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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">This article is about melatonin as a supplement and medication. For its role as a hormone, see <a href="/wiki/Melatonin" title="Melatonin">Melatonin</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" style="border-spacing:2px;"><caption class="infobox-title">Melatonin</caption><tbody><tr><td colspan="2" class="infobox-image notheme" style="background-color: #f8f9fa;"><a href="/wiki/File:Melatonin.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/7/74/Melatonin.svg/220px-Melatonin.svg.png" decoding="async" width="220" height="163" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/7/74/Melatonin.svg/330px-Melatonin.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/7/74/Melatonin.svg/440px-Melatonin.svg.png 2x" data-file-width="270" data-file-height="200" /></a></td></tr><tr><td colspan="2" class="infobox-image notheme" style="background-color: #f8f9fa;"><a href="/wiki/File:Melatonin_molecule_ball.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/2/24/Melatonin_molecule_ball.png/220px-Melatonin_molecule_ball.png" decoding="async" width="220" height="151" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/2/24/Melatonin_molecule_ball.png/330px-Melatonin_molecule_ball.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/2/24/Melatonin_molecule_ball.png/440px-Melatonin_molecule_ball.png 2x" data-file-width="2000" data-file-height="1375" /></a></td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd">Clinical data</th></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;">Pronunciation</th><td class="infobox-data"><a href="/wiki/Help:IPA/English" title="Help:IPA/English">/ˌmɛləˈtoʊnɪn/</a> <span data-nosnippet="" id="ooui-php-1" class="ext-phonos-PhonosButton noexcerpt ext-phonos-PhonosButton-emptylabel oo-ui-widget oo-ui-widget-enabled oo-ui-buttonElement oo-ui-buttonElement-frameless oo-ui-iconElement oo-ui-buttonWidget" data-ooui="{"_":"mw.Phonos.PhonosButton","href":"\/\/upload.wikimedia.org\/wikipedia\/commons\/transcoded\/f\/f6\/En-melatonin.oga\/En-melatonin.oga.mp3","rel":["nofollow"],"framed":false,"icon":"volumeUp","data":{"ipa":"","text":"","lang":"en","wikibase":"","file":"En-melatonin.oga"},"classes":["ext-phonos-PhonosButton","noexcerpt","ext-phonos-PhonosButton-emptylabel"]}"><a role="button" tabindex="0" href="//upload.wikimedia.org/wikipedia/commons/transcoded/f/f6/En-melatonin.oga/En-melatonin.oga.mp3" rel="nofollow" aria-label="Play audio" title="Play audio" class="oo-ui-buttonElement-button"></a><a href="/wiki/File:En-melatonin.oga" title="File:En-melatonin.oga">ⓘ</a> </td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Drug_nomenclature#Trade_names" title="Drug nomenclature">Trade names</a></th><td class="infobox-data">Circadin, Slenyto, others<a href="#cite_note-1">[1]</a></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;">Other names</th><td class="infobox-data">N-Acetyl-5-methoxy tryptamine<a href="#cite_note-2">[2]</a></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/American_Society_of_Health-System_Pharmacists" title="American Society of Health-System Pharmacists">AHFS</a>/<a href="/wiki/Drugs.com" title="Drugs.com">Drugs.com</a></th><td class="infobox-data"><a rel="nofollow" class="external text" href="https://www.drugs.com/cdi/melatonin.html">Consumer Drug Information</a></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Regulation_of_therapeutic_goods" title="Regulation of therapeutic goods">License data</a></th><td class="infobox-data"><style data-mw-deduplicate="TemplateStyles:r1126788409">.mw-parser-output .plainlist ol,.mw-parser-output .plainlist ul{line-height:inherit;list-style:none;margin:0;padding:0}.mw-parser-output .plainlist ol li,.mw-parser-output .plainlist ul li{margin-bottom:0}</style><div class="plainlist"> <ul><li><abbr class="country-name" title="United States">US</abbr> <a href="/wiki/DailyMed" title="DailyMed">DailyMed</a>: <a rel="nofollow" class="external text" href="https://dailymed.nlm.nih.gov/dailymed/search.cfm?labeltype=all&query=Melatonin">Melatonin</a></li></ul></div> </td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Pregnancy_category" title="Pregnancy category">Pregnancy category</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"> <ul><li><abbr class="country-name" title="Australia">AU</abbr>: B3<a href="#cite_note-Melatonin_AusPAR-3">[3]</a></li> <li class="mw-empty-elt"></li></ul> </div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Substance_dependence" title="Substance dependence">Dependence liability</a></th><td class="infobox-data">Physical: Low<a href="#cite_note-auto-4">[4]</a> Psychological: Low<a href="#cite_note-auto-4">[4]</a></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Addiction" title="Addiction">Addiction liability</a></th><td class="infobox-data">Low / none<a href="#cite_note-auto-4">[4]</a></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Route_of_administration" title="Route of administration">Routes of administration</a></th><td class="infobox-data"><a href="/wiki/Oral_administration" title="Oral administration">By mouth</a>, <a href="/wiki/Sublingual" class="mw-redirect" title="Sublingual">sublingual</a>, <a href="/wiki/Transdermal_patch" title="Transdermal patch">transdermal</a></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Drug_class" title="Drug class">Drug class</a></th><td class="infobox-data"><a href="/wiki/Melatonin_receptor_agonist" title="Melatonin receptor agonist">Melatonin receptor agonist</a></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Anatomical_Therapeutic_Chemical_Classification_System" title="Anatomical Therapeutic Chemical Classification System">ATC code</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><a href="/wiki/ATC_code_N05" title="ATC code N05">N05CH01</a> (<a rel="nofollow" class="external text" href="https://www.whocc.no/atc_ddd_index/?code=N05CH01">WHO</a>) </li></ul></div></td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd"><a href="/wiki/Physiological" class="mw-redirect" title="Physiological">Physiological</a> data</th></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;">Source <a href="/wiki/Tissue_(biology)" title="Tissue (biology)">tissues</a></th><td class="infobox-data"><a href="/wiki/Pineal_gland" title="Pineal gland">Pineal gland</a></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;">Target tissues</th><td class="infobox-data">Widespread, including <a href="/wiki/Brain" title="Brain">brain</a>, <a href="/wiki/Retina" title="Retina">retina</a>, and <a href="/wiki/Circulatory_system" title="Circulatory system">circulatory system</a></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Receptor_(biochemistry)" title="Receptor (biochemistry)">Receptors</a></th><td class="infobox-data"><a href="/wiki/Melatonin_receptor" title="Melatonin receptor">Melatonin receptor</a></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Precursor_(chemistry)" title="Precursor (chemistry)">Precursor</a></th><td class="infobox-data"><a href="/wiki/N-Acetylserotonin" title="N-Acetylserotonin">N-Acetylserotonin</a></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Drug_metabolism" title="Drug metabolism">Metabolism</a></th><td class="infobox-data"><a href="/wiki/Liver" title="Liver">Liver</a> via <a href="/wiki/CYP1A2" title="CYP1A2">CYP1A2</a> mediated 6-hydroxylation</td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd">Legal status</th></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Regulation_of_therapeutic_goods" title="Regulation of therapeutic goods">Legal status</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"> <ul><li><abbr class="country-name" title="Australia">AU</abbr>: <a href="/wiki/Standard_for_the_Uniform_Scheduling_of_Medicines_and_Poisons#Schedule_4" title="Standard for the Uniform Scheduling of Medicines and Poisons">S4</a> (Prescription only)<a href="#cite_note-Melatonin_AusPAR-3">[3]</a><a href="#cite_note-5">[5]</a></li> <li><abbr class="country-name" title="Canada">CA</abbr>: <a href="/wiki/Over-the-counter_drug" title="Over-the-counter drug">OTC</a></li> <li><abbr class="country-name" title="United Kingdom">UK</abbr>: <a href="/wiki/Prescription_drug" title="Prescription drug">POM</a> (Prescription only)</li> <li><abbr class="country-name" title="United States">US</abbr>: <a href="/wiki/Over-the-counter_drug" title="Over-the-counter drug">OTC</a></li> <li><abbr class="country-name" title="European Union">EU</abbr>: Rx, OTC</li> <li>In general: ℞ (Prescription only)</li></ul></div> </td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd"><a href="/wiki/Pharmacokinetics" title="Pharmacokinetics">Pharmacokinetic</a> data</th></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Bioavailability" title="Bioavailability">Bioavailability</a></th><td class="infobox-data">2.5–50%<a href="#cite_note-TordjmanS-6">[6]</a><a href="#cite_note-pmid33540815-7">[7]</a><a href="#cite_note-Circadin-Label-8">[8]</a></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Plasma_protein_binding" title="Plasma protein binding">Protein binding</a></th><td class="infobox-data">60%<a href="#cite_note-Circadin-Label-8">[8]</a></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Drug_metabolism" title="Drug metabolism">Metabolism</a></th><td class="infobox-data"><a href="/wiki/Liver" title="Liver">Liver</a> via <a href="/wiki/CYP1A2" title="CYP1A2">CYP1A2</a> mediated 6-hydroxylation</td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Metabolite" title="Metabolite">Metabolites</a></th><td class="infobox-data"><a href="/wiki/6-Hydroxymelatonin" title="6-Hydroxymelatonin">6-Hydroxymelatonin</a>, <a href="/wiki/N-acetyl-5-hydroxytryptamine" class="mw-redirect" title="N-acetyl-5-hydroxytryptamine">N-acetyl-5-hydroxytryptamine</a>, <a href="/wiki/5-methoxytryptamine" class="mw-redirect" title="5-methoxytryptamine">5-methoxytryptamine</a></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Biological_half-life" title="Biological half-life">Elimination half-life</a></th><td class="infobox-data"><abbr title="Immediate-release">IR</abbr>: 20–60 minutes<a href="#cite_note-pmid33540815-7">[7]</a><a href="#cite_note-Auld2017-9">[9]</a><a href="#cite_note-pmid18368944-10">[10]</a> <abbr title="Prolonged-release">PR</abbr>: 3.5–4 hours<a href="#cite_note-pmid23044640-11">[11]</a><a href="#cite_note-Circadin-Label-8">[8]</a></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Excretion" title="Excretion">Excretion</a></th><td class="infobox-data"><a href="/wiki/Kidney" title="Kidney">Kidney</a></td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd">Identifiers</th></tr><tr><td colspan="2" class="infobox-full-data"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold;"><div><a href="/wiki/IUPAC_nomenclature_of_chemistry" title="IUPAC nomenclature of chemistry">IUPAC name</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all; text-align:left; padding-left:1.5em; text-indent:-1.5em;"><li style="line-height: inherit; margin: 0"><div style="font-size: 97%;">N-[2-(5-Methoxy-1H-indol-3-yl)ethyl]acetamide</div></li></ul> </div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/CAS_Registry_Number" title="CAS Registry Number">CAS Number</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=73-31-4">73-31-4</a> <img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" />Y</li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/PubChem#CID" title="PubChem">PubChem</a> <abbr title="Compound ID">CID</abbr></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/896">896</a></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Guide_to_Pharmacology" title="Guide to Pharmacology">IUPHAR/BPS</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><a rel="nofollow" class="external text" href="https://www.guidetopharmacology.org/GRAC/LigandDisplayForward?ligandId=224">224</a></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/DrugBank" title="DrugBank">DrugBank</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><a rel="nofollow" class="external text" href="https://www.drugbank.ca/drugs/DB01065">DB01065</a> <img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" />Y</li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/ChemSpider" title="ChemSpider">ChemSpider</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><a rel="nofollow" class="external text" href="https://www.chemspider.com/Chemical-Structure.872.html">872</a> <img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" />Y</li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Unique_Ingredient_Identifier" title="Unique Ingredient Identifier">UNII</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><a rel="nofollow" class="external text" href="https://precision.fda.gov/uniisearch/srs/unii/JL5DK93RCL">JL5DK93RCL</a></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/KEGG" title="KEGG">KEGG</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><a rel="nofollow" class="external text" href="https://www.kegg.jp/entry/D08170">D08170</a> <img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" />Y</li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/ChEBI" title="ChEBI">ChEBI</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:16796">CHEBI:16796</a> <img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" />Y</li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/ChEMBL" title="ChEMBL">ChEMBL</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chembldb/index.php/compound/inspect/ChEMBL45">ChEMBL45</a> <img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" />Y</li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/NIAID_ChemDB" title="NIAID ChemDB">NIAID ChemDB</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><a rel="nofollow" class="external text" href="https://chemdb.niaid.nih.gov/CompoundDetails.aspx?AIDSNO=160011">160011</a></li></ul></div></td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd">Chemical and physical data</th></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Chemical_formula" title="Chemical formula">Formula</a></th><td class="infobox-data">C13H16N2O2</td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Molar_mass" title="Molar mass">Molar mass</a></th><td class="infobox-data">232.283 g·mol−1</td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;">3D model (<a href="/wiki/JSmol" class="mw-redirect" title="JSmol">JSmol</a>)</th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><a rel="nofollow" class="external text" href="https://chemapps.stolaf.edu/jmol/jmol.php?model=COC1%3DCC2%3DC%28NC%3DC2CCNC%28C%29%3DO%29C%3DC1">Interactive image</a></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Melting_point" title="Melting point">Melting point</a></th><td class="infobox-data">117 °C (243 °F)</td></tr><tr><td colspan="2" class="infobox-full-data"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold;"><div><a href="/wiki/Simplified_molecular-input_line-entry_system" class="mw-redirect" title="Simplified molecular-input line-entry system">SMILES</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="word-wrap:break-word; text-indent:-1.5em; text-align:left; padding-left:1.5em; font-size:97%; line-height:120%;">COC1=CC2=C(NC=C2CCNC(C)=O)C=C1</div></li></ul> </div></td></tr><tr><td colspan="2" class="infobox-full-data"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold;"><div><a href="/wiki/International_Chemical_Identifier" title="International Chemical Identifier">InChI</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="word-wrap:break-word; text-indent:-1.5em; text-align:left; padding-left:1.5em; font-size:97%; line-height:120%;">InChI=1S/C13H16N2O2/c1-9(16)14-6-5-10-8-15-13-4-3-11(17-2)7-12(10)13/h3-4,7-8,15H,5-6H2,1-2H3,(H,14,16) <img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" />Y</div></li><li style="line-height: inherit; margin: 0"><div style="word-wrap:break-word; text-indent:-1.5em; text-align:left; padding-left:1.5em; font-size:97%; line-height:120%;">Key:DRLFMBDRBRZALE-UHFFFAOYSA-N <img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" />Y</div></li></ul> </div></td></tr><tr><td colspan="2" class="infobox-below"><style data-mw-deduplicate="TemplateStyles:r886047488">.mw-parser-output .nobold{font-weight:normal}</style>  <a class="external text" href="https://en.wikipedia.org/w/index.php?title=Special:ComparePages&rev1=646778032&page2=Melatonin+as+a+medication+and+supplement">(verify)</a></td></tr></tbody></table> Melatonin is a <a href="/wiki/Natural_product" title="Natural product">naturally occurring</a> <a href="/wiki/Hormone" title="Hormone">hormone</a> produced in the brain that is also used as a <a href="/wiki/Dietary_supplement" title="Dietary supplement">dietary supplement</a> and <a href="/wiki/Medication" title="Medication">medication</a>.<a href="#cite_note-Auld2017-9">[9]</a><a href="#cite_note-Faraone2014-12">[12]</a> As a hormone, melatonin is released by the <a href="/wiki/Pineal_gland" title="Pineal gland">pineal gland</a> and is involved in <a href="/wiki/Sleep%E2%80%93wake_cycle" class="mw-redirect" title="Sleep–wake cycle">sleep–wake cycles</a>.<a href="#cite_note-Auld2017-9">[9]</a><a href="#cite_note-Faraone2014-12">[12]</a> As a supplement, it is often used for the attempted short-term treatment of disrupted sleep patterns, such as from <a href="/wiki/Jet_lag" title="Jet lag">jet lag</a> or <a href="/wiki/Shift_work" title="Shift work">shift work</a>, and is typically taken <a href="/wiki/Oral_administration" title="Oral administration">orally</a>.<a href="#cite_note-Buscemi_2004-13">[13]</a><a href="#cite_note-AFP2017-14">[14]</a><a href="#cite_note-BNF76-15">[15]</a> There is evidence of its benefit for this use, but is not strong.<a href="#cite_note-Bra2015-16">[16]</a> A 2017 review found that sleep onset occurred six minutes faster with use on average, but found no change in total time asleep.<a href="#cite_note-AFP2017-14">[14]</a> Side effects from melatonin supplements are minimal at low doses for short durations (the studies reported about equally for both melatonin and placebo).<a href="#cite_note-Auld2017-9">[9]</a><a href="#cite_note-Drugs2019-17">[17]</a> Side effects of melatonin are rare but may occur in 1 to 10 patients in 1,000.<a href="#cite_note-Drugs2019-17">[17]</a><a href="#cite_note-Circadin-Label-8">[8]</a> They may include <a href="/wiki/Somnolence" title="Somnolence">somnolence</a>, <a href="/wiki/Headache" title="Headache">headaches</a>, <a href="/wiki/Nausea" title="Nausea">nausea</a>, <a href="/wiki/Diarrhea" title="Diarrhea">diarrhea</a>, abnormal <a href="/wiki/Dream" title="Dream">dreams</a>, <a href="/wiki/Irritability" title="Irritability">irritability</a>, <a href="/wiki/Psychomotor_agitation" title="Psychomotor agitation">restlessness</a>, <a href="/wiki/Insomnia" title="Insomnia">insomnia</a>, <a href="/wiki/Anxiety" title="Anxiety">anxiety</a>, <a href="/wiki/Migraine" title="Migraine">migraine</a>, <a href="/wiki/Lethargy" title="Lethargy">lethargy</a>, <a href="/wiki/Psychomotor_agitation" title="Psychomotor agitation">hyperactivity</a>, <a href="/wiki/Dizziness" title="Dizziness">dizziness</a>, <a href="/wiki/Hypertension" title="Hypertension">hypertension</a>, <a href="/wiki/Abdominal_pain" title="Abdominal pain">abdominal pain</a>, <a href="/wiki/Heartburn" title="Heartburn">heartburn</a>, <a href="/wiki/Mouth_ulcers" class="mw-redirect" title="Mouth ulcers">mouth ulcers</a>, <a href="/wiki/Dry_mouth" class="mw-redirect" title="Dry mouth">dry mouth</a>, <a href="/wiki/Hyperbilirubinaemia" class="mw-redirect" title="Hyperbilirubinaemia">hyperbilirubinaemia</a>, <a href="/wiki/Dermatitis" title="Dermatitis">dermatitis</a>, <a href="/wiki/Night_sweats" title="Night sweats">night sweats</a>, <a href="/wiki/Pruritus" class="mw-redirect" title="Pruritus">pruritus</a>, <a href="/wiki/Rash" title="Rash">rash</a>, <a href="/wiki/Xeroderma" title="Xeroderma">dry skin</a>, <a href="/wiki/Pain" title="Pain">pain</a> in the extremities, symptoms of <a href="/wiki/Menopause" title="Menopause">menopause</a>, <a href="/wiki/Chest_pain" title="Chest pain">chest pain</a>, <a href="/wiki/Glycosuria" title="Glycosuria">glycosuria</a> (sugar in the urine), <a href="/wiki/Proteinuria" title="Proteinuria">proteinuria</a> (protein in the urine), abnormal liver function tests, <a href="/wiki/Weight_gain" title="Weight gain">weight gain</a>, <a href="/wiki/Mood_swing" title="Mood swing">mood swings</a>, <a href="/wiki/Aggression" title="Aggression">aggression</a>, and <a href="/wiki/Grogginess" class="mw-redirect" title="Grogginess">grogginess</a> after awakening.<a href="#cite_note-Circadin-Label-8">[8]</a><a href="#cite_note-Slenyto_EPAR-18">[18]</a><a href="#cite_note-Drugs2019-17">[17]</a><a href="#cite_note-HC2015-19">[19]</a><a href="#cite_note-HC2018Oral-20">[20]</a> Its use is not recommended during <a href="/wiki/Pregnancy" title="Pregnancy">pregnancy</a> or <a href="/wiki/Breastfeeding" title="Breastfeeding">breastfeeding</a> or for those with <a href="/wiki/Liver_disease" title="Liver disease">liver disease</a>.<a href="#cite_note-BNF76-15">[15]</a><a href="#cite_note-HC2018Oral-20">[20]</a> Melatonin acts as an <a href="/wiki/Agonist" title="Agonist">agonist</a> of the <a href="/wiki/Melatonin_receptor" title="Melatonin receptor">melatonin</a> <a href="/wiki/MT1_receptor" class="mw-redirect" title="MT1 receptor">MT1</a> and <a href="/wiki/MT2_receptor" class="mw-redirect" title="MT2 receptor">MT2 receptors</a>, the <a href="/wiki/Biological_target" title="Biological target">biological targets</a> of <a href="/wiki/Endogenous" class="mw-redirect" title="Endogenous">endogenous</a> melatonin.<a href="#cite_note-pmid34225973-21">[21]</a> It is thought to activate these receptors in the <a href="/wiki/Suprachiasmatic_nucleus" title="Suprachiasmatic nucleus">suprachiasmatic nucleus</a> of the <a href="/wiki/Hypothalamus" title="Hypothalamus">hypothalamus</a> in the <a href="/wiki/Brain" title="Brain">brain</a> to regulate the <a href="/wiki/Circadian_clock" title="Circadian clock">circadian clock</a> and sleep–wake cycles.<a href="#cite_note-pmid34225973-21">[21]</a> Immediate-release melatonin has a short <a href="/wiki/Elimination_half-life" class="mw-redirect" title="Elimination half-life">elimination half-life</a> of about 20 to 50 minutes.<a href="#cite_note-drugbank-22">[22]</a><a href="#cite_note-Auld2017-9">[9]</a><a href="#cite_note-pmid18368944-10">[10]</a> Prolonged-release melatonin used as a medication has a half-life of 3.5 to 4 hours.<a href="#cite_note-pmid23044640-11">[11]</a><a href="#cite_note-Circadin-Label-8">[8]</a> Melatonin was discovered in 1958.<a href="#cite_note-Auld2017-9">[9]</a> It is sold <a href="/wiki/Over-the-counter_drug" title="Over-the-counter drug">over-the-counter</a> in Canada and the United States;<a href="#cite_note-Drugs2019-17">[17]</a><a href="#cite_note-HC2015-19">[19]</a> in the United Kingdom, it is a <a href="/wiki/Prescription-only" class="mw-redirect" title="Prescription-only">prescription-only</a> medication.<a href="#cite_note-BNF76-15">[15]</a> In Australia and the European Union, it is indicated for difficulty sleeping in people over the age of 54.<a href="#cite_note-23">[23]</a><a href="#cite_note-Circadin-Label-8">[8]</a> In the European Union, it is indicated for the treatment of insomnia in children and adolescents.<a href="#cite_note-Slenyto_EPAR-18">[18]</a> The U.S. <a href="/wiki/Food_and_Drug_Administration" title="Food and Drug Administration">Food and Drug Administration</a> (FDA) treats melatonin as a dietary supplement and, as such, has not approved it for any medical uses.<a href="#cite_note-Drugs2019-17">[17]</a> It was approved for medical use in the European Union in 2007.<a href="#cite_note-Circadin-Label-8">[8]</a> Besides melatonin, certain <a href="/wiki/Synthetic_compound" class="mw-redirect" title="Synthetic compound">synthetic</a> <a href="/wiki/Melatonin_receptor_agonist" title="Melatonin receptor agonist">melatonin receptor agonists</a> like <a href="/wiki/Ramelteon" title="Ramelteon">ramelteon</a>, <a href="/wiki/Tasimelteon" title="Tasimelteon">tasimelteon</a>, and <a href="/wiki/Agomelatine" title="Agomelatine">agomelatine</a> are also used in medicine.<a href="#cite_note-pmid27500861-24">[24]</a><a href="#cite_note-pmid29487083-25">[25]</a> In 2021, it was the 257th most commonly prescribed medication in the United States, with more than one million prescriptions.<a href="#cite_note-Top_300_of_2021-26">[26]</a><a href="#cite_note-Clincalc_Melatonin-27">[27]</a> <style data-mw-deduplicate="TemplateStyles:r886046785">.mw-parser-output .toclimit-2 .toclevel-1 ul,.mw-parser-output .toclimit-3 .toclevel-2 ul,.mw-parser-output .toclimit-4 .toclevel-3 ul,.mw-parser-output .toclimit-5 .toclevel-4 ul,.mw-parser-output .toclimit-6 .toclevel-5 ul,.mw-parser-output .toclimit-7 .toclevel-6 ul{display:none}</style><div class="toclimit-3"><meta property="mw:PageProp/toc" /></div> <div class="mw-heading mw-heading2"><h2 id="Medical_uses">Medical uses</h2>[<a href="/w/index.php?title=Melatonin_as_a_medication_and_supplement&action=edit&section=1" title="Edit section: Medical uses">edit</a>]</div> <div class="mw-heading mw-heading3"><h3 id="Insomnia">Insomnia</h3>[<a href="/w/index.php?title=Melatonin_as_a_medication_and_supplement&action=edit&section=2" title="Edit section: Insomnia">edit</a>]</div> There is no good evidence that melatonin helps treat insomnia and its attempted use for this purpose is recommended against by the <a href="/wiki/American_Academy_of_Sleep_Medicine" title="American Academy of Sleep Medicine">American Academy of Sleep Medicine</a>.<a href="#cite_note-pseudo-28">[28]</a> A <a href="/wiki/Prolonged-release" class="mw-redirect" title="Prolonged-release">prolonged-release</a> form of melatonin is approved for use as a medication in <a href="/wiki/Europe" title="Europe">Europe</a> for the treatment of insomnia in certain people.<a href="#cite_note-pmid23044640-11">[11]</a><a href="#cite_note-pmid18808316-29">[29]</a> <div class="mw-heading mw-heading3"><h3 id="Circadian_rhythm_sleep_disorders">Circadian rhythm sleep disorders</h3>[<a href="/w/index.php?title=Melatonin_as_a_medication_and_supplement&action=edit&section=3" title="Edit section: Circadian rhythm sleep disorders">edit</a>]</div> Melatonin may be useful in the treatment of <a href="/wiki/Delayed_sleep_phase_disorder" title="Delayed sleep phase disorder">delayed sleep phase syndrome</a>.<a href="#cite_note-Auld2017-9">[9]</a> Melatonin is known to reduce <a href="/wiki/Jet_lag" title="Jet lag">jet lag</a>, especially in eastward travel. However, if it is not taken at the correct time, it can instead delay adaptation.<a href="#cite_note-pubmed12076414-30">[30]</a> Melatonin appears to have limited use against the sleep problems of people who work <a href="/wiki/Shift_work" title="Shift work">shift work</a>.<a href="#cite_note-Cochrane2014-31">[31]</a> Tentative evidence suggests that it increases the length of time people are able to sleep.<a href="#cite_note-Cochrane2014-31">[31]</a> <div class="mw-heading mw-heading3"><h3 id="REM_sleep_behavior_disorder">REM sleep behavior disorder</h3>[<a href="/w/index.php?title=Melatonin_as_a_medication_and_supplement&action=edit&section=4" title="Edit section: REM sleep behavior disorder">edit</a>]</div> Melatonin is a safer alternative than <a href="/wiki/Clonazepam" title="Clonazepam">clonazepam</a> in the treatment of <a href="/wiki/REM_sleep_behavior_disorder" class="mw-redirect" title="REM sleep behavior disorder">REM sleep behavior disorder</a> – a condition associated with the <a href="/wiki/Synucleinopathy" title="Synucleinopathy">synucleinopathies</a> like <a href="/wiki/Parkinson%27s_disease" title="Parkinson's disease">Parkinson's disease</a> and <a href="/wiki/Dementia_with_Lewy_bodies" title="Dementia with Lewy bodies">dementia with Lewy bodies</a>.<a href="#cite_note-McCarter2013-32">[32]</a><a href="#cite_note-McKeithConsensus2017-33">[33]</a><a href="#cite_note-Boot2015-34">[34]</a> However, clonazepam may be more effective.<a href="#cite_note-pmid33410930-35">[35]</a> In any case, the quality of evidence for both treatments is very low and it is unclear whether either is definitely effective.<a href="#cite_note-pmid33410930-35">[35]</a> <div class="mw-heading mw-heading3"><h3 id="Dementia">Dementia</h3>[<a href="/w/index.php?title=Melatonin_as_a_medication_and_supplement&action=edit&section=5" title="Edit section: Dementia">edit</a>]</div> A 2020 <a href="/wiki/Cochrane_review" class="mw-redirect" title="Cochrane review">Cochrane review</a> found no evidence that melatonin helped sleep problems in people with moderate to severe <a href="/wiki/Dementia" title="Dementia">dementia</a> due to <a href="/wiki/Alzheimer%27s_disease" title="Alzheimer's disease">Alzheimer's disease</a>.<a href="#cite_note-36">[36]</a> A 2019 review found that while melatonin may improve sleep in <a href="/wiki/Minimal_cognitive_impairment" class="mw-redirect" title="Minimal cognitive impairment">minimal cognitive impairment</a>, after the onset of Alzheimer's disease it has little to no effect.<a href="#cite_note-:1-37">[37]</a> Melatonin may, however, help with <a href="/wiki/Sundowning" title="Sundowning">sundowning</a> (increased confusion and restlessness at night) in people with dementia.<a href="#cite_note-38">[38]</a> <div class="mw-heading mw-heading3"><h3 id="Available_forms">Available forms</h3>[<a href="/w/index.php?title=Melatonin_as_a_medication_and_supplement&action=edit&section=6" title="Edit section: Available forms">edit</a>]</div> <figure typeof="mw:File/Thumb"><a href="/wiki/File:Walgreens_Melatonin-2010-20-07.jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/4/44/Walgreens_Melatonin-2010-20-07.jpg/200px-Walgreens_Melatonin-2010-20-07.jpg" decoding="async" width="200" height="300" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/4/44/Walgreens_Melatonin-2010-20-07.jpg/300px-Walgreens_Melatonin-2010-20-07.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/4/44/Walgreens_Melatonin-2010-20-07.jpg/400px-Walgreens_Melatonin-2010-20-07.jpg 2x" data-file-width="1872" data-file-height="2808" /></a><figcaption>A bottle of melatonin tablets. Melatonin is also available in timed-release and in liquid forms.</figcaption></figure> A <a href="/wiki/Prolonged-release" class="mw-redirect" title="Prolonged-release">prolonged-release</a> 2 mg <a href="/wiki/Oral_administration" title="Oral administration">oral</a> formulation of melatonin sold under the brand name Circadin is approved for use in the <a href="/wiki/European_Union" title="European Union">European Union</a> in the short-term treatment of <a href="/wiki/Insomnia" title="Insomnia">insomnia</a> in people age 55 and older.<a href="#cite_note-pmid23044640-11">[11]</a><a href="#cite_note-pmid18808316-29">[29]</a><a href="#cite_note-Circadin-Label-8">[8]</a> Melatonin is also available as an <a href="/wiki/Over-the-counter" class="mw-redirect" title="Over-the-counter">over-the-counter</a> <a href="/wiki/Dietary_supplement" title="Dietary supplement">dietary supplement</a> in many countries. It is available in both immediate-release and less commonly prolonged-release forms. The compound is available in supplements at doses ranging from 0.3 mg to 10 mg or more. It is also possible to buy raw melatonin powder by the weight.<a href="#cite_note-39">[39]</a> Immediate-release formulations of melatonin cause blood levels of melatonin to reach their peak in about an hour. The hormone may be administered orally, as capsules, gummies, tablets, oral films, or liquids.<a href="#cite_note-:0-40">[40]</a> It is also available for use <a href="/wiki/Sublingual_administration" title="Sublingual administration">sublingually</a>, or as <a href="/wiki/Transdermal_patch" title="Transdermal patch">transdermal patches</a>.<a href="#cite_note-41">[41]</a> Several inhalation-based melatonin products with a wide range of doses are being sold but the safety remains to be evaluated.<a href="#cite_note-:0-40">[40]</a> The American Academy of Sleep Medicine (AASM) said that the melatonin content in unregulated (without a <a href="/wiki/United_States_Pharmacopeia" title="United States Pharmacopeia">USP</a> verified mark) supplements can diverge widely from the claimed amount; a study found that the melatonin content ranged from one half to four times the stated dose.<a href="#cite_note-brooks-42">[42]</a> <div class="mw-heading mw-heading2"><h2 id="Contraindications">Contraindications</h2>[<a href="/w/index.php?title=Melatonin_as_a_medication_and_supplement&action=edit&section=7" title="Edit section: Contraindications">edit</a>]</div> <a href="/wiki/Contraindication" title="Contraindication">Contraindications</a> of melatonin include <a href="/wiki/Hypersensitivity_reaction" class="mw-redirect" title="Hypersensitivity reaction">hypersensitivity reactions</a> among others.<a href="#cite_note-Circadin-Label-8">[8]</a> It is not recommended in people with <a href="/wiki/Autoimmune_disease" title="Autoimmune disease">autoimmune diseases</a> due to lack of data in these individuals.<a href="#cite_note-Circadin-Label-8">[8]</a> Prolonged-release pharmaceutical melatonin (Circadin) contains <a href="/wiki/Lactose" title="Lactose">lactose</a> and should not be used in people with the <a href="/wiki/Lactose_intolerance" title="Lactose intolerance">lactase deficiency</a> or <a href="/wiki/Glucose%E2%80%93galactose_malabsorption" class="mw-redirect" title="Glucose–galactose malabsorption">glucose–galactose malabsorption</a>.<a href="#cite_note-Circadin-Label-8">[8]</a> Use of melatonin is also not recommend in women who are <a href="/wiki/Pregnancy" title="Pregnancy">pregnant</a> or <a href="/wiki/Breastfeeding" title="Breastfeeding">breastfeeding</a> or in people with <a href="/wiki/Liver_disease" title="Liver disease">liver disease</a>.<a href="#cite_note-BNF76-15">[15]</a><a href="#cite_note-HC2018Oral-20">[20]</a> <div class="mw-heading mw-heading2"><h2 id="Adverse_effects">Adverse effects</h2>[<a href="/w/index.php?title=Melatonin_as_a_medication_and_supplement&action=edit&section=8" title="Edit section: Adverse effects">edit</a>]</div> Melatonin appears to cause very few <a href="/wiki/Adverse_effect_(medicine)" class="mw-redirect" title="Adverse effect (medicine)">side effects</a> as tested in the short term, up to three months, at low doses.[<a href="/wiki/Wikipedia:Please_clarify" title="Wikipedia:Please clarify">clarification needed</a>][<a href="/wiki/Wikipedia:Accuracy_dispute#Disputed_statement" title="Wikipedia:Accuracy dispute">dubious</a> – <a href="/wiki/Talk:Melatonin_as_a_medication_and_supplement#Dubious" title="Talk:Melatonin as a medication and supplement">discuss</a>] Two systematic reviews found no adverse effects of exogenous melatonin in several clinical trials, and comparative trials found the adverse effects headaches, dizziness, nausea, and drowsiness were reported about equally for both melatonin and <a href="/wiki/Placebo" title="Placebo">placebo</a>.<a href="#cite_note-pmid16423108-43">[43]</a><a href="#cite_note-Buscemi2006-44">[44]</a> Prolonged-release melatonin is safe with long-term use of up to 12 months.<a href="#cite_note-pmid23044640-11">[11]</a> Although not recommended for long-term use beyond this,<a href="#cite_note-45">[45]</a> low-dose melatonin is generally safer, and a better alternative, than many prescription and over-the-counter sleep aids if a sleeping medication must be used for an extended period of time.[<a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed">citation needed</a>] Low doses of melatonin are usually sufficient to produce a <a href="/wiki/Hypnotic" title="Hypnotic">hypnotic</a> effect in most people. Higher doses do not appear to result in a stronger effect but instead appear to cause drowsiness for a longer period of time.<a href="#cite_note-46">[46]</a> There is emerging evidence that the timing of taking exogenous melatonin in relation to food is also an important factor.<a href="#cite_note-pmid31901302-47">[47]</a> Specifically, taking exogenous melatonin shortly after a meal is correlated with impaired glucose tolerance. Therefore, Rubio-Sastre and colleagues recommend waiting at least 2 hours after the last meal before taking a melatonin supplement.<a href="#cite_note-Rubio-Sastre_2014-48">[48]</a> Melatonin can cause <a href="/wiki/Nausea" title="Nausea">nausea</a>, next-day <a href="/wiki/Grogginess" class="mw-redirect" title="Grogginess">grogginess</a>, and irritability.<a href="#cite_note-49">[49]</a> In <a href="/wiki/Autoimmune_disorders" class="mw-redirect" title="Autoimmune disorders">autoimmune disorders</a>, evidence is conflicting whether melatonin supplementation may ameliorate or exacerbate symptoms due to <a href="/wiki/Immunomodulator" class="mw-redirect" title="Immunomodulator">immunomodulation</a>.<a href="#cite_note-Morera2001-50">[50]</a><a href="#cite_note-Terry2008-51">[51]</a>[<a href="/wiki/Wikipedia:Manual_of_Style/Dates_and_numbers#Chronological_items" title="Wikipedia:Manual of Style/Dates and numbers">needs update</a>] Melatonin can lower <a href="/wiki/Follicle-stimulating_hormone" title="Follicle-stimulating hormone">follicle-stimulating hormone</a> levels.<a href="#cite_note-pmid16921343-52">[52]</a> Melatonin's effects on human reproduction remain unclear.<a href="#cite_note-pmid19905996-53">[53]</a> Some supplemental melatonin users report an increase in <a href="/wiki/Vivid_dreaming" class="mw-redirect" title="Vivid dreaming">vivid dreaming</a>. Extremely high doses of melatonin increased <a href="/wiki/REM_sleep" class="mw-redirect" title="REM sleep">REM sleep</a> time and dream activity in people both with and without <a href="/wiki/Narcolepsy" title="Narcolepsy">narcolepsy</a>.<a href="#cite_note-Lewis-54">[54]</a> Increased use of melatonin in the 21st century has significantly increased reports of melatonin overdose, calls to poison control centers, and related emergency department visits for children. The number of children who unintentionally ingested melatonin supplements in the US has increased 530% from 2012 to 2021. Over 4,000 reported ingestions required a hospital stay, and 287 children required intensive care. The <a href="/wiki/American_Academy_of_Sleep_Medicine" title="American Academy of Sleep Medicine">American Academy of Sleep Medicine</a> says there is little evidence that melatonin supplementation is effective in treating insomnia in healthy children.<a href="#cite_note-brooks-42">[42]</a> <div class="mw-heading mw-heading2"><h2 id="Overdose">Overdose</h2>[<a href="/w/index.php?title=Melatonin_as_a_medication_and_supplement&action=edit&section=9" title="Edit section: Overdose">edit</a>]</div> Melatonin appears to be relatively safe in <a href="/wiki/Overdose" class="mw-redirect" title="Overdose">overdose</a>.<a href="#cite_note-Circadin-Label-8">[8]</a> It has been administered at daily doses of up to 300 mg without causing clinically significant adverse reactions in the literature.<a href="#cite_note-Circadin-Label-8">[8]</a> The most commonly reported adverse effect of melatonin overdose is <a href="/wiki/Somnolence" title="Somnolence">somnolence</a>.<a href="#cite_note-Circadin-Label-8">[8]</a> Upon melatonin overdose, <a href="/wiki/Drowsiness" class="mw-redirect" title="Drowsiness">drowsiness</a> may be expected and the compound should be cleared within 12 hours.<a href="#cite_note-Circadin-Label-8">[8]</a> No special treatment is needed for melatonin overdose.<a href="#cite_note-Circadin-Label-8">[8]</a> <div class="mw-heading mw-heading2"><h2 id="Interactions">Interactions</h2>[<a href="/w/index.php?title=Melatonin_as_a_medication_and_supplement&action=edit&section=10" title="Edit section: Interactions">edit</a>]</div> Melatonin is <a href="/wiki/Metabolism" title="Metabolism">metabolized</a> mainly by <a href="/wiki/CYP1A" class="mw-redirect" title="CYP1A">CYP1A</a> <a href="/wiki/Enzyme" title="Enzyme">enzymes</a>. As such, <a href="/wiki/Enzyme_inhibitor" title="Enzyme inhibitor">inhibitors</a> and <a href="/wiki/Enzyme_inducer" title="Enzyme inducer">inducers</a> of CYP1A enzymes, such as <a href="/wiki/CYP1A2" title="CYP1A2">CYP1A2</a>, can modify melatonin metabolism and exposure.<a href="#cite_note-Circadin-Label-8">[8]</a> As an example, the CYP1A2 and <a href="/wiki/CYP2C19" title="CYP2C19">CYP2C19</a> inhibitor <a href="/wiki/Fluvoxamine" title="Fluvoxamine">fluvoxamine</a> increases melatonin peak levels by 12-fold and overall exposure by 17-fold and this combination should be avoided.<a href="#cite_note-Circadin-Label-8">[8]</a> CYP1A2 inducers like <a href="/wiki/Cigarette_smoking" class="mw-redirect" title="Cigarette smoking">cigarette smoking</a>, <a href="/wiki/Carbamazepine" title="Carbamazepine">carbamazepine</a>, and <a href="/wiki/Rifampicin" title="Rifampicin">rifampicin</a> may reduce melatonin exposure due to induction of CYP1A2.<a href="#cite_note-Circadin-Label-8">[8]</a> In those taking <a href="/wiki/Warfarin" title="Warfarin">warfarin</a>, some evidence suggests there may exist a potentiating interaction, increasing the <a href="/wiki/Anticoagulant" title="Anticoagulant">anticoagulant</a> effect of warfarin and the risk of bleeding.<a href="#cite_note-55">[55]</a> <div class="mw-heading mw-heading2"><h2 id="Pharmacology">Pharmacology</h2>[<a href="/w/index.php?title=Melatonin_as_a_medication_and_supplement&action=edit&section=11" title="Edit section: Pharmacology">edit</a>]</div> <div class="mw-heading mw-heading3"><h3 id="Pharmacodynamics">Pharmacodynamics</h3>[<a href="/w/index.php?title=Melatonin_as_a_medication_and_supplement&action=edit&section=12" title="Edit section: Pharmacodynamics">edit</a>]</div> Melatonin acts as an <a href="/wiki/Agonist" title="Agonist">agonist</a> of the <a href="/wiki/Melatonin_receptor" title="Melatonin receptor">melatonin</a> <a href="/wiki/MT1_receptor" class="mw-redirect" title="MT1 receptor">MT1</a> and <a href="/wiki/MT2_receptor" class="mw-redirect" title="MT2 receptor">MT2 receptors</a>, the <a href="/wiki/Biological_target" title="Biological target">biological targets</a> of <a href="/wiki/Endogenous" class="mw-redirect" title="Endogenous">endogenous</a> melatonin.<a href="#cite_note-pmid34225973-21">[21]</a> Endogenous melatonin is normally secreted from the <a href="/wiki/Pineal_gland" title="Pineal gland">pineal gland</a> of the brain.<a href="#cite_note-pmid34225973-21">[21]</a> Melatonin is thought to activate melatonin receptors in the <a href="/wiki/Suprachiasmatic_nucleus" title="Suprachiasmatic nucleus">suprachiasmatic nucleus</a> of the <a href="/wiki/Hypothalamus" title="Hypothalamus">hypothalamus</a> to regulate the <a href="/wiki/Circadian_clock" title="Circadian clock">circadian clock</a> and sleep–wake cycles.<a href="#cite_note-pmid34225973-21">[21]</a> When used several hours before sleep according to the <a href="/wiki/Phase_response_curve" title="Phase response curve">phase response curve</a> for melatonin in humans, small amounts (0.3 mg<a href="#cite_note-pmid16295212-56">[56]</a>) of melatonin shift the circadian clock earlier, thus promoting earlier sleep onset and morning awakening.<a href="#cite_note-isbn_3-8055-9120-9-57">[57]</a> <div class="mw-heading mw-heading3"><h3 id="Pharmacokinetics">Pharmacokinetics</h3>[<a href="/w/index.php?title=Melatonin_as_a_medication_and_supplement&action=edit&section=13" title="Edit section: Pharmacokinetics">edit</a>]</div> <div class="mw-heading mw-heading4"><h4 id="Absorption">Absorption</h4>[<a href="/w/index.php?title=Melatonin_as_a_medication_and_supplement&action=edit&section=14" title="Edit section: Absorption">edit</a>]</div> The <a href="/wiki/Bioavailability" title="Bioavailability">bioavailability</a> of melatonin is between 2.5 and 50%.<a href="#cite_note-TordjmanS-6">[6]</a><a href="#cite_note-pmid33540815-7">[7]</a> Melatonin is rapidly <a href="/wiki/Absorption_(pharmacokinetics)" class="mw-redirect" title="Absorption (pharmacokinetics)">absorbed</a> and <a href="/wiki/Distribution_(pharmacology)" title="Distribution (pharmacology)">distributed</a>, reaching <a href="/wiki/Cmax_(pharmacology)" title="Cmax (pharmacology)">peak plasma concentrations</a> after 60 minutes of administration, and is then <a href="/wiki/Elimination_(pharmacology)" title="Elimination (pharmacology)">eliminated</a>.<a href="#cite_note-TordjmanS-6">[6]</a> Usual doses of exogenous melatonin of 1 to 12 mg produce melatonin concentrations 10 to 100 times higher than endogenous peak levels.<a href="#cite_note-pmid33540815-7">[7]</a> <div class="mw-heading mw-heading4"><h4 id="Distribution">Distribution</h4>[<a href="/w/index.php?title=Melatonin_as_a_medication_and_supplement&action=edit&section=15" title="Edit section: Distribution">edit</a>]</div> The <a href="/wiki/Plasma_protein_binding" title="Plasma protein binding">plasma protein binding</a> of melatonin is approximately 60%.<a href="#cite_note-Circadin-Label-8">[8]</a><a href="#cite_note-pmid33540815-7">[7]</a> It is mainly bound to <a href="/wiki/Human_serum_albumin" title="Human serum albumin">albumin</a>, <a href="/wiki/Alpha-1_acid_glycoprotein" class="mw-redirect" title="Alpha-1 acid glycoprotein">α1-acid glycoprotein</a>, and <a href="/wiki/High-density_lipoprotein" title="High-density lipoprotein">high-density lipoprotein</a>.<a href="#cite_note-Circadin-Label-8">[8]</a> The <a href="/wiki/Membrane_transport_protein" title="Membrane transport protein">membrane transport proteins</a> that move melatonin across a membrane include, but are not limited to, <a href="/wiki/Glucose_transporter" title="Glucose transporter">glucose transporters</a>, including <a href="/wiki/GLUT1" title="GLUT1">GLUT1</a>, and the <a href="/w/index.php?title=Proton-driven_oligopeptide_transporter&action=edit&redlink=1" class="new" title="Proton-driven oligopeptide transporter (page does not exist)">proton-driven oligopeptide transporters</a> <a href="/wiki/Peptide_transporter_1" title="Peptide transporter 1">PEPT1</a> and <a href="/wiki/SLC15A2" title="SLC15A2">PEPT2</a>.<a href="#cite_note-IUPHAR_–_melatonin_receptors_review-58">[58]</a><a href="#cite_note-Melatonin_transporters_–_2017_review-59">[59]</a> <div class="mw-heading mw-heading4"><h4 id="Metabolism">Metabolism</h4>[<a href="/w/index.php?title=Melatonin_as_a_medication_and_supplement&action=edit&section=16" title="Edit section: Metabolism">edit</a>]</div> Melatonin is <a href="/wiki/Metabolism" title="Metabolism">metabolized</a> in the <a href="/wiki/Liver" title="Liver">liver</a> by <a href="/wiki/Cytochrome_P450" title="Cytochrome P450">cytochrome P450</a> <a href="/wiki/Enzyme" title="Enzyme">enzyme</a> <a href="/wiki/CYP1A2" title="CYP1A2">CYP1A2</a> to <a href="/wiki/6-hydroxymelatonin" class="mw-redirect" title="6-hydroxymelatonin">6-hydroxymelatonin</a>. <a href="/wiki/Metabolite" title="Metabolite">Metabolites</a> are <a href="/wiki/Conjugation_(biochemistry)" class="mw-redirect" title="Conjugation (biochemistry)">conjugated</a> with <a href="/wiki/Sulfuric_acid" title="Sulfuric acid">sulfuric acid</a> or <a href="/wiki/Glucuronic_acid" title="Glucuronic acid">glucuronic acid</a> for <a href="/wiki/Excretion" title="Excretion">excretion</a> in the <a href="/wiki/Urine" title="Urine">urine</a>. Some of the metabolites formed via the reaction of melatonin with a <a href="/wiki/Radical_(chemistry)" title="Radical (chemistry)">free radical</a> include <a href="/wiki/Cyclic_3-hydroxymelatonin" title="Cyclic 3-hydroxymelatonin">cyclic 3-hydroxymelatonin</a>, <a href="/wiki/N1-acetyl-N2-formyl-5-methoxykynuramine" class="mw-redirect" title="N1-acetyl-N2-formyl-5-methoxykynuramine">N1-acetyl-N2-formyl-5-methoxykynuramine</a> (AFMK), and <a href="/wiki/N1-acetyl-5-methoxykynuramine" class="mw-redirect" title="N1-acetyl-5-methoxykynuramine">N1-acetyl-5-methoxykynuramine</a> (AMK).<a href="#cite_note-IUPHAR_–_melatonin_receptors_review-58">[58]</a><a href="#cite_note-Melatonin_transporters_–_2017_review-59">[59]</a> <div class="mw-heading mw-heading4"><h4 id="Elimination">Elimination</h4>[<a href="/w/index.php?title=Melatonin_as_a_medication_and_supplement&action=edit&section=17" title="Edit section: Elimination">edit</a>]</div> In humans, 90% of orally administered exogenous melatonin is cleared in a single passage through the liver, a small amount is excreted in urine, and a small amount is found in saliva.<a href="#cite_note-Buscemi_2004-13">[13]</a> Melatonin is excreted in the urine 2 to 5% as the unchanged drug.<a href="#cite_note-TordjmanS-6">[6]</a><a href="#cite_note-Circadin-Label-8">[8]</a> Melatonin has an <a href="/wiki/Elimination_half-life" class="mw-redirect" title="Elimination half-life">elimination half-life</a> of about 20 to 60 minutes.<a href="#cite_note-drugbank-22">[22]</a><a href="#cite_note-pmid33540815-7">[7]</a><a href="#cite_note-Auld2017-9">[9]</a><a href="#cite_note-pmid18368944-10">[10]</a> The half-life of prolonged-release melatonin (Circadin) is 3.5 to 4 hours.<a href="#cite_note-pmid23044640-11">[11]</a><a href="#cite_note-Circadin-Label-8">[8]</a> <div class="mw-heading mw-heading2"><h2 id="Chemistry">Chemistry</h2>[<a href="/w/index.php?title=Melatonin_as_a_medication_and_supplement&action=edit&section=18" title="Edit section: Chemistry">edit</a>]</div> Melatonin, also known as N-acetyl-5-methoxytryptamine, is a <a href="/wiki/Substituted_tryptamine" title="Substituted tryptamine">substituted tryptamine</a> and a <a href="/wiki/Chemical_derivative" class="mw-redirect" title="Chemical derivative">derivative</a> of <a href="/wiki/Serotonin" title="Serotonin">serotonin</a> (5-hydroxytryptamine). It is structurally related to <a href="/wiki/N-acetylserotonin" class="mw-redirect" title="N-acetylserotonin">N-acetylserotonin</a> (normelatonin; N-acetyl-5-hydroxytryptamine), which is the <a href="/wiki/Chemical_intermediate" class="mw-redirect" title="Chemical intermediate">chemical intermediate</a> between serotonin and melatonin in the body. <a href="/wiki/Synthetic_compound" class="mw-redirect" title="Synthetic compound">Synthetic</a> <a href="/wiki/Melatonin_receptor_agonist" title="Melatonin receptor agonist">melatonin receptor agonists</a> used in medicine like <a href="/wiki/Ramelteon" title="Ramelteon">ramelteon</a>, <a href="/wiki/Tasimelteon" title="Tasimelteon">tasimelteon</a>, <a href="/wiki/Agomelatine" title="Agomelatine">agomelatine</a>, and <a href="/wiki/Piromelatine" title="Piromelatine">piromelatine</a> (still in clinical trials) are <a href="/wiki/Structural_analog" title="Structural analog">analogues</a> of melatonin. <div class="mw-heading mw-heading2"><h2 id="History">History</h2>[<a href="/w/index.php?title=Melatonin_as_a_medication_and_supplement&action=edit&section=19" title="Edit section: History">edit</a>]</div> The first <a href="/wiki/Patent" title="Patent">patent</a> for its use in circadian rhythm disorders was granted in 1987 to Roger V Short and Stuart Armstrong at <a href="/wiki/Monash_University" title="Monash University">Monash University</a>,<a href="#cite_note-60">[60]</a> and the first patent for its use as a low-dose sleep aid was granted to <a href="/wiki/Richard_Wurtman" title="Richard Wurtman">Richard Wurtman</a> at <a href="/wiki/MIT" class="mw-redirect" title="MIT">MIT</a> in 1995.<a href="#cite_note-61">[61]</a> Around the same time, the hormone got a lot of press as a possible treatment for many illnesses.<a href="#cite_note-pmid16077149-62">[62]</a> The <a href="/wiki/New_England_Journal_of_Medicine" class="mw-redirect" title="New England Journal of Medicine">New England Journal of Medicine</a> editorialized in 2000: "With these recent careful and precise observations in blind persons, the true potential of melatonin is becoming evident, and the importance of the timing of treatment is becoming clear."<a href="#cite_note-pmid11027748-63">[63]</a> It was approved for medical use in the European Union in 2007.<a href="#cite_note-Circadin-Label-8">[8]</a> <div class="mw-heading mw-heading2"><h2 id="Society_and_culture">Society and culture</h2>[<a href="/w/index.php?title=Melatonin_as_a_medication_and_supplement&action=edit&section=20" title="Edit section: Society and culture">edit</a>]</div> Melatonin is categorized by the US <a href="/wiki/Food_and_Drug_Administration" title="Food and Drug Administration">Food and Drug Administration</a> (FDA) as a dietary supplement, and is sold over-the-counter in both the US and Canada.<a href="#cite_note-Buscemi_2004-13">[13]</a> FDA regulations applying to medications are not applicable to melatonin,<a href="#cite_note-Altun2007-64">[64]</a> though the FDA has found false claims that it cures cancer.<a href="#cite_note-fda-65">[65]</a> As melatonin may cause harm in combination with certain medications or in the case of certain disorders, a doctor or pharmacist should be consulted before making a decision to take melatonin.<a href="#cite_note-pubmed12076414-30">[30]</a> In many countries, melatonin is recognized as a <a href="/wiki/Neurohormone" title="Neurohormone">neurohormone</a> and it cannot be sold over-the-counter.<a href="#cite_note-Toxicology-66">[66]</a> According to <a href="/wiki/Harriet_Hall" title="Harriet Hall">Harriet Hall</a> caution is advisable, since quality control is a documented problem. 71% of products did not contain within 10% of the labelled amount of melatonin, with variations ranging from -83% to +478%, lot-to-lot variability was as high as 465%, and the discrepancies were not correlated to any manufacturer or product type. To make matters worse, 8 out of 31 products were contaminated with the neurotransmitter serotonin.<a href="#cite_note-67">[67]</a><a href="#cite_note-68">[68]</a> Formerly, melatonin was derived from animal pineal tissue, such as bovine. It is now synthetic, which limits the risk of contamination or the means of transmitting infectious material.<a href="#cite_note-Altun2007-64">[64]</a><a href="#cite_note-69">[69]</a> Melatonin is the most popular over-the-counter sleep remedy in the United States, resulting in sales in excess of US$400 million during 2017.<a href="#cite_note-70">[70]</a> In 2021, it was the 257th most commonly prescribed medication in the US, with more than 1 million prescriptions.<a href="#cite_note-Top_300_of_2021-26">[26]</a><a href="#cite_note-Clincalc_Melatonin-27">[27]</a> Beverages and snacks containing melatonin were being sold in grocery stores, convenience stores, and clubs in May 2011.<a href="#cite_note-NYTimes_May_2011-71">[71]</a> The FDA considered whether these food products could continue to be sold with the label "dietary supplements". On 13 January 2010, it issued a Warning Letter to Innovative Beverage, creators of several beverages marketed as drinks, stating that melatonin, while legal as a dietary supplement, was not approved as a <a href="/wiki/Food_additive" title="Food additive">food additive</a>.<a href="#cite_note-FDAwarning-72">[72]</a> <a href="/wiki/Bebida_Beverage_Company" title="Bebida Beverage Company">Bebida Beverage Company</a> received a warning letter in 2015 for selling a melatonin-containing beverage.<a href="#cite_note-73">[73]</a> <div class="mw-heading mw-heading2"><h2 id="Research">Research</h2>[<a href="/w/index.php?title=Melatonin_as_a_medication_and_supplement&action=edit&section=21" title="Edit section: Research">edit</a>]</div> Some research supports an <a href="/wiki/Antidepressant" title="Antidepressant">antidepressant</a> and <a href="/wiki/Anxiolytic" title="Anxiolytic">anxiolytic</a> effect of melatonin.<a href="#cite_note-74">[74]</a><a href="#cite_note-75">[75]</a> It has also been used to aid in the treatment of manic episodes in <a href="/wiki/Bipolar_disorder" title="Bipolar disorder">bipolar disorder</a>, although evidence for its effectiveness is still inconsistent.<a href="#cite_note-repurposed2021-76">[76]</a> Other studies have shown that melatonin may help reduce some types of headaches, <a href="/wiki/Epigastric_pain" class="mw-redirect" title="Epigastric pain">epigastric pain</a> and <a href="/wiki/Heartburn" title="Heartburn">heartburn</a>.<a href="#cite_note-77">[77]</a><a href="#cite_note-Evars05-78">[78]</a><a href="#cite_note-Kandil10-79">[79]</a> There have also been studies trying to prove the effectiveness of melatonin in relation to <a href="/wiki/Epilepsy" title="Epilepsy">epilepsy</a>, <a href="/wiki/Dysmenorrhea" title="Dysmenorrhea">dysmenorrhea</a>, <a href="/wiki/Delirium" title="Delirium">delirium</a>, and <a href="/wiki/Tinnitus" title="Tinnitus">tinnitus</a>, but little to no beneficial role has been found.<a href="#cite_note-BrigoIgwe2016-80">[80]</a><a href="#cite_note-pmid27000311-81">[81]</a><a href="#cite_note-82">[82]</a><a href="#cite_note-83">[83]</a> Melatonin has also been tested as a treatment for cancer, but the National Cancer Institute found insufficient evidence for it. However, further research found it to slightly improve survival of patients and to alleviate chemotherapy-related side effects.<a href="#cite_note-84">[84]</a><a href="#cite_note-lim-85">[85]</a><a href="#cite_note-Posadzki2018-86">[86]</a><a href="#cite_note-wang2012-87">[87]</a> Both animal<a href="#cite_note-pmid10082913-88">[88]</a> and human<a href="#cite_note-pmid9008723-89">[89]</a><a href="#cite_note-90">[90]</a><a href="#cite_note-pmid9541644-91">[91]</a> studies have shown melatonin to protect against radiation-induced cellular damage. Melatonin and its metabolites protect organisms from <a href="/wiki/Oxidative_stress" title="Oxidative stress">oxidative stress</a> by scavenging <a href="/wiki/Reactive_oxygen_species" title="Reactive oxygen species">reactive oxygen species</a> which are generated during exposure.<a href="#cite_note-Tan_Manchester-92">[92]</a> Nearly 70% of biological damage caused by ionizing radiation is estimated to be attributable to the creation of free radicals, especially the <a href="/wiki/Hydroxyl_radical" title="Hydroxyl radical">hydroxyl radical</a> that attacks <a href="/wiki/DNA" title="DNA">DNA</a>, proteins, and <a href="/wiki/Cellular_membrane" class="mw-redirect" title="Cellular membrane">cellular membranes</a>. 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style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Alcohol_(chemistry)" title="Alcohol (chemistry)">Alcohols</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/2M2B" class="mw-redirect" title="2M2B">2M2B</a></li> <li><a href="/wiki/Chloralodol" title="Chloralodol">Chloralodol</a></li> <li><a href="/wiki/Alcohol_(drug)" title="Alcohol (drug)">Ethanol (alcohol)</a></li> <li><a href="/wiki/Diethylpropanediol" class="mw-redirect" title="Diethylpropanediol">Diethylpropanediol</a></li> <li><a href="/wiki/Ethchlorvynol" title="Ethchlorvynol">Ethchlorvynol</a></li> <li><a href="/wiki/Methylpentynol" title="Methylpentynol">Methylpentynol</a></li> <li><a href="/wiki/2,2,2-Trichloroethanol" title="2,2,2-Trichloroethanol">Trichloroethanol</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Barbiturate" title="Barbiturate">Barbiturates</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/Allobarbital" title="Allobarbital">Allobarbital</a></li> <li><a href="/wiki/Amobarbital" title="Amobarbital">Amobarbital</a></li> <li><a href="/wiki/Aprobarbital" title="Aprobarbital">Aprobarbital</a></li> <li><a href="/wiki/Barbital" title="Barbital">Barbital</a></li> <li><a href="/wiki/Butabarbital" title="Butabarbital">Butabarbital</a></li> <li><a href="/wiki/Butobarbital" title="Butobarbital">Butobarbital</a></li> <li><a href="/wiki/Cyclobarbital" title="Cyclobarbital">Cyclobarbital</a></li> <li><a href="/wiki/Ethallobarbital" title="Ethallobarbital">Ethallobarbital</a></li> <li><a href="/wiki/Heptabarb" title="Heptabarb">Heptabarb</a></li> <li><a href="/wiki/Hexobarbital" title="Hexobarbital">Hexobarbital</a></li> <li><a href="/wiki/Mephobarbital" class="mw-redirect" title="Mephobarbital">Mephobarbital</a></li> <li><a href="/wiki/Methohexital" title="Methohexital">Methohexital</a></li> <li><a href="/wiki/Narcobarbital" title="Narcobarbital">Narcobarbital</a></li> <li><a href="/wiki/Pentobarbital" title="Pentobarbital">Pentobarbital</a></li> <li><a href="/wiki/Phenallymal" class="mw-redirect" title="Phenallymal">Phenallymal</a></li> <li><a href="/wiki/Phenobarbital" title="Phenobarbital">Phenobarbital</a></li> <li><a href="/wiki/Propylbarbital" title="Propylbarbital">Propylbarbital</a></li> <li><a href="/wiki/Proxibarbal" class="mw-redirect" title="Proxibarbal">Proxibarbal</a></li> <li><a href="/wiki/Reposal" title="Reposal">Reposal</a></li> <li><a href="/wiki/Secobarbital" title="Secobarbital">Secobarbital</a></li> <li><a href="/wiki/Talbutal" title="Talbutal">Talbutal</a></li> <li><a href="/wiki/Thiamylal" title="Thiamylal">Thiamylal</a></li> <li><a href="/wiki/Sodium_thiopental" title="Sodium thiopental">Thiopental</a></li> <li><a href="/wiki/Thiotetrabarbital" title="Thiotetrabarbital">Thiotetrabarbital</a></li> <li><a href="/wiki/Vinbarbital" title="Vinbarbital">Vinbarbital</a></li> <li><a href="/wiki/Vinylbital" title="Vinylbital">Vinylbital</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Benzodiazepine" title="Benzodiazepine">Benzodiazepines</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/Brotizolam" title="Brotizolam">Brotizolam</a></li> <li><a href="/wiki/Cinolazepam" title="Cinolazepam">Cinolazepam</a></li> <li><a href="/wiki/Climazolam" title="Climazolam">Climazolam</a></li> <li><a href="/wiki/Clonazolam" title="Clonazolam">Clonazolam</a></li> <li><a href="/wiki/Doxefazepam" title="Doxefazepam">Doxefazepam</a></li> <li><a href="/wiki/Estazolam" title="Estazolam">Estazolam</a></li> <li><a href="/wiki/Flubromazolam" title="Flubromazolam">Flubromazolam</a></li> <li><a href="/wiki/Flunitrazolam" title="Flunitrazolam">Flunitrazolam</a></li> <li><a href="/wiki/Flunitrazepam" title="Flunitrazepam">Flunitrazepam</a></li> <li><a href="/wiki/Flurazepam" title="Flurazepam">Flurazepam</a></li> <li><a href="/wiki/Flutemazepam" title="Flutemazepam">Flutemazepam</a></li> <li><a href="/wiki/Flutoprazepam" title="Flutoprazepam">Flutoprazepam</a></li> <li><a href="/wiki/Loprazolam" title="Loprazolam">Loprazolam</a></li> <li><a href="/wiki/Lormetazepam" title="Lormetazepam">Lormetazepam</a></li> <li><a href="/wiki/Midazolam" title="Midazolam">Midazolam</a></li> <li><a href="/wiki/Nimetazepam" title="Nimetazepam">Nimetazepam</a></li> <li><a href="/wiki/Nitemazepam" title="Nitemazepam">Nitemazepam</a></li> <li><a href="/wiki/Nitrazepam" title="Nitrazepam">Nitrazepam</a></li> <li><a href="/wiki/Nitrazolam" title="Nitrazolam">Nitrazolam</a></li> <li><a href="/wiki/Quazepam" title="Quazepam">Quazepam</a></li> <li><a href="/wiki/Temazepam" title="Temazepam">Temazepam</a></li> <li><a href="/wiki/Triazolam" title="Triazolam">Triazolam</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Carbamate" title="Carbamate">Carbamates</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/Carisoprodol" title="Carisoprodol">Carisoprodol</a></li> <li><a href="/wiki/Emylcamate" title="Emylcamate">Emylcamate</a></li> <li><a href="/wiki/Ethinamate" title="Ethinamate">Ethinamate</a></li> <li><a href="/wiki/Hexapropymate" title="Hexapropymate">Hexapropymate</a></li> <li><a href="/wiki/Meprobamate" title="Meprobamate">Meprobamate</a></li> <li><a href="/wiki/Methocarbamol" title="Methocarbamol">Methocarbamol</a></li> <li><a href="/wiki/Phenprobamate" title="Phenprobamate">Phenprobamate</a></li> <li><a href="/wiki/Procymate" title="Procymate">Procymate</a></li> <li><a href="/wiki/Tybamate" title="Tybamate">Tybamate</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Imidazole" title="Imidazole">Imidazoles</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/Etomidate" title="Etomidate">Etomidate</a></li> <li><a href="/wiki/Metomidate" title="Metomidate">Metomidate</a></li> <li><a href="/wiki/Propoxate" title="Propoxate">Propoxate</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Monoureide" class="mw-redirect" title="Monoureide">Monoureides</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/Acecarbromal" title="Acecarbromal">Acecarbromal</a></li> <li><a href="/wiki/Apronal" title="Apronal">Apronal (apronalide)</a></li> <li><a href="/wiki/Bromisoval" title="Bromisoval">Bromisoval</a></li> <li><a href="/w/index.php?title=Capuride&action=edit&redlink=1" class="new" title="Capuride (page does not exist)">Capuride</a></li> <li><a href="/wiki/Carbromal" title="Carbromal">Carbromal</a></li> <li><a href="/w/index.php?title=Ectylurea&action=edit&redlink=1" class="new" title="Ectylurea (page does not exist)">Ectylurea</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Neuroactive_steroid" class="mw-redirect" title="Neuroactive steroid">Neuroactive steroids</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/Acebrochol" title="Acebrochol">Acebrochol</a></li> <li><a href="/wiki/Allopregnanolone" title="Allopregnanolone">Allopregnanolone</a></li> <li><a href="/wiki/Alfadolone" title="Alfadolone">Alphadolone</a></li> <li><a href="/wiki/Alphaxolone" class="mw-redirect" title="Alphaxolone">Alphaxolone</a></li> <li><a href="/wiki/Eltanolone" class="mw-redirect" title="Eltanolone">Eltanolone</a></li> <li><a href="/wiki/Hydroxydione" title="Hydroxydione">Hydroxydione</a></li> <li><a href="/wiki/Minaxolone" title="Minaxolone">Minaxolone</a></li> <li><a href="/wiki/Progesterone" title="Progesterone">Progesterone</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Nonbenzodiazepine" title="Nonbenzodiazepine">Nonbenzodiazepines</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/Eszopiclone" title="Eszopiclone">Eszopiclone</a></li> <li><a href="/wiki/Indiplon" title="Indiplon">Indiplon</a></li> <li><a href="/wiki/Lirequinil" title="Lirequinil">Lirequinil</a></li> <li><a href="/wiki/Necopidem" title="Necopidem">Necopidem</a></li> <li><a href="/wiki/Pazinaclone" title="Pazinaclone">Pazinaclone</a></li> <li><a href="/wiki/Saripidem" title="Saripidem">Saripidem</a></li> <li><a href="/wiki/Suproclone" title="Suproclone">Suproclone</a></li> <li><a href="/wiki/Suriclone" title="Suriclone">Suriclone</a></li> <li><a href="/wiki/Zaleplon" title="Zaleplon">Zaleplon</a></li> <li><a href="/wiki/Zolpidem" title="Zolpidem">Zolpidem</a></li> <li><a href="/wiki/Zopiclone" title="Zopiclone">Zopiclone</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Phenol" title="Phenol">Phenols</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/Propofol" title="Propofol">Propofol</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Piperidinedione" class="mw-redirect" title="Piperidinedione">Piperidinediones</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/Glutethimide" title="Glutethimide">Glutethimide</a></li> <li><a href="/wiki/Methyprylon" title="Methyprylon">Methyprylon</a></li> <li><a href="/wiki/Pyrithyldione" title="Pyrithyldione">Pyrithyldione</a></li> <li><a href="/wiki/Piperidione" title="Piperidione">Piperidione</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Quinazolinone" title="Quinazolinone">Quinazolinones</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/Afloqualone" title="Afloqualone">Afloqualone</a></li> <li><a href="/wiki/Cloroqualone" title="Cloroqualone">Cloroqualone</a></li> <li><a href="/wiki/Diproqualone" title="Diproqualone">Diproqualone</a></li> <li><a href="/wiki/Etaqualone" title="Etaqualone">Etaqualone</a></li> <li><a href="/wiki/Mebroqualone" title="Mebroqualone">Mebroqualone</a></li> <li><a href="/wiki/Mecloqualone" title="Mecloqualone">Mecloqualone</a></li> <li><a href="/wiki/Methaqualone" title="Methaqualone">Methaqualone</a></li> <li><a href="/wiki/Methylmethaqualone" title="Methylmethaqualone">Methylmethaqualone</a></li> <li><a href="/wiki/Nitromethaqualone" title="Nitromethaqualone">Nitromethaqualone</a></li> <li><a href="/wiki/SL-164" title="SL-164">SL-164</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;">Others</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Acetophenone" title="Acetophenone">Acetophenone</a></li> <li><a href="/wiki/Acetylglycinamide_chloral_hydrate" title="Acetylglycinamide chloral hydrate">Acetylglycinamide chloral hydrate</a></li> <li><a href="/wiki/Bromide" title="Bromide">Bromide</a> compounds <ul><li><a href="/wiki/Lithium_bromide" title="Lithium bromide">Lithium bromide</a></li> <li><a href="/wiki/Potassium_bromide" title="Potassium bromide">Potassium bromide</a></li> <li><a href="/wiki/Sodium_bromide" title="Sodium bromide">Sodium bromide</a></li></ul></li> <li><a href="/wiki/Centalun" title="Centalun">Centalun</a></li> <li><a href="/wiki/Chloral_betaine" title="Chloral betaine">Chloral betaine</a></li> <li><a href="/wiki/Chloral_hydrate" title="Chloral hydrate">Chloral hydrate</a></li> <li><a href="/wiki/Chloralose" title="Chloralose">Chloralose</a></li> <li><a href="/wiki/Clomethiazole" title="Clomethiazole">Clomethiazole</a></li> <li><a href="/wiki/Dichloralphenazone" title="Dichloralphenazone">Dichloralphenazone</a></li> <li><a href="/wiki/Gaboxadol" title="Gaboxadol">Gaboxadol</a></li> <li><a href="/wiki/Kavalactone" title="Kavalactone">Kavalactones</a></li> <li><a href="/wiki/Loreclezole" title="Loreclezole">Loreclezole</a></li> <li><a href="/wiki/Paraldehyde" title="Paraldehyde">Paraldehyde</a></li> <li><a href="/wiki/Petrichloral" title="Petrichloral">Petrichloral</a></li> <li><a href="/w/index.php?title=Sulfonylalkane&action=edit&redlink=1" class="new" title="Sulfonylalkane (page does not exist)">Sulfonylalkanes</a> <ul><li><a href="/wiki/Sulfonmethane" title="Sulfonmethane">Sulfonmethane (sulfonal)</a></li> <li><a href="/wiki/Tetronal" title="Tetronal">Tetronal</a></li> <li><a href="/wiki/Trional" title="Trional">Trional</a></li></ul></li> <li><a href="/wiki/Triclofos" title="Triclofos">Triclofos</a></li> <li><a href="/wiki/Sesquiterpene" title="Sesquiterpene">Sesquiterpene</a> <ul><li><a href="/wiki/Isovaleramide" title="Isovaleramide">Isovaleramide</a></li> <li><a href="/wiki/Isovaleric_acid" title="Isovaleric acid">Isovaleric acid</a></li> <li><a href="/wiki/Valerenic_acid" title="Valerenic acid">Valerenic acid</a></li></ul></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/GABAB_receptor" title="GABAB receptor">GABAB</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/1,4-Butanediol" title="1,4-Butanediol">1,4-Butanediol</a></li> <li><a href="/wiki/4-Fluorophenibut" title="4-Fluorophenibut">4-Fluorophenibut</a></li> <li><a href="/wiki/Aceburic_acid" title="Aceburic acid">Aceburic acid</a></li> <li><a href="/wiki/Baclofen" title="Baclofen">Baclofen</a></li> <li><a href="/wiki/GABOB" class="mw-redirect" title="GABOB">GABOB</a></li> <li><a href="/wiki/Gamma-Hydroxybutyric_acid" class="mw-redirect" title="Gamma-Hydroxybutyric acid">GHB</a> (<a href="/wiki/Sodium_oxybate" title="Sodium oxybate">sodium oxybate</a>)</li> <li><a href="/wiki/Gamma-Butyrolactone" class="mw-redirect" title="Gamma-Butyrolactone">GBL</a></li> <li><a href="/wiki/Gamma-Valerolactone" class="mw-redirect" title="Gamma-Valerolactone">GVL</a></li> <li><a href="/wiki/Phenibut" title="Phenibut">Phenibut</a></li> <li><a href="/wiki/Tolibut" title="Tolibut">Tolibut</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/H1_receptor" class="mw-redirect" title="H1 receptor">H1</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Histamine_antagonist" class="mw-redirect" title="Histamine antagonist">Antihistamines</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/Captodiame" title="Captodiame">Captodiame</a></li> <li><a href="/wiki/Cyproheptadine" title="Cyproheptadine">Cyproheptadine</a></li> <li><a href="/wiki/Diphenhydramine" title="Diphenhydramine">Diphenhydramine</a></li> <li><a href="/wiki/Doxylamine" title="Doxylamine">Doxylamine</a></li> <li><a href="/wiki/Hydroxyzine" title="Hydroxyzine">Hydroxyzine</a></li> <li><a href="/wiki/Methapyrilene" title="Methapyrilene">Methapyrilene</a></li> <li><a href="/wiki/Perlapine" title="Perlapine">Perlapine</a></li> <li><a href="/wiki/Pheniramine" title="Pheniramine">Pheniramine</a></li> <li><a href="/wiki/Promethazine" title="Promethazine">Promethazine</a></li> <li><a href="/wiki/Propiomazine" title="Propiomazine">Propiomazine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Antidepressant" title="Antidepressant">Antidepressants</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/Serotonin_antagonists_and_reuptake_inhibitors" class="mw-redirect" title="Serotonin antagonists and reuptake inhibitors">Serotonin antagonists and reuptake inhibitors</a> <ul><li><a href="/wiki/Etoperidone" title="Etoperidone">Etoperidone</a></li> <li><a href="/wiki/Nefazodone" title="Nefazodone">Nefazodone</a></li> <li><a href="/wiki/Trazodone" title="Trazodone">Trazodone</a></li></ul></li> <li><a href="/wiki/Tricyclic_antidepressant" title="Tricyclic antidepressant">Tricyclic antidepressants</a> <ul><li><a href="/wiki/Amitriptyline" title="Amitriptyline">Amitriptyline</a></li> <li><a href="/wiki/Doxepin" title="Doxepin">Doxepin</a></li> <li><a href="/wiki/Trimipramine" title="Trimipramine">Trimipramine</a>, etc.</li></ul></li> <li><a href="/wiki/Tetracyclic_antidepressant" title="Tetracyclic antidepressant">Tetracyclic antidepressants</a> <ul><li><a href="/wiki/Mianserin" title="Mianserin">Mianserin</a></li> <li><a href="/wiki/Mirtazapine" title="Mirtazapine">Mirtazapine</a>, etc.</li></ul></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Antipsychotic" title="Antipsychotic">Antipsychotics</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/Typical_antipsychotic" title="Typical antipsychotic">Typical antipsychotics</a> <ul><li><a href="/wiki/Chlorpromazine" title="Chlorpromazine">Chlorpromazine</a></li> <li><a href="/wiki/Thioridazine" title="Thioridazine">Thioridazine</a>, etc.</li></ul></li> <li><a href="/wiki/Atypical_antipsychotic" title="Atypical antipsychotic">Atypical antipsychotics</a> <ul><li><a href="/wiki/Olanzapine" title="Olanzapine">Olanzapine</a></li> <li><a href="/wiki/Quetiapine" title="Quetiapine">Quetiapine</a></li> <li><a href="/wiki/Risperidone" title="Risperidone">Risperidone</a>, etc.</li></ul></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Alpha-2_adrenergic_receptor" title="Alpha-2 adrenergic receptor">α2-Adrenergic</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/Clonidine" title="Clonidine">Clonidine</a></li> <li><a href="/wiki/Detomidine" title="Detomidine">Detomidine</a></li> <li><a href="/wiki/Dexmedetomidine" title="Dexmedetomidine">Dexmedetomidine</a></li> <li><a href="/wiki/Lofexidine" title="Lofexidine">Lofexidine</a></li> <li><a href="/wiki/Medetomidine" title="Medetomidine">Medetomidine</a></li> <li><a href="/wiki/Romifidine" title="Romifidine">Romifidine</a></li> <li><a href="/wiki/Tizanidine" title="Tizanidine">Tizanidine</a></li> <li><a href="/wiki/Xylazine" title="Xylazine">Xylazine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/5-HT2A_receptor" title="5-HT2A receptor">5-HT2A</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Antidepressant" title="Antidepressant">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/Trazodone" title="Trazodone">Trazodone</a></li> <li><a href="/wiki/Tricyclic_antidepressant" title="Tricyclic antidepressant">Tricyclic antidepressants</a> <ul><li><a href="/wiki/Amitriptyline" title="Amitriptyline">Amitriptyline</a></li> <li><a href="/wiki/Doxepin" title="Doxepin">Doxepin</a></li> <li><a href="/wiki/Trimipramine" title="Trimipramine">Trimipramine</a>, etc.</li></ul></li> <li><a href="/wiki/Tetracyclic_antidepressant" title="Tetracyclic antidepressant">Tetracyclic antidepressants</a> <ul><li><a href="/wiki/Mianserin" title="Mianserin">Mianserin</a></li> <li><a href="/wiki/Mirtazapine" title="Mirtazapine">Mirtazapine</a>, etc.</li></ul></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Antipsychotic" title="Antipsychotic">Antipsychotics</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/Typical_antipsychotic" title="Typical antipsychotic">Typical antipsychotics</a> <ul><li><a href="/wiki/Chlorpromazine" title="Chlorpromazine">Chlorpromazine</a></li> <li><a href="/wiki/Thioridazine" title="Thioridazine">Thioridazine</a>, etc.</li></ul></li> <li><a href="/wiki/Atypical_antipsychotic" title="Atypical antipsychotic">Atypical antipsychotics</a> <ul><li><a href="/wiki/Olanzapine" title="Olanzapine">Olanzapine</a></li> <li><a href="/wiki/Quetiapine" title="Quetiapine">Quetiapine</a></li> <li><a href="/wiki/Risperidone" title="Risperidone">Risperidone</a>, etc.</li></ul></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;">Others</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Niaprazine" title="Niaprazine">Niaprazine</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Melatonin_receptor" title="Melatonin receptor">Melatonin</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/Agomelatine" title="Agomelatine">Agomelatine</a></li> <li><a href="/wiki/Melatonin_(medication)" class="mw-redirect" title="Melatonin (medication)">Melatonin</a></li> <li><a href="/wiki/Ramelteon" title="Ramelteon">Ramelteon</a></li> <li><a href="/wiki/Tasimelteon" title="Tasimelteon">Tasimelteon</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Orexin_receptor" title="Orexin receptor">Orexin</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/Daridorexant" title="Daridorexant">Daridorexant</a></li> <li><a href="/wiki/Lemborexant" title="Lemborexant">Lemborexant</a></li> <li><a href="/wiki/Suvorexant" title="Suvorexant">Suvorexant</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Gabapentinoid" title="Gabapentinoid"><abbr title="alpha2delta subunit">α2δ</abbr> <abbr title="voltage-gated calcium channel">VDCC</abbr></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/Gabapentin" title="Gabapentin">Gabapentin</a></li> <li><a href="/wiki/Gabapentin_enacarbil" title="Gabapentin enacarbil">Gabapentin enacarbil</a></li> <li><a href="/wiki/Mirogabalin" title="Mirogabalin">Mirogabalin</a></li> <li><a href="/wiki/Phenibut" title="Phenibut">Phenibut</a></li> <li><a href="/wiki/Pregabalin" title="Pregabalin">Pregabalin</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;">Others</th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Cannabidiol" title="Cannabidiol">Cannabidiol</a> <ul><li><a href="/wiki/Cannabis_(drug)" title="Cannabis (drug)">Cannabis</a></li></ul></li> <li><a href="/w/index.php?title=Chlorophenylalkyldiol&action=edit&redlink=1" class="new" title="Chlorophenylalkyldiol (page does not exist)">Chlorophenylalkyldiols</a> <ul><li><a href="/wiki/Fenpentadiol" title="Fenpentadiol">Fenpentadiol</a></li> <li><a href="/wiki/Metaglycodol" title="Metaglycodol">Metaglycodol</a></li> <li><a href="/wiki/Phenaglycodol" title="Phenaglycodol">Phenaglycodol</a></li></ul></li> <li><a href="/wiki/2,2-Diethyl-1,3-propanediol" class="mw-redirect" title="2,2-Diethyl-1,3-propanediol">Diethylpropanediol</a></li> <li><a href="/wiki/Evoxine" title="Evoxine">Evoxine</a></li> <li><a href="/wiki/Fenadiazole" title="Fenadiazole">Fenadiazole</a></li> <li><a href="/wiki/Guaifenesin" title="Guaifenesin">Guaifenesin</a>-related <a href="/wiki/Muscle_relaxant" title="Muscle relaxant">muscle relaxants</a> <ul><li><a href="/wiki/Chlorphenesin" class="mw-redirect" title="Chlorphenesin">Chlorphenesin</a></li> <li><a href="/wiki/Mephenesin" title="Mephenesin">Mephenesin</a></li> <li><a href="/wiki/Mephenoxalone" title="Mephenoxalone">Mephenoxalone</a></li> <li><a href="/wiki/Metaxalone" title="Metaxalone">Metaxalone</a></li> <li><a href="/wiki/Methocarbamol" title="Methocarbamol">Methocarbamol</a></li></ul></li> <li><a href="/wiki/Midaflur" title="Midaflur">Midaflur</a></li> <li><a href="/wiki/Opioid" title="Opioid">Opioids</a> (e.g., <a href="/wiki/Morphine" title="Morphine">morphine</a>)</li> <li><a href="/wiki/Passiflora" title="Passiflora">Passion flower</a></li> <li><a href="/wiki/Scopolamine" title="Scopolamine">Scopolamine</a></li> <li><a href="/wiki/Trazodone" title="Trazodone">Trazodone</a></li> <li><a href="/wiki/UMB68" class="mw-redirect" title="UMB68">UMB68</a></li> <li><a href="/wiki/Valnoctamide" title="Valnoctamide">Valnoctamide</a></li></ul> </div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"></div><div role="navigation" class="navbox" aria-labelledby="Insomnia_medications" 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:Insomnia_medications" title="Template:Insomnia medications"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Insomnia_medications" title="Template talk:Insomnia medications"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Insomnia_medications" title="Special:EditPage/Template:Insomnia medications"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Insomnia_medications" style="font-size:114%;margin:0 4em"><a href="/wiki/Hypnotic" title="Hypnotic">Insomnia medications</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/GABAA_receptor_positive_allosteric_modulator" title="GABAA receptor positive allosteric modulator">GABAA receptor positive modulators</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/Benzodiazepine" title="Benzodiazepine">Benzodiazepines</a>: <a href="/wiki/Brotizolam" title="Brotizolam">Brotizolam</a></li> <li><a href="/wiki/Cinolazepam" title="Cinolazepam">Cinolazepam</a></li> <li><a href="/wiki/Climazolam" title="Climazolam">Climazolam</a></li> <li><a href="/wiki/Clorazepate" title="Clorazepate">Clorazepate</a></li> <li><a href="/wiki/Doxefazepam" title="Doxefazepam">Doxefazepam</a></li> <li><a href="/wiki/Estazolam" title="Estazolam">Estazolam</a></li> <li><a href="/wiki/Etizolam" title="Etizolam">Etizolam</a></li> <li><a href="/wiki/Flunitrazepam" title="Flunitrazepam">Flunitrazepam</a></li> <li><a href="/wiki/Flurazepam" title="Flurazepam">Flurazepam</a></li> <li><a href="/wiki/Flutoprazepam" title="Flutoprazepam">Flutoprazepam</a></li> <li><a href="/wiki/Haloxazolam" title="Haloxazolam">Haloxazolam</a></li> <li><a href="/wiki/Loprazolam" title="Loprazolam">Loprazolam</a></li> <li><a href="/wiki/Lormetazepam" title="Lormetazepam">Lormetazepam</a></li> <li><a href="/wiki/Midazolam" title="Midazolam">Midazolam</a></li> <li><a href="/wiki/Nimetazepam" title="Nimetazepam">Nimetazepam</a></li> <li><a href="/wiki/Nitrazepam" title="Nitrazepam">Nitrazepam</a></li> <li><a href="/wiki/Quazepam" title="Quazepam">Quazepam</a></li> <li><a href="/wiki/Temazepam" title="Temazepam">Temazepam</a></li> <li><a href="/wiki/Triazolam" title="Triazolam">Triazolam</a></li></ul> <ul><li><a href="/wiki/Nonbenzodiazepine" title="Nonbenzodiazepine">Nonbenzodiazepines</a>/<a href="/wiki/Z-drug" class="mw-redirect" title="Z-drug">Z-drugs</a>: <a href="/wiki/Eszopiclone" title="Eszopiclone">Eszopiclone</a></li> <li><a href="/wiki/Zaleplon" title="Zaleplon">Zaleplon</a></li> <li><a href="/wiki/Zolpidem" title="Zolpidem">Zolpidem</a></li> <li><a href="/wiki/Zopiclone" title="Zopiclone">Zopiclone</a></li></ul> <ul><li>Others: <a href="/wiki/Alcohol_(chemistry)" title="Alcohol (chemistry)">Alcohols</a> (e.g., <a href="/wiki/Ethchlorvynol" title="Ethchlorvynol">ethchlorvynol</a>, <a href="/wiki/Tert-Amyl_alcohol" title="Tert-Amyl alcohol">amylene hydrate</a>, <a href="/wiki/Ethanol" title="Ethanol">ethanol</a>)</li> <li><a href="/wiki/Barbiturate" title="Barbiturate">Barbiturates</a> (e.g., <a href="/wiki/Amobarbital" title="Amobarbital">amobarbital</a>, <a href="/wiki/Pentobarbital" title="Pentobarbital">pentobarbital</a>, <a href="/wiki/Phenobarbital" title="Phenobarbital">phenobarbital</a>, <a href="/wiki/Secobarbital" title="Secobarbital">secobarbital</a>)</li> <li><a href="/wiki/Bromide" title="Bromide">Bromides</a> (e.g., <a href="/wiki/Potassium_bromide" title="Potassium bromide">potassium bromide</a>, <a href="/wiki/Sodium_bromide" title="Sodium bromide">sodium bromide</a>)</li> <li><a href="/wiki/Carbamate" title="Carbamate">Carbamates</a> (e.g., <a href="/wiki/Meprobamate" title="Meprobamate">meprobamate</a>)</li> <li><a href="/wiki/Chloral_hydrate" title="Chloral hydrate">Chloral hydrate</a></li> <li><a href="/wiki/Clomethiazole" title="Clomethiazole">Clomethiazole</a></li> <li><a href="/wiki/Kava" title="Kava">Kava</a></li> <li><a href="/wiki/Neurosteroid" title="Neurosteroid">Neurosteroids</a> (e.g., <a href="/wiki/Progesterone_(medication)" title="Progesterone (medication)">progesterone</a>, <a href="/wiki/Zuranolone" title="Zuranolone">zuranolone</a>†)</li> <li><a href="/wiki/Paraldehyde" title="Paraldehyde">Paraldehyde</a></li> <li><a href="/wiki/Piperidinedione" class="mw-redirect" title="Piperidinedione">Piperidinediones</a> (e.g., <a href="/wiki/Glutethimide" title="Glutethimide">glutethimide</a>)</li> <li><a href="/wiki/Quinazolinone" title="Quinazolinone">Quinazolinones</a> (e.g., <a href="/wiki/Methaqualone" title="Methaqualone">methaqualone</a>)</li> <li><a href="/wiki/Sulfonmethane" title="Sulfonmethane">Sulfonmethane</a></li> <li><a href="/wiki/Valerian_(herb)" title="Valerian (herb)">Valerian</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/H1_antagonist" title="H1 antagonist">Antihistamines</a> (<a href="/wiki/H1_receptor" class="mw-redirect" title="H1 receptor">H1 receptor</a> <a href="/wiki/Inverse_agonist" title="Inverse agonist">inverse agonists</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/Alimemazine" title="Alimemazine">Alimemazine</a></li> <li><a href="/wiki/Captodiame" title="Captodiame">Captodiame</a></li> <li><a href="/wiki/Dimenhydrinate" title="Dimenhydrinate">Dimenhydrinate</a></li> <li><a href="/wiki/Diphenhydramine" title="Diphenhydramine">Diphenhydramine</a></li> <li><a href="/wiki/Doxylamine" title="Doxylamine">Doxylamine</a></li> <li><a href="/wiki/Etodroxizine" title="Etodroxizine">Etodroxizine</a></li> <li><a href="/wiki/Hydroxyzine" title="Hydroxyzine">Hydroxyzine</a></li> <li><a href="/wiki/Meclizine" title="Meclizine">Meclizine</a></li> <li><a href="/wiki/Methapyrilene" title="Methapyrilene">Methapyrilene</a></li> <li><a href="/wiki/Pheniramine" title="Pheniramine">Pheniramine</a></li> <li><a href="/wiki/Phenyltoloxamine" title="Phenyltoloxamine">Phenyltoloxamine</a></li> <li><a href="/wiki/Pimethixene" title="Pimethixene">Pimethixene</a></li> <li><a href="/wiki/Promethazine" title="Promethazine">Promethazine</a></li> <li><a href="/wiki/Propiomazine" title="Propiomazine">Propiomazine</a></li> <li><a href="/wiki/Pyrilamine" class="mw-redirect" title="Pyrilamine">Pyrilamine</a></li> <li><a href="/wiki/Tricyclic_antidepressant" title="Tricyclic antidepressant">Tricyclic antidepressants</a> (e.g., <a href="/wiki/Amitriptyline" title="Amitriptyline">amitriptyline</a>, <a href="/wiki/Doxepin" title="Doxepin">doxepin</a>, <a href="/wiki/Trimipramine" title="Trimipramine">trimipramine</a>)</li> <li><a href="/wiki/Tetracyclic_antidepressant" title="Tetracyclic antidepressant">Tetracyclic antidepressants</a> (e.g., <a href="/wiki/Mirtazapine" title="Mirtazapine">mirtazapine</a>)</li> <li><a href="/wiki/Triprolidine" title="Triprolidine">Triprolidine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Orexin_receptor_antagonist" class="mw-redirect" title="Orexin receptor antagonist">Orexin receptor antagonists</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Daridorexant" title="Daridorexant">Daridorexant</a></li> <li><a href="/wiki/Lemborexant" title="Lemborexant">Lemborexant</a></li> <li><a href="/wiki/Seltorexant" title="Seltorexant">Seltorexant</a>†</li> <li><a href="/wiki/Suvorexant" title="Suvorexant">Suvorexant</a></li> <li><a href="/wiki/Vornorexant" title="Vornorexant">Vornorexant</a>†</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Melatonin_receptor_agonist" title="Melatonin receptor agonist">Melatonin receptor agonists</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/Melatonin_(medication)" class="mw-redirect" title="Melatonin (medication)">Melatonin</a></li> <li><a href="/wiki/Ramelteon" title="Ramelteon">Ramelteon</a></li> <li><a href="/wiki/Tasimelteon" title="Tasimelteon">Tasimelteon</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Miscellaneous</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Antipsychotic" title="Antipsychotic">Antipsychotics</a> (e.g., <a href="/wiki/Quetiapine" title="Quetiapine">quetiapine</a>, <a href="/wiki/Olanzapine" title="Olanzapine">olanzapine</a>, <a href="/wiki/Risperidone" title="Risperidone">risperidone</a>, <a href="/wiki/Chlorpromazine" title="Chlorpromazine">chlorpromazine</a>)</li> <li><a href="/wiki/Withania_somnifera" title="Withania somnifera">Ashwagandha</a></li> <li><a href="/wiki/Benzoctamine" title="Benzoctamine">Benzoctamine</a></li> <li><a href="/wiki/Cannabinoid" title="Cannabinoid">Cannabinoids</a> (e.g., <a href="/wiki/Cannabis_(drug)" title="Cannabis (drug)">cannabis</a>, <a href="/wiki/Dronabinol" title="Dronabinol">dronabinol (<abbr title="tetrahydrocannabinol">THC</abbr>)</a>, <a href="/wiki/Nabilone" title="Nabilone">nabilone</a>)</li> <li><a href="/wiki/Chamomile" title="Chamomile">Chamomile</a></li> <li><a href="/wiki/Fenadiazole" title="Fenadiazole">Fenadiazole</a></li> <li><a href="/wiki/Gabapentinoid" title="Gabapentinoid">Gabapentinoids</a> (e.g., <a href="/wiki/Gabapentin" title="Gabapentin">gabapentin</a>, <a href="/wiki/Pregabalin" title="Pregabalin">pregabalin</a>, <a href="/wiki/Phenibut" title="Phenibut">phenibut</a>)</li> <li><a href="/wiki/Hops" title="Hops">Hops</a></li> <li><a href="/wiki/Lavandula" title="Lavandula">Lavender</a></li> <li><a href="/wiki/Menthyl_isovalerate" title="Menthyl isovalerate">Menthyl isovalerate</a></li> <li><a href="/wiki/Niaprazine" title="Niaprazine">Niaprazine</a></li> <li><a href="/wiki/Opioid" title="Opioid">Opioids</a> (e.g., <a href="/wiki/Hydrocodone" title="Hydrocodone">hydrocodone</a>, <a href="/wiki/Oxycodone" title="Oxycodone">oxycodone</a>, <a href="/wiki/Morphine" title="Morphine">morphine</a>)</li> <li><a href="/wiki/Passiflora" title="Passiflora">Passion flower</a></li> <li><a href="/wiki/Scopolamine" title="Scopolamine">Scopolamine</a></li> <li><a href="/wiki/Neurotransmitter#Serotonin_precursors" title="Neurotransmitter">Serotonin precursors</a> (<a href="/wiki/Tryptophan" title="Tryptophan">tryptophan</a>, <a href="/wiki/5-hydroxytryptophan" class="mw-redirect" title="5-hydroxytryptophan"><abbr title="5-hydroxytryptophan">5-HTP</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 5-hydroxytryptophan)</li> <li><a href="/wiki/Sodium_oxybate" title="Sodium oxybate">Sodium oxybate (<abbr title="γ-aminobutyric acid">GHB</abbr>)</a></li> <li><a href="/wiki/Sympatholytic" title="Sympatholytic">Sympatholytics</a> (e.g., <a href="/wiki/Clonidine" title="Clonidine">clonidine</a>, <a href="/wiki/Guanfacine" title="Guanfacine">guanfacine</a>, <a href="/wiki/Prazosin" title="Prazosin">prazosin</a>)</li> <li><a href="/wiki/Theanine" title="Theanine">Theanine</a></li> <li><a href="/wiki/Trazodone" title="Trazodone">Trazodone</a></li> <li><a href="/wiki/Tricyclic_antidepressant" title="Tricyclic antidepressant">Tricyclic antidepressants</a> (e.g., <a href="/wiki/Amitriptyline" title="Amitriptyline">amitriptyline</a>, <a href="/wiki/Doxepin" title="Doxepin">doxepin</a>, <a href="/wiki/Trimipramine" title="Trimipramine">trimipramine</a>)</li> <li><a href="/wiki/Tetracyclic_antidepressant" title="Tetracyclic antidepressant">Tetracyclic antidepressants</a> (e.g., <a href="/wiki/Mirtazapine" title="Mirtazapine">mirtazapine</a>)</li> <li><a href="/wiki/Valnoctamide" title="Valnoctamide">Valnoctamide</a></li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"><div class="hlist"> <ul><li>#<a href="/wiki/WHO_Model_List_of_Essential_Medicines" title="WHO Model List of Essential Medicines">WHO-EM</a></li> <li>‡<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>†<a href="/wiki/Phases_of_clinical_research#Phase_III" title="Phases of clinical research">Phase III</a></li> <li>§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="Dietary_supplements" 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:Dietary_supplement" title="Template:Dietary supplement"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Dietary_supplement" title="Template talk:Dietary supplement"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Dietary_supplement" title="Special:EditPage/Template:Dietary supplement"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Dietary_supplements" style="font-size:114%;margin:0 4em"><a href="/wiki/Dietary_supplement" title="Dietary supplement">Dietary supplements</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%">Types</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/Bodybuilding_supplement" title="Bodybuilding supplement">Bodybuilding supplement</a></li> <li><a href="/wiki/Energy_drink" title="Energy drink">Energy drink</a></li> <li><a href="/wiki/Energy_bar" title="Energy bar">Energy bar</a></li> <li><a href="/wiki/Essential_fatty_acid" title="Essential fatty acid">Fatty acids</a></li> <li><a href="/wiki/Herbal_medicine" title="Herbal medicine">Herbal supplements</a></li> <li><a href="/wiki/Mineral_(nutrient)" title="Mineral (nutrient)">Minerals</a></li> <li><a href="/wiki/Prebiotic_(nutrition)" title="Prebiotic (nutrition)">Prebiotics</a></li> <li><a href="/wiki/Probiotic" title="Probiotic">Probiotics</a> (<a href="/wiki/Lactobacillus" title="Lactobacillus">Lactobacillus</a></li> <li><a href="/wiki/Bifidobacterium" title="Bifidobacterium">Bifidobacterium</a>)</li> <li><a href="/wiki/Protein_supplement" title="Protein supplement">Protein supplements</a></li> <li><a href="/wiki/Vitamin" title="Vitamin">Vitamins</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Vitamin" title="Vitamin">Vitamins</a> and <a href="/wiki/Mineral_(nutrient)" title="Mineral (nutrient)">chemical elements ("minerals")</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/Vitamin_A" title="Vitamin A">Retinol (Vitamin A)</a></li> <li><a href="/wiki/B_vitamins" title="B vitamins">B vitamins</a> <ul><li><a href="/wiki/Thiamine" title="Thiamine">Thiamine (B1)</a></li> <li><a href="/wiki/Riboflavin" title="Riboflavin">Riboflavin (B2)</a></li> <li><a href="/wiki/Niacin_(nutrient)" class="mw-redirect" title="Niacin (nutrient)">Niacin (B3)</a></li> <li><a href="/wiki/Pantothenic_acid" title="Pantothenic acid">Pantothenic acid (B5)</a></li> <li><a href="/wiki/Vitamin_B6" title="Vitamin B6">Pyridoxine (B6)</a></li> <li><a href="/wiki/Biotin" title="Biotin">Biotin (B7)</a></li> <li><a href="/wiki/Folate" title="Folate">Folic acid (B9)</a></li> <li><a href="/wiki/Cyanocobalamin" title="Cyanocobalamin">Cyanocobalamin (B12)</a></li></ul></li> <li><a href="/wiki/Vitamin_C" title="Vitamin C">Ascorbic acid (Vitamin C)</a></li> <li><a href="/wiki/Vitamin_D" title="Vitamin D">Ergocalciferol and Cholecalciferol (Vitamin D)</a></li> <li><a href="/wiki/Vitamin_E" title="Vitamin E">Tocopherol (Vitamin E)</a></li> <li><a href="/wiki/Vitamin_K" title="Vitamin K">Naphthoquinone (Vitamin K)</a></li></ul> <ul><li><a href="/wiki/Calcium_supplement" title="Calcium supplement">Calcium</a></li> <li><a href="/wiki/Choline" title="Choline">Choline</a></li> <li><a href="/wiki/Chromium" title="Chromium">Chromium</a></li> <li><a href="/wiki/Cobalt" title="Cobalt">Cobalt</a></li> <li><a href="/wiki/Copper" title="Copper">Copper</a></li> <li><a href="/wiki/Fluorine" title="Fluorine">Fluorine</a></li> <li><a href="/wiki/Iodine" title="Iodine">Iodine</a></li> <li><a href="/wiki/Iron" title="Iron">Iron</a></li> <li><a href="/wiki/Magnesium" title="Magnesium">Magnesium</a></li> <li><a href="/wiki/Manganese" title="Manganese">Manganese</a></li> <li><a href="/wiki/Molybdenum" title="Molybdenum">Molybdenum</a></li> <li><a href="/wiki/Phosphorus" title="Phosphorus">Phosphorus</a></li> <li><a href="/wiki/Potassium" title="Potassium">Potassium</a></li> <li><a href="/wiki/Selenium" title="Selenium">Selenium</a></li> <li><a href="/wiki/Sodium" title="Sodium">Sodium</a></li> <li><a href="/wiki/Sulfur" title="Sulfur">Sulfur</a></li> <li><a href="/wiki/Zinc" title="Zinc">Zinc</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Other common ingredients</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/Arginine_alpha-ketoglutarate" title="Arginine alpha-ketoglutarate">AAKG</a></li> <li><a href="/wiki/Beta-Hydroxy_beta-methylbutyric_acid" class="mw-redirect" title="Beta-Hydroxy beta-methylbutyric acid">β-hydroxy β-methylbutyrate</a></li> <li><a href="/wiki/Carnitine" title="Carnitine">Carnitine</a></li> <li><a href="/wiki/Chondroitin_sulfate" title="Chondroitin sulfate">Chondroitin sulfate</a></li> <li><a href="/wiki/Cod_liver_oil" title="Cod liver oil">Cod liver oil</a></li> <li><a href="/wiki/Copper_gluconate" title="Copper gluconate">Copper gluconate</a></li> <li><a href="/wiki/Creatine" title="Creatine">Creatine</a></li> <li><a href="/wiki/Dietary_fiber" title="Dietary fiber">Dietary fiber</a></li> <li><a href="/wiki/Echinacea#Medicinal_effects" title="Echinacea">Echinacea</a></li> <li><a href="/wiki/Ephedra_(medicine)" title="Ephedra (medicine)">Ephedra</a></li> <li><a href="/wiki/Fish_oil" title="Fish oil">Fish oil</a></li> <li><a href="/wiki/Folate" title="Folate">Folic acid</a></li> <li><a href="/wiki/Ginseng" title="Ginseng">Ginseng</a></li> <li><a href="/wiki/Glucosamine" title="Glucosamine">Glucosamine</a></li> <li><a href="/wiki/Glutamine" title="Glutamine">Glutamine</a></li> <li><a href="/wiki/Grape_seed_extract" title="Grape seed extract">Grape seed extract</a></li> <li><a href="/wiki/Guarana" title="Guarana">Guarana</a></li> <li><a href="/wiki/Iron_supplement" title="Iron supplement">Iron supplements</a></li> <li><a href="/wiki/Lonicera_japonica" title="Lonicera japonica">Japanese honeysuckle</a></li> <li><a href="/wiki/Krill_oil" title="Krill oil">Krill oil</a></li> <li><a href="/wiki/Lingzhi_(mushroom)" title="Lingzhi (mushroom)">Lingzhi</a></li> <li><a href="/wiki/Linseed_oil" title="Linseed oil">Linseed oil</a></li> <li><a href="/wiki/Lipoic_acid" title="Lipoic acid">Lipoic acid</a></li> <li><a href="/wiki/Silybum_marianum#Health_benefits" title="Silybum marianum">Milk thistle</a></li> <li><a href="/wiki/Melatonin_(supplement)" class="mw-redirect" title="Melatonin (supplement)">Melatonin</a></li> <li><a href="/wiki/Red_yeast_rice" title="Red yeast rice">Red yeast rice</a></li> <li><a href="/wiki/Royal_jelly" title="Royal jelly">Royal jelly</a></li> <li><a href="/wiki/Saw_palmetto_extract" title="Saw palmetto extract">Saw palmetto</a></li> <li><a href="/wiki/Spirulina_(dietary_supplement)" title="Spirulina (dietary supplement)">Spirulina</a></li> <li><a href="/wiki/Hypericum_perforatum#Medicinal_uses" title="Hypericum perforatum">St John's wort</a></li> <li><a href="/wiki/Taurine" title="Taurine">Taurine</a></li> <li><a href="/wiki/Wheatgrass" title="Wheatgrass">Wheatgrass</a></li> <li><a href="/wiki/Goji" title="Goji">Wolfberry</a></li> <li><a href="/wiki/Yohimbine" title="Yohimbine">Yohimbine</a></li> <li><a href="/wiki/Zinc_gluconate" title="Zinc gluconate">Zinc gluconate</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Related articles</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/Codex_Alimentarius" title="Codex Alimentarius">Codex Alimentarius</a></li> <li><a href="/wiki/Enzyte" title="Enzyte">Enzyte</a></li> <li><a href="/wiki/Hadacol" title="Hadacol">Hadacol</a></li> <li><a href="/wiki/Herbal_tea" title="Herbal tea">Herbal tea</a></li> <li><a href="/wiki/Nutraceutical" title="Nutraceutical">Nutraceutical</a></li> <li><a href="/wiki/Multivitamin" title="Multivitamin">Multivitamin</a></li> <li><a href="/wiki/Nutrition" title="Nutrition">Nutrition</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_modulators" style="padding:3px"><table class="nowraplinks hlist mw-collapsible mw-collapsed navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template: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_modulators" 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">MT1</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</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li>Agonists: <a href="/wiki/2-Iodomelatonin" title="2-Iodomelatonin">2-Iodomelatonin</a></li> <li><a href="/wiki/6-Hydroxymelatonin" title="6-Hydroxymelatonin">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>Antagonists: <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">MT2</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</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li>Agonists: <a href="/wiki/2-Iodomelatonin" title="2-Iodomelatonin">2-Iodomelatonin</a></li> <li><a href="/wiki/6-Hydroxymelatonin" title="6-Hydroxymelatonin">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>Antagonists: <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>Agonists: <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">MT3</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)</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>Antagonists: <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">MT3</abbr>)</li> <li><a href="/wiki/Prazosin" title="Prazosin">Prazosin</a> (of <abbr title="melatonin receptor 1C">MT3</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>See also: <a href="/wiki/Template:Receptor_modulators" title="Template:Receptor modulators">Receptor/signaling modulators</a></li> <li><a href="/wiki/Template:Adrenergics" class="mw-redirect" title="Template:Adrenergics">Adrenergics</a></li> <li><a href="/wiki/Template:Dopaminergics" class="mw-redirect" title="Template:Dopaminergics">Dopaminergics</a></li> <li><a href="/wiki/Template:Serotonergics" class="mw-redirect" title="Template:Serotonergics">Serotonergics</a></li> <li><a href="/wiki/Template:Monoamine_metabolism_modulators" title="Template:Monoamine metabolism modulators">Monoamine metabolism modulators</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="Tryptamines" 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: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="Tryptamines" 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="/wiki/1-Methylpsilocin" title="1-Methylpsilocin">1-Methylpsilocin</a></li> <li><a href="/wiki/2-HO-NMT" title="2-HO-NMT">2-HO-NMT</a></li> <li><a href="/wiki/2-Me-DET" title="2-Me-DET">2-Me-DET</a></li> <li><a href="/wiki/2-Methyl-5-hydroxytryptamine" title="2-Methyl-5-hydroxytryptamine">2-Methyl-5-HT</a></li> <li><a href="/wiki/2,N,N-TMT" title="2,N,N-TMT">2,N,N-TMT</a></li> <li><a href="/wiki/1-(2-Dimethylaminoethyl)dihydropyrano(3,2-e)indole" class="mw-redirect" title="1-(2-Dimethylaminoethyl)dihydropyrano(3,2-e)indole">4,5-DHP-DMT</a></li> <li><a href="/wiki/4-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="/wiki/4-Hydroxy-5-methoxydimethyltryptamine" title="4-Hydroxy-5-methoxydimethyltryptamine">4-HO-5-MeO-DMT</a></li> <li><a href="/w/index.php?title=4-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="/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="/wiki/5-Carboxamidotryptamine" title="5-Carboxamidotryptamine">5-CT</a></li> <li><a href="/wiki/5-Chloro-DMT" title="5-Chloro-DMT">5-Chloro-DMT</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="/wiki/5-HO-DiPT" title="5-HO-DiPT">5-HO-DiPT</a></li> <li><a href="/wiki/5-Hydroxytryptophan" title="5-Hydroxytryptophan">5-HTP (oxitriptan)</a></li> <li><a href="/wiki/5-MeO-2-TMT" title="5-MeO-2-TMT">5-MeO-2-TMT</a></li> <li><a href="/w/index.php?title=5-MeO-34MPEMT&action=edit&redlink=1" class="new" title="5-MeO-34MPEMT (page does not exist)">5-MeO-34MPEMT</a></li> <li><a href="/wiki/5-Methoxy-7,N,N-trimethyltryptamine" title="5-Methoxy-7,N,N-trimethyltryptamine">5-MeO-7,N,N-TMT</a></li> <li><a href="/wiki/5-MeO-DALT" title="5-MeO-DALT">5-MeO-DALT</a></li> <li><a href="/wiki/5-MeO-DBT" title="5-MeO-DBT">5-MeO-DBT</a></li> <li><a href="/wiki/5-MeO-DET" title="5-MeO-DET">5-MeO-DET</a></li> <li><a href="/wiki/5-Methoxy-N,N-diisopropyltryptamine" class="mw-redirect" title="5-Methoxy-N,N-diisopropyltryptamine">5-MeO-DiPT</a></li> <li><a href="/wiki/5-MeO-DMT" title="5-MeO-DMT">5-MeO-DMT</a></li> <li><a href="/wiki/5-MeO-DPT" title="5-MeO-DPT">5-MeO-DPT</a></li> <li><a href="/wiki/5-MeO-EiPT" title="5-MeO-EiPT">5-MeO-EiPT</a></li> <li><a href="/wiki/5-MeO-EPT" title="5-MeO-EPT">5-MeO-EPT</a></li> <li><a href="/wiki/5-MeO-MALT" title="5-MeO-MALT">5-MeO-MALT</a></li> <li><a href="/wiki/5-MeO-MET" title="5-MeO-MET">5-MeO-MET</a></li> <li><a href="/wiki/5-MeO-MiPT" title="5-MeO-MiPT">5-MeO-MiPT</a></li> <li><a href="/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-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-Methoxytryptamine" title="5-Methoxytryptamine">5-Methoxytryptamine (5-MT; mexamine)</a></li> <li><a href="/wiki/5,N,N-TMT" title="5,N,N-TMT">5-Methyl-DMT</a></li> <li><a href="/w/index.php?title=5-Methyltryptamine&action=edit&redlink=1" class="new" title="5-Methyltryptamine (page does not exist)">5-Methyltryptamine</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-(Nonyloxy)tryptamine</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="/wiki/6-MeO-DMT" title="6-MeO-DMT">6-MeO-DMT</a></li> <li><a href="/wiki/7,N,N-TMT" title="7,N,N-TMT">7-Methyl-DMT</a></li> <li><a href="/wiki/Acetryptine" title="Acetryptine">Acetryptine (5-AT)</a></li> <li><a href="/wiki/Aeruginascin" title="Aeruginascin">Aeruginascin (4-PO-TMT)</a></li> <li><a href="/wiki/AGH-107" title="AGH-107">AGH-107</a></li> <li><a href="/wiki/AGH-192" title="AGH-192">AGH-192</a></li> <li><a href="/wiki/AH-494" title="AH-494">AH-494</a></li> <li><a href="/w/index.php?title=ALiPT&action=edit&redlink=1" class="new" title="ALiPT (page does not exist)">ALiPT</a></li> <li><a href="/wiki/Alpertine" title="Alpertine">Alpertine</a></li> <li><a href="/wiki/Baeocystin" title="Baeocystin">Baeocystin (4-PO-NMT)</a></li> <li><a href="/wiki/Benzotript" title="Benzotript">Benzotript (4-chlorobenzoyl-L-tryptophan)</a></li> <li><a href="/wiki/Bufotenidine" title="Bufotenidine">Bufotenidine (5-HTQ)</a></li> <li><a href="/wiki/Bufotenin" title="Bufotenin">Bufotenin (5-HO-DMT)</a></li> <li><a href="/wiki/Convolutindole_A" title="Convolutindole A">Convolutindole A</a></li> <li><a href="/wiki/CP-132,484" title="CP-132,484">CP-132,484</a></li> <li><a href="/wiki/DALT" title="DALT">DALT</a></li> <li><a href="/wiki/Dibutyltryptamine" title="Dibutyltryptamine">DBT</a></li> <li><a href="/wiki/Desformylflustrabromine" title="Desformylflustrabromine">Desformylflustrabromine</a></li> <li><a href="/wiki/Diethyltryptamine" title="Diethyltryptamine">DET</a></li> <li><a href="/wiki/Diisopropyltryptamine" class="mw-redirect" title="Diisopropyltryptamine">DiPT</a></li> <li><a href="/wiki/Dimethyltryptamine" class="mw-redirect" title="Dimethyltryptamine">DMT</a></li> <li><a href="/wiki/Dipropyltryptamine" title="Dipropyltryptamine">DPT</a></li> <li><a href="/wiki/E-6801" title="E-6801">E-6801</a></li> <li><a href="/wiki/E-6837" title="E-6837">E-6837</a></li> <li><a href="/wiki/Ethylisopropyltryptamine" title="Ethylisopropyltryptamine">EiPT</a></li> <li><a href="/wiki/EMDT" title="EMDT">EMDT</a></li> <li><a href="/wiki/Ethylpropyltryptamine" title="Ethylpropyltryptamine">EPT</a></li> <li><a href="/wiki/Ethocybin" title="Ethocybin">Ethocybin (4-PO-DET)</a></li> <li><a href="/wiki/FGIN-127" title="FGIN-127">FGIN-127</a></li> <li><a href="/wiki/FGIN-143" title="FGIN-143">FGIN-143</a></li> <li><a href="/wiki/FT-104" title="FT-104">FT-104</a></li> <li><a href="/wiki/HIOC" title="HIOC">HIOC</a></li> <li><a href="/wiki/Idalopirdine" title="Idalopirdine">Idalopirdine</a></li> <li><a href="/w/index.php?title=Indolylethylfentanyl&action=edit&redlink=1" class="new" title="Indolylethylfentanyl (page does not exist)">Indolylethylfentanyl</a></li> <li><a href="/wiki/Indorenate" title="Indorenate">Indorenate</a></li> <li><a href="/wiki/4-HO-DiPT" title="4-HO-DiPT">Iprocin (4-HO-DiPT)</a></li> <li><a href="/wiki/Lespedamine" title="Lespedamine">Lespedamine</a></li> <li><a href="/wiki/N-Methyl-N-ethyltryptamine" title="N-Methyl-N-ethyltryptamine">MET</a></li> <li><a href="/wiki/Methylbutyltryptamine" title="Methylbutyltryptamine">Methylbutyltryptamine</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/Milipertine" title="Milipertine">Milipertine</a></li> <li><a href="/wiki/MS-245" title="MS-245">MS-245</a></li> <li><a href="/wiki/Methylbutyltryptamine#MSBT" title="Methylbutyltryptamine">MSBT</a></li> <li><a href="/wiki/N-Feruloylserotonin" title="N-Feruloylserotonin">N-Feruloylserotonin (moschamine)</a></li> <li><a href="/wiki/N-Ethyltryptamine" title="N-Ethyltryptamine">NET</a></li> <li><a href="/wiki/N-Methyltryptamine" title="N-Methyltryptamine">NMT</a></li> <li><a href="/wiki/Norbaeocystin" title="Norbaeocystin">Norbaeocystin (4-PO-T)</a></li> <li><a href="/wiki/N-t-Butyltryptamine" title="N-t-Butyltryptamine">NTBT</a></li> <li><a href="/wiki/O-4310" title="O-4310">O-4310</a></li> <li><a href="/wiki/O-Pivalylbufotenine" title="O-Pivalylbufotenine">O-Pivalylbufotenine</a></li> <li><a href="/wiki/Oxypertine" title="Oxypertine">Oxypertine</a></li> <li><a href="/wiki/Propylisopropyltryptamine" title="Propylisopropyltryptamine">PiPT</a></li> <li><a href="/wiki/Psilacetin" class="mw-redirect" title="Psilacetin">Psilacetin (O-acetylpsilocin; 4-AcO-DMT)</a></li> <li><a href="/wiki/Psilocin" title="Psilocin">Psilocin (4-HO-DMT)</a></li> <li><a href="/wiki/Psilocybin" title="Psilocybin">Psilocybin (4-PO-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</a></li> <li><a href="/wiki/Tryptophan" title="Tryptophan">Tryptophan</a></li> <li><a href="/wiki/Yuremamine" title="Yuremamine">Yuremamine</a></li> <li><a href="/w/index.php?title=Z2876442907&action=edit&redlink=1" class="new" title="Z2876442907 (page does not exist)">Z2876442907</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/N-Acetyltryptamine" title="N-Acetyltryptamine">N-Acetyltryptamines</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/2-Iodomelatonin" title="2-Iodomelatonin">2-Iodomelatonin</a></li> <li><a href="/w/index.php?title=2-Phenylmelatonin&action=edit&redlink=1" class="new" title="2-Phenylmelatonin (page does not exist)">2-Phenylmelatonin</a></li> <li><a href="/w/index.php?title=5-Methoxyluzindole&action=edit&redlink=1" class="new" title="5-Methoxyluzindole (page does not exist)">5-Methoxyluzindole</a></li> <li><a href="/w/index.php?title=6-Chloromelatonin&action=edit&redlink=1" class="new" title="6-Chloromelatonin (page does not exist)">6-Chloromelatonin</a></li> <li><a href="/w/index.php?title=6-Fluoromelatonin&action=edit&redlink=1" class="new" title="6-Fluoromelatonin (page does not exist)">6-Fluoromelatonin</a></li> <li><a href="/wiki/6-Hydroxymelatonin" title="6-Hydroxymelatonin">6-Hydroxymelatonin</a></li> <li><a href="/w/index.php?title=6-Methoxymelatonin&action=edit&redlink=1" class="new" title="6-Methoxymelatonin (page does not exist)">6-Methoxymelatonin</a></li> <li><a href="/w/index.php?title=6,7-Dichloro-2-methylmelatonin&action=edit&redlink=1" class="new" title="6,7-Dichloro-2-methylmelatonin (page does not exist)">6,7-Dichloro-2-methylmelatonin</a></li> <li><a href="/wiki/%CE%91-Methylmelatonin" title="Α-Methylmelatonin">α-Methylmelatonin</a></li> <li><a href="/wiki/Luzindole" title="Luzindole">Luzindole</a></li> <li><a href="/wiki/Melatonin" title="Melatonin">Melatonin</a></li> <li><a href="/wiki/N-Acetylserotonin" title="N-Acetylserotonin">Normelatonin (N-acetylserotonin; NAS)</a></li> <li><a href="/wiki/N-Acetyltryptamine" title="N-Acetyltryptamine">N-Acetyltryptamine</a></li> <li><a href="/w/index.php?title=N-Butanoylmelatonin&action=edit&redlink=1" class="new" title="N-Butanoylmelatonin (page does not exist)">N-Butanoylmelatonin</a></li> <li><a href="/w/index.php?title=N-Propionylmelatonin&action=edit&redlink=1" class="new" title="N-Propionylmelatonin (page does not exist)">N-Propionylmelatonin</a></li> <li><a href="/wiki/Piromelatine" title="Piromelatine">Piromelatine</a></li> <li><a href="/wiki/TIK-301" title="TIK-301">TIK-301</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/%CE%91-Alkyltryptamine" class="mw-redirect" title="Α-Alkyltryptamine">α-Alkyltryptamines</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/2,%CE%B1-Dimethyltryptamine" title="2,α-Dimethyltryptamine">2,α-DMT</a></li> <li><a href="/wiki/4-HO-%CE%B1MT" title="4-HO-αMT">4-HO-αMT</a></li> <li><a href="/wiki/4-HO-MPMI" title="4-HO-MPMI">4-HO-MPMI (lucigenol)</a></li> <li><a href="/wiki/4-Methyl-%CE%B1-ethyltryptamine" title="4-Methyl-α-ethyltryptamine">4-Me-αET</a></li> <li><a href="/wiki/4-Me-%CE%B1MT" class="mw-redirect" title="4-Me-αMT">4-Me-αMT</a></li> <li><a href="/wiki/5-Chloro-%CE%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="/w/index.php?title=5-MeO-%CE%B1,N,N-TMT&action=edit&redlink=1" class="new" title="5-MeO-α,N,N-TMT (page does not exist)">5-MeO-α,N,N-TMT</a></li> <li><a href="/wiki/5-MeO-AET" title="5-MeO-AET">5-MeO-αET </a></li> <li><a href="/wiki/5-MeO-aMT" title="5-MeO-aMT">5-MeO-αMT</a></li> <li><a href="/wiki/5-MeO-MPMI" title="5-MeO-MPMI">5-MeO-MPMI</a></li> <li><a href="/w/index.php?title=5-Methyl-AET&action=edit&redlink=1" class="new" title="5-Methyl-AET (page does not exist)">5-Methyl-αET</a></li> <li><a href="/wiki/6-Fluoro-AMT" title="6-Fluoro-AMT">6-Fluoro-αMT</a></li> <li><a href="/wiki/7-Chloro-AMT" title="7-Chloro-AMT">7-Chloro-αMT</a></li> <li><a href="/wiki/7-Methyl-%CE%B1-ethyltryptamine" title="7-Methyl-α-ethyltryptamine">7-Methyl-αET</a></li> <li><a href="/wiki/%CE%91-Methyl-5-hydroxytryptophan" title="Α-Methyl-5-hydroxytryptophan">α-Methyl-5-HTP</a></li> <li><a href="/wiki/%CE%91-Methylmelatonin" title="Α-Methylmelatonin">α-Methylmelatonin</a></li> <li><a href="/wiki/%CE%91-Methylserotonin" title="Α-Methylserotonin">α-Methylserotonin (5-HO-αMT)</a></li> <li><a href="/wiki/%CE%91-Methyltryptophan" title="Α-Methyltryptophan">α-Methyltryptophan (αMTP)</a></li> <li><a href="/wiki/Alpha,N-DMT" class="mw-redirect" title="Alpha,N-DMT">α,N-DMT (N-methyl-αMT)</a></li> <li><a href="/wiki/%CE%91,N,N-Trimethyltryptamine" title="Α,N,N-Trimethyltryptamine">α,N,N-TMT</a></li> <li><a href="/wiki/Alpha,N,O-TMS" class="mw-redirect" title="Alpha,N,O-TMS">α,N,O-TMS</a></li> <li><a href="/wiki/%CE%91-Ethyltryptamine" title="Α-Ethyltryptamine">αET (etryptamine)</a></li> <li><a href="/wiki/%CE%91-Methyltryptamine" title="Α-Methyltryptamine">αMT</a></li> <li><a href="/wiki/AL-37350A" title="AL-37350A">AL-37350A (4,5-DHP-αMT)</a></li> <li><a href="/wiki/BNC-210" title="BNC-210">BNC-210</a></li> <li><a href="/wiki/BW-723C86" title="BW-723C86">BW-723C86</a></li> <li><a href="/wiki/CP-135807" title="CP-135807">CP-135807</a></li> <li><a href="/wiki/Indolylpropylaminopentane" title="Indolylpropylaminopentane">IPAP (α,N-DPT)</a></li> <li><a href="/wiki/MPMI_(drug)" title="MPMI (drug)">MPMI</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Triptan" title="Triptan">Triptans</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Almotriptan" title="Almotriptan">Almotriptan</a></li> <li><a href="/wiki/Donitriptan" title="Donitriptan">Donitriptan</a></li> <li><a href="/wiki/Eletriptan" title="Eletriptan">Eletriptan</a></li> <li><a href="/wiki/Frovatriptan" title="Frovatriptan">Frovatriptan</a></li> <li><a href="/wiki/L-694247" title="L-694247">L-694247</a></li> <li><a href="/wiki/Rizatriptan" title="Rizatriptan">Rizatriptan</a></li> <li><a href="/wiki/Sumatriptan" title="Sumatriptan">Sumatriptan</a></li> <li><a href="/wiki/Zolmitriptan" title="Zolmitriptan">Zolmitriptan</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Cyclic_compound" title="Cyclic compound">Cyclized tryptamines</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Bay_R_1531" title="Bay R 1531">Bay R 1531</a></li> <li><a href="/wiki/Ciclindole" title="Ciclindole">Ciclindole</a></li> <li><a href="/wiki/Cyclic_3-hydroxymelatonin" title="Cyclic 3-hydroxymelatonin">Cyclic 3-OHM</a></li> <li><a href="/wiki/Ergoline" title="Ergoline">Ergolines</a> and <a href="/wiki/Lysergamide" class="mw-redirect" title="Lysergamide">lysergamides</a> (e.g., <a href="/wiki/Lysergic_acid_diethylamide" class="mw-redirect" title="Lysergic acid diethylamide">LSD</a>)</li> <li><a href="/wiki/Flucindole" title="Flucindole">Flucindole</a></li> <li><a href="/wiki/Harmala_alkaloid" title="Harmala alkaloid">Harmala alkaloids</a> and <a href="/wiki/%CE%92-carboline" class="mw-redirect" title="Β-carboline">β-carbolines</a> (e.g., <a href="/wiki/6-MeO-THH" title="6-MeO-THH">6-MeO-THH</a>, <a href="/wiki/9-Methyl-%CE%B2-carboline" title="9-Methyl-β-carboline">9-Me-BC</a>, <a href="/wiki/%CE%92-carboline" class="mw-redirect" title="Β-carboline">β-carboline (norharman)</a>, <a href="/wiki/Harmaline" title="Harmaline">harmaline</a>, <a href="/wiki/Harmalol" title="Harmalol">harmalol</a>, <a href="/wiki/Harmane" title="Harmane">harmane</a>, <a href="/wiki/Harmine" title="Harmine">harmine</a>, <a href="/wiki/Pinoline" title="Pinoline">pinoline</a>, <a href="/wiki/Tetrahydroharmine" title="Tetrahydroharmine">tetrahydroharmine</a>, <a href="/wiki/Tryptoline" title="Tryptoline">tryptoline</a>)</li> <li><a href="/wiki/Iboga-type_alkaloid" title="Iboga-type alkaloid">Iboga alkaloids</a> and related (e.g., <a href="/wiki/DM-506" title="DM-506">DM-506 (ibogaminalog)</a>, <a href="/wiki/Ibogaine" title="Ibogaine">ibogaine</a>, <a href="/wiki/Ibogamine" title="Ibogamine">ibogamine</a>, <a href="/wiki/Noribogaine" title="Noribogaine">noribogaine</a>, <a href="/wiki/Tabernanthalog" title="Tabernanthalog">tabernanthalog</a>, <a href="/wiki/Tabernanthine" title="Tabernanthine">tabernanthine</a>)</li> <li><a href="/wiki/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;">Related compounds</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="/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" 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/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/Pirlindole" title="Pirlindole">Pirlindole</a></li> <li><a href="/wiki/(R)-69" title="(R)-69">(R)-69 (3IQ)</a></li> <li><a href="/wiki/Ro60-0175" title="Ro60-0175">Ro60-0175</a></li> <li><a href="/wiki/Ro60-0213" title="Ro60-0213">Ro60-0213</a></li> <li><a href="/wiki/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/Substituted_benzofuran" title="Substituted benzofuran">Substituted benzofurans</a> (e.g., <a href="/w/index.php?title=3-(2-aminopropyl)benzofuran&action=edit&redlink=1" class="new" title="3-(2-aminopropyl)benzofuran (page does not exist)">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="/w/index.php?title=Mebfap&action=edit&redlink=1" class="new" title="Mebfap (page does not exist)">mebfap</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/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/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> <style data-mw-deduplicate="TemplateStyles:r1130092004">.mw-parser-output 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