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</div> </div> </div> </nav> <h1 id="firstHeading" class="firstHeading mw-first-heading"><span class="mw-page-title-main">Triptan</span></h1> <div id="p-lang-btn" class="vector-dropdown mw-portlet mw-portlet-lang" > <input type="checkbox" id="p-lang-btn-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-p-lang-btn" class="vector-dropdown-checkbox mw-interlanguage-selector" aria-label="Go to an article in another language. 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href="https://ca.wikipedia.org/wiki/Triptan" title="Triptan – Catalan" lang="ca" hreflang="ca" data-title="Triptan" 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/Triptan" title="Triptan – Czech" lang="cs" hreflang="cs" data-title="Triptan" data-language-autonym="Čeština" data-language-local-name="Czech" class="interlanguage-link-target"><span>Čeština</span></a></li><li class="interlanguage-link interwiki-da mw-list-item"><a href="https://da.wikipedia.org/wiki/Triptaner" title="Triptaner – Danish" lang="da" hreflang="da" data-title="Triptaner" data-language-autonym="Dansk" data-language-local-name="Danish" class="interlanguage-link-target"><span>Dansk</span></a></li><li class="interlanguage-link interwiki-de mw-list-item"><a href="https://de.wikipedia.org/wiki/Triptane" title="Triptane – German" lang="de" hreflang="de" data-title="Triptane" 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/Tript%C3%A1n" title="Triptán – Spanish" lang="es" hreflang="es" data-title="Triptán" data-language-autonym="Español" data-language-local-name="Spanish" class="interlanguage-link-target"><span>Español</span></a></li><li class="interlanguage-link interwiki-fa mw-list-item"><a href="https://fa.wikipedia.org/wiki/%D8%AA%D8%B1%DB%8C%D9%BE%D8%AA%D8%A7%D9%86_(%D8%AE%D8%A7%D9%86%D9%88%D8%A7%D8%AF%D9%87_%D8%AF%D8%A7%D8%B1%D9%88%DB%8C%DB%8C)" title="تریپتان (خانواده دارویی) – Persian" lang="fa" hreflang="fa" data-title="تریپتان (خانواده دارویی)" 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/Triptan" title="Triptan – French" lang="fr" hreflang="fr" data-title="Triptan" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target"><span>Français</span></a></li><li class="interlanguage-link interwiki-ko mw-list-item"><a href="https://ko.wikipedia.org/wiki/%ED%8A%B8%EB%A6%BD%ED%83%84" title="트립탄 – Korean" lang="ko" hreflang="ko" data-title="트립탄" data-language-autonym="한국어" data-language-local-name="Korean" class="interlanguage-link-target"><span>한국어</span></a></li><li class="interlanguage-link interwiki-id mw-list-item"><a href="https://id.wikipedia.org/wiki/Triptan" title="Triptan – Indonesian" lang="id" hreflang="id" data-title="Triptan" data-language-autonym="Bahasa Indonesia" data-language-local-name="Indonesian" class="interlanguage-link-target"><span>Bahasa Indonesia</span></a></li><li class="interlanguage-link interwiki-it mw-list-item"><a href="https://it.wikipedia.org/wiki/Triptani" title="Triptani – Italian" lang="it" hreflang="it" data-title="Triptani" data-language-autonym="Italiano" data-language-local-name="Italian" class="interlanguage-link-target"><span>Italiano</span></a></li><li class="interlanguage-link interwiki-mk mw-list-item"><a href="https://mk.wikipedia.org/wiki/%D0%A2%D1%80%D0%B8%D0%BF%D1%82%D0%B0%D0%BD" title="Триптан – Macedonian" lang="mk" hreflang="mk" data-title="Триптан" data-language-autonym="Македонски" data-language-local-name="Macedonian" class="interlanguage-link-target"><span>Македонски</span></a></li><li class="interlanguage-link interwiki-ja mw-list-item"><a href="https://ja.wikipedia.org/wiki/%E3%83%88%E3%83%AA%E3%83%97%E3%82%BF%E3%83%B3_(%E5%8C%BB%E8%96%AC%E5%93%81)" title="トリプタン (医薬品) – Japanese" lang="ja" hreflang="ja" data-title="トリプタン (医薬品)" data-language-autonym="日本語" data-language-local-name="Japanese" class="interlanguage-link-target"><span>日本語</span></a></li><li class="interlanguage-link interwiki-no mw-list-item"><a href="https://no.wikipedia.org/wiki/Triptan" title="Triptan – Norwegian Bokmål" lang="nb" hreflang="nb" data-title="Triptan" data-language-autonym="Norsk bokmål" data-language-local-name="Norwegian Bokmål" class="interlanguage-link-target"><span>Norsk bokmål</span></a></li><li class="interlanguage-link interwiki-pl mw-list-item"><a href="https://pl.wikipedia.org/wiki/Tryptany" title="Tryptany – Polish" lang="pl" hreflang="pl" data-title="Tryptany" 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/Triptano" title="Triptano – Portuguese" lang="pt" hreflang="pt" data-title="Triptano" 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/Triptan" title="Triptan – Romanian" lang="ro" hreflang="ro" data-title="Triptan" data-language-autonym="Română" data-language-local-name="Romanian" class="interlanguage-link-target"><span>Română</span></a></li><li class="interlanguage-link interwiki-sl mw-list-item"><a href="https://sl.wikipedia.org/wiki/Triptani" title="Triptani – Slovenian" lang="sl" hreflang="sl" data-title="Triptani" data-language-autonym="Slovenščina" data-language-local-name="Slovenian" class="interlanguage-link-target"><span>Slovenščina</span></a></li><li class="interlanguage-link interwiki-fi mw-list-item"><a href="https://fi.wikipedia.org/wiki/Triptaanit" title="Triptaanit – Finnish" lang="fi" hreflang="fi" data-title="Triptaanit" 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/Triptaner" title="Triptaner – Swedish" lang="sv" hreflang="sv" data-title="Triptaner" 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/Triptan" title="Triptan – Turkish" lang="tr" hreflang="tr" data-title="Triptan" 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%D1%80%D0%B8%D0%BF%D1%82%D0%B0%D0%BD%D0%B8" title="Триптани – Ukrainian" lang="uk" hreflang="uk" data-title="Триптани" data-language-autonym="Українська" data-language-local-name="Ukrainian" class="interlanguage-link-target"><span>Українська</span></a></li> </ul> <div class="after-portlet after-portlet-lang"><span class="wb-langlinks-edit wb-langlinks-link"><a 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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/Tryptan" class="mw-redirect" title="Tryptan">Tryptan</a> (the trade name of amino acid tryptophan) or the hydrocarbon <a href="/wiki/Triptane" title="Triptane">triptane</a> or <a href="/wiki/Oxitriptan" title="Oxitriptan">Oxitriptan</a>.</div> <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"><tbody><tr><th colspan="2" class="infobox-above" style="background-color: #ddbbee">Triptans</th></tr><tr><td colspan="2" class="infobox-subheader"><i><a href="/wiki/Drug_class" title="Drug class">Drug class</a></i></td></tr><tr><td colspan="2" class="infobox-image"><span class="mw-default-size skin-invert-image" typeof="mw:File/Frameless"><a href="/wiki/File:Sumatriptan.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/3/38/Sumatriptan.svg/280px-Sumatriptan.svg.png" decoding="async" width="280" height="175" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/3/38/Sumatriptan.svg/420px-Sumatriptan.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/3/38/Sumatriptan.svg/560px-Sumatriptan.svg.png 2x" data-file-width="640" data-file-height="400" /></a></span><div class="infobox-caption"><a href="/wiki/Chemical_structure" title="Chemical structure">Chemical structure</a> of <a href="/wiki/Sumatriptan" title="Sumatriptan">sumatriptan</a>, the prototypical triptan</div></td></tr><tr><th colspan="2" class="infobox-header" style="background: #e8e8e8;">Class identifiers</th></tr><tr><th scope="row" class="infobox-label">Use</th><td class="infobox-data"><a href="/wiki/Migraine" title="Migraine">Migraine</a>, <a href="/wiki/Cluster_headache" title="Cluster headache">cluster headache</a></td></tr><tr><th scope="row" class="infobox-label"><a href="/wiki/Anatomical_Therapeutic_Chemical_Classification_System" title="Anatomical Therapeutic Chemical Classification System">ATC code</a></th><td class="infobox-data"><a href="/wiki/ATC_code_N02CC" class="mw-redirect" title="ATC code N02CC">N02CC</a></td></tr><tr><th scope="row" class="infobox-label"><a href="/wiki/Biological_target" title="Biological target">Biological target</a></th><td class="infobox-data"><a href="/wiki/5-HT1B_receptor" title="5-HT1B receptor">5-HT<sub>1B</sub> receptor</a>,<br /><a href="/wiki/5-HT1D_receptor" title="5-HT1D receptor">5-HT<sub>1D</sub> receptor</a></td></tr><tr><th colspan="2" class="infobox-header" style="background: #e8e8e8;">Legal status</th></tr><tr><td colspan="2" class="infobox-below" style="background: #e8e8e8; text-align: center"><a href="https://www.wikidata.org/wiki/Q423866" class="extiw" title="d:Q423866">In Wikidata</a></td></tr></tbody></table> <p><b>Triptans</b> are a family of <a href="/wiki/Tryptamine" title="Tryptamine">tryptamine</a>-based <a href="/wiki/Medication" title="Medication">drugs</a> used as <a href="/wiki/Abortive_medication" class="mw-redirect" title="Abortive medication">abortive medication</a> in the treatment of <a href="/wiki/Migraine" title="Migraine">migraines</a> and <a href="/wiki/Cluster_headache" title="Cluster headache">cluster headaches</a>. This drug class was first commercially introduced in the 1990s. While effective at treating individual headaches, they do not provide preventive treatment and are not considered a <a href="/wiki/Cure" title="Cure">cure</a>. They are not effective for the treatment of <a href="/wiki/Tension_headache" title="Tension headache">tension–type headache</a>,<sup id="cite_ref-Mutschler_1-0" class="reference"><a href="#cite_note-Mutschler-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> except in persons who also experience migraines.<sup id="cite_ref-Green_2015_2-0" class="reference"><a href="#cite_note-Green_2015-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> Triptans do not relieve other kinds of <a href="/wiki/Pain" title="Pain">pain</a>. </p><p>The drugs of this class act as <a href="/wiki/Agonists" class="mw-redirect" title="Agonists">agonists</a> for <a href="/wiki/Serotonin" title="Serotonin">serotonin</a> <a href="/wiki/5-HT1B_receptor" title="5-HT1B receptor">5-HT<sub>1B</sub></a> and <a href="/wiki/5-HT1D_receptor" title="5-HT1D receptor">5-HT<sub>1D</sub></a> receptors at blood vessels and nerve endings in the brain. The first clinically available triptan was <a href="/wiki/Sumatriptan" title="Sumatriptan">sumatriptan</a>, which has been marketed since 1991. Triptans have largely replaced <a href="/wiki/Ergotamine" title="Ergotamine">ergotamines</a>, an older class of medications used to relieve migraine and cluster headaches.<sup id="cite_ref-3" class="reference"><a href="#cite_note-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Medical_uses">Medical uses</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Triptan&action=edit&section=1" title="Edit section: Medical uses"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <table class="wikitable" style="float:right; margin:auto 1em auto 1em;"> <caption>Examples of triptans </caption> <tbody><tr> <td style="vertical-align:bottom"><span class="skin-invert-image" typeof="mw:File"><a href="/wiki/File:Sumatriptan.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/3/38/Sumatriptan.svg/150px-Sumatriptan.svg.png" decoding="async" width="150" height="94" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/3/38/Sumatriptan.svg/225px-Sumatriptan.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/3/38/Sumatriptan.svg/300px-Sumatriptan.svg.png 2x" data-file-width="640" data-file-height="400" /></a></span><br /><a href="/wiki/Sumatriptan" title="Sumatriptan">sumatriptan</a> </td> <td style="vertical-align:bottom"><span class="skin-invert-image" typeof="mw:File"><a href="/wiki/File:Rizatriptan.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/a/af/Rizatriptan.png/150px-Rizatriptan.png" decoding="async" width="150" height="90" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/af/Rizatriptan.png/225px-Rizatriptan.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/af/Rizatriptan.png/300px-Rizatriptan.png 2x" data-file-width="2940" data-file-height="1761" /></a></span><br /><a href="/wiki/Rizatriptan" title="Rizatriptan">rizatriptan</a> </td> <td style="vertical-align:bottom"><span class="skin-invert-image" typeof="mw:File"><a href="/wiki/File:Naratriptan_structure.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/9/90/Naratriptan_structure.png/150px-Naratriptan_structure.png" decoding="async" width="150" height="96" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/9/90/Naratriptan_structure.png/225px-Naratriptan_structure.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/9/90/Naratriptan_structure.png/300px-Naratriptan_structure.png 2x" data-file-width="553" data-file-height="355" /></a></span><br /><a href="/wiki/Naratriptan" title="Naratriptan">naratriptan</a> </td></tr> <tr> <td style="vertical-align:bottom"><span class="skin-invert-image" typeof="mw:File"><a href="/wiki/File:Eletriptan_skeletal.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/7/78/Eletriptan_skeletal.svg/150px-Eletriptan_skeletal.svg.png" decoding="async" width="150" height="77" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/7/78/Eletriptan_skeletal.svg/225px-Eletriptan_skeletal.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/7/78/Eletriptan_skeletal.svg/300px-Eletriptan_skeletal.svg.png 2x" data-file-width="826" data-file-height="425" /></a></span><br /><a href="/wiki/Eletriptan" title="Eletriptan">eletriptan</a> </td> <td style="vertical-align:bottom"><span class="skin-invert-image" typeof="mw:File"><a href="/wiki/File:Donitriptan.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/8/8c/Donitriptan.svg/150px-Donitriptan.svg.png" decoding="async" width="150" height="72" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/8/8c/Donitriptan.svg/225px-Donitriptan.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/8/8c/Donitriptan.svg/300px-Donitriptan.svg.png 2x" data-file-width="2115" data-file-height="1020" /></a></span><br /><a href="/wiki/Donitriptan" title="Donitriptan">donitriptan</a> </td> <td style="vertical-align:bottom"><span class="skin-invert-image" typeof="mw:File"><a href="/wiki/File:Almotriptan_skeletal.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/9/95/Almotriptan_skeletal.svg/150px-Almotriptan_skeletal.svg.png" decoding="async" width="150" height="87" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/9/95/Almotriptan_skeletal.svg/225px-Almotriptan_skeletal.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/9/95/Almotriptan_skeletal.svg/300px-Almotriptan_skeletal.svg.png 2x" data-file-width="695" data-file-height="405" /></a></span><br /><a href="/wiki/Almotriptan" title="Almotriptan">almotriptan</a> </td></tr> <tr> <td style="vertical-align:bottom"><span class="skin-invert-image" typeof="mw:File"><a href="/wiki/File:Frovatriptan_structure.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/e/e4/Frovatriptan_structure.svg/150px-Frovatriptan_structure.svg.png" decoding="async" width="150" height="98" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/e4/Frovatriptan_structure.svg/225px-Frovatriptan_structure.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/e/e4/Frovatriptan_structure.svg/300px-Frovatriptan_structure.svg.png 2x" data-file-width="512" data-file-height="336" /></a></span><br /><a href="/wiki/Frovatriptan" title="Frovatriptan">frovatriptan</a> </td> <td style="vertical-align:bottom"><span class="skin-invert-image" typeof="mw:File"><a href="/wiki/File:Avitriptan.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/f/f5/Avitriptan.png/150px-Avitriptan.png" decoding="async" width="150" height="76" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/f/f5/Avitriptan.png/225px-Avitriptan.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/f/f5/Avitriptan.png/300px-Avitriptan.png 2x" data-file-width="2490" data-file-height="1254" /></a></span><br /><a href="/wiki/Avitriptan" title="Avitriptan">avitriptan</a> </td> <td style="vertical-align:bottom"><span class="skin-invert-image" typeof="mw:File"><a href="/wiki/File:Zolmitriptan.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/9/94/Zolmitriptan.svg/150px-Zolmitriptan.svg.png" decoding="async" width="150" height="82" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/9/94/Zolmitriptan.svg/225px-Zolmitriptan.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/9/94/Zolmitriptan.svg/300px-Zolmitriptan.svg.png 2x" data-file-width="1697" data-file-height="932" /></a></span><br /><a href="/wiki/Zolmitriptan" title="Zolmitriptan">zolmitriptan</a> </td></tr> <tr> <td style="vertical-align:bottom"><span class="skin-invert-image" typeof="mw:File"><a href="/wiki/File:LY334370.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/1/1a/LY334370.svg/150px-LY334370.svg.png" decoding="async" width="150" height="99" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/1/1a/LY334370.svg/225px-LY334370.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/1/1a/LY334370.svg/300px-LY334370.svg.png 2x" data-file-width="720" data-file-height="475" /></a></span><br /><a href="/wiki/LY-334370" title="LY-334370">LY-334370</a> </td> <td style="vertical-align:bottom"><span class="skin-invert-image" typeof="mw:File"><a href="/wiki/File:L_694_247.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/e/e1/L_694_247.svg/150px-L_694_247.svg.png" decoding="async" width="150" height="87" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/e1/L_694_247.svg/225px-L_694_247.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/e/e1/L_694_247.svg/300px-L_694_247.svg.png 2x" data-file-width="450" data-file-height="261" /></a></span><br /><a href="/wiki/L-694247" title="L-694247">L-694247</a> </td> <td> </td></tr></tbody></table> <div class="mw-heading mw-heading3"><h3 id="Migraine">Migraine</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Triptan&action=edit&section=2" title="Edit section: Migraine"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Triptans are used for the treatment of severe migraine attacks or those that do not respond to <a href="/wiki/NSAID" class="mw-redirect" title="NSAID">NSAIDs</a><sup id="cite_ref-pmid17405970_4-0" class="reference"><a href="#cite_note-pmid17405970-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> or other <a href="/wiki/Over-the-counter_drug" title="Over-the-counter drug">over-the-counter</a> drugs.<sup id="cite_ref-pmid11112243_5-0" class="reference"><a href="#cite_note-pmid11112243-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> Triptans are a mid-line treatment suitable for many migraineurs with typical attacks. They may not work for atypical or unusually severe migraine attacks, transformed migraine, or status migrainosus (continuous migraine). </p><p>Triptans are highly effective, reducing the symptoms or aborting the attack within 30 to 90 minutes in 70–80% of patients.<sup id="cite_ref-6" class="reference"><a href="#cite_note-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> </p><p>A test measuring a person's skin <a href="/wiki/Allodynia" title="Allodynia">sensitivity</a> during a migraine may indicate whether the individual will respond to treatment with triptans.<sup id="cite_ref-7" class="reference"><a href="#cite_note-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> Triptans are most effective in those with no skin sensitivity; with skin sensitivity, it is best to take triptans within twenty minutes of the headache's onset.<sup id="cite_ref-8" class="reference"><a href="#cite_note-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> </p><p>Oral <a href="/wiki/Rizatriptan" title="Rizatriptan">rizatriptan</a> and nasal <a href="/wiki/Zolmitriptan" title="Zolmitriptan">zolmitriptan</a> are the most used triptans for migraines in children.<sup id="cite_ref-9" class="reference"><a href="#cite_note-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading4"><h4 id="Correct_timing_of_intake">Correct timing of intake</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Triptan&action=edit&section=3" title="Edit section: Correct timing of intake"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Triptans should be taken as soon as possible after the onset of pain. In case of migraine with <a href="/wiki/Aura_(migraine)" class="mw-redirect" title="Aura (migraine)">aura</a> they are to be taken after the aura and with the onset of pain.<sup id="cite_ref-AC_10-0" class="reference"><a href="#cite_note-AC-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> If taken too early, they may not have the full effect on symptom reduction, and in case of an aura, they can worsen the aura. It is assumed that blood vessels are <a href="/wiki/Vasoconstriction" title="Vasoconstriction">constricted</a> during the aura phase and <a href="/wiki/Vasodilation" title="Vasodilation">dilated</a> during the pain phase, so a constrictive medication like a triptan is not recommended during the aura.<sup id="cite_ref-11" class="reference"><a href="#cite_note-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Cluster_headache">Cluster headache</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Triptan&action=edit&section=4" title="Edit section: Cluster headache"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Triptans are effective for the treatment of <a href="/wiki/Cluster_headache" title="Cluster headache">cluster headache</a>. This has been demonstrated for <a href="/wiki/Subcutaneous_injection" class="mw-redirect" title="Subcutaneous injection">subcutaneous</a> sumatriptan and <a href="/wiki/Intranasal" class="mw-redirect" title="Intranasal">intranasal</a> zolmitriptan, the former of which is more effective according to a 2013 <a href="/wiki/Cochrane_review" class="mw-redirect" title="Cochrane review">Cochrane review</a>. Tablets were not considered appropriate in this review.<sup id="cite_ref-12" class="reference"><a href="#cite_note-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Altitude_sickness">Altitude sickness</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Triptan&action=edit&section=5" title="Edit section: Altitude sickness"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>A single <a href="/wiki/Randomized_controlled_trial" title="Randomized controlled trial">randomized controlled trial</a> found that sumatriptan may be able to prevent <a href="/wiki/Altitude_sickness" title="Altitude sickness">altitude sickness</a>.<sup id="cite_ref-pmid17557349_13-0" class="reference"><a href="#cite_note-pmid17557349-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Available_forms">Available forms</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Triptan&action=edit&section=6" title="Edit section: Available forms"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>All marketed triptans are available in <a href="/wiki/Oral_administration" title="Oral administration">oral</a> form; some in form of <a href="/wiki/Sublingual" class="mw-redirect" title="Sublingual">sublingual</a> tablets.<sup id="cite_ref-AC_10-1" class="reference"><a href="#cite_note-AC-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> Sumatriptan and zolmitriptan are also available as <a href="/wiki/Nasal_spray" title="Nasal spray">nasal sprays</a>.<sup id="cite_ref-AC_10-2" class="reference"><a href="#cite_note-AC-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-14" class="reference"><a href="#cite_note-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup> For sumatriptan, a number of other application forms are marketed: <a href="/wiki/Suppositories" class="mw-redirect" title="Suppositories">suppositories</a>, a subcutaneous injection,<sup id="cite_ref-AC_10-3" class="reference"><a href="#cite_note-AC-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> an <a href="/wiki/Iontophoretic" class="mw-redirect" title="Iontophoretic">iontophoretic</a> transdermal patch, which uses low voltage controlled by a pre-programmed microchip to deliver a single dose of sumatriptan through the skin within 30 minutes;<sup id="cite_ref-:0_15-0" class="reference"><a href="#cite_note-:0-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup> a drug-device combination containing sumatriptan powder that is "breath powered" allowing the user to blow sumatriptan powder in to their nostrils;<sup id="cite_ref-16" class="reference"><a href="#cite_note-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup> as well as a needle-free injection system that works with air pressure.<sup id="cite_ref-Zogenix_17-0" class="reference"><a href="#cite_note-Zogenix-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup> </p> <table class="wikitable"> <caption>Formulations<sup id="cite_ref-18" class="reference"><a href="#cite_note-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup> </caption> <tbody><tr> <th>Tablet </th> <th>Oral disintegrating tablets </th> <th>Nasal spray </th> <th>Subcutaneous injection </th> <th>Rectal suppository </th></tr> <tr> <td>all triptans </td> <td>rizatriptan </td> <td>sumatriptan </td> <td>sumatriptan </td> <td>sumatriptan </td></tr> <tr> <td> </td> <td>zolmitriptan </td> <td>zolmitriptan </td> <td> </td> <td> </td></tr></tbody></table> <div class="mw-heading mw-heading2"><h2 id="Contraindications">Contraindications</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Triptan&action=edit&section=7" title="Edit section: Contraindications"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>All triptans are contraindicated in patients with <a href="/wiki/Cardiovascular_disease" title="Cardiovascular disease">cardiovascular diseases</a> (<a href="/wiki/Coronary_spasm" class="mw-redirect" title="Coronary spasm">coronary spasms</a>, symptomatic <a href="/wiki/Coronary_artery_disease" title="Coronary artery disease">coronary artery disease</a>, after a <a href="/wiki/Heart_attack" class="mw-redirect" title="Heart attack">heart attack</a> or <a href="/wiki/Stroke" title="Stroke">stroke</a>, uncontrolled <a href="/wiki/Hypertension" title="Hypertension">hypertension</a>, <a href="/wiki/Raynaud%27s_disease" class="mw-redirect" title="Raynaud's disease">Raynaud's disease</a>, <a href="/wiki/Peripheral_artery_disease" title="Peripheral artery disease">peripheral artery disease</a>).<sup id="cite_ref-19" class="reference"><a href="#cite_note-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-20" class="reference"><a href="#cite_note-20"><span class="cite-bracket">[</span>20<span class="cite-bracket">]</span></a></sup> Most triptans are also contraindicated during pregnancy and breastfeeding and for patients younger than 18; but sumatriptan and zolmitriptan nasal sprays are also approved for youths over 12.<sup id="cite_ref-Mutschler_1-1" class="reference"><a href="#cite_note-Mutschler-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> In spite of expert opinion and evidence to the contrary, the FDA and some other drug governance bodies have stated that <a href="/wiki/Monoamine_oxidase_inhibitor" title="Monoamine oxidase inhibitor">monoamine oxidase inhibitors</a> are contraindicated for sumatriptan, zolmitriptan and rizatriptan,<sup id="cite_ref-Ferrari_21-0" class="reference"><a href="#cite_note-Ferrari-21"><span class="cite-bracket">[</span>21<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Goodman_22-0" class="reference"><a href="#cite_note-Goodman-22"><span class="cite-bracket">[</span>22<span class="cite-bracket">]</span></a></sup> and combination with <a href="/wiki/Ergot_alkaloid" class="mw-redirect" title="Ergot alkaloid">ergot alkaloids</a> such as <a href="/wiki/Ergotamine" title="Ergotamine">ergotamine</a> for all substances.<sup id="cite_ref-AC_10-4" class="reference"><a href="#cite_note-AC-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> </p><p>At least two triptans (sumatriptan and rizatriptan) have been listed under the unacceptable medication by the <a href="/wiki/Canadian_Blood_Services" title="Canadian Blood Services">Canadian Blood Services</a> as a potential risk to the recipient; hence, donors are required not to have taken the medication for the last 72 hours.<sup id="cite_ref-23" class="reference"><a href="#cite_note-23"><span class="cite-bracket">[</span>23<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Adverse_effects">Adverse effects</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Triptan&action=edit&section=8" title="Edit section: Adverse effects"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Triptans have few side effects if used in correct dosage and frequency. The most common adverse effect is recurrence of migraine. A <a href="/wiki/Systematic_review" title="Systematic review">systematic review</a> found that "rizatriptan 10 mg was the only triptan with a recurrence rate greater than that of placebo".<sup id="cite_ref-pmid17883520_24-0" class="reference"><a href="#cite_note-pmid17883520-24"><span class="cite-bracket">[</span>24<span class="cite-bracket">]</span></a></sup> </p><p>There is a theoretical risk of coronary spasm in patients with established heart disease, and cardiac events after taking triptans may rarely occur.<sup id="cite_ref-pmid9827245_25-0" class="reference"><a href="#cite_note-pmid9827245-25"><span class="cite-bracket">[</span>25<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Interactions">Interactions</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Triptan&action=edit&section=9" title="Edit section: Interactions"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Combination of triptans with other serotonergic drugs such as ergot alkaloids, monoamine oxidase inhibitors, <a href="/wiki/Selective_serotonin_reuptake_inhibitor" title="Selective serotonin reuptake inhibitor">selective serotonin reuptake inhibitors</a> (SSRIs), <a href="/wiki/Serotonin%E2%80%93norepinephrine_reuptake_inhibitor" title="Serotonin–norepinephrine reuptake inhibitor">serotonin–norepinephrine reuptake inhibitors</a> (SNRIs) or <a href="/wiki/St_John%27s_wort" class="mw-redirect" title="St John's wort">St John's wort</a> has been alleged to induce symptoms of a <a href="/wiki/Serotonin_syndrome" title="Serotonin syndrome">serotonin syndrome</a> (a syndrome of changes in mental status, autonomic instability, neuromuscular abnormalities, and gastrointestinal symptoms),<sup id="cite_ref-Mutschler_1-2" class="reference"><a href="#cite_note-Mutschler-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-AC_10-5" class="reference"><a href="#cite_note-AC-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> whereas scientific studies indicate there is no potential for life-threatening serotonin syndrome in patients taking triptans and SSRI or SNRIs at the same time, although the FDA has officially stated otherwise.<sup id="cite_ref-Rolan_2012_pp._949–957_26-0" class="reference"><a href="#cite_note-Rolan_2012_pp._949–957-26"><span class="cite-bracket">[</span>26<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-27" class="reference"><a href="#cite_note-27"><span class="cite-bracket">[</span>27<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-28" class="reference"><a href="#cite_note-28"><span class="cite-bracket">[</span>28<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-29" class="reference"><a href="#cite_note-29"><span class="cite-bracket">[</span>29<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-30" class="reference"><a href="#cite_note-30"><span class="cite-bracket">[</span>30<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-31" class="reference"><a href="#cite_note-31"><span class="cite-bracket">[</span>31<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-FDA_ALERT_[7/2006]:_32-0" class="reference"><a href="#cite_note-FDA_ALERT_[7/2006]:-32"><span class="cite-bracket">[</span>32<span class="cite-bracket">]</span></a></sup> Combining triptans with ergot alkaloids is contraindicated because of the danger of coronary spasms.<sup id="cite_ref-AC_10-6" class="reference"><a href="#cite_note-AC-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> </p><p>In a study from <a href="/wiki/Harvard_Medical_School" title="Harvard Medical School">Harvard Medical School</a> and the <a href="/wiki/University_of_Florida_College_of_Medicine" title="University of Florida College of Medicine">University of Florida College of Medicine</a> involving 47,968 patients and published on 26 February 2018, concomitant use of a <a href="/wiki/Selective_serotonin_reuptake_inhibitor" title="Selective serotonin reuptake inhibitor">selective serotonin reuptake inhibitor</a> or <a href="/wiki/Selective_norepinephrine_reuptake_inhibitor" title="Selective norepinephrine reuptake inhibitor">selective norepinephrine reuptake inhibitor</a> for <a href="/wiki/Major_depressive_disorder" title="Major depressive disorder">depression</a> with a triptan for <a href="/wiki/Migraine" title="Migraine">migraine</a> did not demonstrate an increased risk of the <a href="/wiki/Serotonin_syndrome" title="Serotonin syndrome">serotonin syndrome</a>.<sup id="cite_ref-33" class="reference"><a href="#cite_note-33"><span class="cite-bracket">[</span>33<span class="cite-bracket">]</span></a></sup> </p><p><a href="/wiki/Pharmacokinetic" class="mw-redirect" title="Pharmacokinetic">Pharmacokinetic</a> interactions (for example, mediated by <a href="/wiki/Cytochrome_P450" title="Cytochrome P450">CYP</a> liver enzymes or <a href="/wiki/Transporter_protein" class="mw-redirect" title="Transporter protein">transporter proteins</a>) are different for the individual substances; for most triptans, they are mild to absent. Eletriptan blood plasma levels are increased by strong inhibitors of <a href="/wiki/CYP3A4" title="CYP3A4">CYP3A4</a>, and frovatriptan levels by <a href="/wiki/CYP1A2" title="CYP1A2">CYP1A2</a> inhibitors such as <a href="/wiki/Fluvoxamine" title="Fluvoxamine">fluvoxamine</a>.<sup id="cite_ref-AC_10-7" class="reference"><a href="#cite_note-AC-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Pharmacology">Pharmacology</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Triptan&action=edit&section=10" title="Edit section: Pharmacology"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Mechanism_of_action">Mechanism of action</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Triptan&action=edit&section=11" title="Edit section: Mechanism of action"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">Further information: <a href="/wiki/Discovery_and_development_of_triptans" title="Discovery and development of triptans">Discovery and development of triptans</a> and <a href="/wiki/Serotonin_receptor_agonist" title="Serotonin receptor agonist">Serotonin receptor agonist</a></div> <p>Their action is attributed to their <a href="/wiki/Receptor_agonist" class="mw-redirect" title="Receptor agonist">agonist</a><sup id="cite_ref-Tepper_34-0" class="reference"><a href="#cite_note-Tepper-34"><span class="cite-bracket">[</span>34<span class="cite-bracket">]</span></a></sup> effects on <a href="/wiki/Serotonin" title="Serotonin">serotonin</a> <a href="/wiki/5-HT1B_receptor" title="5-HT1B receptor">5-HT<sub>1B</sub></a> and <a href="/wiki/5-HT1D_receptor" title="5-HT1D receptor">5-HT<sub>1D</sub> receptors</a> in blood vessels (causing their <a href="/wiki/Vasoconstriction" title="Vasoconstriction">constriction</a>) and nerve endings in the brain, and subsequent inhibition of pro-inflammatory <a href="/wiki/Neuropeptide" title="Neuropeptide">neuropeptide</a> release, including <a href="/wiki/CGRP" class="mw-redirect" title="CGRP">CGRP</a> and <a href="/wiki/Substance_P" title="Substance P">substance P</a>. Triptans are <a href="/wiki/Ligand_(biochemistry)#Receptor.2Fligand_binding_affinity" title="Ligand (biochemistry)">selective</a> agents for 5-HT<sub>1B</sub> and 5-HT<sub>1D</sub><sup id="cite_ref-Tepper_34-1" class="reference"><a href="#cite_note-Tepper-34"><span class="cite-bracket">[</span>34<span class="cite-bracket">]</span></a></sup> and have low or even no <a href="/wiki/Ligand_(biochemistry)#Receptor.2Fligand_binding_affinity" title="Ligand (biochemistry)">affinity</a> for other types of 5-HT receptors.<sup id="cite_ref-Goodman_22-1" class="reference"><a href="#cite_note-Goodman-22"><span class="cite-bracket">[</span>22<span class="cite-bracket">]</span></a></sup> </p><p>5-HT receptors are classified into seven different families named 5-HT<sub>1</sub> to 5-HT<sub>7</sub>. All receptors are <a href="/wiki/G_protein_coupled_receptors" class="mw-redirect" title="G protein coupled receptors">G protein coupled receptors</a> with seven transmembrane domains with the one exception of 5-HT<sub>3</sub> receptor which is a <a href="/wiki/Ligand_gated_ion_channel" class="mw-redirect" title="Ligand gated ion channel">ligand gated ion channel</a>. There is a high <a href="/wiki/Homology_(biology)" title="Homology (biology)">homology</a> in the amino acid sequence within each family. Each family couples to the same <a href="/wiki/Second_messenger_systems" class="mw-redirect" title="Second messenger systems">second messenger systems</a>. Subtypes of 5-HT<sub>1</sub> are the 5-HT<sub>1A</sub>, 5-HT<sub>1B</sub>, 5-HT<sub>1D</sub>, 5-HT<sub>1E</sub> and 5-HT<sub>1F</sub> receptors. All 5-HT<sub>1D</sub> receptors are coupled to inhibition of <a href="/wiki/Adenylate_cyclase" class="mw-redirect" title="Adenylate cyclase">adenylate cyclase</a>. 5-HT<sub>1B</sub> and 5-HT<sub>1D</sub> receptors have been difficult to distinguish on a pharmacological basis. After cloning two distinct genes for 5-HT<sub>1B</sub> and 5-HT<sub>1D</sub> receptors, a better insight into distribution and expression in different tissues was gained, except in brain tissue where they are overlapping in several areas.<sup id="cite_ref-Hamel,_E._1999_35-0" class="reference"><a href="#cite_note-Hamel,_E._1999-35"><span class="cite-bracket">[</span>35<span class="cite-bracket">]</span></a></sup> </p> <style data-mw-deduplicate="TemplateStyles:r1251242444">.mw-parser-output .ambox{border:1px solid #a2a9b1;border-left:10px solid #36c;background-color:#fbfbfb;box-sizing:border-box}.mw-parser-output .ambox+link+.ambox,.mw-parser-output .ambox+link+style+.ambox,.mw-parser-output .ambox+link+link+.ambox,.mw-parser-output .ambox+.mw-empty-elt+link+.ambox,.mw-parser-output .ambox+.mw-empty-elt+link+style+.ambox,.mw-parser-output .ambox+.mw-empty-elt+link+link+.ambox{margin-top:-1px}html body.mediawiki .mw-parser-output .ambox.mbox-small-left{margin:4px 1em 4px 0;overflow:hidden;width:238px;border-collapse:collapse;font-size:88%;line-height:1.25em}.mw-parser-output .ambox-speedy{border-left:10px solid #b32424;background-color:#fee7e6}.mw-parser-output .ambox-delete{border-left:10px solid #b32424}.mw-parser-output .ambox-content{border-left:10px solid #f28500}.mw-parser-output .ambox-style{border-left:10px solid #fc3}.mw-parser-output .ambox-move{border-left:10px solid #9932cc}.mw-parser-output .ambox-protection{border-left:10px solid #a2a9b1}.mw-parser-output .ambox .mbox-text{border:none;padding:0.25em 0.5em;width:100%}.mw-parser-output .ambox .mbox-image{border:none;padding:2px 0 2px 0.5em;text-align:center}.mw-parser-output .ambox .mbox-imageright{border:none;padding:2px 0.5em 2px 0;text-align:center}.mw-parser-output .ambox .mbox-empty-cell{border:none;padding:0;width:1px}.mw-parser-output .ambox .mbox-image-div{width:52px}@media(min-width:720px){.mw-parser-output .ambox{margin:0 10%}}@media print{body.ns-0 .mw-parser-output .ambox{display:none!important}}</style><table class="box-Technical plainlinks metadata ambox ambox-style ambox-technical" role="presentation"><tbody><tr><td class="mbox-image"><div class="mbox-image-div"><span typeof="mw:File"><span><img alt="" src="//upload.wikimedia.org/wikipedia/en/thumb/f/f2/Edit-clear.svg/40px-Edit-clear.svg.png" decoding="async" width="40" height="40" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/f2/Edit-clear.svg/60px-Edit-clear.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/f2/Edit-clear.svg/80px-Edit-clear.svg.png 2x" data-file-width="48" data-file-height="48" /></span></span></div></td><td class="mbox-text"><div class="mbox-text-span">This section <b>may be too technical for most readers to understand</b>.<span class="hide-when-compact"> Please <a class="external text" href="https://en.wikipedia.org/w/index.php?title=Triptan&action=edit">help improve it</a> to <a href="/wiki/Wikipedia:Make_technical_articles_understandable" title="Wikipedia:Make technical articles understandable">make it understandable to non-experts</a>, without removing the technical details.</span> <span class="date-container"><i>(<span class="date">October 2016</span>)</i></span><span class="hide-when-compact"><i> (<small><a href="/wiki/Help:Maintenance_template_removal" title="Help:Maintenance template removal">Learn how and when to remove this message</a></small>)</i></span></div></td></tr></tbody></table> <p>Most <a href="/wiki/Mammalian" class="mw-redirect" title="Mammalian">mammalian</a> species, including humans, have 5-HT<sub>1D</sub> binding sites widely distributed throughout the <a href="/wiki/Central_nervous_system" title="Central nervous system">central nervous system</a>. 5-HT<sub>1D</sub> receptors are found in all areas of the brain but they differ in quantity at each area.<sup id="cite_ref-Lowther_36-0" class="reference"><a href="#cite_note-Lowther-36"><span class="cite-bracket">[</span>36<span class="cite-bracket">]</span></a></sup> An important initiator of head pain is suggested to be the activation of <a href="/wiki/Trigeminovascular" class="mw-redirect" title="Trigeminovascular">trigeminovascular</a> <a href="/wiki/Afferent_nerve_fiber" title="Afferent nerve fiber">afferent</a> nerves which upon activation releases neuropeptides such as CGRP, substance P and <a href="/wiki/Neurokinin_A" title="Neurokinin A">neurokinin A</a>. Also they are thought to promote neurogenic inflammatory response important for sensitization of <a href="/wiki/Sensory_neuron" title="Sensory neuron">sensory</a> afferents, and also transmission and generation of head pain centrally. 5-HT<sub>1D</sub> has been found responsible for inhibition of neurogenic inflammation upon administration with sumatriptan and other related compounds that act on prejunctional 5-HT<sub>1D</sub> receptors.<sup id="cite_ref-Hamel,_E._1999_35-1" class="reference"><a href="#cite_note-Hamel,_E._1999-35"><span class="cite-bracket">[</span>35<span class="cite-bracket">]</span></a></sup> </p><p>All triptans, like the older drug <a href="/wiki/Dihydroergotamine" title="Dihydroergotamine">dihydroergotamine</a>, have agonistic effects on the 5-HT<sub>1D</sub> receptor. Comparison of sumatriptan and dihydroergotamine showed that dihydroergotamine has high affinity and sumatriptan has medium affinity for 5-HT<sub>1D</sub>.<sup id="cite_ref-Tepper_34-2" class="reference"><a href="#cite_note-Tepper-34"><span class="cite-bracket">[</span>34<span class="cite-bracket">]</span></a></sup> Triptans have at least three modes of action. These antimigraine mechanisms are: </p> <ol><li><a href="/wiki/Vasoconstriction" title="Vasoconstriction">vasoconstriction</a> of pain producing intra cranial extracerebral vessels by a direct effect on vascular smooth muscle. Sumatriptan and rizatriptan have been shown to cause vasoconstriction in the human <a href="/wiki/Middle_meningeal_arteries" class="mw-redirect" title="Middle meningeal arteries">middle meningeal arteries</a>.</li> <li>inhibition of vasoactive neuropeptide release by trigeminal terminals innervating intracranial vessels and the dura mater. The trigeminocervical complex has 5-HT<sub>1D</sub> receptors that bind dihydroergotamine and triptans in humans. Rizatriptan has been shown to block dural vasodilation and plasma protein extravasation by inhibiting the release of CGRP via activation of receptors on preganglionic trigeminal sensory nerver terminals. Sumatriptan is shown to inhibit potassium stimulated CGRP secretion from cultured trigeminal neurons in a dose dependant manner and may also inhibit the release of substance P.</li> <li>inhibition of <a href="/wiki/Nociceptive" class="mw-redirect" title="Nociceptive">nociceptive</a> <a href="/wiki/Neurotransmission" title="Neurotransmission">neurotransmission</a> within the trigeminocervical complex in the <a href="/wiki/Brainstem" title="Brainstem">brainstem</a> and upper cervical spinal column. Rizatriptan has central trigeminal antinociceptive activity.</li></ol> <p>Other possibilities of triptans in antimigraine effects are modulation of <a href="/wiki/Nitric_oxide" title="Nitric oxide">nitric oxide</a> dependent <a href="/wiki/Signal_transduction_pathways" class="mw-redirect" title="Signal transduction pathways">signal transduction pathways</a>, nitric oxide scavenging in the brain, and sodium dependent cell metabolic activity.<sup id="cite_ref-37" class="reference"><a href="#cite_note-37"><span class="cite-bracket">[</span>37<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Tepper_34-3" class="reference"><a href="#cite_note-Tepper-34"><span class="cite-bracket">[</span>34<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Pharmacokinetics">Pharmacokinetics</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Triptan&action=edit&section=12" title="Edit section: Pharmacokinetics"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Triptans have a wide variety of <a href="/wiki/Pharmacokinetic" class="mw-redirect" title="Pharmacokinetic">pharmacokinetic</a> properties. <a href="/wiki/Bioavailability" title="Bioavailability">Bioavailability</a> is between 14% and 70%, <a href="/wiki/Biological_half-life" title="Biological half-life">biological half-life</a> (T<sub>1/2</sub>) is between 2 and 26 hours. Their good ability to cross the <a href="/wiki/Blood%E2%80%93brain_barrier" title="Blood–brain barrier">blood–brain barrier</a> and the rather long half life of some triptans may result in lower frequencies of migraine recurrence.<sup id="cite_ref-Goodman_22-2" class="reference"><a href="#cite_note-Goodman-22"><span class="cite-bracket">[</span>22<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Bigal_38-0" class="reference"><a href="#cite_note-Bigal-38"><span class="cite-bracket">[</span>38<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Armstrong_39-0" class="reference"><a href="#cite_note-Armstrong-39"><span class="cite-bracket">[</span>39<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Mathew_40-0" class="reference"><a href="#cite_note-Mathew-40"><span class="cite-bracket">[</span>40<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Comparison">Comparison</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Triptan&action=edit&section=13" title="Edit section: Comparison"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <table class="wikitable" style="margin: 1em auto 1em auto;"> <caption>Comparative pharmacology of triptans, oral formulations<sup id="cite_ref-Goodman_22-3" class="reference"><a href="#cite_note-Goodman-22"><span class="cite-bracket">[</span>22<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Bigal_38-1" class="reference"><a href="#cite_note-Bigal-38"><span class="cite-bracket">[</span>38<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Armstrong_39-1" class="reference"><a href="#cite_note-Armstrong-39"><span class="cite-bracket">[</span>39<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Mathew_40-1" class="reference"><a href="#cite_note-Mathew-40"><span class="cite-bracket">[</span>40<span class="cite-bracket">]</span></a></sup> </caption> <tbody><tr> <th>Drug</th> <th>Brand</th> <th>Company</th> <th>Receptor agonist</th> <th>5-HT<sub>1D</sub> affinity<br />(pKI in <a href="/wiki/Nanomolar" class="mw-redirect" title="Nanomolar">nM</a>)<sup id="cite_ref-Deleu_41-0" class="reference"><a href="#cite_note-Deleu-41"><span class="cite-bracket">[</span>41<span class="cite-bracket">]</span></a></sup></th> <th><a href="/wiki/Bioavailability" title="Bioavailability">Bioavailability</a> (%)</th> <th><a href="/wiki/Partition_coefficient" title="Partition coefficient">log D<sub>pH 7.4</sub></a></th> <th><a href="/wiki/Cmax_(pharmacology)" title="Cmax (pharmacology)">T<sub>max</sub></a> (h)</th> <th><a href="/wiki/Elimination_half-life" class="mw-redirect" title="Elimination half-life">T<sub>1/2</sub></a> (h)</th> <th>Metabolism</th> <th>Dose (mg) </th></tr> <tr> <td><a href="/wiki/Sumatriptan" title="Sumatriptan">Sumatriptan</a> </td> <td align="center">Imitrex </td> <td align="center"><a href="/wiki/Glaxo_Smith_Kline" class="mw-redirect" title="Glaxo Smith Kline">Glaxo Smith Kline</a> </td> <td align="center">5-HT<sub>1B/D</sub> </td> <td align="center">7.9–8.5 </td> <td align="center">14–17 </td> <td align="center">–1.3 </td> <td align="center">2–2.5 </td> <td align="center">2.5 </td> <td align="center"><a href="/wiki/MAO-A" class="mw-redirect" title="MAO-A">MAO-A</a> </td> <td align="center">25, <br /> 50, <br /> 100 </td></tr> <tr> <td><a href="/wiki/Zolmitriptan" title="Zolmitriptan">Zolmitriptan</a> </td> <td align="center">Zomig </td> <td align="center"><a rel="nofollow" class="external text" href="https://www.astrazeneca.com/media-centre/press-releases/2017/astrazeneca-enters-agreement-with-grunenthal-to-divest-rights-to-migraine-treatment-zomig-07062017.html">Grünenthal</a><sup id="cite_ref-42" class="reference"><a href="#cite_note-42"><span class="cite-bracket">[</span>42<span class="cite-bracket">]</span></a></sup> </td> <td align="center">5-HT<sub>1B/D</sub> </td> <td align="center">9.2 </td> <td align="center">40 </td> <td align="center">–0.7 </td> <td align="center">1.5–2 </td> <td align="center">2–3 </td> <td align="center"><a href="/wiki/MAO-A" class="mw-redirect" title="MAO-A">MAO-A</a> <br /> <a href="/wiki/CYP1A2" title="CYP1A2">CYP1A2</a> </td> <td align="center">2.5, <br /> 5 </td></tr> <tr> <td><a href="/wiki/Naratriptan" title="Naratriptan">Naratriptan</a> </td> <td align="center">Amerge </td> <td align="center"><a href="/wiki/Glaxo_Smith_Kline" class="mw-redirect" title="Glaxo Smith Kline">Glaxo Smith Kline</a> </td> <td align="center">5-HT<sub>1B/D</sub> </td> <td align="center">8.3 </td> <td align="center">70 </td> <td align="center">–0.2 </td> <td align="center">2–3 </td> <td align="center">6 </td> <td align="center">many CYPs <br /> <a href="/wiki/MAO-A" class="mw-redirect" title="MAO-A">MAO-A</a> </td> <td align="center">1, <br /> 2.5 </td></tr> <tr> <td><a href="/wiki/Rizatriptan" title="Rizatriptan">Rizatriptan</a> </td> <td align="center">Maxalt </td> <td align="center">Merck </td> <td align="center">5-HT<sub>1B/D</sub> </td> <td align="center">7.7 </td> <td align="center">45 </td> <td align="center">–0.7 </td> <td align="center">1–1.5 </td> <td align="center">2–2.5 </td> <td align="center"><a href="/wiki/MAO-A" class="mw-redirect" title="MAO-A">MAO-A</a> </td> <td align="center">5, <br /> 10 </td></tr> <tr> <td><a href="/wiki/Almotriptan" title="Almotriptan">Almotriptan</a> </td> <td align="center">Axert </td> <td align="center">Almirall-Prodesfarma </td> <td align="center">5-HT<sub>1B/D</sub> <br /> 5-HT<sub>1F</sub><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. (October 2016)">citation needed</span></a></i>]</sup> </td> <td align="center">7.8 </td> <td align="center">70 </td> <td align="center">+0.35 </td> <td align="center">2.5 </td> <td align="center">3.6 </td> <td align="center"><a href="/wiki/CYP2D6" title="CYP2D6">CYP2D6</a> <br /> <a href="/wiki/CYP3A4" title="CYP3A4">CYP3A4</a> <br /> <a href="/wiki/MAO-A" class="mw-redirect" title="MAO-A">MAO-A</a> </td> <td align="center">6.25, <br /> 12.5 </td></tr> <tr> <td><a href="/wiki/Eletriptan" title="Eletriptan">Eletriptan</a> </td> <td align="center">Relpax </td> <td align="center"><a href="/wiki/Pfizer" title="Pfizer">Pfizer</a> </td> <td align="center">5-HT<sub>1B/D</sub> <br /> 5-HT<sub>1F</sub><sup id="cite_ref-relpax_spc_43-0" class="reference"><a href="#cite_note-relpax_spc-43"><span class="cite-bracket">[</span>43<span class="cite-bracket">]</span></a></sup> </td> <td align="center">8.9 </td> <td align="center">50 </td> <td align="center">+0.5 </td> <td align="center">1–2 </td> <td align="center">3.6–5.5 </td> <td align="center"><a href="/wiki/CYP3A4" title="CYP3A4">CYP3A4</a> </td> <td align="center">20, <br /> 40, <br /> 80 </td></tr> <tr> <td><a href="/wiki/Frovatriptan" title="Frovatriptan">Frovatriptan</a> </td> <td align="center">Frova </td> <td align="center">Vernalis </td> <td align="center">5-HT<sub>1B/D</sub> </td> <td align="center">8.4 </td> <td align="center">24–30 </td> <td align="center"> </td> <td align="center">2–4 </td> <td align="center">26 </td> <td align="center"><a href="/wiki/CYP1A2" title="CYP1A2">CYP1A2</a> </td> <td align="center">2.5 </td></tr></tbody></table> <p>Zolmitriptan is different from the other triptans because it is converted to an active N-desmethyl metabolite which has higher affinity for the 5-HT<sub>1D</sub> and 5-HT<sub>1B</sub> receptors; both substances have a biological half-life of 2 to 3 hours.<sup id="cite_ref-Goodman_22-4" class="reference"><a href="#cite_note-Goodman-22"><span class="cite-bracket">[</span>22<span class="cite-bracket">]</span></a></sup> In studies, newer triptans are mostly compared to sumatriptan.<sup id="cite_ref-Ferrari_21-1" class="reference"><a href="#cite_note-Ferrari-21"><span class="cite-bracket">[</span>21<span class="cite-bracket">]</span></a></sup> They are better than sumatriptan for their longer half-life in plasma and higher oral <a href="/wiki/Bioavailability" title="Bioavailability">bioavailability</a>,<sup id="cite_ref-Foyes_44-0" class="reference"><a href="#cite_note-Foyes-44"><span class="cite-bracket">[</span>44<span class="cite-bracket">]</span></a></sup> but have a higher potential for <a href="/wiki/Central_nervous" class="mw-redirect" title="Central nervous">central nervous</a> side effects.<sup id="cite_ref-Mutschler_1-3" class="reference"><a href="#cite_note-Mutschler-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> </p><p><a href="/wiki/Donitriptan" title="Donitriptan">Donitriptan</a> and <a href="/wiki/Avitriptan" title="Avitriptan">avitriptan</a> were never marketed. </p> <div class="mw-heading mw-heading2"><h2 id="History">History</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Triptan&action=edit&section=14" title="Edit section: History"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">Further information: <a href="/wiki/Discovery_and_development_of_triptans" title="Discovery and development of triptans">Discovery and development of triptans</a></div> <p>The history of triptans began with the proposed existence of then unknown serotonin (5-hydroxytryptamine, 5-HT). In the late 1940s two groups of investigators, one in Italy and the other in the United States, identified a substance that was called <i>serotonin</i> in the US and <i>enteramine</i> in Italy. In the early 1950s it was confirmed that both substances were the same. In the mid-1950s it was proposed that serotonin had a role as a <a href="/wiki/Neurotransmitter" title="Neurotransmitter">neurotransmitter</a> in the central nervous system (CNS) of animals. Investigations of the mechanism of action were not very successful as experimental techniques were lacking.<sup id="cite_ref-Foyes_44-1" class="reference"><a href="#cite_note-Foyes-44"><span class="cite-bracket">[</span>44<span class="cite-bracket">]</span></a></sup> </p><p>Later in the 1960s, studies showed that <a href="/wiki/Vasoconstriction" title="Vasoconstriction">vasoconstriction</a> caused by 5-HT, <a href="/wiki/Noradrenaline" class="mw-redirect" title="Noradrenaline">noradrenaline</a> and <a href="/wiki/Ergotamine" title="Ergotamine">ergotamine</a> could reduce migraine attacks. Patrick P.A. Humphrey among others at <a href="/wiki/Glaxo" class="mw-redirect" title="Glaxo">Glaxo</a> started researching the 5-HT receptor to discover a more direct 5-HT <a href="/wiki/Agonist" title="Agonist">agonist</a> with fewer side effects. </p><p>They continued developing and working on a desirable action on 5-HT by 5-HT<sub>1</sub> receptor activation for an anti-migraine drug. Continued work led to the <a href="/wiki/Drug_development" title="Drug development">development</a> of sumatriptan, now known as the first 5-HT<sub>1</sub> agonist, selective for the 5-HT<sub>1D/B</sub> receptors and also the 5-HT<sub>1F</sub> receptor with less affinity. By 1991 sumatriptan became available in clinical use in the Netherlands and in the US in 1993. However, there was always a debate about its mechanism of action, and it still remains unclear today. Later, Mike Moskowitz proposed a theory about "neuronal extravasation", and this was the first clue that sumatriptan might have a direct <a href="/wiki/Neuronal" class="mw-redirect" title="Neuronal">neuronal</a> effect in migraine attacks.<sup id="cite_ref-45" class="reference"><a href="#cite_note-45"><span class="cite-bracket">[</span>45<span class="cite-bracket">]</span></a></sup> </p><p>Sumatriptan became a prototype for other triptans that have been developed for improved selectivity for the 5-HT<sub>1D/B</sub> receptors.<sup id="cite_ref-Foyes_44-2" class="reference"><a href="#cite_note-Foyes-44"><span class="cite-bracket">[</span>44<span class="cite-bracket">]</span></a></sup> </p> <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=Triptan&action=edit&section=15" 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=Triptan&action=edit&section=16" title="Edit section: Legal status"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>These drugs have been available only by prescription (US, Canada and UK), but sumatriptan became available over-the-counter in the UK in June 2006.<sup id="cite_ref-BBC_generic_46-0" class="reference"><a href="#cite_note-BBC_generic-46"><span class="cite-bracket">[</span>46<span class="cite-bracket">]</span></a></sup> The brand name of the OTC product in the UK is Imigran Recovery. The patent on Imitrex STATDose expired in December 2006, and injectable sumatriptan became available as a generic formula in August 2008.<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. (April 2010)">citation needed</span></a></i>]</sup> Sumavel Dosepro is a needle-free delivery of injectable sumatriptan that was approved in the US by the FDA in July 2009.<sup id="cite_ref-Zogenix_17-1" class="reference"><a href="#cite_note-Zogenix-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup> Sumatriptan became available as a generic in the US in late 2009. It used to be sold over-the-counter in Romania under the Imigran brand; however, as of August 2014 prescription is required. Zecuity, a sumatriptan transdermal patch, was approved by the US FDA in January 2013.<sup id="cite_ref-:0_15-1" class="reference"><a href="#cite_note-:0-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup> The sumatriptan nasal powder was approved by the FDA in January 2016 and became available in the U.S. May 2016.<sup id="cite_ref-47" class="reference"><a href="#cite_note-47"><span class="cite-bracket">[</span>47<span class="cite-bracket">]</span></a></sup> <a href="/wiki/Naratriptan" title="Naratriptan">Naratriptan</a> is available OTC in Germany and Brazil. </p> <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=Triptan&action=edit&section=17" title="Edit section: References"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <dl><dt>Notes</dt></dl> <style data-mw-deduplicate="TemplateStyles:r1239543626">.mw-parser-output .reflist{margin-bottom:0.5em;list-style-type:decimal}@media screen{.mw-parser-output .reflist{font-size:90%}}.mw-parser-output .reflist .references{font-size:100%;margin-bottom:0;list-style-type:inherit}.mw-parser-output .reflist-columns-2{column-width:30em}.mw-parser-output .reflist-columns-3{column-width:25em}.mw-parser-output .reflist-columns{margin-top:0.3em}.mw-parser-output .reflist-columns ol{margin-top:0}.mw-parser-output .reflist-columns li{page-break-inside:avoid;break-inside:avoid-column}.mw-parser-output .reflist-upper-alpha{list-style-type:upper-alpha}.mw-parser-output .reflist-upper-roman{list-style-type:upper-roman}.mw-parser-output .reflist-lower-alpha{list-style-type:lower-alpha}.mw-parser-output .reflist-lower-greek{list-style-type:lower-greek}.mw-parser-output .reflist-lower-roman{list-style-type:lower-roman}</style><div class="reflist reflist-columns references-column-width" style="column-width: 35em;"> <ol class="references"> <li id="cite_note-Mutschler-1"><span class="mw-cite-backlink">^ <a href="#cite_ref-Mutschler_1-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Mutschler_1-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-Mutschler_1-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-Mutschler_1-3"><sup><i><b>d</b></i></sup></a></span> <span class="reference-text"><style data-mw-deduplicate="TemplateStyles:r1238218222">.mw-parser-output cite.citation{font-style:inherit;word-wrap:break-word}.mw-parser-output .citation q{quotes:"\"""\"""'""'"}.mw-parser-output .citation:target{background-color:rgba(0,127,255,0.133)}.mw-parser-output .id-lock-free.id-lock-free a{background:url("//upload.wikimedia.org/wikipedia/commons/6/65/Lock-green.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-limited.id-lock-limited a,.mw-parser-output .id-lock-registration.id-lock-registration a{background:url("//upload.wikimedia.org/wikipedia/commons/d/d6/Lock-gray-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-subscription.id-lock-subscription a{background:url("//upload.wikimedia.org/wikipedia/commons/a/aa/Lock-red-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .cs1-ws-icon a{background:url("//upload.wikimedia.org/wikipedia/commons/4/4c/Wikisource-logo.svg")right 0.1em center/12px no-repeat}body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-free a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-limited a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-registration a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-subscription a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .cs1-ws-icon a{background-size:contain;padding:0 1em 0 0}.mw-parser-output .cs1-code{color:inherit;background:inherit;border:none;padding:inherit}.mw-parser-output .cs1-hidden-error{display:none;color:var(--color-error,#d33)}.mw-parser-output .cs1-visible-error{color:var(--color-error,#d33)}.mw-parser-output .cs1-maint{display:none;color:#085;margin-left:0.3em}.mw-parser-output .cs1-kern-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right{padding-right:0.2em}.mw-parser-output .citation .mw-selflink{font-weight:inherit}@media screen{.mw-parser-output .cs1-format{font-size:95%}html.skin-theme-clientpref-night .mw-parser-output .cs1-maint{color:#18911f}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .cs1-maint{color:#18911f}}</style><cite id="CITEREFMutschlerGerd_GeisslingerHeyo_K._KroemerSabine_Menzel2013" class="citation book cs1 cs1-prop-foreign-lang-source">Mutschler, Ernst; Gerd Geisslinger; Heyo K. Kroemer; Sabine Menzel; Peter Ruth (2013). <i>Arzneimittelwirkungen</i> (in German) (10 ed.). Stuttgart: Wissenschaftliche Verlagsgesellschaft. pp. <span class="nowrap">233–</span>4. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-3-8047-2898-1" title="Special:BookSources/978-3-8047-2898-1"><bdi>978-3-8047-2898-1</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Arzneimittelwirkungen&rft.place=Stuttgart&rft.pages=%3Cspan+class%3D%22nowrap%22%3E233-%3C%2Fspan%3E4&rft.edition=10&rft.pub=Wissenschaftliche+Verlagsgesellschaft&rft.date=2013&rft.isbn=978-3-8047-2898-1&rft.aulast=Mutschler&rft.aufirst=Ernst&rft.au=Gerd+Geisslinger&rft.au=Heyo+K.+Kroemer&rft.au=Sabine+Menzel&rft.au=Peter+Ruth&rfr_id=info%3Asid%2Fen.wikipedia.org%3ATriptan" class="Z3988"></span></span> </li> <li id="cite_note-Green_2015-2"><span class="mw-cite-backlink"><b><a href="#cite_ref-Green_2015_2-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFGreen2015" class="citation book cs1">Green, Mark W. (2015). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=h-acBAAAQBAJ&pg=PA44">"Overview of Migraine: Recognition, Diagnosis, and Pathophysiology"</a>. In Diamond, Seymour; Cady, Roger K.; Diamond, Merle L.; Green, Mark W.; Martin, Vincent T. (eds.). <i>Headache and Migraine Biology and Management</i>. 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"The triptans - A summary". <i>CNS Drugs</i>. <b>12</b> (5): <span class="nowrap">403–</span>417. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.2165%2F00023210-199912050-00007">10.2165/00023210-199912050-00007</a>. <a href="/wiki/S2CID_(identifier)" class="mw-redirect" title="S2CID (identifier)">S2CID</a> <a rel="nofollow" class="external text" href="https://api.semanticscholar.org/CorpusID:72149615">72149615</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=CNS+Drugs&rft.atitle=The+triptans+-+A+summary&rft.volume=12&rft.issue=5&rft.pages=%3Cspan+class%3D%22nowrap%22%3E403-%3C%2Fspan%3E417&rft.date=1999&rft_id=info%3Adoi%2F10.2165%2F00023210-199912050-00007&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A72149615%23id-name%3DS2CID&rft.au=Tepper+S.+J.&rft.au=Rapoport+A.+M.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ATriptan" class="Z3988"></span></li></ul> <div class="navbox-styles"><style data-mw-deduplicate="TemplateStyles:r1129693374">.mw-parser-output .hlist dl,.mw-parser-output .hlist ol,.mw-parser-output .hlist ul{margin:0;padding:0}.mw-parser-output .hlist dd,.mw-parser-output .hlist dt,.mw-parser-output .hlist li{margin:0;display:inline}.mw-parser-output .hlist.inline,.mw-parser-output .hlist.inline dl,.mw-parser-output .hlist.inline ol,.mw-parser-output .hlist.inline ul,.mw-parser-output .hlist dl dl,.mw-parser-output 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0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Serotonin" title="Serotonin">Serotonergics</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Ergoline" title="Ergoline">Ergolines</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Dihydroergocryptine" title="Dihydroergocryptine">Dihydroergocryptine</a></li> <li><a href="/wiki/Dihydroergotamine" title="Dihydroergotamine">Dihydroergotamine</a></li> <li><a href="/wiki/Ergotamine" title="Ergotamine">Ergotamine</a> (<a href="/wiki/Ergotamine/caffeine" title="Ergotamine/caffeine">+caffeine</a>, <a href="/wiki/Ergotamine/chlorcyclizine/caffeine" title="Ergotamine/chlorcyclizine/caffeine">+chlorcyclizine/caffeine</a>)</li> <li><a href="/wiki/Lisuride" title="Lisuride">Lisuride</a></li> <li><a href="/wiki/Methylergometrine" title="Methylergometrine">Methylergometrine</a></li> <li><a href="/wiki/Methysergide" title="Methysergide">Methysergide</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Serotonin_receptor_agonist" title="Serotonin receptor agonist">5-HT<sub>1</sub> agonists</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a class="mw-selflink selflink">Triptans</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/Almotriptan" title="Almotriptan">Almotriptan</a></li> <li><a href="/wiki/Avitriptan" title="Avitriptan">Avitriptan</a></li> <li><a href="/wiki/Donitriptan" title="Donitriptan">Donitriptan</a></li> <li><a href="/wiki/Eletriptan" title="Eletriptan">Eletriptan</a></li> <li><a href="/wiki/Frovatriptan" title="Frovatriptan">Frovatriptan</a></li> <li><a href="/wiki/Naratriptan" title="Naratriptan">Naratriptan</a></li> <li><a href="/wiki/Rizatriptan" title="Rizatriptan">Rizatriptan</a> (<a href="/wiki/Meloxicam/rizatriptan" title="Meloxicam/rizatriptan">+meloxicam</a>)</li> <li><a href="/wiki/Sumatriptan" title="Sumatriptan">Sumatriptan</a></li> <li><a href="/wiki/Zolmitriptan" title="Zolmitriptan">Zolmitriptan</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Ditan" title="Ditan">Ditans</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Alniditan" title="Alniditan">Alniditan</a><sup>§</sup></li> <li><a href="/wiki/Lasmiditan" title="Lasmiditan">Lasmiditan</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Others</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Dimetotiazine" title="Dimetotiazine">Dimetotiazine</a></li> <li><a href="/wiki/Dotarizine" title="Dotarizine">Dotarizine</a></li> <li><a href="/wiki/Iprazochrome" title="Iprazochrome">Iprazochrome</a></li> <li><a href="/wiki/Oxetorone" title="Oxetorone">Oxetorone</a></li> <li><a href="/wiki/Pizotifen" title="Pizotifen">Pizotifen</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Calcitonin_gene-related_peptide_receptor_antagonist" title="Calcitonin gene-related peptide receptor antagonist">CGRP-R antagonists</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Rimegepant" title="Rimegepant">Rimegepant</a></li> <li><a href="/wiki/Ubrogepant" title="Ubrogepant">Ubrogepant</a></li> <li><a href="/wiki/Zavegepant" title="Zavegepant">Zavegepant</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Others</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Paracetamol" title="Paracetamol">Paracetamol</a><sup>#</sup></li> <li><a href="/wiki/Amidrine" title="Amidrine">Amidrine</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Prevention_of_migraines" class="mw-redirect" title="Prevention of migraines">Prophylactic</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Calcium_channel_blocker" title="Calcium channel blocker">Calcium channel blockers</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Dotarizine" title="Dotarizine">Dotarizine</a></li> <li><a href="/wiki/Lomerizine" title="Lomerizine">Lomerizine</a></li> <li><a href="/wiki/Verapamil" title="Verapamil">Verapamil</a></li> <li><a href="/wiki/Flunarizine" title="Flunarizine">Flunarizine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Progestogen" title="Progestogen">Progestogens</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/Flumedroxone_acetate" title="Flumedroxone acetate">Flumedroxone acetate</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Sympatholytic" title="Sympatholytic">Sympatholytics</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Beta_blocker" title="Beta blocker">Beta blockers</a> <ul><li><a href="/wiki/Propranolol" title="Propranolol">Propranolol</a><sup>#</sup></li> <li><a href="/wiki/Timolol" title="Timolol">Timolol</a></li></ul></li> <li><a href="/wiki/Clonidine" title="Clonidine">Clonidine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Tricyclic_antidepressant" title="Tricyclic antidepressant">Tricyclic antidepressants</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/Amitriptyline" title="Amitriptyline">Amitriptyline</a></li> <li><a href="/wiki/Nortriptyline" title="Nortriptyline">Nortriptyline</a></li> <li><a href="/wiki/Imipramine" title="Imipramine">Imipramine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Anticonvulsant" title="Anticonvulsant">Anticonvulsants</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Carbamazepine" title="Carbamazepine">Carbamazepine</a></li> <li><a href="/wiki/Oxcarbazepine" title="Oxcarbazepine">Oxcarbazepine</a></li> <li><a href="/wiki/Topiramate" title="Topiramate">Topiramate</a></li> <li><a href="/wiki/Valproate" title="Valproate">Valproate</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Anti-<a href="/wiki/Calcitonin_gene-related_peptide" title="Calcitonin gene-related peptide">CGRP</a>/<a href="/wiki/CALCRL" title="CALCRL">CGRP-R</a> <a href="/wiki/Monoclonal_antibody" title="Monoclonal antibody">mAbs</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/Eptinezumab" title="Eptinezumab">Eptinezumab</a></li> <li><a href="/wiki/Erenumab" title="Erenumab">Erenumab</a></li> <li><a href="/wiki/Fremanezumab" title="Fremanezumab">Fremanezumab</a></li> <li><a href="/wiki/Galcanezumab" title="Galcanezumab">Galcanezumab</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Calcitonin_gene-related_peptide_receptor_antagonist" title="Calcitonin gene-related peptide receptor antagonist">CGRP-R antagonists</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Atogepant" title="Atogepant">Atogepant</a></li> <li><a href="/wiki/Rimegepant" title="Rimegepant">Rimegepant</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><td colspan="2" class="navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"><div class="hlist"> <ul><li><sup>#</sup><a href="/wiki/WHO_Model_List_of_Essential_Medicines" title="WHO Model List of Essential Medicines">WHO-EM</a></li> <li><sup>‡</sup><a href="/wiki/List_of_withdrawn_drugs" title="List of withdrawn drugs">Withdrawn</a> from market</li> <li><a href="/wiki/Clinical_trial" title="Clinical trial">Clinical trials</a>: <ul><li><sup>†</sup><a href="/wiki/Phases_of_clinical_research#Phase_III" title="Phases of clinical research">Phase III</a></li> <li><sup>§</sup>Never to phase III</li></ul></li></ul> </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="Tryptamines232" style="padding:3px"><table class="nowraplinks mw-collapsible mw-collapsed navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Tryptamines" title="Template:Tryptamines"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Tryptamines" title="Template talk:Tryptamines"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Tryptamines" title="Special:EditPage/Template:Tryptamines"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Tryptamines232" style="font-size:114%;margin:0 4em"><a href="/wiki/Substituted_tryptamine" title="Substituted tryptamine">Tryptamines</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Substituted_tryptamine" title="Substituted tryptamine">Tryptamines</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/w/index.php?title=1-Methyltryptamine&action=edit&redlink=1" class="new" title="1-Methyltryptamine (page does not exist)">1-Methyl-T</a></li> <li><a href="/wiki/1-Methylpsilocin" title="1-Methylpsilocin">1-Methylpsilocin</a></li> <li><a href="/wiki/2-HO-NMT" title="2-HO-NMT">2-HO-NMT</a></li> <li><a href="/wiki/2-Me-DET" title="2-Me-DET">2-Me-DET</a></li> <li><a href="/wiki/2-Methyl-5-hydroxytryptamine" title="2-Methyl-5-hydroxytryptamine">2-Methyl-5-HT</a></li> <li><a href="/wiki/2,N,N-TMT" title="2,N,N-TMT">2,<i>N</i>,<i>N</i>-TMT</a></li> <li><a href="/wiki/1-(2-Dimethylaminoethyl)dihydropyrano(3,2-e)indole" class="mw-redirect" title="1-(2-Dimethylaminoethyl)dihydropyrano(3,2-e)indole">4,5-DHP-DMT</a></li> <li><a href="/wiki/4,5-Dihydroxytryptamine" title="4,5-Dihydroxytryptamine">4,5-DHT</a></li> <li><a href="/wiki/4-AcO-DALT" title="4-AcO-DALT">4-AcO-DALT</a></li> <li><a href="/wiki/4-Acetoxy-DET" class="mw-redirect" title="4-Acetoxy-DET">4-AcO-DET</a></li> <li><a href="/wiki/4-Acetoxy-DiPT" title="4-Acetoxy-DiPT">4-AcO-DiPT</a></li> <li><a href="/wiki/4-AcO-DPT" title="4-AcO-DPT">4-AcO-DPT</a></li> <li><a href="/w/index.php?title=4-AcO-EPT&action=edit&redlink=1" class="new" title="4-AcO-EPT (page does not exist)">4-AcO-EPT</a></li> <li><a href="/w/index.php?title=4-AcO-MALT&action=edit&redlink=1" class="new" title="4-AcO-MALT (page does not exist)">4-AcO-MALT</a></li> <li><a href="/wiki/4-Acetoxy-MET" class="mw-redirect" title="4-Acetoxy-MET">4-AcO-MET</a></li> <li><a href="/wiki/4-Acetoxy-MiPT" class="mw-redirect" title="4-Acetoxy-MiPT">4-AcO-MiPT</a></li> <li><a href="/w/index.php?title=4-AcO-NMT&action=edit&redlink=1" class="new" title="4-AcO-NMT (page does not exist)">4-AcO-NMT</a></li> <li><a href="/w/index.php?title=4-AcO-TMT&action=edit&redlink=1" class="new" title="4-AcO-TMT (page does not exist)">4-AcO-TMT</a></li> <li><a href="/wiki/4-Fluoro-5-methoxy-DMT" title="4-Fluoro-5-methoxy-DMT">4-F-5-MeO-DMT</a></li> <li><a href="/w/index.php?title=4-Fluorotryptamine&action=edit&redlink=1" class="new" title="4-Fluorotryptamine (page does not exist)">4-Fluoro-T</a></li> <li><a href="/wiki/4-Hydroxy-5-methoxytryptamine" title="4-Hydroxy-5-methoxytryptamine">4-HO-5-MeO-T</a></li> <li><a href="/w/index.php?title=4-HO-DALT&action=edit&redlink=1" class="new" title="4-HO-DALT (page does not exist)">4-HO-DALT</a></li> <li><a href="/wiki/4-HO-DBT" title="4-HO-DBT">4-HO-DBT</a></li> <li><a href="/wiki/4-HO-DET" title="4-HO-DET">4-HO-DET</a></li> <li><a href="/wiki/4-HO-DiPT" title="4-HO-DiPT">4-HO-DiPT</a></li> <li><a href="/wiki/4-HO-DPT" title="4-HO-DPT">4-HO-DPT</a></li> <li><a href="/wiki/4-HO-DSBT" title="4-HO-DSBT">4-HO-DSBT</a></li> <li><a href="/wiki/4-HO-EPT" title="4-HO-EPT">4-HO-EPT</a></li> <li><a href="/wiki/4-HO-MALT" title="4-HO-MALT">4-HO-MALT</a></li> <li><a href="/wiki/4-HO-MET" title="4-HO-MET">4-HO-MET</a></li> <li><a href="/wiki/4-HO-McPT" title="4-HO-McPT">4-HO-McPT</a></li> <li><a href="/wiki/4-HO-McPeT" title="4-HO-McPeT">4-HO-McPeT</a></li> <li><a href="/wiki/4-HO-MiPT" title="4-HO-MiPT">4-HO-MiPT</a></li> <li><a href="/wiki/4-HO-MPT" title="4-HO-MPT">4-HO-MPT</a></li> <li><a href="/w/index.php?title=4-HO-MsBT&action=edit&redlink=1" class="new" title="4-HO-MsBT (page does not exist)">4-HO-MsBT</a></li> <li><a href="/wiki/4-HO-NALT" title="4-HO-NALT">4-HO-NALT</a></li> <li><a href="/wiki/4-HO-NMT" class="mw-redirect" title="4-HO-NMT">4-HO-NMT</a></li> <li><a href="/wiki/4-HO-PiPT" title="4-HO-PiPT">4-HO-PiPT</a></li> <li><a href="/wiki/4-HO-pyr-T" title="4-HO-pyr-T">4-HO-pyr-T</a></li> <li><a href="/wiki/4-HO-TMT" title="4-HO-TMT">4-HO-TMT</a></li> <li><a href="/wiki/4-Hydroxytryptamine" title="4-Hydroxytryptamine">4-HT</a></li> <li><a href="/w/index.php?title=4-MeO-DiPT&action=edit&redlink=1" class="new" title="4-MeO-DiPT (page does not exist)">4-MeO-DiPT</a></li> <li><a href="/wiki/4-MeO-DMT" title="4-MeO-DMT">4-MeO-DMT</a></li> <li><a href="/wiki/4-MeO-MiPT" title="4-MeO-MiPT">4-MeO-MiPT</a></li> <li><a href="/w/index.php?title=4-MeO-T&action=edit&redlink=1" class="new" title="4-MeO-T (page does not exist)">4-MeO-T</a></li> <li><a href="/wiki/4-PrO-DMT" title="4-PrO-DMT">4-PrO-DMT</a></li> <li><a href="/wiki/4,5-MDO-DMT" title="4,5-MDO-DMT">4,5-MDO-DMT</a></li> <li><a href="/wiki/4,5-MDO-DiPT" title="4,5-MDO-DiPT">4,5-MDO-DiPT</a></li> <li><a href="/wiki/5-Benzyloxytryptamine" title="5-Benzyloxytryptamine">5-BT</a></li> <li><a href="/wiki/5-Bromo-DMT" title="5-Bromo-DMT">5-Bromo-DMT</a></li> <li><a href="/w/index.php?title=5-Bromotryptamine&action=edit&redlink=1" class="new" title="5-Bromotryptamine (page does not exist)">5-Bromo-T</a></li> <li><a href="/wiki/5-Chloro-DMT" title="5-Chloro-DMT">5-Chloro-DMT</a></li> <li><a href="/w/index.php?title=5-Chlorotryptamine&action=edit&redlink=1" class="new" title="5-Chlorotryptamine (page does not exist)">5-Chloro-T</a></li> <li><a href="/wiki/5-Carboxamidotryptamine" title="5-Carboxamidotryptamine">5-CT</a></li> <li><a href="/wiki/5-Ethoxy-DMT" title="5-Ethoxy-DMT">5-Ethoxy-DMT</a></li> <li><a href="/wiki/5-Ethyl-DMT" title="5-Ethyl-DMT">5-Ethyl-DMT</a></li> <li><a href="/wiki/5-Fluoro-DET" title="5-Fluoro-DET">5-Fluoro-DET</a></li> <li><a href="/wiki/5-Fluoro-DMT" title="5-Fluoro-DMT">5-Fluoro-DMT</a></li> <li><a href="/wiki/5-Fluoro-EPT" title="5-Fluoro-EPT">5-Fluoro-EPT</a></li> <li><a href="/wiki/5-Fluoro-MET" title="5-Fluoro-MET">5-Fluoro-MET</a></li> <li><a href="/w/index.php?title=5-Fluorotryptamine&action=edit&redlink=1" class="new" title="5-Fluorotryptamine (page does not exist)">5-Fluoro-T</a></li> <li><a href="/wiki/5-HO-DiPT" title="5-HO-DiPT">5-HO-DiPT</a></li> <li><a href="/wiki/5-Hydroxytryptophan" title="5-Hydroxytryptophan">5-HTP (oxitriptan)</a></li> <li><a href="/wiki/5-MeO-2-TMT" title="5-MeO-2-TMT">5-MeO-2-TMT</a></li> <li><a href="/w/index.php?title=5-MeO-34MPEMT&action=edit&redlink=1" class="new" title="5-MeO-34MPEMT (page does not exist)">5-MeO-34MPEMT</a></li> <li><a href="/wiki/5-Methoxy-7,N,N-trimethyltryptamine" title="5-Methoxy-7,N,N-trimethyltryptamine">5-MeO-7,<i>N</i>,<i>N</i>-TMT</a></li> <li><a href="/wiki/5-MeO-DALT" title="5-MeO-DALT">5-MeO-DALT</a></li> <li><a href="/wiki/5-MeO-DBT" title="5-MeO-DBT">5-MeO-DBT</a></li> <li><a href="/wiki/5-MeO-DET" title="5-MeO-DET">5-MeO-DET</a></li> <li><a href="/wiki/5-Methoxy-N,N-diisopropyltryptamine" class="mw-redirect" title="5-Methoxy-N,N-diisopropyltryptamine">5-MeO-DiPT</a></li> <li><a href="/wiki/5-MeO-DMT" title="5-MeO-DMT">5-MeO-DMT</a></li> <li><a href="/wiki/5-MeO-DPT" title="5-MeO-DPT">5-MeO-DPT</a></li> <li><a href="/wiki/5-MeO-EiPT" title="5-MeO-EiPT">5-MeO-EiPT</a></li> <li><a href="/wiki/5-MeO-EPT" title="5-MeO-EPT">5-MeO-EPT</a></li> <li><a href="/wiki/5-MeO-MALT" title="5-MeO-MALT">5-MeO-MALT</a></li> <li><a href="/wiki/5-MeO-MET" title="5-MeO-MET">5-MeO-MET</a></li> <li><a href="/wiki/5-MeO-MiPT" title="5-MeO-MiPT">5-MeO-MiPT</a></li> <li><a href="/w/index.php?title=5-MeO-NET&action=edit&redlink=1" class="new" title="5-MeO-NET (page does not exist)">5-MeO-NET</a></li> <li><a href="/w/index.php?title=5-MeO-NiPT&action=edit&redlink=1" class="new" title="5-MeO-NiPT (page does not exist)">5-MeO-NiPT</a></li> <li><a href="/wiki/5-MeO-NMT" title="5-MeO-NMT">5-MeO-NMT</a></li> <li><a href="/wiki/5-MeO-pyr-T" title="5-MeO-pyr-T">5-MeO-pyr-T</a></li> <li><a href="/wiki/5-MeO-NBpBrT" title="5-MeO-NBpBrT">5-MeO-NBpBrT</a></li> <li><a href="/wiki/5-Methoxytryptamine" title="5-Methoxytryptamine">5-MeO-T (5-MT; mexamine)</a></li> <li><a href="/wiki/5-MeO-T-NBOMe" title="5-MeO-T-NBOMe">5-MeO-T-NBOMe</a></li> <li><a href="/wiki/5-MeS-DMT" title="5-MeS-DMT">5-MeS-DMT</a></li> <li><a href="/wiki/5,N,N-TMT" title="5,N,N-TMT">5-Methyl-DMT</a></li> <li><a href="/wiki/5-Methyltryptamine" title="5-Methyltryptamine">5-Methyl-T</a></li> <li><a href="/w/index.php?title=5-MT-NB3OMe&action=edit&redlink=1" class="new" title="5-MT-NB3OMe (page does not exist)">5-MT-NB3OMe</a></li> <li><a href="/wiki/5-(Nonyloxy)tryptamine" title="5-(Nonyloxy)tryptamine">5-NOT</a></li> <li><a href="/wiki/5,6-MeO-MiPT" title="5,6-MeO-MiPT">5,6-MeO-MiPT</a></li> <li><a href="/wiki/5,6-MDO-DiPT" title="5,6-MDO-DiPT">5,6-MDO-DiPT</a></li> <li><a href="/wiki/5,6-MDO-DMT" title="5,6-MDO-DMT">5,6-MDO-DMT</a></li> <li><a href="/wiki/5,6-MDO-MiPT" title="5,6-MDO-MiPT">5,6-MDO-MiPT</a></li> <li><a href="/wiki/5,6-Dihydroxytryptamine" title="5,6-Dihydroxytryptamine">5,6-DHT</a></li> <li><a href="/wiki/5,7-Dihydroxytryptamine" title="5,7-Dihydroxytryptamine">5,7-DHT</a></li> <li><a href="/wiki/6-Fluoro-DMT" title="6-Fluoro-DMT">6-Fluoro-DMT</a></li> <li><a href="/w/index.php?title=6-Fluorotryptamine&action=edit&redlink=1" class="new" title="6-Fluorotryptamine (page does not exist)">6-Fluoro-T</a></li> <li><a href="/wiki/6-MeO-DMT" title="6-MeO-DMT">6-MeO-DMT</a></li> <li><a href="/w/index.php?title=6-Methoxytryptamine&action=edit&redlink=1" class="new" title="6-Methoxytryptamine (page does not exist)">6-MeO-T</a></li> <li><a href="/w/index.php?title=6-Methyltryptamine&action=edit&redlink=1" class="new" title="6-Methyltryptamine (page does not exist)">6-Methyl-T</a></li> <li><a href="/wiki/6,7-Dihydroxytryptamine" title="6,7-Dihydroxytryptamine">6,7-DHT</a></li> <li><a href="/w/index.php?title=7-Chlorotryptamine&action=edit&redlink=1" class="new" title="7-Chlorotryptamine (page does not exist)">7-Chloro-T</a></li> <li><a href="/w/index.php?title=7-Methoxytryptamine&action=edit&redlink=1" class="new" title="7-Methoxytryptamine (page does not exist)">7-MeO-T</a></li> <li><a href="/wiki/7,N,N-TMT" title="7,N,N-TMT">7-Methyl-DMT</a></li> <li><a href="/w/index.php?title=7-Methyltryptamine&action=edit&redlink=1" class="new" title="7-Methyltryptamine (page does not exist)">7-Methyl-T</a></li> <li><a href="/wiki/Acetryptine" title="Acetryptine">Acetryptine (5-AT)</a></li> <li><a href="/wiki/Aeruginascin" title="Aeruginascin">Aeruginascin (4-PO-TMT)</a></li> <li><a href="/wiki/AGH-107" title="AGH-107">AGH-107</a></li> <li><a href="/wiki/AGH-192" title="AGH-192">AGH-192</a></li> <li><a href="/wiki/AH-494" title="AH-494">AH-494</a></li> <li><a href="/w/index.php?title=ALiPT&action=edit&redlink=1" class="new" title="ALiPT (page does not exist)">ALiPT</a></li> <li><a href="/wiki/Alpertine" title="Alpertine">Alpertine</a></li> <li><a href="/wiki/Baeocystin" title="Baeocystin">Baeocystin (4-PO-NMT)</a></li> <li><a href="/wiki/Benzotript" title="Benzotript">Benzotript (4-chlorobenzoyl-<small>L</small>-tryptophan)</a></li> <li><a href="/wiki/Bufotenidine" title="Bufotenidine">Bufotenidine (5-HTQ)</a></li> <li><a href="/wiki/Bufotenin" title="Bufotenin">Bufotenin (5-HO-DMT)</a></li> <li><a href="/wiki/Convolutindole_A" title="Convolutindole A">Convolutindole A</a></li> <li><a href="/wiki/CP-132,484" title="CP-132,484">CP-132,484</a></li> <li><a href="/wiki/DALT" title="DALT">DALT</a></li> <li><a href="/wiki/Dibutyltryptamine" title="Dibutyltryptamine">DBT</a></li> <li><a href="/wiki/Desformylflustrabromine" title="Desformylflustrabromine">Desformylflustrabromine</a></li> <li><a href="/wiki/Diethyltryptamine" title="Diethyltryptamine">DET</a></li> <li><a href="/wiki/Diisopropyltryptamine" class="mw-redirect" title="Diisopropyltryptamine">DiPT</a></li> <li><a href="/wiki/Dimethyltryptamine" class="mw-redirect" title="Dimethyltryptamine">DMT</a></li> <li><a href="/wiki/Dipropyltryptamine" title="Dipropyltryptamine">DPT</a></li> <li><a href="/wiki/E-6801" title="E-6801">E-6801</a></li> <li><a href="/wiki/E-6837" title="E-6837">E-6837</a></li> <li><a href="/wiki/Ethylisopropyltryptamine" title="Ethylisopropyltryptamine">EiPT</a></li> <li><a href="/wiki/EMDT" title="EMDT">EMDT</a></li> <li><a href="/wiki/Ethylpropyltryptamine" title="Ethylpropyltryptamine">EPT</a></li> <li><a href="/wiki/Ethocybin" title="Ethocybin">Ethocybin (4-PO-DET)</a></li> <li><a href="/wiki/FGIN-127" title="FGIN-127">FGIN-127</a></li> <li><a href="/wiki/FGIN-143" title="FGIN-143">FGIN-143</a></li> <li><a href="/wiki/FT-104" title="FT-104">FT-104</a></li> <li><a href="/wiki/HIOC" title="HIOC">HIOC</a></li> <li><a href="/wiki/Idalopirdine" title="Idalopirdine">Idalopirdine</a></li> <li><a href="/w/index.php?title=Indolylethylfentanyl&action=edit&redlink=1" class="new" title="Indolylethylfentanyl (page does not exist)">Indolylethylfentanyl</a></li> <li><a href="/wiki/Indorenate" title="Indorenate">Indorenate</a></li> <li><a href="/wiki/4-HO-DiPT" title="4-HO-DiPT">Iprocin (4-HO-DiPT)</a></li> <li><a href="/wiki/Isamide" title="Isamide">Isamide</a></li> <li><a href="/wiki/Lespedamine" title="Lespedamine">Lespedamine</a></li> <li><a href="/wiki/Methylbutyltryptamine" title="Methylbutyltryptamine">MBT</a></li> <li><a href="/wiki/N-Methyl-N-ethyltryptamine" title="N-Methyl-N-ethyltryptamine">MET</a></li> <li><a href="/wiki/Milipertine" title="Milipertine">Milipertine</a></li> <li><a href="/wiki/4-HO-MiPT" title="4-HO-MiPT">Miprocin (4-HO-MiPT)</a></li> <li><a href="/wiki/Methylisopropyltryptamine" class="mw-redirect" title="Methylisopropyltryptamine">MiPT</a></li> <li><a href="/wiki/4-Acetoxy-MiPT" class="mw-redirect" title="4-Acetoxy-MiPT">MPT</a></li> <li><a href="/wiki/MS-245" title="MS-245">MS-245</a></li> <li><a href="/wiki/Methylbutyltryptamine#MSBT" title="Methylbutyltryptamine">MSBT</a></li> <li><a href="/wiki/N-Feruloylserotonin" title="N-Feruloylserotonin"><i>N</i>-Feruloylserotonin (moschamine)</a></li> <li><a href="/wiki/NBoc-DMT" title="NBoc-DMT">NBoc-DMT</a></li> <li><a href="/wiki/N-Ethyltryptamine" title="N-Ethyltryptamine">NET/NETP</a></li> <li><a href="/w/index.php?title=N-Isopropyltryptamine&action=edit&redlink=1" class="new" title="N-Isopropyltryptamine (page does not exist)">NiPT</a></li> <li><a href="/wiki/N-Methyltryptamine" title="N-Methyltryptamine">NMT</a></li> <li><a href="/wiki/Norbaeocystin" title="Norbaeocystin">Norbaeocystin (4-PO-T)</a></li> <li><a href="/wiki/N-t-Butyltryptamine" title="N-t-Butyltryptamine">NTBT</a></li> <li><a href="/wiki/O-4310" title="O-4310">O-4310</a></li> <li><a href="/wiki/O-Pivalylbufotenine" title="O-Pivalylbufotenine"><i>O</i>-Pivalylbufotenine</a></li> <li><a href="/wiki/Oxypertine" title="Oxypertine">Oxypertine</a></li> <li><a href="/wiki/Propylisopropyltryptamine" title="Propylisopropyltryptamine">PiPT</a></li> <li><a href="/wiki/Psilacetin" class="mw-redirect" title="Psilacetin">Psilacetin (<i>O</i>-acetylpsilocin; 4-AcO-DMT)</a></li> <li><a href="/wiki/Psilocin" title="Psilocin">Psilocin (4-HO-DMT)</a></li> <li><a href="/wiki/Psilocybin" title="Psilocybin">Psilocybin (4-PO-DMT)</a></li> <li><a href="/wiki/Psilomethoxin" title="Psilomethoxin">Psilomethoxin (4-HO-5-MeO-DMT)</a></li> <li><a href="/wiki/Pyr-T" title="Pyr-T">Pyr-T</a></li> <li><a href="/wiki/RS134-49" title="RS134-49">RS134-49</a></li> <li><a href="/wiki/Serotonin" title="Serotonin">Serotonin (5-HT)</a></li> <li><a href="/wiki/Solypertine" title="Solypertine">Solypertine</a></li> <li><a href="/wiki/ST-1936" title="ST-1936">ST-1936</a></li> <li><a href="/wiki/Tryptamine" title="Tryptamine">Tryptamine (T)</a></li> <li><a href="/wiki/Tryptophan" title="Tryptophan">Tryptophan</a></li> <li><a href="/wiki/Yuremamine" title="Yuremamine">Yuremamine</a></li> <li><a href="/w/index.php?title=Z2876442907&action=edit&redlink=1" class="new" title="Z2876442907 (page does not exist)">Z2876442907</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/N-Acetyltryptamine" title="N-Acetyltryptamine"><i>N</i>-Acetyltryptamines</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/2-Iodomelatonin" title="2-Iodomelatonin">2-Iodomelatonin</a></li> <li><a href="/w/index.php?title=2-Phenylmelatonin&action=edit&redlink=1" class="new" title="2-Phenylmelatonin (page does not exist)">2-Phenylmelatonin</a></li> <li><a href="/w/index.php?title=5-Methoxyluzindole&action=edit&redlink=1" class="new" title="5-Methoxyluzindole (page does not exist)">5-Methoxyluzindole</a></li> <li><a href="/w/index.php?title=6-Chloromelatonin&action=edit&redlink=1" class="new" title="6-Chloromelatonin (page does not exist)">6-Chloromelatonin</a></li> <li><a href="/w/index.php?title=6-Fluoromelatonin&action=edit&redlink=1" class="new" title="6-Fluoromelatonin (page does not exist)">6-Fluoromelatonin</a></li> <li><a href="/wiki/6-Hydroxymelatonin" title="6-Hydroxymelatonin">6-Hydroxymelatonin</a></li> <li><a href="/w/index.php?title=6-Methoxymelatonin&action=edit&redlink=1" class="new" title="6-Methoxymelatonin (page does not exist)">6-Methoxymelatonin</a></li> <li><a href="/w/index.php?title=6,7-Dichloro-2-methylmelatonin&action=edit&redlink=1" class="new" title="6,7-Dichloro-2-methylmelatonin (page does not exist)">6,7-Dichloro-2-methylmelatonin</a></li> <li><a href="/wiki/%CE%91-Methylmelatonin" title="Α-Methylmelatonin">α-Methylmelatonin</a></li> <li><a href="/wiki/Luzindole" title="Luzindole">Luzindole</a></li> <li><a href="/wiki/Melatonin" title="Melatonin">Melatonin</a></li> <li><a href="/wiki/N-Acetylserotonin" title="N-Acetylserotonin">Normelatonin (<i>N</i>-acetylserotonin; NAS)</a></li> <li><a href="/wiki/N-Acetyltryptamine" title="N-Acetyltryptamine"><i>N</i>-Acetyltryptamine</a></li> <li><a href="/w/index.php?title=N-Butanoylmelatonin&action=edit&redlink=1" class="new" title="N-Butanoylmelatonin (page does not exist)"><i>N</i>-Butanoylmelatonin</a></li> <li><a href="/w/index.php?title=N-Propionylmelatonin&action=edit&redlink=1" class="new" title="N-Propionylmelatonin (page does not exist)"><i>N</i>-Propionylmelatonin</a></li> <li><a href="/wiki/Piromelatine" title="Piromelatine">Piromelatine</a></li> <li><a href="/wiki/TIK-301" title="TIK-301">TIK-301</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/%CE%91-Alkyltryptamine" class="mw-redirect" title="Α-Alkyltryptamine">α-Alkyltryptamines</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/2,%CE%B1-Dimethyltryptamine" title="2,α-Dimethyltryptamine">2,α-DMT</a></li> <li><a href="/wiki/4-HO-%CE%B1MT" title="4-HO-αMT">4-HO-αMT</a></li> <li><a href="/wiki/4-HO-MPMI" title="4-HO-MPMI">4-HO-MPMI (lucigenol)</a></li> <li><a href="/wiki/4-Methyl-%CE%B1-ethyltryptamine" title="4-Methyl-α-ethyltryptamine">4-Me-αET</a></li> <li><a href="/wiki/4-Me-%CE%B1MT" class="mw-redirect" title="4-Me-αMT">4-Me-αMT</a></li> <li><a href="/wiki/5-Chloro-%CE%B1ET" title="5-Chloro-αET">5-Chloro-αET</a></li> <li><a href="/wiki/5-Chloro-%CE%B1MT" title="5-Chloro-αMT">5-Chloro-αMT</a></li> <li><a href="/wiki/5-Ethoxy-AMT" class="mw-redirect" title="5-Ethoxy-AMT">5-Ethoxy-αMT</a></li> <li><a href="/wiki/5-Fluoro-AET" title="5-Fluoro-AET">5-Fluoro-αET</a></li> <li><a href="/wiki/5-Fluoro-AMT" title="5-Fluoro-AMT">5-Fluoro-αMT</a></li> <li><a href="/w/index.php?title=5-Isopropoxy-AMT&action=edit&redlink=1" class="new" title="5-Isopropoxy-AMT (page does not exist)">5-iPrO-αMT</a></li> <li><a href="/wiki/5-MeO-%CE%B1,N,N-TMT" class="mw-redirect" title="5-MeO-α,N,N-TMT">5-MeO-α,<i>N</i>,<i>N</i>-TMT</a></li> <li><a href="/wiki/5-MeO-AET" title="5-MeO-AET">5-MeO-αET </a></li> <li><a href="/wiki/5-MeO-aMT" class="mw-redirect" title="5-MeO-aMT">5-MeO-αMT</a></li> <li><a href="/wiki/5-MeO-MPMI" title="5-MeO-MPMI">5-MeO-MPMI</a></li> <li><a href="/w/index.php?title=5-Methyl-AET&action=edit&redlink=1" class="new" title="5-Methyl-AET (page does not exist)">5-Methyl-αET</a></li> <li><a href="/wiki/6-Fluoro-AMT" title="6-Fluoro-AMT">6-Fluoro-αMT</a></li> <li><a href="/wiki/7-Chloro-AMT" title="7-Chloro-AMT">7-Chloro-αMT</a></li> <li><a href="/wiki/7-Methyl-%CE%B1-ethyltryptamine" title="7-Methyl-α-ethyltryptamine">7-Methyl-αET</a></li> <li><a href="/wiki/%CE%91-Methyl-5-hydroxytryptophan" title="Α-Methyl-5-hydroxytryptophan">α-Methyl-5-HTP</a></li> <li><a href="/wiki/%CE%91-Methylmelatonin" title="Α-Methylmelatonin">α-Methylmelatonin</a></li> <li><a href="/wiki/%CE%91-Methylserotonin" title="Α-Methylserotonin">α-Methylserotonin (5-HO-αMT)</a></li> <li><a href="/wiki/%CE%91-Methyltryptophan" title="Α-Methyltryptophan">α-Methyltryptophan (αMTP)</a></li> <li><a href="/wiki/Alpha,N-DMT" class="mw-redirect" title="Alpha,N-DMT">α,<i>N</i>-DMT (<i>N</i>-methyl-αMT)</a></li> <li><a href="/wiki/%CE%91,N,N-Trimethyltryptamine" title="Α,N,N-Trimethyltryptamine">α,<i>N</i>,<i>N</i>-TMT</a></li> <li><a href="/wiki/Alpha,N,O-TMS" class="mw-redirect" title="Alpha,N,O-TMS">α,<i>N</i>,<i>O</i>-TMS</a></li> <li><a href="/wiki/%CE%91-Ethyltryptamine" title="Α-Ethyltryptamine">αET (etryptamine)</a></li> <li><a href="/wiki/%CE%91-Methyltryptamine" title="Α-Methyltryptamine">αMT</a></li> <li><a href="/wiki/AL-37350A" title="AL-37350A">AL-37350A (4,5-DHP-αMT)</a></li> <li><a href="/w/index.php?title=BK-5Br-NM-AMT&action=edit&redlink=1" class="new" title="BK-5Br-NM-AMT (page does not exist)">BK-5Br-NM-AMT</a></li> <li><a href="/w/index.php?title=BK-5Cl-NM-AMT&action=edit&redlink=1" class="new" title="BK-5Cl-NM-AMT (page does not exist)">BK-5Cl-NM-AMT</a></li> <li><a href="/w/index.php?title=BK-5F-NM-AMT&action=edit&redlink=1" class="new" title="BK-5F-NM-AMT (page does not exist)">BK-5F-NM-AMT</a></li> <li><a href="/wiki/BK-NM-AMT" title="BK-NM-AMT">BK-NM-AMT</a></li> <li><a href="/wiki/BNC-210" title="BNC-210">BNC-210</a></li> <li><a href="/wiki/BW-723C86" title="BW-723C86">BW-723C86</a></li> <li><a href="/wiki/CP-135807" title="CP-135807">CP-135807</a></li> <li><a href="/wiki/Indolylpropylaminopentane" title="Indolylpropylaminopentane">IPAP (α,<i>N</i>-DPT)</a></li> <li><a href="/wiki/MPMI_(drug)" title="MPMI (drug)">MPMI</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a class="mw-selflink selflink">Triptans</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Almotriptan" title="Almotriptan">Almotriptan</a></li> <li><a href="/wiki/Donitriptan" title="Donitriptan">Donitriptan</a></li> <li><a href="/wiki/Eletriptan" title="Eletriptan">Eletriptan</a></li> <li><a href="/wiki/Frovatriptan" title="Frovatriptan">Frovatriptan</a></li> <li><a href="/wiki/L-694247" title="L-694247">L-694247</a></li> <li><a href="/wiki/Rizatriptan" title="Rizatriptan">Rizatriptan</a></li> <li><a href="/wiki/Sumatriptan" title="Sumatriptan">Sumatriptan</a></li> <li><a href="/wiki/Zolmitriptan" title="Zolmitriptan">Zolmitriptan</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Cyclic_compound" title="Cyclic compound">Cyclized tryptamines</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Bay_R_1531" title="Bay R 1531">Bay R 1531</a></li> <li><a href="/wiki/Ciclindole" title="Ciclindole">Ciclindole</a></li> <li><a href="/wiki/Cyclic_3-hydroxymelatonin" title="Cyclic 3-hydroxymelatonin">Cyclic 3-OHM</a></li> <li><a href="/wiki/Ergoline" title="Ergoline">Ergolines</a> and <a href="/wiki/Lysergamide" class="mw-redirect" title="Lysergamide">lysergamides</a> (e.g., <a href="/wiki/Lysergic_acid_diethylamide" class="mw-redirect" title="Lysergic acid diethylamide">LSD</a>)</li> <li><a href="/wiki/Flucindole" title="Flucindole">Flucindole</a></li> <li><a href="/wiki/Harmala_alkaloid" title="Harmala alkaloid"><i>Harmala</i> alkaloids</a> and <a href="/wiki/%CE%92-carboline" class="mw-redirect" title="Β-carboline">β-carbolines</a> (e.g., <a href="/wiki/6-MeO-THH" title="6-MeO-THH">6-MeO-THH</a>, <a href="/wiki/9-Methyl-%CE%B2-carboline" title="9-Methyl-β-carboline">9-Me-BC</a>, <a href="/wiki/%CE%92-carboline" class="mw-redirect" title="Β-carboline">β-carboline (norharman)</a>, <a href="/wiki/Harmaline" title="Harmaline">harmaline</a>, <a href="/wiki/Harmalol" title="Harmalol">harmalol</a>, <a href="/wiki/Harmane" title="Harmane">harmane</a>, <a href="/wiki/Harmine" title="Harmine">harmine</a>, <a href="/wiki/Pinoline" title="Pinoline">pinoline</a>, <a href="/wiki/Tetrahydroharmine" title="Tetrahydroharmine">tetrahydroharmine</a>, <a href="/wiki/Tryptoline" title="Tryptoline">tryptoline</a>)</li> <li><a href="/wiki/Iboga-type_alkaloid" title="Iboga-type alkaloid"><i>Iboga</i> alkaloids</a> and related (e.g., <a href="/wiki/DM-506" title="DM-506">DM-506 (ibogaminalog)</a>, <a href="/wiki/Ibogaine" title="Ibogaine">ibogaine</a>, <a href="/wiki/Ibogamine" title="Ibogamine">ibogamine</a>, <a href="/wiki/Noribogaine" title="Noribogaine">noribogaine</a>, <a href="/wiki/Tabernanthalog" title="Tabernanthalog">tabernanthalog</a>, <a href="/wiki/Tabernanthine" title="Tabernanthine">tabernanthine</a>)</li> <li><a href="/wiki/LY-266,097" title="LY-266,097">LY-266,097</a></li> <li><a href="/wiki/Metralindole" title="Metralindole">Metralindole</a></li> <li><a href="/wiki/NDTDI" title="NDTDI">NDTDI</a></li> <li><a href="/wiki/PHA-57378" title="PHA-57378">PHA-57378</a></li> <li><a href="/wiki/PNU-22394" title="PNU-22394">PNU-22394</a></li> <li><a href="/wiki/PNU-181731" title="PNU-181731">PNU-181731</a></li> <li><a href="/wiki/RU-28306" title="RU-28306">RU-28306</a></li> <li><a href="/wiki/Yohimban" title="Yohimban">Yohimbans</a> (e.g., <a href="/wiki/Yohimbine" title="Yohimbine">yohimbine</a>, <a href="/wiki/Rauwolscine" title="Rauwolscine">rauwolscine</a>, <a href="/wiki/Spegatrine" title="Spegatrine">spegatrine</a>, <a href="/wiki/Corynanthine" title="Corynanthine">corynanthine</a>, <a href="/wiki/Ajmalicine" title="Ajmalicine">ajmalicine</a>, <a href="/wiki/Reserpine" title="Reserpine">reserpine</a>, <a href="/wiki/Deserpidine" title="Deserpidine">deserpidine</a>, <a href="/wiki/Rescinnamine" title="Rescinnamine">rescinnamine</a>)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Isotryptamine" title="Isotryptamine">Isotryptamines</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/5-MeO-isoDMT" title="5-MeO-isoDMT">5-MeO-isoDMT</a></li> <li><a href="/wiki/6-MeO-isoDMT" title="6-MeO-isoDMT">6-MeO-isoDMT</a></li> <li><a href="/wiki/AAZ-A-154" class="mw-redirect" title="AAZ-A-154">AAZ-A-154 (DLX-001)</a></li> <li><a href="/wiki/IsoAMT" class="mw-redirect" title="IsoAMT">isoAMT</a></li> <li><a href="/wiki/IsoDMT" title="IsoDMT">isoDMT</a></li> <li><a href="/wiki/Isotryptamine" title="Isotryptamine">Isotryptamine (isoT)</a></li> <li><a href="/wiki/PNU-181731" title="PNU-181731">PNU-181731</a></li> <li><a href="/wiki/Ro60-0175" title="Ro60-0175">Ro60-0175</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;">Related compounds</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/w/index.php?title=2-Azapsilocin&action=edit&redlink=1" class="new" title="2-Azapsilocin (page does not exist)">2-Azapsilocin</a></li> <li><a href="/w/index.php?title=4-Aza-5-MeO-DPT&action=edit&redlink=1" class="new" title="4-Aza-5-MeO-DPT (page does not exist)">4-Aza-5-MeO-DPT</a></li> <li><a href="/w/index.php?title=5-Aza-4-MeO-DiPT&action=edit&redlink=1" class="new" title="5-Aza-4-MeO-DiPT (page does not exist)">5-Aza-4-MeO-DiPT</a></li> <li><a href="/wiki/5-Hydroxyindoleacetic_acid" title="5-Hydroxyindoleacetic acid">5-HIAA</a></li> <li><a href="/wiki/5-Hydroxyindoleacetaldehyde" title="5-Hydroxyindoleacetaldehyde">5-HIAL</a></li> <li><a href="/w/index.php?title=5-Hydroxyindole_thiazoladine_carboxylic_acid&action=edit&redlink=1" class="new" title="5-Hydroxyindole thiazoladine carboxylic acid (page does not exist)">5-HITCA</a></li> <li><a href="/w/index.php?title=5-Methoxyindoleacetaldehyde&action=edit&redlink=1" class="new" title="5-Methoxyindoleacetaldehyde (page does not exist)">5-MIAL</a></li> <li><a href="/w/index.php?title=7-Aza-5-MeO-DiPT&action=edit&redlink=1" class="new" title="7-Aza-5-MeO-DiPT (page does not exist)">7-Aza-5-MeO-DiPT</a></li> <li><a href="/wiki/AAZ-A-154" class="mw-redirect" title="AAZ-A-154">AAZ-A-154</a></li> <li><a href="/wiki/AL-34662" title="AL-34662">AL-34662</a></li> <li><a href="/wiki/AL-38022A" title="AL-38022A">AL-38022A</a></li> <li><a href="/wiki/Substituted_benzofuran" title="Substituted benzofuran">Benzofurans</a> (e.g., <a href="/wiki/3-(2-aminopropyl)benzofuran" class="mw-redirect" title="3-(2-aminopropyl)benzofuran">3-APB</a>, <a href="/wiki/5-MeO-DiBF" title="5-MeO-DiBF">5-MeO-DiBF</a>, <a href="/wiki/Benzofuranylpropylaminopentane" title="Benzofuranylpropylaminopentane">BPAP</a>, <a href="/wiki/Dimemebfe" title="Dimemebfe">dimemebfe</a>, <a href="/wiki/Mebfap" title="Mebfap">mebfap</a>)</li> <li><a href="/wiki/BRL-54443" title="BRL-54443">BRL-54443</a></li> <li><a href="/wiki/CP-94253" title="CP-94253">CP-94253</a></li> <li><a href="/wiki/EMD-386088" title="EMD-386088">EMD-386088</a></li> <li><a href="/w/index.php?title=I-32_(drug)&action=edit&redlink=1" class="new" title="I-32 (drug) (page does not exist)">I-32</a></li> <li><a href="/wiki/Indoleacetaldehyde" class="mw-redirect" title="Indoleacetaldehyde">IAL</a></li> <li><a href="/wiki/Latrepirdine" title="Latrepirdine">Latrepirdine</a></li> <li><a href="/wiki/LY-367,265" title="LY-367,265">LY-367265</a></li> <li>Non-tryptamine <a class="mw-selflink selflink">triptans</a> (e.g., <a href="/wiki/Avitriptan" title="Avitriptan">avitriptan</a>, <a href="/wiki/LY-334370" title="LY-334370">LY-334370</a>, <a href="/wiki/Naratriptan" title="Naratriptan">naratriptan</a>)</li> <li><a href="/wiki/Pirlindole" title="Pirlindole">Pirlindole</a></li> <li><a href="/wiki/(R)-69" title="(R)-69">(<i>R</i>)-69 (3IQ)</a></li> <li><a href="/wiki/Ro60-0213" title="Ro60-0213">Ro60-0213</a></li> <li><a href="/wiki/RU-24,969" title="RU-24,969">RU-24,969</a></li> <li><a href="/wiki/Sertindole" title="Sertindole">Sertindole</a></li> <li><a href="/wiki/SN-22" title="SN-22">SN-22</a></li> <li><a href="/wiki/Tepirindole" title="Tepirindole">Tepirindole</a></li> <li><a href="/wiki/Tetrindole" title="Tetrindole">Tetrindole</a></li> <li><a href="/wiki/VER-3323" title="VER-3323">VER-3323</a></li> <li><a href="/wiki/VU6067416" title="VU6067416">VU6067416</a></li> <li><a href="/wiki/YM-348" title="YM-348">YM-348</a></li></ul> </div></td></tr></tbody></table></div>    </div><noscript><img src="https://login.wikimedia.org/wiki/Special:CentralAutoLogin/start?useformat=desktop&type=1x1&usesul3=0" alt="" width="1" height="1" style="border: none; position: absolute;"></noscript> <div class="printfooter" data-nosnippet="">Retrieved from "<a dir="ltr" href="https://en.wikipedia.org/w/index.php?title=Triptan&oldid=1275791046">https://en.wikipedia.org/w/index.php?title=Triptan&oldid=1275791046</a>"</div></div> <div 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