CINXE.COM

<!DOCTYPE html> <html class="client-nojs vector-feature-language-in-header-enabled vector-feature-language-in-main-page-header-disabled vector-feature-sticky-header-disabled vector-feature-page-tools-pinned-disabled vector-feature-toc-pinned-clientpref-1 vector-feature-main-menu-pinned-disabled vector-feature-limited-width-clientpref-1 vector-feature-limited-width-content-enabled vector-feature-custom-font-size-clientpref-1 vector-feature-appearance-pinned-clientpref-1 vector-feature-night-mode-enabled skin-theme-clientpref-day vector-toc-available" lang="en" dir="ltr"> <head> <meta charset="UTF-8"> <title>Tryptophan - Wikipedia</title> <script>(function(){var className="client-js vector-feature-language-in-header-enabled vector-feature-language-in-main-page-header-disabled vector-feature-sticky-header-disabled vector-feature-page-tools-pinned-disabled vector-feature-toc-pinned-clientpref-1 vector-feature-main-menu-pinned-disabled vector-feature-limited-width-clientpref-1 vector-feature-limited-width-content-enabled vector-feature-custom-font-size-clientpref-1 vector-feature-appearance-pinned-clientpref-1 vector-feature-night-mode-enabled skin-theme-clientpref-day vector-toc-available";var cookie=document.cookie.match(/(?:^|; )enwikimwclientpreferences=([^;]+)/);if(cookie){cookie[1].split('%2C').forEach(function(pref){className=className.replace(new RegExp('(^| )'+pref.replace(/-clientpref-\w+$|[^\w-]+/g,'')+'-clientpref-\\w+( |$)'),'$1'+pref+'$2');});}document.documentElement.className=className;}());RLCONF={"wgBreakFrames":false,"wgSeparatorTransformTable":["",""],"wgDigitTransformTable":["",""],"wgDefaultDateFormat":"dmy", "wgMonthNames":["","January","February","March","April","May","June","July","August","September","October","November","December"],"wgRequestId":"765fa4c1-1eb6-4bd7-bfd6-45018cb8127c","wgCanonicalNamespace":"","wgCanonicalSpecialPageName":false,"wgNamespaceNumber":0,"wgPageName":"Tryptophan","wgTitle":"Tryptophan","wgCurRevisionId":1249994738,"wgRevisionId":1249994738,"wgArticleId":58358,"wgIsArticle":true,"wgIsRedirect":false,"wgAction":"view","wgUserName":null,"wgUserGroups":["*"],"wgCategories":["All articles with dead external links","Articles with dead external links from July 2021","Use dmy dates from September 2020","Chemical articles with multiple compound IDs","Multiple chemicals in an infobox that need indexing","Articles without InChI source","ECHA InfoCard ID from Wikidata","Chemical articles having a data page","Articles containing unverified chemical infoboxes","Chembox image size set","Articles with short description","Short description matches Wikidata", "Alpha-Amino acids","Proteinogenic amino acids","Indole alkaloids","Glucogenic amino acids","Ketogenic amino acids","Aromatic amino acids","Essential amino acids","Tryptamine alkaloids","Dietary supplements","Carbonic anhydrase activators","Monoamine precursors","Serotonin"],"wgPageViewLanguage":"en","wgPageContentLanguage":"en","wgPageContentModel":"wikitext","wgRelevantPageName":"Tryptophan","wgRelevantArticleId":58358,"wgIsProbablyEditable":true,"wgRelevantPageIsProbablyEditable":true,"wgRestrictionEdit":[],"wgRestrictionMove":[],"wgNoticeProject":"wikipedia","wgCiteReferencePreviewsActive":false,"wgFlaggedRevsParams":{"tags":{"status":{"levels":1}}},"wgMediaViewerOnClick":true,"wgMediaViewerEnabledByDefault":true,"wgPopupsFlags":0,"wgVisualEditor":{"pageLanguageCode":"en","pageLanguageDir":"ltr","pageVariantFallbacks":"en"},"wgMFDisplayWikibaseDescriptions":{"search":true,"watchlist":true,"tagline":false,"nearby":true},"wgWMESchemaEditAttemptStepOversample":false,"wgWMEPageLength": 50000,"wgRelatedArticlesCompat":[],"wgCentralAuthMobileDomain":false,"wgEditSubmitButtonLabelPublish":true,"wgULSPosition":"interlanguage","wgULSisCompactLinksEnabled":false,"wgVector2022LanguageInHeader":true,"wgULSisLanguageSelectorEmpty":false,"wgWikibaseItemId":"Q181003","wgCheckUserClientHintsHeadersJsApi":["brands","architecture","bitness","fullVersionList","mobile","model","platform","platformVersion"],"GEHomepageSuggestedEditsEnableTopics":true,"wgGETopicsMatchModeEnabled":false,"wgGEStructuredTaskRejectionReasonTextInputEnabled":false,"wgGELevelingUpEnabledForUser":false};RLSTATE={"ext.globalCssJs.user.styles":"ready","site.styles":"ready","user.styles":"ready","ext.globalCssJs.user":"ready","user":"ready","user.options":"loading","ext.cite.styles":"ready","skins.vector.search.codex.styles":"ready","skins.vector.styles":"ready","skins.vector.icons":"ready","jquery.tablesorter.styles":"ready","jquery.makeCollapsible.styles":"ready","ext.wikimediamessages.styles":"ready", "ext.visualEditor.desktopArticleTarget.noscript":"ready","ext.uls.interlanguage":"ready","wikibase.client.init":"ready","ext.wikimediaBadges":"ready"};RLPAGEMODULES=["ext.cite.ux-enhancements","mediawiki.page.media","site","mediawiki.page.ready","jquery.tablesorter","jquery.makeCollapsible","mediawiki.toc","skins.vector.js","ext.centralNotice.geoIP","ext.centralNotice.startUp","ext.gadget.ReferenceTooltips","ext.gadget.switcher","ext.urlShortener.toolbar","ext.centralauth.centralautologin","mmv.bootstrap","ext.popups","ext.visualEditor.desktopArticleTarget.init","ext.visualEditor.targetLoader","ext.echo.centralauth","ext.eventLogging","ext.wikimediaEvents","ext.navigationTiming","ext.uls.interface","ext.cx.eventlogging.campaigns","ext.cx.uls.quick.actions","wikibase.client.vector-2022","ext.checkUser.clientHints","ext.growthExperiments.SuggestedEditSession","wikibase.sidebar.tracking"];</script> <script>(RLQ=window.RLQ||[]).push(function(){mw.loader.impl(function(){return["user.options@12s5i",function($,jQuery,require,module){mw.user.tokens.set({"patrolToken":"+\\","watchToken":"+\\","csrfToken":"+\\"}); }];});});</script> <link rel="stylesheet" href="/w/load.php?lang=en&modules=ext.cite.styles%7Cext.uls.interlanguage%7Cext.visualEditor.desktopArticleTarget.noscript%7Cext.wikimediaBadges%7Cext.wikimediamessages.styles%7Cjquery.makeCollapsible.styles%7Cjquery.tablesorter.styles%7Cskins.vector.icons%2Cstyles%7Cskins.vector.search.codex.styles%7Cwikibase.client.init&only=styles&skin=vector-2022"> <script async="" src="/w/load.php?lang=en&modules=startup&only=scripts&raw=1&skin=vector-2022"></script> <meta name="ResourceLoaderDynamicStyles" content=""> <link rel="stylesheet" href="/w/load.php?lang=en&modules=site.styles&only=styles&skin=vector-2022"> <meta name="generator" content="MediaWiki 1.44.0-wmf.4"> <meta name="referrer" content="origin"> <meta name="referrer" content="origin-when-cross-origin"> <meta name="robots" content="max-image-preview:standard"> <meta name="format-detection" content="telephone=no"> <meta property="og:image" content="https://upload.wikimedia.org/wikipedia/commons/thumb/0/0c/Tryptophan-from-xtal-3D-sf.png/1200px-Tryptophan-from-xtal-3D-sf.png"> <meta property="og:image:width" content="1200"> <meta property="og:image:height" content="1757"> <meta property="og:image" content="https://upload.wikimedia.org/wikipedia/commons/thumb/0/0c/Tryptophan-from-xtal-3D-sf.png/800px-Tryptophan-from-xtal-3D-sf.png"> <meta property="og:image:width" content="800"> <meta property="og:image:height" content="1171"> <meta property="og:image" content="https://upload.wikimedia.org/wikipedia/commons/thumb/0/0c/Tryptophan-from-xtal-3D-sf.png/640px-Tryptophan-from-xtal-3D-sf.png"> <meta property="og:image:width" content="640"> <meta property="og:image:height" content="937"> <meta name="viewport" content="width=1120"> <meta property="og:title" content="Tryptophan - Wikipedia"> <meta property="og:type" content="website"> <link rel="preconnect" href="//upload.wikimedia.org"> <link rel="alternate" media="only screen and (max-width: 640px)" href="//en.m.wikipedia.org/wiki/Tryptophan"> <link rel="alternate" type="application/x-wiki" title="Edit this page" href="/w/index.php?title=Tryptophan&action=edit"> <link rel="apple-touch-icon" href="/static/apple-touch/wikipedia.png"> <link rel="icon" href="/static/favicon/wikipedia.ico"> <link rel="search" type="application/opensearchdescription+xml" href="/w/rest.php/v1/search" title="Wikipedia (en)"> <link rel="EditURI" type="application/rsd+xml" href="//en.wikipedia.org/w/api.php?action=rsd"> <link rel="canonical" href="https://en.wikipedia.org/wiki/Tryptophan"> <link rel="license" href="https://creativecommons.org/licenses/by-sa/4.0/deed.en"> <link rel="alternate" type="application/atom+xml" title="Wikipedia Atom feed" href="/w/index.php?title=Special:RecentChanges&feed=atom"> <link rel="dns-prefetch" href="//meta.wikimedia.org" /> <link rel="dns-prefetch" href="//login.wikimedia.org"> </head> <body class="skin--responsive skin-vector skin-vector-search-vue mediawiki ltr sitedir-ltr mw-hide-empty-elt ns-0 ns-subject mw-editable page-Tryptophan rootpage-Tryptophan skin-vector-2022 action-view"><a class="mw-jump-link" href="#bodyContent">Jump to content</a> <div class="vector-header-container"> <header class="vector-header mw-header"> <div class="vector-header-start"> <nav class="vector-main-menu-landmark" aria-label="Site"> <div id="vector-main-menu-dropdown" class="vector-dropdown vector-main-menu-dropdown vector-button-flush-left vector-button-flush-right" > <input type="checkbox" id="vector-main-menu-dropdown-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-vector-main-menu-dropdown" class="vector-dropdown-checkbox " aria-label="Main menu" > <label id="vector-main-menu-dropdown-label" for="vector-main-menu-dropdown-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--icon-only " aria-hidden="true" ><span class="vector-icon mw-ui-icon-menu mw-ui-icon-wikimedia-menu"></span> <span class="vector-dropdown-label-text">Main menu</span> </label> <div class="vector-dropdown-content"> <div id="vector-main-menu-unpinned-container" class="vector-unpinned-container"> <div id="vector-main-menu" class="vector-main-menu vector-pinnable-element"> <div class="vector-pinnable-header vector-main-menu-pinnable-header vector-pinnable-header-unpinned" data-feature-name="main-menu-pinned" data-pinnable-element-id="vector-main-menu" data-pinned-container-id="vector-main-menu-pinned-container" data-unpinned-container-id="vector-main-menu-unpinned-container" > <div class="vector-pinnable-header-label">Main menu</div> <button class="vector-pinnable-header-toggle-button vector-pinnable-header-pin-button" data-event-name="pinnable-header.vector-main-menu.pin">move to sidebar</button> <button class="vector-pinnable-header-toggle-button vector-pinnable-header-unpin-button" data-event-name="pinnable-header.vector-main-menu.unpin">hide</button> </div> <div id="p-navigation" class="vector-menu mw-portlet mw-portlet-navigation" > <div class="vector-menu-heading"> Navigation </div> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li id="n-mainpage-description" class="mw-list-item"><a href="/wiki/Main_Page" title="Visit the main page [z]" accesskey="z"><span>Main page</span></a></li><li id="n-contents" class="mw-list-item"><a href="/wiki/Wikipedia:Contents" title="Guides to browsing Wikipedia"><span>Contents</span></a></li><li id="n-currentevents" class="mw-list-item"><a href="/wiki/Portal:Current_events" title="Articles related to current events"><span>Current events</span></a></li><li id="n-randompage" class="mw-list-item"><a href="/wiki/Special:Random" title="Visit a randomly selected article [x]" accesskey="x"><span>Random article</span></a></li><li id="n-aboutsite" class="mw-list-item"><a href="/wiki/Wikipedia:About" title="Learn about Wikipedia and how it works"><span>About Wikipedia</span></a></li><li id="n-contactpage" class="mw-list-item"><a href="//en.wikipedia.org/wiki/Wikipedia:Contact_us" title="How to contact Wikipedia"><span>Contact us</span></a></li> </ul> </div> </div> <div id="p-interaction" class="vector-menu mw-portlet mw-portlet-interaction" > <div class="vector-menu-heading"> Contribute </div> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li id="n-help" class="mw-list-item"><a href="/wiki/Help:Contents" title="Guidance on how to use and edit Wikipedia"><span>Help</span></a></li><li id="n-introduction" class="mw-list-item"><a href="/wiki/Help:Introduction" title="Learn how to edit Wikipedia"><span>Learn to edit</span></a></li><li id="n-portal" class="mw-list-item"><a href="/wiki/Wikipedia:Community_portal" title="The hub for editors"><span>Community portal</span></a></li><li id="n-recentchanges" class="mw-list-item"><a href="/wiki/Special:RecentChanges" title="A list of recent changes to Wikipedia [r]" accesskey="r"><span>Recent changes</span></a></li><li id="n-upload" class="mw-list-item"><a href="/wiki/Wikipedia:File_upload_wizard" title="Add images or other media for use on Wikipedia"><span>Upload file</span></a></li> </ul> </div> </div> </div> </div> </div> </div> </nav> <a href="/wiki/Main_Page" class="mw-logo"> <img class="mw-logo-icon" src="/static/images/icons/wikipedia.png" alt="" aria-hidden="true" height="50" width="50"> <span class="mw-logo-container skin-invert"> <img class="mw-logo-wordmark" alt="Wikipedia" src="/static/images/mobile/copyright/wikipedia-wordmark-en.svg" style="width: 7.5em; height: 1.125em;"> <img class="mw-logo-tagline" alt="The Free Encyclopedia" src="/static/images/mobile/copyright/wikipedia-tagline-en.svg" width="117" height="13" style="width: 7.3125em; height: 0.8125em;"> </span> </a> </div> <div class="vector-header-end"> <div id="p-search" role="search" class="vector-search-box-vue vector-search-box-collapses vector-search-box-show-thumbnail vector-search-box-auto-expand-width vector-search-box"> <a href="/wiki/Special:Search" class="cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--icon-only search-toggle" title="Search Wikipedia [f]" accesskey="f"><span class="vector-icon mw-ui-icon-search mw-ui-icon-wikimedia-search"></span> <span>Search</span> </a> <div class="vector-typeahead-search-container"> <div class="cdx-typeahead-search cdx-typeahead-search--show-thumbnail cdx-typeahead-search--auto-expand-width"> <form action="/w/index.php" id="searchform" class="cdx-search-input cdx-search-input--has-end-button"> <div id="simpleSearch" class="cdx-search-input__input-wrapper" data-search-loc="header-moved"> <div class="cdx-text-input cdx-text-input--has-start-icon"> <input class="cdx-text-input__input" type="search" name="search" placeholder="Search Wikipedia" aria-label="Search Wikipedia" autocapitalize="sentences" title="Search Wikipedia [f]" accesskey="f" id="searchInput" > <span class="cdx-text-input__icon cdx-text-input__start-icon"></span> </div> <input type="hidden" name="title" value="Special:Search"> </div> <button class="cdx-button cdx-search-input__end-button">Search</button> </form> </div> </div> </div> <nav class="vector-user-links vector-user-links-wide" aria-label="Personal tools"> <div class="vector-user-links-main"> <div id="p-vector-user-menu-preferences" class="vector-menu mw-portlet emptyPortlet" > <div class="vector-menu-content"> <ul class="vector-menu-content-list"> </ul> </div> </div> <div id="p-vector-user-menu-userpage" class="vector-menu mw-portlet emptyPortlet" > <div class="vector-menu-content"> <ul class="vector-menu-content-list"> </ul> </div> </div> <nav class="vector-appearance-landmark" aria-label="Appearance"> <div id="vector-appearance-dropdown" class="vector-dropdown " title="Change the appearance of the page's font size, width, and color" > <input type="checkbox" id="vector-appearance-dropdown-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-vector-appearance-dropdown" class="vector-dropdown-checkbox " aria-label="Appearance" > <label id="vector-appearance-dropdown-label" for="vector-appearance-dropdown-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--icon-only " aria-hidden="true" ><span class="vector-icon mw-ui-icon-appearance mw-ui-icon-wikimedia-appearance"></span> <span class="vector-dropdown-label-text">Appearance</span> </label> <div class="vector-dropdown-content"> <div id="vector-appearance-unpinned-container" class="vector-unpinned-container"> </div> </div> </div> </nav> <div id="p-vector-user-menu-notifications" class="vector-menu mw-portlet emptyPortlet" > <div class="vector-menu-content"> <ul class="vector-menu-content-list"> </ul> </div> </div> <div id="p-vector-user-menu-overflow" class="vector-menu mw-portlet" > <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li id="pt-sitesupport-2" class="user-links-collapsible-item mw-list-item user-links-collapsible-item"><a data-mw="interface" href="https://donate.wikimedia.org/wiki/Special:FundraiserRedirector?utm_source=donate&utm_medium=sidebar&utm_campaign=C13_en.wikipedia.org&uselang=en" class=""><span>Donate</span></a> </li> <li id="pt-createaccount-2" class="user-links-collapsible-item mw-list-item user-links-collapsible-item"><a data-mw="interface" href="/w/index.php?title=Special:CreateAccount&returnto=Tryptophan" title="You are encouraged to create an account and log in; however, it is not mandatory" class=""><span>Create account</span></a> </li> <li id="pt-login-2" class="user-links-collapsible-item mw-list-item user-links-collapsible-item"><a data-mw="interface" href="/w/index.php?title=Special:UserLogin&returnto=Tryptophan" title="You're encouraged to log in; however, it's not mandatory. [o]" accesskey="o" class=""><span>Log in</span></a> </li> </ul> </div> </div> </div> <div id="vector-user-links-dropdown" class="vector-dropdown vector-user-menu vector-button-flush-right vector-user-menu-logged-out" title="Log in and more options" > <input type="checkbox" id="vector-user-links-dropdown-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-vector-user-links-dropdown" class="vector-dropdown-checkbox " aria-label="Personal tools" > <label id="vector-user-links-dropdown-label" for="vector-user-links-dropdown-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--icon-only " aria-hidden="true" ><span class="vector-icon mw-ui-icon-ellipsis mw-ui-icon-wikimedia-ellipsis"></span> <span class="vector-dropdown-label-text">Personal tools</span> </label> <div class="vector-dropdown-content"> <div id="p-personal" class="vector-menu mw-portlet mw-portlet-personal user-links-collapsible-item" title="User menu" > <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li id="pt-sitesupport" class="user-links-collapsible-item mw-list-item"><a href="https://donate.wikimedia.org/wiki/Special:FundraiserRedirector?utm_source=donate&utm_medium=sidebar&utm_campaign=C13_en.wikipedia.org&uselang=en"><span>Donate</span></a></li><li id="pt-createaccount" class="user-links-collapsible-item mw-list-item"><a href="/w/index.php?title=Special:CreateAccount&returnto=Tryptophan" title="You are encouraged to create an account and log in; however, it is not mandatory"><span class="vector-icon mw-ui-icon-userAdd mw-ui-icon-wikimedia-userAdd"></span> <span>Create account</span></a></li><li id="pt-login" class="user-links-collapsible-item mw-list-item"><a href="/w/index.php?title=Special:UserLogin&returnto=Tryptophan" title="You're encouraged to log in; however, it's not mandatory. [o]" accesskey="o"><span class="vector-icon mw-ui-icon-logIn mw-ui-icon-wikimedia-logIn"></span> <span>Log in</span></a></li> </ul> </div> </div> <div id="p-user-menu-anon-editor" class="vector-menu mw-portlet mw-portlet-user-menu-anon-editor" > <div class="vector-menu-heading"> Pages for logged out editors <a href="/wiki/Help:Introduction" aria-label="Learn more about editing"><span>learn more</span></a> </div> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li id="pt-anoncontribs" class="mw-list-item"><a href="/wiki/Special:MyContributions" title="A list of edits made from this IP address [y]" accesskey="y"><span>Contributions</span></a></li><li id="pt-anontalk" class="mw-list-item"><a href="/wiki/Special:MyTalk" title="Discussion about edits from this IP address [n]" accesskey="n"><span>Talk</span></a></li> </ul> </div> </div> </div> </div> </nav> </div> </header> </div> <div class="mw-page-container"> <div class="mw-page-container-inner"> <div class="vector-sitenotice-container"> <div id="siteNotice"></div> </div> <div class="vector-column-start"> <div class="vector-main-menu-container"> <div id="mw-navigation"> <nav id="mw-panel" class="vector-main-menu-landmark" aria-label="Site"> <div id="vector-main-menu-pinned-container" class="vector-pinned-container"> </div> </nav> </div> </div> <div class="vector-sticky-pinned-container"> <nav id="mw-panel-toc" aria-label="Contents" data-event-name="ui.sidebar-toc" class="mw-table-of-contents-container vector-toc-landmark"> <div id="vector-toc-pinned-container" class="vector-pinned-container"> <div id="vector-toc" class="vector-toc vector-pinnable-element"> <div class="vector-pinnable-header vector-toc-pinnable-header vector-pinnable-header-pinned" data-feature-name="toc-pinned" data-pinnable-element-id="vector-toc" > <h2 class="vector-pinnable-header-label">Contents</h2> <button class="vector-pinnable-header-toggle-button vector-pinnable-header-pin-button" data-event-name="pinnable-header.vector-toc.pin">move to sidebar</button> <button class="vector-pinnable-header-toggle-button vector-pinnable-header-unpin-button" data-event-name="pinnable-header.vector-toc.unpin">hide</button> </div> <ul class="vector-toc-contents" id="mw-panel-toc-list"> <li id="toc-mw-content-text" class="vector-toc-list-item vector-toc-level-1"> <a href="#" class="vector-toc-link"> <div class="vector-toc-text">(Top)</div> </a> </li> <li id="toc-Function" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Function"> <div class="vector-toc-text"> <span class="vector-toc-numb">1</span> <span>Function</span> </div> </a> <ul id="toc-Function-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Recommended_dietary_allowance" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Recommended_dietary_allowance"> <div class="vector-toc-text"> <span class="vector-toc-numb">2</span> <span>Recommended dietary allowance</span> </div> </a> <button aria-controls="toc-Recommended_dietary_allowance-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> <span class="vector-icon mw-ui-icon-wikimedia-expand"></span> <span>Toggle Recommended dietary allowance subsection</span> </button> <ul id="toc-Recommended_dietary_allowance-sublist" class="vector-toc-list"> <li id="toc-Dietary_sources" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Dietary_sources"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.1</span> <span>Dietary sources</span> </div> </a> <ul id="toc-Dietary_sources-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Medical_use" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Medical_use"> <div class="vector-toc-text"> <span class="vector-toc-numb">3</span> <span>Medical use</span> </div> </a> <button aria-controls="toc-Medical_use-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> <span class="vector-icon mw-ui-icon-wikimedia-expand"></span> <span>Toggle Medical use subsection</span> </button> <ul id="toc-Medical_use-sublist" class="vector-toc-list"> <li id="toc-Depression" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Depression"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.1</span> <span>Depression</span> </div> </a> <ul id="toc-Depression-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Insomnia" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Insomnia"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.2</span> <span>Insomnia</span> </div> </a> <ul id="toc-Insomnia-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Side_effects" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Side_effects"> <div class="vector-toc-text"> <span class="vector-toc-numb">4</span> <span>Side effects</span> </div> </a> <ul id="toc-Side_effects-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Interactions" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Interactions"> <div class="vector-toc-text"> <span class="vector-toc-numb">5</span> <span>Interactions</span> </div> </a> <ul id="toc-Interactions-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Isolation" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Isolation"> <div class="vector-toc-text"> <span class="vector-toc-numb">6</span> <span>Isolation</span> </div> </a> <ul id="toc-Isolation-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Biosynthesis_and_industrial_production" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Biosynthesis_and_industrial_production"> <div class="vector-toc-text"> <span class="vector-toc-numb">7</span> <span>Biosynthesis and industrial production</span> </div> </a> <ul id="toc-Biosynthesis_and_industrial_production-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Society_and_culture" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Society_and_culture"> <div class="vector-toc-text"> <span class="vector-toc-numb">8</span> <span>Society and culture</span> </div> </a> <button aria-controls="toc-Society_and_culture-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> <span class="vector-icon mw-ui-icon-wikimedia-expand"></span> <span>Toggle Society and culture subsection</span> </button> <ul id="toc-Society_and_culture-sublist" class="vector-toc-list"> <li id="toc-Showa_Denko_contamination_scandal" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Showa_Denko_contamination_scandal"> <div class="vector-toc-text"> <span class="vector-toc-numb">8.1</span> <span>Showa Denko contamination scandal</span> </div> </a> <ul id="toc-Showa_Denko_contamination_scandal-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Turkey_meat_and_drowsiness_hypothesis" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Turkey_meat_and_drowsiness_hypothesis"> <div class="vector-toc-text"> <span class="vector-toc-numb">8.2</span> <span>Turkey meat and drowsiness hypothesis</span> </div> </a> <ul id="toc-Turkey_meat_and_drowsiness_hypothesis-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Research" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Research"> <div class="vector-toc-text"> <span class="vector-toc-numb">9</span> <span>Research</span> </div> </a> <button aria-controls="toc-Research-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> <span class="vector-icon mw-ui-icon-wikimedia-expand"></span> <span>Toggle Research subsection</span> </button> <ul id="toc-Research-sublist" class="vector-toc-list"> <li id="toc-Yeast_amino_acid_metabolism" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Yeast_amino_acid_metabolism"> <div class="vector-toc-text"> <span class="vector-toc-numb">9.1</span> <span>Yeast amino acid metabolism</span> </div> </a> <ul id="toc-Yeast_amino_acid_metabolism-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Serotonin_precursor" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Serotonin_precursor"> <div class="vector-toc-text"> <span class="vector-toc-numb">9.2</span> <span>Serotonin precursor</span> </div> </a> <ul id="toc-Serotonin_precursor-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Psychedelic_effects" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Psychedelic_effects"> <div class="vector-toc-text"> <span class="vector-toc-numb">9.3</span> <span>Psychedelic effects</span> </div> </a> <ul id="toc-Psychedelic_effects-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Fluorescence" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Fluorescence"> <div class="vector-toc-text"> <span class="vector-toc-numb">9.4</span> <span>Fluorescence</span> </div> </a> <ul id="toc-Fluorescence-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-See_also" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#See_also"> <div class="vector-toc-text"> <span class="vector-toc-numb">10</span> <span>See also</span> </div> </a> <ul id="toc-See_also-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-References" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#References"> <div class="vector-toc-text"> <span class="vector-toc-numb">11</span> <span>References</span> </div> </a> <ul id="toc-References-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Further_reading" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Further_reading"> <div class="vector-toc-text"> <span class="vector-toc-numb">12</span> <span>Further reading</span> </div> </a> <ul id="toc-Further_reading-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-External_links" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#External_links"> <div class="vector-toc-text"> <span class="vector-toc-numb">13</span> <span>External links</span> </div> </a> <ul id="toc-External_links-sublist" class="vector-toc-list"> </ul> </li> </ul> </div> </div> </nav> </div> </div> <div class="mw-content-container"> <main id="content" class="mw-body"> <header class="mw-body-header vector-page-titlebar"> <nav aria-label="Contents" class="vector-toc-landmark"> <div id="vector-page-titlebar-toc" class="vector-dropdown vector-page-titlebar-toc vector-button-flush-left" > <input type="checkbox" id="vector-page-titlebar-toc-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-vector-page-titlebar-toc" class="vector-dropdown-checkbox " aria-label="Toggle the table of contents" > <label id="vector-page-titlebar-toc-label" for="vector-page-titlebar-toc-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--icon-only " aria-hidden="true" ><span class="vector-icon mw-ui-icon-listBullet mw-ui-icon-wikimedia-listBullet"></span> <span class="vector-dropdown-label-text">Toggle the table of contents</span> </label> <div class="vector-dropdown-content"> <div id="vector-page-titlebar-toc-unpinned-container" class="vector-unpinned-container"> </div> </div> </div> </nav> <h1 id="firstHeading" class="firstHeading mw-first-heading"><span class="mw-page-title-main">Tryptophan</span></h1> <div id="p-lang-btn" class="vector-dropdown mw-portlet mw-portlet-lang" > <input type="checkbox" id="p-lang-btn-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-p-lang-btn" class="vector-dropdown-checkbox mw-interlanguage-selector" aria-label="Go to an article in another language. Available in 63 languages" > <label id="p-lang-btn-label" for="p-lang-btn-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--action-progressive mw-portlet-lang-heading-63" aria-hidden="true" ><span class="vector-icon mw-ui-icon-language-progressive mw-ui-icon-wikimedia-language-progressive"></span> <span class="vector-dropdown-label-text">63 languages</span> </label> <div class="vector-dropdown-content"> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li class="interlanguage-link interwiki-af mw-list-item"><a href="https://af.wikipedia.org/wiki/Triptofaan" title="Triptofaan – Afrikaans" lang="af" hreflang="af" data-title="Triptofaan" data-language-autonym="Afrikaans" data-language-local-name="Afrikaans" class="interlanguage-link-target"><span>Afrikaans</span></a></li><li class="interlanguage-link interwiki-ar mw-list-item"><a href="https://ar.wikipedia.org/wiki/%D8%AA%D8%B1%D9%8A%D8%A8%D8%AA%D9%88%D9%81%D8%A7%D9%86" title="تريبتوفان – Arabic" lang="ar" hreflang="ar" data-title="تريبتوفان" data-language-autonym="العربية" data-language-local-name="Arabic" class="interlanguage-link-target"><span>العربية</span></a></li><li class="interlanguage-link interwiki-az mw-list-item"><a href="https://az.wikipedia.org/wiki/Triptofan" title="Triptofan – Azerbaijani" lang="az" hreflang="az" data-title="Triptofan" data-language-autonym="Azərbaycanca" data-language-local-name="Azerbaijani" class="interlanguage-link-target"><span>Azərbaycanca</span></a></li><li class="interlanguage-link interwiki-azb mw-list-item"><a href="https://azb.wikipedia.org/wiki/%D8%AA%D8%B1%DB%8C%D9%BE%D8%AA%D9%88%D9%81%D8%A7%D9%86" title="تریپتوفان – South Azerbaijani" lang="azb" hreflang="azb" data-title="تریپتوفان" data-language-autonym="تۆرکجه" data-language-local-name="South Azerbaijani" class="interlanguage-link-target"><span>تۆرکجه</span></a></li><li class="interlanguage-link interwiki-bn mw-list-item"><a href="https://bn.wikipedia.org/wiki/%E0%A6%9F%E0%A7%8D%E0%A6%B0%E0%A6%BF%E0%A6%AA%E0%A7%8D%E0%A6%9F%E0%A7%8B%E0%A6%AB%E0%A7%8D%E0%A6%AF%E0%A6%BE%E0%A6%A8" title="ট্রিপ্টোফ্যান – Bangla" lang="bn" hreflang="bn" data-title="ট্রিপ্টোফ্যান" data-language-autonym="বাংলা" data-language-local-name="Bangla" class="interlanguage-link-target"><span>বাংলা</span></a></li><li class="interlanguage-link interwiki-zh-min-nan mw-list-item"><a href="https://zh-min-nan.wikipedia.org/wiki/Tryptophan" title="Tryptophan – Minnan" lang="nan" hreflang="nan" data-title="Tryptophan" data-language-autonym="閩南語 / Bân-lâm-gú" data-language-local-name="Minnan" class="interlanguage-link-target"><span>閩南語 / Bân-lâm-gú</span></a></li><li class="interlanguage-link interwiki-be mw-list-item"><a href="https://be.wikipedia.org/wiki/%D0%A2%D1%80%D1%8B%D0%BF%D1%82%D0%B0%D1%84%D0%B0%D0%BD" title="Трыптафан – Belarusian" lang="be" hreflang="be" data-title="Трыптафан" data-language-autonym="Беларуская" data-language-local-name="Belarusian" class="interlanguage-link-target"><span>Беларуская</span></a></li><li class="interlanguage-link interwiki-be-x-old mw-list-item"><a href="https://be-tarask.wikipedia.org/wiki/%D0%A2%D1%80%D1%8B%D0%BF%D1%82%D0%B0%D1%84%D0%B0%D0%BD" title="Трыптафан – Belarusian (Taraškievica orthography)" lang="be-tarask" hreflang="be-tarask" data-title="Трыптафан" data-language-autonym="Беларуская (тарашкевіца)" data-language-local-name="Belarusian (Taraškievica orthography)" class="interlanguage-link-target"><span>Беларуская (тарашкевіца)</span></a></li><li class="interlanguage-link interwiki-bg mw-list-item"><a href="https://bg.wikipedia.org/wiki/%D0%A2%D1%80%D0%B8%D0%BF%D1%82%D0%BE%D1%84%D0%B0%D0%BD" title="Триптофан – Bulgarian" lang="bg" hreflang="bg" data-title="Триптофан" data-language-autonym="Български" data-language-local-name="Bulgarian" class="interlanguage-link-target"><span>Български</span></a></li><li class="interlanguage-link interwiki-bs mw-list-item"><a href="https://bs.wikipedia.org/wiki/Triptofan" title="Triptofan – Bosnian" lang="bs" hreflang="bs" data-title="Triptofan" data-language-autonym="Bosanski" data-language-local-name="Bosnian" class="interlanguage-link-target"><span>Bosanski</span></a></li><li class="interlanguage-link interwiki-ca mw-list-item"><a href="https://ca.wikipedia.org/wiki/Tript%C3%B2fan" title="Triptòfan – Catalan" lang="ca" hreflang="ca" data-title="Triptòfan" data-language-autonym="Català" data-language-local-name="Catalan" class="interlanguage-link-target"><span>Català</span></a></li><li class="interlanguage-link interwiki-cs mw-list-item"><a href="https://cs.wikipedia.org/wiki/Tryptofan" title="Tryptofan – Czech" lang="cs" hreflang="cs" data-title="Tryptofan" data-language-autonym="Čeština" data-language-local-name="Czech" class="interlanguage-link-target"><span>Čeština</span></a></li><li class="interlanguage-link interwiki-da mw-list-item"><a href="https://da.wikipedia.org/wiki/Tryptophan" title="Tryptophan – Danish" lang="da" hreflang="da" data-title="Tryptophan" data-language-autonym="Dansk" data-language-local-name="Danish" class="interlanguage-link-target"><span>Dansk</span></a></li><li class="interlanguage-link interwiki-de mw-list-item"><a href="https://de.wikipedia.org/wiki/Tryptophan" title="Tryptophan – German" lang="de" hreflang="de" data-title="Tryptophan" data-language-autonym="Deutsch" data-language-local-name="German" class="interlanguage-link-target"><span>Deutsch</span></a></li><li class="interlanguage-link interwiki-et mw-list-item"><a href="https://et.wikipedia.org/wiki/Tr%C3%BCptofaan" title="Trüptofaan – Estonian" lang="et" hreflang="et" data-title="Trüptofaan" data-language-autonym="Eesti" data-language-local-name="Estonian" class="interlanguage-link-target"><span>Eesti</span></a></li><li class="interlanguage-link interwiki-el mw-list-item"><a href="https://el.wikipedia.org/wiki/%CE%A4%CF%81%CF%85%CF%80%CF%84%CE%BF%CF%86%CE%AC%CE%BD%CE%B7" title="Τρυπτοφάνη – Greek" lang="el" hreflang="el" data-title="Τρυπτοφάνη" data-language-autonym="Ελληνικά" data-language-local-name="Greek" class="interlanguage-link-target"><span>Ελληνικά</span></a></li><li class="interlanguage-link interwiki-es mw-list-item"><a href="https://es.wikipedia.org/wiki/Tript%C3%B3fano" title="Triptófano – Spanish" lang="es" hreflang="es" data-title="Triptófano" data-language-autonym="Español" data-language-local-name="Spanish" class="interlanguage-link-target"><span>Español</span></a></li><li class="interlanguage-link interwiki-eo mw-list-item"><a href="https://eo.wikipedia.org/wiki/Triptofano" title="Triptofano – Esperanto" lang="eo" hreflang="eo" data-title="Triptofano" data-language-autonym="Esperanto" data-language-local-name="Esperanto" class="interlanguage-link-target"><span>Esperanto</span></a></li><li class="interlanguage-link interwiki-eu mw-list-item"><a href="https://eu.wikipedia.org/wiki/Triptofano" title="Triptofano – Basque" lang="eu" hreflang="eu" data-title="Triptofano" data-language-autonym="Euskara" data-language-local-name="Basque" class="interlanguage-link-target"><span>Euskara</span></a></li><li class="interlanguage-link interwiki-fa mw-list-item"><a href="https://fa.wikipedia.org/wiki/%D8%AA%D8%B1%DB%8C%D9%BE%D8%AA%D9%88%D9%81%D8%A7%D9%86" title="تریپتوفان – Persian" lang="fa" hreflang="fa" data-title="تریپتوفان" data-language-autonym="فارسی" data-language-local-name="Persian" class="interlanguage-link-target"><span>فارسی</span></a></li><li class="interlanguage-link interwiki-fr mw-list-item"><a href="https://fr.wikipedia.org/wiki/Tryptophane" title="Tryptophane – French" lang="fr" hreflang="fr" data-title="Tryptophane" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target"><span>Français</span></a></li><li class="interlanguage-link interwiki-gl mw-list-item"><a href="https://gl.wikipedia.org/wiki/Tript%C3%B3fano" title="Triptófano – Galician" lang="gl" hreflang="gl" data-title="Triptófano" data-language-autonym="Galego" data-language-local-name="Galician" class="interlanguage-link-target"><span>Galego</span></a></li><li class="interlanguage-link interwiki-ko mw-list-item"><a href="https://ko.wikipedia.org/wiki/%ED%8A%B8%EB%A6%BD%ED%86%A0%ED%8C%90" title="트립토판 – Korean" lang="ko" hreflang="ko" data-title="트립토판" data-language-autonym="한국어" data-language-local-name="Korean" class="interlanguage-link-target"><span>한국어</span></a></li><li class="interlanguage-link interwiki-hy mw-list-item"><a href="https://hy.wikipedia.org/wiki/%D5%8F%D6%80%D5%AB%D5%BA%D5%BF%D5%B8%D6%86%D5%A1%D5%B6" title="Տրիպտոֆան – Armenian" lang="hy" hreflang="hy" data-title="Տրիպտոֆան" data-language-autonym="Հայերեն" data-language-local-name="Armenian" class="interlanguage-link-target"><span>Հայերեն</span></a></li><li class="interlanguage-link interwiki-hr mw-list-item"><a href="https://hr.wikipedia.org/wiki/Triptofan" title="Triptofan – Croatian" lang="hr" hreflang="hr" data-title="Triptofan" data-language-autonym="Hrvatski" data-language-local-name="Croatian" class="interlanguage-link-target"><span>Hrvatski</span></a></li><li class="interlanguage-link interwiki-id mw-list-item"><a href="https://id.wikipedia.org/wiki/Triptofan" title="Triptofan – Indonesian" lang="id" hreflang="id" data-title="Triptofan" data-language-autonym="Bahasa Indonesia" data-language-local-name="Indonesian" class="interlanguage-link-target"><span>Bahasa Indonesia</span></a></li><li class="interlanguage-link interwiki-it mw-list-item"><a href="https://it.wikipedia.org/wiki/Triptofano" title="Triptofano – Italian" lang="it" hreflang="it" data-title="Triptofano" data-language-autonym="Italiano" data-language-local-name="Italian" class="interlanguage-link-target"><span>Italiano</span></a></li><li class="interlanguage-link interwiki-he mw-list-item"><a href="https://he.wikipedia.org/wiki/%D7%98%D7%A8%D7%99%D7%A4%D7%98%D7%95%D7%A4%D7%9F" title="טריפטופן – Hebrew" lang="he" hreflang="he" data-title="טריפטופן" data-language-autonym="עברית" data-language-local-name="Hebrew" class="interlanguage-link-target"><span>עברית</span></a></li><li class="interlanguage-link interwiki-jv mw-list-item"><a href="https://jv.wikipedia.org/wiki/Triptofan" title="Triptofan – Javanese" lang="jv" hreflang="jv" data-title="Triptofan" data-language-autonym="Jawa" data-language-local-name="Javanese" class="interlanguage-link-target"><span>Jawa</span></a></li><li class="interlanguage-link interwiki-ku mw-list-item"><a href="https://ku.wikipedia.org/wiki/Tr%C3%AEptofan" title="Trîptofan – Kurdish" lang="ku" hreflang="ku" data-title="Trîptofan" data-language-autonym="Kurdî" data-language-local-name="Kurdish" class="interlanguage-link-target"><span>Kurdî</span></a></li><li class="interlanguage-link interwiki-la mw-list-item"><a href="https://la.wikipedia.org/wiki/Tryptophanum" title="Tryptophanum – Latin" lang="la" hreflang="la" data-title="Tryptophanum" data-language-autonym="Latina" data-language-local-name="Latin" class="interlanguage-link-target"><span>Latina</span></a></li><li class="interlanguage-link interwiki-lv mw-list-item"><a href="https://lv.wikipedia.org/wiki/Triptof%C4%81ns" title="Triptofāns – Latvian" lang="lv" hreflang="lv" data-title="Triptofāns" data-language-autonym="Latviešu" data-language-local-name="Latvian" class="interlanguage-link-target"><span>Latviešu</span></a></li><li class="interlanguage-link interwiki-lb mw-list-item"><a href="https://lb.wikipedia.org/wiki/Tryptophan" title="Tryptophan – Luxembourgish" lang="lb" hreflang="lb" data-title="Tryptophan" data-language-autonym="Lëtzebuergesch" data-language-local-name="Luxembourgish" class="interlanguage-link-target"><span>Lëtzebuergesch</span></a></li><li class="interlanguage-link interwiki-lt mw-list-item"><a href="https://lt.wikipedia.org/wiki/Triptofanas" title="Triptofanas – Lithuanian" lang="lt" hreflang="lt" data-title="Triptofanas" data-language-autonym="Lietuvių" data-language-local-name="Lithuanian" class="interlanguage-link-target"><span>Lietuvių</span></a></li><li class="interlanguage-link interwiki-hu mw-list-item"><a href="https://hu.wikipedia.org/wiki/Triptof%C3%A1n" title="Triptofán – Hungarian" lang="hu" hreflang="hu" data-title="Triptofán" data-language-autonym="Magyar" data-language-local-name="Hungarian" class="interlanguage-link-target"><span>Magyar</span></a></li><li class="interlanguage-link interwiki-mk mw-list-item"><a href="https://mk.wikipedia.org/wiki/%D0%A2%D1%80%D0%B8%D0%BF%D1%82%D0%BE%D1%84%D0%B0%D0%BD" title="Триптофан – Macedonian" lang="mk" hreflang="mk" data-title="Триптофан" data-language-autonym="Македонски" data-language-local-name="Macedonian" class="interlanguage-link-target"><span>Македонски</span></a></li><li class="interlanguage-link interwiki-ms mw-list-item"><a href="https://ms.wikipedia.org/wiki/Triptofan" title="Triptofan – Malay" lang="ms" hreflang="ms" data-title="Triptofan" data-language-autonym="Bahasa Melayu" data-language-local-name="Malay" class="interlanguage-link-target"><span>Bahasa Melayu</span></a></li><li class="interlanguage-link interwiki-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/Tryptofaan" title="Tryptofaan – Dutch" lang="nl" hreflang="nl" data-title="Tryptofaan" data-language-autonym="Nederlands" data-language-local-name="Dutch" class="interlanguage-link-target"><span>Nederlands</span></a></li><li class="interlanguage-link interwiki-ja mw-list-item"><a href="https://ja.wikipedia.org/wiki/%E3%83%88%E3%83%AA%E3%83%97%E3%83%88%E3%83%95%E3%82%A1%E3%83%B3" title="トリプトファン – Japanese" lang="ja" hreflang="ja" data-title="トリプトファン" data-language-autonym="日本語" data-language-local-name="Japanese" class="interlanguage-link-target"><span>日本語</span></a></li><li class="interlanguage-link interwiki-no mw-list-item"><a href="https://no.wikipedia.org/wiki/Tryptofan" title="Tryptofan – Norwegian Bokmål" lang="nb" hreflang="nb" data-title="Tryptofan" data-language-autonym="Norsk bokmål" data-language-local-name="Norwegian Bokmål" class="interlanguage-link-target"><span>Norsk bokmål</span></a></li><li class="interlanguage-link interwiki-nn mw-list-item"><a href="https://nn.wikipedia.org/wiki/Tryptofan" title="Tryptofan – Norwegian Nynorsk" lang="nn" hreflang="nn" data-title="Tryptofan" data-language-autonym="Norsk nynorsk" data-language-local-name="Norwegian Nynorsk" class="interlanguage-link-target"><span>Norsk nynorsk</span></a></li><li class="interlanguage-link interwiki-oc mw-list-item"><a href="https://oc.wikipedia.org/wiki/Triptofan" title="Triptofan – Occitan" lang="oc" hreflang="oc" data-title="Triptofan" data-language-autonym="Occitan" data-language-local-name="Occitan" class="interlanguage-link-target"><span>Occitan</span></a></li><li class="interlanguage-link interwiki-pl mw-list-item"><a href="https://pl.wikipedia.org/wiki/Tryptofan" title="Tryptofan – Polish" lang="pl" hreflang="pl" data-title="Tryptofan" data-language-autonym="Polski" data-language-local-name="Polish" class="interlanguage-link-target"><span>Polski</span></a></li><li class="interlanguage-link interwiki-pt mw-list-item"><a href="https://pt.wikipedia.org/wiki/Triptofano" title="Triptofano – Portuguese" lang="pt" hreflang="pt" data-title="Triptofano" data-language-autonym="Português" data-language-local-name="Portuguese" class="interlanguage-link-target"><span>Português</span></a></li><li class="interlanguage-link interwiki-ro mw-list-item"><a href="https://ro.wikipedia.org/wiki/Triptofan" title="Triptofan – Romanian" lang="ro" hreflang="ro" data-title="Triptofan" data-language-autonym="Română" data-language-local-name="Romanian" class="interlanguage-link-target"><span>Română</span></a></li><li class="interlanguage-link interwiki-ru mw-list-item"><a href="https://ru.wikipedia.org/wiki/%D0%A2%D1%80%D0%B8%D0%BF%D1%82%D0%BE%D1%84%D0%B0%D0%BD" title="Триптофан – Russian" lang="ru" hreflang="ru" data-title="Триптофан" data-language-autonym="Русский" data-language-local-name="Russian" class="interlanguage-link-target"><span>Русский</span></a></li><li class="interlanguage-link interwiki-simple mw-list-item"><a href="https://simple.wikipedia.org/wiki/Tryptophan" title="Tryptophan – Simple English" lang="en-simple" hreflang="en-simple" data-title="Tryptophan" data-language-autonym="Simple English" data-language-local-name="Simple English" class="interlanguage-link-target"><span>Simple English</span></a></li><li class="interlanguage-link interwiki-sk mw-list-item"><a href="https://sk.wikipedia.org/wiki/Tryptof%C3%A1n" title="Tryptofán – Slovak" lang="sk" hreflang="sk" data-title="Tryptofán" data-language-autonym="Slovenčina" data-language-local-name="Slovak" class="interlanguage-link-target"><span>Slovenčina</span></a></li><li class="interlanguage-link interwiki-sl mw-list-item"><a href="https://sl.wikipedia.org/wiki/Triptofan" title="Triptofan – Slovenian" lang="sl" hreflang="sl" data-title="Triptofan" data-language-autonym="Slovenščina" data-language-local-name="Slovenian" class="interlanguage-link-target"><span>Slovenščina</span></a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/Triptofan" title="Triptofan – Serbian" lang="sr" hreflang="sr" data-title="Triptofan" data-language-autonym="Српски / srpski" data-language-local-name="Serbian" class="interlanguage-link-target"><span>Српски / srpski</span></a></li><li class="interlanguage-link interwiki-sh mw-list-item"><a href="https://sh.wikipedia.org/wiki/Triptofan" title="Triptofan – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Triptofan" data-language-autonym="Srpskohrvatski / српскохрватски" data-language-local-name="Serbo-Croatian" class="interlanguage-link-target"><span>Srpskohrvatski / српскохрватски</span></a></li><li class="interlanguage-link interwiki-su mw-list-item"><a href="https://su.wikipedia.org/wiki/Triptopan" title="Triptopan – Sundanese" lang="su" hreflang="su" data-title="Triptopan" data-language-autonym="Sunda" data-language-local-name="Sundanese" class="interlanguage-link-target"><span>Sunda</span></a></li><li class="interlanguage-link interwiki-fi mw-list-item"><a href="https://fi.wikipedia.org/wiki/Tryptofaani" title="Tryptofaani – Finnish" lang="fi" hreflang="fi" data-title="Tryptofaani" data-language-autonym="Suomi" data-language-local-name="Finnish" class="interlanguage-link-target"><span>Suomi</span></a></li><li class="interlanguage-link interwiki-sv mw-list-item"><a href="https://sv.wikipedia.org/wiki/Tryptofan" title="Tryptofan – Swedish" lang="sv" hreflang="sv" data-title="Tryptofan" data-language-autonym="Svenska" data-language-local-name="Swedish" class="interlanguage-link-target"><span>Svenska</span></a></li><li class="interlanguage-link interwiki-ta mw-list-item"><a href="https://ta.wikipedia.org/wiki/%E0%AE%9F%E0%AE%BF%E0%AE%B0%E0%AE%BF%E0%AE%AA%E0%AF%8D%E0%AE%9F%E0%AF%8B%E0%AE%AA%E0%AE%BE%E0%AE%A9%E0%AF%8D" title="டிரிப்டோபான் – Tamil" lang="ta" hreflang="ta" data-title="டிரிப்டோபான்" data-language-autonym="தமிழ்" data-language-local-name="Tamil" class="interlanguage-link-target"><span>தமிழ்</span></a></li><li class="interlanguage-link interwiki-th mw-list-item"><a href="https://th.wikipedia.org/wiki/%E0%B8%97%E0%B8%A3%E0%B8%B4%E0%B8%9B%E0%B9%82%E0%B8%95%E0%B9%80%E0%B8%9F%E0%B8%99" title="ทริปโตเฟน – Thai" lang="th" hreflang="th" data-title="ทริปโตเฟน" data-language-autonym="ไทย" data-language-local-name="Thai" class="interlanguage-link-target"><span>ไทย</span></a></li><li class="interlanguage-link interwiki-tr mw-list-item"><a href="https://tr.wikipedia.org/wiki/Triptofan" title="Triptofan – Turkish" lang="tr" hreflang="tr" data-title="Triptofan" data-language-autonym="Türkçe" data-language-local-name="Turkish" class="interlanguage-link-target"><span>Türkçe</span></a></li><li class="interlanguage-link interwiki-uk mw-list-item"><a href="https://uk.wikipedia.org/wiki/%D0%A2%D1%80%D0%B8%D0%BF%D1%82%D0%BE%D1%84%D0%B0%D0%BD" title="Триптофан – Ukrainian" lang="uk" hreflang="uk" data-title="Триптофан" data-language-autonym="Українська" data-language-local-name="Ukrainian" class="interlanguage-link-target"><span>Українська</span></a></li><li class="interlanguage-link interwiki-vi mw-list-item"><a href="https://vi.wikipedia.org/wiki/Tryptophan" title="Tryptophan – Vietnamese" lang="vi" hreflang="vi" data-title="Tryptophan" data-language-autonym="Tiếng Việt" data-language-local-name="Vietnamese" class="interlanguage-link-target"><span>Tiếng Việt</span></a></li><li class="interlanguage-link interwiki-war mw-list-item"><a href="https://war.wikipedia.org/wiki/Tryptophan" title="Tryptophan – Waray" lang="war" hreflang="war" data-title="Tryptophan" data-language-autonym="Winaray" data-language-local-name="Waray" class="interlanguage-link-target"><span>Winaray</span></a></li><li class="interlanguage-link interwiki-wuu mw-list-item"><a href="https://wuu.wikipedia.org/wiki/%E8%89%B2%E6%B0%A8%E9%85%B8" title="色氨酸 – Wu" lang="wuu" hreflang="wuu" data-title="色氨酸" data-language-autonym="吴语" data-language-local-name="Wu" class="interlanguage-link-target"><span>吴语</span></a></li><li class="interlanguage-link interwiki-zh-yue mw-list-item"><a href="https://zh-yue.wikipedia.org/wiki/%E8%89%B2%E6%B0%A8%E9%85%B8" title="色氨酸 – Cantonese" lang="yue" hreflang="yue" data-title="色氨酸" data-language-autonym="粵語" data-language-local-name="Cantonese" class="interlanguage-link-target"><span>粵語</span></a></li><li class="interlanguage-link interwiki-zh mw-list-item"><a href="https://zh.wikipedia.org/wiki/%E8%89%B2%E6%B0%A8%E9%85%B8" title="色氨酸 – Chinese" lang="zh" hreflang="zh" data-title="色氨酸" data-language-autonym="中文" data-language-local-name="Chinese" class="interlanguage-link-target"><span>中文</span></a></li> </ul> <div class="after-portlet after-portlet-lang"><span class="wb-langlinks-edit wb-langlinks-link"><a href="https://www.wikidata.org/wiki/Special:EntityPage/Q181003#sitelinks-wikipedia" title="Edit interlanguage links" class="wbc-editpage">Edit links</a></span></div> </div> </div> </div> </header> <div class="vector-page-toolbar"> <div class="vector-page-toolbar-container"> <div id="left-navigation"> <nav aria-label="Namespaces"> <div id="p-associated-pages" class="vector-menu vector-menu-tabs mw-portlet mw-portlet-associated-pages" > <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li id="ca-nstab-main" class="selected vector-tab-noicon mw-list-item"><a href="/wiki/Tryptophan" title="View the content page [c]" accesskey="c"><span>Article</span></a></li><li id="ca-talk" class="vector-tab-noicon mw-list-item"><a href="/wiki/Talk:Tryptophan" rel="discussion" title="Discuss improvements to the content page [t]" accesskey="t"><span>Talk</span></a></li> </ul> </div> </div> <div id="vector-variants-dropdown" class="vector-dropdown emptyPortlet" > <input type="checkbox" id="vector-variants-dropdown-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-vector-variants-dropdown" class="vector-dropdown-checkbox " aria-label="Change language variant" > <label id="vector-variants-dropdown-label" for="vector-variants-dropdown-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet" aria-hidden="true" ><span class="vector-dropdown-label-text">English</span> </label> <div class="vector-dropdown-content"> <div id="p-variants" class="vector-menu mw-portlet mw-portlet-variants emptyPortlet" > <div class="vector-menu-content"> <ul class="vector-menu-content-list"> </ul> </div> </div> </div> </div> </nav> </div> <div id="right-navigation" class="vector-collapsible"> <nav aria-label="Views"> <div id="p-views" class="vector-menu vector-menu-tabs mw-portlet mw-portlet-views" > <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li id="ca-view" class="selected vector-tab-noicon mw-list-item"><a href="/wiki/Tryptophan"><span>Read</span></a></li><li id="ca-edit" class="vector-tab-noicon mw-list-item"><a href="/w/index.php?title=Tryptophan&action=edit" title="Edit this page [e]" accesskey="e"><span>Edit</span></a></li><li id="ca-history" class="vector-tab-noicon mw-list-item"><a href="/w/index.php?title=Tryptophan&action=history" title="Past revisions of this page [h]" accesskey="h"><span>View history</span></a></li> </ul> </div> </div> </nav> <nav class="vector-page-tools-landmark" aria-label="Page tools"> <div id="vector-page-tools-dropdown" class="vector-dropdown vector-page-tools-dropdown" > <input type="checkbox" id="vector-page-tools-dropdown-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-vector-page-tools-dropdown" class="vector-dropdown-checkbox " aria-label="Tools" > <label id="vector-page-tools-dropdown-label" for="vector-page-tools-dropdown-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet" aria-hidden="true" ><span class="vector-dropdown-label-text">Tools</span> </label> <div class="vector-dropdown-content"> <div id="vector-page-tools-unpinned-container" class="vector-unpinned-container"> <div id="vector-page-tools" class="vector-page-tools vector-pinnable-element"> <div class="vector-pinnable-header vector-page-tools-pinnable-header vector-pinnable-header-unpinned" data-feature-name="page-tools-pinned" data-pinnable-element-id="vector-page-tools" data-pinned-container-id="vector-page-tools-pinned-container" data-unpinned-container-id="vector-page-tools-unpinned-container" > <div class="vector-pinnable-header-label">Tools</div> <button class="vector-pinnable-header-toggle-button vector-pinnable-header-pin-button" data-event-name="pinnable-header.vector-page-tools.pin">move to sidebar</button> <button class="vector-pinnable-header-toggle-button vector-pinnable-header-unpin-button" data-event-name="pinnable-header.vector-page-tools.unpin">hide</button> </div> <div id="p-cactions" class="vector-menu mw-portlet mw-portlet-cactions emptyPortlet vector-has-collapsible-items" title="More options" > <div class="vector-menu-heading"> Actions </div> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li id="ca-more-view" class="selected vector-more-collapsible-item mw-list-item"><a href="/wiki/Tryptophan"><span>Read</span></a></li><li id="ca-more-edit" class="vector-more-collapsible-item mw-list-item"><a href="/w/index.php?title=Tryptophan&action=edit" title="Edit this page [e]" accesskey="e"><span>Edit</span></a></li><li id="ca-more-history" class="vector-more-collapsible-item mw-list-item"><a href="/w/index.php?title=Tryptophan&action=history"><span>View history</span></a></li> </ul> </div> </div> <div id="p-tb" class="vector-menu mw-portlet mw-portlet-tb" > <div class="vector-menu-heading"> General </div> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li id="t-whatlinkshere" class="mw-list-item"><a href="/wiki/Special:WhatLinksHere/Tryptophan" title="List of all English Wikipedia pages containing links to this page [j]" accesskey="j"><span>What links here</span></a></li><li id="t-recentchangeslinked" class="mw-list-item"><a href="/wiki/Special:RecentChangesLinked/Tryptophan" rel="nofollow" title="Recent changes in pages linked from this page [k]" accesskey="k"><span>Related changes</span></a></li><li id="t-upload" class="mw-list-item"><a href="/wiki/Wikipedia:File_Upload_Wizard" title="Upload files [u]" accesskey="u"><span>Upload file</span></a></li><li id="t-specialpages" class="mw-list-item"><a href="/wiki/Special:SpecialPages" title="A list of all special pages [q]" accesskey="q"><span>Special pages</span></a></li><li id="t-permalink" class="mw-list-item"><a href="/w/index.php?title=Tryptophan&oldid=1249994738" title="Permanent link to this revision of this page"><span>Permanent link</span></a></li><li id="t-info" class="mw-list-item"><a href="/w/index.php?title=Tryptophan&action=info" title="More information about this page"><span>Page information</span></a></li><li id="t-cite" class="mw-list-item"><a href="/w/index.php?title=Special:CiteThisPage&page=Tryptophan&id=1249994738&wpFormIdentifier=titleform" title="Information on how to cite this page"><span>Cite this page</span></a></li><li id="t-urlshortener" class="mw-list-item"><a href="/w/index.php?title=Special:UrlShortener&url=https%3A%2F%2Fen.wikipedia.org%2Fwiki%2FTryptophan"><span>Get shortened URL</span></a></li><li id="t-urlshortener-qrcode" class="mw-list-item"><a href="/w/index.php?title=Special:QrCode&url=https%3A%2F%2Fen.wikipedia.org%2Fwiki%2FTryptophan"><span>Download QR code</span></a></li> </ul> </div> </div> <div id="p-coll-print_export" class="vector-menu mw-portlet mw-portlet-coll-print_export" > <div class="vector-menu-heading"> Print/export </div> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li id="coll-download-as-rl" class="mw-list-item"><a href="/w/index.php?title=Special:DownloadAsPdf&page=Tryptophan&action=show-download-screen" title="Download this page as a PDF file"><span>Download as PDF</span></a></li><li id="t-print" class="mw-list-item"><a href="/w/index.php?title=Tryptophan&printable=yes" title="Printable version of this page [p]" accesskey="p"><span>Printable version</span></a></li> </ul> </div> </div> <div id="p-wikibase-otherprojects" class="vector-menu mw-portlet mw-portlet-wikibase-otherprojects" > <div class="vector-menu-heading"> In other projects </div> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li class="wb-otherproject-link wb-otherproject-commons mw-list-item"><a href="https://commons.wikimedia.org/wiki/Category:Tryptophan" hreflang="en"><span>Wikimedia Commons</span></a></li><li id="t-wikibase" class="wb-otherproject-link wb-otherproject-wikibase-dataitem mw-list-item"><a href="https://www.wikidata.org/wiki/Special:EntityPage/Q181003" title="Structured data on this page hosted by Wikidata [g]" accesskey="g"><span>Wikidata item</span></a></li> </ul> </div> </div> </div> </div> </div> </div> </nav> </div> </div> </div> <div class="vector-column-end"> <div class="vector-sticky-pinned-container"> <nav class="vector-page-tools-landmark" aria-label="Page tools"> <div id="vector-page-tools-pinned-container" class="vector-pinned-container"> </div> </nav> <nav class="vector-appearance-landmark" aria-label="Appearance"> <div id="vector-appearance-pinned-container" class="vector-pinned-container"> <div id="vector-appearance" class="vector-appearance vector-pinnable-element"> <div class="vector-pinnable-header vector-appearance-pinnable-header vector-pinnable-header-pinned" data-feature-name="appearance-pinned" data-pinnable-element-id="vector-appearance" data-pinned-container-id="vector-appearance-pinned-container" data-unpinned-container-id="vector-appearance-unpinned-container" > <div class="vector-pinnable-header-label">Appearance</div> <button class="vector-pinnable-header-toggle-button vector-pinnable-header-pin-button" data-event-name="pinnable-header.vector-appearance.pin">move to sidebar</button> <button class="vector-pinnable-header-toggle-button vector-pinnable-header-unpin-button" data-event-name="pinnable-header.vector-appearance.unpin">hide</button> </div> </div> </div> </nav> </div> </div> <div id="bodyContent" class="vector-body" aria-labelledby="firstHeading" data-mw-ve-target-container> <div class="vector-body-before-content"> <div class="mw-indicators"> </div> <div id="siteSub" class="noprint">From Wikipedia, the free encyclopedia</div> </div> <div id="contentSub"><div id="mw-content-subtitle"></div></div> <div id="mw-content-text" class="mw-body-content"><div class="mw-content-ltr mw-parser-output" lang="en" dir="ltr"><p class="mw-empty-elt"> </p> <style data-mw-deduplicate="TemplateStyles:r1236090951">.mw-parser-output .hatnote{font-style:italic}.mw-parser-output div.hatnote{padding-left:1.6em;margin-bottom:0.5em}.mw-parser-output .hatnote i{font-style:normal}.mw-parser-output .hatnote+link+.hatnote{margin-top:-0.5em}@media print{body.ns-0 .mw-parser-output .hatnote{display:none!important}}</style><div role="note" class="hatnote navigation-not-searchable">"Tryptan" redirects here. For the type of anti-migraine drug, see <a href="/wiki/Triptan" title="Triptan">Triptan</a>. For the hydrocarbon, see <a href="/wiki/Triptane" title="Triptane">Triptane</a>.</div> <p> <style data-mw-deduplicate="TemplateStyles:r1084375498">.mw-parser-output .ib-chembox{border-collapse:collapse;text-align:left}.mw-parser-output .ib-chembox td,.mw-parser-output .ib-chembox th{border:1px solid #a2a9b1;width:40%}.mw-parser-output .ib-chembox td+td{width:60%}</style> </p> <table class="infobox ib-chembox"> <caption><style data-mw-deduplicate="TemplateStyles:r920966791">.mw-parser-output span.smallcaps{font-variant:small-caps}.mw-parser-output span.smallcaps-smaller{font-size:85%}</style><span class="smallcaps">l</span>-Tryptophan </caption> <tbody><tr> <td colspan="2" style="text-align:center; padding:2px;"><span typeof="mw:File"><a href="/wiki/File:L-Tryptophan_-_L-Tryptophan.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/c/c1/L-Tryptophan_-_L-Tryptophan.svg/220px-L-Tryptophan_-_L-Tryptophan.svg.png" decoding="async" width="220" height="99" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/c/c1/L-Tryptophan_-_L-Tryptophan.svg/330px-L-Tryptophan_-_L-Tryptophan.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/c/c1/L-Tryptophan_-_L-Tryptophan.svg/440px-L-Tryptophan_-_L-Tryptophan.svg.png 2x" data-file-width="277" data-file-height="125" /></a></span><br /><div style="text-align:center;"><a href="/wiki/Skeletal_formula" title="Skeletal formula">Skeletal formula</a> of <small>L</small>-tryptophan</div> </td></tr> <tr> <td colspan="2" class="borderless" style="text-align:center"> <table border="0" style="width:100%;display:inline-table;"> <tbody><tr> <td style="border-right:1px solid #aaa; width:50%;"><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Tryptophan-from-xtal-3D-bs-17.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/c/c9/Tryptophan-from-xtal-3D-bs-17.png/105px-Tryptophan-from-xtal-3D-bs-17.png" decoding="async" width="105" height="176" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/c/c9/Tryptophan-from-xtal-3D-bs-17.png/158px-Tryptophan-from-xtal-3D-bs-17.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/c/c9/Tryptophan-from-xtal-3D-bs-17.png/210px-Tryptophan-from-xtal-3D-bs-17.png 2x" data-file-width="1419" data-file-height="2384" /></a><figcaption></figcaption></figure><div style="text-align:center"><a href="/wiki/Ball-and-stick_model" title="Ball-and-stick model">ball-and-stick model</a><sup id="cite_ref-Görbitz_1-0" class="reference"><a href="#cite_note-Görbitz-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup></div> </td> <td style="width:50%;"><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Tryptophan-from-xtal-3D-sf.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/0/0c/Tryptophan-from-xtal-3D-sf.png/120px-Tryptophan-from-xtal-3D-sf.png" decoding="async" width="120" height="176" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/0/0c/Tryptophan-from-xtal-3D-sf.png/180px-Tryptophan-from-xtal-3D-sf.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/0/0c/Tryptophan-from-xtal-3D-sf.png/240px-Tryptophan-from-xtal-3D-sf.png 2x" data-file-width="1609" data-file-height="2356" /></a><figcaption></figcaption></figure><div style="text-align:center"><a href="/wiki/Space-filling_model" title="Space-filling model">space-filling model</a><sup id="cite_ref-Görbitz_1-1" class="reference"><a href="#cite_note-Görbitz-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup></div> </td></tr></tbody></table> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Names </th></tr> <tr> <td colspan="2" style="text-align:left;"><a href="/wiki/Chemical_nomenclature" title="Chemical nomenclature">IUPAC name</a> <div style="max-width:22em; word-wrap:break-word; padding-left:1.7em;">Tryptophan</div> </td></tr> <tr> <td colspan="2" style="text-align:left;"><a href="/wiki/Chemical_nomenclature#Systematic_name" title="Chemical nomenclature">Systematic IUPAC name</a> <div style="max-width:22em; word-wrap:break-word; padding-left:1.7em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0; max-width:22em;">(2<i>S</i>)-2-amino-3-(1<i>H</i>-indol-3-yl)propanoic acid</div></div> </td></tr> <tr> <td colspan="2" style="text-align:left;">Other names <div style="max-width:22em; word-wrap:break-word; padding-left:1.7em;">2-Amino-3-(1<i>H</i>-indol-3-yl)propanoic acid</div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Identifiers </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/CAS_Registry_Number" title="CAS Registry Number">CAS Number</a></div> </td> <td><style data-mw-deduplicate="TemplateStyles:r1126788409">.mw-parser-output .plainlist ol,.mw-parser-output .plainlist ul{line-height:inherit;list-style:none;margin:0;padding:0}.mw-parser-output .plainlist ol li,.mw-parser-output .plainlist ul li{margin-bottom:0}</style><div class="plainlist"><ul><li><span title="commonchemistry.cas.org"><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=73-22-3">73-22-3</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">3D model (<a href="/wiki/JSmol" class="mw-redirect" title="JSmol">JSmol</a>)</div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="chemapps.stolaf.edu (3D interactive model)"><a rel="nofollow" class="external text" href="https://chemapps.stolaf.edu/jmol/jmol.php?model=c1%5BnH%5Dc2ccccc2c1C%5BC%40H%5D%28N%29C%28%3DO%29O">Interactive image</a></span></li><li><a href="/wiki/Zwitterion" title="Zwitterion">Zwitterion</a>: <span title="chemapps.stolaf.edu (3D interactive model)"><a rel="nofollow" class="external text" href="https://chemapps.stolaf.edu/jmol/jmol.php?model=c1%5BnH%5Dc2ccccc2c1C%5BC%40H%5D%28%5BNH3%2B%5D%29C%28%3DO%29%5BO-%5D">Interactive image</a></span></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ChEBI" title="ChEBI">ChEBI</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.ebi.ac.uk"><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chebi/searchId.do?chebiId=16828">CHEBI:16828</a></span></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ChEMBL" title="ChEMBL">ChEMBL</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.ebi.ac.uk"><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chembldb/index.php/compound/inspect/ChEMBL54976">ChEMBL54976</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ChemSpider" title="ChemSpider">ChemSpider</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.chemspider.com"><a rel="nofollow" class="external text" href="https://www.chemspider.com/Chemical-Structure.6066.html">6066</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><a href="/wiki/DrugBank" title="DrugBank">DrugBank</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.drugbank.ca"><a rel="nofollow" class="external text" href="https://www.drugbank.ca/drugs/DB00150">DB00150</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ECHA_InfoCard" class="mw-redirect" title="ECHA InfoCard"><span title="echa.europa.eu">ECHA InfoCard</span></a> </td> <td><a rel="nofollow" class="external text" href="https://echa.europa.eu/substance-information/-/substanceinfo/100.000.723">100.000.723</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q181003#P2566" title="Edit this at Wikidata"><img alt="Edit this at Wikidata" src="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/10px-OOjs_UI_icon_edit-ltr-progressive.svg.png" decoding="async" width="10" height="10" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/15px-OOjs_UI_icon_edit-ltr-progressive.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/20px-OOjs_UI_icon_edit-ltr-progressive.svg.png 2x" data-file-width="20" data-file-height="20" /></a></span> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/IUPHAR/BPS" class="mw-redirect" title="IUPHAR/BPS">IUPHAR/BPS</a></div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.guidetopharmacology.org"><a rel="nofollow" class="external text" href="http://www.guidetopharmacology.org/GRAC/LigandDisplayForward?tab=summary&ligandId=717">717</a></span></li></ul></div> </td></tr> <tr> <td><a href="/wiki/KEGG" title="KEGG">KEGG</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.kegg.jp"><a rel="nofollow" class="external text" href="https://www.kegg.jp/entry/D00020">D00020</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/PubChem" title="PubChem">PubChem</a> <abbr title="Compound ID">CID</abbr></div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="pubchem.ncbi.nlm.nih.gov"><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/6305">6305</a></span></li></ul></div> </td></tr> <tr> <td><a href="/wiki/Unique_Ingredient_Identifier" title="Unique Ingredient Identifier">UNII</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="precision.fda.gov"><a rel="nofollow" class="external text" href="https://precision.fda.gov/uniisearch/srs/unii/8DUH1N11BX">8DUH1N11BX</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/CompTox_Chemicals_Dashboard" title="CompTox Chemicals Dashboard">CompTox Dashboard</a> <span style="font-weight:normal">(<abbr title="U.S. Environmental Protection Agency">EPA</abbr>)</span></div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="comptox.epa.gov"><a rel="nofollow" class="external text" href="https://comptox.epa.gov/dashboard/chemical/details/DTXSID5021419">DTXSID5021419</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q181003#P3117" title="Edit this at Wikidata"><img alt="Edit this at Wikidata" src="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/10px-OOjs_UI_icon_edit-ltr-progressive.svg.png" decoding="async" width="10" height="10" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/15px-OOjs_UI_icon_edit-ltr-progressive.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/20px-OOjs_UI_icon_edit-ltr-progressive.svg.png 2x" data-file-width="20" data-file-height="20" /></a></span></span></li></ul></div> </td></tr> <tr> <td colspan="2"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold; text-align:left; font-weight:normal; background:transparent;"><div><a href="/wiki/International_Chemical_Identifier" title="International Chemical Identifier">InChI</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.5em; text-align:left;"><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">InChI=1S/C11H12N2O2/c12-9(11(14)15)5-7-6-13-10-4-2-1-3-8(7)10/h1-4,6,9,13H,5,12H2,(H,14,15)/t9-/m0/s1<sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></div><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">Key: QIVBCDIJIAJPQS-VIFPVBQESA-N<sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></div></div></li></ul> </div> </td></tr> <tr> <td colspan="2"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold; text-align:left; font-weight:normal; background:transparent;"><div><a href="/wiki/Simplified_molecular-input_line-entry_system" class="mw-redirect" title="Simplified molecular-input line-entry system">SMILES</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.6em; word-wrap:break-word; text-indent:-1.5em; text-align:left; font-size:97%; line-height:120%;">c1[nH]c2ccccc2c1C[C@H](N)C(=O)O</div></li><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.6em; word-wrap:break-word; text-indent:-1.5em; text-align:left; font-size:97%; line-height:120%;"><a href="/wiki/Zwitterion" title="Zwitterion">Zwitterion</a>: c1[nH]c2ccccc2c1C[C@H]([NH3+])C(=O)[O-]</div></li></ul> </div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Properties </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Chemical_formula" title="Chemical formula">Chemical formula</a></div> </td> <td><span title="Carbon">C</span><sub>11</sub><span title="Hydrogen">H</span><sub>12</sub><span title="Nitrogen">N</span><sub>2</sub><span title="Oxygen">O</span><sub>2</sub> </td></tr> <tr> <td><a href="/wiki/Molar_mass" title="Molar mass">Molar mass</a> </td> <td><span class="nowrap"><span data-sort-value="7002204229000000000♠"></span>204.229</span> g·mol<sup>−1</sup>   </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Aqueous_solution" title="Aqueous solution">Solubility in water</a></div> </td> <td>Soluble: 0.23 g/L at 0 °C,<br /> <p>11.4 g/L at 25 °C,<br /> 17.1 g/L at 50 °C,<br /> 27.95 g/L at 75 °C </p> </td></tr> <tr> <td><a href="/wiki/Solubility" title="Solubility">Solubility</a> </td> <td>Soluble in hot alcohol, alkali hydroxides; insoluble in <a href="/wiki/Chloroform" title="Chloroform">chloroform</a>. </td></tr> <tr> <td><a href="/wiki/Acid_dissociation_constant" title="Acid dissociation constant">Acidity</a> (p<i>K</i><sub>a</sub>) </td> <td>2.38 (carboxyl), 9.39 (amino)<sup id="cite_ref-isbn0-19-855338-2_2-0" class="reference"><a href="#cite_note-isbn0-19-855338-2-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Magnetic_susceptibility" title="Magnetic susceptibility">Magnetic susceptibility</a> (χ)</div> </td> <td>-132.0·10<sup>−6</sup> cm<sup>3</sup>/mol </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Pharmacology </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Anatomical_Therapeutic_Chemical_Classification_System" title="Anatomical Therapeutic Chemical Classification System">ATC code</a></div> </td> <td><a href="/wiki/ATC_code_N06" title="ATC code N06">N06AX02</a> (<span title="www.whocc.no"><a rel="nofollow" class="external text" href="https://www.whocc.no/atc_ddd_index/?code=N06AX02">WHO</a></span>)  </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Supplementary data page </th></tr> <tr> <td colspan="2" style="text-align:center"><a href="/wiki/Tryptophan_(data_page)" title="Tryptophan (data page)">Tryptophan (data page)</a> </td></tr> <tr> <td colspan="2" style="text-align:left; background:#f8eaba; border:1px solid #a2a9b1;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">Except where otherwise noted, data are given for materials in their <a href="/wiki/Standard_state" title="Standard state">standard state</a> (at 25 °C [77 °F], 100 kPa).</div> <div style="margin-top: 0.3em;"></div> <div style="margin-top: 0.3em; text-align: center;"><a href="/wiki/Wikipedia:Chemical_infobox#References" title="Wikipedia:Chemical infobox">Infobox references</a></div> </td></tr> </tbody></table><div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Chemical compound</div> <p><b>Tryptophan</b> (symbol <b>Trp</b> or <b>W</b>)<sup id="cite_ref-IUPAC_3-0" class="reference"><a href="#cite_note-IUPAC-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> is an α-<a href="/wiki/Amino_acid" title="Amino acid">amino acid</a> that is used in the <a href="/wiki/Biosynthesis" title="Biosynthesis">biosynthesis</a> of <a href="/wiki/Protein" title="Protein">proteins</a>. Tryptophan contains an <a href="/wiki/Alpha_and_beta_carbon" class="mw-redirect" title="Alpha and beta carbon"> α</a>-amino group, an α-<a href="/wiki/Carboxylic_acid" title="Carboxylic acid">carboxylic acid</a> group, and a side chain <a href="/wiki/Indole" title="Indole">indole</a>, making it a <a href="/wiki/Polar_molecule" class="mw-redirect" title="Polar molecule">polar molecule</a> with a non-polar <a href="/wiki/Aromatic_hydrocarbon" class="mw-redirect" title="Aromatic hydrocarbon">aromatic</a> <a href="/wiki/Alpha_and_beta_carbon" class="mw-redirect" title="Alpha and beta carbon">beta carbon</a> substituent. Tryptophan is also a precursor to the <a href="/wiki/Neurotransmitter" title="Neurotransmitter">neurotransmitter</a> <a href="/wiki/Serotonin" title="Serotonin">serotonin</a>, the <a href="/wiki/Hormone" title="Hormone">hormone</a> <a href="/wiki/Melatonin" title="Melatonin">melatonin</a>, and <a href="/wiki/Vitamin_B3" title="Vitamin B3">vitamin B<sub>3</sub></a> (niacin).<sup id="cite_ref-4" class="reference"><a href="#cite_note-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> It is <a href="/wiki/Genetic_code" title="Genetic code">encoded</a> by the <a href="/wiki/Codon" class="mw-redirect" title="Codon">codon</a> UGG. </p><p>Like other amino acids, tryptophan is a <a href="/wiki/Zwitterion" title="Zwitterion">zwitterion</a> at <a href="/wiki/Physiological_pH" class="mw-redirect" title="Physiological pH">physiological pH</a> where the amino group is <a href="/wiki/Protonated" class="mw-redirect" title="Protonated">protonated</a> (–<span class="chemf nowrap">NH<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline">+</sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">3</sub></span></span></span>; pK<sub>a</sub> = 9.39) and the carboxylic acid is <a href="/wiki/Deprotonation" title="Deprotonation">deprotonated</a> ( –COO<sup>−</sup>; pK<sub>a</sub> = 2.38).<sup id="cite_ref-PubChem_5-0" class="reference"><a href="#cite_note-PubChem-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> </p><p>Humans and many animals cannot synthesize tryptophan: they need to obtain it through their diet, making it an <a href="/wiki/Essential_amino_acid" title="Essential amino acid">essential amino acid</a>. </p><p>Tryptophan is named after the digestive enzymes <a href="/wiki/Trypsin" title="Trypsin">trypsin</a>, which were used in its first isolation from <a href="/wiki/Casein" title="Casein">casein</a> proteins.<sup id="cite_ref-6" class="reference"><a href="#cite_note-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> It was assigned the <a href="/wiki/List_of_amino_acids_by_one-letter_symbol" class="mw-redirect" title="List of amino acids by one-letter symbol">one-letter symbol</a> W based on the double ring being visually suggestive to the bulky letter.<sup id="cite_ref-:0_7-0" class="reference"><a href="#cite_note-:0-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Function">Function</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Tryptophan&action=edit&section=1" title="Edit section: Function"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure typeof="mw:File/Thumb"><a href="/wiki/File:Tryptophan_metabolism.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/2/24/Tryptophan_metabolism.svg/275px-Tryptophan_metabolism.svg.png" decoding="async" width="275" height="400" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/2/24/Tryptophan_metabolism.svg/413px-Tryptophan_metabolism.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/2/24/Tryptophan_metabolism.svg/550px-Tryptophan_metabolism.svg.png 2x" data-file-width="580" data-file-height="844" /></a><figcaption>Metabolism of <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r920966791"><span class="smallcaps">l</span>-tryptophan into serotonin and melatonin (left) and niacin (right). Transformed functional groups after each chemical reaction are highlighted in red.</figcaption></figure> <p>Amino acids, including tryptophan, are used as building blocks in <a href="/wiki/Protein_biosynthesis" title="Protein biosynthesis">protein biosynthesis</a>, and <a href="/wiki/Protein" title="Protein">proteins</a> are required to sustain life. Tryptophan is among the less common amino acids found in proteins, but it plays important structural or functional roles whenever it occurs. For instance, tryptophan and <a href="/wiki/Tyrosine" title="Tyrosine">tyrosine</a> residues play special roles in "anchoring" <a href="/wiki/Membrane_protein" title="Membrane protein">membrane proteins</a> within the <a href="/wiki/Cell_membrane" title="Cell membrane">cell membrane</a>. Tryptophan, along with other <a href="/wiki/Aromatic_amino_acid" title="Aromatic amino acid">aromatic amino acids</a>, is also important in <a href="/wiki/Glycan-protein_interactions" title="Glycan-protein interactions">glycan-protein interactions</a>. In addition, tryptophan functions as a biochemical <a href="/wiki/Precursor_(chemistry)" title="Precursor (chemistry)">precursor</a> for the following <a href="/wiki/Chemical_compounds" class="mw-redirect" title="Chemical compounds">compounds</a>: </p> <ul><li><a href="/wiki/Serotonin" title="Serotonin">Serotonin</a> (a <a href="/wiki/Neurotransmitter" title="Neurotransmitter">neurotransmitter</a>), synthesized by <a href="/wiki/Tryptophan_hydroxylase" title="Tryptophan hydroxylase">tryptophan hydroxylase</a>.<sup id="cite_ref-pmid6132421_8-0" class="reference"><a href="#cite_note-pmid6132421-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-pmid1704290_9-0" class="reference"><a href="#cite_note-pmid1704290-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup></li> <li><a href="/wiki/Melatonin" title="Melatonin">Melatonin</a> (a <a href="/wiki/Neurohormone" title="Neurohormone">neurohormone</a>) is in turn synthesized from serotonin, via <a href="/wiki/N-Acetyltransferase" class="mw-redirect" title="N-Acetyltransferase">N-acetyltransferase</a> and <a href="/wiki/5-hydroxyindole-O-methyltransferase" class="mw-redirect" title="5-hydroxyindole-O-methyltransferase">5-hydroxyindole-O-methyltransferase</a> enzymes.<sup id="cite_ref-pmid4391290_10-0" class="reference"><a href="#cite_note-pmid4391290-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup></li> <li><a href="/wiki/Kynurenine" title="Kynurenine">Kynurenine</a>, to which tryptophan is mainly (more than 95%) metabolized. Two enzymes, namely <a href="/wiki/Indoleamine_2,3-dioxygenase" title="Indoleamine 2,3-dioxygenase">indoleamine 2,3-dioxygenase</a> (IDO) in the immune system and the brain, and <a href="/wiki/Tryptophan_2,3-dioxygenase" title="Tryptophan 2,3-dioxygenase">tryptophan 2,3-dioxygenase</a> (TDO) in the liver, are responsible for the synthesis of kynurenine from tryptophan. The <a href="/wiki/Kynurenine_pathway" title="Kynurenine pathway">kynurenine pathway</a> of tryptophan catabolism is altered in several diseases, including psychiatric disorders such as <a href="/wiki/Schizophrenia" title="Schizophrenia">schizophrenia</a>,<sup id="cite_ref-Marx-2020_11-0" class="reference"><a href="#cite_note-Marx-2020-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> major depressive disorder,<sup id="cite_ref-Marx-2020_11-1" class="reference"><a href="#cite_note-Marx-2020-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> and <a href="/wiki/Bipolar_disorder" title="Bipolar disorder">bipolar disorder</a>.<sup id="cite_ref-Marx-2020_11-2" class="reference"><a href="#cite_note-Marx-2020-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Bartoli_12-0" class="reference"><a href="#cite_note-Bartoli-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup></li> <li><a href="/wiki/Niacin_(substance)" class="mw-redirect" title="Niacin (substance)">Niacin</a>, also known as vitamin B<sub>3</sub>, is synthesized from tryptophan via <a href="/wiki/Kynurenine" title="Kynurenine">kynurenine</a> and <a href="/wiki/Quinolinic_acid" title="Quinolinic acid">quinolinic acids</a>.<sup id="cite_ref-pmid14284754_13-0" class="reference"><a href="#cite_note-pmid14284754-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup></li> <li><a href="/wiki/Auxin" title="Auxin">Auxins</a> (a class of <a href="/wiki/Phytohormone" class="mw-redirect" title="Phytohormone">phytohormones</a>) are synthesized from tryptophan.<sup id="cite_ref-pmid18394986_14-0" class="reference"><a href="#cite_note-pmid18394986-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup></li></ul> <p>The disorder <a href="/wiki/Fructose_malabsorption" title="Fructose malabsorption">fructose malabsorption</a> causes improper absorption of tryptophan in the intestine, reduced levels of tryptophan in the blood,<sup id="cite_ref-Ledochowski_M,_Widner_B,_Murr_C,_Sperner-Unterweger_B,_Fuchs_D_2001_367–71_15-0" class="reference"><a href="#cite_note-Ledochowski_M,_Widner_B,_Murr_C,_Sperner-Unterweger_B,_Fuchs_D_2001_367–71-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup> and depression.<sup id="cite_ref-16" class="reference"><a href="#cite_note-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup> </p><p>In bacteria that synthesize tryptophan, high cellular levels of this amino acid activate a <a href="/wiki/Repressor" title="Repressor">repressor</a> protein, which binds to the <a href="/wiki/Trp_operon" title="Trp operon">trp operon</a>.<sup id="cite_ref-pmid16285852_17-0" class="reference"><a href="#cite_note-pmid16285852-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup> Binding of this repressor to the tryptophan operon prevents <a href="/wiki/Transcription_(genetics)" class="mw-redirect" title="Transcription (genetics)">transcription</a> of downstream DNA that codes for the enzymes involved in the biosynthesis of tryptophan. So high levels of tryptophan prevent tryptophan synthesis through a <a href="/wiki/Negative_feedback" title="Negative feedback">negative feedback</a> loop, and when the cell's tryptophan levels go down again, transcription from the <a href="/wiki/Trp_operon" title="Trp operon">trp operon</a> resumes. This permits tightly regulated and rapid responses to changes in the cell's internal and external tryptophan levels. </p> <div class="skin-invert-image"> <table role="presentation" cellpadding="0" style="border-spacing:0; clear:left; float:left;"> <tbody><tr> <td><div class="thumb tleft"> <div class="thumbinner" style="width:582px;"> <div style="clear: both; font-weight: bold; font-size: 106.4%; text-align: center; background-color: #F0F8FF;margin-bottom:3px;">Tryptophan metabolism by human gut microbiota <small>(</small><style data-mw-deduplicate="TemplateStyles:r1129693374">.mw-parser-output .hlist dl,.mw-parser-output .hlist ol,.mw-parser-output .hlist ul{margin:0;padding:0}.mw-parser-output .hlist dd,.mw-parser-output .hlist dt,.mw-parser-output .hlist li{margin:0;display:inline}.mw-parser-output .hlist.inline,.mw-parser-output .hlist.inline dl,.mw-parser-output .hlist.inline ol,.mw-parser-output .hlist.inline ul,.mw-parser-output .hlist dl dl,.mw-parser-output .hlist dl ol,.mw-parser-output .hlist dl ul,.mw-parser-output .hlist ol dl,.mw-parser-output .hlist ol ol,.mw-parser-output .hlist ol ul,.mw-parser-output .hlist ul dl,.mw-parser-output .hlist ul ol,.mw-parser-output .hlist ul ul{display:inline}.mw-parser-output .hlist .mw-empty-li{display:none}.mw-parser-output .hlist dt::after{content:": "}.mw-parser-output .hlist dd::after,.mw-parser-output .hlist li::after{content:" · ";font-weight:bold}.mw-parser-output .hlist dd:last-child::after,.mw-parser-output .hlist dt:last-child::after,.mw-parser-output .hlist li:last-child::after{content:none}.mw-parser-output .hlist dd dd:first-child::before,.mw-parser-output .hlist dd dt:first-child::before,.mw-parser-output .hlist dd li:first-child::before,.mw-parser-output .hlist dt dd:first-child::before,.mw-parser-output .hlist dt dt:first-child::before,.mw-parser-output .hlist dt li:first-child::before,.mw-parser-output .hlist li dd:first-child::before,.mw-parser-output .hlist li dt:first-child::before,.mw-parser-output .hlist li li:first-child::before{content:" (";font-weight:normal}.mw-parser-output .hlist dd dd:last-child::after,.mw-parser-output .hlist dd dt:last-child::after,.mw-parser-output .hlist dd li:last-child::after,.mw-parser-output .hlist dt dd:last-child::after,.mw-parser-output .hlist dt dt:last-child::after,.mw-parser-output .hlist dt li:last-child::after,.mw-parser-output .hlist li dd:last-child::after,.mw-parser-output .hlist li dt:last-child::after,.mw-parser-output .hlist li li:last-child::after{content:")";font-weight:normal}.mw-parser-output .hlist ol{counter-reset:listitem}.mw-parser-output .hlist ol>li{counter-increment:listitem}.mw-parser-output .hlist ol>li::before{content:" "counter(listitem)"\a0 "}.mw-parser-output .hlist dd ol>li:first-child::before,.mw-parser-output .hlist dt ol>li:first-child::before,.mw-parser-output .hlist li ol>li:first-child::before{content:" ("counter(listitem)"\a0 "}</style><style data-mw-deduplicate="TemplateStyles:r1239400231">.mw-parser-output .navbar{display:inline;font-size:88%;font-weight:normal}.mw-parser-output .navbar-collapse{float:left;text-align:left}.mw-parser-output .navbar-boxtext{word-spacing:0}.mw-parser-output .navbar ul{display:inline-block;white-space:nowrap;line-height:inherit}.mw-parser-output .navbar-brackets::before{margin-right:-0.125em;content:"[ "}.mw-parser-output .navbar-brackets::after{margin-left:-0.125em;content:" ]"}.mw-parser-output .navbar li{word-spacing:-0.125em}.mw-parser-output .navbar a>span,.mw-parser-output .navbar a>abbr{text-decoration:inherit}.mw-parser-output .navbar-mini abbr{font-variant:small-caps;border-bottom:none;text-decoration:none;cursor:inherit}.mw-parser-output .navbar-ct-full{font-size:114%;margin:0 7em}.mw-parser-output .navbar-ct-mini{font-size:114%;margin:0 4em}html.skin-theme-clientpref-night .mw-parser-output .navbar li a abbr{color:var(--color-base)!important}@media(prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .navbar li a abbr{color:var(--color-base)!important}}@media print{.mw-parser-output .navbar{display:none!important}}</style><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Tryptophan_metabolism_by_human_microbiota" title="Template:Tryptophan metabolism by human microbiota"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Tryptophan_metabolism_by_human_microbiota" title="Template talk:Tryptophan metabolism by human microbiota"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Tryptophan_metabolism_by_human_microbiota" title="Special:EditPage/Template:Tryptophan metabolism by human microbiota"><abbr title="Edit this template">e</abbr></a></li></ul></div><small>)</small></div> <div style="position:relative; width:580px; height:470px; overflow:hidden; border:solid #ccc 1px; background-color:white;"> <div style="left:0px; top:10px; width:600px; position:absolute"> <span typeof="mw:File"><a href="https://commons.wikimedia.org/wiki/File:Microbiota-derived_3-Indolepropionic_acid.svg" title="commons:File:Microbiota-derived 3-Indolepropionic acid.svg"><img alt="Tryptophan metabolism diagram" src="//upload.wikimedia.org/wikipedia/commons/thumb/d/d0/Microbiota-derived_3-Indolepropionic_acid-notext.svg/600px-Microbiota-derived_3-Indolepropionic_acid-notext.svg.png" decoding="async" width="600" height="470" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/d/d0/Microbiota-derived_3-Indolepropionic_acid-notext.svg/900px-Microbiota-derived_3-Indolepropionic_acid-notext.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/d/d0/Microbiota-derived_3-Indolepropionic_acid-notext.svg/1200px-Microbiota-derived_3-Indolepropionic_acid-notext.svg.png 2x" data-file-width="705" data-file-height="552" /></a></span> </div> <div style="text-align:left; font-size:14px; line-height:110%"> <div style="background-color:transparent; color:black"><div id="annotation_205x3" style="position:absolute; left:205px; top:3px; line-height:110%;"><span style="background-color:transparent; color:inherit;"><a class="mw-selflink selflink">Tryptophan</a></span></div> <div id="annotation_127x65" style="position:absolute; left:127px; top:65px; font-size:12px; font-size:12; line-height:14px;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/Clostridium_sporogenes" title="Clostridium sporogenes"><i>Clostridium<br />sporogenes</i></a></span></div> <div id="annotation_252x85" style="position:absolute; left:252px; top:85px; font-size:12px; font-size:12; line-height:14px;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/Lactobacillaceae" title="Lactobacillaceae">Lacto-<br />bacilli</a></span></div> <div id="annotation_292x60" style="position:absolute; left:292px; top:60px; font-size:12px; font-size:12; line-height:14px; text-align:center;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/Tryptophanase" title="Tryptophanase">Tryptophanase</a>-<br />expressing<br />bacteria</span></div> <div id="annotation_148x116" style="position:absolute; left:148px; top:116px; font-size:14px; font-size:14; line-height:16px;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/3-Indolepropionic_acid" title="3-Indolepropionic acid">IPA</a></span></div> <div id="annotation_236x131" style="position:absolute; left:236px; top:131px; font-size:14px; font-size:14; line-height:16px;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/Indole-3-carbaldehyde" title="Indole-3-carbaldehyde">I3A</a></span></div> <div id="annotation_318x115" style="position:absolute; left:318px; top:115px; font-size:14px; font-size:14; line-height:16px;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/Indole" title="Indole">Indole</a></span></div> <div id="annotation_470x174" style="position:absolute; left:470px; top:174px; font-size:18px; font-size:18; line-height:20px; text-align:center;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/Liver" title="Liver">Liver</a></span></div> <div id="annotation_37x301" style="position:absolute; left:37px; top:301px; font-size:18px; font-size:18; line-height:20px;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/Human_brain" title="Human brain">Brain</a></span></div> <div id="annotation_133x352" style="position:absolute; left:133px; top:352px; font-size:14px; font-size:14; line-height:16px;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/3-Indolepropionic_acid" title="3-Indolepropionic acid">IPA</a></span></div> <div id="annotation_236x299" style="position:absolute; left:236px; top:299px; font-size:14px; font-size:14; line-height:16px;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/Indole-3-carbaldehyde" title="Indole-3-carbaldehyde">I3A</a></span></div> <div id="annotation_328x269" style="position:absolute; left:328px; top:269px; font-size:14px; font-size:14; line-height:16px;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/Indole" title="Indole">Indole</a></span></div> <div id="annotation_413x261" style="position:absolute; left:413px; top:261px; font-size:12px; font-size:12; line-height:14px; text-align:center;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/Indoxyl_sulfate" title="Indoxyl sulfate">Indoxyl<br />sulfate</a></span></div> <div id="annotation_350x318" style="position:absolute; left:350px; top:318px; font-size:14px; font-size:14; line-height:16px;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/Activated_charcoal" class="mw-redirect" title="Activated charcoal"><span style="color:red">AST-120</span></a></span></div> <div id="annotation_281x346" style="position:absolute; left:281px; top:346px; font-size:12px; font-size:12; line-height:14px;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/Aryl_hydrocarbon_receptor" title="Aryl hydrocarbon receptor">AhR</a></span></div> <div id="annotation_269x297" style="position:absolute; left:269px; top:297px; font-size:11px; font-size:11; line-height:13px; text-align:center;"><span style="background-color:transparent; color:inherit;">Intestinal<br /><a href="/wiki/Immune_cells" class="mw-redirect" title="Immune cells">immune<br />cells</a></span></div> <div id="annotation_40x209" style="position:absolute; left:40px; top:209px; font-size:18px; font-size:18; line-height:20px; text-align:center;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/Intestinal_epithelium" title="Intestinal epithelium">Intestinal<br />epithelium</a></span></div> <div id="annotation_161.5x231" style="position:absolute; left:161.5px; top:231px; font-size:11px; font-size:11; line-height:13px;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/Pregnane_X_receptor" title="Pregnane X receptor">PXR</a></span></div> <div id="annotation_144x255" style="position:absolute; left:144px; top:255px; font-size:10px; font-size:10; line-height:12px;"><span style="background-color:transparent; color:inherit;">Mucosal homeostasis:<br />↓<a href="/wiki/Tumor_necrosis_factor_alpha" class="mw-redirect" title="Tumor necrosis factor alpha">TNF-α</a><br />↑<a href="/wiki/Tight_junction" title="Tight junction">Junction</a> protein-<br />coding <a href="/wiki/Messenger_RNA" title="Messenger RNA">mRNAs</a></span></div> <div id="annotation_252.5x237" style="position:absolute; left:252.5px; top:237px; font-size:12px; font-size:12; line-height:14px;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/Enteroendocrine_cell#L_cell" title="Enteroendocrine cell">L cell</a></span></div> <div id="annotation_249x265" style="position:absolute; left:249px; top:265px; font-size:12px; font-size:12; line-height:14px;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/Glucagon-like_peptide-1" title="Glucagon-like peptide-1">GLP-1</a></span></div> <div id="annotation_335x227" style="position:absolute; left:335px; top:227px; font-size:12px; font-size:12; line-height:14px;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/Tight_junction" title="Tight junction">T J</a></span></div> <div id="annotation_15x390" style="position:absolute; left:15px; top:390px; font-size:10px; font-size:10; line-height:12px;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/Neuroprotectant" class="mw-redirect" title="Neuroprotectant">Neuroprotectant</a>:<br />↓Activation of <a href="/wiki/Glia" title="Glia">glial cells</a> and <a href="/wiki/Astrocyte" title="Astrocyte">astrocytes</a><br />↓<a href="/wiki/4-Hydroxy-2-nonenal" class="mw-redirect" title="4-Hydroxy-2-nonenal">4-Hydroxy-2-nonenal</a> levels<br />↓<a href="/wiki/DNA_damage" class="mw-redirect" title="DNA damage">DNA damage</a><br />–<a href="/wiki/Antioxidant" title="Antioxidant">Antioxidant</a><br />–Inhibits <a href="/wiki/%CE%92-amyloid" class="mw-redirect" title="Β-amyloid">β-amyloid</a> fibril formation</span></div> <div id="annotation_243x370" style="position:absolute; left:243px; top:370px; font-size:10px; font-size:10; line-height:12px;"><span style="background-color:transparent; color:inherit;">Maintains mucosal reactivity:<br />↑<a href="/wiki/Interleukin_22" title="Interleukin 22">IL-22</a> production</span></div> <div id="annotation_458x290" style="position:absolute; left:458px; top:290px; font-size:10px; font-size:10; line-height:12px;"><span style="background-color:transparent; color:inherit;">Associated with <a href="/wiki/Vascular_disease" title="Vascular disease">vascular disease</a>:<br />↑<a href="/wiki/Oxidative_stress" title="Oxidative stress">Oxidative stress</a><br />↑<a href="/wiki/Smooth_muscle_cell" class="mw-redirect" title="Smooth muscle cell">Smooth muscle cell</a> <a href="/wiki/Cell_proliferation" title="Cell proliferation">proliferation</a><br />↑<a href="/wiki/Aorta" title="Aorta">Aortic wall</a> thickness and <a href="/wiki/Aortic_calcification" class="mw-redirect" title="Aortic calcification">calcification</a></span></div> <div id="annotation_458x391" style="position:absolute; left:458px; top:391px; font-size:10px; font-size:10; line-height:12px;"><span style="background-color:transparent; color:inherit;">Associated with <a href="/wiki/Chronic_kidney_disease" title="Chronic kidney disease">chronic kidney disease</a>:<br />↑<a href="/wiki/Renal_dysfunction" class="mw-redirect" title="Renal dysfunction">Renal dysfunction</a><br />–<a href="/wiki/Uremic_toxin" class="mw-redirect" title="Uremic toxin">Uremic toxin</a></span></div> <div id="annotation_381x448" style="position:absolute; left:381px; top:448px; font-size:18px; font-size:18; line-height:20px;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/Kidney" title="Kidney">Kidneys</a></span></div></div> </div> </div> <div class="thumbcaption" style="clear:left"><div style="float:left;margin-right:0.5em"><span typeof="mw:File"><span title="The image above contains clickable links"><img alt="The image above contains clickable links" src="//upload.wikimedia.org/wikipedia/commons/thumb/e/e6/Interactive_icon.svg/18px-Interactive_icon.svg.png" decoding="async" width="18" height="27" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/e6/Interactive_icon.svg/27px-Interactive_icon.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/e/e6/Interactive_icon.svg/36px-Interactive_icon.svg.png 2x" data-file-width="133" data-file-height="200" /></span></span></div>This diagram shows the biosynthesis of <a href="/wiki/Bioactive_compound" title="Bioactive compound">bioactive compounds</a> (<a href="/wiki/Indole" title="Indole">indole</a> and certain other derivatives) from tryptophan by bacteria in the gut.<sup id="cite_ref-Microbial_biosynthesis_of_bioactive_compounds_18-0" class="reference"><a href="#cite_note-Microbial_biosynthesis_of_bioactive_compounds-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup> Indole is produced from tryptophan by bacteria that express <a href="/wiki/Tryptophanase" title="Tryptophanase">tryptophanase</a>.<sup id="cite_ref-Microbial_biosynthesis_of_bioactive_compounds_18-1" class="reference"><a href="#cite_note-Microbial_biosynthesis_of_bioactive_compounds-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup> <i><a href="/wiki/Clostridium_sporogenes" title="Clostridium sporogenes">Clostridium sporogenes</a></i> metabolizes tryptophan into indole and subsequently <a href="/wiki/3-Indolepropionic_acid" title="3-Indolepropionic acid"><span class="nowrap">3-indolepropionic</span> acid</a> (IPA),<sup id="cite_ref-Microbiome_IPA_19-0" class="reference"><a href="#cite_note-Microbiome_IPA-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup> a highly potent <a href="/wiki/Neuroprotective" class="mw-redirect" title="Neuroprotective">neuroprotective</a> <a href="/wiki/Antioxidant" title="Antioxidant">antioxidant</a> that scavenges <a href="/wiki/Hydroxyl_radical" title="Hydroxyl radical">hydroxyl radicals</a>.<sup id="cite_ref-Microbial_biosynthesis_of_bioactive_compounds_18-2" class="reference"><a href="#cite_note-Microbial_biosynthesis_of_bioactive_compounds-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Human_metabolome_IPA_20-0" class="reference"><a href="#cite_note-Human_metabolome_IPA-20"><span class="cite-bracket">[</span>20<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Indolepropionic_acid_scavenging_21-0" class="reference"><a href="#cite_note-Indolepropionic_acid_scavenging-21"><span class="cite-bracket">[</span>21<span class="cite-bracket">]</span></a></sup> IPA binds to the <a href="/wiki/Pregnane_X_receptor" title="Pregnane X receptor">pregnane X receptor</a> (PXR) in intestinal cells, thereby facilitating mucosal homeostasis and <a href="/wiki/Intestinal_permeability" title="Intestinal permeability">barrier function</a>.<sup id="cite_ref-Microbial_biosynthesis_of_bioactive_compounds_18-3" class="reference"><a href="#cite_note-Microbial_biosynthesis_of_bioactive_compounds-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup> Following <a href="/wiki/Absorption_(pharmacokinetics)" class="mw-redirect" title="Absorption (pharmacokinetics)">absorption</a> from the intestine and <a href="/wiki/Distribution_(pharmacology)" title="Distribution (pharmacology)">distribution</a> to the brain, IPA confers a neuroprotective effect against <a href="/wiki/Cerebral_ischemia" class="mw-redirect" title="Cerebral ischemia">cerebral ischemia</a> and <a href="/wiki/Alzheimer%27s_disease" title="Alzheimer's disease">Alzheimer's disease</a>.<sup id="cite_ref-Microbial_biosynthesis_of_bioactive_compounds_18-4" class="reference"><a href="#cite_note-Microbial_biosynthesis_of_bioactive_compounds-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup> <a href="/wiki/Lactobacillaceae" title="Lactobacillaceae">Lactobacillaceae</a> (<i>Lactobacillus</i> <a href="/wiki/Sensu" title="Sensu">s.l.</a>) species metabolize tryptophan into <a href="/wiki/Indole-3-carboxaldehyde" class="mw-redirect" title="Indole-3-carboxaldehyde">indole-3-aldehyde</a> (I3A) which acts on the <a href="/wiki/Aryl_hydrocarbon_receptor" title="Aryl hydrocarbon receptor">aryl hydrocarbon receptor</a> (AhR) in intestinal immune cells, in turn increasing <a href="/wiki/Interleukin-22" class="mw-redirect" title="Interleukin-22">interleukin-22</a> (IL-22) production.<sup id="cite_ref-Microbial_biosynthesis_of_bioactive_compounds_18-5" class="reference"><a href="#cite_note-Microbial_biosynthesis_of_bioactive_compounds-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup> Indole itself <a href="/wiki/Secretagogue" title="Secretagogue">triggers the secretion</a> of <a href="/wiki/Glucagon-like_peptide-1" title="Glucagon-like peptide-1">glucagon-like peptide-1</a> (GLP-1) in <a href="/wiki/Enteroendocrine_cell#L_cell" title="Enteroendocrine cell">intestinal L cells</a> and acts as a <a href="/wiki/Ligand_(biochemistry)" title="Ligand (biochemistry)">ligand</a> for AhR.<sup id="cite_ref-Microbial_biosynthesis_of_bioactive_compounds_18-6" class="reference"><a href="#cite_note-Microbial_biosynthesis_of_bioactive_compounds-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup> Indole can also be metabolized by the liver into <a href="/wiki/Indoxyl_sulfate" title="Indoxyl sulfate">indoxyl sulfate</a>, a compound that is toxic in high concentrations and associated with <a href="/wiki/Vascular_disease" title="Vascular disease">vascular disease</a> and <a href="/wiki/Renal_dysfunction" class="mw-redirect" title="Renal dysfunction">renal dysfunction</a>.<sup id="cite_ref-Microbial_biosynthesis_of_bioactive_compounds_18-7" class="reference"><a href="#cite_note-Microbial_biosynthesis_of_bioactive_compounds-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup> AST-120 (<a href="/wiki/Activated_charcoal" class="mw-redirect" title="Activated charcoal">activated charcoal</a>), an intestinal <a href="/wiki/Sorbent" title="Sorbent">sorbent</a> that is <a href="/wiki/Oral_administration" title="Oral administration">taken by mouth</a>, <a href="/wiki/Adsorption" title="Adsorption">adsorbs</a> indole, in turn decreasing the concentration of indoxyl sulfate in blood plasma.<sup id="cite_ref-Microbial_biosynthesis_of_bioactive_compounds_18-8" class="reference"><a href="#cite_note-Microbial_biosynthesis_of_bioactive_compounds-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup></div> </div> </div> </td></tr></tbody></table></div> <div style="clear:both;" class=""></div> <div class="mw-heading mw-heading2"><h2 id="Recommended_dietary_allowance">Recommended dietary allowance</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Tryptophan&action=edit&section=2" title="Edit section: Recommended dietary allowance"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>In 2002, the <a href="/wiki/U.S._Institute_of_Medicine" class="mw-redirect" title="U.S. Institute of Medicine">U.S. Institute of Medicine</a> set a <a href="/wiki/Recommended_Dietary_Allowance" class="mw-redirect" title="Recommended Dietary Allowance">Recommended Dietary Allowance</a> (RDA) of 5 mg/kg body weight/day of tryptophan for adults 19 years and over.<sup id="cite_ref-DRItext_22-0" class="reference"><a href="#cite_note-DRItext-22"><span class="cite-bracket">[</span>22<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Dietary_sources">Dietary sources</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Tryptophan&action=edit&section=3" title="Edit section: Dietary sources"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Tryptophan is present in most protein-based foods or dietary proteins. It is particularly plentiful in <a href="/wiki/Chocolate" title="Chocolate">chocolate</a>, <a href="/wiki/Oat" title="Oat">oats</a>, dried <a href="/wiki/Date_Palm" class="mw-redirect" title="Date Palm">dates</a>, <a href="/wiki/Milk" title="Milk">milk</a>, <a href="/wiki/Yogurt" title="Yogurt">yogurt</a>, <a href="/wiki/Cottage_cheese" title="Cottage cheese">cottage cheese</a>, <a href="/wiki/Red_meat" title="Red meat">red meat</a>, <a href="/wiki/Egg_(food)" class="mw-redirect" title="Egg (food)">eggs</a>, <a href="/wiki/Fish" title="Fish">fish</a>, <a href="/wiki/Poultry" title="Poultry">poultry</a>, <a href="/wiki/Sesame" title="Sesame">sesame</a>, <a href="/wiki/Chickpea" title="Chickpea">chickpeas</a>, <a href="/wiki/Almonds" class="mw-redirect" title="Almonds">almonds</a>, <a href="/wiki/Sunflower_seeds" class="mw-redirect" title="Sunflower seeds">sunflower seeds</a>, <a href="/wiki/Pumpkin_seeds" class="mw-redirect" title="Pumpkin seeds">pumpkin seeds</a>, <a href="/wiki/Hemp" title="Hemp">hemp</a> seeds, <a href="/wiki/Buckwheat" title="Buckwheat">buckwheat</a>, <a href="/wiki/Spirulina_(dietary_supplement)" title="Spirulina (dietary supplement)">spirulina</a>, and <a href="/wiki/Peanut" title="Peanut">peanuts</a>. Contrary to the popular belief<sup id="cite_ref-scientificamerican_23-0" class="reference"><a href="#cite_note-scientificamerican-23"><span class="cite-bracket">[</span>23<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-McCue_24-0" class="reference"><a href="#cite_note-McCue-24"><span class="cite-bracket">[</span>24<span class="cite-bracket">]</span></a></sup> that cooked <a href="/wiki/Turkey_meat" title="Turkey meat">turkey</a> contains an abundance of tryptophan, the tryptophan content in turkey is typical of poultry.<sup id="cite_ref-USDA_25-0" class="reference"><a href="#cite_note-USDA-25"><span class="cite-bracket">[</span>25<span class="cite-bracket">]</span></a></sup> </p> <table class="wikitable sortable" style="text-align: center;"> <caption>Tryptophan (Trp) content of various foods<sup id="cite_ref-USDA_25-1" class="reference"><a href="#cite_note-USDA-25"><span class="cite-bracket">[</span>25<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Rambali_26-0" class="reference"><a href="#cite_note-Rambali-26"><span class="cite-bracket">[</span>26<span class="cite-bracket">]</span></a></sup> </caption> <tbody><tr> <th scope="col">Food </th> <th scope="col">Tryptophan <br />[g/100 g of food] </th> <th scope="col">Protein <br />[g/100 g of food] </th> <th scope="col">Tryptophan/protein <br />[%] </th></tr> <tr> <td style="text-align: left;"><a href="/wiki/Egg_white" title="Egg white">Egg white</a>, dried</td> <td>1.00</td> <td>81.10</td> <td>1.23 </td></tr> <tr> <td style="text-align: left;"><a href="/wiki/Spirulina_(dietary_supplement)" title="Spirulina (dietary supplement)">Spirulina</a>, dried</td> <td>0.92</td> <td>57.47</td> <td>1.62 </td></tr> <tr> <td style="text-align: left;"><a href="/wiki/Atlantic_cod" title="Atlantic cod">Cod, Atlantic</a>, dried</td> <td>0.70</td> <td>62.82</td> <td>1.11 </td></tr> <tr> <td style="text-align: left;"><a href="/wiki/Soybeans" class="mw-redirect" title="Soybeans">Soybeans</a>, raw</td> <td>0.59</td> <td>36.49</td> <td>1.62 </td></tr> <tr> <td style="text-align: left;">Cheese, <a href="/wiki/Parmigiano-Reggiano" class="mw-redirect" title="Parmigiano-Reggiano">Parmesan</a></td> <td>0.56</td> <td>37.90</td> <td>1.47 </td></tr> <tr> <td style="text-align: left;"><a href="/wiki/Chia_seed" title="Chia seed">Chia seeds</a>, dried</td> <td>0.44</td> <td>16.50</td> <td>2.64 </td></tr> <tr> <td style="text-align: left;"><a href="/wiki/Sesame_seed" class="mw-redirect" title="Sesame seed">Sesame seed</a></td> <td>0.37</td> <td>17.00</td> <td>2.17 </td></tr> <tr> <td style="text-align: left;"><a href="/wiki/Hemp" title="Hemp">Hemp </a> seed, hulled</td> <td>0.37</td> <td>31.56</td> <td>1.17 </td></tr> <tr> <td style="text-align: left;"><a href="/wiki/Cheddar_cheese" title="Cheddar cheese">Cheese, Cheddar</a></td> <td>0.32</td> <td>24.90</td> <td>1.29 </td></tr> <tr> <td style="text-align: left;"><a href="/wiki/Sunflower_seed" title="Sunflower seed">Sunflower seed</a></td> <td>0.30</td> <td>17.20</td> <td>1.74 </td></tr> <tr> <td style="text-align: left;">Pork, chop</td> <td>0.25</td> <td>19.27</td> <td>1.27 </td></tr> <tr> <td style="text-align: left;"><a href="/wiki/Turkey_meat" title="Turkey meat">Turkey</a></td> <td>0.24</td> <td>21.89</td> <td>1.11 </td></tr> <tr> <td style="text-align: left;"><a href="/wiki/Chicken_(food)" class="mw-redirect" title="Chicken (food)">Chicken</a></td> <td>0.24</td> <td>20.85</td> <td>1.14 </td></tr> <tr> <td style="text-align: left;"><a href="/wiki/Beef" title="Beef">Beef</a></td> <td>0.23</td> <td>20.13</td> <td>1.12 </td></tr> <tr> <td style="text-align: left;"><a href="/wiki/Oat" title="Oat">Oats</a></td> <td>0.23</td> <td>16.89</td> <td>1.39 </td></tr> <tr> <td style="text-align: left;"><a href="/wiki/Salmon" title="Salmon">Salmon</a></td> <td>0.22</td> <td>19.84</td> <td>1.12 </td></tr> <tr> <td style="text-align: left;"><a href="/wiki/Lamb_and_mutton" title="Lamb and mutton">Lamb, chop</a></td> <td>0.21</td> <td>18.33</td> <td>1.17 </td></tr> <tr> <td style="text-align: left;"><a href="/wiki/Perch" title="Perch">Perch, Atlantic</a></td> <td>0.21</td> <td>18.62</td> <td>1.12 </td></tr> <tr> <td style="text-align: left;"><a href="/wiki/Chickpea" title="Chickpea">Chickpeas</a>, raw</td> <td>0.19</td> <td>19.30</td> <td>0.96 </td></tr> <tr> <td style="text-align: left;"><a href="/wiki/Egg_(food)" class="mw-redirect" title="Egg (food)">Egg</a></td> <td>0.17</td> <td>12.58</td> <td>1.33 </td></tr> <tr> <td style="text-align: left;">Wheat flour, white</td> <td>0.13</td> <td>10.33</td> <td>1.23 </td></tr> <tr> <td style="text-align: left;"><a href="/wiki/Baking_chocolate" title="Baking chocolate">Baking chocolate</a>, unsweetened</td> <td>0.13</td> <td>12.90</td> <td>1.23 </td></tr> <tr> <td style="text-align: left;"><a href="/wiki/Milk" title="Milk">Milk</a></td> <td>0.08</td> <td>3.22</td> <td>2.34 </td></tr> <tr> <td style="text-align: left;">Rice, white, medium-grain, cooked</td> <td>0.03</td> <td>2.38</td> <td>1.18 </td></tr> <tr> <td style="text-align: left;"><a href="/wiki/Quinoa" title="Quinoa">Quinoa</a>, uncooked</td> <td>0.17</td> <td>14.12</td> <td>1.20 </td></tr> <tr> <td style="text-align: left;">Quinoa, cooked</td> <td>0.05</td> <td>4.40</td> <td>1.10 </td></tr> <tr> <td style="text-align: left;">Potatoes, russet</td> <td>0.02</td> <td>2.14</td> <td>0.84 </td></tr> <tr> <td style="text-align: left;"><a href="/wiki/Tamarind" title="Tamarind">Tamarind</a></td> <td>0.02</td> <td>2.80</td> <td>0.64 </td></tr> <tr> <td style="text-align: left;"><a href="/wiki/Banana" title="Banana">Banana</a></td> <td>0.01</td> <td>1.03</td> <td>0.87 </td></tr></tbody></table> <div class="mw-heading mw-heading2"><h2 id="Medical_use">Medical use</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Tryptophan&action=edit&section=4" title="Edit section: Medical use"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Depression">Depression</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Tryptophan&action=edit&section=5" title="Edit section: Depression"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Because tryptophan is converted into <a href="/wiki/5-hydroxytryptophan" class="mw-redirect" title="5-hydroxytryptophan">5-hydroxytryptophan</a> (5-HTP) which is then converted into the neurotransmitter serotonin, it has been proposed that consumption of tryptophan or 5-HTP may improve depression symptoms by increasing the level of serotonin in the brain. Tryptophan is sold <a href="/wiki/Over_the_counter" class="mw-redirect" title="Over the counter">over the counter</a> in the <a href="/wiki/United_States" title="United States">United States</a> (after being <a href="#Eosinophilia–myalgia_syndrome">banned to varying extents between 1989 and 2005</a>) and the <a href="/wiki/United_Kingdom" title="United Kingdom">United Kingdom</a> as a <a href="/wiki/Dietary_supplement" title="Dietary supplement">dietary supplement</a> for use as an <a href="/wiki/Antidepressant" title="Antidepressant">antidepressant</a>, <a href="/wiki/Anxiolytic" title="Anxiolytic">anxiolytic</a>, and <a href="/wiki/Sleep_aid" class="mw-redirect" title="Sleep aid">sleep aid</a>. It is also marketed as a <a href="/wiki/Prescription_drug" title="Prescription drug">prescription drug</a> in some European countries for the treatment of <a href="/wiki/Major_depression" class="mw-redirect" title="Major depression">major depression</a>. There is evidence that blood tryptophan levels are unlikely to be altered by changing the diet,<sup id="cite_ref-DOI10.1111/j.1601-5215.2010.00508.x_27-0" class="reference"><a href="#cite_note-DOI10.1111/j.1601-5215.2010.00508.x-27"><span class="cite-bracket">[</span>27<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Fernstrom_28-0" class="reference"><a href="#cite_note-Fernstrom-28"><span class="cite-bracket">[</span>28<span class="cite-bracket">]</span></a></sup> but consuming purified tryptophan increases the serotonin level in the brain, whereas eating foods containing tryptophan does not.<sup id="cite_ref-Wurtman_1980_29-0" class="reference"><a href="#cite_note-Wurtman_1980-29"><span class="cite-bracket">[</span>29<span class="cite-bracket">]</span></a></sup> </p><p>In 2001 a <a href="/wiki/Cochrane_review" class="mw-redirect" title="Cochrane review">Cochrane review</a> of the effect of 5-HTP and tryptophan on depression was published. The authors included only studies of a high rigor and included both 5-HTP and tryptophan in their review because of the limited data on either. Of 108 studies of 5-HTP and tryptophan on depression published between 1966 and 2000, only two met the authors' quality standards for inclusion, totaling 64 study participants. The substances were more effective than <a href="/wiki/Placebo" title="Placebo">placebo</a> in the two studies included but the authors state that "the evidence was of insufficient quality to be conclusive" and note that "because alternative antidepressants exist which have been proven to be effective and safe, the clinical usefulness of 5-HTP and tryptophan is limited at present".<sup id="cite_ref-pmid11687048_30-0" class="reference"><a href="#cite_note-pmid11687048-30"><span class="cite-bracket">[</span>30<span class="cite-bracket">]</span></a></sup> The use of tryptophan as an <a href="/wiki/Adjuvant_therapy" title="Adjuvant therapy">adjunctive therapy</a> in addition to standard treatment for mood and anxiety disorders is not supported by the scientific evidence.<sup id="cite_ref-pmid11687048_30-1" class="reference"><a href="#cite_note-pmid11687048-30"><span class="cite-bracket">[</span>30<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Ravindran_31-0" class="reference"><a href="#cite_note-Ravindran-31"><span class="cite-bracket">[</span>31<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Insomnia">Insomnia</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Tryptophan&action=edit&section=6" title="Edit section: Insomnia"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The <a href="/wiki/American_Academy_of_Sleep_Medicine" title="American Academy of Sleep Medicine">American Academy of Sleep Medicine</a>'s 2017 <a href="/wiki/Clinical_practice_guideline" class="mw-redirect" title="Clinical practice guideline">clinical practice guidelines</a> recommended against the use of tryptophan in the treatment of insomnia due to poor effectiveness.<sup id="cite_ref-pmid27998379_32-0" class="reference"><a href="#cite_note-pmid27998379-32"><span class="cite-bracket">[</span>32<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Side_effects">Side effects</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Tryptophan&action=edit&section=7" title="Edit section: Side effects"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Potential <a href="/wiki/Side_effect" title="Side effect">side effects</a> of tryptophan supplementation include <a href="/wiki/Nausea" title="Nausea">nausea</a>, <a href="/wiki/Diarrhea" title="Diarrhea">diarrhea</a>, <a href="/wiki/Drowsiness" class="mw-redirect" title="Drowsiness">drowsiness</a>, <a href="/wiki/Lightheadedness" title="Lightheadedness">lightheadedness</a>, <a href="/wiki/Headache" title="Headache">headache</a>, <a href="/wiki/Xerostomia" title="Xerostomia">dry mouth</a>, <a href="/wiki/Blurred_vision" title="Blurred vision">blurred vision</a>, <a href="/wiki/Sedation" title="Sedation">sedation</a>, <a href="/wiki/Euphoria" title="Euphoria">euphoria</a>, and <a href="/wiki/Nystagmus" title="Nystagmus">nystagmus</a> (involuntary eye movements).<sup id="cite_ref-pmid23077196_33-0" class="reference"><a href="#cite_note-pmid23077196-33"><span class="cite-bracket">[</span>33<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-pmid22589230_34-0" class="reference"><a href="#cite_note-pmid22589230-34"><span class="cite-bracket">[</span>34<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Interactions">Interactions</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Tryptophan&action=edit&section=8" title="Edit section: Interactions"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Tryptophan taken as a dietary supplement (such as in tablet form) has the potential to cause <a href="/wiki/Serotonin_syndrome" title="Serotonin syndrome">serotonin syndrome</a> when combined with antidepressants of the <a href="/wiki/Monoamine_oxidase_inhibitor" title="Monoamine oxidase inhibitor">MAOI</a> or <a href="/wiki/Selective_serotonin_reuptake_inhibitor" title="Selective serotonin reuptake inhibitor">SSRI</a> class or other strongly serotonergic drugs.<sup id="cite_ref-pmid22589230_34-1" class="reference"><a href="#cite_note-pmid22589230-34"><span class="cite-bracket">[</span>34<span class="cite-bracket">]</span></a></sup> Because tryptophan supplementation has not been thoroughly studied in a clinical setting, its <a href="/wiki/Drug_interaction" title="Drug interaction">interactions</a> with other drugs are not well known.<sup id="cite_ref-pmid11687048_30-2" class="reference"><a href="#cite_note-pmid11687048-30"><span class="cite-bracket">[</span>30<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Isolation">Isolation</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Tryptophan&action=edit&section=9" title="Edit section: Isolation"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The isolation of tryptophan was first reported by <a href="/wiki/Frederick_Hopkins" class="mw-redirect" title="Frederick Hopkins">Frederick Hopkins</a> in 1901.<sup id="cite_ref-pmid16992614_35-0" class="reference"><a href="#cite_note-pmid16992614-35"><span class="cite-bracket">[</span>35<span class="cite-bracket">]</span></a></sup> Hopkins recovered tryptophan from <a href="/wiki/Hydrolysis" title="Hydrolysis">hydrolysed</a> <a href="/wiki/Casein" title="Casein">casein</a>, recovering 4–8 g of tryptophan from 600 g of crude casein.<sup id="cite_ref-Cox_1943_36-0" class="reference"><a href="#cite_note-Cox_1943-36"><span class="cite-bracket">[</span>36<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Biosynthesis_and_industrial_production">Biosynthesis and industrial production</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Tryptophan&action=edit&section=10" title="Edit section: Biosynthesis and industrial production"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>As an essential amino acid, tryptophan is not synthesized from simpler substances in humans and other animals, so it needs to be present in the diet in the form of tryptophan-containing proteins. Plants and <a href="/wiki/Microorganism" title="Microorganism">microorganisms</a> commonly synthesize tryptophan from <a href="/wiki/Shikimic_acid" title="Shikimic acid">shikimic acid</a> or <a href="/wiki/Anthranilic_acid" title="Anthranilic acid">anthranilate</a>:<sup id="cite_ref-pmid7640526_37-0" class="reference"><a href="#cite_note-pmid7640526-37"><span class="cite-bracket">[</span>37<span class="cite-bracket">]</span></a></sup> anthranilate condenses with <a href="/wiki/Phosphoribosylpyrophosphate" class="mw-redirect" title="Phosphoribosylpyrophosphate">phosphoribosylpyrophosphate</a> (PRPP), generating <a href="/wiki/Pyrophosphate" title="Pyrophosphate">pyrophosphate</a> as a by-product. The ring of the <a href="/wiki/Ribose" title="Ribose">ribose</a> <a href="/wiki/Moiety_(chemistry)" title="Moiety (chemistry)">moiety</a> is opened and subjected to reductive <a href="/wiki/Decarboxylation" title="Decarboxylation">decarboxylation</a>, producing indole-3-glycerol phosphate; this, in turn, is transformed into <a href="/wiki/Indole" title="Indole">indole</a>. In the last step, <a href="/wiki/Tryptophan_synthase" title="Tryptophan synthase">tryptophan synthase</a> <a href="/wiki/Catalysis" title="Catalysis">catalyzes</a> the formation of tryptophan from indole and the amino acid <a href="/wiki/Serine" title="Serine">serine</a>. </p> <dl><dd><span typeof="mw:File"><a href="/wiki/File:Tryptophan_biosynthesis_(en).svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/9/93/Tryptophan_biosynthesis_%28en%29.svg/900px-Tryptophan_biosynthesis_%28en%29.svg.png" decoding="async" width="900" height="328" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/9/93/Tryptophan_biosynthesis_%28en%29.svg/1350px-Tryptophan_biosynthesis_%28en%29.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/9/93/Tryptophan_biosynthesis_%28en%29.svg/1800px-Tryptophan_biosynthesis_%28en%29.svg.png 2x" data-file-width="1173" data-file-height="427" /></a></span></dd></dl> <p>The industrial production of tryptophan is also <a href="/wiki/Biosynthesis" title="Biosynthesis">biosynthetic</a> and is based on the <a href="/wiki/Industrial_fermentation" title="Industrial fermentation">fermentation</a> of <a href="/wiki/Serine" title="Serine">serine</a> and <a href="/wiki/Indole" title="Indole">indole</a> using either wild-type or <a href="/wiki/Genetically_modified_bacterium" class="mw-redirect" title="Genetically modified bacterium">genetically modified bacteria</a> such as <i><a href="/wiki/Bacillus_amyloliquefaciens" title="Bacillus amyloliquefaciens">B. amyloliquefaciens</a></i>, <i><a href="/wiki/Bacillus_subtilis" title="Bacillus subtilis">B. subtilis</a></i>, <i><a href="/wiki/Corynebacterium_glutamicum" title="Corynebacterium glutamicum">C. glutamicum</a></i> or <i><a href="/wiki/Escherichia_coli" title="Escherichia coli">E. coli</a></i>. These strains carry <a href="/wiki/Mutation" title="Mutation">mutations</a> that prevent the reuptake of <a href="/wiki/Aromatic_amino_acids" class="mw-redirect" title="Aromatic amino acids">aromatic amino acids</a> or multiple/overexpressed <a href="/wiki/Trp_operon" title="Trp operon">trp operons</a>. The conversion is catalyzed by the enzyme <a href="/wiki/Tryptophan_synthase" title="Tryptophan synthase">tryptophan synthase</a>.<sup id="cite_ref-pmid12523387_38-0" class="reference"><a href="#cite_note-pmid12523387-38"><span class="cite-bracket">[</span>38<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-pmid22138494_39-0" class="reference"><a href="#cite_note-pmid22138494-39"><span class="cite-bracket">[</span>39<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-pmid18725290_40-0" class="reference"><a href="#cite_note-pmid18725290-40"><span class="cite-bracket">[</span>40<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Society_and_culture">Society and culture</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Tryptophan&action=edit&section=11" title="Edit section: Society and culture"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Showa_Denko_contamination_scandal">Showa Denko contamination scandal</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Tryptophan&action=edit&section=12" title="Edit section: Showa Denko contamination scandal"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>There was a large <a href="/wiki/Outbreak" class="mw-redirect" title="Outbreak">outbreak</a> of <a href="/wiki/Eosinophilia-myalgia_syndrome" class="mw-redirect" title="Eosinophilia-myalgia syndrome">eosinophilia-myalgia syndrome</a> (EMS) in the U.S. in 1989, with more than 1,500 cases reported to the <a href="/wiki/Centers_for_Disease_Control_and_Prevention" title="Centers for Disease Control and Prevention">CDC</a> and at least 37 deaths.<sup id="cite_ref-41" class="reference"><a href="#cite_note-41"><span class="cite-bracket">[</span>41<span class="cite-bracket">]</span></a></sup> After preliminary investigation revealed that the outbreak was linked to intake of tryptophan, the U.S. <a href="/wiki/Food_and_Drug_Administration" title="Food and Drug Administration">Food and Drug Administration</a> (FDA) recalled tryptophan supplements in 1989 and banned most public sales in 1990,<sup id="cite_ref-FDA_Tryptophan_Info_42-0" class="reference"><a href="#cite_note-FDA_Tryptophan_Info-42"><span class="cite-bracket">[</span>42<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-43" class="reference"><a href="#cite_note-43"><span class="cite-bracket">[</span>43<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-44" class="reference"><a href="#cite_note-44"><span class="cite-bracket">[</span>44<span class="cite-bracket">]</span></a></sup> with other countries following suit.<sup id="cite_ref-45" class="reference"><a href="#cite_note-45"><span class="cite-bracket">[</span>45<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-46" class="reference"><a href="#cite_note-46"><span class="cite-bracket">[</span>46<span class="cite-bracket">]</span></a></sup> </p><p>Subsequent studies suggested that EMS was linked to specific batches of <small>L</small>-tryptophan supplied by a single large Japanese manufacturer, <a href="/wiki/Showa_Denko" title="Showa Denko">Showa Denko</a>.<sup id="cite_ref-FDA_Tryptophan_Info_42-1" class="reference"><a href="#cite_note-FDA_Tryptophan_Info-42"><span class="cite-bracket">[</span>42<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-pmid2355442_47-0" class="reference"><a href="#cite_note-pmid2355442-47"><span class="cite-bracket">[</span>47<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-pmid8496862_48-0" class="reference"><a href="#cite_note-pmid8496862-48"><span class="cite-bracket">[</span>48<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-pmid8895184_49-0" class="reference"><a href="#cite_note-pmid8895184-49"><span class="cite-bracket">[</span>49<span class="cite-bracket">]</span></a></sup> It eventually became clear that recent batches of Showa Denko's <small>L</small>-tryptophan were contaminated by trace impurities, which were subsequently thought to be responsible for the 1989 EMS outbreak.<sup id="cite_ref-FDA_Tryptophan_Info_42-2" class="reference"><a href="#cite_note-FDA_Tryptophan_Info-42"><span class="cite-bracket">[</span>42<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-pmid2270484_50-0" class="reference"><a href="#cite_note-pmid2270484-50"><span class="cite-bracket">[</span>50<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-pmid1544609_51-0" class="reference"><a href="#cite_note-pmid1544609-51"><span class="cite-bracket">[</span>51<span class="cite-bracket">]</span></a></sup> However, other evidence suggests that tryptophan itself may be a potentially major contributory factor in EMS.<sup id="cite_ref-pmid16307217_52-0" class="reference"><a href="#cite_note-pmid16307217-52"><span class="cite-bracket">[</span>52<span class="cite-bracket">]</span></a></sup> There are also claims that a precursor reached sufficient concentrations to form a toxic <a href="/wiki/Dimer_(chemistry)" class="mw-redirect" title="Dimer (chemistry)">dimer</a>.<sup id="cite_ref-pred_53-0" class="reference"><a href="#cite_note-pred-53"><span class="cite-bracket">[</span>53<span class="cite-bracket">]</span></a></sup> </p><p>The FDA loosened its restrictions on sales and marketing of tryptophan in February 2001,<sup id="cite_ref-FDA_Tryptophan_Info_42-3" class="reference"><a href="#cite_note-FDA_Tryptophan_Info-42"><span class="cite-bracket">[</span>42<span class="cite-bracket">]</span></a></sup> but continued to limit the importation of tryptophan not intended for an exempted use until 2005.<sup id="cite_ref-54" class="reference"><a href="#cite_note-54"><span class="cite-bracket">[</span>54<span class="cite-bracket">]</span></a></sup> </p><p>The fact that the Showa Denko facility used <a href="/wiki/Genetically_engineered" class="mw-redirect" title="Genetically engineered">genetically engineered</a> bacteria to produce the contaminated batches of <small>L</small>-tryptophan later found to have caused the outbreak of eosinophilia-myalgia syndrome has been cited as evidence of a need for "close monitoring of the chemical purity of biotechnology-derived products".<sup id="cite_ref-pmid7765187_55-0" class="reference"><a href="#cite_note-pmid7765187-55"><span class="cite-bracket">[</span>55<span class="cite-bracket">]</span></a></sup> Those calling for purity monitoring have, in turn, been criticized as anti-<a href="/wiki/Genetically_modified_organism" title="Genetically modified organism">GMO</a> activists who overlook possible non-GMO causes of contamination and threaten the development of biotech.<sup id="cite_ref-Science2000_56-0" class="reference"><a href="#cite_note-Science2000-56"><span class="cite-bracket">[</span>56<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Turkey_meat_and_drowsiness_hypothesis">Turkey meat and drowsiness hypothesis</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Tryptophan&action=edit&section=13" title="Edit section: Turkey meat and drowsiness hypothesis"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">See also: <a href="/wiki/Postprandial_somnolence#Turkey_and_tryptophan" title="Postprandial somnolence">Postprandial somnolence § Turkey and tryptophan</a></div> <p>A common assertion in the US and the UK<sup id="cite_ref-57" class="reference"><a href="#cite_note-57"><span class="cite-bracket">[</span>57<span class="cite-bracket">]</span></a></sup> is that heavy consumption of <a href="/wiki/Turkey_meat" title="Turkey meat">turkey meat</a>—as seen during <a href="/wiki/Thanksgiving_(United_States)" title="Thanksgiving (United States)">Thanksgiving</a> and <a href="/wiki/Christmas" title="Christmas">Christmas</a>—results in <a href="/wiki/Somnolence" title="Somnolence">drowsiness</a>, due to high levels of tryptophan contained in turkey.<sup id="cite_ref-McCue_24-1" class="reference"><a href="#cite_note-McCue-24"><span class="cite-bracket">[</span>24<span class="cite-bracket">]</span></a></sup> However, the amount of tryptophan in turkey is comparable with that of other meats.<sup id="cite_ref-scientificamerican_23-1" class="reference"><a href="#cite_note-scientificamerican-23"><span class="cite-bracket">[</span>23<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-USDA_25-2" class="reference"><a href="#cite_note-USDA-25"><span class="cite-bracket">[</span>25<span class="cite-bracket">]</span></a></sup> <a href="/wiki/Postprandial_somnolence" title="Postprandial somnolence">Drowsiness after eating</a> may be caused by other foods eaten with the turkey, particularly <a href="/wiki/Carbohydrate" title="Carbohydrate">carbohydrates</a>.<sup id="cite_ref-HighBeam_Research_Interview_58-0" class="reference"><a href="#cite_note-HighBeam_Research_Interview-58"><span class="cite-bracket">[</span>58<span class="cite-bracket">]</span></a></sup> Ingestion of a meal rich in carbohydrates triggers the release of <a href="/wiki/Insulin" title="Insulin">insulin</a>.<sup id="cite_ref-pmid3279747_59-0" class="reference"><a href="#cite_note-pmid3279747-59"><span class="cite-bracket">[</span>59<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-pmid12499331_60-0" class="reference"><a href="#cite_note-pmid12499331-60"><span class="cite-bracket">[</span>60<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-pmid17284739_61-0" class="reference"><a href="#cite_note-pmid17284739-61"><span class="cite-bracket">[</span>61<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Banks-2012_62-0" class="reference"><a href="#cite_note-Banks-2012-62"><span class="cite-bracket">[</span>62<span class="cite-bracket">]</span></a></sup> Insulin in turn stimulates the uptake of large neutral <a href="/wiki/Branched-chain_amino_acids" class="mw-redirect" title="Branched-chain amino acids">branched-chain amino acids</a> (BCAA), but not tryptophan, into muscle, increasing the ratio of tryptophan to BCAA in the blood stream. The resulting increased tryptophan ratio reduces competition at the <a href="/wiki/Large_neutral_amino_acid_transporter" class="mw-redirect" title="Large neutral amino acid transporter">large neutral amino acid transporter</a> (which transports both BCAA and aromatic amino acids), resulting in more uptake of tryptophan across the <a href="/wiki/Blood%E2%80%93brain_barrier" title="Blood–brain barrier">blood–brain barrier</a> into the <a href="/wiki/Cerebrospinal_fluid" title="Cerebrospinal fluid">cerebrospinal fluid</a> (CSF).<sup id="cite_ref-Banks-2012_62-1" class="reference"><a href="#cite_note-Banks-2012-62"><span class="cite-bracket">[</span>62<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-pmid1148286_63-0" class="reference"><a href="#cite_note-pmid1148286-63"><span class="cite-bracket">[</span>63<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-pmid6538743_64-0" class="reference"><a href="#cite_note-pmid6538743-64"><span class="cite-bracket">[</span>64<span class="cite-bracket">]</span></a></sup> Once in the CSF, tryptophan is converted into <a href="/wiki/Serotonin" title="Serotonin">serotonin</a> in the <a href="/wiki/Raphe_nuclei" title="Raphe nuclei">raphe nuclei</a> by the normal enzymatic pathway.<sup id="cite_ref-pmid12499331_60-1" class="reference"><a href="#cite_note-pmid12499331-60"><span class="cite-bracket">[</span>60<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-pmid5120086_65-0" class="reference"><a href="#cite_note-pmid5120086-65"><span class="cite-bracket">[</span>65<span class="cite-bracket">]</span></a></sup> The resultant serotonin is further metabolised into the hormone <a href="/wiki/Melatonin" title="Melatonin">melatonin</a>—which is an important mediator of the <a href="/wiki/Circadian_rhythm" title="Circadian rhythm">circadian rhythm</a><sup id="cite_ref-66" class="reference"><a href="#cite_note-66"><span class="cite-bracket">[</span>66<span class="cite-bracket">]</span></a></sup>—by the <a href="/wiki/Pineal_gland" title="Pineal gland">pineal gland</a>.<sup id="cite_ref-pmid4391290_10-1" class="reference"><a href="#cite_note-pmid4391290-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> Hence, these data suggest that "feast-induced drowsiness"—or <a href="/wiki/Postprandial_somnolence" title="Postprandial somnolence">postprandial somnolence</a>—may be the result of a heavy meal rich in carbohydrates, which indirectly increases the production of melatonin in the brain, and thereby promotes sleep.<sup id="cite_ref-pmid3279747_59-1" class="reference"><a href="#cite_note-pmid3279747-59"><span class="cite-bracket">[</span>59<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-pmid12499331_60-2" class="reference"><a href="#cite_note-pmid12499331-60"><span class="cite-bracket">[</span>60<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-pmid17284739_61-1" class="reference"><a href="#cite_note-pmid17284739-61"><span class="cite-bracket">[</span>61<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-pmid5120086_65-1" class="reference"><a href="#cite_note-pmid5120086-65"><span class="cite-bracket">[</span>65<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Research">Research</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Tryptophan&action=edit&section=14" title="Edit section: Research"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Yeast_amino_acid_metabolism">Yeast amino acid metabolism</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Tryptophan&action=edit&section=15" title="Edit section: Yeast amino acid metabolism"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>In 1912 <a href="/wiki/Felix_Ehrlich" title="Felix Ehrlich">Felix Ehrlich</a> demonstrated that <a href="/wiki/Yeast" title="Yeast">yeast</a> metabolizes the natural amino acids essentially by splitting off <a href="/wiki/Carbon_dioxide" title="Carbon dioxide">carbon dioxide</a> and replacing the <a href="/wiki/Amine" title="Amine">amino group</a> with a <a href="/wiki/Hydroxyl" class="mw-redirect" title="Hydroxyl">hydroxyl group</a>. By this <a href="/wiki/Chemical_reaction" title="Chemical reaction">reaction</a>, tryptophan gives rise to <a href="/wiki/Tryptophol" title="Tryptophol">tryptophol</a>.<sup id="cite_ref-67" class="reference"><a href="#cite_note-67"><span class="cite-bracket">[</span>67<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Serotonin_precursor">Serotonin precursor</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Tryptophan&action=edit&section=16" title="Edit section: Serotonin precursor"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Tryptophan affects brain serotonin synthesis when given orally in a purified form and is used to modify serotonin levels for research.<sup id="cite_ref-Wurtman_1980_29-1" class="reference"><a href="#cite_note-Wurtman_1980-29"><span class="cite-bracket">[</span>29<span class="cite-bracket">]</span></a></sup> Low brain serotonin level is induced by administration of tryptophan-poor protein in a technique called <a href="/wiki/Acute_tryptophan_depletion" title="Acute tryptophan depletion">acute tryptophan depletion</a>.<sup id="cite_ref-pmid23428157_68-0" class="reference"><a href="#cite_note-pmid23428157-68"><span class="cite-bracket">[</span>68<span class="cite-bracket">]</span></a></sup> Studies using this method have evaluated the effect of serotonin on mood and social behavior, finding that serotonin reduces aggression and increases agreeableness.<sup id="cite_ref-pmid23440461_69-0" class="reference"><a href="#cite_note-pmid23440461-69"><span class="cite-bracket">[</span>69<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Psychedelic_effects">Psychedelic effects</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Tryptophan&action=edit&section=17" title="Edit section: Psychedelic effects"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">See also: <a href="/wiki/5-Hydroxytryptophan#Psychedelic_effects" title="5-Hydroxytryptophan">5-Hydroxytryptophan § Psychedelic effects</a></div> <p>Tryptophan produces the <a href="/wiki/Head-twitch_response" title="Head-twitch response">head-twitch response</a> (HTR) in rodents when administered at sufficiently high doses.<sup id="cite_ref-HalberstadtGeyer2018_70-0" class="reference"><a href="#cite_note-HalberstadtGeyer2018-70"><span class="cite-bracket">[</span>70<span class="cite-bracket">]</span></a></sup> The HTR is induced by <a href="/wiki/Serotonergic_psychedelic" class="mw-redirect" title="Serotonergic psychedelic">serotonergic psychedelics</a> like <a href="/wiki/Lysergic_acid_diethylamide" class="mw-redirect" title="Lysergic acid diethylamide">lysergic acid diethylamide</a> (LSD) and <a href="/wiki/Psilocybin" title="Psilocybin">psilocybin</a> and is a behavioral proxy of psychedelic effects.<sup id="cite_ref-CanalMorgan2012_71-0" class="reference"><a href="#cite_note-CanalMorgan2012-71"><span class="cite-bracket">[</span>71<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-KozlenkovGonzález-Maeso2013_72-0" class="reference"><a href="#cite_note-KozlenkovGonzález-Maeso2013-72"><span class="cite-bracket">[</span>72<span class="cite-bracket">]</span></a></sup> Tryptophan is converted into the <a href="/wiki/Trace_amine" title="Trace amine">trace amine</a> <a href="/wiki/Tryptamine" title="Tryptamine">tryptamine</a> and tryptamine is <i>N</i>-<a href="/wiki/Methyl_group" title="Methyl group">methylated</a> by <a href="/wiki/Indolethylamine_N-methyltransferase" class="mw-redirect" title="Indolethylamine N-methyltransferase">indolethylamine <i>N</i>-methyltransferase</a> (INMT) into <a href="/wiki/N-methyltryptamine" class="mw-redirect" title="N-methyltryptamine"><i>N</i>-methyltryptamine</a> (NMT) and <a href="/wiki/Dimethyltryptamine" class="mw-redirect" title="Dimethyltryptamine"><i>N</i>,<i>N</i>-dimethyltryptamine</a> (<i>N</i>,<i>N</i>-DMT), which are known serotonergic psychedelics.<sup id="cite_ref-HalberstadtGeyer2018_70-1" class="reference"><a href="#cite_note-HalberstadtGeyer2018-70"><span class="cite-bracket">[</span>70<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-CarbonaroGatch2016_73-0" class="reference"><a href="#cite_note-CarbonaroGatch2016-73"><span class="cite-bracket">[</span>73<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Barker2018_74-0" class="reference"><a href="#cite_note-Barker2018-74"><span class="cite-bracket">[</span>74<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-CameronOlson2018_75-0" class="reference"><a href="#cite_note-CameronOlson2018-75"><span class="cite-bracket">[</span>75<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-ColosimoBorsellinoKrider2024_76-0" class="reference"><a href="#cite_note-ColosimoBorsellinoKrider2024-76"><span class="cite-bracket">[</span>76<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-AraújoCarvalhoBastosMde2015_77-0" class="reference"><a href="#cite_note-AraújoCarvalhoBastosMde2015-77"><span class="cite-bracket">[</span>77<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Fluorescence">Fluorescence</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Tryptophan&action=edit&section=18" title="Edit section: Fluorescence"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">Main article: <a href="/wiki/Fluorescence_spectroscopy#Tryptophan_fluorescence" title="Fluorescence spectroscopy">Fluorescence spectroscopy § Tryptophan fluorescence</a></div> <p>Tryptophan is an important intrinsic fluorescent probe (amino acid), which can be used to estimate the nature of the microenvironment around the tryptophan residue. Most of the intrinsic fluorescence emissions of a folded protein are due to excitation of tryptophan residues. </p> <div class="mw-heading mw-heading2"><h2 id="See_also">See also</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Tryptophan&action=edit&section=19" title="Edit section: See also"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a href="/wiki/5-Hydroxytryptophan" title="5-Hydroxytryptophan">5-Hydroxytryptophan</a> (5-HTP)</li> <li><a href="/wiki/%CE%91-Methyltryptophan" title="Α-Methyltryptophan">α-Methyltryptophan</a></li> <li><a href="/wiki/Acree%E2%80%93Rosenheim_reaction" title="Acree–Rosenheim reaction">Acree–Rosenheim reaction</a></li> <li><a href="/wiki/Adamkiewicz_reaction" title="Adamkiewicz reaction">Adamkiewicz reaction</a></li> <li><a href="/wiki/Attenuator_(genetics)" title="Attenuator (genetics)">Attenuator (genetics)</a></li> <li><a href="/wiki/N,N-Dimethyltryptamine" title="N,N-Dimethyltryptamine"><i>N</i>,<i>N</i>-Dimethyltryptamine</a></li> <li><a href="/wiki/Hopkins%E2%80%93Cole_reaction" title="Hopkins–Cole reaction">Hopkins–Cole reaction</a></li> <li><a href="/wiki/Serotonin" title="Serotonin">Serotonin</a></li> <li><a href="/wiki/Tryptamine" title="Tryptamine">Tryptamine</a></li></ul> <div class="mw-heading mw-heading2"><h2 id="References">References</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Tryptophan&action=edit&section=20" title="Edit section: References"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1239543626">.mw-parser-output .reflist{margin-bottom:0.5em;list-style-type:decimal}@media screen{.mw-parser-output .reflist{font-size:90%}}.mw-parser-output .reflist .references{font-size:100%;margin-bottom:0;list-style-type:inherit}.mw-parser-output .reflist-columns-2{column-width:30em}.mw-parser-output .reflist-columns-3{column-width:25em}.mw-parser-output .reflist-columns{margin-top:0.3em}.mw-parser-output .reflist-columns ol{margin-top:0}.mw-parser-output .reflist-columns li{page-break-inside:avoid;break-inside:avoid-column}.mw-parser-output .reflist-upper-alpha{list-style-type:upper-alpha}.mw-parser-output .reflist-upper-roman{list-style-type:upper-roman}.mw-parser-output .reflist-lower-alpha{list-style-type:lower-alpha}.mw-parser-output .reflist-lower-greek{list-style-type:lower-greek}.mw-parser-output .reflist-lower-roman{list-style-type:lower-roman}</style><div class="reflist"> <div class="mw-references-wrap mw-references-columns"><ol class="references"> <li id="cite_note-Görbitz-1"><span class="mw-cite-backlink">^ <a href="#cite_ref-Görbitz_1-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Görbitz_1-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><style data-mw-deduplicate="TemplateStyles:r1238218222">.mw-parser-output cite.citation{font-style:inherit;word-wrap:break-word}.mw-parser-output .citation q{quotes:"\"""\"""'""'"}.mw-parser-output .citation:target{background-color:rgba(0,127,255,0.133)}.mw-parser-output .id-lock-free.id-lock-free a{background:url("//upload.wikimedia.org/wikipedia/commons/6/65/Lock-green.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-limited.id-lock-limited a,.mw-parser-output .id-lock-registration.id-lock-registration a{background:url("//upload.wikimedia.org/wikipedia/commons/d/d6/Lock-gray-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-subscription.id-lock-subscription a{background:url("//upload.wikimedia.org/wikipedia/commons/a/aa/Lock-red-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .cs1-ws-icon a{background:url("//upload.wikimedia.org/wikipedia/commons/4/4c/Wikisource-logo.svg")right 0.1em center/12px no-repeat}body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-free a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-limited a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-registration a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-subscription a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .cs1-ws-icon a{background-size:contain;padding:0 1em 0 0}.mw-parser-output .cs1-code{color:inherit;background:inherit;border:none;padding:inherit}.mw-parser-output .cs1-hidden-error{display:none;color:var(--color-error,#d33)}.mw-parser-output .cs1-visible-error{color:var(--color-error,#d33)}.mw-parser-output .cs1-maint{display:none;color:#085;margin-left:0.3em}.mw-parser-output .cs1-kern-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right{padding-right:0.2em}.mw-parser-output .citation .mw-selflink{font-weight:inherit}@media screen{.mw-parser-output .cs1-format{font-size:95%}html.skin-theme-clientpref-night .mw-parser-output .cs1-maint{color:#18911f}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .cs1-maint{color:#18911f}}</style><cite id="CITEREFGörbitzTörnroosDay2012" class="citation journal cs1">Görbitz CH, Törnroos KW, Day GM (2012). "Single-crystal investigation of L-tryptophan with <i>Z<span class="nowrap" style="padding-left:0.05em;">′</span></i> = 16". <i><a href="/wiki/Acta_Crystallographica_Section_B" title="Acta Crystallographica Section B">Acta Crystallographica Section B</a></i>. <b>68</b> (Pt 5): 549–557. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1107%2FS0108768112033484">10.1107/S0108768112033484</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/22992800">22992800</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Acta+Crystallographica+Section+B&rft.atitle=Single-crystal+investigation+of+L-tryptophan+with+Z%3Cspan+class%3D%22nowrap%22+style%3D%22padding-left%3A0.05em%3B%22%3E%E2%80%B2%3C%2Fspan%3E+%3D+16&rft.volume=68&rft.issue=Pt+5&rft.pages=549-557&rft.date=2012&rft_id=info%3Adoi%2F10.1107%2FS0108768112033484&rft_id=info%3Apmid%2F22992800&rft.aulast=G%C3%B6rbitz&rft.aufirst=C.+H.&rft.au=T%C3%B6rnroos%2C+K.+W.&rft.au=Day%2C+G.+M.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ATryptophan" class="Z3988"></span></span> </li> <li id="cite_note-isbn0-19-855338-2-2"><span class="mw-cite-backlink"><b><a href="#cite_ref-isbn0-19-855338-2_2-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFDawson1969" class="citation book cs1">Dawson RM, et al. (1969). <span class="id-lock-registration" title="Free registration required"><a rel="nofollow" class="external text" href="https://archive.org/details/dataforbiochemic00daws"><i>Data for Biochemical Research</i></a></span>. Oxford: Clarendon Press. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/0-19-855338-2" title="Special:BookSources/0-19-855338-2"><bdi>0-19-855338-2</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Data+for+Biochemical+Research&rft.place=Oxford&rft.pub=Clarendon+Press&rft.date=1969&rft.isbn=0-19-855338-2&rft.aulast=Dawson&rft.aufirst=RM&rft_id=https%3A%2F%2Farchive.org%2Fdetails%2Fdataforbiochemic00daws&rfr_id=info%3Asid%2Fen.wikipedia.org%3ATryptophan" class="Z3988"></span></span> </li> <li id="cite_note-IUPAC-3"><span class="mw-cite-backlink"><b><a href="#cite_ref-IUPAC_3-0">^</a></b></span> <span class="reference-text"> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://iupac.qmul.ac.uk/AminoAcid/AA1n2.html">"Nomenclature and Symbolism for Amino Acids and Peptides"</a>. IUPAC-IUB Joint Commission on Biochemical Nomenclature. 1983. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20211202124922/https://iupac.qmul.ac.uk/AminoAcid/AA1n2.html">Archived</a> from the original on 2 December 2021<span class="reference-accessdate">. Retrieved <span class="nowrap">22 October</span> 2022</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=Nomenclature+and+Symbolism+for+Amino+Acids+and+Peptides&rft.pub=IUPAC-IUB+Joint+Commission+on+Biochemical+Nomenclature&rft.date=1983&rft_id=https%3A%2F%2Fiupac.qmul.ac.uk%2FAminoAcid%2FAA1n2.html&rfr_id=info%3Asid%2Fen.wikipedia.org%3ATryptophan" class="Z3988"></span></span> </li> <li id="cite_note-4"><span class="mw-cite-backlink"><b><a href="#cite_ref-4">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFSlominskiSemakPisarchikSweatman2002" class="citation journal cs1">Slominski A, Semak I, Pisarchik A, Sweatman T, Szczesniewski A, Wortsman J (2002). <a rel="nofollow" class="external text" href="https://doi.org/10.1016%2Fs0014-5793%2801%2903319-1">"Conversion of L-tryptophan to serotonin and melatonin in human melanoma cells"</a>. <i>FEBS Letters</i>. <b>511</b> (1–3): 102–6. <a href="/wiki/Bibcode_(identifier)" class="mw-redirect" title="Bibcode (identifier)">Bibcode</a>:<a rel="nofollow" class="external text" href="https://ui.adsabs.harvard.edu/abs/2002FEBSL.511..102S">2002FEBSL.511..102S</a>. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://doi.org/10.1016%2Fs0014-5793%2801%2903319-1">10.1016/s0014-5793(01)03319-1</a></span>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/11821057">11821057</a>. <a href="/wiki/S2CID_(identifier)" class="mw-redirect" title="S2CID (identifier)">S2CID</a> <a rel="nofollow" class="external text" href="https://api.semanticscholar.org/CorpusID:7820568">7820568</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=FEBS+Letters&rft.atitle=Conversion+of+L-tryptophan+to+serotonin+and+melatonin+in+human+melanoma+cells&rft.volume=511&rft.issue=1%E2%80%933&rft.pages=102-6&rft.date=2002&rft_id=info%3Adoi%2F10.1016%2Fs0014-5793%2801%2903319-1&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A7820568%23id-name%3DS2CID&rft_id=info%3Apmid%2F11821057&rft_id=info%3Abibcode%2F2002FEBSL.511..102S&rft.aulast=Slominski&rft.aufirst=A&rft.au=Semak%2C+I&rft.au=Pisarchik%2C+A&rft.au=Sweatman%2C+T&rft.au=Szczesniewski%2C+A&rft.au=Wortsman%2C+J&rft_id=https%3A%2F%2Fdoi.org%2F10.1016%252Fs0014-5793%252801%252903319-1&rfr_id=info%3Asid%2Fen.wikipedia.org%3ATryptophan" class="Z3988"></span></span> </li> <li id="cite_note-PubChem-5"><span class="mw-cite-backlink"><b><a href="#cite_ref-PubChem_5-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/L-tryptophan#section=Ecological-Information">"L-tryptophan | C11H12N2O2 - PubChem"</a>. <i>pubchem.ncbi.nlm.nih.gov</i><span class="reference-accessdate">. Retrieved <span class="nowrap">22 December</span> 2016</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=pubchem.ncbi.nlm.nih.gov&rft.atitle=L-tryptophan+%7C+C11H12N2O2+-+PubChem&rft_id=https%3A%2F%2Fpubchem.ncbi.nlm.nih.gov%2Fcompound%2FL-tryptophan%23section%3DEcological-Information&rfr_id=info%3Asid%2Fen.wikipedia.org%3ATryptophan" class="Z3988"></span></span> </li> <li id="cite_note-6"><span class="mw-cite-backlink"><b><a href="#cite_ref-6">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFCurzon1987" class="citation cs2">Curzon G (31 December 1987), Bender DA, Joseph MH, Kochen W, Steinhart H (eds.), <a rel="nofollow" class="external text" href="https://www.degruyter.com/document/doi/10.1515/9783110854657-004/html">"Hopkins and the Discovery of Tryptophan"</a>, <i>Progress in Tryptophan and Serotonin Research 1986</i>, Berlin, Boston: De Gruyter, pp. XXIX–XL, <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1515%2F9783110854657-004">10.1515/9783110854657-004</a>, <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-3-11-085465-7" title="Special:BookSources/978-3-11-085465-7"><bdi>978-3-11-085465-7</bdi></a><span class="reference-accessdate">, retrieved <span class="nowrap">19 February</span> 2024</span></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Progress+in+Tryptophan+and+Serotonin+Research+1986&rft.atitle=Hopkins+and+the+Discovery+of+Tryptophan&rft.pages=XXIX-XL&rft.date=1987-12-31&rft_id=info%3Adoi%2F10.1515%2F9783110854657-004&rft.isbn=978-3-11-085465-7&rft.aulast=Curzon&rft.aufirst=G.&rft_id=https%3A%2F%2Fwww.degruyter.com%2Fdocument%2Fdoi%2F10.1515%2F9783110854657-004%2Fhtml&rfr_id=info%3Asid%2Fen.wikipedia.org%3ATryptophan" class="Z3988"></span></span> </li> <li id="cite_note-:0-7"><span class="mw-cite-backlink"><b><a href="#cite_ref-:0_7-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation journal cs1"><a rel="nofollow" class="external text" href="https://www.jbc.org/article/S0021-9258(19)34176-6/pdf">"IUPAC-IUB Commission on Biochemical Nomenclature A One-Letter Notation for Amino Acid Sequences"</a>. <i>Journal of Biological Chemistry</i>. <b>243</b> (13): 3557–3559. 10 July 1968. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://doi.org/10.1016%2FS0021-9258%2819%2934176-6">10.1016/S0021-9258(19)34176-6</a></span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Journal+of+Biological+Chemistry&rft.atitle=IUPAC-IUB+Commission+on+Biochemical+Nomenclature+A+One-Letter+Notation+for+Amino+Acid+Sequences&rft.volume=243&rft.issue=13&rft.pages=3557-3559&rft.date=1968-07-10&rft_id=info%3Adoi%2F10.1016%2FS0021-9258%2819%2934176-6&rft_id=https%3A%2F%2Fwww.jbc.org%2Farticle%2FS0021-9258%2819%2934176-6%2Fpdf&rfr_id=info%3Asid%2Fen.wikipedia.org%3ATryptophan" class="Z3988"></span></span> </li> <li id="cite_note-pmid6132421-8"><span class="mw-cite-backlink"><b><a href="#cite_ref-pmid6132421_8-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFFernstrom1983" class="citation journal cs1">Fernstrom JD (1983). "Role of precursor availability in control of monoamine biosynthesis in brain". <i>Physiological Reviews</i>. <b>63</b> (2): 484–546. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1152%2Fphysrev.1983.63.2.484">10.1152/physrev.1983.63.2.484</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/6132421">6132421</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Physiological+Reviews&rft.atitle=Role+of+precursor+availability+in+control+of+monoamine+biosynthesis+in+brain&rft.volume=63&rft.issue=2&rft.pages=484-546&rft.date=1983&rft_id=info%3Adoi%2F10.1152%2Fphysrev.1983.63.2.484&rft_id=info%3Apmid%2F6132421&rft.aulast=Fernstrom&rft.aufirst=JD&rfr_id=info%3Asid%2Fen.wikipedia.org%3ATryptophan" class="Z3988"></span></span> </li> <li id="cite_note-pmid1704290-9"><span class="mw-cite-backlink"><b><a href="#cite_ref-pmid1704290_9-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFSchaechterWurtman1990" class="citation journal cs1">Schaechter JD, Wurtman RJ (1990). <a rel="nofollow" class="external text" href="https://web.archive.org/web/20200809154957/http://wurtmanlab.mit.edu/static/pdf/790.pdf">"Serotonin release varies with brain tryptophan levels"</a> <span class="cs1-format">(PDF)</span>. <i>Brain Research</i>. <b>532</b> (1–2): 203–10. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2F0006-8993%2890%2991761-5">10.1016/0006-8993(90)91761-5</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/1704290">1704290</a>. <a href="/wiki/S2CID_(identifier)" class="mw-redirect" title="S2CID (identifier)">S2CID</a> <a rel="nofollow" class="external text" href="https://api.semanticscholar.org/CorpusID:8451316">8451316</a>. Archived from <a rel="nofollow" class="external text" href="http://wurtmanlab.mit.edu/static/pdf/790.pdf">the original</a> <span class="cs1-format">(PDF)</span> on 9 August 2020<span class="reference-accessdate">. Retrieved <span class="nowrap">30 May</span> 2014</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Brain+Research&rft.atitle=Serotonin+release+varies+with+brain+tryptophan+levels&rft.volume=532&rft.issue=1%E2%80%932&rft.pages=203-10&rft.date=1990&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A8451316%23id-name%3DS2CID&rft_id=info%3Apmid%2F1704290&rft_id=info%3Adoi%2F10.1016%2F0006-8993%2890%2991761-5&rft.aulast=Schaechter&rft.aufirst=JD&rft.au=Wurtman%2C+RJ&rft_id=http%3A%2F%2Fwurtmanlab.mit.edu%2Fstatic%2Fpdf%2F790.pdf&rfr_id=info%3Asid%2Fen.wikipedia.org%3ATryptophan" class="Z3988"></span></span> </li> <li id="cite_note-pmid4391290-10"><span class="mw-cite-backlink">^ <a href="#cite_ref-pmid4391290_10-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-pmid4391290_10-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFWurtmanAnton-Tay1969" class="citation journal cs1">Wurtman RJ, Anton-Tay F (1969). <a rel="nofollow" class="external text" href="https://web.archive.org/web/20140531104922/http://wurtmanlab.mit.edu/static/pdf/104.pdf">"The mammalian pineal as a neuroendocrine transducer"</a> <span class="cs1-format">(PDF)</span>. <i>Recent Progress in Hormone Research</i>. <b>25</b>: 493–522. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2Fb978-0-12-571125-8.50014-4">10.1016/b978-0-12-571125-8.50014-4</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-12-571125-8" title="Special:BookSources/978-0-12-571125-8"><bdi>978-0-12-571125-8</bdi></a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/4391290">4391290</a>. Archived from <a rel="nofollow" class="external text" href="http://wurtmanlab.mit.edu/static/pdf/104.pdf">the original</a> <span class="cs1-format">(PDF)</span> on 31 May 2014.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Recent+Progress+in+Hormone+Research&rft.atitle=The+mammalian+pineal+as+a+neuroendocrine+transducer&rft.volume=25&rft.pages=493-522&rft.date=1969&rft_id=info%3Apmid%2F4391290&rft_id=info%3Adoi%2F10.1016%2Fb978-0-12-571125-8.50014-4&rft.isbn=978-0-12-571125-8&rft.aulast=Wurtman&rft.aufirst=RJ&rft.au=Anton-Tay%2C+F&rft_id=http%3A%2F%2Fwurtmanlab.mit.edu%2Fstatic%2Fpdf%2F104.pdf&rfr_id=info%3Asid%2Fen.wikipedia.org%3ATryptophan" class="Z3988"></span></span> </li> <li id="cite_note-Marx-2020-11"><span class="mw-cite-backlink">^ <a href="#cite_ref-Marx-2020_11-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Marx-2020_11-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-Marx-2020_11-2"><sup><i><b>c</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFMarxMcGuinnessRocksRuusunen2020" class="citation journal cs1">Marx W, McGuinness AJ, Rocks T, Ruusunen A, Cleminson J, Walker AJ, Gomes-da-Costa S, Lane M, Sanches M, Diaz AP, Tseng PT (23 November 2020). <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/33230205">"The kynurenine pathway in major depressive disorder, bipolar disorder, and schizophrenia: a meta-analysis of 101 studies"</a>. <i>Molecular Psychiatry</i>. <b>26</b> (8): 4158–4178. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1038%2Fs41380-020-00951-9">10.1038/s41380-020-00951-9</a>. <a href="/wiki/ISSN_(identifier)" class="mw-redirect" title="ISSN (identifier)">ISSN</a> <a rel="nofollow" class="external text" href="https://search.worldcat.org/issn/1476-5578">1476-5578</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/33230205">33230205</a>. <a href="/wiki/S2CID_(identifier)" class="mw-redirect" title="S2CID (identifier)">S2CID</a> <a rel="nofollow" class="external text" href="https://api.semanticscholar.org/CorpusID:227132820">227132820</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Molecular+Psychiatry&rft.atitle=The+kynurenine+pathway+in+major+depressive+disorder%2C+bipolar+disorder%2C+and+schizophrenia%3A+a+meta-analysis+of+101+studies&rft.volume=26&rft.issue=8&rft.pages=4158-4178&rft.date=2020-11-23&rft.issn=1476-5578&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A227132820%23id-name%3DS2CID&rft_id=info%3Apmid%2F33230205&rft_id=info%3Adoi%2F10.1038%2Fs41380-020-00951-9&rft.aulast=Marx&rft.aufirst=Wolfgang&rft.au=McGuinness%2C+Amelia+J.&rft.au=Rocks%2C+Tetyana&rft.au=Ruusunen%2C+Anu&rft.au=Cleminson%2C+Jasmine&rft.au=Walker%2C+Adam+J.&rft.au=Gomes-da-Costa%2C+Susana&rft.au=Lane%2C+Melissa&rft.au=Sanches%2C+Marsal&rft.au=Diaz%2C+Alexandre+P.&rft.au=Tseng%2C+Ping-Tao&rft_id=https%3A%2F%2Fpubmed.ncbi.nlm.nih.gov%2F33230205&rfr_id=info%3Asid%2Fen.wikipedia.org%3ATryptophan" class="Z3988"></span></span> </li> <li id="cite_note-Bartoli-12"><span class="mw-cite-backlink"><b><a href="#cite_ref-Bartoli_12-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFBartoliMisiakCalloviniCavaleri2020" class="citation journal cs1">Bartoli F, Misiak B, Callovini T, Cavaleri D, Cioni RM, Crocamo C, Savitz JB, Carrà G (19 October 2020). "The kynurenine pathway in bipolar disorder: a meta-analysis on the peripheral blood levels of tryptophan and related metabolites". <i>Molecular Psychiatry</i>. <b>26</b> (7): 3419–3429. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1038%2Fs41380-020-00913-1">10.1038/s41380-020-00913-1</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/33077852">33077852</a>. <a href="/wiki/S2CID_(identifier)" class="mw-redirect" title="S2CID (identifier)">S2CID</a> <a rel="nofollow" class="external text" href="https://api.semanticscholar.org/CorpusID:224314102">224314102</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Molecular+Psychiatry&rft.atitle=The+kynurenine+pathway+in+bipolar+disorder%3A+a+meta-analysis+on+the+peripheral+blood+levels+of+tryptophan+and+related+metabolites.&rft.volume=26&rft.issue=7&rft.pages=3419-3429&rft.date=2020-10-19&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A224314102%23id-name%3DS2CID&rft_id=info%3Apmid%2F33077852&rft_id=info%3Adoi%2F10.1038%2Fs41380-020-00913-1&rft.aulast=Bartoli&rft.aufirst=F&rft.au=Misiak%2C+B&rft.au=Callovini%2C+T&rft.au=Cavaleri%2C+D&rft.au=Cioni%2C+RM&rft.au=Crocamo%2C+C&rft.au=Savitz%2C+JB&rft.au=Carr%C3%A0%2C+G&rfr_id=info%3Asid%2Fen.wikipedia.org%3ATryptophan" class="Z3988"></span></span> </li> <li id="cite_note-pmid14284754-13"><span class="mw-cite-backlink"><b><a href="#cite_ref-pmid14284754_13-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFIkedaTsujiNakamuraIchiyama1965" class="citation journal cs1">Ikeda M, Tsuji H, Nakamura S, Ichiyama A, Nishizuka Y, Hayaishi O (1965). <a rel="nofollow" class="external text" href="https://doi.org/10.1016%2FS0021-9258%2818%2997589-7">"Studies on the biosynthesis of nicotinamide adenine dinucleotide. II. A role of picolinic carboxylase in the biosynthesis of nicotinamide adenine dinucleotide from tryptophan in mammals"</a>. <i>The Journal of Biological Chemistry</i>. <b>240</b> (3): 1395–401. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://doi.org/10.1016%2FS0021-9258%2818%2997589-7">10.1016/S0021-9258(18)97589-7</a></span>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/14284754">14284754</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=The+Journal+of+Biological+Chemistry&rft.atitle=Studies+on+the+biosynthesis+of+nicotinamide+adenine+dinucleotide.+II.+A+role+of+picolinic+carboxylase+in+the+biosynthesis+of+nicotinamide+adenine+dinucleotide+from+tryptophan+in+mammals&rft.volume=240&rft.issue=3&rft.pages=1395-401&rft.date=1965&rft_id=info%3Adoi%2F10.1016%2FS0021-9258%2818%2997589-7&rft_id=info%3Apmid%2F14284754&rft.aulast=Ikeda&rft.aufirst=M&rft.au=Tsuji%2C+H&rft.au=Nakamura%2C+S&rft.au=Ichiyama%2C+A&rft.au=Nishizuka%2C+Y&rft.au=Hayaishi%2C+O&rft_id=https%3A%2F%2Fdoi.org%2F10.1016%252FS0021-9258%252818%252997589-7&rfr_id=info%3Asid%2Fen.wikipedia.org%3ATryptophan" class="Z3988"></span></span> </li> <li id="cite_note-pmid18394986-14"><span class="mw-cite-backlink"><b><a href="#cite_ref-pmid18394986_14-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFPalmeNagy2008" class="citation journal cs1">Palme K, Nagy F (2008). <a rel="nofollow" class="external text" href="https://doi.org/10.1016%2Fj.cell.2008.03.014">"A new gene for auxin synthesis"</a>. <i>Cell</i>. <b>133</b> (1): 31–2. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://doi.org/10.1016%2Fj.cell.2008.03.014">10.1016/j.cell.2008.03.014</a></span>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/18394986">18394986</a>. <a href="/wiki/S2CID_(identifier)" class="mw-redirect" title="S2CID (identifier)">S2CID</a> <a rel="nofollow" class="external text" href="https://api.semanticscholar.org/CorpusID:9949830">9949830</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Cell&rft.atitle=A+new+gene+for+auxin+synthesis&rft.volume=133&rft.issue=1&rft.pages=31-2&rft.date=2008&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A9949830%23id-name%3DS2CID&rft_id=info%3Apmid%2F18394986&rft_id=info%3Adoi%2F10.1016%2Fj.cell.2008.03.014&rft.aulast=Palme&rft.aufirst=K&rft.au=Nagy%2C+F&rft_id=https%3A%2F%2Fdoi.org%2F10.1016%252Fj.cell.2008.03.014&rfr_id=info%3Asid%2Fen.wikipedia.org%3ATryptophan" class="Z3988"></span></span> </li> <li id="cite_note-Ledochowski_M,_Widner_B,_Murr_C,_Sperner-Unterweger_B,_Fuchs_D_2001_367–71-15"><span class="mw-cite-backlink"><b><a href="#cite_ref-Ledochowski_M,_Widner_B,_Murr_C,_Sperner-Unterweger_B,_Fuchs_D_2001_367–71_15-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFLedochowskiWidnerMurrSperner-Unterweger2001" class="citation journal cs1">Ledochowski M, Widner B, Murr C, Sperner-Unterweger B, Fuchs D (2001). <a rel="nofollow" class="external text" href="https://web.archive.org/web/20160419160203/http://www.lactose.at/pdf/works/11336160.pdf">"Fructose malabsorption is associated with decreased plasma tryptophan"</a> <span class="cs1-format">(PDF)</span>. <i>Scandinavian Journal of Gastroenterology</i>. <b>36</b> (4): 367–71. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1080%2F003655201300051135">10.1080/003655201300051135</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/11336160">11336160</a>. Archived from <a rel="nofollow" class="external text" href="http://www.lactose.at/pdf/works/11336160.pdf">the original</a> <span class="cs1-format">(PDF)</span> on 19 April 2016.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Scandinavian+Journal+of+Gastroenterology&rft.atitle=Fructose+malabsorption+is+associated+with+decreased+plasma+tryptophan&rft.volume=36&rft.issue=4&rft.pages=367-71&rft.date=2001&rft_id=info%3Adoi%2F10.1080%2F003655201300051135&rft_id=info%3Apmid%2F11336160&rft.aulast=Ledochowski&rft.aufirst=M&rft.au=Widner%2C+B&rft.au=Murr%2C+C&rft.au=Sperner-Unterweger%2C+B&rft.au=Fuchs%2C+D&rft_id=http%3A%2F%2Fwww.lactose.at%2Fpdf%2Fworks%2F11336160.pdf&rfr_id=info%3Asid%2Fen.wikipedia.org%3ATryptophan" class="Z3988"></span></span> </li> <li id="cite_note-16"><span class="mw-cite-backlink"><b><a href="#cite_ref-16">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFLedochowskiSperner-UnterwegerWidnerFuchs1998" class="citation journal cs1">Ledochowski M, Sperner-Unterweger B, Widner B, Fuchs D (June 1998). "Fructose malabsorption is associated with early signs of mental depression". <i>European Journal of Medical Research</i>. <b>3</b> (6): 295–8. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/9620891">9620891</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=European+Journal+of+Medical+Research&rft.atitle=Fructose+malabsorption+is+associated+with+early+signs+of+mental+depression&rft.volume=3&rft.issue=6&rft.pages=295-8&rft.date=1998-06&rft_id=info%3Apmid%2F9620891&rft.aulast=Ledochowski&rft.aufirst=M&rft.au=Sperner-Unterweger%2C+B&rft.au=Widner%2C+B&rft.au=Fuchs%2C+D&rfr_id=info%3Asid%2Fen.wikipedia.org%3ATryptophan" class="Z3988"></span></span> </li> <li id="cite_note-pmid16285852-17"><span class="mw-cite-backlink"><b><a href="#cite_ref-pmid16285852_17-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFGollnickBabitzkeAntsonYanofsky2005" class="citation journal cs1">Gollnick P, Babitzke P, Antson A, Yanofsky C (2005). "Complexity in regulation of tryptophan biosynthesis in Bacillus subtilis". <i>Annual Review of Genetics</i>. <b>39</b>: 47–68. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1146%2Fannurev.genet.39.073003.093745">10.1146/annurev.genet.39.073003.093745</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/16285852">16285852</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Annual+Review+of+Genetics&rft.atitle=Complexity+in+regulation+of+tryptophan+biosynthesis+in+Bacillus+subtilis&rft.volume=39&rft.pages=47-68&rft.date=2005&rft_id=info%3Adoi%2F10.1146%2Fannurev.genet.39.073003.093745&rft_id=info%3Apmid%2F16285852&rft.aulast=Gollnick&rft.aufirst=P&rft.au=Babitzke%2C+P&rft.au=Antson%2C+A&rft.au=Yanofsky%2C+C&rfr_id=info%3Asid%2Fen.wikipedia.org%3ATryptophan" class="Z3988"></span></span> </li> <li id="cite_note-Microbial_biosynthesis_of_bioactive_compounds-18"><span class="mw-cite-backlink">^ <a href="#cite_ref-Microbial_biosynthesis_of_bioactive_compounds_18-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Microbial_biosynthesis_of_bioactive_compounds_18-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-Microbial_biosynthesis_of_bioactive_compounds_18-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-Microbial_biosynthesis_of_bioactive_compounds_18-3"><sup><i><b>d</b></i></sup></a> <a href="#cite_ref-Microbial_biosynthesis_of_bioactive_compounds_18-4"><sup><i><b>e</b></i></sup></a> <a href="#cite_ref-Microbial_biosynthesis_of_bioactive_compounds_18-5"><sup><i><b>f</b></i></sup></a> <a href="#cite_ref-Microbial_biosynthesis_of_bioactive_compounds_18-6"><sup><i><b>g</b></i></sup></a> <a href="#cite_ref-Microbial_biosynthesis_of_bioactive_compounds_18-7"><sup><i><b>h</b></i></sup></a> <a href="#cite_ref-Microbial_biosynthesis_of_bioactive_compounds_18-8"><sup><i><b>i</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFZhangDavies2016" class="citation journal cs1">Zhang LS, Davies SS (April 2016). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4840492">"Microbial metabolism of dietary components to bioactive metabolites: opportunities for new therapeutic interventions"</a>. <i>Genome Med</i>. <b>8</b> (1): 46. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://doi.org/10.1186%2Fs13073-016-0296-x">10.1186/s13073-016-0296-x</a></span>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4840492">4840492</a></span>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/27102537">27102537</a>. <q><i>Lactobacillus</i> spp. convert tryptophan to indole-3-aldehyde (I3A) through unidentified enzymes [125]. <i>Clostridium sporogenes</i> convert tryptophan to IPA [6], likely via a tryptophan deaminase. ... IPA also potently scavenges hydroxyl radicals</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Genome+Med&rft.atitle=Microbial+metabolism+of+dietary+components+to+bioactive+metabolites%3A+opportunities+for+new+therapeutic+interventions&rft.volume=8&rft.issue=1&rft.pages=46&rft.date=2016-04&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC4840492%23id-name%3DPMC&rft_id=info%3Apmid%2F27102537&rft_id=info%3Adoi%2F10.1186%2Fs13073-016-0296-x&rft.aulast=Zhang&rft.aufirst=LS&rft.au=Davies%2C+SS&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC4840492&rfr_id=info%3Asid%2Fen.wikipedia.org%3ATryptophan" class="Z3988"></span><br /><a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4840492/table/Tab2/">Table 2: Microbial metabolites: their synthesis, mechanisms of action, and effects on health and disease</a><br /><a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4840492/figure/Fig1/">Figure 1: Molecular mechanisms of action of indole and its metabolites on host physiology and disease</a></span> </li> <li id="cite_note-Microbiome_IPA-19"><span class="mw-cite-backlink"><b><a href="#cite_ref-Microbiome_IPA_19-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFWikoffAnforaLiuSchultz2009" class="citation journal cs1">Wikoff WR, Anfora AT, Liu J, Schultz PG, Lesley SA, Peters EC, <a href="/wiki/Gary_Siuzdak" title="Gary Siuzdak">Siuzdak G</a> (March 2009). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2656143">"Metabolomics analysis reveals large effects of gut microflora on mammalian blood metabolites"</a>. <i>Proc. Natl. Acad. Sci. U.S.A</i>. <b>106</b> (10): 3698–3703. <a href="/wiki/Bibcode_(identifier)" class="mw-redirect" title="Bibcode (identifier)">Bibcode</a>:<a rel="nofollow" class="external text" href="https://ui.adsabs.harvard.edu/abs/2009PNAS..106.3698W">2009PNAS..106.3698W</a>. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://doi.org/10.1073%2Fpnas.0812874106">10.1073/pnas.0812874106</a></span>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2656143">2656143</a></span>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/19234110">19234110</a>. <q>Production of IPA was shown to be completely dependent on the presence of gut microflora and could be established by colonization with the bacterium <i>Clostridium sporogenes</i>.</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Proc.+Natl.+Acad.+Sci.+U.S.A.&rft.atitle=Metabolomics+analysis+reveals+large+effects+of+gut+microflora+on+mammalian+blood+metabolites&rft.volume=106&rft.issue=10&rft.pages=3698-3703&rft.date=2009-03&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC2656143%23id-name%3DPMC&rft_id=info%3Apmid%2F19234110&rft_id=info%3Adoi%2F10.1073%2Fpnas.0812874106&rft_id=info%3Abibcode%2F2009PNAS..106.3698W&rft.aulast=Wikoff&rft.aufirst=WR&rft.au=Anfora%2C+AT&rft.au=Liu%2C+J&rft.au=Schultz%2C+PG&rft.au=Lesley%2C+SA&rft.au=Peters%2C+EC&rft.au=Siuzdak%2C+G&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC2656143&rfr_id=info%3Asid%2Fen.wikipedia.org%3ATryptophan" class="Z3988"></span><br /><a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2656143/figure/F2/">IPA metabolism diagram</a></span> </li> <li id="cite_note-Human_metabolome_IPA-20"><span class="mw-cite-backlink"><b><a href="#cite_ref-Human_metabolome_IPA_20-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="http://www.hmdb.ca/metabolites/HMDB02302">"3-Indolepropionic acid"</a>. <i>Human Metabolome Database</i>. University of Alberta<span class="reference-accessdate">. Retrieved <span class="nowrap">12 June</span> 2018</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=Human+Metabolome+Database&rft.atitle=3-Indolepropionic+acid&rft_id=http%3A%2F%2Fwww.hmdb.ca%2Fmetabolites%2FHMDB02302&rfr_id=info%3Asid%2Fen.wikipedia.org%3ATryptophan" class="Z3988"></span></span> </li> <li id="cite_note-Indolepropionic_acid_scavenging-21"><span class="mw-cite-backlink"><b><a href="#cite_ref-Indolepropionic_acid_scavenging_21-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFChyanPoeggelerOmarChain1999" class="citation journal cs1">Chyan YJ, Poeggeler B, Omar RA, Chain DG, Frangione B, Ghiso J, Pappolla MA (July 1999). <a rel="nofollow" class="external text" href="https://doi.org/10.1074%2Fjbc.274.31.21937">"Potent neuroprotective properties against the Alzheimer beta-amyloid by an endogenous melatonin-related indole structure, indole-3-propionic acid"</a>. <i>J. Biol. Chem</i>. <b>274</b> (31): 21937–21942. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://doi.org/10.1074%2Fjbc.274.31.21937">10.1074/jbc.274.31.21937</a></span>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/10419516">10419516</a>. <a href="/wiki/S2CID_(identifier)" class="mw-redirect" title="S2CID (identifier)">S2CID</a> <a rel="nofollow" class="external text" href="https://api.semanticscholar.org/CorpusID:6630247">6630247</a>. <q>[Indole-3-propionic acid (IPA)] has previously been identified in the plasma and cerebrospinal fluid of humans, but its functions are not known. ... In kinetic competition experiments using free radical-trapping agents, the capacity of IPA to scavenge hydroxyl radicals exceeded that of melatonin, an indoleamine considered to be the most potent naturally occurring scavenger of free radicals. In contrast with other antioxidants, IPA was not converted to reactive intermediates with pro-oxidant activity.</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=J.+Biol.+Chem.&rft.atitle=Potent+neuroprotective+properties+against+the+Alzheimer+beta-amyloid+by+an+endogenous+melatonin-related+indole+structure%2C+indole-3-propionic+acid&rft.volume=274&rft.issue=31&rft.pages=21937-21942&rft.date=1999-07&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A6630247%23id-name%3DS2CID&rft_id=info%3Apmid%2F10419516&rft_id=info%3Adoi%2F10.1074%2Fjbc.274.31.21937&rft.aulast=Chyan&rft.aufirst=YJ&rft.au=Poeggeler%2C+B&rft.au=Omar%2C+RA&rft.au=Chain%2C+DG&rft.au=Frangione%2C+B&rft.au=Ghiso%2C+J&rft.au=Pappolla%2C+MA&rft_id=https%3A%2F%2Fdoi.org%2F10.1074%252Fjbc.274.31.21937&rfr_id=info%3Asid%2Fen.wikipedia.org%3ATryptophan" class="Z3988"></span></span> </li> <li id="cite_note-DRItext-22"><span class="mw-cite-backlink"><b><a href="#cite_ref-DRItext_22-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFInstitute_of_Medicine2002" class="citation book cs1"><a href="/wiki/Institute_of_Medicine" class="mw-redirect" title="Institute of Medicine">Institute of Medicine</a> (2002). <a rel="nofollow" class="external text" href="https://www.nap.edu/read/10490/chapter/12">"Protein and Amino Acids"</a>. <i>Dietary Reference Intakes for Energy, Carbohydrates, Fiber, Fat, Fatty Acids, Cholesterol, Protein, and Amino Acids</i>. Washington, DC: The National Academies Press. pp. 589–768. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.17226%2F10490">10.17226/10490</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-309-08525-0" title="Special:BookSources/978-0-309-08525-0"><bdi>978-0-309-08525-0</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Protein+and+Amino+Acids&rft.btitle=Dietary+Reference+Intakes+for+Energy%2C+Carbohydrates%2C+Fiber%2C+Fat%2C+Fatty+Acids%2C+Cholesterol%2C+Protein%2C+and+Amino+Acids&rft.place=Washington%2C+DC&rft.pages=589-768&rft.pub=The+National+Academies+Press&rft.date=2002&rft_id=info%3Adoi%2F10.17226%2F10490&rft.isbn=978-0-309-08525-0&rft.au=Institute+of+Medicine&rft_id=https%3A%2F%2Fwww.nap.edu%2Fread%2F10490%2Fchapter%2F12&rfr_id=info%3Asid%2Fen.wikipedia.org%3ATryptophan" class="Z3988"></span></span> </li> <li id="cite_note-scientificamerican-23"><span class="mw-cite-backlink">^ <a href="#cite_ref-scientificamerican_23-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-scientificamerican_23-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFBallantyne2007" class="citation magazine cs1">Ballantyne C (21 November 2007). <a rel="nofollow" class="external text" href="http://www.scientificamerican.com/article.cfm?id=fact-or-fiction-does-turkey-make-you-sleepy">"Does Turkey Make You Sleepy?"</a>. <i>Scientific American</i><span class="reference-accessdate">. Retrieved <span class="nowrap">6 June</span> 2013</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Scientific+American&rft.atitle=Does+Turkey+Make+You+Sleepy%3F&rft.date=2007-11-21&rft.aulast=Ballantyne&rft.aufirst=C&rft_id=http%3A%2F%2Fwww.scientificamerican.com%2Farticle.cfm%3Fid%3Dfact-or-fiction-does-turkey-make-you-sleepy&rfr_id=info%3Asid%2Fen.wikipedia.org%3ATryptophan" class="Z3988"></span></span> </li> <li id="cite_note-McCue-24"><span class="mw-cite-backlink">^ <a href="#cite_ref-McCue_24-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-McCue_24-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFMcCue" class="citation web cs1">McCue K. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20070404111342/http://www.chemistry.org/portal/a/c/s/1/feature_ent.html?DOC=enthusiasts%5cent_tryptophan.html">"Chemistry.org: Thanksgiving, Turkey, and Tryptophan"</a>. Archived from <a rel="nofollow" class="external text" href="http://www.chemistry.org/portal/a/c/s/1/feature_ent.html?DOC=enthusiasts%5Cent_tryptophan.html">the original</a> on 4 April 2007<span class="reference-accessdate">. Retrieved <span class="nowrap">17 August</span> 2007</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=Chemistry.org%3A+Thanksgiving%2C+Turkey%2C+and+Tryptophan&rft.aulast=McCue&rft.aufirst=K&rft_id=http%3A%2F%2Fwww.chemistry.org%2Fportal%2Fa%2Fc%2Fs%2F1%2Ffeature_ent.html%3FDOC%3Denthusiasts%255Cent_tryptophan.html&rfr_id=info%3Asid%2Fen.wikipedia.org%3ATryptophan" class="Z3988"></span></span> </li> <li id="cite_note-USDA-25"><span class="mw-cite-backlink">^ <a href="#cite_ref-USDA_25-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-USDA_25-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-USDA_25-2"><sup><i><b>c</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFHolden" class="citation web cs1">Holden J. <a rel="nofollow" class="external text" href="https://www.ars.usda.gov/ba/bhnrc/ndl">"USDA National Nutrient Database for Standard Reference, Release 22"</a>. Nutrient Data Laboratory, Agricultural Research Service, United States Department of Agriculture<span class="reference-accessdate">. Retrieved <span class="nowrap">29 November</span> 2009</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=USDA+National+Nutrient+Database+for+Standard+Reference%2C+Release+22&rft.pub=Nutrient+Data+Laboratory%2C+Agricultural+Research+Service%2C+United+States+Department+of+Agriculture&rft.aulast=Holden&rft.aufirst=Joanne&rft_id=http%3A%2F%2Fwww.ars.usda.gov%2Fba%2Fbhnrc%2Fndl&rfr_id=info%3Asid%2Fen.wikipedia.org%3ATryptophan" class="Z3988"></span></span> </li> <li id="cite_note-Rambali-26"><span class="mw-cite-backlink"><b><a href="#cite_ref-Rambali_26-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFRambaliVan_AndelSchenkWolterink2002" class="citation journal cs1">Rambali B, Van Andel I, Schenk E, Wolterink G, van de Werken G, Stevenson H, Vleeming W (2002). <a rel="nofollow" class="external text" href="https://web.archive.org/web/20051108071725/http://rivm.nl/bibliotheek/rapporten/650270002.pdf">"[The contribution of cocoa additive to cigarette smoking addiction]"</a> <span class="cs1-format">(PDF)</span>. <i>RIVM</i> (report 650270002/2002). The National Institute for Public Health and the Environment (Netherlands). Archived from <a rel="nofollow" class="external text" href="http://rivm.nl/bibliotheek/rapporten/650270002.pdf">the original</a> <span class="cs1-format">(PDF)</span> on 8 November 2005.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=RIVM&rft.atitle=%5BThe+contribution+of+cocoa+additive+to+cigarette+smoking+addiction%5D&rft.issue=report+650270002%2F2002&rft.date=2002&rft.aulast=Rambali&rft.aufirst=B&rft.au=Van+Andel%2C+I&rft.au=Schenk%2C+E&rft.au=Wolterink%2C+G&rft.au=van+de+Werken%2C+G&rft.au=Stevenson%2C+H&rft.au=Vleeming%2C+W&rft_id=http%3A%2F%2Frivm.nl%2Fbibliotheek%2Frapporten%2F650270002.pdf&rfr_id=info%3Asid%2Fen.wikipedia.org%3ATryptophan" class="Z3988"></span></span> </li> <li id="cite_note-DOI10.1111/j.1601-5215.2010.00508.x-27"><span class="mw-cite-backlink"><b><a href="#cite_ref-DOI10.1111/j.1601-5215.2010.00508.x_27-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFSohWalter2011" class="citation journal cs1">Soh NL, Walter GT (2011). "Tryptophan and depression: can diet alone be the answer?". <i>Acta Neuropsychiatrica</i>. <b>23</b> (1): 1601–5215. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1111%2Fj.1601-5215.2010.00508.x">10.1111/j.1601-5215.2010.00508.x</a>. <a href="/wiki/S2CID_(identifier)" class="mw-redirect" title="S2CID (identifier)">S2CID</a> <a rel="nofollow" class="external text" href="https://api.semanticscholar.org/CorpusID:145779393">145779393</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Acta+Neuropsychiatrica&rft.atitle=Tryptophan+and+depression%3A+can+diet+alone+be+the+answer%3F&rft.volume=23&rft.issue=1&rft.pages=1601-5215&rft.date=2011&rft_id=info%3Adoi%2F10.1111%2Fj.1601-5215.2010.00508.x&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A145779393%23id-name%3DS2CID&rft.aulast=Soh&rft.aufirst=NL&rft.au=Walter%2C+GT&rfr_id=info%3Asid%2Fen.wikipedia.org%3ATryptophan" class="Z3988"></span></span> </li> <li id="cite_note-Fernstrom-28"><span class="mw-cite-backlink"><b><a href="#cite_ref-Fernstrom_28-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFFernstrom2012" class="citation journal cs1">Fernstrom JD (2012). <a rel="nofollow" class="external text" href="https://doi.org/10.3945%2Fjn.111.157065">"Effects and side effects associated with the non-nutritional use of tryptophan by humans"</a>. <i>The Journal of Nutrition</i>. <b>142</b> (12): 2236S–2244S. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://doi.org/10.3945%2Fjn.111.157065">10.3945/jn.111.157065</a></span>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/23077193">23077193</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=The+Journal+of+Nutrition&rft.atitle=Effects+and+side+effects+associated+with+the+non-nutritional+use+of+tryptophan+by+humans&rft.volume=142&rft.issue=12&rft.pages=2236S-2244S&rft.date=2012&rft_id=info%3Adoi%2F10.3945%2Fjn.111.157065&rft_id=info%3Apmid%2F23077193&rft.aulast=Fernstrom&rft.aufirst=JD&rft_id=https%3A%2F%2Fdoi.org%2F10.3945%252Fjn.111.157065&rfr_id=info%3Asid%2Fen.wikipedia.org%3ATryptophan" class="Z3988"></span></span> </li> <li id="cite_note-Wurtman_1980-29"><span class="mw-cite-backlink">^ <a href="#cite_ref-Wurtman_1980_29-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Wurtman_1980_29-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFWurtmanHeftiMelamed1980" class="citation journal cs1">Wurtman RJ, Hefti F, Melamed E (1980). "Precursor control of neurotransmitter synthesis". <i>Pharmacological Reviews</i>. <b>32</b> (4): 315–35. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/6115400">6115400</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Pharmacological+Reviews&rft.atitle=Precursor+control+of+neurotransmitter+synthesis&rft.volume=32&rft.issue=4&rft.pages=315-35&rft.date=1980&rft_id=info%3Apmid%2F6115400&rft.aulast=Wurtman&rft.aufirst=RJ&rft.au=Hefti%2C+F&rft.au=Melamed%2C+E&rfr_id=info%3Asid%2Fen.wikipedia.org%3ATryptophan" class="Z3988"></span></span> </li> <li id="cite_note-pmid11687048-30"><span class="mw-cite-backlink">^ <a href="#cite_ref-pmid11687048_30-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-pmid11687048_30-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-pmid11687048_30-2"><sup><i><b>c</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFShawTurnerDel_Mar2002" class="citation journal cs1">Shaw K, Turner J, Del Mar C (2002). Shaw KA (ed.). <a rel="nofollow" class="external text" href="https://espace.library.uq.edu.au/view/UQ:209937/UQ209937_OA.pdf">"Tryptophan and 5-hydroxytryptophan for depression"</a> <span class="cs1-format">(PDF)</span>. <i>The Cochrane Database of Systematic Reviews</i>. <b>2010</b> (1): CD003198. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2F14651858.CD003198">10.1002/14651858.CD003198</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/11869656">11869656</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=The+Cochrane+Database+of+Systematic+Reviews&rft.atitle=Tryptophan+and+5-hydroxytryptophan+for+depression&rft.volume=2010&rft.issue=1&rft.pages=CD003198&rft.date=2002&rft_id=info%3Adoi%2F10.1002%2F14651858.CD003198&rft_id=info%3Apmid%2F11869656&rft.aulast=Shaw&rft.aufirst=K&rft.au=Turner%2C+J&rft.au=Del+Mar%2C+C&rft_id=https%3A%2F%2Fespace.library.uq.edu.au%2Fview%2FUQ%3A209937%2FUQ209937_OA.pdf&rfr_id=info%3Asid%2Fen.wikipedia.org%3ATryptophan" class="Z3988"></span></span> </li> <li id="cite_note-Ravindran-31"><span class="mw-cite-backlink"><b><a href="#cite_ref-Ravindran_31-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFRavindranda_Silva2013" class="citation journal cs1">Ravindran AV, da Silva TL (September 2013). "Complementary and alternative therapies as add-on to pharmacotherapy for mood and anxiety disorders: a systematic review". <i>Journal of Affective Disorders</i>. <b>150</b> (3): 707–19. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2Fj.jad.2013.05.042">10.1016/j.jad.2013.05.042</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/23769610">23769610</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Journal+of+Affective+Disorders&rft.atitle=Complementary+and+alternative+therapies+as+add-on+to+pharmacotherapy+for+mood+and+anxiety+disorders%3A+a+systematic+review&rft.volume=150&rft.issue=3&rft.pages=707-19&rft.date=2013-09&rft_id=info%3Adoi%2F10.1016%2Fj.jad.2013.05.042&rft_id=info%3Apmid%2F23769610&rft.aulast=Ravindran&rft.aufirst=AV&rft.au=da+Silva%2C+TL&rfr_id=info%3Asid%2Fen.wikipedia.org%3ATryptophan" class="Z3988"></span></span> </li> <li id="cite_note-pmid27998379-32"><span class="mw-cite-backlink"><b><a href="#cite_ref-pmid27998379_32-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFSateiaBuysseKrystalNeubauer2017" class="citation journal cs1">Sateia MJ, Buysse DJ, Krystal AD, Neubauer DN, Heald JL (February 2017). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5263087">"Clinical Practice Guideline for the Pharmacologic Treatment of Chronic Insomnia in Adults: An American Academy of Sleep Medicine Clinical Practice Guideline"</a>. <i>J Clin Sleep Med</i>. <b>13</b> (2): 307–349. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.5664%2Fjcsm.6470">10.5664/jcsm.6470</a>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5263087">5263087</a></span>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/27998379">27998379</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=J+Clin+Sleep+Med&rft.atitle=Clinical+Practice+Guideline+for+the+Pharmacologic+Treatment+of+Chronic+Insomnia+in+Adults%3A+An+American+Academy+of+Sleep+Medicine+Clinical+Practice+Guideline&rft.volume=13&rft.issue=2&rft.pages=307-349&rft.date=2017-02&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC5263087%23id-name%3DPMC&rft_id=info%3Apmid%2F27998379&rft_id=info%3Adoi%2F10.5664%2Fjcsm.6470&rft.aulast=Sateia&rft.aufirst=MJ&rft.au=Buysse%2C+DJ&rft.au=Krystal%2C+AD&rft.au=Neubauer%2C+DN&rft.au=Heald%2C+JL&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC5263087&rfr_id=info%3Asid%2Fen.wikipedia.org%3ATryptophan" class="Z3988"></span></span> </li> <li id="cite_note-pmid23077196-33"><span class="mw-cite-backlink"><b><a href="#cite_ref-pmid23077196_33-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFKimuraBierTaylor2012" class="citation journal cs1">Kimura T, Bier DM, Taylor CL (December 2012). <a rel="nofollow" class="external text" href="https://doi.org/10.3945%2Fjn.112.160846">"Summary of workshop discussions on establishing upper limits for amino acids with specific attention to available data for the essential amino acids leucine and tryptophan"</a>. <i>The Journal of Nutrition</i>. <b>142</b> (12): 2245S–2248S. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://doi.org/10.3945%2Fjn.112.160846">10.3945/jn.112.160846</a></span>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/23077196">23077196</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=The+Journal+of+Nutrition&rft.atitle=Summary+of+workshop+discussions+on+establishing+upper+limits+for+amino+acids+with+specific+attention+to+available+data+for+the+essential+amino+acids+leucine+and+tryptophan&rft.volume=142&rft.issue=12&rft.pages=2245S-2248S&rft.date=2012-12&rft_id=info%3Adoi%2F10.3945%2Fjn.112.160846&rft_id=info%3Apmid%2F23077196&rft.aulast=Kimura&rft.aufirst=T&rft.au=Bier%2C+DM&rft.au=Taylor%2C+CL&rft_id=https%3A%2F%2Fdoi.org%2F10.3945%252Fjn.112.160846&rfr_id=info%3Asid%2Fen.wikipedia.org%3ATryptophan" class="Z3988"></span></span> </li> <li id="cite_note-pmid22589230-34"><span class="mw-cite-backlink">^ <a href="#cite_ref-pmid22589230_34-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-pmid22589230_34-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFHowland2012" class="citation journal cs1">Howland RH (June 2012). "Dietary supplement drug therapies for depression". <i>Journal of Psychosocial Nursing and Mental Health Services</i>. <b>50</b> (6): 13–6. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.3928%2F02793695-20120508-06">10.3928/02793695-20120508-06</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/22589230">22589230</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Journal+of+Psychosocial+Nursing+and+Mental+Health+Services&rft.atitle=Dietary+supplement+drug+therapies+for+depression&rft.volume=50&rft.issue=6&rft.pages=13-6&rft.date=2012-06&rft_id=info%3Adoi%2F10.3928%2F02793695-20120508-06&rft_id=info%3Apmid%2F22589230&rft.aulast=Howland&rft.aufirst=RH&rfr_id=info%3Asid%2Fen.wikipedia.org%3ATryptophan" class="Z3988"></span></span> </li> <li id="cite_note-pmid16992614-35"><span class="mw-cite-backlink"><b><a href="#cite_ref-pmid16992614_35-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFHopkinsCole1901" class="citation journal cs1">Hopkins FG, Cole SW (December 1901). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1540554">"A contribution to the chemistry of proteids: Part I. A preliminary study of a hitherto undescribed product of tryptic digestion"</a>. <i>The Journal of Physiology</i>. <b>27</b> (4–5): 418–428. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1113%2Fjphysiol.1901.sp000880">10.1113/jphysiol.1901.sp000880</a>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1540554">1540554</a></span>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/16992614">16992614</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=The+Journal+of+Physiology&rft.atitle=A+contribution+to+the+chemistry+of+proteids%3A+Part+I.+A+preliminary+study+of+a+hitherto+undescribed+product+of+tryptic+digestion&rft.volume=27&rft.issue=4%E2%80%935&rft.pages=418-428&rft.date=1901-12&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC1540554%23id-name%3DPMC&rft_id=info%3Apmid%2F16992614&rft_id=info%3Adoi%2F10.1113%2Fjphysiol.1901.sp000880&rft.aulast=Hopkins&rft.aufirst=FG&rft.au=Cole%2C+SW&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC1540554&rfr_id=info%3Asid%2Fen.wikipedia.org%3ATryptophan" class="Z3988"></span></span> </li> <li id="cite_note-Cox_1943-36"><span class="mw-cite-backlink"><b><a href="#cite_ref-Cox_1943_36-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFCoxKing1930" class="citation journal cs1">Cox G, King H (1930). <a rel="nofollow" class="external text" href="http://www.orgsyn.org/demo.aspx?prep=CV2P0612">"L-Tryptophane"</a>. <i>Org. Synth</i>. <b>10</b>: 100. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.15227%2Forgsyn.010.0100">10.15227/orgsyn.010.0100</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Org.+Synth.&rft.atitle=L-Tryptophane&rft.volume=10&rft.pages=100&rft.date=1930&rft_id=info%3Adoi%2F10.15227%2Forgsyn.010.0100&rft.aulast=Cox&rft.aufirst=G.J.&rft.au=King%2C+H.&rft_id=http%3A%2F%2Fwww.orgsyn.org%2Fdemo.aspx%3Fprep%3DCV2P0612&rfr_id=info%3Asid%2Fen.wikipedia.org%3ATryptophan" class="Z3988"></span></span> </li> <li id="cite_note-pmid7640526-37"><span class="mw-cite-backlink"><b><a href="#cite_ref-pmid7640526_37-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFRadwanskiLast1995" class="citation journal cs1">Radwanski ER, Last RL (1995). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC160888">"Tryptophan biosynthesis and metabolism: biochemical and molecular genetics"</a>. <i>The Plant Cell</i>. <b>7</b> (7): 921–34. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1105%2Ftpc.7.7.921">10.1105/tpc.7.7.921</a>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC160888">160888</a></span>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/7640526">7640526</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=The+Plant+Cell&rft.atitle=Tryptophan+biosynthesis+and+metabolism%3A+biochemical+and+molecular+genetics&rft.volume=7&rft.issue=7&rft.pages=921-34&rft.date=1995&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC160888%23id-name%3DPMC&rft_id=info%3Apmid%2F7640526&rft_id=info%3Adoi%2F10.1105%2Ftpc.7.7.921&rft.aulast=Radwanski&rft.aufirst=ER&rft.au=Last%2C+RL&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC160888&rfr_id=info%3Asid%2Fen.wikipedia.org%3ATryptophan" class="Z3988"></span></span> </li> <li id="cite_note-pmid12523387-38"><span class="mw-cite-backlink"><b><a href="#cite_ref-pmid12523387_38-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFIkeda2002" class="citation book cs1">Ikeda M (2002). "Amino acid production processes". <i>Microbial Production of l-Amino Acids</i>. Advances in Biochemical Engineering/Biotechnology. Vol. 79. pp. 1–35. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1007%2F3-540-45989-8_1">10.1007/3-540-45989-8_1</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-3-540-43383-5" title="Special:BookSources/978-3-540-43383-5"><bdi>978-3-540-43383-5</bdi></a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/12523387">12523387</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Amino+acid+production+processes&rft.btitle=Microbial+Production+of+l-Amino+Acids&rft.series=Advances+in+Biochemical+Engineering%2FBiotechnology&rft.pages=1-35&rft.date=2002&rft_id=info%3Apmid%2F12523387&rft_id=info%3Adoi%2F10.1007%2F3-540-45989-8_1&rft.isbn=978-3-540-43383-5&rft.aulast=Ikeda&rft.aufirst=M&rfr_id=info%3Asid%2Fen.wikipedia.org%3ATryptophan" class="Z3988"></span></span> </li> <li id="cite_note-pmid22138494-39"><span class="mw-cite-backlink"><b><a href="#cite_ref-pmid22138494_39-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFBeckerWittmann2012" class="citation journal cs1">Becker J, Wittmann C (2012). "Bio-based production of chemicals, materials and fuels -Corynebacterium glutamicum as versatile cell factory". <i>Current Opinion in Biotechnology</i>. <b>23</b> (4): 631–40. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2Fj.copbio.2011.11.012">10.1016/j.copbio.2011.11.012</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/22138494">22138494</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Current+Opinion+in+Biotechnology&rft.atitle=Bio-based+production+of+chemicals%2C+materials+and+fuels+-Corynebacterium+glutamicum+as+versatile+cell+factory&rft.volume=23&rft.issue=4&rft.pages=631-40&rft.date=2012&rft_id=info%3Adoi%2F10.1016%2Fj.copbio.2011.11.012&rft_id=info%3Apmid%2F22138494&rft.aulast=Becker&rft.aufirst=J&rft.au=Wittmann%2C+C&rfr_id=info%3Asid%2Fen.wikipedia.org%3ATryptophan" class="Z3988"></span></span> </li> <li id="cite_note-pmid18725290-40"><span class="mw-cite-backlink"><b><a href="#cite_ref-pmid18725290_40-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFConradoVarnerDeLisa2008" class="citation journal cs1">Conrado RJ, Varner JD, DeLisa MP (2008). "Engineering the spatial organization of metabolic enzymes: mimicking nature's synergy". <i>Current Opinion in Biotechnology</i>. <b>19</b> (5): 492–9. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2Fj.copbio.2008.07.006">10.1016/j.copbio.2008.07.006</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/18725290">18725290</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Current+Opinion+in+Biotechnology&rft.atitle=Engineering+the+spatial+organization+of+metabolic+enzymes%3A+mimicking+nature%27s+synergy&rft.volume=19&rft.issue=5&rft.pages=492-9&rft.date=2008&rft_id=info%3Adoi%2F10.1016%2Fj.copbio.2008.07.006&rft_id=info%3Apmid%2F18725290&rft.aulast=Conrado&rft.aufirst=RJ&rft.au=Varner%2C+JD&rft.au=DeLisa%2C+MP&rfr_id=info%3Asid%2Fen.wikipedia.org%3ATryptophan" class="Z3988"></span></span> </li> <li id="cite_note-41"><span class="mw-cite-backlink"><b><a href="#cite_ref-41">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFAllenVarga2014" class="citation book cs1">Allen J, Varga J (2014). "Eosinophilia–Myalgia Syndrome". In Wexler P (ed.). <i>Encyclopedia of Toxicology</i> (3rd ed.). Burlington: Elsevier Science. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-12-386455-0" title="Special:BookSources/978-0-12-386455-0"><bdi>978-0-12-386455-0</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Eosinophilia%E2%80%93Myalgia+Syndrome&rft.btitle=Encyclopedia+of+Toxicology&rft.place=Burlington&rft.edition=3rd&rft.pub=Elsevier+Science&rft.date=2014&rft.isbn=978-0-12-386455-0&rft.aulast=Allen&rft.aufirst=J.A.&rft.au=Varga%2C+J&rfr_id=info%3Asid%2Fen.wikipedia.org%3ATryptophan" class="Z3988"></span></span> </li> <li id="cite_note-FDA_Tryptophan_Info-42"><span class="mw-cite-backlink">^ <a href="#cite_ref-FDA_Tryptophan_Info_42-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-FDA_Tryptophan_Info_42-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-FDA_Tryptophan_Info_42-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-FDA_Tryptophan_Info_42-3"><sup><i><b>d</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://web.archive.org/web/20050225100757/http://www.cfsan.fda.gov/~dms/ds-tryp1.html">"Information Paper on L-tryptophan and 5-hydroxy-L-tryptophan"</a>. FU. S. Food and Drug Administration, Center for Food Safety and Applied Nutrition, Office of Nutritional Products, Labeling, and Dietary Supplements. 1 February 2001. Archived from <a rel="nofollow" class="external text" href="http://www.cfsan.fda.gov/~dms/ds-tryp1.html">the original</a> on 25 February 2005<span class="reference-accessdate">. Retrieved <span class="nowrap">8 February</span> 2012</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=Information+Paper+on+L-tryptophan+and+5-hydroxy-L-tryptophan&rft.pub=FU.+S.+Food+and+Drug+Administration%2C+Center+for+Food+Safety+and+Applied+Nutrition%2C+Office+of+Nutritional+Products%2C+Labeling%2C+and+Dietary+Supplements&rft.date=2001-02-01&rft_id=http%3A%2F%2Fwww.cfsan.fda.gov%2F~dms%2Fds-tryp1.html&rfr_id=info%3Asid%2Fen.wikipedia.org%3ATryptophan" class="Z3988"></span></span> </li> <li id="cite_note-43"><span class="mw-cite-backlink"><b><a href="#cite_ref-43">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="http://www.webmd.com/vitamins-and-supplements/l-tryptophan-uses-and-risks#1">"L-tryptophan: Uses and Risks"</a>. <i><a href="/wiki/WebMD" title="WebMD">WebMD</a></i>. 12 May 2017<span class="reference-accessdate">. Retrieved <span class="nowrap">5 June</span> 2017</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=WebMD&rft.atitle=L-tryptophan%3A+Uses+and+Risks&rft.date=2017-05-12&rft_id=http%3A%2F%2Fwww.webmd.com%2Fvitamins-and-supplements%2Fl-tryptophan-uses-and-risks%231&rfr_id=info%3Asid%2Fen.wikipedia.org%3ATryptophan" class="Z3988"></span></span> </li> <li id="cite_note-44"><span class="mw-cite-backlink"><b><a href="#cite_ref-44">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFAltman1990" class="citation news cs1">Altman LK (27 April 1990). <a rel="nofollow" class="external text" href="https://www.nytimes.com/1990/04/27/us/studies-tie-disorder-to-maker-of-food-supplement.html">"Studies Tie Disorder to Maker of Food Supplement"</a>. <i>The New York Times</i>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=The+New+York+Times&rft.atitle=Studies+Tie+Disorder+to+Maker+of+Food+Supplement&rft.date=1990-04-27&rft.aulast=Altman&rft.aufirst=Lawrence+K.&rft_id=https%3A%2F%2Fwww.nytimes.com%2F1990%2F04%2F27%2Fus%2Fstudies-tie-disorder-to-maker-of-food-supplement.html&rfr_id=info%3Asid%2Fen.wikipedia.org%3ATryptophan" class="Z3988"></span></span> </li> <li id="cite_note-45"><span class="mw-cite-backlink"><b><a href="#cite_ref-45">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFCastotBidaultBourneriasCarlier1991" class="citation journal cs1">Castot A, Bidault I, Bournerias I, Carlier P, Efthymiou ML (1991). "["Eosinophilia-myalgia" syndrome due to L-tryptophan containing products. Cooperative evaluation of French Regional Centers of Pharmacovigilance. Analysis of 24 cases]". <i>Thérapie</i>. <b>46</b> (5): 355–65. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/1754978">1754978</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Th%C3%A9rapie&rft.atitle=%5B%22Eosinophilia-myalgia%22+syndrome+due+to+L-tryptophan+containing+products.+Cooperative+evaluation+of+French+Regional+Centers+of+Pharmacovigilance.+Analysis+of+24+cases%5D.&rft.volume=46&rft.issue=5&rft.pages=355-65&rft.date=1991&rft_id=info%3Apmid%2F1754978&rft.aulast=Castot&rft.aufirst=A&rft.au=Bidault%2C+I&rft.au=Bournerias%2C+I&rft.au=Carlier%2C+P&rft.au=Efthymiou%2C+ML&rfr_id=info%3Asid%2Fen.wikipedia.org%3ATryptophan" class="Z3988"></span></span> </li> <li id="cite_note-46"><span class="mw-cite-backlink"><b><a href="#cite_ref-46">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://cot.food.gov.uk/sites/default/files/cot/tryptophanamend200401.pdf">"COT Statement on Tryptophan and the Eosinophilia-Myalgia Syndrome"</a> <span class="cs1-format">(PDF)</span>. UK Committee on Toxicity of Chemicals in Food, Consumer Products and the Environment. June 2004.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=COT+Statement+on+Tryptophan+and+the+Eosinophilia-Myalgia+Syndrome&rft.pub=UK+Committee+on+Toxicity+of+Chemicals+in+Food%2C+Consumer+Products+and+the+Environment&rft.date=2004-06&rft_id=https%3A%2F%2Fcot.food.gov.uk%2Fsites%2Fdefault%2Ffiles%2Fcot%2Ftryptophanamend200401.pdf&rfr_id=info%3Asid%2Fen.wikipedia.org%3ATryptophan" class="Z3988"></span></span> </li> <li id="cite_note-pmid2355442-47"><span class="mw-cite-backlink"><b><a href="#cite_ref-pmid2355442_47-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFSlutskerHoeslyMillerWilliams1990" class="citation journal cs1">Slutsker L, Hoesly FC, Miller L, Williams LP, Watson JC, Fleming DW (July 1990). "Eosinophilia-myalgia syndrome associated with exposure to tryptophan from a single manufacturer". <i>JAMA</i>. <b>264</b> (2): 213–7. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1001%2Fjama.264.2.213">10.1001/jama.264.2.213</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/2355442">2355442</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=JAMA&rft.atitle=Eosinophilia-myalgia+syndrome+associated+with+exposure+to+tryptophan+from+a+single+manufacturer&rft.volume=264&rft.issue=2&rft.pages=213-7&rft.date=1990-07&rft_id=info%3Adoi%2F10.1001%2Fjama.264.2.213&rft_id=info%3Apmid%2F2355442&rft.aulast=Slutsker&rft.aufirst=L&rft.au=Hoesly%2C+FC&rft.au=Miller%2C+L&rft.au=Williams%2C+LP&rft.au=Watson%2C+JC&rft.au=Fleming%2C+DW&rfr_id=info%3Asid%2Fen.wikipedia.org%3ATryptophan" class="Z3988"></span></span> </li> <li id="cite_note-pmid8496862-48"><span class="mw-cite-backlink"><b><a href="#cite_ref-pmid8496862_48-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFBackHenningKallenbachBrix1993" class="citation journal cs1">Back EE, Henning KJ, Kallenbach LR, Brix KA, Gunn RA, Melius JM (April 1993). "Risk factors for developing eosinophilia myalgia syndrome among L-tryptophan users in New York". <i>The Journal of Rheumatology</i>. <b>20</b> (4): 666–72. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/8496862">8496862</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=The+Journal+of+Rheumatology&rft.atitle=Risk+factors+for+developing+eosinophilia+myalgia+syndrome+among+L-tryptophan+users+in+New+York&rft.volume=20&rft.issue=4&rft.pages=666-72&rft.date=1993-04&rft_id=info%3Apmid%2F8496862&rft.aulast=Back&rft.aufirst=EE&rft.au=Henning%2C+KJ&rft.au=Kallenbach%2C+LR&rft.au=Brix%2C+KA&rft.au=Gunn%2C+RA&rft.au=Melius%2C+JM&rfr_id=info%3Asid%2Fen.wikipedia.org%3ATryptophan" class="Z3988"></span></span> </li> <li id="cite_note-pmid8895184-49"><span class="mw-cite-backlink"><b><a href="#cite_ref-pmid8895184_49-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFKilbournePhilenKambFalk1996" class="citation journal cs1">Kilbourne EM, Philen RM, Kamb ML, Falk H (October 1996). "Tryptophan produced by Showa Denko and epidemic eosinophilia-myalgia syndrome". <i>The Journal of Rheumatology. Supplement</i>. <b>46</b>: 81–8, discussion 89–91. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/8895184">8895184</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=The+Journal+of+Rheumatology.+Supplement&rft.atitle=Tryptophan+produced+by+Showa+Denko+and+epidemic+eosinophilia-myalgia+syndrome&rft.volume=46&rft.pages=81-8%2C+discussion+89-91&rft.date=1996-10&rft_id=info%3Apmid%2F8895184&rft.aulast=Kilbourne&rft.aufirst=EM&rft.au=Philen%2C+RM&rft.au=Kamb%2C+ML&rft.au=Falk%2C+H&rfr_id=info%3Asid%2Fen.wikipedia.org%3ATryptophan" class="Z3988"></span></span> </li> <li id="cite_note-pmid2270484-50"><span class="mw-cite-backlink"><b><a href="#cite_ref-pmid2270484_50-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFMayenoLinFooteLoegering1990" class="citation journal cs1">Mayeno AN, Lin F, Foote CS, Loegering DA, Ames MM, Hedberg CW, Gleich GJ (December 1990). "Characterization of "peak E," a novel amino acid associated with eosinophilia-myalgia syndrome". <i>Science</i>. <b>250</b> (4988): 1707–8. <a href="/wiki/Bibcode_(identifier)" class="mw-redirect" title="Bibcode (identifier)">Bibcode</a>:<a rel="nofollow" class="external text" href="https://ui.adsabs.harvard.edu/abs/1990Sci...250.1707M">1990Sci...250.1707M</a>. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1126%2Fscience.2270484">10.1126/science.2270484</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/2270484">2270484</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Science&rft.atitle=Characterization+of+%22peak+E%2C%22+a+novel+amino+acid+associated+with+eosinophilia-myalgia+syndrome&rft.volume=250&rft.issue=4988&rft.pages=1707-8&rft.date=1990-12&rft_id=info%3Apmid%2F2270484&rft_id=info%3Adoi%2F10.1126%2Fscience.2270484&rft_id=info%3Abibcode%2F1990Sci...250.1707M&rft.aulast=Mayeno&rft.aufirst=AN&rft.au=Lin%2C+F&rft.au=Foote%2C+CS&rft.au=Loegering%2C+DA&rft.au=Ames%2C+MM&rft.au=Hedberg%2C+CW&rft.au=Gleich%2C+GJ&rfr_id=info%3Asid%2Fen.wikipedia.org%3ATryptophan" class="Z3988"></span></span> </li> <li id="cite_note-pmid1544609-51"><span class="mw-cite-backlink"><b><a href="#cite_ref-pmid1544609_51-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFItoHosakiTorigoeSakimoto1992" class="citation journal cs1">Ito J, Hosaki Y, Torigoe Y, Sakimoto K (January 1992). "Identification of substances formed by decomposition of peak E substance in tryptophan". <i>Food and Chemical Toxicology</i>. <b>30</b> (1): 71–81. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2F0278-6915%2892%2990139-C">10.1016/0278-6915(92)90139-C</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/1544609">1544609</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Food+and+Chemical+Toxicology&rft.atitle=Identification+of+substances+formed+by+decomposition+of+peak+E+substance+in+tryptophan&rft.volume=30&rft.issue=1&rft.pages=71-81&rft.date=1992-01&rft_id=info%3Adoi%2F10.1016%2F0278-6915%2892%2990139-C&rft_id=info%3Apmid%2F1544609&rft.aulast=Ito&rft.aufirst=J&rft.au=Hosaki%2C+Y&rft.au=Torigoe%2C+Y&rft.au=Sakimoto%2C+K&rfr_id=info%3Asid%2Fen.wikipedia.org%3ATryptophan" class="Z3988"></span></span> </li> <li id="cite_note-pmid16307217-52"><span class="mw-cite-backlink"><b><a href="#cite_ref-pmid16307217_52-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFSmithGarrett2005" class="citation journal cs1">Smith MJ, Garrett RH (November 2005). "A heretofore undisclosed crux of eosinophilia-myalgia syndrome: compromised histamine degradation". <i>Inflammation Research</i>. <b>54</b> (11): 435–50. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1007%2Fs00011-005-1380-7">10.1007/s00011-005-1380-7</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/16307217">16307217</a>. <a href="/wiki/S2CID_(identifier)" class="mw-redirect" title="S2CID (identifier)">S2CID</a> <a rel="nofollow" class="external text" href="https://api.semanticscholar.org/CorpusID:7785345">7785345</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Inflammation+Research&rft.atitle=A+heretofore+undisclosed+crux+of+eosinophilia-myalgia+syndrome%3A+compromised+histamine+degradation&rft.volume=54&rft.issue=11&rft.pages=435-50&rft.date=2005-11&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A7785345%23id-name%3DS2CID&rft_id=info%3Apmid%2F16307217&rft_id=info%3Adoi%2F10.1007%2Fs00011-005-1380-7&rft.aulast=Smith&rft.aufirst=MJ&rft.au=Garrett%2C+RH&rfr_id=info%3Asid%2Fen.wikipedia.org%3ATryptophan" class="Z3988"></span></span> </li> <li id="cite_note-pred-53"><span class="mw-cite-backlink"><b><a href="#cite_ref-pred_53-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFMichael_Predator_Carlton" class="citation web cs1">Michael Predator Carlton. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20070624165916/http://conway.cat.org.au/%7Epredator/mol.html">"Molecular Biology and Genetic Engineering explained by someone who's done it"</a>. Archived from <a rel="nofollow" class="external text" href="http://conway.cat.org.au/%7Epredator/mol.html">the original</a> on 24 June 2007.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=Molecular+Biology+and+Genetic+Engineering+explained+by+someone+who%27s+done+it&rft.au=Michael+Predator+Carlton&rft_id=http%3A%2F%2Fconway.cat.org.au%2F%257Epredator%2Fmol.html&rfr_id=info%3Asid%2Fen.wikipedia.org%3ATryptophan" class="Z3988"></span></span> </li> <li id="cite_note-54"><span class="mw-cite-backlink"><b><a href="#cite_ref-54">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFAllenPetersonSufitHinchcliff2011" class="citation journal cs1">Allen JA, Peterson A, Sufit R, Hinchcliff ME, Mahoney JM, Wood TA, Miller FW, Whitfield ML, Varga J (November 2011). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3848710">"Post-epidemic eosinophilia-myalgia syndrome associated with L-tryptophan"</a>. <i>Arthritis and Rheumatism</i>. <b>63</b> (11): 3633–9. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2Fart.30514">10.1002/art.30514</a>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3848710">3848710</a></span>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/21702023">21702023</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Arthritis+and+Rheumatism&rft.atitle=Post-epidemic+eosinophilia-myalgia+syndrome+associated+with+L-tryptophan.&rft.volume=63&rft.issue=11&rft.pages=3633-9&rft.date=2011-11&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC3848710%23id-name%3DPMC&rft_id=info%3Apmid%2F21702023&rft_id=info%3Adoi%2F10.1002%2Fart.30514&rft.aulast=Allen&rft.aufirst=JA&rft.au=Peterson%2C+A&rft.au=Sufit%2C+R&rft.au=Hinchcliff%2C+ME&rft.au=Mahoney%2C+JM&rft.au=Wood%2C+TA&rft.au=Miller%2C+FW&rft.au=Whitfield%2C+ML&rft.au=Varga%2C+J&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC3848710&rfr_id=info%3Asid%2Fen.wikipedia.org%3ATryptophan" class="Z3988"></span></span> </li> <li id="cite_note-pmid7765187-55"><span class="mw-cite-backlink"><b><a href="#cite_ref-pmid7765187_55-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFMayenoGleich1994" class="citation journal cs1">Mayeno AN, Gleich GJ (September 1994). "Eosinophilia-myalgia syndrome and tryptophan production: a cautionary tale". <i>Trends in Biotechnology</i>. <b>12</b> (9): 346–52. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2F0167-7799%2894%2990035-3">10.1016/0167-7799(94)90035-3</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/7765187">7765187</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Trends+in+Biotechnology&rft.atitle=Eosinophilia-myalgia+syndrome+and+tryptophan+production%3A+a+cautionary+tale&rft.volume=12&rft.issue=9&rft.pages=346-52&rft.date=1994-09&rft_id=info%3Adoi%2F10.1016%2F0167-7799%2894%2990035-3&rft_id=info%3Apmid%2F7765187&rft.aulast=Mayeno&rft.aufirst=AN&rft.au=Gleich%2C+GJ&rfr_id=info%3Asid%2Fen.wikipedia.org%3ATryptophan" class="Z3988"></span></span> </li> <li id="cite_note-Science2000-56"><span class="mw-cite-backlink"><b><a href="#cite_ref-Science2000_56-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFRaphals1990" class="citation journal cs1">Raphals P (November 1990). "Does medical mystery threaten biotech?". <i>Science</i>. <b>250</b> (4981): 619. <a href="/wiki/Bibcode_(identifier)" class="mw-redirect" title="Bibcode (identifier)">Bibcode</a>:<a rel="nofollow" class="external text" href="https://ui.adsabs.harvard.edu/abs/1990Sci...250..619R">1990Sci...250..619R</a>. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1126%2Fscience.2237411">10.1126/science.2237411</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/2237411">2237411</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Science&rft.atitle=Does+medical+mystery+threaten+biotech%3F&rft.volume=250&rft.issue=4981&rft.pages=619&rft.date=1990-11&rft_id=info%3Apmid%2F2237411&rft_id=info%3Adoi%2F10.1126%2Fscience.2237411&rft_id=info%3Abibcode%2F1990Sci...250..619R&rft.aulast=Raphals&rft.aufirst=P&rfr_id=info%3Asid%2Fen.wikipedia.org%3ATryptophan" class="Z3988"></span></span> </li> <li id="cite_note-57"><span class="mw-cite-backlink"><b><a href="#cite_ref-57">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFHarding2023" class="citation news cs1">Harding N (21 December 2023). <a rel="nofollow" class="external text" href="https://www.telegraph.co.uk/health-fitness/wellbeing/sleep/why-christmas-foods-negatively-affect-sleep-quality/">"How to stop Christmas food from ruining your sleep"</a>. <i>The Telegraph</i>. <a href="/wiki/ISSN_(identifier)" class="mw-redirect" title="ISSN (identifier)">ISSN</a> <a rel="nofollow" class="external text" href="https://search.worldcat.org/issn/0307-1235">0307-1235</a><span class="reference-accessdate">. Retrieved <span class="nowrap">25 December</span> 2023</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=The+Telegraph&rft.atitle=How+to+stop+Christmas+food+from+ruining+your+sleep&rft.date=2023-12-21&rft.issn=0307-1235&rft.aulast=Harding&rft.aufirst=Nick&rft_id=https%3A%2F%2Fwww.telegraph.co.uk%2Fhealth-fitness%2Fwellbeing%2Fsleep%2Fwhy-christmas-foods-negatively-affect-sleep-quality%2F&rfr_id=info%3Asid%2Fen.wikipedia.org%3ATryptophan" class="Z3988"></span></span> </li> <li id="cite_note-HighBeam_Research_Interview-58"><span class="mw-cite-backlink"><b><a href="#cite_ref-HighBeam_Research_Interview_58-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation journal cs1"><a rel="nofollow" class="external text" href="https://www.questia.com/read/1G1-12520128">"Food & mood. (neuroscience professor Richard Wurtman) (Interview)"</a>. <i>Nutrition Action Healthletter</i>. September 1992.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Nutrition+Action+Healthletter&rft.atitle=Food+%26+mood.+%28neuroscience+professor+Richard+Wurtman%29+%28Interview%29&rft.date=1992-09&rft_id=https%3A%2F%2Fwww.questia.com%2Fread%2F1G1-12520128&rfr_id=info%3Asid%2Fen.wikipedia.org%3ATryptophan" class="Z3988"></span><sup class="noprint Inline-Template"><span style="white-space: nowrap;">[<i><a href="/wiki/Wikipedia:Link_rot" title="Wikipedia:Link rot"><span title=" Dead link tagged July 2021">dead link</span></a></i><span style="visibility:hidden; color:transparent; padding-left:2px">‍</span>]</span></sup></span> </li> <li id="cite_note-pmid3279747-59"><span class="mw-cite-backlink">^ <a href="#cite_ref-pmid3279747_59-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-pmid3279747_59-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFLyonsTruswell1988" class="citation journal cs1">Lyons PM, Truswell AS (March 1988). <a rel="nofollow" class="external text" href="https://doi.org/10.1093%2Fajcn%2F47.3.433">"Serotonin precursor influenced by type of carbohydrate meal in healthy adults"</a>. <i>The American Journal of Clinical Nutrition</i>. <b>47</b> (3): 433–9. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://doi.org/10.1093%2Fajcn%2F47.3.433">10.1093/ajcn/47.3.433</a></span>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/3279747">3279747</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=The+American+Journal+of+Clinical+Nutrition&rft.atitle=Serotonin+precursor+influenced+by+type+of+carbohydrate+meal+in+healthy+adults&rft.volume=47&rft.issue=3&rft.pages=433-9&rft.date=1988-03&rft_id=info%3Adoi%2F10.1093%2Fajcn%2F47.3.433&rft_id=info%3Apmid%2F3279747&rft.aulast=Lyons&rft.aufirst=PM&rft.au=Truswell%2C+AS&rft_id=https%3A%2F%2Fdoi.org%2F10.1093%252Fajcn%252F47.3.433&rfr_id=info%3Asid%2Fen.wikipedia.org%3ATryptophan" class="Z3988"></span></span> </li> <li id="cite_note-pmid12499331-60"><span class="mw-cite-backlink">^ <a href="#cite_ref-pmid12499331_60-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-pmid12499331_60-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-pmid12499331_60-2"><sup><i><b>c</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFWurtmanWurtmanReganMcDermott2003" class="citation journal cs1">Wurtman RJ, Wurtman JJ, Regan MM, McDermott JM, Tsay RH, Breu JJ (January 2003). <a rel="nofollow" class="external text" href="https://doi.org/10.1093%2Fajcn%2F77.1.128">"Effects of normal meals rich in carbohydrates or proteins on plasma tryptophan and tyrosine ratios"</a>. <i>The American Journal of Clinical Nutrition</i>. <b>77</b> (1): 128–32. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://doi.org/10.1093%2Fajcn%2F77.1.128">10.1093/ajcn/77.1.128</a></span>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/12499331">12499331</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=The+American+Journal+of+Clinical+Nutrition&rft.atitle=Effects+of+normal+meals+rich+in+carbohydrates+or+proteins+on+plasma+tryptophan+and+tyrosine+ratios&rft.volume=77&rft.issue=1&rft.pages=128-32&rft.date=2003-01&rft_id=info%3Adoi%2F10.1093%2Fajcn%2F77.1.128&rft_id=info%3Apmid%2F12499331&rft.aulast=Wurtman&rft.aufirst=RJ&rft.au=Wurtman%2C+JJ&rft.au=Regan%2C+MM&rft.au=McDermott%2C+JM&rft.au=Tsay%2C+RH&rft.au=Breu%2C+JJ&rft_id=https%3A%2F%2Fdoi.org%2F10.1093%252Fajcn%252F77.1.128&rfr_id=info%3Asid%2Fen.wikipedia.org%3ATryptophan" class="Z3988"></span></span> </li> <li id="cite_note-pmid17284739-61"><span class="mw-cite-backlink">^ <a href="#cite_ref-pmid17284739_61-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-pmid17284739_61-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFAfaghiO'ConnorChow2007" class="citation journal cs1">Afaghi A, O'Connor H, Chow CM (February 2007). <a rel="nofollow" class="external text" href="https://doi.org/10.1093%2Fajcn%2F85.2.426">"High-glycemic-index carbohydrate meals shorten sleep onset"</a>. <i>The American Journal of Clinical Nutrition</i>. <b>85</b> (2): 426–30. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://doi.org/10.1093%2Fajcn%2F85.2.426">10.1093/ajcn/85.2.426</a></span>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/17284739">17284739</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=The+American+Journal+of+Clinical+Nutrition&rft.atitle=High-glycemic-index+carbohydrate+meals+shorten+sleep+onset&rft.volume=85&rft.issue=2&rft.pages=426-30&rft.date=2007-02&rft_id=info%3Adoi%2F10.1093%2Fajcn%2F85.2.426&rft_id=info%3Apmid%2F17284739&rft.aulast=Afaghi&rft.aufirst=A&rft.au=O%27Connor%2C+H&rft.au=Chow%2C+CM&rft_id=https%3A%2F%2Fdoi.org%2F10.1093%252Fajcn%252F85.2.426&rfr_id=info%3Asid%2Fen.wikipedia.org%3ATryptophan" class="Z3988"></span></span> </li> <li id="cite_note-Banks-2012-62"><span class="mw-cite-backlink">^ <a href="#cite_ref-Banks-2012_62-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Banks-2012_62-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFBanksOwenErickson2012" class="citation journal cs1">Banks WA, Owen JB, Erickson MA (2012). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4134675">"Insulin in the Brain: There and Back Again"</a>. <i>Pharmacology & Therapeutics</i>. <b>136</b> (1): 82–93. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2Fj.pharmthera.2012.07.006">10.1016/j.pharmthera.2012.07.006</a>. <a href="/wiki/ISSN_(identifier)" class="mw-redirect" title="ISSN (identifier)">ISSN</a> <a rel="nofollow" class="external text" href="https://search.worldcat.org/issn/0163-7258">0163-7258</a>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4134675">4134675</a></span>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/22820012">22820012</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Pharmacology+%26+Therapeutics&rft.atitle=Insulin+in+the+Brain%3A+There+and+Back+Again&rft.volume=136&rft.issue=1&rft.pages=82-93&rft.date=2012&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC4134675%23id-name%3DPMC&rft.issn=0163-7258&rft_id=info%3Apmid%2F22820012&rft_id=info%3Adoi%2F10.1016%2Fj.pharmthera.2012.07.006&rft.aulast=Banks&rft.aufirst=WA&rft.au=Owen%2C+JB&rft.au=Erickson%2C+MA&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC4134675&rfr_id=info%3Asid%2Fen.wikipedia.org%3ATryptophan" class="Z3988"></span></span> </li> <li id="cite_note-pmid1148286-63"><span class="mw-cite-backlink"><b><a href="#cite_ref-pmid1148286_63-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFPardridgeOldendorf1975" class="citation journal cs1">Pardridge WM, <a href="/wiki/William_H._Oldendorf" title="William H. Oldendorf">Oldendorf WH</a> (August 1975). "Kinetic analysis of blood-brain barrier transport of amino acids". <i>Biochimica et Biophysica Acta (BBA) - Biomembranes</i>. <b>401</b> (1): 128–36. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2F0005-2736%2875%2990347-8">10.1016/0005-2736(75)90347-8</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/1148286">1148286</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Biochimica+et+Biophysica+Acta+%28BBA%29+-+Biomembranes&rft.atitle=Kinetic+analysis+of+blood-brain+barrier+transport+of+amino+acids&rft.volume=401&rft.issue=1&rft.pages=128-36&rft.date=1975-08&rft_id=info%3Adoi%2F10.1016%2F0005-2736%2875%2990347-8&rft_id=info%3Apmid%2F1148286&rft.aulast=Pardridge&rft.aufirst=WM&rft.au=Oldendorf%2C+WH&rfr_id=info%3Asid%2Fen.wikipedia.org%3ATryptophan" class="Z3988"></span></span> </li> <li id="cite_note-pmid6538743-64"><span class="mw-cite-backlink"><b><a href="#cite_ref-pmid6538743_64-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFMaherGlaeserWurtman1984" class="citation journal cs1">Maher TJ, Glaeser BS, Wurtman RJ (May 1984). "Diurnal variations in plasma concentrations of basic and neutral amino acids and in red cell concentrations of aspartate and glutamate: effects of dietary protein intake". <i>The American Journal of Clinical Nutrition</i>. <b>39</b> (5): 722–9. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1093%2Fajcn%2F39.5.722">10.1093/ajcn/39.5.722</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/6538743">6538743</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=The+American+Journal+of+Clinical+Nutrition&rft.atitle=Diurnal+variations+in+plasma+concentrations+of+basic+and+neutral+amino+acids+and+in+red+cell+concentrations+of+aspartate+and+glutamate%3A+effects+of+dietary+protein+intake&rft.volume=39&rft.issue=5&rft.pages=722-9&rft.date=1984-05&rft_id=info%3Adoi%2F10.1093%2Fajcn%2F39.5.722&rft_id=info%3Apmid%2F6538743&rft.aulast=Maher&rft.aufirst=TJ&rft.au=Glaeser%2C+BS&rft.au=Wurtman%2C+RJ&rfr_id=info%3Asid%2Fen.wikipedia.org%3ATryptophan" class="Z3988"></span></span> </li> <li id="cite_note-pmid5120086-65"><span class="mw-cite-backlink">^ <a href="#cite_ref-pmid5120086_65-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-pmid5120086_65-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFFernstromWurtman1971" class="citation journal cs1">Fernstrom JD, Wurtman RJ (1971). "Brain serotonin content: increase following ingestion of carbohydrate diet". <i>Science</i>. <b>174</b> (4013): 1023–5. <a href="/wiki/Bibcode_(identifier)" class="mw-redirect" title="Bibcode (identifier)">Bibcode</a>:<a rel="nofollow" class="external text" href="https://ui.adsabs.harvard.edu/abs/1971Sci...174.1023F">1971Sci...174.1023F</a>. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1126%2Fscience.174.4013.1023">10.1126/science.174.4013.1023</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/5120086">5120086</a>. <a href="/wiki/S2CID_(identifier)" class="mw-redirect" title="S2CID (identifier)">S2CID</a> <a rel="nofollow" class="external text" href="https://api.semanticscholar.org/CorpusID:14345137">14345137</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Science&rft.atitle=Brain+serotonin+content%3A+increase+following+ingestion+of+carbohydrate+diet&rft.volume=174&rft.issue=4013&rft.pages=1023-5&rft.date=1971&rft_id=info%3Adoi%2F10.1126%2Fscience.174.4013.1023&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A14345137%23id-name%3DS2CID&rft_id=info%3Apmid%2F5120086&rft_id=info%3Abibcode%2F1971Sci...174.1023F&rft.aulast=Fernstrom&rft.aufirst=JD&rft.au=Wurtman%2C+RJ&rfr_id=info%3Asid%2Fen.wikipedia.org%3ATryptophan" class="Z3988"></span></span> </li> <li id="cite_note-66"><span class="mw-cite-backlink"><b><a href="#cite_ref-66">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFAtul_Khullar2012" class="citation journal cs1">Atul Khullar MD (10 July 2012). <a rel="nofollow" class="external text" href="https://www.psychiatrictimes.com/view/role-melatonin-circadian-rhythm-sleep-wake-cycle">"The Role of Melatonin in the Circadian Rhythm Sleep-Wake Cycle"</a>. <i>Psychiatric Times</i>. <b>29</b> (7).</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Psychiatric+Times&rft.atitle=The+Role+of+Melatonin+in+the+Circadian+Rhythm+Sleep-Wake+Cycle&rft.volume=29&rft.issue=7&rft.date=2012-07-10&rft.aulast=Atul+Khullar&rft.aufirst=M.+D.&rft_id=https%3A%2F%2Fwww.psychiatrictimes.com%2Fview%2Frole-melatonin-circadian-rhythm-sleep-wake-cycle&rfr_id=info%3Asid%2Fen.wikipedia.org%3ATryptophan" class="Z3988"></span></span> </li> <li id="cite_note-67"><span class="mw-cite-backlink"><b><a href="#cite_ref-67">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFJackson1930" class="citation journal cs1">Jackson RW (1930). <a rel="nofollow" class="external text" href="http://www.jbc.org/content/88/3/659.full.pdf">"A synthesis of tryptophol"</a> <span class="cs1-format">(PDF)</span>. <i>Journal of Biological Chemistry</i>. <b>88</b> (3): 659–662. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://doi.org/10.1016%2FS0021-9258%2818%2976755-0">10.1016/S0021-9258(18)76755-0</a></span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Journal+of+Biological+Chemistry&rft.atitle=A+synthesis+of+tryptophol&rft.volume=88&rft.issue=3&rft.pages=659-662&rft.date=1930&rft_id=info%3Adoi%2F10.1016%2FS0021-9258%2818%2976755-0&rft.aulast=Jackson&rft.aufirst=RW&rft_id=http%3A%2F%2Fwww.jbc.org%2Fcontent%2F88%2F3%2F659.full.pdf&rfr_id=info%3Asid%2Fen.wikipedia.org%3ATryptophan" class="Z3988"></span></span> </li> <li id="cite_note-pmid23428157-68"><span class="mw-cite-backlink"><b><a href="#cite_ref-pmid23428157_68-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFYoung2013" class="citation journal cs1">Young SN (September 2013). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3756112">"Acute tryptophan depletion in humans: a review of theoretical, practical and ethical aspects"</a>. <i>Journal of Psychiatry & Neuroscience</i>. <b>38</b> (5): 294–305. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1503%2Fjpn.120209">10.1503/jpn.120209</a>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3756112">3756112</a></span>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/23428157">23428157</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Journal+of+Psychiatry+%26+Neuroscience&rft.atitle=Acute+tryptophan+depletion+in+humans%3A+a+review+of+theoretical%2C+practical+and+ethical+aspects&rft.volume=38&rft.issue=5&rft.pages=294-305&rft.date=2013-09&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC3756112%23id-name%3DPMC&rft_id=info%3Apmid%2F23428157&rft_id=info%3Adoi%2F10.1503%2Fjpn.120209&rft.aulast=Young&rft.aufirst=SN&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC3756112&rfr_id=info%3Asid%2Fen.wikipedia.org%3ATryptophan" class="Z3988"></span></span> </li> <li id="cite_note-pmid23440461-69"><span class="mw-cite-backlink"><b><a href="#cite_ref-pmid23440461_69-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFYoung2013" class="citation journal cs1">Young SN (2013). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3638380">"The effect of raising and lowering tryptophan levels on human mood and social behaviour"</a>. <i>Philosophical Transactions of the Royal Society of London. Series B, Biological Sciences</i>. <b>368</b> (1615): 20110375. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1098%2Frstb.2011.0375">10.1098/rstb.2011.0375</a>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3638380">3638380</a></span>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/23440461">23440461</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Philosophical+Transactions+of+the+Royal+Society+of+London.+Series+B%2C+Biological+Sciences&rft.atitle=The+effect+of+raising+and+lowering+tryptophan+levels+on+human+mood+and+social+behaviour&rft.volume=368&rft.issue=1615&rft.pages=20110375&rft.date=2013&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC3638380%23id-name%3DPMC&rft_id=info%3Apmid%2F23440461&rft_id=info%3Adoi%2F10.1098%2Frstb.2011.0375&rft.aulast=Young&rft.aufirst=SN&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC3638380&rfr_id=info%3Asid%2Fen.wikipedia.org%3ATryptophan" class="Z3988"></span></span> </li> <li id="cite_note-HalberstadtGeyer2018-70"><span class="mw-cite-backlink">^ <a href="#cite_ref-HalberstadtGeyer2018_70-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-HalberstadtGeyer2018_70-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFHalberstadtGeyer2018" class="citation journal cs1">Halberstadt AL, Geyer MA (2018). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5787039">"Effect of Hallucinogens on Unconditioned Behavior"</a>. <i>Curr Top Behav Neurosci</i>. Current Topics in Behavioral Neurosciences. <b>36</b>: 159–199. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1007%2F7854_2016_466">10.1007/7854_2016_466</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-3-662-55878-2" title="Special:BookSources/978-3-662-55878-2"><bdi>978-3-662-55878-2</bdi></a>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5787039">5787039</a></span>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/28224459">28224459</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Curr+Top+Behav+Neurosci&rft.atitle=Effect+of+Hallucinogens+on+Unconditioned+Behavior&rft.volume=36&rft.pages=159-199&rft.date=2018&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC5787039%23id-name%3DPMC&rft_id=info%3Apmid%2F28224459&rft_id=info%3Adoi%2F10.1007%2F7854_2016_466&rft.isbn=978-3-662-55878-2&rft.aulast=Halberstadt&rft.aufirst=AL&rft.au=Geyer%2C+MA&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC5787039&rfr_id=info%3Asid%2Fen.wikipedia.org%3ATryptophan" class="Z3988"></span></span> </li> <li id="cite_note-CanalMorgan2012-71"><span class="mw-cite-backlink"><b><a href="#cite_ref-CanalMorgan2012_71-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFCanalMorgan2012" class="citation journal cs1">Canal CE, Morgan D (2012). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3722587">"Head-twitch response in rodents induced by the hallucinogen 2,5-dimethoxy-4-iodoamphetamine: a comprehensive history, a re-evaluation of mechanisms, and its utility as a model"</a>. <i>Drug Test Anal</i>. <b>4</b> (7–8): 556–576. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2Fdta.1333">10.1002/dta.1333</a>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3722587">3722587</a></span>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/22517680">22517680</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Drug+Test+Anal&rft.atitle=Head-twitch+response+in+rodents+induced+by+the+hallucinogen+2%2C5-dimethoxy-4-iodoamphetamine%3A+a+comprehensive+history%2C+a+re-evaluation+of+mechanisms%2C+and+its+utility+as+a+model&rft.volume=4&rft.issue=7%E2%80%938&rft.pages=556-576&rft.date=2012&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC3722587%23id-name%3DPMC&rft_id=info%3Apmid%2F22517680&rft_id=info%3Adoi%2F10.1002%2Fdta.1333&rft.aulast=Canal&rft.aufirst=CE&rft.au=Morgan%2C+D&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC3722587&rfr_id=info%3Asid%2Fen.wikipedia.org%3ATryptophan" class="Z3988"></span></span> </li> <li id="cite_note-KozlenkovGonzález-Maeso2013-72"><span class="mw-cite-backlink"><b><a href="#cite_ref-KozlenkovGonzález-Maeso2013_72-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFKozlenkovGonzález-Maeso2013" class="citation book cs1">Kozlenkov A, González-Maeso J (2013). "Animal Models and Hallucinogenic Drugs". <i>The Neuroscience of Hallucinations</i>. New York, NY: Springer New York. pp. 253–277. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1007%2F978-1-4614-4121-2_14">10.1007/978-1-4614-4121-2_14</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1-4614-4120-5" title="Special:BookSources/978-1-4614-4120-5"><bdi>978-1-4614-4120-5</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Animal+Models+and+Hallucinogenic+Drugs&rft.btitle=The+Neuroscience+of+Hallucinations&rft.place=New+York%2C+NY&rft.pages=253-277&rft.pub=Springer+New+York&rft.date=2013&rft_id=info%3Adoi%2F10.1007%2F978-1-4614-4121-2_14&rft.isbn=978-1-4614-4120-5&rft.aulast=Kozlenkov&rft.aufirst=Alexey&rft.au=Gonz%C3%A1lez-Maeso%2C+Javier&rfr_id=info%3Asid%2Fen.wikipedia.org%3ATryptophan" class="Z3988"></span></span> </li> <li id="cite_note-CarbonaroGatch2016-73"><span class="mw-cite-backlink"><b><a href="#cite_ref-CarbonaroGatch2016_73-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFCarbonaroGatch2016" class="citation journal cs1">Carbonaro TM, Gatch MB (September 2016). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5048497">"Neuropharmacology of N,N-dimethyltryptamine"</a>. <i>Brain Res Bull</i>. <b>126</b> (Pt 1): 74–88. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2Fj.brainresbull.2016.04.016">10.1016/j.brainresbull.2016.04.016</a>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5048497">5048497</a></span>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/27126737">27126737</a>. <q>Endogenous DMT is synthesized from the essential amino acid tryptophan, which is decarboxylated to tryptamine. Tryptamine is then transmethylated by the enzyme indolethylamine-N-methyltransferase (INMT) (using S-adenosyl methionine as a substrate), which catalyzes the addition of methyl groups resulting in the production of N-methyltryptamine (NMT) and DMT. NMT can also act as a substrate for INMT-dependent DMT biosynthesis (Barker et al., 1981).</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Brain+Res+Bull&rft.atitle=Neuropharmacology+of+N%2CN-dimethyltryptamine&rft.volume=126&rft.issue=Pt+1&rft.pages=74-88&rft.date=2016-09&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC5048497%23id-name%3DPMC&rft_id=info%3Apmid%2F27126737&rft_id=info%3Adoi%2F10.1016%2Fj.brainresbull.2016.04.016&rft.aulast=Carbonaro&rft.aufirst=TM&rft.au=Gatch%2C+MB&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC5048497&rfr_id=info%3Asid%2Fen.wikipedia.org%3ATryptophan" class="Z3988"></span></span> </li> <li id="cite_note-Barker2018-74"><span class="mw-cite-backlink"><b><a href="#cite_ref-Barker2018_74-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFBarker2018" class="citation journal cs1">Barker SA (2018). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6088236">"N, N-Dimethyltryptamine (DMT), an Endogenous Hallucinogen: Past, Present, and Future Research to Determine Its Role and Function"</a>. <i>Front Neurosci</i>. <b>12</b>: 536. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://doi.org/10.3389%2Ffnins.2018.00536">10.3389/fnins.2018.00536</a></span>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6088236">6088236</a></span>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/30127713">30127713</a>. <q>After the discovery of an indole-N-methyl transferase (INMT; Axelrod, 1961) in rat brain, researchers were soon examining whether the conversion of tryptophan (2, Figure 2) to tryptamine (TA; 3, Figure 2) could be converted to DMT in the brain and other tissues from several mammalian species. Numerous studies subsequently demonstrated the biosynthesis of DMT in mammalian tissue preparations in vitro and in vivo (Saavedra and Axelrod, 1972; Saavedra et al., 1973). In 1972, Juan Saavedra and Julius Axelrod reported that intracisternally administered TA was converted to N-methyltryptamine (NMT; 4, Figure 2) and DMT in the rat, the first demonstration of DMT's formation by brain tissue in vivo.</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Front+Neurosci&rft.atitle=N%2C+N-Dimethyltryptamine+%28DMT%29%2C+an+Endogenous+Hallucinogen%3A+Past%2C+Present%2C+and+Future+Research+to+Determine+Its+Role+and+Function&rft.volume=12&rft.pages=536&rft.date=2018&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC6088236%23id-name%3DPMC&rft_id=info%3Apmid%2F30127713&rft_id=info%3Adoi%2F10.3389%2Ffnins.2018.00536&rft.aulast=Barker&rft.aufirst=SA&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC6088236&rfr_id=info%3Asid%2Fen.wikipedia.org%3ATryptophan" class="Z3988"></span></span> </li> <li id="cite_note-CameronOlson2018-75"><span class="mw-cite-backlink"><b><a href="#cite_ref-CameronOlson2018_75-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFCameronOlson2018" class="citation journal cs1">Cameron LP, Olson DE (October 2018). <a rel="nofollow" class="external text" href="https://shaunlacob.com/wp-content/uploads/2020/12/Dark-Classics-DMT.pdf">"Dark Classics in Chemical Neuroscience: N, N-Dimethyltryptamine (DMT)"</a> <span class="cs1-format">(PDF)</span>. <i>ACS Chem Neurosci</i>. <b>9</b> (10): 2344–2357. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1021%2Facschemneuro.8b00101">10.1021/acschemneuro.8b00101</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/30036036">30036036</a>. <q>Like serotonin and melatonin, DMT is a product of tryptophan metabolism.25 Following tryptophan decarboxylation, tryptamine is methylated by an N-methyltransferase (i.e., INMT) with S-adenosylmethionine serving as the methyl donor. A second enzymatic methylation produces DMT (Figure 3A).26 [...] The enzyme indolethylamine N-methyltransferase (INMT) catalyzes the methylation of a variety of biogenic amines, and is responsible for converting tryptamine into DMT in mammals.140</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=ACS+Chem+Neurosci&rft.atitle=Dark+Classics+in+Chemical+Neuroscience%3A+N%2C+N-Dimethyltryptamine+%28DMT%29&rft.volume=9&rft.issue=10&rft.pages=2344-2357&rft.date=2018-10&rft_id=info%3Adoi%2F10.1021%2Facschemneuro.8b00101&rft_id=info%3Apmid%2F30036036&rft.aulast=Cameron&rft.aufirst=LP&rft.au=Olson%2C+DE&rft_id=https%3A%2F%2Fshaunlacob.com%2Fwp-content%2Fuploads%2F2020%2F12%2FDark-Classics-DMT.pdf&rfr_id=info%3Asid%2Fen.wikipedia.org%3ATryptophan" class="Z3988"></span></span> </li> <li id="cite_note-ColosimoBorsellinoKrider2024-76"><span class="mw-cite-backlink"><b><a href="#cite_ref-ColosimoBorsellinoKrider2024_76-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFColosimoBorsellinoKriderMarquez2024" class="citation journal cs1">Colosimo FA, Borsellino P, Krider RI, Marquez RE, Vida TA (26 February 2024). <a rel="nofollow" class="external text" href="https://doi.org/10.3390%2Fpsychoactives3010007">"The Clinical Potential of Dimethyltryptamine: Breakthroughs into the Other Side of Mental Illness, Neurodegeneration, and Consciousness"</a>. <i>Psychoactives</i>. <b>3</b> (1). MDPI AG: 93–122. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://doi.org/10.3390%2Fpsychoactives3010007">10.3390/psychoactives3010007</a></span>. <a href="/wiki/ISSN_(identifier)" class="mw-redirect" title="ISSN (identifier)">ISSN</a> <a rel="nofollow" class="external text" href="https://search.worldcat.org/issn/2813-1851">2813-1851</a>. <q>The metabolism of DMT within the body begins with its synthesis. Endogenous DMT is made from tryptophan after decarboxylation transforms it into tryptamine [22,25]. Tryptamine then undergoes transmethylation mediated by indolethylamine-N-methyltransferase (INMT) with S-adenosyl methionine (SAM) as a substrate, morphing into N-methyltryptamine (NMT) and eventually producing N,N-DMT [26]. Intriguingly, INMT is distributed widely across the body, predominantly in the lungs, thyroid, and adrenal glands, with a dense presence in the anterior horn of the spinal cord. Within the cerebral domain, regions such as the uncus, medulla, amygdala, frontal cortex, fronto-parietal lobe, and temporal lobe exhibit INMT activity, primarily localized in the soma [26]. INMT transcripts are found in specific brain regions, including the cerebral cortex, pineal gland, and choroid plexus, in both rats and humans. Although the rat brain is capable of synthesizing and releasing DMT at concentrations similar to established monoamine neurotransmitters like serotonin [27], the possibility that DMT is an authentic neurotransmitter is still speculative. This issue has been controversial for decades [28] and requires the demonstration of an activity-dependent release (i.e., Ca2+-stimulated) of DMT at a synaptic cleft to be fully established in the human brain.</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Psychoactives&rft.atitle=The+Clinical+Potential+of+Dimethyltryptamine%3A+Breakthroughs+into+the+Other+Side+of+Mental+Illness%2C+Neurodegeneration%2C+and+Consciousness&rft.volume=3&rft.issue=1&rft.pages=93-122&rft.date=2024-02-26&rft_id=info%3Adoi%2F10.3390%2Fpsychoactives3010007&rft.issn=2813-1851&rft.aulast=Colosimo&rft.aufirst=Frankie+A.&rft.au=Borsellino%2C+Philip&rft.au=Krider%2C+Reese+I.&rft.au=Marquez%2C+Raul+E.&rft.au=Vida%2C+Thomas+A.&rft_id=https%3A%2F%2Fdoi.org%2F10.3390%252Fpsychoactives3010007&rfr_id=info%3Asid%2Fen.wikipedia.org%3ATryptophan" class="Z3988"></span></span> </li> <li id="cite_note-AraújoCarvalhoBastosMde2015-77"><span class="mw-cite-backlink"><b><a href="#cite_ref-AraújoCarvalhoBastosMde2015_77-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFAraújoCarvalhoBastos_MdeGuedes_de_Pinho2015" class="citation journal cs1">Araújo AM, Carvalho F, Bastos Mde L, Guedes de Pinho P, Carvalho M (August 2015). "The hallucinogenic world of tryptamines: an updated review". <i>Arch Toxicol</i>. <b>89</b> (8): 1151–1173. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1007%2Fs00204-015-1513-x">10.1007/s00204-015-1513-x</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/25877327">25877327</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Arch+Toxicol&rft.atitle=The+hallucinogenic+world+of+tryptamines%3A+an+updated+review&rft.volume=89&rft.issue=8&rft.pages=1151-1173&rft.date=2015-08&rft_id=info%3Adoi%2F10.1007%2Fs00204-015-1513-x&rft_id=info%3Apmid%2F25877327&rft.aulast=Ara%C3%BAjo&rft.aufirst=AM&rft.au=Carvalho%2C+F&rft.au=Bastos+Mde%2C+L&rft.au=Guedes+de+Pinho%2C+P&rft.au=Carvalho%2C+M&rfr_id=info%3Asid%2Fen.wikipedia.org%3ATryptophan" class="Z3988"></span></span> </li> </ol></div></div> <div class="mw-heading mw-heading2"><h2 id="Further_reading">Further reading</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Tryptophan&action=edit&section=21" title="Edit section: Further reading"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1239549316">.mw-parser-output .refbegin{margin-bottom:0.5em}.mw-parser-output .refbegin-hanging-indents>ul{margin-left:0}.mw-parser-output .refbegin-hanging-indents>ul>li{margin-left:0;padding-left:3.2em;text-indent:-3.2em}.mw-parser-output .refbegin-hanging-indents ul,.mw-parser-output .refbegin-hanging-indents ul li{list-style:none}@media(max-width:720px){.mw-parser-output .refbegin-hanging-indents>ul>li{padding-left:1.6em;text-indent:-1.6em}}.mw-parser-output .refbegin-columns{margin-top:0.3em}.mw-parser-output .refbegin-columns ul{margin-top:0}.mw-parser-output .refbegin-columns li{page-break-inside:avoid;break-inside:avoid-column}@media screen{.mw-parser-output .refbegin{font-size:90%}}</style><div class="refbegin" style=""> <ul><li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFWoodRillingSanfeyBhagwagar2006" class="citation journal cs1">Wood RM, Rilling JK, Sanfey AG, Bhagwagar Z, Rogers RD (May 2006). <a rel="nofollow" class="external text" href="https://doi.org/10.1038%2Fsj.npp.1300932">"Effects of tryptophan depletion on the performance of an iterated Prisoner's Dilemma game in healthy adults"</a>. <i>Neuropsychopharmacology</i>. <b>31</b> (5): 1075–84. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://doi.org/10.1038%2Fsj.npp.1300932">10.1038/sj.npp.1300932</a></span>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/16407905">16407905</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Neuropsychopharmacology&rft.atitle=Effects+of+tryptophan+depletion+on+the+performance+of+an+iterated+Prisoner%27s+Dilemma+game+in+healthy+adults&rft.volume=31&rft.issue=5&rft.pages=1075-84&rft.date=2006-05&rft_id=info%3Adoi%2F10.1038%2Fsj.npp.1300932&rft_id=info%3Apmid%2F16407905&rft.aulast=Wood&rft.aufirst=RM&rft.au=Rilling%2C+JK&rft.au=Sanfey%2C+AG&rft.au=Bhagwagar%2C+Z&rft.au=Rogers%2C+RD&rft_id=https%3A%2F%2Fdoi.org%2F10.1038%252Fsj.npp.1300932&rfr_id=info%3Asid%2Fen.wikipedia.org%3ATryptophan" class="Z3988"></span></li></ul> </div> <div class="mw-heading mw-heading2"><h2 id="External_links">External links</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Tryptophan&action=edit&section=22" title="Edit section: External links"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239549316"><div class="refbegin" style=""> <ul><li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="http://www.genome.jp/dbget-bin/www_bget?path:hsa00380">"KEGG PATHWAY: Tryptophan metabolism - Homo sapiens"</a>. KEGG: Kyoto Encyclopedia of Genes and Genomes. 23 August 2006<span class="reference-accessdate">. Retrieved <span class="nowrap">20 April</span> 2008</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=KEGG+PATHWAY%3A+Tryptophan+metabolism+-+Homo+sapiens&rft.pub=KEGG%3A+Kyoto+Encyclopedia+of+Genes+and+Genomes&rft.date=2006-08-23&rft_id=http%3A%2F%2Fwww.genome.jp%2Fdbget-bin%2Fwww_bget%3Fpath%3Ahsa00380&rfr_id=info%3Asid%2Fen.wikipedia.org%3ATryptophan" class="Z3988"></span></li> <li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFG._P._Moss" class="citation web cs1">G. P. Moss. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20030913143004/http://www.chem.qmul.ac.uk/iubmb/enzyme/reaction/AminoAcid/TrpCat1.html">"Tryptophan Catabolism (early stages)"</a>. Nomenclature Committee of the International Union of Biochemistry and Molecular Biology (NC-IUBMB). Archived from <a rel="nofollow" class="external text" href="http://www.chem.qmul.ac.uk/iubmb/enzyme/reaction/AminoAcid/TrpCat1.html">the original</a> on 13 September 2003<span class="reference-accessdate">. Retrieved <span class="nowrap">20 April</span> 2008</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=Tryptophan+Catabolism+%28early+stages%29&rft.pub=Nomenclature+Committee+of+the+International+Union+of+Biochemistry+and+Molecular+Biology+%28NC-IUBMB%29&rft.au=G.+P.+Moss&rft_id=http%3A%2F%2Fwww.chem.qmul.ac.uk%2Fiubmb%2Fenzyme%2Freaction%2FAminoAcid%2FTrpCat1.html&rfr_id=info%3Asid%2Fen.wikipedia.org%3ATryptophan" class="Z3988"></span></li> <li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFG._P._Moss" class="citation web cs1">G. P. Moss. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20030913191403/http://www.chem.qmul.ac.uk/iubmb/enzyme/reaction/AminoAcid/TrpCat2.html">"Tryptophan Catabolism (later stages)"</a>. Nomenclature Committee of the International Union of Biochemistry and Molecular Biology (NC-IUBMB). Archived from <a rel="nofollow" class="external text" href="http://www.chem.qmul.ac.uk/iubmb/enzyme/reaction/AminoAcid/TrpCat2.html">the original</a> on 13 September 2003<span class="reference-accessdate">. Retrieved <span class="nowrap">20 April</span> 2008</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=Tryptophan+Catabolism+%28later+stages%29&rft.pub=Nomenclature+Committee+of+the+International+Union+of+Biochemistry+and+Molecular+Biology+%28NC-IUBMB%29&rft.au=G.+P.+Moss&rft_id=http%3A%2F%2Fwww.chem.qmul.ac.uk%2Fiubmb%2Fenzyme%2Freaction%2FAminoAcid%2FTrpCat2.html&rfr_id=info%3Asid%2Fen.wikipedia.org%3ATryptophan" class="Z3988"></span></li> <li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFB._MikkelsonD._P._Mikkelson2007" class="citation web cs1">B. Mikkelson, D. P. Mikkelson (22 November 2007). <a rel="nofollow" class="external text" href="http://www.snopes.com/food/ingredient/turkey.asp">"Turkey Causes Sleepiness"</a>. <i>Urban Legends Reference Pages</i>. Snopes.com<span class="reference-accessdate">. Retrieved <span class="nowrap">20 April</span> 2008</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=Urban+Legends+Reference+Pages&rft.atitle=Turkey+Causes+Sleepiness&rft.date=2007-11-22&rft.au=B.+Mikkelson&rft.au=D.+P.+Mikkelson&rft_id=http%3A%2F%2Fwww.snopes.com%2Ffood%2Fingredient%2Fturkey.asp&rfr_id=info%3Asid%2Fen.wikipedia.org%3ATryptophan" class="Z3988"></span></li></ul> </div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><style data-mw-deduplicate="TemplateStyles:r1236075235">.mw-parser-output .navbox{box-sizing:border-box;border:1px solid #a2a9b1;width:100%;clear:both;font-size:88%;text-align:center;padding:1px;margin:1em auto 0}.mw-parser-output .navbox .navbox{margin-top:0}.mw-parser-output .navbox+.navbox,.mw-parser-output .navbox+.navbox-styles+.navbox{margin-top:-1px}.mw-parser-output .navbox-inner,.mw-parser-output .navbox-subgroup{width:100%}.mw-parser-output .navbox-group,.mw-parser-output .navbox-title,.mw-parser-output .navbox-abovebelow{padding:0.25em 1em;line-height:1.5em;text-align:center}.mw-parser-output .navbox-group{white-space:nowrap;text-align:right}.mw-parser-output .navbox,.mw-parser-output .navbox-subgroup{background-color:#fdfdfd}.mw-parser-output .navbox-list{line-height:1.5em;border-color:#fdfdfd}.mw-parser-output .navbox-list-with-group{text-align:left;border-left-width:2px;border-left-style:solid}.mw-parser-output tr+tr>.navbox-abovebelow,.mw-parser-output tr+tr>.navbox-group,.mw-parser-output tr+tr>.navbox-image,.mw-parser-output tr+tr>.navbox-list{border-top:2px solid #fdfdfd}.mw-parser-output .navbox-title{background-color:#ccf}.mw-parser-output .navbox-abovebelow,.mw-parser-output .navbox-group,.mw-parser-output .navbox-subgroup .navbox-title{background-color:#ddf}.mw-parser-output .navbox-subgroup .navbox-group,.mw-parser-output .navbox-subgroup .navbox-abovebelow{background-color:#e6e6ff}.mw-parser-output .navbox-even{background-color:#f7f7f7}.mw-parser-output .navbox-odd{background-color:transparent}.mw-parser-output .navbox .hlist td dl,.mw-parser-output .navbox .hlist td ol,.mw-parser-output .navbox .hlist td ul,.mw-parser-output .navbox td.hlist dl,.mw-parser-output .navbox td.hlist ol,.mw-parser-output .navbox td.hlist ul{padding:0.125em 0}.mw-parser-output .navbox .navbar{display:block;font-size:100%}.mw-parser-output .navbox-title .navbar{float:left;text-align:left;margin-right:0.5em}body.skin--responsive .mw-parser-output .navbox-image img{max-width:none!important}@media print{body.ns-0 .mw-parser-output .navbox{display:none!important}}</style><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"></div><div role="navigation" class="navbox" aria-labelledby="Encoded_(proteinogenic)_amino_acids" style="padding:3px"><table class="nowraplinks hlist mw-collapsible autocollapse navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="3"><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:Proteinogenic_amino_acids" title="Template:Proteinogenic amino acids"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Proteinogenic_amino_acids" title="Template talk:Proteinogenic amino acids"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Proteinogenic_amino_acids" title="Special:EditPage/Template:Proteinogenic amino acids"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Encoded_(proteinogenic)_amino_acids" style="font-size:114%;margin:0 4em"><a href="/wiki/Proteinogenic_amino_acid" title="Proteinogenic amino acid">Encoded (proteinogenic) amino acids</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%">General topics</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/Protein" title="Protein">Protein</a></li> <li><a href="/wiki/Peptide" title="Peptide">Peptide</a></li> <li><a href="/wiki/Genetic_code" title="Genetic code">Genetic code</a></li></ul> </div></td><td class="noviewer navbox-image" rowspan="2" style="width:1px;padding:0 0 0 2px"><div><span typeof="mw:File"><a href="/wiki/File:L-amino_acid_any.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/0/0e/L-amino_acid_any.png/182px-L-amino_acid_any.png" decoding="async" width="182" height="160" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/0/0e/L-amino_acid_any.png/273px-L-amino_acid_any.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/0/0e/L-amino_acid_any.png/364px-L-amino_acid_any.png 2x" data-file-width="728" data-file-height="640" /></a></span></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">By properties</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Aliphatic_compound" title="Aliphatic compound">Aliphatic</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/Branched-chain_amino_acid" title="Branched-chain amino acid">Branched-chain amino acids</a> (<a href="/wiki/Valine" title="Valine">Valine</a></li> <li><a href="/wiki/Isoleucine" title="Isoleucine">Isoleucine</a></li> <li><a href="/wiki/Leucine" title="Leucine">Leucine</a>)</li> <li><a href="/wiki/Methionine" title="Methionine">Methionine</a></li> <li><a href="/wiki/Alanine" title="Alanine">Alanine</a></li> <li><a href="/wiki/Proline" title="Proline">Proline</a></li> <li><a href="/wiki/Glycine" title="Glycine">Glycine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Aromatic_amino_acid" title="Aromatic amino acid">Aromatic</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/Histidine" title="Histidine">Histidine</a></li> <li><a href="/wiki/Tyrosine" title="Tyrosine">Tyrosine</a></li> <li><a class="mw-selflink selflink">Tryptophan</a></li> <li><a href="/wiki/Phenylalanine" title="Phenylalanine">Phenylalanine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Chemical_polarity" title="Chemical polarity">Polar</a>, uncharged</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/Asparagine" title="Asparagine">Asparagine</a></li> <li><a href="/wiki/Glutamine" title="Glutamine">Glutamine</a></li> <li><a href="/wiki/Serine" title="Serine">Serine</a></li> <li><a href="/wiki/Threonine" title="Threonine">Threonine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Positive charge (p<i>K</i><sub>a</sub>)</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/Lysine" title="Lysine">Lysine</a> (≈10.8)</li> <li><a href="/wiki/Arginine" title="Arginine">Arginine</a> (≈12.5)</li> <li><a href="/wiki/Histidine" title="Histidine">Histidine</a> (≈6.1)</li> <li><a href="/wiki/Pyrrolysine" title="Pyrrolysine">Pyrrolysine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Negative charge (p<i>K</i><sub>a</sub>)</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/Aspartic_acid" title="Aspartic acid">Aspartic acid</a> (≈3.9)</li> <li><a href="/wiki/Glutamic_acid" title="Glutamic acid">Glutamic acid</a> (≈4.1)</li> <li><a href="/wiki/Selenocysteine" title="Selenocysteine">Selenocysteine</a> (≈5.4)</li> <li><a href="/wiki/Cysteine" title="Cysteine">Cysteine</a> (≈8.3)</li> <li><a href="/wiki/Tyrosine" title="Tyrosine">Tyrosine</a> (≈10.1)</li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><td class="navbox-abovebelow" colspan="3"><div><div class="hlist" style="font-size:88%;"> <ul><li><b><a href="/wiki/Amino_acids" class="mw-redirect" title="Amino acids">Amino acids</a> types</b>: <a href="/wiki/Template:Encoded_amino_acids" class="mw-redirect" title="Template:Encoded amino acids">Encoded (proteins)</a></li> <li><a href="/wiki/Essential_amino_acids" class="mw-redirect" title="Essential amino acids">Essential</a></li> <li><a href="/wiki/Template:Non-proteinogenic_amino_acids" title="Template:Non-proteinogenic amino acids">Non-proteinogenic</a></li> <li><a href="/wiki/Ketogenic_amino_acids" class="mw-redirect" title="Ketogenic amino acids">Ketogenic</a></li> <li><a href="/wiki/Glucogenic_amino_acids" class="mw-redirect" title="Glucogenic amino acids">Glucogenic</a></li> <li><a href="/wiki/Secondary_amino_acid" title="Secondary amino acid">Secondary amino</a></li> <li><a href="/wiki/Imino_acid" title="Imino acid">Imino acids</a></li> <li><a href="/wiki/D-amino_acids" class="mw-redirect" title="D-amino acids">D-amino acids</a></li> <li><a href="/wiki/Dehydroamino_acid" title="Dehydroamino acid">Dehydroamino acids</a></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="Amino_acid_metabolism_metabolic_intermediates" style="padding:3px"><table class="nowraplinks mw-collapsible mw-collapsed navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Amino_acid_metabolism_intermediates" title="Template:Amino acid metabolism intermediates"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Amino_acid_metabolism_intermediates" title="Template talk:Amino acid metabolism intermediates"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Amino_acid_metabolism_intermediates" title="Special:EditPage/Template:Amino acid metabolism intermediates"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Amino_acid_metabolism_metabolic_intermediates" style="font-size:114%;margin:0 4em"><a href="/wiki/Amino_acid" title="Amino acid">Amino acid</a> <a href="/wiki/Amino_acid_synthesis" title="Amino acid synthesis">metabolism</a> <a href="/wiki/Metabolic_intermediate" title="Metabolic intermediate">metabolic intermediates</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Ketogenic_amino_acid" title="Ketogenic amino acid">K</a>→<a href="/wiki/Acetyl-CoA" title="Acetyl-CoA">acetyl-CoA</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%"><a href="/wiki/Lysine" title="Lysine">lysine</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/Saccharopine" title="Saccharopine">Saccharopine</a></li> <li><a href="/wiki/Allysine" title="Allysine">Allysine</a></li> <li><a href="/wiki/Alpha-Aminoadipic_acid" class="mw-redirect" title="Alpha-Aminoadipic acid">α-Aminoadipic acid</a></li> <li><a href="/wiki/2-Oxoadipic_acid" title="2-Oxoadipic acid">2-Oxoadipic acid</a></li> <li><a href="/wiki/Glutaryl-CoA" title="Glutaryl-CoA">Glutaryl-CoA</a></li> <li><a href="/wiki/Glutaconyl-CoA" title="Glutaconyl-CoA">Glutaconyl-CoA</a></li> <li><a href="/wiki/Crotonyl-CoA" title="Crotonyl-CoA">Crotonyl-CoA</a></li> <li><a href="/wiki/Beta-Hydroxybutyryl-CoA" class="mw-redirect" title="Beta-Hydroxybutyryl-CoA">β-Hydroxybutyryl-CoA</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Leucine" title="Leucine">leucine</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/Beta-Hydroxy_beta-methylbutyric_acid" class="mw-redirect" title="Beta-Hydroxy beta-methylbutyric acid">β-Hydroxy β-methylbutyric acid</a></li> <li><a href="/wiki/Beta-Hydroxy_beta-methylbutyryl-CoA" class="mw-redirect" title="Beta-Hydroxy beta-methylbutyryl-CoA">β-Hydroxy β-methylbutyryl-CoA</a></li> <li><a href="/wiki/Isovaleryl-CoA" title="Isovaleryl-CoA">Isovaleryl-CoA</a></li> <li><a href="/wiki/Alpha-Ketoisocaproic_acid" class="mw-redirect" title="Alpha-Ketoisocaproic acid">α-Ketoisocaproic acid</a></li> <li><a href="/wiki/Beta-Ketoisocaproic_acid" class="mw-redirect" title="Beta-Ketoisocaproic acid">β-Ketoisocaproic acid</a></li> <li><a href="/w/index.php?title=Beta-Ketoisocaproyl-CoA&action=edit&redlink=1" class="new" title="Beta-Ketoisocaproyl-CoA (page does not exist)">β-Ketoisocaproyl-CoA</a></li> <li><a href="/wiki/%CE%92-Leucine" title="Β-Leucine">β-Leucine</a></li> <li><a href="/wiki/Methylcrotonyl-CoA" title="Methylcrotonyl-CoA">β-Methylcrotonyl-CoA</a></li> <li><a href="/wiki/%CE%92-Methylglutaconyl-CoA" class="mw-redirect" title="Β-Methylglutaconyl-CoA">β-Methylglutaconyl-CoA</a></li> <li><a href="/wiki/HMG-CoA" title="HMG-CoA">β-Hydroxy β-methylglutaryl-CoA</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a class="mw-selflink selflink">tryptophan</a>→<a href="/wiki/Alanine" title="Alanine">alanine</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/N%27-Formylkynurenine" title="N'-Formylkynurenine"><i>N</i>′-Formylkynurenine</a></li> <li><a href="/wiki/Kynurenine" title="Kynurenine">Kynurenine</a></li> <li><a href="/wiki/Anthranilic_acid" title="Anthranilic acid">Anthranilic acid</a></li> <li><a href="/wiki/3-Hydroxykynurenine" title="3-Hydroxykynurenine">3-Hydroxykynurenine</a></li> <li><a href="/wiki/3-Hydroxyanthranilic_acid" title="3-Hydroxyanthranilic acid">3-Hydroxyanthranilic acid</a></li> <li><a href="/wiki/2-Amino-3-carboxymuconic_semialdehyde" title="2-Amino-3-carboxymuconic semialdehyde">2-Amino-3-carboxymuconic semialdehyde</a></li> <li><a href="/wiki/2-Aminomuconic_semialdehyde" title="2-Aminomuconic semialdehyde">2-Aminomuconic semialdehyde</a></li> <li><a href="/wiki/2-Aminomuconic_acid" title="2-Aminomuconic acid">2-Aminomuconic acid</a></li> <li><a href="/wiki/Glutaryl-CoA" title="Glutaryl-CoA">Glutaryl-CoA</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Glucogenic_amino_acid" title="Glucogenic amino acid">G</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%">G→<a href="/wiki/Pyruvate" class="mw-redirect" title="Pyruvate">pyruvate</a>→ <br /><a href="/wiki/Citrate" class="mw-redirect" title="Citrate">citrate</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th id="glycine→serine→" scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Glycine" title="Glycine">glycine</a>→<br /><a href="/wiki/Serine" title="Serine">serine</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/3-Phosphoglyceric_acid" title="3-Phosphoglyceric acid">3-Phosphoglyceric acid</a></li></ul> <ul><li><a href="/wiki/Glycine" title="Glycine">glycine</a>→<a href="/wiki/Creatine" title="Creatine">creatine</a>: <a href="/wiki/Glycocyamine" title="Glycocyamine">Glycocyamine</a></li> <li><a href="/wiki/Phosphocreatine" title="Phosphocreatine">Phosphocreatine</a></li> <li><a href="/wiki/Creatinine" title="Creatinine">Creatinine</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">G→<a href="/wiki/Glutamate" class="mw-redirect" title="Glutamate">glutamate</a>→<br /><a href="/wiki/Alpha-Ketoglutaric_acid" class="mw-redirect" title="Alpha-Ketoglutaric acid">α-ketoglutarate</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Histidine" title="Histidine">histidine</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/Urocanic_acid" title="Urocanic acid">Urocanic acid</a></li> <li><a href="/wiki/Imidazol-4-one-5-propionic_acid" title="Imidazol-4-one-5-propionic acid">Imidazol-4-one-5-propionic acid</a></li> <li><a href="/wiki/Formiminoglutamic_acid" title="Formiminoglutamic acid">Formiminoglutamic acid</a></li> <li><a href="/wiki/Glutamate-1-semialdehyde" title="Glutamate-1-semialdehyde">Glutamate-1-semialdehyde</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Proline" title="Proline">proline</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/1-Pyrroline-5-carboxylic_acid" title="1-Pyrroline-5-carboxylic acid">1-Pyrroline-5-carboxylic acid</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Arginine" title="Arginine">arginine</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/Agmatine" title="Agmatine">Agmatine</a></li> <li><a href="/wiki/Ornithine" title="Ornithine">Ornithine</a></li> <li><a href="/wiki/Citrulline" title="Citrulline">Citrulline</a></li> <li><a href="/wiki/Cadaverine" title="Cadaverine">Cadaverine</a></li> <li><a href="/wiki/Putrescine" title="Putrescine">Putrescine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">other</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/Cysteine" title="Cysteine">cysteine</a>+<a href="/wiki/Glutamate" class="mw-redirect" title="Glutamate">glutamate</a>→<a href="/wiki/Glutathione" title="Glutathione">glutathione</a>: <a href="/wiki/Gamma-Glutamylcysteine" class="mw-redirect" title="Gamma-Glutamylcysteine">γ-Glutamylcysteine</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">G→<a href="/wiki/Propionyl-CoA" title="Propionyl-CoA">propionyl-CoA</a>→<br /><a href="/wiki/Succinyl-CoA" title="Succinyl-CoA">succinyl-CoA</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Valine" title="Valine">valine</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/Alpha-Ketoisovaleric_acid" class="mw-redirect" title="Alpha-Ketoisovaleric acid">α-Ketoisovaleric acid</a></li> <li><a href="/wiki/Isobutyryl-CoA" title="Isobutyryl-CoA">Isobutyryl-CoA</a></li> <li><a href="/wiki/Methacrylyl-CoA" title="Methacrylyl-CoA">Methacrylyl-CoA</a></li> <li><a href="/wiki/3-Hydroxyisobutyryl-CoA" title="3-Hydroxyisobutyryl-CoA">3-Hydroxyisobutyryl-CoA</a></li> <li><a href="/wiki/3-Hydroxyisobutyric_acid" title="3-Hydroxyisobutyric acid">3-Hydroxyisobutyric acid</a></li> <li><a href="/wiki/2-Methyl-3-oxopropanoic_acid" class="mw-redirect" title="2-Methyl-3-oxopropanoic acid">2-Methyl-3-oxopropanoic acid</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Isoleucine" title="Isoleucine">isoleucine</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/2,3-Dihydroxy-3-methylpentanoic_acid" title="2,3-Dihydroxy-3-methylpentanoic acid">2,3-Dihydroxy-3-methylpentanoic acid</a></li> <li><a href="/wiki/2-Methylbutyryl-CoA" title="2-Methylbutyryl-CoA">2-Methylbutyryl-CoA</a></li> <li><a href="/wiki/Tiglyl-CoA" title="Tiglyl-CoA">Tiglyl-CoA</a></li> <li><a href="/wiki/2-Methylacetoacetyl-CoA" title="2-Methylacetoacetyl-CoA">2-Methylacetoacetyl-CoA</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Methionine" title="Methionine">methionine</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><i><a href="/wiki/Methionine#Generation_of_homocysteine" title="Methionine">generation of homocysteine</a>:</i> <a href="/wiki/S-Adenosyl_methionine" title="S-Adenosyl methionine"><i>S</i>-Adenosyl methionine</a></li> <li><a href="/wiki/S-Adenosyl-L-homocysteine" title="S-Adenosyl-L-homocysteine"><i>S</i>-Adenosyl-<span class="smallcaps"><span style="font-variant: small-caps; text-transform: lowercase;">L</span></span>-homocysteine</a></li> <li><a href="/wiki/Homocysteine" title="Homocysteine">Homocysteine</a></li></ul> <ul><li><i><a href="/wiki/Methionine#Conversion_to_cysteine" title="Methionine">conversion to cysteine</a>:</i> <a href="/wiki/Cystathionine" title="Cystathionine">Cystathionine</a></li> <li><a href="/wiki/Alpha-Ketobutyric_acid" class="mw-redirect" title="Alpha-Ketobutyric acid">α-Ketobutyric acid</a> + <a href="/wiki/Cysteine" title="Cysteine">Cysteine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Threonine" title="Threonine">threonine</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/Alpha-Ketobutyric_acid" class="mw-redirect" title="Alpha-Ketobutyric acid">α-Ketobutyric acid</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Propionyl-CoA" title="Propionyl-CoA">propionyl-CoA</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/Methylmalonyl-CoA" title="Methylmalonyl-CoA">Methylmalonyl-CoA</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">G→<a href="/wiki/Fumarate" class="mw-redirect" title="Fumarate">fumarate</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Phenylalanine" title="Phenylalanine">phenylalanine</a>→<a href="/wiki/Tyrosine" title="Tyrosine">tyrosine</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/4-Hydroxyphenylpyruvic_acid" title="4-Hydroxyphenylpyruvic acid">4-Hydroxyphenylpyruvic acid</a></li> <li><a href="/wiki/Homogentisic_acid" title="Homogentisic acid">Homogentisic acid</a></li> <li><a href="/wiki/4-Maleylacetoacetic_acid" title="4-Maleylacetoacetic acid">4-Maleylacetoacetic acid</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">G→<a href="/wiki/Oxaloacetate" class="mw-redirect" title="Oxaloacetate">oxaloacetate</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><i>see <a href="/wiki/Urea_cycle" title="Urea cycle">urea cycle</a></i></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Other</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Cysteine_metabolism" title="Cysteine metabolism">Cysteine metabolism</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/Cysteine_sulfinic_acid" title="Cysteine sulfinic acid">Cysteine sulfinic acid</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"></div><div role="navigation" class="navbox" aria-labelledby="Neurotransmitter_metabolic_intermediates" 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:Neurotransmitter_metabolism_intermediates" title="Template:Neurotransmitter metabolism intermediates"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Neurotransmitter_metabolism_intermediates" title="Template talk:Neurotransmitter metabolism intermediates"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Neurotransmitter_metabolism_intermediates" title="Special:EditPage/Template:Neurotransmitter metabolism intermediates"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Neurotransmitter_metabolic_intermediates" style="font-size:114%;margin:0 4em"><a href="/wiki/Neurotransmitter" title="Neurotransmitter">Neurotransmitter</a> <a href="/wiki/Metabolic_intermediate" title="Metabolic intermediate">metabolic intermediates</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Catecholamine" title="Catecholamine">Catecholamines</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%"><a href="/wiki/Anabolism" title="Anabolism">Anabolism</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/Phenylalanine" title="Phenylalanine">Phenylalanine</a> → <a href="/wiki/Tyrosine" title="Tyrosine">Tyrosine</a> → <a href="/wiki/L-DOPA" title="L-DOPA">DOPA (levodopa)</a> → <a href="/wiki/Dopamine" title="Dopamine">Dopamine</a> → <a href="/wiki/Norepinephrine" title="Norepinephrine">Norepinephrine</a> → <a href="/wiki/Epinephrine" class="mw-redirect" title="Epinephrine">Epinephrine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Catabolism" title="Catabolism">Catabolism</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Dopamine" title="Dopamine">Dopamine</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/3,4-Dihydroxyphenylacetaldehyde" title="3,4-Dihydroxyphenylacetaldehyde">3,4-Dihydroxyphenylacetaldehyde (DOPAL)</a></li> <li><a href="/wiki/3,4-Dihydroxyphenylacetic_acid" title="3,4-Dihydroxyphenylacetic acid">3,4-Dihydroxyphenylacetic acid (DOPAC)</a></li> <li><a href="/wiki/Homovanillyl_alcohol" title="Homovanillyl alcohol">Homovanillyl alcohol</a></li> <li><a href="/wiki/Hydroxytyrosol" title="Hydroxytyrosol">Hydroxytyrosol (3,4-dihydroxyphenylethanol; DOPET)</a></li> <li><a href="/wiki/3-Methoxytyramine" title="3-Methoxytyramine">3-Methoxytyramine (3-MT)</a></li> <li><a href="/wiki/Homovanillic_acid" title="Homovanillic acid">Homovanillic acid (HVA)</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Norepinephrine" title="Norepinephrine">Norepinephrine</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/3,4-Dihydroxyphenylglycolaldehyde" title="3,4-Dihydroxyphenylglycolaldehyde">3,4-Dihydroxyphenylglycolaldehyde (DOPEGAL, DHMAL)</a></li> <li><a href="/wiki/3,4-Dihydroxymandelic_acid" title="3,4-Dihydroxymandelic acid">3,4-Dihydroxymandelic acid (DHMA)</a></li> <li><a href="/wiki/Normetanephrine" title="Normetanephrine">Normetanephrine</a></li> <li><a href="/w/index.php?title=3-Methoxy-4-hydroxymandelaldehyde&action=edit&redlink=1" class="new" title="3-Methoxy-4-hydroxymandelaldehyde (page does not exist)">3-Methoxy-4-hydroxymandelaldehyde (MHMAL)</a></li> <li><a href="/wiki/Vanillylmandelic_acid" title="Vanillylmandelic acid">Vanillylmandelic acid (VMA)</a></li> <li><a href="/wiki/Dihydroxyphenylethylene_glycol" title="Dihydroxyphenylethylene glycol">3,4-Dihydroxyphenylethylene glycol (DOPEG, DHPG)</a></li> <li><a href="/wiki/3-Methoxy-4-hydroxyphenylglycol" title="3-Methoxy-4-hydroxyphenylglycol">3-Methoxy-4-hydroxyphenylglycol (MHPG, MOPEG)</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Epinephrine" class="mw-redirect" title="Epinephrine">Epinephrine</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/3,4-Dihydroxyphenylglycolaldehyde" title="3,4-Dihydroxyphenylglycolaldehyde">3,4-Dihydroxyphenylglycolaldehyde (DOPEGAL, DHMAL)</a></li> <li><a href="/wiki/Metanephrine" title="Metanephrine">Metanephrine</a></li> <li><a href="/w/index.php?title=3-Methoxy-4-hydroxymandelaldehyde&action=edit&redlink=1" class="new" title="3-Methoxy-4-hydroxymandelaldehyde (page does not exist)">3-Methoxy-4-hydroxymandelaldehyde (MHMAL)</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a class="mw-selflink selflink">Tryptophan</a>→<a href="/wiki/Serotonin" title="Serotonin">Serotonin</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%"><a href="/wiki/Anabolism" title="Anabolism">Anabolism</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 class="mw-selflink selflink">Tryptophan</a></li> <li><a href="/wiki/5-Hydroxytryptophan" title="5-Hydroxytryptophan">5-Hydroxytryptophan (5-HTP)</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Catabolism" title="Catabolism">Catabolism</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/5-Hydroxyindoleacetaldehyde" title="5-Hydroxyindoleacetaldehyde">5-Hydroxyindoleacetaldehyde (5-HIAL)</a></li> <li><a href="/wiki/5-Hydroxyindoleacetic_acid" title="5-Hydroxyindoleacetic acid">5-Hydroxyindoleacetic acid (5-HIAA)</a></li> <li><a href="/w/index.php?title=5-Hydroxytryptophol&action=edit&redlink=1" class="new" title="5-Hydroxytryptophol (page does not exist)">5-Hydroxytryptophol (5-HTOL)</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Serotonin" title="Serotonin">Serotonin</a>→<a href="/wiki/Melatonin" title="Melatonin">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/N-Acetylserotonin" title="N-Acetylserotonin"><i>N</i>-Acetylserotonin (NAS; normelatonin)</a></li> <li><a href="/wiki/5-Methoxytryptamine" title="5-Methoxytryptamine">5-Methoxytryptamine (5-MT)</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-Methoxyindoleacetaldehyde (5-MIAL)</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Trace_amine" title="Trace amine">Trace amines</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="/w/index.php?title=3-Methoxy-4-hydroxyphenylacetaldehyde&action=edit&redlink=1" class="new" title="3-Methoxy-4-hydroxyphenylacetaldehyde (page does not exist)">3-Methoxy-4-hydroxyphenylacetaldehyde (HMPAL)</a></li> <li><a href="/wiki/4-Hydroxyphenylacetaldehyde" title="4-Hydroxyphenylacetaldehyde">4-Hydroxyphenylacetaldehyde (HPAL)</a></li> <li><a href="/wiki/Indole-3-acetaldehyde" title="Indole-3-acetaldehyde">Indoleacetaldehyde (IAL)</a></li> <li><a href="/w/index.php?title=Phenacetaldehyde&action=edit&redlink=1" class="new" title="Phenacetaldehyde (page does not exist)">Phenacetaldehyde (PAL)</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/%CE%93-Aminobutyric_acid" class="mw-redirect" title="Γ-Aminobutyric acid">GABA</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/Glutamate" class="mw-redirect" title="Glutamate">Glutamate</a></li> <li><a href="/wiki/Putrescine" title="Putrescine">Putrescine</a></li> <li><a href="/wiki/%CE%93-Aminobutyraldehyde" title="Γ-Aminobutyraldehyde">γ-Aminobutyraldehyde (GABAL)</a></li> <li><a href="/wiki/N-Acetylputrescine" title="N-Acetylputrescine"><i>N</i>-Acetylputrescine</a></li> <li><a href="/wiki/N-Acetyl-%CE%B3-aminobutyraldehyde" title="N-Acetyl-γ-aminobutyraldehyde"><i>N</i>-Acetyl-γ-aminobutyraldehyde (<i>N</i>-acetyl-GABAL)</a></li> <li><a href="/wiki/N-Acetyl-%CE%B3-aminobutyric_acid" title="N-Acetyl-γ-aminobutyric acid"><i>N</i>-Acetyl-γ-aminobutyric acid (<i>N</i>-acetyl-GABA)</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="Serotonin_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:Serotonin_receptor_modulators" title="Template:Serotonin receptor modulators"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Serotonin_receptor_modulators" title="Template talk:Serotonin receptor modulators"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Serotonin_receptor_modulators" title="Special:EditPage/Template:Serotonin receptor modulators"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Serotonin_receptor_modulators" style="font-size:114%;margin:0 4em"><a href="/wiki/5-HT_receptor" title="5-HT receptor">Serotonin 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/5-HT1_receptor" title="5-HT1 receptor">5-HT<sub>1</sub></a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/5-HT1A_receptor" title="5-HT1A receptor">5-HT<sub>1A</sub></a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><td colspan="2" class="navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i>Agonists:</i> <a href="/wiki/8-OH-DPAT" title="8-OH-DPAT">8-OH-DPAT</a></li> <li><a href="/wiki/Adatanserin" title="Adatanserin">Adatanserin</a></li> <li><a href="/wiki/Amphetamine" title="Amphetamine">Amphetamine</a></li> <li><a href="/wiki/Antidepressant" title="Antidepressant">Antidepressants</a> (e.g., <a href="/wiki/Etoperidone" title="Etoperidone">etoperidone</a>, <a href="/wiki/Hydroxynefazodone" title="Hydroxynefazodone">hydroxynefazodone</a>, <a href="/wiki/Nefazodone" title="Nefazodone">nefazodone</a>, <a href="/wiki/Trazodone" title="Trazodone">trazodone</a>, <a href="/wiki/Triazoledione" title="Triazoledione">triazoledione</a>, <a href="/wiki/Vilazodone" title="Vilazodone">vilazodone</a>, <a href="/wiki/Vortioxetine" title="Vortioxetine">vortioxetine</a>)</li> <li><a href="/wiki/Atypical_antipsychotic" title="Atypical antipsychotic">Atypical antipsychotics</a> (e.g., <a href="/wiki/Aripiprazole" title="Aripiprazole">aripiprazole</a>, <a href="/wiki/Asenapine" title="Asenapine">asenapine</a>, <a href="/wiki/Brexpiprazole" title="Brexpiprazole">brexpiprazole</a>, <a href="/wiki/Cariprazine" title="Cariprazine">cariprazine</a>, <a href="/wiki/Clozapine" title="Clozapine">clozapine</a>, <a href="/wiki/Lurasidone" title="Lurasidone">lurasidone</a>, <a href="/wiki/Quetiapine" title="Quetiapine">quetiapine</a>, <a href="/wiki/Ziprasidone" title="Ziprasidone">ziprasidone</a>)</li> <li><a href="/wiki/Azapirone" title="Azapirone">Azapirones</a> (e.g., <a href="/wiki/Buspirone" title="Buspirone">buspirone</a>, <a href="/wiki/Eptapirone" title="Eptapirone">eptapirone</a>, <a href="/wiki/Gepirone" title="Gepirone">gepirone</a>, <a href="/wiki/Perospirone" title="Perospirone">perospirone</a>, <a href="/wiki/Tandospirone" title="Tandospirone">tandospirone</a>)</li> <li><a href="/wiki/Bay_R_1531" title="Bay R 1531">Bay R 1531</a></li> <li><a href="/wiki/Befiradol" title="Befiradol">Befiradol</a></li> <li><a href="/wiki/BMY-14802" title="BMY-14802">BMY-14802</a></li> <li><a href="/wiki/Cannabidiol" title="Cannabidiol">Cannabidiol</a></li> <li><a href="/wiki/Dimemebfe" title="Dimemebfe">Dimemebfe</a></li> <li><a href="/wiki/Dopamine" title="Dopamine">Dopamine</a></li> <li><a href="/wiki/Ebalzotan" title="Ebalzotan">Ebalzotan</a></li> <li><a href="/wiki/Eltoprazine" title="Eltoprazine">Eltoprazine</a></li> <li><a href="/wiki/Enciprazine" title="Enciprazine">Enciprazine</a></li> <li><a href="/wiki/Ergoline" title="Ergoline">Ergolines</a> (e.g., <a href="/wiki/Bromocriptine" title="Bromocriptine">bromocriptine</a>, <a href="/wiki/Cabergoline" title="Cabergoline">cabergoline</a>, <a href="/wiki/Dihydroergotamine" title="Dihydroergotamine">dihydroergotamine</a>, <a href="/wiki/Ergotamine" title="Ergotamine">ergotamine</a>, <a href="/wiki/Lisuride" title="Lisuride">lisuride</a>, <a href="/wiki/LSD" title="LSD">LSD</a>, <a href="/wiki/Methylergometrine" title="Methylergometrine">methylergometrine (methylergonovine)</a>, <a href="/wiki/Methysergide" title="Methysergide">methysergide</a>, <a href="/wiki/Pergolide" title="Pergolide">pergolide</a>)</li> <li><a href="/wiki/F-11,461" title="F-11,461">F-11,461</a></li> <li><a href="/w/index.php?title=F-12826&action=edit&redlink=1" class="new" title="F-12826 (page does not exist)">F-12826</a></li> <li><a href="/w/index.php?title=F-13714&action=edit&redlink=1" class="new" title="F-13714 (page does not exist)">F-13714</a></li> <li><a href="/w/index.php?title=F-14679&action=edit&redlink=1" class="new" title="F-14679 (page does not exist)">F-14679</a></li> <li><a href="/wiki/F-15063" title="F-15063">F-15063</a></li> <li><a href="/wiki/F-15,599" title="F-15,599">F-15,599</a></li> <li><a href="/wiki/Flesinoxan" title="Flesinoxan">Flesinoxan</a></li> <li><a href="/wiki/Flibanserin" title="Flibanserin">Flibanserin</a></li> <li><a href="/wiki/Flumexadol" title="Flumexadol">Flumexadol</a></li> <li><a href="/wiki/Hypidone" title="Hypidone">Hypidone</a></li> <li><a href="/wiki/Lesopitron" title="Lesopitron">Lesopitron</a></li> <li><a href="/wiki/LY-293284" title="LY-293284">LY-293284</a></li> <li><a href="/w/index.php?title=LY-301317&action=edit&redlink=1" class="new" title="LY-301317 (page does not exist)">LY-301317</a></li> <li><a href="/wiki/Meta-Chlorophenylpiperazine" title="Meta-Chlorophenylpiperazine">mCPP</a></li> <li><a href="/wiki/Osemozotan" title="Osemozotan">MKC-242</a></li> <li><a href="/wiki/Naluzotan" title="Naluzotan">Naluzotan</a></li> <li><a href="/wiki/NBUMP" title="NBUMP">NBUMP</a></li> <li><a href="/wiki/Osemozotan" title="Osemozotan">Osemozotan</a></li> <li><a href="/wiki/Oxaflozane" title="Oxaflozane">Oxaflozane</a></li> <li><a href="/wiki/Pardoprunox" title="Pardoprunox">Pardoprunox</a></li> <li><a href="/wiki/Piclozotan" title="Piclozotan">Piclozotan</a></li> <li><a href="/wiki/Rauwolscine" title="Rauwolscine">Rauwolscine</a></li> <li><a href="/wiki/Repinotan" title="Repinotan">Repinotan</a></li> <li><a href="/wiki/Roxindole" title="Roxindole">Roxindole</a></li> <li><a href="/wiki/RU-24,969" title="RU-24,969">RU-24,969</a></li> <li><a href="/wiki/S-14,506" title="S-14,506">S-14,506</a></li> <li><a href="/wiki/S-14671" title="S-14671">S-14671</a></li> <li><a href="/wiki/S-15535" title="S-15535">S-15535</a></li> <li><a href="/wiki/Sarizotan" title="Sarizotan">Sarizotan</a></li> <li><a href="/wiki/Serotonin" title="Serotonin">Serotonin (5-HT)</a></li> <li><a href="/w/index.php?title=SSR-181507&action=edit&redlink=1" class="new" title="SSR-181507 (page does not exist)">SSR-181507</a></li> <li><a href="/wiki/Sunepitron" title="Sunepitron">Sunepitron</a></li> <li><a href="/wiki/Substituted_tryptamine" title="Substituted tryptamine">Tryptamines</a> (e.g., <a href="/wiki/5-Carboxamidotryptamine" title="5-Carboxamidotryptamine">5-CT</a>, <a href="/wiki/5-MeO-DMT" title="5-MeO-DMT">5-MeO-DMT</a>, <a href="/wiki/5-Methoxytryptamine" title="5-Methoxytryptamine">5-MT</a>, <a href="/wiki/Bufotenin" title="Bufotenin">bufotenin</a>, <a href="/wiki/N,N-Dimethyltryptamine" title="N,N-Dimethyltryptamine">DMT</a>, <a href="/wiki/Indorenate" title="Indorenate">indorenate</a>, <a href="/wiki/N-Methylserotonin" title="N-Methylserotonin">N-Me-5-HT</a>, <a href="/wiki/Psilocin" title="Psilocin">psilocin</a>, <a href="/wiki/Psilocybin" title="Psilocybin">psilocybin</a>)</li> <li><a href="/wiki/TGBA01AD" title="TGBA01AD">TGBA01AD</a></li> <li><a href="/wiki/U-92,016-A" title="U-92,016-A">U-92,016-A</a></li> <li><a href="/wiki/Urapidil" title="Urapidil">Urapidil</a></li> <li><a href="/wiki/Vilazodone" title="Vilazodone">Vilazodone</a></li> <li><a href="/wiki/Xaliproden" title="Xaliproden">Xaliproden</a></li> <li><a href="/wiki/Yohimbine" title="Yohimbine">Yohimbine</a></li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i>Antagonists:</i> <a href="/wiki/Atypical_antipsychotic" title="Atypical antipsychotic">Atypical antipsychotics</a> (e.g., <a href="/wiki/Iloperidone" title="Iloperidone">iloperidone</a>, <a href="/wiki/Risperidone" title="Risperidone">risperidone</a>, <a href="/wiki/Sertindole" title="Sertindole">sertindole</a>)</li> <li><a href="/w/index.php?title=AV965&action=edit&redlink=1" class="new" title="AV965 (page does not exist)">AV965</a></li> <li><a href="/wiki/Beta_blocker" title="Beta blocker">Beta blockers</a> (e.g., <a href="/wiki/Alprenolol" title="Alprenolol">alprenolol</a>, <a href="/wiki/Carteolol" title="Carteolol">carteolol</a>, <a href="/wiki/Cyanopindolol" title="Cyanopindolol">cyanopindolol</a>, <a href="/wiki/Iodocyanopindolol" title="Iodocyanopindolol">iodocyanopindolol</a>, <a href="/wiki/Isamoltane" title="Isamoltane">isamoltane</a>, <a href="/wiki/Oxprenolol" title="Oxprenolol">oxprenolol</a>, <a href="/wiki/Penbutolol" title="Penbutolol">penbutolol</a>, <a href="/wiki/Pindobind" title="Pindobind">pindobind</a>, <a href="/wiki/Pindolol" title="Pindolol">pindolol</a>, <a href="/wiki/Propranolol" title="Propranolol">propranolol</a>, <a href="/wiki/Tertatolol" title="Tertatolol">tertatolol</a>)</li> <li><a href="/wiki/BMY-7,378" class="mw-redirect" title="BMY-7,378">BMY-7,378</a></li> <li><a href="/wiki/CSP-2503" title="CSP-2503">CSP-2503</a></li> <li><a href="/wiki/Dotarizine" title="Dotarizine">Dotarizine</a></li> <li><a href="/wiki/Ergoline" title="Ergoline">Ergolines</a> (e.g., <a href="/wiki/Metergoline" title="Metergoline">metergoline</a>)</li> <li><a href="/w/index.php?title=FCE-24379&action=edit&redlink=1" class="new" title="FCE-24379 (page does not exist)">FCE-24379</a></li> <li><a href="/wiki/Flopropione" title="Flopropione">Flopropione</a></li> <li><a href="/w/index.php?title=GR-46611&action=edit&redlink=1" class="new" title="GR-46611 (page does not exist)">GR-46611</a></li> <li><a href="/wiki/Isamoltane" title="Isamoltane">Isamoltane</a></li> <li><a href="/wiki/Lecozotan" title="Lecozotan">Lecozotan</a></li> <li><a href="/wiki/Mefway_(18F)" title="Mefway (18F)">Mefway</a></li> <li><a href="/wiki/Metitepine" title="Metitepine">Metitepine (methiothepin)</a></li> <li><a href="/wiki/MIN-117" title="MIN-117">MIN-117 (WF-516)</a></li> <li><a href="/wiki/MPPF" title="MPPF">MPPF</a></li> <li><a href="/wiki/NAN-190" title="NAN-190">NAN-190</a></li> <li><a href="/wiki/Robalzotan" title="Robalzotan">Robalzotan</a></li> <li><a href="/wiki/S-15535" title="S-15535">S-15535</a></li> <li><a href="/wiki/SB-649,915" title="SB-649,915">SB-649,915</a></li> <li><a href="/w/index.php?title=SDZ_216-525&action=edit&redlink=1" class="new" title="SDZ 216-525 (page does not exist)">SDZ 216-525</a></li> <li><a href="/wiki/Spiperone" title="Spiperone">Spiperone</a></li> <li><a href="/wiki/Spiramide" title="Spiramide">Spiramide</a></li> <li><a href="/wiki/Spiroxatrine" title="Spiroxatrine">Spiroxatrine</a></li> <li><a href="/wiki/UH-301" title="UH-301">UH-301</a></li> <li><a href="/wiki/WAY-100135" title="WAY-100135">WAY-100135</a></li> <li><a href="/wiki/WAY-100635" title="WAY-100635">WAY-100635</a></li> <li><a href="/wiki/Xylamidine" title="Xylamidine">Xylamidine</a></li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i>Unknown/unsorted:</i> <a href="/wiki/Acetryptine" title="Acetryptine">Acetryptine</a></li> <li><a href="/wiki/Carvedilol" title="Carvedilol">Carvedilol</a></li> <li><a href="/wiki/Ergoline" title="Ergoline">Ergolines</a> (e.g., <a href="/wiki/Ergometrine" title="Ergometrine">ergometrine (ergonovine)</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/5-HT1B_receptor" title="5-HT1B receptor">5-HT<sub>1B</sub></a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><td colspan="2" class="navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i>Agonists:</i> <a href="/wiki/Anpirtoline" title="Anpirtoline">Anpirtoline</a></li> <li><a href="/wiki/CGS-12066A" title="CGS-12066A">CGS-12066A</a></li> <li><a href="/wiki/CP-93129" title="CP-93129">CP-93129</a></li> <li><a href="/wiki/CP-94253" title="CP-94253">CP-94253</a></li> <li><a href="/wiki/CP-122,288" title="CP-122,288">CP-122,288</a></li> <li><a href="/wiki/CP-135807" title="CP-135807">CP-135807</a></li> <li><a href="/wiki/Eltoprazine" title="Eltoprazine">Eltoprazine</a></li> <li><a href="/wiki/Ergoline" title="Ergoline">Ergolines</a> (e.g., <a href="/wiki/Bromocriptine" title="Bromocriptine">bromocriptine</a>, <a href="/wiki/Dihydroergotamine" title="Dihydroergotamine">dihydroergotamine</a>, <a href="/wiki/Ergotamine" title="Ergotamine">ergotamine</a>, <a href="/wiki/Methylergometrine" title="Methylergometrine">methylergometrine (methylergonovine)</a>, <a href="/wiki/Methysergide" title="Methysergide">methysergide</a>, <a href="/wiki/Pergolide" title="Pergolide">pergolide</a>)</li> <li><a href="/wiki/Meta-Chlorophenylpiperazine" title="Meta-Chlorophenylpiperazine">mCPP</a></li> <li><a href="/wiki/RU-24,969" title="RU-24,969">RU-24,969</a></li> <li><a href="/wiki/Serotonin" title="Serotonin">Serotonin (5-HT)</a></li> <li><a href="/wiki/Triptan" title="Triptan">Triptans</a> (e.g., <a href="/wiki/Avitriptan" title="Avitriptan">avitriptan</a>, <a href="/wiki/Donitriptan" title="Donitriptan">donitriptan</a>, <a href="/wiki/Eletriptan" title="Eletriptan">eletriptan</a>, <a href="/wiki/Sumatriptan" title="Sumatriptan">sumatriptan</a>, <a href="/wiki/Zolmitriptan" title="Zolmitriptan">zolmitriptan</a>)</li> <li><a href="/wiki/Trifluoromethylphenylpiperazine" title="Trifluoromethylphenylpiperazine">TFMPP</a></li> <li><a href="/wiki/Substituted_tryptamine" title="Substituted tryptamine">Tryptamines</a> (e.g., <a href="/wiki/5-Benzyloxytryptamine" title="5-Benzyloxytryptamine">5-BT</a>, <a href="/wiki/5-Carboxamidotryptamine" title="5-Carboxamidotryptamine">5-CT</a>, <a href="/wiki/5-Methoxytryptamine" title="5-Methoxytryptamine">5-MT</a>, <a href="/wiki/N,N-Dimethyltryptamine" title="N,N-Dimethyltryptamine">DMT</a>)</li> <li><a href="/wiki/Vortioxetine" title="Vortioxetine">Vortioxetine</a></li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i>Antagonists:</i> <a href="/wiki/AR-A000002" title="AR-A000002">AR-A000002</a></li> <li><a href="/wiki/Beta_blocker" title="Beta blocker">Beta blockers</a> (e.g., <a href="/wiki/Alprenolol" title="Alprenolol">alprenolol</a>, <a href="/wiki/Carteolol" title="Carteolol">carteolol</a>, <a href="/wiki/Isamoltane" title="Isamoltane">isamoltane</a>, <a href="/wiki/Oxprenolol" title="Oxprenolol">oxprenolol</a>, <a href="/wiki/Penbutolol" title="Penbutolol">penbutolol</a>, <a href="/wiki/Propranolol" title="Propranolol">propranolol</a>, <a href="/wiki/Tertatolol" title="Tertatolol">tertatolol</a>)</li> <li><a href="/wiki/Elzasonan" title="Elzasonan">Elzasonan</a></li> <li><a href="/wiki/Ergoline" title="Ergoline">Ergolines</a> (e.g., <a href="/wiki/Metergoline" title="Metergoline">metergoline</a>)</li> <li><a href="/wiki/GR-127935" title="GR-127935">GR-127935</a></li> <li><a href="/wiki/Isamoltane" title="Isamoltane">Isamoltane</a></li> <li><a href="/wiki/LY-393558" title="LY-393558">LY-393558</a></li> <li><a href="/wiki/Metitepine" title="Metitepine">Metitepine (methiothepin)</a></li> <li><a href="/wiki/SB-216641" title="SB-216641">SB-216641</a></li> <li><a href="/w/index.php?title=SB-224289&action=edit&redlink=1" class="new" title="SB-224289 (page does not exist)">SB-224289</a></li> <li><a href="/wiki/SB-236057" title="SB-236057">SB-236057</a></li> <li><a href="/wiki/Yohimbine" title="Yohimbine">Yohimbine</a></li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i>Unknown/unsorted:</i> <a href="/wiki/Ergoline" title="Ergoline">Ergolines</a> (e.g., <a href="/wiki/Cabergoline" title="Cabergoline">cabergoline</a>, <a href="/wiki/Ergometrine" title="Ergometrine">ergometrine (ergonovine)</a>, <a href="/wiki/Lisuride" title="Lisuride">lisuride</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/5-HT1D_receptor" title="5-HT1D receptor">5-HT<sub>1D</sub></a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><td colspan="2" class="navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i>Agonists:</i> <a href="/wiki/CP-122,288" title="CP-122,288">CP-122,288</a></li> <li><a href="/wiki/CP-135807" title="CP-135807">CP-135807</a></li> <li><a href="/w/index.php?title=CP-286601&action=edit&redlink=1" class="new" title="CP-286601 (page does not exist)">CP-286601</a></li> <li><a href="/wiki/Ergoline" title="Ergoline">Ergolines</a> (e.g., <a href="/wiki/Bromocriptine" title="Bromocriptine">bromocriptine</a>, <a href="/wiki/Cabergoline" title="Cabergoline">cabergoline</a>, <a href="/wiki/Dihydroergotamine" title="Dihydroergotamine">dihydroergotamine</a>, <a href="/wiki/Ergotamine" title="Ergotamine">ergotamine</a>, <a href="/wiki/LSD" title="LSD">LSD</a>, <a href="/wiki/Methysergide" title="Methysergide">methysergide</a>)</li> <li><a href="/w/index.php?title=GR-46611&action=edit&redlink=1" class="new" title="GR-46611 (page does not exist)">GR-46611</a></li> <li><a href="/wiki/L-694247" title="L-694247">L-694247</a></li> <li><a href="/w/index.php?title=L-772405&action=edit&redlink=1" class="new" title="L-772405 (page does not exist)">L-772405</a></li> <li><a href="/wiki/Meta-Chlorophenylpiperazine" title="Meta-Chlorophenylpiperazine">mCPP</a></li> <li><a href="/w/index.php?title=PNU-109291&action=edit&redlink=1" class="new" title="PNU-109291 (page does not exist)">PNU-109291</a></li> <li><a href="/wiki/PNU-142633" title="PNU-142633">PNU-142633</a></li> <li><a href="/wiki/Serotonin" title="Serotonin">Serotonin (5-HT)</a></li> <li><a href="/wiki/TGBA01AD" title="TGBA01AD">TGBA01AD</a></li> <li><a href="/wiki/Triptan" title="Triptan">Triptans</a> (e.g., <a href="/wiki/Almotriptan" title="Almotriptan">almotriptan</a>, <a href="/wiki/Avitriptan" title="Avitriptan">avitriptan</a>, <a href="/wiki/Donitriptan" title="Donitriptan">donitriptan</a>, <a href="/wiki/Eletriptan" title="Eletriptan">eletriptan</a>, <a href="/wiki/Frovatriptan" title="Frovatriptan">frovatriptan</a>, <a href="/wiki/Naratriptan" title="Naratriptan">naratriptan</a>, <a href="/wiki/Rizatriptan" title="Rizatriptan">rizatriptan</a>, <a href="/wiki/Sumatriptan" title="Sumatriptan">sumatriptan</a>, <a href="/wiki/Zolmitriptan" title="Zolmitriptan">zolmitriptan</a>)</li> <li><a href="/wiki/Substituted_tryptamine" title="Substituted tryptamine">Tryptamines</a> (e.g., <a href="/wiki/5-Benzyloxytryptamine" title="5-Benzyloxytryptamine">5-BT</a>, <a href="/wiki/5-Carboxamidotryptamine" title="5-Carboxamidotryptamine">5-CT</a>, <a href="/wiki/5-Ethyl-DMT" title="5-Ethyl-DMT">5-Et-DMT</a>, <a href="/wiki/5-Methoxytryptamine" title="5-Methoxytryptamine">5-MT</a>, <a href="/wiki/5-(Nonyloxy)tryptamine" title="5-(Nonyloxy)tryptamine">5-(nonyloxy)tryptamine</a>, <a href="/wiki/N,N-Dimethyltryptamine" title="N,N-Dimethyltryptamine">DMT</a>)</li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i>Antagonists:</i> <a href="/wiki/Alniditan" title="Alniditan">Alniditan</a></li> <li><a href="/wiki/BRL-15,572" title="BRL-15,572">BRL-15,572</a></li> <li><a href="/wiki/Elzasonan" title="Elzasonan">Elzasonan</a></li> <li><a href="/wiki/Ergoline" title="Ergoline">Ergolines</a> (e.g., <a href="/wiki/Metergoline" title="Metergoline">metergoline</a>)</li> <li><a href="/wiki/GR-127935" title="GR-127935">GR-127935</a></li> <li><a href="/wiki/Ketanserin" title="Ketanserin">Ketanserin</a></li> <li><a href="/wiki/LY-310762" title="LY-310762">LY-310762</a></li> <li><a href="/wiki/LY-367642" title="LY-367642">LY-367642</a></li> <li><a href="/wiki/LY-393558" title="LY-393558">LY-393558</a></li> <li><a href="/wiki/LY-456219" title="LY-456219">LY-456219</a></li> <li><a href="/wiki/LY-456220" title="LY-456220">LY-456220</a></li> <li><a href="/wiki/Metitepine" title="Metitepine">Metitepine (methiothepin)</a></li> <li><a href="/wiki/Mianserin" title="Mianserin">Mianserin</a></li> <li><a href="/wiki/Ritanserin" title="Ritanserin">Ritanserin</a></li> <li><a href="/wiki/Yohimbine" title="Yohimbine">Yohimbine</a></li> <li><a href="/wiki/Ziprasidone" title="Ziprasidone">Ziprasidone</a></li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i>Unknown/unsorted:</i> <a href="/wiki/Acetryptine" title="Acetryptine">Acetryptine</a></li> <li><a href="/wiki/Ergoline" title="Ergoline">Ergolines</a> (e.g., <a href="/wiki/Lisuride" title="Lisuride">lisuride</a>, <a href="/wiki/Lysergol" title="Lysergol">lysergol</a>, <a href="/wiki/Pergolide" title="Pergolide">pergolide</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/5-HT1E_receptor" title="5-HT1E receptor">5-HT<sub>1E</sub></a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><td colspan="2" class="navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i>Agonists:</i> <a href="/wiki/BRL-54443" title="BRL-54443">BRL-54443</a></li> <li><a href="/wiki/Ergoline" title="Ergoline">Ergolines</a> (e.g., <a href="/wiki/Methysergide" title="Methysergide">methysergide</a>)</li> <li><a href="/wiki/Serotonin" title="Serotonin">Serotonin (5-HT)</a></li> <li><a href="/wiki/Triptan" title="Triptan">Triptans</a> (e.g., <a href="/wiki/Eletriptan" title="Eletriptan">eletriptan</a>)</li> <li><a href="/wiki/Substituted_tryptamine" title="Substituted tryptamine">Tryptamines</a> (e.g., <a href="/wiki/Tryptamine" title="Tryptamine">tryptamine</a>)</li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i>Antagonists:</i> <a href="/wiki/Metitepine" title="Metitepine">Metitepine (methiothepin)</a></li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i>Unknown/unsorted:</i> <a href="/wiki/Ergoline" title="Ergoline">Ergolines</a> (e.g., <a href="/wiki/Ergometrine" title="Ergometrine">ergometrine (ergonovine)</a>, <a href="/wiki/Lysergol" title="Lysergol">lysergol</a>, <a href="/wiki/Methylergometrine" title="Methylergometrine">methylergometrine (methylergonovine)</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/5-HT1F_receptor" title="5-HT1F receptor">5-HT<sub>1F</sub></a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><td colspan="2" class="navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i>Agonists:</i> <a href="/wiki/BRL-54443" title="BRL-54443">BRL-54443</a></li> <li><a href="/wiki/CP-122,288" title="CP-122,288">CP-122,288</a></li> <li><a href="/wiki/Ergoline" title="Ergoline">Ergolines</a> (e.g., <a href="/wiki/Bromocriptine" title="Bromocriptine">bromocriptine</a>, <a href="/wiki/Lysergol" title="Lysergol">lysergol</a>, <a href="/wiki/Methylergometrine" title="Methylergometrine">methylergometrine (methylergonovine)</a> <a href="/wiki/Methysergide" title="Methysergide">methysergide</a>)</li> <li><a href="/wiki/Lasmiditan" title="Lasmiditan">Lasmiditan</a></li> <li><a href="/wiki/LY-334370" title="LY-334370">LY-334370</a></li> <li><a href="/wiki/Serotonin" title="Serotonin">Serotonin (5-HT)</a></li> <li><a href="/wiki/Triptan" title="Triptan">Triptans</a> (e.g., <a href="/wiki/Eletriptan" title="Eletriptan">eletriptan</a>, <a href="/wiki/Naratriptan" title="Naratriptan">naratriptan</a>, <a href="/wiki/Sumatriptan" title="Sumatriptan">sumatriptan</a>)</li> <li><a href="/wiki/Substituted_tryptamine" title="Substituted tryptamine">Tryptamines</a> (e.g., <a href="/wiki/5-Methoxytryptamine" title="5-Methoxytryptamine">5-MT</a>)</li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i>Antagonists:</i> <a href="/wiki/Metitepine" title="Metitepine">Metitepine (methiothepin)</a></li> <li><a href="/wiki/Mianserin" title="Mianserin">Mianserin</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/5-HT2_receptor" title="5-HT2 receptor">5-HT<sub>2</sub></a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/5-HT2A_receptor" title="5-HT2A receptor">5-HT<sub>2A</sub></a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><td colspan="2" class="navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i>Agonists:</i> 25H/NB series (e.g., <a href="/wiki/25I-NBF" title="25I-NBF">25I-NBF</a>, <a href="/wiki/25I-NBMD" title="25I-NBMD">25I-NBMD</a>, <a href="/wiki/25I-NBOH" title="25I-NBOH">25I-NBOH</a>, <a href="/wiki/25I-NBOMe" title="25I-NBOMe">25I-NBOMe</a>, <a href="/wiki/25B-NBOMe" title="25B-NBOMe">25B-NBOMe</a>, <a href="/wiki/25C-NBOMe" title="25C-NBOMe">25C-NBOMe</a>, <a href="/wiki/25TFM-NBOMe" title="25TFM-NBOMe">25TFM-NBOMe</a>, <a href="/wiki/2CBCB-NBOMe" title="2CBCB-NBOMe">2CBCB-NBOMe</a>, <a href="/wiki/25CN-NBOH" title="25CN-NBOH">25CN-NBOH</a>, <a href="/wiki/2CBFly-NBOMe" title="2CBFly-NBOMe">2CBFly-NBOMe</a>)</li> <li><a href="/wiki/2C_(psychedelics)" title="2C (psychedelics)">2Cs</a> (e.g., <a href="/wiki/2C-B" title="2C-B">2C-B</a>, <a href="/wiki/2C-E" title="2C-E">2C-E</a>, <a href="/wiki/2C-I" title="2C-I">2C-I</a>, <a href="/wiki/2C-T-2" title="2C-T-2">2C-T-2</a>, <a href="/wiki/2C-T-7" title="2C-T-7">2C-T-7</a>, <a href="/wiki/2C-T-21" title="2C-T-21">2C-T-21</a>)</li> <li><a href="/wiki/2C-B-FLY" title="2C-B-FLY">2C-B-FLY</a></li> <li><a href="/wiki/2CB-Ind" title="2CB-Ind">2CB-Ind</a></li> <li><a href="/wiki/5-Methoxytryptamine" title="5-Methoxytryptamine">5-Methoxytryptamines</a> (<a href="/wiki/5-MeO-DET" title="5-MeO-DET">5-MeO-DET</a>, <a href="/wiki/5-Methoxy-N,N-diisopropyltryptamine" class="mw-redirect" title="5-Methoxy-N,N-diisopropyltryptamine">5-MeO-DiPT</a>, <a href="/wiki/5-MeO-DMT" title="5-MeO-DMT">5-MeO-DMT</a>, <a href="/wiki/5-MeO-DPT" title="5-MeO-DPT">5-MeO-DPT</a>, <a href="/wiki/5-Methoxytryptamine" title="5-Methoxytryptamine">5-MT</a>)</li> <li><a href="/wiki/Substituted_alpha-alkyltryptamine" class="mw-redirect" title="Substituted alpha-alkyltryptamine">α-Alkyltryptamines</a> (e.g., <a href="/wiki/5-Chloro-%CE%B1MT" title="5-Chloro-αMT">5-Cl-αMT</a>, <a href="/wiki/5-Fluoro-AMT" title="5-Fluoro-AMT">5-Fl-αMT</a>, <a href="/wiki/5-MeO-AET" title="5-MeO-AET">5-MeO-αET</a>, <a href="/wiki/5-MeO-aMT" title="5-MeO-aMT">5-MeO-αMT</a>, <a href="/wiki/Alpha-Methylserotonin" class="mw-redirect" title="Alpha-Methylserotonin">α-Me-5-HT</a>, <a href="/wiki/Alpha-Ethyltryptamine" class="mw-redirect" title="Alpha-Ethyltryptamine">αET</a>, <a href="/wiki/Alpha-Methyltryptamine" class="mw-redirect" title="Alpha-Methyltryptamine">αMT</a>)</li> <li><a href="/wiki/AL-34662" title="AL-34662">AL-34662</a></li> <li><a href="/wiki/AL-37350A" title="AL-37350A">AL-37350A</a></li> <li><a href="/wiki/Bromo-DragonFLY" title="Bromo-DragonFLY">Bromo-DragonFLY</a></li> <li><a href="/wiki/Dimemebfe" title="Dimemebfe">Dimemebfe</a></li> <li><a href="/wiki/DMBMPP" title="DMBMPP">DMBMPP</a></li> <li><a href="/wiki/DOx" title="DOx">DOx</a> (e.g., <a href="/wiki/2,5-Dimethoxy-4-bromoamphetamine" title="2,5-Dimethoxy-4-bromoamphetamine">DOB</a>, <a href="/wiki/2,5-Dimethoxy-4-chloroamphetamine" title="2,5-Dimethoxy-4-chloroamphetamine">DOC</a>, <a href="/wiki/2,5-Dimethoxy-4-iodoamphetamine" title="2,5-Dimethoxy-4-iodoamphetamine">DOI</a>, <a href="/wiki/2,5-Dimethoxy-4-methylamphetamine" title="2,5-Dimethoxy-4-methylamphetamine">DOM</a>)</li> <li><a href="/wiki/Efavirenz" title="Efavirenz">Efavirenz</a></li> <li><a href="/wiki/Ergoline" title="Ergoline">Ergolines</a> (e.g., <a href="/wiki/1P-LSD" title="1P-LSD">1P-LSD</a>, <a href="/wiki/ALD-52" title="ALD-52">ALD-52</a>, <a href="/wiki/Bromocriptine" title="Bromocriptine">bromocriptine</a>, <a href="/wiki/Cabergoline" title="Cabergoline">cabergoline</a>, <a href="/wiki/Ergine" title="Ergine">ergine (LSA)</a>, <a href="/wiki/Ergometrine" title="Ergometrine">ergometrine (ergonovine)</a>, <a href="/wiki/Ergotamine" title="Ergotamine">ergotamine</a>, <a href="/wiki/Lisuride" title="Lisuride">lisuride</a>, <a href="/wiki/Lysergic_acid_2,4-dimethylazetidide" title="Lysergic acid 2,4-dimethylazetidide">LA-SS-Az</a>, <a href="/wiki/Lysergic_acid_2-butyl_amide" title="Lysergic acid 2-butyl amide">LSB</a>, <a href="/wiki/LSD" title="LSD">LSD</a>, <a href="/wiki/LSD-Pip" title="LSD-Pip">LSD-Pip</a>, <a href="/wiki/Lysergic_acid_hydroxyethylamide" title="Lysergic acid hydroxyethylamide">LSH</a>, <a href="/wiki/Lysergic_acid_3-pentyl_amide" title="Lysergic acid 3-pentyl amide">LSP</a>, <a href="/wiki/Methylergometrine" title="Methylergometrine">methylergometrine (methylergonovine)</a>, <a href="/wiki/Pergolide" title="Pergolide">pergolide</a>)</li> <li><a href="/wiki/Flumexadol" title="Flumexadol">Flumexadol</a></li> <li><a href="/wiki/IHCH-7113" title="IHCH-7113">IHCH-7113</a></li> <li><a href="/wiki/Jimscaline" title="Jimscaline">Jimscaline</a></li> <li><a href="/wiki/Lorcaserin" title="Lorcaserin">Lorcaserin</a></li> <li><a href="/wiki/Substituted_methylenedioxyphenethylamine" title="Substituted methylenedioxyphenethylamine">MDxx</a> (e.g., <a href="/wiki/3,4-Methylenedioxyamphetamine" title="3,4-Methylenedioxyamphetamine">MDA (tenamfetamine)</a>, <a href="/wiki/MDMA" title="MDMA">MDMA (midomafetamine)</a>, <a href="/wiki/3,4-Methylenedioxy-N-hydroxyamphetamine" title="3,4-Methylenedioxy-N-hydroxyamphetamine">MDOH</a>, <a href="/wiki/MMDA_(drug)" title="MMDA (drug)">MMDA</a>)</li> <li><a href="/wiki/O-4310" title="O-4310">O-4310</a></li> <li><a href="/wiki/Oxaflozane" title="Oxaflozane">Oxaflozane</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/RH-34" title="RH-34">RH-34</a></li> <li><a href="/wiki/SCHEMBL5334361" title="SCHEMBL5334361">SCHEMBL5334361</a></li> <li><a href="/wiki/Substituted_phenethylamine" title="Substituted phenethylamine">Phenethylamines</a> (e.g., <a href="/wiki/Lophophine" title="Lophophine">lophophine</a>, <a href="/wiki/Mescaline" title="Mescaline">mescaline</a>)</li> <li><a href="/wiki/Piperazine" title="Piperazine">Piperazines</a> (e.g., <a href="/wiki/Benzylpiperazine" title="Benzylpiperazine">BZP</a>, <a href="/wiki/Quipazine" title="Quipazine">quipazine</a>, <a href="/wiki/Trifluoromethylphenylpiperazine" title="Trifluoromethylphenylpiperazine">TFMPP</a>)</li> <li><a href="/wiki/Serotonin" title="Serotonin">Serotonin (5-HT)</a></li> <li><a href="/wiki/TCB-2" title="TCB-2">TCB-2</a></li> <li><a href="/wiki/TFMFly" title="TFMFly">TFMFly</a></li> <li><a href="/wiki/Substituted_tryptamine" title="Substituted tryptamine">Tryptamines</a> (e.g., <a href="/wiki/5-Benzyloxytryptamine" title="5-Benzyloxytryptamine">5-BT</a>, <a href="/wiki/5-Carboxamidotryptamine" title="5-Carboxamidotryptamine">5-CT</a>, <a href="/wiki/Bufotenin" title="Bufotenin">bufotenin</a>, <a href="/wiki/Diethyltryptamine" title="Diethyltryptamine">DET</a>, <a href="/wiki/Diisopropyltryptamine" class="mw-redirect" title="Diisopropyltryptamine">DiPT</a>, <a href="/wiki/N,N-Dimethyltryptamine" title="N,N-Dimethyltryptamine">DMT</a>, <a href="/wiki/Dipropyltryptamine" title="Dipropyltryptamine">DPT</a>, <a href="/wiki/Psilocin" title="Psilocin">psilocin</a>, <a href="/wiki/Psilocybin" title="Psilocybin">psilocybin</a>, <a href="/wiki/Tryptamine" title="Tryptamine">tryptamine</a>)</li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i>Antagonists:</i> <a href="/wiki/5-I-R91150" title="5-I-R91150">5-I-R91150</a></li> <li><a href="/wiki/5-MeO-NBpBrT" title="5-MeO-NBpBrT">5-MeO-NBpBrT</a></li> <li><a href="/wiki/AC-90179" title="AC-90179">AC-90179</a></li> <li><a href="/wiki/Adatanserin" title="Adatanserin">Adatanserin</a></li> <li><a href="/wiki/Altanserin" title="Altanserin">Altanserin</a></li> <li><a href="/wiki/Antihistamine" title="Antihistamine">Antihistamines</a> (e.g., <a href="/wiki/Cyproheptadine" title="Cyproheptadine">cyproheptadine</a>, <a href="/wiki/Hydroxyzine" title="Hydroxyzine">hydroxyzine</a>, <a href="/wiki/Ketotifen" title="Ketotifen">ketotifen</a>, <a href="/wiki/Perlapine" title="Perlapine">perlapine</a>)</li> <li><a href="/wiki/9-Aminomethyl-9,10-dihydroanthracene" title="9-Aminomethyl-9,10-dihydroanthracene">AMDA</a></li> <li><a href="/wiki/Atypical_antipsychotic" title="Atypical antipsychotic">Atypical antipsychotics</a> (e.g., <a href="/wiki/Amperozide" title="Amperozide">amperozide</a>, <a href="/wiki/Aripiprazole" title="Aripiprazole">aripiprazole</a>, <a href="/wiki/Asenapine" title="Asenapine">asenapine</a>, <a href="/wiki/Blonanserin" title="Blonanserin">blonanserin</a>, <a href="/wiki/Brexpiprazole" title="Brexpiprazole">brexpiprazole</a>, <a href="/wiki/Carpipramine" title="Carpipramine">carpipramine</a>, <a href="/wiki/Clocapramine" title="Clocapramine">clocapramine</a>, <a href="/wiki/Clorotepine" title="Clorotepine">clorotepine</a>, <a href="/wiki/Clozapine" title="Clozapine">clozapine</a>, <a href="/wiki/Fluperlapine" title="Fluperlapine">fluperlapine</a>, <a href="/wiki/Gevotroline" title="Gevotroline">gevotroline</a>, <a href="/wiki/Iloperidone" title="Iloperidone">iloperidone</a>, <a href="/wiki/Lurasidone" title="Lurasidone">lurasidone</a>, <a href="/wiki/Melperone" title="Melperone">melperone</a>, <a href="/wiki/Mosapramine" title="Mosapramine">mosapramine</a>, <a href="/wiki/Ocaperidone" title="Ocaperidone">ocaperidone</a>, <a href="/wiki/Olanzapine" title="Olanzapine">olanzapine</a>, <a href="/wiki/Paliperidone" title="Paliperidone">paliperidone</a>, <a href="/wiki/Quetiapine" title="Quetiapine">quetiapine</a>, <a href="/wiki/Risperidone" title="Risperidone">risperidone</a>, <a href="/wiki/Sertindole" title="Sertindole">sertindole</a>, <a href="/wiki/Zicronapine" title="Zicronapine">zicronapine</a>, <a href="/wiki/Ziprasidone" title="Ziprasidone">ziprasidone</a>, <a href="/wiki/Zotepine" title="Zotepine">zotepine</a>)</li> <li><a href="/wiki/Chlorprothixene" title="Chlorprothixene">Chlorprothixene</a></li> <li><a href="/wiki/Cinanserin" title="Cinanserin">Cinanserin</a></li> <li><a href="/wiki/CSP-2503" title="CSP-2503">CSP-2503</a></li> <li><a href="/wiki/Deramciclane" title="Deramciclane">Deramciclane</a></li> <li><a href="/wiki/Dotarizine" title="Dotarizine">Dotarizine</a></li> <li><a href="/wiki/Eplivanserin" title="Eplivanserin">Eplivanserin</a></li> <li><a href="/wiki/Ergoline" title="Ergoline">Ergolines</a> (e.g., <a href="/wiki/Amesergide" title="Amesergide">amesergide</a>, <a href="/w/index.php?title=LY-53857&action=edit&redlink=1" class="new" title="LY-53857 (page does not exist)">LY-53857</a>, <a href="/wiki/LY-215,840" title="LY-215,840">LY-215,840</a>, <a href="/wiki/Mesulergine" title="Mesulergine">mesulergine</a>, <a href="/wiki/Metergoline" title="Metergoline">metergoline</a>, <a href="/wiki/Methysergide" title="Methysergide">methysergide</a>, <a href="/wiki/Sergolexole" title="Sergolexole">sergolexole</a>)</li> <li><a href="/wiki/Fananserin" title="Fananserin">Fananserin</a></li> <li><a href="/wiki/Flibanserin" title="Flibanserin">Flibanserin</a></li> <li><a href="/wiki/Glemanserin" title="Glemanserin">Glemanserin</a></li> <li><a href="/w/index.php?title=Irindalone&action=edit&redlink=1" class="new" title="Irindalone (page does not exist)">Irindalone</a></li> <li><a href="/wiki/Ketanserin" title="Ketanserin">Ketanserin</a></li> <li><a href="/wiki/KML-010" title="KML-010">KML-010</a></li> <li><a href="/w/index.php?title=Landipirdine&action=edit&redlink=1" class="new" title="Landipirdine (page does not exist)">Landipirdine</a></li> <li><a href="/wiki/LY-393558" title="LY-393558">LY-393558</a></li> <li><a href="/wiki/Meta-Chlorophenylpiperazine" title="Meta-Chlorophenylpiperazine">mCPP</a></li> <li><a href="/wiki/Medifoxamine" title="Medifoxamine">Medifoxamine</a></li> <li><a href="/wiki/Metitepine" title="Metitepine">Metitepine (methiothepin)</a></li> <li><a href="/wiki/MIN-117" title="MIN-117">MIN-117 (WF-516)</a></li> <li><a href="/wiki/Naftidrofuryl" title="Naftidrofuryl">Naftidrofuryl</a></li> <li><a href="/wiki/Nantenine" title="Nantenine">Nantenine</a></li> <li><a href="/wiki/Nelotanserin" title="Nelotanserin">Nelotanserin</a></li> <li><a href="/wiki/Opiranserin" title="Opiranserin">Opiranserin (VVZ-149)</a></li> <li><a href="/wiki/Pelanserin" title="Pelanserin">Pelanserin</a></li> <li><a href="/wiki/Phenoxybenzamine" title="Phenoxybenzamine">Phenoxybenzamine</a></li> <li><a href="/wiki/Pimavanserin" title="Pimavanserin">Pimavanserin</a></li> <li><a href="/wiki/Pirenperone" title="Pirenperone">Pirenperone</a></li> <li><a href="/wiki/Pizotifen" title="Pizotifen">Pizotifen</a></li> <li><a href="/wiki/Pruvanserin" title="Pruvanserin">Pruvanserin</a></li> <li><a href="/wiki/Rauwolscine" title="Rauwolscine">Rauwolscine</a></li> <li><a href="/wiki/Ritanserin" title="Ritanserin">Ritanserin</a></li> <li><a href="/wiki/Roluperidone" title="Roluperidone">Roluperidone</a></li> <li><a href="/wiki/S-14671" title="S-14671">S-14671</a></li> <li><a href="/wiki/Sarpogrelate" title="Sarpogrelate">Sarpogrelate</a></li> <li><a href="/wiki/Serotonin_antagonist_and_reuptake_inhibitor" title="Serotonin antagonist and reuptake inhibitor">Serotonin antagonists and reuptake inhibitors</a> (e.g., <a href="/wiki/Etoperidone" title="Etoperidone">etoperidone</a>, <a href="/wiki/Hydroxynefazodone" title="Hydroxynefazodone">hydroxynefazodone</a>, <a href="/wiki/Lubazodone" title="Lubazodone">lubazodone</a>, <a href="/wiki/Mepiprazole" title="Mepiprazole">mepiprazole</a>, <a href="/wiki/Nefazodone" title="Nefazodone">nefazodone</a>, <a href="/wiki/Triazoledione" title="Triazoledione">triazoledione</a>, <a href="/wiki/Trazodone" title="Trazodone">trazodone</a>)</li> <li><a href="/w/index.php?title=SR-46349B&action=edit&redlink=1" class="new" title="SR-46349B (page does not exist)">SR-46349B</a></li> <li><a href="/wiki/TGBA01AD" title="TGBA01AD">TGBA01AD</a></li> <li><a href="/wiki/Teniloxazine" title="Teniloxazine">Teniloxazine</a></li> <li><a href="/w/index.php?title=Temanogrel&action=edit&redlink=1" class="new" title="Temanogrel (page does not exist)">Temanogrel</a></li> <li><a href="/wiki/Tetracyclic_antidepressant" title="Tetracyclic antidepressant">Tetracyclic antidepressants</a> (e.g., <a href="/wiki/Amoxapine" title="Amoxapine">amoxapine</a>, <a href="/wiki/Aptazapine" title="Aptazapine">aptazapine</a>, <a href="/wiki/Esmirtazapine" title="Esmirtazapine">esmirtazapine</a>, <a href="/wiki/Maprotiline" title="Maprotiline">maprotiline</a>, <a href="/wiki/Mianserin" title="Mianserin">mianserin</a>, <a href="/wiki/Mirtazapine" title="Mirtazapine">mirtazapine</a>)</li> <li><a href="/wiki/Tricyclic_antidepressant" title="Tricyclic antidepressant">Tricyclic antidepressants</a> (e.g., <a href="/wiki/Amitriptyline" title="Amitriptyline">amitriptyline</a>)</li> <li><a href="/wiki/Typical_antipsychotic" title="Typical antipsychotic">Typical antipsychotics</a> (e.g., <a href="/wiki/Chlorpromazine" title="Chlorpromazine">chlorpromazine</a>, <a href="/wiki/Fluphenazine" title="Fluphenazine">fluphenazine</a>, <a href="/wiki/Haloperidol" title="Haloperidol">haloperidol</a>, <a href="/wiki/Loxapine" title="Loxapine">loxapine</a>, <a href="/wiki/Perphenazine" title="Perphenazine">perphenazine</a>, <a href="/wiki/Pimozide" title="Pimozide">pimozide</a>, <a href="/wiki/Pipamperone" title="Pipamperone">pipamperone</a>, <a href="/wiki/Prochlorperazine" title="Prochlorperazine">prochlorperazine</a>, <a href="/wiki/Setoperone" title="Setoperone">setoperone</a>, <a href="/wiki/Spiperone" title="Spiperone">spiperone</a>, <a href="/wiki/Spiramide" title="Spiramide">spiramide</a>, <a href="/wiki/Thioridazine" title="Thioridazine">thioridazine</a>, <a href="/wiki/Tiotixene" title="Tiotixene">thiothixene</a>, <a href="/wiki/Trifluoperazine" title="Trifluoperazine">trifluoperazine</a>)</li> <li><a href="/wiki/Volinanserin" title="Volinanserin">Volinanserin</a></li> <li><a href="/wiki/Xylamidine" title="Xylamidine">Xylamidine</a></li> <li><a href="/wiki/Yohimbine" title="Yohimbine">Yohimbine</a></li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i>Unknown/unsorted:</i> <a href="/wiki/Ergoline" title="Ergoline">Ergolines</a> (e.g., <a href="/wiki/Dihydroergotamine" title="Dihydroergotamine">dihydroergotamine</a>, <a href="/wiki/Nicergoline" title="Nicergoline">nicergoline</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/5-HT2B_receptor" title="5-HT2B receptor">5-HT<sub>2B</sub></a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><td colspan="2" class="navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i>Agonists:</i> <a href="/wiki/4-Methylaminorex" title="4-Methylaminorex">4-Methylaminorex</a></li> <li><a href="/wiki/Aminorex" title="Aminorex">Aminorex</a></li> <li><a href="/wiki/Substituted_amphetamine" title="Substituted amphetamine">Amphetamines</a> (e.g., <a href="/wiki/Chlorphentermine" title="Chlorphentermine">chlorphentermine</a>, <a href="/wiki/Cloforex" title="Cloforex">cloforex</a>, <a href="/wiki/Dexfenfluramine" title="Dexfenfluramine">dexfenfluramine</a>, <a href="/wiki/Fenfluramine" title="Fenfluramine">fenfluramine</a>, <a href="/wiki/Levofenfluramine" title="Levofenfluramine">levofenfluramine</a>, <a href="/wiki/Norfenfluramine" title="Norfenfluramine">norfenfluramine</a>)</li> <li><a href="/wiki/BW-723C86" title="BW-723C86">BW-723C86</a></li> <li><a href="/wiki/DOx" title="DOx">DOx</a> (e.g., <a href="/wiki/2,5-Dimethoxy-4-bromoamphetamine" title="2,5-Dimethoxy-4-bromoamphetamine">DOB</a>, <a href="/wiki/2,5-Dimethoxy-4-chloroamphetamine" title="2,5-Dimethoxy-4-chloroamphetamine">DOC</a>, <a href="/wiki/2,5-Dimethoxy-4-iodoamphetamine" title="2,5-Dimethoxy-4-iodoamphetamine">DOI</a>, <a href="/wiki/2,5-Dimethoxy-4-methylamphetamine" title="2,5-Dimethoxy-4-methylamphetamine">DOM</a>)</li> <li><a href="/wiki/Ergoline" title="Ergoline">Ergolines</a> (e.g., <a href="/wiki/Cabergoline" title="Cabergoline">cabergoline</a>, <a href="/wiki/Dihydroergocryptine" title="Dihydroergocryptine">dihydroergocryptine</a>, <a href="/wiki/Dihydroergotamine" title="Dihydroergotamine">dihydroergotamine</a>, <a href="/wiki/Ergotamine" title="Ergotamine">ergotamine</a>, <a href="/wiki/Methylergometrine" title="Methylergometrine">methylergometrine (methylergonovine)</a>, <a href="/wiki/Methysergide" title="Methysergide">methysergide</a>, <a href="/wiki/Pergolide" title="Pergolide">pergolide</a>)</li> <li><a href="/wiki/Lorcaserin" title="Lorcaserin">Lorcaserin</a></li> <li><a href="/wiki/Substituted_methylenedioxyphenethylamine" title="Substituted methylenedioxyphenethylamine">MDxx</a> (e.g., <a href="/wiki/3,4-Methylenedioxyamphetamine" title="3,4-Methylenedioxyamphetamine">MDA (tenamfetamine)</a>, <a href="/wiki/MDMA" title="MDMA">MDMA (midomafetamine)</a>, <a href="/wiki/3,4-Methylenedioxy-N-hydroxyamphetamine" title="3,4-Methylenedioxy-N-hydroxyamphetamine">MDOH</a>, <a href="/wiki/MMDA_(drug)" title="MMDA (drug)">MMDA</a>)</li> <li><a href="/wiki/Substituted_piperazine" title="Substituted piperazine">Piperazines</a> (e.g., <a href="/wiki/Trifluoromethylphenylpiperazine" title="Trifluoromethylphenylpiperazine">TFMPP</a>)</li> <li><a href="/wiki/PNU-22394" title="PNU-22394">PNU-22394</a></li> <li><a href="/wiki/Ro60-0175" title="Ro60-0175">Ro60-0175</a></li> <li><a href="/wiki/Serotonin" title="Serotonin">Serotonin (5-HT)</a></li> <li><a href="/wiki/Substituted_tryptamine" title="Substituted tryptamine">Tryptamines</a> (e.g., <a href="/wiki/5-Benzyloxytryptamine" title="5-Benzyloxytryptamine">5-BT</a>, <a href="/wiki/5-Carboxamidotryptamine" title="5-Carboxamidotryptamine">5-CT</a>, <a href="/wiki/5-Methoxytryptamine" title="5-Methoxytryptamine">5-MT</a>, <a href="/wiki/Alpha-Methylserotonin" class="mw-redirect" title="Alpha-Methylserotonin">α-Me-5-HT</a>, <a href="/wiki/Bufotenin" title="Bufotenin">bufotenin</a>, <a href="/wiki/Diethyltryptamine" title="Diethyltryptamine">DET</a>, <a href="/wiki/Diisopropyltryptamine" class="mw-redirect" title="Diisopropyltryptamine">DiPT</a>, <a href="/wiki/N,N-Dimethyltryptamine" title="N,N-Dimethyltryptamine">DMT</a>, <a href="/wiki/Dipropyltryptamine" title="Dipropyltryptamine">DPT</a>, <a href="/wiki/Psilocin" title="Psilocin">psilocin</a>, <a href="/wiki/Psilocybin" title="Psilocybin">psilocybin</a>, <a href="/wiki/Tryptamine" title="Tryptamine">tryptamine</a>)</li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i>Antagonists:</i> <a href="/wiki/Agomelatine" title="Agomelatine">Agomelatine</a></li> <li><a href="/wiki/Atypical_antipsychotic" title="Atypical antipsychotic">Atypical antipsychotics</a> (e.g., <a href="/wiki/Amisulpride" title="Amisulpride">amisulpride</a>, <a href="/wiki/Aripiprazole" title="Aripiprazole">aripiprazole</a>, <a href="/wiki/Asenapine" title="Asenapine">asenapine</a>, <a href="/wiki/Brexpiprazole" title="Brexpiprazole">brexpiprazole</a>, <a href="/wiki/Cariprazine" title="Cariprazine">cariprazine</a>, <a href="/wiki/Clozapine" title="Clozapine">clozapine</a>, <a href="/w/index.php?title=N-desalkylquetiapine&action=edit&redlink=1" class="new" title="N-desalkylquetiapine (page does not exist)">N-desalkylquetiapine (norquetiapine)</a>, <a href="/wiki/Desmethylclozapine" title="Desmethylclozapine">N-desmethylclozapine (norclozapine)</a>, <a href="/wiki/Olanzapine" title="Olanzapine">olanzapine</a>, <a href="/wiki/Pipamperone" title="Pipamperone">pipamperone</a>, <a href="/wiki/Quetiapine" title="Quetiapine">quetiapine</a>, <a href="/wiki/Risperidone" title="Risperidone">risperidone</a>, <a href="/wiki/Ziprasidone" title="Ziprasidone">ziprasidone</a>)</li> <li><a href="/wiki/Cyproheptadine" title="Cyproheptadine">Cyproheptadine</a></li> <li><a href="/wiki/EGIS-7625" title="EGIS-7625">EGIS-7625</a></li> <li><a href="/wiki/Ergoline" title="Ergoline">Ergolines</a> (e.g., <a href="/wiki/Amesergide" title="Amesergide">amesergide</a>, <a href="/wiki/Bromocriptine" title="Bromocriptine">bromocriptine</a>, <a href="/wiki/Lisuride" title="Lisuride">lisuride</a>, <a href="/w/index.php?title=LY-53857&action=edit&redlink=1" class="new" title="LY-53857 (page does not exist)">LY-53857</a>, <a href="/wiki/LY-272,015" title="LY-272,015">LY-272015</a>, <a href="/wiki/Mesulergine" title="Mesulergine">mesulergine</a>)</li> <li><a href="/wiki/Ketanserin" title="Ketanserin">Ketanserin</a></li> <li><a href="/wiki/LY-393558" title="LY-393558">LY-393558</a></li> <li><a href="/wiki/Meta-Chlorophenylpiperazine" title="Meta-Chlorophenylpiperazine">mCPP</a></li> <li><a href="/wiki/Metadoxine" title="Metadoxine">Metadoxine</a></li> <li><a href="/wiki/Metitepine" title="Metitepine">Metitepine (methiothepin)</a></li> <li><a href="/wiki/Pirenperone" title="Pirenperone">Pirenperone</a></li> <li><a href="/wiki/Pizotifen" title="Pizotifen">Pizotifen</a></li> <li><a href="/wiki/Propranolol" title="Propranolol">Propranolol</a></li> <li><a href="/wiki/PRX-08066" title="PRX-08066">PRX-08066</a></li> <li><a href="/wiki/Rauwolscine" title="Rauwolscine">Rauwolscine</a></li> <li><a href="/wiki/Ritanserin" title="Ritanserin">Ritanserin</a></li> <li><a href="/wiki/RS-127445" title="RS-127445">RS-127445</a></li> <li><a href="/wiki/Sarpogrelate" title="Sarpogrelate">Sarpogrelate</a></li> <li><a href="/wiki/SB-200646" title="SB-200646">SB-200646</a></li> <li><a href="/wiki/SB-204741" title="SB-204741">SB-204741</a></li> <li><a href="/wiki/SB-206553" title="SB-206553">SB-206553</a></li> <li><a href="/wiki/SB-215505" title="SB-215505">SB-215505</a></li> <li><a href="/w/index.php?title=SB-221284&action=edit&redlink=1" class="new" title="SB-221284 (page does not exist)">SB-221284</a></li> <li><a href="/wiki/SB-228357" title="SB-228357">SB-228357</a></li> <li><a href="/wiki/SDZ_SER-082" title="SDZ SER-082">SDZ SER-082</a></li> <li><a href="/wiki/Tegaserod" title="Tegaserod">Tegaserod</a></li> <li><a href="/wiki/Tetracyclic_antidepressant" title="Tetracyclic antidepressant">Tetracyclic antidepressants</a> (e.g., <a href="/wiki/Amoxapine" title="Amoxapine">amoxapine</a>, <a href="/wiki/Mianserin" title="Mianserin">mianserin</a>, <a href="/wiki/Mirtazapine" title="Mirtazapine">mirtazapine</a>)</li> <li><a href="/wiki/Trazodone" title="Trazodone">Trazodone</a></li> <li><a href="/wiki/Typical_antipsychotic" title="Typical antipsychotic">Typical antipsychotics</a> (e.g., <a href="/wiki/Chlorpromazine" title="Chlorpromazine">chlorpromazine</a>)</li> <li><a href="/wiki/TIK-301" title="TIK-301">TIK-301</a></li> <li><a href="/wiki/Yohimbine" title="Yohimbine">Yohimbine</a></li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i>Unknown/unsorted:</i> <a href="/wiki/Ergoline" title="Ergoline">Ergolines</a> (e.g., <a href="/wiki/Ergometrine" title="Ergometrine">ergometrine (ergonovine)</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/5-HT2C_receptor" title="5-HT2C receptor">5-HT<sub>2C</sub></a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><td colspan="2" class="navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i>Agonists:</i> <a href="/wiki/2C_(psychedelics)" title="2C (psychedelics)">2Cs</a> (e.g., <a href="/wiki/2C-B" title="2C-B">2C-B</a>, <a href="/wiki/2C-E" title="2C-E">2C-E</a>, <a href="/wiki/2C-I" title="2C-I">2C-I</a>, <a href="/wiki/2C-T-2" title="2C-T-2">2C-T-2</a>, <a href="/wiki/2C-T-7" title="2C-T-7">2C-T-7</a>, <a href="/wiki/2C-T-21" title="2C-T-21">2C-T-21</a>)</li> <li><a href="/wiki/5-Methoxytryptamine" title="5-Methoxytryptamine">5-Methoxytryptamines</a> (<a href="/wiki/5-MeO-DET" title="5-MeO-DET">5-MeO-DET</a>, <a href="/wiki/5-Methoxy-N,N-diisopropyltryptamine" class="mw-redirect" title="5-Methoxy-N,N-diisopropyltryptamine">5-MeO-DiPT</a>, <a href="/wiki/5-MeO-DMT" title="5-MeO-DMT">5-MeO-DMT</a>, <a href="/wiki/5-MeO-DPT" title="5-MeO-DPT">5-MeO-DPT</a>, <a href="/wiki/5-Methoxytryptamine" title="5-Methoxytryptamine">5-MT</a>)</li> <li><a href="/wiki/Substituted_alpha-alkyltryptamine" class="mw-redirect" title="Substituted alpha-alkyltryptamine">α-Alkyltryptamines</a> (e.g., <a href="/wiki/5-Chloro-%CE%B1MT" title="5-Chloro-αMT">5-Cl-αMT</a>, <a href="/wiki/5-Fluoro-AMT" title="5-Fluoro-AMT">5-Fl-αMT</a>, <a href="/wiki/5-MeO-AET" title="5-MeO-AET">5-MeO-αET</a>, <a href="/wiki/5-MeO-aMT" title="5-MeO-aMT">5-MeO-αMT</a>, <a href="/wiki/Alpha-Methylserotonin" class="mw-redirect" title="Alpha-Methylserotonin">α-Me-5-HT</a>, <a href="/wiki/Alpha-Ethyltryptamine" class="mw-redirect" title="Alpha-Ethyltryptamine">αET</a>, <a href="/wiki/Alpha-Methyltryptamine" class="mw-redirect" title="Alpha-Methyltryptamine">αMT</a>)</li> <li><a href="/wiki/A-372159" title="A-372159">A-372159</a></li> <li><a href="/wiki/AL-38022A" title="AL-38022A">AL-38022A</a></li> <li><a href="/wiki/Alstonine" title="Alstonine">Alstonine</a></li> <li><a href="/wiki/CP-809101" title="CP-809101">CP-809101</a></li> <li><a href="/wiki/Dimemebfe" title="Dimemebfe">Dimemebfe</a></li> <li><a href="/wiki/DOx" title="DOx">DOx</a> (e.g., <a href="/wiki/2,5-Dimethoxy-4-bromoamphetamine" title="2,5-Dimethoxy-4-bromoamphetamine">DOB</a>, <a href="/wiki/2,5-Dimethoxy-4-chloroamphetamine" title="2,5-Dimethoxy-4-chloroamphetamine">DOC</a>, <a href="/wiki/2,5-Dimethoxy-4-iodoamphetamine" title="2,5-Dimethoxy-4-iodoamphetamine">DOI</a>, <a href="/wiki/2,5-Dimethoxy-4-methylamphetamine" title="2,5-Dimethoxy-4-methylamphetamine">DOM</a>)</li> <li><a href="/wiki/Ergoline" title="Ergoline">Ergolines</a> (e.g., <a href="/wiki/ALD-52" title="ALD-52">ALD-52</a>, <a href="/wiki/Cabergoline" title="Cabergoline">cabergoline</a>, <a href="/wiki/Dihydroergotamine" title="Dihydroergotamine">dihydroergotamine</a>, <a href="/wiki/Ergine" title="Ergine">ergine (LSA)</a>, <a href="/wiki/Ergotamine" title="Ergotamine">ergotamine</a>, <a href="/wiki/Lisuride" title="Lisuride">lisuride</a>, <a href="/wiki/Lysergic_acid_2,4-dimethylazetidide" title="Lysergic acid 2,4-dimethylazetidide">LA-SS-Az</a>, <a href="/wiki/Lysergic_acid_2-butyl_amide" title="Lysergic acid 2-butyl amide">LSB</a>, <a href="/wiki/LSD" title="LSD">LSD</a>, <a href="/wiki/LSD-Pip" title="LSD-Pip">LSD-Pip</a>, <a href="/wiki/Lysergic_acid_hydroxyethylamide" title="Lysergic acid hydroxyethylamide">LSH</a>, <a href="/wiki/Lysergic_acid_3-pentyl_amide" title="Lysergic acid 3-pentyl amide">LSP</a>, <a href="/wiki/Pergolide" title="Pergolide">pergolide</a>)</li> <li><a href="/wiki/Flumexadol" title="Flumexadol">Flumexadol</a></li> <li><a href="/wiki/Lorcaserin" title="Lorcaserin">Lorcaserin</a></li> <li><a href="/wiki/Substituted_methylenedioxyphenethylamine" title="Substituted methylenedioxyphenethylamine">MDxx</a> (e.g., <a href="/wiki/3,4-Methylenedioxyamphetamine" title="3,4-Methylenedioxyamphetamine">MDA (tenamfetamine)</a>, <a href="/wiki/MDMA" title="MDMA">MDMA (midomafetamine)</a>, <a href="/wiki/3,4-Methylenedioxy-N-hydroxyamphetamine" title="3,4-Methylenedioxy-N-hydroxyamphetamine">MDOH</a>, <a href="/wiki/MMDA_(drug)" title="MMDA (drug)">MMDA</a>)</li> <li><a href="/wiki/MK-212" title="MK-212">MK-212</a></li> <li><a href="/wiki/ORG-12962" title="ORG-12962">ORG-12962</a></li> <li><a href="/wiki/ORG-37684" title="ORG-37684">ORG-37684</a></li> <li><a href="/wiki/Oxaflozane" title="Oxaflozane">Oxaflozane</a></li> <li><a href="/wiki/PHA-57378" title="PHA-57378">PHA-57378</a></li> <li><a href="/wiki/Substituted_phenethylamine" title="Substituted phenethylamine">Phenethylamines</a> (e.g., <a href="/wiki/Lophophine" title="Lophophine">lophophine</a>, <a href="/wiki/Mescaline" title="Mescaline">mescaline</a>)</li> <li><a href="/wiki/Piperazine" title="Piperazine">Piperazines</a> (e.g., <a href="/wiki/Aripiprazole" title="Aripiprazole">aripiprazole</a>, <a href="/wiki/Benzylpiperazine" title="Benzylpiperazine">BZP</a>, <a href="/wiki/Meta-Chlorophenylpiperazine" title="Meta-Chlorophenylpiperazine">mCPP</a>, <a href="/wiki/Quipazine" title="Quipazine">quipazine</a>, <a href="/wiki/Trifluoromethylphenylpiperazine" title="Trifluoromethylphenylpiperazine">TFMPP</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/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/Serotonin" title="Serotonin">Serotonin (5-HT)</a></li> <li><a href="/wiki/Substituted_tryptamine" title="Substituted tryptamine">Tryptamines</a> (e.g., <a href="/wiki/5-Benzyloxytryptamine" title="5-Benzyloxytryptamine">5-BT</a>, <a href="/wiki/5-Carboxamidotryptamine" title="5-Carboxamidotryptamine">5-CT</a>, <a href="/wiki/Bufotenin" title="Bufotenin">bufotenin</a>, <a href="/wiki/Diethyltryptamine" title="Diethyltryptamine">DET</a>, <a href="/wiki/Diisopropyltryptamine" class="mw-redirect" title="Diisopropyltryptamine">DiPT</a>, <a href="/wiki/N,N-Dimethyltryptamine" title="N,N-Dimethyltryptamine">DMT</a>, <a href="/wiki/Dipropyltryptamine" title="Dipropyltryptamine">DPT</a>, <a href="/wiki/Psilocin" title="Psilocin">psilocin</a>, <a href="/wiki/Psilocybin" title="Psilocybin">psilocybin</a>, <a href="/wiki/Tryptamine" title="Tryptamine">tryptamine</a>)</li> <li><a href="/wiki/Vabicaserin" title="Vabicaserin">Vabicaserin</a></li> <li><a href="/wiki/WAY-629" title="WAY-629">WAY-629</a></li> <li><a href="/wiki/WAY-161503" title="WAY-161503">WAY-161503</a></li> <li><a href="/wiki/YM-348" title="YM-348">YM-348</a></li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i>Antagonists:</i> <a href="/wiki/Adatanserin" title="Adatanserin">Adatanserin</a></li> <li><a href="/wiki/Agomelatine" title="Agomelatine">Agomelatine</a></li> <li><a href="/wiki/Atypical_antipsychotic" title="Atypical antipsychotic">Atypical antipsychotics</a> (e.g., <a href="/wiki/Asenapine" title="Asenapine">asenapine</a>, <a href="/wiki/Clorotepine" title="Clorotepine">clorotepine</a>, <a href="/wiki/Clozapine" title="Clozapine">clozapine</a>, <a href="/wiki/Fluperlapine" title="Fluperlapine">fluperlapine</a>, <a href="/wiki/Iloperidone" title="Iloperidone">iloperidone</a>, <a href="/wiki/Melperone" title="Melperone">melperone</a>, <a href="/wiki/Olanzapine" title="Olanzapine">olanzapine</a>, <a href="/wiki/Paliperidone" title="Paliperidone">paliperidone</a>, <a href="/wiki/Quetiapine" title="Quetiapine">quetiapine</a>, <a href="/wiki/Risperidone" title="Risperidone">risperidone</a>, <a href="/wiki/Sertindole" title="Sertindole">sertindole</a>, <a href="/wiki/Ziprasidone" title="Ziprasidone">ziprasidone</a>, <a href="/wiki/Zotepine" title="Zotepine">zotepine</a>)</li> <li><a href="/wiki/Captodiame" title="Captodiame">Captodiame</a></li> <li><a href="/wiki/6-Chloro-5-ethoxy-N-(pyridin-2-yl)indoline-1-carboxamide" title="6-Chloro-5-ethoxy-N-(pyridin-2-yl)indoline-1-carboxamide">CEPC</a></li> <li><a href="/wiki/Cinanserin" title="Cinanserin">Cinanserin</a></li> <li><a href="/wiki/Cyproheptadine" title="Cyproheptadine">Cyproheptadine</a></li> <li><a href="/wiki/Deramciclane" title="Deramciclane">Deramciclane</a></li> <li><a href="/wiki/Desmetramadol" title="Desmetramadol">Desmetramadol</a></li> <li><a href="/wiki/Dotarizine" title="Dotarizine">Dotarizine</a></li> <li><a href="/wiki/Eltoprazine" title="Eltoprazine">Eltoprazine</a></li> <li><a href="/wiki/Ergoline" title="Ergoline">Ergolines</a> (e.g., <a href="/wiki/Amesergide" title="Amesergide">amesergide</a>, <a href="/wiki/Bromocriptine" title="Bromocriptine">bromocriptine</a>, <a href="/w/index.php?title=LY-53857&action=edit&redlink=1" class="new" title="LY-53857 (page does not exist)">LY-53857</a>, <a href="/wiki/LY-215,840" title="LY-215,840">LY-215,840</a>, <a href="/wiki/Mesulergine" title="Mesulergine">mesulergine</a>, <a href="/wiki/Metergoline" title="Metergoline">metergoline</a>, <a href="/wiki/Methysergide" title="Methysergide">methysergide</a>, <a href="/wiki/Sergolexole" title="Sergolexole">sergolexole</a>)</li> <li><a href="/wiki/Etoperidone" title="Etoperidone">Etoperidone</a></li> <li><a href="/wiki/Fluoxetine" title="Fluoxetine">Fluoxetine</a></li> <li><a href="/w/index.php?title=FR-260010&action=edit&redlink=1" class="new" title="FR-260010 (page does not exist)">FR-260010</a></li> <li><a href="/w/index.php?title=Irindalone&action=edit&redlink=1" class="new" title="Irindalone (page does not exist)">Irindalone</a></li> <li><a href="/wiki/Ketanserin" title="Ketanserin">Ketanserin</a></li> <li><a href="/wiki/Ketotifen" title="Ketotifen">Ketotifen</a></li> <li><a href="/wiki/Latrepirdine" title="Latrepirdine">Latrepirdine (dimebolin)</a></li> <li><a href="/wiki/Medifoxamine" title="Medifoxamine">Medifoxamine</a></li> <li><a href="/wiki/Metitepine" title="Metitepine">Metitepine (methiothepin)</a></li> <li><a href="/wiki/Nefazodone" title="Nefazodone">Nefazodone</a></li> <li><a href="/wiki/Pirenperone" title="Pirenperone">Pirenperone</a></li> <li><a href="/wiki/Pizotifen" title="Pizotifen">Pizotifen</a></li> <li><a href="/wiki/Propranolol" title="Propranolol">Propranolol</a></li> <li><a href="/wiki/Ritanserin" title="Ritanserin">Ritanserin</a></li> <li><a href="/wiki/RS-102221" title="RS-102221">RS-102221</a></li> <li><a href="/wiki/S-14671" title="S-14671">S-14671</a></li> <li><a href="/wiki/SB-200646" title="SB-200646">SB-200646</a></li> <li><a href="/wiki/SB-206553" title="SB-206553">SB-206553</a></li> <li><a href="/w/index.php?title=SB-221284&action=edit&redlink=1" class="new" title="SB-221284 (page does not exist)">SB-221284</a></li> <li><a href="/wiki/SB-228357" title="SB-228357">SB-228357</a></li> <li><a href="/wiki/SB-242084" title="SB-242084">SB-242084</a></li> <li><a href="/wiki/SB-243213" title="SB-243213">SB-243213</a></li> <li><a href="/wiki/SDZ_SER-082" title="SDZ SER-082">SDZ SER-082</a></li> <li><a href="/wiki/Tedatioxetine" title="Tedatioxetine">Tedatioxetine</a></li> <li><a href="/wiki/Tetracyclic_antidepressant" title="Tetracyclic antidepressant">Tetracyclic antidepressants</a> (e.g., <a href="/wiki/Amoxapine" title="Amoxapine">amoxapine</a>, <a href="/wiki/Aptazapine" title="Aptazapine">aptazapine</a>, <a href="/wiki/Esmirtazapine" title="Esmirtazapine">esmirtazapine</a>, <a href="/wiki/Maprotiline" title="Maprotiline">maprotiline</a>, <a href="/wiki/Mianserin" title="Mianserin">mianserin</a>, <a href="/wiki/Mirtazapine" title="Mirtazapine">mirtazapine</a>)</li> <li><a href="/wiki/TIK-301" title="TIK-301">TIK-301</a></li> <li><a href="/wiki/Tramadol" title="Tramadol">Tramadol</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/Nortriptyline" title="Nortriptyline">nortriptyline</a>)</li> <li><a href="/wiki/Typical_antipsychotic" title="Typical antipsychotic">Typical antipsychotics</a> (e.g., <a href="/wiki/Chlorpromazine" title="Chlorpromazine">chlorpromazine</a>, <a href="/wiki/Loxapine" title="Loxapine">loxapine</a>, <a href="/wiki/Pimozide" title="Pimozide">pimozide</a>, <a href="/wiki/Pipamperone" title="Pipamperone">pipamperone</a>, <a href="/wiki/Thioridazine" title="Thioridazine">thioridazine</a>)</li> <li><a href="/wiki/Xylamidine" title="Xylamidine">Xylamidine</a></li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i>Unknown/unsorted:</i> <a href="/wiki/Efavirenz" title="Efavirenz">Efavirenz</a></li> <li><a href="/wiki/Ergoline" title="Ergoline">Ergolines</a> (e.g., <a href="/wiki/Ergometrine" title="Ergometrine">ergometrine (ergonovine)</a>, <a href="/wiki/Methylergometrine" title="Methylergometrine">methylergometrine (methylergonovine)</a>)</li></ul> </div></td></tr></tbody></table><div></div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/5-HT3_receptor" title="5-HT3 receptor">5-HT<sub>3</sub></a><sub>–<a href="/wiki/5-HT7_receptor" title="5-HT7 receptor">7</a></sub></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/5-HT3_receptor" title="5-HT3 receptor">5-HT<sub>3</sub></a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><td colspan="2" class="navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i>Agonists:</i> <a href="/wiki/Alcohol_(chemistry)" title="Alcohol (chemistry)">Alcohols</a> (e.g., <a href="/wiki/N-Butanol" class="mw-redirect" title="N-Butanol">butanol</a>, <a href="/wiki/Alcohol_(drug)" title="Alcohol (drug)">ethanol (alcohol)</a>, <a href="/wiki/2,2,2-Trichloroethanol" title="2,2,2-Trichloroethanol">trichloroethanol</a>)</li> <li><a href="/wiki/Chlorophenylbiguanide" title="Chlorophenylbiguanide">m-CPBG</a></li> <li><a href="/wiki/Phenylbiguanide" title="Phenylbiguanide">Phenylbiguanide</a></li> <li><a href="/wiki/Piperazine" title="Piperazine">Piperazines</a> (e.g., <a href="/wiki/Benzylpiperazine" title="Benzylpiperazine">BZP</a>, <a href="/wiki/Meta-Chlorophenylpiperazine" title="Meta-Chlorophenylpiperazine">mCPP</a>, <a href="/wiki/Quipazine" title="Quipazine">quipazine</a>)</li> <li><a href="/wiki/RS-56812" title="RS-56812">RS-56812</a></li> <li><a href="/wiki/Serotonin" title="Serotonin">Serotonin (5-HT)</a></li> <li><a href="/wiki/SR-57227" title="SR-57227">SR-57227</a></li> <li><a href="/w/index.php?title=SR-57227A&action=edit&redlink=1" class="new" title="SR-57227A (page does not exist)">SR-57227A</a></li> <li><a href="/wiki/Substituted_tryptamine" title="Substituted tryptamine">Tryptamines</a> (e.g., <a href="/wiki/2-Methyl-5-hydroxytryptamine" title="2-Methyl-5-hydroxytryptamine">2-Me-5-HT</a>, <a href="/wiki/5-Carboxamidotryptamine" title="5-Carboxamidotryptamine">5-CT</a>, <a href="/wiki/Bufotenidine" title="Bufotenidine">bufotenidine (5-HTQ)</a>)</li> <li><a href="/wiki/Inhalational_anaesthetic" class="mw-redirect" title="Inhalational anaesthetic">Volatiles/gases</a> (e.g., <a href="/wiki/Halothane" title="Halothane">halothane</a>, <a href="/wiki/Isoflurane" title="Isoflurane">isoflurane</a>, <a href="/wiki/Toluene" title="Toluene">toluene</a>, <a href="/wiki/1,1,1-Trichloroethane" title="1,1,1-Trichloroethane">trichloroethane</a>)</li> <li><a href="/wiki/YM-31636" title="YM-31636">YM-31636</a></li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i>Antagonists:</i> <a href="/wiki/Alosetron" title="Alosetron">Alosetron</a></li> <li><a href="/wiki/Anpirtoline" title="Anpirtoline">Anpirtoline</a></li> <li><a href="/w/index.php?title=Arazasetron&action=edit&redlink=1" class="new" title="Arazasetron (page does not exist)">Arazasetron</a></li> <li><a href="/wiki/AS-8112" title="AS-8112">AS-8112</a></li> <li><a href="/wiki/Atypical_antipsychotic" title="Atypical antipsychotic">Atypical antipsychotics</a> (e.g., <a href="/wiki/Clozapine" title="Clozapine">clozapine</a>, <a href="/wiki/Olanzapine" title="Olanzapine">olanzapine</a>, <a href="/wiki/Quetiapine" title="Quetiapine">quetiapine</a>)</li> <li><a href="/wiki/Azasetron" title="Azasetron">Azasetron</a></li> <li><a href="/wiki/Batanopride" title="Batanopride">Batanopride</a></li> <li><a href="/wiki/Bemesetron" title="Bemesetron">Bemesetron (MDL-72222)</a></li> <li><a href="/wiki/Bupropion" title="Bupropion">Bupropion</a></li> <li><a href="/wiki/Cilansetron" title="Cilansetron">Cilansetron</a></li> <li><a href="/wiki/CSP-2503" title="CSP-2503">CSP-2503</a></li> <li><a href="/wiki/Dazopride" title="Dazopride">Dazopride</a></li> <li><a href="/wiki/Dolasetron" title="Dolasetron">Dolasetron</a></li> <li><a href="/wiki/Galanolactone" title="Galanolactone">Galanolactone</a></li> <li><a href="/wiki/Granisetron" title="Granisetron">Granisetron</a></li> <li><a href="/wiki/Hydroxybupropion" title="Hydroxybupropion">Hydroxybupropion</a></li> <li><a href="/wiki/Lerisetron" title="Lerisetron">Lerisetron</a></li> <li><a href="/wiki/Memantine" title="Memantine">Memantine</a></li> <li><a href="/wiki/Ondansetron" title="Ondansetron">Ondansetron</a></li> <li><a href="/wiki/Palonosetron" title="Palonosetron">Palonosetron</a></li> <li><a href="/wiki/Ramosetron" title="Ramosetron">Ramosetron</a></li> <li><a href="/wiki/Renzapride" title="Renzapride">Renzapride</a></li> <li><a href="/wiki/Ricasetron" title="Ricasetron">Ricasetron</a></li> <li><a href="/wiki/Tedatioxetine" title="Tedatioxetine">Tedatioxetine</a></li> <li><a href="/wiki/Tetracyclic_antidepressant" title="Tetracyclic antidepressant">Tetracyclic antidepressants</a> (e.g., <a href="/wiki/Amoxapine" title="Amoxapine">amoxapine</a>, <a href="/wiki/Mianserin" title="Mianserin">mianserin</a>, <a href="/wiki/Mirtazapine" title="Mirtazapine">mirtazapine</a>)</li> <li><a href="/wiki/Thujone" title="Thujone">Thujone</a></li> <li><a href="/wiki/Tropanserin" title="Tropanserin">Tropanserin</a></li> <li><a href="/wiki/Tropisetron" title="Tropisetron">Tropisetron</a></li> <li><a href="/wiki/Typical_antipsychotic" title="Typical antipsychotic">Typical antipsychotics</a> (e.g., <a href="/wiki/Loxapine" title="Loxapine">loxapine</a>)</li> <li><a href="/wiki/Inhalational_anaesthetic" class="mw-redirect" title="Inhalational anaesthetic">Volatiles/gases</a> (e.g., <a href="/wiki/Nitrous_oxide" title="Nitrous oxide">nitrous oxide</a>, <a href="/wiki/Sevoflurane" title="Sevoflurane">sevoflurane</a>, <a href="/wiki/Xenon" title="Xenon">xenon</a>)</li> <li><a href="/wiki/Vortioxetine" title="Vortioxetine">Vortioxetine</a></li> <li><a href="/wiki/Zacopride" title="Zacopride">Zacopride</a></li> <li><a href="/wiki/Zatosetron" title="Zatosetron">Zatosetron</a></li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i>Unknown/unsorted:</i> <a href="/w/index.php?title=LY-53857&action=edit&redlink=1" class="new" title="LY-53857 (page does not exist)">LY-53857</a></li> <li><a href="/wiki/Piperazine" title="Piperazine">Piperazines</a> (e.g., <a href="/wiki/Naphthylpiperazine" title="Naphthylpiperazine">naphthylpiperazine</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/5-HT4_receptor" title="5-HT4 receptor">5-HT<sub>4</sub></a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><td colspan="2" class="navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i>Agonists:</i> <a href="/wiki/5-Methoxytryptamine" title="5-Methoxytryptamine">5-MT</a></li> <li><a href="/wiki/BIMU8" title="BIMU8">BIMU8</a></li> <li><a href="/wiki/Capeserod" title="Capeserod">Capeserod</a></li> <li><a href="/wiki/Cinitapride" title="Cinitapride">Cinitapride</a></li> <li><a href="/wiki/Cisapride" title="Cisapride">Cisapride</a></li> <li><a href="/wiki/CJ-033466" title="CJ-033466">CJ-033466</a></li> <li><a href="/wiki/Dazopride" title="Dazopride">Dazopride</a></li> <li><a href="/wiki/Metoclopramide" title="Metoclopramide">Metoclopramide</a></li> <li><a href="/w/index.php?title=Minesapride&action=edit&redlink=1" class="new" title="Minesapride (page does not exist)">Minesapride</a></li> <li><a href="/wiki/Mosapride" title="Mosapride">Mosapride</a></li> <li><a href="/wiki/Prucalopride" title="Prucalopride">Prucalopride</a></li> <li><a href="/wiki/PRX-03140" title="PRX-03140">PRX-03140</a></li> <li><a href="/wiki/Renzapride" title="Renzapride">Renzapride</a></li> <li><a href="/wiki/RS-67,333" title="RS-67,333">RS-67,333</a></li> <li><a href="/w/index.php?title=RS-67,506&action=edit&redlink=1" class="new" title="RS-67,506 (page does not exist)">RS-67,506</a></li> <li><a href="/wiki/Serotonin" title="Serotonin">Serotonin (5-HT)</a></li> <li><a href="/wiki/Tegaserod" title="Tegaserod">Tegaserod</a></li> <li><a href="/w/index.php?title=Usmarapride&action=edit&redlink=1" class="new" title="Usmarapride (page does not exist)">Usmarapride</a></li> <li><a href="/wiki/Velusetrag" title="Velusetrag">Velusetrag</a></li> <li><a href="/wiki/Zacopride" title="Zacopride">Zacopride</a></li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i>Antagonists:</i> <a href="/wiki/GR-113808" title="GR-113808">GR-113808</a></li> <li><a href="/w/index.php?title=GR-125487&action=edit&redlink=1" class="new" title="GR-125487 (page does not exist)">GR-125487</a></li> <li><a href="/wiki/Lysine" title="Lysine">L-Lysine</a></li> <li><a href="/wiki/Piboserod" title="Piboserod">Piboserod</a></li> <li><a href="/w/index.php?title=RS-39604&action=edit&redlink=1" class="new" title="RS-39604 (page does not exist)">RS-39604</a></li> <li><a href="/w/index.php?title=RS-67532&action=edit&redlink=1" class="new" title="RS-67532 (page does not exist)">RS-67532</a></li> <li><a href="/w/index.php?title=SB-203186&action=edit&redlink=1" class="new" title="SB-203186 (page does not exist)">SB-203186</a></li> <li><a href="/wiki/SB-204070" title="SB-204070">SB-204070</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/5-HT5A_receptor" title="5-HT5A receptor">5-HT<sub>5A</sub></a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><td colspan="2" class="navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i>Agonists:</i> <a href="/wiki/Ergoline" title="Ergoline">Ergolines</a> (e.g., <a href="/wiki/2-Bromo-LSD" title="2-Bromo-LSD">2-Br-LSD (BOL-148)</a>, <a href="/wiki/Ergotamine" title="Ergotamine">ergotamine</a>, <a href="/wiki/LSD" title="LSD">LSD</a>)</li> <li><a href="/wiki/Serotonin" title="Serotonin">Serotonin (5-HT)</a></li> <li><a href="/wiki/Substituted_tryptamine" title="Substituted tryptamine">Tryptamines</a> (e.g., <a href="/wiki/5-Carboxamidotryptamine" title="5-Carboxamidotryptamine">5-CT</a>)</li> <li><a href="/wiki/Valerenic_acid" title="Valerenic acid">Valerenic acid</a></li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i>Antagonists:</i> <a href="/wiki/Asenapine" title="Asenapine">Asenapine</a></li> <li><a href="/wiki/Latrepirdine" title="Latrepirdine">Latrepirdine (dimebolin)</a></li> <li><a href="/wiki/Metitepine" title="Metitepine">Metitepine (methiothepin)</a></li> <li><a href="/wiki/Ritanserin" title="Ritanserin">Ritanserin</a></li> <li><a href="/wiki/SB-699551" title="SB-699551">SB-699551</a></li></ul> <ul><li><i>Unknown/unsorted:</i> <a href="/wiki/Ergoline" title="Ergoline">Ergolines</a> (e.g., <a href="/wiki/Metergoline" title="Metergoline">metergoline</a>, <a href="/wiki/Methysergide" title="Methysergide">methysergide</a>)</li> <li><a href="/wiki/Piperazine" title="Piperazine">Piperazines</a> (e.g., <a href="/wiki/Naphthylpiperazine" title="Naphthylpiperazine">naphthylpiperazine</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/5-HT6_receptor" title="5-HT6 receptor">5-HT<sub>6</sub></a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><td colspan="2" class="navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i>Agonists:</i> <a href="/wiki/Ergoline" title="Ergoline">Ergolines</a> (e.g., <a href="/wiki/Dihydroergocryptine" title="Dihydroergocryptine">dihydroergocryptine</a>, <a href="/wiki/Dihydroergotamine" title="Dihydroergotamine">dihydroergotamine</a>, <a href="/wiki/Ergotamine" title="Ergotamine">ergotamine</a>, <a href="/wiki/Lisuride" title="Lisuride">lisuride</a>, <a href="/wiki/LSD" title="LSD">LSD</a>, <a href="/wiki/Mesulergine" title="Mesulergine">mesulergine</a>, <a href="/wiki/Metergoline" title="Metergoline">metergoline</a>, <a href="/wiki/Methysergide" title="Methysergide">methysergide</a>)</li> <li><a href="/wiki/Hypidone" title="Hypidone">Hypidone</a></li> <li><a href="/wiki/Serotonin" title="Serotonin">Serotonin (5-HT)</a></li> <li><a href="/wiki/Substituted_tryptamine" title="Substituted tryptamine">Tryptamines</a> (e.g., <a href="/wiki/2-Methyl-5-hydroxytryptamine" title="2-Methyl-5-hydroxytryptamine">2-Me-5-HT</a>, <a href="/wiki/5-Benzyloxytryptamine" title="5-Benzyloxytryptamine">5-BT</a>, <a href="/wiki/5-Carboxamidotryptamine" title="5-Carboxamidotryptamine">5-CT</a>, <a href="/wiki/5-Methoxytryptamine" title="5-Methoxytryptamine">5-MT</a>, <a href="/wiki/Bufotenin" title="Bufotenin">Bufotenin</a>, <a href="/wiki/E-6801" title="E-6801">E-6801</a>, <a href="/wiki/E-6837" title="E-6837">E-6837</a>, <a href="/wiki/EMD-386088" title="EMD-386088">EMD-386088</a>, <a href="/wiki/EMDT" title="EMDT">EMDT</a>, <a href="/w/index.php?title=LY-586713&action=edit&redlink=1" class="new" title="LY-586713 (page does not exist)">LY-586713</a>, <a href="/w/index.php?title=N-Methyl-5-HT&action=edit&redlink=1" class="new" title="N-Methyl-5-HT (page does not exist)">N-Me-5-HT</a>, <a href="/wiki/ST-1936" title="ST-1936">ST-1936</a>, <a href="/wiki/Tryptamine" title="Tryptamine">tryptamine</a>)</li> <li><a href="/wiki/WAY-181187" title="WAY-181187">WAY-181187</a></li> <li><a href="/wiki/WAY-208466" title="WAY-208466">WAY-208466</a></li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i>Antagonists:</i> <a href="/w/index.php?title=ABT-354&action=edit&redlink=1" class="new" title="ABT-354 (page does not exist)">ABT-354</a></li> <li><a href="/wiki/Atypical_antipsychotic" title="Atypical antipsychotic">Atypical antipsychotics</a> (e.g., <a href="/wiki/Aripiprazole" title="Aripiprazole">aripiprazole</a>, <a href="/wiki/Asenapine" title="Asenapine">asenapine</a>, <a href="/wiki/Clorotepine" title="Clorotepine">clorotepine</a>, <a href="/wiki/Clozapine" title="Clozapine">clozapine</a>, <a href="/wiki/Fluperlapine" title="Fluperlapine">fluperlapine</a>, <a href="/wiki/Iloperidone" title="Iloperidone">iloperidone</a>, <a href="/wiki/Olanzapine" title="Olanzapine">olanzapine</a>, <a href="/wiki/Tiospirone" title="Tiospirone">tiospirone</a>)</li> <li><a href="/wiki/AVN-101" title="AVN-101">AVN-101</a></li> <li><a href="/wiki/AVN-211" title="AVN-211">AVN-211</a></li> <li><a href="/wiki/AVN-322" title="AVN-322">AVN-322</a></li> <li><a href="/wiki/AVN-397" title="AVN-397">AVN-397</a></li> <li><a href="/w/index.php?title=BGC20-760&action=edit&redlink=1" class="new" title="BGC20-760 (page does not exist)">BGC20-760</a></li> <li><a href="/w/index.php?title=BVT-5182&action=edit&redlink=1" class="new" title="BVT-5182 (page does not exist)">BVT-5182</a></li> <li><a href="/w/index.php?title=BVT-74316&action=edit&redlink=1" class="new" title="BVT-74316 (page does not exist)">BVT-74316</a></li> <li><a href="/wiki/Cerlapirdine" title="Cerlapirdine">Cerlapirdine</a></li> <li><a href="/wiki/EGIS-12,233" title="EGIS-12,233">EGIS-12,233</a></li> <li><a href="/w/index.php?title=GW-742457&action=edit&redlink=1" class="new" title="GW-742457 (page does not exist)">GW-742457</a></li> <li><a href="/wiki/Idalopirdine" title="Idalopirdine">Idalopirdine</a></li> <li><a href="/wiki/Ketanserin" title="Ketanserin">Ketanserin</a></li> <li><a href="/w/index.php?title=Landipirdine&action=edit&redlink=1" class="new" title="Landipirdine (page does not exist)">Landipirdine</a></li> <li><a href="/wiki/Latrepirdine" title="Latrepirdine">Latrepirdine (dimebolin)</a></li> <li><a href="/wiki/Masupirdine" title="Masupirdine">Masupirdine</a></li> <li><a href="/wiki/Metitepine" title="Metitepine">Metitepine (methiothepin)</a></li> <li><a href="/wiki/MS-245" title="MS-245">MS-245</a></li> <li><a href="/wiki/PRX-07034" title="PRX-07034">PRX-07034</a></li> <li><a href="/wiki/Ritanserin" title="Ritanserin">Ritanserin</a></li> <li><a href="/wiki/Ro_04-6790" title="Ro 04-6790">Ro 04-6790</a></li> <li><a href="/w/index.php?title=Ro_63-0563&action=edit&redlink=1" class="new" title="Ro 63-0563 (page does not exist)">Ro 63-0563</a></li> <li><a href="/wiki/SB-258585" title="SB-258585">SB-258585</a></li> <li><a href="/wiki/SB-271046" title="SB-271046">SB-271046</a></li> <li><a href="/wiki/SB-357134" title="SB-357134">SB-357134</a></li> <li><a href="/wiki/SB-399885" title="SB-399885">SB-399885</a></li> <li><a href="/wiki/Intepirdine" title="Intepirdine">SB-742457</a></li> <li><a href="/wiki/Tetracyclic_antidepressant" title="Tetracyclic antidepressant">Tetracyclic antidepressants</a> (e.g., <a href="/wiki/Amoxapine" title="Amoxapine">amoxapine</a>, <a href="/wiki/Mianserin" title="Mianserin">mianserin</a>)</li> <li><a href="/wiki/Tricyclic_antidepressant" title="Tricyclic antidepressant">Tricyclic antidepressants</a> (e.g., <a href="/wiki/Amitriptyline" title="Amitriptyline">amitriptyline</a>, <a href="/wiki/Clomipramine" title="Clomipramine">clomipramine</a>, <a href="/wiki/Doxepin" title="Doxepin">doxepin</a>, <a href="/wiki/Nortriptyline" title="Nortriptyline">nortriptyline</a>)</li> <li><a href="/wiki/Typical_antipsychotic" title="Typical antipsychotic">Typical antipsychotics</a> (e.g., <a href="/wiki/Chlorpromazine" title="Chlorpromazine">chlorpromazine</a>, <a href="/wiki/Loxapine" title="Loxapine">loxapine</a>)</li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i>Unknown/unsorted:</i> <a href="/wiki/Ergoline" title="Ergoline">Ergolines</a> (e.g., <a href="/wiki/2-Bromo-LSD" title="2-Bromo-LSD">2-Br-LSD (BOL-148)</a>, <a href="/wiki/Bromocriptine" title="Bromocriptine">bromocriptine</a>, <a href="/wiki/Lergotrile" title="Lergotrile">lergotrile</a>, <a href="/wiki/Pergolide" title="Pergolide">pergolide</a>)</li> <li><a href="/wiki/Piperazine" title="Piperazine">Piperazines</a> (e.g., <a href="/wiki/Naphthylpiperazine" title="Naphthylpiperazine">naphthylpiperazine</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/5-HT7_receptor" title="5-HT7 receptor">5-HT<sub>7</sub></a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><td colspan="2" class="navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i>Agonists:</i> <a href="/wiki/8-OH-DPAT" title="8-OH-DPAT">8-OH-DPAT</a></li> <li><a href="/wiki/AS-19_(drug)" title="AS-19 (drug)">AS-19</a></li> <li><a href="/wiki/Bifeprunox" title="Bifeprunox">Bifeprunox</a></li> <li><a href="/wiki/E-55888" title="E-55888">E-55888</a></li> <li><a href="/wiki/Ergoline" title="Ergoline">Ergolines</a> (e.g., <a href="/wiki/LSD" title="LSD">LSD</a>)</li> <li><a href="/wiki/LP-12" title="LP-12">LP-12</a></li> <li><a href="/wiki/LP-44" title="LP-44">LP-44</a></li> <li><a href="/wiki/LP-211" title="LP-211">LP-211</a></li> <li><a href="/wiki/RU-24,969" title="RU-24,969">RU-24,969</a></li> <li><a href="/wiki/Sarizotan" title="Sarizotan">Sarizotan</a></li> <li><a href="/wiki/Serotonin" title="Serotonin">Serotonin (5-HT)</a></li> <li><a href="/wiki/Triptan" title="Triptan">Triptans</a> (e.g., <a href="/wiki/Frovatriptan" title="Frovatriptan">frovatriptan</a>)</li> <li><a href="/wiki/Substituted_tryptamine" title="Substituted tryptamine">Tryptamines</a> (e.g., <a href="/wiki/5-Carboxamidotryptamine" title="5-Carboxamidotryptamine">5-CT</a>, <a href="/wiki/5-Methoxytryptamine" title="5-Methoxytryptamine">5-MT</a>, <a href="/wiki/Bufotenin" title="Bufotenin">bufotenin</a>, <a href="/wiki/N-Methylserotonin" title="N-Methylserotonin">N-Me-5-HT</a>)</li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i>Antagonists:</i> <a href="/wiki/Atypical_antipsychotic" title="Atypical antipsychotic">Atypical antipsychotics</a> (e.g., <a href="/wiki/Amisulpride" title="Amisulpride">amisulpride</a>, <a href="/wiki/Aripiprazole" title="Aripiprazole">aripiprazole</a>, <a href="/wiki/Asenapine" title="Asenapine">asenapine</a>, <a href="/wiki/Brexpiprazole" title="Brexpiprazole">brexpiprazole</a>, <a href="/wiki/Clorotepine" title="Clorotepine">clorotepine</a>, <a href="/wiki/Clozapine" title="Clozapine">clozapine</a>, <a href="/wiki/Fluperlapine" title="Fluperlapine">fluperlapine</a>, <a href="/wiki/Olanzapine" title="Olanzapine">olanzapine</a>, <a href="/wiki/Risperidone" title="Risperidone">risperidone</a>, <a href="/wiki/Sertindole" title="Sertindole">sertindole</a>, <a href="/wiki/Tiospirone" title="Tiospirone">tiospirone</a>, <a href="/wiki/Ziprasidone" title="Ziprasidone">ziprasidone</a>, <a href="/wiki/Zotepine" title="Zotepine">zotepine</a>)</li> <li><a href="/wiki/Butaclamol" title="Butaclamol">Butaclamol</a></li> <li><a href="/wiki/DR-4485" title="DR-4485">DR-4485</a></li> <li><a href="/wiki/EGIS-12,233" title="EGIS-12,233">EGIS-12,233</a></li> <li><a href="/wiki/Ergoline" title="Ergoline">Ergolines</a> (e.g., <a href="/wiki/2-Bromo-LSD" title="2-Bromo-LSD">2-Br-LSD (BOL-148)</a>, <a href="/wiki/Amesergide" title="Amesergide">amesergide</a>, <a href="/wiki/Bromocriptine" title="Bromocriptine">bromocriptine</a>, <a href="/wiki/Cabergoline" title="Cabergoline">cabergoline</a>, <a href="/wiki/Dihydroergotamine" title="Dihydroergotamine">dihydroergotamine</a>, <a href="/wiki/Ergotamine" title="Ergotamine">ergotamine</a>, <a href="/w/index.php?title=LY-53857&action=edit&redlink=1" class="new" title="LY-53857 (page does not exist)">LY-53857</a>, <a href="/wiki/LY-215,840" title="LY-215,840">LY-215,840</a>, <a href="/wiki/Mesulergine" title="Mesulergine">mesulergine</a>, <a href="/wiki/Metergoline" title="Metergoline">metergoline</a>, <a href="/wiki/Methysergide" title="Methysergide">methysergide</a>, <a href="/wiki/Sergolexole" title="Sergolexole">sergolexole</a>)</li> <li><a href="/wiki/JNJ-18038683" title="JNJ-18038683">JNJ-18038683</a></li> <li><a href="/wiki/Ketanserin" title="Ketanserin">Ketanserin</a></li> <li><a href="/wiki/LY-215,840" title="LY-215,840">LY-215,840</a></li> <li><a href="/wiki/Metitepine" title="Metitepine">Metitepine (methiothepin)</a></li> <li><a href="/wiki/Ritanserin" title="Ritanserin">Ritanserin</a></li> <li><a href="/wiki/SB-258719" title="SB-258719">SB-258719</a></li> <li><a href="/w/index.php?title=SB-258741&action=edit&redlink=1" class="new" title="SB-258741 (page does not exist)">SB-258741</a></li> <li><a href="/wiki/SB-269970" title="SB-269970">SB-269970</a></li> <li><a href="/w/index.php?title=SB-656104&action=edit&redlink=1" class="new" title="SB-656104 (page does not exist)">SB-656104</a></li> <li><a href="/w/index.php?title=SB-656104A&action=edit&redlink=1" class="new" title="SB-656104A (page does not exist)">SB-656104A</a></li> <li><a href="/w/index.php?title=SB-691673&action=edit&redlink=1" class="new" title="SB-691673 (page does not exist)">SB-691673</a></li> <li><a href="/w/index.php?title=SLV-313&action=edit&redlink=1" class="new" title="SLV-313 (page does not exist)">SLV-313</a></li> <li><a href="/w/index.php?title=SLV-314&action=edit&redlink=1" class="new" title="SLV-314 (page does not exist)">SLV-314</a></li> <li><a href="/wiki/Spiperone" title="Spiperone">Spiperone</a></li> <li><a href="/w/index.php?title=SSR-181507&action=edit&redlink=1" class="new" title="SSR-181507 (page does not exist)">SSR-181507</a></li> <li><a href="/wiki/Tetracyclic_antidepressant" title="Tetracyclic antidepressant">Tetracyclic antidepressants</a> (e.g., <a href="/wiki/Amoxapine" title="Amoxapine">amoxapine</a>, <a href="/wiki/Maprotiline" title="Maprotiline">maprotiline</a>, <a href="/wiki/Mianserin" title="Mianserin">mianserin</a>, <a href="/wiki/Mirtazapine" title="Mirtazapine">mirtazapine</a>)</li> <li><a href="/wiki/Tricyclic_antidepressant" title="Tricyclic antidepressant">Tricyclic antidepressants</a> (e.g., <a href="/wiki/Amitriptyline" title="Amitriptyline">amitriptyline</a>, <a href="/wiki/Clomipramine" title="Clomipramine">clomipramine</a>, <a href="/wiki/Imipramine" title="Imipramine">imipramine</a>)</li> <li><a href="/wiki/Typical_antipsychotic" title="Typical antipsychotic">Typical antipsychotics</a> (e.g., <a href="/wiki/Acetophenazine" title="Acetophenazine">acetophenazine</a>, <a href="/wiki/Chlorpromazine" title="Chlorpromazine">chlorpromazine</a>, <a href="/wiki/Chlorprothixene" title="Chlorprothixene">chlorprothixene</a>, <a href="/wiki/Fluphenazine" title="Fluphenazine">fluphenazine</a>, <a href="/wiki/Loxapine" title="Loxapine">loxapine</a>, <a href="/wiki/Pimozide" title="Pimozide">pimozide</a>)</li> <li><a href="/wiki/Vortioxetine" title="Vortioxetine">Vortioxetine</a></li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i>Unknown/unsorted:</i> <a href="/wiki/Ergoline" title="Ergoline">Ergolines</a> (e.g., <a href="/wiki/Lisuride" title="Lisuride">lisuride</a>, <a href="/wiki/Pergolide" title="Pergolide">pergolide</a>)</li> <li><a href="/wiki/Piperazine" title="Piperazine">Piperazines</a> (e.g., <a href="/wiki/Naphthylpiperazine" title="Naphthylpiperazine">naphthylpiperazine</a>)</li></ul> </div></td></tr></tbody></table><div></div></td></tr></tbody></table><div></div></td></tr><tr><td class="navbox-abovebelow" colspan="2"><div> <ul><li><small><i><b>See also:</b> <a href="/wiki/Template:Receptor_modulators" title="Template:Receptor modulators">Receptor/signaling modulators</a></i></small></li> <li><small><i><a href="/wiki/Template:Adrenergic_receptor_modulators" title="Template:Adrenergic receptor modulators">Adrenergics</a></i></small></li> <li><small><i><a href="/wiki/Template:Dopamine_receptor_modulators" title="Template:Dopamine receptor modulators">Dopaminergics</a></i></small></li> <li><small><i><a href="/wiki/Template:Melatonin_receptor_modulators" title="Template:Melatonin receptor modulators">Melatonergics</a></i></small></li> <li><small><i><a href="/wiki/Template:Monoamine_reuptake_inhibitors" title="Template:Monoamine reuptake inhibitors">Monoamine reuptake inhibitors</a> and <a href="/wiki/Template:Monoamine_releasing_agents" title="Template:Monoamine releasing agents">releasing agents</a></i></small></li> <li><small><i><a href="/wiki/Template:Monoamine_metabolism_modulators" title="Template:Monoamine metabolism modulators">Monoamine metabolism modulators</a></i></small></li> <li><small><i><a href="/wiki/Template:Monoamine_neurotoxins" title="Template:Monoamine neurotoxins">Monoamine neurotoxins</a></i></small></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,<i>N</i>,<i>N</i>-TMT</a></li> <li><a href="/wiki/1-(2-Dimethylaminoethyl)dihydropyrano(3,2-e)indole" class="mw-redirect" title="1-(2-Dimethylaminoethyl)dihydropyrano(3,2-e)indole">4,5-DHP-DMT</a></li> <li><a href="/wiki/4-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,<i>N</i>,<i>N</i>-TMT</a></li> <li><a href="/wiki/5-MeO-DALT" title="5-MeO-DALT">5-MeO-DALT</a></li> <li><a href="/wiki/5-MeO-DBT" title="5-MeO-DBT">5-MeO-DBT</a></li> <li><a href="/wiki/5-MeO-DET" title="5-MeO-DET">5-MeO-DET</a></li> <li><a href="/wiki/5-Methoxy-N,N-diisopropyltryptamine" class="mw-redirect" title="5-Methoxy-N,N-diisopropyltryptamine">5-MeO-DiPT</a></li> <li><a href="/wiki/5-MeO-DMT" title="5-MeO-DMT">5-MeO-DMT</a></li> <li><a href="/wiki/5-MeO-DPT" title="5-MeO-DPT">5-MeO-DPT</a></li> <li><a href="/wiki/5-MeO-EiPT" title="5-MeO-EiPT">5-MeO-EiPT</a></li> <li><a href="/wiki/5-MeO-EPT" title="5-MeO-EPT">5-MeO-EPT</a></li> <li><a href="/wiki/5-MeO-MALT" title="5-MeO-MALT">5-MeO-MALT</a></li> <li><a href="/wiki/5-MeO-MET" title="5-MeO-MET">5-MeO-MET</a></li> <li><a href="/wiki/5-MeO-MiPT" title="5-MeO-MiPT">5-MeO-MiPT</a></li> <li><a href="/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-<small>L</small>-tryptophan)</a></li> <li><a href="/wiki/Bufotenidine" title="Bufotenidine">Bufotenidine (5-HTQ)</a></li> <li><a href="/wiki/Bufotenin" title="Bufotenin">Bufotenin (5-HO-DMT)</a></li> <li><a href="/wiki/Convolutindole_A" title="Convolutindole A">Convolutindole A</a></li> <li><a href="/wiki/CP-132,484" title="CP-132,484">CP-132,484</a></li> <li><a href="/wiki/DALT" title="DALT">DALT</a></li> <li><a href="/wiki/Dibutyltryptamine" title="Dibutyltryptamine">DBT</a></li> <li><a href="/wiki/Desformylflustrabromine" title="Desformylflustrabromine">Desformylflustrabromine</a></li> <li><a href="/wiki/Diethyltryptamine" title="Diethyltryptamine">DET</a></li> <li><a href="/wiki/Diisopropyltryptamine" class="mw-redirect" title="Diisopropyltryptamine">DiPT</a></li> <li><a href="/wiki/Dimethyltryptamine" class="mw-redirect" title="Dimethyltryptamine">DMT</a></li> <li><a href="/wiki/Dipropyltryptamine" title="Dipropyltryptamine">DPT</a></li> <li><a href="/wiki/E-6801" title="E-6801">E-6801</a></li> <li><a href="/wiki/E-6837" title="E-6837">E-6837</a></li> <li><a href="/wiki/Ethylisopropyltryptamine" title="Ethylisopropyltryptamine">EiPT</a></li> <li><a href="/wiki/EMDT" title="EMDT">EMDT</a></li> <li><a href="/wiki/Ethylpropyltryptamine" title="Ethylpropyltryptamine">EPT</a></li> <li><a href="/wiki/Ethocybin" title="Ethocybin">Ethocybin (4-PO-DET)</a></li> <li><a href="/wiki/FGIN-127" title="FGIN-127">FGIN-127</a></li> <li><a href="/wiki/FGIN-143" title="FGIN-143">FGIN-143</a></li> <li><a href="/wiki/FT-104" title="FT-104">FT-104</a></li> <li><a href="/wiki/HIOC" title="HIOC">HIOC</a></li> <li><a href="/wiki/Idalopirdine" title="Idalopirdine">Idalopirdine</a></li> <li><a href="/w/index.php?title=Indolylethylfentanyl&action=edit&redlink=1" class="new" title="Indolylethylfentanyl (page does not exist)">Indolylethylfentanyl</a></li> <li><a href="/wiki/Indorenate" title="Indorenate">Indorenate</a></li> <li><a href="/wiki/4-HO-DiPT" title="4-HO-DiPT">Iprocin (4-HO-DiPT)</a></li> <li><a href="/wiki/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"><i>N</i>-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"><i>O</i>-Pivalylbufotenine</a></li> <li><a href="/wiki/Oxypertine" title="Oxypertine">Oxypertine</a></li> <li><a href="/wiki/Propylisopropyltryptamine" title="Propylisopropyltryptamine">PiPT</a></li> <li><a href="/wiki/Psilacetin" class="mw-redirect" title="Psilacetin">Psilacetin (<i>O</i>-acetylpsilocin; 4-AcO-DMT)</a></li> <li><a href="/wiki/Psilocin" title="Psilocin">Psilocin (4-HO-DMT)</a></li> <li><a href="/wiki/Psilocybin" title="Psilocybin">Psilocybin (4-PO-DMT)</a></li> <li><a href="/wiki/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 class="mw-selflink selflink">Tryptophan</a></li> <li><a href="/wiki/Yuremamine" title="Yuremamine">Yuremamine</a></li> <li><a href="/w/index.php?title=Z2876442907&action=edit&redlink=1" class="new" title="Z2876442907 (page does not exist)">Z2876442907</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/N-Acetyltryptamine" title="N-Acetyltryptamine"><i>N</i>-Acetyltryptamines</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/2-Iodomelatonin" title="2-Iodomelatonin">2-Iodomelatonin</a></li> <li><a href="/w/index.php?title=2-Phenylmelatonin&action=edit&redlink=1" class="new" title="2-Phenylmelatonin (page does not exist)">2-Phenylmelatonin</a></li> <li><a href="/w/index.php?title=5-Methoxyluzindole&action=edit&redlink=1" class="new" title="5-Methoxyluzindole (page does not exist)">5-Methoxyluzindole</a></li> <li><a href="/w/index.php?title=6-Chloromelatonin&action=edit&redlink=1" class="new" title="6-Chloromelatonin (page does not exist)">6-Chloromelatonin</a></li> <li><a href="/w/index.php?title=6-Fluoromelatonin&action=edit&redlink=1" class="new" title="6-Fluoromelatonin (page does not exist)">6-Fluoromelatonin</a></li> <li><a href="/wiki/6-Hydroxymelatonin" title="6-Hydroxymelatonin">6-Hydroxymelatonin</a></li> <li><a href="/w/index.php?title=6-Methoxymelatonin&action=edit&redlink=1" class="new" title="6-Methoxymelatonin (page does not exist)">6-Methoxymelatonin</a></li> <li><a href="/w/index.php?title=6,7-Dichloro-2-methylmelatonin&action=edit&redlink=1" class="new" title="6,7-Dichloro-2-methylmelatonin (page does not exist)">6,7-Dichloro-2-methylmelatonin</a></li> <li><a href="/wiki/%CE%91-Methylmelatonin" title="Α-Methylmelatonin">α-Methylmelatonin</a></li> <li><a href="/wiki/Luzindole" title="Luzindole">Luzindole</a></li> <li><a href="/wiki/Melatonin" title="Melatonin">Melatonin</a></li> <li><a href="/wiki/N-Acetylserotonin" title="N-Acetylserotonin">Normelatonin (<i>N</i>-acetylserotonin; NAS)</a></li> <li><a href="/wiki/N-Acetyltryptamine" title="N-Acetyltryptamine"><i>N</i>-Acetyltryptamine</a></li> <li><a href="/w/index.php?title=N-Butanoylmelatonin&action=edit&redlink=1" class="new" title="N-Butanoylmelatonin (page does not exist)"><i>N</i>-Butanoylmelatonin</a></li> <li><a href="/w/index.php?title=N-Propionylmelatonin&action=edit&redlink=1" class="new" title="N-Propionylmelatonin (page does not exist)"><i>N</i>-Propionylmelatonin</a></li> <li><a href="/wiki/Piromelatine" title="Piromelatine">Piromelatine</a></li> <li><a href="/wiki/TIK-301" title="TIK-301">TIK-301</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/%CE%91-Alkyltryptamine" class="mw-redirect" title="Α-Alkyltryptamine">α-Alkyltryptamines</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/2,%CE%B1-Dimethyltryptamine" title="2,α-Dimethyltryptamine">2,α-DMT</a></li> <li><a href="/wiki/4-HO-%CE%B1MT" title="4-HO-αMT">4-HO-αMT</a></li> <li><a href="/wiki/4-HO-MPMI" title="4-HO-MPMI">4-HO-MPMI (lucigenol)</a></li> <li><a href="/wiki/4-Methyl-%CE%B1-ethyltryptamine" title="4-Methyl-α-ethyltryptamine">4-Me-αET</a></li> <li><a href="/wiki/4-Me-%CE%B1MT" class="mw-redirect" title="4-Me-αMT">4-Me-αMT</a></li> <li><a href="/wiki/5-Chloro-%CE%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,<i>N</i>,<i>N</i>-TMT</a></li> <li><a href="/wiki/5-MeO-AET" title="5-MeO-AET">5-MeO-αET </a></li> <li><a href="/wiki/5-MeO-aMT" title="5-MeO-aMT">5-MeO-αMT</a></li> <li><a href="/wiki/5-MeO-MPMI" title="5-MeO-MPMI">5-MeO-MPMI</a></li> <li><a href="/w/index.php?title=5-Methyl-AET&action=edit&redlink=1" class="new" title="5-Methyl-AET (page does not exist)">5-Methyl-αET</a></li> <li><a href="/wiki/6-Fluoro-AMT" title="6-Fluoro-AMT">6-Fluoro-αMT</a></li> <li><a href="/wiki/7-Chloro-AMT" title="7-Chloro-AMT">7-Chloro-αMT</a></li> <li><a href="/wiki/7-Methyl-%CE%B1-ethyltryptamine" title="7-Methyl-α-ethyltryptamine">7-Methyl-αET</a></li> <li><a href="/wiki/%CE%91-Methyl-5-hydroxytryptophan" title="Α-Methyl-5-hydroxytryptophan">α-Methyl-5-HTP</a></li> <li><a href="/wiki/%CE%91-Methylmelatonin" title="Α-Methylmelatonin">α-Methylmelatonin</a></li> <li><a href="/wiki/%CE%91-Methylserotonin" title="Α-Methylserotonin">α-Methylserotonin (5-HO-αMT)</a></li> <li><a href="/wiki/%CE%91-Methyltryptophan" title="Α-Methyltryptophan">α-Methyltryptophan (αMTP)</a></li> <li><a href="/wiki/Alpha,N-DMT" class="mw-redirect" title="Alpha,N-DMT">α,<i>N</i>-DMT (<i>N</i>-methyl-αMT)</a></li> <li><a href="/wiki/%CE%91,N,N-Trimethyltryptamine" title="Α,N,N-Trimethyltryptamine">α,<i>N</i>,<i>N</i>-TMT</a></li> <li><a href="/wiki/Alpha,N,O-TMS" class="mw-redirect" title="Alpha,N,O-TMS">α,<i>N</i>,<i>O</i>-TMS</a></li> <li><a href="/wiki/%CE%91-Ethyltryptamine" title="Α-Ethyltryptamine">αET (etryptamine)</a></li> <li><a href="/wiki/%CE%91-Methyltryptamine" title="Α-Methyltryptamine">αMT</a></li> <li><a href="/wiki/AL-37350A" title="AL-37350A">AL-37350A (4,5-DHP-αMT)</a></li> <li><a href="/wiki/BNC-210" title="BNC-210">BNC-210</a></li> <li><a href="/wiki/BW-723C86" title="BW-723C86">BW-723C86</a></li> <li><a href="/wiki/CP-135807" title="CP-135807">CP-135807</a></li> <li><a href="/wiki/Indolylpropylaminopentane" title="Indolylpropylaminopentane">IPAP (α,<i>N</i>-DPT)</a></li> <li><a href="/wiki/MPMI_(drug)" title="MPMI (drug)">MPMI</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Triptan" title="Triptan">Triptans</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Almotriptan" title="Almotriptan">Almotriptan</a></li> <li><a href="/wiki/Donitriptan" title="Donitriptan">Donitriptan</a></li> <li><a href="/wiki/Eletriptan" title="Eletriptan">Eletriptan</a></li> <li><a href="/wiki/Frovatriptan" title="Frovatriptan">Frovatriptan</a></li> <li><a href="/wiki/L-694247" title="L-694247">L-694247</a></li> <li><a href="/wiki/Rizatriptan" title="Rizatriptan">Rizatriptan</a></li> <li><a href="/wiki/Sumatriptan" title="Sumatriptan">Sumatriptan</a></li> <li><a href="/wiki/Zolmitriptan" title="Zolmitriptan">Zolmitriptan</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Cyclic_compound" title="Cyclic compound">Cyclized tryptamines</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Bay_R_1531" title="Bay R 1531">Bay R 1531</a></li> <li><a href="/wiki/Ciclindole" title="Ciclindole">Ciclindole</a></li> <li><a href="/wiki/Cyclic_3-hydroxymelatonin" title="Cyclic 3-hydroxymelatonin">Cyclic 3-OHM</a></li> <li><a href="/wiki/Ergoline" title="Ergoline">Ergolines</a> and <a href="/wiki/Lysergamide" class="mw-redirect" title="Lysergamide">lysergamides</a> (e.g., <a href="/wiki/Lysergic_acid_diethylamide" class="mw-redirect" title="Lysergic acid diethylamide">LSD</a>)</li> <li><a href="/wiki/Flucindole" title="Flucindole">Flucindole</a></li> <li><a href="/wiki/Harmala_alkaloid" title="Harmala alkaloid"><i>Harmala</i> alkaloids</a> and <a href="/wiki/%CE%92-carboline" class="mw-redirect" title="Β-carboline">β-carbolines</a> (e.g., <a href="/wiki/6-MeO-THH" title="6-MeO-THH">6-MeO-THH</a>, <a href="/wiki/9-Methyl-%CE%B2-carboline" title="9-Methyl-β-carboline">9-Me-BC</a>, <a href="/wiki/%CE%92-carboline" class="mw-redirect" title="Β-carboline">β-carboline (norharman)</a>, <a href="/wiki/Harmaline" title="Harmaline">harmaline</a>, <a href="/wiki/Harmalol" title="Harmalol">harmalol</a>, <a href="/wiki/Harmane" title="Harmane">harmane</a>, <a href="/wiki/Harmine" title="Harmine">harmine</a>, <a href="/wiki/Pinoline" title="Pinoline">pinoline</a>, <a href="/wiki/Tetrahydroharmine" title="Tetrahydroharmine">tetrahydroharmine</a>, <a href="/wiki/Tryptoline" title="Tryptoline">tryptoline</a>)</li> <li><a href="/wiki/Iboga-type_alkaloid" title="Iboga-type alkaloid"><i>Iboga</i> alkaloids</a> and related (e.g., <a href="/wiki/DM-506" title="DM-506">DM-506 (ibogaminalog)</a>, <a href="/wiki/Ibogaine" title="Ibogaine">ibogaine</a>, <a href="/wiki/Ibogamine" title="Ibogamine">ibogamine</a>, <a href="/wiki/Noribogaine" title="Noribogaine">noribogaine</a>, <a href="/wiki/Tabernanthalog" title="Tabernanthalog">tabernanthalog</a>, <a href="/wiki/Tabernanthine" title="Tabernanthine">tabernanthine</a>)</li> <li><a href="/wiki/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">(<i>R</i>)-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> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"></div><div role="navigation" class="navbox" aria-labelledby="Chocolate" style="padding:3px"><table class="nowraplinks mw-collapsible autocollapse navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2" style="background: #7B3F00; color: white;"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Chocolate" title="Template:Chocolate"><abbr title="View this template" style="color: white">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Chocolate" title="Template talk:Chocolate"><abbr title="Discuss this template" style="color: white">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Chocolate" title="Special:EditPage/Template:Chocolate"><abbr title="Edit this template" style="color: white">e</abbr></a></li></ul></div><div id="Chocolate" style="font-size:114%;margin:0 4em"><a href="/wiki/Chocolate" title="Chocolate"><span style="color:white">Chocolate</span></a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%;background: #7B3F00; color: white;"><a href="/wiki/Cocoa_bean" title="Cocoa bean"><span style="color:white">Cocoa bean</span></a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Chocolate_liquor" title="Chocolate liquor">Chocolate liquor</a></li> <li><a href="/wiki/Cocoa_butter" title="Cocoa butter">Cocoa butter</a></li> <li><a href="/wiki/Cocoa_solids" title="Cocoa solids">Cocoa solids</a></li> <li><i><a href="/wiki/Theobroma_cacao" title="Theobroma cacao">Theobroma cacao</a></i></li> <li><a href="/wiki/Types_of_cocoa_beans" title="Types of cocoa beans">Types</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;background: #7B3F00; color: white;">Components</th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Anandamide" title="Anandamide">Anandamide</a></li> <li><a href="/wiki/Caffeine" title="Caffeine">Caffeine</a></li> <li><a href="/wiki/Endorphins" title="Endorphins">Endorphins</a></li> <li><a href="/wiki/Enkephalin" title="Enkephalin">Enkephalin</a></li> <li><a href="/wiki/Flavan-3-ol" title="Flavan-3-ol">Flavan-3-ol</a></li> <li><a href="/wiki/Lecithin" title="Lecithin">Lecithin</a></li> <li><a href="/wiki/Phenethylamine" title="Phenethylamine">Phenethylamine</a></li> <li><a href="/wiki/Phenylalanine" title="Phenylalanine">Phenylalanine</a></li> <li><a href="/wiki/Salsolinol" title="Salsolinol">Salsolinol</a></li> <li><a href="/wiki/Tetramethylpyrazine" title="Tetramethylpyrazine">Tetramethylpyrazine</a></li> <li><a href="/wiki/Theobromine" title="Theobromine">Theobromine</a></li> <li><a href="/wiki/Theophylline" title="Theophylline">Theophylline</a></li> <li><a href="/wiki/Tryptamine" title="Tryptamine">Tryptamine</a></li> <li><a class="mw-selflink selflink">Tryptophan</a></li> <li><a href="/wiki/Tyramine" title="Tyramine">Tyramine</a></li> <li><a href="/wiki/Tyrosine" title="Tyrosine">Tyrosine</a></li> <li><a href="/wiki/Valeric_acid" title="Valeric acid">Valeric acid</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;background: #7B3F00; color: white;"><a href="/wiki/Types_of_chocolate" title="Types of chocolate"><span style="color:white">Types</span></a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Baking_chocolate" title="Baking chocolate">Baking</a></li> <li><a href="/wiki/Dark_chocolate" title="Dark chocolate">Dark</a></li> <li><a href="/wiki/Gianduja_(chocolate)" title="Gianduja (chocolate)">Gianduja</a></li> <li><a href="/wiki/Milk_chocolate" title="Milk chocolate">Milk</a></li> <li><a href="/wiki/Organic_chocolate" title="Organic chocolate">Organic</a></li> <li><a href="/wiki/Raw_chocolate" title="Raw chocolate">Raw</a></li> <li><a href="/wiki/Ruby_chocolate" title="Ruby chocolate">Ruby</a></li> <li><a href="/wiki/White_chocolate" title="White chocolate">White</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;background: #7B3F00; color: white;">Products</th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Caff%C3%A8_mocha" title="Caffè mocha">Caffè mocha</a></li> <li><a href="/wiki/Chocolate_bar" title="Chocolate bar">Chocolate bar</a> <ul><li><a href="/wiki/List_of_chocolate_bar_brands" title="List of chocolate bar brands">Brands</a></li></ul></li> <li><a href="/wiki/Chocolate_biscuit" title="Chocolate biscuit">Chocolate biscuit</a></li> <li><a href="/wiki/Chocolate_brownie" title="Chocolate brownie">Chocolate brownie</a></li> <li><a href="/wiki/Chocolate_cake" title="Chocolate cake">Chocolate cake</a></li> <li><a href="/wiki/Chocolate_chip_cookie" title="Chocolate chip cookie">Chocolate chip cookie</a></li> <li><a href="/wiki/Chocolate_chip" title="Chocolate chip">Chocolate chip</a></li> <li><a href="/wiki/Chocolate_coin" title="Chocolate coin">Chocolate coins</a></li> <li><a href="/wiki/Chocolate_crackles" title="Chocolate crackles">Chocolate crackles</a></li> <li><a href="/wiki/Chocolate_gravy" title="Chocolate gravy">Chocolate gravy</a></li> <li><a href="/wiki/Chocolate_ice_cream" title="Chocolate ice cream">Chocolate ice cream</a></li> <li><a href="/wiki/Chocolate_liqueur" title="Chocolate liqueur">Chocolate liqueur</a></li> <li><a href="/wiki/Chocolate_milk" title="Chocolate milk">Chocolate milk</a></li> <li><a href="/wiki/Chocolate_pudding" title="Chocolate pudding">Chocolate pudding</a></li> <li><a href="/wiki/Chocolate_spread" title="Chocolate spread">Chocolate spread</a></li> <li><a href="/wiki/Chocolate_syrup" title="Chocolate syrup">Chocolate syrup</a></li> <li><a href="/wiki/Chocolate_truffle" title="Chocolate truffle">Chocolate truffle</a></li> <li><a href="/wiki/Cioccolato_di_Modica" title="Cioccolato di Modica">Cioccolato di Modica</a></li> <li><a href="/wiki/Fudge" title="Fudge">Fudge</a></li> <li><a href="/wiki/Ganache" title="Ganache">Ganache</a></li> <li><a href="/wiki/Hot_chocolate" title="Hot chocolate">Hot chocolate</a></li> <li><a href="/wiki/List_of_chocolate_drinks" title="List of chocolate drinks">Other beverages</a></li> <li><a href="/wiki/List_of_chocolate-covered_foods" title="List of chocolate-covered foods">Chocolate-covered foods</a></li> <li><a href="/wiki/Mint_chocolate" title="Mint chocolate">Mint chocolate</a></li> <li><a href="/wiki/Mole_(sauce)" title="Mole (sauce)">Mole</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;background: #7B3F00; color: white;">Processes</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Aerated_chocolate" title="Aerated chocolate">Aerated chocolate</a></li> <li><a href="/wiki/Broma_process" title="Broma process">Broma process</a></li> <li><a href="/wiki/Conching" title="Conching">Conching</a></li> <li><a href="/wiki/Dutch_process_cocoa" title="Dutch process cocoa">Dutch process</a></li> <li><a href="/wiki/Enrober" title="Enrober">Enrober</a></li> <li><a href="/wiki/Sugar_crust" title="Sugar crust">Sugar crust</a></li> <li><a href="/wiki/Tempered_chocolate" title="Tempered chocolate">Tempering</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;background: #7B3F00; color: white;">Industry</th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Bean-to-bar" title="Bean-to-bar">Bean-to-bar</a> <ul><li><a href="/wiki/List_of_bean-to-bar_chocolate_manufacturers" title="List of bean-to-bar chocolate manufacturers">Manufacturers</a></li></ul></li> <li><a href="/wiki/Big_Chocolate" title="Big Chocolate">Big Chocolate</a></li> <li><a href="/wiki/Chocolaterie" title="Chocolaterie">Chocolaterie</a></li> <li><a href="/wiki/Chocolatier" title="Chocolatier">Chocolatier</a></li> <li><a href="/wiki/C%C3%B4te_d%27Ivoire%E2%80%93Ghana_Cocoa_Initiative" title="Côte d'Ivoire–Ghana Cocoa Initiative">Côte d'Ivoire–Ghana Cocoa Initiative</a></li> <li><i><a href="/wiki/The_Dark_Side_of_Chocolate" title="The Dark Side of Chocolate">The Dark Side of Chocolate</a></i></li> <li><a href="/wiki/Environmental_impact_of_cocoa_production" title="Environmental impact of cocoa production">Environmental impact</a></li> <li><a href="/wiki/European_Cocoa_and_Chocolate_Directive" title="European Cocoa and Chocolate Directive">European Cocoa and Chocolate Directive</a></li> <li><a href="/wiki/Fair_trade_cocoa" title="Fair trade cocoa">Fair trade cocoa</a> <ul><li><a href="/wiki/Child_labour_in_cocoa_production" title="Child labour in cocoa production">Child labour in cocoa production</a></li></ul></li> <li><a href="/wiki/Harkin%E2%80%93Engel_Protocol" title="Harkin–Engel Protocol">Harkin–Engel Protocol</a></li> <li><a href="/wiki/International_Cocoa_Organization" title="International Cocoa Organization">International Cocoa Organization</a></li> <li><a href="/wiki/International_Cocoa_Quarantine_Centre" title="International Cocoa Quarantine Centre">International Cocoa Quarantine Centre</a></li> <li><a href="/wiki/Chocolate_industry_in_the_Philippines" title="Chocolate industry in the Philippines">Philippine chocolate industry</a></li> <li><a href="/wiki/Cocoa_production_in_Ghana" title="Cocoa production in Ghana">Production in Ghana</a> <ul><li><a href="/wiki/Ghana_Cocoa_Board" title="Ghana Cocoa Board">Ghana Cocoa Board</a></li></ul></li> <li><a href="/wiki/Cocoa_production_in_Ivory_Coast" title="Cocoa production in Ivory Coast">Production in Ivory Coast</a></li> <li><a href="/wiki/Cocoa_production_in_Nigeria" title="Cocoa production in Nigeria">Production in Nigeria</a></li> <li><a href="/wiki/Cocoa_production_in_S%C3%A3o_Tom%C3%A9_and_Pr%C3%ADncipe" title="Cocoa production in São Tomé and Príncipe">Production in São Tomé and Príncipe</a></li> <li><a href="/wiki/World_Cocoa_Foundation" title="World Cocoa Foundation">World Cocoa Foundation</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;background: #7B3F00; color: white;">By country</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Belgian_chocolate" title="Belgian chocolate">Belgium</a></li> <li><a href="/wiki/French_chocolate" title="French chocolate">France</a></li> <li><a href="/wiki/Swiss_chocolate" title="Swiss chocolate">Switzerland</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;background: #7B3F00; color: white;">Other topics</th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Chocolate_addiction" title="Chocolate addiction">Chocolate addiction</a></li> <li><a href="/wiki/Chocolate_bloom" title="Chocolate bloom">Chocolate bloom</a></li> <li><a href="/wiki/Chocolate_fountain" title="Chocolate fountain">Chocolate fountain</a></li> <li><a href="/wiki/List_of_chocolate_museums" title="List of chocolate museums">Chocolate museums</a></li> <li><a href="/wiki/List_of_chocolatiers" title="List of chocolatiers">Chocolatiers</a></li> <li><a href="/wiki/Cocoa_smuggling" title="Cocoa smuggling">Cocoa smuggling</a></li> <li><a href="/wiki/History_of_chocolate" title="History of chocolate">History</a></li> <li><a href="/wiki/Chocolate_in_savory_cooking" title="Chocolate in savory cooking">In savory cooking</a></li> <li>Military chocolate <ul><li><a href="/wiki/Military_chocolate_(Switzerland)" title="Military chocolate (Switzerland)">Switzerland</a></li> <li><a href="/wiki/Military_chocolate_(United_States)" title="Military chocolate (United States)">United States</a></li></ul></li></ul> </div></td></tr><tr><td class="navbox-abovebelow" colspan="2" style="background: #7B3F00; color: white;"><div><div class="plainlist"> <ul><li><span class="noviewer" typeof="mw:File"><span title="Category"><img alt="" src="//upload.wikimedia.org/wikipedia/en/thumb/9/96/Symbol_category_class.svg/16px-Symbol_category_class.svg.png" decoding="async" width="16" height="16" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/9/96/Symbol_category_class.svg/23px-Symbol_category_class.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/9/96/Symbol_category_class.svg/31px-Symbol_category_class.svg.png 2x" data-file-width="180" data-file-height="185" /></span></span> <b><a href="/wiki/Category:Chocolate" title="Category:Chocolate"><span style="color:white">Category</span></a></b></li> <li><span class="noviewer" typeof="mw:File"><span title="Outline"><img alt="" src="//upload.wikimedia.org/wikipedia/commons/thumb/4/41/Global_thinking.svg/10px-Global_thinking.svg.png" decoding="async" width="10" height="16" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/4/41/Global_thinking.svg/15px-Global_thinking.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/4/41/Global_thinking.svg/21px-Global_thinking.svg.png 2x" data-file-width="130" data-file-height="200" /></span></span> <b><a href="/wiki/Outline_of_chocolate" title="Outline of chocolate"><span style="color:white">Outline</span></a></b></li></ul> </div></div></td></tr></tbody></table></div> <div 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"><style data-mw-deduplicate="TemplateStyles:r1038841319">.mw-parser-output .tooltip-dotted{border-bottom:1px dotted;cursor:help}</style><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1038841319"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1038841319"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1038841319"></div><div role="navigation" class="navbox authority-control" aria-label="Navbox" style="padding:3px"><table class="nowraplinks hlist navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Help:Authority_control" title="Help:Authority control">Authority control databases</a>: National <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q181003#identifiers" title="Edit this at Wikidata"><img alt="Edit this at Wikidata" src="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/10px-OOjs_UI_icon_edit-ltr-progressive.svg.png" decoding="async" width="10" height="10" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/15px-OOjs_UI_icon_edit-ltr-progressive.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/20px-OOjs_UI_icon_edit-ltr-progressive.svg.png 2x" data-file-width="20" data-file-height="20" /></a></span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"><ul><li><span class="uid"><span class="rt-commentedText tooltip tooltip-dotted" title="Tryptophan"><a rel="nofollow" class="external text" href="https://id.loc.gov/authorities/sh86000850">United States</a></span></span></li><li><span class="uid"><span class="rt-commentedText tooltip tooltip-dotted" title="Tryptophane"><a rel="nofollow" class="external text" href="https://catalogue.bnf.fr/ark:/12148/cb122624834">France</a></span></span></li><li><span class="uid"><span class="rt-commentedText tooltip tooltip-dotted" title="Tryptophane"><a rel="nofollow" class="external text" href="https://data.bnf.fr/ark:/12148/cb122624834">BnF data</a></span></span></li><li><span class="uid"><a rel="nofollow" class="external text" href="https://id.ndl.go.jp/auth/ndlna/00573319">Japan</a></span></li><li><span class="uid"><span class="rt-commentedText tooltip tooltip-dotted" title="tryptofan"><a rel="nofollow" class="external text" href="https://aleph.nkp.cz/F/?func=find-c&local_base=aut&ccl_term=ica=ph126775&CON_LNG=ENG">Czech Republic</a></span></span></li><li><span class="uid"><a rel="nofollow" class="external text" href="http://olduli.nli.org.il/F/?func=find-b&local_base=NLX10&find_code=UID&request=987007539178205171">Israel</a></span></li></ul></div></td></tr></tbody></table></div>    </div><noscript><img src="https://login.wikimedia.org/wiki/Special:CentralAutoLogin/start?type=1x1" alt="" width="1" height="1" style="border: none; position: absolute;"></noscript> <div class="printfooter" data-nosnippet="">Retrieved from "<a dir="ltr" href="https://en.wikipedia.org/w/index.php?title=Tryptophan&oldid=1249994738">https://en.wikipedia.org/w/index.php?title=Tryptophan&oldid=1249994738</a>"</div></div> <div id="catlinks" class="catlinks" data-mw="interface"><div id="mw-normal-catlinks" class="mw-normal-catlinks"><a href="/wiki/Help:Category" title="Help:Category">Categories</a>: <ul><li><a href="/wiki/Category:Alpha-Amino_acids" title="Category:Alpha-Amino acids">Alpha-Amino acids</a></li><li><a href="/wiki/Category:Proteinogenic_amino_acids" title="Category:Proteinogenic amino acids">Proteinogenic amino acids</a></li><li><a href="/wiki/Category:Indole_alkaloids" title="Category:Indole alkaloids">Indole alkaloids</a></li><li><a href="/wiki/Category:Glucogenic_amino_acids" title="Category:Glucogenic amino acids">Glucogenic amino acids</a></li><li><a href="/wiki/Category:Ketogenic_amino_acids" title="Category:Ketogenic amino acids">Ketogenic amino acids</a></li><li><a href="/wiki/Category:Aromatic_amino_acids" title="Category:Aromatic amino acids">Aromatic amino acids</a></li><li><a href="/wiki/Category:Essential_amino_acids" title="Category:Essential amino acids">Essential amino acids</a></li><li><a href="/wiki/Category:Tryptamine_alkaloids" title="Category:Tryptamine alkaloids">Tryptamine alkaloids</a></li><li><a href="/wiki/Category:Dietary_supplements" title="Category:Dietary supplements">Dietary supplements</a></li><li><a href="/wiki/Category:Carbonic_anhydrase_activators" title="Category:Carbonic anhydrase activators">Carbonic anhydrase activators</a></li><li><a href="/wiki/Category:Monoamine_precursors" title="Category:Monoamine precursors">Monoamine precursors</a></li><li><a href="/wiki/Category:Serotonin" title="Category:Serotonin">Serotonin</a></li></ul></div><div id="mw-hidden-catlinks" class="mw-hidden-catlinks mw-hidden-cats-hidden">Hidden categories: <ul><li><a href="/wiki/Category:All_articles_with_dead_external_links" title="Category:All articles with dead external links">All articles with dead external links</a></li><li><a href="/wiki/Category:Articles_with_dead_external_links_from_July_2021" title="Category:Articles with dead external links from July 2021">Articles with dead external links from July 2021</a></li><li><a href="/wiki/Category:Use_dmy_dates_from_September_2020" title="Category:Use dmy dates from September 2020">Use dmy dates from September 2020</a></li><li><a href="/wiki/Category:Chemical_articles_with_multiple_compound_IDs" title="Category:Chemical articles with multiple compound IDs">Chemical articles with multiple compound IDs</a></li><li><a href="/wiki/Category:Multiple_chemicals_in_an_infobox_that_need_indexing" title="Category:Multiple chemicals in an infobox that need indexing">Multiple chemicals in an infobox that need indexing</a></li><li><a href="/wiki/Category:Articles_without_InChI_source" title="Category:Articles without InChI source">Articles without InChI source</a></li><li><a href="/wiki/Category:ECHA_InfoCard_ID_from_Wikidata" title="Category:ECHA InfoCard ID from Wikidata">ECHA InfoCard ID from Wikidata</a></li><li><a href="/wiki/Category:Chemical_articles_having_a_data_page" title="Category:Chemical articles having a data page">Chemical articles having a data page</a></li><li><a href="/wiki/Category:Articles_containing_unverified_chemical_infoboxes" title="Category:Articles containing unverified chemical infoboxes">Articles containing unverified chemical infoboxes</a></li><li><a href="/wiki/Category:Chembox_image_size_set" title="Category:Chembox image size set">Chembox image size set</a></li><li><a href="/wiki/Category:Articles_with_short_description" title="Category:Articles with short description">Articles with short description</a></li><li><a href="/wiki/Category:Short_description_matches_Wikidata" title="Category:Short description matches Wikidata">Short description matches Wikidata</a></li></ul></div></div> </div> </main> </div> <div class="mw-footer-container"> <footer id="footer" class="mw-footer" > <ul id="footer-info"> <li id="footer-info-lastmod"> This page was last edited on 7 October 2024, at 22:39<span class="anonymous-show"> (UTC)</span>.</li> <li id="footer-info-copyright">Text is available under the <a href="/wiki/Wikipedia:Text_of_the_Creative_Commons_Attribution-ShareAlike_4.0_International_License" title="Wikipedia:Text of the Creative Commons Attribution-ShareAlike 4.0 International License">Creative Commons Attribution-ShareAlike 4.0 License</a>; additional terms may apply. By using this site, you agree to the <a href="https://foundation.wikimedia.org/wiki/Special:MyLanguage/Policy:Terms_of_Use" class="extiw" title="foundation:Special:MyLanguage/Policy:Terms of Use">Terms of Use</a> and <a href="https://foundation.wikimedia.org/wiki/Special:MyLanguage/Policy:Privacy_policy" class="extiw" title="foundation:Special:MyLanguage/Policy:Privacy policy">Privacy Policy</a>. Wikipedia® is a registered trademark of the <a rel="nofollow" class="external text" href="https://wikimediafoundation.org/">Wikimedia Foundation, Inc.</a>, a non-profit organization.</li> </ul> <ul id="footer-places"> <li id="footer-places-privacy"><a href="https://foundation.wikimedia.org/wiki/Special:MyLanguage/Policy:Privacy_policy">Privacy policy</a></li> <li id="footer-places-about"><a href="/wiki/Wikipedia:About">About Wikipedia</a></li> <li id="footer-places-disclaimers"><a href="/wiki/Wikipedia:General_disclaimer">Disclaimers</a></li> <li id="footer-places-contact"><a href="//en.wikipedia.org/wiki/Wikipedia:Contact_us">Contact Wikipedia</a></li> <li id="footer-places-wm-codeofconduct"><a href="https://foundation.wikimedia.org/wiki/Special:MyLanguage/Policy:Universal_Code_of_Conduct">Code of Conduct</a></li> <li id="footer-places-developers"><a href="https://developer.wikimedia.org">Developers</a></li> <li id="footer-places-statslink"><a href="https://stats.wikimedia.org/#/en.wikipedia.org">Statistics</a></li> <li id="footer-places-cookiestatement"><a href="https://foundation.wikimedia.org/wiki/Special:MyLanguage/Policy:Cookie_statement">Cookie statement</a></li> <li id="footer-places-mobileview"><a href="//en.m.wikipedia.org/w/index.php?title=Tryptophan&mobileaction=toggle_view_mobile" class="noprint stopMobileRedirectToggle">Mobile view</a></li> </ul> <ul id="footer-icons" class="noprint"> <li id="footer-copyrightico"><a href="https://wikimediafoundation.org/" class="cdx-button cdx-button--fake-button cdx-button--size-large cdx-button--fake-button--enabled"><img src="/static/images/footer/wikimedia-button.svg" width="84" height="29" alt="Wikimedia Foundation" loading="lazy"></a></li> <li id="footer-poweredbyico"><a href="https://www.mediawiki.org/" class="cdx-button cdx-button--fake-button cdx-button--size-large cdx-button--fake-button--enabled"><img src="/w/resources/assets/poweredby_mediawiki.svg" alt="Powered by MediaWiki" width="88" height="31" loading="lazy"></a></li> </ul> </footer> </div> </div> </div> <div class="vector-settings" id="p-dock-bottom"> <ul></ul> </div><script>(RLQ=window.RLQ||[]).push(function(){mw.config.set({"wgHostname":"mw-web.codfw.main-f69cdc8f6-strzt","wgBackendResponseTime":193,"wgPageParseReport":{"limitreport":{"cputime":"1.940","walltime":"2.339","ppvisitednodes":{"value":15328,"limit":1000000},"postexpandincludesize":{"value":614103,"limit":2097152},"templateargumentsize":{"value":49168,"limit":2097152},"expansiondepth":{"value":25,"limit":100},"expensivefunctioncount":{"value":11,"limit":500},"unstrip-depth":{"value":1,"limit":20},"unstrip-size":{"value":391300,"limit":5000000},"entityaccesscount":{"value":1,"limit":400},"timingprofile":["100.00% 1795.689 1 -total"," 36.67% 658.467 1 Template:Chembox"," 34.66% 622.340 1 Template:Reflist"," 23.88% 428.768 60 Template:Cite_journal"," 21.21% 380.896 1 Template:Chembox_Identifiers"," 12.80% 229.867 5 Template:Chembox_headerbar"," 12.61% 226.465 15 Template:Trim"," 9.86% 177.133 18 Template:Main_other"," 8.80% 158.086 1 Template:Chembox_parametercheck"," 7.54% 135.358 16 Template:Navbox"]},"scribunto":{"limitreport-timeusage":{"value":"0.976","limit":"10.000"},"limitreport-memusage":{"value":11937475,"limit":52428800}},"cachereport":{"origin":"mw-web.codfw.main-f69cdc8f6-fvkzk","timestamp":"20241122140419","ttl":2592000,"transientcontent":false}}});});</script> <script type="application/ld+json">{"@context":"https:\/\/schema.org","@type":"Article","name":"Tryptophan","url":"https:\/\/en.wikipedia.org\/wiki\/Tryptophan","sameAs":"http:\/\/www.wikidata.org\/entity\/Q181003","mainEntity":"http:\/\/www.wikidata.org\/entity\/Q181003","author":{"@type":"Organization","name":"Contributors to Wikimedia projects"},"publisher":{"@type":"Organization","name":"Wikimedia Foundation, Inc.","logo":{"@type":"ImageObject","url":"https:\/\/www.wikimedia.org\/static\/images\/wmf-hor-googpub.png"}},"datePublished":"2002-06-18T21:42:32Z","dateModified":"2024-10-07T22:39:51Z","image":"https:\/\/upload.wikimedia.org\/wikipedia\/commons\/0\/0c\/Tryptophan-from-xtal-3D-sf.png","headline":"chemical compound"}</script> </body> </html>