamine</a></li> <li><a href="/wiki/Pseudoephedrine" title="Pseudoephedrine">Pseudoephedrine</a></li> <li><a href="/wiki/Ropinirole" title="Ropinirole">Ropinirole</a></li> <li><a href="/wiki/Salbutamol" title="Salbutamol">Salbutamol</a> (<a href="/wiki/Levosalbutamol" title="Levosalbutamol">Levosalbutamol</a>)</li> <li><a href="/wiki/Sibutramine" title="Sibutramine">Sibutramine</a></li> <li><a href="/wiki/Solriamfetol" title="Solriamfetol">Solriamfetol</a></li> <li><a href="/wiki/Synephrine" title="Synephrine">Synephrine</a></li> <li><a href="/wiki/Theodrenaline" title="Theodrenaline">Theodrenaline</a></li> <li><a href="/wiki/Tiflorex" title="Tiflorex">Tiflorex</a></li> <li><a href="/wiki/Tranylcypromine" title="Tranylcypromine">Tranylcypromine</a></li> <li><a href="/wiki/Tyramine" title="Tyramine">Tyramine</a></li> <li><a href="/wiki/Tyrosine" title="Tyrosine">Tyrosine</a></li> <li><a href="/wiki/Xylopropamine" title="Xylopropamine">Xylopropamine</a></li> <li><a href="/wiki/Zylofuramine" title="Zylofuramine">Zylofuramine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Substituted_phenylmorpholine" title="Substituted phenylmorpholine">Phenylmorpholines</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/3-Fluorophenmetrazine" title="3-Fluorophenmetrazine">3-Fluorophenmetrazine</a></li> <li><a href="/wiki/Fenbutrazate" title="Fenbutrazate">Fenbutrazate</a></li> <li><a href="/wiki/Fenmetramide" title="Fenmetramide">Fenmetramide</a></li> <li><a href="/wiki/G-130" title="G-130">G-130</a></li> <li><a href="/wiki/Manifaxine" title="Manifaxine">Manifaxine</a></li> <li><a href="/wiki/Morazone" title="Morazone">Morazone</a></li> <li><a href="/wiki/Morforex" title="Morforex">Morforex</a></li> <li><a href="/wiki/Oxaflozane" title="Oxaflozane">Oxaflozane</a></li> <li><a href="/wiki/PD-128,907" title="PD-128,907">PD-128,907</a></li> <li><a href="/wiki/Phendimetrazine" title="Phendimetrazine">Phendimetrazine</a></li> <li><a href="/wiki/Phenmetrazine" title="Phenmetrazine">Phenmetrazine</a></li> <li><a href="/wiki/2-Phenyl-3,6-dimethylmorpholine" title="2-Phenyl-3,6-dimethylmorpholine">2-Phenyl-3,6-dimethylmorpholine</a></li> <li><a href="/wiki/Pseudophenmetrazine" title="Pseudophenmetrazine">Pseudophenmetrazine</a></li> <li><a href="/wiki/Radafaxine" title="Radafaxine">Radafaxine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Piperazine" title="Piperazine">Piperazines</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/2C-B-BZP" title="2C-B-BZP">2C-B-BZP</a></li> <li><a href="/wiki/1-(3-chlorophenyl)-4-(2-phenylethyl)piperazine" class="mw-redirect" title="1-(3-chlorophenyl)-4-(2-phenylethyl)piperazine">3C-PEP</a></li> <li><a href="/wiki/Benzylpiperazine" title="Benzylpiperazine">BZP</a></li> <li><a href="/wiki/CM156" title="CM156">CM156</a></li> <li><a href="/wiki/DBL-583" title="DBL-583">DBL-583</a></li> <li><a href="/wiki/GBR-12783" title="GBR-12783">GBR-12783</a></li> <li><a href="/wiki/GBR-12935" title="GBR-12935">GBR-12935</a></li> <li><a href="/wiki/GBR-13069" title="GBR-13069">GBR-13069</a></li> <li><a href="/wiki/GBR-13098" title="GBR-13098">GBR-13098</a></li> <li><a href="/wiki/GBR-13119" title="GBR-13119">GBR-13119</a></li> <li><a href="/wiki/JJC8-088" title="JJC8-088">JJC8-088</a></li> <li><a href="/wiki/Para-Methoxyphenylpiperazine" title="Para-Methoxyphenylpiperazine">MeOPP</a></li> <li><a href="/wiki/Methylbenzylpiperazine" title="Methylbenzylpiperazine">MBZP</a></li> <li><a href="/wiki/Ortho-Methylphenylpiperazine" title="Ortho-Methylphenylpiperazine">oMPP</a></li> <li><a href="/wiki/Vanoxerine" title="Vanoxerine">Vanoxerine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Piperidine" title="Piperidine">Piperidines</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/1-Benzyl-4-(2-(diphenylmethoxy)ethyl)piperidine" title="1-Benzyl-4-(2-(diphenylmethoxy)ethyl)piperidine">1-Benzyl-4-(2-(diphenylmethoxy)ethyl)piperidine</a></li> <li><a href="/wiki/2-Benzylpiperidine" title="2-Benzylpiperidine">2-Benzylpiperidine</a></li> <li><a href="/wiki/2-Methyl-3-phenylpiperidine" title="2-Methyl-3-phenylpiperidine">2-Methyl-3-phenylpiperidine</a></li> <li><a href="/wiki/3,4-Dichloromethylphenidate" title="3,4-Dichloromethylphenidate">3,4-Dichloromethylphenidate</a></li> <li><a href="/wiki/4-Benzylpiperidine" title="4-Benzylpiperidine">4-Benzylpiperidine</a></li> <li><a href="/wiki/4-Fluoromethylphenidate" title="4-Fluoromethylphenidate">4-Fluoromethylphenidate</a></li> <li><a href="/wiki/4-Methylmethylphenidate" title="4-Methylmethylphenidate">4-Methylmethylphenidate</a></li> <li><a href="/wiki/Desoxypipradrol" title="Desoxypipradrol">Desoxypipradrol</a></li> <li><a href="/wiki/Difemetorex" title="Difemetorex">Difemetorex</a></li> <li><a href="/wiki/Diphenylpyraline" title="Diphenylpyraline">Diphenylpyraline</a></li> <li><a href="/wiki/HDEP-28" title="HDEP-28">Ethylnaphthidate</a></li> <li><a href="/wiki/Ethylphenidate" title="Ethylphenidate">Ethylphenidate</a></li> <li><a href="/wiki/HDMP-28" title="HDMP-28">Methylnaphthidate</a></li> <li><a href="/wiki/Isopropylphenidate" title="Isopropylphenidate">Isopropylphenidate</a></li> <li><a href="/wiki/JZ-IV-10" title="JZ-IV-10">JZ-IV-10</a></li> <li><a href="/wiki/Methylphenidate" title="Methylphenidate">Methylphenidate</a> (<a href="/wiki/Dexmethylphenidate" title="Dexmethylphenidate">Dexmethylphenidate</a>)</li> <li><a href="/wiki/(%2B)-CPCA" title="(+)-CPCA">Nocaine</a></li> <li><a href="/wiki/Levophacetoperane" title="Levophacetoperane">Phacetoperane</a></li> <li><a href="/wiki/Pipradrol" title="Pipradrol">Pipradrol</a></li> <li><a href="/wiki/Propylphenidate" title="Propylphenidate">Propylphenidate</a></li> <li><a href="/wiki/Serdexmethylphenidate" title="Serdexmethylphenidate">Serdexmethylphenidate</a></li> <li><a href="/wiki/SCH-5472" title="SCH-5472">SCH-5472</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Pyrrolidine" title="Pyrrolidine">Pyrrolidines</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/2-Diphenylmethylpyrrolidine" title="2-Diphenylmethylpyrrolidine">2-Diphenylmethylpyrrolidine</a></li> <li><a href="/wiki/4-Chloro-alpha-pyrrolidinovalerophenone" class="mw-redirect" title="4-Chloro-alpha-pyrrolidinovalerophenone">4-Cl-PVP</a></li> <li><a href="/wiki/5-DBFPV" title="5-DBFPV">5-DBFPV</a></li> <li><a href="/wiki/Alpha-Pyrrolidinopropiophenone" class="mw-redirect" title="Alpha-Pyrrolidinopropiophenone">α-PPP</a></li> <li><a href="/wiki/Alpha-Pyrrolidinobutiophenone" class="mw-redirect" title="Alpha-Pyrrolidinobutiophenone">α-PBP</a></li> <li><a href="/wiki/%CE%91-PCYP" title="Α-PCYP">α-PCYP</a></li> <li><a href="/wiki/%CE%91-PHiP" title="Α-PHiP">α-PHiP</a></li> <li><a href="/wiki/Alpha-Pyrrolidinohexiophenone" class="mw-redirect" title="Alpha-Pyrrolidinohexiophenone">α-PHP</a></li> <li><a href="/wiki/%CE%91-Pyrrolidinoheptaphenone" title="Α-Pyrrolidinoheptaphenone">α-PHPP</a></li> <li><a href="/wiki/Alpha-Pyrrolidinopentiophenone" class="mw-redirect" title="Alpha-Pyrrolidinopentiophenone">α-PVP</a></li> <li><a href="/wiki/Alpha-Pyrrolidinopentiothiophenone" class="mw-redirect" title="Alpha-Pyrrolidinopentiothiophenone">α-PVT</a></li> <li><a href="/wiki/Diphenylprolinol" title="Diphenylprolinol">Diphenylprolinol</a></li> <li><a href="/wiki/3%27,4%27-Dimethoxy-%CE%B1-Pyrrolidinopentiophenone" class="mw-redirect" title="3',4'-Dimethoxy-α-Pyrrolidinopentiophenone">DMPVP</a></li> <li><a href="/wiki/4%27-Fluoro-%CE%B1-Pyrrolidinooctanophenone" class="mw-redirect" title="4'-Fluoro-α-Pyrrolidinooctanophenone">FPOP</a></li> <li><a href="/wiki/4%27-Fluoro-%CE%B1-Pyrrolidinopentiophenone" class="mw-redirect" title="4'-Fluoro-α-Pyrrolidinopentiophenone">FPVP</a></li> <li><a href="/wiki/3%27,4%27-Methylenedioxy-%CE%B1-pyrrolidinopropiophenone" title="3',4'-Methylenedioxy-α-pyrrolidinopropiophenone">MDPPP</a></li> <li><a href="/wiki/3%27,4%27-Methylenedioxy-%CE%B1-pyrrolidinobutiophenone" title="3',4'-Methylenedioxy-α-pyrrolidinobutiophenone">MDPBP</a></li> <li><a href="/wiki/4%27-Methyl-a-pyrrolidinobutiophenone" class="mw-redirect" title="4'-Methyl-a-pyrrolidinobutiophenone">MPBP</a></li> <li><a href="/wiki/4%27-Methyl-%CE%B1-pyrrolidinohexiophenone" title="4'-Methyl-α-pyrrolidinohexiophenone">MPHP</a></li> <li><a href="/wiki/4%27-Methyl-%CE%B1-pyrrolidinopropiophenone" title="4'-Methyl-α-pyrrolidinopropiophenone">MPPP</a></li> <li><a href="/wiki/4%27-Methoxy-%CE%B1-Pyrrolidinopentiophenone" class="mw-redirect" title="4'-Methoxy-α-Pyrrolidinopentiophenone">MOPVP</a></li> <li><a href="/wiki/4%27-Methoxy-%CE%B1-pyrrolidinopropiophenone" title="4'-Methoxy-α-pyrrolidinopropiophenone">MOPPP</a></li> <li><a href="/wiki/Indapyrophenidone" title="Indapyrophenidone">Indapyrophenidone</a></li> <li><a href="/wiki/Methylenedioxypyrovalerone" title="Methylenedioxypyrovalerone">MDPV</a></li> <li><a href="/wiki/Naphyrone" title="Naphyrone">Naphyrone</a></li> <li><a href="/wiki/Phenylethylpyrrolidine" title="Phenylethylpyrrolidine">PEP</a></li> <li><a href="/wiki/Picilorex" title="Picilorex">Picilorex</a></li> <li><a href="/wiki/Prolintane" title="Prolintane">Prolintane</a></li> <li><a href="/wiki/Pyrovalerone" title="Pyrovalerone">Pyrovalerone</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Racetam" title="Racetam">Racetams</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Oxiracetam" title="Oxiracetam">Oxiracetam</a></li> <li><a href="/wiki/Phenylpiracetam" title="Phenylpiracetam">Phenylpiracetam</a></li> <li><a href="/wiki/Phenylpiracetam_hydrazide" title="Phenylpiracetam hydrazide">Phenylpiracetam hydrazide</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Tropane" title="Tropane">Tropanes</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/4-fluorotropacocaine" class="mw-redirect" title="4-fluorotropacocaine">4-fluorotropacocaine</a></li> <li><a href="/wiki/4%27-Fluorococaine" class="mw-redirect" title="4'-Fluorococaine">4'-Fluorococaine</a></li> <li><a href="/wiki/Altropane" title="Altropane">Altropane (IACFT)</a></li> <li><a href="/wiki/Brasofensine" title="Brasofensine">Brasofensine</a></li> <li><a href="/wiki/WIN_35428" class="mw-redirect" title="WIN 35428">CFT (WIN 35,428)</a></li> <li><a href="/wiki/RTI-55" title="RTI-55">β-CIT (RTI-55)</a></li> <li><a href="/wiki/Cocaethylene" title="Cocaethylene">Cocaethylene</a></li> <li><a href="/wiki/Cocaine" title="Cocaine">Cocaine</a></li> <li><a href="/wiki/Dichloropane" title="Dichloropane">Dichloropane (RTI-111)</a></li> <li><a href="/wiki/Difluoropine" title="Difluoropine">Difluoropine</a></li> <li><a href="/wiki/FE-%CE%B2-CPPIT" title="FE-β-CPPIT">FE-β-CPPIT</a></li> <li><a href="/wiki/FP-%CE%B2-CPPIT" title="FP-β-CPPIT">FP-β-CPPIT</a></li> <li><a href="/wiki/Ioflupane_(123I)" title="Ioflupane (123I)">Ioflupane (123I)</a></li> <li><a href="/wiki/Norcocaine" title="Norcocaine">Norcocaine</a></li> <li><a href="/wiki/2-Propanoyl-3-(4-isopropylphenyl)-tropane" title="2-Propanoyl-3-(4-isopropylphenyl)-tropane">PIT</a></li> <li><a href="/wiki/2%CE%B2-Propanoyl-3%CE%B2-(4-tolyl)-tropane" title="2β-Propanoyl-3β-(4-tolyl)-tropane">PTT</a></li> <li><a href="/wiki/RTI-31" title="RTI-31">RTI-31</a></li> <li><a href="/wiki/RTI-32" title="RTI-32">RTI-32</a></li> <li><a href="/wiki/RTI-51" title="RTI-51">RTI-51</a></li> <li><a href="/wiki/RTI-112" title="RTI-112">RTI-112</a></li> <li><a href="/wiki/RTI-113" title="RTI-113">RTI-113</a></li> <li><a href="/wiki/RTI-120" title="RTI-120">RTI-120</a></li> <li><a href="/wiki/RTI-121" title="RTI-121">RTI-121 (IPCIT)</a></li> <li><a href="/wiki/RTI-126" title="RTI-126">RTI-126</a></li> <li><a href="/wiki/RTI-150" title="RTI-150">RTI-150</a></li> <li><a href="/wiki/RTI-177" title="RTI-177">RTI-177</a></li> <li><a href="/wiki/RTI-229" title="RTI-229">RTI-229</a></li> <li><a href="/wiki/(-)-2%CE%B2-(3-(4-Methylphenyl)isoxazol-5-yl)-3%CE%B2-(4-chlorophenyl)tropane" class="mw-redirect" title="(-)-2β-(3-(4-Methylphenyl)isoxazol-5-yl)-3β-(4-chlorophenyl)tropane">RTI-336</a></li> <li><a href="/wiki/RTI-354" class="mw-redirect" title="RTI-354">RTI-354</a></li> <li><a href="/wiki/RTI-371" title="RTI-371">RTI-371</a></li> <li><a href="/wiki/RTI-386" class="mw-redirect" title="RTI-386">RTI-386</a></li> <li><a href="/wiki/Salicylmethylecgonine" title="Salicylmethylecgonine">Salicylmethylecgonine</a></li> <li><a href="/wiki/Tesofensine" title="Tesofensine">Tesofensine</a></li> <li><a href="/wiki/Troparil" title="Troparil">Troparil (β-CPT, WIN 35,065-2)</a></li> <li><a href="/wiki/Tropoxane" title="Tropoxane">Tropoxane</a></li> <li><a href="/wiki/2%CE%B2-Propanoyl-3%CE%B2-(2-naphthyl)-tropane" title="2β-Propanoyl-3β-(2-naphthyl)-tropane">WF-23</a></li> <li><a href="/wiki/2%CE%B1-(Propanoyl)-3%CE%B2-(2-(6-methoxynaphthyl))-tropane" title="2α-(Propanoyl)-3β-(2-(6-methoxynaphthyl))-tropane">WF-33</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Substituted_tryptamine" title="Substituted tryptamine">Tryptamines</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/4-HO-%CE%B1MT" title="4-HO-αMT">4-HO-αMT</a></li> <li><a href="/wiki/4-Methyl-%CE%B1ET" class="mw-redirect" title="4-Methyl-αET">4-Methyl-αET</a></li> <li><a href="/wiki/4-Methyl-%CE%B1MT" class="mw-redirect" title="4-Methyl-αMT">4-Methyl-αMT</a></li> <li><a href="/wiki/5-Chloro-%CE%B1MT" title="5-Chloro-αMT">5-Chloro-αMT</a></li> <li><a href="/wiki/5-Fluoro-%CE%B1MT" class="mw-redirect" title="5-Fluoro-αMT">5-Fluoro-αMT</a></li> <li><a href="/wiki/5-MeO-%CE%B1ET" class="mw-redirect" title="5-MeO-αET">5-MeO-αET</a></li> <li><a href="/wiki/5-MeO-%CE%B1MT" class="mw-redirect" title="5-MeO-αMT">5-MeO-αMT</a></li> <li><a href="/wiki/5-Methoxy-N,N-diisopropyltryptamine" class="mw-redirect" title="5-Methoxy-N,N-diisopropyltryptamine">5-MeO-DIPT</a></li> <li><a href="/wiki/6-Fluoro-%CE%B1MT" class="mw-redirect" title="6-Fluoro-αMT">6-Fluoro-αMT</a></li> <li><a href="/wiki/7-Methyl-%CE%B1ET" class="mw-redirect" title="7-Methyl-αET">7-Methyl-αET</a></li> <li><a href="/wiki/%CE%91-Ethyltryptamine" title="Α-Ethyltryptamine">αET</a></li> <li><a href="/wiki/%CE%91-Methyltryptamine" title="Α-Methyltryptamine">αMT</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Others</th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/2-MDP" title="2-MDP">2-MDP</a></li> <li><a href="/wiki/3,3-Diphenylcyclobutanamine" title="3,3-Diphenylcyclobutanamine">3,3-Diphenylcyclobutanamine</a></li> <li><a href="/wiki/Amfonelic_acid" title="Amfonelic acid">Amfonelic acid</a></li> <li><a href="/wiki/Amineptine" title="Amineptine">Amineptine</a></li> <li><a href="/wiki/Amiphenazole" title="Amiphenazole">Amiphenazole</a></li> <li><a href="/wiki/Atipamezole" title="Atipamezole">Atipamezole</a></li> <li><a href="/wiki/Atomoxetine" title="Atomoxetine">Atomoxetine</a></li> <li><a href="/wiki/Bemegride" title="Bemegride">Bemegride</a></li> <li><a href="/wiki/Benzydamine" title="Benzydamine">Benzydamine</a></li> <li><a href="/wiki/Butyltolylquinuclidine" title="Butyltolylquinuclidine">BTQ</a></li> <li><a href="/wiki/BTS_74,398" title="BTS 74,398">BTS 74,398</a></li> <li><a href="/wiki/Centanafadine" title="Centanafadine">Centanafadine</a></li> <li><a href="/wiki/Ciclazindol" title="Ciclazindol">Ciclazindol</a></li> <li><a href="/wiki/Clofenciclan" title="Clofenciclan">Clofenciclan</a></li> <li><a href="/wiki/Cropropamide" class="mw-redirect" title="Cropropamide">Cropropamide</a></li> <li><a href="/wiki/Crotetamide" class="mw-redirect" title="Crotetamide">Crotetamide</a></li> <li><a href="/wiki/D-161" title="D-161">D-161</a></li> <li><a href="/wiki/Desipramine" title="Desipramine">Desipramine</a></li> <li><a href="/wiki/Diclofensine" title="Diclofensine">Diclofensine</a></li> <li><a href="/wiki/Dimethocaine" title="Dimethocaine">Dimethocaine</a></li> <li><a href="/wiki/Efaroxan" title="Efaroxan">Efaroxan</a></li> <li><a href="/wiki/Etamivan" title="Etamivan">Etamivan</a></li> <li><a href="/wiki/Fenisorex" title="Fenisorex">Fenisorex</a></li> <li><a href="/wiki/Fenpentadiol" title="Fenpentadiol">Fenpentadiol</a></li> <li><a href="/wiki/Gamfexine" title="Gamfexine">Gamfexine</a></li> <li><a href="/wiki/Gilutensin" class="mw-redirect" title="Gilutensin">Gilutensin</a></li> <li><a href="/wiki/GSK1360707F" title="GSK1360707F">GSK1360707F</a></li> <li><a href="/wiki/GYKI-52895" class="mw-redirect" title="GYKI-52895">GYKI-52895</a></li> <li><a href="/wiki/Hexacyclonate" title="Hexacyclonate">Hexacyclonate</a></li> <li><a href="/wiki/Idazoxan" title="Idazoxan">Idazoxan</a></li> <li><a href="/wiki/Indanorex" title="Indanorex">Indanorex</a></li> <li><a href="/wiki/Indatraline" title="Indatraline">Indatraline</a></li> <li><a href="/wiki/JNJ-7925476" title="JNJ-7925476">JNJ-7925476</a></li> <li><a href="/wiki/Lazabemide" title="Lazabemide">Lazabemide</a></li> <li><a href="/wiki/Leptacline" title="Leptacline">Leptacline</a></li> <li><a href="/wiki/Lomevactone" title="Lomevactone">Lomevactone</a></li> <li><a href="/wiki/LR-5182" title="LR-5182">LR-5182</a></li> <li><a href="/wiki/Mazindol" title="Mazindol">Mazindol</a></li> <li><a href="/wiki/Meclofenoxate" title="Meclofenoxate">Meclofenoxate</a></li> <li><a href="/wiki/Medifoxamine" title="Medifoxamine">Medifoxamine</a></li> <li><a href="/wiki/Mefexamide" title="Mefexamide">Mefexamide</a></li> <li><a href="/wiki/Methamnetamine" title="Methamnetamine">Methamnetamine</a></li> <li><a href="/wiki/Methastyridone" title="Methastyridone">Methastyridone</a></li> <li><a href="/wiki/Methiopropamine" title="Methiopropamine">Methiopropamine</a></li> <li><a href="/wiki/Naphthylaminopropane" title="Naphthylaminopropane">Naphthylaminopropane</a></li> <li><a href="/wiki/Nefopam" title="Nefopam">Nefopam</a></li> <li><a href="/wiki/Nikethamide" title="Nikethamide">Nikethamide</a></li> <li><a href="/wiki/Nomifensine" title="Nomifensine">Nomifensine</a></li> <li><a href="/wiki/O-2172" title="O-2172">O-2172</a></li> <li><a href="/wiki/Oxaprotiline" title="Oxaprotiline">Oxaprotiline</a></li> <li><a href="/wiki/PNU-99,194" title="PNU-99,194">PNU-99,194</a></li> <li><a href="/wiki/PRC200" class="mw-redirect" title="PRC200">PRC200-SS</a></li> <li><a href="/wiki/Rasagiline" title="Rasagiline">Rasagiline</a></li> <li><a href="/wiki/Rauwolscine" title="Rauwolscine">Rauwolscine</a></li> <li><a href="/wiki/Rubidium_chloride" title="Rubidium chloride">Rubidium chloride</a></li> <li><a href="/wiki/Setazindol" title="Setazindol">Setazindol</a></li> <li><a href="/wiki/Tametraline" title="Tametraline">Tametraline</a></li> <li><a href="/wiki/Tandamine" title="Tandamine">Tandamine</a></li> <li><a href="/wiki/Thiopropamine" title="Thiopropamine">Thiopropamine</a></li> <li><a href="/wiki/Thiothinone" title="Thiothinone">Thiothinone</a></li> <li><a href="/wiki/Trazium" title="Trazium">Trazium</a></li> <li><a href="/wiki/UH-232" title="UH-232">UH-232</a></li> <li><a href="/wiki/Yohimbine" title="Yohimbine">Yohimbine</a></li></ul> </div></td></tr><tr><td class="navbox-abovebelow" colspan="2" style="font-style:italic"><div><a href="/wiki/ATC_code" class="mw-redirect" title="ATC code">ATC code</a>: <a href="/wiki/ATC_code_N06#N06B" title="ATC code N06">N06B</a></div></td></tr></tbody></table></div></div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235" /></div><div role="navigation" class="navbox" aria-labelledby="Pharmacodynamics105" style="padding:3px"><table class="nowraplinks mw-collapsible mw-collapsed navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2" style="background:#e8e8ff;background:#ccccff"><div id="Pharmacodynamics105" style="font-size:114%;margin:0 4em"><a href="/wiki/Pharmacodynamics" title="Pharmacodynamics">Pharmacodynamics</a></div></th></tr><tr><td colspan="2" class="navbox-list navbox-odd" style="width:100%;padding:0;font-size:114%"><div style="padding:0px"> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374" /><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235" /></div><div role="navigation" class="navbox" aria-labelledby="Monoaminergic_neurotoxins598" style="padding:3px"><table class="nowraplinks mw-collapsible mw-collapsed navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374" /><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231" /><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Monoaminergic_neurotoxins" title="Template:Monoaminergic neurotoxins"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Monoaminergic_neurotoxins" title="Template talk:Monoaminergic neurotoxins"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Monoaminergic_neurotoxins" title="Special:EditPage/Template:Monoaminergic neurotoxins"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Monoaminergic_neurotoxins598" style="font-size:114%;margin:0 4em"><a href="/wiki/Monoaminergic_neurotoxin" class="mw-redirect" title="Monoaminergic neurotoxin">Monoaminergic neurotoxins</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Dopaminergic" title="Dopaminergic">Dopaminergic</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/2%E2%80%B2-CH3-MPTP" title="2′-CH3-MPTP">2′-CH3-MPTP (2′-methyl-MPTP)</a></li> <li><a href="/wiki/2,4,5-Trihydroxyamphetamine" title="2,4,5-Trihydroxyamphetamine">2,4,5-THA</a></li> <li><a href="/wiki/2,4,5-Trihydroxymethamphetamine" title="2,4,5-Trihydroxymethamphetamine">2,4,5-THMA</a></li> <li><a href="/wiki/4-Methylmethamphetamine" title="4-Methylmethamphetamine">4-MMA</a></li> <li><a href="/w/index.php?title=5-S-Cysteinyldopamine&action=edit&redlink=1" class="new" title="5-S-Cysteinyldopamine (page does not exist)">5-S-Cysteinyldopamine</a></li> <li><a href="/wiki/5,6-Dihydroxytryptamine" title="5,6-Dihydroxytryptamine">5,6-DHT</a></li> <li><a href="/wiki/6-Hydroxydopa" title="6-Hydroxydopa">6-Hydroxydopa</a></li> <li><a href="/w/index.php?title=6-Hydroxydopamine_quinone&action=edit&redlink=1" class="new" title="6-Hydroxydopamine quinone (page does not exist)">6-OHDA quinone</a></li> <li><a href="/wiki/6,7-Dihydroxytryptamine" title="6,7-Dihydroxytryptamine">6,7-DHT</a></li> <li><a href="/wiki/Aldehyde_dehydrogenase_inhibitor" class="mw-redirect" title="Aldehyde dehydrogenase inhibitor">ALDH inhibitors</a> (e.g., <a href="/wiki/Disulfiram" title="Disulfiram">disulfiram</a>, <a href="/wiki/Methylmercury" title="Methylmercury">methylmercury</a>)</li> <li><a href="/wiki/Amphetamine" title="Amphetamine">Amphetamine</a></li> <li><a href="/wiki/Benomyl" title="Benomyl">Benomyl</a></li> <li><a href="/wiki/Daidzin" title="Daidzin">Daidzin</a></li> <li><a href="/wiki/Dieldrin" title="Dieldrin">Dieldrin</a></li> <li><a href="/w/index.php?title=DOPA_quinone&action=edit&redlink=1" class="new" title="DOPA quinone (page does not exist)">DOPA quinone</a></li> <li><a href="/wiki/3,4-Dihydroxyphenylacetaldehyde" title="3,4-Dihydroxyphenylacetaldehyde">DOPAL</a></li> <li><a href="/w/index.php?title=DOPAL_quinone&action=edit&redlink=1" class="new" title="DOPAL quinone (page does not exist)">DOPAL quinone</a></li> <li><a href="/wiki/Dopamine" title="Dopamine">Dopamine</a></li> <li><a href="/w/index.php?title=Dopamine_quinone&action=edit&redlink=1" class="new" title="Dopamine quinone (page does not exist)">Dopamine quinone</a></li> <li><a href="/wiki/Fenpropathrin" title="Fenpropathrin">Fenpropathrin</a></li> <li><a href="/wiki/Haloperidol" title="Haloperidol">Haloperidol</a></li> <li><a href="/wiki/HPP%2B" title="HPP+">HPP+</a></li> <li><a href="/wiki/HPTP" title="HPTP">HPTP</a></li> <li><a href="/wiki/Mancozeb" title="Mancozeb">Mancozeb</a></li> <li><a href="/wiki/Maneb" title="Maneb">Maneb</a></li> <li><a href="/wiki/Mephedrone" title="Mephedrone">Mephedrone</a></li> <li><a href="/wiki/Methamphetamine" title="Methamphetamine">Methamphetamine</a></li> <li><a href="/wiki/Methcathinone" title="Methcathinone">Methcathinone</a></li> <li><a href="/wiki/Methylone" title="Methylone">Methylone</a></li> <li><a href="/wiki/MPP%2B" title="MPP+">MPP+ (cyperquat)</a></li> <li><a href="/wiki/MPTP" title="MPTP">MPTP</a></li> <li><a href="/w/index.php?title=N-Methylnorsalsolinol&action=edit&redlink=1" class="new" title="N-Methylnorsalsolinol (page does not exist)">N-Methylnorsalsolinol</a></li> <li><a href="/wiki/Norsalsolinol" title="Norsalsolinol">Norsalsolinol</a></li> <li><a href="/wiki/Oxidopamine" title="Oxidopamine">Oxidopamine (6-OHDA)</a></li> <li><a href="/wiki/Paraquat" title="Paraquat">Paraquat</a></li> <li><a href="/wiki/Rotenone" title="Rotenone">Rotenone</a></li> <li><a href="/wiki/Salsolinol" title="Salsolinol">Salsolinol</a></li> <li><a href="/wiki/Zinc_bis(dimethyldithiocarbamate)" title="Zinc bis(dimethyldithiocarbamate)">Ziram</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Noradrenergic" class="mw-redirect" title="Noradrenergic">Noradrenergic</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/2%E2%80%B2-NH2-MPTP" title="2′-NH2-MPTP">2′-NH2-MPTP (2′-amino-MPTP)</a></li> <li><a href="/wiki/2,4,5-Trihydroxyamphetamine" title="2,4,5-Trihydroxyamphetamine">2,4,5-THA</a></li> <li><a href="/wiki/4,5-Dihydroxytryptamine" title="4,5-Dihydroxytryptamine">4,5-DHT</a></li> <li><a href="/wiki/5,6-Dihydroxytryptamine" title="5,6-Dihydroxytryptamine">5,6-DHT</a></li> <li><a href="/wiki/5,7-Dihydroxytryptamine" title="5,7-Dihydroxytryptamine">5,7-DHT</a></li> <li><a href="/wiki/6-Hydroxydopa" title="6-Hydroxydopa">6-Hydroxydopa</a></li> <li><a href="/wiki/3,4-Dihydroxyphenylglycolaldehyde" title="3,4-Dihydroxyphenylglycolaldehyde">DOPEGAL</a></li> <li><a href="/wiki/DSP-4" title="DSP-4">DSP-4</a></li> <li><a href="/wiki/3,4-Methylenedioxyamphetamine" title="3,4-Methylenedioxyamphetamine">MDA (tenamfetamine)</a></li> <li><a href="/wiki/Oxidopamine" title="Oxidopamine">Oxidopamine (6-OHDA)</a></li> <li><a href="/wiki/Xylamine" title="Xylamine">Xylamine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Serotonin" title="Serotonin">Serotonergic</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/2%E2%80%B2-NH2-MPTP" title="2′-NH2-MPTP">2′-NH2-MPTP (2′-amino-MPTP)</a></li> <li><a href="/wiki/2,4-Dichloroamphetamine" title="2,4-Dichloroamphetamine">2,4-DCA</a></li> <li><a href="/wiki/2,4,5-Trihydroxyamphetamine" title="2,4,5-Trihydroxyamphetamine">2,4,5-THA</a></li> <li><a href="/wiki/2,4,5-Trihydroxymethamphetamine" title="2,4,5-Trihydroxymethamphetamine">2,4,5-THMA</a></li> <li><a href="/wiki/3-Chloroamphetamine" title="3-Chloroamphetamine">3-CA</a></li> <li><a href="/wiki/3,4-Dichloroamphetamine" title="3,4-Dichloroamphetamine">3,4-DCA</a></li> <li><a href="/wiki/4-Chlorophenylisobutylamine" title="4-Chlorophenylisobutylamine">4-CAB (α-ethyl-PCA)</a></li> <li><a href="/wiki/Para-Chloromethamphetamine" title="Para-Chloromethamphetamine">4-CMA</a></li> <li><a href="/wiki/4-Hydroxy-5-methoxytryptamine" title="4-Hydroxy-5-methoxytryptamine">4-HO-5-MeO-T</a></li> <li><a href="/wiki/4,5-Dihydroxytryptamine" title="4,5-Dihydroxytryptamine">4,5-DHT</a></li> <li><a href="/wiki/5-Iodo-2-aminoindane" class="mw-redirect" title="5-Iodo-2-aminoindane">5-IAI</a></li> <li><a href="/wiki/5-MAPB" title="5-MAPB">5-MAPB</a></li> <li><a href="/wiki/5,6-Dihydroxytryptamine" title="5,6-Dihydroxytryptamine">5,6-DHT</a></li> <li><a href="/wiki/5,7-Dihydroxytryptamine" title="5,7-Dihydroxytryptamine">5,7-DHT</a></li> <li><a href="/wiki/6,7-Dihydroxytryptamine" title="6,7-Dihydroxytryptamine">6,7-DHT</a></li> <li><a href="/wiki/Alpha-Ethyltryptamine" class="mw-redirect" title="Alpha-Ethyltryptamine">αET</a></li> <li><a href="/wiki/Fenfluramine" title="Fenfluramine">Fenfluramine</a></li> <li><a href="/wiki/Haloperidol" title="Haloperidol">Haloperidol</a></li> <li><a href="/wiki/3,4-Dihydroxyamphetamine" class="mw-redirect" title="3,4-Dihydroxyamphetamine">HHA (α-methyldopamine)</a></li> <li><a href="/wiki/3,4-Dihydroxymethamphetamine" title="3,4-Dihydroxymethamphetamine">HHMA (α-methylepinine, α,N-dimethyldopamine)</a></li> <li><a href="/wiki/HPP%2B" title="HPP+">HPP+</a></li> <li><a href="/wiki/HPTP" title="HPTP">HPTP</a></li> <li><a href="/wiki/MBDB" title="MBDB">MBDB</a></li> <li><a href="/wiki/3,4-Methylenedioxyamphetamine" title="3,4-Methylenedioxyamphetamine">MDA (tenamfetamine)</a></li> <li><a href="/wiki/3,4-Methylenedioxymethamphetamine" class="mw-redirect" title="3,4-Methylenedioxymethamphetamine">MDMA (midomafetamine)</a></li> <li><a href="/wiki/Mephedrone" title="Mephedrone">Mephedrone</a></li> <li><a href="/wiki/Methamphetamine" title="Methamphetamine">Methamphetamine</a></li> <li><a href="/wiki/Methylone" title="Methylone">Methylone</a></li> <li><a href="/wiki/Norfenfluramine" title="Norfenfluramine">Norfenfluramine</a></li> <li><a href="/wiki/Para-Bromoamphetamine" title="Para-Bromoamphetamine">PBA</a></li> <li><a href="/wiki/Para-Bromomethamphetamine" title="Para-Bromomethamphetamine">PBMA</a></li> <li><a href="/wiki/Para-Chloroamphetamine" title="Para-Chloroamphetamine">PCA</a></li> <li><a href="/wiki/Para-Chloromethamphetamine" title="Para-Chloromethamphetamine">PCMA</a></li> <li><a href="/wiki/Para-Iodoamphetamine" title="Para-Iodoamphetamine">PIA</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;">Unsorted</th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/5-Hydroxyindoleacetaldehyde" title="5-Hydroxyindoleacetaldehyde">5-HIAL</a></li> <li><a href="/w/index.php?title=RHPP%2B&action=edit&redlink=1" class="new" title="RHPP+ (page does not exist)">RHPP+</a></li> <li><a href="/w/index.php?title=RHPTP&action=edit&redlink=1" class="new" title="RHPTP (page does not exist)">RHPTP</a></li></ul> </div></td></tr><tr><td class="navbox-abovebelow" colspan="2"><div>See also: <a href="/wiki/Template:Receptor_modulators" title="Template:Receptor modulators">Receptor/signaling modulators</a> • <a href="/wiki/Template:Adrenergics" class="mw-redirect" title="Template:Adrenergics">Adrenergics</a> • <a href="/wiki/Template:Dopaminergics" class="mw-redirect" title="Template:Dopaminergics">Dopaminergics</a> • <a href="/wiki/Template:Melatonergics" class="mw-redirect" title="Template:Melatonergics">Melatonergics</a> • <a href="/wiki/Template:Serotonergics" class="mw-redirect" title="Template:Serotonergics">Serotonergics</a> • <a href="/wiki/Template:Monoamine_reuptake_inhibitors" title="Template:Monoamine reuptake inhibitors">Monoamine reuptake inhibitors</a> • <a href="/wiki/Template:Monoamine_releasing_agents" title="Template:Monoamine releasing agents">Monoamine releasing agents</a> • <a href="/wiki/Template:Monoamine_metabolism_modulators" title="Template:Monoamine metabolism modulators">Monoamine metabolism modulators</a></div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374" /><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235" /></div><div role="navigation" class="navbox" aria-labelledby="Monoamine_releasing_agents1712" style="padding:3px"><table class="nowraplinks mw-collapsible mw-collapsed navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374" /><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231" /><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Monoamine_releasing_agents" title="Template:Monoamine releasing agents"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Monoamine_releasing_agents" title="Template talk:Monoamine releasing agents"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Monoamine_releasing_agents" title="Special:EditPage/Template:Monoamine releasing agents"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Monoamine_releasing_agents1712" style="font-size:114%;margin:0 4em"><a href="/wiki/Monoamine_releasing_agent" title="Monoamine releasing agent">Monoamine releasing agents</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Dopamine_releasing_agents" class="mw-redirect" title="Dopamine releasing agents"><abbr title="Dopamine releasing agents">DRAs</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Dopamine releasing agents</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><td colspan="2" class="navbox-list navbox-odd" style="width:100%;padding:0;text-align: left;"><div style="padding:0 0.25em"> <ul><li>Morpholines: <a href="/wiki/Fenbutrazate" title="Fenbutrazate">Fenbutrazate</a></li> <li><a href="/wiki/Fenmetramide" title="Fenmetramide">Fenmetramide</a></li> <li><a href="/wiki/Morazone" title="Morazone">Morazone</a></li> <li><a href="/wiki/Morforex" title="Morforex">Morforex</a></li> <li><a href="/wiki/Phendimetrazine" title="Phendimetrazine">Phendimetrazine</a></li> <li><a href="/wiki/Phenmetrazine" title="Phenmetrazine">Phenmetrazine</a></li> <li><a href="/wiki/Pseudophenmetrazine" title="Pseudophenmetrazine">Pseudophenmetrazine</a></li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-even" style="width:100%;padding:0;text-align: left;"><div style="padding:0 0.25em"> <ul><li>Oxazolines: <a href="/wiki/4-Methylaminorex" title="4-Methylaminorex">4-MAR</a></li> <li><a href="/wiki/Aminorex" title="Aminorex">Aminorex</a></li> <li><a href="/wiki/Clominorex" title="Clominorex">Clominorex</a></li> <li><a href="/wiki/Cyclazodone" title="Cyclazodone">Cyclazodone</a></li> <li><a href="/wiki/Fenozolone" title="Fenozolone">Fenozolone</a></li> <li><a href="/wiki/Fluminorex" title="Fluminorex">Fluminorex</a></li> <li><a href="/wiki/Pemoline" title="Pemoline">Pemoline</a></li> <li><a href="/wiki/Thozalinone" title="Thozalinone">Thozalinone</a></li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-odd" style="width:100%;padding:0;text-align: left;"><div style="padding:0 0.25em"> <ul><li>Phenethylamines: <a href="/wiki/Phenylethanolamine" title="Phenylethanolamine">2-OH-PEA</a></li> <li><a href="/wiki/4-Chlorophenylisobutylamine" title="4-Chlorophenylisobutylamine">4-CAB</a></li> <li><a href="/wiki/4-Fluoroamphetamine" title="4-Fluoroamphetamine">4-FA</a></li> <li><a href="/wiki/4-Fluoromethamphetamine" title="4-Fluoromethamphetamine">4-FMA</a></li> <li><a href="/wiki/4-Methylamphetamine" title="4-Methylamphetamine">4-MA</a></li> <li><a href="/wiki/4-Methylmethamphetamine" title="4-Methylmethamphetamine">4-MMA</a></li> <li><a href="/wiki/Alfetamine" title="Alfetamine">Alfetamine</a></li> <li><a href="/wiki/Amfecloral" title="Amfecloral">Amfecloral</a></li> <li><a href="/wiki/Amfepentorex" title="Amfepentorex">Amfepentorex</a></li> <li><a href="/wiki/Amfepramone" title="Amfepramone">Amfepramone</a></li> <li><a href="/wiki/Amphetamine" title="Amphetamine">Amphetamine</a> (<a href="/wiki/Dextroamphetamine" title="Dextroamphetamine">Dextroamphetamine</a></li> <li><a href="/wiki/Levoamphetamine" title="Levoamphetamine">Levoamphetamine</a>)</li> <li><a href="/wiki/Amphetaminil" class="mw-redirect" title="Amphetaminil">Amphetaminil</a></li> <li><a href="/wiki/%CE%92-Methylphenethylamine" title="Β-Methylphenethylamine">β-Me-PEA</a></li> <li><a href="/wiki/1,3-Benzodioxolylbutanamine" title="1,3-Benzodioxolylbutanamine">BDB</a></li> <li><a href="/wiki/BOH_(drug)" title="BOH (drug)">BOH</a></li> <li><a href="/wiki/Benzphetamine" title="Benzphetamine">Benzphetamine</a></li> <li><a href="/wiki/Buphedrone" title="Buphedrone">Buphedrone</a></li> <li><a href="/wiki/Butylone" title="Butylone">Butylone</a></li> <li><a href="/wiki/Cathine" title="Cathine">Cathine</a></li> <li><a href="/wiki/Cathinone" title="Cathinone">Cathinone</a></li> <li><a href="/wiki/Clobenzorex" title="Clobenzorex">Clobenzorex</a></li> <li><a href="/wiki/Clortermine" title="Clortermine">Clortermine</a></li> <li><a href="/wiki/D-Deprenyl" title="D-Deprenyl">D-Deprenyl</a></li> <li><a href="/wiki/Dimethoxyamphetamine" title="Dimethoxyamphetamine">DMA</a></li> <li><a href="/wiki/Dimethoxymethamphetamine" class="mw-redirect" title="Dimethoxymethamphetamine">DMMA</a></li> <li><a href="/wiki/Dimethylamphetamine" title="Dimethylamphetamine">Dimethylamphetamine</a></li> <li><a href="/wiki/Ephedrine" title="Ephedrine">Ephedrine</a></li> <li><a href="/wiki/Ethcathinone" title="Ethcathinone">Ethcathinone</a></li> <li><a href="/wiki/1,3-Benzodioxolyl-N-ethylbutanamine" title="1,3-Benzodioxolyl-N-ethylbutanamine">EBDB</a></li> <li><a href="/wiki/Ethylone" title="Ethylone">Ethylone</a></li> <li><a href="/wiki/Etilamfetamine" title="Etilamfetamine">Etilamfetamine</a></li> <li><a href="/wiki/Famprofazone" title="Famprofazone">Famprofazone</a></li> <li><a href="/wiki/Fenethylline" title="Fenethylline">Fenethylline</a></li> <li><a href="/wiki/Fenproporex" title="Fenproporex">Fenproporex</a></li> <li><a href="/wiki/Flephedrone" title="Flephedrone">Flephedrone</a></li> <li><a href="/wiki/Fludorex" title="Fludorex">Fludorex</a></li> <li><a href="/wiki/Furfenorex" title="Furfenorex">Furfenorex</a></li> <li><a href="/wiki/Hordenine" title="Hordenine">Hordenine</a></li> <li><a href="/wiki/4-Hydroxyamphetamine" title="4-Hydroxyamphetamine">4-Hydroxyamphetamine</a></li> <li><a href="/wiki/Iofetamine_(123I)" title="Iofetamine (123I)">Iofetamine (123I)</a></li> <li><a href="/wiki/Lisdexamfetamine" title="Lisdexamfetamine">Lisdexamfetamine</a></li> <li><a href="/wiki/Lophophine" title="Lophophine">Lophophine</a></li> <li><a href="/wiki/Mefenorex" title="Mefenorex">Mefenorex</a></li> <li><a href="/wiki/Mephedrone" title="Mephedrone">Mephedrone</a></li> <li><a href="/wiki/Metamfepramone" title="Metamfepramone">Metamfepramone</a></li> <li><a href="/wiki/Methamphetamine" title="Methamphetamine">Methamphetamine</a> <ul><li><a href="/wiki/Dextromethamphetamine" class="mw-redirect" title="Dextromethamphetamine">Dextromethamphetamine</a></li> <li><a href="/wiki/Levomethamphetamine" class="mw-redirect" title="Levomethamphetamine">Levomethamphetamine</a></li></ul></li> <li><a href="/wiki/Methcathinone" title="Methcathinone">Methcathinone</a></li> <li><a href="/wiki/Methedrone" title="Methedrone">Methedrone</a></li> <li><a href="/wiki/MMDA_(drug)" title="MMDA (drug)">MMDA</a></li> <li><a href="/wiki/MMDMA" title="MMDMA">MMDMA</a></li> <li><a href="/wiki/1,3-Benzodioxolyl-N-methylbutanamine" class="mw-redirect" title="1,3-Benzodioxolyl-N-methylbutanamine">MBDB</a></li> <li><a href="/wiki/3,4-Methylenedioxyamphetamine" title="3,4-Methylenedioxyamphetamine">MDA (tenamfetamine)</a></li> <li><a href="/wiki/Methylenedioxyethylamphetamine" class="mw-redirect" title="Methylenedioxyethylamphetamine">MDEA</a></li> <li><a class="mw-selflink selflink">MDMA (midomafetamine)</a></li> <li><a href="/wiki/Methylenedioxymethylphenethylamine" class="mw-redirect" title="Methylenedioxymethylphenethylamine">MDMPEA</a></li> <li><a href="/wiki/Methylenedioxyhydroxyamphetamine" class="mw-redirect" title="Methylenedioxyhydroxyamphetamine">MDOH</a></li> <li><a href="/wiki/Methylenedioxyphenethylamine" class="mw-redirect" title="Methylenedioxyphenethylamine">MDPEA</a></li> <li><a href="/wiki/Methylone" title="Methylone">Methylone</a></li> <li><a href="/wiki/Morforex" title="Morforex">Morforex</a></li> <li><a href="/wiki/Ortetamine" title="Ortetamine">Ortetamine</a></li> <li><a href="/wiki/Para-Bromoamphetamine" title="Para-Bromoamphetamine">pBA</a></li> <li><a href="/wiki/Para-Chloroamphetamine" title="Para-Chloroamphetamine">pCA</a></li> <li><a href="/wiki/Para-Iodoamphetamine" title="Para-Iodoamphetamine">pIA</a></li> <li><a href="/wiki/Pholedrine" title="Pholedrine">Pholedrine</a></li> <li><a href="/wiki/Phenethylamine" title="Phenethylamine">Phenethylamine</a></li> <li><a href="/wiki/Pholedrine" title="Pholedrine">Pholedrine</a></li> <li><a href="/wiki/Phenpromethamine" title="Phenpromethamine">Phenpromethamine</a></li> <li><a href="/wiki/Prenylamine" title="Prenylamine">Prenylamine</a></li> <li><a href="/wiki/Propylamphetamine" title="Propylamphetamine">Propylamphetamine</a></li> <li><a href="/wiki/Pseudoephedrine" title="Pseudoephedrine">Pseudoephedrine</a></li> <li><a href="/wiki/Tiflorex" title="Tiflorex">Tiflorex</a></li> <li><a href="/wiki/Tyramine" title="Tyramine">Tyramine</a></li> <li><a href="/wiki/Xylopropamine" title="Xylopropamine">Xylopropamine</a></li> <li><a href="/wiki/Zylofuramine" title="Zylofuramine">Zylofuramine</a></li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-even" style="width:100%;padding:0;text-align: left;"><div style="padding:0 0.25em"> <ul><li>Piperazines: <a href="/wiki/2C-B-BZP" title="2C-B-BZP">2C-B-BZP</a></li> <li><a href="/wiki/Benzylpiperazine" title="Benzylpiperazine">BZP</a></li> <li><a href="/wiki/Methylbenzylpiperazine" title="Methylbenzylpiperazine">MBZP</a></li> <li><a href="/wiki/Methylenedioxybenzylpiperazine" title="Methylenedioxybenzylpiperazine">MDBZP</a></li> <li><a href="/wiki/Para-Methoxyphenylpiperazine" title="Para-Methoxyphenylpiperazine">MeOPP</a></li> <li><a href="/wiki/Ortho-Methylphenylpiperazine" title="Ortho-Methylphenylpiperazine">oMPP</a></li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-odd" style="width:100%;padding:0;text-align: left;"><div style="padding:0 0.25em"> <ul><li>Others: <a href="/wiki/2-Amino-1,2-dihydronaphthalene" title="2-Amino-1,2-dihydronaphthalene">2-ADN</a></li> <li><a href="/wiki/2-Aminoindane" title="2-Aminoindane">2-AI</a></li> <li><a href="/wiki/2-Aminotetralin" title="2-Aminotetralin">2-AT</a></li> <li><a href="/wiki/4-Benzylpiperidine" title="4-Benzylpiperidine">4-BP</a></li> <li><a href="/wiki/5-APDI" title="5-APDI">5-APDI</a></li> <li><a href="/wiki/5-IAI" title="5-IAI">5-IAI</a></li> <li><a href="/wiki/Amineptine" title="Amineptine">Amineptine</a></li> <li><a href="/wiki/Clofenciclan" title="Clofenciclan">Clofenciclan</a></li> <li><a href="/wiki/Cyclopentamine" title="Cyclopentamine">Cyclopentamine</a></li> <li><a href="/wiki/Cypenamine" title="Cypenamine">Cypenamine</a></li> <li><a href="/wiki/Cyprodenate" title="Cyprodenate">Cyprodenate</a></li> <li><a href="/wiki/Feprosidnine" title="Feprosidnine">Feprosidnine</a></li> <li><a href="/wiki/Gilutensin" class="mw-redirect" title="Gilutensin">Gilutensin</a></li> <li><a href="/wiki/Heptaminol" title="Heptaminol">Heptaminol</a></li> <li><a href="/wiki/Hexacyclonate" title="Hexacyclonate">Hexacyclonate</a></li> <li><a href="/wiki/Indanorex" title="Indanorex">Indanorex</a></li> <li><a href="/wiki/Isometheptene" title="Isometheptene">Isometheptene</a></li> <li><a href="/wiki/Methylhexanamine" title="Methylhexanamine">Methylhexanamine</a></li> <li><a href="/wiki/Naphthylaminopropane" title="Naphthylaminopropane">Naphthylaminopropane</a></li> <li><a href="/wiki/Octodrine" title="Octodrine">Octodrine</a></li> <li><a href="/wiki/Phthalimidopropiophenone" title="Phthalimidopropiophenone">Phthalimidopropiophenone</a></li> <li><a href="/wiki/Phenylbiguanide" title="Phenylbiguanide">Phenylbiguanide</a></li> <li><a href="/wiki/Propylhexedrine" title="Propylhexedrine">Propylhexedrine</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Norepinephrine_releasing_agents" class="mw-redirect" title="Norepinephrine releasing agents"><abbr title="Norepinephrine releasing agents">NRAs</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Norepinephrine releasing agents</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><td colspan="2" class="navbox-list navbox-even" style="width:100%;padding:0;text-align: left;"><div style="padding:0 0.25em"> <ul><li>Morpholines: <a href="/wiki/Fenbutrazate" title="Fenbutrazate">Fenbutrazate</a></li> <li><a href="/wiki/Fenmetramide" title="Fenmetramide">Fenmetramide</a></li> <li><a href="/wiki/Morazone" title="Morazone">Morazone</a></li> <li><a href="/wiki/Morforex" title="Morforex">Morforex</a></li> <li><a href="/wiki/Phendimetrazine" title="Phendimetrazine">Phendimetrazine</a></li> <li><a href="/wiki/Phenmetrazine" title="Phenmetrazine">Phenmetrazine</a></li> <li><a href="/wiki/Pseudophenmetrazine" title="Pseudophenmetrazine">Pseudophenmetrazine</a></li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-odd" style="width:100%;padding:0;text-align: left;"><div style="padding:0 0.25em"> <ul><li>Oxazolines: <a href="/wiki/4-Methylaminorex" title="4-Methylaminorex">4-MAR</a></li> <li><a href="/wiki/Aminorex" title="Aminorex">Aminorex</a></li> <li><a href="/wiki/Clominorex" title="Clominorex">Clominorex</a></li> <li><a href="/wiki/Cyclazodone" title="Cyclazodone">Cyclazodone</a></li> <li><a href="/wiki/Fenozolone" title="Fenozolone">Fenozolone</a></li> <li><a href="/wiki/Fluminorex" title="Fluminorex">Fluminorex</a></li> <li><a href="/wiki/Pemoline" title="Pemoline">Pemoline</a></li> <li><a href="/wiki/Thozalinone" title="Thozalinone">Thozalinone</a></li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-even" style="width:100%;padding:0;text-align: left;"><div style="padding:0 0.25em"> <ul><li>Phenethylamines: <a href="/wiki/Phenylethanolamine" title="Phenylethanolamine">2-OH-PEA</a></li> <li><a href="/wiki/4-Chlorophenylisobutylamine" title="4-Chlorophenylisobutylamine">4-CAB</a></li> <li><a href="/wiki/4-Fluoroamphetamine" title="4-Fluoroamphetamine">4-FA</a></li> <li><a href="/wiki/4-Fluoromethamphetamine" title="4-Fluoromethamphetamine">4-FMA</a></li> <li><a href="/wiki/4-Methylamphetamine" title="4-Methylamphetamine">4-MA</a></li> <li><a href="/wiki/4-Methylmethamphetamine" title="4-Methylmethamphetamine">4-MMA</a></li> <li><a href="/wiki/Alfetamine" title="Alfetamine">Alfetamine</a></li> <li><a href="/wiki/Amfecloral" title="Amfecloral">Amfecloral</a></li> <li><a href="/wiki/Amfepentorex" title="Amfepentorex">Amfepentorex</a></li> <li><a href="/wiki/Amfepramone" title="Amfepramone">Amfepramone</a></li> <li><a href="/wiki/Amphetamine" title="Amphetamine">Amphetamine</a> <ul><li><a href="/wiki/Dextroamphetamine" title="Dextroamphetamine">Dextroamphetamine</a></li> <li><a href="/wiki/Levoamphetamine" title="Levoamphetamine">Levoamphetamine</a></li></ul></li> <li><a href="/wiki/Amphetaminil" class="mw-redirect" title="Amphetaminil">Amphetaminil</a></li> <li><a href="/wiki/%CE%92-Methylphenethylamine" title="Β-Methylphenethylamine">β-Me-PEA</a></li> <li><a href="/wiki/1,3-Benzodioxolylbutanamine" title="1,3-Benzodioxolylbutanamine">BDB</a></li> <li><a href="/wiki/Benzphetamine" title="Benzphetamine">Benzphetamine</a></li> <li><a href="/wiki/BOH_(drug)" title="BOH (drug)">BOH</a></li> <li><a href="/wiki/Buphedrone" title="Buphedrone">Buphedrone</a></li> <li><a href="/wiki/Butylone" title="Butylone">Butylone</a></li> <li><a href="/wiki/Cathine" title="Cathine">Cathine</a></li> <li><a href="/wiki/Cathinone" title="Cathinone">Cathinone</a></li> <li><a href="/wiki/Clobenzorex" title="Clobenzorex">Clobenzorex</a></li> <li><a href="/wiki/Clortermine" title="Clortermine">Clortermine</a></li> <li><a href="/wiki/Dimethylamphetamine" title="Dimethylamphetamine">Dimethylamphetamine</a></li> <li><a href="/wiki/Dimethoxyamphetamine" title="Dimethoxyamphetamine">DMA</a></li> <li><a href="/wiki/Dimethoxymethamphetamine" class="mw-redirect" title="Dimethoxymethamphetamine">DMMA</a></li> <li><a href="/wiki/1,3-Benzodioxolyl-N-ethylbutanamine" title="1,3-Benzodioxolyl-N-ethylbutanamine">EBDB</a></li> <li><a href="/wiki/Ephedrine" title="Ephedrine">Ephedrine</a></li> <li><a href="/wiki/Ethcathinone" title="Ethcathinone">Ethcathinone</a></li> <li><a href="/wiki/Ethylone" title="Ethylone">Ethylone</a></li> <li><a href="/wiki/Etilamfetamine" title="Etilamfetamine">Etilamfetamine</a></li> <li><a href="/wiki/Famprofazone" title="Famprofazone">Famprofazone</a></li> <li><a href="/wiki/Fenethylline" title="Fenethylline">Fenethylline</a></li> <li><a href="/wiki/Fenproporex" title="Fenproporex">Fenproporex</a></li> <li><a href="/wiki/Flephedrone" title="Flephedrone">Flephedrone</a></li> <li><a href="/wiki/Fludorex" title="Fludorex">Fludorex</a></li> <li><a href="/wiki/Furfenorex" title="Furfenorex">Furfenorex</a></li> <li><a href="/wiki/Hordenine" title="Hordenine">Hordenine</a></li> <li><a href="/wiki/4-Hydroxyamphetamine" title="4-Hydroxyamphetamine">4-Hydroxyamphetamine</a></li> <li><a href="/wiki/5-APDI" title="5-APDI">5-APDI</a> (IAP)</li> <li><a href="/wiki/Iofetamine_(123I)" title="Iofetamine (123I)">Iofetamine (123I)</a></li> <li><a href="/wiki/Lisdexamfetamine" title="Lisdexamfetamine">Lisdexamfetamine</a></li> <li><a href="/wiki/Lophophine" title="Lophophine">Lophophine</a></li> <li><a href="/wiki/1,3-Benzodioxolyl-N-methylbutanamine" class="mw-redirect" title="1,3-Benzodioxolyl-N-methylbutanamine">MBDB</a></li> <li><a href="/wiki/3,4-Methylenedioxyamphetamine" title="3,4-Methylenedioxyamphetamine">MDA (tenamfetamine)</a></li> <li><a href="/wiki/Methylenedioxyethylamphetamine" class="mw-redirect" title="Methylenedioxyethylamphetamine">MDEA</a></li> <li><a class="mw-selflink selflink">MDMA (midomafetamine)</a></li> <li><a href="/wiki/Metamfepramone" title="Metamfepramone">Metamfepramone</a></li> <li><a href="/wiki/Methylenedioxymethylphenethylamine" class="mw-redirect" title="Methylenedioxymethylphenethylamine">MDMPEA</a></li> <li><a href="/wiki/Methylenedioxyhydroxyamphetamine" class="mw-redirect" title="Methylenedioxyhydroxyamphetamine">MDOH</a></li> <li><a href="/wiki/Methylenedioxyphenethylamine" class="mw-redirect" title="Methylenedioxyphenethylamine">MDPEA</a></li> <li><a href="/wiki/Mefenorex" title="Mefenorex">Mefenorex</a></li> <li><a href="/wiki/Mephedrone" title="Mephedrone">Mephedrone</a></li> <li><a href="/wiki/Mephentermine" title="Mephentermine">Mephentermine</a></li> <li><a href="/wiki/Methamphetamine" title="Methamphetamine">Methamphetamine</a> <ul><li><a href="/wiki/Dextromethamphetamine" class="mw-redirect" title="Dextromethamphetamine">Dextromethamphetamine</a></li> <li><a href="/wiki/Levomethamphetamine" class="mw-redirect" title="Levomethamphetamine">Levomethamphetamine</a></li></ul></li> <li><a href="/wiki/Methcathinone" title="Methcathinone">Methcathinone</a></li> <li><a href="/wiki/Methedrone" title="Methedrone">Methedrone</a></li> <li><a href="/wiki/Methylone" title="Methylone">Methylone</a></li> <li><a href="/wiki/Morforex" title="Morforex">Morforex</a></li> <li><a href="/wiki/Naphthylaminopropane" title="Naphthylaminopropane">Naphthylaminopropane</a></li> <li><a href="/wiki/Ortetamine" title="Ortetamine">Ortetamine</a></li> <li><a href="/wiki/Para-Bromoamphetamine" title="Para-Bromoamphetamine">pBA</a></li> <li><a href="/wiki/Para-Chloroamphetamine" title="Para-Chloroamphetamine">pCA</a></li> <li><a href="/wiki/Pentorex" title="Pentorex">Pentorex</a></li> <li><a href="/wiki/Phenethylamine" title="Phenethylamine">Phenethylamine</a></li> <li><a href="/wiki/Pholedrine" title="Pholedrine">Pholedrine</a></li> <li><a href="/wiki/Phenpromethamine" title="Phenpromethamine">Phenpromethamine</a></li> <li><a href="/wiki/Phentermine" title="Phentermine">Phentermine</a></li> <li><a href="/wiki/Phenylpropanolamine" title="Phenylpropanolamine">Phenylpropanolamine</a></li> <li><a href="/wiki/Para-Iodoamphetamine" title="Para-Iodoamphetamine">pIA</a></li> <li><a href="/wiki/Prenylamine" title="Prenylamine">Prenylamine</a></li> <li><a href="/wiki/Propylamphetamine" title="Propylamphetamine">Propylamphetamine</a></li> <li><a href="/wiki/Pseudoephedrine" title="Pseudoephedrine">Pseudoephedrine</a></li> <li><a href="/wiki/Selegiline" title="Selegiline">Selegiline</a> (also <a href="/wiki/D-Deprenyl" title="D-Deprenyl">D-Deprenyl</a>)</li> <li><a href="/wiki/Tiflorex" title="Tiflorex">Tiflorex</a></li> <li><a href="/wiki/Tyramine" title="Tyramine">Tyramine</a></li> <li><a href="/wiki/Xylopropamine" title="Xylopropamine">Xylopropamine</a></li> <li><a href="/wiki/Zylofuramine" title="Zylofuramine">Zylofuramine</a></li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-odd" style="width:100%;padding:0;text-align: left;"><div style="padding:0 0.25em"> <ul><li>Piperazines: <a href="/wiki/2C-B-BZP" title="2C-B-BZP">2C-B-BZP</a></li> <li><a href="/wiki/Benzylpiperazine" title="Benzylpiperazine">BZP</a></li> <li><a href="/wiki/Methylbenzylpiperazine" title="Methylbenzylpiperazine">MBZP</a></li> <li><a href="/wiki/Meta-Chlorophenylpiperazine" title="Meta-Chlorophenylpiperazine">mCPP</a></li> <li><a href="/wiki/Methylenedioxybenzylpiperazine" title="Methylenedioxybenzylpiperazine">MDBZP</a></li> <li><a href="/wiki/Para-Methoxyphenylpiperazine" title="Para-Methoxyphenylpiperazine">MeOPP</a></li> <li><a href="/wiki/Ortho-Methylphenylpiperazine" title="Ortho-Methylphenylpiperazine">oMPP</a></li> <li><a href="/wiki/Para-Fluorophenylpiperazine" title="Para-Fluorophenylpiperazine">pFPP</a></li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-even" style="width:100%;padding:0;text-align: left;"><div style="padding:0 0.25em"> <ul><li>Others: <a href="/wiki/2-Amino-1,2-dihydronaphthalene" title="2-Amino-1,2-dihydronaphthalene">2-ADN</a></li> <li><a href="/wiki/2-Aminoindane" title="2-Aminoindane">2-AI</a></li> <li><a href="/wiki/2-Aminotetralin" title="2-Aminotetralin">2-AT</a></li> <li><a href="/wiki/2-Benzylpiperidine" title="2-Benzylpiperidine">2-BP</a></li> <li><a href="/wiki/4-Benzylpiperidine" title="4-Benzylpiperidine">4-BP</a></li> <li><a href="/wiki/5-IAI" title="5-IAI">5-IAI</a></li> <li><a href="/wiki/Clofenciclan" title="Clofenciclan">Clofenciclan</a></li> <li><a href="/wiki/Cyclopentamine" title="Cyclopentamine">Cyclopentamine</a></li> <li><a href="/wiki/Cypenamine" title="Cypenamine">Cypenamine</a></li> <li><a href="/wiki/Cyprodenate" title="Cyprodenate">Cyprodenate</a></li> <li><a href="/wiki/Feprosidnine" title="Feprosidnine">Feprosidnine</a></li> <li><a href="/wiki/Gilutensin" class="mw-redirect" title="Gilutensin">Gilutensin</a></li> <li><a href="/wiki/Heptaminol" title="Heptaminol">Heptaminol</a></li> <li><a href="/wiki/Hexacyclonate" title="Hexacyclonate">Hexacyclonate</a></li> <li><a href="/wiki/Indanorex" title="Indanorex">Indanorex</a></li> <li><a href="/wiki/Isometheptene" title="Isometheptene">Isometheptene</a></li> <li><a href="/wiki/Methylhexanamine" title="Methylhexanamine">Methylhexanamine</a></li> <li><a href="/wiki/Octodrine" title="Octodrine">Octodrine</a></li> <li><a href="/wiki/Phthalimidopropiophenone" title="Phthalimidopropiophenone">Phthalimidopropiophenone</a></li> <li><a href="/wiki/Propylhexedrine" title="Propylhexedrine">Propylhexedrine</a></li> <li><a href="/wiki/Tuaminoheptane" title="Tuaminoheptane">Tuaminoheptane</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Serotonin_releasing_agents" class="mw-redirect" title="Serotonin releasing agents"><abbr title="Serotonin releasing agents">SRAs</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Serotonin releasing agents</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><td colspan="2" class="navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li>Aminoindanes: <a href="/wiki/5-IAI" title="5-IAI">5-IAI</a></li> <li><a href="/wiki/1-Aminomethyl-5-methoxyindane" title="1-Aminomethyl-5-methoxyindane">AMMI</a></li> <li><a href="/wiki/Ethyltrifluoromethylaminoindane" title="Ethyltrifluoromethylaminoindane">ETAI</a></li> <li><a href="/wiki/MDAI" title="MDAI">MDAI</a></li> <li><a href="/wiki/MDMAI" title="MDMAI">MDMAI</a></li> <li><a href="/wiki/MMAI" title="MMAI">MMAI</a></li> <li><a href="/wiki/Trifluoromethylaminoindane" title="Trifluoromethylaminoindane">TAI</a></li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li>Aminotetralins: <a href="/wiki/6-CAT" title="6-CAT">6-CAT</a></li> <li><a href="/wiki/8-OH-DPAT" title="8-OH-DPAT">8-OH-DPAT</a></li> <li><a href="/wiki/MDAT" title="MDAT">MDAT</a></li> <li><a href="/wiki/MDMAT" title="MDMAT">MDMAT</a></li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li>Oxazolines: <a href="/wiki/4-Methylaminorex" title="4-Methylaminorex">4-Methylaminorex</a></li> <li><a href="/wiki/Aminorex" title="Aminorex">Aminorex</a></li> <li><a href="/wiki/Clominorex" title="Clominorex">Clominorex</a></li> <li><a href="/wiki/Fluminorex" title="Fluminorex">Fluminorex</a></li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li>Phenethylamines: <a href="/wiki/2-Methyl-MDA" title="2-Methyl-MDA">2-Methyl-MDA</a></li> <li><a href="/wiki/4-Chlorophenylisobutylamine" title="4-Chlorophenylisobutylamine">4-CAB</a></li> <li><a href="/wiki/4-Fluoroamphetamine" title="4-Fluoroamphetamine">4-FA</a></li> <li><a href="/wiki/4-Fluoromethamphetamine" title="4-Fluoromethamphetamine">4-FMA</a></li> <li><a href="/wiki/4-Hydroxyamphetamine" title="4-Hydroxyamphetamine">4-HA</a></li> <li><a href="/wiki/4-Methylthioamphetamine" title="4-Methylthioamphetamine">4-MTA</a></li> <li><a href="/wiki/5-APDB" title="5-APDB">5-APDB</a></li> <li><a href="/wiki/5-Methyl-MDA" title="5-Methyl-MDA">5-Methyl-MDA</a></li> <li><a href="/wiki/6-APDB" title="6-APDB">6-APDB</a></li> <li><a href="/wiki/6-Methyl-MDA" title="6-Methyl-MDA">6-Methyl-MDA</a></li> <li><a href="/wiki/3-Methoxy-4-methyl-%CE%B1-ethylphenethylamine" class="mw-redirect" title="3-Methoxy-4-methyl-α-ethylphenethylamine">AEMMA</a></li> <li><a href="/wiki/Amiflamine" title="Amiflamine">Amiflamine</a></li> <li><a href="/wiki/Benzodioxolylbutanamine" class="mw-redirect" title="Benzodioxolylbutanamine">BDB</a></li> <li><a href="/wiki/BOH_(drug)" title="BOH (drug)">BOH</a></li> <li><a href="/wiki/4-Bromomethcathinone" title="4-Bromomethcathinone">Brephedrone</a></li> <li><a href="/wiki/Butylone" title="Butylone">Butylone</a></li> <li><a href="/wiki/Chlorphentermine" title="Chlorphentermine">Chlorphentermine</a></li> <li><a href="/wiki/Cloforex" title="Cloforex">Cloforex</a></li> <li><a href="/wiki/Amfepramone" title="Amfepramone">Amfepramone</a></li> <li><a href="/wiki/Metamfepramone" title="Metamfepramone">Metamfepramone</a></li> <li><a href="/wiki/3,4-Dichloroamphetamine" title="3,4-Dichloroamphetamine">DCA</a></li> <li><a href="/wiki/Dexfenfluramine" title="Dexfenfluramine">Dexfenfluramine</a></li> <li><a href="/wiki/DFMDA" title="DFMDA">DFMDA</a></li> <li><a href="/wiki/Dimethoxyamphetamine" title="Dimethoxyamphetamine">DMA</a></li> <li><a href="/wiki/Dimethoxymethamphetamine" class="mw-redirect" title="Dimethoxymethamphetamine">DMMA</a></li> <li><a href="/wiki/Ethylbenzodioxolylbutanamine" class="mw-redirect" title="Ethylbenzodioxolylbutanamine">EBDB</a></li> <li><a href="/wiki/EDMA" title="EDMA">EDMA</a></li> <li><a href="/wiki/Ethylone" title="Ethylone">Ethylone</a></li> <li><a href="/wiki/Etolorex" title="Etolorex">Etolorex</a></li> <li><a href="/wiki/Fenfluramine" title="Fenfluramine">Fenfluramine</a></li> <li><a href="/wiki/Flephedrone" title="Flephedrone">Flephedrone</a></li> <li><a href="/wiki/Flucetorex" title="Flucetorex">Flucetorex</a></li> <li><a href="/wiki/Indanylaminopropane" class="mw-redirect" title="Indanylaminopropane">IAP</a></li> <li><a href="/wiki/Iofetamine" class="mw-redirect" title="Iofetamine">Iofetamine</a></li> <li><a href="/wiki/Levofenfluramine" title="Levofenfluramine">Levofenfluramine</a></li> <li><a href="/wiki/Lophophine" title="Lophophine">Lophophine</a></li> <li><a href="/wiki/Methylbenzodioxolylbutanamine" class="mw-redirect" title="Methylbenzodioxolylbutanamine">MBDB</a></li> <li><a href="/wiki/3,4-Methylenedioxyamphetamine" title="3,4-Methylenedioxyamphetamine">MDA (tenamfetamine)</a></li> <li><a href="/wiki/Methylenedioxyethylamphetamine" class="mw-redirect" title="Methylenedioxyethylamphetamine">MDEA</a></li> <li><a href="/wiki/Methylenedioxyhydroxymethamphetamine" class="mw-redirect" title="Methylenedioxyhydroxymethamphetamine">MDHMA</a></li> <li><a class="mw-selflink selflink">MDMA (midomafetamine)</a></li> <li><a href="/wiki/Methylenedioxymethylphenethylamine" class="mw-redirect" title="Methylenedioxymethylphenethylamine">MDMPEA</a></li> <li><a href="/wiki/Methylenedioxyhydroxyamphetamine" class="mw-redirect" title="Methylenedioxyhydroxyamphetamine">MDOH</a></li> <li><a href="/wiki/Methylenedioxyphenethylamine" class="mw-redirect" title="Methylenedioxyphenethylamine">MDPEA</a></li> <li><a href="/wiki/Mephedrone" title="Mephedrone">Mephedrone</a></li> <li><a href="/wiki/Methedrone" title="Methedrone">Methedrone</a></li> <li><a href="/wiki/Methylone" title="Methylone">Methylone</a></li> <li><a href="/wiki/3-Methoxy-4-methylamphetamine" title="3-Methoxy-4-methylamphetamine">MMA</a></li> <li><a href="/wiki/MMDA_(drug)" title="MMDA (drug)">MMDA</a></li> <li><a href="/wiki/MMDMA" title="MMDMA">MMDMA</a></li> <li><a href="/wiki/3-Methoxy-4-methylmethamphetamine" class="mw-redirect" title="3-Methoxy-4-methylmethamphetamine">MMMA</a></li> <li><a href="/wiki/Naphthylaminopropane" title="Naphthylaminopropane">NAP</a></li> <li><a href="/wiki/Norfenfluramine" title="Norfenfluramine">Norfenfluramine</a></li> <li><a href="/wiki/4-Trifluoromethylamphetamine" class="mw-redirect" title="4-Trifluoromethylamphetamine">4-TFMA</a></li> <li><a href="/wiki/Para-Bromoamphetamine" title="Para-Bromoamphetamine">pBA</a></li> <li><a href="/wiki/Para-Chloroamphetamine" title="Para-Chloroamphetamine">pCA</a></li> <li><a href="/wiki/Para-Iodoamphetamine" title="Para-Iodoamphetamine">pIA</a></li> <li><a href="/wiki/Para-Methoxyamphetamine" title="Para-Methoxyamphetamine">PMA</a></li> <li><a href="/wiki/Para-Methoxyethylamphetamine" class="mw-redirect" title="Para-Methoxyethylamphetamine">PMEA</a></li> <li><a href="/wiki/Para-Methoxymethamphetamine" title="Para-Methoxymethamphetamine">PMMA</a></li> <li><a href="/wiki/Tetralinylaminopropane" class="mw-redirect" title="Tetralinylaminopropane">TAP</a></li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li>Piperazines: <a href="/wiki/2C-B-BZP" title="2C-B-BZP">2C-B-BZP</a></li> <li><a href="/w/index.php?title=3-Methoxyphenylpiperazine&action=edit&redlink=1" class="new" title="3-Methoxyphenylpiperazine (page does not exist)">3-MeOPP</a></li> <li><a href="/wiki/Benzylpiperazine" title="Benzylpiperazine">BZP</a></li> <li><a href="/wiki/3,4-Dichlorophenylpiperazine" class="mw-redirect" title="3,4-Dichlorophenylpiperazine">DCPP</a></li> <li><a href="/wiki/Methylbenzylpiperazine" title="Methylbenzylpiperazine">MBZP</a></li> <li><a href="/wiki/Meta-Chlorophenylpiperazine" title="Meta-Chlorophenylpiperazine">mCPP</a></li> <li><a href="/wiki/Methylenedioxybenzylpiperazine" title="Methylenedioxybenzylpiperazine">MDBZP</a></li> <li><a href="/wiki/Para-Methoxyphenylpiperazine" title="Para-Methoxyphenylpiperazine">MeOPP</a></li> <li><a href="/wiki/Mepiprazole" title="Mepiprazole">Mepiprazole</a></li> <li><a href="/wiki/Ortho-Methylphenylpiperazine" title="Ortho-Methylphenylpiperazine">oMPP</a></li> <li><a href="/wiki/Para-Chlorophenylpiperazine" title="Para-Chlorophenylpiperazine">pCPP</a></li> <li><a href="/wiki/Para-Fluorophenylpiperazine" title="Para-Fluorophenylpiperazine">pFPP</a></li> <li><a href="/wiki/1-(4-Trifluoromethyl-phenyl)-piperazine" class="mw-redirect" title="1-(4-Trifluoromethyl-phenyl)-piperazine">pTFMPP</a></li> <li><a href="/wiki/Trifluoromethylphenylpiperazine" title="Trifluoromethylphenylpiperazine">TFMPP</a></li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li>Tryptamines: <a href="/wiki/4-Methyl-AET" class="mw-redirect" title="4-Methyl-AET">4-Methyl-αET</a></li> <li><a href="/wiki/4-Methyl-AMT" class="mw-redirect" title="4-Methyl-AMT">4-Methyl-αMT</a></li> <li><a href="/wiki/5-Carboxamidotryptamine" title="5-Carboxamidotryptamine">5-CT</a></li> <li><a href="/wiki/5-MeO-AET" title="5-MeO-AET">5-MeO-αET</a></li> <li><a href="/wiki/5-MeO-AMT" title="5-MeO-AMT">5-MeO-αMT</a></li> <li><a href="/wiki/5-Methoxytryptamine" title="5-Methoxytryptamine">5-MT</a></li> <li><a href="/wiki/Alpha-Ethyltryptamine" class="mw-redirect" title="Alpha-Ethyltryptamine">αET</a></li> <li><a href="/wiki/Alpha-Methyltryptamine" class="mw-redirect" title="Alpha-Methyltryptamine">αMT</a></li> <li><a href="/wiki/Dimethyltryptamine" class="mw-redirect" title="Dimethyltryptamine">DMT</a></li> <li><a href="/wiki/Tryptamine" title="Tryptamine">Tryptamine</a></li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li>Others: <a href="/wiki/Indeloxazine" title="Indeloxazine">Indeloxazine</a></li> <li><a href="/wiki/Viqualine" title="Viqualine">Viqualine</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;">Others</th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li>DAT modulators: Agonist-like: <a href="/wiki/SoRI-9804" title="SoRI-9804">SoRI-9804</a></li> <li><a href="/w/index.php?title=SoRI-20040&action=edit&redlink=1" class="new" title="SoRI-20040 (page does not exist)">SoRI-20040</a>; Antagonist-like: <a href="/wiki/SoRI-20041" title="SoRI-20041">SoRI-20041</a></li></ul> <ul><li>Adrenergic release blockers: <a href="/wiki/Bethanidine" title="Bethanidine">Bethanidine</a></li> <li><a href="/wiki/Bretylium" title="Bretylium">Bretylium</a></li> <li><a href="/wiki/Guanadrel" title="Guanadrel">Guanadrel</a></li> <li><a href="/wiki/Guanazodine" title="Guanazodine">Guanazodine</a></li> <li><a href="/wiki/Guanethidine" title="Guanethidine">Guanethidine</a></li> <li><a href="/wiki/Guanoxan" title="Guanoxan">Guanoxan</a></li></ul> </div></td></tr><tr><td class="navbox-abovebelow" colspan="2"><div>See also: <a href="/wiki/Template:Receptor_modulators" title="Template:Receptor modulators">Receptor/signaling modulators</a> • <a href="/wiki/Template:Monoamine_reuptake_inhibitors" title="Template:Monoamine reuptake inhibitors">Monoamine reuptake inhibitors</a> • <a href="/wiki/Template:Adrenergics" class="mw-redirect" title="Template:Adrenergics">Adrenergics</a> • <a href="/wiki/Template:Dopaminergics" class="mw-redirect" title="Template:Dopaminergics">Dopaminergics</a> • <a href="/wiki/Template:Serotonergics" class="mw-redirect" title="Template:Serotonergics">Serotonergics</a> • <a href="/wiki/Template:Monoamine_metabolism_modulators" title="Template:Monoamine metabolism modulators">Monoamine metabolism modulators</a> • <a href="/wiki/Template:Monoamine_neurotoxins" class="mw-redirect" title="Template:Monoamine neurotoxins">Monoamine neurotoxins</a></div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374" /><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235" /></div><div role="navigation" class="navbox" aria-labelledby="Serotonin_receptor_modulators871" style="padding:3px"><table class="nowraplinks hlist mw-collapsible mw-collapsed navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374" /><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231" /><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Serotonin_receptor_modulators" title="Template:Serotonin receptor modulators"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Serotonin_receptor_modulators" title="Template talk:Serotonin receptor modulators"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Serotonin_receptor_modulators" title="Special:EditPage/Template:Serotonin receptor modulators"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Serotonin_receptor_modulators871" style="font-size:114%;margin:0 4em"><a href="/wiki/5-HT_receptor" title="5-HT receptor">Serotonin receptor</a> <a href="/wiki/Receptor_modulator" title="Receptor modulator">modulators</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/5-HT1_receptor" title="5-HT1 receptor">5-HT1</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/5-HT1A_receptor" title="5-HT1A receptor">5-HT1A</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><td colspan="2" class="navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li>Agonists: <a href="/wiki/8-OH-DPAT" title="8-OH-DPAT">8-OH-DPAT</a></li> <li><a href="/wiki/Adatanserin" title="Adatanserin">Adatanserin</a></li> <li><a href="/wiki/Amphetamine" title="Amphetamine">Amphetamine</a></li> <li><a href="/wiki/Antidepressant" title="Antidepressant">Antidepressants</a> (e.g., <a href="/wiki/Etoperidone" title="Etoperidone">etoperidone</a>, <a href="/wiki/Hydroxynefazodone" title="Hydroxynefazodone">hydroxynefazodone</a>, <a href="/wiki/Nefazodone" title="Nefazodone">nefazodone</a>, <a href="/wiki/Trazodone" title="Trazodone">trazodone</a>, <a href="/wiki/Triazoledione" title="Triazoledione">triazoledione</a>, <a href="/wiki/Vilazodone" title="Vilazodone">vilazodone</a>, <a href="/wiki/Vortioxetine" title="Vortioxetine">vortioxetine</a>)</li> <li><a href="/wiki/Atypical_antipsychotic" title="Atypical antipsychotic">Atypical antipsychotics</a> (e.g., <a href="/wiki/Aripiprazole" title="Aripiprazole">aripiprazole</a>, <a href="/wiki/Asenapine" title="Asenapine">asenapine</a>, <a href="/wiki/Brexpiprazole" title="Brexpiprazole">brexpiprazole</a>, <a href="/wiki/Cariprazine" title="Cariprazine">cariprazine</a>, <a href="/wiki/Clozapine" title="Clozapine">clozapine</a>, <a href="/wiki/Lurasidone" title="Lurasidone">lurasidone</a>, <a href="/wiki/Quetiapine" title="Quetiapine">quetiapine</a>, <a href="/wiki/Ziprasidone" title="Ziprasidone">ziprasidone</a>)</li> <li><a href="/wiki/Azapirone" title="Azapirone">Azapirones</a> (e.g., <a href="/wiki/Buspirone" title="Buspirone">buspirone</a>, <a href="/wiki/Eptapirone" title="Eptapirone">eptapirone</a>, <a href="/wiki/Gepirone" title="Gepirone">gepirone</a>, <a href="/wiki/Perospirone" title="Perospirone">perospirone</a>, <a href="/wiki/Tandospirone" title="Tandospirone">tandospirone</a>)</li> <li><a href="/wiki/Bay_R_1531" title="Bay R 1531">Bay R 1531</a></li> <li><a href="/wiki/Befiradol" title="Befiradol">Befiradol</a></li> <li><a href="/wiki/BMY-14802" title="BMY-14802">BMY-14802</a></li> <li><a href="/wiki/Cannabidiol" title="Cannabidiol">Cannabidiol</a></li> <li><a href="/wiki/Dimemebfe" title="Dimemebfe">Dimemebfe</a></li> <li><a href="/wiki/Dopamine" title="Dopamine">Dopamine</a></li> <li><a href="/wiki/Ebalzotan" title="Ebalzotan">Ebalzotan</a></li> <li><a href="/wiki/Eltoprazine" title="Eltoprazine">Eltoprazine</a></li> <li><a href="/wiki/Enciprazine" title="Enciprazine">Enciprazine</a></li> <li><a href="/wiki/Ergoline" title="Ergoline">Ergolines</a> (e.g., <a href="/wiki/Bromocriptine" title="Bromocriptine">bromocriptine</a>, <a href="/wiki/Cabergoline" title="Cabergoline">cabergoline</a>, <a href="/wiki/Dihydroergotamine" title="Dihydroergotamine">dihydroergotamine</a>, <a href="/wiki/Ergotamine" title="Ergotamine">ergotamine</a>, <a href="/wiki/Lisuride" title="Lisuride">lisuride</a>, <a href="/wiki/LSD" title="LSD">LSD</a>, <a href="/wiki/Methylergometrine" title="Methylergometrine">methylergometrine (methylergonovine)</a>, <a href="/wiki/Methysergide" title="Methysergide">methysergide</a>, <a href="/wiki/Pergolide" title="Pergolide">pergolide</a>)</li> <li><a href="/wiki/F-11,461" title="F-11,461">F-11,461</a></li> <li><a href="/w/index.php?title=F-12826&action=edit&redlink=1" class="new" title="F-12826 (page does not exist)">F-12826</a></li> <li><a href="/w/index.php?title=F-13714&action=edit&redlink=1" class="new" title="F-13714 (page does not exist)">F-13714</a></li> <li><a href="/w/index.php?title=F-14679&action=edit&redlink=1" class="new" title="F-14679 (page does not exist)">F-14679</a></li> <li><a href="/wiki/F-15063" title="F-15063">F-15063</a></li> <li><a href="/wiki/F-15,599" title="F-15,599">F-15,599</a></li> <li><a href="/wiki/Flesinoxan" title="Flesinoxan">Flesinoxan</a></li> <li><a href="/wiki/Flibanserin" title="Flibanserin">Flibanserin</a></li> <li><a href="/wiki/Flumexadol" title="Flumexadol">Flumexadol</a></li> <li><a href="/wiki/Hypidone" title="Hypidone">Hypidone</a></li> <li><a href="/wiki/Lesopitron" title="Lesopitron">Lesopitron</a></li> <li><a href="/wiki/LY-293284" title="LY-293284">LY-293284</a></li> <li><a href="/w/index.php?title=LY-301317&action=edit&redlink=1" class="new" title="LY-301317 (page does not exist)">LY-301317</a></li> <li><a href="/wiki/Meta-Chlorophenylpiperazine" title="Meta-Chlorophenylpiperazine">mCPP</a></li> <li><a href="/wiki/Osemozotan" title="Osemozotan">MKC-242</a></li> <li><a href="/wiki/Naluzotan" title="Naluzotan">Naluzotan</a></li> <li><a href="/wiki/NBUMP" title="NBUMP">NBUMP</a></li> <li><a href="/wiki/Osemozotan" title="Osemozotan">Osemozotan</a></li> <li><a href="/wiki/Oxaflozane" title="Oxaflozane">Oxaflozane</a></li> <li><a href="/wiki/Pardoprunox" title="Pardoprunox">Pardoprunox</a></li> <li><a href="/wiki/Piclozotan" title="Piclozotan">Piclozotan</a></li> <li><a href="/wiki/Rauwolscine" title="Rauwolscine">Rauwolscine</a></li> <li><a href="/wiki/Repinotan" title="Repinotan">Repinotan</a></li> <li><a href="/wiki/Roxindole" title="Roxindole">Roxindole</a></li> <li><a href="/wiki/RU-24,969" title="RU-24,969">RU-24,969</a></li> <li><a href="/wiki/S-14,506" title="S-14,506">S-14,506</a></li> <li><a href="/wiki/S-14671" title="S-14671">S-14671</a></li> <li><a href="/wiki/S-15535" title="S-15535">S-15535</a></li> <li><a href="/wiki/Sarizotan" title="Sarizotan">Sarizotan</a></li> <li><a href="/wiki/Serotonin" title="Serotonin">Serotonin (5-HT)</a></li> <li><a href="/w/index.php?title=SSR-181507&action=edit&redlink=1" class="new" title="SSR-181507 (page does not exist)">SSR-181507</a></li> <li><a href="/wiki/Sunepitron" title="Sunepitron">Sunepitron</a></li> <li><a href="/wiki/Substituted_tryptamine" title="Substituted tryptamine">Tryptamines</a> (e.g., <a href="/wiki/5-Carboxamidotryptamine" title="5-Carboxamidotryptamine">5-CT</a>, <a href="/wiki/5-MeO-DMT" title="5-MeO-DMT">5-MeO-DMT</a>, <a href="/wiki/5-Methoxytryptamine" title="5-Methoxytryptamine">5-MT</a>, <a href="/wiki/Bufotenin" title="Bufotenin">bufotenin</a>, <a href="/wiki/N,N-Dimethyltryptamine" title="N,N-Dimethyltryptamine">DMT</a>, <a href="/wiki/Indorenate" title="Indorenate">indorenate</a>, <a href="/wiki/N-Methylserotonin" title="N-Methylserotonin">N-Me-5-HT</a>, <a href="/wiki/Psilocin" title="Psilocin">psilocin</a>, <a href="/wiki/Psilocybin" title="Psilocybin">psilocybin</a>)</li> <li><a href="/wiki/TGBA01AD" title="TGBA01AD">TGBA01AD</a></li> <li><a href="/wiki/U-92,016-A" title="U-92,016-A">U-92,016-A</a></li> <li><a href="/wiki/Urapidil" title="Urapidil">Urapidil</a></li> <li><a href="/wiki/Vilazodone" title="Vilazodone">Vilazodone</a></li> <li><a href="/wiki/Xaliproden" title="Xaliproden">Xaliproden</a></li> <li><a href="/wiki/Yohimbine" title="Yohimbine">Yohimbine</a></li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li>Antagonists: <a href="/wiki/Atypical_antipsychotic" title="Atypical antipsychotic">Atypical antipsychotics</a> (e.g., <a href="/wiki/Iloperidone" title="Iloperidone">iloperidone</a>, <a href="/wiki/Risperidone" title="Risperidone">risperidone</a>, <a href="/wiki/Sertindole" title="Sertindole">sertindole</a>)</li> <li><a href="/w/index.php?title=AV965&action=edit&redlink=1" class="new" title="AV965 (page does not exist)">AV965</a></li> <li><a href="/wiki/Beta_blocker" title="Beta blocker">Beta blockers</a> (e.g., <a href="/wiki/Alprenolol" title="Alprenolol">alprenolol</a>, <a href="/wiki/Carteolol" title="Carteolol">carteolol</a>, <a href="/wiki/Cyanopindolol" title="Cyanopindolol">cyanopindolol</a>, <a href="/wiki/Iodocyanopindolol" title="Iodocyanopindolol">iodocyanopindolol</a>, <a href="/wiki/Isamoltane" title="Isamoltane">isamoltane</a>, <a href="/wiki/Oxprenolol" title="Oxprenolol">oxprenolol</a>, <a href="/wiki/Penbutolol" title="Penbutolol">penbutolol</a>, <a href="/wiki/Pindobind" title="Pindobind">pindobind</a>, <a href="/wiki/Pindolol" title="Pindolol">pindolol</a>, <a href="/wiki/Propranolol" title="Propranolol">propranolol</a>, <a href="/wiki/Tertatolol" title="Tertatolol">tertatolol</a>)</li> <li><a href="/wiki/BMY-7,378" class="mw-redirect" title="BMY-7,378">BMY-7,378</a></li> <li><a href="/wiki/CSP-2503" title="CSP-2503">CSP-2503</a></li> <li><a href="/wiki/Dotarizine" title="Dotarizine">Dotarizine</a></li> <li><a href="/wiki/Ergoline" title="Ergoline">Ergolines</a> (e.g., <a href="/wiki/Metergoline" title="Metergoline">metergoline</a>)</li> <li><a href="/w/index.php?title=FCE-24379&action=edit&redlink=1" class="new" title="FCE-24379 (page does not exist)">FCE-24379</a></li> <li><a href="/wiki/Flopropione" title="Flopropione">Flopropione</a></li> <li><a href="/w/index.php?title=GR-46611&action=edit&redlink=1" class="new" title="GR-46611 (page does not exist)">GR-46611</a></li> <li><a href="/wiki/Isamoltane" title="Isamoltane">Isamoltane</a></li> <li><a href="/wiki/Lecozotan" title="Lecozotan">Lecozotan</a></li> <li><a href="/wiki/Mefway_(18F)" title="Mefway (18F)">Mefway</a></li> <li><a href="/wiki/Metitepine" title="Metitepine">Metitepine (methiothepin)</a></li> <li><a href="/wiki/MIN-117" title="MIN-117">MIN-117 (WF-516)</a></li> <li><a href="/wiki/MPPF" title="MPPF">MPPF</a></li> <li><a href="/wiki/NAN-190" title="NAN-190">NAN-190</a></li> <li><a href="/wiki/Robalzotan" title="Robalzotan">Robalzotan</a></li> <li><a href="/wiki/S-15535" title="S-15535">S-15535</a></li> <li><a href="/wiki/SB-649,915" title="SB-649,915">SB-649,915</a></li> <li><a href="/w/index.php?title=SDZ_216-525&action=edit&redlink=1" class="new" title="SDZ 216-525 (page does not exist)">SDZ 216-525</a></li> <li><a href="/wiki/Spiperone" title="Spiperone">Spiperone</a></li> <li><a href="/wiki/Spiramide" title="Spiramide">Spiramide</a></li> <li><a href="/wiki/Spiroxatrine" title="Spiroxatrine">Spiroxatrine</a></li> <li><a href="/wiki/UH-301" title="UH-301">UH-301</a></li> <li><a href="/wiki/WAY-100135" title="WAY-100135">WAY-100135</a></li> <li><a href="/wiki/WAY-100635" title="WAY-100635">WAY-100635</a></li> <li><a href="/wiki/Xylamidine" title="Xylamidine">Xylamidine</a></li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li>Unknown/unsorted: <a href="/wiki/Acetryptine" title="Acetryptine">Acetryptine</a></li> <li><a href="/wiki/Carvedilol" title="Carvedilol">Carvedilol</a></li> <li><a href="/wiki/Ergoline" title="Ergoline">Ergolines</a> (e.g., <a href="/wiki/Ergometrine" class="mw-redirect" title="Ergometrine">ergometrine (ergonovine)</a>)</li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/5-HT1B_receptor" title="5-HT1B receptor">5-HT1B</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><td colspan="2" class="navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li>Agonists: <a href="/wiki/Anpirtoline" title="Anpirtoline">Anpirtoline</a></li> <li><a href="/wiki/CGS-12066A" title="CGS-12066A">CGS-12066A</a></li> <li><a href="/wiki/CP-93129" title="CP-93129">CP-93129</a></li> <li><a href="/wiki/CP-94253" title="CP-94253">CP-94253</a></li> <li><a href="/wiki/CP-122,288" title="CP-122,288">CP-122,288</a></li> <li><a href="/wiki/CP-135807" title="CP-135807">CP-135807</a></li> <li><a href="/wiki/Eltoprazine" title="Eltoprazine">Eltoprazine</a></li> <li><a href="/wiki/Ergoline" title="Ergoline">Ergolines</a> (e.g., <a href="/wiki/Bromocriptine" title="Bromocriptine">bromocriptine</a>, <a href="/wiki/Dihydroergotamine" title="Dihydroergotamine">dihydroergotamine</a>, <a href="/wiki/Ergotamine" title="Ergotamine">ergotamine</a>, <a href="/wiki/Methylergometrine" title="Methylergometrine">methylergometrine (methylergonovine)</a>, <a href="/wiki/Methysergide" title="Methysergide">methysergide</a>, <a href="/wiki/Pergolide" title="Pergolide">pergolide</a>)</li> <li><a href="/wiki/Meta-Chlorophenylpiperazine" title="Meta-Chlorophenylpiperazine">mCPP</a></li> <li><a href="/wiki/RU-24,969" title="RU-24,969">RU-24,969</a></li> <li><a href="/wiki/Serotonin" title="Serotonin">Serotonin (5-HT)</a></li> <li><a href="/wiki/Triptan" title="Triptan">Triptans</a> (e.g., <a href="/wiki/Avitriptan" title="Avitriptan">avitriptan</a>, <a href="/wiki/Donitriptan" title="Donitriptan">donitriptan</a>, <a href="/wiki/Eletriptan" title="Eletriptan">eletriptan</a>, <a href="/wiki/Sumatriptan" title="Sumatriptan">sumatriptan</a>, <a href="/wiki/Zolmitriptan" title="Zolmitriptan">zolmitriptan</a>)</li> <li><a href="/wiki/Trifluoromethylphenylpiperazine" title="Trifluoromethylphenylpiperazine">TFMPP</a></li> <li><a href="/wiki/Substituted_tryptamine" title="Substituted tryptamine">Tryptamines</a> (e.g., <a href="/wiki/5-Benzyloxytryptamine" title="5-Benzyloxytryptamine">5-BT</a>, <a href="/wiki/5-Carboxamidotryptamine" title="5-Carboxamidotryptamine">5-CT</a>, <a href="/wiki/5-Methoxytryptamine" title="5-Methoxytryptamine">5-MT</a>, <a href="/wiki/N,N-Dimethyltryptamine" title="N,N-Dimethyltryptamine">DMT</a>)</li> <li><a href="/wiki/Vortioxetine" title="Vortioxetine">Vortioxetine</a></li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li>Antagonists: <a href="/wiki/AR-A000002" title="AR-A000002">AR-A000002</a></li> <li><a href="/wiki/Beta_blocker" title="Beta blocker">Beta blockers</a> (e.g., <a href="/wiki/Alprenolol" title="Alprenolol">alprenolol</a>, <a href="/wiki/Carteolol" title="Carteolol">carteolol</a>, <a href="/wiki/Isamoltane" title="Isamoltane">isamoltane</a>, <a href="/wiki/Oxprenolol" title="Oxprenolol">oxprenolol</a>, <a href="/wiki/Penbutolol" title="Penbutolol">penbutolol</a>, <a href="/wiki/Propranolol" title="Propranolol">propranolol</a>, <a href="/wiki/Tertatolol" title="Tertatolol">tertatolol</a>)</li> <li><a href="/wiki/Elzasonan" title="Elzasonan">Elzasonan</a></li> <li><a href="/wiki/Ergoline" title="Ergoline">Ergolines</a> (e.g., <a href="/wiki/Metergoline" title="Metergoline">metergoline</a>)</li> <li><a href="/wiki/GR-127935" title="GR-127935">GR-127935</a></li> <li><a href="/wiki/Isamoltane" title="Isamoltane">Isamoltane</a></li> <li><a href="/wiki/LY-393558" title="LY-393558">LY-393558</a></li> <li><a href="/wiki/Metitepine" title="Metitepine">Metitepine (methiothepin)</a></li> <li><a href="/wiki/SB-216641" title="SB-216641">SB-216641</a></li> <li><a href="/wiki/SB-224289" title="SB-224289">SB-224289</a></li> <li><a href="/wiki/SB-236057" title="SB-236057">SB-236057</a></li> <li><a href="/wiki/Yohimbine" title="Yohimbine">Yohimbine</a></li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li>Unknown/unsorted: <a href="/wiki/Ergoline" title="Ergoline">Ergolines</a> (e.g., <a href="/wiki/Cabergoline" title="Cabergoline">cabergoline</a>, <a href="/wiki/Ergometrine" class="mw-redirect" title="Ergometrine">ergometrine (ergonovine)</a>, <a href="/wiki/Lisuride" title="Lisuride">lisuride</a>)</li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/5-HT1D_receptor" title="5-HT1D receptor">5-HT1D</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><td colspan="2" class="navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li>Agonists: <a href="/wiki/CP-122,288" title="CP-122,288">CP-122,288</a></li> <li><a href="/wiki/CP-135807" title="CP-135807">CP-135807</a></li> <li><a href="/w/index.php?title=CP-286601&action=edit&redlink=1" class="new" title="CP-286601 (page does not exist)">CP-286601</a></li> <li><a href="/wiki/Ergoline" title="Ergoline">Ergolines</a> (e.g., <a href="/wiki/Bromocriptine" title="Bromocriptine">bromocriptine</a>, <a href="/wiki/Cabergoline" title="Cabergoline">cabergoline</a>, <a href="/wiki/Dihydroergotamine" title="Dihydroergotamine">dihydroergotamine</a>, <a href="/wiki/Ergotamine" title="Ergotamine">ergotamine</a>, <a href="/wiki/LSD" title="LSD">LSD</a>, <a href="/wiki/Methysergide" title="Methysergide">methysergide</a>)</li> <li><a href="/w/index.php?title=GR-46611&action=edit&redlink=1" class="new" title="GR-46611 (page does not exist)">GR-46611</a></li> <li><a href="/wiki/L-694247" title="L-694247">L-694247</a></li> <li><a href="/w/index.php?title=L-772405&action=edit&redlink=1" class="new" title="L-772405 (page does not exist)">L-772405</a></li> <li><a href="/wiki/Meta-Chlorophenylpiperazine" title="Meta-Chlorophenylpiperazine">mCPP</a></li> <li><a href="/w/index.php?title=PNU-109291&action=edit&redlink=1" class="new" title="PNU-109291 (page does not exist)">PNU-109291</a></li> <li><a href="/wiki/PNU-142633" title="PNU-142633">PNU-142633</a></li> <li><a href="/wiki/Serotonin" title="Serotonin">Serotonin (5-HT)</a></li> <li><a href="/wiki/TGBA01AD" title="TGBA01AD">TGBA01AD</a></li> <li><a href="/wiki/Triptan" title="Triptan">Triptans</a> (e.g., <a href="/wiki/Almotriptan" title="Almotriptan">almotriptan</a>, <a href="/wiki/Avitriptan" title="Avitriptan">avitriptan</a>, <a href="/wiki/Donitriptan" title="Donitriptan">donitriptan</a>, <a href="/wiki/Eletriptan" title="Eletriptan">eletriptan</a>, <a href="/wiki/Frovatriptan" title="Frovatriptan">frovatriptan</a>, <a href="/wiki/Naratriptan" title="Naratriptan">naratriptan</a>, <a href="/wiki/Rizatriptan" title="Rizatriptan">rizatriptan</a>, <a href="/wiki/Sumatriptan" title="Sumatriptan">sumatriptan</a>, <a href="/wiki/Zolmitriptan" title="Zolmitriptan">zolmitriptan</a>)</li> <li><a href="/wiki/Substituted_tryptamine" title="Substituted tryptamine">Tryptamines</a> (e.g., <a href="/wiki/5-Benzyloxytryptamine" title="5-Benzyloxytryptamine">5-BT</a>, <a href="/wiki/5-Carboxamidotryptamine" title="5-Carboxamidotryptamine">5-CT</a>, <a href="/wiki/5-Ethyl-DMT" title="5-Ethyl-DMT">5-Et-DMT</a>, <a href="/wiki/5-Methoxytryptamine" title="5-Methoxytryptamine">5-MT</a>, <a href="/wiki/5-(Nonyloxy)tryptamine" title="5-(Nonyloxy)tryptamine">5-(nonyloxy)tryptamine</a>, <a href="/wiki/N,N-Dimethyltryptamine" title="N,N-Dimethyltryptamine">DMT</a>)</li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li>Antagonists: <a href="/wiki/Alniditan" title="Alniditan">Alniditan</a></li> <li><a href="/wiki/BRL-15,572" title="BRL-15,572">BRL-15,572</a></li> <li><a href="/wiki/Elzasonan" title="Elzasonan">Elzasonan</a></li> <li><a href="/wiki/Ergoline" title="Ergoline">Ergolines</a> (e.g., <a href="/wiki/Metergoline" title="Metergoline">metergoline</a>)</li> <li><a href="/wiki/GR-127935" title="GR-127935">GR-127935</a></li> <li><a href="/wiki/Ketanserin" title="Ketanserin">Ketanserin</a></li> <li><a href="/wiki/LY-310762" title="LY-310762">LY-310762</a></li> <li><a href="/wiki/LY-367642" title="LY-367642">LY-367642</a></li> <li><a href="/wiki/LY-393558" title="LY-393558">LY-393558</a></li> <li><a href="/wiki/LY-456219" title="LY-456219">LY-456219</a></li> <li><a href="/wiki/LY-456220" title="LY-456220">LY-456220</a></li> <li><a href="/wiki/Metitepine" title="Metitepine">Metitepine (methiothepin)</a></li> <li><a href="/wiki/Mianserin" title="Mianserin">Mianserin</a></li> <li><a href="/wiki/Ritanserin" title="Ritanserin">Ritanserin</a></li> <li><a href="/wiki/Yohimbine" title="Yohimbine">Yohimbine</a></li> <li><a href="/wiki/Ziprasidone" title="Ziprasidone">Ziprasidone</a></li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li>Unknown/unsorted: <a href="/wiki/Acetryptine" title="Acetryptine">Acetryptine</a></li> <li><a href="/wiki/Ergoline" title="Ergoline">Ergolines</a> (e.g., <a href="/wiki/Lisuride" title="Lisuride">lisuride</a>, <a href="/wiki/Lysergol" title="Lysergol">lysergol</a>, <a href="/wiki/Pergolide" title="Pergolide">pergolide</a>)</li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/5-HT1E_receptor" title="5-HT1E receptor">5-HT1E</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><td colspan="2" class="navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li>Agonists: <a href="/wiki/BRL-54443" title="BRL-54443">BRL-54443</a></li> <li><a href="/wiki/Ergoline" title="Ergoline">Ergolines</a> (e.g., <a href="/wiki/Methysergide" title="Methysergide">methysergide</a>)</li> <li><a href="/wiki/Serotonin" title="Serotonin">Serotonin (5-HT)</a></li> <li><a href="/wiki/Triptan" title="Triptan">Triptans</a> (e.g., <a href="/wiki/Eletriptan" title="Eletriptan">eletriptan</a>)</li> <li><a href="/wiki/Substituted_tryptamine" title="Substituted tryptamine">Tryptamines</a> (e.g., <a href="/wiki/Tryptamine" title="Tryptamine">tryptamine</a>)</li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li>Antagonists: <a href="/wiki/Metitepine" title="Metitepine">Metitepine (methiothepin)</a></li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li>Unknown/unsorted: <a href="/wiki/Ergoline" title="Ergoline">Ergolines</a> (e.g., <a href="/wiki/Ergometrine" class="mw-redirect" title="Ergometrine">ergometrine (ergonovine)</a>, <a href="/wiki/Lysergol" title="Lysergol">lysergol</a>, <a href="/wiki/Methylergometrine" title="Methylergometrine">methylergometrine (methylergonovine)</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/5-HT1F_receptor" title="5-HT1F receptor">5-HT1F</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><td colspan="2" class="navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li>Agonists: <a href="/wiki/BRL-54443" title="BRL-54443">BRL-54443</a></li> <li><a href="/wiki/CP-122,288" title="CP-122,288">CP-122,288</a></li> <li><a href="/wiki/Ergoline" title="Ergoline">Ergolines</a> (e.g., <a href="/wiki/Bromocriptine" title="Bromocriptine">bromocriptine</a>, <a href="/wiki/Lysergol" title="Lysergol">lysergol</a>, <a href="/wiki/Methylergometrine" title="Methylergometrine">methylergometrine (methylergonovine)</a> <a href="/wiki/Methysergide" title="Methysergide">methysergide</a>)</li> <li><a href="/wiki/Lasmiditan" title="Lasmiditan">Lasmiditan</a></li> <li><a href="/wiki/LY-334370" title="LY-334370">LY-334370</a></li> <li><a href="/wiki/Serotonin" title="Serotonin">Serotonin (5-HT)</a></li> <li><a href="/wiki/Triptan" title="Triptan">Triptans</a> (e.g., <a href="/wiki/Eletriptan" title="Eletriptan">eletriptan</a>, <a href="/wiki/Naratriptan" title="Naratriptan">naratriptan</a>, <a href="/wiki/Sumatriptan" title="Sumatriptan">sumatriptan</a>)</li> <li><a href="/wiki/Substituted_tryptamine" title="Substituted tryptamine">Tryptamines</a> (e.g., <a href="/wiki/5-Methoxytryptamine" title="5-Methoxytryptamine">5-MT</a>)</li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li>Antagonists: <a href="/wiki/Metitepine" title="Metitepine">Metitepine (methiothepin)</a></li> <li><a href="/wiki/Mianserin" title="Mianserin">Mianserin</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/5-HT2_receptor" title="5-HT2 receptor">5-HT2</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/5-HT2A_receptor" title="5-HT2A receptor">5-HT2A</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><td colspan="2" class="navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li>Agonists: 25H/NB series (e.g., <a href="/wiki/25I-NBF" title="25I-NBF">25I-NBF</a>, <a href="/wiki/25I-NBMD" title="25I-NBMD">25I-NBMD</a>, <a href="/wiki/25I-NBOH" title="25I-NBOH">25I-NBOH</a>, <a href="/wiki/25I-NBOMe" title="25I-NBOMe">25I-NBOMe</a>, <a href="/wiki/25B-NBOMe" title="25B-NBOMe">25B-NBOMe</a>, <a href="/wiki/25C-NBOMe" title="25C-NBOMe">25C-NBOMe</a>, <a href="/wiki/25TFM-NBOMe" title="25TFM-NBOMe">25TFM-NBOMe</a>, <a href="/wiki/2CBCB-NBOMe" title="2CBCB-NBOMe">2CBCB-NBOMe</a>, <a href="/wiki/25CN-NBOH" title="25CN-NBOH">25CN-NBOH</a>, <a href="/wiki/2CBFly-NBOMe" title="2CBFly-NBOMe">2CBFly-NBOMe</a>)</li> <li><a href="/wiki/2C_(psychedelics)" title="2C (psychedelics)">2Cs</a> (e.g., <a href="/wiki/2C-B" title="2C-B">2C-B</a>, <a href="/wiki/2C-E" title="2C-E">2C-E</a>, <a href="/wiki/2C-I" title="2C-I">2C-I</a>, <a href="/wiki/2C-T-2" title="2C-T-2">2C-T-2</a>, <a href="/wiki/2C-T-7" title="2C-T-7">2C-T-7</a>, <a href="/wiki/2C-T-21" title="2C-T-21">2C-T-21</a>)</li> <li><a href="/wiki/2C-B-FLY" title="2C-B-FLY">2C-B-FLY</a></li> <li><a href="/wiki/2CB-Ind" title="2CB-Ind">2CB-Ind</a></li> <li><a href="/wiki/5-Methoxytryptamine" title="5-Methoxytryptamine">5-Methoxytryptamines</a> (<a href="/wiki/5-MeO-DET" title="5-MeO-DET">5-MeO-DET</a>, <a href="/wiki/5-Methoxy-N,N-diisopropyltryptamine" class="mw-redirect" title="5-Methoxy-N,N-diisopropyltryptamine">5-MeO-DiPT</a>, <a href="/wiki/5-MeO-DMT" title="5-MeO-DMT">5-MeO-DMT</a>, <a href="/wiki/5-MeO-DPT" title="5-MeO-DPT">5-MeO-DPT</a>, <a href="/wiki/5-Methoxytryptamine" title="5-Methoxytryptamine">5-MT</a>)</li> <li><a href="/wiki/Substituted_alpha-alkyltryptamine" class="mw-redirect" title="Substituted alpha-alkyltryptamine">α-Alkyltryptamines</a> (e.g., <a href="/wiki/5-Chloro-%CE%B1MT" title="5-Chloro-αMT">5-Cl-αMT</a>, <a href="/wiki/5-Fluoro-AMT" title="5-Fluoro-AMT">5-Fl-αMT</a>, <a href="/wiki/5-MeO-AET" title="5-MeO-AET">5-MeO-αET</a>, <a href="/wiki/5-MeO-aMT" class="mw-redirect" title="5-MeO-aMT">5-MeO-αMT</a>, <a href="/wiki/Alpha-Methylserotonin" class="mw-redirect" title="Alpha-Methylserotonin">α-Me-5-HT</a>, <a href="/wiki/Alpha-Ethyltryptamine" class="mw-redirect" title="Alpha-Ethyltryptamine">αET</a>, <a href="/wiki/Alpha-Methyltryptamine" class="mw-redirect" title="Alpha-Methyltryptamine">αMT</a>)</li> <li><a href="/wiki/AL-34662" title="AL-34662">AL-34662</a></li> <li><a href="/wiki/AL-37350A" title="AL-37350A">AL-37350A</a></li> <li><a href="/wiki/Bromo-DragonFLY" title="Bromo-DragonFLY">Bromo-DragonFLY</a></li> <li><a href="/wiki/Dimemebfe" title="Dimemebfe">Dimemebfe</a></li> <li><a href="/wiki/DMBMPP" title="DMBMPP">DMBMPP</a></li> <li><a href="/wiki/DOx" title="DOx">DOx</a> (e.g., <a href="/wiki/2,5-Dimethoxy-4-bromoamphetamine" title="2,5-Dimethoxy-4-bromoamphetamine">DOB</a>, <a href="/wiki/2,5-Dimethoxy-4-chloroamphetamine" title="2,5-Dimethoxy-4-chloroamphetamine">DOC</a>, <a href="/wiki/2,5-Dimethoxy-4-iodoamphetamine" title="2,5-Dimethoxy-4-iodoamphetamine">DOI</a>, <a href="/wiki/2,5-Dimethoxy-4-methylamphetamine" title="2,5-Dimethoxy-4-methylamphetamine">DOM</a>)</li> <li><a href="/wiki/Efavirenz" title="Efavirenz">Efavirenz</a></li> <li><a href="/wiki/Ergoline" title="Ergoline">Ergolines</a> (e.g., <a href="/wiki/1P-LSD" title="1P-LSD">1P-LSD</a>, <a href="/wiki/ALD-52" title="ALD-52">ALD-52</a>, <a href="/wiki/Bromocriptine" title="Bromocriptine">bromocriptine</a>, <a href="/wiki/Cabergoline" title="Cabergoline">cabergoline</a>, <a href="/wiki/Ergine" title="Ergine">ergine (LSA)</a>, <a href="/wiki/Ergometrine" class="mw-redirect" title="Ergometrine">ergometrine (ergonovine)</a>, <a href="/wiki/Ergotamine" title="Ergotamine">ergotamine</a>, <a href="/wiki/Lisuride" title="Lisuride">lisuride</a>, <a href="/wiki/Lysergic_acid_2,4-dimethylazetidide" title="Lysergic acid 2,4-dimethylazetidide">LA-SS-Az</a>, <a href="/wiki/Lysergic_acid_2-butyl_amide" title="Lysergic acid 2-butyl amide">LSB</a>, <a href="/wiki/LSD" title="LSD">LSD</a>, <a href="/wiki/LSD-Pip" title="LSD-Pip">LSD-Pip</a>, <a href="/wiki/Lysergic_acid_hydroxyethylamide" title="Lysergic acid hydroxyethylamide">LSH</a>, <a href="/wiki/Lysergic_acid_3-pentyl_amide" title="Lysergic acid 3-pentyl amide">LSP</a>, <a href="/wiki/Methylergometrine" title="Methylergometrine">methylergometrine (methylergonovine)</a>, <a href="/wiki/Pergolide" title="Pergolide">pergolide</a>)</li> <li><a href="/wiki/Flumexadol" title="Flumexadol">Flumexadol</a></li> <li><a href="/wiki/IHCH-7113" title="IHCH-7113">IHCH-7113</a></li> <li><a href="/wiki/Jimscaline" title="Jimscaline">Jimscaline</a></li> <li><a href="/wiki/Lorcaserin" title="Lorcaserin">Lorcaserin</a></li> <li><a href="/wiki/Substituted_methylenedioxyphenethylamine" title="Substituted methylenedioxyphenethylamine">MDxx</a> (e.g., <a href="/wiki/3,4-Methylenedioxyamphetamine" title="3,4-Methylenedioxyamphetamine">MDA (tenamfetamine)</a>, <a class="mw-selflink selflink">MDMA (midomafetamine)</a>, <a href="/wiki/3,4-Methylenedioxy-N-hydroxyamphetamine" title="3,4-Methylenedioxy-N-hydroxyamphetamine">MDOH</a>, <a href="/wiki/MMDA_(drug)" title="MMDA (drug)">MMDA</a>)</li> <li><a href="/wiki/O-4310" title="O-4310">O-4310</a></li> <li><a href="/wiki/Oxaflozane" title="Oxaflozane">Oxaflozane</a></li> <li><a href="/wiki/PHA-57378" title="PHA-57378">PHA-57378</a></li> <li><a href="/wiki/PNU-22394" title="PNU-22394">PNU-22394</a></li> <li><a href="/wiki/PNU-181731" title="PNU-181731">PNU-181731</a></li> <li><a href="/wiki/RH-34" title="RH-34">RH-34</a></li> <li><a href="/wiki/SCHEMBL5334361" title="SCHEMBL5334361">SCHEMBL5334361</a></li> <li><a href="/wiki/Substituted_phenethylamine" title="Substituted phenethylamine">Phenethylamines</a> (e.g., <a href="/wiki/Lophophine" title="Lophophine">lophophine</a>, <a href="/wiki/Mescaline" title="Mescaline">mescaline</a>)</li> <li><a href="/wiki/Piperazine" title="Piperazine">Piperazines</a> (e.g., <a href="/wiki/Benzylpiperazine" title="Benzylpiperazine">BZP</a>, <a href="/wiki/Quipazine" title="Quipazine">quipazine</a>, <a href="/wiki/Trifluoromethylphenylpiperazine" title="Trifluoromethylphenylpiperazine">TFMPP</a>)</li> <li><a href="/wiki/Serotonin" title="Serotonin">Serotonin (5-HT)</a></li> <li><a href="/wiki/TCB-2" title="TCB-2">TCB-2</a></li> <li><a href="/wiki/TFMFly" title="TFMFly">TFMFly</a></li> <li><a href="/wiki/Substituted_tryptamine" title="Substituted tryptamine">Tryptamines</a> (e.g., <a href="/wiki/5-Benzyloxytryptamine" title="5-Benzyloxytryptamine">5-BT</a>, <a href="/wiki/5-Carboxamidotryptamine" title="5-Carboxamidotryptamine">5-CT</a>, <a href="/wiki/Bufotenin" title="Bufotenin">bufotenin</a>, <a href="/wiki/Diethyltryptamine" title="Diethyltryptamine">DET</a>, <a href="/wiki/Diisopropyltryptamine" class="mw-redirect" title="Diisopropyltryptamine">DiPT</a>, <a href="/wiki/N,N-Dimethyltryptamine" title="N,N-Dimethyltryptamine">DMT</a>, <a href="/wiki/Dipropyltryptamine" title="Dipropyltryptamine">DPT</a>, <a href="/wiki/Psilocin" title="Psilocin">psilocin</a>, <a href="/wiki/Psilocybin" title="Psilocybin">psilocybin</a>, <a href="/wiki/Tryptamine" title="Tryptamine">tryptamine</a>)</li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li>Antagonists: <a href="/wiki/5-I-R91150" title="5-I-R91150">5-I-R91150</a></li> <li><a href="/wiki/5-MeO-NBpBrT" title="5-MeO-NBpBrT">5-MeO-NBpBrT</a></li> <li><a href="/wiki/AC-90179" title="AC-90179">AC-90179</a></li> <li><a href="/wiki/Adatanserin" title="Adatanserin">Adatanserin</a></li> <li><a href="/wiki/Altanserin" title="Altanserin">Altanserin</a></li> <li><a href="/wiki/Antihistamine" title="Antihistamine">Antihistamines</a> (e.g., <a href="/wiki/Cyproheptadine" title="Cyproheptadine">cyproheptadine</a>, <a href="/wiki/Hydroxyzine" title="Hydroxyzine">hydroxyzine</a>, <a href="/wiki/Ketotifen" title="Ketotifen">ketotifen</a>, <a href="/wiki/Perlapine" title="Perlapine">perlapine</a>)</li> <li><a href="/wiki/9-Aminomethyl-9,10-dihydroanthracene" title="9-Aminomethyl-9,10-dihydroanthracene">AMDA</a></li> <li><a href="/wiki/Atypical_antipsychotic" title="Atypical antipsychotic">Atypical antipsychotics</a> (e.g., <a href="/wiki/Amperozide" title="Amperozide">amperozide</a>, <a href="/wiki/Aripiprazole" title="Aripiprazole">aripiprazole</a>, <a href="/wiki/Asenapine" title="Asenapine">asenapine</a>, <a href="/wiki/Blonanserin" title="Blonanserin">blonanserin</a>, <a href="/wiki/Brexpiprazole" title="Brexpiprazole">brexpiprazole</a>, <a href="/wiki/Carpipramine" title="Carpipramine">carpipramine</a>, <a href="/wiki/Clocapramine" title="Clocapramine">clocapramine</a>, <a href="/wiki/Clorotepine" title="Clorotepine">clorotepine</a>, <a href="/wiki/Clozapine" title="Clozapine">clozapine</a>, <a href="/wiki/Fluperlapine" title="Fluperlapine">fluperlapine</a>, <a href="/wiki/Gevotroline" title="Gevotroline">gevotroline</a>, <a href="/wiki/Iloperidone" title="Iloperidone">iloperidone</a>, <a href="/wiki/Lurasidone" title="Lurasidone">lurasidone</a>, <a href="/wiki/Melperone" title="Melperone">melperone</a>, <a href="/wiki/Mosapramine" title="Mosapramine">mosapramine</a>, <a href="/wiki/Ocaperidone" title="Ocaperidone">ocaperidone</a>, <a href="/wiki/Olanzapine" title="Olanzapine">olanzapine</a>, <a href="/wiki/Paliperidone" title="Paliperidone">paliperidone</a>, <a href="/wiki/Quetiapine" title="Quetiapine">quetiapine</a>, <a href="/wiki/Risperidone" title="Risperidone">risperidone</a>, <a href="/wiki/Sertindole" title="Sertindole">sertindole</a>, <a href="/wiki/Zicronapine" title="Zicronapine">zicronapine</a>, <a href="/wiki/Ziprasidone" title="Ziprasidone">ziprasidone</a>, <a href="/wiki/Zotepine" title="Zotepine">zotepine</a>)</li> <li><a href="/wiki/Chlorprothixene" title="Chlorprothixene">Chlorprothixene</a></li> <li><a href="/wiki/Cinanserin" title="Cinanserin">Cinanserin</a></li> <li><a href="/wiki/CSP-2503" title="CSP-2503">CSP-2503</a></li> <li><a href="/wiki/Deramciclane" title="Deramciclane">Deramciclane</a></li> <li><a href="/wiki/Dotarizine" title="Dotarizine">Dotarizine</a></li> <li><a href="/wiki/Eplivanserin" title="Eplivanserin">Eplivanserin</a></li> <li><a href="/wiki/Ergoline" title="Ergoline">Ergolines</a> (e.g., <a href="/wiki/Amesergide" title="Amesergide">amesergide</a>, <a href="/w/index.php?title=LY-53857&action=edit&redlink=1" class="new" title="LY-53857 (page does not exist)">LY-53857</a>, <a href="/wiki/LY-215,840" title="LY-215,840">LY-215,840</a>, <a href="/wiki/Mesulergine" title="Mesulergine">mesulergine</a>, <a href="/wiki/Metergoline" title="Metergoline">metergoline</a>, <a href="/wiki/Methysergide" title="Methysergide">methysergide</a>, <a href="/wiki/Sergolexole" title="Sergolexole">sergolexole</a>)</li> <li><a href="/wiki/Fananserin" title="Fananserin">Fananserin</a></li> <li><a href="/wiki/Flibanserin" title="Flibanserin">Flibanserin</a></li> <li><a href="/wiki/Glemanserin" title="Glemanserin">Glemanserin</a></li> <li><a href="/w/index.php?title=Irindalone&action=edit&redlink=1" class="new" title="Irindalone (page does not exist)">Irindalone</a></li> <li><a href="/wiki/Ketanserin" title="Ketanserin">Ketanserin</a></li> <li><a href="/wiki/KML-010" title="KML-010">KML-010</a></li> <li><a href="/w/index.php?title=Landipirdine&action=edit&redlink=1" class="new" title="Landipirdine (page does not exist)">Landipirdine</a></li> <li><a href="/wiki/LY-393558" title="LY-393558">LY-393558</a></li> <li><a href="/wiki/Meta-Chlorophenylpiperazine" title="Meta-Chlorophenylpiperazine">mCPP</a></li> <li><a href="/wiki/Medifoxamine" title="Medifoxamine">Medifoxamine</a></li> <li><a href="/wiki/Metitepine" title="Metitepine">Metitepine (methiothepin)</a></li> <li><a href="/wiki/MIN-117" title="MIN-117">MIN-117 (WF-516)</a></li> <li><a href="/wiki/Naftidrofuryl" title="Naftidrofuryl">Naftidrofuryl</a></li> <li><a href="/wiki/Nantenine" title="Nantenine">Nantenine</a></li> <li><a href="/wiki/Nelotanserin" title="Nelotanserin">Nelotanserin</a></li> <li><a href="/wiki/Opiranserin" title="Opiranserin">Opiranserin (VVZ-149)</a></li> <li><a href="/wiki/Pelanserin" title="Pelanserin">Pelanserin</a></li> <li><a href="/wiki/Phenoxybenzamine" title="Phenoxybenzamine">Phenoxybenzamine</a></li> <li><a href="/wiki/Pimavanserin" title="Pimavanserin">Pimavanserin</a></li> <li><a href="/wiki/Pirenperone" title="Pirenperone">Pirenperone</a></li> <li><a href="/wiki/Pizotifen" title="Pizotifen">Pizotifen</a></li> <li><a href="/wiki/Pruvanserin" title="Pruvanserin">Pruvanserin</a></li> <li><a href="/wiki/Rauwolscine" title="Rauwolscine">Rauwolscine</a></li> <li><a href="/wiki/Ritanserin" title="Ritanserin">Ritanserin</a></li> <li><a href="/wiki/Roluperidone" title="Roluperidone">Roluperidone</a></li> <li><a href="/wiki/S-14671" title="S-14671">S-14671</a></li> <li><a href="/wiki/Sarpogrelate" title="Sarpogrelate">Sarpogrelate</a></li> <li><a href="/wiki/Serotonin_antagonist_and_reuptake_inhibitor" title="Serotonin antagonist and reuptake inhibitor">Serotonin antagonists and reuptake inhibitors</a> (e.g., <a href="/wiki/Etoperidone" title="Etoperidone">etoperidone</a>, <a href="/wiki/Hydroxynefazodone" title="Hydroxynefazodone">hydroxynefazodone</a>, <a href="/wiki/Lubazodone" title="Lubazodone">lubazodone</a>, <a href="/wiki/Mepiprazole" title="Mepiprazole">mepiprazole</a>, <a href="/wiki/Nefazodone" title="Nefazodone">nefazodone</a>, <a href="/wiki/Triazoledione" title="Triazoledione">triazoledione</a>, <a href="/wiki/Trazodone" title="Trazodone">trazodone</a>)</li> <li><a href="/w/index.php?title=SR-46349B&action=edit&redlink=1" class="new" title="SR-46349B (page does not exist)">SR-46349B</a></li> <li><a href="/wiki/TGBA01AD" title="TGBA01AD">TGBA01AD</a></li> <li><a href="/wiki/Teniloxazine" title="Teniloxazine">Teniloxazine</a></li> <li><a href="/w/index.php?title=Temanogrel&action=edit&redlink=1" class="new" title="Temanogrel (page does not exist)">Temanogrel</a></li> <li><a href="/wiki/Tetracyclic_antidepressant" title="Tetracyclic antidepressant">Tetracyclic antidepressants</a> (e.g., <a href="/wiki/Amoxapine" title="Amoxapine">amoxapine</a>, <a href="/wiki/Aptazapine" title="Aptazapine">aptazapine</a>, <a href="/wiki/Esmirtazapine" title="Esmirtazapine">esmirtazapine</a>, <a href="/wiki/Maprotiline" title="Maprotiline">maprotiline</a>, <a href="/wiki/Mianserin" title="Mianserin">mianserin</a>, <a href="/wiki/Mirtazapine" title="Mirtazapine">mirtazapine</a>)</li> <li><a href="/wiki/Tricyclic_antidepressant" title="Tricyclic antidepressant">Tricyclic antidepressants</a> (e.g., <a href="/wiki/Amitriptyline" title="Amitriptyline">amitriptyline</a>)</li> <li><a href="/wiki/Typical_antipsychotic" title="Typical antipsychotic">Typical antipsychotics</a> (e.g., <a href="/wiki/Chlorpromazine" title="Chlorpromazine">chlorpromazine</a>, <a href="/wiki/Fluphenazine" title="Fluphenazine">fluphenazine</a>, <a href="/wiki/Haloperidol" title="Haloperidol">haloperidol</a>, <a href="/wiki/Loxapine" title="Loxapine">loxapine</a>, <a href="/wiki/Perphenazine" title="Perphenazine">perphenazine</a>, <a href="/wiki/Pimozide" title="Pimozide">pimozide</a>, <a href="/wiki/Pipamperone" title="Pipamperone">pipamperone</a>, <a href="/wiki/Prochlorperazine" title="Prochlorperazine">prochlorperazine</a>, <a href="/wiki/Setoperone" title="Setoperone">setoperone</a>, <a href="/wiki/Spiperone" title="Spiperone">spiperone</a>, <a href="/wiki/Spiramide" title="Spiramide">spiramide</a>, <a href="/wiki/Thioridazine" title="Thioridazine">thioridazine</a>, <a href="/wiki/Tiotixene" title="Tiotixene">thiothixene</a>, <a href="/wiki/Trifluoperazine" title="Trifluoperazine">trifluoperazine</a>)</li> <li><a href="/wiki/Volinanserin" title="Volinanserin">Volinanserin</a></li> <li><a href="/wiki/Xylamidine" title="Xylamidine">Xylamidine</a></li> <li><a href="/wiki/Yohimbine" title="Yohimbine">Yohimbine</a></li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li>Unknown/unsorted: <a href="/wiki/Ergoline" title="Ergoline">Ergolines</a> (e.g., <a href="/wiki/Dihydroergotamine" title="Dihydroergotamine">dihydroergotamine</a>, <a href="/wiki/Nicergoline" title="Nicergoline">nicergoline</a>)</li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/5-HT2B_receptor" title="5-HT2B receptor">5-HT2B</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><td colspan="2" class="navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li>Agonists: <a href="/wiki/4-Methylaminorex" title="4-Methylaminorex">4-Methylaminorex</a></li> <li><a href="/wiki/Aminorex" title="Aminorex">Aminorex</a></li> <li><a href="/wiki/Substituted_amphetamine" title="Substituted amphetamine">Amphetamines</a> (e.g., <a href="/wiki/Chlorphentermine" title="Chlorphentermine">chlorphentermine</a>, <a href="/wiki/Cloforex" title="Cloforex">cloforex</a>, <a href="/wiki/Dexfenfluramine" title="Dexfenfluramine">dexfenfluramine</a>, <a href="/wiki/Fenfluramine" title="Fenfluramine">fenfluramine</a>, <a href="/wiki/Levofenfluramine" title="Levofenfluramine">levofenfluramine</a>, <a href="/wiki/Norfenfluramine" title="Norfenfluramine">norfenfluramine</a>)</li> <li><a href="/wiki/BW-723C86" title="BW-723C86">BW-723C86</a></li> <li><a href="/wiki/DOx" title="DOx">DOx</a> (e.g., <a href="/wiki/2,5-Dimethoxy-4-bromoamphetamine" title="2,5-Dimethoxy-4-bromoamphetamine">DOB</a>, <a href="/wiki/2,5-Dimethoxy-4-chloroamphetamine" title="2,5-Dimethoxy-4-chloroamphetamine">DOC</a>, <a href="/wiki/2,5-Dimethoxy-4-iodoamphetamine" title="2,5-Dimethoxy-4-iodoamphetamine">DOI</a>, <a href="/wiki/2,5-Dimethoxy-4-methylamphetamine" title="2,5-Dimethoxy-4-methylamphetamine">DOM</a>)</li> <li><a href="/wiki/Ergoline" title="Ergoline">Ergolines</a> (e.g., <a href="/wiki/Cabergoline" title="Cabergoline">cabergoline</a>, <a href="/wiki/Dihydroergocryptine" title="Dihydroergocryptine">dihydroergocryptine</a>, <a href="/wiki/Dihydroergotamine" title="Dihydroergotamine">dihydroergotamine</a>, <a href="/wiki/Ergotamine" title="Ergotamine">ergotamine</a>, <a href="/wiki/Methylergometrine" title="Methylergometrine">methylergometrine (methylergonovine)</a>, <a href="/wiki/Methysergide" title="Methysergide">methysergide</a>, <a href="/wiki/Pergolide" title="Pergolide">pergolide</a>)</li> <li><a href="/wiki/Lorcaserin" title="Lorcaserin">Lorcaserin</a></li> <li><a href="/wiki/Substituted_methylenedioxyphenethylamine" title="Substituted methylenedioxyphenethylamine">MDxx</a> (e.g., <a href="/wiki/3,4-Methylenedioxyamphetamine" title="3,4-Methylenedioxyamphetamine">MDA (tenamfetamine)</a>, <a class="mw-selflink selflink">MDMA (midomafetamine)</a>, <a href="/wiki/3,4-Methylenedioxy-N-hydroxyamphetamine" title="3,4-Methylenedioxy-N-hydroxyamphetamine">MDOH</a>, <a href="/wiki/MMDA_(drug)" title="MMDA (drug)">MMDA</a>)</li> <li><a href="/wiki/Substituted_piperazine" title="Substituted piperazine">Piperazines</a> (e.g., <a href="/wiki/Trifluoromethylphenylpiperazine" title="Trifluoromethylphenylpiperazine">TFMPP</a>)</li> <li><a href="/wiki/PNU-22394" title="PNU-22394">PNU-22394</a></li> <li><a href="/wiki/Ro60-0175" title="Ro60-0175">Ro60-0175</a></li> <li><a href="/wiki/Serotonin" title="Serotonin">Serotonin (5-HT)</a></li> <li><a href="/wiki/Substituted_tryptamine" title="Substituted tryptamine">Tryptamines</a> (e.g., <a href="/wiki/5-Benzyloxytryptamine" title="5-Benzyloxytryptamine">5-BT</a>, <a href="/wiki/5-Carboxamidotryptamine" title="5-Carboxamidotryptamine">5-CT</a>, <a href="/wiki/5-Methoxytryptamine" title="5-Methoxytryptamine">5-MT</a>, <a href="/wiki/Alpha-Methylserotonin" class="mw-redirect" title="Alpha-Methylserotonin">α-Me-5-HT</a>, <a href="/wiki/Bufotenin" title="Bufotenin">bufotenin</a>, <a href="/wiki/Diethyltryptamine" title="Diethyltryptamine">DET</a>, <a href="/wiki/Diisopropyltryptamine" class="mw-redirect" title="Diisopropyltryptamine">DiPT</a>, <a href="/wiki/N,N-Dimethyltryptamine" title="N,N-Dimethyltryptamine">DMT</a>, <a href="/wiki/Dipropyltryptamine" title="Dipropyltryptamine">DPT</a>, <a href="/wiki/Psilocin" title="Psilocin">psilocin</a>, <a href="/wiki/Psilocybin" title="Psilocybin">psilocybin</a>, <a href="/wiki/Tryptamine" title="Tryptamine">tryptamine</a>)</li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li>Antagonists: <a href="/wiki/Agomelatine" title="Agomelatine">Agomelatine</a></li> <li><a href="/wiki/Atypical_antipsychotic" title="Atypical antipsychotic">Atypical antipsychotics</a> (e.g., <a href="/wiki/Amisulpride" title="Amisulpride">amisulpride</a>, <a href="/wiki/Aripiprazole" title="Aripiprazole">aripiprazole</a>, <a href="/wiki/Asenapine" title="Asenapine">asenapine</a>, <a href="/wiki/Brexpiprazole" title="Brexpiprazole">brexpiprazole</a>, <a href="/wiki/Cariprazine" title="Cariprazine">cariprazine</a>, <a href="/wiki/Clozapine" title="Clozapine">clozapine</a>, <a href="/w/index.php?title=N-desalkylquetiapine&action=edit&redlink=1" class="new" title="N-desalkylquetiapine (page does not exist)">N-desalkylquetiapine (norquetiapine)</a>, <a href="/wiki/Desmethylclozapine" title="Desmethylclozapine">N-desmethylclozapine (norclozapine)</a>, <a href="/wiki/Olanzapine" title="Olanzapine">olanzapine</a>, <a href="/wiki/Pipamperone" title="Pipamperone">pipamperone</a>, <a href="/wiki/Quetiapine" title="Quetiapine">quetiapine</a>, <a href="/wiki/Risperidone" title="Risperidone">risperidone</a>, <a href="/wiki/Ziprasidone" title="Ziprasidone">ziprasidone</a>)</li> <li><a href="/wiki/Cyproheptadine" title="Cyproheptadine">Cyproheptadine</a></li> <li><a href="/wiki/EGIS-7625" title="EGIS-7625">EGIS-7625</a></li> <li><a href="/wiki/Ergoline" title="Ergoline">Ergolines</a> (e.g., <a href="/wiki/Amesergide" title="Amesergide">amesergide</a>, <a href="/wiki/Bromocriptine" title="Bromocriptine">bromocriptine</a>, <a href="/wiki/Lisuride" title="Lisuride">lisuride</a>, <a href="/w/index.php?title=LY-53857&action=edit&redlink=1" class="new" title="LY-53857 (page does not exist)">LY-53857</a>, <a href="/wiki/LY-272,015" title="LY-272,015">LY-272015</a>, <a href="/wiki/Mesulergine" title="Mesulergine">mesulergine</a>)</li> <li><a href="/wiki/Ketanserin" title="Ketanserin">Ketanserin</a></li> <li><a href="/wiki/LY-393558" title="LY-393558">LY-393558</a></li> <li><a href="/wiki/Meta-Chlorophenylpiperazine" title="Meta-Chlorophenylpiperazine">mCPP</a></li> <li><a href="/wiki/Metadoxine" title="Metadoxine">Metadoxine</a></li> <li><a href="/wiki/Metitepine" title="Metitepine">Metitepine (methiothepin)</a></li> <li><a href="/wiki/Pirenperone" title="Pirenperone">Pirenperone</a></li> <li><a href="/wiki/Pizotifen" title="Pizotifen">Pizotifen</a></li> <li><a href="/wiki/Propranolol" title="Propranolol">Propranolol</a></li> <li><a href="/wiki/PRX-08066" title="PRX-08066">PRX-08066</a></li> <li><a href="/wiki/Rauwolscine" title="Rauwolscine">Rauwolscine</a></li> <li><a href="/wiki/Ritanserin" title="Ritanserin">Ritanserin</a></li> <li><a href="/wiki/RS-127445" title="RS-127445">RS-127445</a></li> <li><a href="/wiki/Sarpogrelate" title="Sarpogrelate">Sarpogrelate</a></li> <li><a href="/wiki/SB-200646" title="SB-200646">SB-200646</a></li> <li><a href="/wiki/SB-204741" title="SB-204741">SB-204741</a></li> <li><a href="/wiki/SB-206553" title="SB-206553">SB-206553</a></li> <li><a href="/wiki/SB-215505" title="SB-215505">SB-215505</a></li> <li><a href="/wiki/SB-221284" title="SB-221284">SB-221284</a></li> <li><a href="/wiki/SB-228357" title="SB-228357">SB-228357</a></li> <li><a href="/wiki/SDZ_SER-082" title="SDZ SER-082">SDZ SER-082</a></li> <li><a href="/wiki/Tegaserod" title="Tegaserod">Tegaserod</a></li> <li><a href="/wiki/Tetracyclic_antidepressant" title="Tetracyclic antidepressant">Tetracyclic antidepressants</a> (e.g., <a href="/wiki/Amoxapine" title="Amoxapine">amoxapine</a>, <a href="/wiki/Mianserin" title="Mianserin">mianserin</a>, <a href="/wiki/Mirtazapine" title="Mirtazapine">mirtazapine</a>)</li> <li><a href="/wiki/Trazodone" title="Trazodone">Trazodone</a></li> <li><a href="/wiki/Typical_antipsychotic" title="Typical antipsychotic">Typical antipsychotics</a> (e.g., <a href="/wiki/Chlorpromazine" title="Chlorpromazine">chlorpromazine</a>)</li> <li><a href="/wiki/TIK-301" title="TIK-301">TIK-301</a></li> <li><a href="/wiki/Yohimbine" title="Yohimbine">Yohimbine</a></li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li>Unknown/unsorted: <a href="/wiki/Ergoline" title="Ergoline">Ergolines</a> (e.g., <a href="/wiki/Ergometrine" class="mw-redirect" title="Ergometrine">ergometrine (ergonovine)</a>)</li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/5-HT2C_receptor" title="5-HT2C receptor">5-HT2C</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><td colspan="2" class="navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li>Agonists: <a href="/wiki/2C_(psychedelics)" title="2C (psychedelics)">2Cs</a> (e.g., <a href="/wiki/2C-B" title="2C-B">2C-B</a>, <a href="/wiki/2C-E" title="2C-E">2C-E</a>, <a href="/wiki/2C-I" title="2C-I">2C-I</a>, <a href="/wiki/2C-T-2" title="2C-T-2">2C-T-2</a>, <a href="/wiki/2C-T-7" title="2C-T-7">2C-T-7</a>, <a href="/wiki/2C-T-21" title="2C-T-21">2C-T-21</a>)</li> <li><a href="/wiki/5-Methoxytryptamine" title="5-Methoxytryptamine">5-Methoxytryptamines</a> (<a href="/wiki/5-MeO-DET" title="5-MeO-DET">5-MeO-DET</a>, <a href="/wiki/5-Methoxy-N,N-diisopropyltryptamine" class="mw-redirect" title="5-Methoxy-N,N-diisopropyltryptamine">5-MeO-DiPT</a>, <a href="/wiki/5-MeO-DMT" title="5-MeO-DMT">5-MeO-DMT</a>, <a href="/wiki/5-MeO-DPT" title="5-MeO-DPT">5-MeO-DPT</a>, <a href="/wiki/5-Methoxytryptamine" title="5-Methoxytryptamine">5-MT</a>)</li> <li><a href="/wiki/Substituted_alpha-alkyltryptamine" class="mw-redirect" title="Substituted alpha-alkyltryptamine">α-Alkyltryptamines</a> (e.g., <a href="/wiki/5-Chloro-%CE%B1MT" title="5-Chloro-αMT">5-Cl-αMT</a>, <a href="/wiki/5-Fluoro-AMT" title="5-Fluoro-AMT">5-Fl-αMT</a>, <a href="/wiki/5-MeO-AET" title="5-MeO-AET">5-MeO-αET</a>, <a href="/wiki/5-MeO-aMT" class="mw-redirect" title="5-MeO-aMT">5-MeO-αMT</a>, <a href="/wiki/Alpha-Methylserotonin" class="mw-redirect" title="Alpha-Methylserotonin">α-Me-5-HT</a>, <a href="/wiki/Alpha-Ethyltryptamine" class="mw-redirect" title="Alpha-Ethyltryptamine">αET</a>, <a href="/wiki/Alpha-Methyltryptamine" class="mw-redirect" title="Alpha-Methyltryptamine">αMT</a>)</li> <li><a href="/wiki/A-372159" title="A-372159">A-372159</a></li> <li><a href="/wiki/AL-38022A" title="AL-38022A">AL-38022A</a></li> <li><a href="/wiki/Alstonine" title="Alstonine">Alstonine</a></li> <li><a href="/wiki/CP-809101" title="CP-809101">CP-809101</a></li> <li><a href="/wiki/Dimemebfe" title="Dimemebfe">Dimemebfe</a></li> <li><a href="/wiki/DOx" title="DOx">DOx</a> (e.g., <a href="/wiki/2,5-Dimethoxy-4-bromoamphetamine" title="2,5-Dimethoxy-4-bromoamphetamine">DOB</a>, <a href="/wiki/2,5-Dimethoxy-4-chloroamphetamine" title="2,5-Dimethoxy-4-chloroamphetamine">DOC</a>, <a href="/wiki/2,5-Dimethoxy-4-iodoamphetamine" title="2,5-Dimethoxy-4-iodoamphetamine">DOI</a>, <a href="/wiki/2,5-Dimethoxy-4-methylamphetamine" title="2,5-Dimethoxy-4-methylamphetamine">DOM</a>)</li> <li><a href="/wiki/Ergoline" title="Ergoline">Ergolines</a> (e.g., <a href="/wiki/ALD-52" title="ALD-52">ALD-52</a>, <a href="/wiki/Cabergoline" title="Cabergoline">cabergoline</a>, <a href="/wiki/Dihydroergotamine" title="Dihydroergotamine">dihydroergotamine</a>, <a href="/wiki/Ergine" title="Ergine">ergine (LSA)</a>, <a href="/wiki/Ergotamine" title="Ergotamine">ergotamine</a>, <a href="/wiki/Lisuride" title="Lisuride">lisuride</a>, <a href="/wiki/Lysergic_acid_2,4-dimethylazetidide" title="Lysergic acid 2,4-dimethylazetidide">LA-SS-Az</a>, <a href="/wiki/Lysergic_acid_2-butyl_amide" title="Lysergic acid 2-butyl amide">LSB</a>, <a href="/wiki/LSD" title="LSD">LSD</a>, <a href="/wiki/LSD-Pip" title="LSD-Pip">LSD-Pip</a>, <a href="/wiki/Lysergic_acid_hydroxyethylamide" title="Lysergic acid hydroxyethylamide">LSH</a>, <a href="/wiki/Lysergic_acid_3-pentyl_amide" title="Lysergic acid 3-pentyl amide">LSP</a>, <a href="/wiki/Pergolide" title="Pergolide">pergolide</a>)</li> <li><a href="/wiki/Flumexadol" title="Flumexadol">Flumexadol</a></li> <li><a href="/wiki/Lorcaserin" title="Lorcaserin">Lorcaserin</a></li> <li><a href="/wiki/Substituted_methylenedioxyphenethylamine" title="Substituted methylenedioxyphenethylamine">MDxx</a> (e.g., <a href="/wiki/3,4-Methylenedioxyamphetamine" title="3,4-Methylenedioxyamphetamine">MDA (tenamfetamine)</a>, <a class="mw-selflink selflink">MDMA (midomafetamine)</a>, <a href="/wiki/3,4-Methylenedioxy-N-hydroxyamphetamine" title="3,4-Methylenedioxy-N-hydroxyamphetamine">MDOH</a>, <a href="/wiki/MMDA_(drug)" title="MMDA (drug)">MMDA</a>)</li> <li><a href="/wiki/MK-212" title="MK-212">MK-212</a></li> <li><a href="/wiki/ORG-12962" title="ORG-12962">ORG-12962</a></li> <li><a href="/wiki/ORG-37684" title="ORG-37684">ORG-37684</a></li> <li><a href="/wiki/Oxaflozane" title="Oxaflozane">Oxaflozane</a></li> <li><a href="/wiki/PHA-57378" title="PHA-57378">PHA-57378</a></li> <li><a href="/wiki/Substituted_phenethylamine" title="Substituted phenethylamine">Phenethylamines</a> (e.g., <a href="/wiki/Lophophine" title="Lophophine">lophophine</a>, <a href="/wiki/Mescaline" title="Mescaline">mescaline</a>)</li> <li><a href="/wiki/Piperazine" title="Piperazine">Piperazines</a> (e.g., <a href="/wiki/Aripiprazole" title="Aripiprazole">aripiprazole</a>, <a href="/wiki/Benzylpiperazine" title="Benzylpiperazine">BZP</a>, <a href="/wiki/Meta-Chlorophenylpiperazine" title="Meta-Chlorophenylpiperazine">mCPP</a>, <a href="/wiki/Quipazine" title="Quipazine">quipazine</a>, <a href="/wiki/Trifluoromethylphenylpiperazine" title="Trifluoromethylphenylpiperazine">TFMPP</a>)</li> <li><a href="/wiki/PNU-22394" title="PNU-22394">PNU-22394</a></li> <li><a href="/wiki/PNU-181731" title="PNU-181731">PNU-181731</a></li> <li><a href="/wiki/Ro60-0175" title="Ro60-0175">Ro60-0175</a></li> <li><a href="/wiki/Ro60-0213" title="Ro60-0213">Ro60-0213</a></li> <li><a href="/wiki/Serotonin" title="Serotonin">Serotonin (5-HT)</a></li> <li><a href="/wiki/Substituted_tryptamine" title="Substituted tryptamine">Tryptamines</a> (e.g., <a href="/wiki/5-Benzyloxytryptamine" title="5-Benzyloxytryptamine">5-BT</a>, <a href="/wiki/5-Carboxamidotryptamine" title="5-Carboxamidotryptamine">5-CT</a>, <a href="/wiki/Bufotenin" title="Bufotenin">bufotenin</a>, <a href="/wiki/Diethyltryptamine" title="Diethyltryptamine">DET</a>, <a href="/wiki/Diisopropyltryptamine" class="mw-redirect" title="Diisopropyltryptamine">DiPT</a>, <a href="/wiki/N,N-Dimethyltryptamine" title="N,N-Dimethyltryptamine">DMT</a>, <a href="/wiki/Dipropyltryptamine" title="Dipropyltryptamine">DPT</a>, <a href="/wiki/Psilocin" title="Psilocin">psilocin</a>, <a href="/wiki/Psilocybin" title="Psilocybin">psilocybin</a>, <a href="/wiki/Tryptamine" title="Tryptamine">tryptamine</a>)</li> <li><a href="/wiki/Vabicaserin" title="Vabicaserin">Vabicaserin</a></li> <li><a href="/wiki/WAY-629" title="WAY-629">WAY-629</a></li> <li><a href="/wiki/WAY-161503" title="WAY-161503">WAY-161503</a></li> <li><a href="/wiki/YM-348" title="YM-348">YM-348</a></li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li>Antagonists: <a href="/wiki/Adatanserin" title="Adatanserin">Adatanserin</a></li> <li><a href="/wiki/Agomelatine" title="Agomelatine">Agomelatine</a></li> <li><a href="/wiki/Atypical_antipsychotic" title="Atypical antipsychotic">Atypical antipsychotics</a> (e.g., <a href="/wiki/Asenapine" title="Asenapine">asenapine</a>, <a href="/wiki/Clorotepine" title="Clorotepine">clorotepine</a>, <a href="/wiki/Clozapine" title="Clozapine">clozapine</a>, <a href="/wiki/Fluperlapine" title="Fluperlapine">fluperlapine</a>, <a href="/wiki/Iloperidone" title="Iloperidone">iloperidone</a>, <a href="/wiki/Melperone" title="Melperone">melperone</a>, <a href="/wiki/Olanzapine" title="Olanzapine">olanzapine</a>, <a href="/wiki/Paliperidone" title="Paliperidone">paliperidone</a>, <a href="/wiki/Quetiapine" title="Quetiapine">quetiapine</a>, <a href="/wiki/Risperidone" title="Risperidone">risperidone</a>, <a href="/wiki/Sertindole" title="Sertindole">sertindole</a>, <a href="/wiki/Ziprasidone" title="Ziprasidone">ziprasidone</a>, <a href="/wiki/Zotepine" title="Zotepine">zotepine</a>)</li> <li><a href="/wiki/Captodiame" title="Captodiame">Captodiame</a></li> <li><a href="/wiki/6-Chloro-5-ethoxy-N-(pyridin-2-yl)indoline-1-carboxamide" title="6-Chloro-5-ethoxy-N-(pyridin-2-yl)indoline-1-carboxamide">CEPC</a></li> <li><a href="/wiki/Cinanserin" title="Cinanserin">Cinanserin</a></li> <li><a href="/wiki/Cyproheptadine" title="Cyproheptadine">Cyproheptadine</a></li> <li><a href="/wiki/Deramciclane" title="Deramciclane">Deramciclane</a></li> <li><a href="/wiki/Desmetramadol" title="Desmetramadol">Desmetramadol</a></li> <li><a href="/wiki/Dotarizine" title="Dotarizine">Dotarizine</a></li> <li><a href="/wiki/Eltoprazine" title="Eltoprazine">Eltoprazine</a></li> <li><a href="/wiki/Ergoline" title="Ergoline">Ergolines</a> (e.g., <a href="/wiki/Amesergide" title="Amesergide">amesergide</a>, <a href="/wiki/Bromocriptine" title="Bromocriptine">bromocriptine</a>, <a href="/w/index.php?title=LY-53857&action=edit&redlink=1" class="new" title="LY-53857 (page does not exist)">LY-53857</a>, <a href="/wiki/LY-215,840" title="LY-215,840">LY-215,840</a>, <a href="/wiki/Mesulergine" title="Mesulergine">mesulergine</a>, <a href="/wiki/Metergoline" title="Metergoline">metergoline</a>, <a href="/wiki/Methysergide" title="Methysergide">methysergide</a>, <a href="/wiki/Sergolexole" title="Sergolexole">sergolexole</a>)</li> <li><a href="/wiki/Etoperidone" title="Etoperidone">Etoperidone</a></li> <li><a href="/wiki/Fluoxetine" title="Fluoxetine">Fluoxetine</a></li> <li><a href="/w/index.php?title=FR-260010&action=edit&redlink=1" class="new" title="FR-260010 (page does not exist)">FR-260010</a></li> <li><a href="/w/index.php?title=Irindalone&action=edit&redlink=1" class="new" title="Irindalone (page does not exist)">Irindalone</a></li> <li><a href="/wiki/Ketanserin" title="Ketanserin">Ketanserin</a></li> <li><a href="/wiki/Ketotifen" title="Ketotifen">Ketotifen</a></li> <li><a href="/wiki/Latrepirdine" title="Latrepirdine">Latrepirdine (dimebolin)</a></li> <li><a href="/wiki/Medifoxamine" title="Medifoxamine">Medifoxamine</a></li> <li><a href="/wiki/Metitepine" title="Metitepine">Metitepine (methiothepin)</a></li> <li><a href="/wiki/Nefazodone" title="Nefazodone">Nefazodone</a></li> <li><a href="/wiki/Pirenperone" title="Pirenperone">Pirenperone</a></li> <li><a href="/wiki/Pizotifen" title="Pizotifen">Pizotifen</a></li> <li><a href="/wiki/Propranolol" title="Propranolol">Propranolol</a></li> <li><a href="/wiki/Ritanserin" title="Ritanserin">Ritanserin</a></li> <li><a href="/wiki/RS-102221" title="RS-102221">RS-102221</a></li> <li><a href="/wiki/S-14671" title="S-14671">S-14671</a></li> <li><a href="/wiki/SB-200646" title="SB-200646">SB-200646</a></li> <li><a href="/wiki/SB-206553" title="SB-206553">SB-206553</a></li> <li><a href="/wiki/SB-221284" title="SB-221284">SB-221284</a></li> <li><a href="/wiki/SB-228357" title="SB-228357">SB-228357</a></li> <li><a href="/wiki/SB-242084" title="SB-242084">SB-242084</a></li> <li><a href="/wiki/SB-243213" title="SB-243213">SB-243213</a></li> <li><a href="/wiki/SDZ_SER-082" title="SDZ SER-082">SDZ SER-082</a></li> <li><a href="/wiki/Tedatioxetine" title="Tedatioxetine">Tedatioxetine</a></li> <li><a href="/wiki/Tetracyclic_antidepressant" title="Tetracyclic antidepressant">Tetracyclic antidepressants</a> (e.g., <a href="/wiki/Amoxapine" title="Amoxapine">amoxapine</a>, <a href="/wiki/Aptazapine" title="Aptazapine">aptazapine</a>, <a href="/wiki/Esmirtazapine" title="Esmirtazapine">esmirtazapine</a>, <a href="/wiki/Maprotiline" title="Maprotiline">maprotiline</a>, <a href="/wiki/Mianserin" title="Mianserin">mianserin</a>, <a href="/wiki/Mirtazapine" title="Mirtazapine">mirtazapine</a>)</li> <li><a href="/wiki/TIK-301" title="TIK-301">TIK-301</a></li> <li><a href="/wiki/Tramadol" title="Tramadol">Tramadol</a></li> <li><a href="/wiki/Trazodone" title="Trazodone">Trazodone</a></li> <li><a href="/wiki/Tricyclic_antidepressant" title="Tricyclic antidepressant">Tricyclic antidepressants</a> (e.g., <a href="/wiki/Amitriptyline" title="Amitriptyline">amitriptyline</a>, <a href="/wiki/Nortriptyline" title="Nortriptyline">nortriptyline</a>)</li> <li><a href="/wiki/Typical_antipsychotic" title="Typical antipsychotic">Typical antipsychotics</a> (e.g., <a href="/wiki/Chlorpromazine" title="Chlorpromazine">chlorpromazine</a>, <a href="/wiki/Loxapine" title="Loxapine">loxapine</a>, <a href="/wiki/Pimozide" title="Pimozide">pimozide</a>, <a href="/wiki/Pipamperone" title="Pipamperone">pipamperone</a>, <a href="/wiki/Thioridazine" title="Thioridazine">thioridazine</a>)</li> <li><a href="/wiki/Xylamidine" title="Xylamidine">Xylamidine</a></li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li>Unknown/unsorted: <a href="/wiki/Efavirenz" title="Efavirenz">Efavirenz</a></li> <li><a href="/wiki/Ergoline" title="Ergoline">Ergolines</a> (e.g., <a href="/wiki/Ergometrine" class="mw-redirect" title="Ergometrine">ergometrine (ergonovine)</a>, <a href="/wiki/Methylergometrine" title="Methylergometrine">methylergometrine (methylergonovine)</a>)</li></ul> </div></td></tr></tbody></table><div></div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/5-HT3_receptor" title="5-HT3 receptor">5-HT3</a>–<a href="/wiki/5-HT7_receptor" title="5-HT7 receptor">7</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/5-HT3_receptor" title="5-HT3 receptor">5-HT3</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><td colspan="2" class="navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li>Agonists: <a href="/wiki/Alcohol_(chemistry)" title="Alcohol (chemistry)">Alcohols</a> (e.g., <a href="/wiki/N-Butanol" class="mw-redirect" title="N-Butanol">butanol</a>, <a href="/wiki/Alcohol_(drug)" title="Alcohol (drug)">ethanol (alcohol)</a>, <a href="/wiki/2,2,2-Trichloroethanol" title="2,2,2-Trichloroethanol">trichloroethanol</a>)</li> <li><a href="/wiki/Chlorophenylbiguanide" title="Chlorophenylbiguanide">m-CPBG</a></li> <li><a href="/wiki/Phenylbiguanide" title="Phenylbiguanide">Phenylbiguanide</a></li> <li><a href="/wiki/Piperazine" title="Piperazine">Piperazines</a> (e.g., <a href="/wiki/Benzylpiperazine" title="Benzylpiperazine">BZP</a>, <a href="/wiki/Meta-Chlorophenylpiperazine" title="Meta-Chlorophenylpiperazine">mCPP</a>, <a href="/wiki/Quipazine" title="Quipazine">quipazine</a>)</li> <li><a href="/wiki/RS-56812" title="RS-56812">RS-56812</a></li> <li><a href="/wiki/Serotonin" title="Serotonin">Serotonin (5-HT)</a></li> <li><a href="/wiki/SR-57227" title="SR-57227">SR-57227</a></li> <li><a href="/w/index.php?title=SR-57227A&action=edit&redlink=1" class="new" title="SR-57227A (page does not exist)">SR-57227A</a></li> <li><a href="/wiki/Substituted_tryptamine" title="Substituted tryptamine">Tryptamines</a> (e.g., <a href="/wiki/2-Methyl-5-hydroxytryptamine" title="2-Methyl-5-hydroxytryptamine">2-Me-5-HT</a>, <a href="/wiki/5-Carboxamidotryptamine" title="5-Carboxamidotryptamine">5-CT</a>, <a href="/wiki/Bufotenidine" title="Bufotenidine">bufotenidine (5-HTQ)</a>)</li> <li><a href="/wiki/Inhalational_anaesthetic" class="mw-redirect" title="Inhalational anaesthetic">Volatiles/gases</a> (e.g., <a href="/wiki/Halothane" title="Halothane">halothane</a>, <a href="/wiki/Isoflurane" title="Isoflurane">isoflurane</a>, <a href="/wiki/Toluene" title="Toluene">toluene</a>, <a href="/wiki/1,1,1-Trichloroethane" title="1,1,1-Trichloroethane">trichloroethane</a>)</li> <li><a href="/wiki/YM-31636" title="YM-31636">YM-31636</a></li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li>Antagonists: <a href="/wiki/Alosetron" title="Alosetron">Alosetron</a></li> <li><a href="/wiki/Anpirtoline" title="Anpirtoline">Anpirtoline</a></li> <li><a href="/w/index.php?title=Arazasetron&action=edit&redlink=1" class="new" title="Arazasetron (page does not exist)">Arazasetron</a></li> <li><a href="/wiki/AS-8112" title="AS-8112">AS-8112</a></li> <li><a href="/wiki/Atypical_antipsychotic" title="Atypical antipsychotic">Atypical antipsychotics</a> (e.g., <a href="/wiki/Clozapine" title="Clozapine">clozapine</a>, <a href="/wiki/Olanzapine" title="Olanzapine">olanzapine</a>, <a href="/wiki/Quetiapine" title="Quetiapine">quetiapine</a>)</li> <li><a href="/wiki/Azasetron" title="Azasetron">Azasetron</a></li> <li><a href="/wiki/Batanopride" title="Batanopride">Batanopride</a></li> <li><a href="/wiki/Bemesetron" title="Bemesetron">Bemesetron (MDL-72222)</a></li> <li><a href="/wiki/Bupropion" title="Bupropion">Bupropion</a></li> <li><a href="/wiki/Cilansetron" title="Cilansetron">Cilansetron</a></li> <li><a href="/wiki/CSP-2503" title="CSP-2503">CSP-2503</a></li> <li><a href="/wiki/Dazopride" title="Dazopride">Dazopride</a></li> <li><a href="/wiki/Dolasetron" title="Dolasetron">Dolasetron</a></li> <li><a href="/wiki/Galanolactone" title="Galanolactone">Galanolactone</a></li> <li><a href="/wiki/Granisetron" title="Granisetron">Granisetron</a></li> <li><a href="/wiki/Hydroxybupropion" title="Hydroxybupropion">Hydroxybupropion</a></li> <li><a href="/wiki/Lerisetron" title="Lerisetron">Lerisetron</a></li> <li><a href="/wiki/Memantine" title="Memantine">Memantine</a></li> <li><a href="/wiki/Ondansetron" title="Ondansetron">Ondansetron</a></li> <li><a href="/wiki/Palonosetron" title="Palonosetron">Palonosetron</a></li> <li><a href="/wiki/Ramosetron" title="Ramosetron">Ramosetron</a></li> <li><a href="/wiki/Renzapride" title="Renzapride">Renzapride</a></li> <li><a href="/wiki/Ricasetron" title="Ricasetron">Ricasetron</a></li> <li><a href="/wiki/Tedatioxetine" title="Tedatioxetine">Tedatioxetine</a></li> <li><a href="/wiki/Tetracyclic_antidepressant" title="Tetracyclic antidepressant">Tetracyclic antidepressants</a> (e.g., <a href="/wiki/Amoxapine" title="Amoxapine">amoxapine</a>, <a href="/wiki/Mianserin" title="Mianserin">mianserin</a>, <a href="/wiki/Mirtazapine" title="Mirtazapine">mirtazapine</a>)</li> <li><a href="/wiki/Thujone" title="Thujone">Thujone</a></li> <li><a href="/wiki/Tropanserin" title="Tropanserin">Tropanserin</a></li> <li><a href="/wiki/Tropisetron" title="Tropisetron">Tropisetron</a></li> <li><a href="/wiki/Typical_antipsychotic" title="Typical antipsychotic">Typical antipsychotics</a> (e.g., <a href="/wiki/Loxapine" title="Loxapine">loxapine</a>)</li> <li><a href="/wiki/Inhalational_anaesthetic" class="mw-redirect" title="Inhalational anaesthetic">Volatiles/gases</a> (e.g., <a href="/wiki/Nitrous_oxide" title="Nitrous oxide">nitrous oxide</a>, <a href="/wiki/Sevoflurane" title="Sevoflurane">sevoflurane</a>, <a href="/wiki/Xenon" title="Xenon">xenon</a>)</li> <li><a href="/wiki/Vortioxetine" title="Vortioxetine">Vortioxetine</a></li> <li><a href="/wiki/Zacopride" title="Zacopride">Zacopride</a></li> <li><a href="/wiki/Zatosetron" title="Zatosetron">Zatosetron</a></li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li>Unknown/unsorted: <a href="/w/index.php?title=LY-53857&action=edit&redlink=1" class="new" title="LY-53857 (page does not exist)">LY-53857</a></li> <li><a href="/wiki/Piperazine" title="Piperazine">Piperazines</a> (e.g., <a href="/wiki/Naphthylpiperazine" title="Naphthylpiperazine">naphthylpiperazine</a>)</li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/5-HT4_receptor" title="5-HT4 receptor">5-HT4</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><td colspan="2" class="navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li>Agonists: <a href="/wiki/5-Methoxytryptamine" title="5-Methoxytryptamine">5-MT</a></li> <li><a href="/wiki/BIMU8" title="BIMU8">BIMU8</a></li> <li><a href="/wiki/Capeserod" title="Capeserod">Capeserod</a></li> <li><a href="/wiki/Cinitapride" title="Cinitapride">Cinitapride</a></li> <li><a href="/wiki/Cisapride" title="Cisapride">Cisapride</a></li> <li><a href="/wiki/CJ-033466" title="CJ-033466">CJ-033466</a></li> <li><a href="/wiki/Dazopride" title="Dazopride">Dazopride</a></li> <li><a href="/wiki/Metoclopramide" title="Metoclopramide">Metoclopramide</a></li> <li><a href="/w/index.php?title=Minesapride&action=edit&redlink=1" class="new" title="Minesapride (page does not exist)">Minesapride</a></li> <li><a href="/wiki/Mosapride" title="Mosapride">Mosapride</a></li> <li><a href="/wiki/Prucalopride" title="Prucalopride">Prucalopride</a></li> <li><a href="/wiki/PRX-03140" title="PRX-03140">PRX-03140</a></li> <li><a href="/wiki/Renzapride" title="Renzapride">Renzapride</a></li> <li><a href="/wiki/RS-67,333" title="RS-67,333">RS-67,333</a></li> <li><a href="/w/index.php?title=RS-67,506&action=edit&redlink=1" class="new" title="RS-67,506 (page does not exist)">RS-67,506</a></li> <li><a href="/wiki/Serotonin" title="Serotonin">Serotonin (5-HT)</a></li> <li><a href="/wiki/Tegaserod" title="Tegaserod">Tegaserod</a></li> <li><a href="/w/index.php?title=Usmarapride&action=edit&redlink=1" class="new" title="Usmarapride (page does not exist)">Usmarapride</a></li> <li><a href="/wiki/Velusetrag" title="Velusetrag">Velusetrag</a></li> <li><a href="/wiki/Zacopride" title="Zacopride">Zacopride</a></li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li>Antagonists: <a href="/wiki/GR-113808" title="GR-113808">GR-113808</a></li> <li><a href="/w/index.php?title=GR-125487&action=edit&redlink=1" class="new" title="GR-125487 (page does not exist)">GR-125487</a></li> <li><a href="/wiki/Lysine" title="Lysine">L-Lysine</a></li> <li><a href="/wiki/Piboserod" title="Piboserod">Piboserod</a></li> <li><a href="/w/index.php?title=RS-39604&action=edit&redlink=1" class="new" title="RS-39604 (page does not exist)">RS-39604</a></li> <li><a href="/w/index.php?title=RS-67532&action=edit&redlink=1" class="new" title="RS-67532 (page does not exist)">RS-67532</a></li> <li><a href="/w/index.php?title=SB-203186&action=edit&redlink=1" class="new" title="SB-203186 (page does not exist)">SB-203186</a></li> <li><a href="/wiki/SB-204070" title="SB-204070">SB-204070</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/5-HT5A_receptor" title="5-HT5A receptor">5-HT5A</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><td colspan="2" class="navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li>Agonists: <a href="/wiki/Ergoline" title="Ergoline">Ergolines</a> (e.g., <a href="/wiki/2-Bromo-LSD" title="2-Bromo-LSD">2-Br-LSD (BOL-148)</a>, <a href="/wiki/Ergotamine" title="Ergotamine">ergotamine</a>, <a href="/wiki/LSD" title="LSD">LSD</a>)</li> <li><a href="/wiki/Serotonin" title="Serotonin">Serotonin (5-HT)</a></li> <li><a href="/wiki/Substituted_tryptamine" title="Substituted tryptamine">Tryptamines</a> (e.g., <a href="/wiki/5-Carboxamidotryptamine" title="5-Carboxamidotryptamine">5-CT</a>)</li> <li><a href="/wiki/Valerenic_acid" title="Valerenic acid">Valerenic acid</a></li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li>Antagonists: <a href="/wiki/Asenapine" title="Asenapine">Asenapine</a></li> <li><a href="/wiki/Latrepirdine" title="Latrepirdine">Latrepirdine (dimebolin)</a></li> <li><a href="/wiki/Metitepine" title="Metitepine">Metitepine (methiothepin)</a></li> <li><a href="/wiki/Ritanserin" title="Ritanserin">Ritanserin</a></li> <li><a href="/wiki/SB-699551" title="SB-699551">SB-699551</a></li></ul> <ul><li>Unknown/unsorted: <a href="/wiki/Ergoline" title="Ergoline">Ergolines</a> (e.g., <a href="/wiki/Metergoline" title="Metergoline">metergoline</a>, <a href="/wiki/Methysergide" title="Methysergide">methysergide</a>)</li> <li><a href="/wiki/Piperazine" title="Piperazine">Piperazines</a> (e.g., <a href="/wiki/Naphthylpiperazine" title="Naphthylpiperazine">naphthylpiperazine</a>)</li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/5-HT6_receptor" title="5-HT6 receptor">5-HT6</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><td colspan="2" class="navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li>Agonists: <a href="/wiki/Ergoline" title="Ergoline">Ergolines</a> (e.g., <a href="/wiki/Dihydroergocryptine" title="Dihydroergocryptine">dihydroergocryptine</a>, <a href="/wiki/Dihydroergotamine" title="Dihydroergotamine">dihydroergotamine</a>, <a href="/wiki/Ergotamine" title="Ergotamine">ergotamine</a>, <a href="/wiki/Lisuride" title="Lisuride">lisuride</a>, <a href="/wiki/LSD" title="LSD">LSD</a>, <a href="/wiki/Mesulergine" title="Mesulergine">mesulergine</a>, <a href="/wiki/Metergoline" title="Metergoline">metergoline</a>, <a href="/wiki/Methysergide" title="Methysergide">methysergide</a>)</li> <li><a href="/wiki/Hypidone" title="Hypidone">Hypidone</a></li> <li><a href="/wiki/Serotonin" title="Serotonin">Serotonin (5-HT)</a></li> <li><a href="/wiki/Substituted_tryptamine" title="Substituted tryptamine">Tryptamines</a> (e.g., <a href="/wiki/2-Methyl-5-hydroxytryptamine" title="2-Methyl-5-hydroxytryptamine">2-Me-5-HT</a>, <a href="/wiki/5-Benzyloxytryptamine" title="5-Benzyloxytryptamine">5-BT</a>, <a href="/wiki/5-Carboxamidotryptamine" title="5-Carboxamidotryptamine">5-CT</a>, <a href="/wiki/5-Methoxytryptamine" title="5-Methoxytryptamine">5-MT</a>, <a href="/wiki/Bufotenin" title="Bufotenin">Bufotenin</a>, <a href="/wiki/E-6801" title="E-6801">E-6801</a>, <a href="/wiki/E-6837" title="E-6837">E-6837</a>, <a href="/wiki/EMD-386088" title="EMD-386088">EMD-386088</a>, <a href="/wiki/EMDT" title="EMDT">EMDT</a>, <a href="/w/index.php?title=LY-586713&action=edit&redlink=1" class="new" title="LY-586713 (page does not exist)">LY-586713</a>, <a href="/w/index.php?title=N-Methyl-5-HT&action=edit&redlink=1" class="new" title="N-Methyl-5-HT (page does not exist)">N-Me-5-HT</a>, <a href="/wiki/ST-1936" title="ST-1936">ST-1936</a>, <a href="/wiki/Tryptamine" title="Tryptamine">tryptamine</a>)</li> <li><a href="/wiki/WAY-181187" title="WAY-181187">WAY-181187</a></li> <li><a href="/wiki/WAY-208466" title="WAY-208466">WAY-208466</a></li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li>Antagonists: <a href="/w/index.php?title=ABT-354&action=edit&redlink=1" class="new" title="ABT-354 (page does not exist)">ABT-354</a></li> <li><a href="/wiki/Atypical_antipsychotic" title="Atypical antipsychotic">Atypical antipsychotics</a> (e.g., <a href="/wiki/Aripiprazole" title="Aripiprazole">aripiprazole</a>, <a href="/wiki/Asenapine" title="Asenapine">asenapine</a>, <a href="/wiki/Clorotepine" title="Clorotepine">clorotepine</a>, <a href="/wiki/Clozapine" title="Clozapine">clozapine</a>, <a href="/wiki/Fluperlapine" title="Fluperlapine">fluperlapine</a>, <a href="/wiki/Iloperidone" title="Iloperidone">iloperidone</a>, <a href="/wiki/Olanzapine" title="Olanzapine">olanzapine</a>, <a href="/wiki/Tiospirone" title="Tiospirone">tiospirone</a>)</li> <li><a href="/wiki/AVN-101" class="mw-redirect" title="AVN-101">AVN-101</a></li> <li><a href="/wiki/AVN-211" title="AVN-211">AVN-211</a></li> <li><a href="/wiki/AVN-322" title="AVN-322">AVN-322</a></li> <li><a href="/wiki/AVN-397" title="AVN-397">AVN-397</a></li> <li><a href="/w/index.php?title=BGC20-760&action=edit&redlink=1" class="new" title="BGC20-760 (page does not exist)">BGC20-760</a></li> <li><a href="/w/index.php?title=BVT-5182&action=edit&redlink=1" class="new" title="BVT-5182 (page does not exist)">BVT-5182</a></li> <li><a href="/w/index.php?title=BVT-74316&action=edit&redlink=1" class="new" title="BVT-74316 (page does not exist)">BVT-74316</a></li> <li><a href="/wiki/Cerlapirdine" title="Cerlapirdine">Cerlapirdine</a></li> <li><a href="/wiki/EGIS-12,233" title="EGIS-12,233">EGIS-12,233</a></li> <li><a href="/w/index.php?title=GW-742457&action=edit&redlink=1" class="new" title="GW-742457 (page does not exist)">GW-742457</a></li> <li><a href="/wiki/Idalopirdine" title="Idalopirdine">Idalopirdine</a></li> <li><a href="/wiki/Ketanserin" title="Ketanserin">Ketanserin</a></li> <li><a href="/w/index.php?title=Landipirdine&action=edit&redlink=1" class="new" title="Landipirdine (page does not exist)">Landipirdine</a></li> <li><a href="/wiki/Latrepirdine" title="Latrepirdine">Latrepirdine (dimebolin)</a></li> <li><a href="/wiki/Masupirdine" title="Masupirdine">Masupirdine</a></li> <li><a href="/wiki/Metitepine" title="Metitepine">Metitepine (methiothepin)</a></li> <li><a href="/wiki/MS-245" title="MS-245">MS-245</a></li> <li><a href="/wiki/PRX-07034" title="PRX-07034">PRX-07034</a></li> <li><a href="/wiki/Ritanserin" title="Ritanserin">Ritanserin</a></li> <li><a href="/wiki/Ro_04-6790" title="Ro 04-6790">Ro 04-6790</a></li> <li><a href="/w/index.php?title=Ro_63-0563&action=edit&redlink=1" class="new" title="Ro 63-0563 (page does not exist)">Ro 63-0563</a></li> <li><a href="/wiki/SB-258585" title="SB-258585">SB-258585</a></li> <li><a href="/wiki/SB-271046" title="SB-271046">SB-271046</a></li> <li><a href="/wiki/SB-357134" title="SB-357134">SB-357134</a></li> <li><a href="/wiki/SB-399885" title="SB-399885">SB-399885</a></li> <li><a href="/wiki/Intepirdine" title="Intepirdine">SB-742457</a></li> <li><a href="/wiki/Tetracyclic_antidepressant" title="Tetracyclic antidepressant">Tetracyclic antidepressants</a> (e.g., <a href="/wiki/Amoxapine" title="Amoxapine">amoxapine</a>, <a href="/wiki/Mianserin" title="Mianserin">mianserin</a>)</li> <li><a href="/wiki/Tricyclic_antidepressant" title="Tricyclic antidepressant">Tricyclic antidepressants</a> (e.g., <a href="/wiki/Amitriptyline" title="Amitriptyline">amitriptyline</a>, <a href="/wiki/Clomipramine" title="Clomipramine">clomipramine</a>, <a href="/wiki/Doxepin" title="Doxepin">doxepin</a>, <a href="/wiki/Nortriptyline" title="Nortriptyline">nortriptyline</a>)</li> <li><a href="/wiki/Typical_antipsychotic" title="Typical antipsychotic">Typical antipsychotics</a> (e.g., <a href="/wiki/Chlorpromazine" title="Chlorpromazine">chlorpromazine</a>, <a href="/wiki/Loxapine" title="Loxapine">loxapine</a>)</li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li>Unknown/unsorted: <a href="/wiki/Ergoline" title="Ergoline">Ergolines</a> (e.g., <a href="/wiki/2-Bromo-LSD" title="2-Bromo-LSD">2-Br-LSD (BOL-148)</a>, <a href="/wiki/Bromocriptine" title="Bromocriptine">bromocriptine</a>, <a href="/wiki/Lergotrile" title="Lergotrile">lergotrile</a>, <a href="/wiki/Pergolide" title="Pergolide">pergolide</a>)</li> <li><a href="/wiki/Piperazine" title="Piperazine">Piperazines</a> (e.g., <a href="/wiki/Naphthylpiperazine" title="Naphthylpiperazine">naphthylpiperazine</a>)</li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/5-HT7_receptor" title="5-HT7 receptor">5-HT7</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><td colspan="2" class="navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li>Agonists: <a href="/wiki/8-OH-DPAT" title="8-OH-DPAT">8-OH-DPAT</a></li> <li><a href="/wiki/AS-19_(drug)" title="AS-19 (drug)">AS-19</a></li> <li><a href="/wiki/Bifeprunox" title="Bifeprunox">Bifeprunox</a></li> <li><a href="/wiki/E-55888" title="E-55888">E-55888</a></li> <li><a href="/wiki/Ergoline" title="Ergoline">Ergolines</a> (e.g., <a href="/wiki/LSD" title="LSD">LSD</a>)</li> <li><a href="/wiki/LP-12" title="LP-12">LP-12</a></li> <li><a href="/wiki/LP-44" title="LP-44">LP-44</a></li> <li><a href="/wiki/LP-211" title="LP-211">LP-211</a></li> <li><a href="/wiki/RU-24,969" title="RU-24,969">RU-24,969</a></li> <li><a href="/wiki/Sarizotan" title="Sarizotan">Sarizotan</a></li> <li><a href="/wiki/Serotonin" title="Serotonin">Serotonin (5-HT)</a></li> <li><a href="/wiki/Triptan" title="Triptan">Triptans</a> (e.g., <a href="/wiki/Frovatriptan" title="Frovatriptan">frovatriptan</a>)</li> <li><a href="/wiki/Substituted_tryptamine" title="Substituted tryptamine">Tryptamines</a> (e.g., <a href="/wiki/5-Carboxamidotryptamine" title="5-Carboxamidotryptamine">5-CT</a>, <a href="/wiki/5-Methoxytryptamine" title="5-Methoxytryptamine">5-MT</a>, <a href="/wiki/Bufotenin" title="Bufotenin">bufotenin</a>, <a href="/wiki/N-Methylserotonin" title="N-Methylserotonin">N-Me-5-HT</a>)</li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li>Antagonists: <a href="/wiki/Atypical_antipsychotic" title="Atypical antipsychotic">Atypical antipsychotics</a> (e.g., <a href="/wiki/Amisulpride" title="Amisulpride">amisulpride</a>, <a href="/wiki/Aripiprazole" title="Aripiprazole">aripiprazole</a>, <a href="/wiki/Asenapine" title="Asenapine">asenapine</a>, <a href="/wiki/Brexpiprazole" title="Brexpiprazole">brexpiprazole</a>, <a href="/wiki/Clorotepine" title="Clorotepine">clorotepine</a>, <a href="/wiki/Clozapine" title="Clozapine">clozapine</a>, <a href="/wiki/Fluperlapine" title="Fluperlapine">fluperlapine</a>, <a href="/wiki/Olanzapine" title="Olanzapine">olanzapine</a>, <a href="/wiki/Risperidone" title="Risperidone">risperidone</a>, <a href="/wiki/Sertindole" title="Sertindole">sertindole</a>, <a href="/wiki/Tiospirone" title="Tiospirone">tiospirone</a>, <a href="/wiki/Ziprasidone" title="Ziprasidone">ziprasidone</a>, <a href="/wiki/Zotepine" title="Zotepine">zotepine</a>)</li> <li><a href="/wiki/Butaclamol" title="Butaclamol">Butaclamol</a></li> <li><a href="/wiki/DR-4485" title="DR-4485">DR-4485</a></li> <li><a href="/wiki/EGIS-12,233" title="EGIS-12,233">EGIS-12,233</a></li> <li><a href="/wiki/Ergoline" title="Ergoline">Ergolines</a> (e.g., <a href="/wiki/2-Bromo-LSD" title="2-Bromo-LSD">2-Br-LSD (BOL-148)</a>, <a href="/wiki/Amesergide" title="Amesergide">amesergide</a>, <a href="/wiki/Bromocriptine" title="Bromocriptine">bromocriptine</a>, <a href="/wiki/Cabergoline" title="Cabergoline">cabergoline</a>, <a href="/wiki/Dihydroergotamine" title="Dihydroergotamine">dihydroergotamine</a>, <a href="/wiki/Ergotamine" title="Ergotamine">ergotamine</a>, <a href="/w/index.php?title=LY-53857&action=edit&redlink=1" class="new" title="LY-53857 (page does not exist)">LY-53857</a>, <a href="/wiki/LY-215,840" title="LY-215,840">LY-215,840</a>, <a href="/wiki/Mesulergine" title="Mesulergine">mesulergine</a>, <a href="/wiki/Metergoline" title="Metergoline">metergoline</a>, <a href="/wiki/Methysergide" title="Methysergide">methysergide</a>, <a href="/wiki/Sergolexole" title="Sergolexole">sergolexole</a>)</li> <li><a href="/wiki/JNJ-18038683" title="JNJ-18038683">JNJ-18038683</a></li> <li><a href="/wiki/Ketanserin" title="Ketanserin">Ketanserin</a></li> <li><a href="/wiki/LY-215,840" title="LY-215,840">LY-215,840</a></li> <li><a href="/wiki/Metitepine" title="Metitepine">Metitepine (methiothepin)</a></li> <li><a href="/wiki/Ritanserin" title="Ritanserin">Ritanserin</a></li> <li><a href="/wiki/SB-258719" title="SB-258719">SB-258719</a></li> <li><a href="/w/index.php?title=SB-258741&action=edit&redlink=1" class="new" title="SB-258741 (page does not exist)">SB-258741</a></li> <li><a href="/wiki/SB-269970" title="SB-269970">SB-269970</a></li> <li><a href="/w/index.php?title=SB-656104&action=edit&redlink=1" class="new" title="SB-656104 (page does not exist)">SB-656104</a></li> <li><a href="/w/index.php?title=SB-656104A&action=edit&redlink=1" class="new" title="SB-656104A (page does not exist)">SB-656104A</a></li> <li><a href="/w/index.php?title=SB-691673&action=edit&redlink=1" class="new" title="SB-691673 (page does not exist)">SB-691673</a></li> <li><a href="/w/index.php?title=SLV-313&action=edit&redlink=1" class="new" title="SLV-313 (page does not exist)">SLV-313</a></li> <li><a href="/w/index.php?title=SLV-314&action=edit&redlink=1" class="new" title="SLV-314 (page does not exist)">SLV-314</a></li> <li><a href="/wiki/Spiperone" title="Spiperone">Spiperone</a></li> <li><a href="/w/index.php?title=SSR-181507&action=edit&redlink=1" class="new" title="SSR-181507 (page does not exist)">SSR-181507</a></li> <li><a href="/wiki/Tetracyclic_antidepressant" title="Tetracyclic antidepressant">Tetracyclic antidepressants</a> (e.g., <a href="/wiki/Amoxapine" title="Amoxapine">amoxapine</a>, <a href="/wiki/Maprotiline" title="Maprotiline">maprotiline</a>, <a href="/wiki/Mianserin" title="Mianserin">mianserin</a>, <a href="/wiki/Mirtazapine" title="Mirtazapine">mirtazapine</a>)</li> <li><a href="/wiki/Tricyclic_antidepressant" title="Tricyclic antidepressant">Tricyclic antidepressants</a> (e.g., <a href="/wiki/Amitriptyline" title="Amitriptyline">amitriptyline</a>, <a href="/wiki/Clomipramine" title="Clomipramine">clomipramine</a>, <a href="/wiki/Imipramine" title="Imipramine">imipramine</a>)</li> <li><a href="/wiki/Typical_antipsychotic" title="Typical antipsychotic">Typical antipsychotics</a> (e.g., <a href="/wiki/Acetophenazine" title="Acetophenazine">acetophenazine</a>, <a href="/wiki/Chlorpromazine" title="Chlorpromazine">chlorpromazine</a>, <a href="/wiki/Chlorprothixene" title="Chlorprothixene">chlorprothixene</a>, <a href="/wiki/Fluphenazine" title="Fluphenazine">fluphenazine</a>, <a href="/wiki/Loxapine" title="Loxapine">loxapine</a>, <a href="/wiki/Pimozide" title="Pimozide">pimozide</a>)</li> <li><a href="/wiki/Vortioxetine" title="Vortioxetine">Vortioxetine</a></li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li>Unknown/unsorted: <a href="/wiki/Ergoline" title="Ergoline">Ergolines</a> (e.g., <a href="/wiki/Lisuride" title="Lisuride">lisuride</a>, <a href="/wiki/Pergolide" title="Pergolide">pergolide</a>)</li> <li><a href="/wiki/Piperazine" title="Piperazine">Piperazines</a> (e.g., <a href="/wiki/Naphthylpiperazine" title="Naphthylpiperazine">naphthylpiperazine</a>)</li></ul> </div></td></tr></tbody></table><div></div></td></tr></tbody></table><div></div></td></tr><tr><td class="navbox-abovebelow" colspan="2"><div> <ul><li>See also: <a href="/wiki/Template:Receptor_modulators" title="Template:Receptor modulators">Receptor/signaling modulators</a></li> <li><a href="/wiki/Template:Adrenergic_receptor_modulators" title="Template:Adrenergic receptor modulators">Adrenergics</a></li> <li><a href="/wiki/Template:Dopamine_receptor_modulators" title="Template:Dopamine receptor modulators">Dopaminergics</a></li> <li><a href="/wiki/Template:Melatonin_receptor_modulators" title="Template:Melatonin receptor modulators">Melatonergics</a></li> <li><a href="/wiki/Template:Monoamine_reuptake_inhibitors" title="Template:Monoamine reuptake inhibitors">Monoamine reuptake inhibitors</a> and <a href="/wiki/Template:Monoamine_releasing_agents" title="Template:Monoamine releasing agents">releasing agents</a></li> <li><a href="/wiki/Template:Monoamine_metabolism_modulators" title="Template:Monoamine metabolism modulators">Monoamine metabolism modulators</a></li> <li><a href="/wiki/Template:Monoamine_neurotoxins" class="mw-redirect" title="Template:Monoamine neurotoxins">Monoamine neurotoxins</a></li></ul> </div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374" /><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235" /></div><div role="navigation" class="navbox" aria-labelledby="Sigma_receptor_modulators212" style="padding:3px"><table class="nowraplinks hlist mw-collapsible mw-collapsed navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374" /><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231" /><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Sigma_receptor_modulators" title="Template:Sigma receptor modulators"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Sigma_receptor_modulators" title="Template talk:Sigma receptor modulators"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Sigma_receptor_modulators" title="Special:EditPage/Template:Sigma receptor modulators"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Sigma_receptor_modulators212" style="font-size:114%;margin:0 4em"><a href="/wiki/Sigma_receptor" title="Sigma receptor">Sigma receptor</a> <a href="/wiki/Receptor_modulator" title="Receptor modulator">modulators</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Sigma-1_receptor" title="Sigma-1 receptor">σ1</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li>Agonists: <a href="/wiki/3-PPP" title="3-PPP">3-PPP</a></li> <li><a href="/wiki/4-PPBP" title="4-PPBP">4-PPBP</a></li> <li><a href="/wiki/5-MeO-DMT" title="5-MeO-DMT">5-MeO-DMT</a></li> <li><a href="/wiki/Alazocine" title="Alazocine">Alazocine (SKF-10047)</a></li> <li><a href="/wiki/Amantadine" title="Amantadine">Amantadine</a></li> <li><a href="/wiki/Arketamine" title="Arketamine">Arketamine</a></li> <li><a href="/w/index.php?title=BD-737&action=edit&redlink=1" class="new" title="BD-737 (page does not exist)">BD-737</a></li> <li><a href="/wiki/BD-1052" class="mw-redirect" title="BD-1052">BD-1052</a></li> <li><a href="/wiki/Blarcamesine" title="Blarcamesine">Blarcamesine</a></li> <li><a href="/wiki/Captodiame" title="Captodiame">Captodiame</a></li> <li><a href="/wiki/Citalopram" title="Citalopram">Citalopram</a></li> <li><a href="/wiki/Calcitonin_gene-related_peptide" title="Calcitonin gene-related peptide"><abbr title="Calcitonin gene-related peptide">CGRP</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Calcitonin gene-related peptide</li> <li><a href="/wiki/Cloperastine" title="Cloperastine">Cloperastine</a></li> <li><a href="/wiki/Cocaine" title="Cocaine">Cocaine</a></li> <li><a href="/wiki/Cutamesine" title="Cutamesine">Cutamesine (SA-4503)</a></li> <li><a href="/wiki/Cyclazocine" title="Cyclazocine">Cyclazocine</a></li> <li><a href="/wiki/Dehydroepiandrosterone" title="Dehydroepiandrosterone">Dehydroepiandrosterone (DHEA)</a> (<a href="/wiki/Prasterone" title="Prasterone">prasterone</a>)</li> <li><a href="/wiki/Dehydroepiandrosterone_sulfate" title="Dehydroepiandrosterone sulfate">Dehydroepiandrosterone sulfate (DHEA-S)</a> (<a href="/wiki/Prasterone_sulfate" title="Prasterone sulfate">prasterone sulfate</a>)</li> <li><a href="/wiki/Dextrallorphan" title="Dextrallorphan">Dextrallorphan</a></li> <li><a href="/wiki/Dextromethorphan" title="Dextromethorphan">Dextromethorphan (DXM)</a></li> <li><a href="/wiki/Dextrorphan" title="Dextrorphan">Dextrorphan (DXO)</a></li> <li><a href="/wiki/Dimemorfan" title="Dimemorfan">Dimemorfan</a></li> <li><a href="/wiki/Dimethyltryptamine" class="mw-redirect" title="Dimethyltryptamine">Dimethyltryptamine (DMT)</a></li> <li><a href="/wiki/Ditolylguanidine" title="Ditolylguanidine">Ditolylguanidine (DTG)</a></li> <li><a href="/wiki/Donepezil" title="Donepezil">Donepezil</a></li> <li><a href="/wiki/Eliprodil" title="Eliprodil">Eliprodil</a></li> <li><a href="/wiki/Escitalopram" title="Escitalopram">Escitalopram</a></li> <li><a href="/wiki/Fabomotizole" title="Fabomotizole">Fabomotizole (afobazole)</a></li> <li><a href="/wiki/Fluoxetine" title="Fluoxetine">Fluoxetine</a></li> <li><a href="/wiki/Fluvoxamine" title="Fluvoxamine">Fluvoxamine</a></li> <li><a href="/wiki/Ifenprodil" title="Ifenprodil">Ifenprodil</a></li> <li><a href="/wiki/Igmesine" title="Igmesine">Igmesine (JO-1784)</a></li> <li><a href="/w/index.php?title=IPAB_(drug)&action=edit&redlink=1" class="new" title="IPAB (drug) (page does not exist)">IPAB</a></li> <li><a href="/wiki/Ketamine" title="Ketamine">Ketamine</a></li> <li><a href="/wiki/L-687384" class="mw-redirect" title="L-687384">L-687384</a></li> <li><a class="mw-selflink selflink"><abbr title="Methylenedioxymethamphetamine">MDMA</abbr> (midomafetamine)</a></li> <li><a href="/wiki/Memantine" title="Memantine">Memantine</a></li> <li><a href="/wiki/Methamphetamine" title="Methamphetamine">Methamphetamine</a></li> <li><a href="/wiki/Methoxetamine" title="Methoxetamine">Methoxetamine</a></li> <li><a href="/wiki/Methylphenidate" title="Methylphenidate">Methylphenidate</a></li> <li><a href="/wiki/Nepinalone" title="Nepinalone">Nepinalone</a></li> <li><a href="/wiki/Neuropeptide_Y" title="Neuropeptide Y">Neuropeptide Y</a></li> <li><a href="/wiki/Noscapine" title="Noscapine">Noscapine</a></li> <li><a href="/w/index.php?title=OPC-14523&action=edit&redlink=1" class="new" title="OPC-14523 (page does not exist)">OPC-14523</a></li> <li><a href="/wiki/Opipramol" title="Opipramol">Opipramol</a></li> <li><a href="/wiki/Pentazocine" title="Pentazocine">Pentazocine</a></li> <li><a href="/wiki/Pentoxyverine" title="Pentoxyverine">Pentoxyverine (carbetapentane)</a></li> <li><a href="/wiki/PRE-084" title="PRE-084">PRE-084</a></li> <li><a href="/wiki/Pregnenolone" title="Pregnenolone">Pregnenolone</a></li> <li><a href="/wiki/Pregnenolone_sulfate" title="Pregnenolone sulfate">Pregnenolone sulfate</a></li> <li><a href="/wiki/Pridopidine" title="Pridopidine">Pridopidine</a></li> <li><a href="/wiki/Racemethorphan" class="mw-redirect" title="Racemethorphan">Racemethorphan (methorphan)</a></li> <li><a href="/wiki/Racemorphan" title="Racemorphan">Racemorphan (morphanol)</a></li> <li><a href="/w/index.php?title=UMB-23&action=edit&redlink=1" class="new" title="UMB-23 (page does not exist)">UMB-23</a></li> <li><a href="/w/index.php?title=UMB-82&action=edit&redlink=1" class="new" title="UMB-82 (page does not exist)">UMB-82</a></li></ul> <ul><li>Antagonists: <a href="/wiki/3-PPP" title="3-PPP">3-PPP</a></li> <li><a href="/wiki/AC-927" class="mw-redirect" title="AC-927">AC-927</a></li> <li><a href="/wiki/BD-1008" class="mw-redirect" title="BD-1008">BD-1008</a></li> <li><a href="/wiki/BD-1031" class="mw-redirect" title="BD-1031">BD-1031</a></li> <li><a href="/wiki/BD-1047" title="BD-1047">BD-1047</a></li> <li><a href="/wiki/BD-1060" class="mw-redirect" title="BD-1060">BD-1060</a></li> <li><a href="/wiki/BD-1063" class="mw-redirect" title="BD-1063">BD-1063</a></li> <li><a href="/wiki/BD-1067" class="mw-redirect" title="BD-1067">BD-1067</a></li> <li><a href="/wiki/BMY-14802" title="BMY-14802">BMY-14802 (BMS-181100)</a></li> <li><a href="/wiki/CM-156" class="mw-redirect" title="CM-156">CM-156</a></li> <li><a href="/w/index.php?title=Dup-734&action=edit&redlink=1" class="new" title="Dup-734 (page does not exist)">Dup-734</a></li> <li><a href="/w/index.php?title=E-5842&action=edit&redlink=1" class="new" title="E-5842 (page does not exist)">E-5842</a></li> <li><a href="/wiki/E-52862" title="E-52862">E-52862 (S1RA)</a></li> <li><a href="/wiki/Haloperidol" title="Haloperidol">Haloperidol</a></li> <li><a href="/w/index.php?title=LR-132&action=edit&redlink=1" class="new" title="LR-132 (page does not exist)">LR-132</a></li> <li><a href="/w/index.php?title=LR-172&action=edit&redlink=1" class="new" title="LR-172 (page does not exist)">LR-172</a></li> <li><a href="/wiki/MS-377" title="MS-377">MS-377</a></li> <li><a href="/wiki/NE-100" title="NE-100">NE-100</a></li> <li><a href="/w/index.php?title=NPC-16377&action=edit&redlink=1" class="new" title="NPC-16377 (page does not exist)">NPC-16377</a></li> <li><a href="/wiki/Panamesine" title="Panamesine">Panamesine (EMD-57455)</a></li> <li><a href="/w/index.php?title=PD-144418&action=edit&redlink=1" class="new" title="PD-144418 (page does not exist)">PD-144418</a></li> <li><a href="/wiki/Pentazocine" title="Pentazocine">Pentazocine</a></li> <li><a href="/wiki/Progesterone" title="Progesterone">Progesterone</a></li> <li><a href="/wiki/Rimcazole" title="Rimcazole">Rimcazole (BW-234U)</a></li> <li><a href="/wiki/Sertraline" title="Sertraline">Sertraline</a></li> <li><a href="/w/index.php?title=SR-31742A&action=edit&redlink=1" class="new" title="SR-31742A (page does not exist)">SR-31742A</a></li></ul> <ul><li>Allosteric modulators: <a href="/wiki/Phenytoin" title="Phenytoin">Phenytoin</a>; Positive: <a href="/wiki/Methylphenylpiracetam" title="Methylphenylpiracetam">Methylphenylpiracetam</a></li> <li><a href="/w/index.php?title=SOMCL-668&action=edit&redlink=1" class="new" title="SOMCL-668 (page does not exist)">SOMCL-668</a></li></ul> <ul><li>Unknown/unsorted: <a href="/w/index.php?title=3-Methoxydextrallorphan&action=edit&redlink=1" class="new" title="3-Methoxydextrallorphan (page does not exist)">3-Methoxydextrallorphan</a></li> <li><a href="/wiki/3-MeO-PCP" title="3-MeO-PCP">3-MeO-PCP</a></li> <li><a href="/wiki/4C-T-2" title="4C-T-2">4C-T-2</a></li> <li><a href="/w/index.php?title=4-IBP&action=edit&redlink=1" class="new" title="4-IBP (page does not exist)">4-IBP</a></li> <li><a href="/w/index.php?title=4-IPBS&action=edit&redlink=1" class="new" title="4-IPBS (page does not exist)">4-IPBS</a></li> <li><a href="/wiki/4-MeO-PCP" title="4-MeO-PCP">4-MeO-PCP</a></li> <li><a href="/wiki/5-MeO-DALT" title="5-MeO-DALT">5-MeO-DALT</a></li> <li><a href="/wiki/5-MeO-DiPT" title="5-MeO-DiPT">5-MeO-DiPT</a></li> <li><a href="/wiki/Amitriptyline" title="Amitriptyline">Amitriptyline</a></li> <li><a href="/w/index.php?title=Azidopamil&action=edit&redlink=1" class="new" title="Azidopamil (page does not exist)">Azidopamil</a></li> <li><a href="/wiki/Chlorpromazine" title="Chlorpromazine">Chlorpromazine</a></li> <li><a href="/wiki/Clemastine" title="Clemastine">Clemastine</a></li> <li><a href="/wiki/Clomipramine" title="Clomipramine">Clomipramine</a></li> <li><a href="/wiki/Clorgiline" title="Clorgiline">Clorgiline</a></li> <li><a href="/wiki/D-Deprenyl" title="D-Deprenyl">D-Deprenyl</a></li> <li><a href="/wiki/N,N-Diisopropyltryptamine" class="mw-redirect" title="N,N-Diisopropyltryptamine"><abbr title="N,N-Diisopropyltryptamine">DiPT</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip N,N-Diisopropyltryptamine</li> <li><a href="/wiki/N,N-Dipropyltryptamine" class="mw-redirect" title="N,N-Dipropyltryptamine"><abbr title="N,N-Dipropyltryptamine">DPT</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip N,N-Dipropyltryptamine</li> <li><a href="/wiki/Ibogaine" title="Ibogaine">Ibogaine</a></li> <li><a href="/wiki/Imipramine" title="Imipramine">Imipramine</a></li> <li><a href="/w/index.php?title=KCR-12-83.1&action=edit&redlink=1" class="new" title="KCR-12-83.1 (page does not exist)">KCR-12-83.1</a></li> <li><a href="/wiki/Nemonapride" title="Nemonapride">Nemonapride</a></li> <li><a href="/wiki/Noribogaine" title="Noribogaine">Noribogaine</a></li> <li><a href="/w/index.php?title=RHL-033&action=edit&redlink=1" class="new" title="RHL-033 (page does not exist)">RHL-033</a></li> <li><a href="/wiki/RS-67,333" title="RS-67,333">RS-67,333</a></li> <li><a href="/wiki/RTI-55" title="RTI-55">RTI-55</a></li> <li><a href="/wiki/Saffron" title="Saffron">Saffron</a></li> <li><a href="/wiki/Safinamide" title="Safinamide">Safinamide</a></li> <li><a href="/wiki/Selegiline" title="Selegiline">Selegiline</a></li> <li><a href="/w/index.php?title=Spipethiane&action=edit&redlink=1" class="new" title="Spipethiane (page does not exist)">Spipethiane</a></li> <li><a href="/wiki/Trifluoperazine" title="Trifluoperazine">Trifluoperazine</a></li> <li><a href="/wiki/W-18_(drug)" title="W-18 (drug)">W-18</a></li> <li><a href="/wiki/YKP10A" class="mw-redirect" title="YKP10A">YKP10A</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Sigma-2_receptor" title="Sigma-2 receptor">σ2</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li>Agonists: <a href="/wiki/3-PPP" title="3-PPP">3-PPP</a></li> <li><a href="/wiki/Arketamine" title="Arketamine">Arketamine</a></li> <li><a href="/wiki/BD-1047" title="BD-1047">BD-1047</a></li> <li><a href="/wiki/BD1063" title="BD1063">BD1063</a></li> <li><a href="/wiki/Ditolylguanidine" title="Ditolylguanidine">Ditolylguanidine (DTG)</a></li> <li><a href="/w/index.php?title=DKR-1005&action=edit&redlink=1" class="new" title="DKR-1005 (page does not exist)">DKR-1005</a></li> <li><a href="/w/index.php?title=DKR-1051&action=edit&redlink=1" class="new" title="DKR-1051 (page does not exist)">DKR-1051</a></li> <li><a href="/wiki/Haloperidol" title="Haloperidol">Haloperidol</a></li> <li><a href="/wiki/Ifenprodil" title="Ifenprodil">Ifenprodil</a></li> <li><a href="/wiki/Ketamine" title="Ketamine">Ketamine</a></li> <li><a class="mw-selflink selflink"><abbr title="Methylenedioxymethamphetamine">MDMA</abbr> (midomafetamine)</a></li> <li><a href="/wiki/Methamphetamine" title="Methamphetamine">Methamphetamine</a></li> <li><a href="/w/index.php?title=OPC-14523&action=edit&redlink=1" class="new" title="OPC-14523 (page does not exist)">OPC-14523</a></li> <li><a href="/wiki/Opipramol" title="Opipramol">Opipramol</a></li> <li><a href="/wiki/PB-28" title="PB-28">PB-28</a></li> <li><a href="/wiki/Phencyclidine" title="Phencyclidine">Phencyclidine</a></li> <li><a href="/wiki/Siramesine" title="Siramesine">Siramesine (Lu 28-179)</a></li> <li><a href="/w/index.php?title=UKH-1114&action=edit&redlink=1" class="new" title="UKH-1114 (page does not exist)">UKH-1114</a></li></ul> <ul><li>Antagonists: <a href="/wiki/AC-927" class="mw-redirect" title="AC-927">AC-927</a></li> <li><a href="/wiki/BD-1008" class="mw-redirect" title="BD-1008">BD-1008</a></li> <li><a href="/wiki/BD-1067" class="mw-redirect" title="BD-1067">BD-1067</a></li> <li><a href="/wiki/CM-156" class="mw-redirect" title="CM-156">CM-156</a></li> <li><a href="/w/index.php?title=CT-1812&action=edit&redlink=1" class="new" title="CT-1812 (page does not exist)">CT-1812</a></li> <li><a href="/w/index.php?title=LR-172&action=edit&redlink=1" class="new" title="LR-172 (page does not exist)">LR-172</a></li> <li><a href="/wiki/MIN-101" class="mw-redirect" title="MIN-101">MIN-101</a></li> <li><a href="/wiki/Panamesine" title="Panamesine">Panamesine (EMD-57455)</a></li> <li><a href="/w/index.php?title=SAS-0132&action=edit&redlink=1" class="new" title="SAS-0132 (page does not exist)">SAS-0132</a></li></ul> <ul><li>Unknown/unsorted: <a href="/w/index.php?title=3-Methoxydextrallorphan&action=edit&redlink=1" class="new" title="3-Methoxydextrallorphan (page does not exist)">3-Methoxydextrallorphan</a></li> <li><a href="/wiki/3-MeO-PCE" title="3-MeO-PCE">3-MeO-PCE</a></li> <li><a href="/wiki/4-MeO-PCP" title="4-MeO-PCP">4-MeO-PCP</a></li> <li><a href="/wiki/5-MeO-DALT" title="5-MeO-DALT">5-MeO-DALT</a></li> <li><a href="/wiki/5-MeO-DiPT" title="5-MeO-DiPT">5-MeO-DiPT</a></li> <li><a href="/wiki/Clemastine" title="Clemastine">Clemastine</a></li> <li><a href="/wiki/N,N-Diisopropyltryptamine" class="mw-redirect" title="N,N-Diisopropyltryptamine"><abbr title="N,N-Diisopropyltryptamine">DiPT</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip N,N-Diisopropyltryptamine</li> <li><a href="/wiki/N,N-Dipropyltryptamine" class="mw-redirect" title="N,N-Dipropyltryptamine"><abbr title="N,N-Dipropyltryptamine">DPT</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip N,N-Dipropyltryptamine</li> <li><a href="/wiki/Ibogaine" title="Ibogaine">Ibogaine</a></li> <li><a href="/wiki/Lu_29-252" title="Lu 29-252">Lu 29-252</a></li> <li><a href="/wiki/Nemonapride" title="Nemonapride">Nemonapride</a></li> <li><a href="/wiki/Nepinalone" title="Nepinalone">Nepinalone</a></li> <li><a href="/wiki/Noribogaine" title="Noribogaine">Noribogaine</a></li> <li><a href="/wiki/Pentazocine" title="Pentazocine">Pentazocine</a></li> <li><a href="/wiki/RS-67,333" title="RS-67,333">RS-67,333</a></li> <li><a href="/wiki/Safinamide" title="Safinamide">Safinamide</a></li> <li><a href="/wiki/3,4,5-Trimethoxyamphetamine" title="3,4,5-Trimethoxyamphetamine"><abbr title="3,4,5-Trimethoxyamphetamine">TMA</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip 3,4,5-Trimethoxyamphetamine</li> <li><a href="/w/index.php?title=UMB-23&action=edit&redlink=1" class="new" title="UMB-23 (page does not exist)">UMB-23</a></li> <li><a href="/w/index.php?title=UMB-82&action=edit&redlink=1" class="new" title="UMB-82 (page does not exist)">UMB-82</a></li> <li><a href="/wiki/W-18_(drug)" title="W-18 (drug)">W-18</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;">Unsorted</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li>Agonists: <a href="/wiki/Berberine" title="Berberine">Berberine</a></li> <li><a href="/wiki/Ethylketazocine" title="Ethylketazocine">Ethylketazocine</a></li> <li><a href="/wiki/Fourphit" title="Fourphit">Fourphit</a></li> <li><a href="/wiki/Metaphit" title="Metaphit">Metaphit</a></li> <li><a href="/wiki/Naluzotan" title="Naluzotan">Naluzotan</a></li> <li><a href="/wiki/Tapentadol" title="Tapentadol">Tapentadol</a></li> <li><a href="/wiki/Tenocyclidine" title="Tenocyclidine">Tenocyclidine</a></li></ul> <ul><li>Antagonists: <a href="/w/index.php?title=AHD1&action=edit&redlink=1" class="new" title="AHD1 (page does not exist)">AHD1</a></li> <li><a href="/w/index.php?title=AZ66&action=edit&redlink=1" class="new" title="AZ66 (page does not exist)">AZ66</a></li> <li><a href="/wiki/Lamotrigine" title="Lamotrigine">Lamotrigine</a></li> <li><a href="/wiki/Naloxone" title="Naloxone">Naloxone</a></li> <li><a href="/w/index.php?title=SM-21&action=edit&redlink=1" class="new" title="SM-21 (page does not exist)">SM-21</a></li> <li><a href="/w/index.php?title=UMB-100&action=edit&redlink=1" class="new" title="UMB-100 (page does not exist)">UMB-100</a></li> <li><a href="/w/index.php?title=UMB-101&action=edit&redlink=1" class="new" title="UMB-101 (page does not exist)">UMB-101</a></li> <li><a href="/w/index.php?title=UMB-103&action=edit&redlink=1" class="new" title="UMB-103 (page does not exist)">UMB-103</a></li> <li><a href="/w/index.php?title=UMB-116&action=edit&redlink=1" class="new" title="UMB-116 (page does not exist)">UMB-116</a></li> <li><a href="/w/index.php?title=YZ-011&action=edit&redlink=1" class="new" title="YZ-011 (page does not exist)">YZ-011</a></li> <li><a href="/w/index.php?title=YZ-069&action=edit&redlink=1" class="new" title="YZ-069 (page does not exist)">YZ-069</a></li> <li><a href="/w/index.php?title=YZ-185&action=edit&redlink=1" class="new" title="YZ-185 (page does not exist)">YZ-185</a></li></ul> <ul><li>Allosteric modulators: <a href="/wiki/SKF-83959" class="mw-redirect" title="SKF-83959">SKF-83959</a></li></ul> <ul><li>Unknown/unsorted: <a href="/wiki/18-Methoxycoronaridine" title="18-Methoxycoronaridine">18-Methoxycoronaridine</a></li> <li><a href="/w/index.php?title=BMY-13980&action=edit&redlink=1" class="new" title="BMY-13980 (page does not exist)">BMY-13980</a></li> <li><a href="/wiki/Butaclamol" title="Butaclamol">Butaclamol</a></li> <li><a href="/wiki/Caramiphen" title="Caramiphen">Caramiphen</a></li> <li><a href="/w/index.php?title=Carvotroline&action=edit&redlink=1" class="new" title="Carvotroline (page does not exist)">Carvotroline</a></li> <li><a href="/wiki/Chlorphenamine" title="Chlorphenamine">Chlorphenamine (chlorpheniramine)</a></li> <li><a href="/wiki/Chlorpromazine" title="Chlorpromazine">Chlorpromazine</a></li> <li><a href="/wiki/Cinnarizine" title="Cinnarizine">Cinnarizine</a></li> <li><a href="/w/index.php?title=Cinuperone&action=edit&redlink=1" class="new" title="Cinuperone (page does not exist)">Cinuperone</a></li> <li><a href="/wiki/Clocapramine" title="Clocapramine">Clocapramine</a></li> <li><a href="/wiki/Dezocine" title="Dezocine">Dezocine</a></li> <li><a href="/w/index.php?title=EMD-59983&action=edit&redlink=1" class="new" title="EMD-59983 (page does not exist)">EMD-59983</a></li> <li><a href="/wiki/Hypericin" title="Hypericin">Hypericin</a> (<a href="/wiki/St._John%27s_wort" class="mw-redirect" title="St. John's wort">St. John's wort</a>)</li> <li><a href="/wiki/Fluphenazine" title="Fluphenazine">Fluphenazine</a></li> <li><a href="/wiki/Gevotroline" title="Gevotroline">Gevotroline (WY-47384)</a></li> <li><a href="/wiki/Mepyramine" title="Mepyramine">Mepyramine (pyrilamine)</a></li> <li><a href="/wiki/Molindone" title="Molindone">Molindone</a></li> <li><a href="/wiki/Perphenazine" title="Perphenazine">Perphenazine</a></li> <li><a href="/wiki/Pimozide" title="Pimozide">Pimozide</a></li> <li><a href="/wiki/Proadifen" title="Proadifen">Proadifen</a></li> <li><a href="/wiki/Promethazine" title="Promethazine">Promethazine</a></li> <li><a href="/wiki/Propranolol" title="Propranolol">Propranolol</a></li> <li><a href="/wiki/Quinidine" title="Quinidine">Quinidine</a></li> <li><a href="/wiki/Remoxipride" title="Remoxipride">Remoxipride</a></li> <li><a href="/w/index.php?title=SL_82.0715&action=edit&redlink=1" class="new" title="SL 82.0715 (page does not exist)">SL 82.0715</a></li> <li><a href="/w/index.php?title=SR-31747A&action=edit&redlink=1" class="new" title="SR-31747A (page does not exist)">SR-31747A</a></li> <li><a href="/wiki/Tiospirone" title="Tiospirone">Tiospirone (BMY-13859)</a></li> <li><a href="/wiki/Venlafaxine" title="Venlafaxine">Venlafaxine</a></li></ul> </div></td></tr><tr><td class="navbox-abovebelow" colspan="2"><div>See also: <a href="/wiki/Template:Receptor_modulators" title="Template:Receptor modulators">Receptor/signaling modulators</a></div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374" /><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235" /></div><div role="navigation" class="navbox" aria-labelledby="Trace_amine-associated_receptor_modulators1416" style="padding:3px"><table class="nowraplinks hlist mw-collapsible mw-collapsed navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374" /><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231" /><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:TAAR_modulators" title="Template:TAAR modulators"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:TAAR_modulators" title="Template talk:TAAR modulators"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:TAAR_modulators" title="Special:EditPage/Template:TAAR modulators"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Trace_amine-associated_receptor_modulators1416" style="font-size:114%;margin:0 4em"><a href="/wiki/Trace_amine-associated_receptor" title="Trace amine-associated receptor">Trace amine-associated receptor</a> <a href="/wiki/Receptor_modulator" title="Receptor modulator">modulators</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align: center;"><a href="/wiki/Trace_amine-associated_receptor_1" class="mw-redirect" title="Trace amine-associated receptor 1"><abbr title="Trace amine-associated receptor 1">TAAR1</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Trace amine-associated receptor 1</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%;text-align: center;"><a href="/wiki/Agonist" title="Agonist">Agonists</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%;text-align: center;"><a href="/wiki/Trace_amine" title="Trace amine">Endogenous</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Monoamine_neurotransmitter" title="Monoamine neurotransmitter">Monoamine neurotransmitters</a> <ul><li><a href="/wiki/Dopamine" title="Dopamine">Dopamine</a></li> <li><a href="/wiki/Histamine" title="Histamine">Histamine</a></li> <li><a href="/wiki/Epinephrine" class="mw-redirect" title="Epinephrine">Epinephrine (adrenaline)</a></li> <li><a href="/wiki/Norepinephrine" title="Norepinephrine">Norepinephrine (noradrenaline)</a></li> <li><a href="/wiki/Serotonin" title="Serotonin">Serotonin</a></li></ul></li> <li><a href="/wiki/Trace_amine" title="Trace amine">Trace amines</a> <ul><li><a href="/wiki/3-Iodothyronamine" title="3-Iodothyronamine">3-Iodothyronamine</a></li> <li><a href="/wiki/3-Methoxytyramine" title="3-Methoxytyramine">3-Methoxytyramine</a></li> <li><a href="/wiki/N-Methylphenethylamine" title="N-Methylphenethylamine">N-Methylphenethylamine</a></li> <li><a href="/wiki/N-Methyltyramine" title="N-Methyltyramine">N-Methyltyramine</a></li> <li><a href="/wiki/Meta-Octopamine" class="mw-redirect" title="Meta-Octopamine">m-Octopamine</a></li> <li><a href="/wiki/Para-Octopamine" class="mw-redirect" title="Para-Octopamine">p-Octopamine</a></li> <li><a href="/wiki/Phenethylamine" title="Phenethylamine">β-Phenethylamine</a></li> <li><a href="/wiki/Phenylethanolamine" title="Phenylethanolamine">Phenylethanolamine</a></li> <li><a href="/wiki/Synephrine" title="Synephrine">Synephrine</a></li> <li><a href="/wiki/Tryptamine" title="Tryptamine">Tryptamine</a></li> <li><a href="/wiki/Meta-Tyramine" title="Meta-Tyramine">m-Tyramine</a></li> <li><a href="/wiki/Para-Tyramine" class="mw-redirect" title="Para-Tyramine">p-Tyramine</a></li></ul></li> <li>Others <ul><li><a href="/wiki/Cyclohexylamine" title="Cyclohexylamine">Cyclohexylamine</a></li> <li><a href="/w/index.php?title=Isoamylamine&action=edit&redlink=1" class="new" title="Isoamylamine (page does not exist)">Isoamylamine</a></li> <li><a href="/wiki/Trimethylamine" title="Trimethylamine">Trimethylamine</a></li></ul></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align: center;"><a href="/wiki/Exogenous" class="mw-redirect" title="Exogenous">Exogenous</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/2C-B" title="2C-B">2C-B</a></li> <li><a href="/wiki/2C-B-Fly" class="mw-redirect" title="2C-B-Fly">2C-B-Fly</a></li> <li><a href="/wiki/2C-E" title="2C-E">2C-E</a></li> <li><a href="/wiki/2C-H" title="2C-H">2C-H</a></li> <li><a href="/wiki/2C-P" title="2C-P">2C-P</a></li> <li><a href="/wiki/2C-T-7" title="2C-T-7">2C-T-7</a></li> <li><a href="/wiki/A-77636" title="A-77636">A-77636</a></li> <li><a href="/wiki/2-Aminoindane" title="2-Aminoindane">2-Aminoindane</a></li> <li><a href="/wiki/Amphetamine" title="Amphetamine">Amphetamine</a></li> <li><a href="/w/index.php?title=AP163&action=edit&redlink=1" class="new" title="AP163 (page does not exist)">AP163</a></li> <li><a href="/wiki/Apomorphine" title="Apomorphine">Apomorphine</a></li> <li><a href="/wiki/Asenapine" title="Asenapine">Asenapine</a></li> <li><a href="/wiki/Bromocriptine" title="Bromocriptine">Bromocriptine</a></li> <li><a href="/wiki/Cathinone" title="Cathinone">Cathinone</a></li> <li><a href="/wiki/Chlorpromazine" title="Chlorpromazine">Chlorpromazine</a></li> <li><a href="/wiki/Clonidine" title="Clonidine">Clonidine</a></li> <li><a href="/wiki/Cyproheptadine" title="Cyproheptadine">Cyproheptadine</a></li> <li><a href="/wiki/Dihydroergotamine" title="Dihydroergotamine">Dihydroergotamine</a></li> <li><a href="/wiki/Dimethyltryptamine" class="mw-redirect" title="Dimethyltryptamine">Dimethyltryptamine</a></li> <li><a href="/wiki/2,5-Dimethoxy-4-bromoamphetamine" title="2,5-Dimethoxy-4-bromoamphetamine">DOB</a></li> <li><a href="/wiki/2,5-Dimethoxy-4-ethylamphetamine" title="2,5-Dimethoxy-4-ethylamphetamine">DOET</a></li> <li><a href="/wiki/2,5-Dimethoxy-4-iodoamphetamine" title="2,5-Dimethoxy-4-iodoamphetamine">DOI</a></li> <li><a href="/wiki/2,5-Dimethoxy-4-methylamphetamine" title="2,5-Dimethoxy-4-methylamphetamine">DOM</a></li> <li><a href="/wiki/N,N-Dimethylphenethylamine" title="N,N-Dimethylphenethylamine">N,N-Dimethylphenethylamine</a></li> <li><a href="/wiki/Ergometrine" class="mw-redirect" title="Ergometrine">Ergometrine</a></li> <li><a href="/wiki/Fenoldopam" title="Fenoldopam">Fenoldopam</a></li> <li><a href="/wiki/Fenoterol" title="Fenoterol">Fenoterol</a></li> <li><a href="/wiki/4-Fluoroamphetamine" title="4-Fluoroamphetamine">4-Fluoroamphetamine</a></li> <li><a href="/wiki/Guanabenz" title="Guanabenz">Guanabenz</a></li> <li><a href="/wiki/Guanfacine" title="Guanfacine">Guanfacine</a></li> <li><a href="/wiki/Halostachine" title="Halostachine">Halostachine</a></li> <li><a href="/wiki/Higenamine" title="Higenamine">Higenamine</a></li> <li><a href="/wiki/Hordenine" title="Hordenine">Hordenine</a></li> <li><a href="/wiki/4-Hydroxyamphetamine" title="4-Hydroxyamphetamine">4-Hydroxyamphetamine (norpholedrine)</a></li> <li><a href="/wiki/Idazoxan" title="Idazoxan">Idazoxan</a></li> <li><a href="/wiki/5-Iodo-2-aminoindane" class="mw-redirect" title="5-Iodo-2-aminoindane">5-Iodo-2-aminoindane</a></li> <li><a href="/wiki/Isoprenaline" title="Isoprenaline">Isoprenaline</a></li> <li><a href="/wiki/Isopropyloctopamine" class="mw-redirect" title="Isopropyloctopamine">Isopropyloctopamine</a></li> <li><a href="/wiki/Lisuride" title="Lisuride">Lisuride</a></li> <li><a href="/wiki/LK00764" title="LK00764">LK00764</a></li> <li><a href="/wiki/Lysergic_acid_diethylamide" class="mw-redirect" title="Lysergic acid diethylamide">LSD</a></li> <li><a href="/wiki/3,4-Methylenedioxyamphetamine" title="3,4-Methylenedioxyamphetamine">MDA (tenamfetamine)</a></li> <li><a href="/wiki/Methylenedioxyaminoindane" class="mw-redirect" title="Methylenedioxyaminoindane">MDAI</a></li> <li><a class="mw-selflink selflink">MDMA (midomafetamine)</a></li> <li><a href="/wiki/Mescaline" title="Mescaline">Mescaline</a></li> <li><a href="/wiki/Metergoline" title="Metergoline">Metergoline</a></li> <li><a href="/wiki/N-Methyl-2-AI" class="mw-redirect" title="N-Methyl-2-AI">N-Methyl-2-AI</a></li> <li><a href="/wiki/2-Methylphenethylamine" title="2-Methylphenethylamine">2-Methylphenethylamine</a></li> <li><a href="/wiki/3-Methylphenethylamine" title="3-Methylphenethylamine">3-Methylphenethylamine</a></li> <li><a href="/wiki/4-Methylphenethylamine" title="4-Methylphenethylamine">4-Methylphenethylamine</a></li> <li><a href="/wiki/%CE%92-Methylphenethylamine" title="Β-Methylphenethylamine">β-Methylphenethylamine</a></li> <li><a href="/wiki/Methamphetamine" title="Methamphetamine">Methamphetamine</a></li> <li><a href="/wiki/3-Methoxyamphetamine" title="3-Methoxyamphetamine">MMA</a></li> <li><a href="/wiki/MPTP" title="MPTP">MPTP</a></li> <li><a href="/wiki/Naphazoline" title="Naphazoline">Naphazoline</a></li> <li><a href="/wiki/Nomifensine" title="Nomifensine">Nomifensine</a></li> <li><a href="/wiki/Norfenfluramine" title="Norfenfluramine">Norfenfluramine</a></li> <li><a href="/wiki/Oxymetazoline" title="Oxymetazoline">Oxymetazoline</a></li> <li><a href="/wiki/Phentermine" title="Phentermine">Phentermine</a></li> <li><a href="/wiki/Phentolamine" title="Phentolamine">Phentolamine</a></li> <li><a href="/wiki/O-Phenyl-3-iodotyramine" title="O-Phenyl-3-iodotyramine">o-PIT</a></li> <li><a href="/wiki/Psilocin" title="Psilocin">Psilocin</a></li> <li><a href="/wiki/Ralmitaront" title="Ralmitaront">Ralmitaront (RG-7906, RO6889450)</a></li> <li><a href="/wiki/RG-7351" title="RG-7351">RG-7351</a></li> <li><a href="/wiki/RG-7410" title="RG-7410">RG-7410</a></li> <li><a href="/wiki/RO5073012" title="RO5073012">RO5073012</a></li> <li><a href="/wiki/RO5166017" title="RO5166017">RO5166017</a></li> <li><a href="/wiki/RO5203648" title="RO5203648">RO5203648</a></li> <li><a href="/wiki/RO5256390" title="RO5256390">RO5256390</a></li> <li><a href="/wiki/RO5263397" title="RO5263397">RO5263397</a></li> <li><a href="/w/index.php?title=S18616&action=edit&redlink=1" class="new" title="S18616 (page does not exist)">S18616</a></li> <li><a href="/wiki/Selegiline" title="Selegiline">Selegiline (L-deprenyl)</a></li> <li><a href="/wiki/Solriamfetol" title="Solriamfetol">Solriamfetol</a></li> <li><a href="/wiki/Tolazoline" title="Tolazoline">Tolazoline</a></li> <li><a href="/wiki/Ulotaront" title="Ulotaront">Ulotaront (SEP-363856)</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align: center;"><a href="/wiki/Receptor_antagonist" title="Receptor antagonist">Antagonists</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Compound_22_(TAAR1_antagonist)" title="Compound 22 (TAAR1 antagonist)">Compound 22</a></li> <li><a href="/wiki/EPPTB" title="EPPTB">EPPTB (RO-5212773)</a></li> <li><a href="/wiki/RTI-7470-44" title="RTI-7470-44">RTI-7470-44</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align: center;"><a href="/wiki/Inverse_agonist" title="Inverse agonist">Inverse agonists</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/EPPTB" title="EPPTB">EPPTB (RO-5212773)</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align: center;"><a href="/wiki/Trace_amine-associated_receptor_5" class="mw-redirect" title="Trace amine-associated receptor 5"><abbr title="Trace amine-associated receptor 5">TAAR5</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Trace amine-associated receptor 5</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th id="Agonists32" scope="row" class="navbox-group" style="width:1%;text-align: center;"><a href="/wiki/Agonist" title="Agonist">Agonists</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/N,N-Dimethylethylamine" title="N,N-Dimethylethylamine">N,N-Dimethylethylamine</a></li> <li><a href="/wiki/Trimethylamine" title="Trimethylamine">Trimethylamine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align: center;"><a href="/wiki/Inverse_agonist" title="Inverse agonist">Inverse agonists</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/3-Iodothyronamine" title="3-Iodothyronamine">3-Iodothyronamine</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><td class="navbox-abovebelow" colspan="2"><div>Notes: (1) TAAR1 activity of ligands varies significantly between species. Some agents that are TAAR1 ligands in some species are not in other species. This navbox includes all TAAR1 ligands regardless of species. (2) See the individual pages for references, as well as the <a href="/wiki/Trace_amine#List_of_trace_amines" title="Trace amine">List of trace amines</a>, <a href="/wiki/Trace_amine-associated_receptor" title="Trace amine-associated receptor">TAAR</a>, and <a href="/wiki/TAAR1" title="TAAR1">TAAR1</a> pages. See also: <a href="/wiki/Template:Receptor_modulators" title="Template:Receptor modulators">Receptor/signaling modulators</a></div></td></tr></tbody></table></div></div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374" /><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235" /></div><div role="navigation" class="navbox" aria-labelledby="Phenethylamines352" style="padding:3px"><table class="nowraplinks mw-collapsible mw-collapsed navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374" /><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231" /><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Phenethylamines" title="Template:Phenethylamines"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Phenethylamines" title="Template talk:Phenethylamines"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Phenethylamines" title="Special:EditPage/Template:Phenethylamines"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Phenethylamines352" style="font-size:114%;margin:0 4em"><a href="/wiki/Substituted_phenethylamine" title="Substituted phenethylamine">Phenethylamines</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Substituted_phenethylamine" title="Substituted phenethylamine">Phenethylamines</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li>Psychedelics: <a href="/wiki/25B-NBOMe" title="25B-NBOMe">25B-NBOMe</a></li> <li><a href="/wiki/25C-NBOMe" title="25C-NBOMe">25C-NBOMe</a></li> <li><a href="/wiki/25D-NBOMe" title="25D-NBOMe">25D-NBOMe</a></li> <li><a href="/wiki/25I-NBOMe" title="25I-NBOMe">25I-NBOMe</a></li> <li><a href="/wiki/25N-NBOMe" title="25N-NBOMe">25N-NBOMe</a></li> <li><a href="/wiki/2C-B" title="2C-B">2C-B</a></li> <li><a href="/w/index.php?title=2C-B-AN&action=edit&redlink=1" class="new" title="2C-B-AN (page does not exist)">2C-B-AN</a></li> <li><a href="/w/index.php?title=2C-Bn&action=edit&redlink=1" class="new" title="2C-Bn (page does not exist)">2C-Bn</a></li> <li><a href="/w/index.php?title=2C-Bu&action=edit&redlink=1" class="new" title="2C-Bu (page does not exist)">2C-Bu</a></li> <li><a href="/wiki/2C-C" title="2C-C">2C-C</a></li> <li><a href="/w/index.php?title=2C-CN&action=edit&redlink=1" class="new" title="2C-CN (page does not exist)">2C-CN</a></li> <li><a href="/wiki/2C-CP" title="2C-CP">2C-CP</a></li> <li><a href="/wiki/2C-D" title="2C-D">2C-D</a></li> <li><a href="/wiki/2C-E" title="2C-E">2C-E</a></li> <li><a href="/wiki/2C-EF" title="2C-EF">2C-EF</a></li> <li><a href="/wiki/2C-F" title="2C-F">2C-F</a></li> <li><a href="/wiki/2C-G" title="2C-G">2C-G</a></li> <li><a href="/wiki/2C-G-1" class="mw-redirect" title="2C-G-1">2C-G-1</a></li> <li><a href="/wiki/2C-G-2" class="mw-redirect" title="2C-G-2">2C-G-2</a></li> <li><a href="/wiki/2C-G-3" class="mw-redirect" title="2C-G-3">2C-G-3</a></li> <li><a href="/wiki/2C-G-4" class="mw-redirect" title="2C-G-4">2C-G-4</a></li> <li><a href="/wiki/2C-G-5" class="mw-redirect" title="2C-G-5">2C-G-5</a></li> <li><a href="/wiki/2C-G-6" class="mw-redirect" title="2C-G-6">2C-G-6</a></li> <li><a href="/wiki/2C-G-N" class="mw-redirect" title="2C-G-N">2C-G-N</a></li> <li><a href="/wiki/2C-H" title="2C-H">2C-H</a></li> <li><a href="/wiki/2C-I" title="2C-I">2C-I</a></li> <li><a href="/wiki/2C-iP" title="2C-iP">2C-iP</a></li> <li><a href="/wiki/2C-N" title="2C-N">2C-N</a></li> <li><a href="/w/index.php?title=2C-NH2&action=edit&redlink=1" class="new" title="2C-NH2 (page does not exist)">2C-NH2</a></li> <li><a href="/wiki/2C-O" class="mw-redirect" title="2C-O">2C-O</a></li> <li><a href="/wiki/2C-O-4" title="2C-O-4">2C-O-4</a></li> <li><a href="/wiki/2C-P" title="2C-P">2C-P</a></li> <li><a href="/w/index.php?title=2C-Ph&action=edit&redlink=1" class="new" title="2C-Ph (page does not exist)">2C-Ph</a></li> <li><a href="/wiki/2C-SE" class="mw-redirect" title="2C-SE">2C-SE</a></li> <li><a href="/wiki/2C-T" title="2C-T">2C-T</a></li> <li><a href="/wiki/2C-T-2" title="2C-T-2">2C-T-2</a></li> <li><a href="/wiki/2C-T-3" title="2C-T-3">2C-T-3</a></li> <li><a href="/wiki/2C-T-4" title="2C-T-4">2C-T-4</a></li> <li><a href="/w/index.php?title=2C-T-5&action=edit&redlink=1" class="new" title="2C-T-5 (page does not exist)">2C-T-5</a></li> <li><a href="/w/index.php?title=2C-T-6&action=edit&redlink=1" class="new" title="2C-T-6 (page does not exist)">2C-T-6</a></li> <li><a href="/wiki/2C-T-7" title="2C-T-7">2C-T-7</a></li> <li><a href="/wiki/2C-T-8" title="2C-T-8">2C-T-8</a></li> <li><a href="/wiki/2C-T-9" class="mw-redirect" title="2C-T-9">2C-T-9</a></li> <li><a href="/w/index.php?title=2C-T-10&action=edit&redlink=1" class="new" title="2C-T-10 (page does not exist)">2C-T-10</a></li> <li><a href="/w/index.php?title=2C-T-11&action=edit&redlink=1" class="new" title="2C-T-11 (page does not exist)">2C-T-11</a></li> <li><a href="/w/index.php?title=2C-T-12&action=edit&redlink=1" class="new" title="2C-T-12 (page does not exist)">2C-T-12</a></li> <li><a href="/wiki/2C-T-13" title="2C-T-13">2C-T-13</a></li> <li><a href="/w/index.php?title=2C-T-14&action=edit&redlink=1" class="new" title="2C-T-14 (page does not exist)">2C-T-14</a></li> <li><a href="/wiki/2C-T-15" title="2C-T-15">2C-T-15</a></li> <li><a href="/wiki/2C-T-16" title="2C-T-16">2C-T-16</a></li> <li><a href="/wiki/2C-T-17" title="2C-T-17">2C-T-17</a></li> <li><a href="/w/index.php?title=2C-T-18&action=edit&redlink=1" class="new" title="2C-T-18 (page does not exist)">2C-T-18</a></li> <li><a href="/wiki/2C-T-19" title="2C-T-19">2C-T-19</a></li> <li><a href="/w/index.php?title=2C-T-20&action=edit&redlink=1" class="new" title="2C-T-20 (page does not exist)">2C-T-20</a></li> <li><a href="/wiki/2C-T-21" title="2C-T-21">2C-T-21</a></li> <li><a href="/w/index.php?title=2C-T-22&action=edit&redlink=1" class="new" title="2C-T-22 (page does not exist)">2C-T-22</a></li> <li><a href="/w/index.php?title=2C-T-22.5&action=edit&redlink=1" class="new" title="2C-T-22.5 (page does not exist)">2C-T-22.5</a></li> <li><a href="/w/index.php?title=2C-T-23&action=edit&redlink=1" class="new" title="2C-T-23 (page does not exist)">2C-T-23</a></li> <li><a href="/w/index.php?title=2C-T-24&action=edit&redlink=1" class="new" title="2C-T-24 (page does not exist)">2C-T-24</a></li> <li><a href="/w/index.php?title=2C-T-25&action=edit&redlink=1" class="new" title="2C-T-25 (page does not exist)">2C-T-25</a></li> <li><a href="/wiki/2C-T-27" title="2C-T-27">2C-T-27</a></li> <li><a href="/wiki/2C-T-28" title="2C-T-28">2C-T-28</a></li> <li><a href="/w/index.php?title=2C-T-30&action=edit&redlink=1" class="new" title="2C-T-30 (page does not exist)">2C-T-30</a></li> <li><a href="/w/index.php?title=2C-T-31&action=edit&redlink=1" class="new" title="2C-T-31 (page does not exist)">2C-T-31</a></li> <li><a href="/w/index.php?title=2C-T-32&action=edit&redlink=1" class="new" title="2C-T-32 (page does not exist)">2C-T-32</a></li> <li><a href="/wiki/2C-T-33" title="2C-T-33">2C-T-33</a></li> <li><a href="/wiki/2C-TFE" title="2C-TFE">2C-TFE</a></li> <li><a href="/wiki/2C-TFM" title="2C-TFM">2C-TFM</a></li> <li><a href="/wiki/2C-YN" title="2C-YN">2C-YN</a></li> <li><a href="/wiki/2C-V" title="2C-V">2C-V</a></li> <li><a href="/wiki/Allylescaline" title="Allylescaline">Allylescaline</a></li> <li><a href="/wiki/DESOXY" title="DESOXY">DESOXY</a></li> <li><a href="/wiki/Escaline" title="Escaline">Escaline</a></li> <li><a href="/wiki/Isoproscaline" title="Isoproscaline">Isoproscaline</a></li> <li><a href="/wiki/Jimscaline" title="Jimscaline">Jimscaline</a></li> <li><a href="/wiki/Macromerine" title="Macromerine">Macromerine</a></li> <li><a href="/wiki/3-Methoxy-4-ethoxyphenethylamine" title="3-Methoxy-4-ethoxyphenethylamine">MEPEA</a></li> <li><a href="/wiki/Mescaline" title="Mescaline">Mescaline</a></li> <li><a href="/wiki/Metaescaline" title="Metaescaline">Metaescaline</a></li> <li><a href="/wiki/Methallylescaline" title="Methallylescaline">Methallylescaline</a></li> <li><a href="/wiki/Proscaline" title="Proscaline">Proscaline</a></li> <li><a href="/wiki/Psi-2C-T-4" class="mw-redirect" title="Psi-2C-T-4">Psi-2C-T-4</a></li> <li><a href="/wiki/TCB-2" title="TCB-2">TCB-2</a></li></ul> <ul><li>Stimulants: <a href="/wiki/Phenylethanolamine" title="Phenylethanolamine">Phenylethanolamine</a></li> <li><a href="/wiki/Hordenine" title="Hordenine">Hordenine</a></li> <li><a href="/wiki/Phenethylamine" title="Phenethylamine">Phenethylamine</a></li> <li><a href="/wiki/Phenpromethamine" title="Phenpromethamine">Phenpromethamine</a></li> <li><a href="/wiki/Amphetamine" title="Amphetamine">α-Methylphenethylamine</a> (amphetamine)</li> <li><a href="/wiki/%CE%92-Methylphenethylamine" title="Β-Methylphenethylamine">β-Methylphenethylamine</a></li> <li><a href="/wiki/M-Methylphenethylamine" class="mw-redirect" title="M-Methylphenethylamine">m-Methylphenethylamine</a></li> <li><a href="/wiki/N-Methylphenethylamine" title="N-Methylphenethylamine">N-Methylphenethylamine</a></li> <li><a href="/wiki/O-Methylphenethylamine" class="mw-redirect" title="O-Methylphenethylamine">o-Methylphenethylamine</a></li> <li><a href="/wiki/P-Methylphenethylamine" class="mw-redirect" title="P-Methylphenethylamine">p-Methylphenethylamine</a></li> <li><a href="/wiki/Methylphenidate" title="Methylphenidate">Methylphenidate</a></li></ul> <ul><li>Entactogens: <a href="/wiki/Lophophine" title="Lophophine">Lophophine</a></li> <li><a href="/wiki/Methylenedioxyphenethylamine" class="mw-redirect" title="Methylenedioxyphenethylamine">MDPEA</a></li> <li><a href="/wiki/Methylenedioxymethylphenethylamine" class="mw-redirect" title="Methylenedioxymethylphenethylamine">MDMPEA</a> Others: <a href="/wiki/BOH_(drug)" title="BOH (drug)">BOH</a></li> <li><a href="/wiki/3,4-Dimethoxyphenethylamine" title="3,4-Dimethoxyphenethylamine">DMPEA</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Substituted_amphetamine" title="Substituted amphetamine">Amphetamines</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li>Psychedelics: <a href="/wiki/3C-AL" title="3C-AL">3C-AL</a></li> <li><a href="/wiki/3C-BZ" title="3C-BZ">3C-BZ</a></li> <li><a href="/wiki/3C-E" title="3C-E">3C-E</a></li> <li><a href="/wiki/3C-MAL" title="3C-MAL">3C-MAL</a></li> <li><a href="/wiki/3C-P" title="3C-P">3C-P</a></li> <li><a href="/wiki/Aleph_(psychedelic)" title="Aleph (psychedelic)">Aleph</a></li> <li><a href="/wiki/Beatrice_(psychedelic)" title="Beatrice (psychedelic)">Beatrice</a></li> <li><a href="/wiki/Bromo-DragonFLY" title="Bromo-DragonFLY">Bromo-DragonFLY</a></li> <li><a href="/wiki/D-Deprenyl" title="D-Deprenyl">D-Deprenyl</a></li> <li><a href="/wiki/Dimethoxyamphetamine" title="Dimethoxyamphetamine">DMA</a></li> <li><a href="/wiki/4-Methyl-2,5-methoxyphenylcyclopropylamine" class="mw-redirect" title="4-Methyl-2,5-methoxyphenylcyclopropylamine">DMCPA</a></li> <li><a href="/wiki/DMMDA" title="DMMDA">DMMDA</a></li> <li><a href="/wiki/2,5-Dimethoxy-4-bromoamphetamine" title="2,5-Dimethoxy-4-bromoamphetamine">DOB</a></li> <li><a href="/wiki/2,5-Dimethoxy-4-chloroamphetamine" title="2,5-Dimethoxy-4-chloroamphetamine">DOC</a></li> <li><a href="/wiki/2,5-Dimethoxy-4-fluoroethylamphetamine" class="mw-redirect" title="2,5-Dimethoxy-4-fluoroethylamphetamine">DOEF</a></li> <li><a href="/wiki/2,5-Dimethoxy-4-ethylamphetamine" title="2,5-Dimethoxy-4-ethylamphetamine">DOET</a></li> <li><a href="/wiki/2,5-Dimethoxy-4-iodoamphetamine" title="2,5-Dimethoxy-4-iodoamphetamine">DOI</a></li> <li><a href="/wiki/2,5-Dimethoxy-4-methylamphetamine" title="2,5-Dimethoxy-4-methylamphetamine">DOM</a></li> <li><a href="/wiki/2,5-Dimethoxy-4-nitroamphetamine" title="2,5-Dimethoxy-4-nitroamphetamine">DON</a></li> <li><a href="/wiki/2,5-Dimethoxy-4-propylamphetamine" title="2,5-Dimethoxy-4-propylamphetamine">DOPR</a></li> <li><a href="/wiki/2,5-Dimethoxy-4-trifluoromethylamphetamine" title="2,5-Dimethoxy-4-trifluoromethylamphetamine">DOTFM</a></li> <li><a href="/wiki/Ganesha_(psychedelic)" title="Ganesha (psychedelic)">Ganesha</a></li> <li><a href="/wiki/MMDA_(drug)" title="MMDA (drug)">MMDA</a></li> <li><a href="/wiki/MMDA-2" title="MMDA-2">MMDA-2</a></li> <li><a href="/wiki/Psi-DOM" class="mw-redirect" title="Psi-DOM">Psi-DOM</a></li> <li><a href="/wiki/Trimethoxyamphetamine" class="mw-redirect" title="Trimethoxyamphetamine">TMA</a></li> <li><a href="/wiki/Tetramethoxyamphetamine" class="mw-redirect" title="Tetramethoxyamphetamine">TeMA</a></li> <li><a href="/wiki/ZDCM-04" title="ZDCM-04">ZDCM-04</a> Stimulants: <a href="/wiki/2-Fluoroamphetamine" title="2-Fluoroamphetamine">2-FA</a></li> <li><a href="/wiki/2-Fluoromethamphetamine" title="2-Fluoromethamphetamine">2-FMA</a></li> <li><a href="/wiki/3-Fluoroamphetamine" title="3-Fluoroamphetamine">3-FA</a></li> <li><a href="/wiki/3-Fluoromethamphetamine" title="3-Fluoromethamphetamine">3-FMA</a></li> <li><a href="/wiki/Acridorex" title="Acridorex">Acridorex</a></li> <li><a href="/wiki/Alfetamine" title="Alfetamine">Alfetamine</a></li> <li><a href="/wiki/Amfecloral" title="Amfecloral">Amfecloral</a></li> <li><a href="/wiki/Amfepentorex" title="Amfepentorex">Amfepentorex</a></li> <li><a href="/wiki/Amphetamine" title="Amphetamine">Amphetamine</a> (<a href="/wiki/Dextroamphetamine" title="Dextroamphetamine">Dextroamphetamine</a>, <a href="/wiki/Levoamphetamine" title="Levoamphetamine">Levoamphetamine</a>)</li> <li><a href="/wiki/Amphetaminil" class="mw-redirect" title="Amphetaminil">Amphetaminil</a></li> <li><a href="/wiki/Benfluorex" title="Benfluorex">Benfluorex</a></li> <li><a href="/wiki/Benzphetamine" title="Benzphetamine">Benzphetamine</a></li> <li><a href="/wiki/Cathine" title="Cathine">Cathine</a></li> <li><a href="/wiki/Clobenzorex" title="Clobenzorex">Clobenzorex</a></li> <li><a href="/wiki/Dimethylamphetamine" title="Dimethylamphetamine">Dimethylamphetamine</a></li> <li><a href="/wiki/Ephedrine" title="Ephedrine">Ephedrine</a></li> <li><a href="/wiki/Etilamfetamine" title="Etilamfetamine">Etilamfetamine</a></li> <li><a href="/wiki/Fencamfamin" title="Fencamfamin">Fencamfamin</a></li> <li><a href="/wiki/Fencamine" title="Fencamine">Fencamine</a></li> <li><a href="/wiki/Fenethylline" title="Fenethylline">Fenethylline</a></li> <li><a href="/wiki/Fenfluramine" title="Fenfluramine">Fenfluramine</a> (<a href="/wiki/Dexfenfluramine" title="Dexfenfluramine">Dexfenfluramine</a>, <a href="/wiki/Levofenfluramine" title="Levofenfluramine">Levofenfluramine</a>)</li> <li><a href="/wiki/Fenproporex" title="Fenproporex">Fenproporex</a></li> <li><a href="/wiki/Flucetorex" title="Flucetorex">Flucetorex</a></li> <li><a href="/wiki/Fludorex" title="Fludorex">Fludorex</a></li> <li><a href="/wiki/Formetorex" title="Formetorex">Formetorex</a></li> <li><a href="/wiki/Furfenorex" title="Furfenorex">Furfenorex</a></li> <li><a href="/wiki/Gepefrine" title="Gepefrine">Gepefrine</a></li> <li><a href="/wiki/4-Hydroxyamphetamine" title="4-Hydroxyamphetamine">4-Hydroxyamphetamine</a></li> <li><a href="/wiki/Iofetamine" class="mw-redirect" title="Iofetamine">Iofetamine</a></li> <li><a href="/wiki/Isopropylamphetamine" title="Isopropylamphetamine">Isopropylamphetamine</a></li> <li><a href="/wiki/Lefetamine" title="Lefetamine">Lefetamine</a></li> <li><a href="/wiki/Lisdexamfetamine" title="Lisdexamfetamine">Lisdexamfetamine</a></li> <li><a href="/wiki/Mefenorex" title="Mefenorex">Mefenorex</a></li> <li><a href="/wiki/Metaraminol" title="Metaraminol">Metaraminol</a></li> <li><a href="/wiki/Methamphetamine" title="Methamphetamine">Methamphetamine</a> (Dextromethamphetamine, <a href="/wiki/Levomethamphetamine" class="mw-redirect" title="Levomethamphetamine">Levomethamphetamine</a>)</li> <li><a href="/wiki/Methoxyphenamine" title="Methoxyphenamine">Methoxyphenamine</a></li> <li><a href="/wiki/3-Methoxy-4-methylamphetamine" title="3-Methoxy-4-methylamphetamine">MMA</a></li> <li><a href="/wiki/Morforex" title="Morforex">Morforex</a></li> <li><a href="/wiki/Norfenfluramine" title="Norfenfluramine">Norfenfluramine</a></li> <li><a href="/wiki/L-Norpseudoephedrine" title="L-Norpseudoephedrine">L-Norpseudoephedrine</a></li> <li><a href="/wiki/N,alpha-Diethylphenylethylamine" class="mw-redirect" title="N,alpha-Diethylphenylethylamine">N,alpha-Diethylphenylethylamine</a></li> <li><a href="/wiki/Oxifentorex" title="Oxifentorex">Oxifentorex</a></li> <li><a href="/wiki/Oxilofrine" title="Oxilofrine">Oxilofrine</a></li> <li><a href="/wiki/Ortetamine" title="Ortetamine">Ortetamine</a></li> <li><a href="/wiki/Para-Bromoamphetamine" title="Para-Bromoamphetamine">PBA</a></li> <li><a href="/wiki/Para-Chloroamphetamine" title="Para-Chloroamphetamine">PCA</a></li> <li><a href="/wiki/4-Fluoroamphetamine" title="4-Fluoroamphetamine">PFA</a></li> <li><a href="/wiki/4-Fluoromethamphetamine" title="4-Fluoromethamphetamine">PFMA</a></li> <li><a href="/wiki/Para-Iodoamphetamine" title="Para-Iodoamphetamine">PIA</a></li> <li><a href="/wiki/Para-Methoxyamphetamine" title="Para-Methoxyamphetamine">PMA</a></li> <li><a href="/wiki/Para-Methoxy-N-ethylamphetamine" title="Para-Methoxy-N-ethylamphetamine">PMEA</a></li> <li><a href="/wiki/Para-Methoxy-N-methylamphetamine" class="mw-redirect" title="Para-Methoxy-N-methylamphetamine">PMMA</a></li> <li><a href="/wiki/Phenylpropanolamine" title="Phenylpropanolamine">Phenylpropanolamine</a></li> <li><a href="/wiki/Pholedrine" title="Pholedrine">Pholedrine</a></li> <li><a href="/wiki/Prenylamine" title="Prenylamine">Prenylamine</a></li> <li><a href="/wiki/Propylamphetamine" title="Propylamphetamine">Propylamphetamine</a></li> <li><a href="/wiki/Pseudoephedrine" title="Pseudoephedrine">Pseudoephedrine</a></li> <li><a href="/wiki/Sibutramine" title="Sibutramine">Sibutramine</a></li> <li><a href="/wiki/Tiflorex" title="Tiflorex">Tiflorex</a></li> <li><a href="/wiki/Tranylcypromine" title="Tranylcypromine">Tranylcypromine</a></li> <li><a href="/wiki/Xylopropamine" title="Xylopropamine">Xylopropamine</a></li> <li><a href="/wiki/Zylofuramine" title="Zylofuramine">Zylofuramine</a> Entactogens: <a href="/wiki/4-Fluoroamphetamine" title="4-Fluoroamphetamine">4-FA</a></li> <li><a href="/wiki/4-Fluoromethamphetamine" title="4-Fluoromethamphetamine">4-FMA</a></li> <li><a href="/wiki/4-Methylamphetamine" title="4-Methylamphetamine">4-MA</a></li> <li><a href="/wiki/4-Methylmethamphetamine" title="4-Methylmethamphetamine">4-MMA</a></li> <li><a href="/wiki/4-Methylthioamphetamine" title="4-Methylthioamphetamine">4-MTA</a></li> <li><a href="/wiki/5-APB" title="5-APB">5-APB</a></li> <li><a href="/wiki/5-APDB" title="5-APDB">5-APDB</a></li> <li><a href="/wiki/5-EAPB" title="5-EAPB">5-EAPB</a></li> <li><a href="/wiki/5-IT" class="mw-redirect" title="5-IT">5-IT</a></li> <li><a href="/wiki/5-MAPB" title="5-MAPB">5-MAPB</a></li> <li><a href="/wiki/5-MAPDB" title="5-MAPDB">5-MAPDB</a></li> <li><a href="/wiki/6-APB" title="6-APB">6-APB</a></li> <li><a href="/wiki/6-APDB" title="6-APDB">6-APDB</a></li> <li><a href="/wiki/6-Chloro-MDMA" title="6-Chloro-MDMA">6-Chloro-MDMA</a></li> <li><a href="/wiki/6-EAPB" title="6-EAPB">6-EAPB</a></li> <li><a href="/wiki/6-IT" class="mw-redirect" title="6-IT">6-IT</a></li> <li><a href="/wiki/6-MAPB" title="6-MAPB">6-MAPB</a></li> <li><a href="/wiki/6-MAPDB" title="6-MAPDB">6-MAPDB</a></li> <li><a href="/wiki/Ethylidenedioxyamphetamine" class="mw-redirect" title="Ethylidenedioxyamphetamine">EDA</a></li> <li><a href="/wiki/Indanylaminopropane" class="mw-redirect" title="Indanylaminopropane">IAP</a></li> <li><a href="/wiki/2,3-Methylenedioxyamphetamine" title="2,3-Methylenedioxyamphetamine">2,3-MDA</a></li> <li><a href="/wiki/3,4-Methylenedioxyamphetamine" title="3,4-Methylenedioxyamphetamine">3,4-MDA (tenamfetamine)</a></li> <li><a href="/wiki/Methylenedioxyethylamphetamine" class="mw-redirect" title="Methylenedioxyethylamphetamine">MDEA</a></li> <li><a href="/wiki/Methylenedioxyhydroxylmethamphetamine" class="mw-redirect" title="Methylenedioxyhydroxylmethamphetamine">MDHMA</a></li> <li><a class="mw-selflink selflink">MDMA (midomafetamine)</a></li> <li><a href="/wiki/Methylenedioxyhydroxyamphetamine" class="mw-redirect" title="Methylenedioxyhydroxyamphetamine">MDOH</a></li> <li><a href="/wiki/Methamnetamine" title="Methamnetamine">Methamnetamine</a></li> <li><a href="/wiki/MMDMA" title="MMDMA">MMDMA</a></li> <li><a href="/wiki/Naphthylaminopropane" title="Naphthylaminopropane">Naphthylaminopropane</a></li> <li><a href="/wiki/Tetralinylaminopropane" class="mw-redirect" title="Tetralinylaminopropane">TAP</a> Others: <a href="/wiki/3,4-Dichloroamphetamine" title="3,4-Dichloroamphetamine">3,4-DCA</a></li> <li><a href="/wiki/Amiflamine" title="Amiflamine">Amiflamine</a></li> <li><a href="/wiki/DiFMDA" class="mw-redirect" title="DiFMDA">DiFMDA</a></li> <li><a href="/wiki/Selegiline" title="Selegiline">Selegiline</a> (also <a href="/wiki/D-Deprenyl" title="D-Deprenyl">D-Deprenyl</a>)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Phentermine" title="Phentermine">Phentermines</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li>Stimulants: <a href="/wiki/Chlorphentermine" title="Chlorphentermine">Chlorphentermine</a></li> <li><a href="/wiki/Cloforex" title="Cloforex">Cloforex</a></li> <li><a href="/wiki/Clortermine" title="Clortermine">Clortermine</a></li> <li><a href="/wiki/Etolorex" title="Etolorex">Etolorex</a></li> <li><a href="/wiki/Mephentermine" title="Mephentermine">Mephentermine</a></li> <li><a href="/wiki/Pentorex" title="Pentorex">Pentorex</a></li> <li><a href="/wiki/Phentermine" title="Phentermine">Phentermine</a> Entactogens: <a href="/wiki/Methylenedioxyphentermine" class="mw-redirect" title="Methylenedioxyphentermine">MDPH</a></li> <li><a href="/wiki/Methylenedioxymethylphentermine" class="mw-redirect" title="Methylenedioxymethylphentermine">MDMPH</a> Others: <a href="/wiki/Cericlamine" title="Cericlamine">Cericlamine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Substituted_cathinone" title="Substituted cathinone">Cathinones</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li>Stimulants: <a href="/wiki/3-Fluoromethcathinone" title="3-Fluoromethcathinone">3-FMC</a></li> <li><a href="/wiki/4-Methylcathinone" title="4-Methylcathinone">4-MC</a></li> <li><a href="/wiki/4-Bromomethcathinone" title="4-Bromomethcathinone">4-BMC</a></li> <li><a href="/wiki/4-Chloromethcathinone" title="4-Chloromethcathinone">4-CMC</a></li> <li><a href="/wiki/4-Ethylmethcathinone" title="4-Ethylmethcathinone">4-EMC</a></li> <li><a href="/wiki/Flephedrone" title="Flephedrone">4-FMC</a></li> <li><a href="/wiki/4-Methylethcathinone" title="4-Methylethcathinone">4-MEC</a></li> <li><a href="/wiki/4-Methylbuphedrone" title="4-Methylbuphedrone">4-MeMABP</a></li> <li><a href="/wiki/4-Methylpentedrone" title="4-Methylpentedrone">4-MPD</a></li> <li><a href="/wiki/Amfepramone" title="Amfepramone">Amfepramone</a></li> <li><a href="/wiki/Benzedrone" title="Benzedrone">Benzedrone</a></li> <li><a href="/wiki/Brephedrone" class="mw-redirect" title="Brephedrone">Brephedrone</a></li> <li><a href="/wiki/Buphedrone" title="Buphedrone">Buphedrone</a></li> <li><a href="/wiki/Bupropion" title="Bupropion">Bupropion</a></li> <li><a href="/wiki/Cathinone" title="Cathinone">Cathinone</a></li> <li><a href="/wiki/Dimethylcathinone" class="mw-redirect" title="Dimethylcathinone">Dimethylcathinone</a></li> <li><a href="/wiki/Ethcathinone" title="Ethcathinone">Ethcathinone</a></li> <li><a href="/wiki/Eutylone" title="Eutylone">Eutylone</a></li> <li><a href="/wiki/Hydroxybupropion" title="Hydroxybupropion">Hydroxybupropion</a></li> <li><a href="/wiki/Methcathinone" title="Methcathinone">Methcathinone</a></li> <li><a href="/wiki/Methedrone" title="Methedrone">Methedrone</a></li> <li><a href="/wiki/N-Ethylbuphedrone" title="N-Ethylbuphedrone">NEB</a></li> <li><a href="/wiki/N-Ethylhexedrone" title="N-Ethylhexedrone">N-Ethylhexedrone</a></li> <li><a href="/wiki/N-Ethylpentedrone" title="N-Ethylpentedrone">N-Ethylpentedrone</a></li> <li><a href="/wiki/Pentedrone" title="Pentedrone">Pentedrone</a></li> <li><a href="/wiki/Pentylone" title="Pentylone">Pentylone</a></li> <li><a href="/wiki/Radafaxine" title="Radafaxine">Radafaxine</a> Entactogens: <a href="/wiki/3,4-Dimethylmethcathinone" title="3,4-Dimethylmethcathinone">3,4-DMMC</a></li> <li><a href="/wiki/3-Methylmethcathinone" title="3-Methylmethcathinone">3-MMC</a></li> <li><a href="/wiki/Butylone" title="Butylone">Butylone</a></li> <li><a href="/wiki/Ethylone" title="Ethylone">Ethylone</a></li> <li><a href="/wiki/Methylone" title="Methylone">Methylone</a></li> <li><a href="/wiki/Methylenedioxycathinone" title="Methylenedioxycathinone">Methylenedioxycathinone</a></li> <li><a href="/wiki/Mephedrone" title="Mephedrone">Mephedrone</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Phenylisobutylamine" title="Phenylisobutylamine">Phenylisobutylamines</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li>Entactogens: <a href="/wiki/4-Chlorophenylisobutylamine" title="4-Chlorophenylisobutylamine">4-CAB</a></li> <li><a href="/wiki/4-Methylphenylisobutylamine" title="4-Methylphenylisobutylamine">4-MAB</a></li> <li><a href="/wiki/Ariadne_(psychedelic)" class="mw-redirect" title="Ariadne (psychedelic)">Ariadne</a></li> <li><a href="/wiki/Benzodioxolylbutanamine" class="mw-redirect" title="Benzodioxolylbutanamine">BDB</a></li> <li><a href="/wiki/Butylone" title="Butylone">Butylone</a></li> <li><a href="/wiki/Ethylbenzodioxolylbutanamine" class="mw-redirect" title="Ethylbenzodioxolylbutanamine">EBDB</a></li> <li><a href="/wiki/Eutylone" title="Eutylone">Eutylone</a></li> <li><a href="/wiki/MBDB" title="MBDB">MBDB</a> Stimulants: <a href="/wiki/Phenylisobutylamine" title="Phenylisobutylamine">Phenylisobutylamine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Phenylethylpyrrolidine" title="Phenylethylpyrrolidine">Phenylalkylpyrrolidines</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li>Stimulants: <a href="/wiki/Alpha-Pyrrolidinobutiophenone" class="mw-redirect" title="Alpha-Pyrrolidinobutiophenone">α-PBP</a></li> <li><a href="/wiki/Alpha-Pyrrolidinohexiophenone" class="mw-redirect" title="Alpha-Pyrrolidinohexiophenone">α-PHP</a></li> <li><a href="/wiki/Alpha-Pyrrolidinopropiophenone" class="mw-redirect" title="Alpha-Pyrrolidinopropiophenone">α-PPP</a></li> <li><a href="/wiki/Alpha-Pyrrolidinopentiophenone" class="mw-redirect" title="Alpha-Pyrrolidinopentiophenone">α-PVP</a></li> <li><a href="/wiki/3%27,4%27-Methylenedioxy-%CE%B1-pyrrolidinobutiophenone" title="3',4'-Methylenedioxy-α-pyrrolidinobutiophenone">MDPBP</a></li> <li><a href="/wiki/3%27,4%27-Methylenedioxy-%CE%B1-pyrrolidinopropiophenone" title="3',4'-Methylenedioxy-α-pyrrolidinopropiophenone">MDPPP</a></li> <li><a href="/wiki/3,4-Methylenedioxypyrovalerone" class="mw-redirect" title="3,4-Methylenedioxypyrovalerone">MDPV</a></li> <li><a href="/wiki/4%27-Methyl-%CE%B1-pyrrolidinobutiophenone" title="4'-Methyl-α-pyrrolidinobutiophenone">4-MePBP</a></li> <li><a href="/wiki/4%27-Methyl-%CE%B1-pyrrolidinohexiophenone" title="4'-Methyl-α-pyrrolidinohexiophenone">4-MePHP</a></li> <li><a href="/wiki/4%27-Methyl-%CE%B1-pyrrolidinopropiophenone" title="4'-Methyl-α-pyrrolidinopropiophenone">4-MePPP</a></li> <li><a href="/wiki/4%27-Methoxy-%CE%B1-pyrrolidinopropiophenone" title="4'-Methoxy-α-pyrrolidinopropiophenone">MOPPP</a></li> <li><a href="/wiki/4%27-Methoxy-%CE%B1-pyrrolidinopentiophenone" title="4'-Methoxy-α-pyrrolidinopentiophenone">MOPVP</a></li> <li><a href="/wiki/4%27-Methyl-%CE%B1-pyrrolidinobutiophenone" title="4'-Methyl-α-pyrrolidinobutiophenone">MPBP</a></li> <li><a href="/wiki/4%27-Methyl-%CE%B1-pyrrolidinohexiophenone" title="4'-Methyl-α-pyrrolidinohexiophenone">MPHP</a></li> <li><a href="/wiki/4%27-Methyl-%CE%B1-pyrrolidinopropiophenone" title="4'-Methyl-α-pyrrolidinopropiophenone">MPPP</a></li> <li><a href="/wiki/Naphyrone" title="Naphyrone">Naphyrone</a></li> <li><a href="/wiki/Phenylethylpyrrolidine" title="Phenylethylpyrrolidine">PEP</a></li> <li><a href="/wiki/Prolintane" title="Prolintane">Prolintane</a></li> <li><a href="/wiki/Pyrovalerone" title="Pyrovalerone">Pyrovalerone</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Catecholamine" title="Catecholamine">Catecholamines</a> (and close relatives)</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/6-Fluoronorepinephrine" title="6-Fluoronorepinephrine">6-FNE</a></li> <li><a href="/wiki/6-Hydroxydopamine" class="mw-redirect" title="6-Hydroxydopamine">6-OHDA</a></li> <li><a href="/wiki/Alpha-Methyldopamine" class="mw-redirect" title="Alpha-Methyldopamine">a-Me-DA</a></li> <li><a href="/wiki/Alpha-Methyltyramine" class="mw-redirect" title="Alpha-Methyltyramine">a-Me-TRA</a></li> <li><a href="/wiki/Adrenochrome" title="Adrenochrome">Adrenochrome</a></li> <li><a href="/wiki/Ciladopa" title="Ciladopa">Ciladopa</a></li> <li><a href="/wiki/D-DOPA" title="D-DOPA">D-DOPA</a> (Dextrodopa)</li> <li><a href="/wiki/Dimetofrine" title="Dimetofrine">Dimetofrine</a></li> <li><a href="/wiki/Dopamine" title="Dopamine">Dopamine</a></li> <li><a href="/wiki/Epinephrine_(neurotransmitter)" class="mw-redirect" title="Epinephrine (neurotransmitter)">Epinephrine</a></li> <li><a href="/wiki/Epinine" class="mw-redirect" title="Epinine">Epinine</a></li> <li><a href="/wiki/Etilefrine" title="Etilefrine">Etilefrine</a></li> <li><a href="/wiki/Ethylnorepinephrine" title="Ethylnorepinephrine">Ethylnorepinephrine</a></li> <li><a href="/wiki/Fenclonine" title="Fenclonine">Fenclonine</a></li> <li><a href="/wiki/Ibopamine" title="Ibopamine">Ibopamine</a></li> <li><a href="/wiki/Isoprenaline" title="Isoprenaline">Isoprenaline</a></li> <li><a href="/wiki/Isoetarine" title="Isoetarine">Isoetarine</a></li> <li><a href="/wiki/L-DOPA" title="L-DOPA">L-DOPA</a> (Levodopa)</li> <li><a href="/wiki/L-DOPS" class="mw-redirect" title="L-DOPS">L-DOPS</a> (Droxidopa)</li> <li><a href="/wiki/L-Phenylalanine" class="mw-redirect" title="L-Phenylalanine">L-Phenylalanine</a></li> <li><a href="/wiki/L-Tyrosine" class="mw-redirect" title="L-Tyrosine">L-Tyrosine</a></li> <li><a href="/wiki/Meta-Tyramine" title="Meta-Tyramine">m-Tyramine</a></li> <li><a href="/wiki/Metanephrine" title="Metanephrine">Metanephrine</a></li> <li><a href="/wiki/Metaraminol" title="Metaraminol">Metaraminol</a></li> <li><a href="/wiki/Metaterol" title="Metaterol">Metaterol</a></li> <li><a href="/wiki/Metirosine" class="mw-redirect" title="Metirosine">Metirosine</a></li> <li><a href="/wiki/Methyldopa" title="Methyldopa">Methyldopa</a></li> <li><a href="/wiki/N,N-Dimethyldopamine" title="N,N-Dimethyldopamine">N,N-Dimethyldopamine</a></li> <li><a href="/wiki/Nordefrin" class="mw-redirect" title="Nordefrin">Nordefrin</a> (<a href="/wiki/Levonordefrin" class="mw-redirect" title="Levonordefrin">Levonordefrin</a>)</li> <li><a href="/wiki/Norepinephrine" title="Norepinephrine">Norepinephrine</a></li> <li><a href="/wiki/Norfenefrine" title="Norfenefrine">Norfenefrine</a> (m-Octopamine)</li> <li><a href="/wiki/Normetanephrine" title="Normetanephrine">Normetanephrine</a></li> <li><a href="/wiki/Orciprenaline" title="Orciprenaline">Orciprenaline</a></li> <li><a href="/wiki/Octopamine" title="Octopamine">p-Octopamine</a></li> <li><a href="/wiki/Tyramine" title="Tyramine">p-Tyramine</a></li> <li><a href="/wiki/Phenylephrine" title="Phenylephrine">Phenylephrine</a></li> <li><a href="/wiki/Synephrine" title="Synephrine">Synephrine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Miscellaneous</th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/AL-LAD" title="AL-LAD">AL-LAD</a></li> <li><a href="/wiki/Amidephrine" title="Amidephrine">Amidephrine</a></li> <li><a href="/wiki/Arbutamine" title="Arbutamine">Arbutamine</a></li> <li><a href="/wiki/Cafedrine" title="Cafedrine">Cafedrine</a></li> <li><a href="/wiki/Denopamine" title="Denopamine">Denopamine</a></li> <li><a href="/wiki/Desvenlafaxine" title="Desvenlafaxine">Desvenlafaxine</a></li> <li><a href="/wiki/Diphenidine" title="Diphenidine">Diphenidine</a></li> <li><a href="/wiki/Dizocilpine" title="Dizocilpine">Dizocilpine</a></li> <li><a href="/wiki/Dobutamine" title="Dobutamine">Dobutamine</a></li> <li><a href="/wiki/Dopexamine" title="Dopexamine">Dopexamine</a></li> <li><a href="/wiki/Ephenidine" title="Ephenidine">Ephenidine</a></li> <li><a href="/wiki/Etafedrine" title="Etafedrine">Etafedrine</a></li> <li><a href="/wiki/ETH-LAD" title="ETH-LAD">ETH-LAD</a></li> <li><a href="/wiki/Famprofazone" title="Famprofazone">Famprofazone</a></li> <li><a href="/wiki/Fluorolintane" title="Fluorolintane">Fluorolintane</a></li> <li><a href="/wiki/Hexapradol" title="Hexapradol">Hexapradol</a></li> <li><a href="/wiki/IP-LAD" class="mw-redirect" title="IP-LAD">IP-LAD</a></li> <li><a href="/wiki/Lysergic_acid_amide" class="mw-redirect" title="Lysergic acid amide">Lysergic acid amide</a></li> <li><a href="/wiki/Lysergic_acid_2-butyl_amide" title="Lysergic acid 2-butyl amide">Lysergic acid 2-butyl amide</a></li> <li><a href="/wiki/Lysergic_acid_2,4-dimethylazetidide" title="Lysergic acid 2,4-dimethylazetidide">Lysergic acid 2,4-dimethylazetidide</a></li> <li><a href="/wiki/LSD" title="LSD">Lysergic acid diethylamide</a></li> <li><a href="/wiki/Methoxamine" title="Methoxamine">Methoxamine</a></li> <li><a href="/wiki/Methoxphenidine" title="Methoxphenidine">Methoxphenidine</a></li> <li><a href="/wiki/MT-45" title="MT-45">MT-45</a></li> <li><a href="/wiki/PARGY-LAD" title="PARGY-LAD">PARGY-LAD</a></li> <li><a href="/wiki/Phenibut" title="Phenibut">Phenibut</a></li> <li><a href="/wiki/PRO-LAD" title="PRO-LAD">PRO-LAD</a></li> <li><a href="/wiki/Pronethalol" title="Pronethalol">Pronethalol</a></li> <li><a href="/wiki/Salbutamol" title="Salbutamol">Salbutamol</a> (<a href="/wiki/Levosalbutamol" title="Levosalbutamol">Levosalbutamol</a>)</li> <li><a href="/wiki/Solriamfetol" title="Solriamfetol">Solriamfetol</a></li> <li><a href="/wiki/Theodrenaline" title="Theodrenaline">Theodrenaline</a></li> <li><a href="/wiki/Thiamphenicol" title="Thiamphenicol">Thiamphenicol</a></li> <li><a href="/wiki/UWA-101" title="UWA-101">UWA-101</a></li> <li><a href="/wiki/Venlafaxine" title="Venlafaxine">Venlafaxine</a></li></ul> </div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374" /><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235" /><style data-mw-deduplicate="TemplateStyles:r1038841319">.mw-parser-output .tooltip-dotted{border-bottom:1px dotted;cursor:help}</style></div><div role="navigation" class="navbox authority-control" aria-label="Navbox863" style="padding:3px"><table class="nowraplinks hlist navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Help:Authority_control" title="Help:Authority control">Authority control databases</a>: National <a href="https://www.wikidata.org/wiki/Q69488#identifiers" title="Edit this at Wikidata"><img alt="Edit this at Wikidata" src="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/10px-OOjs_UI_icon_edit-ltr-progressive.svg.png" decoding="async" width="10" height="10" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/15px-OOjs_UI_icon_edit-ltr-progressive.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/20px-OOjs_UI_icon_edit-ltr-progressive.svg.png 2x" data-file-width="20" data-file-height="20" /></a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"><ul><li><a rel="nofollow" class="external text" href="https://d-nb.info/gnd/4359402-5">Germany</a></li><li><a rel="nofollow" class="external text" href="https://id.loc.gov/authorities/sh89002646">United States</a></li><li><a rel="nofollow" class="external text" href="https://aleph.nkp.cz/F/?func=find-c&local_base=aut&ccl_term=ica=ph215900&CON_LNG=ENG">Czech Republic</a></li><li><a rel="nofollow" class="external text" href="https://www.nli.org.il/en/authorities/987007546564105171">Israel</a></li></ul></div></td></tr></tbody></table></div>    </div><noscript><img src="https://login.wikimedia.org/wiki/Special:CentralAutoLogin/start?useformat=desktop&type=1x1&usesul3=0" alt="" width="1" height="1" style="border: none; position: absolute;"></noscript> <div class="printfooter" data-nosnippet="">Retrieved from "<a dir="ltr" href="https://en.wikipedia.org/w/index.php?title=MDMA&oldid=1278008831">https://en.wikipedia.org/w/index.php?title=MDMA&oldid=1278008831</a>"</div></div> <div id="catlinks" class="catlinks" data-mw="interface"><div id="mw-normal-catlinks" class="mw-normal-catlinks"><a href="/wiki/Help:Category" title="Help:Category">Categories</a>: <ul><li><a href="/wiki/Category:Drugs_not_assigned_an_ATC_code" title="Category:Drugs not assigned 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