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vector-toc-level-2"> <a class="vector-toc-link" href="#Psychiatric_effects_and_perceptual_disturbances"> <div class="vector-toc-text"> 2.2 Psychiatric effects and perceptual disturbances </div> </a> <ul id="toc-Psychiatric_effects_and_perceptual_disturbances-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Theory_of_mind_network_and_default_mode_network" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Theory_of_mind_network_and_default_mode_network"> <div class="vector-toc-text"> 2.3 Theory of mind network and default mode network </div> </a> <ul id="toc-Theory_of_mind_network_and_default_mode_network-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Group_perceptions" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Group_perceptions"> <div class="vector-toc-text"> 2.4 Group perceptions </div> </a> <ul id="toc-Group_perceptions-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Adverse_effects" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Adverse_effects"> <div class="vector-toc-text"> 2.5 Adverse effects </div> </a> <ul id="toc-Adverse_effects-sublist" class="vector-toc-list"> <li id="toc-Toxicity" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Toxicity"> <div class="vector-toc-text"> 2.5.1 Toxicity </div> </a> <ul id="toc-Toxicity-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Psychiatric" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Psychiatric"> <div class="vector-toc-text"> 2.5.2 Psychiatric </div> </a> <ul id="toc-Psychiatric-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Tolerance_and_dependence" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Tolerance_and_dependence"> <div class="vector-toc-text"> 2.5.3 Tolerance and dependence </div> </a> <ul id="toc-Tolerance_and_dependence-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> </ul> </li> <li id="toc-Cultural_significance_and_"mystical"_experiences" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Cultural_significance_and_"mystical"_experiences"> <div class="vector-toc-text"> 3 Cultural significance and "mystical" experiences </div> </a> <button aria-controls="toc-Cultural_significance_and_"mystical"_experiences-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> Toggle Cultural significance and "mystical" experiences subsection </button> <ul id="toc-Cultural_significance_and_"mystical"_experiences-sublist" class="vector-toc-list"> <li id="toc-Available_forms" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Available_forms"> <div class="vector-toc-text"> 3.1 Available forms </div> </a> <ul id="toc-Available_forms-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"> 4 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-Physical_properties" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Physical_properties"> <div class="vector-toc-text"> 4.1 Physical properties </div> </a> <ul id="toc-Physical_properties-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Structural_analogues" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Structural_analogues"> <div class="vector-toc-text"> 4.2 Structural analogues </div> </a> <ul id="toc-Structural_analogues-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Laboratory_synthesis" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Laboratory_synthesis"> <div class="vector-toc-text"> 4.3 Laboratory synthesis </div> </a> <ul id="toc-Laboratory_synthesis-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Biosynthesis" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Biosynthesis"> <div class="vector-toc-text"> 4.4 Biosynthesis </div> </a> <ul id="toc-Biosynthesis-sublist" class="vector-toc-list"> </ul> </li> </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"> 5 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"> 5.1 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"> 5.2 Pharmacokinetics </div> </a> <ul id="toc-Pharmacokinetics-sublist" class="vector-toc-list"> <li id="toc-Absorption" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Absorption"> <div class="vector-toc-text"> 5.2.1 Absorption </div> </a> <ul id="toc-Absorption-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Distribution" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Distribution"> <div class="vector-toc-text"> 5.2.2 Distribution </div> </a> <ul id="toc-Distribution-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Metabolism" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Metabolism"> <div class="vector-toc-text"> 5.2.3 Metabolism </div> </a> <ul id="toc-Metabolism-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Elimination" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Elimination"> <div class="vector-toc-text"> 5.2.4 Elimination </div> </a> <ul id="toc-Elimination-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Miscellaneous" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Miscellaneous"> <div class="vector-toc-text"> 5.2.5 Miscellaneous </div> </a> <ul id="toc-Miscellaneous-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Analytical_methods" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Analytical_methods"> <div class="vector-toc-text"> 5.3 Analytical methods </div> </a> <ul id="toc-Analytical_methods-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Natural_occurrence" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Natural_occurrence"> <div class="vector-toc-text"> 6 Natural occurrence </div> </a> <ul id="toc-Natural_occurrence-sublist" class="vector-toc-list"> </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"> 7 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"> 7.1 Legal status </div> </a> <ul id="toc-Legal_status-sublist" class="vector-toc-list"> <li id="toc-Advocacy_for_tolerance" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Advocacy_for_tolerance"> <div class="vector-toc-text"> 7.1.1 Advocacy for tolerance </div> </a> <ul id="toc-Advocacy_for_tolerance-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Usage" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Usage"> <div class="vector-toc-text"> 7.2 Usage </div> </a> <ul id="toc-Usage-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Research" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Research"> <div class="vector-toc-text"> 8 Research </div> </a> <button aria-controls="toc-Research-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> Toggle Research subsection </button> <ul id="toc-Research-sublist" class="vector-toc-list"> <li id="toc-Depression" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Depression"> <div class="vector-toc-text"> 8.1 Depression </div> </a> <ul id="toc-Depression-sublist" class="vector-toc-list"> </ul> </li> </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"> 9 See also </div> </a> <ul id="toc-See_also-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Explanatory_notes" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Explanatory_notes"> <div class="vector-toc-text"> 10 Explanatory notes </div> </a> <ul id="toc-Explanatory_notes-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"> 11 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"> 12 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">Psilocybin</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 48 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-48" aria-hidden="true" > 48 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/%D8%B3%D9%8A%D9%84%D9%88%D8%B3%D9%8A%D8%A8%D9%8A%D9%86" title="سيلوسيبين – Arabic" lang="ar" hreflang="ar" data-title="سيلوسيبين" data-language-autonym="العربية" data-language-local-name="Arabic" class="interlanguage-link-target">العربية</a></li><li class="interlanguage-link interwiki-ast mw-list-item"><a href="https://ast.wikipedia.org/wiki/Psilocibina" title="Psilocibina – Asturian" lang="ast" hreflang="ast" data-title="Psilocibina" data-language-autonym="Asturianu" data-language-local-name="Asturian" class="interlanguage-link-target">Asturianu</a></li><li class="interlanguage-link interwiki-azb mw-list-item"><a href="https://azb.wikipedia.org/wiki/%D8%B3%DB%8C%D9%84%D9%88%D8%B3%D8%A7%DB%8C%D8%A8%DB%8C%D9%86" title="سیلوسایبین – South Azerbaijani" lang="azb" hreflang="azb" data-title="سیلوسایبین" 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/%D0%9F%D1%81%D0%B8%D0%BB%D0%BE%D1%86%D0%B8%D0%B1%D0%B8%D0%BD" title="Псилоцибин – Bulgarian" lang="bg" hreflang="bg" data-title="Псилоцибин" data-language-autonym="Български" data-language-local-name="Bulgarian" class="interlanguage-link-target">Български</a></li><li class="interlanguage-link interwiki-ca mw-list-item"><a href="https://ca.wikipedia.org/wiki/Psilocibina" title="Psilocibina – Catalan" lang="ca" hreflang="ca" data-title="Psilocibina" 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/Psilocybin" title="Psilocybin – Czech" lang="cs" hreflang="cs" data-title="Psilocybin" 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/Psilocybin" title="Psilocybin – Welsh" lang="cy" hreflang="cy" data-title="Psilocybin" 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/Psilocybin" title="Psilocybin – Danish" lang="da" hreflang="da" data-title="Psilocybin" 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/Psilocybin" title="Psilocybin – German" lang="de" hreflang="de" data-title="Psilocybin" 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/Psilots%C3%BCbiin" title="Psilotsübiin – Estonian" lang="et" hreflang="et" data-title="Psilotsübiin" 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/%CE%A8%CE%B9%CE%BB%CE%BF%CE%BA%CF%85%CE%B2%CE%AF%CE%BD%CE%B7" title="Ψιλοκυβίνη – Greek" lang="el" hreflang="el" data-title="Ψιλοκυβίνη" data-language-autonym="Ελληνικά" data-language-local-name="Greek" class="interlanguage-link-target">Ελληνικά</a></li><li class="interlanguage-link interwiki-es mw-list-item"><a href="https://es.wikipedia.org/wiki/Psilocibina" title="Psilocibina – Spanish" lang="es" hreflang="es" data-title="Psilocibina" 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/Psilocibino" title="Psilocibino – Esperanto" lang="eo" hreflang="eo" data-title="Psilocibino" 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/Psilozibina" title="Psilozibina – Basque" lang="eu" hreflang="eu" data-title="Psilozibina" 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%B3%DB%8C%D9%84%D9%88%D8%B3%D8%A7%DB%8C%D8%A8%DB%8C%D9%86" title="سیلوسایبین – Persian" lang="fa" hreflang="fa" data-title="سیلوسایبین" data-language-autonym="فارسی" data-language-local-name="Persian" class="interlanguage-link-target">فارسی</a></li><li class="interlanguage-link interwiki-fr mw-list-item"><a href="https://fr.wikipedia.org/wiki/Psilocybine" title="Psilocybine – French" lang="fr" hreflang="fr" data-title="Psilocybine" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target">Français</a></li><li class="interlanguage-link interwiki-ga mw-list-item"><a href="https://ga.wikipedia.org/wiki/Silic%C3%ADbin" title="Silicíbin – Irish" lang="ga" hreflang="ga" data-title="Silicíbin" 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/Psilocibina" title="Psilocibina – Galician" lang="gl" hreflang="gl" data-title="Psilocibina" 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/%EC%8B%A4%EB%A1%9C%EC%8B%9C%EB%B9%88" title="실로시빈 – Korean" lang="ko" hreflang="ko" data-title="실로시빈" 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%B8%E0%A4%BE%E0%A4%87%E0%A4%B2%E0%A5%8B%E0%A4%B8%E0%A4%BE%E0%A4%87%E0%A4%AC%E0%A4%BF%E0%A4%A8" title="साइलोसाइबिन – Hindi" lang="hi" hreflang="hi" data-title="साइलोसाइबिन" 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/Psilocibin" title="Psilocibin – Croatian" lang="hr" hreflang="hr" data-title="Psilocibin" data-language-autonym="Hrvatski" data-language-local-name="Croatian" class="interlanguage-link-target">Hrvatski</a></li><li class="interlanguage-link interwiki-io mw-list-item"><a href="https://io.wikipedia.org/wiki/Psilocibino" title="Psilocibino – Ido" lang="io" hreflang="io" data-title="Psilocibino" data-language-autonym="Ido" data-language-local-name="Ido" class="interlanguage-link-target">Ido</a></li><li class="interlanguage-link interwiki-id mw-list-item"><a href="https://id.wikipedia.org/wiki/Psilosibin" title="Psilosibin – Indonesian" lang="id" hreflang="id" data-title="Psilosibin" data-language-autonym="Bahasa Indonesia" data-language-local-name="Indonesian" class="interlanguage-link-target">Bahasa Indonesia</a></li><li class="interlanguage-link interwiki-ia mw-list-item"><a href="https://ia.wikipedia.org/wiki/Psilocybina" title="Psilocybina – Interlingua" lang="ia" hreflang="ia" data-title="Psilocybina" data-language-autonym="Interlingua" data-language-local-name="Interlingua" class="interlanguage-link-target">Interlingua</a></li><li class="interlanguage-link interwiki-it mw-list-item"><a href="https://it.wikipedia.org/wiki/Psilocibina" title="Psilocibina – Italian" lang="it" hreflang="it" data-title="Psilocibina" 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/%D7%A4%D7%A1%D7%99%D7%9C%D7%95%D7%A6%D7%99%D7%91%D7%99%D7%9F" title="פסילוציבין – Hebrew" lang="he" hreflang="he" data-title="פסילוציבין" data-language-autonym="עברית" data-language-local-name="Hebrew" class="interlanguage-link-target">עברית</a></li><li class="interlanguage-link interwiki-lv mw-list-item"><a href="https://lv.wikipedia.org/wiki/Psilocib%C4%ABns" title="Psilocibīns – Latvian" lang="lv" hreflang="lv" data-title="Psilocibīns" 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/Psilocibinas" title="Psilocibinas – Lithuanian" lang="lt" hreflang="lt" data-title="Psilocibinas" data-language-autonym="Lietuvių" data-language-local-name="Lithuanian" class="interlanguage-link-target">Lietuvių</a></li><li class="interlanguage-link interwiki-lfn mw-list-item"><a href="https://lfn.wikipedia.org/wiki/Silosibina" title="Silosibina – Lingua Franca Nova" lang="lfn" hreflang="lfn" data-title="Silosibina" data-language-autonym="Lingua Franca Nova" data-language-local-name="Lingua Franca Nova" class="interlanguage-link-target">Lingua Franca Nova</a></li><li class="interlanguage-link interwiki-hu mw-list-item"><a href="https://hu.wikipedia.org/wiki/Pszilocibin" title="Pszilocibin – Hungarian" lang="hu" hreflang="hu" data-title="Pszilocibin" data-language-autonym="Magyar" data-language-local-name="Hungarian" class="interlanguage-link-target">Magyar</a></li><li class="interlanguage-link interwiki-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/Psilocybine" title="Psilocybine – Dutch" lang="nl" hreflang="nl" data-title="Psilocybine" 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%82%B7%E3%83%AD%E3%82%B7%E3%83%93%E3%83%B3" title="シロシビン – Japanese" lang="ja" hreflang="ja" data-title="シロシビン" 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/Psilocybin" title="Psilocybin – Norwegian Bokmål" lang="nb" hreflang="nb" data-title="Psilocybin" data-language-autonym="Norsk bokmål" data-language-local-name="Norwegian Bokmål" class="interlanguage-link-target">Norsk bokmål</a></li><li class="interlanguage-link interwiki-pl mw-list-item"><a href="https://pl.wikipedia.org/wiki/Psylocybina" title="Psylocybina – Polish" lang="pl" hreflang="pl" data-title="Psylocybina" 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/Psilocibina" title="Psilocibina – Portuguese" lang="pt" hreflang="pt" data-title="Psilocibina" 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/Psilocibin%C4%83" title="Psilocibină – Romanian" lang="ro" hreflang="ro" data-title="Psilocibină" data-language-autonym="Română" data-language-local-name="Romanian" class="interlanguage-link-target">Română</a></li><li class="interlanguage-link interwiki-ru mw-list-item"><a href="https://ru.wikipedia.org/wiki/%D0%9F%D1%81%D0%B8%D0%BB%D0%BE%D1%86%D0%B8%D0%B1%D0%B8%D0%BD" title="Псилоцибин – Russian" lang="ru" hreflang="ru" data-title="Псилоцибин" data-language-autonym="Русский" data-language-local-name="Russian" class="interlanguage-link-target">Русский</a></li><li class="interlanguage-link interwiki-simple mw-list-item"><a href="https://simple.wikipedia.org/wiki/Psilocybin" title="Psilocybin – Simple English" lang="en-simple" hreflang="en-simple" data-title="Psilocybin" 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/Psilocyb%C3%ADn" title="Psilocybín – Slovak" lang="sk" hreflang="sk" data-title="Psilocybín" 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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">Psilocybin <abbr title="International nonproprietary name">INN</abbr>: Psilocybine</caption><tbody><tr><td colspan="2" class="infobox-image"><a href="/wiki/File:Psilocybin,_Kekul%C3%A9,_skeletal_formula_of_canonical_psilocybin.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/9/97/Psilocybin%2C_Kekul%C3%A9%2C_skeletal_formula_of_canonical_psilocybin.svg/200px-Psilocybin%2C_Kekul%C3%A9%2C_skeletal_formula_of_canonical_psilocybin.svg.png" decoding="async" width="200" height="154" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/9/97/Psilocybin%2C_Kekul%C3%A9%2C_skeletal_formula_of_canonical_psilocybin.svg/300px-Psilocybin%2C_Kekul%C3%A9%2C_skeletal_formula_of_canonical_psilocybin.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/9/97/Psilocybin%2C_Kekul%C3%A9%2C_skeletal_formula_of_canonical_psilocybin.svg/400px-Psilocybin%2C_Kekul%C3%A9%2C_skeletal_formula_of_canonical_psilocybin.svg.png 2x" data-file-width="343" data-file-height="264" /></a><div class="infobox-caption">Kekulé, skeletal formula of canonical psilocybin</div></td></tr><tr><td colspan="2" class="infobox-image"><a href="/wiki/File:Psilocybin_zwitterion_3D_ball.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/0/00/Psilocybin_zwitterion_3D_ball.png/200px-Psilocybin_zwitterion_3D_ball.png" decoding="async" width="200" height="170" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/0/00/Psilocybin_zwitterion_3D_ball.png/300px-Psilocybin_zwitterion_3D_ball.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/0/00/Psilocybin_zwitterion_3D_ball.png/400px-Psilocybin_zwitterion_3D_ball.png 2x" data-file-width="2000" data-file-height="1696" /></a><div class="infobox-caption">Ball-and-stick model of canonical psilocybin</div></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"><a href="/wiki/Help:IPA/English" title="Help:IPA/English">/ˌsaɪləˈsaɪbɪn/</a> <a href="/wiki/Help:Pronunciation_respelling_key" title="Help:Pronunciation respelling key">sy-lə-SY-bin</a>, <a href="/wiki/Help:IPA/English" title="Help:IPA/English">/ˌsɪl-/</a> </td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;">Other names</th><td class="infobox-data">Psilocybine; Psilocibin; Psylocybin; Psilotsibin; Psilocin phosphate; Psilocin phosphate ester; O-Phosphoryl-4-hydroxy-N,N-dimethyltryptamine; 4-Phosphoryloxy-N,N-dimethyltryptamine; 4-Phosphoryl-N,N-dimethyltryptamine; 4-PO-DMT; COMP360; COMP-360, Psilocybin (<a href="/wiki/United_States_Adopted_Name" title="United States Adopted Name">USAN</a> <abbr title="United States">US</abbr>)</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">Low<a href="#cite_note-JohnsonGriffithsHendricks2018-1">[1]</a><a href="#cite_note-Passie2002-2">[2]</a><a href="#cite_note-Chen2008-3">[3]</a><a href="#cite_note-Amsterdam2010-4">[4]</a><a href="#cite_note-Nutt2010-5">[5]</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<a href="#cite_note-JohnsonGriffithsHendricks2018-1">[1]</a><a href="#cite_note-Nicholas2006-6">[6]</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"><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><a href="/wiki/Oral_administration" title="Oral administration">By mouth</a>,</li> <li><a href="/wiki/Intravenous_administration" class="mw-redirect" title="Intravenous administration">intravenous</a><a href="#cite_note-LoweToyangSteele2021-7">[7]</a></li></ul> </div></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/Serotonergic_psychedelic" class="mw-redirect" title="Serotonergic psychedelic">Serotonergic psychedelic</a>; <a href="/wiki/Hallucinogen" title="Hallucinogen">Hallucinogen</a>; <a href="/wiki/Serotonin_receptor_agonist" title="Serotonin receptor agonist">Serotonin receptor agonist</a>; <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/Agonist" title="Agonist">agonist</a><a href="#cite_note-SzafoniGręblowskiGrabowska2024-8">[8]</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"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><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>: S9/S8 (Controlled Drug)</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-9">[9]</a></li> <li><abbr class="country-name" title="Canada">CA</abbr>: <a href="/wiki/Controlled_Drugs_and_Substances_Act#Schedule_III" title="Controlled Drugs and Substances Act">Schedule III</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></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>: 52.7 ± 20.4% (as <a href="/wiki/Psilocin" title="Psilocin">psilocin</a>) (n=3)<a href="#cite_note-DoddNormanEyre2023-10">[10]</a><a href="#cite_note-MacCallumLoPistawka2022-11">[11]</a><a href="#cite_note-HaslerBourquinBrenneisen1997-12">[12]</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">66%<a href="#cite_note-ČamparaKovačić2024-13">[13]</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>, other <a href="/wiki/Tissue_(biology)" title="Tissue (biology)">tissues</a>:<a href="#cite_note-MacCallumLoPistawka2022-11">[11]</a><a href="#cite_note-DoddNormanEyre2023-10">[10]</a><a href="#cite_note-LoweToyangSteele2021-7">[7]</a><a href="#cite_note-CoppolaBevioneMondola2022-20">[20]</a> • <a href="/wiki/Dephosphorylation" title="Dephosphorylation">Dephosphorylation</a> (<a href="/wiki/Alkaline_phosphatase" title="Alkaline phosphatase"><abbr title="alkaline phosphatase">ALP</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 alkaline phosphatase) • <a href="/wiki/Demethylation" title="Demethylation">Demethylation</a> and <a href="/wiki/Deamination" title="Deamination">deamination</a> (<a href="/wiki/Monoamine_oxidase" title="Monoamine oxidase"><abbr title="monoamine oxidase">MAO</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 monoamine oxidase) • <a href="/wiki/Oxidation" class="mw-redirect" title="Oxidation">Oxidation</a> (<a href="/wiki/Aldehyde_dehydrogenase" title="Aldehyde dehydrogenase"><abbr title="aldehyde dehydrogenase">ALDH</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 aldehyde dehydrogenase) • <a href="/wiki/Glucuronidation" title="Glucuronidation">Glucuronidation</a> (<a href="/wiki/UDP-glucuronyltransferase" class="mw-redirect" title="UDP-glucuronyltransferase"><abbr title="UDP-glucuronyltransferases">UGTs</abbr></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/Psilocin" title="Psilocin">Psilocin</a><a href="#cite_note-MacCallumLoPistawka2022-11">[11]</a><a href="#cite_note-DoddNormanEyre2023-10">[10]</a><a href="#cite_note-LoweToyangSteele2021-7">[7]</a> • Psilocin-O-glucuronide<a href="#cite_note-DoddNormanEyre2023-10">[10]</a><a href="#cite_note-LoweToyangSteele2021-7">[7]</a> • 4-Hydroxyindole-3-acetaldehyde<a href="#cite_note-DoddNormanEyre2023-10">[10]</a><a href="#cite_note-LoweToyangSteele2021-7">[7]</a> • 4-Hydroxyindole-3-acetic acid (4-HIAA)<a href="#cite_note-DoddNormanEyre2023-10">[10]</a><a href="#cite_note-LoweToyangSteele2021-7">[7]</a> • 4-Hydroxytryptophol<a href="#cite_note-DoddNormanEyre2023-10">[10]</a><a href="#cite_note-LoweToyangSteele2021-7">[7]</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>: 20–50 min<a href="#cite_note-MacCallumLoPistawka2022-11">[11]</a><a href="#cite_note-HolzeSinghLiechti2024-14">[14]</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"><a href="/wiki/Oral_administration" title="Oral administration">Oral</a> (as <a href="/wiki/Psilocin" title="Psilocin">psilocin</a>): 2.1–4.7 h (range 1.2–18.6 h)<a href="#cite_note-DoddNormanEyre2023-10">[10]</a><a href="#cite_note-OttovanderHeijdenSchoones2025-15">[15]</a><a href="#cite_note-Manzano-NunezGomezToledo-Mendoza2025-16">[16]</a> <a href="/wiki/Intravenous_administration" class="mw-redirect" title="Intravenous administration"><abbr title="Intravenous administration">IV</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 Intravenous administration (as psilocin): 1.2 h (range 1.8–4.5 h)<a href="#cite_note-DoddNormanEyre2023-10">[10]</a><a href="#cite_note-Passie2002-2">[2]</a></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"><a href="/wiki/Oral_administration" title="Oral administration">Oral</a>: 4–6 h (range 3–12 h)<a href="#cite_note-MacCallumLoPistawka2022-11">[11]</a><a href="#cite_note-YerubandiThomasBhuiya2024-17">[17]</a><a href="#cite_note-GeigerWurstDaniels2018-18">[18]</a> <a href="/wiki/Intravenous_injection" class="mw-redirect" title="Intravenous injection"><abbr title="Intravenous injection">IV</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 Intravenous injection: 15–30 min (1 mg)<a href="#cite_note-Passie2002-2">[2]</a><a href="#cite_note-HaslerBourquinBrenneisen1997-12">[12]</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/Urine" title="Urine">Urine</a> (mainly as psilocin-O-glucuronide, 2–4% as unchanged psilocin)<a href="#cite_note-DoddNormanEyre2023-10">[10]</a><a href="#cite_note-LoweToyangSteele2021-7">[7]</a><a href="#cite_note-TylšPáleníčekHoráček2014-19">[19]</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%;">[3-[2-(dimethylamino)ethyl]-1H-indol-4-yl] dihydrogen phosphate</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=520-52-5">520-52-5</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/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/10624">10624</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/DB11664">DB11664</a></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.10178.html">10178</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/2RV7212BP0">2RV7212BP0</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/D12881">D12881</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:8614">CHEBI:8614</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/ChEMBL194378">ChEMBL194378</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/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/DTXSID0048898">DTXSID0048898</a> <a href="https://www.wikidata.org/wiki/Q208118#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 scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/ECHA_InfoCard" class="mw-redirect" title="ECHA InfoCard">ECHA InfoCard</a></th><td class="infobox-data"><a rel="nofollow" class="external text" href="https://echa.europa.eu/substance-information/-/substanceinfo/100.007.542">100.007.542</a> <a href="https://www.wikidata.org/wiki/Q208118#P2566" 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></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">C12H17N2O4P</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">284.252 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=CN%28C%29CCC1%3DCNC2%3DC1C%28%3DCC%3DC2%29OP%28%3DO%29%28O%29O">Interactive image</a></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Melting_point" title="Melting point">Melting point</a></th><td class="infobox-data">220–228 °C (428–442 °F) <a href="#cite_note-Merck-21">[21]</a></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%;">CN(C)CCC1=CNC2=C1C(=CC=C2)OP(=O)(O)O</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/C12H17N2O4P/c1-14(2)7-6-9-8-13-10-4-3-5-11(12(9)10)18-19(15,16)17/h3-5,8,13H,6-7H2,1-2H3,(H2,15,16,17) <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:QVDSEJDULKLHCG-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=479504713&page2=Psilocybin">(verify)</a></td></tr></tbody></table> Psilocybin, also known as 4-phosphoryloxy-N,N-dimethyltryptamine (4-PO-DMT)<a href="#cite_note-23">[a]</a> is a <a href="/wiki/Natural_product" title="Natural product">naturally occurring</a> <a href="/wiki/Psychedelic_drug" title="Psychedelic drug">psychedelic</a> <a href="/wiki/Chemical_compound" title="Chemical compound">compound</a> produced by more than <a href="/wiki/List_of_psilocybin_mushroom_species" title="List of psilocybin mushroom species">200 species</a> of <a href="/wiki/Mushroom" title="Mushroom">mushrooms</a>.<a href="#cite_note-GeigerWurstDaniels2018-18">[18]</a> Effects include <a href="/wiki/Euphoria" title="Euphoria">euphoria</a>, <a href="/wiki/Hallucination" title="Hallucination">hallucinations</a>, changes in <a href="/wiki/Perception" title="Perception">perception</a>, a distorted <a href="/wiki/Sense_of_time" class="mw-redirect" title="Sense of time">sense of time</a>,<a href="#cite_note-:1-24">[23]</a> and perceived <a href="/wiki/Spiritual_experiences" class="mw-redirect" title="Spiritual experiences">spiritual experiences</a>. It can also cause <a href="/wiki/Adverse_reaction" class="mw-redirect" title="Adverse reaction">adverse reactions</a> such as <a href="/wiki/Nausea" title="Nausea">nausea</a> and <a href="/wiki/Panic_attack" title="Panic attack">panic attacks</a>. Its effects depend on <a href="/wiki/Set_and_setting" title="Set and setting">set and setting</a> and one's expectations.<a href="#cite_note-MacCallumLoPistawka2022-11">[11]</a><a href="#cite_note-FradetKellyDonnelly2025-25">[24]</a> Psilocybin is a <a href="/wiki/Prodrug" title="Prodrug">prodrug</a> of <a href="/wiki/Psilocin" title="Psilocin">psilocin</a>.<a href="#cite_note-GeigerWurstDaniels2018-18">[18]</a> That is, the compound itself is biologically inactive but quickly converted by the body to psilocin.<a href="#cite_note-GeigerWurstDaniels2018-18">[18]</a> Psilocybin is transformed into psilocin by <a href="/wiki/Dephosphorylation" title="Dephosphorylation">dephosphorylation</a> mediated via <a href="/wiki/Phosphatase" title="Phosphatase">phosphatase</a> <a href="/wiki/Enzyme" title="Enzyme">enzymes</a>.<a href="#cite_note-Nichols2020-26">[25]</a><a href="#cite_note-GeigerWurstDaniels2018-18">[18]</a> Psilocin is <a href="/wiki/Structural_analog" title="Structural analog">chemically related</a> to the <a href="/wiki/Neurotransmitter" title="Neurotransmitter">neurotransmitter</a> <a href="/wiki/Serotonin" title="Serotonin">serotonin</a> and acts as a <a href="/wiki/Binding_selectivity" title="Binding selectivity">non-selective</a> <a href="/wiki/Agonist" title="Agonist">agonist</a> of the <a href="/wiki/Serotonin_receptor" class="mw-redirect" title="Serotonin receptor">serotonin receptors</a>.<a href="#cite_note-GeigerWurstDaniels2018-18">[18]</a> Activation of one serotonin receptor, the serotonin <a href="/wiki/5-HT2A_receptor" title="5-HT2A receptor">5-HT2A receptor</a>, is specifically responsible for the hallucinogenic effects of psilocin and other <a href="/wiki/Serotonergic_psychedelic" class="mw-redirect" title="Serotonergic psychedelic">serotonergic psychedelics</a>.<a href="#cite_note-GeigerWurstDaniels2018-18">[18]</a> Psilocybin is usually taken <a href="/wiki/Oral_administration" title="Oral administration">orally</a>.<a href="#cite_note-GeigerWurstDaniels2018-18">[18]</a> By this <a href="/wiki/Route_of_administration" title="Route of administration">route</a>, its <a href="/wiki/Onset_of_action" title="Onset of action">onset</a> is about 20 to 50 minutes, <a href="/wiki/Tmax_(pharmacology)" class="mw-redirect" title="Tmax (pharmacology)">peak effects</a> occur after around 60 to 90 minutes, and its <a href="/wiki/Duration_of_action" class="mw-redirect" title="Duration of action">duration</a> is about 4 to 6 hours.<a href="#cite_note-MacCallumLoPistawka2022-11">[11]</a><a href="#cite_note-YerubandiThomasBhuiya2024-17">[17]</a><a href="#cite_note-GeigerWurstDaniels2018-18">[18]</a><a href="#cite_note-HolzeSinghLiechti2024-14">[14]</a> Imagery in <a href="/wiki/Cave_painting" title="Cave painting">cave paintings</a> and <a href="/wiki/Rock_art" title="Rock art">rock art</a> of modern-day <a href="/wiki/Algeria" title="Algeria">Algeria</a> and <a href="/wiki/Spain" title="Spain">Spain</a> suggests that human use of <a href="/wiki/Psilocybin_mushroom" title="Psilocybin mushroom">psilocybin mushrooms</a> predates recorded history.<a href="#cite_note-27">[26]</a> In <a href="/wiki/Mesoamerica" title="Mesoamerica">Mesoamerica</a>, the mushrooms had long been consumed in spiritual and <a href="/wiki/Divinatory" class="mw-redirect" title="Divinatory">divinatory</a> ceremonies before Spanish chroniclers first documented their use in the 16th century. In 1958, the Swiss chemist <a href="/wiki/Albert_Hofmann" title="Albert Hofmann">Albert Hofmann</a> isolated psilocybin and psilocin from the mushroom <a href="/wiki/Psilocybe_mexicana" title="Psilocybe mexicana">Psilocybe mexicana</a>. His employer, <a href="/wiki/Sandoz" title="Sandoz">Sandoz</a>, marketed and sold pure psilocybin to physicians and clinicians worldwide for use in <a href="/wiki/Psychedelic_therapy" title="Psychedelic therapy">psychedelic therapy</a>. Increasingly restrictive drug laws of the <a href="/wiki/Single_Convention_on_Narcotic_Drugs" title="Single Convention on Narcotic Drugs">1960s</a> and the <a href="/wiki/Convention_on_Psychotropic_Substances" title="Convention on Psychotropic Substances">1970s</a> curbed scientific research into the effects of psilocybin and other hallucinogens, but its popularity as an <a href="/wiki/Entheogen" title="Entheogen">entheogen</a> (spirituality-enhancing agent) grew in the next decade, owing largely to the increased availability of information on how to cultivate psilocybin mushrooms. Possession of psilocybin-containing mushrooms <a href="/wiki/Legal_status_of_psilocybin_mushrooms" title="Legal status of psilocybin mushrooms">has been outlawed</a> in most countries, and psilocybin has been classified as a <a href="/wiki/Convention_on_Psychotropic_Substances#Schedule_I" title="Convention on Psychotropic Substances">Schedule I controlled substance</a> under the 1971 United Nations <a href="/wiki/Convention_on_Psychotropic_Substances" title="Convention on Psychotropic Substances">Convention on Psychotropic Substances</a>. Psilocybin is being studied as a possible medicine in the treatment of <a href="/wiki/Psychiatric_disorder" class="mw-redirect" title="Psychiatric disorder">psychiatric disorders</a> such as <a href="/wiki/Depression_(mood)" title="Depression (mood)">depression</a> and <a href="/wiki/Obsessive%E2%80%93compulsive_disorder" title="Obsessive–compulsive disorder">obsessive–compulsive disorder</a> and other <a href="/wiki/Medical_condition" class="mw-redirect" title="Medical condition">conditions</a> such as <a href="/wiki/Cluster_headache" title="Cluster headache">cluster headaches</a>.<a href="#cite_note-MaddenFloodYoungShing2024-28">[27]</a> It is in late-stage <a href="/wiki/Clinical_trial" title="Clinical trial">clinical trials</a> for <a href="/wiki/Treatment-resistant_depression" title="Treatment-resistant depression">treatment-resistant depression</a>.<a href="#cite_note-MelaniBonasoBiso2025-29">[28]</a><a href="#cite_note-Najib2024-30">[29]</a><a href="#cite_note-AdisInsight-31">[30]</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="History">History</h2>[<a href="/w/index.php?title=Psilocybin&action=edit&section=1" title="Edit section: History">edit</a>]</div> <div class="mw-heading mw-heading3"><h3 id="Early">Early</h3>[<a href="/w/index.php?title=Psilocybin&action=edit&section=2" title="Edit section: Early">edit</a>]</div> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:Psilocybe_Mushrooms_statues.jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a4/Psilocybe_Mushrooms_statues.jpg/220px-Psilocybe_Mushrooms_statues.jpg" decoding="async" width="220" height="141" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a4/Psilocybe_Mushrooms_statues.jpg/330px-Psilocybe_Mushrooms_statues.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a4/Psilocybe_Mushrooms_statues.jpg/440px-Psilocybe_Mushrooms_statues.jpg 2x" data-file-width="605" data-file-height="389" /></a><figcaption><a href="/wiki/Maya_architecture" title="Maya architecture">Mayan</a> "mushroom stones" of <a href="/wiki/Guatemala" title="Guatemala">Guatemala</a>.</figcaption></figure> There is evidence to suggest that psychoactive mushrooms have been used by humans in religious ceremonies for thousands of years. The <a href="/wiki/Tassili_Mushroom_Figure" title="Tassili Mushroom Figure">Tassili Mushroom Figure</a> was discovered in <a href="/wiki/Tassili" class="mw-redirect" title="Tassili">Tassili</a>, <a href="/wiki/Algeria" title="Algeria">Algeria</a>, and is believed to depict psychedelic mushrooms and the transformation of the user under their influence. The paintings are said to date back to 9000-7000 BC.<a href="#cite_note-32">[31]</a> 6,000-year-old <a href="/wiki/Pictographs" class="mw-redirect" title="Pictographs">pictographs</a> discovered near the Spanish town of <a href="/wiki/Villar_del_Humo" title="Villar del Humo">Villar del Humo</a> illustrate several mushrooms that have been tentatively identified as <a href="/wiki/Psilocybe_hispanica" title="Psilocybe hispanica">Psilocybe hispanica</a>, a hallucinogenic species native to the area.<a href="#cite_note-Akers2011-33">[32]</a> Some scholars have also interpreted archaeological <a href="/wiki/Artifact_(archaeology)" title="Artifact (archaeology)">artifacts</a> from <a href="/wiki/Mexico" title="Mexico">Mexico</a> and the so-called <a href="/wiki/Maya_architecture" title="Maya architecture">Mayan</a> "mushroom stones" of <a href="/wiki/Guatemala" title="Guatemala">Guatemala</a> as evidence of ritual and ceremonial use of psychoactive mushrooms in the <a href="/wiki/Maya_civilization" title="Maya civilization">Mayan</a> and <a href="/wiki/Aztec" class="mw-redirect" title="Aztec">Aztec</a> cultures of <a href="/wiki/Mesoamerica" title="Mesoamerica">Mesoamerica</a>.<a href="#cite_note-Stamets_1996-34">[33]</a>: 11  In <a href="/wiki/Nahuatl" title="Nahuatl">Nahuatl</a>, the language of the Aztecs, the mushrooms were called teonanácatl—literally "divine mushroom": the agglutinative form of teō(tl) ("god", "sacred") and nanācatl ("mushroom") in Nahuatl.[<a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed">citation needed</a>] After Spanish explorers of the <a href="/wiki/New_World" title="New World">New World</a> arrived in the 16th century, chroniclers reported the use of mushrooms by the natives for ceremonial and religious purposes. According to the <a href="/wiki/Dominican_Order" title="Dominican Order">Dominican</a> friar <a href="/wiki/Diego_Dur%C3%A1n" title="Diego Durán">Diego Durán</a> in The History of the Indies of New Spain (published c. 1581), mushrooms were eaten in festivities conducted on the occasion of Aztec emperor <a href="/wiki/Moctezuma_II" title="Moctezuma II">Moctezuma II</a>'s accession to the throne in 1502. The <a href="/wiki/Franciscan" class="mw-redirect" title="Franciscan">Franciscan</a> friar <a href="/wiki/Bernardino_de_Sahag%C3%BAn" title="Bernardino de Sahagún">Bernardino de Sahagún</a> wrote of witnessing mushroom use in the <a href="/wiki/Florentine_Codex" title="Florentine Codex">Florentine Codex</a> (published 1545–1590),<a href="#cite_note-Marley2010-35">[34]</a>: 164  and described how some merchants would celebrate upon returning from a successful business trip by consuming mushrooms to evoke revelatory visions.<a href="#cite_note-Hofmann2009-36">[35]</a>: 118  After the <a href="/wiki/Spanish_conquest_of_the_Aztec_Empire" title="Spanish conquest of the Aztec Empire">defeat of the Aztecs</a>, the Spanish forbade traditional religious practices and rituals that they considered "pagan idolatry", including ceremonial mushroom use. For the next four centuries, the Indians of <a href="/wiki/Mesoamerica" title="Mesoamerica">Mesoamerica</a> hid their use of <a href="/wiki/Entheogens" class="mw-redirect" title="Entheogens">entheogens</a> from the Spanish authorities.<a href="#cite_note-Marley2010-35">[34]</a>: 165  Dozens of species of psychedelic mushrooms are found in Europe, but there is little documented usage of them in <a href="/wiki/Old_World" title="Old World">Old World</a> history besides the use of <a href="/wiki/Amanita_muscaria" title="Amanita muscaria">Amanita muscaria</a> among Siberian peoples.<a href="#cite_note-nyberg1-37">[36]</a><a href="#cite_note-38">[37]</a> The few existing accounts that mention psilocybin mushrooms typically lack sufficient information to allow species identification, focusing on their effects. For example, Flemish botanist <a href="/wiki/Carolus_Clusius" title="Carolus Clusius">Carolus Clusius</a> (1526–1609) described the bolond gomba ("crazy mushroom"), used in rural <a href="/wiki/Hungary" title="Hungary">Hungary</a> to prepare love potions. English botanist <a href="/wiki/John_Parkinson_(botanist)" title="John Parkinson (botanist)">John Parkinson</a> included details about a "foolish mushroom" in his 1640 <a href="/wiki/Herbal" title="Herbal">herbal</a> Theatricum Botanicum.<a href="#cite_note-Gartz_1997-39">[38]</a>: 10–12  The first reliably documented report of intoxication with Psilocybe semilanceata—Europe's most common and widespread psychedelic mushroom—involved a British family in 1799, who prepared a meal with mushrooms they had picked in London's <a href="/wiki/Green_Park" title="Green Park">Green Park</a>.<a href="#cite_note-Gartz_1997-39">[38]</a>: 16  <div class="mw-heading mw-heading3"><h3 id="Modern">Modern</h3>[<a href="/w/index.php?title=Psilocybin&action=edit&section=3" title="Edit section: Modern">edit</a>]</div> <figure class="mw-default-size mw-halign-left" typeof="mw:File/Thumb"><a href="/wiki/File:Albert_Hofmann_Oct_1993.jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/a/aa/Albert_Hofmann_Oct_1993.jpg/220px-Albert_Hofmann_Oct_1993.jpg" decoding="async" width="220" height="174" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/aa/Albert_Hofmann_Oct_1993.jpg/330px-Albert_Hofmann_Oct_1993.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/aa/Albert_Hofmann_Oct_1993.jpg/440px-Albert_Hofmann_Oct_1993.jpg 2x" data-file-width="480" data-file-height="379" /></a><figcaption>Albert Hofmann (shown here in 1993) purified psilocybin and psilocin from Psilocybe mexicana in the late 1950s.</figcaption></figure> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:Golden_teacher_kookoskuidussa_3.jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/6/62/Golden_teacher_kookoskuidussa_3.jpg/220px-Golden_teacher_kookoskuidussa_3.jpg" decoding="async" width="220" height="147" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/62/Golden_teacher_kookoskuidussa_3.jpg/330px-Golden_teacher_kookoskuidussa_3.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/62/Golden_teacher_kookoskuidussa_3.jpg/440px-Golden_teacher_kookoskuidussa_3.jpg 2x" data-file-width="4272" data-file-height="2848" /></a><figcaption>The increasing availability of information on growing techniques eventually made it possible for amateurs to grow psilocybin mushrooms (<a href="/wiki/Psilocybe_cubensis" title="Psilocybe cubensis">Psilocybe cubensis</a> pictured) without access to laboratory equipment.</figcaption></figure> American banker and amateur <a href="/wiki/Ethnomycologist" class="mw-redirect" title="Ethnomycologist">ethnomycologist</a> <a href="/wiki/R._Gordon_Wasson" title="R. Gordon Wasson">R. Gordon Wasson</a> and his wife, <a href="/wiki/Valentina_Pavlovna_Wasson" title="Valentina Pavlovna Wasson">Valentina P. Wasson</a>, a physician, studied the ritual use of psychoactive mushrooms by the native population in the <a href="/wiki/Mazatec" title="Mazatec">Mazatec</a> village <a href="/wiki/Huautla_de_Jim%C3%A9nez" title="Huautla de Jiménez">Huautla de Jiménez</a>, Mexico. In 1957, Wasson described the <a href="/wiki/Psychedelic_experience" title="Psychedelic experience">psychedelic visions</a> he experienced during these rituals in "<a href="/wiki/Seeking_the_Magic_Mushroom" title="Seeking the Magic Mushroom">Seeking the Magic Mushroom</a>", an article published in the American weekly <a href="/wiki/Life_(magazine)" title="Life (magazine)">Life</a> magazine.<a href="#cite_note-Wasson1957-40">[39]</a> Later the same year they were accompanied on a follow-up expedition by French mycologist <a href="/wiki/Roger_Heim" title="Roger Heim">Roger Heim</a>, who identified several of the mushrooms as Psilocybe species.<a href="#cite_note-Heim1957-41">[40]</a> Heim cultivated the mushrooms in France and sent samples for analysis to <a href="/wiki/Albert_Hofmann" title="Albert Hofmann">Albert Hofmann</a>, a chemist employed by the Swiss pharmaceutical company <a href="/wiki/Sandoz" title="Sandoz">Sandoz</a> (now Novartis). Hofmann—who had synthesized <a href="/wiki/Lysergic_acid_diethylamide" class="mw-redirect" title="Lysergic acid diethylamide">lysergic acid diethylamide</a> (LSD) in 1938—led a research group that isolated and identified the psychoactive alkaloids psilocybin and psilocin from <a href="/wiki/Psilocybe_mexicana" title="Psilocybe mexicana">Psilocybe mexicana</a>, publishing their results in 1958.<a href="#cite_note-Hofmann2009-36">[35]</a>: 128  The team was aided in the discovery process by Hofmann's willingness to ingest mushroom extracts to help verify the presence of the active compounds.<a href="#cite_note-Hofmann2009-36">[35]</a>: 126–127  Next, Hofmann's team synthesized several <a href="/wiki/Structural_analog" title="Structural analog">structural analogs</a> of these compounds to examine how these structural changes affect psychoactivity. This research led to the development of <a href="/wiki/Ethocybin" title="Ethocybin">ethocybin</a> and <a href="/wiki/CZ-74" class="mw-redirect" title="CZ-74">CZ-74</a>. Because these compounds' physiological effects last only about three and a half hours (about half as long as psilocybin's), they proved more manageable for use in <a href="/wiki/Psychedelic_therapy#Psycholytic_therapy" title="Psychedelic therapy">psycholytic therapy</a>.<a href="#cite_note-Stafford1992-42">[41]</a>: 237  Sandoz also marketed and sold pure psilocybin under the name Indocybin to clinicians and researchers worldwide.<a href="#cite_note-Marley2010-35">[34]</a>: 166  There were no reports of serious complications when psilocybin was used in this way.<a href="#cite_note-Passie2002-2">[2]</a> In the early 1960s, <a href="/wiki/Harvard_University" title="Harvard University">Harvard University</a> became a testing ground for psilocybin through the efforts of Timothy Leary and his associates <a href="/wiki/Ralph_Metzner" title="Ralph Metzner">Ralph Metzner</a> and Richard Alpert (who later changed his name to <a href="/wiki/Ram_Dass" title="Ram Dass">Ram Dass</a>). Leary obtained synthesized psilocybin from Hofmann through Sandoz Pharmaceuticals. Some studies, such as the <a href="/wiki/Concord_Prison_Experiment" title="Concord Prison Experiment">Concord Prison Experiment</a>, suggested promising results using psilocybin in <a href="/wiki/Clinical_psychiatry" class="mw-redirect" title="Clinical psychiatry">clinical psychiatry</a>.<a href="#cite_note-Leary1963-43">[42]</a><a href="#cite_note-Leary1965-44">[43]</a> But according to a 2008 review of safety guidelines in human hallucinogenic research, Leary's and Alpert's well-publicized termination from Harvard and later advocacy of hallucinogen use "further undermined an objective scientific approach to studying these compounds".<a href="#cite_note-Johnson2008-45">[44]</a> In response to concerns about the increase in unauthorized use of psychedelic drugs by the general public, psilocybin and other hallucinogenic drugs were unfavorably covered in the press and faced increasingly restrictive laws. In the U.S., laws passed in 1966 that prohibited the production, trade, or ingestion of hallucinogenic drugs; Sandoz stopped producing LSD and psilocybin the same year.<a href="#cite_note-Matsushima2009-46">[45]</a> In 1970, Congress passed "The Federal Comprehensive Drug Abuse Prevention and Control Act" that made LSD, peyote, psilocybin, and other hallucinogens illegal to use for any purpose, including scientific research.<a href="#cite_note-47">[46]</a> United States politicians' agenda against LSD usage had swept psilocybin along with it into the <a href="/wiki/Schedule_I_controlled_substance" class="mw-redirect" title="Schedule I controlled substance">Schedule I category</a> of illicit drugs. Such restrictions on the use of these drugs in human research made funding for such projects difficult to obtain, and scientists who worked with psychedelic drugs faced being "professionally marginalized".<a href="#cite_note-Griffiths2010-48">[47]</a> Although Hofmann tested these compounds <a href="/wiki/Self-experimentation" title="Self-experimentation">on himself</a>, he never advocated their legalization or medical use. In his 1979 book LSD—mein Sorgenkind (LSD—My Problem Child), he described the problematic use of these hallucinogens as inebriants.<a href="#cite_note-Hofmann2009-36">[35]</a>: 79–116  Despite the legal restrictions on psilocybin use, the 1970s witnessed the emergence of psilocybin as the "entheogen of choice".<a href="#cite_note-Ott_1993-49">[48]</a>: 276  This was due in large part to wide dissemination of information on the topic, which included works such as those by <a href="/wiki/Carlos_Castaneda" title="Carlos Castaneda">Carlos Castaneda</a> and several books that taught the technique of growing psilocybin mushrooms. One of the most popular of the latter group, Psilocybin: Magic Mushroom Grower's Guide, was published in 1976 under the pseudonyms O. T. Oss and O. N. Oeric by Jeremy Bigwood, <a href="/wiki/Dennis_Jon_McKenna" class="mw-redirect" title="Dennis Jon McKenna">Dennis J. McKenna</a>, K. Harrison McKenna, and Terence McKenna. Over 100,000 copies were sold by 1981.<a href="#cite_note-Oeric1991-50">[49]</a> As ethnobiologist <a href="/wiki/Jonathan_Ott" title="Jonathan Ott">Jonathan Ott</a> explains, "These authors adapted San Antonio's technique (for producing edible mushrooms by casing <a href="/wiki/Mycelial" class="mw-redirect" title="Mycelial">mycelial</a> cultures on a rye grain substrate; San Antonio 1971) to the production of Psilocybe [Stropharia] cubensis. The new technique involved the use of ordinary kitchen implements, and for the first time the layperson was able to produce a potent entheogen in his own home, without access to sophisticated technology, equipment or chemical supplies."<a href="#cite_note-Ott_1993-49">[48]</a>: 290  San Antonio's technique describes a method to grow the common edible mushroom <a href="/wiki/Agaricus_bisporus" title="Agaricus bisporus">Agaricus bisporus</a>.<a href="#cite_note-51">[50]</a> Because of lack of clarity about laws concerning psilocybin mushrooms, specifically in the form of sclerotia (also known as "truffles"), in the late 1990s and early 2000s European retailers commercialized and marketed them in <a href="/wiki/Smartshop" class="mw-redirect" title="Smartshop">smartshops</a> in the Netherlands, the UK, and online. Several websites<a href="#cite_note-52">[b]</a> emerged that contributed to the accessibility of information on the mushrooms' description, use, and effects, and users exchanged mushroom experiences. Since 2001, six <a href="/wiki/EU" class="mw-redirect" title="EU">EU</a> countries have tightened their legislation on psilocybin mushrooms in response to concerns about their prevalence and increasing usage.<a href="#cite_note-EMCDDA-53">[51]</a> In the 1990s, hallucinogens and their effects on human consciousness were again the subject of scientific study, particularly in Europe. Advances in <a href="/wiki/Neuropharmacology" title="Neuropharmacology">neuropharmacology</a> and <a href="/wiki/Neuropsychology" title="Neuropsychology">neuropsychology</a> and the availability of brain imaging techniques have provided impetus for using drugs like psilocybin to probe the "neural underpinnings of psychotic symptom formation including ego disorders and hallucinations".<a href="#cite_note-Studerus2011-54">[52]</a> Recent studies in the U.S. have attracted attention from the popular press and brought psilocybin back into the limelight.<a href="#cite_note-Keim2008-55">[53]</a><a href="#cite_note-Miller2008-56">[54]</a> <div class="mw-heading mw-heading2"><h2 id="Reported_effects">Reported effects</h2>[<a href="/w/index.php?title=Psilocybin&action=edit&section=4" title="Edit section: Reported effects">edit</a>]</div> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:Timothy-Leary-Los-Angeles-1989.jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/c/c7/Timothy-Leary-Los-Angeles-1989.jpg" decoding="async" width="172" height="221" class="mw-file-element" data-file-width="172" data-file-height="221" /></a><figcaption>American psychologist and <a href="/wiki/Counterculture_of_the_1960s" title="Counterculture of the 1960s">counterculture</a> figure <a href="/wiki/Timothy_Leary" title="Timothy Leary">Timothy Leary</a> conducted early experiments into the effects of psychedelic drugs, including psilocybin (1989 photo).</figcaption></figure> The effects of psilocybin are highly variable and depend on the mindset and environment in which the user has the experience: factors commonly referred to as <a href="/wiki/Set_and_setting" title="Set and setting">set and setting</a>. In the early 1960s, <a href="/wiki/Timothy_Leary" title="Timothy Leary">Timothy Leary</a> and colleagues at Harvard University investigated the role of set and setting on the effects of psilocybin. They administered the drug to 175 volunteers (from various backgrounds) in an environment intended to be similar to a comfortable living room. 98 of the subjects were given questionnaires to assess their experiences and the contribution of background and situational factors. Individuals who had experience with psilocybin prior to the study reported more pleasant experiences than those for whom the drug was novel. Group size, dosage, preparation, and expectancy were important determinants of the drug response. In general, those in groups of more than eight felt that the groups were less supportive, and their experiences less pleasant. Conversely, smaller groups (fewer than six) were seen as more supportive and reported more positive reactions to the drug in those groups. Leary and colleagues proposed that psilocybin heightens suggestibility, making an individual more receptive to interpersonal interactions and environmental stimuli.<a href="#cite_note-Leary1963-43">[42]</a> These findings were affirmed in a later review by Jos ten Berge (1999), who concluded that dosage, set, and setting were fundamental factors in determining the outcome of experiments that tested the effects of psychedelic drugs on artists' creativity.<a href="#cite_note-Berge1999-57">[55]</a> After ingesting psilocybin, the user may experience a wide range of emotional effects which can include: feelings of disorientation, lethargy, giddiness, <a href="/wiki/Euphoria" title="Euphoria">euphoria</a>, joy, and <a href="/wiki/Depression_(mood)" title="Depression (mood)">depression</a>. In one study, 31% of volunteers given a high dose reported feelings of significant fear and 17% experienced transient <a href="/wiki/Paranoia" title="Paranoia">paranoia</a>.<a href="#cite_note-Amsterdam2011-58">[56]</a> In studies at <a href="/wiki/Johns_Hopkins_University" title="Johns Hopkins University">Johns Hopkins</a>, among those given a moderate dose (but still enough to "give a high probability of a profound and beneficial experience"), negative experiences were rare, whereas one-third of those given a high dose experienced anxiety or paranoia.<a href="#cite_note-59">[57]</a><a href="#cite_note-Hopkins2011-60">[58]</a> Low doses can induce hallucinatory effects. <a href="/wiki/Closed-eye_hallucination" title="Closed-eye hallucination">Closed-eye hallucinations</a> may occur, where the affected individual sees multicolored geometric shapes and vivid imaginative sequences.<a href="#cite_note-Hasler2004-61">[59]</a> Some individuals report <a href="/wiki/Synesthesia" title="Synesthesia">synesthesia</a>, such as tactile sensations when viewing colors.<a href="#cite_note-Ballesteros_2006-62">[60]</a>: 175  At higher doses, psilocybin can lead to "intensification of <a href="/wiki/Affective" class="mw-redirect" title="Affective">affective</a> responses, enhanced ability for introspection, <a href="/wiki/Regression_(psychology)" title="Regression (psychology)">regression</a> to primitive and childlike thinking, and activation of vivid memory traces with pronounced emotional undertones".<a href="#cite_note-Studerus2011-54">[52]</a> Open-eye visual <a href="/wiki/Hallucination" title="Hallucination">hallucinations</a> are common, and may be very detailed, although <a href="/wiki/Pseudohallucination" title="Pseudohallucination">rarely confused with reality.</a><a href="#cite_note-Hasler2004-61">[59]</a> <div class="mw-heading mw-heading3"><h3 id="Physical_effects">Physical effects</h3>[<a href="/w/index.php?title=Psilocybin&action=edit&section=5" title="Edit section: Physical effects">edit</a>]</div> Common responses include <a href="/wiki/Mydriasis" title="Mydriasis">pupil dilation</a> (93%); changes in <a href="/wiki/Heart_rate" title="Heart rate">heart rate</a> (100%), including increases (56%), decreases (13%), and variable responses (31%); changes in <a href="/wiki/Blood_pressure" title="Blood pressure">blood pressure</a> (84%), including <a href="/wiki/Hypotension" title="Hypotension">hypotension</a> (34%), <a href="/wiki/Hypertension" title="Hypertension">hypertension</a> (28%), and general instability (22%); changes in <a href="/wiki/Stretch_reflex" title="Stretch reflex">stretch reflex</a> (86%), including increases (80%) and decreases (6%); nausea (44%); <a href="/wiki/Tremor" title="Tremor">tremor</a> (25%); and <a href="/wiki/Dysmetria" title="Dysmetria">dysmetria</a> (16%) (inability to properly direct or limit motions).<a href="#cite_note-64">[c]</a> The temporary increases in blood pressure caused by the drug can be a risk factor for users with pre-existing hypertension.<a href="#cite_note-Hasler2004-61">[59]</a> These qualitative somatic effects caused by psilocybin have been corroborated by several early clinical studies.<a href="#cite_note-65">[62]</a> A 2005 magazine survey of clubgoers in the UK found that nausea or vomiting was experienced by over a quarter of those who had used psilocybin mushrooms in the last year, although this effect is caused by the mushroom rather than psilocybin itself.<a href="#cite_note-Amsterdam2011-58">[56]</a> In one study, administration of gradually increasing dosages of psilocybin daily for 21 days had no measurable effect on <a href="/wiki/Electrolyte" title="Electrolyte">electrolyte</a> levels, <a href="/wiki/Blood_sugar" class="mw-redirect" title="Blood sugar">blood sugar</a> levels, or <a href="/wiki/Liver_function_tests" title="Liver function tests">liver toxicity tests</a>.<a href="#cite_note-Passie2002-2">[2]</a> <div class="mw-heading mw-heading3"><h3 id="Psychiatric_effects_and_perceptual_disturbances">Psychiatric effects and perceptual disturbances</h3>[<a href="/w/index.php?title=Psilocybin&action=edit&section=6" title="Edit section: Psychiatric effects and perceptual disturbances">edit</a>]</div> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:Prefrontal_cortex.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/a/ab/Prefrontal_cortex.png/220px-Prefrontal_cortex.png" decoding="async" width="220" height="136" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/ab/Prefrontal_cortex.png/330px-Prefrontal_cortex.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/ab/Prefrontal_cortex.png/440px-Prefrontal_cortex.png 2x" data-file-width="450" data-file-height="278" /></a><figcaption>The ability of psilocybin to cause perceptual distortions is linked to its influence on the activity of the <a href="/wiki/Prefrontal_cortex" title="Prefrontal cortex">prefrontal cortex</a>.</figcaption></figure> Psilocybin is known to strongly influence the subjective experience of the <a href="/wiki/Time_perception" title="Time perception">passage of time</a>.<a href="#cite_note-Heimann1994-66">[63]</a><a href="#cite_note-:1-24">[23]</a> Users often feel as if time is slowed down, resulting in the perception that "minutes appear to be hours" or "time is standing still".<a href="#cite_note-Wittmann2007-67">[64]</a> Studies have demonstrated that psilocybin significantly impairs subjects' ability to gauge time intervals longer than 2.5 seconds, impairs their ability to synchronize to inter-beat intervals longer than 2 seconds, and reduces their preferred <a href="/wiki/Tapping_rate" title="Tapping rate">tapping rate</a>.<a href="#cite_note-Wittmann2007-67">[64]</a><a href="#cite_note-Wackermann2008-68">[65]</a> These results are consistent with the drug's role in affecting <a href="/wiki/Prefrontal_cortex" title="Prefrontal cortex">prefrontal cortex</a> activity,<a href="#cite_note-Carter2005-69">[66]</a> and the role that the prefrontal cortex is known to play in time perception.<a href="#cite_note-Harrington1999-70">[67]</a> However, the neurochemical basis of psilocybin's effects on the perception of time are not known with certainty.<a href="#cite_note-Coull2011-71">[68]</a> Users having a pleasant experience can feel a sense of connection to others, nature, and the universe; other perceptions and emotions are also often intensified. Users having an unpleasant experience (a "<a href="/wiki/Bad_trip" title="Bad trip">bad trip</a>") describe a reaction accompanied by fear, other unpleasant feelings, and occasionally by dangerous behavior. In general, the phrase "bad trip" is used to describe a reaction that is characterized primarily by fear or other unpleasant emotions, not just a transitory experience of such feelings. A variety of factors may contribute to a psilocybin user experiencing a bad trip, including "tripping" during an emotional or physical low or in a non-supportive environment (see: <a href="/wiki/Set_and_setting" title="Set and setting">set and setting</a>). Ingesting psilocybin in combination with other drugs, including <a href="/wiki/Alcohol_(drug)" title="Alcohol (drug)">alcohol</a>, can also increase the likelihood of a bad trip.<a href="#cite_note-Amsterdam2011-58">[56]</a><a href="#cite_note-Attema2007-72">[69]</a> Other than the duration of the experience, the effects of psilocybin are similar to comparable dosages of <a href="/wiki/Lysergic_acid_diethylamide" class="mw-redirect" title="Lysergic acid diethylamide">lysergic acid diethylamide</a> (LSD) or mescaline. However, in the Psychedelics Encyclopedia, author <a href="/wiki/Peter_Stafford" title="Peter Stafford">Peter Stafford</a> noted, "The psilocybin experience seems to be warmer, not as forceful and less isolating. It tends to build connections between people, who are generally much more in communication than when they use LSD."<a href="#cite_note-Stafford1992-42">[41]</a>: 273  <div class="mw-heading mw-heading3"><h3 id="Theory_of_mind_network_and_default_mode_network">Theory of mind network and default mode network</h3>[<a href="/w/index.php?title=Psilocybin&action=edit&section=7" title="Edit section: Theory of mind network and default mode network">edit</a>]</div> Psychedelics, including psilocybin, have been shown to affect different clusters of brain regions known as the "theory of mind network" (ToMN) and the <a href="/wiki/Default_mode_network" title="Default mode network">default mode network</a> (DMN).<a href="#cite_note-:0-73">[70]</a> The ToMN involves making inferences and understanding social situations based on patterns<a href="#cite_note-74">[71]</a> whereas, the DMN relates more to introspection and one's sense of self.<a href="#cite_note-:0-73">[70]</a> The DMN in particular is related to increased rumination and worsening self-image in patients with major depressive disorder (MDD).<a href="#cite_note-75">[72]</a> In studies done with single use psilocybin, areas of the DMN showed decreased functional connectivity (communication between areas of the brain). This provides functional insight into the work of psilocybin in increasing one's sense of connection to one's surroundings, as the areas of the brain involved in introspection decrease in functionality under the effects of the drug.<a href="#cite_note-76">[73]</a> Conversely, areas of the brain involved in the ToMN showed increased activity and functional activation in response to psychedelics. These results were not unique to psilocybin and there was no significant difference in brain activation found in similar trials of mescaline and LSD. Information and studies into the DMN and ToMN are relatively sparse and their connections to other psychiatric illnesses and the use of psychedelics is still largely unknown.<a href="#cite_note-:0-73">[70]</a> <div class="mw-heading mw-heading3"><h3 id="Group_perceptions">Group perceptions</h3>[<a href="/w/index.php?title=Psilocybin&action=edit&section=8" title="Edit section: Group perceptions">edit</a>]</div> Through further <a href="/wiki/Anthropological" class="mw-redirect" title="Anthropological">anthropological</a> studies regarding "personal insights"<a href="#cite_note-77">[74]</a> and the psychosocial effects of psilocybin, it can be seen in many traditional societies that powerful mind-active substances such as psilocybin are regularly "consumed ritually for therapeutic purposes or for transcending normal, everyday reality".<a href="#cite_note-Batchelder_2001-78">[75]</a> Positive effects that psilocybin has on individuals can be observed by taking on an anthropological approach and moving away from the Western biomedical view; this is aided by the studies done by Leary.<a href="#cite_note-79">[76]</a> Within certain traditional societies, where the use of psilocybin is frequent for shamanic healing rituals, group collectives praise their guide, healer and shaman for helping alleviate their pains, aches and hurt. They do this through a group ritual practice where the group, or just the guide, ingests psilocybin to help extract any "toxic psychic residues or sorcerous implants"<a href="#cite_note-Batchelder_2001-78">[75]</a> found in one's body. Group therapies using "classic" psychedelics are becoming more commonly used in the Western world in clinical practice.<a href="#cite_note-80">[77]</a> This is speculated to grow, provided the evidence remains indicative of their safety and efficacy.<a href="#cite_note-81">[78]</a> In social sense, the group is shaped by their experiences surrounding psilocybin and how they view the plant collectively. As mentioned in the anthropology article,<a href="#cite_note-Batchelder_2001-78">[75]</a> the group partakes in a "journey" together, thus adding to the spiritual, social body where roles, hierarchies and gender are subjectively understood.<a href="#cite_note-Batchelder_2001-78">[75]</a> <div class="mw-heading mw-heading3"><h3 id="Adverse_effects">Adverse effects</h3>[<a href="/w/index.php?title=Psilocybin&action=edit&section=9" title="Edit section: Adverse effects">edit</a>]</div> Most of the comparatively few fatal incidents that are associated with psychedelic mushroom usage involve the simultaneous use of other drugs, especially <a href="/wiki/Ethanol" title="Ethanol">alcohol</a>. A common <a href="/wiki/Adverse_effect" title="Adverse effect">adverse effect</a> resulting from psilocybin mushroom use involves "bad trips" or <a href="/wiki/Panic_attack" title="Panic attack">panic reactions</a>, in which affected individuals become anxious, confused, agitated, or disoriented.<a href="#cite_note-nida-82">[79]</a> Accidents, <a href="/wiki/Self-injury" class="mw-redirect" title="Self-injury">self-injury</a>, or <a href="/wiki/Suicide" title="Suicide">suicide</a> attempts can result from serious cases of acute <a href="/wiki/Psychotic_episodes" class="mw-redirect" title="Psychotic episodes">psychotic episodes</a>.<a href="#cite_note-Amsterdam2011-58">[56]</a> Although no studies have linked psilocybin with <a href="/wiki/Birth_defects" class="mw-redirect" title="Birth defects">birth defects</a>,<a href="#cite_note-Pagliaro2012-83">[80]</a> it is recommended that pregnant women avoid its usage.<a href="#cite_note-Schaefer2001-84">[81]</a> <div class="mw-heading mw-heading4"><h4 id="Toxicity">Toxicity</h4>[<a href="/w/index.php?title=Psilocybin&action=edit&section=10" title="Edit section: Toxicity">edit</a>]</div> Psilocybin has low <a href="/wiki/Toxicity" title="Toxicity">toxicity</a>, indicating that it has low potential for inducing life-threatening events like breathing or heart problems.<a href="#cite_note-nida-82">[79]</a> Research shows that health risks may develop with use of psilocybin. Nonetheless, hospitalizations from it are rare, and overdoses are generally mild and self-limiting.<a href="#cite_note-nida-82">[79]</a> A review regarding the management of psychedelic overdoses suggested that psilocybin-related overdose management should prioritize managing the immediate adverse effects, such as anxiety and paranoia, rather than specific pharmacological interventions, as psilocybin's physiological toxicity tends to be rather limited.<a href="#cite_note-Reinert2020-85">[82]</a> One analysis of people hospitalized from psilocybin poisoning found high urine concentrations of <a href="/wiki/Phenethylamine" title="Phenethylamine">phenethylamine</a> (PEA), indicating that PEA may contribute to the effects of psilocybin poisoning.<a href="#cite_note-Reinert2020-85">[82]</a> In rats, the <a href="/wiki/Median_lethal_dose" title="Median lethal dose">median lethal dose</a> (LD50) when administered orally is 280 milligrams per kilogram (mg/kg), approximately one and a half times that of <a href="/wiki/Caffeine" title="Caffeine">caffeine</a>. The lethal dose of psilocybin when administered <a href="/wiki/Intravenously" class="mw-redirect" title="Intravenously">intravenously</a> in mice is 285 mg/kg and in rats is 280 mg/kg.<a href="#cite_note-Merck-21">[21]</a> When administered <a href="/wiki/Intravenously" class="mw-redirect" title="Intravenously">intravenously</a> in rabbits, psilocybin's LD50 is approximately 12.5 mg/kg.<a href="#cite_note-Merck13th-86">[83]</a> Psilocybin comprises approximately 1% of the weight of Psilocybe cubensis mushrooms, and so nearly 1.7 kilograms (3.7 lb) of dried mushrooms, or 17 kilograms (37 lb) of fresh mushrooms, would be required for a 60-kilogram (130 lb) person to reach the 280 mg/kg LD50 value of rats.<a href="#cite_note-Amsterdam2011-58">[56]</a> Based on the results of animal studies, the <a href="/wiki/Lethal_dose" title="Lethal dose">lethal dose</a> of psilocybin has been extrapolated to be 6 grams, 1000 times greater than the <a href="/wiki/Effective_dose_(pharmacology)" title="Effective dose (pharmacology)">effective dose</a> of 6 milligrams.<a href="#cite_note-Gable2004-87">[84]</a> The <a href="/wiki/Registry_of_Toxic_Effects_of_Chemical_Substances" title="Registry of Toxic Effects of Chemical Substances">Registry of Toxic Effects of Chemical Substances</a> assigns psilocybin a relatively high <a href="/wiki/Therapeutic_index" title="Therapeutic index">therapeutic index</a> of 641 (higher values correspond to a better safety profile); for comparison, the therapeutic indices of <a href="/wiki/Aspirin" title="Aspirin">aspirin</a> and <a href="/wiki/Nicotine" title="Nicotine">nicotine</a> are 199 and 21, respectively.<a href="#cite_note-Strassman2008-88">[85]</a> The lethal dose from psilocybin toxicity alone is unknown, and has rarely been documented—as of 2011<a class="external text" href="https://en.wikipedia.org/w/index.php?title=Psilocybin&action=edit">[update]</a>, only two cases attributed to overdosing on hallucinogenic mushrooms (without concurrent use of other drugs) have been reported in the scientific literature and may involve other factors aside from psilocybin.<a href="#cite_note-Amsterdam2011-58">[56]</a><a href="#cite_note-91">[d]</a> <div class="mw-heading mw-heading4"><h4 id="Psychiatric">Psychiatric</h4>[<a href="/w/index.php?title=Psilocybin&action=edit&section=11" title="Edit section: Psychiatric">edit</a>]</div> Panic reactions can occur after consumption of psilocybin-containing mushrooms, especially if the ingestion is accidental or otherwise unexpected. Reactions characterized by violent behavior, suicidal thoughts,<a href="#cite_note-Peden1982-92">[88]</a> schizophrenia-like <a href="/wiki/Psychosis" title="Psychosis">psychosis</a>,<a href="#cite_note-Vollenweider1998-93">[89]</a><a href="#cite_note-Hyde1978-94">[90]</a> and <a href="/wiki/Convulsion" title="Convulsion">convulsions</a><a href="#cite_note-Mack1983-95">[91]</a> have been reported in the literature. A 2005 survey, conducted in the United Kingdom, found that almost a quarter of those who had used psilocybin mushrooms in the past year had experienced a panic attack.<a href="#cite_note-Amsterdam2011-58">[56]</a> [<a href="/wiki/Wikipedia:Verifiability" title="Wikipedia:Verifiability">failed verification</a>] Other adverse effects, less frequently reported, include paranoia, <a href="/wiki/Confusion" title="Confusion">confusion</a>, prolonged <a href="/wiki/Derealization" title="Derealization">derealization</a> (disconnection from reality), and <a href="/wiki/Mania" title="Mania">mania</a>.<a href="#cite_note-CarhartHarris2010-96">[92]</a> Psilocybin usage can temporarily induce a state of <a href="/wiki/Depersonalization-derealization_disorder" title="Depersonalization-derealization disorder">depersonalization disorder</a>.<a href="#cite_note-Simeon2011-97">[93]</a> Usage by those with <a href="/wiki/Schizophrenia" title="Schizophrenia">schizophrenia</a> can induce acute psychotic states requiring hospitalization.<a href="#cite_note-98">[94]</a> The similarity of psilocybin-induced symptoms to those of schizophrenia has made the drug a useful research tool in behavioral and <a href="/wiki/Neuroimaging" title="Neuroimaging">neuroimaging</a> studies of this psychotic disorder.<a href="#cite_note-Geyer1998-99">[95]</a><a href="#cite_note-Vollenweider2001-100">[96]</a><a href="#cite_note-Geyer2008-101">[97]</a> In both cases, psychotic symptoms are thought to arise from a "deficient gating of sensory and cognitive information" in the brain that ultimately lead to "cognitive fragmentation and psychosis".<a href="#cite_note-Vollenweider2001-100">[96]</a> <a href="/wiki/Flashback_(psychology)" title="Flashback (psychology)">Flashbacks</a> (spontaneous recurrences of a previous psilocybin experience) can occur long after having used psilocybin mushrooms. <a href="/wiki/Hallucinogen_persisting_perception_disorder" title="Hallucinogen persisting perception disorder">Hallucinogen persisting perception disorder</a> (HPPD) is characterized by a continual presence of visual disturbances similar to those generated by psychedelic substances. Neither flashbacks nor HPPD are commonly associated with psilocybin usage,<a href="#cite_note-Amsterdam2011-58">[56]</a> and correlations between HPPD and psychedelics are further obscured by <a href="/wiki/Polydrug_use" class="mw-redirect" title="Polydrug use">polydrug use</a> and other variables.<a href="#cite_note-Myers1998-102">[98]</a> <div class="mw-heading mw-heading4"><h4 id="Tolerance_and_dependence">Tolerance and dependence</h4>[<a href="/w/index.php?title=Psilocybin&action=edit&section=12" title="Edit section: Tolerance and dependence">edit</a>]</div> <figure class="skin-invert-image" typeof="mw:File/Thumb"><a href="/wiki/File:Drug_danger_and_dependence-no_title.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/9/9d/Drug_danger_and_dependence-no_title.svg/600px-Drug_danger_and_dependence-no_title.svg.png" decoding="async" width="600" height="271" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/9/9d/Drug_danger_and_dependence-no_title.svg/900px-Drug_danger_and_dependence-no_title.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/9/9d/Drug_danger_and_dependence-no_title.svg/1200px-Drug_danger_and_dependence-no_title.svg.png 2x" data-file-width="870" data-file-height="393" /></a><figcaption>Chart of dependence potential and effective dose/lethal dose ratio of several <a href="/wiki/Psychoactive_drug" title="Psychoactive drug">psychoactive drugs</a>.<a href="#cite_note-Fish2006-103">[99]</a></figcaption></figure> <a href="/wiki/Drug_tolerance" title="Drug tolerance">Tolerance</a> to psilocybin builds and dissipates quickly; ingesting psilocybin more than about once a week can lead to diminished effects. Tolerance dissipates after a few days, so doses can be spaced several days apart to avoid the effect.<a href="#cite_note-Nicholas2006-6">[6]</a> A <a href="/wiki/Cross-tolerance" title="Cross-tolerance">cross-tolerance</a> can develop between psilocybin and the pharmacologically similar LSD,<a href="#cite_note-Passie2008-104">[100]</a> and between psilocybin and <a href="/wiki/Phenethylamine" title="Phenethylamine">phenethylamines</a> such as <a href="/wiki/Mescaline" title="Mescaline">mescaline</a> and <a href="/wiki/2,5-dimethoxy-4-methylamphetamine" class="mw-redirect" title="2,5-dimethoxy-4-methylamphetamine">DOM</a>.<a href="#cite_note-HalberstadtGeyer2011-105">[101]</a> Repeated use of psilocybin does not lead to <a href="/wiki/Physical_dependence" title="Physical dependence">physical dependence</a>.<a href="#cite_note-Passie2002-2">[2]</a> A 2008 study concluded that, based on US data from the period 2000–2002, adolescent-onset (defined here as ages 11–17) usage of hallucinogenic drugs (including psilocybin) did not increase the risk of <a href="/wiki/Drug_dependence" class="mw-redirect" title="Drug dependence">drug dependence</a> in adulthood; this was in contrast to adolescent usage of <a href="/wiki/Cannabis_(drug)" title="Cannabis (drug)">cannabis</a>, <a href="/wiki/Cocaine" title="Cocaine">cocaine</a>, <a href="/wiki/Inhalant" title="Inhalant">inhalants</a>, <a href="/wiki/Anxiolytic" title="Anxiolytic">anxiolytic</a> medicines, and <a href="/wiki/Stimulant" title="Stimulant">stimulants</a>, all of which were associated with "an excess risk of developing clinical features associated with drug dependence".<a href="#cite_note-Chen2008-3">[3]</a> Likewise, a 2010 Dutch study ranked the relative harm of psilocybin mushrooms compared to a selection of 19 <a href="/wiki/Recreational_drugs" class="mw-redirect" title="Recreational drugs">recreational drugs</a>, including alcohol, cannabis, cocaine, <a href="/wiki/MDMA" title="MDMA">ecstasy</a>, <a href="/wiki/Heroin" title="Heroin">heroin</a>, and <a href="/wiki/Tobacco" title="Tobacco">tobacco</a>. Psilocybin mushrooms were ranked as the illicit drug with the lowest harm,<a href="#cite_note-Amsterdam2010-4">[4]</a> corroborating conclusions reached earlier by expert groups in the United Kingdom.<a href="#cite_note-Nutt2010-5">[5]</a> <div class="mw-heading mw-heading2"><h2 id="Cultural_significance_and_"mystical"_experiences">Cultural significance and "mystical" experiences</h2>[<a href="/w/index.php?title=Psilocybin&action=edit&section=13" title="Edit section: Cultural significance and "mystical" experiences">edit</a>]</div> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:Johns_Hopkins_psilocybin_session_room-SessionRm_2176x.jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/9/90/Johns_Hopkins_psilocybin_session_room-SessionRm_2176x.jpg/220px-Johns_Hopkins_psilocybin_session_room-SessionRm_2176x.jpg" decoding="async" width="220" height="165" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/9/90/Johns_Hopkins_psilocybin_session_room-SessionRm_2176x.jpg/330px-Johns_Hopkins_psilocybin_session_room-SessionRm_2176x.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/9/90/Johns_Hopkins_psilocybin_session_room-SessionRm_2176x.jpg/440px-Johns_Hopkins_psilocybin_session_room-SessionRm_2176x.jpg 2x" data-file-width="2048" data-file-height="1536" /></a><figcaption>In their studies on the psilocybin experience, Johns Hopkins researchers use peaceful music and a comfortable room to help ensure a comfortable setting, and experienced guides to monitor and reassure the volunteers.</figcaption></figure> Psilocybin mushrooms have been and continue to be used in <a href="/wiki/Indigenous_peoples_of_the_Americas" title="Indigenous peoples of the Americas">Indigenous American</a> cultures in religious, <a href="/wiki/Divinatory" class="mw-redirect" title="Divinatory">divinatory</a>, or <a href="/wiki/Spirituality" title="Spirituality">spiritual</a> contexts. Reflecting the meaning of the word <a href="/wiki/Entheogen" title="Entheogen">entheogen</a> ("the god within"), the mushrooms are revered as powerful spiritual <a href="/wiki/Sacrament" title="Sacrament">sacraments</a> that provide access to sacred worlds. Typically used in small group community settings, they enhance <a href="/wiki/Group_cohesion" class="mw-redirect" title="Group cohesion">group cohesion</a> and reaffirm traditional values.<a href="#cite_note-Winkelman2007-106">[102]</a> <a href="/wiki/Terence_McKenna" title="Terence McKenna">Terence McKenna</a> documented the worldwide practices of psilocybin mushroom usage as part of a cultural <a href="/wiki/Ethos" title="Ethos">ethos</a> relating to the Earth and mysteries of nature, and suggested that mushrooms enhanced <a href="/wiki/Self-awareness" title="Self-awareness">self-awareness</a> and a sense of contact with a "Transcendent Other"—reflecting a deeper understanding of our connectedness with nature.<a href="#cite_note-McKenna1992-107">[103]</a> Psychedelic drugs can induce states of <a href="/wiki/Consciousness" title="Consciousness">consciousness</a> that have lasting personal meaning and spiritual significance in individuals who are religious or spiritually inclined; these states are called <a href="/wiki/Mystical_experience" class="mw-redirect" title="Mystical experience">mystical experiences</a>. Some scholars have proposed that many of the qualities of a drug-induced mystical experience are indistinguishable from mystical experiences achieved through <a href="/wiki/Religious_experience#Causes_of_religious_experiences" title="Religious experience">non-drug techniques</a>, such as meditation or <a href="/wiki/Holotropic_breathwork" class="mw-redirect" title="Holotropic breathwork">holotropic breathwork</a>.<a href="#cite_note-James1997-108">[104]</a><a href="#cite_note-Metzner1998-109">[105]</a> In the 1960s, <a href="/wiki/Walter_Pahnke" title="Walter Pahnke">Walter Pahnke</a> and colleagues systematically evaluated mystical experiences (which they called "mystical consciousness") by categorizing their common features. These categories, according to Pahnke, "describe the core of a universal psychological experience, free from culturally determined philosophical or theological interpretations", and allow researchers to assess mystical experiences on a qualitative, numerical scale.<a href="#cite_note-Pahnke1969-110">[106]</a> In the 1962 <a href="/wiki/Marsh_Chapel_Experiment" title="Marsh Chapel Experiment">Marsh Chapel Experiment</a>, which was run by Pahnke at the <a href="/wiki/Harvard_Divinity_School" title="Harvard Divinity School">Harvard Divinity School</a> under the supervision of Timothy Leary,<a href="#cite_note-Pahnke1966-111">[107]</a> almost all of the graduate degree <a href="/wiki/Seminary" title="Seminary">divinity</a> student volunteers who received psilocybin reported profound religious experiences.<a href="#cite_note-Griffiths2008-112">[108]</a> One of the participants was religious scholar <a href="/wiki/Huston_Smith" title="Huston Smith">Huston Smith</a>, author of several textbooks on <a href="/wiki/Comparative_religion" title="Comparative religion">comparative religion</a>; he later described his experience as "the most powerful cosmic homecoming I have ever experienced."<a href="#cite_note-Smith2000-113">[109]</a> In a 25-year followup to the experiment, all of the subjects given psilocybin described their experience as having elements of "a genuine mystical nature and characterized it as one of the high points of their spiritual life".<a href="#cite_note-Doblin_1991-114">[110]</a>: 13  Psychedelic researcher <a href="/wiki/Rick_Doblin" title="Rick Doblin">Rick Doblin</a> considered the study partially flawed due to incorrect implementation of the <a href="/wiki/Double-blind" class="mw-redirect" title="Double-blind">double-blind</a> procedure, and several imprecise questions in the mystical experience questionnaire. Nevertheless, he said that the study cast "a considerable doubt on the assertion that mystical experiences catalyzed by drugs are in any way inferior to non-drug mystical experiences in both their immediate content and long-term effects".<a href="#cite_note-Doblin_1991-114">[110]</a>: 24  This sentiment was echoed by psychiatrist William A. Richards, who in a 2007 review stated "[psychedelic] mushroom use may constitute one technology for evoking revelatory experiences that are similar, if not identical, to those that occur through so-called spontaneous alterations of brain chemistry."<a href="#cite_note-Richards2008-115">[111]</a> A group of researchers from <a href="/wiki/Johns_Hopkins_School_of_Medicine" title="Johns Hopkins School of Medicine">Johns Hopkins School of Medicine</a> led by <a href="/wiki/Roland_Griffiths" title="Roland Griffiths">Roland Griffiths</a> conducted a study to assess the immediate and long-term psychological effects of the psilocybin experience, using a modified version of the mystical experience questionnaire and a rigorous double-blind procedure.<a href="#cite_note-Griffiths2006-116">[112]</a> When asked in an interview about the similarity of his work with Leary's, Griffiths explained the difference: "We are conducting rigorous, systematic research with psilocybin under carefully monitored conditions, a route which Dr. Leary abandoned in the early 1960s."<a href="#cite_note-JHMed:_Griffiths_Interview-117">[113]</a> The <a href="/wiki/National_Institute_of_Drug_Abuse" class="mw-redirect" title="National Institute of Drug Abuse">National Institute of Drug Abuse</a>-funded study, published in 2006, has been praised by experts for the soundness of its experimental design.<a href="#cite_note-118">[e]</a> In the experiment, 36 volunteers without prior experience with hallucinogens were given psilocybin and <a href="/wiki/Methylphenidate" title="Methylphenidate">methylphenidate</a> (Ritalin) in separate sessions; the methylphenidate sessions served as a <a href="/wiki/Scientific_control" title="Scientific control">control</a> and psychoactive <a href="/wiki/Placebo" title="Placebo">placebo</a>. The degree of mystical experience was measured using a questionnaire developed by Ralph W. Hood;<a href="#cite_note-Hood1975-119">[114]</a> 61% of subjects reported a "complete mystical experience" after their psilocybin session, while only 13% reported such an outcome after their experience with methylphenidate. Two months after taking psilocybin, 79% of the participants reported moderately to greatly increased <a href="/wiki/Life_satisfaction" title="Life satisfaction">life satisfaction</a> and sense of well-being. About 36% of participants also had a strong to extreme "experience of fear" or <a href="/wiki/Dysphoria" title="Dysphoria">dysphoria</a> (i.e., a "bad trip") at some point during the psilocybin session (which was not reported by any subject during the methylphenidate session); about one-third of these (13% of the total) reported that this dysphoria dominated the entire session. These negative effects were reported to be easily managed by the researchers and did not have a lasting negative effect on the subject's sense of well-being.<a href="#cite_note-urlMedical_News-120">[115]</a> A follow-up study conducted 14 months after the original psilocybin session confirmed that participants continued to attribute deep personal meaning to the experience. Almost one-third of the subjects reported that the experience was the single most meaningful or spiritually significant event of their lives, and over two-thirds reported it among their five most spiritually significant events. About two-thirds indicated that the experience increased their sense of well-being or life satisfaction.<a href="#cite_note-Griffiths2008-112">[108]</a> Even after 14 months, those who reported mystical experiences scored on average 4 percentage points higher on the personality trait of <a href="/wiki/Openness_to_experience" title="Openness to experience">Openness/Intellect</a>; personality traits are normally stable across the lifespan for adults. Likewise, in a recent (2010) web-based questionnaire study designed to investigate user perceptions of the benefits and harms of hallucinogenic drug use, 60% of the 503 psilocybin users reported that their use of psilocybin had a long-term positive impact on their sense of well-being.<a href="#cite_note-Amsterdam2011-58">[56]</a><a href="#cite_note-CarhartHarris2010-96">[92]</a> While many recent studies have concluded that psilocybin can cause mystical-type experiences having substantial and sustained personal meaning and spiritual significance, not all the medical community agree. <a href="/wiki/Paul_R._McHugh" title="Paul R. McHugh">Paul R. McHugh</a>, formerly director of the Department of Psychiatry and Behavioral Science at Johns Hopkins, responded as follows in a book review: "The unmentioned fact in The Harvard Psychedelic Club is that LSD, psilocybin, mescaline, and the like produce not a "higher consciousness" but rather a particular kind of "lower consciousness" known well to psychiatrists and neurologists—namely, '<a href="/wiki/Toxic" class="mw-redirect" title="Toxic">toxic</a> <a href="/wiki/Delirium" title="Delirium">delirium</a>.'"<a href="#cite_note-121">[116]</a> <div class="mw-heading mw-heading3"><h3 id="Available_forms">Available forms</h3>[<a href="/w/index.php?title=Psilocybin&action=edit&section=14" title="Edit section: Available forms">edit</a>]</div> Although psilocybin may be prepared synthetically, outside of the research setting it is not typically used in this form. The psilocybin present in certain species of mushrooms can be ingested in several ways: by consuming fresh or dried fruit bodies, by preparing an <a href="/wiki/Herbal_tea" title="Herbal tea">herbal tea</a>, or by combining with other foods to mask the bitter taste.<a href="#cite_note-EMCDDA-53">[51]</a> In rare cases people have injected mushroom extracts <a href="/wiki/Intravenous" class="mw-redirect" title="Intravenous">intravenously</a>.<a href="#cite_note-Amsterdam2011-58">[56]</a> <div class="mw-heading mw-heading2"><h2 id="Chemistry">Chemistry</h2>[<a href="/w/index.php?title=Psilocybin&action=edit&section=15" title="Edit section: Chemistry">edit</a>]</div> <div class="mw-heading mw-heading3"><h3 id="Physical_properties">Physical properties</h3>[<a href="/w/index.php?title=Psilocybin&action=edit&section=16" title="Edit section: Physical properties">edit</a>]</div> <figure class="skin-invert-image" typeof="mw:File/Thumb"><a href="/wiki/File:Serotonin.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/f/f0/Serotonin.svg/200px-Serotonin.svg.png" decoding="async" width="200" height="145" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/f/f0/Serotonin.svg/300px-Serotonin.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/f/f0/Serotonin.svg/400px-Serotonin.svg.png 2x" data-file-width="512" data-file-height="372" /></a><figcaption>The neurotransmitter <a href="/wiki/Serotonin" title="Serotonin">serotonin</a> is structurally similar to psilocybin.</figcaption></figure> Psilocybin is a naturally-occurring <a href="/wiki/Substituted_tryptamine" title="Substituted tryptamine">substituted tryptamine</a> that features an <a href="/wiki/Indole" title="Indole">indole</a> ring linked to an <a href="/wiki/Ethylamine" title="Ethylamine">aminoethyl</a> <a href="/wiki/Substituent" title="Substituent">substituent</a>. It is structurally related to <a href="/wiki/Serotonin" title="Serotonin">serotonin</a>, a <a href="/wiki/Monoamine_neurotransmitter" title="Monoamine neurotransmitter">monoamine neurotransmitter</a> which is a derivative of the <a href="/wiki/Amino_acid" title="Amino acid">amino acid</a> <a href="/wiki/Tryptophan" title="Tryptophan">tryptophan</a>. Psilocybin is a member of the general class of tryptophan-based compounds that originally functioned as <a href="/wiki/Antioxidant" title="Antioxidant">antioxidants</a> in earlier life forms before assuming more complex functions in multicellular organisms, including humans.<a href="#cite_note-Azmitia2010-122">[117]</a> Other related indole-containing psychedelic compounds include <a href="/wiki/Dimethyltryptamine" class="mw-redirect" title="Dimethyltryptamine">dimethyltryptamine</a>, found in many plant species and in trace amounts in some mammals, and <a href="/wiki/Bufotenin" title="Bufotenin">bufotenin</a>, found in the skin of certain amphibians, especially the <a href="/wiki/Colorado_River_toad" title="Colorado River toad">Colorado River toad</a>.<a href="#cite_note-Wurst2002-123">[118]</a>: 10–13  Psilocybin is a white, crystalline solid that is soluble in water, <a href="/wiki/Methanol" title="Methanol">methanol</a> and <a href="/wiki/Ethanol" title="Ethanol">ethanol</a> but insoluble in nonpolar organic <a href="/wiki/Solvent" title="Solvent">solvents</a> such as <a href="/wiki/Chloroform" title="Chloroform">chloroform</a> and <a href="/wiki/Petroleum_ether" title="Petroleum ether">petroleum ether</a>.<a href="#cite_note-Wurst2002-123">[118]</a>: 15  It has a <a href="/wiki/Melting_point" title="Melting point">melting point</a> between 220 and 228 °C (428 and 442 °F),<a href="#cite_note-Merck13th-86">[83]</a> and an <a href="/wiki/Ammonia" title="Ammonia">ammonia</a>-like taste.<a href="#cite_note-HSDB-124">[119]</a> Its <a href="/wiki/PKa" class="mw-redirect" title="PKa">pKa</a> values are estimated to be 1.3 and 6.5 for the two successive <a href="/wiki/Phosphate" title="Phosphate">phosphate</a> <a href="/wiki/Hydroxy_group" title="Hydroxy group">hydroxy groups</a> and 10.4 for the <a href="/wiki/Dimethylamine" title="Dimethylamine">dimethylamine</a> nitrogen, so it typically exists as a <a href="/wiki/Zwitterion" title="Zwitterion">zwitterionic</a> structure.<a href="#cite_note-HSDB-124">[119]</a> There are two known crystalline polymorphs of psilocybin, as well as reported <a href="/wiki/Water_of_crystallization" title="Water of crystallization">hydrated phases</a>.<a href="#cite_note-125">[120]</a> Psilocybin rapidly oxidizes upon exposure to light—an important consideration when using it as an analytical <a href="/wiki/Standard_solution" title="Standard solution">standard</a>.<a href="#cite_note-Anastos2006-126">[121]</a> <div class="mw-heading mw-heading3"><h3 id="Structural_analogues">Structural analogues</h3>[<a href="/w/index.php?title=Psilocybin&action=edit&section=17" title="Edit section: Structural analogues">edit</a>]</div> <a href="/wiki/Structural_analogue" class="mw-redirect" title="Structural analogue">Structural analogues</a> of psilocybin (4-PO-DMT; O-phosphorylpsilocin) and <a href="/wiki/Psilocin" title="Psilocin">psilocin</a> (4-HO-DMT) include <a href="/wiki/Dimethyltryptamine" class="mw-redirect" title="Dimethyltryptamine">dimethyltryptamine</a> (DMT), <a href="/wiki/5-hydroxytryptamine" class="mw-redirect" title="5-hydroxytryptamine">5-hydroxytryptamine</a> (5-HT), <a href="/wiki/Bufotenin" title="Bufotenin">bufotenin</a> (5-HO-DMT), <a href="/wiki/4-AcO-DMT" title="4-AcO-DMT">4-AcO-DMT</a> (psilacetin; O-acetylpsilocin), <a href="/wiki/4-PrO-DMT" title="4-PrO-DMT">4-PrO-DMT</a> (O-propionylpsilocin), <a href="/wiki/Psilomethoxin" title="Psilomethoxin">psilomethoxin</a> (4-HO-5-MeO-DMT; 5-methoxypsilocin), <a href="/wiki/Ethocybin" title="Ethocybin">ethocybin</a> (4-PO-DET), <a href="/wiki/Baeocystin" title="Baeocystin">baeocystin</a> (4-PO-NMT), <a href="/wiki/Aeruginascin" title="Aeruginascin">aeruginascin</a> (4-PO-TMT), and <a href="/wiki/Norbaeocystin" title="Norbaeocystin">norbaeocystin</a> (4-PO-T), among others. <div class="mw-heading mw-heading3"><h3 id="Laboratory_synthesis">Laboratory synthesis</h3>[<a href="/w/index.php?title=Psilocybin&action=edit&section=18" title="Edit section: Laboratory synthesis">edit</a>]</div> <a href="/wiki/Albert_Hofmann" title="Albert Hofmann">Albert Hofmann</a> et al. were the first team to synthesize psilocybin in 1958. Since that time, various chemists have improved the methods for the laboratory synthesis and purification of psilocybin. In particular, Shirota et al. reported a novel method in 2003 for the synthesis of psilocybin at the gram scale from 4-hydroxyindole that does not require <a href="/wiki/Chromatographic" class="mw-redirect" title="Chromatographic">chromatographic</a> purification. Fricke et al. described an enzymatic pathway for the synthesis of psilocybin and psilocin, publishing their results in 2017. Sherwood et al. significantly improved upon Shirota's method (producing at the kilogram scale while employing less expensive reagents), publishing their results in 2020.<a href="#cite_note-Serreau2023-127">[122]</a> <div class="mw-heading mw-heading3"><h3 id="Biosynthesis">Biosynthesis</h3>[<a href="/w/index.php?title=Psilocybin&action=edit&section=19" title="Edit section: Biosynthesis">edit</a>]</div> <a href="/wiki/Isotopic_labeling" title="Isotopic labeling">Isotopic labeling</a> experiments from the 1960s suggested that the <a href="/wiki/Biosynthesis" title="Biosynthesis">biosynthesis</a> of psilocybin was a four-step process:<a href="#cite_note-Agurell1968-128">[123]</a> <ol><li><a href="/wiki/Decarboxylation" title="Decarboxylation">Decarboxylation</a> of <a href="/wiki/Tryptophan" title="Tryptophan">tryptophan</a> to <a href="/wiki/Tryptamine" title="Tryptamine">tryptamine</a></li> <li>N,N-Dimethylation of tryptamine at the N9 position to <a href="/wiki/Dimethyltryptamine" class="mw-redirect" title="Dimethyltryptamine">dimethyltryptamine</a></li> <li>4-<a href="/wiki/Hydroxylation" title="Hydroxylation">Hydroxylation</a> of dimethyltryptamine to <a href="/wiki/Psilocin" title="Psilocin">psilocin</a></li> <li>O-<a href="/wiki/Phosphorylation" title="Phosphorylation">Phosphorylation</a> of psilocin to psilocybin</li></ol> This process can be seen in the following diagram:<a href="#cite_note-Fricke2017-129">[124]</a> <figure class="mw-default-size mw-halign-center skin-invert-image" typeof="mw:File/Thumb"><a href="/wiki/File:Biosynthesis_of_psilocybin.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/9/9b/Biosynthesis_of_psilocybin.svg/550px-Biosynthesis_of_psilocybin.svg.png" decoding="async" width="550" height="122" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/9/9b/Biosynthesis_of_psilocybin.svg/825px-Biosynthesis_of_psilocybin.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/9/9b/Biosynthesis_of_psilocybin.svg/1100px-Biosynthesis_of_psilocybin.svg.png 2x" data-file-width="512" data-file-height="114" /></a><figcaption>Biosynthetic route previously thought to lead to psilocybin. It has recently been shown that 4-hydroxylation and O-phosphorylation immediately follow decarboxylation, and neither dimethyltryptamine nor psilocin are intermediates, although spontaneously generated psilocin can be converted back to psilocybin.<a href="#cite_note-Fricke2017-129">[124]</a></figcaption></figure><div style="clear:left;" class=""></div> More recent research has demonstrated that—at least in P. cubensis—O-phosphorylation is in fact the third step, and that neither dimethyltryptamine nor psilocin are intermediates.<a href="#cite_note-Fricke2017-129">[124]</a> The sequence of the intermediate steps has been shown to involve four enzymes (PsiD, PsiH, PsiK, and PsiM) in P. cubensis and P. cyanescens, although it is possible that the biosynthetic pathway differs between species.<a href="#cite_note-Wurst2002-123">[118]</a>: 12–13 <a href="#cite_note-Fricke2017-129">[124]</a> These enzymes are encoded in <a href="/wiki/Metabolic_gene_cluster" title="Metabolic gene cluster">gene clusters</a> in Psilocybe, Panaeolus, and Gymnopilus.<a href="#cite_note-Reynolds2018-130">[125]</a> <a href="/wiki/Escherichia_coli" title="Escherichia coli">Escherichia coli</a> has been genetically modified to manufacture large amounts of psilocybin.<a href="#cite_note-131">[126]</a> Psilocybin can be produced de novo in GM yeast.<a href="#cite_note-Milne2020-132">[127]</a><a href="#cite_note-Wong2022-133">[128]</a> <div class="mw-heading mw-heading2"><h2 id="Pharmacology">Pharmacology</h2>[<a href="/w/index.php?title=Psilocybin&action=edit&section=20" title="Edit section: Pharmacology">edit</a>]</div> <div class="mw-heading mw-heading3"><h3 id="Pharmacodynamics">Pharmacodynamics</h3>[<a href="/w/index.php?title=Psilocybin&action=edit&section=21" title="Edit section: Pharmacodynamics">edit</a>]</div> <table class="wikitable sortable floatright" style="font-size:small;"> <caption>Psilocin at molecular targets </caption> <tbody><tr> <th>Target</th> <th>Affinity (Ki, nM) </th></tr> <tr> <td><a href="/wiki/5-HT1A_receptor" title="5-HT1A receptor">5-HT1A</a></td> <td>49–567 </td></tr> <tr> <td><a href="/wiki/5-HT1B_receptor" title="5-HT1B receptor">5-HT1B</a></td> <td>31–305 </td></tr> <tr> <td><a href="/wiki/5-HT1D_receptor" title="5-HT1D receptor">5-HT1D</a></td> <td>19–36 </td></tr> <tr> <td><a href="/wiki/5-HT1E_receptor" title="5-HT1E receptor">5-HT1E</a></td> <td>44 </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>6.0–340 (Ki) 2.4–721 (<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) 16–98% (<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-HT2B_receptor" title="5-HT2B receptor">5-HT2B</a></td> <td>4.6–410 (Ki) 2.4–>20,000 (<abbr title="half-maximal effective concentration">EC50</abbr>) 38–84% (<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>10–141 </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>70–84 </td></tr> <tr> <td><a href="/wiki/5-HT6_receptor" title="5-HT6 receptor">5-HT6</a></td> <td>57–72 </td></tr> <tr> <td><a href="/wiki/5-HT7_receptor" title="5-HT7 receptor">5-HT7</a></td> <td>3.5–72 </td></tr> <tr> <td><a href="/wiki/Alpha-1A_adrenergic_receptor" title="Alpha-1A adrenergic receptor">α1A</a>–<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-2A_adrenergic_receptor" title="Alpha-2A adrenergic receptor">α2A</a></td> <td>2,044 </td></tr> <tr> <td><a href="/wiki/Alpha-2B_adrenergic_receptor" title="Alpha-2B adrenergic receptor">α2B</a></td> <td>1,271 </td></tr> <tr> <td><a href="/wiki/Alpha-2C_adrenergic_receptor" title="Alpha-2C adrenergic receptor">α2C</a></td> <td>4,404 </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>20–>14,000 </td></tr> <tr> <td><a href="/wiki/D2_receptor" class="mw-redirect" title="D2 receptor">D2</a></td> <td>3,700–>10,000 </td></tr> <tr> <td><a href="/wiki/D3_receptor" class="mw-redirect" title="D3 receptor">D3</a></td> <td>101–8,900 </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>1,600–>10,000 </td></tr> <tr> <td><a href="/wiki/H2_receptor" class="mw-redirect" title="H2 receptor">H2</a>–<a href="/wiki/H4_receptor" class="mw-redirect" title="H4 receptor">H4</a></td> <td>>10,000 </td></tr> <tr> <td><a href="/wiki/Muscarinic_acetylcholine_M1_receptor" class="mw-redirect" title="Muscarinic acetylcholine M1 receptor">M1</a>–<a href="/wiki/Muscarinic_acetylcholine_M5_receptor" class="mw-redirect" title="Muscarinic acetylcholine M5 receptor">M5</a></td> <td>>10,000 </td></tr> <tr> <td><a href="/wiki/Sigma-1_receptor" title="Sigma-1 receptor">σ1</a></td> <td>>10,000 </td></tr> <tr> <td><a href="/wiki/Sigma-2_receptor" title="Sigma-2 receptor">σ2</a></td> <td>>10,000 </td></tr> <tr> <td><a href="/wiki/I1_receptor" class="mw-redirect" title="I1 receptor">I2</a></td> <td>792 </td></tr> <tr> <td><a href="/wiki/TAAR1" title="TAAR1">TAAR1</a></td> <td>1,400 (Ki) (rat) 17,000 (Ki) (mouse) 920–2,700 (<abbr title="half-maximal effective concentration">EC50</abbr>) (rodent) >30,000 (<abbr title="half-maximal effective concentration">EC50</abbr>) (human) </td></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>3,800–>10,000 (Ki) 662–3,900 (<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) 561 (<abbr title="half-maximal effective concentration">EC50</abbr>) 54% (<abbr title="maximal efficacy">Emax</abbr>) </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>13,000 (Ki) 14,000 (<abbr title="half-maximal inhibitory concentration">IC50</abbr>) >10,000 (<abbr title="half-maximal effective concentration">EC50</abbr>) </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>6,000–>30,000 (Ki) >100,000 (<abbr title="half-maximal inhibitory concentration">IC50</abbr>) >10,000 (<abbr title="half-maximal effective concentration">EC50</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 psilocin interacts with the site. Sources: <a href="#cite_note-BindingDB-Psilocin-134">[129]</a><a href="#cite_note-BindingDB-Psilocybin-135">[130]</a><a href="#cite_note-PDSP-Psilocin-136">[131]</a><a href="#cite_note-PDSP-Psilocybin-137">[132]</a><a href="#cite_note-HolzeSinghLiechti2024-14">[14]</a><a href="#cite_note-DoddNormanEyre2023-10">[10]</a><a href="#cite_note-TylšPáleníčekHoráček2014-19">[19]</a><a href="#cite_note-WojtasGołembiowska2023-138">[133]</a><a href="#cite_note-RickliMoningHoener2016-139">[134]</a><a href="#cite_note-Ray2010-140">[135]</a><a href="#cite_note-RothmanPartillaBaumann2012-141">[136]</a><a href="#cite_note-BloughLandavazoDecker2014-142">[137]</a><a href="#cite_note-Wsół2023-143">[138]</a><a href="#cite_note-GainetdinovHoenerBerry2018-144">[139]</a> </td></tr></tbody></table> Psilocybin is a <a href="/wiki/Serotonergic_psychedelic" class="mw-redirect" title="Serotonergic psychedelic">serotonergic psychedelic</a> that acts as a <a href="/wiki/Prodrug" title="Prodrug">prodrug</a> of <a href="/wiki/Psilocin" title="Psilocin">psilocin</a>, the <a href="/wiki/Active_metabolite" title="Active metabolite">active form</a> of the drug.<a href="#cite_note-HolzeSinghLiechti2024-14">[14]</a><a href="#cite_note-DoddNormanEyre2023-10">[10]</a> Psilocin is a close <a href="/wiki/Structural_analog" title="Structural analog">analogue</a> of the <a href="/wiki/Monoamine_neurotransmitter" title="Monoamine neurotransmitter">monoamine neurotransmitter</a> <a href="/wiki/Serotonin" title="Serotonin">serotonin</a> and, like serotonin, acts as a <a href="/wiki/Binding_selectivity" title="Binding selectivity">non-selective</a> <a href="/wiki/Agonist" title="Agonist">agonist</a> of the <a href="/wiki/Serotonin_receptor" class="mw-redirect" title="Serotonin receptor">serotonin receptors</a>, including behaving as a <a href="/wiki/Partial_agonist" title="Partial agonist">partial agonist</a> of the serotonin <a href="/wiki/5-HT2A_receptor" title="5-HT2A receptor">5-HT2A receptor</a>.<a href="#cite_note-HolzeSinghLiechti2024-14">[14]</a><a href="#cite_note-DoddNormanEyre2023-10">[10]</a><a href="#cite_note-TylšPáleníčekHoráček2014-19">[19]</a> It shows high <a href="/wiki/Affinity_(pharmacology)" class="mw-redirect" title="Affinity (pharmacology)">affinity</a> for most of the serotonin receptors, with the notable exception of the serotonin <a href="/wiki/5-HT3_receptor" title="5-HT3 receptor">5-HT3 receptor</a>.<a href="#cite_note-HolzeSinghLiechti2024-14">[14]</a><a href="#cite_note-DoddNormanEyre2023-10">[10]</a><a href="#cite_note-TylšPáleníčekHoráček2014-19">[19]</a> Psilocin's affinity for the serotonin 5-HT2A receptor is 15-fold higher in humans than in rats due to species differences.<a href="#cite_note-TylšPáleníčekHoráček2014-19">[19]</a><a href="#cite_note-GallaherChenShih1993-145">[140]</a> In addition to interacting with the serotonin receptors, psilocin is a <a href="/wiki/Partial_monoamine_releasing_agent" class="mw-redirect" title="Partial monoamine releasing agent">partial</a> <a href="/wiki/Serotonin_releasing_agent" title="Serotonin releasing agent">serotonin releasing agent</a> with lower <a href="/wiki/Potency_(pharmacology)" title="Potency (pharmacology)">potency</a>.<a href="#cite_note-RothmanPartillaBaumann2012-141">[136]</a><a href="#cite_note-BloughLandavazoDecker2014-142">[137]</a> Unlike certain other psychedelics such as <a href="/wiki/LSD" title="LSD">LSD</a>, it appears to show little affinity for many other <a href="/wiki/Biological_target" title="Biological target">targets</a>, such as <a href="/wiki/Dopamine_receptor" title="Dopamine receptor">dopamine receptors</a>.<a href="#cite_note-GeigerWurstDaniels2018-18">[18]</a><a href="#cite_note-HolzeSinghLiechti2024-14">[14]</a><a href="#cite_note-FradetKellyDonnelly2025-25">[24]</a><a href="#cite_note-RickliMoningHoener2016-139">[134]</a><a href="#cite_note-BindingDB-Psilocin-134">[129]</a><a href="#cite_note-PDSP-Psilocin-136">[131]</a> Psilocin is an agonist of the mouse and rat but not human <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-GainetdinovHoenerBerry2018-144">[139]</a><a href="#cite_note-RickliMoningHoener2016-139">[134]</a><a href="#cite_note-ShaharBotvinnikEsh-Zuntz2022-146">[141]</a> Psilocybin's and psilocin's psychedelic effects are mediated specifically by agonism of the serotonin 5-HT2A receptor.<a href="#cite_note-HolzeSinghLiechti2024-14">[14]</a><a href="#cite_note-DoddNormanEyre2023-10">[10]</a> <a href="/wiki/Binding_selectivity" title="Binding selectivity">Selective</a> serotonin 5-HT2A receptor <a href="/wiki/Receptor_antagonist" title="Receptor antagonist">antagonists</a> like <a href="/wiki/Volinanserin" title="Volinanserin">volinanserin</a> block the <a href="/wiki/Head-twitch_response" title="Head-twitch response">head-twitch response</a> (HTR), a behavioral proxy of psychedelic-like effects, induced by psilocybin in rodents, and the HTR is similarly absent in serotonin 5-HT2A receptor <a href="/wiki/Knockout_mice" class="mw-redirect" title="Knockout mice">knockout mice</a>.<a href="#cite_note-DoddNormanEyre2023-10">[10]</a><a href="#cite_note-TylšPáleníčekHoráček2014-19">[19]</a><a href="#cite_note-Erkizia-SantamaríaAlles-PascualHorrillo2022-147">[142]</a><a href="#cite_note-ShaharBotvinnikEsh-Zuntz2022-146">[141]</a> There is a significant relationship between psilocybin's hallucinogenic effects and serotonin 5-HT2A receptor <a href="/wiki/Receptor_occupancy" class="mw-redirect" title="Receptor occupancy">occupancy</a> in humans.<a href="#cite_note-HolzeSinghLiechti2024-14">[14]</a><a href="#cite_note-HalberstadtGeyer2011-105">[101]</a><a href="#cite_note-MadsenFisherBurmester2019-148">[143]</a> Psilocybin's psychedelic effects can be blocked by serotonin 5-HT2A receptor antagonists like <a href="/wiki/Ketanserin" title="Ketanserin">ketanserin</a> and <a href="/wiki/Risperidone" title="Risperidone">risperidone</a> in humans.<a href="#cite_note-Canal2018-149">[144]</a><a href="#cite_note-HolzeSinghLiechti2024-14">[14]</a><a href="#cite_note-DoddNormanEyre2023-10">[10]</a><a href="#cite_note-HalberstadtGeyer2011-105">[101]</a><a href="#cite_note-Vollenweider1998-93">[89]</a> Activation of serotonin 5-HT2A receptors in <a href="/wiki/Layer_V" class="mw-redirect" title="Layer V">layer V</a> of the <a href="/wiki/Medial_prefrontal_cortex" class="mw-redirect" title="Medial prefrontal cortex">medial prefrontal cortex</a> (mPFC) and consequent <a href="/wiki/Glutamate" class="mw-redirect" title="Glutamate">glutamate</a> release in this area has been especially implicated in the hallucinogenic effects of psilocybin and other serotonergic psychedelics.<a href="#cite_note-DeGregorioEnnsNuñez2018-150">[145]</a><a href="#cite_note-MarekSchoepp2021-151">[146]</a><a href="#cite_note-Halberstadt2015-152">[147]</a><a href="#cite_note-HalberstadtGeyer2018-153">[148]</a><a href="#cite_note-WillinsMeltzer1997-154">[149]</a> In addition, region-dependent alterations in brain glutamate levels may be related to the experience of <a href="/wiki/Ego_dissolution" class="mw-redirect" title="Ego dissolution">ego dissolution</a>.<a href="#cite_note-MasonKuypersMüller2020-155">[150]</a> Serotonin <a href="/wiki/5-HT1A_receptor" title="5-HT1A receptor">5-HT1A receptor</a> activation seems to inhibit the hallucinogenic effects of psilocybin and other psychedelics.<a href="#cite_note-HalmanKongSarris2024-156">[151]</a><a href="#cite_note-BrandtKavanaghTwamley2018-157">[152]</a><a href="#cite_note-PokornyPrellerKraehenmann2016-158">[153]</a><a href="#cite_note-Strassman1996-159">[154]</a> Although serotonin 5-HT2A receptor agonism mediates the <a href="/wiki/Hallucinogen" title="Hallucinogen">hallucinogenic</a> effects of psilocybin and psilocin, activation of other serotonin receptors also appears to contribute to these compounds' <a href="/wiki/Psychoactive_drug" title="Psychoactive drug">psychoactive</a> and behavioral effects.<a href="#cite_note-HalberstadtGeyer2011-105">[101]</a><a href="#cite_note-DoddNormanEyre2023-10">[10]</a><a href="#cite_note-TylšPáleníčekHoráček2014-19">[19]</a><a href="#cite_note-CameronBenetatosLewis2023-160">[155]</a><a href="#cite_note-CordnerPrandovszkyPedicini2022-161">[156]</a><a href="#cite_note-SinghShaharWolf2022-162">[157]</a> Some of psilocybin's non-hallucinogenic behavioral effects in animals can be reversed by antagonists of the serotonin 5-HT1A, <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-DoddNormanEyre2023-10">[10]</a><a href="#cite_note-TylšPáleníčekHoráček2014-19">[19]</a> Psilocybin produces profoundly <a href="/wiki/Hypolocomotion" class="mw-redirect" title="Hypolocomotion">decreased locotomotor</a> and <a href="/wiki/Exploration" title="Exploration">investigatory behavior</a> in rodents, and this appears to be dependent on serotonin 5-HT1A receptor activation but not on activation of the serotonin 5-HT2A or 5-HT2C receptors.<a href="#cite_note-Halberstadt2015-152">[147]</a><a href="#cite_note-HalberstadtGeyer2018-153">[148]</a><a href="#cite_note-HalberstadtKoedoodPowell2011-163">[158]</a> In addition, the serotonin <a href="/wiki/5-HT1B_receptor" title="5-HT1B receptor">5-HT1B receptor</a> has been found to be required for psilocybin's persisting <a href="/wiki/Antidepressant" title="Antidepressant">antidepressant</a>- and <a href="/wiki/Anxiolytic" title="Anxiolytic">anxiolytic</a>-like effects as well as acute hypolocomotion in animals.<a href="#cite_note-FleuryNautiyal2024-164">[159]</a> In humans, ketanserin blocked psilocybin's hallucinogenic effects but not all of its cognitive and behavioral effects.<a href="#cite_note-HalberstadtGeyer2011-105">[101]</a> Serotonin 5-HT2C receptor activation and downstream inhibition of the <a href="/wiki/Mesolimbic_pathway" title="Mesolimbic pathway">mesolimbic dopamine pathway</a> may be involved in the limited <a href="/wiki/Addictive_potential" class="mw-redirect" title="Addictive potential">addictive potential</a> of serotonergic psychedelics like psilocybin.<a href="#cite_note-CanalMurnane2017-165">[160]</a> In addition to its psychedelic effects, psilocin has been found to produce <a href="/wiki/Psychoplastogen" title="Psychoplastogen">psychoplastogenic</a> effects in animals, including <a href="/wiki/Dendritogenesis" class="mw-redirect" title="Dendritogenesis">dendritogenesis</a>, <a href="/wiki/Spinogenesis" class="mw-redirect" title="Spinogenesis">spinogenesis</a>, and <a href="/wiki/Synaptogenesis" title="Synaptogenesis">synaptogenesis</a>.<a href="#cite_note-HatzipantelisOlson2024-166">[161]</a><a href="#cite_note-DoddNormanEyre2023-10">[10]</a><a href="#cite_note-LyGrebCameron2018-167">[162]</a> It has been found to promote <a href="/wiki/Neuroplasticity" title="Neuroplasticity">neuroplasticity</a> in the brain in a rapid, robust, and sustained manner with a single dose.<a href="#cite_note-HatzipantelisOlson2024-166">[161]</a><a href="#cite_note-DoddNormanEyre2023-10">[10]</a> These effects appear to be mediated by <a href="/wiki/Intracellular" class="mw-redirect" title="Intracellular">intracellular</a> serotonin 5-HT2A receptor activation.<a href="#cite_note-HatzipantelisOlson2024-166">[161]</a><a href="#cite_note-DoddNormanEyre2023-10">[10]</a><a href="#cite_note-VargasDunlapDong2023-168">[163]</a><a href="#cite_note-LyGrebCameron2018-167">[162]</a> The psychoplastogenic effects of psilocybin and other serotonergic psychedelics may be involved in their potential therapeutic benefits in the treatment of <a href="/wiki/Psychiatric_disorder" class="mw-redirect" title="Psychiatric disorder">psychiatric disorders</a> such as <a href="/wiki/Depression_(mood)" title="Depression (mood)">depression</a>.<a href="#cite_note-VargasMeyerAvanes2021-169">[164]</a><a href="#cite_note-Olson2021-170">[165]</a><a href="#cite_note-DeVos2021-171">[166]</a> They may also be involved in the effects of <a href="/wiki/Microdosing" title="Microdosing">microdosing</a>.<a href="#cite_note-CalderHasler2023-172">[167]</a> Psilocin has also been reported to act as a highly <a href="/wiki/Potency_(pharmacology)" title="Potency (pharmacology)">potent</a> <a href="/wiki/Positive_allosteric_modulator" class="mw-redirect" title="Positive allosteric modulator">positive allosteric modulator</a> of the <a href="/wiki/Tropomyosin_receptor_kinase_B" title="Tropomyosin receptor kinase B">tropomyosin receptor kinase B</a> (TrkB), one of the <a href="/wiki/Receptor_(biochemistry)" title="Receptor (biochemistry)">receptors</a> of <a href="/wiki/Brain-derived_neurotrophic_factor" title="Brain-derived neurotrophic factor">brain-derived neurotrophic factor</a> (BDNF).<a href="#cite_note-HatzipantelisOlson2024-166">[161]</a><a href="#cite_note-FradetKellyDonnelly2025-25">[24]</a><a href="#cite_note-MolinerGirychBrunello2023-173">[168]</a> But psilocybin has been found to inhibit <a href="/wiki/Hippocampus" title="Hippocampus">hippocampal</a> <a href="/wiki/Neurogenesis" title="Neurogenesis">neurogenesis</a> in rodents.<a href="#cite_note-HatzipantelisOlson2024-166">[161]</a> Psilocybin produces profound <a href="/wiki/Anti-inflammatory" title="Anti-inflammatory">anti-inflammatory</a> effects mediated by serotonin 5-HT2A receptor activation in <a href="/wiki/Preclinical_research" class="mw-redirect" title="Preclinical research">preclinical studies</a>.<a href="#cite_note-FlanaganNichols2022-174">[169]</a><a href="#cite_note-WulffNicholsThompson2023-175">[170]</a><a href="#cite_note-Kinderlehrer2025-176">[171]</a> These effects have a potency similar to that of <a href="/wiki/(R)-DOI" class="mw-redirect" title="(R)-DOI">(R)-DOI</a>, and its anti-inflammatory effects occur at far lower doses than those that produce hallucinogen-like effects in animals.<a href="#cite_note-Nichols2022-177">[172]</a><a href="#cite_note-FlanaganNichols2022-174">[169]</a><a href="#cite_note-WulffNicholsThompson2023-175">[170]</a><a href="#cite_note-FlanaganBillacLandry2021-178">[173]</a> Psilocybin's anti-inflammatory effects might be involved in its potential antidepressant benefits and might also have other therapeutic applications, such as treatment of <a href="/wiki/Asthma" title="Asthma">asthma</a> and <a href="/wiki/Neuroinflammation" title="Neuroinflammation">neuroinflammation</a>.<a href="#cite_note-FlanaganNichols2022-174">[169]</a><a href="#cite_note-WulffNicholsThompson2023-175">[170]</a><a href="#cite_note-FlanaganNichols2018-179">[174]</a> They may also be involved in microdosing effects.<a href="#cite_note-KuypersErritzoeKnudsen2019-180">[175]</a><a href="#cite_note-Kinderlehrer2025-176">[171]</a> But psychedelics have been found to have anti-inflammatory effects only in the setting of preexisting <a href="/wiki/Inflammation" title="Inflammation">inflammation</a> and may be <a href="/wiki/Pro-inflammatory" class="mw-redirect" title="Pro-inflammatory">pro-inflammatory</a> outside that context.<a href="#cite_note-LowNgLim2024-181">[176]</a> Psilocybin has been found to have a large, long-lasting impact on the <a href="/wiki/Gut_microbiome" class="mw-redirect" title="Gut microbiome">intestinal microbiome</a> and to influence the <a href="/wiki/Gut%E2%80%93brain_axis" title="Gut–brain axis">gut–brain axis</a> in animals.<a href="#cite_note-KellyClarkeHarkin2023-182">[177]</a><a href="#cite_note-CalderMockFriedli2023-183">[178]</a><a href="#cite_note-ReedFoldi2024-184">[179]</a><a href="#cite_note-CordnerPrandovszkyPedicini2022-161">[156]</a><a href="#cite_note-XuKissJones2024-185">[180]</a> These effects are partially but not fully dependent on its activation of the serotonin 5-HT2A and/or 5-HT2C receptors.<a href="#cite_note-CordnerPrandovszkyPedicini2022-161">[156]</a> Some of psilocybin's behavioral and potential therapeutic effects may be mediated by changes to the gut microbiome.<a href="#cite_note-CordnerPrandovszkyPedicini2022-161">[156]</a><a href="#cite_note-ReedFoldi2024-184">[179]</a><a href="#cite_note-ReedFoldi2024-184">[179]</a><a href="#cite_note-CordnerPrandovszkyPedicini2022-161">[156]</a> Transplantation of intestinal contents of psilocybin-treated rodents to untreated rodents resulted in behavioral changes consistent with those of psilocybin administration.<a href="#cite_note-CordnerPrandovszkyPedicini2022-161">[156]</a> Psilocybin and other psychedelics produce <a href="/wiki/Sympathomimetic" class="mw-redirect" title="Sympathomimetic">sympathomimetic</a> effects, such as increased <a href="/wiki/Heart_rate" title="Heart rate">heart rate</a> and <a href="/wiki/Blood_pressure" title="Blood pressure">blood pressure</a>, by activating the serotonin 5-HT2A receptor.<a href="#cite_note-Wsół2023-143">[138]</a><a href="#cite_note-NeumannDheinKirchhefer2024-186">[181]</a><a href="#cite_note-LeyHolzeArikci2023-187">[182]</a> Long-term repeated use of psilocybin may result in risk of <a href="/wiki/Cardiac_valvulopathy" class="mw-redirect" title="Cardiac valvulopathy">cardiac valvulopathy</a> and other <a href="/wiki/Health_complication" class="mw-redirect" title="Health complication">complications</a> by activating serotonin 5-HT2B receptors.<a href="#cite_note-GeigerWurstDaniels2018-18">[18]</a><a href="#cite_note-TagenMantuanivanHeerden2023-188">[183]</a><a href="#cite_note-RouaudCalderHasler2024-189">[184]</a><a href="#cite_note-Wsół2023-143">[138]</a><a href="#cite_note-NeumannDheinKirchhefer2024-186">[181]</a> There is little or no acute <a href="/wiki/Drug_tolerance" title="Drug tolerance">tolerance</a> with psilocybin, and hence its <a href="/wiki/Duration_of_action" class="mw-redirect" title="Duration of action">duration</a> is dictated by <a href="/wiki/Pharmacokinetics" title="Pharmacokinetics">pharmacokinetics</a> rather than by <a href="/wiki/Pharmacodynamics" title="Pharmacodynamics">pharmacodynamics</a>.<a href="#cite_note-HolzeSinghLiechti2024-14">[14]</a><a href="#cite_note-HolzeBeckerKolaczynska2023-190">[185]</a> Conversely, tolerance and <a href="/wiki/Tachyphylaxis" title="Tachyphylaxis">tachyphylaxis</a> rapidly develop to psilocybin's psychedelic effects with repeated administration in humans.<a href="#cite_note-GeigerWurstDaniels2018-18">[18]</a><a href="#cite_note-Nichols2004-191">[186]</a><a href="#cite_note-Halberstadt2015-152">[147]</a><a href="#cite_note-HalberstadtGeyer2011-105">[101]</a> In addition, there is <a href="/wiki/Cross-tolerance" title="Cross-tolerance">cross-tolerance</a> with the hallucinogenic effects of other psychedelics such as LSD.<a href="#cite_note-GeigerWurstDaniels2018-18">[18]</a><a href="#cite_note-Nichols2004-191">[186]</a><a href="#cite_note-Halberstadt2015-152">[147]</a><a href="#cite_note-HalberstadtGeyer2011-105">[101]</a> Psilocybin produces <a href="/wiki/Downregulation" class="mw-redirect" title="Downregulation">downregulation</a> of the serotonin 5-HT2A receptor in the brain in animals, an effect thought to be responsible for the development of tolerance to its psychedelic effects.<a href="#cite_note-GeigerWurstDaniels2018-18">[18]</a><a href="#cite_note-Nichols2004-191">[186]</a><a href="#cite_note-Halberstadt2015-152">[147]</a><a href="#cite_note-HalberstadtGeyer2011-105">[101]</a> Serotonin 5-HT2A receptors appear to slowly return over the course of days to weeks after psilocybin administration.<a href="#cite_note-GeigerWurstDaniels2018-18">[18]</a> <div class="mw-heading mw-heading3"><h3 id="Pharmacokinetics">Pharmacokinetics</h3>[<a href="/w/index.php?title=Psilocybin&action=edit&section=22" title="Edit section: Pharmacokinetics">edit</a>]</div> <div class="mw-heading mw-heading4"><h4 id="Absorption">Absorption</h4>[<a href="/w/index.php?title=Psilocybin&action=edit&section=23" title="Edit section: Absorption">edit</a>]</div> There has been little research on psilocybin's <a href="/wiki/Bioavailability" title="Bioavailability">bioavailability</a>.<a href="#cite_note-OttovanderHeijdenSchoones2025-15">[15]</a> Its <a href="/wiki/Oral_administration" title="Oral administration">oral</a> bioavailability, as its <a href="/wiki/Active_metabolite" title="Active metabolite">active form</a> <a href="/wiki/Psilocin" title="Psilocin">psilocin</a>, was about 55.0% (± ~20%) relative to <a href="/wiki/Intravenous_administration" class="mw-redirect" title="Intravenous administration">intravenous administration</a> in one small older study (n=3).<a href="#cite_note-OttovanderHeijdenSchoones2025-15">[15]</a><a href="#cite_note-DoddNormanEyre2023-10">[10]</a><a href="#cite_note-MacCallumLoPistawka2022-11">[11]</a><a href="#cite_note-HaslerBourquinBrenneisen1997-12">[12]</a> After oral administration, psilocybin is detectable in the blood circulation within 20 to 40 minutes, and psilocin is detectable after 30 minutes.<a href="#cite_note-MacCallumLoPistawka2022-11">[11]</a><a href="#cite_note-TylšPáleníčekHoráček2014-19">[19]</a> The mean <a href="/wiki/Tmax_(pharmacology)" class="mw-redirect" title="Tmax (pharmacology)">time to peak</a> levels for psilocin is 1.05 to 3.71 hours in different studies, with most around 2 hours and the upper limit of 3.71 hours being an <a href="/wiki/Outlier" title="Outlier">outlier</a>.<a href="#cite_note-OttovanderHeijdenSchoones2025-15">[15]</a><a href="#cite_note-Manzano-NunezGomezToledo-Mendoza2025-16">[16]</a><a href="#cite_note-TylšPáleníčekHoráček2014-19">[19]</a> Psilocybin, in terms of psilocin, shows clear linear or <a href="/wiki/Dose_dependence" class="mw-redirect" title="Dose dependence">dose-dependent</a> <a href="/wiki/Pharmacokinetics" title="Pharmacokinetics">pharmacokinetics</a>.<a href="#cite_note-OttovanderHeijdenSchoones2025-15">[15]</a><a href="#cite_note-HolzeSinghLiechti2024-14">[14]</a><a href="#cite_note-DoddNormanEyre2023-10">[10]</a><a href="#cite_note-MacCallumLoPistawka2022-11">[11]</a><a href="#cite_note-HolzeBeckerKolaczynska2023-190">[185]</a><a href="#cite_note-BrownNicholasCozzi2017-192">[187]</a> Maximal concentrations of psilocin were 11 ng/mL, 17 ng/mL, and 21 ng/mL with oral psilocybin doses of 15, 25, and 30 mg psilocybin, respectively.<a href="#cite_note-HolzeBeckerKolaczynska2023-190">[185]</a> The maximal levels of psilocin have been found to range from 8.2 ng/mL to 37.6 ng/mL across a dose range of 14 to 42 mg.<a href="#cite_note-Manzano-NunezGomezToledo-Mendoza2025-16">[16]</a> The dose-normalized peak concentration of psilocin is about 0.8 ng/mL/mg.<a href="#cite_note-OttovanderHeijdenSchoones2025-15">[15]</a> The <a href="/wiki/Interindividual_variability" class="mw-redirect" title="Interindividual variability">interindividual variability</a> in the pharmacokinetics of psilocybin is relatively small.<a href="#cite_note-HolzeBeckerKolaczynska2023-190">[185]</a> There is a very strong positive correlation between dose and psilocin peak levels (R2 = 0.95).<a href="#cite_note-Manzano-NunezGomezToledo-Mendoza2025-16">[16]</a> The effects of food on the pharmacokinetics of psilocybin have not been reported and are unknown, but no clear sign of food effects has been observed in preliminary analyses.<a href="#cite_note-OttovanderHeijdenSchoones2025-15">[15]</a> It has also been said that food might delay <a href="/wiki/Absorption_(pharmacokinetics)" class="mw-redirect" title="Absorption (pharmacokinetics)">absorption</a>, reduce peak levels, and reduce bioavailability.<a href="#cite_note-FradetKellyDonnelly2025-25">[24]</a> <div class="mw-heading mw-heading4"><h4 id="Distribution">Distribution</h4>[<a href="/w/index.php?title=Psilocybin&action=edit&section=24" title="Edit section: Distribution">edit</a>]</div> Psilocin, the active form of psilocybin, is extensively <a href="/wiki/Distribution_(pharmacology)" title="Distribution (pharmacology)">distributed</a> to all <a href="/wiki/Tissue_(biology)" title="Tissue (biology)">tissues</a> through the <a href="/wiki/Bloodstream" class="mw-redirect" title="Bloodstream">bloodstream</a>.<a href="#cite_note-MacCallumLoPistawka2022-11">[11]</a> Its <a href="/wiki/Volume_of_distribution" title="Volume of distribution">volume of distribution</a> is 505 to 1,267 L.<a href="#cite_note-OttovanderHeijdenSchoones2025-15">[15]</a> Psilocybin itself is <a href="/wiki/Hydrophilic" class="mw-redirect" title="Hydrophilic">hydrophilic</a> due to its <a href="/wiki/Phosphate" title="Phosphate">phosphate</a> <a href="/wiki/Functional_group" title="Functional group">group</a> and cannot easily cross the <a href="/wiki/Blood%E2%80%93brain_barrier" title="Blood–brain barrier">blood–brain barrier</a>.<a href="#cite_note-FradetKellyDonnelly2025-25">[24]</a><a href="#cite_note-MacCallumLoPistawka2022-11">[11]</a> Conversely, psilocin is <a href="/wiki/Lipophilic" class="mw-redirect" title="Lipophilic">lipophilic</a> and readily crosses the blood–brain barrier to exert effects in the <a href="/wiki/Central_nervous_system" title="Central nervous system">central nervous system</a>.<a href="#cite_note-MacCallumLoPistawka2022-11">[11]</a> The <a href="/wiki/Plasma_protein_binding" title="Plasma protein binding">plasma protein binding</a> of psilocybin is 66% and hence it is moderately plasma protein-bound.<a href="#cite_note-ČamparaKovačić2024-13">[13]</a> <figure class="mw-halign-right skin-invert-image" typeof="mw:File/Thumb"><a href="/wiki/File:Psilocin_intramolecular_hydrogen_bond_and_pseudo-ring_system.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/d/d1/Psilocin_intramolecular_hydrogen_bond_and_pseudo-ring_system.png/300px-Psilocin_intramolecular_hydrogen_bond_and_pseudo-ring_system.png" decoding="async" width="300" height="138" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/d/d1/Psilocin_intramolecular_hydrogen_bond_and_pseudo-ring_system.png/450px-Psilocin_intramolecular_hydrogen_bond_and_pseudo-ring_system.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/d/d1/Psilocin_intramolecular_hydrogen_bond_and_pseudo-ring_system.png/600px-Psilocin_intramolecular_hydrogen_bond_and_pseudo-ring_system.png 2x" data-file-width="1023" data-file-height="470" /></a><figcaption>Theoretical <a href="/wiki/Intramolecular_force" title="Intramolecular force">intramolecular</a> <a href="/wiki/Hydrogen_bond" title="Hydrogen bond">hydrogen bond</a> and <a href="/wiki/Ring_(chemistry)#Rings_and_ring_systems" title="Ring (chemistry)">pseudo-ring system</a> occurring with <a href="/wiki/Psilocin" title="Psilocin">psilocin</a> (4-HO-DMT) but not with <a href="/wiki/Bufotenin" title="Bufotenin">bufotenin</a> (5-HO-DMT).<a href="#cite_note-GumpperNichols2024-193">[188]</a><a href="#cite_note-McBride2000-194">[189]</a></figcaption></figure> Psilocin (4-HO-DMT) is a close <a href="/wiki/Positional_isomer" class="mw-redirect" title="Positional isomer">positional isomer</a> of <a href="/wiki/Bufotenin" title="Bufotenin">bufotenin</a> (5-HO-DMT), which shows <a href="/wiki/Peripherally_selective_drug" title="Peripherally selective drug">peripheral selectivity</a>, and might be expected to have similarly restricted lipophilicity and blood–brain barrier permeability.<a href="#cite_note-GumpperNichols2024-193">[188]</a><a href="#cite_note-McBride2000-194">[189]</a> But psilocin appears to form a <a href="/wiki/Tricyclic_compound" class="mw-redirect" title="Tricyclic compound">tricyclic</a> <a href="/wiki/Ring_(chemistry)#Rings_and_ring_systems" title="Ring (chemistry)">pseudo-ring system</a> wherein its <a href="/wiki/Hydroxyl_group" class="mw-redirect" title="Hydroxyl group">hydroxyl group</a> and <a href="/wiki/Amine" title="Amine">amine</a> interact through <a href="/wiki/Hydrogen_bond" title="Hydrogen bond">hydrogen bonding</a>.<a href="#cite_note-GumpperNichols2024-193">[188]</a><a href="#cite_note-McBride2000-194">[189]</a><a href="#cite_note-PlazasFaraone2023-195">[190]</a><a href="#cite_note-LenzDörnerTrottmann2022-196">[191]</a> This in turn makes psilocin much less <a href="/wiki/Polarity" class="mw-disambig" title="Polarity">polar</a>, more lipophilic, and more able to cross the blood–brain barrier and exert central actions than it would be otherwise.<a href="#cite_note-GumpperNichols2024-193">[188]</a><a href="#cite_note-McBride2000-194">[189]</a><a href="#cite_note-PlazasFaraone2023-195">[190]</a><a href="#cite_note-LenzDörnerTrottmann2022-196">[191]</a> It may also protect psilocin from metabolism by <a href="/wiki/Monoamine_oxidase" title="Monoamine oxidase">monoamine oxidase</a> (MAO).<a href="#cite_note-GumpperNichols2024-193">[188]</a> In contrast, bufotenin is not able to achieve this pseudo-ring system.<a href="#cite_note-GumpperNichols2024-193">[188]</a><a href="#cite_note-McBride2000-194">[189]</a><a href="#cite_note-PlazasFaraone2023-195">[190]</a><a href="#cite_note-LenzDörnerTrottmann2022-196">[191]</a> Accordingly, bufotenin is less lipophilic than psilocin in terms of <a href="/wiki/Partition_coefficient" title="Partition coefficient">partition coefficient</a>.<a href="#cite_note-GumpperNichols2024-193">[188]</a><a href="#cite_note-McBride2000-194">[189]</a> But bufotenin does still show significant central permeability and, like psilocybin, can produce robust hallucinogenic effects in humans.<a href="#cite_note-McBride2000-194">[189]</a><a href="#cite_note-PlazasFaraone2023-195">[190]</a><a href="#cite_note-ShenJiangWinter2010-197">[192]</a><a href="#cite_note-Ott2001a-198">[193]</a> <div class="mw-heading mw-heading4"><h4 id="Metabolism">Metabolism</h4>[<a href="/w/index.php?title=Psilocybin&action=edit&section=25" title="Edit section: Metabolism">edit</a>]</div> <figure class="mw-halign-right skin-invert-image" typeof="mw:File/Thumb"><a href="/wiki/File:Metabolism_of_psilocybin_in_humans_and_mice.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/f/f7/Metabolism_of_psilocybin_in_humans_and_mice.png/500px-Metabolism_of_psilocybin_in_humans_and_mice.png" decoding="async" width="500" height="400" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/f/f7/Metabolism_of_psilocybin_in_humans_and_mice.png/750px-Metabolism_of_psilocybin_in_humans_and_mice.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/f/f7/Metabolism_of_psilocybin_in_humans_and_mice.png/1000px-Metabolism_of_psilocybin_in_humans_and_mice.png 2x" data-file-width="1544" data-file-height="1236" /></a><figcaption><a href="/wiki/Drug_metabolism" title="Drug metabolism">Metabolism</a> of psilocybin and <a href="/wiki/Psilocin" title="Psilocin">psilocin</a> in humans and mice.<a href="#cite_note-ThomannKolaczynskaStoeckmann2024-199">[194]</a><a href="#cite_note-FradetKellyDonnelly2025-25">[24]</a></figcaption></figure> Psilocybin is <a href="/wiki/Dephosphorylation" title="Dephosphorylation">dephosphorylated</a> into its <a href="/wiki/Active_metabolite" title="Active metabolite">active form</a> <a href="/wiki/Psilocin" title="Psilocin">psilocin</a> in the body.<a href="#cite_note-MacCallumLoPistawka2022-11">[11]</a><a href="#cite_note-DoddNormanEyre2023-10">[10]</a><a href="#cite_note-LoweToyangSteele2021-7">[7]</a> Psilocybin is <a href="/wiki/Metabolism" title="Metabolism">metabolized</a> in the <a href="/wiki/Intestine" class="mw-redirect" title="Intestine">intestines</a>, <a href="/wiki/Liver" title="Liver">liver</a>, <a href="/wiki/Kidney" title="Kidney">kidneys</a>, <a href="/wiki/Blood" title="Blood">blood</a>, and other <a href="/wiki/Tissue_(biology)" title="Tissue (biology)">tissues</a> and <a href="/wiki/Bodily_fluid" class="mw-redirect" title="Bodily fluid">bodily fluids</a>.<a href="#cite_note-OttovanderHeijdenSchoones2025-15">[15]</a><a href="#cite_note-Dinis-Oliveira2017-200">[195]</a><a href="#cite_note-ThomannKolaczynskaStoeckmann2024-199">[194]</a> There is significant <a href="/wiki/First-pass_metabolism" class="mw-redirect" title="First-pass metabolism">first-pass metabolism</a> of psilocybin and psilocin with <a href="/wiki/Oral_administration" title="Oral administration">oral administration</a>.<a href="#cite_note-OttovanderHeijdenSchoones2025-15">[15]</a><a href="#cite_note-ThomannKolaczynskaStoeckmann2024-199">[194]</a> No psilocybin has been detected in the blood in humans after oral administration, suggesting virtually complete dephosphorylation into psilocin with the first pass.<a href="#cite_note-OttovanderHeijdenSchoones2025-15">[15]</a><a href="#cite_note-DoddNormanEyre2023-10">[10]</a><a href="#cite_note-LoweToyangSteele2021-7">[7]</a><a href="#cite_note-ThomannKolaczynskaStoeckmann2024-199">[194]</a> The <a href="/wiki/Competitive_inhibitor" class="mw-redirect" title="Competitive inhibitor">competitive</a> <a href="/wiki/Phosphatase_inhibitor" class="mw-redirect" title="Phosphatase inhibitor">phosphatase inhibitor</a> β-glycerolphosphate, which inhibits psilocybin dephosphorylation, greatly attenuates the behavioral effects of psilocybin in rodents.<a href="#cite_note-TylšPáleníčekHoráček2014-19">[19]</a><a href="#cite_note-ThomannKolaczynskaStoeckmann2024-199">[194]</a><a href="#cite_note-Horita1963-201">[196]</a> Psilocybin undergoes dephosphorylation into psilocin via the <a href="/wiki/Acid" title="Acid">acidic</a> environment of the <a href="/wiki/Stomach" title="Stomach">stomach</a> or the actions of <a href="/wiki/Alkaline_phosphatase" title="Alkaline phosphatase">alkaline phosphatase</a> (ALP) and non-specific <a href="/wiki/Esterase" title="Esterase">esterases</a> in tissues and fluids.<a href="#cite_note-PepeHesamidelaCerda2023-202">[197]</a><a href="#cite_note-Dinis-Oliveira2017-200">[195]</a><a href="#cite_note-TylšPáleníčekHoráček2014-19">[19]</a> Psilocin is <a href="/wiki/Demethylation" title="Demethylation">demethylated</a> and <a href="/wiki/Oxidative_deamination" title="Oxidative deamination">oxidatively deaminated</a> by <a href="/wiki/Monoamine_oxidase" title="Monoamine oxidase">monoamine oxidase</a> (MAO), specifically <a href="/wiki/Monoamine_oxidase_A" title="Monoamine oxidase A">monoamine oxidase A</a> (MAO-A), into 4-hydroxyindole-3-acetaldehyde (4-HIAL or 4-HIA).<a href="#cite_note-DoddNormanEyre2023-10">[10]</a><a href="#cite_note-LoweToyangSteele2021-7">[7]</a><a href="#cite_note-ChenWangYong2025-203">[198]</a> 4-HIAL is then further oxidated into 4-hydroxyindole-3-acetic acid (4-HIAA) by <a href="/wiki/Aldehyde_dehydrogenase" title="Aldehyde dehydrogenase">aldehyde dehydrogenase</a> (ALDH) or into 4-hydroxytryptophol (4-HTOL or 4-HTP) by <a href="/wiki/Alcohol_dehydrogenase" title="Alcohol dehydrogenase">alcohol dehydrogenase</a> (ALD).<a href="#cite_note-DoddNormanEyre2023-10">[10]</a><a href="#cite_note-LoweToyangSteele2021-7">[7]</a> Deamination of psilocin by MAO-A appears to be responsible for about 4% or 33% of its metabolism in different studies.<a href="#cite_note-ThomannKolaczynskaStoeckmann2024-199">[194]</a><a href="#cite_note-HolzeBeckerKolaczynska2023-190">[185]</a><a href="#cite_note-TylšPáleníčekHoráček2014-19">[19]</a> In contrast to psilocin, its metabolites 4-HIAA and 4-HTP showed no affinity for or activation of multiple serotonin receptors and are considered inactive.<a href="#cite_note-DoddNormanEyre2023-10">[10]</a><a href="#cite_note-FradetKellyDonnelly2025-25">[24]</a><a href="#cite_note-ThomannKolaczynskaStoeckmann2024-199">[194]</a> Based on in vitro studies, it has been estimated that MAO-A is responsible for about 81% of psilocin's <a href="/wiki/Phase_I_metabolism" class="mw-redirect" title="Phase I metabolism">phase I</a> hepatic metabolism.<a href="#cite_note-ChenWangYong2025-203">[198]</a> Psilocin and its metabolites are also <a href="/wiki/Glucuronidation" title="Glucuronidation">glucuronidated</a> by <a href="/wiki/UDP-glucuronyltransferase" class="mw-redirect" title="UDP-glucuronyltransferase">UDP-glucuronyltransferases</a> (UGTs).<a href="#cite_note-OttovanderHeijdenSchoones2025-15">[15]</a><a href="#cite_note-DoddNormanEyre2023-10">[10]</a><a href="#cite_note-LoweToyangSteele2021-7">[7]</a><a href="#cite_note-ThomannKolaczynskaStoeckmann2024-199">[194]</a> <a href="/wiki/UGT1A10" title="UGT1A10">UGT1A10</a> and <a href="/wiki/UGT1A9" title="UGT1A9">UGT1A9</a> appear to be the most involved.<a href="#cite_note-OttovanderHeijdenSchoones2025-15">[15]</a><a href="#cite_note-DoddNormanEyre2023-10">[10]</a><a href="#cite_note-TylšPáleníčekHoráček2014-19">[19]</a> Psilocybin's glucuronidated metabolites include psilocin-O-glucuronide and 4-HIAA-O-glucuronide.<a href="#cite_note-DoddNormanEyre2023-10">[10]</a><a href="#cite_note-LoweToyangSteele2021-7">[7]</a><a href="#cite_note-ThomannKolaczynskaStoeckmann2024-199">[194]</a> Approximately 80% of psilocin in <a href="/wiki/Blood_plasma" title="Blood plasma">blood plasma</a> is in <a href="/wiki/Conjugation_(biochemistry)" class="mw-redirect" title="Conjugation (biochemistry)">conjugated</a> form, and conjugated psilocin levels are about fourfold higher than levels of free psilocin.<a href="#cite_note-ThomannKolaczynskaStoeckmann2024-199">[194]</a><a href="#cite_note-TylšPáleníčekHoráček2014-19">[19]</a> Plasma 4-HIAA levels are also much higher than those of free psilocin.<a href="#cite_note-DoddNormanEyre2023-10">[10]</a> <a href="/wiki/Norpsilocin" title="Norpsilocin">Norpsilocin</a> (4-HO-NMT), formed from psilocin via demethylation mediated by the <a href="/wiki/Cytochrome_P450" title="Cytochrome P450">cytochrome P450</a> <a href="/wiki/Enzyme" title="Enzyme">enzyme</a> <a href="/wiki/CYP2D6" title="CYP2D6">CYP2D6</a>, is known to occur in mice <a href="/wiki/In_vivo" title="In vivo">in vivo</a> and with human recombinant CYP2D6 <a href="/wiki/In_vitro" title="In vitro">in vitro</a> but was not detected in humans in vivo.<a href="#cite_note-ThomannKolaczynskaStoeckmann2024-199">[194]</a> An oxidized psilocin metabolite of unknown <a href="/wiki/Chemical_structure" title="Chemical structure">chemical structure</a> is also formed by hydroxyindole oxidase activity of CYP2D6.<a href="#cite_note-ThomannKolaczynskaStoeckmann2024-199">[194]</a><a href="#cite_note-TylšPáleníčekHoráček2014-19">[19]</a> Oxidized psilocin is possibly a <a href="/wiki/Quinone" title="Quinone">quinone</a>-type structure like psilocin iminoquinone (4-hydroxy-5-oxo-N,N-DMT) or psilocin hydroquinone (4,5-dihydroxy-N,N-DMT).<a href="#cite_note-ThomannKolaczynskaStoeckmann2024-199">[194]</a><a href="#cite_note-TylšPáleníčekHoráček2014-19">[19]</a> Additional metabolites formed by CYP2D6 may also be present.<a href="#cite_note-ThomannKolaczynskaStoeckmann2024-199">[194]</a> Besides CYP2D6, <a href="/wiki/CYP3A4" title="CYP3A4">CYP3A4</a> showed minor activity in metabolizing psilocin, though the produced metabolite is unknown.<a href="#cite_note-ThomannKolaczynskaStoeckmann2024-199">[194]</a> Other <a href="/wiki/Cytochrome_P450" title="Cytochrome P450">cytochrome P450</a> <a href="/wiki/Enzyme" title="Enzyme">enzymes</a> besides CYP2D6 and CYP3A4 appear unlikely to be involved in psilocin metabolism.<a href="#cite_note-ThomannKolaczynskaStoeckmann2024-199">[194]</a> CYP2D6 <a href="/wiki/Pharmacogenomics" title="Pharmacogenomics">metabolizer phenotypes</a> do not modify psilocin exposure in humans, suggesting that CYP2D6 is not critically involved in psilocin metabolism and is unlikely to result in interindividual differences in psilocin kinetics or effects.<a href="#cite_note-FradetKellyDonnelly2025-25">[24]</a><a href="#cite_note-ThomannKolaczynskaStoeckmann2024-199">[194]</a> Psilocybin and psilocin might inhibit <a href="/wiki/CYP3A4" title="CYP3A4">CYP3A4</a> and <a href="/wiki/CYP2A6" title="CYP2A6">CYP2A6</a> to some extent, respectively.<a href="#cite_note-Manzano-NunezGomezToledo-Mendoza2025-16">[16]</a> <div class="mw-heading mw-heading4"><h4 id="Elimination">Elimination</h4>[<a href="/w/index.php?title=Psilocybin&action=edit&section=26" title="Edit section: Elimination">edit</a>]</div> Psilocybin is <a href="/wiki/Elimination_(pharmacology)" title="Elimination (pharmacology)">eliminated</a> 80 to 85% in <a href="/wiki/Urine" title="Urine">urine</a> and 15 to 20% in <a href="/wiki/Bile" title="Bile">bile</a>.<a href="#cite_note-FradetKellyDonnelly2025-25">[24]</a> It is <a href="/wiki/Excretion" title="Excretion">excreted</a> mainly in urine as psilocin-O-glucuronide.<a href="#cite_note-FradetKellyDonnelly2025-25">[24]</a><a href="#cite_note-Dinis-Oliveira2017-200">[195]</a> The drug was eliminated approximately 20% and 80% as psilocin O-glucuronide in different studies.<a href="#cite_note-OttovanderHeijdenSchoones2025-15">[15]</a><a href="#cite_note-Dinis-Oliveira2017-200">[195]</a><a href="#cite_note-TylšPáleníčekHoráček2014-19">[19]</a><a href="#cite_note-HolzeBeckerKolaczynska2023-190">[185]</a> The amount <a href="/wiki/Excretion" title="Excretion">excreted</a> as unchanged psilocin in urine is 1.5 to 3.4%.<a href="#cite_note-OttovanderHeijdenSchoones2025-15">[15]</a><a href="#cite_note-Dinis-Oliveira2017-200">[195]</a><a href="#cite_note-DoddNormanEyre2023-10">[10]</a><a href="#cite_note-HolzeBeckerKolaczynska2023-190">[185]</a> Studies conflict on the deaminated metabolites of psilocin, with one study finding that only 4% of psilocin is metabolized into 4-HIAA, 4-HIAL, and 4-HTOL<a href="#cite_note-TylšPáleníčekHoráček2014-19">[19]</a> and another that psilocybin is excreted 33% in urine as 4-HIAA.<a href="#cite_note-ThomannKolaczynskaStoeckmann2024-199">[194]</a><a href="#cite_note-HolzeBeckerKolaczynska2023-190">[185]</a> Findings also conflict on whether psilocybin can be detected in urine.<a href="#cite_note-OttovanderHeijdenSchoones2025-15">[15]</a><a href="#cite_note-LoweToyangSteele2021-7">[7]</a><a href="#cite_note-TylšPáleníčekHoráček2014-19">[19]</a> A majority of psilocybin and its metabolites is excreted within 3 hours with oral administration and elimination is almost complete within 24 hours.<a href="#cite_note-TylšPáleníčekHoráček2014-19">[19]</a><a href="#cite_note-LoweToyangSteele2021-7">[7]</a><a href="#cite_note-HolzeBeckerKolaczynska2023-190">[185]</a> The <a href="/wiki/Elimination_half-life" class="mw-redirect" title="Elimination half-life">elimination half-life</a> of psilocybin, as psilocin, is 2.1 to 4.7 hours on average (range 1.2–18.6 hours) <a href="/wiki/Oral_administration" title="Oral administration">orally</a> and 1.2 hours (range 1.8–4.5 hours) <a href="/wiki/Intravenous_administration" class="mw-redirect" title="Intravenous administration">intravenously</a>.<a href="#cite_note-OttovanderHeijdenSchoones2025-15">[15]</a><a href="#cite_note-Manzano-NunezGomezToledo-Mendoza2025-16">[16]</a><a href="#cite_note-DoddNormanEyre2023-10">[10]</a><a href="#cite_note-TylšPáleníčekHoráček2014-19">[19]</a> Psilocin's elimination half-life in mice is 0.9 hours, much faster than in humans.<a href="#cite_note-ThomannKolaczynskaStoeckmann2024-199">[194]</a> Psilocin O-glucuronide's half-life is about 4 hours in humans and approximately 1 hour in mice.<a href="#cite_note-ThomannKolaczynskaStoeckmann2024-199">[194]</a> No dose adjustment of psilocin is thought to be required as psilocin is inactivated mainly via metabolism as opposed to renal elimination.<a href="#cite_note-OttovanderHeijdenSchoones2025-15">[15]</a><a href="#cite_note-FradetKellyDonnelly2025-25">[24]</a><a href="#cite_note-HolzeBeckerKolaczynska2023-190">[185]</a> Accordingly, <a href="/wiki/Glomerular_filtration_rate" title="Glomerular filtration rate">glomerular filtration rate</a> (GFR) did not affect the pharmacokinetics of psilocybin.<a href="#cite_note-OttovanderHeijdenSchoones2025-15">[15]</a><a href="#cite_note-FradetKellyDonnelly2025-25">[24]</a><a href="#cite_note-HolzeBeckerKolaczynska2023-190">[185]</a> <div class="mw-heading mw-heading4"><h4 id="Miscellaneous">Miscellaneous</h4>[<a href="/w/index.php?title=Psilocybin&action=edit&section=27" title="Edit section: Miscellaneous">edit</a>]</div> The <a href="/wiki/Onset_of_action" title="Onset of action">onset of action</a> of psilocybin taken orally is about 20 to 50 minutes and peak subjective effects occur at about 1.0 to 2.2 hours (60–130 minutes).<a href="#cite_note-MacCallumLoPistawka2022-11">[11]</a><a href="#cite_note-HolzeSinghLiechti2024-14">[14]</a> The time to offset of psilocybin orally is about 6 to 7 hours on average.<a href="#cite_note-HolzeBeckerKolaczynska2023-190">[185]</a> The <a href="/wiki/Duration_of_action" class="mw-redirect" title="Duration of action">duration of action</a> of psilocybin is about 4 to 6 hours (range 3–12 hours) orally.<a href="#cite_note-MacCallumLoPistawka2022-11">[11]</a><a href="#cite_note-HolzeSinghLiechti2024-14">[14]</a><a href="#cite_note-YerubandiThomasBhuiya2024-17">[17]</a> A small dose of 1 mg by <a href="/wiki/Intravenous_injection" class="mw-redirect" title="Intravenous injection">intravenous injection</a> had a duration of 15 to 30 minutes.<a href="#cite_note-Passie2002-2">[2]</a><a href="#cite_note-HaslerBourquinBrenneisen1997-12">[12]</a> The psychoactive effects and duration of psilocybin are strongly correlated with psilocin levels.<a href="#cite_note-HolzeSinghLiechti2024-14">[14]</a><a href="#cite_note-HolzeBeckerKolaczynska2023-190">[185]</a><a href="#cite_note-DoddNormanEyre2023-10">[10]</a> Single doses of psilocybin of 3 to 30 mg have been found to dose-dependently occupy the serotonin 5-HT2A receptor in humans as assessed by <a href="/wiki/Medical_imaging" title="Medical imaging">imaging</a> studies.<a href="#cite_note-DoddNormanEyre2023-10">[10]</a> The <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 for occupancy of the serotonin 5-HT2A receptor by psilocin in terms of circulating levels has been found to be 1.97 ng/mL.<a href="#cite_note-DoddNormanEyre2023-10">[10]</a> <a href="/wiki/Body_weight" class="mw-redirect" title="Body weight">Body weight</a> and <a href="/wiki/Body_mass_index" title="Body mass index">body mass index</a> do not appear to affect the pharmacokinetics of psilocybin.<a href="#cite_note-HolzeSinghLiechti2024-14">[14]</a><a href="#cite_note-FradetKellyDonnelly2025-25">[24]</a><a href="#cite_note-HolzeBeckerKolaczynska2023-190">[185]</a> This suggests that body weight-adjusted dosing of psilocybin is unnecessary and may actually be counterproductive and that fixed-dosing should be preferred.<a href="#cite_note-FradetKellyDonnelly2025-25">[24]</a><a href="#cite_note-HolzeBeckerKolaczynska2023-190">[185]</a> Similarly, <a href="/wiki/Age" class="mw-disambig" title="Age">age</a> does not affect the pharmacokinetics of psilocybin.<a href="#cite_note-OttovanderHeijdenSchoones2025-15">[15]</a> <a href="/wiki/Sex" title="Sex">Sex</a> has not been tested.<a href="#cite_note-OttovanderHeijdenSchoones2025-15">[15]</a> <div class="mw-heading mw-heading3"><h3 id="Analytical_methods">Analytical methods</h3>[<a href="/w/index.php?title=Psilocybin&action=edit&section=28" title="Edit section: Analytical methods">edit</a>]</div> Several relatively simple <a href="/wiki/Chemical_test" title="Chemical test">chemical tests</a>—commercially available as <a href="/wiki/Reagent_testing" title="Reagent testing">reagent testing</a> kits—can be used to assess the presence of psilocybin in <a href="/wiki/Extract" title="Extract">extracts</a> prepared from mushrooms. The drug reacts in the <a href="/wiki/Marquis_test" class="mw-redirect" title="Marquis test">Marquis test</a> to produce a yellow color, and a green color in the <a href="/wiki/Mandelin_reagent" title="Mandelin reagent">Mandelin reagent</a>.<a href="#cite_note-Levine2003-204">[199]</a> Neither of these tests, however, is specific for psilocybin; for example, the Marquis test will react with many classes of controlled drugs, such as those containing <a href="/wiki/Primary_amine" class="mw-redirect" title="Primary amine">primary amino</a> groups and unsubstituted <a href="/wiki/Benzene_ring" class="mw-redirect" title="Benzene ring">benzene rings</a>, including <a href="/wiki/Amphetamine" title="Amphetamine">amphetamine</a> and <a href="/wiki/Methamphetamine" title="Methamphetamine">methamphetamine</a>.<a href="#cite_note-Cole2003-205">[200]</a> <a href="/wiki/Ehrlich%27s_reagent" title="Ehrlich's reagent">Ehrlich's reagent</a> and <a href="/wiki/DMACA_reagent" class="mw-redirect" title="DMACA reagent">DMACA reagent</a> are used as chemical sprays to detect the drug after <a href="/wiki/Thin_layer_chromatography" class="mw-redirect" title="Thin layer chromatography">thin layer chromatography</a>.<a href="#cite_note-Bresinsky1989-206">[201]</a> Many modern techniques of <a href="/wiki/Analytical_chemistry" title="Analytical chemistry">analytical chemistry</a> have been used to quantify psilocybin levels in mushroom samples. Although the earliest methods commonly used <a href="/wiki/Gas_chromatography" title="Gas chromatography">gas chromatography</a>, the high temperature required to <a href="/wiki/Volatility_(chemistry)" title="Volatility (chemistry)">vaporize</a> the psilocybin sample prior to analysis causes it to spontaneously lose its phosphoryl group and become psilocin—making it difficult to chemically discriminate between the two drugs. In <a href="/wiki/Forensic_toxicology" title="Forensic toxicology">forensic toxicology</a>, techniques involving <a href="/wiki/Gas_chromatography-mass_spectrometry" class="mw-redirect" title="Gas chromatography-mass spectrometry">gas chromatography coupled to mass spectrometry</a> (GC–MS) are the most widely used due to their high sensitivity and ability to separate compounds in complex biological mixtures.<a href="#cite_note-Kamata2010-207">[202]</a> These techniques include <a href="/wiki/Ion_mobility_spectrometry" title="Ion mobility spectrometry">ion mobility spectrometry</a>,<a href="#cite_note-Keller1999-208">[203]</a> <a href="/wiki/Capillary_zone_electrophoresis" class="mw-redirect" title="Capillary zone electrophoresis">capillary zone electrophoresis</a>,<a href="#cite_note-Pedersen1997-209">[204]</a> <a href="/wiki/Ultraviolet_spectroscopy" class="mw-redirect" title="Ultraviolet spectroscopy">ultraviolet spectroscopy</a>,<a href="#cite_note-Lee1985-210">[205]</a> and <a href="/wiki/Infrared_spectroscopy" title="Infrared spectroscopy">infrared spectroscopy</a>.<a href="#cite_note-Wurst1992-211">[206]</a> <a href="/wiki/High-performance_liquid_chromatography" title="High-performance liquid chromatography">High-performance liquid chromatography</a> (HPLC) is used with ultraviolet,<a href="#cite_note-Anastos2006-126">[121]</a> <a href="/wiki/Fluorescence_spectroscopy" title="Fluorescence spectroscopy">fluorescence</a>,<a href="#cite_note-Saito2004-212">[207]</a> <a href="/wiki/Electrochemical" class="mw-redirect" title="Electrochemical">electrochemical</a>,<a href="#cite_note-Lindenblatt1998-213">[208]</a> and <a href="/wiki/Electrospray_ionization" title="Electrospray ionization">electrospray</a> mass spectrometric detection methods.<a href="#cite_note-RodriguezCruz2005-214">[209]</a> Various chromatographic methods have been developed to detect psilocin in <a href="/wiki/Body_fluids" class="mw-redirect" title="Body fluids">body fluids</a>: the rapid emergency drug identification system (REMEDi HS), a <a href="/wiki/Drug_screening" class="mw-redirect" title="Drug screening">drug screening</a> method based on HPLC;<a href="#cite_note-Sticht2000-215">[210]</a> HPLC with electrochemical detection;<a href="#cite_note-Lindenblatt1998-213">[208]</a><a href="#cite_note-Kysilka1990-216">[211]</a> GC–MS;<a href="#cite_note-Grieshaber2001-217">[212]</a><a href="#cite_note-Sticht2000-215">[210]</a> and <a href="/wiki/Liquid_chromatography%E2%80%93mass_spectrometry" title="Liquid chromatography–mass spectrometry">liquid chromatography coupled to mass spectrometry</a>.<a href="#cite_note-Kamata2003-218">[213]</a> Although the determination of psilocin levels in urine can be performed without sample clean-up (i.e., removing potential contaminants that make it difficult to accurately assess concentration), the analysis in <a href="/wiki/Blood_plasma" title="Blood plasma">plasma</a> or <a href="/wiki/Blood_serum" class="mw-redirect" title="Blood serum">serum</a> requires a preliminary <a href="/wiki/Liquid-liquid_extraction" class="mw-redirect" title="Liquid-liquid extraction">extraction</a>, followed by <a href="/wiki/Derivatization" title="Derivatization">derivatization</a> of the extracts in the case of GC–MS. A specific <a href="/wiki/Immunoassay" title="Immunoassay">immunoassay</a> has also been developed to detect psilocin in whole blood samples.<a href="#cite_note-Albers2004-219">[214]</a> A 2009 publication reported using HPLC to quickly separate forensically important illicit drugs including psilocybin and psilocin, which were identifiable within about half a minute of analysis time.<a href="#cite_note-Lurie2009-220">[215]</a> These analytical techniques to determine psilocybin concentrations in body fluids are, however, not routinely available, and not typically used in <a href="/wiki/Clinical_chemistry" title="Clinical chemistry">clinical</a> settings.<a href="#cite_note-Attema2007-72">[69]</a> <div class="mw-heading mw-heading2"><h2 id="Natural_occurrence">Natural occurrence</h2>[<a href="/w/index.php?title=Psilocybin&action=edit&section=29" title="Edit section: Natural occurrence">edit</a>]</div> <table class="wikitable" style="max-width:16em; float:right; margin:0.5em;"> <caption>Maximum reported psilocybin concentrations (% dry weight) in 12 Psilocybe species<a href="#cite_note-Stamets_1996-34">[33]</a>: 39  </caption> <tbody><tr> <th scope="col">Species </th> <th scope="col">% psilocybin </th></tr> <tr> <td><a href="/wiki/Psilocybe_azurescens" title="Psilocybe azurescens">P. azurescens</a> </td> <td style="text-align: center;">1.78 </td></tr> <tr> <td><a href="/wiki/Psilocybe_serbica" title="Psilocybe serbica">P. serbica</a> </td> <td style="text-align: center;">1.34 </td></tr> <tr> <td><a href="/wiki/Psilocybe_semilanceata" title="Psilocybe semilanceata">P. semilanceata</a> </td> <td style="text-align: center;">0.98 </td></tr> <tr> <td><a href="/wiki/Psilocybe_baeocystis" title="Psilocybe baeocystis">P. baeocystis</a> </td> <td style="text-align: center;">0.85 </td></tr> <tr> <td><a href="/wiki/Psilocybe_cyanescens" title="Psilocybe cyanescens">P. cyanescens</a> </td> <td style="text-align: center;">0.85 </td></tr> <tr> <td><a href="/wiki/P._tampanensis" class="mw-redirect" title="P. tampanensis">P. tampanensis</a> </td> <td style="text-align: center;">0.68 </td></tr> <tr> <td><a href="/wiki/P._cubensis" class="mw-redirect" title="P. cubensis">P. cubensis</a> </td> <td style="text-align: center;">0.63 </td></tr> <tr> <td><a href="/wiki/Psilocybe_weilii" class="mw-redirect" title="Psilocybe weilii">P. weilii</a> </td> <td style="text-align: center;">0.61 </td></tr> <tr> <td><a href="/wiki/Psilocybe_hoogshagenii" title="Psilocybe hoogshagenii">P. hoogshagenii</a> </td> <td style="text-align: center;">0.60 </td></tr> <tr> <td><a href="/wiki/Psilocybe_stuntzii" title="Psilocybe stuntzii">P. stuntzii</a> </td> <td style="text-align: center;">0.36 </td></tr> <tr> <td><a href="/wiki/Psilocybe_cyanofibrillosa" title="Psilocybe cyanofibrillosa">P. cyanofibrillosa</a> </td> <td style="text-align: center;">0.21 </td></tr> <tr> <td><a href="/wiki/Psilocybe_liniformans" title="Psilocybe liniformans">P. liniformans</a> </td> <td style="text-align: center;">0.16 </td></tr></tbody></table> Psilocybin is present in varying concentrations in over 200 species of <a href="/wiki/Basidiomycota" title="Basidiomycota">Basidiomycota</a> mushrooms. In a 2000 review on the worldwide distribution of hallucinogenic mushrooms, <a href="/wiki/Gast%C3%B3n_Guzm%C3%A1n" title="Gastón Guzmán">Gastón Guzmán</a> and colleagues considered these to be distributed amongst the following <a href="/wiki/Genera" class="mw-redirect" title="Genera">genera</a>: <a href="/wiki/Psilocybe" title="Psilocybe">Psilocybe</a> (116 species), <a href="/wiki/Gymnopilus" title="Gymnopilus">Gymnopilus</a> (14), <a href="/wiki/Panaeolus" title="Panaeolus">Panaeolus</a> (13), <a href="/wiki/Copelandia" title="Copelandia">Copelandia</a> (12), <a href="/wiki/Hypholoma" title="Hypholoma">Hypholoma</a> (6), <a href="/wiki/Pluteus" title="Pluteus">Pluteus</a> (6), <a href="/wiki/Inocybe" title="Inocybe">Inocybe</a> (6), <a href="/wiki/Conocybe" title="Conocybe">Conocybe</a> (4), <a href="/wiki/Panaeolina" title="Panaeolina">Panaeolina</a> (4), <a href="/wiki/Gerronema" title="Gerronema">Gerronema</a> (2), and <a href="/wiki/Galerina" title="Galerina">Galerina</a> (1 species).<a href="#cite_note-Guzman2000-221">[216]</a> Guzmán increased his estimate of the number of psilocybin-containing Psilocybe to 144 species in a 2005 review. The majority of these are found in Mexico (53 species), with the remainder distributed in the United States and Canada (22), Europe (16), Asia (15), Africa (4), and Australia and associated islands (19).<a href="#cite_note-Guzman2005-222">[217]</a> The diversity of psilocybin mushrooms is reported to have been increased by horizontal transfer of the psilocybin <a href="/wiki/Metabolic_gene_cluster" title="Metabolic gene cluster">gene cluster</a> between unrelated mushroom species.<a href="#cite_note-223">[218]</a><a href="#cite_note-Reynolds2018-130">[125]</a> In general, psilocybin-containing species are dark-spored, <a href="/wiki/Lamella_(mycology)" title="Lamella (mycology)">gilled</a> mushrooms that grow in meadows and woods of the <a href="/wiki/Subtropic" class="mw-redirect" title="Subtropic">subtropics</a> and <a href="/wiki/Tropics" title="Tropics">tropics</a>, usually in soils rich in <a href="/wiki/Humus" title="Humus">humus</a> and plant debris.<a href="#cite_note-Wurst2002-123">[118]</a>: 5  Psilocybin mushrooms occur on all continents, but the majority of species are found in <a href="/wiki/Tropical_and_subtropical_moist_broadleaf_forests" title="Tropical and subtropical moist broadleaf forests">subtropical humid forests</a>.<a href="#cite_note-Guzman2000-221">[216]</a> Psilocybe species commonly found in the tropics include <a href="/wiki/Psilocybe_cubensis" title="Psilocybe cubensis">P. cubensis</a> and <a href="/wiki/Psilocybe_subcubensis" title="Psilocybe subcubensis">P. subcubensis</a>. <a href="/wiki/Psilocybe_semilanceata" title="Psilocybe semilanceata">P. semilanceata</a>—considered by Guzmán to be the world's most widely distributed psilocybin mushroom<a href="#cite_note-Guzman1983-224">[219]</a>—is found in Europe, North America, Asia, South America, Australia and New Zealand, but is entirely absent from Mexico.<a href="#cite_note-Guzman2005-222">[217]</a> Although the presence or absence of psilocybin is not of much use as a <a href="/wiki/Chemotaxonomy" title="Chemotaxonomy">chemotaxonomical</a> marker at the <a href="/wiki/Family_(biology)" title="Family (biology)">familial</a> level or higher, it is used to classify <a href="/wiki/Taxa" class="mw-redirect" title="Taxa">taxa</a> of lower taxonomic groups.<a href="#cite_note-Saupe1981-225">[220]</a> <figure class="mw-default-size mw-halign-center skin-invert-image" typeof="mw:File/Thumb"><a href="/wiki/File:Pschoactive_Psilocybe_distribution.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/0/03/Pschoactive_Psilocybe_distribution.png/550px-Pschoactive_Psilocybe_distribution.png" decoding="async" width="550" height="272" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/0/03/Pschoactive_Psilocybe_distribution.png/825px-Pschoactive_Psilocybe_distribution.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/0/03/Pschoactive_Psilocybe_distribution.png/1100px-Pschoactive_Psilocybe_distribution.png 2x" data-file-width="1166" data-file-height="577" /></a><figcaption>Global distribution of over 100 psychoactive species of genus Psilocybe mushrooms.<a href="#cite_note-Guzmán_1998-226">[221]</a></figcaption></figure> <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 tright"><div class="thumbinner multiimageinner" style="width:169px;max-width:169px"><div class="trow"><div class="tsingle" style="width:167px;max-width:167px"><div class="thumbimage"><a href="/wiki/File:Psilocybe_mexicana_313748.jpg" class="mw-file-description"><img alt="The mushroom Psilocybe mexicana" src="//upload.wikimedia.org/wikipedia/commons/thumb/9/98/Psilocybe_mexicana_313748.jpg/165px-Psilocybe_mexicana_313748.jpg" decoding="async" width="165" height="124" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/9/98/Psilocybe_mexicana_313748.jpg/248px-Psilocybe_mexicana_313748.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/9/98/Psilocybe_mexicana_313748.jpg/330px-Psilocybe_mexicana_313748.jpg 2x" data-file-width="3648" data-file-height="2736" /></a></div><div class="thumbcaption">Psilocybin was first isolated from <a href="/wiki/Psilocybe_mexicana" title="Psilocybe mexicana">Psilocybe mexicana</a>.</div></div></div><div class="trow"><div class="tsingle" style="width:167px;max-width:167px"><div class="thumbimage"><a href="/wiki/File:Psilocybe_semilanceata_6514.jpg" class="mw-file-description"><img alt="The mushroom Psilocybe semilanceata" src="//upload.wikimedia.org/wikipedia/commons/thumb/4/4a/Psilocybe_semilanceata_6514.jpg/165px-Psilocybe_semilanceata_6514.jpg" decoding="async" width="165" height="165" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/4/4a/Psilocybe_semilanceata_6514.jpg/248px-Psilocybe_semilanceata_6514.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/4/4a/Psilocybe_semilanceata_6514.jpg/330px-Psilocybe_semilanceata_6514.jpg 2x" data-file-width="1280" data-file-height="1280" /></a></div><div class="thumbcaption"><a href="/wiki/Psilocybe_semilanceata" title="Psilocybe semilanceata">P. semilanceata</a> is common in Europe, Canada, and the United States.</div></div></div></div></div> Both the <a href="/wiki/Pileus_(mycology)" title="Pileus (mycology)">caps</a> and the <a href="/wiki/Stipe_(mycology)" title="Stipe (mycology)">stems</a> contain psychoactive compounds, although the caps consistently contain more. The <a href="/wiki/Spore" title="Spore">spores</a> of these mushrooms do not contain psilocybin or psilocin.<a href="#cite_note-Keller1999-208">[203]</a><a href="#cite_note-Wurst1984-227">[222]</a><a href="#cite_note-Kysilka1989-228">[223]</a> The total <a href="/wiki/Potency_(pharmacology)" title="Potency (pharmacology)">potency</a> varies greatly between species and even between specimens of a species collected or grown from the same strain.<a href="#cite_note-Bigwood1982-229">[224]</a> Because most psilocybin biosynthesis occurs early in the formation of <a href="/wiki/Basidiocarp" title="Basidiocarp">fruit bodies</a> or <a href="/wiki/Sclerotia" class="mw-redirect" title="Sclerotia">sclerotia</a>, younger, smaller mushrooms tend to have a higher concentration of the drug than larger, mature mushrooms.<a href="#cite_note-Gartz1992-230">[225]</a> In general, the psilocybin content of mushrooms is quite variable (ranging from almost nothing to 2.5% of the <a href="/wiki/Dry_matter" title="Dry matter">dry weight</a>)<a href="#cite_note-231">[226]</a><a href="#cite_note-Stafford1992-42">[41]</a>: 248  and depends on species, strain, growth and drying conditions, and mushroom size.<a href="#cite_note-Stamets_1996-34">[33]</a>: 36–41, 52  Cultivated mushrooms have less variability in psilocybin content than wild mushrooms.<a href="#cite_note-urlEMCDDA-232">[227]</a> The drug is more stable in dried than fresh mushrooms; dried mushrooms retain their potency for months or even years,<a href="#cite_note-Stamets_1996-34">[33]</a>: 51–5  while mushrooms stored fresh for four weeks contain only traces of the original psilocybin.<a href="#cite_note-Amsterdam2011-58">[56]</a> The psilocybin contents of dried <a href="/wiki/Herbarium" title="Herbarium">herbarium</a> specimens of Psilocybe semilanceata in one study were shown to decrease with the increasing age of the sample: collections dated 11, 33, or 118 years old contained 0.84%, 0.67%, and 0.014% (all dry weight), respectively.<a href="#cite_note-Ohenoja1987-233">[228]</a> Mature <a href="/wiki/Mycelia" class="mw-redirect" title="Mycelia">mycelia</a> contain some psilocybin, while young mycelia (recently <a href="/wiki/Germinated" class="mw-redirect" title="Germinated">germinated</a> from spores) lack appreciable amounts.<a href="#cite_note-Gross2000-234">[229]</a> Many species of mushrooms containing psilocybin also contain lesser amounts of the analog compounds <a href="/wiki/Baeocystin" title="Baeocystin">baeocystin</a> and <a href="/wiki/Norbaeocystin" title="Norbaeocystin">norbaeocystin</a>,<a href="#cite_note-Stamets_1996-34">[33]</a>: 38  chemicals thought to be biogenic <a href="/wiki/Precursor_(chemistry)" title="Precursor (chemistry)">precursors</a>.<a href="#cite_note-Ballesteros_2006-62">[60]</a>: 170  Although most species of psilocybin-containing mushrooms bruise blue when handled or damaged due to the <a href="/wiki/Redox" title="Redox">oxidization</a> of phenolic compounds, this reaction is not a definitive method of identification or determining a mushroom's potency.<a href="#cite_note-Bigwood1982-229">[224]</a><a href="#cite_note-Stamets_1996-34">[33]</a>: 56–58  <div class="mw-heading mw-heading2"><h2 id="Society_and_culture">Society and culture</h2>[<a href="/w/index.php?title=Psilocybin&action=edit&section=30" title="Edit section: Society and culture">edit</a>]</div> <div class="mw-heading mw-heading3"><h3 id="Legal_status">Legal status</h3>[<a href="/w/index.php?title=Psilocybin&action=edit&section=31" title="Edit section: Legal status">edit</a>]</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">Further information: <a href="/wiki/Legal_status_of_psilocybin_mushrooms" title="Legal status of psilocybin mushrooms">Legal status of psilocybin mushrooms</a> and <a href="/wiki/Psilocybin_decriminalization_in_the_United_States" title="Psilocybin decriminalization in the United States">Psilocybin decriminalization in the United States</a></div> <div class="excerpt-block"><style data-mw-deduplicate="TemplateStyles:r1066933788">.mw-parser-output .excerpt-hat .mw-editsection-like{font-style:normal}</style><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable dablink excerpt-hat selfref">This section is an excerpt from <a href="/wiki/Legal_status_of_psilocybin_mushrooms" title="Legal status of psilocybin mushrooms">Legal status of psilocybin mushrooms</a>.[<a class="external text" href="https://en.wikipedia.org/w/index.php?title=Legal_status_of_psilocybin_mushrooms&action=edit">edit</a>]</div><div class="excerpt"> <figure typeof="mw:File/Thumb"><a href="/wiki/File:Legality_of_psilocybin_mushrooms_map.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/9/90/Legality_of_psilocybin_mushrooms_map.svg/300px-Legality_of_psilocybin_mushrooms_map.svg.png" decoding="async" width="300" height="154" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/9/90/Legality_of_psilocybin_mushrooms_map.svg/450px-Legality_of_psilocybin_mushrooms_map.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/9/90/Legality_of_psilocybin_mushrooms_map.svg/600px-Legality_of_psilocybin_mushrooms_map.svg.png 2x" data-file-width="863" data-file-height="443" /></a><figcaption>Legality of activities with psilocybin mushrooms by country <style data-mw-deduplicate="TemplateStyles:r981673959">.mw-parser-output .legend{page-break-inside:avoid;break-inside:avoid-column}.mw-parser-output .legend-color{display:inline-block;min-width:1.25em;height:1.25em;line-height:1.25;margin:1px 0;text-align:center;border:1px solid black;background-color:transparent;color:black}.mw-parser-output .legend-text{}</style><div class="legend">  Legal</div><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r981673959"><div class="legend">  Legal for medical use and decriminalized</div><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r981673959"><div class="legend">  Ambiguous/partially legal/decriminalized</div><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r981673959"><div class="legend">  Illegal state with decriminalized cities</div><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r981673959"><div class="legend">  Illegal</div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r981673959"><div class="legend">  No information</div></figcaption></figure> The <a href="/wiki/Legal_status_of_psilocybin_mushrooms" title="Legal status of psilocybin mushrooms">legal status of unauthorised actions with psilocybin mushrooms</a> varies worldwide. Psilocybin and <a href="/wiki/Psilocin" title="Psilocin">psilocin</a> are listed as <a href="/wiki/Schedule_I_drug" class="mw-redirect" title="Schedule I drug">Schedule I drugs</a> under the United Nations 1971 <a href="/wiki/Convention_on_Psychotropic_Substances" title="Convention on Psychotropic Substances">Convention on Psychotropic Substances</a>.<a href="#cite_note-Legal_status_of_psilocybin_mushrooms_:0-235">[230]</a> Schedule I drugs are defined as drugs with a high potential for abuse or drugs that have no recognized medical uses. However, psilocybin mushrooms have had numerous medicinal<a href="#cite_note-236">[231]</a><a href="#cite_note-237">[232]</a><a href="#cite_note-238">[233]</a> and religious uses in <a href="/wiki/Psilocybin_mushroom#Early" title="Psilocybin mushroom">dozens of cultures throughout history</a> and have a significantly lower potential for abuse than other Schedule I drugs.<a href="#cite_note-239">[234]</a> Psilocybin mushrooms are not regulated by UN treaties.<a href="#cite_note-240">[235]</a> Many countries, however, have some level of regulation or prohibition of psilocybin mushrooms (for example, the US <a href="/wiki/Psychotropic_Substances_Act_(United_States)" title="Psychotropic Substances Act (United States)">Psychotropic Substances Act</a>, the UK <a href="/wiki/Misuse_of_Drugs_Act_1971" title="Misuse of Drugs Act 1971">Misuse of Drugs Act 1971</a>, and the Canadian <a href="/wiki/Controlled_Drugs_and_Substances_Act" title="Controlled Drugs and Substances Act">Controlled Drugs and Substances Act</a>). In some jurisdictions, Psilocybe spores are legal to sell and possess, because they contain neither psilocybin nor psilocin.<a href="#cite_note-241">[236]</a> In other jurisdictions, they are banned because they are items that are used in drug manufacture. A few jurisdictions (such as the US states of California,<a href="#cite_note-242">[237]</a> Georgia,<a href="#cite_note-243">[238]</a> and Idaho<a href="#cite_note-244">[239]</a>) have specifically prohibited the sale and possession of psilocybin mushroom spores. Cultivation of psilocybin mushrooms is considered drug manufacture in most jurisdictions and is often severely penalized, though some countries and one US state (New Mexico) has ruled that growing psilocybin mushrooms does not qualify as "manufacturing" a controlled substance.<a href="#cite_note-245">[240]</a></div></div> <div class="mw-heading mw-heading4"><h4 id="Advocacy_for_tolerance">Advocacy for tolerance</h4>[<a href="/w/index.php?title=Psilocybin&action=edit&section=32" title="Edit section: Advocacy for tolerance">edit</a>]</div> Despite being illegal in many typically Western countries, such as the UK, Australia and some US states, less conservative governments opt to nurture the legal use of psilocybin and other psychedelic drugs. In Amsterdam, Netherlands, authorities provide education and promotion on the safe use of psychedelic drugs, such as psilocybin, in an aim to reduce public harm.<a href="#cite_note-246">[241]</a> Similarly, religious groups like America's Uniao do Vegetal, UDV,<a href="#cite_note-Pollan_2018-247">[242]</a> use psychedelics in traditional ceremonies.<a href="#cite_note-248">[243]</a> A report from the U.S. Government Accountability Office (GAO) notes that people may petition the DEA for exemptions to use psilocybin for religious purposes.<a href="#cite_note-249">[244]</a> From 1 July 2023, the Australian medicines regulator has permitted psychiatrists to prescribe psilocybin for the therapeutic treatment of treatment-resistant depression.<a href="#cite_note-250">[245]</a> Advocates for legalization argue there is a lack of evidence of harm,<a href="#cite_note-251">[246]</a><a href="#cite_note-Johansen_2015-252">[247]</a> and potential use in treating certain mental health conditions. Research is difficult to conduct because of the legal status of psychoactive substances.<a href="#cite_note-Johnson_2018-253">[248]</a> Advocates for legalization also promote the utility of "<a href="/wiki/Ego_dissolution" class="mw-redirect" title="Ego dissolution">ego dissolution</a>"<a href="#cite_note-Pollan_2018-247">[242]</a> and argue bans are cultural discrimination against traditional users.<a href="#cite_note-254">[249]</a> In 2024, after calls for regulatory and legal change to expand terminally ill populations' access to controlled substances, two legal cases related to expanded access began moving through the federal courts under <a href="/wiki/Right-to-try_law" title="Right-to-try law">right-to-try law</a>. The Advanced Integrative Medicine Science (AIMS) Institute in concert with the NPA filed a series of lawsuits seeking both the rescheduling of and expanded right-to-try access to psilocybin.<a href="#cite_note-255">[250]</a> <div class="mw-heading mw-heading3"><h3 id="Usage">Usage</h3>[<a href="/w/index.php?title=Psilocybin&action=edit&section=33" title="Edit section: Usage">edit</a>]</div> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:Dried_Cubensis.jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/4/4e/Dried_Cubensis.jpg/220px-Dried_Cubensis.jpg" decoding="async" width="220" height="156" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/4/4e/Dried_Cubensis.jpg/330px-Dried_Cubensis.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/4/4e/Dried_Cubensis.jpg/440px-Dried_Cubensis.jpg 2x" data-file-width="1929" data-file-height="1371" /></a><figcaption>Dried Psilocybe mushrooms showing the characteristic blue bruising on the stems.</figcaption></figure> A 2009 national survey of drug use by the <a href="/wiki/US_Department_of_Health_and_Human_Services" class="mw-redirect" title="US Department of Health and Human Services">US Department of Health and Human Services</a> concluded that the number of first-time psilocybin mushroom users in the United States was roughly equivalent to the number of first-time users of cannabis.<a href="#cite_note-Bone2011-256">[251]</a> A June 2024 report by the <a href="/wiki/RAND_Corporation" title="RAND Corporation">RAND Corporation</a> suggests the total number of use days for psychedelics is two orders of magnitude smaller than it is for cannabis, and unlike people who use cannabis and many other drugs, infrequent users of psychedelics account for most of the total days of use.<a href="#cite_note-Kilmer_2024-257">[252]</a> The 2024 report by the RAND Corporation suggests psilocybin mushrooms may be the most prevalent psychedelic drug among adults in the United States.<a href="#cite_note-Kilmer_2024-257">[252]</a> In European countries, the lifetime prevalence estimates of psychedelic mushroom usage among young adults (15–34 years) range from 0.3% to 14.1%.<a href="#cite_note-EMDCCA2011-258">[253]</a> In modern Mexico, traditional ceremonial use survives among several indigenous groups, including the <a href="/wiki/Nahuas" title="Nahuas">Nahuas</a>, the <a href="/wiki/Matlatzinca_people" title="Matlatzinca people">Matlatzinca</a>, the <a href="/wiki/Totonacs" class="mw-redirect" title="Totonacs">Totonacs</a>, the <a href="/wiki/Mazatecs" class="mw-redirect" title="Mazatecs">Mazatecs</a>, <a href="/wiki/Mixe_people" title="Mixe people">Mixes</a>, <a href="/wiki/Zapotec_peoples" title="Zapotec peoples">Zapotecs</a>, and the <a href="/wiki/Chatinos" title="Chatinos">Chatino</a>. Although hallucinogenic Psilocybe species are abundant in low-lying areas of Mexico, most ceremonial use takes places in mountainous areas of elevations greater than 1,500 meters (4,900 ft). Guzmán suggests this is a vestige of Spanish colonial influence from several hundred years earlier, when mushroom use was persecuted by the <a href="/wiki/Catholic_Church" title="Catholic Church">Catholic Church</a>.<a href="#cite_note-Guzman2008-259">[254]</a> <div class="mw-heading mw-heading2"><h2 id="Research">Research</h2>[<a href="/w/index.php?title=Psilocybin&action=edit&section=34" title="Edit section: Research">edit</a>]</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/Psychedelic_therapy" title="Psychedelic therapy">Psychedelic therapy</a> and <a href="/wiki/List_of_investigational_hallucinogens_and_entactogens" title="List of investigational hallucinogens and entactogens">List of investigational hallucinogens and entactogens</a></div> Psilocybin has been a subject of clinical research since the early 1960s, when the <a href="/wiki/Harvard_Psilocybin_Project" title="Harvard Psilocybin Project">Harvard Psilocybin Project</a> evaluated the <a href="/wiki/Psilocybin_therapy" title="Psilocybin therapy">potential value of psilocybin</a> as a treatment for certain <a href="/wiki/Personality_disorder" title="Personality disorder">personality disorders</a>.<a href="#cite_note-Wark2009-260">[255]</a> Beginning in the 2000s, psilocybin has been investigated for its possible role in the treatment of <a href="/wiki/Nicotine_dependence" title="Nicotine dependence">nicotine dependence</a>, <a href="/wiki/Alcohol_dependence" title="Alcohol dependence">alcohol dependence</a>, <a href="/wiki/Obsessive%E2%80%93compulsive_disorder" title="Obsessive–compulsive disorder">obsessive–compulsive disorder</a> (OCD), <a href="/wiki/Cluster_headache" title="Cluster headache">cluster headache</a>, <a href="/wiki/Psycho-oncology#Psychological" title="Psycho-oncology">cancer-related existential distress</a>,<a href="#cite_note-Serreau2023-127">[122]</a><a href="#cite_note-Goel2022-261">[256]</a> <a href="/wiki/Anxiety_disorder" title="Anxiety disorder">anxiety disorders</a>, and certain <a href="/wiki/Mood_disorder" title="Mood disorder">mood disorders</a>.<a href="#cite_note-Marley2010-35">[34]</a>: 179–81 <a href="#cite_note-DosSantos2016-262">[257]</a><a href="#cite_note-Ross2016-263">[258]</a> It is also being studied in people with <a href="/wiki/Parkinson%27s_disease" title="Parkinson's disease">Parkinson's disease</a>.<a href="#cite_note-BradleySakaiFernandes2023-264">[259]</a><a href="#cite_note-BradleySakaiFernandes-Osterhold2024-265">[260]</a> In 2018, the United States <a href="/wiki/Food_and_Drug_Administration" title="Food and Drug Administration">Food and Drug Administration</a> (FDA) granted <a href="/wiki/Breakthrough_therapy" title="Breakthrough therapy">breakthrough therapy</a> designation for psilocybin-assisted therapy for <a href="/wiki/Treatment-resistant_depression" title="Treatment-resistant depression">treatment-resistant depression</a>.<a href="#cite_note-Compasspathways2018-266">[261]</a><a href="#cite_note-Staines2019-267">[262]</a> A systematic review published in 2021 found that the use of psilocybin as a pharmaceutical substance was associated with reduced intensity of depression symptoms.<a href="#cite_note-Wieckiewicz2021-268">[263]</a> The role of psilocybin as a possible <a href="/wiki/Psychoplastogen" title="Psychoplastogen">psychoplastogen</a> is also being examined.<a href="#cite_note-VargasMeyerAvanes2021-169">[164]</a><a href="#cite_note-Olson2021-170">[165]</a><a href="#cite_note-DeVos2021-171">[166]</a> It is under development by <a href="/wiki/Compass_Pathways" title="Compass Pathways">Compass Pathways</a>, <a href="/wiki/Cybin" title="Cybin">Cybin</a>, and several other companies.<a href="#cite_note-RheeDavoudianSanacora2023-269">[264]</a><a href="#cite_note-AdayBarnettGrossman2023-270">[265]</a> <div class="mw-heading mw-heading3"><h3 id="Depression">Depression</h3>[<a href="/w/index.php?title=Psilocybin&action=edit&section=35" title="Edit section: Depression">edit</a>]</div> <a href="/wiki/Clinical_trial" title="Clinical trial">Clinical trials</a>, including both <a href="/wiki/Open-label_study" class="mw-redirect" title="Open-label study">open-label trials</a> and <a href="/wiki/Blinded_experiment" title="Blinded experiment">double-blind</a> <a href="/wiki/Randomized_controlled_trial" title="Randomized controlled trial">randomized controlled trials</a>, have found that single doses of psilocybin produce rapid and long-lasting <a href="/wiki/Antidepressant" title="Antidepressant">antidepressant</a> effects outperforming <a href="/wiki/Placebo" title="Placebo">placebo</a> in people with <a href="/wiki/Major_depressive_disorder" title="Major depressive disorder">major depressive disorder</a> and <a href="/wiki/Treatment-resistant_depression" title="Treatment-resistant depression">treatment-resistant depression</a>.<a href="#cite_note-WangKimChoi2024-271">[266]</a> Combined with brief <a href="/wiki/Psychotherapy" title="Psychotherapy">psychological support</a> in a <a href="/wiki/Phases_of_clinical_research#Phase_2" title="Phases of clinical research">phase 2</a> trial, it has been found to produce <a href="/wiki/Dose_dependency" class="mw-redirect" title="Dose dependency">dose-dependent</a> improvements in depressive symptoms, with 25 mg (a moderate dose) more effective than 10 mg (a low dose) and 10 mg more effective than 1 mg (non-psychoactive and equivalent to <a href="/wiki/Placebo" title="Placebo">placebo</a>).<a href="#cite_note-WangKimChoi2024-271">[266]</a><a href="#cite_note-GoodwinAaronsonAlvarez2022-272">[267]</a> The antidepressant effects of psilocybin with psychological support have been found to last at least 6 weeks following a single dose.<a href="#cite_note-WangKimChoi2024-271">[266]</a><a href="#cite_note-GoodwinAaronsonAlvarez2022-272">[267]</a><a href="#cite_note-RaisonSanacoraWoolley2023-273">[268]</a> However, some trials have not found psilocybin to significantly outperform placebo in the treatment of depression.<a href="#cite_note-WangKimChoi2024-271">[266]</a> In addition, a phase 2 trial found that two 25 mg doses of psilocybin 3 weeks apart versus daily treatment with the <a href="/wiki/Selective_serotonin_reuptake_inhibitor" title="Selective serotonin reuptake inhibitor">selective serotonin reuptake inhibitor</a> (SSRI) <a href="/wiki/Escitalopram" title="Escitalopram">escitalopram</a> (Lexapro) for 6 weeks (plus two putatively non-psychoactive 1 mg doses of psilocybin 3 weeks apart) did not show a <a href="/wiki/Statistical_significance" title="Statistical significance">statistically significant</a> difference in reduction of depressive symptoms between groups.<a href="#cite_note-WangKimChoi2024-271">[266]</a><a href="#cite_note-Carhart-HarrisGiribaldiWatts2021-274">[269]</a> However, reductions in depressive symptoms were numerically greater with psilocybin, some <a href="/wiki/Outcome_measure" title="Outcome measure">secondary measures</a> favored psilocybin, and the rate of <a href="/wiki/Remission_(medicine)" title="Remission (medicine)">remission</a> was statistically higher with psilocybin (57% with psilocybin vs. 28% with escitalopram).<a href="#cite_note-WangKimChoi2024-271">[266]</a><a href="#cite_note-Carhart-HarrisGiribaldiWatts2021-274">[269]</a> In any case, the antidepressant <a href="/wiki/Effect_size" title="Effect size">effect size</a> of psilocybin over escitalopram appears to be small.<a href="#cite_note-HsuTsaiKao2024-275">[270]</a> <a href="/wiki/Unblinding" class="mw-redirect" title="Unblinding">Functional unblinding</a> by their psychoactive effects and <a href="/wiki/Subject-expectancy_effect" title="Subject-expectancy effect">positive psychological expectancy effects</a> (i.e., the <a href="/wiki/Placebo_effect" class="mw-redirect" title="Placebo effect">placebo effect</a>) are major limitations and sources of <a href="/wiki/Bias" title="Bias">bias</a> of clinical trials of psilocybin and other psychedelics for treatment of depression.<a href="#cite_note-MuthukumaraswamyForsythLumley2021-276">[271]</a><a href="#cite_note-LedwosRosenblatBlumberger2022-277">[272]</a><a href="#cite_note-HovmandPoulsenArnfred2023-278">[273]</a><a href="#cite_note-SzigetiHeifets2024-279">[274]</a> Relatedly, most of the therapeutic benefit of conventional <a href="/wiki/Antidepressant" title="Antidepressant">antidepressants</a> like the SSRIs for depression appears to be attributable to the <a href="/wiki/Placebo_response" class="mw-redirect" title="Placebo response">placebo response</a>.<a href="#cite_note-Kirsch2019-280">[275]</a><a href="#cite_note-HengartnerPlöderl2018-281">[276]</a> It has been proposed that psychedelics like psilocybin may in fact act as <a href="/wiki/Active_placebo" title="Active placebo">active</a> "super <a href="/wiki/Placebo" title="Placebo">placebos</a>" when used for therapeutic purposes.<a href="#cite_note-DupuisVeissière2022-282">[277]</a><a href="#cite_note-vanElkYaden2022-283">[278]</a> As of September 2024, psilocybin and other psychedelics (excluding <a href="/wiki/MDMA" title="MDMA">MDMA</a>) have only been assessed in up to phase 2 clinical trials for psychiatric disorders and have not yet completed larger and more rigorous <a href="/wiki/Phases_of_clinical_research#Phase_III" title="Phases of clinical research">phase 3</a> trials or received regulatory approval for medical use.<a href="#cite_note-AdisInsight-31">[30]</a><a href="#cite_note-WangKimChoi2024-271">[266]</a><a href="#cite_note-YaoGuoLu2024-284">[279]</a> A potential risk of frequent repeated use of psilocybin and other serotonergic psychedelics for psychiatric disorders is <a href="/wiki/Cardiac_fibrosis" title="Cardiac fibrosis">cardiac fibrosis</a> and <a href="/wiki/Valvular_heart_disease" title="Valvular heart disease">valvulopathy</a> caused by <a href="/wiki/Serotonin" title="Serotonin">serotonin</a> <a href="/wiki/5-HT2B_receptor" title="5-HT2B receptor">5-HT2B receptor</a> activation.<a href="#cite_note-TagenMantuanivanHeerden2023-188">[183]</a><a href="#cite_note-RouaudCalderHasler2024-189">[184]</a> However, single high doses or widely spaced doses (e.g., months) are widely thought to be safe and concerns about cardiac toxicity apply more to chronic <a href="/wiki/Psychedelic_microdosing" title="Psychedelic microdosing">psychedelic microdosing</a> or very frequent use (e.g., weekly).<a href="#cite_note-TagenMantuanivanHeerden2023-188">[183]</a><a href="#cite_note-RouaudCalderHasler2024-189">[184]</a> <div class="mw-heading mw-heading2"><h2 id="See_also">See also</h2>[<a href="/w/index.php?title=Psilocybin&action=edit&section=36" title="Edit section: See also">edit</a>]</div> <style data-mw-deduplicate="TemplateStyles:r1266661725">.mw-parser-output .portalbox{padding:0;margin:0.5em 0;display:table;box-sizing:border-box;max-width:175px;list-style:none}.mw-parser-output .portalborder{border:1px solid var(--border-color-base,#a2a9b1);padding:0.1em;background:var(--background-color-neutral-subtle,#f8f9fa)}.mw-parser-output .portalbox-entry{display:table-row;font-size:85%;line-height:110%;height:1.9em;font-style:italic;font-weight:bold}.mw-parser-output .portalbox-image{display:table-cell;padding:0.2em;vertical-align:middle;text-align:center}.mw-parser-output .portalbox-link{display:table-cell;padding:0.2em 0.2em 0.2em 0.3em;vertical-align:middle}@media(min-width:720px){.mw-parser-output .portalleft{margin:0.5em 1em 0.5em 0}.mw-parser-output .portalright{clear:right;float:right;margin:0.5em 0 0.5em 1em}}</style><ul role="navigation" aria-label="Portals" class="noprint portalbox portalborder portalright"> <li class="portalbox-entry"><img alt="" src="//upload.wikimedia.org/wikipedia/commons/thumb/4/42/Karl_Johanssvamp%2C_Iduns_kokbok.png/25px-Karl_Johanssvamp%2C_Iduns_kokbok.png" decoding="async" width="25" height="28" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/4/42/Karl_Johanssvamp%2C_Iduns_kokbok.png/38px-Karl_Johanssvamp%2C_Iduns_kokbok.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/4/42/Karl_Johanssvamp%2C_Iduns_kokbok.png/51px-Karl_Johanssvamp%2C_Iduns_kokbok.png 2x" data-file-width="1105" data-file-height="1215" /><a href="/wiki/Portal:Fungi" title="Portal:Fungi">Fungi portal</a></li></ul> <ul><li><a href="/wiki/List_of_entheogens" class="mw-redirect" title="List of entheogens">List of entheogens</a></li> <li><a href="/wiki/4-AcO-DMT" title="4-AcO-DMT">4-AcO-DMT</a> (psilacetin)</li> <li><a href="/wiki/Mushroom_edible" title="Mushroom edible">Mushroom edible</a></li> <li><a href="/wiki/Psychedelic_microdosing" title="Psychedelic microdosing">Psychedelic microdosing</a></li> <li><a href="/wiki/Psychoactive_plant" title="Psychoactive plant">Psychoactive plant</a></li> <li><a href="/wiki/Stoned_ape_theory" title="Stoned ape theory">Stoned ape theory</a></li> <li><a href="/wiki/Soma_(drink)" title="Soma (drink)">Soma (drink)</a></li></ul> <div class="mw-heading mw-heading2"><h2 id="Explanatory_notes">Explanatory notes</h2>[<a href="/w/index.php?title=Psilocybin&action=edit&section=37" title="Edit section: Explanatory notes">edit</a>]</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 .reflist-columns-3{column-width:25em}.mw-parser-output .reflist-columns{margin-top:0.3em}.mw-parser-output .reflist-columns ol{margin-top:0}.mw-parser-output .reflist-columns li{page-break-inside:avoid;break-inside:avoid-column}.mw-parser-output .reflist-upper-alpha{list-style-type:upper-alpha}.mw-parser-output .reflist-upper-roman{list-style-type:upper-roman}.mw-parser-output .reflist-lower-alpha{list-style-type:lower-alpha}.mw-parser-output .reflist-lower-greek{list-style-type:lower-greek}.mw-parser-output .reflist-lower-roman{list-style-type:lower-roman}</style><div class="reflist reflist-lower-alpha"> <div class="mw-references-wrap"><ol class="references"> <li id="cite_note-23"><a href="#cite_ref-23">^</a> Synonyms and alternate spellings of psilocybin include 4-PO-DMT (PO: <a href="/wiki/Phosphate" title="Phosphate">phosphate</a>; DMT: <a href="/wiki/Dimethyltryptamine" class="mw-redirect" title="Dimethyltryptamine">dimethyltryptamine</a>), psilocybine, psilocibin, psilocybinum, psilotsibin, and psilocin phosphate ester, among others.<a href="#cite_note-Pubchem-22">[22]</a> </li> <li id="cite_note-52"><a href="#cite_ref-52">^</a> The <a href="/wiki/EMCDDA" class="mw-redirect" title="EMCDDA">EMCDDA</a> lists the general-purpose websites <a href="/wiki/Erowid" title="Erowid">Erowid</a>, <a href="/wiki/Lycaeum" class="mw-redirect" title="Lycaeum">Lycaeum</a>, <a rel="nofollow" class="external text" href="http://www.mycotopia.net">Mycotopia</a>, <a rel="nofollow" class="external text" href="https://www.shroomery.org">The Shroomery</a>, <a rel="nofollow" class="external text" href="http://www.mushroomjohn.com">MushroomJohn</a> and <a rel="nofollow" class="external text" href="http://www.entheogenreview.com">The Entheogen Review</a>. Regional sites focusing on hallucinogenic mushrooms listed were <a rel="nofollow" class="external text" href="http://www.mushroom.dk">Copenhagen Mushroom Link</a> (Denmark), <a rel="nofollow" class="external text" href="http://www.champis.fr.tc">Champis</a> (France), <a rel="nofollow" class="external text" href="https://www.daath.hu">Daath</a> (Hungary), <a rel="nofollow" class="external text" href="http://www.gratisweb·com/delysid">Delysid</a> (Spain), <a rel="nofollow" class="external text" href="https://enteogeneos.com.sapo.pt">Enteogeneos</a> (Portugal), <a rel="nofollow" class="external text" href="http://drogy.jinak.cz/houbicky">Kouzelné houbičky</a> (Czech Republic), <a rel="nofollow" class="external text" href="http://www.norshroom.org">Norshroom</a> (Norway), <a rel="nofollow" class="external text" href="http://planetahongo.tripod.com">Planetahongo</a> (Spain), <a rel="nofollow" class="external text" href="http://knarkkorven.magiskamolekyler.org/svampinfo/index.html">Svampinfo</a> (Sweden), and <a rel="nofollow" class="external text" href="http://trippi.info/taikasieniforum">Taikasieniforum</a> (Finland). It also listed <a rel="nofollow" class="external text" href="http://www.magic-mushrooms.net">Magic-Mushrooms.net</a>. The report detailed several additional sites selling <a href="/wiki/Spore_print" title="Spore print">spore prints</a> in 2006, but noted that many of these had ceased operation. </li> <li id="cite_note-64"><a href="#cite_ref-64">^</a> Percentages are derived from a <a href="/wiki/Blind_experiment#Double-blind_trials" class="mw-redirect" title="Blind experiment">non-blind</a> clinical study of 30 individuals who were given a dosage of 8–12 milligrams of psilocybin; from Passie (2002),<a href="#cite_note-Passie2002-2">[2]</a> citing Quentin (1960).<a href="#cite_note-Quentin1960-63">[61]</a> </li> <li id="cite_note-91"><a href="#cite_ref-91">^</a> One of the reported fatalities, that of a 22-year-old French man who died in 1993,<a href="#cite_note-Gerault1996-89">[86]</a> was later challenged in the literature by Jochen Gartz and colleagues, who concluded "the few reported data concerning the victim are insufficient to exclude other possible causes of the fatality".<a href="#cite_note-Gartz1996-90">[87]</a> </li> <li id="cite_note-118"><a href="#cite_ref-118">^</a> The academic communities' approval for the methodology employed is exemplified by the quartet of commentaries published in the journal <a href="/wiki/Psychopharmacology_(journal)" title="Psychopharmacology (journal)">Psychopharmacology</a> titled "<a rel="nofollow" class="external text" href="http://www.hopkinsmedicine.org/Press_releases/2006/GriffithsCommentaries.pdf">Commentary on: Psilocybin can occasion mystical-type experiences having substantial and sustained personal meaning and spiritual experience by Griffiths et al.</a>", by HD Kleber (pp. 291–292), DE Nichols (pp. 284–286), CR Schuster (pp. 289–290), and SH Snyder (pp. 287–288). </li> </ol></div></div> <div class="mw-heading mw-heading2"><h2 id="References">References</h2>[<a href="/w/index.php?title=Psilocybin&action=edit&section=38" title="Edit section: References">edit</a>]</div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239543626"><div class="reflist"> <div class="mw-references-wrap mw-references-columns"><ol class="references"> <li id="cite_note-JohnsonGriffithsHendricks2018-1">^ <a href="#cite_ref-JohnsonGriffithsHendricks2018_1-0">a</a> <a href="#cite_ref-JohnsonGriffithsHendricks2018_1-1">b</a> <style data-mw-deduplicate="TemplateStyles:r1238218222">.mw-parser-output cite.citation{font-style:inherit;word-wrap:break-word}.mw-parser-output .citation q{quotes:"\"""\"""'""'"}.mw-parser-output .citation:target{background-color:rgba(0,127,255,0.133)}.mw-parser-output .id-lock-free.id-lock-free a{background:url("//upload.wikimedia.org/wikipedia/commons/6/65/Lock-green.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-limited.id-lock-limited a,.mw-parser-output .id-lock-registration.id-lock-registration a{background:url("//upload.wikimedia.org/wikipedia/commons/d/d6/Lock-gray-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-subscription.id-lock-subscription a{background:url("//upload.wikimedia.org/wikipedia/commons/a/aa/Lock-red-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .cs1-ws-icon a{background:url("//upload.wikimedia.org/wikipedia/commons/4/4c/Wikisource-logo.svg")right 0.1em center/12px no-repeat}body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-free a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-limited a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-registration a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-subscription a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .cs1-ws-icon a{background-size:contain;padding:0 1em 0 0}.mw-parser-output .cs1-code{color:inherit;background:inherit;border:none;padding:inherit}.mw-parser-output .cs1-hidden-error{display:none;color:var(--color-error,#d33)}.mw-parser-output .cs1-visible-error{color:var(--color-error,#d33)}.mw-parser-output .cs1-maint{display:none;color:#085;margin-left:0.3em}.mw-parser-output .cs1-kern-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right{padding-right:0.2em}.mw-parser-output .citation .mw-selflink{font-weight:inherit}@media screen{.mw-parser-output .cs1-format{font-size:95%}html.skin-theme-clientpref-night .mw-parser-output .cs1-maint{color:#18911f}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .cs1-maint{color:#18911f}}</style><cite id="CITEREFJohnsonGriffithsHendricksHenningfield2018" class="citation journal cs1">Johnson MW, Griffiths RR, Hendricks PS, Henningfield JE (November 2018). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6791528">"The abuse potential of medical psilocybin according to the 8 factors of the Controlled Substances Act"</a>. Neuropharmacology. 142: 143–166. <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.2018.05.012">10.1016/j.neuropharm.2018.05.012</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/PMC6791528">6791528</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/29753748">29753748</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=The+abuse+potential+of+medical+psilocybin+according+to+the+8+factors+of+the+Controlled+Substances+Act&rft.volume=142&rft.pages=%3Cspan+class%3D%22nowrap%22%3E143-%3C%2Fspan%3E166&rft.date=2018-11&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC6791528%23id-name%3DPMC&rft_id=info%3Apmid%2F29753748&rft_id=info%3Adoi%2F10.1016%2Fj.neuropharm.2018.05.012&rft.aulast=Johnson&rft.aufirst=MW&rft.au=Griffiths%2C+RR&rft.au=Hendricks%2C+PS&rft.au=Henningfield%2C+JE&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC6791528&rfr_id=info%3Asid%2Fen.wikipedia.org%3APsilocybin" class="Z3988"> </li> <li id="cite_note-Passie2002-2">^ <a href="#cite_ref-Passie2002_2-0">a</a> <a href="#cite_ref-Passie2002_2-1">b</a> <a href="#cite_ref-Passie2002_2-2">c</a> <a href="#cite_ref-Passie2002_2-3">d</a> <a href="#cite_ref-Passie2002_2-4">e</a> <a href="#cite_ref-Passie2002_2-5">f</a> <a href="#cite_ref-Passie2002_2-6">g</a> <a href="#cite_ref-Passie2002_2-7">h</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFPassieSeifertSchneiderEmrich2002" class="citation journal cs1">Passie T, Seifert J, Schneider U, Emrich HM (October 2002). 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Psychopharmacology. 172 (2): 145–156. <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%2Fs00213-003-1640-6">10.1007/s00213-003-1640-6</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/14615876">14615876</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:15263504">15263504</a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20200418005513/https://maps.org/research-archive/w3pb/2004/2004_Hasler_20465_2.pdf">Archived</a> (PDF) from the original on April 18, 2020. Retrieved April 10, 2019.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Psychopharmacology&rft.atitle=Acute+psychological+and+physiological+effects+of+psilocybin+in+healthy+humans%3A+a+double-blind%2C+placebo-controlled+dose-effect+study&rft.volume=172&rft.issue=2&rft.pages=%3Cspan+class%3D%22nowrap%22%3E145-%3C%2Fspan%3E156&rft.date=2004-03&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A15263504%23id-name%3DS2CID&rft_id=info%3Apmid%2F14615876&rft_id=info%3Adoi%2F10.1007%2Fs00213-003-1640-6&rft.aulast=Hasler&rft.aufirst=F&rft.au=Grimberg%2C+U&rft.au=Benz%2C+MA&rft.au=Huber%2C+T&rft.au=Vollenweider%2C+FX&rft_id=http%3A%2F%2Fwww.maps.org%2Fresearch-archive%2Fw3pb%2F2004%2F2004_Hasler_20465_2.pdf&rfr_id=info%3Asid%2Fen.wikipedia.org%3APsilocybin" class="Z3988"> </li> <li id="cite_note-Ballesteros_2006-62">^ <a href="#cite_ref-Ballesteros_2006_62-0">a</a> <a href="#cite_ref-Ballesteros_2006_62-1">b</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFBallesterosRamónIturraldeMartínez-Arrieta2006" class="citation book cs1">Ballesteros S, Ramón MF, Iturralde MJ, Martínez-Arrieta R (2006). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=ovGcMmz5emUC&pg=PA167">"Natural sources of drugs of abuse: magic mushrooms"</a>. In Cole SM (ed.). New Research on Street Drugs. New York, New York: <a href="/wiki/Nova_Science_Publishers" title="Nova Science Publishers">Nova Science Publishers</a>. pp. 167–186. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1-59454-961-8" title="Special:BookSources/978-1-59454-961-8"><bdi>978-1-59454-961-8</bdi></a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20170404021804/https://books.google.com/books?id=ovGcMmz5emUC&pg=PA167">Archived</a> from the original on April 4, 2017. Retrieved February 27, 2016.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Natural+sources+of+drugs+of+abuse%3A+magic+mushrooms&rft.btitle=New+Research+on+Street+Drugs&rft.place=New+York%2C+New+York&rft.pages=%3Cspan+class%3D%22nowrap%22%3E167-%3C%2Fspan%3E186&rft.pub=Nova+Science+Publishers&rft.date=2006&rft.isbn=978-1-59454-961-8&rft.aulast=Ballesteros&rft.aufirst=S&rft.au=Ram%C3%B3n%2C+MF&rft.au=Iturralde%2C+MJ&rft.au=Mart%C3%ADnez-Arrieta%2C+R&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DovGcMmz5emUC%26pg%3DPA167&rfr_id=info%3Asid%2Fen.wikipedia.org%3APsilocybin" class="Z3988"> </li> <li id="cite_note-Quentin1960-63"><a href="#cite_ref-Quentin1960_63-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFQuentin1960" class="citation thesis cs1 cs1-prop-foreign-lang-source">Quentin AM (1960). La Psilocybine en Psychiatrie Clinique et Experimentale [Psilocybin in Clinical and Experimental Psychiatry] (PhD thesis) (in French). Paris, France: Paris University Medical Dissertation.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Adissertation&rft.title=La+Psilocybine+en+Psychiatrie+Clinique+et+Experimentale&rft.degree=PhD&rft.inst=Paris+University+Medical+Dissertation&rft.date=1960&rft.aulast=Quentin&rft.aufirst=AM&rfr_id=info%3Asid%2Fen.wikipedia.org%3APsilocybin" class="Z3988"> </li> <li id="cite_note-65"><a href="#cite_ref-65">^</a> See for example: <ul><li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFIsbell1959" class="citation journal cs1">Isbell H (1959). "Comparison of the reactions induced by psilocybin and LSD-25 in man". Psychopharmacologia. 1 (1): 29–38. <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%2FBF00408109">10.1007/BF00408109</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/14405870">14405870</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:19508675">19508675</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Psychopharmacologia&rft.atitle=Comparison+of+the+reactions+induced+by+psilocybin+and+LSD-25+in+man&rft.volume=1&rft.issue=1&rft.pages=%3Cspan+class%3D%22nowrap%22%3E29-%3C%2Fspan%3E38&rft.date=1959&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A19508675%23id-name%3DS2CID&rft_id=info%3Apmid%2F14405870&rft_id=info%3Adoi%2F10.1007%2FBF00408109&rft.aulast=Isbell&rft.aufirst=H&rfr_id=info%3Asid%2Fen.wikipedia.org%3APsilocybin" class="Z3988"></li> <li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFHollisterPrusmackPaulsenRosenquist1960" class="citation journal cs1">Hollister LE, Prusmack JJ, Paulsen A, Rosenquist N (November 1960). 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"Some observations on psilocybin, a new hallucinogen, in volunteer subjects". Comprehensive Psychiatry. 1: 8–17. <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%2FS0010-440X%2860%2980045-4">10.1016/S0010-440X(60)80045-4</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/14420328">14420328</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Comprehensive+Psychiatry&rft.atitle=Some+observations+on+psilocybin%2C+a+new+hallucinogen%2C+in+volunteer+subjects&rft.volume=1&rft.pages=%3Cspan+class%3D%22nowrap%22%3E8-%3C%2Fspan%3E17&rft.date=1960-02&rft_id=info%3Adoi%2F10.1016%2FS0010-440X%2860%2980045-4&rft_id=info%3Apmid%2F14420328&rft.aulast=Malitz&rft.aufirst=S&rft.au=Esecover%2C+H&rft.au=Wilkens%2C+B&rft.au=Hoch%2C+PH&rfr_id=info%3Asid%2Fen.wikipedia.org%3APsilocybin" class="Z3988">[<a href="/wiki/Wikipedia:Link_rot" title="Wikipedia:Link rot">permanent dead link</a>‍]</li> <li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFRinkelAtwellDimascioBrown1960" class="citation journal cs1">Rinkel M, Atwell CR, Dimascio A, Brown J (February 1960). "Experimental psychiatry. V. Psilocybine, a new psychotogenic drug". 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Expert Review of Clinical Pharmacology (Review). 13 (8): 847–856. <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%2F17512433.2020.1794811">10.1080/17512433.2020.1794811</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/32648791">32648791</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:220472473">220472473</a>.</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+Clinical+Pharmacology&rft.atitle=Management+of+overdoses+of+salvia%2C+kratom%2C+and+psilocybin+mushrooms%3A+a+literature+review&rft.volume=13&rft.issue=8&rft.pages=%3Cspan+class%3D%22nowrap%22%3E847-%3C%2Fspan%3E856&rft.date=2020-08&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A220472473%23id-name%3DS2CID&rft_id=info%3Apmid%2F32648791&rft_id=info%3Adoi%2F10.1080%2F17512433.2020.1794811&rft.aulast=Reinert&rft.aufirst=JP&rft.au=Colunga%2C+K&rft.au=Etuk%2C+A&rft.au=Richardson%2C+V&rft.au=Dunn%2C+RL&rfr_id=info%3Asid%2Fen.wikipedia.org%3APsilocybin" class="Z3988"> </li> <li id="cite_note-Merck13th-86">^ <a href="#cite_ref-Merck13th_86-0">a</a> <a href="#cite_ref-Merck13th_86-1">b</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFO'NeilSmithHeckelmanObenchain2001" class="citation book cs1">O'Neil MJ, Smith A, Heckelman PE, Obenchain JR, Gallipeau JR, D'Arecca MA, eds. 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The World Journal of Biological Psychiatry. 5 (1): 49–53. <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%2F15622970410029908">10.1080/15622970410029908</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/15048636">15048636</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:44321700">44321700</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=The+World+Journal+of+Biological+Psychiatry&rft.atitle=Khat+and+mushrooms+associated+with+psychosis&rft.volume=5&rft.issue=1&rft.pages=%3Cspan+class%3D%22nowrap%22%3E49-%3C%2Fspan%3E53&rft.date=2004-01&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A44321700%23id-name%3DS2CID&rft_id=info%3Apmid%2F15048636&rft_id=info%3Adoi%2F10.1080%2F15622970410029908&rft.aulast=Nielen&rft.aufirst=RJ&rft.au=van+der+Heijden%2C+FM&rft.au=Tuinier%2C+S&rft.au=Verhoeven%2C+WM&rfr_id=info%3Asid%2Fen.wikipedia.org%3APsilocybin" class="Z3988"> </li> <li id="cite_note-Geyer1998-99"><a href="#cite_ref-Geyer1998_99-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFGeyer1998" class="citation journal cs1">Geyer MA (July 1998). 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Neuropsychopharmacology. 44 (7): 1328–1334. <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%2Fs41386-019-0324-9">10.1038/s41386-019-0324-9</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/PMC6785028">6785028</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/30685771">30685771</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=Psychedelic+effects+of+psilocybin+correlate+with+serotonin+2A+receptor+occupancy+and+plasma+psilocin+levels&rft.volume=44&rft.issue=7&rft.pages=%3Cspan+class%3D%22nowrap%22%3E1328-%3C%2Fspan%3E1334&rft.date=2019-06&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC6785028%23id-name%3DPMC&rft_id=info%3Apmid%2F30685771&rft_id=info%3Adoi%2F10.1038%2Fs41386-019-0324-9&rft.aulast=Madsen&rft.aufirst=MK&rft.au=Fisher%2C+PM&rft.au=Burmester%2C+D&rft.au=Dyssegaard%2C+A&rft.au=Stenb%C3%A6k%2C+DS&rft.au=Kristiansen%2C+S&rft.au=Johansen%2C+SS&rft.au=Lehel%2C+S&rft.au=Linnet%2C+K&rft.au=Svarer%2C+C&rft.au=Erritzoe%2C+D&rft.au=Ozenne%2C+B&rft.au=Knudsen%2C+GM&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC6785028&rfr_id=info%3Asid%2Fen.wikipedia.org%3APsilocybin" class="Z3988"> </li> <li id="cite_note-Canal2018-149"><a href="#cite_ref-Canal2018_149-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFCanal2018" class="citation journal cs1">Canal CE (2018). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6136989">"Serotonergic Psychedelics: Experimental Approaches for Assessing Mechanisms of Action"</a>. Handb Exp Pharmacol. Handbook of Experimental Pharmacology. 252: 227–260. <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_107">10.1007/164_2018_107</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/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/PMC6136989">6136989</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/29532180">29532180</a>. <q>Reports from clinical trials conclude that the psychedelic effects of psilocybin and LSD are mediated by 5-HT2A receptors, because they are blocked by ketanserin (40 mg, P.O.), typically viewed as a selective 5-HT2A antagonist (Kometer et al. 2012; Kraehenmann et al. 2017; Preller et al. 2017; Quednow et al. 2012). Haloperidol, typically viewed as a selective dopamine D2 antagonist, is much less effective than ketanserin at blocking psilocybin's effects, but risperidone, an antipsychotic with combined D2/5-HT2 activity, is as effective as ketanserin (Vollenweider et al. 1998).</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Handb+Exp+Pharmacol&rft.atitle=Serotonergic+Psychedelics%3A+Experimental+Approaches+for+Assessing+Mechanisms+of+Action&rft.volume=252&rft.pages=%3Cspan+class%3D%22nowrap%22%3E227-%3C%2Fspan%3E260&rft.date=2018&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC6136989%23id-name%3DPMC&rft_id=info%3Apmid%2F29532180&rft_id=info%3Adoi%2F10.1007%2F164_2018_107&rft.isbn=978-3-030-10560-0&rft.aulast=Canal&rft.aufirst=CE&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC6136989&rfr_id=info%3Asid%2Fen.wikipedia.org%3APsilocybin" class="Z3988"> </li> <li id="cite_note-DeGregorioEnnsNuñez2018-150"><a href="#cite_ref-DeGregorioEnnsNuñez2018_150-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFDe_GregorioEnnsNuñezPosa2018" class="citation book cs1">De Gregorio D, Enns JP, Nuñez NA, Posa L, Gobbi G (2018). "D-Lysergic acid diethylamide, psilocybin, and other classic hallucinogens: Mechanism of action and potential therapeutic applications in mood disorders". Psychedelic Neuroscience. Progress in Brain Research. Vol. 242. pp. 69–96. <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%2Fbs.pbr.2018.07.008">10.1016/bs.pbr.2018.07.008</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-12-814255-4" title="Special:BookSources/978-0-12-814255-4"><bdi>978-0-12-814255-4</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/30471683">30471683</a>. <q>Noteworthy, the activation of postsynaptic 5HT2A receptor in layer V of the medial prefrontal cortex (mPFC) is considered to be responsible for the visual hallucinations produced by LSD and other psychedelic drugs such as psilocybin (Jakab and Goldman-Rakic, 1998; Vollenweider and Kometer, 2010) (see Fig. 2). [...] Although the classic hallucinogens LSD and psilocybin do not have a direct affinity for glutamate receptors, several animal studies have highlighted that glutamate carries a significant weight of the overall downstream effects of LSD and hallucinogenic action. The activation of postsynaptic cortical 5HT2A increases extracellular glutamate release in the synaptic cleft which is reversed by selective 5-HT2A antagonists (Vollenweider et al., 1998), AMPA (α-amino-3-hydroxyl-5-methyl4-isoxazole-propionic acid) receptor antagonists (Zhang and Marek, 2008), agonists and positive allosteric modulators of mGluR2 (metabotropic glutamate receptor 2) (Benneyworth et al., 2007), and selective antagonists of the NR2B subunit of NMDA (N-methyl-D-aspartate) receptors (Lambe and Aghajanian, 2006). In particular, microdialysis in rats confirmed that systemic hallucinogen administration leads to a time-dependent increase in prefrontal cortex (PFC) glutamate levels, an effect which is blocked by administration with the selective 5HT2A antagonist M100907 (Muschamp et al., 2004).</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=D-Lysergic+acid+diethylamide%2C+psilocybin%2C+and+other+classic+hallucinogens%3A+Mechanism+of+action+and+potential+therapeutic+applications+in+mood+disorders&rft.btitle=Psychedelic+Neuroscience&rft.series=Progress+in+Brain+Research&rft.pages=%3Cspan+class%3D%22nowrap%22%3E69-%3C%2Fspan%3E96&rft.date=2018&rft_id=info%3Apmid%2F30471683&rft_id=info%3Adoi%2F10.1016%2Fbs.pbr.2018.07.008&rft.isbn=978-0-12-814255-4&rft.aulast=De+Gregorio&rft.aufirst=D&rft.au=Enns%2C+JP&rft.au=Nu%C3%B1ez%2C+NA&rft.au=Posa%2C+L&rft.au=Gobbi%2C+G&rfr_id=info%3Asid%2Fen.wikipedia.org%3APsilocybin" class="Z3988"> <code class="cs1-code">{{<a href="/wiki/Template:Cite_book" title="Template:Cite book">cite book</a>}}</code>: <code class="cs1-code">|journal=</code> ignored (<a href="/wiki/Help:CS1_errors#periodical_ignored" title="Help:CS1 errors">help</a>) </li> <li id="cite_note-MarekSchoepp2021-151"><a href="#cite_ref-MarekSchoepp2021_151-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFMarekSchoepp2021" class="citation book cs1">Marek GJ, Schoepp DD (2021). "Cortical influences of serotonin and glutamate on layer V pyramidal neurons". 5-HT Interaction with Other Neurotransmitters: Experimental Evidence and Therapeutic Relevance - Part B. Progress in Brain Research. Vol. 261. pp. 341–378. <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%2Fbs.pbr.2020.11.002">10.1016/bs.pbr.2020.11.002</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-444-64258-5" title="Special:BookSources/978-0-444-64258-5"><bdi>978-0-444-64258-5</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/33785135">33785135</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Cortical+influences+of+serotonin+and+glutamate+on+layer+V+pyramidal+neurons&rft.btitle=5-HT+Interaction+with+Other+Neurotransmitters%3A+Experimental+Evidence+and+Therapeutic+Relevance+-+Part+B&rft.series=Progress+in+Brain+Research&rft.pages=%3Cspan+class%3D%22nowrap%22%3E341-%3C%2Fspan%3E378&rft.date=2021&rft_id=info%3Apmid%2F33785135&rft_id=info%3Adoi%2F10.1016%2Fbs.pbr.2020.11.002&rft.isbn=978-0-444-64258-5&rft.aulast=Marek&rft.aufirst=GJ&rft.au=Schoepp%2C+DD&rfr_id=info%3Asid%2Fen.wikipedia.org%3APsilocybin" class="Z3988"> <code class="cs1-code">{{<a href="/wiki/Template:Cite_book" title="Template:Cite book">cite book</a>}}</code>: <code class="cs1-code">|journal=</code> ignored (<a href="/wiki/Help:CS1_errors#periodical_ignored" title="Help:CS1 errors">help</a>) </li> <li id="cite_note-Halberstadt2015-152">^ <a href="#cite_ref-Halberstadt2015_152-0">a</a> <a href="#cite_ref-Halberstadt2015_152-1">b</a> <a href="#cite_ref-Halberstadt2015_152-2">c</a> <a href="#cite_ref-Halberstadt2015_152-3">d</a> <a href="#cite_ref-Halberstadt2015_152-4">e</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFHalberstadt2015" class="citation journal cs1">Halberstadt AL (January 2015). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4642895">"Recent advances in the neuropsychopharmacology of serotonergic hallucinogens"</a>. Behav Brain Res. 277: 99–120. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2Fj.bbr.2014.07.016">10.1016/j.bbr.2014.07.016</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/PMC4642895">4642895</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/25036425">25036425</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Behav+Brain+Res&rft.atitle=Recent+advances+in+the+neuropsychopharmacology+of+serotonergic+hallucinogens&rft.volume=277&rft.pages=%3Cspan+class%3D%22nowrap%22%3E99-%3C%2Fspan%3E120&rft.date=2015-01&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC4642895%23id-name%3DPMC&rft_id=info%3Apmid%2F25036425&rft_id=info%3Adoi%2F10.1016%2Fj.bbr.2014.07.016&rft.aulast=Halberstadt&rft.aufirst=AL&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC4642895&rfr_id=info%3Asid%2Fen.wikipedia.org%3APsilocybin" class="Z3988"> </li> <li id="cite_note-HalberstadtGeyer2018-153">^ <a href="#cite_ref-HalberstadtGeyer2018_153-0">a</a> <a href="#cite_ref-HalberstadtGeyer2018_153-1">b</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFHalberstadtGeyer2018" class="citation journal cs1">Halberstadt AL, Geyer MA (2018). <a rel="nofollow" class="external text" href="https://web.archive.org/web/20170829193524id_/http://www.ouramazingworld.org/uploads/4/3/8/6/43860587/halberstadt2016.pdf">"Effect of Hallucinogens on Unconditioned Behavior"</a> (PDF). Curr Top Behav Neurosci. Current Topics in Behavioral Neurosciences. 36: 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>Compared with phenylalkylamines, tryptamine hallucinogens produce a disparate profile of effects in the mouse BPM. Administration of psilocin or 5-MeO-DMT produces a profound suppression of locomotor activity, investigatory holepokes and rearings, and center duration in C57BL/6J mice (Halberstadt et al. 2011). Most of these effects are blocked by pretreatment with the 5-HT1A antagonist WAY-100635, whereas the 5-HT2C antagonist SB242084 is ineffective.</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Curr+Top+Behav+Neurosci&rft.atitle=Effect+of+Hallucinogens+on+Unconditioned+Behavior&rft.volume=36&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&rft_id=https%3A%2F%2Fweb.archive.org%2Fweb%2F20170829193524id_%2Fhttp%3A%2F%2Fwww.ouramazingworld.org%2Fuploads%2F4%2F3%2F8%2F6%2F43860587%2Fhalberstadt2016.pdf&rfr_id=info%3Asid%2Fen.wikipedia.org%3APsilocybin" class="Z3988"> </li> <li id="cite_note-WillinsMeltzer1997-154"><a href="#cite_ref-WillinsMeltzer1997_154-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFWillinsMeltzer1997" class="citation journal cs1">Willins DL, Meltzer HY (August 1997). "Direct injection of 5-HT2A receptor agonists into the medial prefrontal cortex produces a head-twitch response in rats". J Pharmacol Exp Ther. 282 (2): 699–706. <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%2FS0022-3565%2824%2936840-5">10.1016/S0022-3565(24)36840-5</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/9262333">9262333</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=J+Pharmacol+Exp+Ther&rft.atitle=Direct+injection+of+5-HT2A+receptor+agonists+into+the+medial+prefrontal+cortex+produces+a+head-twitch+response+in+rats&rft.volume=282&rft.issue=2&rft.pages=%3Cspan+class%3D%22nowrap%22%3E699-%3C%2Fspan%3E706&rft.date=1997-08&rft_id=info%3Adoi%2F10.1016%2FS0022-3565%2824%2936840-5&rft_id=info%3Apmid%2F9262333&rft.aulast=Willins&rft.aufirst=DL&rft.au=Meltzer%2C+HY&rfr_id=info%3Asid%2Fen.wikipedia.org%3APsilocybin" class="Z3988"> </li> <li id="cite_note-MasonKuypersMüller2020-155"><a href="#cite_ref-MasonKuypersMüller2020_155-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFMasonKuypersMüllerReckweg2020" class="citation journal cs1">Mason NL, Kuypers KP, Müller F, Reckweg J, Tse DH, Toennes SW, et al. (November 2020). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7547711">"Me, myself, bye: regional alterations in glutamate and the experience of ego dissolution with psilocybin"</a>. Neuropsychopharmacology. 45 (12): 2003–2011. <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%2Fs41386-020-0718-8">10.1038/s41386-020-0718-8</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/PMC7547711">7547711</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/32446245">32446245</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=Me%2C+myself%2C+bye%3A+regional+alterations+in+glutamate+and+the+experience+of+ego+dissolution+with+psilocybin&rft.volume=45&rft.issue=12&rft.pages=%3Cspan+class%3D%22nowrap%22%3E2003-%3C%2Fspan%3E2011&rft.date=2020-11&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC7547711%23id-name%3DPMC&rft_id=info%3Apmid%2F32446245&rft_id=info%3Adoi%2F10.1038%2Fs41386-020-0718-8&rft.aulast=Mason&rft.aufirst=NL&rft.au=Kuypers%2C+KP&rft.au=M%C3%BCller%2C+F&rft.au=Reckweg%2C+J&rft.au=Tse%2C+DH&rft.au=Toennes%2C+SW&rft.au=Hutten%2C+NR&rft.au=Jansen%2C+JF&rft.au=Stiers%2C+P&rft.au=Feilding%2C+A&rft.au=Ramaekers%2C+JG&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC7547711&rfr_id=info%3Asid%2Fen.wikipedia.org%3APsilocybin" class="Z3988"> </li> <li id="cite_note-HalmanKongSarris2024-156"><a href="#cite_ref-HalmanKongSarris2024_156-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFHalmanKongSarrisPerkins2024" class="citation journal cs1">Halman A, Kong G, Sarris J, Perkins D (January 2024). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10851641">"Drug-drug interactions involving classic psychedelics: A systematic review"</a>. J Psychopharmacol. 38 (1): 3–18. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1177%2F02698811231211219">10.1177/02698811231211219</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/PMC10851641">10851641</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/37982394">37982394</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=J+Psychopharmacol&rft.atitle=Drug-drug+interactions+involving+classic+psychedelics%3A+A+systematic+review&rft.volume=38&rft.issue=1&rft.pages=%3Cspan+class%3D%22nowrap%22%3E3-%3C%2Fspan%3E18&rft.date=2024-01&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC10851641%23id-name%3DPMC&rft_id=info%3Apmid%2F37982394&rft_id=info%3Adoi%2F10.1177%2F02698811231211219&rft.aulast=Halman&rft.aufirst=A&rft.au=Kong%2C+G&rft.au=Sarris%2C+J&rft.au=Perkins%2C+D&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC10851641&rfr_id=info%3Asid%2Fen.wikipedia.org%3APsilocybin" class="Z3988"> </li> <li id="cite_note-BrandtKavanaghTwamley2018-157"><a href="#cite_ref-BrandtKavanaghTwamley2018_157-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFBrandtKavanaghTwamleyWestphal2018" class="citation journal cs1">Brandt SD, Kavanagh PV, Twamley B, Westphal F, Elliott SP, Wallach J, et al. (February 2018). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6230476">"Return of the lysergamides. Part IV: Analytical and pharmacological characterization of lysergic acid morpholide (LSM-775)"</a>. Drug Test Anal. 10 (2): 310–322. <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%2Fdta.2222">10.1002/dta.2222</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/PMC6230476">6230476</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/28585392">28585392</a>. <q>Additionally, pretreatment with the 5‐HT1A agonist buspirone (20 mg p.o.) markedly attenuates the visual effects of psilocybin in human volunteers.59 Although buspirone failed to completely block the hallucinogenic effects of psilocybin, the limited inhibition is not necessarily surprising because buspirone is a low efficacy 5‐HT1A partial agonist.60 The level of 5‐HT1A activation produced by buspirone may not be sufficient to completely counteract the stimulation of 5‐HT2A receptors by psilocin (the active metabolite of psilocybin). Another consideration is that psilocin acts as a 5‐HT1A agonist.30 If 5‐HT1A activation by psilocin buffers its hallucinogenic effects similar to DMT58 then competition between psilocin and a weaker partial agonist such as buspirone would limit attenuation of the hallucinogenic response.</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Drug+Test+Anal&rft.atitle=Return+of+the+lysergamides.+Part+IV%3A+Analytical+and+pharmacological+characterization+of+lysergic+acid+morpholide+%28LSM-775%29&rft.volume=10&rft.issue=2&rft.pages=%3Cspan+class%3D%22nowrap%22%3E310-%3C%2Fspan%3E322&rft.date=2018-02&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC6230476%23id-name%3DPMC&rft_id=info%3Apmid%2F28585392&rft_id=info%3Adoi%2F10.1002%2Fdta.2222&rft.aulast=Brandt&rft.aufirst=SD&rft.au=Kavanagh%2C+PV&rft.au=Twamley%2C+B&rft.au=Westphal%2C+F&rft.au=Elliott%2C+SP&rft.au=Wallach%2C+J&rft.au=Stratford%2C+A&rft.au=Klein%2C+LM&rft.au=McCorvy%2C+JD&rft.au=Nichols%2C+DE&rft.au=Halberstadt%2C+AL&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC6230476&rfr_id=info%3Asid%2Fen.wikipedia.org%3APsilocybin" class="Z3988"> </li> <li id="cite_note-PokornyPrellerKraehenmann2016-158"><a href="#cite_ref-PokornyPrellerKraehenmann2016_158-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFPokornyPrellerKraehenmannVollenweider2016" class="citation journal cs1">Pokorny T, Preller KH, Kraehenmann R, Vollenweider FX (April 2016). 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(December 2022). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9714399">"ACNP 61st Annual Meeting: Poster Abstracts P271-P540: P314. Psilocybin Alters Behavior and the Intestinal Microbiota in a Wild Type Mouse Model by Mechanisms That Are Not Fully Dependent on 5HT2A and 5HT2C Receptors"</a>. Neuropsychopharmacology. 47 (Suppl 1): 220–370 (245–246). <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%2Fs41386-022-01485-0">10.1038/s41386-022-01485-0</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/PMC9714399">9714399</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/36456694">36456694</a>. <q>Psilocybin induced a robust head twitch response, increased exploratory behavior in the elevated plus maze, increased social behavior in the social interaction test, and decreased immobility in the forced swim test. Co-administration of ketanserin fully blocked the head twitch response without significantly altering psilocybin's effects on other behavioral outcomes. In a separate cohort, treatment with psilocybin produced broad alteration of the intestinal microbiome, with particularly marked changes in the large intestine that were only partially blocked by pre-treatment with ketanserin. Finally, transplantation of intestinal contents from psilocybin-treated mice to naive untreated mice resulted in behavioral changes consistent with the effects of psilocybin treatment. [...] Our findings demonstrate that a single dose of psilocybin leads to behavioral changes in mice that are relevant for studies of resilience and affective disorders. Our results further indicate that the behavioral changes may not be fully dependent on psilocybin's agonism of 5HT2A and 5HT2C receptors. Further, psilocybin appears to broadly alter the intestinal microbiome and transplantation of intestinal contents reproduces behavioral change associated with psilocybin treatment, suggesting a previously unknown microbiome-gut-brain mechanism of action.</q></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=ACNP+61st+Annual+Meeting%3A+Poster+Abstracts+P271-P540%3A+P314.+Psilocybin+Alters+Behavior+and+the+Intestinal+Microbiota+in+a+Wild+Type+Mouse+Model+by+Mechanisms+That+Are+Not+Fully+Dependent+on+5HT2A+and+5HT2C+Receptors&rft.volume=47&rft.issue=Suppl+1&rft.pages=220-370+%28245-246%29&rft.date=2022-12&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC9714399%23id-name%3DPMC&rft_id=info%3Apmid%2F36456694&rft_id=info%3Adoi%2F10.1038%2Fs41386-022-01485-0&rft.aulast=Cordner&rft.aufirst=Z&rft.au=Prandovszky%2C+E&rft.au=Pedicini%2C+M&rft.au=Liu%2C+H&rft.au=Macias%2C+L&rft.au=Pletnikov%2C+M&rft.au=Tamashiro%2C+K&rft.au=Yolken%2C+R&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC9714399&rfr_id=info%3Asid%2Fen.wikipedia.org%3APsilocybin" class="Z3988"> </li> <li id="cite_note-SinghShaharWolf2022-162"><a href="#cite_ref-SinghShaharWolf2022_162-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFSinghBotvinnikShaharWolf2022" class="citation journal cs1">Singh S, Botvinnik A, Shahar O, Wolf G, Lotan A, Lerer B, et al. 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"Psychedelics and Anti-inflammatory Activity in Animal Models". Curr Top Behav Neurosci. Current Topics in Behavioral Neurosciences. 56: 229–245. <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_2022_367">10.1007/7854_2022_367</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-3-031-12183-8" title="Special:BookSources/978-3-031-12183-8"><bdi>978-3-031-12183-8</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/35546383">35546383</a>. <q>In our rodent acute asthma model, psilocin, the active metabolite of psilocybin, displays a similar anti-AHR efficacy and potency to that of (R)-DOI. Surprisingly, other tryptamines with very similar structures like N,N-dimethyltryptamine (DMT) and 5-methoxy-N,N-dimethyltryptamine (5-MeO-DMT) show no efficacy to reduce OVA-induced AHR.</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Curr+Top+Behav+Neurosci&rft.atitle=Psychedelics+and+Anti-inflammatory+Activity+in+Animal+Models&rft.volume=56&rft.pages=%3Cspan+class%3D%22nowrap%22%3E229-%3C%2Fspan%3E245&rft.date=2022&rft_id=info%3Apmid%2F35546383&rft_id=info%3Adoi%2F10.1007%2F7854_2022_367&rft.isbn=978-3-031-12183-8&rft.aulast=Flanagan&rft.aufirst=TW&rft.au=Nichols%2C+CD&rfr_id=info%3Asid%2Fen.wikipedia.org%3APsilocybin" class="Z3988"> </li> <li id="cite_note-WulffNicholsThompson2023-175">^ <a href="#cite_ref-WulffNicholsThompson2023_175-0">a</a> <a href="#cite_ref-WulffNicholsThompson2023_175-1">b</a> <a href="#cite_ref-WulffNicholsThompson2023_175-2">c</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFWulffNicholsThompson2023" class="citation journal cs1">Wulff AB, Nichols CD, Thompson SM (June 2023). <a rel="nofollow" class="external text" href="https://doi.org/10.1016%2Fj.neuropharm.2023.109504">"Preclinical perspectives on the mechanisms underlying the therapeutic actions of psilocybin in psychiatric disorders"</a>. Neuropharmacology. 231: 109504. <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.2023.109504">10.1016/j.neuropharm.2023.109504</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/36921889">36921889</a>. <q>Interestingly, the anti-inflammatory effects of psychedelics acting at 5-HT2A receptors do not correlate with activation of either Gαq or β-arrestin recruitment (Flanagan et al., 2020), indicating psychedelics can recruit different effector pathways from those underlying behaviors for biological effects. [...] Psilocybin and certain other psychedelics have potent anti-inflammatory effects in preclinical models of human disease that could contribute to their efficacy. For example, delivery of psilocin directly to the lungs of rats via nebulization potently suppressed inflammation and restored normal breathing in a model of allergic asthma (Flanagan et al., 2020). The amount of psilocybin necessary for full effect was far below the threshold to produce behavioral effects, suggesting that sub-behavioral levels of psilocybin or other psychedelic may represent a new therapeutic strategy to treat inflammatory disorders. Interestingly, as mentioned above, neither the Gαq or β-arrestin signaling pathways seem to be involved in these effects (Flanagan et al., 2020).</q></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=Preclinical+perspectives+on+the+mechanisms+underlying+the+therapeutic+actions+of+psilocybin+in+psychiatric+disorders&rft.volume=231&rft.pages=109504&rft.date=2023-06&rft_id=info%3Adoi%2F10.1016%2Fj.neuropharm.2023.109504&rft_id=info%3Apmid%2F36921889&rft.aulast=Wulff&rft.aufirst=AB&rft.au=Nichols%2C+CD&rft.au=Thompson%2C+SM&rft_id=https%3A%2F%2Fdoi.org%2F10.1016%252Fj.neuropharm.2023.109504&rfr_id=info%3Asid%2Fen.wikipedia.org%3APsilocybin" class="Z3988"> </li> <li id="cite_note-Kinderlehrer2025-176">^ <a href="#cite_ref-Kinderlehrer2025_176-0">a</a> <a href="#cite_ref-Kinderlehrer2025_176-1">b</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFKinderlehrer2025" class="citation journal cs1">Kinderlehrer DA (2025). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11787777">"Mushrooms, Microdosing, and Mental Illness: The Effect of Psilocybin on Neurotransmitters, Neuroinflammation, and Neuroplasticity"</a>. 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Neuropharmacology. 219: 109232. <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.2022.109232">10.1016/j.neuropharm.2022.109232</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/36007854">36007854</a>. <q>Remarkably, the IC50 dose for (R)-DOI in this prophylactic paradigm is ∼0.005 mg/kg, administered via nebulization or by intraperitoneal injection (Flanagan et al., 2021). This is > 50x less than the behavioral threshold dose. We have also shown that the drug psilocin, the active form of the prodrug psilocybin, has virtually the same potency as (R)-DOI (Flanagan et al., 2021), indicating that the effects are not limited to (R)-DOI or are chemotype dependent.</q></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=Psychedelics+as+potent+anti-inflammatory+therapeutics&rft.volume=219&rft.pages=109232&rft.date=2022-11&rft_id=info%3Adoi%2F10.1016%2Fj.neuropharm.2022.109232&rft_id=info%3Apmid%2F36007854&rft.aulast=Nichols&rft.aufirst=CD&rft_id=https%3A%2F%2Fdoi.org%2F10.1016%252Fj.neuropharm.2022.109232&rfr_id=info%3Asid%2Fen.wikipedia.org%3APsilocybin" class="Z3988"> </li> <li id="cite_note-FlanaganBillacLandry2021-178"><a href="#cite_ref-FlanaganBillacLandry2021_178-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFFlanaganBillacLandrySebastian2021" class="citation journal cs1">Flanagan TW, Billac GB, Landry AN, Sebastian MN, Cormier SA, Nichols CD (April 2021). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8033619">"Structure-Activity Relationship Analysis of Psychedelics in a Rat Model of Asthma Reveals the Anti-Inflammatory Pharmacophore"</a>. ACS Pharmacol Transl Sci. 4 (2): 488–502. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1021%2Facsptsci.0c00063">10.1021/acsptsci.0c00063</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/PMC8033619">8033619</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/33860179">33860179</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=ACS+Pharmacol+Transl+Sci&rft.atitle=Structure-Activity+Relationship+Analysis+of+Psychedelics+in+a+Rat+Model+of+Asthma+Reveals+the+Anti-Inflammatory+Pharmacophore&rft.volume=4&rft.issue=2&rft.pages=%3Cspan+class%3D%22nowrap%22%3E488-%3C%2Fspan%3E502&rft.date=2021-04&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC8033619%23id-name%3DPMC&rft_id=info%3Apmid%2F33860179&rft_id=info%3Adoi%2F10.1021%2Facsptsci.0c00063&rft.aulast=Flanagan&rft.aufirst=TW&rft.au=Billac%2C+GB&rft.au=Landry%2C+AN&rft.au=Sebastian%2C+MN&rft.au=Cormier%2C+SA&rft.au=Nichols%2C+CD&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC8033619&rfr_id=info%3Asid%2Fen.wikipedia.org%3APsilocybin" class="Z3988"> </li> <li id="cite_note-FlanaganNichols2018-179"><a href="#cite_ref-FlanaganNichols2018_179-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFFlanaganNichols2018" class="citation journal cs1">Flanagan TW, Nichols CD (August 2018). <a rel="nofollow" class="external text" href="http://usdbiology.com/cliff/Courses/Advanced%20Seminars%20in%20Neuroendocrinology/Therapeutic%20Effects%20of%20Psychedelics%2019/Flanagan%20Nichols%2018%20IntRevPsychiatry%20Psychedelics%20as%20anti-inflammatory%20agents.pdf">"Psychedelics as anti-inflammatory agents"</a> (PDF). Int Rev Psychiatry. 30 (4): 363–375. <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%2F09540261.2018.1481827">10.1080/09540261.2018.1481827</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/30102081">30102081</a>. <q>We have previously speculated that the anti-inflammatory effects of psychedelics mediated through serotonin 5-HT2A receptor activation are a key component of not only the anti-depressant effects of psilocybin, but also contribute to its long-lasting effects after only a single treatment (Kyzar, Nichols, Gainetdinov, Nichols, & Kalueff, 2017).</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Int+Rev+Psychiatry&rft.atitle=Psychedelics+as+anti-inflammatory+agents&rft.volume=30&rft.issue=4&rft.pages=%3Cspan+class%3D%22nowrap%22%3E363-%3C%2Fspan%3E375&rft.date=2018-08&rft_id=info%3Adoi%2F10.1080%2F09540261.2018.1481827&rft_id=info%3Apmid%2F30102081&rft.aulast=Flanagan&rft.aufirst=TW&rft.au=Nichols%2C+CD&rft_id=http%3A%2F%2Fusdbiology.com%2Fcliff%2FCourses%2FAdvanced%2520Seminars%2520in%2520Neuroendocrinology%2FTherapeutic%2520Effects%2520of%2520Psychedelics%252019%2FFlanagan%2520Nichols%252018%2520IntRevPsychiatry%2520Psychedelics%2520as%2520anti-inflammatory%2520agents.pdf&rfr_id=info%3Asid%2Fen.wikipedia.org%3APsilocybin" class="Z3988"> </li> <li id="cite_note-KuypersErritzoeKnudsen2019-180"><a href="#cite_ref-KuypersErritzoeKnudsen2019_180-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFKuypersNgErritzoeKnudsen2019" class="citation journal cs1">Kuypers KP, Ng L, Erritzoe D, Knudsen GM, Nichols CD, Nichols DE, et al. (September 2019). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6732823">"Microdosing psychedelics: More questions than answers? An overview and suggestions for future research"</a>. J Psychopharmacol. 33 (9): 1039–1057. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1177%2F0269881119857204">10.1177/0269881119857204</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/PMC6732823">6732823</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/31303095">31303095</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=J+Psychopharmacol&rft.atitle=Microdosing+psychedelics%3A+More+questions+than+answers%3F+An+overview+and+suggestions+for+future+research&rft.volume=33&rft.issue=9&rft.pages=%3Cspan+class%3D%22nowrap%22%3E1039-%3C%2Fspan%3E1057&rft.date=2019-09&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC6732823%23id-name%3DPMC&rft_id=info%3Apmid%2F31303095&rft_id=info%3Adoi%2F10.1177%2F0269881119857204&rft.aulast=Kuypers&rft.aufirst=KP&rft.au=Ng%2C+L&rft.au=Erritzoe%2C+D&rft.au=Knudsen%2C+GM&rft.au=Nichols%2C+CD&rft.au=Nichols%2C+DE&rft.au=Pani%2C+L&rft.au=Soula%2C+A&rft.au=Nutt%2C+D&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC6732823&rfr_id=info%3Asid%2Fen.wikipedia.org%3APsilocybin" class="Z3988"> </li> <li id="cite_note-LowNgLim2024-181"><a href="#cite_ref-LowNgLim2024_181-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFLowNgLimGoh2024" class="citation journal cs1">Low ZX, Ng WS, Lim ES, Goh BH, Kumari Y (September 2024). <a rel="nofollow" class="external text" href="https://doi.org/10.1016%2Fj.pnpbp.2024.111139">"The immunomodulatory effects of classical psychedelics: A systematic review of preclinical studies"</a>. Prog Neuropsychopharmacol Biol Psychiatry. 136: 111139. <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.pnpbp.2024.111139">10.1016/j.pnpbp.2024.111139</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/39251080">39251080</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Prog+Neuropsychopharmacol+Biol+Psychiatry&rft.atitle=The+immunomodulatory+effects+of+classical+psychedelics%3A+A+systematic+review+of+preclinical+studies&rft.volume=136&rft.pages=111139&rft.date=2024-09&rft_id=info%3Adoi%2F10.1016%2Fj.pnpbp.2024.111139&rft_id=info%3Apmid%2F39251080&rft.aulast=Low&rft.aufirst=ZX&rft.au=Ng%2C+WS&rft.au=Lim%2C+ES&rft.au=Goh%2C+BH&rft.au=Kumari%2C+Y&rft_id=https%3A%2F%2Fdoi.org%2F10.1016%252Fj.pnpbp.2024.111139&rfr_id=info%3Asid%2Fen.wikipedia.org%3APsilocybin" class="Z3988"> </li> <li id="cite_note-KellyClarkeHarkin2023-182"><a href="#cite_ref-KellyClarkeHarkin2023_182-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFKellyClarkeHarkinCorr2023" class="citation journal cs1">Kelly JR, Clarke G, Harkin A, Corr SC, Galvin S, Pradeep V, et al. 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Int J Clin Health Psychol. 23 (2): 100349. <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.ijchp.2022.100349">10.1016/j.ijchp.2022.100349</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/PMC9791138">9791138</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/36605409">36605409</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Int+J+Clin+Health+Psychol&rft.atitle=Seeking+the+Psilocybiome%3A+Psychedelics+meet+the+microbiota-gut-brain+axis&rft.volume=23&rft.issue=2&rft.pages=100349&rft.date=2023&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC9791138%23id-name%3DPMC&rft_id=info%3Apmid%2F36605409&rft_id=info%3Adoi%2F10.1016%2Fj.ijchp.2022.100349&rft.aulast=Kelly&rft.aufirst=JR&rft.au=Clarke%2C+G&rft.au=Harkin%2C+A&rft.au=Corr%2C+SC&rft.au=Galvin%2C+S&rft.au=Pradeep%2C+V&rft.au=Cryan%2C+JF&rft.au=O%27Keane%2C+V&rft.au=Dinan%2C+TG&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC9791138&rfr_id=info%3Asid%2Fen.wikipedia.org%3APsilocybin" class="Z3988"> </li> <li id="cite_note-CalderMockFriedli2023-183"><a href="#cite_ref-CalderMockFriedli2023_183-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFCalderMockFriedliPasi2023" class="citation journal cs1">Calder A, Mock S, Friedli N, Pasi P, Hasler G (October 2023). "Psychedelics in the treatment of eating disorders: Rationale and potential mechanisms". Eur Neuropsychopharmacol. 75: 1–14. <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.euroneuro.2023.05.008">10.1016/j.euroneuro.2023.05.008</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/37352816">37352816</a>. <q>Interestingly, both EDs and mood disorders are often comorbid with gastrointestinal symptoms and reduced diversity of the gut microbiome. (Lam et al., 2017) A dysregulated microbiome may constitute a development or maintenance factor for AN in particular. (Butler et al., 2021) It has been suggested that psychedelics exert some of their long-term effects via the microbiome. (Kuypers, 2019) Psilocybin has been shown to diversify the intestinal microbiome in mice, and this diversification appeared to be responsible for lasting antidepressant-like behavioral effects. (Cordner et al., 2022) Normalization of the gut microbiome may thus assist with recovery from both EDs and comorbid mood disorders, and presents an intriguing avenue for future research. (Kleiman et al., 2015)</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Eur+Neuropsychopharmacol&rft.atitle=Psychedelics+in+the+treatment+of+eating+disorders%3A+Rationale+and+potential+mechanisms&rft.volume=75&rft.pages=%3Cspan+class%3D%22nowrap%22%3E1-%3C%2Fspan%3E14&rft.date=2023-10&rft_id=info%3Adoi%2F10.1016%2Fj.euroneuro.2023.05.008&rft_id=info%3Apmid%2F37352816&rft.aulast=Calder&rft.aufirst=A&rft.au=Mock%2C+S&rft.au=Friedli%2C+N&rft.au=Pasi%2C+P&rft.au=Hasler%2C+G&rfr_id=info%3Asid%2Fen.wikipedia.org%3APsilocybin" class="Z3988"> </li> <li id="cite_note-ReedFoldi2024-184">^ <a href="#cite_ref-ReedFoldi2024_184-0">a</a> <a href="#cite_ref-ReedFoldi2024_184-1">b</a> <a href="#cite_ref-ReedFoldi2024_184-2">c</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFReedFoldi2024" class="citation journal cs1">Reed F, Foldi CJ (February 2024). 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(1981), the 360 MHz proton NMR, the amine pKa values and the octanol–water Log P values were determined experimentally and compared for both psilocin and bufotenine (Figure 3a). The side chain protons in the NMR for bufotenine were shown to be rapidly rotating with no preference for gauche or trans conformations, whereas the side chain for psilocin was less mobile and was determined to favour a gauche (80%) versus trans (20%) conformation. Because psilocin is a weaker base but is also more lipid soluble, it was proposed that psilocin formed an intramolecular hydrogen bond, as illustrated in Figure 3a. In the energy-minimized structure of this conformation, the length of the hydrogen bond is 1.88 Å. The weaker pKa of psilocin relative to bufotenine means that psilocin is less highly ionized at pH 7.4—that is, 8.5% free base versus 0.53% for bufotenine at pH 7.4. 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Front Psychiatry. 10: 407. <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.2019.00407">10.3389/fpsyt.2019.00407</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/PMC6584108">6584108</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/31249537">31249537</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Front+Psychiatry&rft.atitle=Placebo+Effect+in+the+Treatment+of+Depression+and+Anxiety&rft.volume=10&rft.pages=407&rft.date=2019&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC6584108%23id-name%3DPMC&rft_id=info%3Apmid%2F31249537&rft_id=info%3Adoi%2F10.3389%2Ffpsyt.2019.00407&rft.aulast=Kirsch&rft.aufirst=I&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC6584108&rfr_id=info%3Asid%2Fen.wikipedia.org%3APsilocybin" class="Z3988"> </li> <li id="cite_note-HengartnerPlöderl2018-281"><a href="#cite_ref-HengartnerPlöderl2018_281-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFHengartnerPlöderl2018" class="citation journal cs1">Hengartner MP, Plöderl M (July 2018). "False Beliefs in Academic Psychiatry: The Case of Antidepressant Drugs". Ethical Human Psychology and Psychiatry. 20 (1): 6–16. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1891%2F1559-4343.20.1.6">10.1891/1559-4343.20.1.6</a>. <a href="/wiki/EISSN_(identifier)" class="mw-redirect" title="EISSN (identifier)">eISSN</a> <a rel="nofollow" class="external text" href="https://search.worldcat.org/issn/1938-9000">1938-9000</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/1559-4343">1559-4343</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:149608377">149608377</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Ethical+Human+Psychology+and+Psychiatry&rft.atitle=False+Beliefs+in+Academic+Psychiatry%3A+The+Case+of+Antidepressant+Drugs&rft.volume=20&rft.issue=1&rft.pages=%3Cspan+class%3D%22nowrap%22%3E6-%3C%2Fspan%3E16&rft.date=2018-07&rft.issn=1559-4343&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A149608377%23id-name%3DS2CID&rft.eissn=1938-9000&rft_id=info%3Adoi%2F10.1891%2F1559-4343.20.1.6&rft.aulast=Hengartner&rft.aufirst=MP&rft.au=Pl%C3%B6derl%2C+M&rfr_id=info%3Asid%2Fen.wikipedia.org%3APsilocybin" class="Z3988"> </li> <li id="cite_note-DupuisVeissière2022-282"><a href="#cite_ref-DupuisVeissière2022_282-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFDupuisVeissière2022" class="citation journal cs1">Dupuis D, Veissière S (October 2022). "Culture, context, and ethics in the therapeutic use of hallucinogens: Psychedelics as active super-placebos?". Transcult Psychiatry. 59 (5): 571–578. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1177%2F13634615221131465">10.1177/13634615221131465</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/36263513">36263513</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Transcult+Psychiatry&rft.atitle=Culture%2C+context%2C+and+ethics+in+the+therapeutic+use+of+hallucinogens%3A+Psychedelics+as+active+super-placebos%3F&rft.volume=59&rft.issue=5&rft.pages=%3Cspan+class%3D%22nowrap%22%3E571-%3C%2Fspan%3E578&rft.date=2022-10&rft_id=info%3Adoi%2F10.1177%2F13634615221131465&rft_id=info%3Apmid%2F36263513&rft.aulast=Dupuis&rft.aufirst=D&rft.au=Veissi%C3%A8re%2C+S&rfr_id=info%3Asid%2Fen.wikipedia.org%3APsilocybin" class="Z3988"> </li> <li id="cite_note-vanElkYaden2022-283"><a href="#cite_ref-vanElkYaden2022_283-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFvan_ElkYaden2022" class="citation journal cs1">van Elk M, Yaden DB (September 2022). "Pharmacological, neural, and psychological mechanisms underlying psychedelics: A critical review". Neurosci Biobehav Rev. 140: 104793. <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.2022.104793">10.1016/j.neubiorev.2022.104793</a>. <a href="/wiki/Hdl_(identifier)" class="mw-redirect" title="Hdl (identifier)">hdl</a>:<a rel="nofollow" class="external text" href="https://hdl.handle.net/1887%2F3515020">1887/3515020</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/35878791">35878791</a>. <q>In addition, the strong prior expectations that many people have about psychedelics directly contribute to the psychedelic experience and as a consequence it has been suggested that psychedelics may act as a 'super-placebo' (Hartogsohn, 2016). Specifically, strong prior expectations (e.g., that a specific intervention will likely trigger a mystical experience) will increase the likelihood of having e.g., a mystical-type experience (Maij et al., 2019), and this placebo-effect is further boosted by the psychedelic-induced suggestibility.</q></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=Pharmacological%2C+neural%2C+and+psychological+mechanisms+underlying+psychedelics%3A+A+critical+review&rft.volume=140&rft.pages=104793&rft.date=2022-09&rft_id=info%3Ahdl%2F1887%2F3515020&rft_id=info%3Apmid%2F35878791&rft_id=info%3Adoi%2F10.1016%2Fj.neubiorev.2022.104793&rft.aulast=van+Elk&rft.aufirst=M&rft.au=Yaden%2C+DB&rfr_id=info%3Asid%2Fen.wikipedia.org%3APsilocybin" class="Z3988"> </li> <li id="cite_note-YaoGuoLu2024-284"><a href="#cite_ref-YaoGuoLu2024_284-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFYaoGuoLuLiu2024" class="citation journal cs1">Yao Y, Guo D, Lu TS, Liu FL, Huang SH, Diao MQ, et al. 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Psychiatry Res. 335: 115886. <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.psychres.2024.115886">10.1016/j.psychres.2024.115886</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/38574699">38574699</a>.</cite><span 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href="https://web.archive.org/web/20210813065107/https://www.usonainstitute.org/wp-content/uploads/2018/12/psilocybin-ib-v4-1.pdf">Psilocybin Investigator's Brochure, Version 4.1</a> (Usona Institute, Madison, Wisconsin, 2021)</li> <li><a rel="nofollow" class="external text" href="https://adisinsight.springer.com/drugs/800050861">Psilocybin (COMP-360) - COMPASS Pathways - AdisInsight</a></li></ul> <div class="navbox-styles"><style data-mw-deduplicate="TemplateStyles:r1129693374">.mw-parser-output .hlist dl,.mw-parser-output .hlist ol,.mw-parser-output .hlist ul{margin:0;padding:0}.mw-parser-output .hlist dd,.mw-parser-output .hlist dt,.mw-parser-output .hlist li{margin:0;display:inline}.mw-parser-output .hlist.inline,.mw-parser-output .hlist.inline dl,.mw-parser-output .hlist.inline ol,.mw-parser-output .hlist.inline ul,.mw-parser-output .hlist dl dl,.mw-parser-output .hlist dl ol,.mw-parser-output .hlist dl ul,.mw-parser-output .hlist ol dl,.mw-parser-output .hlist ol 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<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" class="mw-redirect" 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="/w/index.php?title=2C-T-27&action=edit&redlink=1" class="new" title="2C-T-27 (page does not exist)">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="/w/index.php?title=2C-T-33&action=edit&redlink=1" class="new" title="2C-T-33 (page does not exist)">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 href="/wiki/MDMA" title="MDMA">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 class="mw-selflink selflink">(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="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 class="mw-selflink selflink">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="/w/index.php?title=SB-224289&action=edit&redlink=1" class="new" title="SB-224289 (page does not exist)">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 href="/wiki/MDMA" title="MDMA">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 class="mw-selflink selflink">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 href="/wiki/MDMA" title="MDMA">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 class="mw-selflink selflink">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 href="/wiki/MDMA" title="MDMA">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 class="mw-selflink selflink">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" 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="Tryptamines232" 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:Tryptamines" title="Template:Tryptamines"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Tryptamines" title="Template talk:Tryptamines"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Tryptamines" title="Special:EditPage/Template:Tryptamines"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Tryptamines232" style="font-size:114%;margin:0 4em"><a href="/wiki/Substituted_tryptamine" title="Substituted tryptamine">Tryptamines</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><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="/w/index.php?title=1-Methyltryptamine&action=edit&redlink=1" class="new" title="1-Methyltryptamine (page does not exist)">1-Methyl-T</a></li> <li><a href="/wiki/1-Methylpsilocin" title="1-Methylpsilocin">1-Methylpsilocin</a></li> <li><a href="/wiki/2-HO-NMT" title="2-HO-NMT">2-HO-NMT</a></li> <li><a href="/wiki/2-Me-DET" title="2-Me-DET">2-Me-DET</a></li> <li><a href="/wiki/2-Methyl-5-hydroxytryptamine" title="2-Methyl-5-hydroxytryptamine">2-Methyl-5-HT</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/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/4,5-Dihydroxytryptamine" title="4,5-Dihydroxytryptamine">4,5-DHT</a></li> <li><a href="/wiki/4-AcO-DALT" title="4-AcO-DALT">4-AcO-DALT</a></li> <li><a href="/wiki/4-Acetoxy-DET" class="mw-redirect" title="4-Acetoxy-DET">4-AcO-DET</a></li> <li><a href="/wiki/4-Acetoxy-DiPT" title="4-Acetoxy-DiPT">4-AcO-DiPT</a></li> <li><a href="/wiki/4-AcO-DPT" title="4-AcO-DPT">4-AcO-DPT</a></li> <li><a href="/w/index.php?title=4-AcO-EPT&action=edit&redlink=1" class="new" title="4-AcO-EPT (page does not exist)">4-AcO-EPT</a></li> <li><a href="/w/index.php?title=4-AcO-MALT&action=edit&redlink=1" class="new" title="4-AcO-MALT (page does not exist)">4-AcO-MALT</a></li> <li><a href="/wiki/4-Acetoxy-MET" class="mw-redirect" title="4-Acetoxy-MET">4-AcO-MET</a></li> <li><a href="/wiki/4-Acetoxy-MiPT" class="mw-redirect" title="4-Acetoxy-MiPT">4-AcO-MiPT</a></li> <li><a href="/w/index.php?title=4-AcO-NMT&action=edit&redlink=1" class="new" title="4-AcO-NMT (page does not exist)">4-AcO-NMT</a></li> <li><a href="/w/index.php?title=4-AcO-TMT&action=edit&redlink=1" class="new" title="4-AcO-TMT (page does not exist)">4-AcO-TMT</a></li> <li><a href="/wiki/4-Fluoro-5-methoxy-DMT" title="4-Fluoro-5-methoxy-DMT">4-F-5-MeO-DMT</a></li> <li><a href="/w/index.php?title=4-Fluorotryptamine&action=edit&redlink=1" class="new" title="4-Fluorotryptamine (page does not exist)">4-Fluoro-T</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="/w/index.php?title=4-HO-DALT&action=edit&redlink=1" class="new" title="4-HO-DALT (page does not exist)">4-HO-DALT</a></li> <li><a href="/wiki/4-HO-DBT" title="4-HO-DBT">4-HO-DBT</a></li> <li><a href="/wiki/4-HO-DET" title="4-HO-DET">4-HO-DET</a></li> <li><a href="/wiki/4-HO-DiPT" title="4-HO-DiPT">4-HO-DiPT</a></li> <li><a href="/wiki/4-HO-DPT" title="4-HO-DPT">4-HO-DPT</a></li> <li><a href="/wiki/4-HO-DSBT" title="4-HO-DSBT">4-HO-DSBT</a></li> <li><a href="/wiki/4-HO-EPT" title="4-HO-EPT">4-HO-EPT</a></li> <li><a href="/wiki/4-HO-MALT" title="4-HO-MALT">4-HO-MALT</a></li> <li><a href="/wiki/4-HO-MET" title="4-HO-MET">4-HO-MET</a></li> <li><a href="/wiki/4-HO-McPT" title="4-HO-McPT">4-HO-McPT</a></li> <li><a href="/wiki/4-HO-McPeT" title="4-HO-McPeT">4-HO-McPeT</a></li> <li><a href="/wiki/4-HO-MiPT" title="4-HO-MiPT">4-HO-MiPT</a></li> <li><a href="/wiki/4-HO-MPT" title="4-HO-MPT">4-HO-MPT</a></li> <li><a href="/w/index.php?title=4-HO-MsBT&action=edit&redlink=1" class="new" title="4-HO-MsBT (page does not exist)">4-HO-MsBT</a></li> <li><a href="/wiki/4-HO-NALT" title="4-HO-NALT">4-HO-NALT</a></li> <li><a href="/wiki/4-HO-NMT" class="mw-redirect" title="4-HO-NMT">4-HO-NMT</a></li> <li><a href="/wiki/4-HO-PiPT" title="4-HO-PiPT">4-HO-PiPT</a></li> <li><a href="/wiki/4-HO-pyr-T" title="4-HO-pyr-T">4-HO-pyr-T</a></li> <li><a href="/wiki/4-HO-TMT" title="4-HO-TMT">4-HO-TMT</a></li> <li><a href="/wiki/4-Hydroxytryptamine" title="4-Hydroxytryptamine">4-HT</a></li> <li><a href="/w/index.php?title=4-MeO-DiPT&action=edit&redlink=1" class="new" title="4-MeO-DiPT (page does not exist)">4-MeO-DiPT</a></li> <li><a href="/wiki/4-MeO-DMT" title="4-MeO-DMT">4-MeO-DMT</a></li> <li><a href="/wiki/4-MeO-MiPT" title="4-MeO-MiPT">4-MeO-MiPT</a></li> <li><a href="/w/index.php?title=4-MeO-T&action=edit&redlink=1" class="new" title="4-MeO-T (page does not exist)">4-MeO-T</a></li> <li><a href="/wiki/4-PrO-DMT" title="4-PrO-DMT">4-PrO-DMT</a></li> <li><a href="/wiki/4,5-MDO-DMT" title="4,5-MDO-DMT">4,5-MDO-DMT</a></li> <li><a href="/wiki/4,5-MDO-DiPT" title="4,5-MDO-DiPT">4,5-MDO-DiPT</a></li> <li><a href="/wiki/5-Benzyloxytryptamine" title="5-Benzyloxytryptamine">5-BT</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=5-Bromotryptamine&action=edit&redlink=1" class="new" title="5-Bromotryptamine (page does not exist)">5-Bromo-T</a></li> <li><a href="/wiki/5-Chloro-DMT" title="5-Chloro-DMT">5-Chloro-DMT</a></li> <li><a href="/w/index.php?title=5-Chlorotryptamine&action=edit&redlink=1" class="new" title="5-Chlorotryptamine (page does not exist)">5-Chloro-T</a></li> <li><a href="/wiki/5-Carboxamidotryptamine" title="5-Carboxamidotryptamine">5-CT</a></li> <li><a href="/wiki/5-Ethoxy-DMT" title="5-Ethoxy-DMT">5-Ethoxy-DMT</a></li> <li><a href="/wiki/5-Ethyl-DMT" title="5-Ethyl-DMT">5-Ethyl-DMT</a></li> <li><a href="/wiki/5-Fluoro-DET" title="5-Fluoro-DET">5-Fluoro-DET</a></li> <li><a href="/wiki/5-Fluoro-DMT" title="5-Fluoro-DMT">5-Fluoro-DMT</a></li> <li><a href="/wiki/5-Fluoro-EPT" title="5-Fluoro-EPT">5-Fluoro-EPT</a></li> <li><a href="/wiki/5-Fluoro-MET" title="5-Fluoro-MET">5-Fluoro-MET</a></li> <li><a href="/w/index.php?title=5-Fluorotryptamine&action=edit&redlink=1" class="new" title="5-Fluorotryptamine (page does not exist)">5-Fluoro-T</a></li> <li><a href="/wiki/5-HO-DiPT" title="5-HO-DiPT">5-HO-DiPT</a></li> <li><a href="/wiki/5-Hydroxytryptophan" title="5-Hydroxytryptophan">5-HTP (oxitriptan)</a></li> <li><a href="/wiki/5-MeO-2-TMT" title="5-MeO-2-TMT">5-MeO-2-TMT</a></li> <li><a href="/w/index.php?title=5-MeO-34MPEMT&action=edit&redlink=1" class="new" title="5-MeO-34MPEMT (page does not exist)">5-MeO-34MPEMT</a></li> <li><a href="/wiki/5-Methoxy-7,N,N-trimethyltryptamine" title="5-Methoxy-7,N,N-trimethyltryptamine">5-MeO-7,N,N-TMT</a></li> <li><a href="/wiki/5-MeO-DALT" title="5-MeO-DALT">5-MeO-DALT</a></li> <li><a href="/wiki/5-MeO-DBT" title="5-MeO-DBT">5-MeO-DBT</a></li> <li><a href="/wiki/5-MeO-DET" title="5-MeO-DET">5-MeO-DET</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/5-MeO-DMT" title="5-MeO-DMT">5-MeO-DMT</a></li> <li><a href="/wiki/5-MeO-DPT" title="5-MeO-DPT">5-MeO-DPT</a></li> <li><a href="/wiki/5-MeO-EiPT" title="5-MeO-EiPT">5-MeO-EiPT</a></li> <li><a href="/wiki/5-MeO-EPT" title="5-MeO-EPT">5-MeO-EPT</a></li> <li><a href="/wiki/5-MeO-MALT" title="5-MeO-MALT">5-MeO-MALT</a></li> <li><a href="/wiki/5-MeO-MET" title="5-MeO-MET">5-MeO-MET</a></li> <li><a href="/wiki/5-MeO-MiPT" title="5-MeO-MiPT">5-MeO-MiPT</a></li> <li><a href="/w/index.php?title=5-MeO-NET&action=edit&redlink=1" class="new" title="5-MeO-NET (page does not exist)">5-MeO-NET</a></li> <li><a href="/w/index.php?title=5-MeO-NiPT&action=edit&redlink=1" class="new" title="5-MeO-NiPT (page does not exist)">5-MeO-NiPT</a></li> <li><a href="/wiki/5-MeO-NMT" title="5-MeO-NMT">5-MeO-NMT</a></li> <li><a href="/wiki/5-MeO-pyr-T" title="5-MeO-pyr-T">5-MeO-pyr-T</a></li> <li><a href="/wiki/5-MeO-NBpBrT" title="5-MeO-NBpBrT">5-MeO-NBpBrT</a></li> <li><a href="/wiki/5-Methoxytryptamine" title="5-Methoxytryptamine">5-MeO-T (5-MT; mexamine)</a></li> <li><a href="/wiki/5-MeO-T-NBOMe" title="5-MeO-T-NBOMe">5-MeO-T-NBOMe</a></li> <li><a href="/wiki/5-MeS-DMT" title="5-MeS-DMT">5-MeS-DMT</a></li> <li><a href="/wiki/5,N,N-TMT" title="5,N,N-TMT">5-Methyl-DMT</a></li> <li><a href="/wiki/5-Methyltryptamine" title="5-Methyltryptamine">5-Methyl-T</a></li> <li><a href="/w/index.php?title=5-MT-NB3OMe&action=edit&redlink=1" class="new" title="5-MT-NB3OMe (page does not exist)">5-MT-NB3OMe</a></li> <li><a href="/wiki/5-(Nonyloxy)tryptamine" title="5-(Nonyloxy)tryptamine">5-NOT</a></li> <li><a href="/wiki/5,6-MeO-MiPT" title="5,6-MeO-MiPT">5,6-MeO-MiPT</a></li> <li><a href="/wiki/5,6-MDO-DiPT" title="5,6-MDO-DiPT">5,6-MDO-DiPT</a></li> <li><a href="/wiki/5,6-MDO-DMT" title="5,6-MDO-DMT">5,6-MDO-DMT</a></li> <li><a href="/wiki/5,6-MDO-MiPT" title="5,6-MDO-MiPT">5,6-MDO-MiPT</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-Fluoro-DMT" title="6-Fluoro-DMT">6-Fluoro-DMT</a></li> <li><a href="/w/index.php?title=6-Fluorotryptamine&action=edit&redlink=1" class="new" title="6-Fluorotryptamine (page does not exist)">6-Fluoro-T</a></li> <li><a href="/wiki/6-MeO-DMT" title="6-MeO-DMT">6-MeO-DMT</a></li> <li><a href="/w/index.php?title=6-Methoxytryptamine&action=edit&redlink=1" class="new" title="6-Methoxytryptamine (page does not exist)">6-MeO-T</a></li> <li><a href="/w/index.php?title=6-Methyltryptamine&action=edit&redlink=1" class="new" title="6-Methyltryptamine (page does not exist)">6-Methyl-T</a></li> <li><a href="/wiki/6,7-Dihydroxytryptamine" title="6,7-Dihydroxytryptamine">6,7-DHT</a></li> <li><a href="/w/index.php?title=7-Chlorotryptamine&action=edit&redlink=1" class="new" title="7-Chlorotryptamine (page does not exist)">7-Chloro-T</a></li> <li><a href="/w/index.php?title=7-Methoxytryptamine&action=edit&redlink=1" class="new" title="7-Methoxytryptamine (page does not exist)">7-MeO-T</a></li> <li><a href="/wiki/7,N,N-TMT" title="7,N,N-TMT">7-Methyl-DMT</a></li> <li><a href="/w/index.php?title=7-Methyltryptamine&action=edit&redlink=1" class="new" title="7-Methyltryptamine (page does not exist)">7-Methyl-T</a></li> <li><a href="/wiki/Acetryptine" title="Acetryptine">Acetryptine (5-AT)</a></li> <li><a href="/wiki/Aeruginascin" title="Aeruginascin">Aeruginascin (4-PO-TMT)</a></li> <li><a href="/wiki/AGH-107" title="AGH-107">AGH-107</a></li> <li><a href="/wiki/AGH-192" title="AGH-192">AGH-192</a></li> <li><a href="/wiki/AH-494" title="AH-494">AH-494</a></li> <li><a href="/w/index.php?title=ALiPT&action=edit&redlink=1" class="new" title="ALiPT (page does not exist)">ALiPT</a></li> <li><a href="/wiki/Alpertine" title="Alpertine">Alpertine</a></li> <li><a href="/wiki/Baeocystin" title="Baeocystin">Baeocystin (4-PO-NMT)</a></li> <li><a href="/wiki/Benzotript" title="Benzotript">Benzotript (4-chlorobenzoyl-L-tryptophan)</a></li> <li><a href="/wiki/Bufotenidine" title="Bufotenidine">Bufotenidine (5-HTQ)</a></li> <li><a href="/wiki/Bufotenin" title="Bufotenin">Bufotenin (5-HO-DMT)</a></li> <li><a href="/wiki/Convolutindole_A" title="Convolutindole A">Convolutindole A</a></li> <li><a href="/wiki/CP-132,484" title="CP-132,484">CP-132,484</a></li> <li><a href="/wiki/DALT" title="DALT">DALT</a></li> <li><a href="/wiki/Dibutyltryptamine" title="Dibutyltryptamine">DBT</a></li> <li><a href="/wiki/Desformylflustrabromine" title="Desformylflustrabromine">Desformylflustrabromine</a></li> <li><a href="/wiki/Diethyltryptamine" title="Diethyltryptamine">DET</a></li> <li><a href="/wiki/Diisopropyltryptamine" class="mw-redirect" title="Diisopropyltryptamine">DiPT</a></li> <li><a href="/wiki/Dimethyltryptamine" class="mw-redirect" title="Dimethyltryptamine">DMT</a></li> <li><a href="/wiki/Dipropyltryptamine" title="Dipropyltryptamine">DPT</a></li> <li><a href="/wiki/E-6801" title="E-6801">E-6801</a></li> <li><a href="/wiki/E-6837" title="E-6837">E-6837</a></li> <li><a href="/wiki/Ethylisopropyltryptamine" title="Ethylisopropyltryptamine">EiPT</a></li> <li><a href="/wiki/EMDT" title="EMDT">EMDT</a></li> <li><a href="/wiki/Ethylpropyltryptamine" title="Ethylpropyltryptamine">EPT</a></li> <li><a href="/wiki/Ethocybin" title="Ethocybin">Ethocybin (4-PO-DET)</a></li> <li><a href="/wiki/FGIN-127" title="FGIN-127">FGIN-127</a></li> <li><a href="/wiki/FGIN-143" title="FGIN-143">FGIN-143</a></li> <li><a href="/wiki/FT-104" title="FT-104">FT-104</a></li> <li><a href="/wiki/HIOC" title="HIOC">HIOC</a></li> <li><a href="/wiki/Idalopirdine" title="Idalopirdine">Idalopirdine</a></li> <li><a href="/w/index.php?title=Indolylethylfentanyl&action=edit&redlink=1" class="new" title="Indolylethylfentanyl (page does not exist)">Indolylethylfentanyl</a></li> <li><a href="/wiki/Indorenate" title="Indorenate">Indorenate</a></li> <li><a href="/wiki/4-HO-DiPT" title="4-HO-DiPT">Iprocin (4-HO-DiPT)</a></li> <li><a href="/wiki/Isamide" title="Isamide">Isamide</a></li> <li><a href="/wiki/Lespedamine" title="Lespedamine">Lespedamine</a></li> <li><a href="/wiki/Methylbutyltryptamine" title="Methylbutyltryptamine">MBT</a></li> <li><a href="/wiki/N-Methyl-N-ethyltryptamine" title="N-Methyl-N-ethyltryptamine">MET</a></li> <li><a href="/wiki/Milipertine" title="Milipertine">Milipertine</a></li> <li><a href="/wiki/4-HO-MiPT" title="4-HO-MiPT">Miprocin (4-HO-MiPT)</a></li> <li><a href="/wiki/Methylisopropyltryptamine" class="mw-redirect" title="Methylisopropyltryptamine">MiPT</a></li> <li><a href="/wiki/4-Acetoxy-MiPT" class="mw-redirect" title="4-Acetoxy-MiPT">MPT</a></li> <li><a href="/wiki/MS-245" title="MS-245">MS-245</a></li> <li><a href="/wiki/Methylbutyltryptamine#MSBT" title="Methylbutyltryptamine">MSBT</a></li> <li><a href="/wiki/N-Feruloylserotonin" title="N-Feruloylserotonin">N-Feruloylserotonin (moschamine)</a></li> <li><a href="/wiki/NBoc-DMT" title="NBoc-DMT">NBoc-DMT</a></li> <li><a href="/wiki/N-Ethyltryptamine" title="N-Ethyltryptamine">NET/NETP</a></li> <li><a href="/w/index.php?title=N-Isopropyltryptamine&action=edit&redlink=1" class="new" title="N-Isopropyltryptamine (page does not exist)">NiPT</a></li> <li><a href="/wiki/N-Methyltryptamine" title="N-Methyltryptamine">NMT</a></li> <li><a href="/wiki/Norbaeocystin" title="Norbaeocystin">Norbaeocystin (4-PO-T)</a></li> <li><a href="/wiki/N-t-Butyltryptamine" title="N-t-Butyltryptamine">NTBT</a></li> <li><a href="/wiki/O-4310" title="O-4310">O-4310</a></li> <li><a href="/wiki/O-Pivalylbufotenine" title="O-Pivalylbufotenine">O-Pivalylbufotenine</a></li> <li><a href="/wiki/Oxypertine" title="Oxypertine">Oxypertine</a></li> <li><a href="/wiki/Propylisopropyltryptamine" title="Propylisopropyltryptamine">PiPT</a></li> <li><a href="/wiki/Psilacetin" class="mw-redirect" title="Psilacetin">Psilacetin (O-acetylpsilocin; 4-AcO-DMT)</a></li> <li><a href="/wiki/Psilocin" title="Psilocin">Psilocin (4-HO-DMT)</a></li> <li><a class="mw-selflink selflink">Psilocybin (4-PO-DMT)</a></li> <li><a href="/wiki/Psilomethoxin" title="Psilomethoxin">Psilomethoxin (4-HO-5-MeO-DMT)</a></li> <li><a href="/wiki/Pyr-T" title="Pyr-T">Pyr-T</a></li> <li><a href="/wiki/RS134-49" title="RS134-49">RS134-49</a></li> <li><a href="/wiki/Serotonin" title="Serotonin">Serotonin (5-HT)</a></li> <li><a href="/wiki/Solypertine" title="Solypertine">Solypertine</a></li> <li><a href="/wiki/ST-1936" title="ST-1936">ST-1936</a></li> <li><a href="/wiki/Tryptamine" title="Tryptamine">Tryptamine (T)</a></li> <li><a href="/wiki/Tryptophan" title="Tryptophan">Tryptophan</a></li> <li><a href="/wiki/Yuremamine" title="Yuremamine">Yuremamine</a></li> <li><a href="/w/index.php?title=Z2876442907&action=edit&redlink=1" class="new" title="Z2876442907 (page does not exist)">Z2876442907</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/N-Acetyltryptamine" title="N-Acetyltryptamine">N-Acetyltryptamines</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-Iodomelatonin" title="2-Iodomelatonin">2-Iodomelatonin</a></li> <li><a href="/w/index.php?title=2-Phenylmelatonin&action=edit&redlink=1" class="new" title="2-Phenylmelatonin (page does not exist)">2-Phenylmelatonin</a></li> <li><a href="/w/index.php?title=5-Methoxyluzindole&action=edit&redlink=1" class="new" title="5-Methoxyluzindole (page does not exist)">5-Methoxyluzindole</a></li> <li><a href="/w/index.php?title=6-Chloromelatonin&action=edit&redlink=1" class="new" title="6-Chloromelatonin (page does not exist)">6-Chloromelatonin</a></li> <li><a href="/w/index.php?title=6-Fluoromelatonin&action=edit&redlink=1" class="new" title="6-Fluoromelatonin (page does not exist)">6-Fluoromelatonin</a></li> <li><a href="/wiki/6-Hydroxymelatonin" title="6-Hydroxymelatonin">6-Hydroxymelatonin</a></li> <li><a href="/w/index.php?title=6-Methoxymelatonin&action=edit&redlink=1" class="new" title="6-Methoxymelatonin (page does not exist)">6-Methoxymelatonin</a></li> <li><a href="/w/index.php?title=6,7-Dichloro-2-methylmelatonin&action=edit&redlink=1" class="new" title="6,7-Dichloro-2-methylmelatonin (page does not exist)">6,7-Dichloro-2-methylmelatonin</a></li> <li><a href="/wiki/%CE%91-Methylmelatonin" title="Α-Methylmelatonin">α-Methylmelatonin</a></li> <li><a href="/wiki/Luzindole" title="Luzindole">Luzindole</a></li> <li><a href="/wiki/Melatonin" title="Melatonin">Melatonin</a></li> <li><a href="/wiki/N-Acetylserotonin" title="N-Acetylserotonin">Normelatonin (N-acetylserotonin; NAS)</a></li> <li><a href="/wiki/N-Acetyltryptamine" title="N-Acetyltryptamine">N-Acetyltryptamine</a></li> <li><a href="/w/index.php?title=N-Butanoylmelatonin&action=edit&redlink=1" class="new" title="N-Butanoylmelatonin (page does not exist)">N-Butanoylmelatonin</a></li> <li><a href="/w/index.php?title=N-Propionylmelatonin&action=edit&redlink=1" class="new" title="N-Propionylmelatonin (page does not exist)">N-Propionylmelatonin</a></li> <li><a href="/wiki/Piromelatine" title="Piromelatine">Piromelatine</a></li> <li><a href="/wiki/TIK-301" title="TIK-301">TIK-301</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/%CE%91-Alkyltryptamine" class="mw-redirect" title="Α-Alkyltryptamine">α-Alkyltryptamines</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,%CE%B1-Dimethyltryptamine" title="2,α-Dimethyltryptamine">2,α-DMT</a></li> <li><a href="/wiki/4-HO-%CE%B1MT" title="4-HO-αMT">4-HO-αMT</a></li> <li><a href="/wiki/4-HO-MPMI" title="4-HO-MPMI">4-HO-MPMI (lucigenol)</a></li> <li><a href="/wiki/4-Methyl-%CE%B1-ethyltryptamine" title="4-Methyl-α-ethyltryptamine">4-Me-αET</a></li> <li><a href="/wiki/4-Me-%CE%B1MT" class="mw-redirect" title="4-Me-αMT">4-Me-αMT</a></li> <li><a href="/wiki/5-Chloro-%CE%B1ET" title="5-Chloro-αET">5-Chloro-αET</a></li> <li><a href="/wiki/5-Chloro-%CE%B1MT" title="5-Chloro-αMT">5-Chloro-αMT</a></li> <li><a href="/wiki/5-Ethoxy-AMT" class="mw-redirect" title="5-Ethoxy-AMT">5-Ethoxy-αMT</a></li> <li><a href="/wiki/5-Fluoro-AET" title="5-Fluoro-AET">5-Fluoro-αET</a></li> <li><a href="/wiki/5-Fluoro-AMT" title="5-Fluoro-AMT">5-Fluoro-αMT</a></li> <li><a href="/w/index.php?title=5-Isopropoxy-AMT&action=edit&redlink=1" class="new" title="5-Isopropoxy-AMT (page does not exist)">5-iPrO-αMT</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-AET" title="5-MeO-AET">5-MeO-αET </a></li> <li><a href="/wiki/5-MeO-aMT" class="mw-redirect" title="5-MeO-aMT">5-MeO-αMT</a></li> <li><a href="/wiki/5-MeO-MPMI" title="5-MeO-MPMI">5-MeO-MPMI</a></li> <li><a href="/w/index.php?title=5-Methyl-AET&action=edit&redlink=1" class="new" title="5-Methyl-AET (page does not exist)">5-Methyl-αET</a></li> <li><a href="/wiki/6-Fluoro-AMT" title="6-Fluoro-AMT">6-Fluoro-αMT</a></li> <li><a href="/wiki/7-Chloro-AMT" title="7-Chloro-AMT">7-Chloro-αMT</a></li> <li><a href="/wiki/7-Methyl-%CE%B1-ethyltryptamine" title="7-Methyl-α-ethyltryptamine">7-Methyl-αET</a></li> <li><a href="/wiki/%CE%91-Methyl-5-hydroxytryptophan" title="Α-Methyl-5-hydroxytryptophan">α-Methyl-5-HTP</a></li> <li><a href="/wiki/%CE%91-Methylmelatonin" title="Α-Methylmelatonin">α-Methylmelatonin</a></li> <li><a href="/wiki/%CE%91-Methylserotonin" title="Α-Methylserotonin">α-Methylserotonin (5-HO-αMT)</a></li> <li><a href="/wiki/%CE%91-Methyltryptophan" title="Α-Methyltryptophan">α-Methyltryptophan (αMTP)</a></li> <li><a href="/wiki/Alpha,N-DMT" class="mw-redirect" title="Alpha,N-DMT">α,N-DMT (N-methyl-αMT)</a></li> <li><a href="/wiki/%CE%91,N,N-Trimethyltryptamine" title="Α,N,N-Trimethyltryptamine">α,N,N-TMT</a></li> <li><a href="/wiki/Alpha,N,O-TMS" class="mw-redirect" title="Alpha,N,O-TMS">α,N,O-TMS</a></li> <li><a href="/wiki/%CE%91-Ethyltryptamine" title="Α-Ethyltryptamine">αET (etryptamine)</a></li> <li><a href="/wiki/%CE%91-Methyltryptamine" title="Α-Methyltryptamine">αMT</a></li> <li><a href="/wiki/AL-37350A" title="AL-37350A">AL-37350A (4,5-DHP-αMT)</a></li> <li><a href="/w/index.php?title=BK-5Br-NM-AMT&action=edit&redlink=1" class="new" title="BK-5Br-NM-AMT (page does not exist)">BK-5Br-NM-AMT</a></li> <li><a href="/w/index.php?title=BK-5Cl-NM-AMT&action=edit&redlink=1" class="new" title="BK-5Cl-NM-AMT (page does not exist)">BK-5Cl-NM-AMT</a></li> <li><a href="/w/index.php?title=BK-5F-NM-AMT&action=edit&redlink=1" class="new" title="BK-5F-NM-AMT (page does not exist)">BK-5F-NM-AMT</a></li> <li><a href="/wiki/BK-NM-AMT" title="BK-NM-AMT">BK-NM-AMT</a></li> <li><a href="/wiki/BNC-210" title="BNC-210">BNC-210</a></li> <li><a href="/wiki/BW-723C86" title="BW-723C86">BW-723C86</a></li> <li><a href="/wiki/CP-135807" title="CP-135807">CP-135807</a></li> <li><a href="/wiki/Indolylpropylaminopentane" title="Indolylpropylaminopentane">IPAP (α,N-DPT)</a></li> <li><a href="/wiki/MPMI_(drug)" title="MPMI (drug)">MPMI</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Triptan" title="Triptan">Triptans</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/Almotriptan" title="Almotriptan">Almotriptan</a></li> <li><a href="/wiki/Donitriptan" title="Donitriptan">Donitriptan</a></li> <li><a href="/wiki/Eletriptan" title="Eletriptan">Eletriptan</a></li> <li><a href="/wiki/Frovatriptan" title="Frovatriptan">Frovatriptan</a></li> <li><a href="/wiki/L-694247" title="L-694247">L-694247</a></li> <li><a href="/wiki/Rizatriptan" title="Rizatriptan">Rizatriptan</a></li> <li><a href="/wiki/Sumatriptan" title="Sumatriptan">Sumatriptan</a></li> <li><a href="/wiki/Zolmitriptan" title="Zolmitriptan">Zolmitriptan</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Cyclic_compound" title="Cyclic compound">Cyclized 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/Bay_R_1531" title="Bay R 1531">Bay R 1531</a></li> <li><a href="/wiki/Ciclindole" title="Ciclindole">Ciclindole</a></li> <li><a href="/wiki/Cyclic_3-hydroxymelatonin" title="Cyclic 3-hydroxymelatonin">Cyclic 3-OHM</a></li> <li><a href="/wiki/Ergoline" title="Ergoline">Ergolines</a> and <a href="/wiki/Lysergamide" class="mw-redirect" title="Lysergamide">lysergamides</a> (e.g., <a href="/wiki/Lysergic_acid_diethylamide" class="mw-redirect" title="Lysergic acid diethylamide">LSD</a>)</li> <li><a href="/wiki/Flucindole" title="Flucindole">Flucindole</a></li> <li><a href="/wiki/Harmala_alkaloid" title="Harmala alkaloid">Harmala alkaloids</a> and <a href="/wiki/%CE%92-carboline" class="mw-redirect" title="Β-carboline">β-carbolines</a> (e.g., <a href="/wiki/6-MeO-THH" title="6-MeO-THH">6-MeO-THH</a>, <a href="/wiki/9-Methyl-%CE%B2-carboline" title="9-Methyl-β-carboline">9-Me-BC</a>, <a href="/wiki/%CE%92-carboline" class="mw-redirect" title="Β-carboline">β-carboline (norharman)</a>, <a href="/wiki/Harmaline" title="Harmaline">harmaline</a>, <a href="/wiki/Harmalol" title="Harmalol">harmalol</a>, <a href="/wiki/Harmane" title="Harmane">harmane</a>, <a href="/wiki/Harmine" title="Harmine">harmine</a>, <a href="/wiki/Pinoline" title="Pinoline">pinoline</a>, <a href="/wiki/Tetrahydroharmine" title="Tetrahydroharmine">tetrahydroharmine</a>, <a href="/wiki/Tryptoline" title="Tryptoline">tryptoline</a>)</li> <li><a href="/wiki/Iboga-type_alkaloid" title="Iboga-type alkaloid">Iboga alkaloids</a> and related (e.g., <a href="/wiki/DM-506" title="DM-506">DM-506 (ibogaminalog)</a>, <a href="/wiki/Ibogaine" title="Ibogaine">ibogaine</a>, <a href="/wiki/Ibogamine" title="Ibogamine">ibogamine</a>, <a href="/wiki/Noribogaine" title="Noribogaine">noribogaine</a>, <a href="/wiki/Tabernanthalog" title="Tabernanthalog">tabernanthalog</a>, <a href="/wiki/Tabernanthine" title="Tabernanthine">tabernanthine</a>)</li> <li><a href="/wiki/LY-266,097" title="LY-266,097">LY-266,097</a></li> <li><a href="/wiki/Metralindole" title="Metralindole">Metralindole</a></li> <li><a href="/wiki/NDTDI" title="NDTDI">NDTDI</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/RU-28306" title="RU-28306">RU-28306</a></li> <li><a href="/wiki/Yohimban" title="Yohimban">Yohimbans</a> (e.g., <a href="/wiki/Yohimbine" title="Yohimbine">yohimbine</a>, <a href="/wiki/Rauwolscine" title="Rauwolscine">rauwolscine</a>, <a href="/wiki/Spegatrine" title="Spegatrine">spegatrine</a>, <a href="/wiki/Corynanthine" title="Corynanthine">corynanthine</a>, <a href="/wiki/Ajmalicine" title="Ajmalicine">ajmalicine</a>, <a href="/wiki/Reserpine" title="Reserpine">reserpine</a>, <a href="/wiki/Deserpidine" title="Deserpidine">deserpidine</a>, <a href="/wiki/Rescinnamine" title="Rescinnamine">rescinnamine</a>)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Isotryptamine" title="Isotryptamine">Isotryptamines</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/5-MeO-isoDMT" title="5-MeO-isoDMT">5-MeO-isoDMT</a></li> <li><a href="/wiki/6-MeO-isoDMT" title="6-MeO-isoDMT">6-MeO-isoDMT</a></li> <li><a href="/wiki/AAZ-A-154" class="mw-redirect" title="AAZ-A-154">AAZ-A-154 (DLX-001)</a></li> <li><a href="/wiki/IsoAMT" class="mw-redirect" title="IsoAMT">isoAMT</a></li> <li><a href="/wiki/IsoDMT" title="IsoDMT">isoDMT</a></li> <li><a href="/wiki/Isotryptamine" title="Isotryptamine">Isotryptamine (isoT)</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></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;">Related compounds</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="/w/index.php?title=2-Azapsilocin&action=edit&redlink=1" class="new" title="2-Azapsilocin (page does not exist)">2-Azapsilocin</a></li> <li><a href="/w/index.php?title=4-Aza-5-MeO-DPT&action=edit&redlink=1" class="new" title="4-Aza-5-MeO-DPT (page does not exist)">4-Aza-5-MeO-DPT</a></li> <li><a href="/w/index.php?title=5-Aza-4-MeO-DiPT&action=edit&redlink=1" class="new" title="5-Aza-4-MeO-DiPT (page does not exist)">5-Aza-4-MeO-DiPT</a></li> <li><a href="/wiki/5-Hydroxyindoleacetic_acid" title="5-Hydroxyindoleacetic acid">5-HIAA</a></li> <li><a href="/wiki/5-Hydroxyindoleacetaldehyde" title="5-Hydroxyindoleacetaldehyde">5-HIAL</a></li> <li><a href="/w/index.php?title=5-Hydroxyindole_thiazoladine_carboxylic_acid&action=edit&redlink=1" class="new" title="5-Hydroxyindole thiazoladine carboxylic acid (page does not exist)">5-HITCA</a></li> <li><a href="/w/index.php?title=5-Methoxyindoleacetaldehyde&action=edit&redlink=1" class="new" title="5-Methoxyindoleacetaldehyde (page does not exist)">5-MIAL</a></li> <li><a href="/w/index.php?title=7-Aza-5-MeO-DiPT&action=edit&redlink=1" class="new" title="7-Aza-5-MeO-DiPT (page does not exist)">7-Aza-5-MeO-DiPT</a></li> <li><a href="/wiki/AAZ-A-154" class="mw-redirect" title="AAZ-A-154">AAZ-A-154</a></li> <li><a href="/wiki/AL-34662" title="AL-34662">AL-34662</a></li> <li><a href="/wiki/AL-38022A" title="AL-38022A">AL-38022A</a></li> <li><a href="/wiki/Substituted_benzofuran" title="Substituted benzofuran">Benzofurans</a> (e.g., <a href="/wiki/3-(2-aminopropyl)benzofuran" class="mw-redirect" title="3-(2-aminopropyl)benzofuran">3-APB</a>, <a href="/wiki/5-MeO-DiBF" title="5-MeO-DiBF">5-MeO-DiBF</a>, <a href="/wiki/Benzofuranylpropylaminopentane" title="Benzofuranylpropylaminopentane">BPAP</a>, <a href="/wiki/Dimemebfe" title="Dimemebfe">dimemebfe</a>, <a href="/wiki/Mebfap" title="Mebfap">mebfap</a>)</li> <li><a href="/wiki/BRL-54443" title="BRL-54443">BRL-54443</a></li> <li><a href="/wiki/CP-94253" title="CP-94253">CP-94253</a></li> <li><a href="/wiki/EMD-386088" title="EMD-386088">EMD-386088</a></li> <li><a href="/w/index.php?title=I-32_(drug)&action=edit&redlink=1" class="new" title="I-32 (drug) (page does not exist)">I-32</a></li> <li><a href="/wiki/Indoleacetaldehyde" class="mw-redirect" title="Indoleacetaldehyde">IAL</a></li> <li><a href="/wiki/Latrepirdine" title="Latrepirdine">Latrepirdine</a></li> <li><a href="/wiki/LY-367,265" title="LY-367,265">LY-367265</a></li> <li>Non-tryptamine <a href="/wiki/Triptan" title="Triptan">triptans</a> (e.g., <a href="/wiki/Avitriptan" title="Avitriptan">avitriptan</a>, <a href="/wiki/LY-334370" title="LY-334370">LY-334370</a>, <a href="/wiki/Naratriptan" title="Naratriptan">naratriptan</a>)</li> <li><a href="/wiki/Pirlindole" title="Pirlindole">Pirlindole</a></li> <li><a href="/wiki/(R)-69" title="(R)-69">(R)-69 (3IQ)</a></li> <li><a href="/wiki/Ro60-0213" title="Ro60-0213">Ro60-0213</a></li> <li><a href="/wiki/RU-24,969" title="RU-24,969">RU-24,969</a></li> <li><a href="/wiki/Sertindole" title="Sertindole">Sertindole</a></li> <li><a href="/wiki/SN-22" title="SN-22">SN-22</a></li> <li><a href="/wiki/Tepirindole" title="Tepirindole">Tepirindole</a></li> <li><a href="/wiki/Tetrindole" title="Tetrindole">Tetrindole</a></li> <li><a href="/wiki/VER-3323" title="VER-3323">VER-3323</a></li> <li><a href="/wiki/VU6067416" title="VU6067416">VU6067416</a></li> <li><a href="/wiki/YM-348" title="YM-348">YM-348</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=Psilocybin&oldid=1276141270">https://en.wikipedia.org/w/index.php?title=Psilocybin&oldid=1276141270</a>"</div></div> <div id="catlinks" class="catlinks" data-mw="interface"><div id="mw-normal-catlinks" class="mw-normal-catlinks"><a 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