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id="toc-Notes" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Notes"> <div class="vector-toc-text"> <span class="vector-toc-numb">6</span> <span>Notes</span> </div> </a> <ul id="toc-Notes-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> </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" > <input type="checkbox" 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Available in 27 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-27" 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">27 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%AA%D9%8A%D8%B1%D8%A7%D9%85%D9%8A%D9%86" title="تيرامين – Arabic" lang="ar" hreflang="ar" data-title="تيرامين" 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%AA%DB%8C%D8%B1%D8%A7%D9%85%DB%8C%D9%86" title="تیرامین – South Azerbaijani" lang="azb" hreflang="azb" data-title="تیرامین" data-language-autonym="تۆرکجه" data-language-local-name="South Azerbaijani" class="interlanguage-link-target"><span>تۆرکجه</span></a></li><li class="interlanguage-link interwiki-bs mw-list-item"><a href="https://bs.wikipedia.org/wiki/Tiramin" title="Tiramin – Bosnian" lang="bs" hreflang="bs" data-title="Tiramin" data-language-autonym="Bosanski" data-language-local-name="Bosnian" class="interlanguage-link-target"><span>Bosanski</span></a></li><li class="interlanguage-link interwiki-ca mw-list-item"><a href="https://ca.wikipedia.org/wiki/Tiramina" title="Tiramina – Catalan" lang="ca" hreflang="ca" data-title="Tiramina" data-language-autonym="Català" data-language-local-name="Catalan" class="interlanguage-link-target"><span>Català</span></a></li><li class="interlanguage-link interwiki-cs mw-list-item"><a href="https://cs.wikipedia.org/wiki/Tyramin" title="Tyramin – Czech" lang="cs" hreflang="cs" data-title="Tyramin" data-language-autonym="Čeština" data-language-local-name="Czech" class="interlanguage-link-target"><span>Čeština</span></a></li><li class="interlanguage-link interwiki-de mw-list-item"><a href="https://de.wikipedia.org/wiki/Tyramin" title="Tyramin – German" lang="de" hreflang="de" data-title="Tyramin" 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/Tiramina" title="Tiramina – Spanish" lang="es" hreflang="es" data-title="Tiramina" data-language-autonym="Español" data-language-local-name="Spanish" class="interlanguage-link-target"><span>Español</span></a></li><li class="interlanguage-link interwiki-eo mw-list-item"><a href="https://eo.wikipedia.org/wiki/Tiramino" title="Tiramino – Esperanto" lang="eo" hreflang="eo" data-title="Tiramino" data-language-autonym="Esperanto" data-language-local-name="Esperanto" class="interlanguage-link-target"><span>Esperanto</span></a></li><li class="interlanguage-link interwiki-fa mw-list-item"><a href="https://fa.wikipedia.org/wiki/%D8%AA%DB%8C%D8%B1%D8%A7%D9%85%DB%8C%D9%86" title="تیرامین – Persian" lang="fa" hreflang="fa" data-title="تیرامین" 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/Tyramine" title="Tyramine – French" lang="fr" hreflang="fr" data-title="Tyramine" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target"><span>Français</span></a></li><li class="interlanguage-link interwiki-ga mw-list-item"><a href="https://ga.wikipedia.org/wiki/Tioraim%C3%ADn" title="Tioraimín – Irish" lang="ga" hreflang="ga" data-title="Tioraimín" data-language-autonym="Gaeilge" data-language-local-name="Irish" class="interlanguage-link-target"><span>Gaeilge</span></a></li><li class="interlanguage-link interwiki-ko mw-list-item"><a href="https://ko.wikipedia.org/wiki/%ED%8B%B0%EB%9D%BC%EB%AF%BC" title="티라민 – Korean" lang="ko" hreflang="ko" data-title="티라민" data-language-autonym="한국어" data-language-local-name="Korean" class="interlanguage-link-target"><span>한국어</span></a></li><li class="interlanguage-link interwiki-it mw-list-item"><a href="https://it.wikipedia.org/wiki/Tiramina" title="Tiramina – Italian" lang="it" hreflang="it" data-title="Tiramina" data-language-autonym="Italiano" data-language-local-name="Italian" class="interlanguage-link-target"><span>Italiano</span></a></li><li class="interlanguage-link interwiki-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/Tyramine" title="Tyramine – Dutch" lang="nl" hreflang="nl" data-title="Tyramine" data-language-autonym="Nederlands" data-language-local-name="Dutch" class="interlanguage-link-target"><span>Nederlands</span></a></li><li class="interlanguage-link interwiki-ja mw-list-item"><a href="https://ja.wikipedia.org/wiki/%E3%83%81%E3%83%A9%E3%83%9F%E3%83%B3" title="チラミン – Japanese" lang="ja" hreflang="ja" data-title="チラミン" 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-pl mw-list-item"><a href="https://pl.wikipedia.org/wiki/Tyramina" title="Tyramina – Polish" lang="pl" hreflang="pl" data-title="Tyramina" 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/Tiramina" title="Tiramina – Portuguese" lang="pt" hreflang="pt" data-title="Tiramina" 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/Tiramin%C4%83" title="Tiramină – Romanian" lang="ro" hreflang="ro" data-title="Tiramină" data-language-autonym="Română" data-language-local-name="Romanian" class="interlanguage-link-target"><span>Română</span></a></li><li class="interlanguage-link interwiki-ru mw-list-item"><a href="https://ru.wikipedia.org/wiki/%D0%A2%D0%B8%D1%80%D0%B0%D0%BC%D0%B8%D0%BD" title="Тирамин – Russian" lang="ru" hreflang="ru" data-title="Тирамин" data-language-autonym="Русский" data-language-local-name="Russian" class="interlanguage-link-target"><span>Русский</span></a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/Tiramin" title="Tiramin – Serbian" lang="sr" hreflang="sr" data-title="Tiramin" 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/Tiramin" title="Tiramin – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Tiramin" 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/Tyramiini" title="Tyramiini – Finnish" lang="fi" hreflang="fi" data-title="Tyramiini" data-language-autonym="Suomi" data-language-local-name="Finnish" class="interlanguage-link-target"><span>Suomi</span></a></li><li class="interlanguage-link interwiki-sv mw-list-item"><a href="https://sv.wikipedia.org/wiki/Tyramin" title="Tyramin – Swedish" lang="sv" hreflang="sv" data-title="Tyramin" data-language-autonym="Svenska" data-language-local-name="Swedish" class="interlanguage-link-target"><span>Svenska</span></a></li><li class="interlanguage-link interwiki-tr mw-list-item"><a href="https://tr.wikipedia.org/wiki/Tiramin" title="Tiramin – Turkish" lang="tr" hreflang="tr" data-title="Tiramin" 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%A2%D0%B8%D1%80%D0%B0%D0%BC%D1%96%D0%BD" title="Тирамін – Ukrainian" lang="uk" hreflang="uk" data-title="Тирамін" data-language-autonym="Українська" data-language-local-name="Ukrainian" class="interlanguage-link-target"><span>Українська</span></a></li><li class="interlanguage-link interwiki-vi mw-list-item"><a href="https://vi.wikipedia.org/wiki/Tyramin" title="Tyramin – Vietnamese" lang="vi" hreflang="vi" data-title="Tyramin" data-language-autonym="Tiếng Việt" data-language-local-name="Vietnamese" class="interlanguage-link-target"><span>Tiếng Việt</span></a></li><li class="interlanguage-link interwiki-zh mw-list-item"><a href="https://zh.wikipedia.org/wiki/%E9%85%AA%E8%83%BA" title="酪胺 – Chinese" lang="zh" hreflang="zh" data-title="酪胺" 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/Q165930#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"> <div id="left-navigation"> <nav aria-label="Namespaces"> <div id="p-associated-pages" class="vector-menu vector-menu-tabs mw-portlet mw-portlet-associated-pages" > <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li 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class="vector-body" aria-labelledby="firstHeading" data-mw-ve-target-container> <div class="vector-body-before-content"> <div class="mw-indicators"> </div> <div id="siteSub" class="noprint">From Wikipedia, the free encyclopedia</div> </div> <div id="contentSub"><div id="mw-content-subtitle"></div></div> <div id="mw-content-text" class="mw-body-content"><div class="mw-content-ltr mw-parser-output" lang="en" dir="ltr"><div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Chemical compound</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">Not to be confused with <a href="/wiki/Amphetamine" title="Amphetamine">thyramine</a>.</div> <p class="mw-empty-elt"> </p> <style data-mw-deduplicate="TemplateStyles:r1257001546">.mw-parser-output .infobox-subbox{padding:0;border:none;margin:-3px;width:auto;min-width:100%;font-size:100%;clear:none;float:none;background-color:transparent}.mw-parser-output .infobox-3cols-child{margin:auto}.mw-parser-output .infobox .navbar{font-size:100%}@media screen{html.skin-theme-clientpref-night .mw-parser-output .infobox-full-data:not(.notheme)>div:not(.notheme)[style]{background:#1f1f23!important;color:#f8f9fa}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .infobox-full-data:not(.notheme) div:not(.notheme){background:#1f1f23!important;color:#f8f9fa}}@media(min-width:640px){body.skin--responsive .mw-parser-output .infobox-table{display:table!important}body.skin--responsive .mw-parser-output .infobox-table>caption{display:table-caption!important}body.skin--responsive .mw-parser-output .infobox-table>tbody{display:table-row-group}body.skin--responsive .mw-parser-output .infobox-table tr{display:table-row!important}body.skin--responsive .mw-parser-output .infobox-table th,body.skin--responsive .mw-parser-output .infobox-table td{padding-left:inherit;padding-right:inherit}}</style><table class="infobox" style="border-spacing:2px;"><caption class="infobox-title"><span title="International nonproprietary name (INN): Tyramine">Tyramine</span></caption><tbody><tr><td colspan="2" class="infobox-image notheme" style="background-color: #f8f9fa;"><span class="mw-default-size" typeof="mw:File/Frameless"><a href="/wiki/File:Tyramine.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/7/72/Tyramine.svg/220px-Tyramine.svg.png" decoding="async" width="220" height="81" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/7/72/Tyramine.svg/330px-Tyramine.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/7/72/Tyramine.svg/440px-Tyramine.svg.png 2x" data-file-width="424" data-file-height="156" /></a></span><div class="infobox-caption"><a href="/wiki/Skeletal_formula" title="Skeletal formula">Skeletal formula</a> of tyramine</div></td></tr><tr><td colspan="2" class="infobox-image notheme" style="background-color: #f8f9fa;"><span class="mw-default-size" typeof="mw:File/Frameless"><a href="/wiki/File:Tyramine-neutral-from-xtal-view-1-3D-bs-17.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/1/1a/Tyramine-neutral-from-xtal-view-1-3D-bs-17.png/220px-Tyramine-neutral-from-xtal-view-1-3D-bs-17.png" decoding="async" width="220" height="192" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/1/1a/Tyramine-neutral-from-xtal-view-1-3D-bs-17.png/330px-Tyramine-neutral-from-xtal-view-1-3D-bs-17.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/1/1a/Tyramine-neutral-from-xtal-view-1-3D-bs-17.png/440px-Tyramine-neutral-from-xtal-view-1-3D-bs-17.png 2x" data-file-width="2294" data-file-height="2000" /></a></span><div class="infobox-caption"><a href="/wiki/Ball-and-stick_model" title="Ball-and-stick model">Ball-and-stick model</a> of the neutral (non-<a href="/wiki/Zwitterion" title="Zwitterion">zwitterionic</a>) form of tyramine found in the <a href="/wiki/Crystal_structure" title="Crystal structure">crystal structure</a><sup id="cite_ref-1" class="reference"><a href="#cite_note-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup></div></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;">Pronunciation</th><td class="infobox-data"><span class="rt-commentedText nowrap"><span class="IPA nopopups noexcerpt" lang="en-fonipa"><a href="/wiki/Help:IPA/English" title="Help:IPA/English">/<span style="border-bottom:1px dotted"><span title="/ˈ/: primary stress follows">ˈ</span><span title="'t' in 'tie'">t</span><span title="/aɪ/: 'i' in 'tide'">aɪ</span><span title="'r' in 'rye'">r</span><span title="/ə/: 'a' in 'about'">ə</span><span title="'m' in 'my'">m</span><span title="/iː/: 'ee' in 'fleece'">iː</span><span title="'n' in 'nigh'">n</span></span>/</a></span></span> <a href="/wiki/Help:Pronunciation_respelling_key" title="Help:Pronunciation respelling key"><i title="English pronunciation respelling"><span style="font-size:90%">TY</span>-rə-meen</i></a> </td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;">Other names</th><td class="infobox-data">Tyramin; 4-Hydroxyphenethylamine; <i>para</i>-Tyramine; <i>p</i>-Tyramine; 4-Tyramine; Mydrial; Uteramin</td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Anatomical_Therapeutic_Chemical_Classification_System" title="Anatomical Therapeutic Chemical Classification System">ATC code</a></th><td class="infobox-data"><style data-mw-deduplicate="TemplateStyles:r1126788409">.mw-parser-output .plainlist ol,.mw-parser-output .plainlist ul{line-height:inherit;list-style:none;margin:0;padding:0}.mw-parser-output .plainlist ol li,.mw-parser-output .plainlist ul li{margin-bottom:0}</style><div class="plainlist"><ul><li>none</li></ul></div></td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd"><a href="/wiki/Pharmacokinetics" title="Pharmacokinetics">Pharmacokinetic</a> data</th></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Drug_metabolism" title="Drug metabolism">Metabolism</a></th><td class="infobox-data"><a href="/wiki/CYP2D6" title="CYP2D6">CYP2D6</a>, <a href="/wiki/Flavin-containing_monooxygenase_3" title="Flavin-containing monooxygenase 3">flavin-containing monooxygenase 3</a>, <a href="/wiki/Monoamine_oxidase_A" title="Monoamine oxidase A">monoamine oxidase A</a>, <a href="/wiki/Monoamine_oxidase_B" title="Monoamine oxidase B">monoamine oxidase B</a>, <a href="/wiki/Phenylethanolamine_N-methyltransferase" title="Phenylethanolamine N-methyltransferase">phenylethanolamine <i>N</i>-methyltransferase</a>, <a href="/wiki/Dopamine_beta-hydroxylase" title="Dopamine beta-hydroxylase">dopamine β-hydroxylase</a>, others</td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Metabolite" title="Metabolite">Metabolites</a></th><td class="infobox-data"><a href="/wiki/4-Hydroxyphenylacetaldehyde" title="4-Hydroxyphenylacetaldehyde">4-Hydroxyphenylacetaldehyde</a>, <a href="/wiki/Dopamine" title="Dopamine">dopamine</a>, <a href="/wiki/N-methyltyramine" class="mw-redirect" title="N-methyltyramine"><i>N</i>-methyltyramine</a>, <a href="/wiki/Octopamine" title="Octopamine">octopamine</a></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%;">4-(2-aminoethyl)phenol</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=51-67-2">51-67-2</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/5610">5610</a></span></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Guide_to_Pharmacology" title="Guide to Pharmacology">IUPHAR/BPS</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.guidetopharmacology.org"><a rel="nofollow" class="external text" href="https://www.guidetopharmacology.org/GRAC/LigandDisplayForward?ligandId=2150">2150</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.5408.html">5408</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/X8ZC7V0OX3">X8ZC7V0OX3</a></span></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/KEGG" title="KEGG">KEGG</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.kegg.jp"><a rel="nofollow" class="external text" href="https://www.kegg.jp/entry/C00483">C00483</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/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:15760">CHEBI:15760</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/ChEMBL" title="ChEMBL">ChEMBL</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.ebi.ac.uk"><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chembldb/index.php/compound/inspect/ChEMBL11608">ChEMBL11608</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/DTXSID2043874">DTXSID2043874</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q165930#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 scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/ECHA_InfoCard" class="mw-redirect" title="ECHA InfoCard"><span title="echa.europa.eu">ECHA InfoCard</span></a></th><td class="infobox-data"><a rel="nofollow" class="external text" href="https://echa.europa.eu/substance-information/-/substanceinfo/100.000.106">100.000.106</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q165930#P2566" title="Edit this at Wikidata"><img alt="Edit this at Wikidata" src="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/10px-OOjs_UI_icon_edit-ltr-progressive.svg.png" decoding="async" width="10" height="10" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/15px-OOjs_UI_icon_edit-ltr-progressive.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/20px-OOjs_UI_icon_edit-ltr-progressive.svg.png 2x" data-file-width="20" data-file-height="20" /></a></span></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>8</sub><span title="Hydrogen">H</span><sub>11</sub><span title="Nitrogen">N</span><span title="Oxygen">O</span></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="7002137181999999999♠"></span>137.182</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=Oc1ccc%28cc1%29CCN">Interactive image</a></span></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Density" title="Density">Density</a></th><td class="infobox-data">1.103 g/cm<sup>3</sup> predicted<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></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Melting_point" title="Melting point">Melting point</a></th><td class="infobox-data">164.5 °C (328.1 °F) <sup id="cite_ref-Merck_3-0" class="reference"><a href="#cite_note-Merck-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Boiling_point" title="Boiling point">Boiling point</a></th><td class="infobox-data">206 °C (403 °F) at 25 mmHg; 166 °C at 2 mmHg<sup id="cite_ref-Merck_3-1" class="reference"><a href="#cite_note-Merck-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup></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%;">Oc1ccc(cc1)CCN</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/C8H11NO/c9-6-5-7-1-3-8(10)4-2-7/h1-4,10H,5-6,9H2<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:DZGWFCGJZKJUFP-UHFFFAOYSA-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></tbody></table> <p><b>Tyramine</b> (<span class="rt-commentedText nowrap"><span class="IPA nopopups noexcerpt" lang="en-fonipa"><a href="/wiki/Help:IPA/English" title="Help:IPA/English">/<span style="border-bottom:1px dotted"><span title="/ˈ/: primary stress follows">ˈ</span><span title="'t' in 'tie'">t</span><span title="/aɪ/: 'i' in 'tide'">aɪ</span><span title="'r' in 'rye'">r</span><span title="/ə/: 'a' in 'about'">ə</span><span title="'m' in 'my'">m</span><span title="/iː/: 'ee' in 'fleece'">iː</span><span title="'n' in 'nigh'">n</span></span>/</a></span></span> <a href="/wiki/Help:Pronunciation_respelling_key" title="Help:Pronunciation respelling key"><i title="English pronunciation respelling"><span style="font-size:90%">TY</span>-rə-meen</i></a>) (also spelled <b>tyramin</b>), also known under several other names,<sup id="cite_ref-4" class="reference"><a href="#cite_note-4"><span class="cite-bracket">[</span>note 1<span class="cite-bracket">]</span></a></sup> is a <a href="/wiki/Natural_product" title="Natural product">naturally</a> occurring <a href="/wiki/Trace_amine" title="Trace amine">trace amine</a> derived from the amino acid <a href="/wiki/Tyrosine" title="Tyrosine">tyrosine</a>.<sup id="cite_ref-pubchem_5-0" class="reference"><a href="#cite_note-pubchem-5"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> Tyramine acts as a <a href="/wiki/Catecholamine" title="Catecholamine">catecholamine</a> <a href="/wiki/Monoamine_releasing_agent" title="Monoamine releasing agent">releasing agent</a>. Notably, it is unable to cross the <a href="/wiki/Blood%E2%80%93brain_barrier" title="Blood–brain barrier">blood-brain barrier</a>, resulting in only non-psychoactive <a href="/wiki/Peripheral_nervous_system" title="Peripheral nervous system">peripheral</a> <a href="/wiki/Sympathomimetic_drug" title="Sympathomimetic drug">sympathomimetic</a> effects following ingestion. A <a href="/wiki/Hypertensive_emergency" title="Hypertensive emergency">hypertensive crisis</a> can result, however, from ingestion of tyramine-rich foods in conjunction with the use of <a href="/wiki/Monoamine_oxidase_inhibitor" title="Monoamine oxidase inhibitor">monoamine oxidase inhibitors</a> (MAOIs). </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Occurrence">Occurrence</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Tyramine&action=edit&section=1" title="Edit section: Occurrence"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Tyramine occurs widely in <a href="/wiki/Plant" title="Plant">plants</a><sup id="cite_ref-6" class="reference"><a href="#cite_note-6"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> and <a href="/wiki/Animal" title="Animal">animals</a>, and is metabolized by various <a href="/wiki/Enzyme" title="Enzyme">enzymes</a>, including <a href="/wiki/Monoamine_oxidase" title="Monoamine oxidase">monoamine oxidases</a>. In foods, it often is produced by the <a href="/wiki/Decarboxylation" title="Decarboxylation">decarboxylation</a> of <a href="/wiki/Tyrosine" title="Tyrosine">tyrosine</a> during <a href="/wiki/Fermentation_(food)" class="mw-redirect" title="Fermentation (food)">fermentation</a> or <a href="/wiki/Decomposition" title="Decomposition">decay</a>. Foods that are fermented, cured, pickled, aged, or spoiled have high amounts of tyramine. Tyramine levels go up when foods are at room temperature or go past their freshness date. </p><p>Specific foods containing considerable amounts of tyramine include:<sup id="cite_ref-7" class="reference"><a href="#cite_note-7"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-8" class="reference"><a href="#cite_note-8"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> </p> <ul><li><b>Strong or aged cheeses</b>: cheddar, Swiss, Parmesan, Stilton, Gorgonzola or blue cheeses, Camembert, feta, Muenster</li> <li><b>Meats that are cured, smoked, or processed</b>: such as salami, pepperoni, dry sausages, hot dogs, bologna, bacon, corned beef, pickled or smoked fish, caviar, aged chicken livers, soups or gravies made from meat extract</li> <li><b>Pickled or fermented foods</b>: sauerkraut, kimchi, tofu (especially <a href="/wiki/Stinky_tofu" title="Stinky tofu">stinky tofu</a>), pickles, miso soup, bean curd, tempeh, sourdough breads</li> <li><b>Condiments</b>: soy, shrimp, fish, miso, teriyaki, and bouillon-based sauces</li> <li><b>Drinks</b>: beer (especially tap or home-brewed), vermouth, red wine, sherry, liqueurs</li> <li><b>Beans, vegetables, and fruits</b>: fermented or pickled vegetables, overripe fruits</li> <li><b>Chocolate</b><sup id="cite_ref-9" class="reference"><a href="#cite_note-9"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup></li></ul> <p>Scientists more and more consider tyramine in food as an aspect of safety.<sup id="cite_ref-10" class="reference"><a href="#cite_note-10"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> They propose projects of regulations aimed to enact control of biogenic amines in food by various strategies, including usage of proper fermentation starters, or preventing their decarboxylase activity.<sup id="cite_ref-11" class="reference"><a href="#cite_note-11"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> Some authors wrote that this has already given positive results, and tyramine content in food is now lower than it has been in the past.<sup id="cite_ref-12" class="reference"><a href="#cite_note-12"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="In_plants">In plants</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Tyramine&action=edit&section=2" title="Edit section: In plants"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><a href="/wiki/Mistletoe" title="Mistletoe">Mistletoe</a> (toxic and not used by humans as a food, but historically used as a medicine).<sup id="cite_ref-13" class="reference"><a href="#cite_note-13"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="In_animals">In animals</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Tyramine&action=edit&section=3" title="Edit section: In animals"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Tyramine also plays a role in animals including: In <a href="/wiki/Behavior" title="Behavior">behavioral</a> and <a href="/wiki/Motor_neuron" title="Motor neuron">motor</a> functions in <i><a href="/wiki/Caenorhabditis_elegans" title="Caenorhabditis elegans">Caenorhabditis elegans</a></i>;<sup id="cite_ref-Alkema-Hunter-Ensor-Ringstad-Horvitz-2005_14-0" class="reference"><a href="#cite_note-Alkema-Hunter-Ensor-Ringstad-Horvitz-2005-14"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup> <i><a href="/wiki/Locusta_migratoria" class="mw-redirect" title="Locusta migratoria">Locusta migratoria</a></i> <a href="/wiki/Swarm_behaviour" title="Swarm behaviour">swarming behaviour</a>;<sup id="cite_ref-Ma-et-al-2015_15-0" class="reference"><a href="#cite_note-Ma-et-al-2015-15"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup> and various nervous roles in <i><a href="/wiki/Rhipicephalus" title="Rhipicephalus">Rhipicephalus</a></i>, <i><a href="/wiki/Honey_bee" title="Honey bee">Apis</a></i>, <i><a href="/wiki/Migratory_locust" title="Migratory locust">Locusta</a></i>, <i><a href="/wiki/Periplaneta" title="Periplaneta">Periplaneta</a></i>, <i><a href="/wiki/Drosophila" title="Drosophila">Drosophila</a></i>, <i><a href="/wiki/Phormia" class="mw-redirect" title="Phormia">Phormia</a></i>, <i><a href="/wiki/Papilio" title="Papilio">Papilio</a></i>, <i><a href="/wiki/Bombyx" title="Bombyx">Bombyx</a></i>, <i><a href="/wiki/Chilo_(moth)" title="Chilo (moth)">Chilo</a></i>, <i><a href="/wiki/Heliothis" title="Heliothis">Heliothis</a></i>, <i><a href="/wiki/Mamestra" title="Mamestra">Mamestra</a></i>, <i><a href="/wiki/Agrotis" title="Agrotis">Agrotis</a></i>, and <i><a href="/wiki/Anopheles" title="Anopheles">Anopheles</a></i>.<sup id="cite_ref-Ohta-Ozoe-2014_16-0" class="reference"><a href="#cite_note-Ohta-Ozoe-2014-16"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Physical_effects_and_pharmacology">Physical effects and pharmacology</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Tyramine&action=edit&section=4" title="Edit section: Physical effects and pharmacology"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Evidence for the presence of tyramine in the human brain has been confirmed by postmortem analysis.<sup id="cite_ref-17" class="reference"><a href="#cite_note-17"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup> Additionally, the possibility that tyramine acts directly as a <a href="/wiki/Neuromodulator" class="mw-redirect" title="Neuromodulator">neuromodulator</a> was revealed by the discovery of a <a href="/wiki/G_protein" title="G protein">G protein</a>-coupled receptor with high affinity for tyramine, called <a href="/wiki/Trace_amine-associated_receptor" title="Trace amine-associated receptor">TAAR1</a>.<sup id="cite_ref-18" class="reference"><a href="#cite_note-18"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-19" class="reference"><a href="#cite_note-19"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup> The TAAR1 receptor is found in the <a href="/wiki/Brain" title="Brain">brain</a>, as well as peripheral tissues, including the <a href="/wiki/Kidney" title="Kidney">kidneys</a>.<sup id="cite_ref-20" class="reference"><a href="#cite_note-20"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup> Tyramine binds to <a href="/wiki/TAAR1" title="TAAR1">TAAR1</a> as an agonist in humans.<sup id="cite_ref-Human_trace_amines_and_hTAARs_October_2016_review_21-0" class="reference"><a href="#cite_note-Human_trace_amines_and_hTAARs_October_2016_review-21"><span class="cite-bracket">[</span>20<span class="cite-bracket">]</span></a></sup> </p><p><span class="anchor" id="Effects"></span> </p><p>Tyramine is physiologically metabolized by <a href="/wiki/Monoamine_oxidase" title="Monoamine oxidase">monoamine oxidases</a> (primarily <a href="/wiki/Monoamine_oxidase_A" title="Monoamine oxidase A">MAO-A</a>), <a href="/wiki/FMO3" class="mw-redirect" title="FMO3">FMO3</a>, <a href="/wiki/PNMT" class="mw-redirect" title="PNMT">PNMT</a>, <a href="/wiki/Dopamine_beta-hydroxylase" title="Dopamine beta-hydroxylase">DBH</a>, and <a href="/wiki/CYP2D6" title="CYP2D6">CYP2D6</a>.<sup id="cite_ref-BRENDA_FMO3_Homo_sapiens_22-0" class="reference"><a href="#cite_note-BRENDA_FMO3_Homo_sapiens-22"><span class="cite-bracket">[</span>21<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-FMO_23-0" class="reference"><a href="#cite_note-FMO-23"><span class="cite-bracket">[</span>22<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Trace_amine_template_1_24-0" class="reference"><a href="#cite_note-Trace_amine_template_1-24"><span class="cite-bracket">[</span>23<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Trace_amine_template_2_25-0" class="reference"><a href="#cite_note-Trace_amine_template_2-25"><span class="cite-bracket">[</span>24<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-CYP2D6_tyramine-dopamine_metabolism_26-0" class="reference"><a href="#cite_note-CYP2D6_tyramine-dopamine_metabolism-26"><span class="cite-bracket">[</span>25<span class="cite-bracket">]</span></a></sup> Human monoamine oxidase enzymes metabolize tyramine into <a href="/wiki/4-hydroxyphenylacetaldehyde" class="mw-redirect" title="4-hydroxyphenylacetaldehyde">4-hydroxyphenylacetaldehyde</a>.<sup id="cite_ref-HMDB_4-Hydroxyphenylacetaldehyde_27-0" class="reference"><a href="#cite_note-HMDB_4-Hydroxyphenylacetaldehyde-27"><span class="cite-bracket">[</span>26<span class="cite-bracket">]</span></a></sup> If monoamine metabolism is compromised by the use of <a href="/wiki/Monoamine_oxidase_inhibitor" title="Monoamine oxidase inhibitor">monoamine oxidase inhibitors</a> (MAOIs) and foods high in tyramine are ingested, a <a href="/wiki/Hypertensive_emergency" title="Hypertensive emergency">hypertensive crisis</a> can result, as tyramine also can displace stored monoamines, such as <a href="/wiki/Dopamine" title="Dopamine">dopamine</a>, <a href="/wiki/Norepinephrine" title="Norepinephrine">norepinephrine</a>, and <a href="/wiki/Epinephrine" class="mw-redirect" title="Epinephrine">epinephrine</a>, from pre-<a href="/wiki/Synaptic_vesicles" class="mw-redirect" title="Synaptic vesicles">synaptic vesicles</a>. Tyramine is considered a "<a href="/wiki/False_neurotransmitter" title="False neurotransmitter">false neurotransmitter</a>", as it enters noradrenergic nerve terminals and displaces large amounts of norepinephrine, which enters the blood stream and causes vasoconstriction. </p><p>Additionally, cocaine has been found to block blood pressure rise that is originally attributed to tyramine, which is explained by the blocking of <a href="/wiki/Adrenaline" title="Adrenaline">adrenaline</a> by cocaine from reabsorption to the brain.<sup id="cite_ref-28" class="reference"><a href="#cite_note-28"><span class="cite-bracket">[</span>27<span class="cite-bracket">]</span></a></sup> </p><p>The first signs of this effect were discovered by a British pharmacist who noticed that his wife, who at the time was on MAOI medication, had severe headaches when eating cheese.<sup id="cite_ref-29" class="reference"><a href="#cite_note-29"><span class="cite-bracket">[</span>28<span class="cite-bracket">]</span></a></sup> For this reason, it is still called the "cheese reaction" or "cheese crisis", although other foods can cause the same problem.<sup id="cite_ref-30" class="reference"><a href="#cite_note-30"><span class="cite-bracket">[</span>29<span class="cite-bracket">]</span></a></sup> </p><p>Most processed cheeses do not contain enough tyramine to cause hypertensive effects, although some aged cheeses (such as <a href="/wiki/Stilton_cheese" title="Stilton cheese">Stilton</a>) do.<sup id="cite_ref-31" class="reference"><a href="#cite_note-31"><span class="cite-bracket">[</span>30<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-32" class="reference"><a href="#cite_note-32"><span class="cite-bracket">[</span>31<span class="cite-bracket">]</span></a></sup> </p><p>A large dietary intake of tyramine (or a dietary intake of tyramine while taking MAO inhibitors) can cause the tyramine pressor response, which is defined as an increase in <a href="/wiki/Systolic_blood_pressure" class="mw-redirect" title="Systolic blood pressure">systolic blood pressure</a> of 30 <a href="/wiki/MmHg" class="mw-redirect" title="MmHg">mmHg</a> or more. The increased release of norepinephrine (noradrenaline) from neuronal cytosol or storage vesicles is thought to cause the <a href="/wiki/Vasoconstriction" title="Vasoconstriction">vasoconstriction</a> and increased heart rate and blood pressure of the pressor response. In severe cases, <a href="/wiki/Adrenergic_crisis" class="mw-redirect" title="Adrenergic crisis">adrenergic crisis</a> can occur.<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Identifying_reliable_sources_(medicine)" title="Wikipedia:Identifying reliable sources (medicine)"><span title="Material near this tag needs references to reliable medical sources. (April 2013)">medical citation needed</span></a></i>]</sup> Although the mechanism is unclear, tyramine ingestion also triggers migraine attacks in sensitive individuals and can even lead to stroke.<sup id="cite_ref-33" class="reference"><a href="#cite_note-33"><span class="cite-bracket">[</span>32<span class="cite-bracket">]</span></a></sup> Vasodilation, dopamine, and circulatory factors are all implicated in the migraines. Double-blind trials suggest that the effects of tyramine on migraine may be <a href="/wiki/Adrenergic" title="Adrenergic">adrenergic</a>.<sup id="cite_ref-34" class="reference"><a href="#cite_note-34"><span class="cite-bracket">[</span>33<span class="cite-bracket">]</span></a></sup> </p><p>Research reveals a possible link between <a href="/wiki/Migraines" class="mw-redirect" title="Migraines">migraines</a> and elevated levels of tyramine. A 2007 review published in Neurological Sciences<sup id="cite_ref-35" class="reference"><a href="#cite_note-35"><span class="cite-bracket">[</span>34<span class="cite-bracket">]</span></a></sup> presented data showing migraine and cluster diseases are characterized by an increase of circulating neurotransmitters and <a href="/wiki/Neuromodulation_(biology)" class="mw-redirect" title="Neuromodulation (biology)">neuromodulators</a> (including tyramine, <a href="/wiki/Octopamine" title="Octopamine">octopamine</a>, and <a href="/wiki/Synephrine" title="Synephrine">synephrine</a>) in the hypothalamus, amygdala, and dopaminergic system. People with migraine are over-represented among those with inadequate natural monoamine oxidase, resulting in similar problems to individuals taking MAO inhibitors. Many migraine attack triggers are high in tyramine.<sup id="cite_ref-36" class="reference"><a href="#cite_note-36"><span class="cite-bracket">[</span>35<span class="cite-bracket">]</span></a></sup> </p><p>If one has had repeated exposure to tyramine, however, there is a decreased pressor response; tyramine is degraded to octopamine, which is subsequently packaged in synaptic vesicles with norepinephrine (noradrenaline).<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (May 2014)">citation needed</span></a></i>]</sup> Therefore, after repeated tyramine exposure, these vesicles contain an increased amount of octopamine and a relatively reduced amount of norepinephrine. When these vesicles are secreted upon tyramine ingestion, there is a decreased pressor response, as less norepinephrine is secreted into the <a href="/wiki/Synapse" title="Synapse">synapse</a>, and octopamine does not activate alpha or beta <a href="/wiki/Adrenergic_receptors" class="mw-redirect" title="Adrenergic receptors">adrenergic receptors</a>.<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Identifying_reliable_sources_(medicine)" title="Wikipedia:Identifying reliable sources (medicine)"><span title="Material near this tag needs references to reliable medical sources. (April 2013)">medical citation needed</span></a></i>]</sup> </p><p>When using a MAO inhibitor (MAOI), an intake of approximately 10 to 25 mg of tyramine is required for a severe reaction, compared to 6 to 10 mg for a mild reaction.<sup id="cite_ref-37" class="reference"><a href="#cite_note-37"><span class="cite-bracket">[</span>36<span class="cite-bracket">]</span></a></sup> </p><p>Tyramine, like <a href="/wiki/Phenethylamine" title="Phenethylamine">phenethylamine</a>, is a <a href="/wiki/Monoaminergic_activity_enhancer" title="Monoaminergic activity enhancer">monoaminergic activity enhancer</a> (MAE) of <a href="/wiki/Serotonin" title="Serotonin">serotonin</a>, <a href="/wiki/Norepinephrine" title="Norepinephrine">norepinephrine</a>, and <a href="/wiki/Dopamine" title="Dopamine">dopamine</a> in addition to its catecholamine-releasing activity.<sup id="cite_ref-ShimazuMiklya2004_38-0" class="reference"><a href="#cite_note-ShimazuMiklya2004-38"><span class="cite-bracket">[</span>37<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Knoll2003_39-0" class="reference"><a href="#cite_note-Knoll2003-39"><span class="cite-bracket">[</span>38<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-KnollMiklyaKnoll1996_40-0" class="reference"><a href="#cite_note-KnollMiklyaKnoll1996-40"><span class="cite-bracket">[</span>39<span class="cite-bracket">]</span></a></sup> That is, it enhances the <a href="/wiki/Action_potential" title="Action potential">action potential</a>-mediated release of these <a href="/wiki/Monoamine_neurotransmitter" title="Monoamine neurotransmitter">monoamine neurotransmitters</a>.<sup id="cite_ref-ShimazuMiklya2004_38-1" class="reference"><a href="#cite_note-ShimazuMiklya2004-38"><span class="cite-bracket">[</span>37<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Knoll2003_39-1" class="reference"><a href="#cite_note-Knoll2003-39"><span class="cite-bracket">[</span>38<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-KnollMiklyaKnoll1996_40-1" class="reference"><a href="#cite_note-KnollMiklyaKnoll1996-40"><span class="cite-bracket">[</span>39<span class="cite-bracket">]</span></a></sup> The compound is active as a MAE at much lower concentrations than the concentrations at which it induces the release of catecholamines.<sup id="cite_ref-ShimazuMiklya2004_38-2" class="reference"><a href="#cite_note-ShimazuMiklya2004-38"><span class="cite-bracket">[</span>37<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Knoll2003_39-2" class="reference"><a href="#cite_note-Knoll2003-39"><span class="cite-bracket">[</span>38<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-KnollMiklyaKnoll1996_40-2" class="reference"><a href="#cite_note-KnollMiklyaKnoll1996-40"><span class="cite-bracket">[</span>39<span class="cite-bracket">]</span></a></sup> The MAE actions of tyramine and other MAEs may be mediated by TAAR1 agonism.<sup id="cite_ref-HarsingKnollMiklya2022_41-0" class="reference"><a href="#cite_note-HarsingKnollMiklya2022-41"><span class="cite-bracket">[</span>40<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-HarsingTimarMiklya2023_42-0" class="reference"><a href="#cite_note-HarsingTimarMiklya2023-42"><span class="cite-bracket">[</span>41<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Biosynthesis">Biosynthesis</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Tyramine&action=edit&section=5" title="Edit section: Biosynthesis"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Biochemically, tyramine is produced by the <a href="/wiki/Decarboxylation" title="Decarboxylation">decarboxylation</a> of <a href="/wiki/Tyrosine" title="Tyrosine">tyrosine</a> via the action of the enzyme <a href="/wiki/Tyrosine_decarboxylase" title="Tyrosine decarboxylase">tyrosine decarboxylase</a>.<sup id="cite_ref-43" class="reference"><a href="#cite_note-43"><span class="cite-bracket">[</span>42<span class="cite-bracket">]</span></a></sup> Tyramine can, in turn, be converted to methylated <a href="/wiki/Alkaloid" title="Alkaloid">alkaloid</a> derivatives <a href="/wiki/N-Methyltyramine" title="N-Methyltyramine"><i>N</i>-methyltyramine</a>, <a href="/wiki/Hordenine" title="Hordenine"><i>N</i>,<i>N</i>-dimethyltyramine</a> (hordenine), and <a href="/wiki/Candicine" title="Candicine"><i>N</i>,<i>N</i>,<i>N</i>-trimethyltyramine</a> (candicine). </p> <ul class="gallery mw-gallery-traditional center"> <li class="gallerybox" style="width: 155px"> <div class="thumb" style="width: 150px; height: 150px;"><span typeof="mw:File"><a href="/wiki/File:Tyramine.svg" class="mw-file-description" title="Tyramine"><img alt="Tyramine" src="//upload.wikimedia.org/wikipedia/commons/thumb/7/72/Tyramine.svg/120px-Tyramine.svg.png" decoding="async" width="120" height="44" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/7/72/Tyramine.svg/180px-Tyramine.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/7/72/Tyramine.svg/240px-Tyramine.svg.png 2x" data-file-width="424" data-file-height="156" /></a></span></div> <div class="gallerytext">Tyramine</div> </li> <li class="gallerybox" style="width: 155px"> <div class="thumb" style="width: 150px; height: 150px;"><span typeof="mw:File"><a href="/wiki/File:Methyltyramine.svg" class="mw-file-description" title="N-Methyltyramine"><img alt="N-Methyltyramine" src="//upload.wikimedia.org/wikipedia/commons/thumb/4/47/Methyltyramine.svg/120px-Methyltyramine.svg.png" decoding="async" width="120" height="56" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/4/47/Methyltyramine.svg/180px-Methyltyramine.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/4/47/Methyltyramine.svg/240px-Methyltyramine.svg.png 2x" data-file-width="512" data-file-height="238" /></a></span></div> <div class="gallerytext"><i>N</i>-Methyltyramine</div> </li> <li class="gallerybox" style="width: 155px"> <div class="thumb" style="width: 150px; height: 150px;"><span typeof="mw:File"><a href="/wiki/File:Dimethyltyramine.svg" class="mw-file-description" title="N,N-Dimethyltyramine (hordenine)"><img alt="N,N-Dimethyltyramine (hordenine)" src="//upload.wikimedia.org/wikipedia/commons/thumb/e/eb/Dimethyltyramine.svg/120px-Dimethyltyramine.svg.png" decoding="async" width="120" height="57" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/eb/Dimethyltyramine.svg/180px-Dimethyltyramine.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/e/eb/Dimethyltyramine.svg/240px-Dimethyltyramine.svg.png 2x" data-file-width="512" data-file-height="244" /></a></span></div> <div class="gallerytext"><i>N</i>,<i>N</i>-Dimethyltyramine (hordenine)</div> </li> <li class="gallerybox" style="width: 155px"> <div class="thumb" style="width: 150px; height: 150px;"><span typeof="mw:File"><a href="/wiki/File:Candicine.svg" class="mw-file-description" title="N,N,N-Trimethyltyramine (candicine)"><img alt="N,N,N-Trimethyltyramine (candicine)" src="//upload.wikimedia.org/wikipedia/commons/thumb/9/9d/Candicine.svg/120px-Candicine.svg.png" decoding="async" width="120" height="55" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/9/9d/Candicine.svg/180px-Candicine.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/9/9d/Candicine.svg/240px-Candicine.svg.png 2x" data-file-width="512" data-file-height="235" /></a></span></div> <div class="gallerytext"><i>N</i>,<i>N</i>,<i>N</i>-Trimethyltyramine (candicine)</div> </li> </ul><p> In humans, tyramine is produced from tyrosine, as shown in the following diagram.</p><div class="skin-invert-image"> <table role="presentation" cellpadding="0" style="border-spacing:0; margin-left: auto; margin-right: auto; border: none;"> <tbody><tr> <td><div class="thumb center" style="margin: 1em auto;"> <div class="thumbinner" style="width:592px;"> <div style="clear: both; font-weight: bold; font-size: 106.4%; text-align: center; background-color: #F0F8FF;margin-bottom:3px;">Biosynthetic pathways for <a href="/wiki/Catecholamine" title="Catecholamine">catecholamines</a> and <a href="/wiki/Trace_amine" title="Trace amine">trace amines</a> in the <a href="/wiki/Human_brain" title="Human brain">human brain</a><sup id="cite_ref-Trace_amine_template_1_24-1" class="reference"><a href="#cite_note-Trace_amine_template_1-24"><span class="cite-bracket">[</span>23<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Trace_amine_template_2_25-1" class="reference"><a href="#cite_note-Trace_amine_template_2-25"><span class="cite-bracket">[</span>24<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-CYP2D6_tyramine-dopamine_metabolism_26-1" class="reference"><a href="#cite_note-CYP2D6_tyramine-dopamine_metabolism-26"><span class="cite-bracket">[</span>25<span class="cite-bracket">]</span></a></sup></div> <div style="position:relative; width:590px; height:465px; overflow:hidden; border:solid #ccc 1px; background-color:white;"> <div style="left:5px; top:0px; width:580px; position:absolute"> <span typeof="mw:File"><a href="https://commons.wikimedia.org/wiki/File:Catecholamine_and_trace_amine_biosynthesis.svg" title="commons:File:Catecholamine and trace amine biosynthesis.svg"><img alt="Graphic of catecholamine and trace amine biosynthesis" src="//upload.wikimedia.org/wikipedia/commons/thumb/4/46/Catecholamine_and_trace_amine_biosynthesis.svg/580px-Catecholamine_and_trace_amine_biosynthesis.svg.png" decoding="async" width="580" height="458" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/4/46/Catecholamine_and_trace_amine_biosynthesis.svg/870px-Catecholamine_and_trace_amine_biosynthesis.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/4/46/Catecholamine_and_trace_amine_biosynthesis.svg/1160px-Catecholamine_and_trace_amine_biosynthesis.svg.png 2x" data-file-width="512" data-file-height="404" /></a></span> </div> <div style="text-align:center; font-size:14px; line-height:110%"> <div style="background-color:transparent; color:black"><div id="annotation_40x60" style="position:absolute; left:40px; top:60px; line-height:110%;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/Phenylalanine" title="Phenylalanine"><small>L</small>-Phenylalanine</a></span></div> <div id="annotation_50x185" style="position:absolute; left:50px; top:185px; line-height:110%;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/Tyrosine" title="Tyrosine"><small>L</small>-Tyrosine</a></span></div> <div id="annotation_60x315" style="position:absolute; left:60px; top:315px; line-height:110%;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/L-DOPA" title="L-DOPA"><small>L</small>-DOPA</a></span></div> <div id="annotation_50x445" style="position:absolute; left:50px; top:445px; line-height:110%;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/Adrenaline" title="Adrenaline">Epinephrine</a></span></div> <div id="annotation_245x60" style="position:absolute; left:245px; top:60px; line-height:110%;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/Phenethylamine" title="Phenethylamine">Phenethylamine</a></span></div> <div id="annotation_245x185" style="position:absolute; left:245px; top:185px; line-height:110%;"><span style="background-color:transparent; color:inherit;"><span style="color:black;background:yellow"><b><i>p</i>-Tyramine</b></span></span></div> <div id="annotation_245x315" style="position:absolute; left:245px; top:315px; line-height:110%;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/Dopamine" title="Dopamine">Dopamine</a></span></div> <div id="annotation_245x445" style="position:absolute; left:245px; top:445px; line-height:110%;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/Norepinephrine" title="Norepinephrine">Norepinephrine</a></span></div> <div id="annotation_415x60" style="position:absolute; left:415px; top:60px; line-height:110%;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/N-Methylphenethylamine" title="N-Methylphenethylamine"><i>N</i>-Methylphenethylamine</a></span></div> <div id="annotation_440x138" style="position:absolute; left:440px; top:138px; line-height:110%;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/N-Methyltyramine" title="N-Methyltyramine"><i>N</i>-Methyltyramine</a></span></div> <div id="annotation_440x228" style="position:absolute; left:440px; top:228px; line-height:110%;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/Octopamine" title="Octopamine"><i>p</i>-Octopamine</a></span></div> <div id="annotation_455x350" style="position:absolute; left:455px; top:350px; line-height:110%;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/Synephrine" title="Synephrine">Synephrine</a></span></div> <div id="annotation_445x445" style="position:absolute; left:445px; top:445px; line-height:110%;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/3-Methoxytyramine" title="3-Methoxytyramine">3-Methoxytyramine</a></span></div> <div id="annotation_167x16" style="position:absolute; left:167px; top:16px; line-height:110%;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/Aromatic_L-amino_acid_decarboxylase" title="Aromatic L-amino acid decarboxylase">AADC</a></span></div> <div id="annotation_167x145" style="position:absolute; left:167px; top:145px; line-height:110%;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/Aromatic_L-amino_acid_decarboxylase" title="Aromatic L-amino acid decarboxylase">AADC</a></span></div> <div id="annotation_167x275" style="position:absolute; left:167px; top:275px; line-height:110%;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/Aromatic_L-amino_acid_decarboxylase" title="Aromatic L-amino acid decarboxylase">AADC</a></span></div> <div id="annotation_164x295" style="position:absolute; left:164px; top:295px; font-size:12px; font-size:12; line-height:14px;"><span style="background-color:transparent; color:inherit;">primary<br />pathway</span></div> <div id="annotation_370x17" style="position:absolute; left:370px; top:17px; line-height:110%;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/Phenylethanolamine_N-methyltransferase" title="Phenylethanolamine N-methyltransferase">PNMT</a></span></div> <div id="annotation_360x120" style="position:absolute; left:360px; top:120px; line-height:110%;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/Phenylethanolamine_N-methyltransferase" title="Phenylethanolamine N-methyltransferase">PNMT</a></span></div> <div id="annotation_445x255" style="position:absolute; left:445px; top:255px; line-height:110%;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/Phenylethanolamine_N-methyltransferase" title="Phenylethanolamine N-methyltransferase">PNMT</a></span></div> <div id="annotation_176x407" style="position:absolute; left:176px; top:407px; line-height:110%;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/Phenylethanolamine_N-methyltransferase" title="Phenylethanolamine N-methyltransferase">PNMT</a></span></div> <div id="annotation_40x90" style="position:absolute; left:40px; top:90px; line-height:110%;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/Biopterin-dependent_aromatic_amino_acid_hydroxylase" title="Biopterin-dependent aromatic amino acid hydroxylase">AAAH</a></span></div> <div id="annotation_40x220" style="position:absolute; left:40px; top:220px; line-height:110%;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/Biopterin-dependent_aromatic_amino_acid_hydroxylase" title="Biopterin-dependent aromatic amino acid hydroxylase">AAAH</a></span></div> <div id="annotation_225x215" style="position:absolute; left:225px; top:215px; line-height:110%;"><span style="background-color:transparent; color:inherit;">brain<br /><a href="/wiki/CYP2D6" title="CYP2D6">CYP2D6</a></span></div> <div id="annotation_291x217" style="position:absolute; left:291px; top:217px; font-size:12px; font-size:12; line-height:14px; text-align:left;"><span style="background-color:transparent; color:inherit;">minor<br />pathway</span></div> <div id="annotation_325x350" style="position:absolute; left:325px; top:350px; line-height:110%;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/Catechol-O-methyltransferase" title="Catechol-O-methyltransferase">COMT</a></span></div> <div id="annotation_250x350" style="position:absolute; left:250px; top:350px; line-height:110%;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/Dopamine_beta-hydroxylase" title="Dopamine beta-hydroxylase">DBH</a></span></div> <div id="annotation_360x185" style="position:absolute; left:360px; top:185px; line-height:110%;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/Dopamine_beta-hydroxylase" title="Dopamine beta-hydroxylase">DBH</a></span></div></div> </div> </div> <div class="thumbcaption" style="clear:left"><div style="float:left;margin-right:0.5em"><span typeof="mw:File"><span title="The image above contains clickable links"><img alt="The image above contains clickable links" src="//upload.wikimedia.org/wikipedia/commons/thumb/e/e6/Interactive_icon.svg/18px-Interactive_icon.svg.png" decoding="async" width="18" height="27" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/e6/Interactive_icon.svg/27px-Interactive_icon.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/e/e6/Interactive_icon.svg/36px-Interactive_icon.svg.png 2x" data-file-width="133" data-file-height="200" /></span></span></div>In humans, <a href="/wiki/Catecholamine" title="Catecholamine">catecholamines</a> and phenethylaminergic <a href="/wiki/Trace_amine" title="Trace amine">trace amines</a> are derived from the <a href="/wiki/Amino_acid" title="Amino acid">amino acid</a> <span class="nowrap"><a href="/wiki/Phenylalanine" title="Phenylalanine">L-phenylalanine</a></span>.</div> </div> </div> </td></tr></tbody></table> </div> <div style="clear:both;" class=""></div> <div class="mw-heading mw-heading2"><h2 id="Chemistry">Chemistry</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Tyramine&action=edit&section=6" title="Edit section: Chemistry"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>In the laboratory, tyramine can be synthesized in various ways, in particular by the decarboxylation of tyrosine.<sup id="cite_ref-44" class="reference"><a href="#cite_note-44"><span class="cite-bracket">[</span>43<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-45" class="reference"><a href="#cite_note-45"><span class="cite-bracket">[</span>44<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-46" class="reference"><a href="#cite_note-46"><span class="cite-bracket">[</span>45<span class="cite-bracket">]</span></a></sup> </p> <figure class="mw-halign-center" typeof="mw:File/Thumb"><a href="/wiki/File:Tyramine_synthesis.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/5/5e/Tyramine_synthesis.png/500px-Tyramine_synthesis.png" decoding="async" width="500" height="94" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/5/5e/Tyramine_synthesis.png/750px-Tyramine_synthesis.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/5/5e/Tyramine_synthesis.png/1000px-Tyramine_synthesis.png 2x" data-file-width="1743" data-file-height="326" /></a><figcaption>Tyrosine decarboxylation</figcaption></figure> <div class="mw-heading mw-heading2"><h2 id="Society_and_culture">Society and culture</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Tyramine&action=edit&section=7" title="Edit section: Society and culture"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Legal_status">Legal status</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Tyramine&action=edit&section=8" title="Edit section: Legal status"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading4"><h4 id="United_States">United States</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Tyramine&action=edit&section=9" title="Edit section: United States"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Tyramine is a Schedule I <a href="/wiki/Controlled_substance" title="Controlled substance">controlled substance</a>, categorized as a <a href="/wiki/Hallucinogen" title="Hallucinogen">hallucinogen</a>, making it illegal to buy, sell, or possess in the state of <a href="/wiki/Florida" title="Florida">Florida</a> without a license at any purity level or any form whatsoever. The language in the Florida <a href="/wiki/Statute" title="Statute">statute</a> says tyramine is illegal in "any material, compound, mixture, or preparation that contains any quantity of [tyramine] or that contains any of [its] <a href="/wiki/Salt_(chemistry)" title="Salt (chemistry)">salts</a>, <a href="/wiki/Isomers" class="mw-redirect" title="Isomers">isomers</a>, including optical, positional, or geometric isomers, and salts of isomers, if the existence of such salts, isomers, and salts of isomers is possible within the specific chemical designation."<sup id="cite_ref-Florida_Statutes_-_Chapter_893_-_DRUG_ABUSE_PREVENTION_AND_CONTROL_47-0" class="reference"><a href="#cite_note-Florida_Statutes_-_Chapter_893_-_DRUG_ABUSE_PREVENTION_AND_CONTROL-47"><span class="cite-bracket">[</span>46<span class="cite-bracket">]</span></a></sup> </p><p>This ban is likely the product of lawmakers overly eager to ban <a href="/wiki/Substituted_phenethylamine" title="Substituted phenethylamine">substituted phenethylamines</a>, which tyramine is, in the mistaken belief that ring-substituted phenethylamines are hallucinogenic drugs like the <a href="/wiki/2C_(psychedelics)" title="2C (psychedelics)">2C series</a> of <a href="/wiki/Psychedelic_drug" title="Psychedelic drug">psychedelic</a> substituted phenethylamines. The further banning of tyramine's <a href="/wiki/Enantiomer" title="Enantiomer">optical isomers</a>, <a href="/wiki/Structural_isomer#Position_isomerism_(regioisomerism)" title="Structural isomer">positional isomers</a>, or <a href="/wiki/Cis%E2%80%93trans_isomerism" title="Cis–trans isomerism">geometric isomers</a>, and salts of isomers where they exist, means that <a href="/wiki/Meta-tyramine" class="mw-redirect" title="Meta-tyramine">meta-tyramine</a> and <a href="/wiki/Phenylethanolamine" title="Phenylethanolamine">phenylethanolamine</a>, a substance found in every living human body, and other common, non-hallucinogenic substances are also illegal to buy, sell, or possess in Florida.<sup id="cite_ref-Florida_Statutes_-_Chapter_893_-_DRUG_ABUSE_PREVENTION_AND_CONTROL_47-1" class="reference"><a href="#cite_note-Florida_Statutes_-_Chapter_893_-_DRUG_ABUSE_PREVENTION_AND_CONTROL-47"><span class="cite-bracket">[</span>46<span class="cite-bracket">]</span></a></sup> Given that tyramine occurs naturally in many foods and drinks (most commonly as a by-product of bacterial fermentation), e.g. wine, cheese, and chocolate, Florida's total ban on the substance may prove difficult to enforce.<sup id="cite_ref-48" class="reference"><a href="#cite_note-48"><span class="cite-bracket">[</span>47<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Notes">Notes</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Tyramine&action=edit&section=10" title="Edit section: Notes"><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"><ol class="references"> <li id="cite_note-4"><span class="mw-cite-backlink"><b><a href="#cite_ref-4">^</a></b></span> <span class="reference-text">Synonyms and alternative names include: <b>4-hydroxyphenethylamine</b>, <b>para-tyramine</b>, <b>mydrial</b>, and <b>uteramin</b>; the latter two names are not commonly used. The <a href="/wiki/IUPAC_nomenclature_of_organic_chemistry" title="IUPAC nomenclature of organic chemistry">IUPAC</a> name is <span class="nowrap">4-(2-aminoethyl)phenol</span>.</span> </li> </ol></div></div> <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=Tyramine&action=edit&section=11" title="Edit section: References"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239543626"><div class="reflist"> <div class="mw-references-wrap mw-references-columns"><ol class="references"> <li id="cite_note-1"><span class="mw-cite-backlink"><b><a href="#cite_ref-1">^</a></b></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="CITEREFCruickshankKennedyShankland2013" class="citation journal cs1">Cruickshank L, Kennedy AR, Shankland N (2013). 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Struct.</a></i> <b>1051</b>: 132–136. <a href="/wiki/Bibcode_(identifier)" class="mw-redirect" title="Bibcode (identifier)">Bibcode</a>:<a rel="nofollow" class="external text" href="https://ui.adsabs.harvard.edu/abs/2013JMoSt1051..132C">2013JMoSt1051..132C</a>. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2Fj.molstruc.2013.08.002">10.1016/j.molstruc.2013.08.002</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=J.+Mol.+Struct.&rft.atitle=Tautomeric+and+ionisation+forms+of+dopamine+and+tyramine+in+the+solid+state&rft.volume=1051&rft.pages=132-136&rft.date=2013&rft_id=info%3Adoi%2F10.1016%2Fj.molstruc.2013.08.002&rft_id=info%3Abibcode%2F2013JMoSt1051..132C&rft.aulast=Cruickshank&rft.aufirst=L&rft.au=Kennedy%2C+AR&rft.au=Shankland%2C+N&rfr_id=info%3Asid%2Fen.wikipedia.org%3ATyramine" class="Z3988"></span></span> </li> <li id="cite_note-2"><span class="mw-cite-backlink"><b><a href="#cite_ref-2">^</a></b></span> <span class="reference-text">SciFinder, Calculated using Advanced Chemistry Development (ACD/Labs) Software V11.02 (© 1994-2021 ACD/Labs)</span> </li> <li id="cite_note-Merck-3"><span class="mw-cite-backlink">^ <a href="#cite_ref-Merck_3-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Merck_3-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text">The Merck Index, 10th Ed. 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Smith (1977) <i>Phytochemistry</i> <b>16</b> 9–18.</span> </li> <li id="cite_note-7"><span class="mw-cite-backlink"><b><a href="#cite_ref-7">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFHall-Flavin2018" class="citation web cs1">Hall-Flavin DK (18 December 2018). <a rel="nofollow" class="external text" href="https://www.mayoclinic.org/diseases-conditions/depression/expert-answers/maois/faq-20058035">"Avoid the combination of high-tyramine foods and MAOIs"</a>. <i>Mayo Clinic</i>.</cite><span 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title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=pubchem.ncbi.nlm.nih.gov&rft.atitle=Tyramine&rft_id=https%3A%2F%2Fpubchem.ncbi.nlm.nih.gov%2Fcompound%2FTyramine%23section%3DMechanism-of-Action&rfr_id=info%3Asid%2Fen.wikipedia.org%3ATyramine" class="Z3988"></span></span> </li> <li id="cite_note-10"><span class="mw-cite-backlink"><b><a href="#cite_ref-10">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFMartuscelliEspositoMastrocola2021" class="citation journal cs1">Martuscelli M, Esposito L, Mastrocola D (January 2021). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7825060">"Biogenic Amines' Content in Safe and Quality Food"</a>. <i>Foods</i>. <b>10</b> (1): 100. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://doi.org/10.3390%2Ffoods10010100">10.3390/foods10010100</a></span>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7825060">7825060</a></span>. <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/33418895">33418895</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Foods&rft.atitle=Biogenic+Amines%27+Content+in+Safe+and+Quality+Food&rft.volume=10&rft.issue=1&rft.pages=100&rft.date=2021-01&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC7825060%23id-name%3DPMC&rft_id=info%3Apmid%2F33418895&rft_id=info%3Adoi%2F10.3390%2Ffoods10010100&rft.aulast=Martuscelli&rft.aufirst=M&rft.au=Esposito%2C+L&rft.au=Mastrocola%2C+D&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC7825060&rfr_id=info%3Asid%2Fen.wikipedia.org%3ATyramine" class="Z3988"></span></span> </li> <li id="cite_note-11"><span class="mw-cite-backlink"><b><a href="#cite_ref-11">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation journal cs1"><a rel="nofollow" class="external text" href="https://doi.org/10.2903%2Fj.efsa.2011.2393">"Scientific Opinion on risk based control of biogenic amine formation in fermented foods"</a>. <i>EFSA Journal</i>. <b>9</b> (10): 2393. 2011. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://doi.org/10.2903%2Fj.efsa.2011.2393">10.2903/j.efsa.2011.2393</a></span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=EFSA+Journal&rft.atitle=Scientific+Opinion+on+risk+based+control+of+biogenic+amine+formation+in+fermented+foods&rft.volume=9&rft.issue=10&rft.pages=2393&rft.date=2011&rft_id=info%3Adoi%2F10.2903%2Fj.efsa.2011.2393&rft_id=https%3A%2F%2Fdoi.org%2F10.2903%252Fj.efsa.2011.2393&rfr_id=info%3Asid%2Fen.wikipedia.org%3ATyramine" class="Z3988"></span></span> </li> <li id="cite_note-12"><span class="mw-cite-backlink"><b><a href="#cite_ref-12">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFFinbergGillman2011" class="citation book cs1">Finberg JP, Gillman K (2011). 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Soc</i>. <b>95</b>: 1123–1128. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1039%2Fct9099501123">10.1039/ct9099501123</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=J.+Chem.+Soc.&rft.atitle=CXXVII.%3FIsolation+and+synthesis+of+p-hydroxyphenylethylamine%2C+an+active+principle+of+ergot+soluble+in+water&rft.volume=95&rft.pages=1123-1128&rft.date=1909&rft_id=info%3Adoi%2F10.1039%2Fct9099501123&rft.aulast=Barger&rft.aufirst=G&rft_id=https%3A%2F%2Fzenodo.org%2Frecord%2F1429723&rfr_id=info%3Asid%2Fen.wikipedia.org%3ATyramine" class="Z3988"></span></span> </li> <li id="cite_note-45"><span class="mw-cite-backlink"><b><a href="#cite_ref-45">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFWaser1925" class="citation journal cs1">Waser E (1925). 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"Reduction of Hydroxymandelonitriles. 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href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://doi.org/10.3389%2Ffmicb.2015.00472">10.3389/fmicb.2015.00472</a></span>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4435245">4435245</a></span>. <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/26042107">26042107</a>.</cite><span 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scope="row" class="navbox-group" style="width:1%;font-weight:normal; text-align: center;">Major excitatory /<br />inhibitory systems</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%;font-weight:normal;">Glutamate system</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/Agmatine" title="Agmatine">Agmatine</a></li> <li><a href="/wiki/Aspartic_acid" title="Aspartic acid">Aspartic acid (aspartate)</a></li> <li><a href="/wiki/Glutamate_(neurotransmitter)" title="Glutamate (neurotransmitter)">Glutamic acid (glutamate)</a></li> <li><a href="/wiki/Glutathione" title="Glutathione">Glutathione</a></li> <li><a href="/wiki/Glycine" title="Glycine">Glycine</a></li> <li><a href="/wiki/S-Nitrosoglutathione" title="S-Nitrosoglutathione">GSNO</a></li> <li><a href="/wiki/Oxidized_glutathione" class="mw-redirect" title="Oxidized glutathione">GSSG</a></li> <li><a href="/wiki/Kynurenic_acid" title="Kynurenic acid">Kynurenic acid</a></li> <li><a href="/wiki/N-Acetylaspartic_acid" title="N-Acetylaspartic acid">NAA</a></li> <li><a href="/wiki/N-Acetylaspartylglutamic_acid" title="N-Acetylaspartylglutamic acid">NAAG</a></li> <li><a href="/wiki/Proline" title="Proline">Proline</a></li> <li><a href="/wiki/Serine" title="Serine">Serine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;font-weight:normal;">GABA system</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/Gamma-Aminobutyric_acid" class="mw-redirect" title="Gamma-Aminobutyric acid">GABA</a></li> <li><a href="/wiki/Gamma-Amino-beta-hydroxybutyric_acid" class="mw-redirect" title="Gamma-Amino-beta-hydroxybutyric acid">GABOB</a></li> <li><a href="/wiki/Gamma-Hydroxybutyric_acid" class="mw-redirect" title="Gamma-Hydroxybutyric acid">GHB</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;font-weight:normal;">Glycine system</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/Alanine" title="Alanine">α-Alanine</a></li> <li><a href="/wiki/%CE%92-Alanine" title="Β-Alanine">β-Alanine</a></li> <li><a href="/wiki/Glycine" title="Glycine">Glycine</a></li> <li><a href="/wiki/Hypotaurine" title="Hypotaurine">Hypotaurine</a></li> <li><a href="/wiki/Proline" title="Proline">Proline</a></li> <li><a href="/wiki/Sarcosine" title="Sarcosine">Sarcosine</a></li> <li><a href="/wiki/Serine" title="Serine">Serine</a></li> <li><a href="/wiki/Taurine" title="Taurine">Taurine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;font-weight:normal;"><a href="/wiki/GHB_receptor" title="GHB receptor">GHB system</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/Gamma-Hydroxybutyric_acid" class="mw-redirect" title="Gamma-Hydroxybutyric acid">GHB</a></li> <li><a href="/wiki/T-HCA" title="T-HCA">T-HCA (GHC)</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;font-weight:normal; text-align: center;"><a href="/wiki/Biogenic_amine" title="Biogenic amine">Biogenic 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 scope="row" class="navbox-group" style="width:4em;font-weight:normal; text-align: center;">Monoamines</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/6-Hydroxymelatonin" title="6-Hydroxymelatonin">6-OHM</a></li> <li><a href="/wiki/Dopamine" title="Dopamine">Dopamine</a></li> <li><a href="/wiki/Adrenaline" title="Adrenaline">Epinephrine (adrenaline)</a></li> <li><a href="/wiki/N-Acetylserotonin" title="N-Acetylserotonin">NAS (normelatonin)</a></li> <li><a href="/wiki/Norepinephrine" title="Norepinephrine">Norepinephrine (noradrenaline)</a></li> <li><a href="/wiki/Serotonin" title="Serotonin">Serotonin (5-HT)</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:4em;font-weight:normal; text-align: center;">Trace amines</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/3-Iodothyronamine" title="3-Iodothyronamine">3-Iodothyronamine</a></li> <li><a href="/wiki/N-Methylphenethylamine" title="N-Methylphenethylamine">N-Methylphenethylamine</a></li> <li><a href="/wiki/N-Methyltryptamine" title="N-Methyltryptamine">N-Methyltryptamine</a></li> <li><a href="/wiki/Norfenefrine" title="Norfenefrine"><i>m</i>-Octopamine</a></li> <li><a href="/wiki/Octopamine" title="Octopamine"><i>p</i>-Octopamine</a></li> <li><a href="/wiki/Phenylethanolamine" title="Phenylethanolamine">Phenylethanolamine</a></li> <li><a href="/wiki/Phenethylamine" title="Phenethylamine">Phenethylamine</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 class="mw-selflink selflink"><i>p</i>-Tyramine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:4em;font-weight:normal; text-align: center;">Others</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/Histamine" title="Histamine">Histamine</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;font-weight:normal; text-align: center;"><a href="/wiki/Neuropeptide" title="Neuropeptide">Neuropeptides</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><td colspan="2" class="navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li>See <a href="/wiki/Template:Neuropeptides" title="Template:Neuropeptides">here</a> instead.</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="text-align: center;;width:1%"><a href="/wiki/Lipid" title="Lipid">Lipid</a>-derived</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 id="Endocannabinoids" scope="row" class="navbox-group" style="width:1%;font-weight:normal; text-align: center;">Endocannabinoids</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-Arachidonoylglycerol" title="2-Arachidonoylglycerol">2-AG</a></li> <li><a href="/wiki/2-Arachidonyl_glyceryl_ether" title="2-Arachidonyl glyceryl ether">2-AGE (noladin ether)</a></li> <li><a href="/w/index.php?title=2-Arachidonoyl_lysophosphatidylinositol&action=edit&redlink=1" class="new" title="2-Arachidonoyl lysophosphatidylinositol (page does not exist)">2-ALPI</a></li> <li><a href="/wiki/2-Oleoylglycerol" title="2-Oleoylglycerol">2-OG</a></li> <li><a href="/wiki/Arachidonoyl_serotonin" title="Arachidonoyl serotonin">AA-5-HT</a></li> <li><a href="/wiki/Anandamide" title="Anandamide">Anandamide (AEA)</a></li> <li><a href="/wiki/Docosatetraenoylethanolamide" title="Docosatetraenoylethanolamide">DEA</a></li> <li><a href="/wiki/Lysophosphatidylinositol" title="Lysophosphatidylinositol">LPI</a></li> <li><a href="/wiki/N-Arachidonoyl_dopamine" title="N-Arachidonoyl dopamine">NADA</a></li> <li><a href="/wiki/N-Arachidonylglycine" title="N-Arachidonylglycine">NAGly</a></li> <li><a href="/wiki/Oleoylethanolamide" title="Oleoylethanolamide">OEA</a></li> <li><a href="/wiki/Oleamide" title="Oleamide">Oleamide</a></li> <li><a href="/wiki/Palmitoylethanolamide" title="Palmitoylethanolamide">PEA</a></li> <li><a href="/wiki/RVD-Hp%CE%B1" title="RVD-Hpα">RVD-Hpα</a></li> <li><a href="/wiki/Stearoylethanolamide" title="Stearoylethanolamide">SEA</a></li> <li><a href="/wiki/Virodhamine" title="Virodhamine">Virodhamine (O-AEA)</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;font-weight:normal; text-align: center;"><a href="/wiki/Neurosteroid" title="Neurosteroid">Neurosteroids</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><td colspan="2" class="navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li>See <a href="/wiki/Template:Steroid_hormones" title="Template:Steroid hormones">here</a> instead.</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="text-align: center;;width:1%"><a href="/wiki/Nucleobase" class="mw-redirect" title="Nucleobase">Nucleobase</a>-derived</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 id="Nucleosides" scope="row" class="navbox-group" style="width:1%;font-weight:normal; text-align: center;">Nucleosides</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="Adenosine_system" scope="row" class="navbox-group" style="width:1%;font-weight:normal; text-align: center;"><a href="/wiki/Adenosine" title="Adenosine">Adenosine</a> system</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/Adenosine_diphosphate" title="Adenosine diphosphate">ADP</a></li> <li><a href="/wiki/Adenosine_monophosphate" title="Adenosine monophosphate">AMP</a></li> <li><a href="/wiki/Adenosine_triphosphate" title="Adenosine triphosphate">ATP</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="text-align: center;;width:1%"><a href="/wiki/Vitamin" title="Vitamin">Vitamin</a>-derived</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"></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="text-align: center;;width:1%">Miscellaneous</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 id="Cholinergic_system" scope="row" class="navbox-group" style="width:1%;font-weight:normal; text-align: center;">Cholinergic system</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/Acetylcholine" title="Acetylcholine">Acetylcholine</a></li></ul> </div></td></tr></tbody></table><div> </div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th id="Gasotransmitters" scope="row" class="navbox-group" style="width:1%;font-weight:normal; text-align: center;">Gasotransmitters</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/Carbon_monoxide" title="Carbon monoxide">Carbon monoxide (CO)</a></li> <li><a href="/wiki/Hydrogen_sulfide" title="Hydrogen sulfide">Hydrogen sulfide (H<sub>2</sub>S)</a></li> <li><a href="/wiki/Nitric_oxide" title="Nitric oxide">Nitric oxide (NO)</a></li></ul> </div></td></tr></tbody></table><div> </div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th id="Candidates" scope="row" class="navbox-group" style="width:1%;font-weight:normal; text-align: center;">Candidates</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/Acetaldehyde" title="Acetaldehyde">Acetaldehyde</a></li> <li><a href="/wiki/Ammonia" title="Ammonia">Ammonia (NH<sub>3</sub>)</a></li> <li><a href="/wiki/Carbonyl_sulfide" title="Carbonyl sulfide">Carbonyl sulfide (COS)</a></li> <li><a href="/wiki/Nitrous_oxide" title="Nitrous oxide">Nitrous oxide (N<sub>2</sub>O)</a></li> <li><a href="/wiki/Sulfur_dioxide" title="Sulfur dioxide">Sulfur dioxide (SO<sub>2</sub>)</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="Monoamine_releasing_agents" style="padding:3px"><table class="nowraplinks mw-collapsible mw-collapsed navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Monoamine_releasing_agents" title="Template:Monoamine releasing agents"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Monoamine_releasing_agents" title="Template talk:Monoamine releasing agents"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Monoamine_releasing_agents" title="Special:EditPage/Template:Monoamine releasing agents"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Monoamine_releasing_agents" style="font-size:114%;margin:0 4em"><a href="/wiki/Monoamine_releasing_agent" title="Monoamine releasing agent">Monoamine releasing agents</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Dopamine_releasing_agents" class="mw-redirect" title="Dopamine releasing agents"><abbr title="Dopamine releasing agents">DRAs</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Dopamine releasing agents</span></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><td colspan="2" class="navbox-list navbox-odd" style="width:100%;padding:0;text-align: left;"><div style="padding:0 0.25em"> <ul><li><i>Morpholines:</i> <a href="/wiki/Fenbutrazate" title="Fenbutrazate">Fenbutrazate</a></li> <li><a href="/wiki/Fenmetramide" title="Fenmetramide">Fenmetramide</a></li> <li><a href="/wiki/Morazone" title="Morazone">Morazone</a></li> <li><a href="/wiki/Morforex" title="Morforex">Morforex</a></li> <li><a href="/wiki/Phendimetrazine" title="Phendimetrazine">Phendimetrazine</a></li> <li><a href="/wiki/Phenmetrazine" title="Phenmetrazine">Phenmetrazine</a></li> <li><a href="/wiki/Pseudophenmetrazine" title="Pseudophenmetrazine">Pseudophenmetrazine</a></li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-even" style="width:100%;padding:0;text-align: left;"><div style="padding:0 0.25em"> <ul><li><i>Oxazolines:</i> <a href="/wiki/4-Methylaminorex" title="4-Methylaminorex">4-MAR</a></li> <li><a href="/wiki/Aminorex" title="Aminorex">Aminorex</a></li> <li><a href="/wiki/Clominorex" title="Clominorex">Clominorex</a></li> <li><a href="/wiki/Cyclazodone" title="Cyclazodone">Cyclazodone</a></li> <li><a href="/wiki/Fenozolone" title="Fenozolone">Fenozolone</a></li> <li><a href="/wiki/Fluminorex" title="Fluminorex">Fluminorex</a></li> <li><a href="/wiki/Pemoline" title="Pemoline">Pemoline</a></li> <li><a href="/wiki/Thozalinone" title="Thozalinone">Thozalinone</a></li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-odd" style="width:100%;padding:0;text-align: left;"><div style="padding:0 0.25em"> <ul><li><i>Phenethylamines:</i> <a href="/wiki/Phenylethanolamine" title="Phenylethanolamine">2-OH-PEA</a></li> <li><a href="/wiki/4-Chlorophenylisobutylamine" title="4-Chlorophenylisobutylamine">4-CAB</a></li> <li><a href="/wiki/4-Fluoroamphetamine" title="4-Fluoroamphetamine">4-FA</a></li> <li><a href="/wiki/4-Fluoromethamphetamine" title="4-Fluoromethamphetamine">4-FMA</a></li> <li><a href="/wiki/4-Methylamphetamine" title="4-Methylamphetamine">4-MA</a></li> <li><a href="/wiki/4-Methylmethamphetamine" class="mw-redirect" title="4-Methylmethamphetamine">4-MMA</a></li> <li><a href="/wiki/Alfetamine" title="Alfetamine">Alfetamine</a></li> <li><a href="/wiki/Amfecloral" title="Amfecloral">Amfecloral</a></li> <li><a href="/wiki/Amfepentorex" title="Amfepentorex">Amfepentorex</a></li> <li><a href="/wiki/Amfepramone" title="Amfepramone">Amfepramone</a></li> <li><a href="/wiki/Amphetamine" title="Amphetamine">Amphetamine</a> (<a href="/wiki/Dextroamphetamine" title="Dextroamphetamine">Dextroamphetamine</a></li> <li><a href="/wiki/Levoamphetamine" title="Levoamphetamine">Levoamphetamine</a>)</li> <li><a href="/wiki/Amphetaminil" class="mw-redirect" title="Amphetaminil">Amphetaminil</a></li> <li><a href="/wiki/%CE%92-Methylphenethylamine" title="Β-Methylphenethylamine">β-Me-PEA</a></li> <li><a href="/wiki/1,3-Benzodioxolylbutanamine" title="1,3-Benzodioxolylbutanamine">BDB</a></li> <li><a href="/wiki/BOH_(drug)" title="BOH (drug)">BOH</a></li> <li><a href="/wiki/Benzphetamine" title="Benzphetamine">Benzphetamine</a></li> <li><a href="/wiki/Buphedrone" title="Buphedrone">Buphedrone</a></li> <li><a href="/wiki/Butylone" title="Butylone">Butylone</a></li> <li><a href="/wiki/Cathine" title="Cathine">Cathine</a></li> <li><a href="/wiki/Cathinone" title="Cathinone">Cathinone</a></li> <li><a href="/wiki/Clobenzorex" title="Clobenzorex">Clobenzorex</a></li> <li><a href="/wiki/Clortermine" title="Clortermine">Clortermine</a></li> <li><a href="/wiki/D-Deprenyl" title="D-Deprenyl">D-Deprenyl</a></li> <li><a href="/wiki/Dimethoxyamphetamine" title="Dimethoxyamphetamine">DMA</a></li> <li><a href="/wiki/Dimethoxymethamphetamine" title="Dimethoxymethamphetamine">DMMA</a></li> <li><a href="/wiki/Dimethylamphetamine" title="Dimethylamphetamine">Dimethylamphetamine</a></li> <li><a href="/wiki/Ephedrine" title="Ephedrine">Ephedrine</a></li> <li><a href="/wiki/Ethcathinone" title="Ethcathinone">Ethcathinone</a></li> <li><a href="/wiki/1,3-Benzodioxolyl-N-ethylbutanamine" title="1,3-Benzodioxolyl-N-ethylbutanamine">EBDB</a></li> <li><a href="/wiki/Ethylone" title="Ethylone">Ethylone</a></li> <li><a href="/wiki/Etilamfetamine" title="Etilamfetamine">Etilamfetamine</a></li> <li><a href="/wiki/Famprofazone" title="Famprofazone">Famprofazone</a></li> <li><a href="/wiki/Fenethylline" title="Fenethylline">Fenethylline</a></li> <li><a href="/wiki/Fenproporex" title="Fenproporex">Fenproporex</a></li> <li><a href="/wiki/Flephedrone" title="Flephedrone">Flephedrone</a></li> <li><a href="/wiki/Fludorex" title="Fludorex">Fludorex</a></li> <li><a href="/wiki/Furfenorex" title="Furfenorex">Furfenorex</a></li> <li><a href="/wiki/Hordenine" title="Hordenine">Hordenine</a></li> <li><a href="/wiki/4-Hydroxyamphetamine" title="4-Hydroxyamphetamine">4-Hydroxyamphetamine</a></li> <li><a href="/wiki/Iofetamine_(123I)" title="Iofetamine (123I)">Iofetamine (123I)</a></li> <li><a href="/wiki/Lisdexamfetamine" title="Lisdexamfetamine">Lisdexamfetamine</a></li> <li><a href="/wiki/Lophophine" title="Lophophine">Lophophine</a></li> <li><a href="/wiki/Mefenorex" title="Mefenorex">Mefenorex</a></li> <li><a href="/wiki/Mephedrone" title="Mephedrone">Mephedrone</a></li> <li><a href="/wiki/Metamfepramone" title="Metamfepramone">Metamfepramone</a></li> <li><a href="/wiki/Methamphetamine" title="Methamphetamine">Methamphetamine</a> <ul><li><a href="/wiki/Dextromethamphetamine" class="mw-redirect" title="Dextromethamphetamine">Dextromethamphetamine</a></li> <li><a href="/wiki/Levomethamphetamine" class="mw-redirect" title="Levomethamphetamine">Levomethamphetamine</a></li></ul></li> <li><a href="/wiki/Methcathinone" title="Methcathinone">Methcathinone</a></li> <li><a href="/wiki/Methedrone" title="Methedrone">Methedrone</a></li> <li><a href="/wiki/MMDA_(drug)" title="MMDA (drug)">MMDA</a></li> <li><a href="/wiki/MMDMA" title="MMDMA">MMDMA</a></li> <li><a href="/wiki/1,3-Benzodioxolyl-N-methylbutanamine" class="mw-redirect" title="1,3-Benzodioxolyl-N-methylbutanamine">MBDB</a></li> <li><a href="/wiki/3,4-Methylenedioxyamphetamine" title="3,4-Methylenedioxyamphetamine">MDA (tenamfetamine)</a></li> <li><a href="/wiki/Methylenedioxyethylamphetamine" class="mw-redirect" title="Methylenedioxyethylamphetamine">MDEA</a></li> <li><a href="/wiki/MDMA" title="MDMA">MDMA (midomafetamine)</a></li> <li><a href="/wiki/Methylenedioxymethylphenethylamine" class="mw-redirect" title="Methylenedioxymethylphenethylamine">MDMPEA</a></li> <li><a href="/wiki/Methylenedioxyhydroxyamphetamine" class="mw-redirect" title="Methylenedioxyhydroxyamphetamine">MDOH</a></li> <li><a href="/wiki/Methylenedioxyphenethylamine" class="mw-redirect" title="Methylenedioxyphenethylamine">MDPEA</a></li> <li><a href="/wiki/Methylone" title="Methylone">Methylone</a></li> <li><a href="/wiki/Morforex" title="Morforex">Morforex</a></li> <li><a href="/wiki/Ortetamine" title="Ortetamine">Ortetamine</a></li> <li><a href="/wiki/Para-Bromoamphetamine" title="Para-Bromoamphetamine"><i>p</i>BA</a></li> <li><a href="/wiki/Para-Chloroamphetamine" title="Para-Chloroamphetamine"><i>p</i>CA</a></li> <li><a href="/wiki/Para-Iodoamphetamine" title="Para-Iodoamphetamine"><i>p</i>IA</a></li> <li><a href="/wiki/Pholedrine" title="Pholedrine">Pholedrine</a></li> <li><a href="/wiki/Phenethylamine" title="Phenethylamine">Phenethylamine</a></li> <li><a href="/wiki/Pholedrine" title="Pholedrine">Pholedrine</a></li> <li><a href="/wiki/Phenpromethamine" title="Phenpromethamine">Phenpromethamine</a></li> <li><a href="/wiki/Prenylamine" title="Prenylamine">Prenylamine</a></li> <li><a href="/wiki/Propylamphetamine" title="Propylamphetamine">Propylamphetamine</a></li> <li><a href="/wiki/Pseudoephedrine" title="Pseudoephedrine">Pseudoephedrine</a></li> <li><a href="/wiki/Tiflorex" title="Tiflorex">Tiflorex</a></li> <li><a class="mw-selflink selflink">Tyramine</a></li> <li><a href="/wiki/Xylopropamine" title="Xylopropamine">Xylopropamine</a></li> <li><a href="/wiki/Zylofuramine" title="Zylofuramine">Zylofuramine</a></li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-even" style="width:100%;padding:0;text-align: left;"><div style="padding:0 0.25em"> <ul><li><i>Piperazines:</i> <a href="/wiki/2C-B-BZP" title="2C-B-BZP">2C-B-BZP</a></li> <li><a href="/wiki/Benzylpiperazine" title="Benzylpiperazine">BZP</a></li> <li><a href="/wiki/Methylbenzylpiperazine" title="Methylbenzylpiperazine">MBZP</a></li> <li><a href="/wiki/Methylenedioxybenzylpiperazine" title="Methylenedioxybenzylpiperazine">MDBZP</a></li> <li><a href="/wiki/Para-Methoxyphenylpiperazine" title="Para-Methoxyphenylpiperazine">MeOPP</a></li> <li><a href="/wiki/Ortho-Methylphenylpiperazine" title="Ortho-Methylphenylpiperazine">oMPP</a></li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-odd" style="width:100%;padding:0;text-align: left;"><div style="padding:0 0.25em"> <ul><li><i>Others:</i> <a href="/wiki/2-Amino-1,2-dihydronaphthalene" title="2-Amino-1,2-dihydronaphthalene">2-ADN</a></li> <li><a href="/wiki/2-Aminoindane" title="2-Aminoindane">2-AI</a></li> <li><a href="/wiki/2-Aminotetralin" title="2-Aminotetralin">2-AT</a></li> <li><a href="/wiki/4-Benzylpiperidine" title="4-Benzylpiperidine">4-BP</a></li> <li><a href="/wiki/5-APDI" title="5-APDI">5-APDI</a></li> <li><a href="/wiki/5-IAI" title="5-IAI">5-IAI</a></li> <li><a href="/wiki/Amineptine" title="Amineptine">Amineptine</a></li> <li><a href="/wiki/Clofenciclan" title="Clofenciclan">Clofenciclan</a></li> <li><a href="/wiki/Cyclopentamine" title="Cyclopentamine">Cyclopentamine</a></li> <li><a href="/wiki/Cypenamine" title="Cypenamine">Cypenamine</a></li> <li><a href="/wiki/Cyprodenate" title="Cyprodenate">Cyprodenate</a></li> <li><a href="/wiki/Feprosidnine" title="Feprosidnine">Feprosidnine</a></li> <li><a href="/wiki/Gilutensin" class="mw-redirect" title="Gilutensin">Gilutensin</a></li> <li><a href="/wiki/Heptaminol" title="Heptaminol">Heptaminol</a></li> <li><a href="/wiki/Hexacyclonate" title="Hexacyclonate">Hexacyclonate</a></li> <li><a href="/wiki/Indanorex" title="Indanorex">Indanorex</a></li> <li><a href="/wiki/Isometheptene" title="Isometheptene">Isometheptene</a></li> <li><a href="/wiki/Methylhexanamine" title="Methylhexanamine">Methylhexanamine</a></li> <li><a href="/wiki/Naphthylaminopropane" title="Naphthylaminopropane">Naphthylaminopropane</a></li> <li><a href="/wiki/Octodrine" title="Octodrine">Octodrine</a></li> <li><a href="/wiki/Phthalimidopropiophenone" title="Phthalimidopropiophenone">Phthalimidopropiophenone</a></li> <li><a href="/wiki/Phenylbiguanide" title="Phenylbiguanide">Phenylbiguanide</a></li> <li><a href="/wiki/Propylhexedrine" title="Propylhexedrine">Propylhexedrine</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Norepinephrine_releasing_agents" class="mw-redirect" title="Norepinephrine releasing agents"><abbr title="Norepinephrine releasing agents">NRAs</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Norepinephrine releasing agents</span></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><td colspan="2" class="navbox-list navbox-even" style="width:100%;padding:0;text-align: left;"><div style="padding:0 0.25em"> <ul><li><i>Morpholines:</i> <a href="/wiki/Fenbutrazate" title="Fenbutrazate">Fenbutrazate</a></li> <li><a href="/wiki/Fenmetramide" title="Fenmetramide">Fenmetramide</a></li> <li><a href="/wiki/Morazone" title="Morazone">Morazone</a></li> <li><a href="/wiki/Morforex" title="Morforex">Morforex</a></li> <li><a href="/wiki/Phendimetrazine" title="Phendimetrazine">Phendimetrazine</a></li> <li><a href="/wiki/Phenmetrazine" title="Phenmetrazine">Phenmetrazine</a></li> <li><a href="/wiki/Pseudophenmetrazine" title="Pseudophenmetrazine">Pseudophenmetrazine</a></li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-odd" style="width:100%;padding:0;text-align: left;"><div style="padding:0 0.25em"> <ul><li><i>Oxazolines:</i> <a href="/wiki/4-Methylaminorex" title="4-Methylaminorex">4-MAR</a></li> <li><a href="/wiki/Aminorex" title="Aminorex">Aminorex</a></li> <li><a href="/wiki/Clominorex" title="Clominorex">Clominorex</a></li> <li><a href="/wiki/Cyclazodone" title="Cyclazodone">Cyclazodone</a></li> <li><a href="/wiki/Fenozolone" title="Fenozolone">Fenozolone</a></li> <li><a href="/wiki/Fluminorex" title="Fluminorex">Fluminorex</a></li> <li><a href="/wiki/Pemoline" title="Pemoline">Pemoline</a></li> <li><a href="/wiki/Thozalinone" title="Thozalinone">Thozalinone</a></li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-even" style="width:100%;padding:0;text-align: left;"><div style="padding:0 0.25em"> <ul><li><i>Phenethylamines:</i> <a href="/wiki/Phenylethanolamine" title="Phenylethanolamine">2-OH-PEA</a></li> <li><a href="/wiki/4-Chlorophenylisobutylamine" title="4-Chlorophenylisobutylamine">4-CAB</a></li> <li><a href="/wiki/4-Fluoroamphetamine" title="4-Fluoroamphetamine">4-FA</a></li> <li><a href="/wiki/4-Fluoromethamphetamine" title="4-Fluoromethamphetamine">4-FMA</a></li> <li><a href="/wiki/4-Methylamphetamine" title="4-Methylamphetamine">4-MA</a></li> <li><a href="/wiki/4-Methylmethamphetamine" class="mw-redirect" title="4-Methylmethamphetamine">4-MMA</a></li> <li><a href="/wiki/Alfetamine" title="Alfetamine">Alfetamine</a></li> <li><a href="/wiki/Amfecloral" title="Amfecloral">Amfecloral</a></li> <li><a href="/wiki/Amfepentorex" title="Amfepentorex">Amfepentorex</a></li> <li><a href="/wiki/Amfepramone" title="Amfepramone">Amfepramone</a></li> <li><a href="/wiki/Amphetamine" title="Amphetamine">Amphetamine</a> <ul><li><a href="/wiki/Dextroamphetamine" title="Dextroamphetamine">Dextroamphetamine</a></li> <li><a href="/wiki/Levoamphetamine" title="Levoamphetamine">Levoamphetamine</a></li></ul></li> <li><a href="/wiki/Amphetaminil" class="mw-redirect" title="Amphetaminil">Amphetaminil</a></li> <li><a href="/wiki/%CE%92-Methylphenethylamine" title="Β-Methylphenethylamine">β-Me-PEA</a></li> <li><a href="/wiki/1,3-Benzodioxolylbutanamine" title="1,3-Benzodioxolylbutanamine">BDB</a></li> <li><a href="/wiki/Benzphetamine" title="Benzphetamine">Benzphetamine</a></li> <li><a href="/wiki/BOH_(drug)" title="BOH (drug)">BOH</a></li> <li><a href="/wiki/Buphedrone" title="Buphedrone">Buphedrone</a></li> <li><a href="/wiki/Butylone" title="Butylone">Butylone</a></li> <li><a href="/wiki/Cathine" title="Cathine">Cathine</a></li> <li><a href="/wiki/Cathinone" title="Cathinone">Cathinone</a></li> <li><a href="/wiki/Clobenzorex" title="Clobenzorex">Clobenzorex</a></li> <li><a href="/wiki/Clortermine" title="Clortermine">Clortermine</a></li> <li><a href="/wiki/Dimethylamphetamine" title="Dimethylamphetamine">Dimethylamphetamine</a></li> <li><a href="/wiki/Dimethoxyamphetamine" title="Dimethoxyamphetamine">DMA</a></li> <li><a href="/wiki/Dimethoxymethamphetamine" title="Dimethoxymethamphetamine">DMMA</a></li> <li><a href="/wiki/1,3-Benzodioxolyl-N-ethylbutanamine" title="1,3-Benzodioxolyl-N-ethylbutanamine">EBDB</a></li> <li><a href="/wiki/Ephedrine" title="Ephedrine">Ephedrine</a></li> <li><a href="/wiki/Ethcathinone" title="Ethcathinone">Ethcathinone</a></li> <li><a href="/wiki/Ethylone" title="Ethylone">Ethylone</a></li> <li><a href="/wiki/Etilamfetamine" title="Etilamfetamine">Etilamfetamine</a></li> <li><a href="/wiki/Famprofazone" title="Famprofazone">Famprofazone</a></li> <li><a href="/wiki/Fenethylline" title="Fenethylline">Fenethylline</a></li> <li><a href="/wiki/Fenproporex" title="Fenproporex">Fenproporex</a></li> <li><a href="/wiki/Flephedrone" title="Flephedrone">Flephedrone</a></li> <li><a href="/wiki/Fludorex" title="Fludorex">Fludorex</a></li> <li><a href="/wiki/Furfenorex" title="Furfenorex">Furfenorex</a></li> <li><a href="/wiki/Hordenine" title="Hordenine">Hordenine</a></li> <li><a href="/wiki/4-Hydroxyamphetamine" title="4-Hydroxyamphetamine">4-Hydroxyamphetamine</a></li> <li><a href="/wiki/5-APDI" title="5-APDI">5-APDI</a> (IAP)</li> <li><a href="/wiki/Iofetamine_(123I)" title="Iofetamine (123I)">Iofetamine (123I)</a></li> <li><a href="/wiki/Lisdexamfetamine" title="Lisdexamfetamine">Lisdexamfetamine</a></li> <li><a href="/wiki/Lophophine" title="Lophophine">Lophophine</a></li> <li><a href="/wiki/1,3-Benzodioxolyl-N-methylbutanamine" class="mw-redirect" title="1,3-Benzodioxolyl-N-methylbutanamine">MBDB</a></li> <li><a href="/wiki/3,4-Methylenedioxyamphetamine" title="3,4-Methylenedioxyamphetamine">MDA (tenamfetamine)</a></li> <li><a href="/wiki/Methylenedioxyethylamphetamine" class="mw-redirect" title="Methylenedioxyethylamphetamine">MDEA</a></li> <li><a href="/wiki/MDMA" title="MDMA">MDMA (midomafetamine)</a></li> <li><a href="/wiki/Metamfepramone" title="Metamfepramone">Metamfepramone</a></li> <li><a href="/wiki/Methylenedioxymethylphenethylamine" class="mw-redirect" title="Methylenedioxymethylphenethylamine">MDMPEA</a></li> <li><a href="/wiki/Methylenedioxyhydroxyamphetamine" class="mw-redirect" title="Methylenedioxyhydroxyamphetamine">MDOH</a></li> <li><a href="/wiki/Methylenedioxyphenethylamine" class="mw-redirect" title="Methylenedioxyphenethylamine">MDPEA</a></li> <li><a href="/wiki/Mefenorex" title="Mefenorex">Mefenorex</a></li> <li><a href="/wiki/Mephedrone" title="Mephedrone">Mephedrone</a></li> <li><a href="/wiki/Mephentermine" title="Mephentermine">Mephentermine</a></li> <li><a href="/wiki/Methamphetamine" title="Methamphetamine">Methamphetamine</a> <ul><li><a href="/wiki/Dextromethamphetamine" class="mw-redirect" title="Dextromethamphetamine">Dextromethamphetamine</a></li> <li><a href="/wiki/Levomethamphetamine" class="mw-redirect" title="Levomethamphetamine">Levomethamphetamine</a></li></ul></li> <li><a href="/wiki/Methcathinone" title="Methcathinone">Methcathinone</a></li> <li><a href="/wiki/Methedrone" title="Methedrone">Methedrone</a></li> <li><a href="/wiki/Methylone" title="Methylone">Methylone</a></li> <li><a href="/wiki/Morforex" title="Morforex">Morforex</a></li> <li><a href="/wiki/Naphthylaminopropane" title="Naphthylaminopropane">Naphthylaminopropane</a></li> <li><a href="/wiki/Ortetamine" title="Ortetamine">Ortetamine</a></li> <li><a href="/wiki/Para-Bromoamphetamine" title="Para-Bromoamphetamine"><i>p</i>BA</a></li> <li><a href="/wiki/Para-Chloroamphetamine" title="Para-Chloroamphetamine"><i>p</i>CA</a></li> <li><a href="/wiki/Pentorex" title="Pentorex">Pentorex</a></li> <li><a href="/wiki/Phenethylamine" title="Phenethylamine">Phenethylamine</a></li> <li><a href="/wiki/Pholedrine" title="Pholedrine">Pholedrine</a></li> <li><a href="/wiki/Phenpromethamine" title="Phenpromethamine">Phenpromethamine</a></li> <li><a href="/wiki/Phentermine" title="Phentermine">Phentermine</a></li> <li><a href="/wiki/Phenylpropanolamine" title="Phenylpropanolamine">Phenylpropanolamine</a></li> <li><a href="/wiki/Para-Iodoamphetamine" title="Para-Iodoamphetamine"><i>p</i>IA</a></li> <li><a href="/wiki/Prenylamine" title="Prenylamine">Prenylamine</a></li> <li><a href="/wiki/Propylamphetamine" title="Propylamphetamine">Propylamphetamine</a></li> <li><a href="/wiki/Pseudoephedrine" title="Pseudoephedrine">Pseudoephedrine</a></li> <li><a href="/wiki/Selegiline" title="Selegiline">Selegiline</a> (also <a href="/wiki/D-Deprenyl" title="D-Deprenyl"><span style="font-size:85%;">D</span>-Deprenyl</a>)</li> <li><a href="/wiki/Tiflorex" title="Tiflorex">Tiflorex</a></li> <li><a class="mw-selflink selflink">Tyramine</a></li> <li><a href="/wiki/Xylopropamine" title="Xylopropamine">Xylopropamine</a></li> <li><a href="/wiki/Zylofuramine" title="Zylofuramine">Zylofuramine</a></li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-odd" style="width:100%;padding:0;text-align: left;"><div style="padding:0 0.25em"> <ul><li><i>Piperazines:</i> <a href="/wiki/2C-B-BZP" title="2C-B-BZP">2C-B-BZP</a></li> <li><a href="/wiki/Benzylpiperazine" title="Benzylpiperazine">BZP</a></li> <li><a href="/wiki/Methylbenzylpiperazine" title="Methylbenzylpiperazine">MBZP</a></li> <li><a href="/wiki/Meta-Chlorophenylpiperazine" title="Meta-Chlorophenylpiperazine">mCPP</a></li> <li><a href="/wiki/Methylenedioxybenzylpiperazine" title="Methylenedioxybenzylpiperazine">MDBZP</a></li> <li><a href="/wiki/Para-Methoxyphenylpiperazine" title="Para-Methoxyphenylpiperazine">MeOPP</a></li> <li><a href="/wiki/Ortho-Methylphenylpiperazine" title="Ortho-Methylphenylpiperazine">oMPP</a></li> <li><a href="/wiki/Para-Fluorophenylpiperazine" title="Para-Fluorophenylpiperazine">pFPP</a></li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-even" style="width:100%;padding:0;text-align: left;"><div style="padding:0 0.25em"> <ul><li><i>Others:</i> <a href="/wiki/2-Amino-1,2-dihydronaphthalene" title="2-Amino-1,2-dihydronaphthalene">2-ADN</a></li> <li><a href="/wiki/2-Aminoindane" title="2-Aminoindane">2-AI</a></li> <li><a href="/wiki/2-Aminotetralin" title="2-Aminotetralin">2-AT</a></li> <li><a href="/wiki/2-Benzylpiperidine" title="2-Benzylpiperidine">2-BP</a></li> <li><a href="/wiki/4-Benzylpiperidine" title="4-Benzylpiperidine">4-BP</a></li> <li><a href="/wiki/5-IAI" title="5-IAI">5-IAI</a></li> <li><a href="/wiki/Clofenciclan" title="Clofenciclan">Clofenciclan</a></li> <li><a href="/wiki/Cyclopentamine" title="Cyclopentamine">Cyclopentamine</a></li> <li><a href="/wiki/Cypenamine" title="Cypenamine">Cypenamine</a></li> <li><a href="/wiki/Cyprodenate" title="Cyprodenate">Cyprodenate</a></li> <li><a href="/wiki/Feprosidnine" title="Feprosidnine">Feprosidnine</a></li> <li><a href="/wiki/Gilutensin" class="mw-redirect" title="Gilutensin">Gilutensin</a></li> <li><a href="/wiki/Heptaminol" title="Heptaminol">Heptaminol</a></li> <li><a href="/wiki/Hexacyclonate" title="Hexacyclonate">Hexacyclonate</a></li> <li><a href="/wiki/Indanorex" title="Indanorex">Indanorex</a></li> <li><a href="/wiki/Isometheptene" title="Isometheptene">Isometheptene</a></li> <li><a href="/wiki/Methylhexanamine" title="Methylhexanamine">Methylhexanamine</a></li> <li><a href="/wiki/Octodrine" title="Octodrine">Octodrine</a></li> <li><a href="/wiki/Phthalimidopropiophenone" title="Phthalimidopropiophenone">Phthalimidopropiophenone</a></li> <li><a href="/wiki/Propylhexedrine" title="Propylhexedrine">Propylhexedrine</a></li> <li><a href="/wiki/Tuaminoheptane" title="Tuaminoheptane">Tuaminoheptane</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Serotonin_releasing_agents" class="mw-redirect" title="Serotonin releasing agents"><abbr title="Serotonin releasing agents">SRAs</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Serotonin releasing agents</span></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><td colspan="2" class="navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i>Aminoindanes:</i> <a href="/wiki/5-IAI" title="5-IAI">5-IAI</a></li> <li><a href="/wiki/1-Aminomethyl-5-methoxyindane" title="1-Aminomethyl-5-methoxyindane">AMMI</a></li> <li><a href="/wiki/Ethyltrifluoromethylaminoindane" title="Ethyltrifluoromethylaminoindane">ETAI</a></li> <li><a href="/wiki/MDAI" title="MDAI">MDAI</a></li> <li><a href="/wiki/MDMAI" title="MDMAI">MDMAI</a></li> <li><a href="/wiki/MMAI" title="MMAI">MMAI</a></li> <li><a href="/wiki/Trifluoromethylaminoindane" title="Trifluoromethylaminoindane">TAI</a></li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i>Aminotetralins:</i> <a href="/wiki/6-CAT" title="6-CAT">6-CAT</a></li> <li><a href="/wiki/8-OH-DPAT" title="8-OH-DPAT">8-OH-DPAT</a></li> <li><a href="/wiki/MDAT" title="MDAT">MDAT</a></li> <li><a href="/wiki/MDMAT" title="MDMAT">MDMAT</a></li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i>Oxazolines:</i> <a href="/wiki/4-Methylaminorex" title="4-Methylaminorex">4-Methylaminorex</a></li> <li><a href="/wiki/Aminorex" title="Aminorex">Aminorex</a></li> <li><a href="/wiki/Clominorex" title="Clominorex">Clominorex</a></li> <li><a href="/wiki/Fluminorex" title="Fluminorex">Fluminorex</a></li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i>Phenethylamines:</i> <a href="/wiki/2-Methyl-MDA" title="2-Methyl-MDA">2-Methyl-MDA</a></li> <li><a href="/wiki/4-Chlorophenylisobutylamine" title="4-Chlorophenylisobutylamine">4-CAB</a></li> <li><a href="/wiki/4-Fluoroamphetamine" title="4-Fluoroamphetamine">4-FA</a></li> <li><a href="/wiki/4-Fluoromethamphetamine" title="4-Fluoromethamphetamine">4-FMA</a></li> <li><a href="/wiki/4-Hydroxyamphetamine" title="4-Hydroxyamphetamine">4-HA</a></li> <li><a href="/wiki/4-Methylthioamphetamine" title="4-Methylthioamphetamine">4-MTA</a></li> <li><a href="/wiki/5-APDB" title="5-APDB">5-APDB</a></li> <li><a href="/wiki/5-Methyl-MDA" title="5-Methyl-MDA">5-Methyl-MDA</a></li> <li><a href="/wiki/6-APDB" title="6-APDB">6-APDB</a></li> <li><a href="/wiki/6-Methyl-MDA" title="6-Methyl-MDA">6-Methyl-MDA</a></li> <li><a href="/wiki/3-Methoxy-4-methyl-%CE%B1-ethylphenethylamine" class="mw-redirect" title="3-Methoxy-4-methyl-α-ethylphenethylamine">AEMMA</a></li> <li><a href="/wiki/Amiflamine" title="Amiflamine">Amiflamine</a></li> <li><a href="/wiki/Benzodioxolylbutanamine" class="mw-redirect" title="Benzodioxolylbutanamine">BDB</a></li> <li><a href="/wiki/BOH_(drug)" title="BOH (drug)">BOH</a></li> <li><a href="/wiki/4-Bromomethcathinone" title="4-Bromomethcathinone">Brephedrone</a></li> <li><a href="/wiki/Butylone" title="Butylone">Butylone</a></li> <li><a href="/wiki/Chlorphentermine" title="Chlorphentermine">Chlorphentermine</a></li> <li><a href="/wiki/Cloforex" title="Cloforex">Cloforex</a></li> <li><a href="/wiki/Amfepramone" title="Amfepramone">Amfepramone</a></li> <li><a href="/wiki/Metamfepramone" title="Metamfepramone">Metamfepramone</a></li> <li><a href="/wiki/3,4-Dichloroamphetamine" title="3,4-Dichloroamphetamine">DCA</a></li> <li><a href="/wiki/Dexfenfluramine" title="Dexfenfluramine">Dexfenfluramine</a></li> <li><a href="/wiki/DFMDA" title="DFMDA">DFMDA</a></li> <li><a href="/wiki/Dimethoxyamphetamine" title="Dimethoxyamphetamine">DMA</a></li> <li><a href="/wiki/Dimethoxymethamphetamine" title="Dimethoxymethamphetamine">DMMA</a></li> <li><a href="/wiki/Ethylbenzodioxolylbutanamine" class="mw-redirect" title="Ethylbenzodioxolylbutanamine">EBDB</a></li> <li><a href="/wiki/EDMA" title="EDMA">EDMA</a></li> <li><a href="/wiki/Ethylone" title="Ethylone">Ethylone</a></li> <li><a href="/wiki/Etolorex" title="Etolorex">Etolorex</a></li> <li><a href="/wiki/Fenfluramine" title="Fenfluramine">Fenfluramine</a></li> <li><a href="/wiki/Flephedrone" title="Flephedrone">Flephedrone</a></li> <li><a href="/wiki/Flucetorex" title="Flucetorex">Flucetorex</a></li> <li><a href="/wiki/Indanylaminopropane" class="mw-redirect" title="Indanylaminopropane">IAP</a></li> <li><a href="/wiki/Iofetamine" class="mw-redirect" title="Iofetamine">Iofetamine</a></li> <li><a href="/wiki/Levofenfluramine" title="Levofenfluramine">Levofenfluramine</a></li> <li><a href="/wiki/Lophophine" title="Lophophine">Lophophine</a></li> <li><a href="/wiki/Methylbenzodioxolylbutanamine" class="mw-redirect" title="Methylbenzodioxolylbutanamine">MBDB</a></li> <li><a href="/wiki/3,4-Methylenedioxyamphetamine" title="3,4-Methylenedioxyamphetamine">MDA (tenamfetamine)</a></li> <li><a href="/wiki/Methylenedioxyethylamphetamine" class="mw-redirect" title="Methylenedioxyethylamphetamine">MDEA</a></li> <li><a href="/wiki/Methylenedioxyhydroxymethamphetamine" class="mw-redirect" title="Methylenedioxyhydroxymethamphetamine">MDHMA</a></li> <li><a href="/wiki/MDMA" title="MDMA">MDMA (midomafetamine)</a></li> <li><a href="/wiki/Methylenedioxymethylphenethylamine" class="mw-redirect" title="Methylenedioxymethylphenethylamine">MDMPEA</a></li> <li><a href="/wiki/Methylenedioxyhydroxyamphetamine" class="mw-redirect" title="Methylenedioxyhydroxyamphetamine">MDOH</a></li> <li><a href="/wiki/Methylenedioxyphenethylamine" class="mw-redirect" title="Methylenedioxyphenethylamine">MDPEA</a></li> <li><a href="/wiki/Mephedrone" title="Mephedrone">Mephedrone</a></li> <li><a href="/wiki/Methedrone" title="Methedrone">Methedrone</a></li> <li><a href="/wiki/Methylone" title="Methylone">Methylone</a></li> <li><a href="/wiki/3-Methoxy-4-methylamphetamine" title="3-Methoxy-4-methylamphetamine">MMA</a></li> <li><a href="/wiki/MMDA_(drug)" title="MMDA (drug)">MMDA</a></li> <li><a href="/wiki/MMDMA" title="MMDMA">MMDMA</a></li> <li><a href="/wiki/3-Methoxy-4-methylmethamphetamine" class="mw-redirect" title="3-Methoxy-4-methylmethamphetamine">MMMA</a></li> <li><a href="/wiki/Naphthylaminopropane" title="Naphthylaminopropane">NAP</a></li> <li><a href="/wiki/Norfenfluramine" title="Norfenfluramine">Norfenfluramine</a></li> <li><a href="/wiki/4-Trifluoromethylamphetamine" class="mw-redirect" title="4-Trifluoromethylamphetamine">4-TFMA</a></li> <li><a href="/wiki/Para-Bromoamphetamine" title="Para-Bromoamphetamine">pBA</a></li> <li><a href="/wiki/Para-Chloroamphetamine" title="Para-Chloroamphetamine">pCA</a></li> <li><a href="/wiki/Para-Iodoamphetamine" title="Para-Iodoamphetamine">pIA</a></li> <li><a href="/wiki/Para-Methoxyamphetamine" title="Para-Methoxyamphetamine">PMA</a></li> <li><a href="/wiki/Para-Methoxyethylamphetamine" class="mw-redirect" title="Para-Methoxyethylamphetamine">PMEA</a></li> <li><a href="/wiki/Para-Methoxymethamphetamine" class="mw-redirect" title="Para-Methoxymethamphetamine">PMMA</a></li> <li><a href="/wiki/Tetralinylaminopropane" class="mw-redirect" title="Tetralinylaminopropane">TAP</a></li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i>Piperazines:</i> <a href="/wiki/2C-B-BZP" title="2C-B-BZP">2C-B-BZP</a></li> <li><a href="/w/index.php?title=3-Methoxyphenylpiperazine&action=edit&redlink=1" class="new" title="3-Methoxyphenylpiperazine (page does not exist)">3-MeOPP</a></li> <li><a href="/wiki/Benzylpiperazine" title="Benzylpiperazine">BZP</a></li> <li><a href="/wiki/3,4-Dichlorophenylpiperazine" class="mw-redirect" title="3,4-Dichlorophenylpiperazine">DCPP</a></li> <li><a href="/wiki/Methylbenzylpiperazine" title="Methylbenzylpiperazine">MBZP</a></li> <li><a href="/wiki/Meta-Chlorophenylpiperazine" title="Meta-Chlorophenylpiperazine">mCPP</a></li> <li><a href="/wiki/Methylenedioxybenzylpiperazine" title="Methylenedioxybenzylpiperazine">MDBZP</a></li> <li><a href="/wiki/Para-Methoxyphenylpiperazine" title="Para-Methoxyphenylpiperazine">MeOPP</a></li> <li><a href="/wiki/Mepiprazole" title="Mepiprazole">Mepiprazole</a></li> <li><a href="/wiki/Ortho-Methylphenylpiperazine" title="Ortho-Methylphenylpiperazine">oMPP</a></li> <li><a href="/wiki/Para-Chlorophenylpiperazine" title="Para-Chlorophenylpiperazine">pCPP</a></li> <li><a href="/wiki/Para-Fluorophenylpiperazine" title="Para-Fluorophenylpiperazine">pFPP</a></li> <li><a href="/wiki/1-(4-Trifluoromethyl-phenyl)-piperazine" class="mw-redirect" title="1-(4-Trifluoromethyl-phenyl)-piperazine">pTFMPP</a></li> <li><a href="/wiki/Trifluoromethylphenylpiperazine" title="Trifluoromethylphenylpiperazine">TFMPP</a></li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i>Tryptamines:</i> <a href="/wiki/4-Methyl-AET" class="mw-redirect" title="4-Methyl-AET">4-Methyl-αET</a></li> <li><a href="/wiki/4-Methyl-AMT" class="mw-redirect" title="4-Methyl-AMT">4-Methyl-αMT</a></li> <li><a href="/wiki/5-Carboxamidotryptamine" title="5-Carboxamidotryptamine">5-CT</a></li> <li><a href="/wiki/5-MeO-AET" title="5-MeO-AET">5-MeO-αET</a></li> <li><a href="/wiki/5-MeO-AMT" class="mw-redirect" title="5-MeO-AMT">5-MeO-αMT</a></li> <li><a href="/wiki/5-Methoxytryptamine" title="5-Methoxytryptamine">5-MT</a></li> <li><a href="/wiki/Alpha-Ethyltryptamine" class="mw-redirect" title="Alpha-Ethyltryptamine">αET</a></li> <li><a href="/wiki/Alpha-Methyltryptamine" class="mw-redirect" title="Alpha-Methyltryptamine">αMT</a></li> <li><a href="/wiki/Dimethyltryptamine" class="mw-redirect" title="Dimethyltryptamine">DMT</a></li> <li><a href="/wiki/Tryptamine" title="Tryptamine">Tryptamine</a></li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i>Others:</i> <a href="/wiki/Indeloxazine" title="Indeloxazine">Indeloxazine</a></li> <li><a href="/wiki/Viqualine" title="Viqualine">Viqualine</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;">Others</th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i>DAT modulators:</i> <i>Agonist-like:</i> <a href="/wiki/SoRI-9804" title="SoRI-9804">SoRI-9804</a></li> <li><a href="/w/index.php?title=SoRI-20040&action=edit&redlink=1" class="new" title="SoRI-20040 (page does not exist)">SoRI-20040</a>; <i>Antagonist-like:</i> <a href="/wiki/SoRI-20041" title="SoRI-20041">SoRI-20041</a></li></ul> <ul><li><i>Adrenergic release blockers:</i> <a href="/wiki/Bethanidine" title="Bethanidine">Bethanidine</a></li> <li><a href="/wiki/Bretylium" title="Bretylium">Bretylium</a></li> <li><a href="/wiki/Guanadrel" title="Guanadrel">Guanadrel</a></li> <li><a href="/wiki/Guanazodine" title="Guanazodine">Guanazodine</a></li> <li><a href="/wiki/Guanethidine" title="Guanethidine">Guanethidine</a></li> <li><a href="/wiki/Guanoxan" title="Guanoxan">Guanoxan</a></li></ul> </div></td></tr><tr><td class="navbox-abovebelow" colspan="2"><div><small><i><b>See also:</b> <a href="/wiki/Template:Receptor_modulators" title="Template:Receptor modulators">Receptor/signaling modulators</a> • <a href="/wiki/Template:Monoamine_reuptake_inhibitors" title="Template:Monoamine reuptake inhibitors">Monoamine reuptake inhibitors</a> • <a href="/wiki/Template:Adrenergics" class="mw-redirect" title="Template:Adrenergics">Adrenergics</a> • <a href="/wiki/Template:Dopaminergics" class="mw-redirect" title="Template:Dopaminergics">Dopaminergics</a> • <a href="/wiki/Template:Serotonergics" class="mw-redirect" title="Template:Serotonergics">Serotonergics</a> • <a href="/wiki/Template:Monoamine_metabolism_modulators" title="Template:Monoamine metabolism modulators">Monoamine metabolism modulators</a> • <a href="/wiki/Template:Monoamine_neurotoxins" title="Template:Monoamine neurotoxins">Monoamine neurotoxins</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="Monoaminergic_activity_enhancers" style="padding:3px"><table class="nowraplinks mw-collapsible mw-collapsed navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Monoaminergic_activity_enhancers" title="Template:Monoaminergic activity enhancers"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Monoaminergic_activity_enhancers" title="Template talk:Monoaminergic activity enhancers"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Monoaminergic_activity_enhancers" title="Special:EditPage/Template:Monoaminergic activity enhancers"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Monoaminergic_activity_enhancers" style="font-size:114%;margin:0 4em"><a href="/wiki/Monoaminergic_activity_enhancer" title="Monoaminergic activity enhancer">Monoaminergic activity enhancers</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Endogenous" class="mw-redirect" title="Endogenous">Endogenous</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Phenylethylamine" class="mw-redirect" title="Phenylethylamine">Phenylethylamine</a> (PEA)</li> <li><a href="/wiki/Tryptamine" title="Tryptamine">Tryptamine</a></li> <li><a class="mw-selflink selflink">Tyramine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Synthetic_compound" class="mw-redirect" title="Synthetic compound">Synthetic</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/4-Fluoroselegiline" title="4-Fluoroselegiline">4-Fluorodeprenyl</a></li> <li><a href="/wiki/Amphetamine" title="Amphetamine">Amphetamine</a> <ul><li><a href="/wiki/Dextroamphetamine" title="Dextroamphetamine">Dextroamphetamine</a></li> <li><a href="/wiki/Levoamphetamine" title="Levoamphetamine">Levoamphetamine</a></li></ul></li> <li><a href="/wiki/Benzofuranylpropylaminopentane" title="Benzofuranylpropylaminopentane">Benzofuranylpropylaminopentane</a> (BPAP)</li> <li><a href="/wiki/Deprenyl" title="Deprenyl">Deprenyl</a> <ul><li><a href="/wiki/D-Deprenyl" title="D-Deprenyl"><small>D</small>-Deprenyl</a></li> <li><a href="/wiki/Selegiline" title="Selegiline">Selegiline</a> (<small>L</small>-deprenyl)</li></ul></li> <li><a href="/wiki/Desmethylselegiline" title="Desmethylselegiline">Desmethylselegiline</a> (DMS)</li> <li><a href="/wiki/Indolylpropylaminopentane" title="Indolylpropylaminopentane">Indolylpropylaminopentane</a> (IPAP)</li> <li><a href="/wiki/Methamphetamine" title="Methamphetamine">Methamphetamine</a> <ul><li><a href="/wiki/Dextromethamphetamine" class="mw-redirect" title="Dextromethamphetamine">Dextromethamphetamine</a></li> <li><a href="/wiki/Levomethamphetamine" class="mw-redirect" title="Levomethamphetamine">Levomethamphetamine</a></li></ul></li> <li><a href="/wiki/Phenylpropylaminopentane" title="Phenylpropylaminopentane">Phenylpropylaminopentane</a> (PPAP)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Receptor_antagonist" title="Receptor antagonist">Antagonists</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/3-F-BPAP" title="3-F-BPAP">3-F-BPAP</a></li> <li><a href="/wiki/EPPTB" title="EPPTB">EPPTB</a></li> <li><a href="/wiki/Rasagiline" title="Rasagiline">Rasagiline</a></li></ul> </div></td></tr><tr><td class="navbox-abovebelow" colspan="2"><div><small><i><b>See also:</b> <a href="/wiki/Template:Receptor_modulators" title="Template:Receptor modulators">Receptor/signaling modulators</a> • <a href="/wiki/Template:Monoamine_releasing_agents" title="Template:Monoamine releasing agents">Monoamine releasing agents</a> • <a href="/wiki/Template:Monoamine_reuptake_inhibitors" title="Template:Monoamine reuptake inhibitors">Monoamine reuptake inhibitors</a> • <a href="/wiki/Template:Monoamine_metabolism_modulators" title="Template:Monoamine metabolism modulators">Monoamine metabolism modulators</a> • <a href="/wiki/Template:TAAR_ligands" title="Template:TAAR ligands">TAAR ligands</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="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="Phenethylamines" 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:Phenethylamines" title="Template:Phenethylamines"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Phenethylamines" title="Template talk:Phenethylamines"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Phenethylamines" title="Special:EditPage/Template:Phenethylamines"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Phenethylamines" style="font-size:114%;margin:0 4em"><a href="/wiki/Substituted_phenethylamine" title="Substituted phenethylamine">Phenethylamines</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Substituted_phenethylamine" title="Substituted phenethylamine">Phenethylamines</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i>Psychedelics:</i> <a href="/wiki/25B-NBOMe" title="25B-NBOMe">25B-NBOMe</a></li> <li><a href="/wiki/25C-NBOMe" title="25C-NBOMe">25C-NBOMe</a></li> <li><a href="/wiki/25D-NBOMe" title="25D-NBOMe">25D-NBOMe</a></li> <li><a href="/wiki/25I-NBOMe" title="25I-NBOMe">25I-NBOMe</a></li> <li><a href="/wiki/25N-NBOMe" title="25N-NBOMe">25N-NBOMe</a></li></ul> <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> <ul><li><a href="/wiki/Allylescaline" title="Allylescaline">Allylescaline</a></li> <li><a href="/wiki/DESOXY" title="DESOXY">DESOXY</a></li> <li><a href="/wiki/Escaline" title="Escaline">Escaline</a></li> <li><a href="/wiki/Isoproscaline" title="Isoproscaline">Isoproscaline</a></li> <li><a href="/wiki/Jimscaline" title="Jimscaline">Jimscaline</a></li> <li><a href="/wiki/Macromerine" title="Macromerine">Macromerine</a></li> <li><a href="/wiki/3-Methoxy-4-ethoxyphenethylamine" title="3-Methoxy-4-ethoxyphenethylamine">MEPEA</a></li> <li><a href="/wiki/Mescaline" title="Mescaline">Mescaline</a></li> <li><a href="/wiki/Metaescaline" title="Metaescaline">Metaescaline</a></li> <li><a href="/wiki/Methallylescaline" title="Methallylescaline">Methallylescaline</a></li> <li><a href="/wiki/Proscaline" title="Proscaline">Proscaline</a></li> <li><a href="/wiki/Psi-2C-T-4" class="mw-redirect" title="Psi-2C-T-4">Psi-2C-T-4</a></li> <li><a href="/wiki/TCB-2" title="TCB-2">TCB-2</a></li></ul> <p><br /><i>Stimulants:</i> <a href="/wiki/Phenylethanolamine" title="Phenylethanolamine">Phenylethanolamine</a> </p> <ul><li><a href="/wiki/Hordenine" title="Hordenine">Hordenine</a></li> <li><a href="/wiki/Phenethylamine" title="Phenethylamine">Phenethylamine</a></li> <li><a href="/wiki/Phenpromethamine" title="Phenpromethamine">Phenpromethamine</a></li> <li><a href="/wiki/Amphetamine" title="Amphetamine">α-Methylphenethylamine</a> (amphetamine)</li> <li><a href="/wiki/%CE%92-Methylphenethylamine" title="Β-Methylphenethylamine">β-Methylphenethylamine</a></li> <li><a href="/wiki/M-Methylphenethylamine" class="mw-redirect" title="M-Methylphenethylamine"><i>m</i>-Methylphenethylamine</a></li> <li><a href="/wiki/N-Methylphenethylamine" title="N-Methylphenethylamine"><i>N</i>-Methylphenethylamine</a></li> <li><a href="/wiki/O-Methylphenethylamine" class="mw-redirect" title="O-Methylphenethylamine"><i>o</i>-Methylphenethylamine</a></li> <li><a href="/wiki/P-Methylphenethylamine" class="mw-redirect" title="P-Methylphenethylamine"><i>p</i>-Methylphenethylamine</a></li> <li><a href="/wiki/Methylphenidate" title="Methylphenidate">Methylphenidate</a></li></ul> <ul><li><i>Entactogens:</i> <a href="/wiki/Lophophine" title="Lophophine">Lophophine</a></li> <li><a href="/wiki/Methylenedioxyphenethylamine" class="mw-redirect" title="Methylenedioxyphenethylamine">MDPEA</a></li> <li><a href="/wiki/Methylenedioxymethylphenethylamine" class="mw-redirect" title="Methylenedioxymethylphenethylamine">MDMPEA</a><br /><i>Others:</i> <a href="/wiki/BOH_(drug)" title="BOH (drug)">BOH</a></li> <li><a href="/wiki/3,4-Dimethoxyphenethylamine" title="3,4-Dimethoxyphenethylamine">DMPEA</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Substituted_amphetamine" title="Substituted amphetamine">Amphetamines</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i>Psychedelics:</i> <a href="/wiki/3C-AL" title="3C-AL">3C-AL</a></li> <li><a href="/wiki/3C-BZ" title="3C-BZ">3C-BZ</a></li> <li><a href="/wiki/3C-E" title="3C-E">3C-E</a></li> <li><a href="/wiki/3C-MAL" title="3C-MAL">3C-MAL</a></li> <li><a href="/wiki/3C-P" title="3C-P">3C-P</a></li> <li><a href="/wiki/Aleph_(psychedelic)" title="Aleph (psychedelic)">Aleph</a></li> <li><a href="/wiki/Beatrice_(psychedelic)" title="Beatrice (psychedelic)">Beatrice</a></li> <li><a href="/wiki/Bromo-DragonFLY" title="Bromo-DragonFLY">Bromo-DragonFLY</a></li> <li><a href="/wiki/D-Deprenyl" title="D-Deprenyl">D-Deprenyl</a></li> <li><a href="/wiki/Dimethoxyamphetamine" title="Dimethoxyamphetamine">DMA</a></li> <li><a href="/wiki/4-Methyl-2,5-methoxyphenylcyclopropylamine" class="mw-redirect" title="4-Methyl-2,5-methoxyphenylcyclopropylamine">DMCPA</a></li> <li><a href="/wiki/DMMDA" title="DMMDA">DMMDA</a></li> <li><a href="/wiki/2,5-Dimethoxy-4-bromoamphetamine" title="2,5-Dimethoxy-4-bromoamphetamine">DOB</a></li> <li><a href="/wiki/2,5-Dimethoxy-4-chloroamphetamine" title="2,5-Dimethoxy-4-chloroamphetamine">DOC</a></li> <li><a href="/wiki/2,5-Dimethoxy-4-fluoroethylamphetamine" class="mw-redirect" title="2,5-Dimethoxy-4-fluoroethylamphetamine">DOEF</a></li> <li><a href="/wiki/2,5-Dimethoxy-4-ethylamphetamine" title="2,5-Dimethoxy-4-ethylamphetamine">DOET</a></li> <li><a href="/wiki/2,5-Dimethoxy-4-iodoamphetamine" title="2,5-Dimethoxy-4-iodoamphetamine">DOI</a></li> <li><a href="/wiki/2,5-Dimethoxy-4-methylamphetamine" title="2,5-Dimethoxy-4-methylamphetamine">DOM</a></li> <li><a href="/wiki/2,5-Dimethoxy-4-nitroamphetamine" title="2,5-Dimethoxy-4-nitroamphetamine">DON</a></li> <li><a href="/wiki/2,5-Dimethoxy-4-propylamphetamine" title="2,5-Dimethoxy-4-propylamphetamine">DOPR</a></li> <li><a href="/wiki/2,5-Dimethoxy-4-trifluoromethylamphetamine" title="2,5-Dimethoxy-4-trifluoromethylamphetamine">DOTFM</a></li> <li><a href="/wiki/Ganesha_(psychedelic)" title="Ganesha (psychedelic)">Ganesha</a></li> <li><a href="/wiki/MMDA_(drug)" title="MMDA (drug)">MMDA</a></li> <li><a href="/wiki/MMDA-2" title="MMDA-2">MMDA-2</a></li> <li><a href="/wiki/Psi-DOM" class="mw-redirect" title="Psi-DOM">Psi-DOM</a></li> <li><a href="/wiki/Trimethoxyamphetamine" title="Trimethoxyamphetamine">TMA</a></li> <li><a href="/wiki/Tetramethoxyamphetamine" class="mw-redirect" title="Tetramethoxyamphetamine">TeMA</a></li> <li><a href="/wiki/ZDCM-04" title="ZDCM-04">ZDCM-04</a><br /><i>Stimulants:</i> <a href="/wiki/2-Fluoroamphetamine" title="2-Fluoroamphetamine">2-FA</a></li> <li><a href="/wiki/2-Fluoromethamphetamine" title="2-Fluoromethamphetamine">2-FMA</a></li> <li><a href="/wiki/3-Fluoroamphetamine" title="3-Fluoroamphetamine">3-FA</a></li> <li><a href="/wiki/3-Fluoromethamphetamine" title="3-Fluoromethamphetamine">3-FMA</a></li> <li><a href="/wiki/Acridorex" title="Acridorex">Acridorex</a></li> <li><a href="/wiki/Alfetamine" title="Alfetamine">Alfetamine</a></li> <li><a href="/wiki/Amfecloral" title="Amfecloral">Amfecloral</a></li> <li><a href="/wiki/Amfepentorex" title="Amfepentorex">Amfepentorex</a></li> <li><a href="/wiki/Amphetamine" title="Amphetamine">Amphetamine</a> (<a href="/wiki/Dextroamphetamine" title="Dextroamphetamine">Dextroamphetamine</a>, <a href="/wiki/Levoamphetamine" title="Levoamphetamine">Levoamphetamine</a>)</li> <li><a href="/wiki/Amphetaminil" class="mw-redirect" title="Amphetaminil">Amphetaminil</a></li> <li><a href="/wiki/Benfluorex" title="Benfluorex">Benfluorex</a></li> <li><a href="/wiki/Benzphetamine" title="Benzphetamine">Benzphetamine</a></li> <li><a href="/wiki/Cathine" title="Cathine">Cathine</a></li> <li><a href="/wiki/Clobenzorex" title="Clobenzorex">Clobenzorex</a></li> <li><a href="/wiki/Dimethylamphetamine" title="Dimethylamphetamine">Dimethylamphetamine</a></li> <li><a href="/wiki/Ephedrine" title="Ephedrine">Ephedrine</a></li> <li><a href="/wiki/Etilamfetamine" title="Etilamfetamine">Etilamfetamine</a></li> <li><a href="/wiki/Fencamfamin" title="Fencamfamin">Fencamfamin</a></li> <li><a href="/wiki/Fencamine" title="Fencamine">Fencamine</a></li> <li><a href="/wiki/Fenethylline" title="Fenethylline">Fenethylline</a></li> <li><a href="/wiki/Fenfluramine" title="Fenfluramine">Fenfluramine</a> (<a href="/wiki/Dexfenfluramine" title="Dexfenfluramine">Dexfenfluramine</a>, <a href="/wiki/Levofenfluramine" title="Levofenfluramine">Levofenfluramine</a>)</li> <li><a href="/wiki/Fenproporex" title="Fenproporex">Fenproporex</a></li> <li><a href="/wiki/Flucetorex" title="Flucetorex">Flucetorex</a></li> <li><a href="/wiki/Fludorex" title="Fludorex">Fludorex</a></li> <li><a href="/wiki/Formetorex" title="Formetorex">Formetorex</a></li> <li><a href="/wiki/Furfenorex" title="Furfenorex">Furfenorex</a></li> <li><a href="/wiki/Gepefrine" title="Gepefrine">Gepefrine</a></li> <li><a href="/wiki/4-Hydroxyamphetamine" title="4-Hydroxyamphetamine">4-Hydroxyamphetamine</a></li> <li><a href="/wiki/Iofetamine" class="mw-redirect" title="Iofetamine">Iofetamine</a></li> <li><a href="/wiki/Isopropylamphetamine" title="Isopropylamphetamine">Isopropylamphetamine</a></li> <li><a href="/wiki/Lefetamine" title="Lefetamine">Lefetamine</a></li> <li><a href="/wiki/Lisdexamfetamine" title="Lisdexamfetamine">Lisdexamfetamine</a></li> <li><a href="/wiki/Mefenorex" title="Mefenorex">Mefenorex</a></li> <li><a href="/wiki/Metaraminol" title="Metaraminol">Metaraminol</a></li> <li><a href="/wiki/Methamphetamine" title="Methamphetamine">Methamphetamine</a> (Dextromethamphetamine, <a href="/wiki/Levomethamphetamine" class="mw-redirect" title="Levomethamphetamine">Levomethamphetamine</a>)</li> <li><a href="/wiki/Methoxyphenamine" title="Methoxyphenamine">Methoxyphenamine</a></li> <li><a href="/wiki/3-Methoxy-4-methylamphetamine" title="3-Methoxy-4-methylamphetamine">MMA</a></li> <li><a href="/wiki/Morforex" title="Morforex">Morforex</a></li> <li><a href="/wiki/Norfenfluramine" title="Norfenfluramine">Norfenfluramine</a></li> <li><a href="/wiki/L-Norpseudoephedrine" title="L-Norpseudoephedrine"><span style="font-size:85%;">L</span>-Norpseudoephedrine</a></li> <li><a href="/wiki/N,alpha-Diethylphenylethylamine" class="mw-redirect" title="N,alpha-Diethylphenylethylamine">N,alpha-Diethylphenylethylamine</a></li> <li><a href="/wiki/Oxifentorex" title="Oxifentorex">Oxifentorex</a></li> <li><a href="/wiki/Oxilofrine" title="Oxilofrine">Oxilofrine</a></li> <li><a href="/wiki/Ortetamine" title="Ortetamine">Ortetamine</a></li> <li><a href="/wiki/Para-Bromoamphetamine" title="Para-Bromoamphetamine">PBA</a></li> <li><a href="/wiki/Para-Chloroamphetamine" title="Para-Chloroamphetamine">PCA</a></li> <li><a href="/wiki/4-Fluoroamphetamine" title="4-Fluoroamphetamine">PFA</a></li> <li><a href="/wiki/4-Fluoromethamphetamine" title="4-Fluoromethamphetamine">PFMA</a></li> <li><a href="/wiki/Para-Iodoamphetamine" title="Para-Iodoamphetamine">PIA</a></li> <li><a href="/wiki/Para-Methoxyamphetamine" title="Para-Methoxyamphetamine">PMA</a></li> <li><a href="/wiki/Para-Methoxy-N-ethylamphetamine" title="Para-Methoxy-N-ethylamphetamine">PMEA</a></li> <li><a href="/wiki/Para-Methoxy-N-methylamphetamine" title="Para-Methoxy-N-methylamphetamine">PMMA</a></li> <li><a href="/wiki/Phenylpropanolamine" title="Phenylpropanolamine">Phenylpropanolamine</a></li> <li><a href="/wiki/Pholedrine" title="Pholedrine">Pholedrine</a></li> <li><a href="/wiki/Prenylamine" title="Prenylamine">Prenylamine</a></li> <li><a href="/wiki/Propylamphetamine" title="Propylamphetamine">Propylamphetamine</a></li> <li><a href="/wiki/Pseudoephedrine" title="Pseudoephedrine">Pseudoephedrine</a></li> <li><a href="/wiki/Sibutramine" title="Sibutramine">Sibutramine</a></li> <li><a href="/wiki/Tiflorex" title="Tiflorex">Tiflorex</a></li> <li><a href="/wiki/Tranylcypromine" title="Tranylcypromine">Tranylcypromine</a></li> <li><a href="/wiki/Xylopropamine" title="Xylopropamine">Xylopropamine</a></li> <li><a href="/wiki/Zylofuramine" title="Zylofuramine">Zylofuramine</a><br /><i>Entactogens:</i> <a href="/wiki/4-Fluoroamphetamine" title="4-Fluoroamphetamine">4-FA</a></li> <li><a href="/wiki/4-Fluoromethamphetamine" title="4-Fluoromethamphetamine">4-FMA</a></li> <li><a href="/wiki/4-Methylamphetamine" title="4-Methylamphetamine">4-MA</a></li> <li><a href="/wiki/4-Methylmethamphetamine" class="mw-redirect" title="4-Methylmethamphetamine">4-MMA</a></li> <li><a href="/wiki/4-Methylthioamphetamine" title="4-Methylthioamphetamine">4-MTA</a></li> <li><a href="/wiki/5-APB" title="5-APB">5-APB</a></li> <li><a href="/wiki/5-APDB" title="5-APDB">5-APDB</a></li> <li><a href="/wiki/5-EAPB" title="5-EAPB">5-EAPB</a></li> <li><a href="/wiki/5-IT" title="5-IT">5-IT</a></li> <li><a href="/wiki/5-MAPB" title="5-MAPB">5-MAPB</a></li> <li><a href="/wiki/5-MAPDB" title="5-MAPDB">5-MAPDB</a></li> <li><a href="/wiki/6-APB" title="6-APB">6-APB</a></li> <li><a href="/wiki/6-APDB" title="6-APDB">6-APDB</a></li> <li><a href="/wiki/6-Chloro-MDMA" title="6-Chloro-MDMA">6-Chloro-MDMA</a></li> <li><a href="/wiki/6-EAPB" title="6-EAPB">6-EAPB</a></li> <li><a href="/wiki/6-IT" class="mw-redirect" title="6-IT">6-IT</a></li> <li><a href="/wiki/6-MAPB" title="6-MAPB">6-MAPB</a></li> <li><a href="/wiki/6-MAPDB" title="6-MAPDB">6-MAPDB</a></li> <li><a href="/wiki/Ethylidenedioxyamphetamine" class="mw-redirect" title="Ethylidenedioxyamphetamine">EDA</a></li> <li><a href="/wiki/Indanylaminopropane" class="mw-redirect" title="Indanylaminopropane">IAP</a></li> <li><a href="/wiki/2,3-Methylenedioxyamphetamine" title="2,3-Methylenedioxyamphetamine">2,3-MDA</a></li> <li><a href="/wiki/3,4-Methylenedioxyamphetamine" title="3,4-Methylenedioxyamphetamine">3,4-MDA (tenamfetamine)</a></li> <li><a href="/wiki/Methylenedioxyethylamphetamine" class="mw-redirect" title="Methylenedioxyethylamphetamine">MDEA</a></li> <li><a href="/wiki/Methylenedioxyhydroxylmethamphetamine" class="mw-redirect" title="Methylenedioxyhydroxylmethamphetamine">MDHMA</a></li> <li><a href="/wiki/MDMA" title="MDMA">MDMA (midomafetamine)</a></li> <li><a href="/wiki/Methylenedioxyhydroxyamphetamine" class="mw-redirect" title="Methylenedioxyhydroxyamphetamine">MDOH</a></li> <li><a href="/wiki/Methamnetamine" title="Methamnetamine">Methamnetamine</a></li> <li><a href="/wiki/MMDMA" title="MMDMA">MMDMA</a></li> <li><a href="/wiki/Naphthylaminopropane" title="Naphthylaminopropane">Naphthylaminopropane</a></li> <li><a href="/wiki/Tetralinylaminopropane" class="mw-redirect" title="Tetralinylaminopropane">TAP</a><br /><i>Others:</i> <a href="/wiki/3,4-Dichloroamphetamine" title="3,4-Dichloroamphetamine">3,4-DCA</a></li> <li><a href="/wiki/Amiflamine" title="Amiflamine">Amiflamine</a></li> <li><a href="/wiki/DiFMDA" class="mw-redirect" title="DiFMDA">DiFMDA</a></li> <li><a href="/wiki/Selegiline" title="Selegiline">Selegiline</a> (also <a href="/wiki/D-Deprenyl" title="D-Deprenyl"><span style="font-size:85%;">D</span>-Deprenyl</a>)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Phentermine" title="Phentermine">Phentermines</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i>Stimulants:</i> <a href="/wiki/Chlorphentermine" title="Chlorphentermine">Chlorphentermine</a></li> <li><a href="/wiki/Cloforex" title="Cloforex">Cloforex</a></li> <li><a href="/wiki/Clortermine" title="Clortermine">Clortermine</a></li> <li><a href="/wiki/Etolorex" title="Etolorex">Etolorex</a></li> <li><a href="/wiki/Mephentermine" title="Mephentermine">Mephentermine</a></li> <li><a href="/wiki/Pentorex" title="Pentorex">Pentorex</a></li> <li><a href="/wiki/Phentermine" title="Phentermine">Phentermine</a><br /><i>Entactogens:</i> <a href="/wiki/Methylenedioxyphentermine" class="mw-redirect" title="Methylenedioxyphentermine">MDPH</a></li> <li><a href="/wiki/Methylenedioxymethylphentermine" class="mw-redirect" title="Methylenedioxymethylphentermine">MDMPH</a><br /><i>Others:</i> <a href="/wiki/Cericlamine" title="Cericlamine">Cericlamine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Substituted_cathinone" title="Substituted cathinone">Cathinones</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i>Stimulants:</i> <a href="/wiki/3-Fluoromethcathinone" title="3-Fluoromethcathinone">3-FMC</a></li> <li><a href="/wiki/4-Methylcathinone" title="4-Methylcathinone">4-MC</a></li> <li><a href="/wiki/4-Bromomethcathinone" title="4-Bromomethcathinone">4-BMC</a></li> <li><a href="/wiki/4-Chloromethcathinone" title="4-Chloromethcathinone">4-CMC</a></li> <li><a href="/wiki/4-Ethylmethcathinone" title="4-Ethylmethcathinone">4-EMC</a></li> <li><a href="/wiki/Flephedrone" title="Flephedrone">4-FMC</a></li> <li><a href="/wiki/4-Methylethcathinone" title="4-Methylethcathinone">4-MEC</a></li> <li><a href="/wiki/4-Methylbuphedrone" title="4-Methylbuphedrone">4-MeMABP</a></li> <li><a href="/wiki/4-Methylpentedrone" title="4-Methylpentedrone">4-MPD</a></li> <li><a href="/wiki/Amfepramone" title="Amfepramone">Amfepramone</a></li> <li><a href="/wiki/Benzedrone" title="Benzedrone">Benzedrone</a></li> <li><a href="/wiki/Brephedrone" class="mw-redirect" title="Brephedrone">Brephedrone</a></li> <li><a href="/wiki/Buphedrone" title="Buphedrone">Buphedrone</a></li> <li><a href="/wiki/Bupropion" title="Bupropion">Bupropion</a></li> <li><a href="/wiki/Cathinone" title="Cathinone">Cathinone</a></li> <li><a href="/wiki/Dimethylcathinone" class="mw-redirect" title="Dimethylcathinone">Dimethylcathinone</a></li> <li><a href="/wiki/Ethcathinone" title="Ethcathinone">Ethcathinone</a></li> <li><a href="/wiki/Eutylone" title="Eutylone">Eutylone</a></li> <li><a href="/wiki/Hydroxybupropion" title="Hydroxybupropion">Hydroxybupropion</a></li> <li><a href="/wiki/Methcathinone" title="Methcathinone">Methcathinone</a></li> <li><a href="/wiki/Methedrone" title="Methedrone">Methedrone</a></li> <li><a href="/wiki/N-Ethylbuphedrone" title="N-Ethylbuphedrone">NEB</a></li> <li><a href="/wiki/N-Ethylhexedrone" title="N-Ethylhexedrone">N-Ethylhexedrone</a></li> <li><a href="/wiki/N-Ethylpentedrone" title="N-Ethylpentedrone">N-Ethylpentedrone</a></li> <li><a href="/wiki/Pentedrone" title="Pentedrone">Pentedrone</a></li> <li><a href="/wiki/Pentylone" title="Pentylone">Pentylone</a></li> <li><a href="/wiki/Radafaxine" title="Radafaxine">Radafaxine</a><br /><i>Entactogens:</i> <a href="/wiki/3,4-Dimethylmethcathinone" title="3,4-Dimethylmethcathinone">3,4-DMMC</a></li> <li><a href="/wiki/3-Methylmethcathinone" title="3-Methylmethcathinone">3-MMC</a></li> <li><a href="/wiki/Butylone" title="Butylone">Butylone</a></li> <li><a href="/wiki/Ethylone" title="Ethylone">Ethylone</a></li> <li><a href="/wiki/Methylone" title="Methylone">Methylone</a></li> <li><a href="/wiki/Methylenedioxycathinone" title="Methylenedioxycathinone">Methylenedioxycathinone</a></li> <li><a href="/wiki/Mephedrone" title="Mephedrone">Mephedrone</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Phenylisobutylamine" title="Phenylisobutylamine">Phenylisobutylamines</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i>Entactogens:</i> <a href="/wiki/4-Chlorophenylisobutylamine" title="4-Chlorophenylisobutylamine">4-CAB</a></li> <li><a href="/wiki/4-Methylphenylisobutylamine" title="4-Methylphenylisobutylamine">4-MAB</a></li> <li><a href="/wiki/Ariadne_(psychedelic)" class="mw-redirect" title="Ariadne (psychedelic)">Ariadne</a></li> <li><a href="/wiki/Benzodioxolylbutanamine" class="mw-redirect" title="Benzodioxolylbutanamine">BDB</a></li> <li><a href="/wiki/Butylone" title="Butylone">Butylone</a></li> <li><a href="/wiki/Ethylbenzodioxolylbutanamine" class="mw-redirect" title="Ethylbenzodioxolylbutanamine">EBDB</a></li> <li><a href="/wiki/Eutylone" title="Eutylone">Eutylone</a></li> <li><a href="/wiki/MBDB" title="MBDB">MBDB</a><br /><i>Stimulants:</i> <a href="/wiki/Phenylisobutylamine" title="Phenylisobutylamine">Phenylisobutylamine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Phenylethylpyrrolidine" title="Phenylethylpyrrolidine">Phenylalkylpyrrolidines</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i>Stimulants:</i> <a href="/wiki/Alpha-Pyrrolidinobutiophenone" class="mw-redirect" title="Alpha-Pyrrolidinobutiophenone">α-PBP</a></li> <li><a href="/wiki/Alpha-Pyrrolidinohexiophenone" class="mw-redirect" title="Alpha-Pyrrolidinohexiophenone">α-PHP</a></li> <li><a href="/wiki/Alpha-Pyrrolidinopropiophenone" class="mw-redirect" title="Alpha-Pyrrolidinopropiophenone">α-PPP</a></li> <li><a href="/wiki/Alpha-Pyrrolidinopentiophenone" class="mw-redirect" title="Alpha-Pyrrolidinopentiophenone">α-PVP</a></li> <li><a href="/wiki/3%27,4%27-Methylenedioxy-%CE%B1-pyrrolidinobutiophenone" title="3',4'-Methylenedioxy-α-pyrrolidinobutiophenone">MDPBP</a></li> <li><a href="/wiki/3%27,4%27-Methylenedioxy-%CE%B1-pyrrolidinopropiophenone" title="3',4'-Methylenedioxy-α-pyrrolidinopropiophenone">MDPPP</a></li> <li><a href="/wiki/3,4-Methylenedioxypyrovalerone" class="mw-redirect" title="3,4-Methylenedioxypyrovalerone">MDPV</a></li> <li><a href="/wiki/4%27-Methyl-%CE%B1-pyrrolidinobutiophenone" title="4'-Methyl-α-pyrrolidinobutiophenone">4-MePBP</a></li> <li><a href="/wiki/4%27-Methyl-%CE%B1-pyrrolidinohexiophenone" title="4'-Methyl-α-pyrrolidinohexiophenone">4-MePHP</a></li> <li><a href="/wiki/4%27-Methyl-%CE%B1-pyrrolidinopropiophenone" title="4'-Methyl-α-pyrrolidinopropiophenone">4-MePPP</a></li> <li><a href="/wiki/4%27-Methoxy-%CE%B1-pyrrolidinopropiophenone" title="4'-Methoxy-α-pyrrolidinopropiophenone">MOPPP</a></li> <li><a href="/wiki/4%27-Methoxy-%CE%B1-pyrrolidinopentiophenone" title="4'-Methoxy-α-pyrrolidinopentiophenone">MOPVP</a></li> <li><a href="/wiki/4%27-Methyl-%CE%B1-pyrrolidinobutiophenone" title="4'-Methyl-α-pyrrolidinobutiophenone">MPBP</a></li> <li><a href="/wiki/4%27-Methyl-%CE%B1-pyrrolidinohexiophenone" title="4'-Methyl-α-pyrrolidinohexiophenone">MPHP</a></li> <li><a href="/wiki/4%27-Methyl-%CE%B1-pyrrolidinopropiophenone" title="4'-Methyl-α-pyrrolidinopropiophenone">MPPP</a></li> <li><a href="/wiki/Naphyrone" title="Naphyrone">Naphyrone</a></li> <li><a href="/wiki/Phenylethylpyrrolidine" title="Phenylethylpyrrolidine">PEP</a></li> <li><a href="/wiki/Prolintane" title="Prolintane">Prolintane</a></li> <li><a href="/wiki/Pyrovalerone" title="Pyrovalerone">Pyrovalerone</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Catecholamine" title="Catecholamine">Catecholamines</a><br /><span style="font-size:85%;">(and close relatives)</span></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/6-Fluoronorepinephrine" title="6-Fluoronorepinephrine">6-FNE</a></li> <li><a href="/wiki/6-Hydroxydopamine" class="mw-redirect" title="6-Hydroxydopamine">6-OHDA</a></li> <li><a href="/wiki/Alpha-Methyldopamine" class="mw-redirect" title="Alpha-Methyldopamine">a-Me-DA</a></li> <li><a href="/wiki/Alpha-Methyltyramine" class="mw-redirect" title="Alpha-Methyltyramine">a-Me-TRA</a></li> <li><a href="/wiki/Adrenochrome" title="Adrenochrome">Adrenochrome</a></li> <li><a href="/wiki/Ciladopa" title="Ciladopa">Ciladopa</a></li> <li><a href="/wiki/D-DOPA" title="D-DOPA"><span style="font-size:85%;">D</span>-DOPA</a> (Dextrodopa)</li> <li><a href="/wiki/Dimetofrine" title="Dimetofrine">Dimetofrine</a></li> <li><a href="/wiki/Dopamine" title="Dopamine">Dopamine</a></li> <li><a href="/wiki/Epinephrine_(neurotransmitter)" class="mw-redirect" title="Epinephrine (neurotransmitter)">Epinephrine</a></li> <li><a href="/wiki/Epinine" class="mw-redirect" title="Epinine">Epinine</a></li> <li><a href="/wiki/Etilefrine" title="Etilefrine">Etilefrine</a></li> <li><a href="/wiki/Ethylnorepinephrine" title="Ethylnorepinephrine">Ethylnorepinephrine</a></li> <li><a href="/wiki/Fenclonine" title="Fenclonine">Fenclonine</a></li> <li><a href="/wiki/Ibopamine" title="Ibopamine">Ibopamine</a></li> <li><a href="/wiki/Isoprenaline" title="Isoprenaline">Isoprenaline</a></li> <li><a href="/wiki/Isoetarine" title="Isoetarine">Isoetarine</a></li> <li><a href="/wiki/L-DOPA" title="L-DOPA"><span style="font-size:85%;">L</span>-DOPA</a> (Levodopa)</li> <li><a href="/wiki/L-DOPS" class="mw-redirect" title="L-DOPS"><span style="font-size:85%;">L</span>-DOPS</a> (Droxidopa)</li> <li><a href="/wiki/L-Phenylalanine" class="mw-redirect" title="L-Phenylalanine"><span style="font-size:85%;">L</span>-Phenylalanine</a></li> <li><a href="/wiki/L-Tyrosine" class="mw-redirect" title="L-Tyrosine"><span style="font-size:85%;">L</span>-Tyrosine</a></li> <li><a href="/wiki/Meta-Tyramine" title="Meta-Tyramine"><i>m</i>-Tyramine</a></li> <li><a href="/wiki/Metanephrine" title="Metanephrine">Metanephrine</a></li> <li><a href="/wiki/Metaraminol" title="Metaraminol">Metaraminol</a></li> <li><a href="/wiki/Metaterol" title="Metaterol">Metaterol</a></li> <li><a href="/wiki/Metirosine" class="mw-redirect" title="Metirosine">Metirosine</a></li> <li><a href="/wiki/Methyldopa" title="Methyldopa">Methyldopa</a></li> <li><a href="/wiki/N,N-Dimethyldopamine" title="N,N-Dimethyldopamine">N,N-Dimethyldopamine</a></li> <li><a href="/wiki/Nordefrin" class="mw-redirect" title="Nordefrin">Nordefrin</a> (<a href="/wiki/Levonordefrin" class="mw-redirect" title="Levonordefrin">Levonordefrin</a>)</li> <li><a href="/wiki/Norepinephrine" title="Norepinephrine">Norepinephrine</a></li> <li><a href="/wiki/Norfenefrine" title="Norfenefrine">Norfenefrine</a> (<i>m</i>-Octopamine)</li> <li><a href="/wiki/Normetanephrine" title="Normetanephrine">Normetanephrine</a></li> <li><a href="/wiki/Orciprenaline" title="Orciprenaline">Orciprenaline</a></li> <li><a href="/wiki/Octopamine" title="Octopamine"><i>p</i>-Octopamine</a></li> <li><a class="mw-selflink selflink"><i>p</i>-Tyramine</a></li> <li><a href="/wiki/Phenylephrine" title="Phenylephrine">Phenylephrine</a></li> <li><a href="/wiki/Synephrine" title="Synephrine">Synephrine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Miscellaneous</th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/AL-LAD" title="AL-LAD">AL-LAD</a></li> <li><a href="/wiki/Amidephrine" title="Amidephrine">Amidephrine</a></li> <li><a href="/wiki/Arbutamine" title="Arbutamine">Arbutamine</a></li> <li><a href="/wiki/Cafedrine" title="Cafedrine">Cafedrine</a></li> <li><a href="/wiki/Denopamine" title="Denopamine">Denopamine</a></li> <li><a href="/wiki/Desvenlafaxine" title="Desvenlafaxine">Desvenlafaxine</a></li> <li><a href="/wiki/Diphenidine" title="Diphenidine">Diphenidine</a></li> <li><a href="/wiki/Dizocilpine" title="Dizocilpine">Dizocilpine</a></li> <li><a href="/wiki/Dobutamine" title="Dobutamine">Dobutamine</a></li> <li><a href="/wiki/Dopexamine" title="Dopexamine">Dopexamine</a></li> <li><a href="/wiki/Ephenidine" title="Ephenidine">Ephenidine</a></li> <li><a href="/wiki/Etafedrine" title="Etafedrine">Etafedrine</a></li> <li><a href="/wiki/ETH-LAD" title="ETH-LAD">ETH-LAD</a></li> <li><a href="/wiki/Famprofazone" title="Famprofazone">Famprofazone</a></li> <li><a href="/wiki/Fluorolintane" title="Fluorolintane">Fluorolintane</a></li> <li><a href="/wiki/Hexapradol" title="Hexapradol">Hexapradol</a></li> <li><a href="/wiki/IP-LAD" class="mw-redirect" title="IP-LAD">IP-LAD</a></li> <li><a href="/wiki/Lysergic_acid_amide" class="mw-redirect" title="Lysergic acid amide">Lysergic acid amide</a></li> <li><a href="/wiki/Lysergic_acid_2-butyl_amide" title="Lysergic acid 2-butyl amide">Lysergic acid 2-butyl amide</a></li> <li><a href="/wiki/Lysergic_acid_2,4-dimethylazetidide" title="Lysergic acid 2,4-dimethylazetidide">Lysergic acid 2,4-dimethylazetidide</a></li> <li><a href="/wiki/LSD" title="LSD">Lysergic acid diethylamide</a></li> <li><a href="/wiki/Methoxamine" title="Methoxamine">Methoxamine</a></li> <li><a href="/wiki/Methoxphenidine" title="Methoxphenidine">Methoxphenidine</a></li> <li><a href="/wiki/MT-45" title="MT-45">MT-45</a></li> <li><a href="/wiki/PARGY-LAD" title="PARGY-LAD">PARGY-LAD</a></li> <li><a href="/wiki/Phenibut" title="Phenibut">Phenibut</a></li> <li><a href="/wiki/PRO-LAD" title="PRO-LAD">PRO-LAD</a></li> <li><a href="/wiki/Pronethalol" title="Pronethalol">Pronethalol</a></li> <li><a href="/wiki/Salbutamol" title="Salbutamol">Salbutamol</a> (<a href="/wiki/Levosalbutamol" title="Levosalbutamol">Levosalbutamol</a>)</li> <li><a href="/wiki/Solriamfetol" title="Solriamfetol">Solriamfetol</a></li> <li><a href="/wiki/Theodrenaline" title="Theodrenaline">Theodrenaline</a></li> <li><a href="/wiki/Thiamphenicol" title="Thiamphenicol">Thiamphenicol</a></li> <li><a href="/wiki/UWA-101" title="UWA-101">UWA-101</a></li> <li><a href="/wiki/Venlafaxine" title="Venlafaxine">Venlafaxine</a></li></ul> </div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"></div><div role="navigation" class="navbox" aria-labelledby="Chocolate" 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" style="background: #7B3F00; color: white;"><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:Chocolate" title="Template:Chocolate"><abbr title="View this template" style="color: white">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Chocolate" title="Template talk:Chocolate"><abbr title="Discuss this template" style="color: white">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Chocolate" title="Special:EditPage/Template:Chocolate"><abbr title="Edit this template" style="color: white">e</abbr></a></li></ul></div><div id="Chocolate" style="font-size:114%;margin:0 4em"><a href="/wiki/Chocolate" title="Chocolate"><span style="color:white">Chocolate</span></a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%;background: #7B3F00; color: white;"><a href="/wiki/Cocoa_bean" title="Cocoa bean"><span style="color:white">Cocoa bean</span></a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Chocolate_liquor" title="Chocolate liquor">Chocolate liquor</a></li> <li><a href="/wiki/Cocoa_butter" title="Cocoa butter">Cocoa butter</a></li> <li><a href="/wiki/Cocoa_solids" title="Cocoa solids">Cocoa solids</a></li> <li><i><a href="/wiki/Theobroma_cacao" title="Theobroma cacao">Theobroma cacao</a></i></li> <li><a href="/wiki/Types_of_cocoa_beans" title="Types of cocoa beans">Types</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;background: #7B3F00; color: white;">Components</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/Anandamide" title="Anandamide">Anandamide</a></li> <li><a href="/wiki/Caffeine" title="Caffeine">Caffeine</a></li> <li><a href="/wiki/Endorphins" title="Endorphins">Endorphins</a></li> <li><a href="/wiki/Enkephalin" title="Enkephalin">Enkephalin</a></li> <li><a href="/wiki/Flavan-3-ol" title="Flavan-3-ol">Flavan-3-ol</a></li> <li><a href="/wiki/Lecithin" title="Lecithin">Lecithin</a></li> <li><a href="/wiki/Phenethylamine" title="Phenethylamine">Phenethylamine</a></li> <li><a href="/wiki/Phenylalanine" title="Phenylalanine">Phenylalanine</a></li> <li><a href="/wiki/Salsolinol" title="Salsolinol">Salsolinol</a></li> <li><a href="/wiki/Tetramethylpyrazine" title="Tetramethylpyrazine">Tetramethylpyrazine</a></li> <li><a href="/wiki/Theobromine" title="Theobromine">Theobromine</a></li> <li><a href="/wiki/Theophylline" title="Theophylline">Theophylline</a></li> <li><a href="/wiki/Tryptamine" title="Tryptamine">Tryptamine</a></li> <li><a href="/wiki/Tryptophan" title="Tryptophan">Tryptophan</a></li> <li><a class="mw-selflink selflink">Tyramine</a></li> <li><a href="/wiki/Tyrosine" title="Tyrosine">Tyrosine</a></li> <li><a href="/wiki/Valeric_acid" title="Valeric acid">Valeric acid</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;background: #7B3F00; color: white;"><a href="/wiki/Types_of_chocolate" title="Types of chocolate"><span style="color:white">Types</span></a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Baking_chocolate" title="Baking chocolate">Baking</a></li> <li><a href="/wiki/Dark_chocolate" title="Dark chocolate">Dark</a></li> <li><a href="/wiki/Gianduja_(chocolate)" title="Gianduja (chocolate)">Gianduja</a></li> <li><a href="/wiki/Milk_chocolate" title="Milk chocolate">Milk</a></li> <li><a href="/wiki/Organic_chocolate" title="Organic chocolate">Organic</a></li> <li><a href="/wiki/Raw_chocolate" title="Raw chocolate">Raw</a></li> <li><a href="/wiki/Ruby_chocolate" title="Ruby chocolate">Ruby</a></li> <li><a href="/wiki/White_chocolate" title="White chocolate">White</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;background: #7B3F00; color: white;">Products</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/Caff%C3%A8_mocha" title="Caffè mocha">Caffè mocha</a></li> <li><a href="/wiki/Chocolate_bar" title="Chocolate bar">Chocolate bar</a> <ul><li><a href="/wiki/List_of_chocolate_bar_brands" title="List of chocolate bar brands">Brands</a></li></ul></li> <li><a href="/wiki/Chocolate_biscuit" title="Chocolate biscuit">Chocolate biscuit</a></li> <li><a href="/wiki/Chocolate_brownie" title="Chocolate brownie">Chocolate brownie</a></li> <li><a href="/wiki/Chocolate_cake" title="Chocolate cake">Chocolate cake</a></li> <li><a href="/wiki/Chocolate_chip_cookie" title="Chocolate chip cookie">Chocolate chip cookie</a></li> <li><a href="/wiki/Chocolate_chip" title="Chocolate chip">Chocolate chip</a></li> <li><a href="/wiki/Chocolate_coin" title="Chocolate coin">Chocolate coins</a></li> <li><a href="/wiki/Chocolate_crackles" title="Chocolate crackles">Chocolate crackles</a></li> <li><a href="/wiki/Chocolate_gravy" title="Chocolate gravy">Chocolate gravy</a></li> <li><a href="/wiki/Chocolate_ice_cream" title="Chocolate ice cream">Chocolate ice cream</a></li> <li><a href="/wiki/Chocolate_liqueur" title="Chocolate liqueur">Chocolate liqueur</a></li> <li><a href="/wiki/Chocolate_milk" title="Chocolate milk">Chocolate milk</a></li> <li><a href="/wiki/Chocolate_pudding" title="Chocolate pudding">Chocolate pudding</a></li> <li><a href="/wiki/Chocolate_spread" title="Chocolate spread">Chocolate spread</a></li> <li><a href="/wiki/Chocolate_syrup" title="Chocolate syrup">Chocolate syrup</a></li> <li><a href="/wiki/Chocolate_truffle" title="Chocolate truffle">Chocolate truffle</a></li> <li><a href="/wiki/Cioccolato_di_Modica" title="Cioccolato di Modica">Cioccolato di Modica</a></li> <li><a href="/wiki/Fudge" title="Fudge">Fudge</a></li> <li><a href="/wiki/Ganache" title="Ganache">Ganache</a></li> <li><a href="/wiki/Hot_chocolate" title="Hot chocolate">Hot chocolate</a></li> <li><a href="/wiki/List_of_chocolate_drinks" title="List of chocolate drinks">Other beverages</a></li> <li><a href="/wiki/List_of_chocolate-covered_foods" title="List of chocolate-covered foods">Chocolate-covered foods</a></li> <li><a href="/wiki/Mint_chocolate" title="Mint chocolate">Mint chocolate</a></li> <li><a href="/wiki/Mole_(sauce)" title="Mole (sauce)">Mole</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;background: #7B3F00; color: white;">Processes</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/Aerated_chocolate" title="Aerated chocolate">Aerated chocolate</a></li> <li><a href="/wiki/Broma_process" title="Broma process">Broma process</a></li> <li><a href="/wiki/Conching" title="Conching">Conching</a></li> <li><a href="/wiki/Dutch_process_cocoa" title="Dutch process cocoa">Dutch process</a></li> <li><a href="/wiki/Enrober" title="Enrober">Enrober</a></li> <li><a href="/wiki/Sugar_crust" title="Sugar crust">Sugar crust</a></li> <li><a href="/wiki/Tempered_chocolate" title="Tempered chocolate">Tempering</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;background: #7B3F00; color: white;">Industry</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/Bean-to-bar" title="Bean-to-bar">Bean-to-bar</a> <ul><li><a href="/wiki/List_of_bean-to-bar_chocolate_manufacturers" title="List of bean-to-bar chocolate manufacturers">Manufacturers</a></li></ul></li> <li><a href="/wiki/Big_Chocolate" title="Big Chocolate">Big Chocolate</a></li> <li><a href="/wiki/Chocolaterie" title="Chocolaterie">Chocolaterie</a></li> <li><a href="/wiki/Chocolatier" title="Chocolatier">Chocolatier</a></li> <li><a href="/wiki/C%C3%B4te_d%27Ivoire%E2%80%93Ghana_Cocoa_Initiative" title="Côte d'Ivoire–Ghana Cocoa Initiative">Côte d'Ivoire–Ghana Cocoa Initiative</a></li> <li><i><a href="/wiki/The_Dark_Side_of_Chocolate" title="The Dark Side of Chocolate">The Dark Side of Chocolate</a></i></li> <li><a href="/wiki/Environmental_impact_of_cocoa_production" title="Environmental impact of cocoa production">Environmental impact</a></li> <li><a href="/wiki/European_Cocoa_and_Chocolate_Directive" title="European Cocoa and Chocolate Directive">European Cocoa and Chocolate Directive</a></li> <li><a href="/wiki/Fair_trade_cocoa" title="Fair trade cocoa">Fair trade cocoa</a> <ul><li><a href="/wiki/Child_labour_in_cocoa_production" title="Child labour in cocoa production">Child labour in cocoa production</a></li></ul></li> <li><a href="/wiki/Harkin%E2%80%93Engel_Protocol" title="Harkin–Engel Protocol">Harkin–Engel Protocol</a></li> <li><a href="/wiki/International_Cocoa_Organization" title="International Cocoa Organization">International Cocoa Organization</a></li> <li><a href="/wiki/International_Cocoa_Quarantine_Centre" title="International Cocoa Quarantine Centre">International Cocoa Quarantine Centre</a></li> <li><a href="/wiki/Chocolate_industry_in_the_Philippines" title="Chocolate industry in the Philippines">Philippine chocolate industry</a></li> <li><a href="/wiki/Cocoa_production_in_Ghana" title="Cocoa production in Ghana">Production in Ghana</a> <ul><li><a href="/wiki/Ghana_Cocoa_Board" title="Ghana Cocoa Board">Ghana Cocoa Board</a></li></ul></li> <li><a href="/wiki/Cocoa_production_in_Ivory_Coast" title="Cocoa production in Ivory Coast">Production in Ivory Coast</a></li> <li><a href="/wiki/Cocoa_production_in_Nigeria" title="Cocoa production in Nigeria">Production in Nigeria</a></li> <li><a href="/wiki/Cocoa_production_in_S%C3%A3o_Tom%C3%A9_and_Pr%C3%ADncipe" title="Cocoa production in São Tomé and Príncipe">Production in São Tomé and Príncipe</a></li> <li><a href="/wiki/World_Cocoa_Foundation" title="World Cocoa Foundation">World Cocoa Foundation</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;background: #7B3F00; color: white;">By country</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/Belgian_chocolate" title="Belgian chocolate">Belgium</a></li> <li><a href="/wiki/French_chocolate" title="French chocolate">France</a></li> <li><a href="/wiki/Swiss_chocolate" title="Swiss chocolate">Switzerland</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;background: #7B3F00; color: white;">Other topics</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/Chocolate_addiction" title="Chocolate addiction">Chocolate addiction</a></li> <li><a href="/wiki/Chocolate_bloom" title="Chocolate bloom">Chocolate bloom</a></li> <li><a href="/wiki/Chocolate_fountain" title="Chocolate fountain">Chocolate fountain</a></li> <li><a href="/wiki/List_of_chocolate_museums" title="List of chocolate museums">Chocolate museums</a></li> <li><a href="/wiki/List_of_chocolatiers" title="List of chocolatiers">Chocolatiers</a></li> <li><a href="/wiki/Cocoa_smuggling" title="Cocoa smuggling">Cocoa smuggling</a></li> <li><a href="/wiki/History_of_chocolate" title="History of chocolate">History</a></li> <li><a href="/wiki/Chocolate_in_savory_cooking" title="Chocolate in savory cooking">In savory cooking</a></li> <li>Military chocolate <ul><li><a href="/wiki/Military_chocolate_(Switzerland)" title="Military chocolate (Switzerland)">Switzerland</a></li> <li><a href="/wiki/Military_chocolate_(United_States)" title="Military chocolate (United States)">United States</a></li></ul></li></ul> </div></td></tr><tr><td class="navbox-abovebelow" colspan="2" style="background: #7B3F00; color: white;"><div><div class="plainlist"> <ul><li><span class="noviewer" typeof="mw:File"><span title="Category"><img alt="" src="//upload.wikimedia.org/wikipedia/en/thumb/9/96/Symbol_category_class.svg/16px-Symbol_category_class.svg.png" decoding="async" width="16" height="16" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/9/96/Symbol_category_class.svg/23px-Symbol_category_class.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/9/96/Symbol_category_class.svg/31px-Symbol_category_class.svg.png 2x" data-file-width="180" data-file-height="185" /></span></span> <b><a href="/wiki/Category:Chocolate" title="Category:Chocolate"><span style="color:white">Category</span></a></b></li> <li><span class="noviewer" typeof="mw:File"><span title="Outline"><img alt="" src="//upload.wikimedia.org/wikipedia/commons/thumb/4/41/Global_thinking.svg/10px-Global_thinking.svg.png" decoding="async" width="10" height="16" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/4/41/Global_thinking.svg/15px-Global_thinking.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/4/41/Global_thinking.svg/21px-Global_thinking.svg.png 2x" data-file-width="130" data-file-height="200" /></span></span> <b><a href="/wiki/Outline_of_chocolate" title="Outline of chocolate"><span style="color:white">Outline</span></a></b></li></ul> </div></div></td></tr></tbody></table></div>    </div><noscript><img src="https://login.wikimedia.org/wiki/Special:CentralAutoLogin/start?type=1x1" alt="" width="1" height="1" style="border: none; position: absolute;"></noscript> <div class="printfooter" data-nosnippet="">Retrieved from "<a dir="ltr" href="https://en.wikipedia.org/w/index.php?title=Tyramine&oldid=1255510460">https://en.wikipedia.org/w/index.php?title=Tyramine&oldid=1255510460</a>"</div></div> <div id="catlinks" class="catlinks" data-mw="interface"><div id="mw-normal-catlinks" class="mw-normal-catlinks"><a href="/wiki/Help:Category" title="Help:Category">Categories</a>: <ul><li><a href="/wiki/Category:Drugs_not_assigned_an_ATC_code" title="Category:Drugs not assigned an ATC code">Drugs not assigned an ATC code</a></li><li><a href="/wiki/Category:Antihypotensive_agents" 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