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class="vector-toc-numb">2</span> <span>History</span> </div> </a> <ul id="toc-History-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Uses" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Uses"> <div class="vector-toc-text"> <span class="vector-toc-numb">3</span> <span>Uses</span> </div> </a> <ul id="toc-Uses-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Mechanism_of_action" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Mechanism_of_action"> <div class="vector-toc-text"> <span class="vector-toc-numb">4</span> <span>Mechanism of action</span> </div> </a> <button aria-controls="toc-Mechanism_of_action-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> <span class="vector-icon mw-ui-icon-wikimedia-expand"></span> <span>Toggle Mechanism of action subsection</span> </button> <ul id="toc-Mechanism_of_action-sublist" class="vector-toc-list"> <li id="toc-Dopaminergic/antidopaminergic" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Dopaminergic/antidopaminergic"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.1</span> <span>Dopaminergic/antidopaminergic</span> </div> </a> <ul id="toc-Dopaminergic/antidopaminergic-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Serotonergic/antiserotonergic" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Serotonergic/antiserotonergic"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.2</span> <span>Serotonergic/antiserotonergic</span> </div> </a> <ul id="toc-Serotonergic/antiserotonergic-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Ergoline_derivatives" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Ergoline_derivatives"> <div class="vector-toc-text"> <span class="vector-toc-numb">5</span> <span>Ergoline derivatives</span> </div> </a> <button aria-controls="toc-Ergoline_derivatives-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> <span class="vector-icon mw-ui-icon-wikimedia-expand"></span> <span>Toggle Ergoline derivatives subsection</span> </button> <ul id="toc-Ergoline_derivatives-sublist" class="vector-toc-list"> <li id="toc-Lysergic_acid_amides" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Lysergic_acid_amides"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.1</span> <span>Lysergic acid amides</span> </div> </a> <ul id="toc-Lysergic_acid_amides-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Peptide_alkaloids" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Peptide_alkaloids"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.2</span> <span>Peptide alkaloids</span> </div> </a> <ul id="toc-Peptide_alkaloids-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Clavines" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Clavines"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.3</span> <span>Clavines</span> </div> </a> <ul id="toc-Clavines-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Others" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Others"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.4</span> <span>Others</span> </div> </a> <ul id="toc-Others-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-See_also" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#See_also"> <div class="vector-toc-text"> <span class="vector-toc-numb">6</span> <span>See also</span> </div> </a> <ul id="toc-See_also-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-References" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#References"> <div class="vector-toc-text"> <span class="vector-toc-numb">7</span> <span>References</span> </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 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#External_links"> <div class="vector-toc-text"> <span class="vector-toc-numb">8</span> <span>External links</span> </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" > 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Available in 18 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-18" aria-hidden="true" ><span class="vector-icon mw-ui-icon-language-progressive mw-ui-icon-wikimedia-language-progressive"></span> <span class="vector-dropdown-label-text">18 languages</span> </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%A5%D8%B1%D8%BA%D9%88%D9%84%D9%8A%D9%86" title="إرغولين – Arabic" lang="ar" hreflang="ar" data-title="إرغولين" data-language-autonym="العربية" data-language-local-name="Arabic" class="interlanguage-link-target"><span>العربية</span></a></li><li class="interlanguage-link interwiki-azb mw-list-item"><a href="https://azb.wikipedia.org/wiki/%D8%A7%D8%B1%D9%82%D9%88%D9%84%DB%8C%D9%86" title="ارقولین – South Azerbaijani" lang="azb" hreflang="azb" data-title="ارقولین" data-language-autonym="تۆرکجه" data-language-local-name="South Azerbaijani" class="interlanguage-link-target"><span>تۆرکجه</span></a></li><li class="interlanguage-link interwiki-de mw-list-item"><a href="https://de.wikipedia.org/wiki/Ergolin" title="Ergolin – German" lang="de" hreflang="de" data-title="Ergolin" data-language-autonym="Deutsch" data-language-local-name="German" class="interlanguage-link-target"><span>Deutsch</span></a></li><li class="interlanguage-link interwiki-es mw-list-item"><a href="https://es.wikipedia.org/wiki/Ergolina" title="Ergolina – Spanish" lang="es" hreflang="es" data-title="Ergolina" data-language-autonym="Español" data-language-local-name="Spanish" class="interlanguage-link-target"><span>Español</span></a></li><li class="interlanguage-link interwiki-fa mw-list-item"><a href="https://fa.wikipedia.org/wiki/%D8%A7%D8%B1%DA%AF%D9%88%D9%84%DB%8C%D9%86" title="ارگولین – Persian" lang="fa" hreflang="fa" data-title="ارگولین" data-language-autonym="فارسی" data-language-local-name="Persian" class="interlanguage-link-target"><span>فارسی</span></a></li><li class="interlanguage-link interwiki-fr mw-list-item"><a href="https://fr.wikipedia.org/wiki/Ergoline" title="Ergoline – French" lang="fr" hreflang="fr" data-title="Ergoline" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target"><span>Français</span></a></li><li class="interlanguage-link interwiki-ja mw-list-item"><a href="https://ja.wikipedia.org/wiki/%E3%82%A8%E3%83%AB%E3%82%B4%E3%83%AA%E3%83%B3" title="エルゴリン – Japanese" lang="ja" hreflang="ja" data-title="エルゴリン" data-language-autonym="日本語" data-language-local-name="Japanese" class="interlanguage-link-target"><span>日本語</span></a></li><li class="interlanguage-link interwiki-no mw-list-item"><a href="https://no.wikipedia.org/wiki/Ergolin" title="Ergolin – Norwegian Bokmål" lang="nb" hreflang="nb" data-title="Ergolin" data-language-autonym="Norsk bokmål" data-language-local-name="Norwegian Bokmål" class="interlanguage-link-target"><span>Norsk bokmål</span></a></li><li class="interlanguage-link interwiki-pl mw-list-item"><a href="https://pl.wikipedia.org/wiki/Ergolina" title="Ergolina – Polish" lang="pl" hreflang="pl" data-title="Ergolina" data-language-autonym="Polski" data-language-local-name="Polish" class="interlanguage-link-target"><span>Polski</span></a></li><li class="interlanguage-link interwiki-pt mw-list-item"><a href="https://pt.wikipedia.org/wiki/Ergolina" title="Ergolina – Portuguese" lang="pt" hreflang="pt" data-title="Ergolina" data-language-autonym="Português" data-language-local-name="Portuguese" class="interlanguage-link-target"><span>Português</span></a></li><li class="interlanguage-link interwiki-ro mw-list-item"><a href="https://ro.wikipedia.org/wiki/Ergolin%C4%83" title="Ergolină – Romanian" lang="ro" hreflang="ro" data-title="Ergolină" data-language-autonym="Română" data-language-local-name="Romanian" class="interlanguage-link-target"><span>Română</span></a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/Ergolin" title="Ergolin – Serbian" lang="sr" hreflang="sr" data-title="Ergolin" data-language-autonym="Српски / srpski" data-language-local-name="Serbian" class="interlanguage-link-target"><span>Српски / srpski</span></a></li><li class="interlanguage-link interwiki-sh mw-list-item"><a href="https://sh.wikipedia.org/wiki/Ergolin" title="Ergolin – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Ergolin" data-language-autonym="Srpskohrvatski / српскохрватски" data-language-local-name="Serbo-Croatian" class="interlanguage-link-target"><span>Srpskohrvatski / српскохрватски</span></a></li><li class="interlanguage-link interwiki-fi mw-list-item"><a href="https://fi.wikipedia.org/wiki/Ergoliini" title="Ergoliini – Finnish" lang="fi" hreflang="fi" data-title="Ergoliini" data-language-autonym="Suomi" data-language-local-name="Finnish" class="interlanguage-link-target"><span>Suomi</span></a></li><li class="interlanguage-link interwiki-ta mw-list-item"><a href="https://ta.wikipedia.org/wiki/%E0%AE%8E%E0%AE%B0%E0%AF%8D%E0%AE%95%E0%AF%8B%E0%AE%B2%E0%AF%88%E0%AE%A9%E0%AF%8D" title="எர்கோலைன் – Tamil" lang="ta" hreflang="ta" data-title="எர்கோலைன்" data-language-autonym="தமிழ்" data-language-local-name="Tamil" class="interlanguage-link-target"><span>தமிழ்</span></a></li><li class="interlanguage-link interwiki-tr mw-list-item"><a href="https://tr.wikipedia.org/wiki/Ergolin" title="Ergolin – Turkish" lang="tr" hreflang="tr" data-title="Ergolin" data-language-autonym="Türkçe" data-language-local-name="Turkish" class="interlanguage-link-target"><span>Türkçe</span></a></li><li class="interlanguage-link interwiki-uk mw-list-item"><a href="https://uk.wikipedia.org/wiki/%D0%95%D1%80%D0%B3%D0%BE%D0%BB%D1%96%D0%BD" title="Ерголін – Ukrainian" lang="uk" hreflang="uk" data-title="Ерголін" data-language-autonym="Українська" data-language-local-name="Ukrainian" class="interlanguage-link-target"><span>Українська</span></a></li><li class="interlanguage-link interwiki-zh mw-list-item"><a href="https://zh.wikipedia.org/wiki/%E9%BA%A5%E8%A7%92%E9%9D%88" title="麥角靈 – Chinese" lang="zh" hreflang="zh" data-title="麥角靈" data-language-autonym="中文" data-language-local-name="Chinese" class="interlanguage-link-target"><span>中文</span></a></li> </ul> <div class="after-portlet after-portlet-lang"><span class="wb-langlinks-edit wb-langlinks-link"><a href="https://www.wikidata.org/wiki/Special:EntityPage/Q424432#sitelinks-wikipedia" title="Edit interlanguage links" class="wbc-editpage">Edit links</a></span></div> </div> </div> </div> </header> <div class="vector-page-toolbar"> <div class="vector-page-toolbar-container"> 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.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"><span title="International nonproprietary name (INN): Ergoline">Ergoline</span></caption><tbody><tr><td colspan="2" class="infobox-image notheme" style="background-color: #f8f9fa;"><span typeof="mw:File"><a href="/wiki/File:Ergoline_Structural_Formulae_V.1.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/8/80/Ergoline_Structural_Formulae_V.1.svg/120px-Ergoline_Structural_Formulae_V.1.svg.png" decoding="async" width="120" height="115" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/8/80/Ergoline_Structural_Formulae_V.1.svg/180px-Ergoline_Structural_Formulae_V.1.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/8/80/Ergoline_Structural_Formulae_V.1.svg/240px-Ergoline_Structural_Formulae_V.1.svg.png 2x" data-file-width="512" data-file-height="490" /></a></span></td></tr><tr><td colspan="2" class="infobox-image notheme" style="background-color: #f8f9fa;"><span typeof="mw:File"><a href="/wiki/File:3D_ergoline_molecule_animation.gif" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/f/fa/3D_ergoline_molecule_animation.gif/180px-3D_ergoline_molecule_animation.gif" decoding="async" width="180" height="201" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/f/fa/3D_ergoline_molecule_animation.gif/270px-3D_ergoline_molecule_animation.gif 1.5x, //upload.wikimedia.org/wikipedia/commons/f/fa/3D_ergoline_molecule_animation.gif 2x" data-file-width="358" data-file-height="400" /></a></span></td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd">Clinical data</th></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Anatomical_Therapeutic_Chemical_Classification_System" title="Anatomical Therapeutic Chemical Classification System">ATC code</a></th><td class="infobox-data"><style data-mw-deduplicate="TemplateStyles:r1126788409">.mw-parser-output .plainlist ol,.mw-parser-output .plainlist ul{line-height:inherit;list-style:none;margin:0;padding:0}.mw-parser-output .plainlist ol li,.mw-parser-output .plainlist ul li{margin-bottom:0}</style><div class="plainlist"><ul><li>none</li></ul></div></td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd">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%;">(6a<i>R</i>)-4,6,6a,7,8,9,10,10a-Octahydroindolo[4,3-<i>fg</i>]quinoline</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><span title="commonchemistry.cas.org"><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=478-88-6">478-88-6</a></span><sup> <span typeof="mw:File"><span><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" /></span></span><span style="display:none">Y</span></sup></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> <span style="font-weight:normal"><abbr title="Compound ID">CID</abbr></span></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="pubchem.ncbi.nlm.nih.gov"><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/6857537">6857537</a></span></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><span title="www.chemspider.com"><a rel="nofollow" class="external text" href="https://www.chemspider.com/Chemical-Structure.5256873.html">5256873</a></span><sup> <span typeof="mw:File"><span><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" /></span></span><span style="display:none">Y</span></sup></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><span title="precision.fda.gov"><a rel="nofollow" class="external text" href="https://precision.fda.gov/uniisearch/srs/unii/D5RC6H62GW">D5RC6H62GW</a></span></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><span title="www.ebi.ac.uk"><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:38484">CHEBI:38484</a></span><sup> <span typeof="mw:File"><span><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" /></span></span><span style="display:none">Y</span></sup></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> <span style="font-weight:normal">(<abbr title="U.S. Environmental Protection Agency">EPA</abbr>)</span></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="comptox.epa.gov"><a rel="nofollow" class="external text" href="https://comptox.epa.gov/dashboard/chemical/details/DTXSID00963944">DTXSID00963944</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q424432#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></span></span></li></ul></div></td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd">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"><span title="Carbon">C</span><sub>14</sub><span title="Hydrogen">H</span><sub>16</sub><span title="Nitrogen">N</span><sub>2</sub></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"><span class="nowrap"><span data-sort-value="7002212296000000000♠"></span>212.296</span> g·mol<sup>−1</sup></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><span title="chemapps.stolaf.edu (3D interactive model)"><a rel="nofollow" class="external text" href="https://chemapps.stolaf.edu/jmol/jmol.php?model=%5BH%5D%5BC%40%40%5D34Cc1c%5BnH%5Dc2cccc%28c12%29%5BC%40%40%5D3%28%5BH%5D%29CCCN4">Interactive image</a></span></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/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%;">[H][C@@]34Cc1c[nH]c2cccc(c12)[C@@]3([H])CCCN4</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/C14H16N2/c1-3-11-10-4-2-6-15-13(10)7-9-8-16-12(5-1)14(9)11/h1,3,5,8,10,13,15-16H,2,4,6-7H2/t10-,13-/m1/s1<sup> <span typeof="mw:File"><span><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" /></span></span><span style="display:none">Y</span></sup></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:RHGUXDUPXYFCTE-ZWNOBZJWSA-N<sup> <span typeof="mw:File"><span><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" /></span></span><span style="display:none">Y</span></sup></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><span class="nobold">  <span class="reflink plainlinks nourlexpansion"><a class="external text" href="https://en.wikipedia.org/w/index.php?title=Special:ComparePages&rev1=446242223&page2=Ergoline">(verify)</a></span></span></td></tr></tbody></table> <p><b>Ergoline</b> is a chemical compound whose structural skeleton is contained in a variety of <a href="/wiki/Alkaloid" title="Alkaloid">alkaloids</a>, referred to as ergoline derivatives or ergoline alkaloids. Ergoline alkaloids, one being <a href="/wiki/Ergine" title="Ergine">ergine</a>, were initially characterized in <a href="/wiki/Ergot" title="Ergot">ergot</a>. Some of these are implicated in the condition <a href="/wiki/Ergotism" title="Ergotism">ergotism</a>, which can take a convulsive form or a gangrenous form. Even so, many ergoline alkaloids have been found to be clinically useful. Annual world production of ergot alkaloids has been estimated at 5,000–8,000 kg of all ergopeptines and 10,000–15,000 kg of <a href="/wiki/Lysergic_acid" title="Lysergic acid">lysergic acid</a>, used primarily in the manufacture of semi-synthetic derivatives.<sup id="cite_ref-:02_1-0" class="reference"><a href="#cite_note-:02-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> </p><p>Others, such as <a href="/wiki/Lysergic_acid_diethylamide" class="mw-redirect" title="Lysergic acid diethylamide">lysergic acid diethylamide</a>, better known as LSD, a <a href="/wiki/Semisynthesis" title="Semisynthesis">semi-synthetic</a> derivative, and <a href="/wiki/Ergine" title="Ergine">ergine</a>, a natural derivative found in <i><a href="/wiki/Argyreia_nervosa" title="Argyreia nervosa">Argyreia nervosa</a></i>, <i><a href="/wiki/Ipomoea_tricolor" title="Ipomoea tricolor">Ipomoea tricolor</a></i> and related species, are known <a href="/wiki/Psychedelic_drug" title="Psychedelic drug">psychedelic</a> substances.<sup id="cite_ref-2" class="reference"><a href="#cite_note-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Natural_occurrence">Natural occurrence</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Ergoline&action=edit&section=1" title="Edit section: Natural occurrence"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Ergoline alkaloids are found in lower <a href="/wiki/Fungi" class="mw-redirect" title="Fungi">fungi</a> and some species of <a href="/wiki/Flowering_plant" title="Flowering plant">flowering plants</a>: the <a href="/wiki/Mexico" title="Mexico">Mexican</a> species <i><a href="/wiki/Turbina_corymbosa" class="mw-redirect" title="Turbina corymbosa">Turbina corymbosa</a></i> and <i><a href="/wiki/Ipomoea_tricolor" title="Ipomoea tricolor">Ipomoea tricolor</a></i> of the <a href="/wiki/Convolvulaceae" title="Convolvulaceae">Convolvulaceae</a> (morning glory) family, the seeds of which were identified as the psychedelic plant drugs known as "ololiuhqui" and "tlitliltzin", respectively.<sup id="cite_ref-Schardl20063_3-0" class="reference"><a href="#cite_note-Schardl20063-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-4" class="reference"><a href="#cite_note-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> The principal alkaloids in the seeds are ergine and its <a href="/wiki/Optical_isomer" class="mw-redirect" title="Optical isomer">optical isomer</a> isoergine, with several other lysergic acid derivatives and clavines present in lesser amounts. The <a href="/wiki/Hawaii" title="Hawaii">Hawaiian</a> species <i><a href="/wiki/Argyreia_nervosa" title="Argyreia nervosa">Argyreia nervosa</a></i> includes similar alkaloids. It is possible, though not proven, that <a href="/wiki/Ergine" title="Ergine">ergine</a> or isoergine are responsible for the <a href="/wiki/Psychedelic_drug" title="Psychedelic drug">psychedelic</a> effects. There may be a fungal origin of the ergoline alkaloids also in the Convolvulaceae. Like the ergot alkaloids in some monocot plants, the ergoline alkaloids found in the plant <i><a href="/wiki/Ipomoea_asarifolia" title="Ipomoea asarifolia">Ipomoea asarifolia</a></i> (Convolvulaceae) are produced by a seed-transmitted <a href="/wiki/Endophyte" title="Endophyte">endophytic</a> <a href="/wiki/Clavicipitaceae" title="Clavicipitaceae">clavicipitaceous</a> <a href="/wiki/Fungus" title="Fungus">fungus</a>.<sup id="cite_ref-5" class="reference"><a href="#cite_note-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="History">History</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Ergoline&action=edit&section=2" title="Edit section: History"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Ergoline <a href="/wiki/Alkaloid" title="Alkaloid">alkaloids</a> were first isolated from <a href="/wiki/Ergot" title="Ergot">ergot</a>, a fungus that infects rye and causes <a href="/wiki/Ergotism" title="Ergotism">ergotism</a> or St. Anthony's fire.<sup id="cite_ref-6" class="reference"><a href="#cite_note-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> Reports of the toxic effects due to ergoline alkaloids date back to the 12th century.<sup id="cite_ref-:12_7-0" class="reference"><a href="#cite_note-:12-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> Ergot also has a long history of medicinal use, which led to attempts to characterize its activity chemically. First reports of its use date back to 1582, where preparations of ergot were used in small doses by midwives to induce strong uterine contractions.<sup id="cite_ref-:02_1-1" class="reference"><a href="#cite_note-:02-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-:12_7-1" class="reference"><a href="#cite_note-:12-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> The first use of ergoline alkaloids in modern medicine was described in 1808 by John Stearns, an American physician, who had reported on the uterine contractile actions of a preparation of ergot as a remedy for "quickening birth".<sup id="cite_ref-:02_1-2" class="reference"><a href="#cite_note-:02-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> </p><p>Attempts to characterize the activity of ergoline alkaloids began in 1907, with the isolation of ergotoxine by G. Barger and F. H. Carrin.<sup id="cite_ref-:2_8-0" class="reference"><a href="#cite_note-:2-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> However, the industrial production of ergot alkaloids didn't begin until 1918, when <a href="/wiki/Arthur_Stoll" title="Arthur Stoll">Arthur Stoll</a> patented the isolation of <a href="/wiki/Ergotamine_tartrate" class="mw-redirect" title="Ergotamine tartrate">ergotamine tartrate</a>, which was marketed by <a href="/wiki/Sandoz" title="Sandoz">Sandoz</a> in 1921. Following the determination of the basic <a href="/wiki/Chemical_structure" title="Chemical structure">chemical structure</a> of the ergot alkaloids in 1930, an era of intensive exploration of synthetic derivatives began and industrial production of ergoline alkaloids exploded, with Sandoz continuing to be the leading company in their production worldwide, up until 1950 when other competitors arose.<sup id="cite_ref-:02_1-3" class="reference"><a href="#cite_note-:02-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-:2_8-1" class="reference"><a href="#cite_note-:2-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> The company, now renamed <a href="/wiki/Novartis" title="Novartis">Novartis</a>, still retains its leadership in the product of ergot alkaloids. In 1943, Arthur Stoll and <a href="/wiki/Albert_Hofmann" title="Albert Hofmann">Albert Hofmann</a> reported the first total synthesis of an ergot alkaloid, ergometrine.<sup id="cite_ref-9" class="reference"><a href="#cite_note-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> Though the synthesis found no industrial application, this was a huge leap forward in the industry. </p> <div class="mw-heading mw-heading2"><h2 id="Uses">Uses</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Ergoline&action=edit&section=3" title="Edit section: Uses"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>There are a variety of clinically useful ergoline derivatives for the purpose of <a href="/wiki/Vasoconstriction" title="Vasoconstriction">vasoconstriction</a>, the treatment of <a href="/wiki/Migraine" title="Migraine">migraines</a>, and treatment of <a href="/wiki/Parkinson%27s_disease" title="Parkinson's disease">Parkinson's disease</a>. Ergoline alkaloids found their place in pharmacology long before modern medicine as preparations of ergot were often used by midwives in the 12th century to stimulate childbirth.<sup id="cite_ref-10" class="reference"><a href="#cite_note-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> Following Arthur Stoll's isolation of ergometrine, the therapeutic use of ergoline derivatives became well explored. </p><p>The induction of uterine contractions via the preparation of ergot was attributed to <a href="/wiki/Ergonovine" class="mw-redirect" title="Ergonovine">ergonovine</a>, an ergoline derivative found in ergot, which is a powerful <a href="/wiki/Oxytocic" class="mw-redirect" title="Oxytocic">oxytocic</a>. From this, <a href="/wiki/Methergine" class="mw-redirect" title="Methergine">methergine</a>, a synthetic derivative, was elucidated.<sup id="cite_ref-:12_7-2" class="reference"><a href="#cite_note-:12-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> While used to facilitate child birth, ergoline derivatives can pass into <a href="/wiki/Breast_milk" title="Breast milk">breast milk</a> and should not be used during breastfeeding.<sup id="cite_ref-kidsgrowth2_11-0" class="reference"><a href="#cite_note-kidsgrowth2-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> They are uterine contractors that can increase the risk of miscarriage during pregnancy.<sup id="cite_ref-Schardl20063_3-1" class="reference"><a href="#cite_note-Schardl20063-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> </p><p>Another example of medically relevant ergoline alkaloids is <a href="/wiki/Ergotamine" title="Ergotamine">ergotamine</a>, an alkaloid also found in ergot. It acts as a <a href="/wiki/Vasoconstriction" title="Vasoconstriction">vasoconstrictor</a> and has been reported to control <a href="/wiki/Migraine" title="Migraine">migraines</a>. From ergotamine, the <a href="/wiki/Anti-migraine" class="mw-redirect" title="Anti-migraine">anti-migraine</a> drugs <a href="/wiki/Dihydroergotamine" title="Dihydroergotamine">dihydroergotamine</a> and <a href="/wiki/Methysergide" title="Methysergide">methysergide</a> were developed by Albert Hofmann.<sup id="cite_ref-12" class="reference"><a href="#cite_note-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup> </p><p>Ergoline derivatives, such as <a href="/wiki/Hydergine" class="mw-redirect" title="Hydergine">hydergine</a>, a mixture of dihydroergotoxine mesylates or ergoline mesylates, have also been used in the treatment of dementia. The use of these alkaloids in the treatment of <a href="/wiki/Parkinson%27s_disease" title="Parkinson's disease">Parkinson's disease</a> has also been prominent. Drugs such as <a href="/wiki/Bromocriptine" title="Bromocriptine">bromocriptine</a> act as a dopamine receptor <a href="/wiki/Agonist" title="Agonist">agonist</a>, stimulating the nerves that control movement.<sup id="cite_ref-:3_13-0" class="reference"><a href="#cite_note-:3-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup> Newer synthetic ergoline derivatives that have been synthesized for the treatment of Parkinson's disease include <a href="/wiki/Pergolide" title="Pergolide">pergolide</a> and <a href="/wiki/Lisuride" title="Lisuride">lisuride</a>, which both act as dopamine agonists as well.<sup id="cite_ref-:3_13-1" class="reference"><a href="#cite_note-:3-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup> </p><p>A famous ergoline derivative is the <a href="/wiki/Psychedelic_drug" title="Psychedelic drug">psychedelic drug</a> <a href="/wiki/LSD" title="LSD">LSD</a>, a <a href="/wiki/Semisynthesis" title="Semisynthesis">semi-synthetic</a> ergoline alkaloid that was discovered by Albert Hofmann. LSD is considered a <a href="/wiki/Schedule_I_controlled_substance" class="mw-redirect" title="Schedule I controlled substance">Schedule I controlled substance</a>. <a href="/wiki/Ergometrine" title="Ergometrine">Ergometrine</a> and <a href="/wiki/Ergotamine" title="Ergotamine">ergotamine</a> are included as schedule I precursors in the <a href="/wiki/United_Nations_Convention_Against_Illicit_Traffic_in_Narcotic_Drugs_and_Psychotropic_Substances" title="United Nations Convention Against Illicit Traffic in Narcotic Drugs and Psychotropic Substances">United Nations Convention Against Illicit Traffic in Narcotic Drugs and Psychotropic Substances</a>.<sup id="cite_ref-http://www.incb.org/pdf/e/list/red.pdf2_14-0" class="reference"><a href="#cite_note-http://www.incb.org/pdf/e/list/red.pdf2-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Mechanism_of_action">Mechanism of action</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Ergoline&action=edit&section=4" title="Edit section: Mechanism of action"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The mechanism of ergoline alkaloids varies for each derivative. A variety of modifications can be made to the ergoline skeleton to produce medically relevant derivatives. Types of potential ergoline-based drugs include <a href="/wiki/Dopaminergic" title="Dopaminergic">dopaminergic</a>, <a href="/wiki/Antidopaminergic" class="mw-redirect" title="Antidopaminergic">antidopaminergic</a>, <a href="/wiki/Serotonin" title="Serotonin">serotonergic</a>, and <a href="/wiki/Antiserotonergic" class="mw-redirect" title="Antiserotonergic">antiserotonergic</a>.<sup id="cite_ref-:4_15-0" class="reference"><a href="#cite_note-:4-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup> Ergoline alkaloids often interfere with multiple receptor sites, leading to negative side effects and adding to the challenge of drug development. </p> <div class="mw-heading mw-heading3"><h3 id="Dopaminergic/antidopaminergic"><span id="Dopaminergic.2Fantidopaminergic"></span>Dopaminergic/antidopaminergic</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Ergoline&action=edit&section=5" title="Edit section: Dopaminergic/antidopaminergic"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Ergolines, such as ergotoxin, have been reported to inhibit the deciduoma reaction, which is reversed through injection of progesterone. Thus, it was concluded that ergotoxin, and related ergolines, act via the <a href="/wiki/Hypothalamus" title="Hypothalamus">hypothalamus</a> and <a href="/wiki/Pituitary_gland" title="Pituitary gland">pituitary gland</a> to inhibit the <a href="/wiki/Secretion" title="Secretion">secretion</a> of <a href="/wiki/Prolactin" title="Prolactin">prolactin</a>.<sup id="cite_ref-:4_15-1" class="reference"><a href="#cite_note-:4-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup> Drugs such as <a href="/wiki/Bromocriptine" title="Bromocriptine">bromocriptine</a> interact with the dopaminergic receptor sites as agonists with selectivity for D<sub>2</sub> receptors, making them effective in treating Parkinson's disease. While the part of the ergoline alkaloid structure responsible for dopaminergic properties has yet to be identified, some reason that it is due to the pyroleethylamine moiety while others assert that it is due to the indoleethylamine partial structure.<sup id="cite_ref-:4_15-2" class="reference"><a href="#cite_note-:4-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup> </p><p>Antidopaminergic ergolines have found use in <a href="/wiki/Antiemetic" title="Antiemetic">antiemetics</a> and in the treatment of <a href="/wiki/Schizophrenia" title="Schizophrenia">schizophrenia</a>. These substances are <a href="/wiki/Neuroleptic" class="mw-redirect" title="Neuroleptic">neuroleptic</a> and are either an antagonist of dopamine at the postsynaptic level at the D<sub>2</sub> receptor site or an agonist of dopamine at the presynaptic level at the D<sub>1</sub> receptor site.<sup id="cite_ref-:4_15-3" class="reference"><a href="#cite_note-:4-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup> The antagonist or agonist behavior of the ergolines are substrate dependent and mixed agonist/antagonist behaviors of ergoline derivatives have been reported.<sup id="cite_ref-:4_15-4" class="reference"><a href="#cite_note-:4-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Serotonergic/antiserotonergic"><span id="Serotonergic.2Fantiserotonergic"></span>Serotonergic/antiserotonergic</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Ergoline&action=edit&section=6" title="Edit section: Serotonergic/antiserotonergic"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The primary challenges of developing serotonergic/antiserotonergic ergolines is attributed to <a href="/wiki/Serotonin" title="Serotonin">serotonin</a>, or 5-HT, acting on various distinct receptor sites. Similarly, ergoline alkaloids have been shown to exhibit both 5-HT agonist and antagonist behaviors for multiple receptors, such as <a href="/wiki/Metergoline" title="Metergoline">metergoline</a>, a 5-HT<sub>1A</sub> agonist/5-HT<sub>2A</sub> antagonist, and <a href="/wiki/Mesulergine" title="Mesulergine">mesulergine</a>, a 5-HT<sub>2A/2C</sub> antagonist.<sup id="cite_ref-:4_15-5" class="reference"><a href="#cite_note-:4-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup> The selectivity and affinity of ergolines for certain 5-HT receptors can be improved by introducing a bulky group on the phenyl ring of the ergoline skeleton, which would prevent the interaction of ergoline derivatives with receptors.<sup id="cite_ref-:4_15-6" class="reference"><a href="#cite_note-:4-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup> This methodology has been used to develop selective 5-HT<sub>1A</sub> and 5-HT<sub>2A</sub> ergolines in particular. </p> <div class="mw-heading mw-heading2"><h2 id="Ergoline_derivatives">Ergoline derivatives</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Ergoline&action=edit&section=7" title="Edit section: Ergoline derivatives"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>There are 3 main classes of ergoline derivatives, the water-soluble <a href="/wiki/Amide" title="Amide">amides</a> of <i><a href="/wiki/Lysergic_acid" title="Lysergic acid">lysergic acid</a></i>, the water-insoluble <i>ergopeptines</i> (i.e., <i>ergo<a href="/wiki/Peptides" class="mw-redirect" title="Peptides">peptides</a></i>), and the <i>clavine</i> group.<sup id="cite_ref-Schardl2006_16-0" class="reference"><a href="#cite_note-Schardl2006-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Lysergic_acid_amides">Lysergic acid amides</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Ergoline&action=edit&section=8" title="Edit section: Lysergic acid amides"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></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">Main article: <a href="/wiki/Lysergamides" title="Lysergamides">Lysergamides</a></div> <ul><li><a href="/wiki/Ergine" title="Ergine">Ergine</a> (LSA, <small>D</small>-lysergic acid amide, LAA, LA-111) <ul><li><a href="/wiki/IUPAC_name" class="mw-redirect" title="IUPAC name">IUPAC name</a>: 9,10-didehydro-6-methylergoline-8beta-carboxamide</li> <li><a href="/wiki/CAS_number" class="mw-redirect" title="CAS number">CAS number</a>: <a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=478-94-4&title=">478-94-4</a></li></ul></li> <li><a href="/wiki/Ergonovine" class="mw-redirect" title="Ergonovine">Ergonovine</a> (ergobasine) <ul><li><a href="/wiki/International_Nonproprietary_Name" class="mw-redirect" title="International Nonproprietary Name">INN</a>: ergometrine</li> <li>IUPAC name: (8beta(S))-9,10-didehydro-N-(2-hydroxy-1-methylethyl)-6-methyl-ergoline-8-carboxamide</li> <li>CAS number: <a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=60-79-7&title=">60-79-7</a></li></ul></li> <li><a href="/wiki/Methergine" class="mw-redirect" title="Methergine">Methergine</a> (ME-277) <ul><li>INN: methylergometrine</li> <li>IUPAC name: (8beta(S))-9,10-didehydro-N-(1-(hydroxymethyl)propyl)-6-methyl-ergoline-8-carboxamide</li> <li>CAS number: <a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=113-42-8&title=">113-42-8</a></li></ul></li> <li><a href="/wiki/Methysergide" title="Methysergide">Methysergide</a> (UML-491) <ul><li>INN: methysergide</li> <li>IUPAC name: (8<i>beta</i>)-9,10-didehydro-<i>N</i>-(1-(hydroxymethyl)propyl)-1,6-dimethyl-ergoline-8-carboxamide</li> <li>CAS number: <a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=361-37-5&title=">361-37-5</a></li></ul></li> <li><a href="/wiki/LSD" title="LSD">LSD</a> (<small>D</small>-lysergic acid diethylamide, LSD-25) <ul><li>INN: lysergide</li> <li>IUPAC name: (8beta)-9,10-didehydro-N,N-diethyl-6-methyl-ergoline-8-carboxamide</li> <li>CAS number: <a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=50-37-3&title=">50-37-3</a></li></ul></li> <li><a href="/wiki/Lysergic_acid_hydroxyethylamide" title="Lysergic acid hydroxyethylamide">LSH</a> (<small>D</small>-lysergic acid α-hydroxyethylamide) <ul><li>IUPAC name: 9,10-didehydro-N-(1-hydroxyethyl)-6-methylergoline-8-carboxamide</li> <li>CAS number: <a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=3343-15-5&title=">3343-15-5</a></li></ul></li></ul> <p>The relationship between these compounds is summarized in the following <a href="/wiki/Structural_formula" title="Structural formula">structural formula</a> and table of substitutions. </p> <figure class="mw-default-size mw-halign-left" typeof="mw:File"><a href="/wiki/File:Ergine_-_Ergines.svg" class="mw-file-description" title="Substituted ergine (structural formula)"><img alt="Substituted ergine (structural formula)" src="//upload.wikimedia.org/wikipedia/commons/thumb/7/71/Ergine_-_Ergines.svg/223px-Ergine_-_Ergines.svg.png" decoding="async" width="223" height="302" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/7/71/Ergine_-_Ergines.svg/335px-Ergine_-_Ergines.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/7/71/Ergine_-_Ergines.svg/446px-Ergine_-_Ergines.svg.png 2x" data-file-width="223" data-file-height="302" /></a><figcaption>Substituted ergine (structural formula)</figcaption></figure> <table class="wikitable" style="float:right"> <tbody><tr> <th>Name</th> <th>R<sup>1</sup></th> <th>R<sup>2</sup></th> <th>R<sup>3</sup> </th></tr> <tr> <td><a href="/wiki/Ergine" title="Ergine">Ergine</a></td> <td>H</td> <td>H</td> <td>H </td></tr> <tr> <td><a href="/wiki/Ergonovine" class="mw-redirect" title="Ergonovine">Ergonovine</a></td> <td>H</td> <td>CH(CH<sub>3</sub>)CH<sub>2</sub>OH</td> <td>H </td></tr> <tr> <td><a href="/wiki/Methergine" class="mw-redirect" title="Methergine">Methergine</a></td> <td>H</td> <td>CH(CH<sub>2</sub>CH<sub>3</sub>)CH<sub>2</sub>OH</td> <td>H </td></tr> <tr> <td><a href="/wiki/Methysergide" title="Methysergide">Methysergide</a></td> <td><a href="/wiki/Methyl" class="mw-redirect" title="Methyl">CH<sub>3</sub></a></td> <td>CH(CH<sub>2</sub>CH<sub>3</sub>)CH<sub>2</sub>OH</td> <td>H </td></tr> <tr> <td><a href="/wiki/LSD" title="LSD">LSD</a></td> <td>H</td> <td><a href="/wiki/Ethyl_group" title="Ethyl group">CH<sub>2</sub>CH<sub>3</sub></a></td> <td>CH<sub>2</sub>CH<sub>3</sub> </td></tr></tbody></table> <div style="clear:both;" class=""></div> <div class="mw-heading mw-heading3"><h3 id="Peptide_alkaloids">Peptide alkaloids</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Ergoline&action=edit&section=9" title="Edit section: Peptide alkaloids"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Peptide ergot alkaloids or <b><a href="/wiki/Ergopeptines" class="mw-redirect" title="Ergopeptines">ergopeptines</a></b> (also known as <i>ergopeptides</i>) are ergoline derivatives that contain a tri<a href="/wiki/Peptide" title="Peptide">peptide</a> structure attached to the basic ergoline ring in the same location as the <a href="/wiki/Amide" title="Amide">amide</a> group of the lysergic acid derivatives. This structure consists of <a href="/wiki/Proline" title="Proline">proline</a> and two other α-amino acids, linked in an unusual <a href="/wiki/Cyclol" title="Cyclol">cyclol</a> formation >N-C(OH)< with the carboxyl carbon of proline, at the juncture between the two <a href="/wiki/Lactam" title="Lactam">lactam</a> rings.<sup id="cite_ref-17" class="reference"><a href="#cite_note-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup> Some of the important ergopeptines are summarized below.<sup id="cite_ref-18" class="reference"><a href="#cite_note-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup> In addition to the following ergopeptines, a commonly encountered term is <b>ergotoxine</b>, which refers to a mixture of equal proportions of <a href="/wiki/Ergocristine" title="Ergocristine">ergocristine</a>, <a href="/wiki/Ergocornine" title="Ergocornine">ergocornine</a> and ergocryptine, the latter being a 2:1 mixture of <i><a href="/wiki/Ergocryptine" title="Ergocryptine">alpha</a></i>- and <a href="/wiki/Beta-Ergocryptine" class="mw-redirect" title="Beta-Ergocryptine"><i>beta</i>-ergocryptine</a>. </p> <ul><li>Ergotoxine group (<a href="/wiki/Valine" title="Valine">valine</a> as the amino acid attached to the ergoline moiety, at R<sup>2</sup> below) <ul><li><a href="/wiki/Ergocristine" title="Ergocristine">Ergocristine</a> <ul><li><a href="/wiki/IUPAC_name" class="mw-redirect" title="IUPAC name">IUPAC name</a>: Ergotaman-3',6',18-trione, 12'-hydroxy-2'-(1-methylethyl)-5'-(phenylmethyl)-, (5'-alpha)-</li> <li><a href="/wiki/CAS_number" class="mw-redirect" title="CAS number">CAS number</a>: <a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=511-08-0&title=">511-08-0</a></li></ul></li> <li><a href="/wiki/Ergocornine" title="Ergocornine">Ergocornine</a> <ul><li>IUPAC name: Ergotaman-3',6',18-trione, 12'-hydroxy-2',5'-bis(1-methylethyl)-, (5'-alpha)-</li> <li>CAS number: <a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=564-36-3&title=">564-36-3</a></li></ul></li> <li><i>alpha</i>-<a href="/wiki/Ergocryptine" title="Ergocryptine">Ergocryptine</a> <ul><li>IUPAC name: Ergotaman-3',6',18-trione, 12'-hydroxy-2'-(1-methylethyl)-5'-(2-methylpropyl)-, (5'alpha)-</li> <li>CAS number: <a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=511-09-1&title=">511-09-1</a></li></ul></li> <li><a href="/wiki/Beta-Ergocryptine" class="mw-redirect" title="Beta-Ergocryptine"><i>beta</i>-Ergocryptine</a> <ul><li>IUPAC name: Ergotaman-3',6',18-trione, 12'-hydroxy-2'-(1-methylethyl)-5'-(1-methylpropyl)-, (5'alpha(<i>S</i>))-</li> <li>CAS number: <a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=20315-46-2&title=">20315-46-2</a></li></ul></li></ul></li> <li>Ergotamine group (<a href="/wiki/Alanine" title="Alanine">alanine</a> at R<sup>2</sup>) <ul><li><a href="/wiki/Ergotamine" title="Ergotamine">Ergotamine</a> <ul><li>IUPAC name: Ergotaman-3',6',18-trione, 12'-hydroxy-2'-methyl-5'-(phenylmethyl)-, (5'-alpha)-</li> <li>CAS number: <a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=113-15-5&title=">113-15-5</a></li></ul></li> <li><a href="/wiki/Ergovaline" title="Ergovaline">Ergovaline</a> <ul><li>IUPAC name: Ergotaman-3',6',18-trione, 12'-hydroxy-2'-methyl-5'-(1-methylethyl)-, (5'alpha)-</li> <li>CAS number: <a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=2873-38-3&title=">2873-38-3</a></li></ul></li> <li><i>alpha</i>-<a href="/wiki/Ergosine" title="Ergosine">Ergosine</a> <ul><li>IUPAC name: Ergotaman-3',6',18-trione, 12'-hydroxy-2'-methyl-5'-(2-methylpropyl)-, (5'-alpha)-</li> <li>CAS number: <a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=561-94-4&title=">561-94-4</a></li></ul></li> <li><a href="/wiki/Beta-Ergosine" class="mw-redirect" title="Beta-Ergosine"><i>beta</i>-Ergosine</a> <ul><li>IUPAC name: Ergotaman-3',6',18-trione, 12'-hydroxy-2'-methyl-5'-(1-methylpropyl)-, (5'-alpha(<i>S</i>))-</li> <li>CAS number: <a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=60192-59-8&title=">60192-59-8</a></li></ul></li></ul></li></ul> <figure class="mw-default-size mw-halign-left" typeof="mw:File"><a href="/wiki/File:Ergopeptine_-_Ergopeptines.svg" class="mw-file-description" title="Ergopeptides (structural formula)"><img alt="Ergopeptides (structural formula)" src="//upload.wikimedia.org/wikipedia/commons/thumb/f/fb/Ergopeptine_-_Ergopeptines.svg/405px-Ergopeptine_-_Ergopeptines.svg.png" decoding="async" width="405" height="439" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/f/fb/Ergopeptine_-_Ergopeptines.svg/608px-Ergopeptine_-_Ergopeptines.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/f/fb/Ergopeptine_-_Ergopeptines.svg/810px-Ergopeptine_-_Ergopeptines.svg.png 2x" data-file-width="405" data-file-height="439" /></a><figcaption>Ergopeptides (structural formula)</figcaption></figure> <table class="wikitable" style="float:right"> <tbody><tr> <th>Name</th> <th>R<sup>1</sup></th> <th>R<sup>2</sup></th> <th>R<sup>3</sup></th> <th>Amino acid at R<sup>2</sup></th> <th>Amino acid at R<sup>3</sup> </th></tr> <tr> <td><a href="/wiki/Ergocristine" title="Ergocristine">Ergocristine</a></td> <td></td> <td><a href="/wiki/Isopropyl" class="mw-redirect" title="Isopropyl">CH(CH<sub>3</sub>)<sub>2</sub></a></td> <td><a href="/wiki/Benzyl" class="mw-redirect" title="Benzyl">benzyl</a></td> <td>Valine</td> <td><a href="/wiki/Phenylalanine" title="Phenylalanine">Phenylalanine</a> </td></tr> <tr> <td><a href="/wiki/Ergocornine" title="Ergocornine">Ergocornine</a></td> <td></td> <td>CH(CH<sub>3</sub>)<sub>2</sub></td> <td>CH(CH<sub>3</sub>)<sub>2</sub></td> <td>Valine</td> <td><a href="/wiki/Valine" title="Valine">Valine</a> </td></tr> <tr> <td><i>alpha</i>-<a href="/wiki/Ergocryptine" title="Ergocryptine">Ergocryptine</a></td> <td></td> <td>CH(CH<sub>3</sub>)<sub>2</sub></td> <td>CH<sub>2</sub>CH(CH<sub>3</sub>)<sub>2</sub></td> <td>Valine</td> <td><a href="/wiki/Leucine" title="Leucine">Leucine</a> </td></tr> <tr> <td><a href="/wiki/Beta-Ergocryptine" class="mw-redirect" title="Beta-Ergocryptine"><i>beta</i>-Ergocryptine</a></td> <td></td> <td>CH(CH<sub>3</sub>)<sub>2</sub></td> <td>CH(CH<sub>3</sub>)CH<sub>2</sub>CH<sub>3</sub> (<i>S</i>)</td> <td>Valine</td> <td><a href="/wiki/Isoleucine" title="Isoleucine">Isoleucine</a> </td></tr> <tr> <td><a href="/wiki/Ergotamine" title="Ergotamine">Ergotamine</a></td> <td></td> <td><a href="/wiki/Methyl" class="mw-redirect" title="Methyl">CH<sub>3</sub></a></td> <td>benzyl</td> <td><a href="/wiki/Alanine" title="Alanine">Alanine</a></td> <td>Phenylalanine </td></tr> <tr> <td><a href="/wiki/Ergovaline" title="Ergovaline">Ergovaline</a></td> <td></td> <td>CH<sub>3</sub></td> <td>CH(CH<sub>3</sub>)<sub>2</sub></td> <td>Alanine</td> <td>Valine </td></tr> <tr> <td><i>alpha</i>-<a href="/wiki/Ergosine" title="Ergosine">Ergosine</a></td> <td></td> <td>CH<sub>3</sub></td> <td>CH<sub>2</sub>CH(CH<sub>3</sub>)<sub>2</sub></td> <td>Alanine</td> <td>Leucine </td></tr> <tr> <td><a href="/wiki/Beta-Ergosine" class="mw-redirect" title="Beta-Ergosine"><i>beta</i>-Ergosine</a></td> <td></td> <td>CH<sub>3</sub></td> <td>CH(CH<sub>3</sub>)CH<sub>2</sub>CH<sub>3</sub> (<i>S</i>)</td> <td>Alanine</td> <td>Isoleucine </td></tr> <tr> <td><a href="/wiki/Bromocriptine" title="Bromocriptine">Bromocriptine</a> (<a href="/wiki/Semisynthetic" class="mw-redirect" title="Semisynthetic">semisynthetic</a>)</td> <td><a href="/wiki/Bromine" title="Bromine">Br</a></td> <td>CH(CH<sub>3</sub>)<sub>2</sub></td> <td>CH<sub>2</sub>CH(CH<sub>3</sub>)<sub>2</sub></td> <td>Valine</td> <td>Leucine </td></tr></tbody></table> <div style="clear:both;" class=""></div> <div class="mw-heading mw-heading3"><h3 id="Clavines">Clavines</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Ergoline&action=edit&section=10" title="Edit section: Clavines"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>A variety of modifications to the basic ergoline are seen in nature, for example <a href="/wiki/Agroclavine" title="Agroclavine">agroclavine</a>, <a href="/wiki/Elymoclavine" title="Elymoclavine">elymoclavine</a>, <a href="/wiki/Lysergol" title="Lysergol">lysergol</a>. Those deriving from <a href="/w/index.php?title=Dimethylergoline&action=edit&redlink=1" class="new" title="Dimethylergoline (page does not exist)">dimethylergoline</a> are referred to as clavines. Examples of clavines, include <a href="/wiki/Festuclavine" title="Festuclavine">festuclavine</a>, <a href="/wiki/Fumigaclavine_A" title="Fumigaclavine A">fumigaclavine A</a>, <a href="/wiki/Fumigaclavine_B" title="Fumigaclavine B">fumigaclavine B</a> and <a href="/wiki/Fumigaclavine_C" title="Fumigaclavine C">fumigaclavine C</a>. </p> <div class="mw-heading mw-heading3"><h3 id="Others">Others</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Ergoline&action=edit&section=11" title="Edit section: Others"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Some synthetic ergoline derivatives do not fall easily into any of the above groups. Some examples are: </p> <ul><li><a href="/wiki/Cabergoline" title="Cabergoline">Cabergoline</a> (<a href="/wiki/International_Nonproprietary_Name" class="mw-redirect" title="International Nonproprietary Name">INN</a>) <ul><li><a href="/wiki/IUPAC_name" class="mw-redirect" title="IUPAC name">IUPAC name</a>: 1-[(6-Allylergolin-8β-yl)-carbonyl]-1-[3-(dimethylamino)propyl]-3-ethylurea</li> <li><a href="/wiki/CAS_number" class="mw-redirect" title="CAS number">CAS number</a>: <a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=81409-90-7&title=">81409-90-7</a></li></ul></li> <li><a href="/wiki/Pergolide" title="Pergolide">Pergolide</a> (INN) <ul><li>IUPAC name: (8β)-8-((methylthio)methyl)-6-propyl-ergoline</li> <li>CAS number: <a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=66104-22-1&title=">66104-22-1</a></li></ul></li> <li><a href="/wiki/Lisuride" title="Lisuride">Lisuride</a> (INN) <ul><li>IUPAC name: 3-(9,10-didehydro-6-methylergolin-8α-yl)-1,1-diethylurea</li> <li>CAS number: <a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=18016-80-3&title=">18016-80-3</a></li></ul></li></ul> <div class="mw-heading mw-heading2"><h2 id="See_also">See also</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Ergoline&action=edit&section=12" title="Edit section: See also"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a href="/wiki/Ergotism" title="Ergotism">Ergotism</a></li> <li><a href="/wiki/Ergot" title="Ergot">Ergot</a></li> <li><a href="/wiki/LSD" title="LSD">LSD</a></li> <li><a href="/wiki/Ergine" title="Ergine">Ergine</a></li> <li><a href="/wiki/Migraine" title="Migraine">Migraine</a></li> <li><a href="/wiki/Albert_Hofmann" title="Albert Hofmann">Albert Hofmann</a></li></ul> <div class="mw-heading mw-heading2"><h2 id="References">References</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Ergoline&action=edit&section=13" title="Edit section: References"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></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"> <div class="mw-references-wrap mw-references-columns"><ol class="references"> <li id="cite_note-:02-1"><span class="mw-cite-backlink">^ <a href="#cite_ref-:02_1-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-:02_1-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-:02_1-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-:02_1-3"><sup><i><b>d</b></i></sup></a></span> <span class="reference-text"><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="CITEREFSchiff2006" class="citation journal cs1">Schiff PL (October 2006). <a rel="nofollow" class="external 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"Ergoline derivatives: receptor affinity and selectivity". <i>Farmaco</i>. <b>54</b> (5): 288–296. <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%2Fs0014-827x%2899%2900028-2">10.1016/s0014-827x(99)00028-2</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/10418123">10418123</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Farmaco&rft.atitle=Ergoline+derivatives%3A+receptor+affinity+and+selectivity&rft.volume=54&rft.issue=5&rft.pages=288-296&rft.date=1999-05&rft_id=info%3Adoi%2F10.1016%2Fs0014-827x%2899%2900028-2&rft_id=info%3Apmid%2F10418123&rft.aulast=Mantegani&rft.aufirst=S&rft.au=Brambilla%2C+E&rft.au=Varasi%2C+M&rfr_id=info%3Asid%2Fen.wikipedia.org%3AErgoline" class="Z3988"></span></span> </li> <li id="cite_note-Schardl2006-16"><span class="mw-cite-backlink"><b><a href="#cite_ref-Schardl2006_16-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFSchardlPanaccioneTudzynski2006" class="citation book cs1">Schardl CL, Panaccione DG, Tudzynski P (2006). <i>Ergot alkaloids – biology and molecular biology</i>. 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Vol. 63. pp. 45–86. <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%2FS1099-4831%2806%2963002-2">10.1016/S1099-4831(06)63002-2</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-12-469563-4" title="Special:BookSources/978-0-12-469563-4"><bdi>978-0-12-469563-4</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/17133714">17133714</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Ergot+alkaloids+%E2%80%93+biology+and+molecular+biology&rft.series=The+Alkaloids%3A+Chemistry+and+Biology&rft.pages=45-86&rft.date=2006&rft_id=info%3Apmid%2F17133714&rft_id=info%3Adoi%2F10.1016%2FS1099-4831%2806%2963002-2&rft.isbn=978-0-12-469563-4&rft.aulast=Schardl&rft.aufirst=CL&rft.au=Panaccione%2C+DG&rft.au=Tudzynski%2C+P&rfr_id=info%3Asid%2Fen.wikipedia.org%3AErgoline" class="Z3988"></span></span> </li> <li id="cite_note-17"><span class="mw-cite-backlink"><b><a href="#cite_ref-17">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFFloss1976" class="citation journal cs1">Floss HG (January 1976). "Biosynthesis of Ergot Alkaloids and Related Compounds". <i>Tetrahedron Report</i>. <b>32</b> (14): 873–912. <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%2F0040-4020%2876%2985047-8">10.1016/0040-4020(76)85047-8</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Tetrahedron+Report&rft.atitle=Biosynthesis+of+Ergot+Alkaloids+and+Related+Compounds&rft.volume=32&rft.issue=14&rft.pages=873-912&rft.date=1976-01&rft_id=info%3Adoi%2F10.1016%2F0040-4020%2876%2985047-8&rft.aulast=Floss&rft.aufirst=HG&rfr_id=info%3Asid%2Fen.wikipedia.org%3AErgoline" class="Z3988"></span></span> </li> <li id="cite_note-18"><span class="mw-cite-backlink"><b><a href="#cite_ref-18">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFYatesPlattnerGarner1985" class="citation journal cs1">Yates SG, Plattner RD, Garner GB (July 1985). <a rel="nofollow" class="external text" href="https://ddr.nal.usda.gov/bitstream/10113/23986/1/IND86034816.pdf">"Detection of ergopeptine alkaloids in endophyte-infected, toxic Ky-31 tall fescue by mass spectrometry/mass spectrometry"</a> <span class="cs1-format">(PDF)</span>. <i>Journal of Agricultural and Food Chemistry</i>. <b>33</b> (4): 719–722. <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%2Fjf00064a038">10.1021/jf00064a038</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Journal+of+Agricultural+and+Food+Chemistry&rft.atitle=Detection+of+ergopeptine+alkaloids+in+endophyte-infected%2C+toxic+Ky-31+tall+fescue+by+mass+spectrometry%2Fmass+spectrometry&rft.volume=33&rft.issue=4&rft.pages=719-722&rft.date=1985-07&rft_id=info%3Adoi%2F10.1021%2Fjf00064a038&rft.aulast=Yates&rft.aufirst=SG&rft.au=Plattner%2C+RD&rft.au=Garner%2C+GB&rft_id=http%3A%2F%2Fddr.nal.usda.gov%2Fbitstream%2F10113%2F23986%2F1%2FIND86034816.pdf&rfr_id=info%3Asid%2Fen.wikipedia.org%3AErgoline" class="Z3988"></span><sup class="noprint Inline-Template"><span style="white-space: nowrap;">[<i><a href="/wiki/Wikipedia:Link_rot" title="Wikipedia:Link rot"><span title=" Dead link tagged December 2016">permanent dead link</span></a></i><span style="visibility:hidden; color:transparent; padding-left:2px">‍</span>]</span></sup></span> </li> </ol></div></div> <div class="mw-heading mw-heading2"><h2 id="External_links">External links</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Ergoline&action=edit&section=14" title="Edit section: External links"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a rel="nofollow" class="external text" href="https://web.archive.org/web/20040411102155/http://www.people.vcu.edu/~asneden/The%20Ergot%20Alkaloids.pdf">The Ergot Alkaloids (A. T. Sneden)</a></li> <li><a rel="nofollow" class="external text" href="https://web.archive.org/web/20040720041016/http://www.world-of-fungi.org/Mostly_Medical/Ziad_Madlom/Ergot_alkaloids.htm">The Ergot Alkaloids Story (Z. Madlom)</a></li> <li><a rel="nofollow" class="external text" href="http://www.tacethno.com/info/claviceps/ergotalkfungi.txt">The Psychoactive Ergot Alkaloids and their occurrence in the Microfungi — M. P. Bock and D. G. Parbery</a></li> <li><a rel="nofollow" class="external text" href="http://www.erowid.org/plants/mushrooms/references/other/1971_hofmann_bulletin-narcotics.shtml">Hofmann, A. <i>Teonanácatl and Ololiuqui, two ancient magic drugs of Mexico</i> Bulletin on Narcotics 1971 1 3</a></li> <li><a rel="nofollow" class="external text" href="http://www.erowid.org/library/books_online/tihkal/tihkal26.shtml">TiHKAL (A & A Shulgin) #26</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 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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" 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‐<br />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-x" scope="row" class="navbox-group" style="width:1%"><a href="/wiki/2C_(psychedelics)" title="2C (psychedelics)">2C-<i>x</i></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">25<i>x</i>-NB<i>x</i></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%">25<i>x</i>-<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%">25<i>x</i>-<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%">25<i>x</i>-<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%">25<i>x</i>-<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%">25<i>x</i>-<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%">25<i>x</i>-<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%">25<i>x</i>-<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%">25<i>x</i>-NM<i>x</i></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-<i>x</i></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-<i>x</i></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">DO<i>x</i></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-<i>x</i></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">MD<em>xx</em></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" 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"><i>alpha</i>-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" 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%"><i>x</i>-<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%"><i>x</i>-<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%"><i>x</i>-<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%"><i>x</i>-<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" title="O-Acetylpsilocin">4-AcO-DMT</a></li> <li><a href="/wiki/4-Hydroxy-5-methoxydimethyltryptamine" 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,<i>N</i>,<i>N</i>-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,<i>N</i>,<i>N</i>-TMT</a></li> <li><a href="/w/index.php?title=5-MeO-%CE%B1,N,N-TMT&action=edit&redlink=1" class="new" title="5-MeO-α,N,N-TMT (page does not exist)">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-<i>N</i>,<i>N</i>-TMT</a></li> <li><a href="/wiki/7,N,N-TMT" title="7,N,N-TMT">7,N,N-TMT</a></li> <li><a href="/wiki/Alpha-N,N-Trimethyltryptamine" class="mw-redirect" title="Alpha-N,N-Trimethyltryptamine">α,N,N-TMT</a></li> <li><a href="/wiki/Bufotenin" title="Bufotenin">(Bufotenin) 5-HO-DMT</a></li> <li><a href="/wiki/N,N-Dimethyltryptamine" title="N,N-Dimethyltryptamine">DMT</a></li> <li><a href="/wiki/Norbaeocystin" title="Norbaeocystin">Norbaeocystin</a></li> <li><a href="/wiki/Psilocin" title="Psilocin">(Psilocin) 4-HO-DMT</a></li> <li><a href="/wiki/Psilocybin" title="Psilocybin">(Psilocybin) 4-PO-DMT</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><i>x</i>-<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%"><i>x</i>-<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%"><i>x</i>-<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><br /><small>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>).</small></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><br /><small>(<a href="/wiki/NMDA_receptor" title="NMDA receptor">NMDAR</a><br /><a href="/wiki/NMDA_receptor_antagonist" title="NMDA receptor antagonist">antagonists</a>)</small></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‐<br />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><br /><small>(<a href="/wiki/Muscarinic_acetylcholine_receptor" title="Muscarinic acetylcholine receptor">mAChR</a><br /><a href="/wiki/Anticholinergic" title="Anticholinergic">antagonists</a>)</small></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><br /><small>(<a href="/wiki/Cannabinoid_receptor_type_1" class="mw-redirect" title="Cannabinoid receptor type 1">CB<sub>1</sub></a> agonists)</small></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-<i>x</i></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 <i>x</i></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-<i>x</i></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-<i>x</i></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">D<sub>2</sub></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><br /><small>Also indirect D<sub>2</sub> 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>).</small></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/GABAA_receptor" title="GABAA receptor">GABA<sub>A</sub></a><br />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> (<i><a href="/wiki/Amanita_muscaria" title="Amanita muscaria">Amanita muscaria</a></i>)</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><br /><small>(Mixed <a href="/wiki/Mechanism_of_action" title="Mechanism of action">MOA</a>)</small></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="Adrenergic_receptor_modulators" 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:Adrenergic_receptor_modulators" title="Template:Adrenergic receptor modulators"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Adrenergic_receptor_modulators" title="Template talk:Adrenergic receptor modulators"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Adrenergic_receptor_modulators" title="Special:EditPage/Template:Adrenergic receptor modulators"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Adrenergic_receptor_modulators" style="font-size:114%;margin:0 4em"><a href="/wiki/Adrenergic_receptor" title="Adrenergic receptor">Adrenergic 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%"><a href="/wiki/Alpha-1_adrenergic_receptor" title="Alpha-1 adrenergic receptor">α<sub>1</sub></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%">Agonists</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/6-Fluoronorepinephrine" title="6-Fluoronorepinephrine">6-FNE</a></li> <li><a href="/wiki/Amidephrine" title="Amidephrine">Amidephrine</a></li> <li><a href="/wiki/Buspirone" title="Buspirone">Buspirone</a></li> <li><a href="/wiki/Cirazoline" title="Cirazoline">Cirazoline</a></li> <li><a href="/wiki/Corbadrine" title="Corbadrine">Corbadrine</a></li> <li><a href="/wiki/Deoxyepinephrine" title="Deoxyepinephrine">Deoxyepinephrine (epinine, <i>N</i>-methyldopamine)</a></li> <li><a href="/wiki/Desglymidodrine" title="Desglymidodrine">Desglymidodrine</a></li> <li><a href="/w/index.php?title=Dexisometheptene&action=edit&redlink=1" class="new" title="Dexisometheptene (page does not exist)">Dexisometheptene</a></li> <li><a href="/wiki/Dipivefrine" title="Dipivefrine">Dipivefrine</a></li> <li><a href="/wiki/Dopamine" title="Dopamine">Dopamine</a></li> <li><a href="/wiki/Droxidopa" title="Droxidopa">Droxidopa (L-DOPS)</a></li> <li><a href="/wiki/Epinephrine" class="mw-redirect" title="Epinephrine">Epinephrine</a></li> <li><a href="/wiki/Etilefrine" title="Etilefrine">Etilefrine</a></li> <li><a href="/wiki/Etilevodopa" title="Etilevodopa">Etilevodopa</a></li> <li><a href="/wiki/Ethylnorepinephrine" title="Ethylnorepinephrine">Ethylnorepinephrine</a></li> <li><a href="/wiki/Ibopamine" title="Ibopamine">Ibopamine</a></li> <li><a href="/wiki/Indanidine" title="Indanidine">Indanidine</a></li> <li><a href="/wiki/Isometheptene" title="Isometheptene">Isometheptene</a></li> <li><a href="/wiki/L-DOPA" title="L-DOPA">L-DOPA (levodopa)</a></li> <li><a href="/wiki/Phenylalanine" title="Phenylalanine">L-Phenylalanine</a></li> <li><a href="/wiki/Tyrosine" title="Tyrosine">L-Tyrosine</a></li> <li><a href="/wiki/Melevodopa" title="Melevodopa">Melevodopa</a></li> <li><a href="/wiki/Metaraminol" title="Metaraminol">Metaraminol</a></li> <li><a href="/wiki/Methoxamine" title="Methoxamine">Methoxamine</a></li> <li><a href="/wiki/Methyldopa" title="Methyldopa">Methyldopa</a></li> <li><a href="/wiki/Midodrine" title="Midodrine">Midodrine</a></li> <li><a href="/wiki/Naphazoline" title="Naphazoline">Naphazoline</a></li> <li><a href="/wiki/Norepinephrine" title="Norepinephrine">Norepinephrine</a></li> <li><a href="/wiki/Octopamine" title="Octopamine">Octopamine</a></li> <li><a href="/wiki/Oxymetazoline" title="Oxymetazoline">Oxymetazoline</a></li> <li><a href="/wiki/Phenylephrine" title="Phenylephrine">Phenylephrine</a></li> <li><a href="/wiki/Phenylpropanolamine" title="Phenylpropanolamine">Phenylpropanolamine</a></li> <li><a href="/wiki/Synephrine" title="Synephrine">Synephrine</a></li> <li><a href="/wiki/Tetryzoline" title="Tetryzoline">Tetryzoline</a></li> <li><a href="/wiki/Tiamenidine" title="Tiamenidine">Tiamenidine</a></li> <li><a href="/wiki/XP21279" class="mw-redirect" title="XP21279">XP21279</a></li> <li><a href="/wiki/Xylometazoline" title="Xylometazoline">Xylometazoline</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Antagonists</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/Abanoquil" title="Abanoquil">Abanoquil</a></li> <li><a href="/wiki/Ajmalicine" title="Ajmalicine">Ajmalicine</a></li> <li><a href="/wiki/Alfuzosin" title="Alfuzosin">Alfuzosin</a></li> <li><a href="/wiki/Anisodamine" title="Anisodamine">Anisodamine</a></li> <li><a href="/wiki/Anisodine" title="Anisodine">Anisodine</a></li> <li><a href="/wiki/Atiprosin" title="Atiprosin">Atiprosin</a></li> <li><a href="/wiki/Atypical_antipsychotic" title="Atypical antipsychotic">Atypical antipsychotics</a> (e.g., <a href="/wiki/Brexpiprazole" title="Brexpiprazole">brexpiprazole</a>, <a href="/wiki/Clozapine" title="Clozapine">clozapine</a>, <a href="/wiki/Olanzapine" title="Olanzapine">olanzapine</a>, <a href="/wiki/Quetiapine" title="Quetiapine">quetiapine</a>, <a href="/wiki/Risperidone" title="Risperidone">risperidone</a>)</li> <li><a href="/wiki/Benoxathian" title="Benoxathian">Benoxathian</a></li> <li><a href="/wiki/Beta_blocker" title="Beta blocker">Beta blockers</a> (e.g., <a href="/wiki/Adimolol" title="Adimolol">adimolol</a>, <a href="/wiki/Amosulalol" title="Amosulalol">amosulalol</a>, <a href="/wiki/Arotinolol" title="Arotinolol">arotinolol</a>, <a href="/wiki/Carvedilol" title="Carvedilol">carvedilol</a>, <a href="/wiki/Eugenodilol" title="Eugenodilol">eugenodilol</a>, <a href="/wiki/Labetalol" title="Labetalol">labetalol</a>)</li> <li><a href="/wiki/Buflomedil" title="Buflomedil">Buflomedil</a></li> <li><a href="/wiki/Bunazosin" title="Bunazosin">Bunazosin</a></li> <li><a href="/wiki/Corynanthine" title="Corynanthine">Corynanthine</a></li> <li><a href="/wiki/Dapiprazole" title="Dapiprazole">Dapiprazole</a></li> <li><a href="/wiki/Domesticine" title="Domesticine">Domesticine</a></li> <li><a href="/wiki/Doxazosin" title="Doxazosin">Doxazosin</a></li> <li><a class="mw-selflink selflink">Ergolines</a> (e.g., <a href="/wiki/Acetergamine" title="Acetergamine">acetergamine</a>, <a href="/wiki/Ergotamine" title="Ergotamine">ergotamine</a>, <a href="/wiki/Dihydroergotamine" title="Dihydroergotamine">dihydroergotamine</a>, <a href="/wiki/Lisuride" title="Lisuride">lisuride</a>, <a href="/wiki/Nicergoline" title="Nicergoline">nicergoline</a>, <a href="/wiki/Terguride" title="Terguride">terguride</a>)</li> <li><a href="/wiki/Etoperidone" title="Etoperidone">Etoperidone</a></li> <li><a href="/wiki/Fenspiride" title="Fenspiride">Fenspiride</a></li> <li><a href="/wiki/Hydroxyzine" title="Hydroxyzine">Hydroxyzine</a></li> <li><a href="/wiki/Indoramin" title="Indoramin">Indoramin</a></li> <li><a href="/wiki/Ketanserin" title="Ketanserin">Ketanserin</a></li> <li><a href="/wiki/L-765,314" title="L-765,314">L-765,314</a></li> <li><a href="/wiki/Meta-Chlorophenylpiperazine" title="Meta-Chlorophenylpiperazine">mCPP</a></li> <li><a href="/wiki/Mepiprazole" title="Mepiprazole">Mepiprazole</a></li> <li><a href="/wiki/Metazosin" title="Metazosin">Metazosin</a></li> <li><a href="/wiki/Monatepil" title="Monatepil">Monatepil</a></li> <li><a href="/wiki/Moxisylyte" title="Moxisylyte">Moxisylyte</a></li> <li><a href="/wiki/Naftopidil" title="Naftopidil">Naftopidil</a></li> <li><a href="/wiki/Nantenine" title="Nantenine">Nantenine</a></li> <li><a href="/wiki/Neldazosin" title="Neldazosin">Neldazosin</a></li> <li><a href="/wiki/Niaprazine" title="Niaprazine">Niaprazine</a></li> <li><a href="/wiki/Niguldipine" title="Niguldipine">Niguldipine</a></li> <li><a href="/wiki/Pardoprunox" title="Pardoprunox">Pardoprunox</a></li> <li><a href="/wiki/Pelanserin" title="Pelanserin">Pelanserin</a></li> <li><a href="/wiki/Perlapine" title="Perlapine">Perlapine</a></li> <li><a href="/wiki/Phendioxan" title="Phendioxan">Phendioxan</a></li> <li><a href="/wiki/Phenoxybenzamine" title="Phenoxybenzamine">Phenoxybenzamine</a></li> <li><a href="/wiki/Phentolamine" title="Phentolamine">Phentolamine</a></li> <li><a href="/wiki/Phenylpiperazine" title="Phenylpiperazine">Phenylpiperazine</a> <a href="/wiki/Antidepressant" title="Antidepressant">antidepressants</a> (e.g., <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>)</li> <li><a href="/wiki/Piperoxan" title="Piperoxan">Piperoxan</a></li> <li><a href="/wiki/Prazosin" title="Prazosin">Prazosin</a></li> <li><a href="/wiki/Quinazosin" title="Quinazosin">Quinazosin</a></li> <li><a href="/wiki/Quinidine" title="Quinidine">Quinidine</a></li> <li><a href="/wiki/Silodosin" title="Silodosin">Silodosin</a></li> <li><a href="/wiki/Spegatrine" title="Spegatrine">Spegatrine</a></li> <li><a href="/wiki/Spiperone" title="Spiperone">Spiperone</a></li> <li><a href="/wiki/Talipexole" title="Talipexole">Talipexole</a></li> <li><a href="/wiki/Tamsulosin" title="Tamsulosin">Tamsulosin</a></li> <li><a href="/wiki/Terazosin" title="Terazosin">Terazosin</a></li> <li><a href="/wiki/Tiodazosin" title="Tiodazosin">Tiodazosin</a></li> <li><a href="/wiki/Tolazoline" title="Tolazoline">Tolazoline</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>)</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/Imipramine" title="Imipramine">imipramine</a>, <a href="/wiki/Trimipramine" title="Trimipramine">trimipramine</a>)</li> <li><a href="/wiki/Trimazosin" title="Trimazosin">Trimazosin</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/Loxapine" title="Loxapine">loxapine</a>, <a href="/wiki/Thioridazine" title="Thioridazine">thioridazine</a>)</li> <li><a href="/wiki/Urapidil" title="Urapidil">Urapidil</a></li> <li><a href="/wiki/WB-4101" title="WB-4101">WB-4101</a></li> <li><a href="/wiki/Zolertine" title="Zolertine">Zolertine</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/Alpha-2_adrenergic_receptor" title="Alpha-2 adrenergic receptor">α<sub>2</sub></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%">Agonists</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/(R)-3-Nitrobiphenyline" title="(R)-3-Nitrobiphenyline">(R)-3-Nitrobiphenyline</a></li> <li><a href="/wiki/4-NEMD" title="4-NEMD">4-NEMD</a></li> <li><a href="/wiki/6-Fluoronorepinephrine" title="6-Fluoronorepinephrine">6-FNE</a></li> <li><a href="/wiki/Amitraz" title="Amitraz">Amitraz</a></li> <li><a href="/wiki/Apraclonidine" title="Apraclonidine">Apraclonidine</a></li> <li><a href="/wiki/Brimonidine" title="Brimonidine">Brimonidine</a></li> <li><a href="/wiki/Clonidine" title="Clonidine">Clonidine</a></li> <li><a href="/wiki/Corbadrine" title="Corbadrine">Corbadrine</a></li> <li><a href="/wiki/Deoxyepinephrine" title="Deoxyepinephrine">Deoxyepinephrine (epinine, <i>N</i>-methyldopamine)</a></li> <li><a href="/wiki/Detomidine" title="Detomidine">Detomidine</a></li> <li><a href="/wiki/Dexmedetomidine" title="Dexmedetomidine">Dexmedetomidine</a></li> <li><a href="/wiki/Dihydroergotamine" title="Dihydroergotamine">Dihydroergotamine</a></li> <li><a href="/wiki/Dipivefrine" title="Dipivefrine">Dipivefrine</a></li> <li><a href="/wiki/Dopamine" title="Dopamine">Dopamine</a></li> <li><a href="/wiki/Droxidopa" title="Droxidopa">Droxidopa (L-DOPS)</a></li> <li><a href="/wiki/Etilevodopa" title="Etilevodopa">Etilevodopa</a></li> <li><a href="/wiki/Ergotamine" title="Ergotamine">Ergotamine</a></li> <li><a href="/wiki/Epinephrine" class="mw-redirect" title="Epinephrine">Epinephrine</a></li> <li><a href="/wiki/Etilefrine" title="Etilefrine">Etilefrine</a></li> <li><a href="/wiki/Ethylnorepinephrine" title="Ethylnorepinephrine">Ethylnorepinephrine</a></li> <li><a href="/wiki/Guanabenz" title="Guanabenz">Guanabenz</a></li> <li><a href="/wiki/Guanfacine" title="Guanfacine">Guanfacine</a></li> <li><a href="/wiki/Guanoxabenz" title="Guanoxabenz">Guanoxabenz</a></li> <li><a href="/wiki/L-DOPA" title="L-DOPA">L-DOPA (levodopa)</a></li> <li><a href="/wiki/Phenylalanine" title="Phenylalanine">L-Phenylalanine</a></li> <li><a href="/wiki/Tyrosine" title="Tyrosine">L-Tyrosine</a></li> <li><a href="/wiki/Ibopamine" title="Ibopamine">Ibopamine</a></li> <li><a href="/wiki/Lofexidine" title="Lofexidine">Lofexidine</a></li> <li><a href="/wiki/Medetomidine" title="Medetomidine">Medetomidine</a></li> <li><a href="/wiki/Melevodopa" title="Melevodopa">Melevodopa</a></li> <li><a href="/wiki/Methyldopa" title="Methyldopa">Methyldopa</a></li> <li><a href="/wiki/Mivazerol" title="Mivazerol">Mivazerol</a></li> <li><a href="/wiki/Moxonidine" title="Moxonidine">Moxonidine</a></li> <li><a href="/wiki/Naphazoline" title="Naphazoline">Naphazoline</a></li> <li><a href="/wiki/Norepinephrine" title="Norepinephrine">Norepinephrine</a></li> <li><a href="/wiki/Oxymetazoline" title="Oxymetazoline">Oxymetazoline</a></li> <li><a href="/wiki/Phenylpropanolamine" title="Phenylpropanolamine">Phenylpropanolamine</a></li> <li><a href="/wiki/Piperoxan" title="Piperoxan">Piperoxan</a></li> <li><a href="/wiki/PS75" title="PS75">PS75</a></li> <li><a href="/w/index.php?title=Rezatomidine&action=edit&redlink=1" class="new" title="Rezatomidine (page does not exist)">Rezatomidine</a></li> <li><a href="/wiki/Rilmenidine" title="Rilmenidine">Rilmenidine</a></li> <li><a href="/wiki/Romifidine" title="Romifidine">Romifidine</a></li> <li><a href="/wiki/Talipexole" title="Talipexole">Talipexole</a></li> <li><a href="/w/index.php?title=Tasipimidine&action=edit&redlink=1" class="new" title="Tasipimidine (page does not exist)">Tasipimidine</a></li> <li><a href="/wiki/Tetryzoline" title="Tetryzoline">Tetryzoline</a></li> <li><a href="/wiki/Tiamenidine" title="Tiamenidine">Tiamenidine</a></li> <li><a href="/wiki/Tizanidine" title="Tizanidine">Tizanidine</a></li> <li><a href="/wiki/Tolonidine" title="Tolonidine">Tolonidine</a></li> <li><a href="/wiki/Urapidil" title="Urapidil">Urapidil</a></li> <li><a href="/wiki/Vatinoxan" class="mw-redirect" title="Vatinoxan">Vatinoxan</a></li> <li><a href="/wiki/XP21279" class="mw-redirect" title="XP21279">XP21279</a></li> <li><a href="/wiki/Xylazine" title="Xylazine">Xylazine</a></li> <li><a href="/wiki/Xylometazoline" title="Xylometazoline">Xylometazoline</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Antagonists</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/Pyrimidinylpiperazine" title="Pyrimidinylpiperazine">1-PP</a></li> <li><a href="/wiki/Adimolol" title="Adimolol">Adimolol</a></li> <li><a href="/wiki/Amesergide" title="Amesergide">Amesergide</a></li> <li><a href="/wiki/Aptazapine" title="Aptazapine">Aptazapine</a></li> <li><a href="/wiki/Atipamezole" title="Atipamezole">Atipamezole</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/Brexpiprazole" title="Brexpiprazole">brexpiprazole</a>, <a href="/wiki/Clozapine" title="Clozapine">clozapine</a>, <a href="/wiki/Lurasidone" title="Lurasidone">lurasidone</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/Zotepine" title="Zotepine">zotepine</a>)</li> <li><a href="/wiki/Azapirone" title="Azapirone">Azapirones</a> (e.g., <a href="/wiki/Buspirone" title="Buspirone">buspirone</a>, <a href="/wiki/Gepirone" title="Gepirone">gepirone</a>, <a href="/wiki/Ipsapirone" title="Ipsapirone">ipsapirone</a>, <a href="/wiki/Tandospirone" title="Tandospirone">tandospirone</a>)</li> <li><a href="/wiki/BRL-44408" title="BRL-44408">BRL-44408</a></li> <li><a href="/wiki/Buflomedil" title="Buflomedil">Buflomedil</a></li> <li><a href="/wiki/Cirazoline" title="Cirazoline">Cirazoline</a></li> <li><a href="/wiki/Efaroxan" title="Efaroxan">Efaroxan</a></li> <li><a href="/wiki/Esmirtazapine" title="Esmirtazapine">Esmirtazapine</a></li> <li><a href="/wiki/Fenmetozole" title="Fenmetozole">Fenmetozole</a></li> <li><a href="/wiki/Fluparoxan" title="Fluparoxan">Fluparoxan</a></li> <li><a href="/wiki/Idazoxan" title="Idazoxan">Idazoxan</a></li> <li><a href="/wiki/Ketanserin" title="Ketanserin">Ketanserin</a></li> <li><a href="/wiki/Lisuride" title="Lisuride">Lisuride</a></li> <li><a href="/wiki/Meta-Chlorophenylpiperazine" title="Meta-Chlorophenylpiperazine">mCPP</a></li> <li><a href="/wiki/Mianserin" title="Mianserin">Mianserin</a></li> <li><a href="/wiki/Mirtazapine" title="Mirtazapine">Mirtazapine</a></li> <li><a href="/wiki/NAN-190" title="NAN-190">NAN-190</a></li> <li><a href="/wiki/Pardoprunox" title="Pardoprunox">Pardoprunox</a></li> <li><a href="/wiki/Phentolamine" title="Phentolamine">Phentolamine</a></li> <li><a href="/wiki/Phenoxybenzamine" title="Phenoxybenzamine">Phenoxybenzamine</a></li> <li><a href="/wiki/Piperoxan" title="Piperoxan">Piperoxan</a></li> <li><a href="/wiki/Piribedil" title="Piribedil">Piribedil</a></li> <li><a href="/wiki/Rauwolscine" title="Rauwolscine">Rauwolscine</a></li> <li><a href="/wiki/Rotigotine" title="Rotigotine">Rotigotine</a></li> <li><a href="/wiki/Setiptiline" title="Setiptiline">Setiptiline</a></li> <li><a href="/wiki/Spegatrine" title="Spegatrine">Spegatrine</a></li> <li><a href="/wiki/Spiroxatrine" title="Spiroxatrine">Spiroxatrine</a></li> <li><a href="/wiki/Sunepitron" title="Sunepitron">Sunepitron</a></li> <li><a href="/wiki/Terguride" title="Terguride">Terguride</a></li> <li><a href="/wiki/Tolazoline" title="Tolazoline">Tolazoline</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/Loxapine" title="Loxapine">loxapine</a>, <a href="/wiki/Thioridazine" title="Thioridazine">thioridazine</a>)</li> <li><a href="/wiki/Yohimbine" title="Yohimbine">Yohimbine</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/%CE%92-adrenergic_receptor" class="mw-redirect" title="Β-adrenergic receptor">β</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%">Agonists</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/Abediterol" title="Abediterol">Abediterol</a></li> <li><a href="/wiki/Alifedrine" title="Alifedrine">Alifedrine</a></li> <li><a href="/wiki/Amibegron" title="Amibegron">Amibegron</a></li> <li><a href="/wiki/Arbutamine" title="Arbutamine">Arbutamine</a></li> <li><a href="/wiki/Arformoterol" title="Arformoterol">Arformoterol</a></li> <li><a href="/wiki/Arotinolol" title="Arotinolol">Arotinolol</a></li> <li><a href="/wiki/Bromoacetylalprenololmenthane" title="Bromoacetylalprenololmenthane">BAAM</a></li> <li><a href="/wiki/Bambuterol" title="Bambuterol">Bambuterol</a></li> <li><a href="/wiki/Befunolol" title="Befunolol">Befunolol</a></li> <li><a href="/wiki/Bitolterol" title="Bitolterol">Bitolterol</a></li> <li><a href="/wiki/Broxaterol" title="Broxaterol">Broxaterol</a></li> <li><a href="/wiki/Buphenine" title="Buphenine">Buphenine</a></li> <li><a href="/wiki/Carbuterol" title="Carbuterol">Carbuterol</a></li> <li><a href="/wiki/Carmoterol" title="Carmoterol">Carmoterol</a></li> <li><a href="/wiki/Cimaterol" title="Cimaterol">Cimaterol</a></li> <li><a href="/wiki/Clenbuterol" title="Clenbuterol">Clenbuterol</a></li> <li><a href="/wiki/Colterol" title="Colterol">Colterol</a></li> <li><a href="/wiki/Corbadrine" title="Corbadrine">Corbadrine</a></li> <li><a href="/wiki/Denopamine" title="Denopamine">Denopamine</a></li> <li><a href="/wiki/Deoxyepinephrine" title="Deoxyepinephrine">Deoxyepinephrine (epinine, <i>N</i>-methyldopamine)</a></li> <li><a href="/wiki/Dipivefrine" title="Dipivefrine">Dipivefrine</a></li> <li><a href="/wiki/Dobutamine" title="Dobutamine">Dobutamine</a></li> <li><a href="/wiki/Dopamine" title="Dopamine">Dopamine</a></li> <li><a href="/wiki/Dopexamine" title="Dopexamine">Dopexamine</a></li> <li><a href="/wiki/Droxidopa" title="Droxidopa">Droxidopa (L-DOPS)</a></li> <li><a href="/wiki/Epinephrine" class="mw-redirect" title="Epinephrine">Epinephrine</a></li> <li><a href="/wiki/Etafedrine" title="Etafedrine">Etafedrine</a></li> <li><a href="/wiki/Etilefrine" title="Etilefrine">Etilefrine</a></li> <li><a href="/wiki/Etilevodopa" title="Etilevodopa">Etilevodopa</a></li> <li><a href="/wiki/Ethylnorepinephrine" title="Ethylnorepinephrine">Ethylnorepinephrine</a></li> <li><a href="/wiki/Eugenodilol" title="Eugenodilol">Eugenodilol</a></li> <li><a href="/wiki/Fenoterol" title="Fenoterol">Fenoterol</a></li> <li><a href="/wiki/Formoterol" title="Formoterol">Formoterol</a></li> <li><a href="/wiki/Hexoprenaline" title="Hexoprenaline">Hexoprenaline</a></li> <li><a href="/wiki/Higenamine" title="Higenamine">Higenamine</a></li> <li><a href="/wiki/Ibopamine" title="Ibopamine">Ibopamine</a></li> <li><a href="/wiki/Indacaterol" title="Indacaterol">Indacaterol</a></li> <li><a href="/wiki/Isoetarine" title="Isoetarine">Isoetarine</a></li> <li><a href="/wiki/Isoprenaline" title="Isoprenaline">Isoprenaline</a></li> <li><a href="/wiki/Isoxsuprine" title="Isoxsuprine">Isoxsuprine</a></li> <li><a href="/wiki/L-DOPA" title="L-DOPA">L-DOPA (levodopa)</a></li> <li><a href="/wiki/Phenylalanine" title="Phenylalanine">L-Phenylalanine</a></li> <li><a href="/wiki/Tyrosine" title="Tyrosine">L-Tyrosine</a></li> <li><a href="/wiki/Levosalbutamol" title="Levosalbutamol">Levosalbutamol</a></li> <li><a href="/wiki/Lubabegron" title="Lubabegron">Lubabegron</a></li> <li><a href="/wiki/Mabuterol" title="Mabuterol">Mabuterol</a></li> <li><a href="/wiki/Melevodopa" title="Melevodopa">Melevodopa</a></li> <li><a href="/wiki/Methoxyphenamine" title="Methoxyphenamine">Methoxyphenamine</a></li> <li><a href="/wiki/Methyldopa" title="Methyldopa">Methyldopa</a></li> <li><a href="/wiki/Mirabegron" title="Mirabegron">Mirabegron</a></li> <li><a href="/wiki/Norepinephrine" title="Norepinephrine">Norepinephrine</a></li> <li><a href="/wiki/Orciprenaline" title="Orciprenaline">Orciprenaline</a></li> <li><a href="/wiki/Oxyfedrine" title="Oxyfedrine">Oxyfedrine</a></li> <li><a href="/wiki/PF-610355" title="PF-610355">PF-610355</a></li> <li><a href="/wiki/Phenylpropanolamine" title="Phenylpropanolamine">Phenylpropanolamine</a></li> <li><a href="/wiki/Pirbuterol" title="Pirbuterol">Pirbuterol</a></li> <li><a href="/wiki/Prenalterol" title="Prenalterol">Prenalterol</a></li> <li><a href="/wiki/Ractopamine" title="Ractopamine">Ractopamine</a></li> <li><a href="/wiki/Procaterol" title="Procaterol">Procaterol</a></li> <li><a href="/wiki/Reproterol" title="Reproterol">Reproterol</a></li> <li><a href="/wiki/Rimiterol" title="Rimiterol">Rimiterol</a></li> <li><a href="/wiki/Ritodrine" title="Ritodrine">Ritodrine</a></li> <li><a href="/wiki/Salbutamol" title="Salbutamol">Salbutamol</a></li> <li><a href="/wiki/Salmeterol" title="Salmeterol">Salmeterol</a></li> <li><a href="/wiki/Solabegron" title="Solabegron">Solabegron</a></li> <li><a href="/wiki/Terbutaline" title="Terbutaline">Terbutaline</a></li> <li><a href="/wiki/Tretoquinol" title="Tretoquinol">Tretoquinol</a></li> <li><a href="/wiki/Tulobuterol" title="Tulobuterol">Tulobuterol</a></li> <li><a href="/wiki/Vibegron" title="Vibegron">Vibegron</a></li> <li><a href="/wiki/Vilanterol" title="Vilanterol">Vilanterol</a></li> <li><a href="/wiki/Xamoterol" title="Xamoterol">Xamoterol</a></li> <li><a href="/wiki/XP21279" class="mw-redirect" title="XP21279">XP21279</a></li> <li><a href="/wiki/Zilpaterol" title="Zilpaterol">Zilpaterol</a></li> <li><a href="/wiki/Zinterol" title="Zinterol">Zinterol</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Antagonists</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/Acebutolol" title="Acebutolol">Acebutolol</a></li> <li><a href="/wiki/Adaprolol" title="Adaprolol">Adaprolol</a></li> <li><a href="/wiki/Adimolol" title="Adimolol">Adimolol</a></li> <li><a href="/wiki/Afurolol" title="Afurolol">Afurolol</a></li> <li><a href="/wiki/Alprenolol" title="Alprenolol">Alprenolol</a></li> <li><a href="/wiki/Alprenoxime" title="Alprenoxime">Alprenoxime</a></li> <li><a href="/wiki/Amosulalol" title="Amosulalol">Amosulalol</a></li> <li><a href="/wiki/Ancarolol" title="Ancarolol">Ancarolol</a></li> <li><a href="/wiki/Arnolol" title="Arnolol">Arnolol</a></li> <li><a href="/wiki/Arotinolol" title="Arotinolol">Arotinolol</a></li> <li><a href="/wiki/Atenolol" title="Atenolol">Atenolol</a></li> <li><a href="/wiki/Befunolol" title="Befunolol">Befunolol</a></li> <li><a href="/wiki/Betaxolol" title="Betaxolol">Betaxolol</a></li> <li><a href="/wiki/Bevantolol" title="Bevantolol">Bevantolol</a></li> <li><a href="/wiki/Bisoprolol" title="Bisoprolol">Bisoprolol</a></li> <li><a href="/wiki/Bopindolol" title="Bopindolol">Bopindolol</a></li> <li><a href="/wiki/Bornaprolol" title="Bornaprolol">Bornaprolol</a></li> <li><a href="/wiki/Brefonalol" title="Brefonalol">Brefonalol</a></li> <li><a href="/wiki/Bucindolol" title="Bucindolol">Bucindolol</a></li> <li><a href="/wiki/Bucumolol" title="Bucumolol">Bucumolol</a></li> <li><a href="/wiki/Bufetolol" title="Bufetolol">Bufetolol</a></li> <li><a href="/wiki/Bufuralol" title="Bufuralol">Bufuralol</a></li> <li><a href="/wiki/Bunitrolol" title="Bunitrolol">Bunitrolol</a></li> <li><a href="/wiki/Bunolol" class="mw-redirect" title="Bunolol">Bunolol</a></li> <li><a href="/wiki/Bupranolol" title="Bupranolol">Bupranolol</a></li> <li><a href="/wiki/Butaxamine" title="Butaxamine">Butaxamine</a></li> <li><a href="/wiki/Butidrine" title="Butidrine">Butidrine</a></li> <li><a href="/wiki/Butofilolol" title="Butofilolol">Butofilolol</a></li> <li><a href="/wiki/Capsinolol" title="Capsinolol">Capsinolol</a></li> <li><a href="/wiki/Carazolol" title="Carazolol">Carazolol</a></li> <li><a href="/wiki/Carpindolol" title="Carpindolol">Carpindolol</a></li> <li><a href="/wiki/Carteolol" title="Carteolol">Carteolol</a></li> <li><a href="/wiki/Carvedilol" title="Carvedilol">Carvedilol</a></li> <li><a href="/wiki/Celiprolol" title="Celiprolol">Celiprolol</a></li> <li><a href="/wiki/Cetamolol" title="Cetamolol">Cetamolol</a></li> <li><a href="/wiki/Cicloprolol" title="Cicloprolol">Cicloprolol</a></li> <li><a href="/wiki/Cinamolol" title="Cinamolol">Cinamolol</a></li> <li><a href="/wiki/Cloranolol" title="Cloranolol">Cloranolol</a></li> <li><a href="/wiki/Cyanopindolol" title="Cyanopindolol">Cyanopindolol</a></li> <li><a href="/wiki/Dalbraminol" title="Dalbraminol">Dalbraminol</a></li> <li><a href="/wiki/Dexpropranolol" class="mw-redirect" title="Dexpropranolol">Dexpropranolol</a></li> <li><a href="/wiki/Diacetolol" title="Diacetolol">Diacetolol</a></li> <li><a href="/wiki/Dichloroisoprenaline" title="Dichloroisoprenaline">Dichloroisoprenaline</a></li> <li><a href="/wiki/Dihydroalprenolol" title="Dihydroalprenolol">Dihydroalprenolol</a></li> <li><a href="/wiki/Dilevalol" class="mw-redirect" title="Dilevalol">Dilevalol</a></li> <li><a href="/wiki/Diprafenone" title="Diprafenone">Diprafenone</a></li> <li><a href="/wiki/Draquinolol" title="Draquinolol">Draquinolol</a></li> <li><a href="/wiki/Ecastolol" title="Ecastolol">Ecastolol</a></li> <li><a href="/wiki/Epanolol" title="Epanolol">Epanolol</a></li> <li><a href="/wiki/Ericolol" title="Ericolol">Ericolol</a></li> <li><a href="/wiki/Ersentilide" title="Ersentilide">Ersentilide</a></li> <li><a href="/wiki/Esatenolol" class="mw-redirect" title="Esatenolol">Esatenolol</a></li> <li><a href="/wiki/Esprolol" class="mw-redirect" title="Esprolol">Esprolol</a></li> <li><a href="/wiki/Eugenodilol" title="Eugenodilol">Eugenodilol</a></li> <li><a href="/wiki/Exaprolol" title="Exaprolol">Exaprolol</a></li> <li><a href="/wiki/Falintolol" title="Falintolol">Falintolol</a></li> <li><a href="/wiki/Flestolol" title="Flestolol">Flestolol</a></li> <li><a href="/wiki/Flusoxolol" title="Flusoxolol">Flusoxolol</a></li> <li><a href="/wiki/Hydroxycarteolol" title="Hydroxycarteolol">Hydroxycarteolol</a></li> <li><a href="/wiki/Hydroxytertatolol" title="Hydroxytertatolol">Hydroxytertatolol</a></li> <li><a href="/wiki/ICI-118,551" title="ICI-118,551">ICI-118,551</a></li> <li><a href="/wiki/Idropranolol" class="mw-redirect" title="Idropranolol">Idropranolol</a></li> <li><a href="/wiki/Indenolol" title="Indenolol">Indenolol</a></li> <li><a href="/wiki/Indopanolol" title="Indopanolol">Indopanolol</a></li> <li><a href="/wiki/Iodocyanopindolol" title="Iodocyanopindolol">Iodocyanopindolol</a></li> <li><a href="/wiki/Iprocrolol" title="Iprocrolol">Iprocrolol</a></li> <li><a href="/wiki/Isoxaprolol" title="Isoxaprolol">Isoxaprolol</a></li> <li><a href="/wiki/Isamoltane" title="Isamoltane">Isamoltane</a></li> <li><a href="/wiki/Labetalol" title="Labetalol">Labetalol</a></li> <li><a href="/wiki/Landiolol" title="Landiolol">Landiolol</a></li> <li><a href="/wiki/Levobetaxolol" title="Levobetaxolol">Levobetaxolol</a></li> <li><a href="/wiki/Levobunolol" title="Levobunolol">Levobunolol</a></li> <li><a href="/wiki/Levomoprolol" title="Levomoprolol">Levomoprolol</a></li> <li><a href="/wiki/Medroxalol" title="Medroxalol">Medroxalol</a></li> <li><a href="/wiki/Mepindolol" title="Mepindolol">Mepindolol</a></li> <li><a href="/wiki/Metipranolol" title="Metipranolol">Metipranolol</a></li> <li><a href="/wiki/Metoprolol" title="Metoprolol">Metoprolol</a></li> <li><a href="/wiki/Moprolol" title="Moprolol">Moprolol</a></li> <li><a href="/wiki/Nadolol" title="Nadolol">Nadolol</a></li> <li><a href="/wiki/Nadoxolol" title="Nadoxolol">Nadoxolol</a></li> <li><a href="/wiki/Nebivolol" title="Nebivolol">Nebivolol</a></li> <li><a href="/wiki/Nifenalol" title="Nifenalol">Nifenalol</a></li> <li><a href="/wiki/Nipradilol" title="Nipradilol">Nipradilol</a></li> <li><a href="/wiki/Oxprenolol" title="Oxprenolol">Oxprenolol</a></li> <li><a href="/wiki/Pacrinolol" title="Pacrinolol">Pacrinolol</a></li> <li><a href="/wiki/Pafenolol" title="Pafenolol">Pafenolol</a></li> <li><a href="/wiki/Pamatolol" title="Pamatolol">Pamatolol</a></li> <li><a href="/wiki/Pargolol" title="Pargolol">Pargolol</a></li> <li><a href="/wiki/Penbutolol" title="Penbutolol">Penbutolol</a></li> <li><a href="/wiki/Pindolol" title="Pindolol">Pindolol</a></li> <li><a href="/wiki/Practolol" title="Practolol">Practolol</a></li> <li><a href="/wiki/Primidolol" title="Primidolol">Primidolol</a></li> <li><a href="/wiki/Procinolol" title="Procinolol">Procinolol</a></li> <li><a href="/wiki/Pronethalol" title="Pronethalol">Pronethalol</a></li> <li><a href="/wiki/Propafenone" title="Propafenone">Propafenone</a></li> <li><a href="/wiki/Propranolol" title="Propranolol">Propranolol</a></li> <li><a href="/wiki/Ridazolol" title="Ridazolol">Ridazolol</a></li> <li><a href="/wiki/Ronactolol" title="Ronactolol">Ronactolol</a></li> <li><a href="/wiki/Soquinolol" title="Soquinolol">Soquinolol</a></li> <li><a href="/wiki/Sotalol" title="Sotalol">Sotalol</a></li> <li><a href="/wiki/Spirendolol" title="Spirendolol">Spirendolol</a></li> <li><a href="/wiki/SR_59230A" title="SR 59230A">SR 59230A</a></li> <li><a href="/wiki/Sulfinalol" title="Sulfinalol">Sulfinalol</a></li> <li><a href="/wiki/Talinolol" title="Talinolol">Talinolol</a></li> <li><a href="/wiki/Tazolol" title="Tazolol">Tazolol</a></li> <li><a href="/wiki/Tertatolol" title="Tertatolol">Tertatolol</a></li> <li><a href="/wiki/Tienoxolol" title="Tienoxolol">Tienoxolol</a></li> <li><a href="/wiki/Tilisolol" title="Tilisolol">Tilisolol</a></li> <li><a href="/wiki/Timolol" title="Timolol">Timolol</a></li> <li><a href="/wiki/Tiprenolol" title="Tiprenolol">Tiprenolol</a></li> <li><a href="/wiki/Tolamolol" title="Tolamolol">Tolamolol</a></li> <li><a href="/wiki/Toliprolol" title="Toliprolol">Toliprolol</a></li> <li><a href="/wiki/Xibenolol" title="Xibenolol">Xibenolol</a></li> <li><a href="/wiki/Xipranolol" title="Xipranolol">Xipranolol</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><td class="navbox-abovebelow" colspan="2"><div> <ul><li><i><b>See also:</b> <a href="/wiki/Template:Receptor_modulators" title="Template:Receptor modulators">Receptor/signaling modulators</a></i></li> <li><i><a href="/wiki/Template:Dopamine_receptor_modulators" title="Template:Dopamine receptor modulators">Dopaminergics</a></i></li> <li><i><a href="/wiki/Template:Serotonin_receptor_modulators" title="Template:Serotonin receptor modulators">Serotonergics</a></i></li> <li><i><a href="/wiki/Template:Monoamine_reuptake_inhibitors" title="Template:Monoamine reuptake inhibitors">Monoamine reuptake inhibitors</a></i></li> <li><i><a href="/wiki/Template:Monoamine_releasing_agents" title="Template:Monoamine releasing agents">Monoamine releasing agents</a></i></li> <li><i><a href="/wiki/Template:Monoamine_metabolism_modulators" title="Template:Monoamine metabolism modulators">Monoamine metabolism modulators</a></i></li> <li><i><a href="/wiki/Template:Monoamine_neurotoxins" title="Template:Monoamine neurotoxins">Monoamine neurotoxins</a></i></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="Human_trace_amine-associated_receptor_ligands" style="padding:3px"><table class="nowraplinks hlist mw-collapsible autocollapse navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:TAAR_ligands" title="Template:TAAR ligands"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:TAAR_ligands" title="Template talk:TAAR ligands"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:TAAR_ligands" title="Special:EditPage/Template:TAAR ligands"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Human_trace_amine-associated_receptor_ligands" style="font-size:114%;margin:0 4em"><a href="/wiki/Human_trace_amine-associated_receptor" class="mw-redirect" title="Human trace amine-associated receptor">Human trace amine-associated receptor</a> <a href="/wiki/Ligand_(biochemistry)" title="Ligand (biochemistry)">ligands</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align: center"><a href="/wiki/TAAR1" title="TAAR1">TAAR1</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:6em;text-align: center"><a href="/wiki/Agonist" title="Agonist">Agonists</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="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:5em;text-align: center"><a href="/wiki/Trace_amine" title="Trace amine">Endogenous</a><sup>†</sup></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0;background:white"><div style="padding:0 0.25em"> <ul><li>Classical <a href="/wiki/Monoamine_neurotransmitter" title="Monoamine neurotransmitter">monoamine neurotransmitters</a> <ul><li><a href="/wiki/Dopamine" title="Dopamine">Dopamine</a></li> <li><a href="/wiki/Histamine" title="Histamine">Histamine</a></li> <li><a href="/wiki/Epinephrine" class="mw-redirect" title="Epinephrine">Epinephrine (adrenaline)</a></li> <li><a href="/wiki/Norepinephrine" title="Norepinephrine">Norepinephrine (noradrenaline)</a></li> <li><a href="/wiki/Serotonin" title="Serotonin">Serotonin</a></li></ul></li> <li><a href="/wiki/Trace_amine" title="Trace amine">Trace amines</a> <ul><li><a href="/wiki/3-Iodothyronamine" title="3-Iodothyronamine">3-Iodothyronamine</a></li> <li><a href="/wiki/3-Methoxytyramine" title="3-Methoxytyramine">3-Methoxytyramine</a></li> <li><a href="/wiki/N-Methylphenethylamine" title="N-Methylphenethylamine"><i>N</i>-Methylphenethylamine</a></li> <li><a href="/wiki/N-Methyltyramine" title="N-Methyltyramine"><i>N</i>-Methyltyramine</a></li> <li><a href="/wiki/Meta-Octopamine" class="mw-redirect" title="Meta-Octopamine"><i>m</i>-Octopamine</a></li> <li><a href="/wiki/Para-Octopamine" class="mw-redirect" title="Para-Octopamine"><i>p</i>-Octopamine</a></li> <li><a href="/wiki/Phenethylamine" title="Phenethylamine">Phenethylamine</a></li> <li><a href="/wiki/Phenylethanolamine" title="Phenylethanolamine">Phenylethanolamine</a></li> <li><a href="/wiki/Synephrine" title="Synephrine">Synephrine</a></li> <li><a href="/wiki/Tryptamine" title="Tryptamine">Tryptamine</a></li> <li><a href="/wiki/Meta-Tyramine" title="Meta-Tyramine"><i>m</i>-Tyramine</a></li> <li><a href="/wiki/Para-Tyramine" class="mw-redirect" title="Para-Tyramine"><i>p</i>-Tyramine</a></li></ul></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:5em;text-align: center">Synthetic and natural<sup>‡</sup></th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0;background:white"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Amphetamine" title="Amphetamine">Amphetamine</a></li> <li><a href="/wiki/2,5-Dimethoxy-4-bromoamphetamine" title="2,5-Dimethoxy-4-bromoamphetamine">DOB</a></li> <li><a href="/wiki/2,5-Dimethoxy-4-ethylamphetamine" title="2,5-Dimethoxy-4-ethylamphetamine">DOET</a></li> <li><a href="/wiki/N,N-Dimethylphenethylamine" title="N,N-Dimethylphenethylamine"><i>N</i>,<i>N</i>-Dimethylphenethylamine</a></li> <li><a href="/wiki/Guanfacine" title="Guanfacine">Guanfacine</a></li> <li><a href="/wiki/Halostachine" title="Halostachine">Halostachine</a></li> <li><a href="/wiki/Higenamine" title="Higenamine">Higenamine</a></li> <li><a href="/wiki/Hordenine" title="Hordenine">Hordenine</a></li> <li><a href="/wiki/4-Hydroxyamphetamine" title="4-Hydroxyamphetamine">4-Hydroxyamphetamine</a></li> <li><a href="/wiki/Isopropyloctopamine" class="mw-redirect" title="Isopropyloctopamine">Isopropyloctopamine</a></li> <li><a href="/wiki/Isoprenaline" title="Isoprenaline">Isoprenaline</a></li> <li><a href="/wiki/3,4-Methylenedioxyamphetamine" title="3,4-Methylenedioxyamphetamine">MDA (tenamfetamine)</a></li> <li><a href="/wiki/MDMA" title="MDMA">MDMA (midomafetamine)</a></li> <li><a href="/wiki/2-Methylphenethylamine" title="2-Methylphenethylamine">2-Methylphenethylamine</a></li> <li><a href="/wiki/3-Methylphenethylamine" title="3-Methylphenethylamine">3-Methylphenethylamine</a></li> <li><a href="/wiki/4-Methylphenethylamine" title="4-Methylphenethylamine">4-Methylphenethylamine</a></li> <li><a href="/wiki/%CE%92-Methylphenethylamine" title="Β-Methylphenethylamine">β-Methylphenethylamine</a></li> <li><a href="/wiki/Methamphetamine" title="Methamphetamine">Methamphetamine</a></li> <li><a href="/wiki/3-Methoxymethamphetamine" title="3-Methoxymethamphetamine">3-MMA</a></li> <li><a href="/wiki/Norfenfluramine" title="Norfenfluramine">Norfenfluramine</a></li> <li><a href="/wiki/Phentermine" title="Phentermine">Phentermine</a></li> <li><a href="/wiki/O-Phenyl-3-iodotyramine" title="O-Phenyl-3-iodotyramine"><i>o</i>-PIT</a></li> <li><a href="/wiki/Propylhexedrine" title="Propylhexedrine">Propylhexedrine</a></li> <li><a href="/wiki/Ralmitaront" title="Ralmitaront">Ralmitaront (RG-7906, RO-6889450)</a></li> <li><a href="/wiki/RG-7351" title="RG-7351">RG-7351</a></li> <li><a href="/wiki/RG-7410" title="RG-7410">RG-7410</a></li> <li><a href="/wiki/RO5166017" title="RO5166017">RO-5166017</a></li> <li><a href="/wiki/RO5256390" title="RO5256390">RO-5256390</a></li> <li><a href="/wiki/RO5263397" title="RO5263397">RO-5263397</a></li> <li><a href="/wiki/Selegiline" title="Selegiline">Selegiline</a></li> <li><a href="/wiki/Solriamfetol" title="Solriamfetol">Solriamfetol</a></li> <li><a href="/wiki/Ulotaront" title="Ulotaront">Ulotaront (SEP-363856)</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:6em;text-align: center"><a href="/wiki/Neutral_antagonist" class="mw-redirect" title="Neutral antagonist">Neutral antagonists</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/RTI-7470-44" title="RTI-7470-44">RTI-7470-44</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:6em;text-align: center"><a href="/wiki/Inverse_agonist" title="Inverse agonist">Inverse agonists</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/EPPTB" title="EPPTB">EPPTB (RO-5212773)</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align: center"><a href="/wiki/TAAR2" title="TAAR2">TAAR2</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:6em;text-align: center">Agonists<sup>‡</sup></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:6em;text-align: center">Neutral antagonists</th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li> </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/TAAR5" title="TAAR5">TAAR5</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:6em;text-align: center">Agonists<sup>‡</sup></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/N,N-Dimethylethylamine" title="N,N-Dimethylethylamine"><i>N</i>,<i>N</i>-Dimethylethylamine</a></li> <li><a href="/wiki/Trimethylamine" title="Trimethylamine">Trimethylamine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:6em;text-align: center">Neutral antagonists</th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li> </li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:6em;text-align: center">Inverse agonists<sup>‡</sup></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/3-Iodothyronamine" title="3-Iodothyronamine">3-Iodothyronamine</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><td class="navbox-abovebelow" colspan="2"><div><div style="float: left;"><small><sup>†</sup> References for all endogenous human TAAR1 ligands are provided at <a href="/wiki/Trace_amine#list" title="Trace amine">List of trace amines</a></small></div> <p><br /> </p> <div style="float: left;"><small><sup>‡</sup> References for synthetic TAAR1 agonists can be found at <a href="/wiki/TAAR1" title="TAAR1">TAAR1</a> or in the associated compound articles. For TAAR2 and TAAR5 agonists and inverse agonists, see <a href="/wiki/Trace_amine-associated_receptor#Receptor_function_and_ligands" title="Trace amine-associated receptor">TAAR</a> for references.</small></div> <p><br /> </p> <small><i><b>See also:</b> <a href="/wiki/Template:Receptor_modulators" title="Template:Receptor modulators">Receptor/signaling modulators</a></i></small></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="Ergolines" style="padding:3px"><table class="nowraplinks mw-collapsible autocollapse navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Ergolines" title="Template:Ergolines"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Ergolines" title="Template talk:Ergolines"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Ergolines" title="Special:EditPage/Template:Ergolines"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Ergolines" style="font-size:114%;margin:0 4em"><a class="mw-selflink selflink">Ergolines</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Lysergic_acid" title="Lysergic acid">Lysergic acid</a><br /> derivatives</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-Bromo-LSD" title="2-Bromo-LSD">2-Bromo-LSD (BOL-148)</a></li> <li><a href="/wiki/Amesergide" title="Amesergide">Amesergide</a></li> <li><a href="/wiki/Bromerguride" title="Bromerguride">Bromerguride (2-bromolisuride)</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/Dihydroergocornine" title="Dihydroergocornine">Dihydroergocornine</a></li> <li><a href="/wiki/Dihydroergocristine" title="Dihydroergocristine">Dihydroergocristine</a></li> <li><a href="/wiki/Dihydroergocryptine" title="Dihydroergocryptine">Dihydroergocryptine</a></li> <li><a href="/w/index.php?title=Dihydroergometrine&action=edit&redlink=1" class="new" title="Dihydroergometrine (page does not exist)">Dihydroergometrine</a> (Dihydroergonovine, Dihydroergobasine)</li> <li><a href="/w/index.php?title=Dihydroergosine&action=edit&redlink=1" class="new" title="Dihydroergosine (page does not exist)">Dihydroergosine</a></li> <li><a href="/wiki/Dihydroergotamine" title="Dihydroergotamine">Dihydroergotamine</a></li> <li><a href="/wiki/Epicriptine" title="Epicriptine">Epicriptine</a></li> <li><a href="/wiki/Ergine" title="Ergine">Ergine</a> (LSA; LA-111; Lysergamide)</li> <li><a href="/wiki/Ergocornine" title="Ergocornine">Ergocornine</a></li> <li><a href="/wiki/Ergocristine" title="Ergocristine">Ergocristine</a></li> <li><a href="/wiki/Ergocryptine" title="Ergocryptine">Ergocryptine</a></li> <li><a href="/wiki/Ergoloid" title="Ergoloid">Ergoloid</a> (Dihydroergotoxine)</li> <li><a href="/wiki/Ergometrine" title="Ergometrine">Ergometrine</a> (Ergonovine, Ergobasine)</li> <li><a href="/wiki/Ergometrinine" title="Ergometrinine">Ergometrinine</a></li> <li><a href="/wiki/Ergostine" title="Ergostine">Ergostine</a></li> <li><a href="/wiki/Ergotamine" title="Ergotamine">Ergotamine</a></li> <li><a href="/wiki/Ergotoxine" class="mw-redirect" title="Ergotoxine">Ergotoxine</a></li> <li><a href="/wiki/Ergovaline" title="Ergovaline">Ergovaline</a></li> <li><a href="/w/index.php?title=Fludihydroergotamine&action=edit&redlink=1" class="new" title="Fludihydroergotamine (page does not exist)">Fludihydroergotamine</a></li> <li><a href="/wiki/Lisuride" title="Lisuride">Lisuride</a></li> <li><a href="/wiki/LY-215,840" title="LY-215,840">LY-215,840</a></li> <li><a href="/wiki/Lysergic_acid_hydroxyethylamide" title="Lysergic acid hydroxyethylamide">LSH</a></li> <li><a href="/wiki/Lysergic_acid" title="Lysergic acid">Lysergic acid</a></li> <li><a href="/wiki/Lysergic_acid_methyl_ester" title="Lysergic acid methyl ester">Lysergic acid methyl ester</a></li> <li><a href="/wiki/Lysergine" title="Lysergine">Lysergine</a></li> <li><a href="/wiki/Lysergol" title="Lysergol">Lysergol</a></li> <li><a href="/w/index.php?title=Mergocriptine&action=edit&redlink=1" class="new" title="Mergocriptine (page does not exist)">Mergocriptine</a></li> <li><a href="/wiki/Mesulergine" title="Mesulergine">Mesulergine</a></li> <li><a href="/wiki/Metergoline" title="Metergoline">Metergoline</a></li> <li><a href="/w/index.php?title=Metergotamine&action=edit&redlink=1" class="new" title="Metergotamine (page does not exist)">Metergotamine</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="/w/index.php?title=Propisergide&action=edit&redlink=1" class="new" title="Propisergide (page does not exist)">Propisergide</a></li> <li><a href="/wiki/Sergolexole" title="Sergolexole">Sergolexole</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Psychedelic_drug" title="Psychedelic drug">Psychedelic</a><br /> <a href="/wiki/Lysergamides" title="Lysergamides">lysergamides</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/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/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="/w/index.php?title=CYP-LAD&action=edit&redlink=1" class="new" title="CYP-LAD (page does not exist)">CYP-LAD</a></li> <li><a href="/wiki/Diallyllysergamide" title="Diallyllysergamide">Diallyllysergamide</a> (DAL)</li> <li><a href="/wiki/Dimethyllysergamide" title="Dimethyllysergamide">Dimethyllysergamide</a> (DAM-57)</li> <li><a href="/wiki/ECPLA" title="ECPLA">ECPLA</a></li> <li><a href="/wiki/Ergonovine" class="mw-redirect" title="Ergonovine">Ergonovine</a></li> <li><a href="/wiki/ETFELA" title="ETFELA">ETFELA</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/LAMPA" title="LAMPA">LAMPA</a></li> <li><a href="/wiki/LAE-32" title="LAE-32">LAE-32</a></li> <li><a href="/wiki/LSD" title="LSD">LSD (lysergide)</a></li> <li><a href="/wiki/LPD-824" title="LPD-824">LPD-824</a></li> <li><a href="/wiki/LSM-775" title="LSM-775">LSM-775</a></li> <li><a href="/wiki/D-Lysergic_acid_N-(%CE%B1-hydroxyethyl)amide" class="mw-redirect" title="D-Lysergic acid N-(α-hydroxyethyl)amide">LSH</a></li> <li><a href="/wiki/LSD-Pip" title="LSD-Pip">LSD-Pip</a></li> <li><a href="/wiki/Lysergic_acid_2-butyl_amide" title="Lysergic acid 2-butyl amide">Lysergic Acid 2-Butylamide</a></li> <li><a href="/wiki/Lysergic_acid_2,4-dimethylazetidide" title="Lysergic acid 2,4-dimethylazetidide">Lysergic Acid 2,4-Dimethylazetidide</a></li> <li><a href="/wiki/Lysergic_acid_3-pentyl_amide" title="Lysergic acid 3-pentyl amide">Lysergic Acid 3-Pentylamide</a></li> <li><a href="/w/index.php?title=Lysergic_acid_cyclobutylamide&action=edit&redlink=1" class="new" title="Lysergic acid cyclobutylamide (page does not exist)">Lysergic acid cyclobutylamide</a></li> <li><a href="/w/index.php?title=Lysergic_acid_cyclopentylamide&action=edit&redlink=1" class="new" title="Lysergic acid cyclopentylamide (page does not exist)">Lysergic acid cyclopentylamide</a></li> <li><a href="/wiki/Methylergometrine" title="Methylergometrine">Methylergometrine</a> (Methylergonovine, Methylergobasine)</li> <li><a href="/wiki/Methylisopropyllysergamide" title="Methylisopropyllysergamide">MIPLA</a></li> <li><a href="/wiki/MLD-41" class="mw-redirect" title="MLD-41">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%">Clavines</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/9-Deacetoxyfumigaclavine_C" title="9-Deacetoxyfumigaclavine C">9-Deacetoxyfumigaclavine C</a></li> <li><a href="/wiki/Agroclavine" title="Agroclavine">Agroclavine</a></li> <li><a href="/wiki/Chanoclavine" title="Chanoclavine">Chanoclavine</a></li> <li><a href="/wiki/Chanoclavine_II" title="Chanoclavine II">Chanoclavine II</a></li> <li><a href="/wiki/Costaclavin" title="Costaclavin">Costaclavin</a></li> <li><a href="/wiki/Cycloclavine" title="Cycloclavine">Cycloclavine</a></li> <li><a href="/wiki/Elymoclavine" title="Elymoclavine">Elymoclavine</a></li> <li><a href="/wiki/Epoxyagroclavine" title="Epoxyagroclavine">Epoxyagroclavine</a></li> <li><a href="/wiki/Festuclavine" title="Festuclavine">Festuclavine</a></li> <li><a href="/wiki/Fumigaclavine_A" title="Fumigaclavine A">Fumigaclavine A</a></li> <li><a href="/wiki/Fumigaclavine_B" title="Fumigaclavine B">Fumigaclavine B</a></li> <li><a href="/wiki/Fumigaclavine_C" title="Fumigaclavine C">Fumigaclavine C</a></li> <li><a href="/wiki/Paliclavine" title="Paliclavine">Paliclavine</a></li> <li><a href="/wiki/Penniclavine" title="Penniclavine">Penniclavine</a></li> <li><a href="/wiki/Setoclavine" title="Setoclavine">Setoclavine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Other<br /> ergolines</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/Acetergamine" title="Acetergamine">Acetergamine</a></li> <li><a href="/w/index.php?title=Brazergoline&action=edit&redlink=1" class="new" title="Brazergoline (page does not exist)">Brazergoline</a></li> <li><a href="/w/index.php?title=Cianergoline&action=edit&redlink=1" class="new" title="Cianergoline (page does not exist)">Cianergoline</a></li> <li><a href="/wiki/CY-208,243" title="CY-208,243">CY-208,243</a></li> <li><a href="/w/index.php?title=Delergotrile&action=edit&redlink=1" class="new" title="Delergotrile (page does not exist)">Delergotrile</a></li> <li><a href="/w/index.php?title=Disulergine&action=edit&redlink=1" class="new" title="Disulergine (page does not exist)">Disulergine</a></li> <li><a href="/w/index.php?title=Dosergoside&action=edit&redlink=1" class="new" title="Dosergoside (page does not exist)">Dosergoside</a></li> <li><a class="mw-selflink selflink">Ergoline</a></li> <li><a href="/w/index.php?title=Etisulergine&action=edit&redlink=1" class="new" title="Etisulergine (page does not exist)">Etisulergine</a></li> <li><a href="/wiki/Lergotrile" title="Lergotrile">Lergotrile</a></li> <li><a href="/wiki/Nicergoline" title="Nicergoline">Nicergoline</a></li> <li><a href="/wiki/Pergolide" title="Pergolide">Pergolide</a></li> <li><a href="/w/index.php?title=Proterguride&action=edit&redlink=1" class="new" title="Proterguride (page does not exist)">Proterguride</a></li> <li><a href="/w/index.php?title=Romergoline&action=edit&redlink=1" class="new" title="Romergoline (page does not exist)">Romergoline</a></li> <li><a href="/wiki/Terguride" title="Terguride">Terguride</a></li> <li><a href="/w/index.php?title=Tiomergine&action=edit&redlink=1" class="new" title="Tiomergine (page does not exist)">Tiomergine</a></li> <li><a href="/w/index.php?title=Voxergolide&action=edit&redlink=1" class="new" title="Voxergolide (page does not exist)">Voxergolide</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Related<br /> 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="/wiki/Adrogolide" class="mw-redirect" title="Adrogolide">Adrogolide</a></li> <li><a href="/w/index.php?title=Naxagolide&action=edit&redlink=1" class="new" title="Naxagolide (page does not exist)">Naxagolide</a></li> <li><a href="/wiki/Quinagolide" title="Quinagolide">Quinagolide</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Natural<br /> sources</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><i><a href="/wiki/Achnatherum_robustum" title="Achnatherum robustum">Achnatherum robustum</a></i> (Sleepy Grass)</li> <li><a href="/wiki/Claviceps" class="mw-redirect" title="Claviceps"><i>Claviceps</i> spp.</a> (Ergot)<br /></li></ul> <p>Morning glory: <i><a href="/wiki/Argyreia_nervosa" title="Argyreia nervosa">Argyreia nervosa</a></i> (Hawaiian Baby Woodrose), <i><a href="/wiki/Ipomoea" title="Ipomoea"><i>Ipomoea</i> spp.</a></i>(Morning Glory, Tlitliltzin, Badoh Negro), <i><a href="/wiki/Turbina_corymbosa" class="mw-redirect" title="Turbina corymbosa">Rivea corymbosa</a></i> (Coaxihuitl, Ololiúqui) </p> </div></td></tr></tbody></table></div>    </div><noscript><img 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