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data-mw-deduplicate="TemplateStyles:r1268415487">.mw-parser-output .ib-chembox{border-collapse:collapse;text-align:left}.mw-parser-output .ib-chembox td,.mw-parser-output .ib-chembox th{border:1px solid #a2a9b1;width:40%}.mw-parser-output .ib-chembox td+td{width:60%}@media screen{html.skin-theme-clientpref-night .mw-parser-output .ib-chembox figure:not(.skin-invert-image):not(.skin-invert):not(.bg-transparent){background:var(--background-color-inverted,#f8f9fa)}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .ib-chembox figure:not(.skin-invert-image):not(.skin-invert):not(.bg-transparent){background:var(--background-color-inverted,#f8f9fa)}}</style> <table class="infobox ib-chembox"> <caption>6-Hydroxymelatonin </caption> <tbody><tr> <td colspan="2" style="text-align:center; padding:2px;"><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:6-Hydroxymelatonin_structure.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/c/ce/6-Hydroxymelatonin_structure.svg/200px-6-Hydroxymelatonin_structure.svg.png" decoding="async" width="200" height="157" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/c/ce/6-Hydroxymelatonin_structure.svg/300px-6-Hydroxymelatonin_structure.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/c/ce/6-Hydroxymelatonin_structure.svg/400px-6-Hydroxymelatonin_structure.svg.png 2x" data-file-width="1150" data-file-height="900" /></a><figcaption></figcaption></figure> </td></tr> <tr> <th colspan="2" style="background: #f8eaba;color:inherit; text-align: center;">Names </th></tr> <tr> <td colspan="2" style="text-align:left;"><a href="/wiki/Preferred_IUPAC_name" title="Preferred IUPAC name">Preferred IUPAC name</a> <div style="max-width:22em; word-wrap:break-word; padding-left:1.7em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0; max-width:22em;"><i>N</i>-[2-(6-Hydroxy-5-methoxy-1<i>H</i>-indol-3-yl)ethyl]acetamide</div></div> </td></tr> <tr> <td colspan="2" style="text-align:left;">Other names <div style="max-width:22em; word-wrap:break-word; padding-left:1.7em;">6-Oxymelatonin</div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba;color:inherit; text-align: center;">Identifiers </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/CAS_Registry_Number" title="CAS Registry Number">CAS Number</a></div> </td> <td><style data-mw-deduplicate="TemplateStyles:r1126788409">.mw-parser-output .plainlist ol,.mw-parser-output .plainlist ul{line-height:inherit;list-style:none;margin:0;padding:0}.mw-parser-output .plainlist ol li,.mw-parser-output .plainlist ul li{margin-bottom:0}</style><div class="plainlist"><ul><li><span title="commonchemistry.cas.org"><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=2208-41-5">2208-41-5</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">3D model (<a href="/wiki/JSmol" class="mw-redirect" title="JSmol">JSmol</a>)</div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><span title="chemapps.stolaf.edu (3D interactive model)"><a rel="nofollow" class="external text" href="https://chemapps.stolaf.edu/jmol/jmol.php?model=CC%28%3DO%29NCCC1%3DCNC2%3DCC%28%3DC%28C%3DC21%29OC%29O">Interactive image</a></span></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ChEBI" title="ChEBI">ChEBI</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><span title="www.ebi.ac.uk"><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chebi/searchId.do?chebiId=198">CHEBI:198</a></span></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ChemSpider" title="ChemSpider">ChemSpider</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><span title="www.chemspider.com"><a rel="nofollow" class="external text" href="https://www.chemspider.com/Chemical-Structure.1794.html">1794</a></span></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ECHA_InfoCard" class="mw-redirect" title="ECHA InfoCard"><span title="echa.europa.eu">ECHA InfoCard</span></a> </td> <td><a rel="nofollow" class="external text" href="https://echa.europa.eu/substance-information/-/substanceinfo/100.164.426">100.164.426</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q20707319#P2566" title="Edit this at Wikidata"><img alt="Edit this at Wikidata" src="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/10px-OOjs_UI_icon_edit-ltr-progressive.svg.png" decoding="async" width="10" height="10" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/15px-OOjs_UI_icon_edit-ltr-progressive.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/20px-OOjs_UI_icon_edit-ltr-progressive.svg.png 2x" data-file-width="20" data-file-height="20" /></a></span> </td></tr> <tr> <td><a href="/wiki/KEGG" title="KEGG">KEGG</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><span title="www.kegg.jp"><a rel="nofollow" class="external text" href="https://www.kegg.jp/entry/C05643">C05643</a></span></li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/PubChem" title="PubChem">PubChem</a> <abbr title="Compound ID">CID</abbr></div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><span title="pubchem.ncbi.nlm.nih.gov"><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/1864">1864</a></span></li></ul></div> </td></tr> <tr> <td><a href="/wiki/Unique_Ingredient_Identifier" title="Unique Ingredient Identifier">UNII</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><span title="precision.fda.gov"><a rel="nofollow" class="external text" href="https://precision.fda.gov/uniisearch/srs/unii/TV437T5077">TV437T5077</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/CompTox_Chemicals_Dashboard" title="CompTox Chemicals Dashboard">CompTox Dashboard</a> <span style="font-weight:normal">(<abbr title="U.S. Environmental Protection Agency">EPA</abbr>)</span></div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><span title="comptox.epa.gov"><a rel="nofollow" class="external text" href="https://comptox.epa.gov/dashboard/chemical/details/DTXSID00176577">DTXSID00176577</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q20707319#P3117" title="Edit this at Wikidata"><img alt="Edit this at Wikidata" src="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/10px-OOjs_UI_icon_edit-ltr-progressive.svg.png" decoding="async" width="10" height="10" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/15px-OOjs_UI_icon_edit-ltr-progressive.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/20px-OOjs_UI_icon_edit-ltr-progressive.svg.png 2x" data-file-width="20" data-file-height="20" /></a></span></span></li></ul></div> </td></tr> <tr> <td colspan="2"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold; text-align:left; font-weight:normal;"><div><a href="/wiki/International_Chemical_Identifier" title="International Chemical Identifier">InChI</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.5em; text-align:left;"><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">InChI=1S/C13H16N2O3/c1-8(16)14-4-3-9-7-15-11-6-12(17)13(18-2)5-10(9)11/h5-7,15,17H,3-4H2,1-2H3,(H,14,16)</div><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">Key: OMYMRCXOJJZYKE-UHFFFAOYSA-N</div></div></li><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.5em; text-align:left;"><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">InChI=1/C13H16N2O3/c1-8(16)14-4-3-9-7-15-11-6-12(17)13(18-2)5-10(9)11/h5-7,15,17H,3-4H2,1-2H3,(H,14,16)</div><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">Key: OMYMRCXOJJZYKE-UHFFFAOYAK</div></div></li></ul> </div> </td></tr> <tr> <td colspan="2"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold; text-align:left; font-weight:normal;"><div><a href="/wiki/Simplified_molecular-input_line-entry_system" class="mw-redirect" title="Simplified molecular-input line-entry system">SMILES</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.6em; word-wrap:break-word; text-indent:-1.5em; text-align:left; font-size:97%; line-height:120%;">CC(=O)NCCC1=CNC2=CC(=C(C=C21)OC)O</div></li></ul> </div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba;color:inherit; text-align: center;">Properties </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Chemical_formula" title="Chemical formula">Chemical formula</a></div> </td> <td><span title="Carbon">C</span><sub>13</sub><span title="Hydrogen">H</span><sub>16</sub><span title="Nitrogen">N</span><sub>2</sub><span title="Oxygen">O</span><sub>3</sub> </td></tr> <tr> <td><a href="/wiki/Molar_mass" title="Molar mass">Molar mass</a> </td> <td><span class="nowrap"><span data-sort-value="7002248282000000000♠"></span>248.282</span> g·mol<sup>−1</sup>   </td></tr> <tr> <td colspan="2" style="text-align:left; background:#f8eaba; color:inherit; border:1px solid #a2a9b1;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">Except where otherwise noted, data are given for materials in their <a href="/wiki/Standard_state" title="Standard state">standard state</a> (at 25 °C [77 °F], 100 kPa).</div> <div style="margin-top: 0.3em;"></div> <div style="margin-top: 0.3em; text-align: center;"><a href="/wiki/Wikipedia:Chemical_infobox#References" title="Wikipedia:Chemical infobox">Infobox references</a></div> </td></tr> </tbody></table><div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Chemical compound</div> <p><b>6-Hydroxymelatonin</b> (<b>6-OHM</b>) is a <a href="/wiki/Natural_product" title="Natural product">naturally occurring</a>, <a href="/wiki/Endogenous" class="mw-redirect" title="Endogenous">endogenous</a>, major <a href="/wiki/Active_metabolite" title="Active metabolite">active metabolite</a> of <a href="/wiki/Melatonin" title="Melatonin">melatonin</a>.<sup id="cite_ref-pmid21358968_1-0" class="reference"><a href="#cite_note-pmid21358968-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> 6-Hydroxymelatonin is produced as a result of the enzymatic conversion of melatonin through <a href="/wiki/Hydroxylation" title="Hydroxylation">hydroxylation</a>.<sup id="cite_ref-:0_2-0" class="reference"><a href="#cite_note-:0-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> Similar to melatonin, 6-OHM is a <a href="/wiki/Full_agonist" class="mw-redirect" title="Full agonist">full agonist</a> of the <a href="/wiki/Melatonin_receptor_1A" title="Melatonin receptor 1A">MT<sub>1</sub></a> and <a href="/wiki/Melatonin_receptor_1B" title="Melatonin receptor 1B">MT<sub>2</sub> receptors</a>.<sup id="cite_ref-pmid2842214_3-0" class="reference"><a href="#cite_note-pmid2842214-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-BrowningBeresford2000_4-0" class="reference"><a href="#cite_note-BrowningBeresford2000-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> It is also an <a href="/wiki/Antioxidant" title="Antioxidant">antioxidant</a> and <a href="/wiki/Neuroprotective" class="mw-redirect" title="Neuroprotective">neuroprotective</a>, and is even more potent in this regard relative to melatonin.<sup id="cite_ref-pmid17828452_5-0" class="reference"><a href="#cite_note-pmid17828452-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-pmid26079042_6-0" class="reference"><a href="#cite_note-pmid26079042-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Role_in_metabolism">Role in metabolism</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=6-Hydroxymelatonin&action=edit&section=1" title="Edit section: Role in metabolism"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The determination of 6-OHM in human urine has been used to track the metabolism and excretion of melatonin using <a href="/wiki/LC-MS/MS" class="mw-redirect" title="LC-MS/MS">LC-MS/MS</a>, providing quantifiable insights into <a href="/wiki/Circadian_rhythm" title="Circadian rhythm">circadian rhythm regulation</a> and its oxidative role as a <a href="/wiki/Biomarker" title="Biomarker">biomarker</a>.<sup id="cite_ref-:02_7-0" class="reference"><a href="#cite_note-:02-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> 6-OHM is one of four of the primary metabolic products of melatonin in the liver and is also a byproduct of its breakdown due to exposure to light. It is known to be very effective in protecting cells from <a href="/wiki/Oxidative_stress" title="Oxidative stress">oxidative damage</a> caused by <a href="/wiki/UV_Radiation" class="mw-redirect" title="UV Radiation">ultraviolet (UV) radiation</a>.<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> Based on comparisons with other melatonin-related compounds, it is suggested that the protective effects of 6-OHM in mitigating oxidative stress are primarily attributed to their ability to scavenge <a href="/wiki/Radical_(chemistry)" title="Radical (chemistry)">free radicals</a>.<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-heading2"><h2 id="See_also">See also</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=6-Hydroxymelatonin&action=edit&section=2" title="Edit section: See also"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a href="/wiki/N-Acetylserotonin" title="N-Acetylserotonin"><i>N</i>-Acetylserotonin</a> (normelatonin)</li> <li><a href="/wiki/5-Methoxytryptamine" title="5-Methoxytryptamine">5-Methoxytryptamine</a></li> <li><a href="/wiki/Melatonin" title="Melatonin">Melatonin</a></li></ul> <div class="mw-heading mw-heading2"><h2 id="References">References</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=6-Hydroxymelatonin&action=edit&section=3" title="Edit section: References"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1239543626">.mw-parser-output .reflist{margin-bottom:0.5em;list-style-type:decimal}@media screen{.mw-parser-output .reflist{font-size:90%}}.mw-parser-output .reflist .references{font-size:100%;margin-bottom:0;list-style-type:inherit}.mw-parser-output .reflist-columns-2{column-width:30em}.mw-parser-output .reflist-columns-3{column-width:25em}.mw-parser-output .reflist-columns{margin-top:0.3em}.mw-parser-output .reflist-columns ol{margin-top:0}.mw-parser-output .reflist-columns li{page-break-inside:avoid;break-inside:avoid-column}.mw-parser-output .reflist-upper-alpha{list-style-type:upper-alpha}.mw-parser-output .reflist-upper-roman{list-style-type:upper-roman}.mw-parser-output .reflist-lower-alpha{list-style-type:lower-alpha}.mw-parser-output .reflist-lower-greek{list-style-type:lower-greek}.mw-parser-output .reflist-lower-roman{list-style-type:lower-roman}</style><div class="reflist reflist-columns references-column-width reflist-columns-2"> <ol class="references"> <li id="cite_note-pmid21358968-1"><span class="mw-cite-backlink"><b><a href="#cite_ref-pmid21358968_1-0">^</a></b></span> <span class="reference-text"><style 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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 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navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%;font-weight:normal; text-align: center;">Major excitatory /<br />inhibitory systems</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%;font-weight:normal;">Glutamate system</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Agmatine" title="Agmatine">Agmatine</a></li> <li><a href="/wiki/Aspartic_acid" title="Aspartic acid">Aspartic acid (aspartate)</a></li> <li><a href="/wiki/Glutamate_(neurotransmitter)" title="Glutamate (neurotransmitter)">Glutamic acid (glutamate)</a></li> <li><a href="/wiki/Glutathione" title="Glutathione">Glutathione</a></li> <li><a href="/wiki/Glycine" title="Glycine">Glycine</a></li> <li><a href="/wiki/S-Nitrosoglutathione" title="S-Nitrosoglutathione">GSNO</a></li> <li><a href="/wiki/Glutathione_disulfide" title="Glutathione disulfide">GSSG</a></li> <li><a href="/wiki/Kynurenic_acid" title="Kynurenic acid">Kynurenic acid</a></li> <li><a href="/wiki/N-Acetylaspartic_acid" title="N-Acetylaspartic acid">NAA</a></li> <li><a href="/wiki/N-Acetylaspartylglutamic_acid" title="N-Acetylaspartylglutamic acid">NAAG</a></li> <li><a href="/wiki/Proline" title="Proline">Proline</a></li> <li><a href="/wiki/Serine" title="Serine">Serine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;font-weight:normal;">GABA system</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/GABA" title="GABA">GABA</a></li> <li><a href="/wiki/%CE%93-Amino-%CE%B2-hydroxybutyric_acid" title="Γ-Amino-β-hydroxybutyric acid">GABOB</a></li> <li><a href="/wiki/%CE%93-Hydroxybutyric_acid" title="Γ-Hydroxybutyric acid">GHB</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;font-weight:normal;">Glycine system</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Alanine" title="Alanine">α-Alanine</a></li> <li><a href="/wiki/%CE%92-Alanine" title="Β-Alanine">β-Alanine</a></li> <li><a href="/wiki/Glycine" title="Glycine">Glycine</a></li> <li><a href="/wiki/Hypotaurine" title="Hypotaurine">Hypotaurine</a></li> <li><a href="/wiki/Proline" title="Proline">Proline</a></li> <li><a href="/wiki/Sarcosine" title="Sarcosine">Sarcosine</a></li> <li><a href="/wiki/Serine" title="Serine">Serine</a></li> <li><a href="/wiki/Taurine" title="Taurine">Taurine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;font-weight:normal;"><a href="/wiki/GHB_receptor" title="GHB receptor">GHB system</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/%CE%93-Hydroxybutyric_acid" title="Γ-Hydroxybutyric acid">GHB</a></li> <li><a href="/wiki/T-HCA" title="T-HCA">T-HCA (GHC)</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;font-weight:normal; text-align: center;"><a href="/wiki/Biogenic_amine" title="Biogenic amine">Biogenic amines</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:4em;font-weight:normal; text-align: center;">Monoamines</th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a class="mw-selflink selflink">6-OHM</a></li> <li><a href="/wiki/Dopamine" title="Dopamine">Dopamine</a></li> <li><a href="/wiki/Adrenaline" title="Adrenaline">Epinephrine (adrenaline)</a></li> <li><a href="/wiki/N-Acetylserotonin" title="N-Acetylserotonin">NAS (normelatonin)</a></li> <li><a href="/wiki/Norepinephrine" title="Norepinephrine">Norepinephrine (noradrenaline)</a></li> <li><a href="/wiki/Serotonin" title="Serotonin">Serotonin (5-HT)</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:4em;font-weight:normal; text-align: center;">Trace amines</th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/3-Iodothyronamine" title="3-Iodothyronamine">3-Iodothyronamine</a></li> <li><a href="/wiki/N-Methylphenethylamine" title="N-Methylphenethylamine">N-Methylphenethylamine</a></li> <li><a href="/wiki/N-Methyltryptamine" title="N-Methyltryptamine">N-Methyltryptamine</a></li> <li><a href="/wiki/Norfenefrine" title="Norfenefrine"><i>m</i>-Octopamine</a></li> <li><a href="/wiki/Octopamine" title="Octopamine"><i>p</i>-Octopamine</a></li> <li><a href="/wiki/Phenylethanolamine" title="Phenylethanolamine">Phenylethanolamine</a></li> <li><a href="/wiki/Phenethylamine" title="Phenethylamine">Phenethylamine</a></li> <li><a href="/wiki/Synephrine" title="Synephrine">Synephrine</a></li> <li><a href="/wiki/Tryptamine" title="Tryptamine">Tryptamine</a></li> <li><a href="/wiki/Meta-Tyramine" title="Meta-Tyramine"><i>m</i>-Tyramine</a></li> <li><a href="/wiki/Tyramine" title="Tyramine"><i>p</i>-Tyramine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:4em;font-weight:normal; text-align: center;">Others</th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Histamine" title="Histamine">Histamine</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;font-weight:normal; text-align: center;"><a href="/wiki/Neuropeptide" title="Neuropeptide">Neuropeptides</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><td colspan="2" class="navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li>See <a href="/wiki/Template:Neuropeptides" title="Template:Neuropeptides">here</a> instead.</li></ul> </div></td></tr></tbody></table><div></div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="text-align: center;;width:1%"><a href="/wiki/Lipid" title="Lipid">Lipid</a>-derived</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th id="Endocannabinoids33" scope="row" class="navbox-group" style="width:1%;font-weight:normal; text-align: center;">Endocannabinoids</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/2-Arachidonoylglycerol" title="2-Arachidonoylglycerol">2-AG</a></li> <li><a href="/wiki/2-Arachidonyl_glyceryl_ether" title="2-Arachidonyl glyceryl ether">2-AGE (noladin ether)</a></li> <li><a href="/w/index.php?title=2-Arachidonoyl_lysophosphatidylinositol&action=edit&redlink=1" class="new" title="2-Arachidonoyl lysophosphatidylinositol (page does not exist)">2-ALPI</a></li> <li><a href="/wiki/2-Oleoylglycerol" title="2-Oleoylglycerol">2-OG</a></li> <li><a href="/wiki/Arachidonoyl_serotonin" title="Arachidonoyl serotonin">AA-5-HT</a></li> <li><a href="/wiki/Anandamide" title="Anandamide">Anandamide (AEA)</a></li> <li><a href="/wiki/Docosatetraenoylethanolamide" title="Docosatetraenoylethanolamide">DEA</a></li> <li><a href="/wiki/Lysophosphatidylinositol" title="Lysophosphatidylinositol">LPI</a></li> <li><a href="/wiki/N-Arachidonoyl_dopamine" title="N-Arachidonoyl dopamine">NADA</a></li> <li><a href="/wiki/N-Arachidonylglycine" title="N-Arachidonylglycine">NAGly</a></li> <li><a href="/wiki/Oleoylethanolamide" title="Oleoylethanolamide">OEA</a></li> <li><a href="/wiki/Oleamide" title="Oleamide">Oleamide</a></li> <li><a href="/wiki/Palmitoylethanolamide" title="Palmitoylethanolamide">PEA</a></li> <li><a href="/wiki/RVD-Hp%CE%B1" title="RVD-Hpα">RVD-Hpα</a></li> <li><a href="/wiki/Stearoylethanolamide" title="Stearoylethanolamide">SEA</a></li> <li><a href="/wiki/Virodhamine" title="Virodhamine">Virodhamine (O-AEA)</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;font-weight:normal; text-align: center;"><a href="/wiki/Neurosteroid" title="Neurosteroid">Neurosteroids</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><td colspan="2" class="navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li>See <a href="/wiki/Template:Steroid_hormones" title="Template:Steroid hormones">here</a> instead.</li></ul> </div></td></tr></tbody></table><div></div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="text-align: center;;width:1%"><a href="/wiki/Nucleobase" class="mw-redirect" title="Nucleobase">Nucleobase</a>-derived</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th id="Nucleosides11" scope="row" class="navbox-group" style="width:1%;font-weight:normal; text-align: center;">Nucleosides</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th id="Adenosine_system20" scope="row" class="navbox-group" style="width:1%;font-weight:normal; text-align: center;"><a href="/wiki/Adenosine" title="Adenosine">Adenosine</a> system</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Adenosine_diphosphate" title="Adenosine diphosphate">ADP</a></li> <li><a href="/wiki/Adenosine_monophosphate" title="Adenosine monophosphate">AMP</a></li> <li><a href="/wiki/Adenosine_triphosphate" title="Adenosine triphosphate">ATP</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="text-align: center;;width:1%"><a href="/wiki/Vitamin" title="Vitamin">Vitamin</a>-derived</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="text-align: center;;width:1%">Miscellaneous</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th id="Cholinergic_system18" scope="row" class="navbox-group" style="width:1%;font-weight:normal; text-align: center;">Cholinergic system</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Acetylcholine" title="Acetylcholine">Acetylcholine</a></li></ul> </div></td></tr></tbody></table><div> </div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th id="Gasotransmitters16" scope="row" class="navbox-group" style="width:1%;font-weight:normal; text-align: center;">Gasotransmitters</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Carbon_monoxide" title="Carbon monoxide">Carbon monoxide (CO)</a></li> <li><a href="/wiki/Hydrogen_sulfide" title="Hydrogen sulfide">Hydrogen sulfide (H<sub>2</sub>S)</a></li> <li><a href="/wiki/Nitric_oxide" title="Nitric oxide">Nitric oxide (NO)</a></li></ul> </div></td></tr></tbody></table><div> </div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th id="Candidates10" scope="row" class="navbox-group" style="width:1%;font-weight:normal; text-align: center;">Candidates</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Acetaldehyde" title="Acetaldehyde">Acetaldehyde</a></li> <li><a href="/wiki/Ammonia" title="Ammonia">Ammonia (NH<sub>3</sub>)</a></li> <li><a href="/wiki/Carbonyl_sulfide" title="Carbonyl sulfide">Carbonyl sulfide (COS)</a></li> <li><a href="/wiki/Nitrous_oxide" title="Nitrous oxide">Nitrous oxide (N<sub>2</sub>O)</a></li> <li><a href="/wiki/Sulfur_dioxide" title="Sulfur dioxide">Sulfur dioxide (SO<sub>2</sub>)</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374" /><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235" /></div><div role="navigation" class="navbox" aria-labelledby="Antioxidants62" style="padding:3px"><table class="nowraplinks mw-collapsible autocollapse navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374" /><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231" /><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Antioxidants" title="Template:Antioxidants"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Antioxidants" title="Template talk:Antioxidants"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Antioxidants" title="Special:EditPage/Template:Antioxidants"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Antioxidants62" style="font-size:114%;margin:0 4em"><a href="/wiki/Antioxidant" title="Antioxidant">Antioxidants</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%">Food antioxidants</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 class="mw-selflink selflink">6-Hydroxymelatonin</a></li> <li><a href="/wiki/Acetylcarnitine" title="Acetylcarnitine">Acetyl-<small>L</small>-carnitine</a> (ALCAR)</li> <li><a href="/wiki/Lipoic_acid" title="Lipoic acid">Alpha-lipoic acid</a> (ALA)</li> <li><a href="/wiki/Vitamin_C" title="Vitamin C">Ascorbic acid</a> (vitamin C)</li> <li><a href="/wiki/Carotenoid" title="Carotenoid">Carotenoids</a> (<a href="/wiki/Vitamin_A" title="Vitamin A">vitamin A</a>)</li> <li><a href="/wiki/Curcumin" title="Curcumin">Curcumin</a></li> <li><a href="/wiki/Edaravone" title="Edaravone">Edaravone</a></li> <li><a href="/wiki/Antioxidant_effect_of_polyphenols_and_natural_phenols" title="Antioxidant effect of polyphenols and natural phenols">Polyphenols</a></li> <li><a href="/wiki/Glutathione" title="Glutathione">Glutathione</a></li> <li><a href="/wiki/Hydroxytyrosol" title="Hydroxytyrosol">Hydroxytyrosol</a></li> <li><a href="/wiki/Carnitine" title="Carnitine"><small>L</small>-carnitine</a></li> <li><a href="/wiki/Ladostigil" title="Ladostigil">Ladostigil</a></li> <li><a href="/wiki/Melatonin" title="Melatonin">Melatonin</a></li> <li><a href="/wiki/Mofegiline" title="Mofegiline">Mofegiline</a></li> <li><a href="/wiki/Acetylcysteine" title="Acetylcysteine"><i>N</i>-Acetylcysteine</a> (NAC)</li> <li><a href="/wiki/N-Acetylserotonin" title="N-Acetylserotonin"><i>N</i>-Acetylserotonin</a> (NAS)</li> <li><a href="/wiki/Oleocanthal" title="Oleocanthal">Oleocanthal</a></li> <li><a href="/wiki/Oleuropein" title="Oleuropein">Oleuropein</a></li> <li><a href="/wiki/Rasagiline" title="Rasagiline">Rasagiline</a></li> <li><a href="/wiki/Resveratrol" title="Resveratrol">Resveratrol</a></li> <li><a href="/wiki/Selegiline" title="Selegiline">Selegiline</a></li> <li><a href="/wiki/Selenium" title="Selenium">Selenium</a></li> <li><a href="/wiki/Tocopherol" title="Tocopherol">Tocopherols</a> (<a href="/wiki/Vitamin_E" title="Vitamin E">vitamin E</a>)</li> <li><a href="/wiki/Tocotrienol" title="Tocotrienol">Tocotrienols</a> (<a href="/wiki/Vitamin_E" title="Vitamin E">vitamin E</a>)</li> <li><a href="/wiki/Tyrosol" title="Tyrosol">Tyrosol</a></li> <li><a href="/wiki/Coenzyme_Q10" title="Coenzyme Q10">Ubiquinone</a> (coenzyme Q)</li> <li><a href="/wiki/Uric_acid" title="Uric acid">Uric acid</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Fuel antioxidants</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/Butylated_hydroxyanisole" title="Butylated hydroxyanisole">Butylated hydroxyanisole</a></li> <li><a href="/wiki/Butylated_hydroxytoluene" title="Butylated hydroxytoluene">Butylated hydroxytoluene</a></li> <li><a href="/wiki/2,6-Di-tert-butylphenol" title="2,6-Di-tert-butylphenol">2,6-Di-<i>tert</i>-butylphenol</a></li> <li><a href="/wiki/1,2-Diaminopropane" title="1,2-Diaminopropane">1,2-Diaminopropane</a></li> <li><a href="/wiki/2,4-Dimethyl-6-tert-butylphenol" title="2,4-Dimethyl-6-tert-butylphenol">2,4-Dimethyl-6-<i>tert</i>-butylphenol</a></li> <li><a href="/wiki/Ethylenediamine" title="Ethylenediamine">Ethylenediamine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Measurements</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/Folin%E2%80%93Ciocalteu_reagent" title="Folin–Ciocalteu reagent">Folin method</a></li> <li><a href="/wiki/Oxygen_radical_absorbance_capacity" title="Oxygen radical absorbance capacity">ORAC</a></li> <li><a href="/wiki/Trolox_equivalent_antioxidant_capacity" title="Trolox equivalent antioxidant capacity">TEAC</a></li> <li><a href="/wiki/Ferric_reducing_ability_of_plasma" title="Ferric reducing ability of plasma">FRAP</a></li></ul> </div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374" /><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235" /></div><div role="navigation" class="navbox" aria-labelledby="Melatonin_receptor_modulators1178" style="padding:3px"><table class="nowraplinks hlist mw-collapsible mw-collapsed navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374" /><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231" /><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Melatonin_receptor_modulators" title="Template:Melatonin receptor modulators"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Melatonin_receptor_modulators" title="Template talk:Melatonin receptor modulators"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Melatonin_receptor_modulators" title="Special:EditPage/Template:Melatonin receptor modulators"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Melatonin_receptor_modulators1178" style="font-size:114%;margin:0 4em"><a href="/wiki/Melatonin_receptor" title="Melatonin receptor">Melatonin receptor</a> <a href="/wiki/Receptor_modulator" title="Receptor modulator">modulators</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Melatonin_receptor_1" class="mw-redirect" title="Melatonin receptor 1"><abbr title="Melatonin receptor 1">MT<sub>1</sub></abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Melatonin receptor 1</span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><b>Agonists:</b> <a href="/wiki/2-Iodomelatonin" title="2-Iodomelatonin">2-Iodomelatonin</a></li> <li><a class="mw-selflink selflink">6-Hydroxymelatonin</a></li> <li><a href="/wiki/Agomelatine" title="Agomelatine">Agomelatine</a></li> <li><a href="/wiki/Fabomotizole" title="Fabomotizole">Fabomotizole (afobazole)</a></li> <li><a href="/wiki/GR-196,429" title="GR-196,429">GR-196,429</a></li> <li><a href="/wiki/Melatonin" title="Melatonin">Melatonin</a></li> <li><a href="/wiki/N-Acetylserotonin" title="N-Acetylserotonin">N-Acetylserotonin (normelatonin)</a></li> <li><a href="/wiki/Piromelatine" title="Piromelatine">Piromelatine</a></li> <li><a href="/wiki/Ramelteon" title="Ramelteon">Ramelteon</a></li> <li><a href="/wiki/Tasimelteon" title="Tasimelteon">Tasimelteon</a></li> <li><a href="/wiki/TIK-301" title="TIK-301">TIK-301 (LY-156,735)</a></li></ul> <ul><li><b>Antagonists:</b> <a href="/wiki/Luzindole" title="Luzindole">Luzindole</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Melatonin_receptor_2" class="mw-redirect" title="Melatonin receptor 2"><abbr title="Melatonin receptor 2">MT<sub>2</sub></abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Melatonin receptor 2</span></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><b>Agonists:</b> <a href="/wiki/2-Iodomelatonin" title="2-Iodomelatonin">2-Iodomelatonin</a></li> <li><a class="mw-selflink selflink">6-Hydroxymelatonin</a></li> <li><a href="/wiki/Agomelatine" title="Agomelatine">Agomelatine</a></li> <li><a href="/wiki/GR-196,429" title="GR-196,429">GR-196,429</a></li> <li><a href="/wiki/Melatonin" title="Melatonin">Melatonin</a></li> <li><a href="/wiki/N-Acetylserotonin" title="N-Acetylserotonin">N-Acetylserotonin (normelatonin)</a></li> <li><a href="/wiki/Piromelatine" title="Piromelatine">Piromelatine</a></li> <li><a href="/wiki/Ramelteon" title="Ramelteon">Ramelteon</a></li> <li><a href="/wiki/Tasimelteon" title="Tasimelteon">Tasimelteon</a></li> <li><a href="/wiki/TIK-301" title="TIK-301">TIK-301 (LY-156,735)</a></li></ul> <ul><li><b>Antagonists:</b> <a href="/wiki/Luzindole" title="Luzindole">Luzindole</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;">Unsorted</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><b>Agonists:</b> <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="/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="/w/index.php?title=8-M-PDOT&action=edit&redlink=1" class="new" title="8-M-PDOT (page does not exist)">8-M-PDOT</a></li> <li><a href="/w/index.php?title=AMMTC&action=edit&redlink=1" class="new" title="AMMTC (page does not exist)">AMMTC</a></li> <li><a href="/w/index.php?title=GR-135,531&action=edit&redlink=1" class="new" title="GR-135,531 (page does not exist)">GR-135,531</a> (of <a href="/wiki/Melatonin_receptor_1C" title="Melatonin receptor 1C"><abbr title="melatonin receptor 1C">MT<sub>3</sub></abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip melatonin receptor 1C</span>)</li> <li><a href="/wiki/N-Acetyltryptamine" title="N-Acetyltryptamine">N-Acetyltryptamine</a></li> <li><a href="/w/index.php?title=N-Butanoylmelatonin&action=edit&redlink=1" class="new" title="N-Butanoylmelatonin (page does not exist)">N-Butanoylmelatonin</a></li> <li><a href="/w/index.php?title=N-Propionylmelatonin&action=edit&redlink=1" class="new" title="N-Propionylmelatonin (page does not exist)">N-Propionylmelatonin</a></li> <li><a href="/w/index.php?title=S-24268&action=edit&redlink=1" class="new" title="S-24268 (page does not exist)">S-24268</a></li> <li><a href="/w/index.php?title=S-25150&action=edit&redlink=1" class="new" title="S-25150 (page does not exist)">S-25150</a></li></ul> <ul><li><b>Antagonists:</b> <a href="/w/index.php?title=4-P-ADOT&action=edit&redlink=1" class="new" title="4-P-ADOT (page does not exist)">4-P-ADOT</a></li> <li><a href="/w/index.php?title=4-P-PDOT&action=edit&redlink=1" class="new" title="4-P-PDOT (page does not exist)">4-P-PDOT</a></li> <li><a href="/w/index.php?title=DH-97&action=edit&redlink=1" class="new" title="DH-97 (page does not exist)">DH-97</a></li> <li><a href="/wiki/N-Acetyltryptamine" title="N-Acetyltryptamine">N-Acetyltryptamine</a> (of <abbr title="melatonin receptor 1C">MT<sub>3</sub></abbr>)</li> <li><a href="/wiki/Prazosin" title="Prazosin">Prazosin</a> (of <abbr title="melatonin receptor 1C">MT<sub>3</sub></abbr>)</li> <li><a href="/w/index.php?title=S-20928&action=edit&redlink=1" class="new" title="S-20928 (page does not exist)">S-20928</a></li> <li><a href="/w/index.php?title=S-22153&action=edit&redlink=1" class="new" title="S-22153 (page does not exist)">S-22153</a></li> <li><a href="/w/index.php?title=S-24601&action=edit&redlink=1" class="new" title="S-24601 (page does not exist)">S-24601</a></li> <li><a href="/w/index.php?title=S-25567&action=edit&redlink=1" class="new" title="S-25567 (page does not exist)">S-25567</a></li> <li><a href="/w/index.php?title=S-26131&action=edit&redlink=1" class="new" title="S-26131 (page does not exist)">S-26131</a></li></ul> </div></td></tr><tr><td class="navbox-abovebelow" colspan="2"><div> <ul><li><i><b>See also:</b> <a href="/wiki/Template:Receptor_modulators" title="Template:Receptor modulators">Receptor/signaling modulators</a></i></li> <li><i><a href="/wiki/Template:Adrenergics" class="mw-redirect" title="Template:Adrenergics">Adrenergics</a></i></li> <li><i><a href="/wiki/Template:Dopaminergics" class="mw-redirect" title="Template:Dopaminergics">Dopaminergics</a></i></li> <li><i><a href="/wiki/Template:Serotonergics" class="mw-redirect" title="Template:Serotonergics">Serotonergics</a></i></li> <li><i><a href="/wiki/Template:Monoamine_metabolism_modulators" title="Template:Monoamine metabolism modulators">Monoamine metabolism modulators</a></i></li></ul> </div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374" /><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235" /></div><div role="navigation" class="navbox" aria-labelledby="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-MeO-pyr-T" class="mw-redirect" title="4-Fluoro-5-MeO-pyr-T">4-F-5-MeO-pyr-T</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="/w/index.php?title=4-HO-NiPT&action=edit&redlink=1" class="new" title="4-HO-NiPT (page does not exist)">4-HO-NiPT</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="/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="/w/index.php?title=5-HO-NiPT&action=edit&redlink=1" class="new" title="5-HO-NiPT (page does not exist)">5-HO-NiPT</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/Bretisilocin" title="Bretisilocin">Bretisilocin (5-fluoro-MET)</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="/wiki/N-Isopropyltryptamine" title="N-Isopropyltryptamine">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 class="mw-selflink selflink">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/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> <li><a href="/wiki/Soclenicant" title="Soclenicant">Soclenicant (BNC-210)</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Triptan" title="Triptan">Triptans</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Almotriptan" title="Almotriptan">Almotriptan</a></li> <li><a href="/wiki/Donitriptan" title="Donitriptan">Donitriptan</a></li> <li><a href="/wiki/Eletriptan" title="Eletriptan">Eletriptan</a></li> <li><a href="/wiki/Frovatriptan" title="Frovatriptan">Frovatriptan</a></li> <li><a href="/wiki/L-694247" title="L-694247">L-694247</a></li> <li><a href="/wiki/Rizatriptan" title="Rizatriptan">Rizatriptan</a></li> <li><a href="/wiki/Sumatriptan" title="Sumatriptan">Sumatriptan</a></li> <li><a href="/wiki/Zolmitriptan" title="Zolmitriptan">Zolmitriptan</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Cyclic_compound" title="Cyclic compound">Cyclized tryptamines</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Bay_R_1531" title="Bay R 1531">Bay R 1531</a></li> <li><a href="/wiki/Ciclindole" title="Ciclindole">Ciclindole</a></li> <li><a href="/wiki/Cyclic_3-hydroxymelatonin" title="Cyclic 3-hydroxymelatonin">Cyclic 3-OHM</a></li> <li><a href="/wiki/Ergoline" title="Ergoline">Ergolines</a> and <a href="/wiki/Lysergamide" class="mw-redirect" title="Lysergamide">lysergamides</a> (e.g., <a href="/wiki/Lysergic_acid_diethylamide" class="mw-redirect" title="Lysergic acid diethylamide">LSD</a>)</li> <li><a href="/wiki/Flucindole" title="Flucindole">Flucindole</a></li> <li><a href="/wiki/Harmala_alkaloid" title="Harmala alkaloid"><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/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> <li><a href="/wiki/Zalsupindole" title="Zalsupindole">Zalsupindole (DLX-001, AAZ-A-154)</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/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><a href="/wiki/Masupirdine" title="Masupirdine">Masupirdine</a></li> <li>Non-tryptamine <a href="/wiki/Triptan" title="Triptan">triptans</a> (e.g., <a href="/wiki/Avitriptan" title="Avitriptan">avitriptan</a>, <a href="/wiki/LY-334370" title="LY-334370">LY-334370</a>, <a href="/wiki/Naratriptan" title="Naratriptan">naratriptan</a>)</li> <li><a href="/wiki/Pirlindole" title="Pirlindole">Pirlindole</a></li> <li><a href="/wiki/(R)-69" title="(R)-69">(<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 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