CINXE.COM

<!DOCTYPE html> <html class="client-nojs vector-feature-language-in-header-enabled vector-feature-language-in-main-page-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-sticky-header-enabled vector-toc-available" lang="en" dir="ltr"> <head> <meta charset="UTF-8"> <title>Epibatidine - Wikipedia</title> <script>(function(){var className="client-js vector-feature-language-in-header-enabled vector-feature-language-in-main-page-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-sticky-header-enabled 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":"817df5ca-59cb-4711-b796-667359ce9ad1","wgCanonicalNamespace":"","wgCanonicalSpecialPageName":false,"wgNamespaceNumber":0,"wgPageName":"Epibatidine","wgTitle":"Epibatidine","wgCurRevisionId":1268918875,"wgRevisionId":1268918875,"wgArticleId":2103074,"wgIsArticle":true,"wgIsRedirect":false,"wgAction":"view","wgUserName":null,"wgUserGroups":["*"],"wgCategories":["Articles with short description","Short description is different from Wikidata","Articles with changed KEGG identifier","ECHA InfoCard ID from Wikidata","Drugs missing an ATC code","Drugs with no legal status","Drugboxes which contain changes to verified fields","Drugboxes which contain changes to watched fields","All articles with unsourced statements","Articles with unsourced statements from May 2018","Articles with unsourced statements from March 2014","Analgesics","Nicotinic agonists","Amphibian toxins","Pyridine alkaloids","Halogen-containing alkaloids","Chloropyridines","Neurotoxins","Halogen-containing natural products","Chlorine-containing natural products"],"wgPageViewLanguage":"en","wgPageContentLanguage":"en","wgPageContentModel":"wikitext","wgRelevantPageName":"Epibatidine","wgRelevantArticleId":2103074,"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":30000,"wgEditSubmitButtonLabelPublish":true,"wgULSPosition":"interlanguage","wgULSisCompactLinksEnabled":false,"wgVector2022LanguageInHeader":true,"wgULSisLanguageSelectorEmpty":false,"wgWikibaseItemId":"Q423783","wgCheckUserClientHintsHeadersJsApi":["brands","architecture","bitness","fullVersionList","mobile","model","platform","platformVersion"],"GEHomepageSuggestedEditsEnableTopics":true,"wgGETopicsMatchModeEnabled":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.makeCollapsible.styles":"ready","ext.wikimediamessages.styles":"ready","ext.visualEditor.desktopArticleTarget.noscript":"ready","ext.uls.interlanguage":"ready","wikibase.client.init":"ready"};RLPAGEMODULES=["ext.cite.ux-enhancements","mediawiki.page.media","site","mediawiki.page.ready","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.quicksurveys.init","ext.growthExperiments.SuggestedEditSession"];</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.wikimediamessages.styles%7Cjquery.makeCollapsible.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.22"> <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/e/e0/Epibatidine_molecule_ball.png/1200px-Epibatidine_molecule_ball.png"> <meta property="og:image:width" content="1200"> <meta property="og:image:height" content="914"> <meta property="og:image" content="https://upload.wikimedia.org/wikipedia/commons/thumb/e/e0/Epibatidine_molecule_ball.png/800px-Epibatidine_molecule_ball.png"> <meta property="og:image:width" content="800"> <meta property="og:image:height" content="610"> <meta property="og:image" content="https://upload.wikimedia.org/wikipedia/commons/thumb/e/e0/Epibatidine_molecule_ball.png/640px-Epibatidine_molecule_ball.png"> <meta property="og:image:width" content="640"> <meta property="og:image:height" content="488"> <meta name="viewport" content="width=1120"> <meta property="og:title" content="Epibatidine - 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/Epibatidine"> <link rel="alternate" type="application/x-wiki" title="Edit this page" href="/w/index.php?title=Epibatidine&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/Epibatidine"> <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="auth.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-Epibatidine rootpage-Epibatidine 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" title="Main menu" > <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><li id="n-specialpages" class="mw-list-item"><a href="/wiki/Special:SpecialPages"><span>Special pages</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/?wmf_source=donate&wmf_medium=sidebar&wmf_campaign=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=Epibatidine" 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=Epibatidine" 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/?wmf_source=donate&wmf_medium=sidebar&wmf_campaign=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=Epibatidine" 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=Epibatidine" 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-History" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#History"> <div class="vector-toc-text"> <span class="vector-toc-numb">1</span> <span>History</span> </div> </a> <ul id="toc-History-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Synthesis" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Synthesis"> <div class="vector-toc-text"> <span class="vector-toc-numb">2</span> <span>Synthesis</span> </div> </a> <button aria-controls="toc-Synthesis-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 Synthesis subsection</span> </button> <ul id="toc-Synthesis-sublist" class="vector-toc-list"> <li id="toc-Synthetic_analogs" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Synthetic_analogs"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.1</span> <span>Synthetic analogs</span> </div> </a> <ul id="toc-Synthetic_analogs-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Chemical_structure" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Chemical_structure"> <div class="vector-toc-text"> <span class="vector-toc-numb">3</span> <span>Chemical structure</span> </div> </a> <ul id="toc-Chemical_structure-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Biological_effects" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Biological_effects"> <div class="vector-toc-text"> <span class="vector-toc-numb">4</span> <span>Biological effects</span> </div> </a> <button aria-controls="toc-Biological_effects-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 Biological effects subsection</span> </button> <ul id="toc-Biological_effects-sublist" class="vector-toc-list"> <li id="toc-Mechanism_of_action" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Mechanism_of_action"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.1</span> <span>Mechanism of action</span> </div> </a> <ul id="toc-Mechanism_of_action-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Symptoms" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Symptoms"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.2</span> <span>Symptoms</span> </div> </a> <ul id="toc-Symptoms-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Pharmacology" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Pharmacology"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.3</span> <span>Pharmacology</span> </div> </a> <ul id="toc-Pharmacology-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Potential_medical_uses" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Potential_medical_uses"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.4</span> <span>Potential medical uses</span> </div> </a> <ul id="toc-Potential_medical_uses-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Antidote" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Antidote"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.5</span> <span>Antidote</span> </div> </a> <ul id="toc-Antidote-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">5</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">6</span> <span>References</span> </div> </a> <ul id="toc-References-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">7</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" title="Table of Contents" > <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">Epibatidine</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 12 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-12" 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">12 languages</span> </label> <div class="vector-dropdown-content"> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li class="interlanguage-link interwiki-da mw-list-item"><a href="https://da.wikipedia.org/wiki/Epibatidin" title="Epibatidin – Danish" lang="da" hreflang="da" data-title="Epibatidin" 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/Epibatidin" title="Epibatidin – German" lang="de" hreflang="de" data-title="Epibatidin" data-language-autonym="Deutsch" data-language-local-name="German" class="interlanguage-link-target"><span>Deutsch</span></a></li><li class="interlanguage-link interwiki-es mw-list-item"><a href="https://es.wikipedia.org/wiki/Epibatidina" title="Epibatidina – Spanish" lang="es" hreflang="es" data-title="Epibatidina" data-language-autonym="Español" data-language-local-name="Spanish" class="interlanguage-link-target"><span>Español</span></a></li><li class="interlanguage-link interwiki-fr mw-list-item"><a href="https://fr.wikipedia.org/wiki/%C3%89pibatidine" title="Épibatidine – French" lang="fr" hreflang="fr" data-title="Épibatidine" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target"><span>Français</span></a></li><li class="interlanguage-link interwiki-it mw-list-item"><a href="https://it.wikipedia.org/wiki/Epibatidina" title="Epibatidina – Italian" lang="it" hreflang="it" data-title="Epibatidina" data-language-autonym="Italiano" data-language-local-name="Italian" class="interlanguage-link-target"><span>Italiano</span></a></li><li class="interlanguage-link interwiki-lt mw-list-item"><a href="https://lt.wikipedia.org/wiki/Epibatidinas" title="Epibatidinas – Lithuanian" lang="lt" hreflang="lt" data-title="Epibatidinas" data-language-autonym="Lietuvių" data-language-local-name="Lithuanian" class="interlanguage-link-target"><span>Lietuvių</span></a></li><li class="interlanguage-link interwiki-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/Epibatidine" title="Epibatidine – Dutch" lang="nl" hreflang="nl" data-title="Epibatidine" data-language-autonym="Nederlands" data-language-local-name="Dutch" class="interlanguage-link-target"><span>Nederlands</span></a></li><li class="interlanguage-link interwiki-pl mw-list-item"><a href="https://pl.wikipedia.org/wiki/Epibatydyna" title="Epibatydyna – Polish" lang="pl" hreflang="pl" data-title="Epibatydyna" 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/Epibatidina" title="Epibatidina – Portuguese" lang="pt" hreflang="pt" data-title="Epibatidina" data-language-autonym="Português" data-language-local-name="Portuguese" class="interlanguage-link-target"><span>Português</span></a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/Epibatidin" title="Epibatidin – Serbian" lang="sr" hreflang="sr" data-title="Epibatidin" 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/Epibatidin" title="Epibatidin – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Epibatidin" data-language-autonym="Srpskohrvatski / српскохрватски" data-language-local-name="Serbo-Croatian" class="interlanguage-link-target"><span>Srpskohrvatski / српскохрватски</span></a></li><li class="interlanguage-link interwiki-fi mw-list-item"><a href="https://fi.wikipedia.org/wiki/Epibatidiini" title="Epibatidiini – Finnish" lang="fi" hreflang="fi" data-title="Epibatidiini" data-language-autonym="Suomi" data-language-local-name="Finnish" class="interlanguage-link-target"><span>Suomi</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/Q423783#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/Epibatidine" 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:Epibatidine" 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/Epibatidine"><span>Read</span></a></li><li id="ca-edit" class="vector-tab-noicon mw-list-item"><a href="/w/index.php?title=Epibatidine&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=Epibatidine&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/Epibatidine"><span>Read</span></a></li><li id="ca-more-edit" class="vector-more-collapsible-item mw-list-item"><a href="/w/index.php?title=Epibatidine&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=Epibatidine&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/Epibatidine" 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/Epibatidine" 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="//en.wikipedia.org/wiki/Wikipedia:File_Upload_Wizard" title="Upload files [u]" accesskey="u"><span>Upload file</span></a></li><li id="t-permalink" class="mw-list-item"><a href="/w/index.php?title=Epibatidine&oldid=1268918875" 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=Epibatidine&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=Epibatidine&id=1268918875&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%2FEpibatidine"><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%2FEpibatidine"><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=Epibatidine&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=Epibatidine&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:Epibatidine" 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/Q423783" 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"><div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Toxic chemical from some poison dart frogs</div> <style data-mw-deduplicate="TemplateStyles:r1236090951">.mw-parser-output .hatnote{font-style:italic}.mw-parser-output div.hatnote{padding-left:1.6em;margin-bottom:0.5em}.mw-parser-output .hatnote i{font-style:normal}.mw-parser-output .hatnote+link+.hatnote{margin-top:-0.5em}@media print{body.ns-0 .mw-parser-output .hatnote{display:none!important}}</style><div role="note" class="hatnote navigation-not-searchable">Not to be confused with <a href="/wiki/Eptifibatide" title="Eptifibatide">Eptifibatide</a>.</div> <div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Pharmaceutical compound</div> <style data-mw-deduplicate="TemplateStyles:r1269284339">@media screen{html.skin-theme-clientpref-night .mw-parser-output .dark_mode_safe img{background-color:var(--background-color-inverted,#f8f9fa)}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .dark_mode_safe img{background-color:var(--background-color-inverted,#f8f9fa)}}</style> <style data-mw-deduplicate="TemplateStyles:r1257001546">.mw-parser-output .infobox-subbox{padding:0;border:none;margin:-3px;width:auto;min-width:100%;font-size:100%;clear:none;float:none;background-color:transparent}.mw-parser-output .infobox-3cols-child{margin:auto}.mw-parser-output .infobox .navbar{font-size:100%}@media screen{html.skin-theme-clientpref-night .mw-parser-output .infobox-full-data:not(.notheme)>div:not(.notheme)[style]{background:#1f1f23!important;color:#f8f9fa}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .infobox-full-data:not(.notheme) div:not(.notheme){background:#1f1f23!important;color:#f8f9fa}}@media(min-width:640px){body.skin--responsive .mw-parser-output .infobox-table{display:table!important}body.skin--responsive .mw-parser-output .infobox-table>caption{display:table-caption!important}body.skin--responsive .mw-parser-output .infobox-table>tbody{display:table-row-group}body.skin--responsive .mw-parser-output .infobox-table tr{display:table-row!important}body.skin--responsive .mw-parser-output .infobox-table th,body.skin--responsive .mw-parser-output .infobox-table td{padding-left:inherit;padding-right:inherit}}</style><table class="infobox" style="border-spacing:2px;"><caption class="infobox-title"><span title="International nonproprietary name (INN): Epibatidine">Epibatidine</span></caption><tbody><tr><td colspan="2" class="infobox-image"><span class="mw-default-size skin-invert-image" typeof="mw:File/Frameless"><a href="/wiki/File:Epibatidine_structure.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/d/db/Epibatidine_structure.svg/250px-Epibatidine_structure.svg.png" decoding="async" width="220" height="96" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/d/db/Epibatidine_structure.svg/330px-Epibatidine_structure.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/d/db/Epibatidine_structure.svg/440px-Epibatidine_structure.svg.png 2x" data-file-width="435" data-file-height="190" /></a></span></td></tr><tr><td colspan="2" class="infobox-image"><span class="mw-default-size dark_mode_safe" typeof="mw:File/Frameless"><a href="/wiki/File:Epibatidine_molecule_ball.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/e/e0/Epibatidine_molecule_ball.png/220px-Epibatidine_molecule_ball.png" decoding="async" width="220" height="168" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/e0/Epibatidine_molecule_ball.png/330px-Epibatidine_molecule_ball.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/e/e0/Epibatidine_molecule_ball.png/440px-Epibatidine_molecule_ball.png 2x" data-file-width="2000" data-file-height="1524" /></a></span></td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd;color:inherit;">Identifiers</th></tr><tr><td colspan="2" class="infobox-full-data"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold;"><div><a href="/wiki/IUPAC_nomenclature_of_chemistry" title="IUPAC nomenclature of chemistry">IUPAC name</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all; text-align:left; padding-left:1.5em; text-indent:-1.5em;"><li style="line-height: inherit; margin: 0"><div style="font-size: 97%;">(1<i>R</i>,2<i>R</i>,4<i>S</i>)-(+)-6-(6-Chloro-3-pyridyl)-7-azabicyclo[2.2.1]heptane</div></li></ul> </div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/CAS_Registry_Number" title="CAS Registry Number">CAS Number</a></th><td class="infobox-data"><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=140111-52-0">140111-52-0</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/PubChem#CID" title="PubChem">PubChem</a> <span style="font-weight:normal"><abbr title="Compound ID">CID</abbr></span></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><span title="pubchem.ncbi.nlm.nih.gov"><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/1204">1204</a></span></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/DrugBank" title="DrugBank">DrugBank</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><span title="www.drugbank.ca"><a rel="nofollow" class="external text" href="https://www.drugbank.ca/drugs/DB07720">DB07720</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/ChemSpider" title="ChemSpider">ChemSpider</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><span title="www.chemspider.com"><a rel="nofollow" class="external text" href="https://www.chemspider.com/Chemical-Structure.10399316.html">10399316</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Unique_Ingredient_Identifier" title="Unique Ingredient Identifier">UNII</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><span title="precision.fda.gov"><a rel="nofollow" class="external text" href="https://precision.fda.gov/uniisearch/srs/unii/M6K314F1XX">M6K314F1XX</a></span></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/KEGG" title="KEGG">KEGG</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><span title="www.kegg.jp"><a rel="nofollow" class="external text" href="https://www.kegg.jp/entry/C11690">C11690</a></span><sup> <span typeof="mw:File"><span><img alt="☒" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/7px-X_mark.svg.png" decoding="async" width="7" height="8" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/11px-X_mark.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/14px-X_mark.svg.png 2x" data-file-width="525" data-file-height="600" /></span></span><span style="display:none">N</span></sup></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/ChEBI" title="ChEBI">ChEBI</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><span title="www.ebi.ac.uk"><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:4803">CHEBI:4803</a></span></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/ChEMBL" title="ChEMBL">ChEMBL</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><span title="www.ebi.ac.uk"><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chembl/explore/compound/ChEMBL298826">ChEMBL298826</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/ECHA_InfoCard" class="mw-redirect" title="ECHA InfoCard"><span title="echa.europa.eu">ECHA InfoCard</span></a></th><td class="infobox-data"><a rel="nofollow" class="external text" href="https://echa.europa.eu/substance-information/-/substanceinfo/100.162.281">100.162.281</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q423783#P2566" title="Edit this at Wikidata"><img alt="Edit this at Wikidata" src="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/10px-OOjs_UI_icon_edit-ltr-progressive.svg.png" decoding="async" width="10" height="10" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/15px-OOjs_UI_icon_edit-ltr-progressive.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/20px-OOjs_UI_icon_edit-ltr-progressive.svg.png 2x" data-file-width="20" data-file-height="20" /></a></span></td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd;color:inherit;">Chemical and physical data</th></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Chemical_formula" title="Chemical formula">Formula</a></th><td class="infobox-data"><span title="Carbon">C</span><sub>11</sub><span title="Hydrogen">H</span><sub>13</sub><span title="Chlorine">Cl</span><span title="Nitrogen">N</span><sub>2</sub></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Molar_mass" title="Molar mass">Molar mass</a></th><td class="infobox-data"><span class="nowrap"><span data-sort-value="7002208690000000000♠"></span>208.69</span> g·mol<sup>−1</sup></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;">3D model (<a href="/wiki/JSmol" class="mw-redirect" title="JSmol">JSmol</a>)</th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><span title="chemapps.stolaf.edu (3D interactive model)"><a rel="nofollow" class="external text" href="https://chemapps.stolaf.edu/jmol/jmol.php?model=ClC1%3DCC%3DC%28%5BC%40%40H%5D2C%5BC%40%5D3%28%5BH%5D%29CC%5BC%40%40%5D2%28%5BH%5D%29N3%29C%3DN1">Interactive image</a></span></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Density" title="Density">Density</a></th><td class="infobox-data">1.2 ± 0.1 g/cm<sup>3</sup> g/cm<sup>3</sup></td></tr><tr><td colspan="2" class="infobox-full-data"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold;"><div><a href="/wiki/Simplified_molecular-input_line-entry_system" class="mw-redirect" title="Simplified molecular-input line-entry system">SMILES</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="word-wrap:break-word; text-indent:-1.5em; text-align:left; padding-left:1.5em; font-size:97%; line-height:120%;">ClC1=CC=C([C@@H]2C[C@]3([H])CC[C@@]2([H])N3)C=N1</div></li></ul> </div></td></tr><tr><td colspan="2" class="infobox-full-data"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold;"><div><a href="/wiki/International_Chemical_Identifier" title="International Chemical Identifier">InChI</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="word-wrap:break-word; text-indent:-1.5em; text-align:left; padding-left:1.5em; font-size:97%; line-height:120%;">InChI=1S/C11H13ClN2/c12-11-4-1-7(6-13-11)9-5-8-2-3-10(9)14-8/h1,4,6,8-10,14H,2-3,5H2/t8-,9+,10+/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></li><li style="line-height: inherit; margin: 0"><div style="word-wrap:break-word; text-indent:-1.5em; text-align:left; padding-left:1.5em; font-size:97%; line-height:120%;">Key:NLPRAJRHRHZCQQ-IVZWLZJFSA-N<sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></div></li></ul> </div></td></tr><tr><td colspan="2" class="infobox-below"><style data-mw-deduplicate="TemplateStyles:r886047488">.mw-parser-output .nobold{font-weight:normal}</style><span class="nobold"> <sup><span typeof="mw:File"><span><img alt="☒" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/7px-X_mark.svg.png" decoding="async" width="7" height="8" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/11px-X_mark.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/14px-X_mark.svg.png 2x" data-file-width="525" data-file-height="600" /></span></span><span style="display:none">N</span><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> <a href="/wiki/Wikipedia:WikiProject_Chemicals/Chembox_validation" title="Wikipedia:WikiProject Chemicals/Chembox validation">(what is this?)</a></span><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r886047488" /><span class="nobold">  <span class="reflink plainlinks nourlexpansion"><a class="external text" href="https://en.wikipedia.org/w/index.php?title=Special:ComparePages&rev1=443729000&page2=Epibatidine">(verify)</a></span></span></td></tr></tbody></table> <p><b>Epibatidine</b> is a chlorinated <a href="/wiki/Alkaloid" title="Alkaloid">alkaloid</a> that is secreted by the <a href="/wiki/Ecuador" title="Ecuador">Ecuadoran</a> frog <i><a href="/wiki/Epipedobates_anthonyi" class="mw-redirect" title="Epipedobates anthonyi">Epipedobates anthonyi</a></i> and <a href="/wiki/Poison_dart_frog" title="Poison dart frog">poison dart frogs</a> from the <i><a href="/wiki/Ameerega" title="Ameerega">Ameerega</a></i> genus.<sup id="cite_ref-1" class="reference"><a href="#cite_note-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> It was discovered by <a href="/wiki/John_W._Daly" title="John W. Daly">John W. Daly</a> in 1974, but its structure was not fully elucidated until 1992. Whether epibatidine occurs naturally remains controversial due to challenges in conclusively identifying the compound from the limited samples collected by Daly. By the time that high-resolution spectrometry was used in 1991, there remained less than one milligram of extract from Daly's samples, raising concerns about possible contamination. Samples from other batches of the same species of frog failed to yield epibatidine.<sup id="cite_ref-H.M._Garraffo_(2009)_2-0" class="reference"><a href="#cite_note-H.M._Garraffo_(2009)-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> </p><p>Epibatidine is toxic. Its toxicity stems from its ability to interact with <a href="/wiki/Nicotinic_acetylcholine_receptor" title="Nicotinic acetylcholine receptor">nicotinic</a> and <a href="/wiki/Muscarinic_acetylcholine_receptor" title="Muscarinic acetylcholine receptor">muscarinic acetylcholine receptors</a>. These receptors are involved in the transmission of painful sensations, and in movement, among other functions. Epibatidine then causes numbness, and, eventually, paralysis. Doses are lethal when the paralysis causes respiratory arrest. Originally, it was thought that epibatidine could be useful as a drug. However, because of its unacceptable <a href="/wiki/Therapeutic_index" title="Therapeutic index">therapeutic index</a>, it is no longer being researched for potential therapeutic uses.<sup id="cite_ref-Schwarcz,_Joe_3-0" class="reference"><a href="#cite_note-Schwarcz,_Joe-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="History">History</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Epibatidine&action=edit&section=1" title="Edit section: History"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Epibatidine was discovered by <a href="/wiki/John_W._Daly" title="John W. Daly">John W. Daly</a> in 1974. It was isolated from the skin of <i>Epipedobates anthonyi</i> frogs collected by Daly and colleague, Charles Myers. Between 1974 and 1979, Daly and Myers collected the skins of nearly 3000 frogs from various sites in Ecuador, after finding that a small injection of a preparation from their skin caused analgesic (painkilling) effects in mice that resembled those of an <a href="/wiki/Opioid" title="Opioid">opioid</a>.<sup id="cite_ref-H.M._Garraffo_(2009)_2-1" class="reference"><a href="#cite_note-H.M._Garraffo_(2009)-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> Despite its common name - Anthony's Poison Arrow frog - suggesting that it was used by natives when hunting,<sup id="cite_ref-Epipedobates_anthonyi_4-0" class="reference"><a href="#cite_note-Epipedobates_anthonyi-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> a paper written by Daly in 2000 claimed that there was no local folklore or folk medicine surrounding the frogs and that they were considered largely unimportant by the locals.<sup id="cite_ref-J.W._Daly_(2000)_5-0" class="reference"><a href="#cite_note-J.W._Daly_(2000)-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> </p> <figure class="mw-default-size mw-halign-left" typeof="mw:File/Thumb"><a href="/wiki/File:Epipedobates_tricolor1.jpg" class="mw-file-description"><img alt="A photo of a Epipedobates tricolor on a leaf" src="//upload.wikimedia.org/wikipedia/commons/thumb/6/6f/Epipedobates_tricolor1.jpg/250px-Epipedobates_tricolor1.jpg" decoding="async" width="220" height="143" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/6f/Epipedobates_tricolor1.jpg/330px-Epipedobates_tricolor1.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/6f/Epipedobates_tricolor1.jpg/500px-Epipedobates_tricolor1.jpg 2x" data-file-width="2496" data-file-height="1626" /></a><figcaption><i>Epipedobates tricolor</i> on a leaf</figcaption></figure> <p>The structure of epibatidine was elucidated in 1992, an effort hindered by <i>E. anthonyi</i> gaining <a href="/wiki/International_Union_for_Conservation_of_Nature" title="International Union for Conservation of Nature">IUCN</a> protected status in 1984.<sup id="cite_ref-J.W._Daly_(2000)_5-1" class="reference"><a href="#cite_note-J.W._Daly_(2000)-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> Furthermore, these frogs do not produce the toxin when bred and reared in captivity, because they do not synthesize epibatidine themselves. Like other poison dart frogs, they instead obtain it through their diet and then sequester it on their skin. Likely dietary sources are beetles, ants, mites, and flies.<sup id="cite_ref-E.N._Lasley_(1999)_6-0" class="reference"><a href="#cite_note-E.N._Lasley_(1999)-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> Daly and Charles noticed that epibatidine was produced from their diet due to their return trip to Ecuador in 1976 when they found that at one site, none of the frogs present produced alkaloids, such as epibatidine; they discovered that only the frogs at certain sites with the dietary means allowed these frogs to produce epibatidine.<sup id="cite_ref-7" class="reference"><a href="#cite_note-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> Overcoming the difficulties, the structure was eventually determined, and the first synthesis of epibatidine was completed in 1993. Many other synthesis methods have been developed since.<sup id="cite_ref-J.W._Daly_(2000)_5-2" class="reference"><a href="#cite_note-J.W._Daly_(2000)-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> </p><p>Because of its analgesic effect, there was intense interest in epibatidine's use as a drug, because it was found not to be an opioid.<sup id="cite_ref-H.M._Garraffo_(2009)_2-2" class="reference"><a href="#cite_note-H.M._Garraffo_(2009)-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> This meant that it could potentially be used without fear of addiction. However, it was soon found that it cannot be used in humans because the dose resulting in toxic symptoms is too low for it to be safe.<sup id="cite_ref-Donnelly-Roberts_8-0" class="reference"><a href="#cite_note-Donnelly-Roberts-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Synthesis">Synthesis</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Epibatidine&action=edit&section=2" title="Edit section: Synthesis"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Several total synthesis routes have been devised due to the relative scarcity of epibatidine in nature.<sup id="cite_ref-9" class="reference"><a href="#cite_note-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> </p><p>After the discovery of the structure of epibatidine, more than fifty ways to synthesize it in the laboratory have been devised. In the first reported example, a nine-step procedure produces the substance as a <a href="/wiki/Racemate" class="mw-redirect" title="Racemate">racemate</a> (in contrast, the naturally occurring compound is the (+)-enantiomer; the (−)-enantiomer does not occur naturally). It was later determined that the (+) and (-) enantiomers had equivalent analgesic as well as toxic effects. The process has proven to be quite productive, with a yield of about 40%.<sup id="cite_ref-Traynor_10-0" class="reference"><a href="#cite_note-Traynor-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-car_11-0" class="reference"><a href="#cite_note-car-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Broka_12-0" class="reference"><a href="#cite_note-Broka-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup> </p><p>An <a href="/wiki/Enantioselective" class="mw-redirect" title="Enantioselective">enantioselective</a> synthesis reported by <a href="/wiki/E_J_Corey" class="mw-redirect" title="E J Corey">E J Corey</a> starting from chloronicotinaldehyde is outlined below: </p> <dl><dd><figure class="mw-halign-left skin-invert-image" typeof="mw:File/Thumb"><a href="/wiki/File:Epibatidine_Corey.svg" class="mw-file-description"><img alt="a chemical reaction seen in the synthesis of epibatidine" src="//upload.wikimedia.org/wikipedia/commons/thumb/1/1a/Epibatidine_Corey.svg/600px-Epibatidine_Corey.svg.png" decoding="async" width="600" height="656" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/1/1a/Epibatidine_Corey.svg/900px-Epibatidine_Corey.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/1/1a/Epibatidine_Corey.svg/1200px-Epibatidine_Corey.svg.png 2x" data-file-width="1449" data-file-height="1584" /></a><figcaption>The chemical synthesis of epibatidine by <a href="/wiki/E_J_Corey" class="mw-redirect" title="E J Corey">Corey</a></figcaption></figure><div style="clear:both;" class=""></div></dd></dl> <p>In addition to Corey's method, other notable methods include those of Broka,<sup id="cite_ref-13" class="reference"><a href="#cite_note-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup> Huang and Shen,<sup id="cite_ref-14" class="reference"><a href="#cite_note-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup> and Clayton and Regan.<sup id="cite_ref-car_11-1" class="reference"><a href="#cite_note-car-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Synthetic_analogs">Synthetic analogs</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Epibatidine&action=edit&section=3" title="Edit section: Synthetic analogs"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>A number of approaches to discovering <a href="/wiki/Structural_analog" title="Structural analog">structural analogs</a> of epibatine that maintain analgesics effects, but without the toxicity, have been attempted.<sup id="cite_ref-Dowd_15-0" class="reference"><a href="#cite_note-Dowd-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup> For example, <a href="/wiki/Abbott_Laboratories" title="Abbott Laboratories">Abbott Laboratories</a> has produced derivatives of epibatidine including <a href="/wiki/Tebanicline" title="Tebanicline">tebanicline</a> (ABT-594).<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> Tebanicline retains analgesic properties while avoiding paralysis by still binding to receptors that control pain perception and having a low affinity for muscle-type nicotinic acetylcholine receptors (nAChR) reducing its paralysis effect.<sup id="cite_ref-17" class="reference"><a href="#cite_note-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup> Other epibatidine analogs include <a href="/wiki/ABT-418" title="ABT-418">ABT-418</a>, <a href="/wiki/Epiboxidine" title="Epiboxidine">epiboxidine</a>, and their derivatives.<sup id="cite_ref-Dowd_15-1" class="reference"><a href="#cite_note-Dowd-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-18" class="reference"><a href="#cite_note-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-19" class="reference"><a href="#cite_note-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-20" class="reference"><a href="#cite_note-20"><span class="cite-bracket">[</span>20<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-21" class="reference"><a href="#cite_note-21"><span class="cite-bracket">[</span>21<span class="cite-bracket">]</span></a></sup> A synthesis of epibatidine, utilizing a microbial hydroxylation of an unactivated carbon in a 7-azanorbornane was published in 1999.<sup id="cite_ref-22" class="reference"><a href="#cite_note-22"><span class="cite-bracket">[</span>22<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Chemical_structure">Chemical structure</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Epibatidine&action=edit&section=4" title="Edit section: Chemical structure"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Epibatidine is a piperidine <a href="/wiki/Pyridine" title="Pyridine">pyridine</a> with a structure similar to that of <a href="/wiki/Nicotine" title="Nicotine">nicotine</a>.<sup id="cite_ref-M._Fisher_23-0" class="reference"><a href="#cite_note-M._Fisher-23"><span class="cite-bracket">[</span>23<span class="cite-bracket">]</span></a></sup> It is a <a href="/wiki/Hygroscopic" class="mw-redirect" title="Hygroscopic">hygroscopic</a> oily substance which is a <a href="/wiki/Base_(chemistry)" title="Base (chemistry)">base</a>. </p> <div class="mw-heading mw-heading2"><h2 id="Biological_effects">Biological effects</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Epibatidine&action=edit&section=5" title="Edit section: Biological effects"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Mechanism_of_action">Mechanism of action</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Epibatidine&action=edit&section=6" title="Edit section: Mechanism of action"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Epibatidine has two mechanisms of action: it can bind to either <a href="/wiki/Nicotinic_acetylcholine_receptor" title="Nicotinic acetylcholine receptor">nicotinic acetylcholine receptors</a> (nAChR) or <a href="/wiki/Muscarinic_acetylcholine_receptor" title="Muscarinic acetylcholine receptor">muscarinic acetylcholine receptors</a> (mAChR). Specifically, the <a href="/wiki/Analgesic" title="Analgesic">analgesic</a> property of epibatidine is believed to take place by its binding to the <a href="/wiki/Alpha-4_beta-2_nicotinic_receptor" title="Alpha-4 beta-2 nicotinic receptor">α4/β2</a> subtype of nicotinic receptors. Epibatidine also binds to the <a href="/wiki/Alpha-3_beta-4_nicotinic_receptor" title="Alpha-3 beta-4 nicotinic receptor">α3/β4</a> subtype and to a much lesser extent <a href="/wiki/Alpha-7_receptor" class="mw-redirect" title="Alpha-7 receptor">α7 receptors</a> (affinity 300-fold less than for <a href="/wiki/Alpha-4_beta-2_nicotinic_receptor" title="Alpha-4 beta-2 nicotinic receptor">α4/β2</a>)<sup id="cite_ref-24" class="reference"><a href="#cite_note-24"><span class="cite-bracket">[</span>24<span class="cite-bracket">]</span></a></sup> The rank order of affinities for the muscle nicotinic receptors is αε > αγ > αδ.<sup id="cite_ref-25" class="reference"><a href="#cite_note-25"><span class="cite-bracket">[</span>25<span class="cite-bracket">]</span></a></sup> </p><p>Nicotinic acetylcholine receptors are found in the post-synaptic membranes of nerve cells. These receptors are an example of ion gated channels where binding by a ligand causes a conformational change allowing ions to cross the membrane into the cell.<sup id="cite_ref-26" class="reference"><a href="#cite_note-26"><span class="cite-bracket">[</span>26<span class="cite-bracket">]</span></a></sup> They propagate neurotransmission in the <a href="/wiki/Central_nervous_system" title="Central nervous system">central</a> and <a href="/wiki/Peripheral_nervous_system" title="Peripheral nervous system">peripheral nervous system</a>. When neurotransmitters bind to these receptors, ion channels open, allowing Na<sup>+</sup> and Ca<sup>2+</sup> ions to move across the membrane. This depolarizes the post-synaptic membrane, inducing an action potential that propagates the signal. This signal will ultimately induce release of <a href="/wiki/Dopamine" title="Dopamine">dopamine</a> and <a href="/wiki/Norepinephrine" title="Norepinephrine">norepinephrine</a>, resulting in an antinociceptive effect on the organism. The usual neurotransmitter for nAChR is acetylcholine. However, other substances (such as epibatidine and <a href="/wiki/Nicotine" title="Nicotine">nicotine</a>) are also able to bind to the receptor and induce a similar, if not identical, response. Epibatidine has an extremely high affinity for nAChRs, depending on the receptor subtype, from 0.05 nM at the α4β2 subtype to 22 nM at the α7 subtype. <a href="/wiki/Affinity_(pharmacology)" class="mw-redirect" title="Affinity (pharmacology)">Affinity</a> as well as <a href="/wiki/Intrinsic_activity" title="Intrinsic activity">efficacy</a> (and thus also <a href="/wiki/Potency_(pharmacology)" title="Potency (pharmacology)">potency</a>) are much higher than for nicotine.<sup id="cite_ref-Traynor_10-1" class="reference"><a href="#cite_note-Traynor-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> </p><p>The <a href="/wiki/Paralytic" class="mw-redirect" title="Paralytic">paralytic</a> property of epibatidine takes place after its binding to <a href="/wiki/Muscle-type_nicotinic_receptor" title="Muscle-type nicotinic receptor">muscle-type nicotinic receptors</a>. </p><p>Low doses of epibatidine will only affect the nAChRs, due to a higher affinity to nAChRs than to mAChRs. Higher doses, however, will cause epibatidine to bind to the mAChRs. </p><p>Both (+)- and (-)-<a href="/wiki/Enantiomer" title="Enantiomer">enantiomers</a> of epibatidine are biologically active, and both have similar binding affinities to nAChRs<sup id="cite_ref-Traynor_10-2" class="reference"><a href="#cite_note-Traynor-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> Only the (+)-enantiomer does not induce tolerance. While this may be a potential therapeutic advantage over morphine, epibatidine has not entered clinical trials because even very small doses are lethal to rodents.<sup id="cite_ref-27" class="reference"><a href="#cite_note-27"><span class="cite-bracket">[</span>27<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Symptoms">Symptoms</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Epibatidine&action=edit&section=7" title="Edit section: Symptoms"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Epibatidine has several toxic consequences. Empirically proven effects include <a href="/wiki/Splanchnic_nerves" title="Splanchnic nerves">splanchnic</a> <a href="/wiki/Sympathetic_nervous_system" title="Sympathetic nervous system">sympathetic</a> nerve discharge and increased arterial pressure.<sup id="cite_ref-M._Fisher_23-1" class="reference"><a href="#cite_note-M._Fisher-23"><span class="cite-bracket">[</span>23<span class="cite-bracket">]</span></a></sup> The nerve discharge effects can cause antinociception partially mediated by agonism of central nicotinic acetylcholine receptors at low doses of epibatidine; 5 μg/kg.<sup id="cite_ref-Daly_28-0" class="reference"><a href="#cite_note-Daly-28"><span class="cite-bracket">[</span>28<span class="cite-bracket">]</span></a></sup> At higher doses, however, epibatidine will cause paralysis and loss of consciousness, coma and eventually death. The <a href="/wiki/Median_lethal_dose" title="Median lethal dose">median lethal dose</a> (LD<sub>50</sub>) of epibatidine lies between 1.46 μg/kg and 13.98 μg/kg.<sup id="cite_ref-29" class="reference"><a href="#cite_note-29"><span class="cite-bracket">[</span>29<span class="cite-bracket">]</span></a></sup> This makes epibatidine somewhat more toxic than <a href="/wiki/Dioxin" title="Dioxin">dioxin</a> (with an average LD<sub>50</sub> of 22.8 μg/kg).<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (May 2018)">citation needed</span></a></i>]</sup> Due to the small difference between its toxic concentration and antinociceptive concentration, its therapeutic uses are very limited. </p><p>In research on mice, administration of doses greater than 5 μg/kg of epibatidine caused a dose-dependent paralyzing effect on the organism. With doses over 5 μg/kg, symptoms included <a href="/wiki/Hypertension" title="Hypertension">hypertension</a> (increased blood pressure), paralysis in the <a href="/wiki/Respiratory" class="mw-redirect" title="Respiratory">respiratory</a> system, seizures, and, ultimately, death. The symptoms do, however, change drastically when lower doses are given. Mice became resistant to pain and heat with none of the negative effects of higher doses. </p> <div class="mw-heading mw-heading3"><h3 id="Pharmacology">Pharmacology</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Epibatidine&action=edit&section=8" title="Edit section: Pharmacology"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Epibatidine most effectively enters the body through injection.<sup id="cite_ref-Sullivan_30-0" class="reference"><a href="#cite_note-Sullivan-30"><span class="cite-bracket">[</span>30<span class="cite-bracket">]</span></a></sup> <i><a href="/wiki/In_vitro" title="In vitro">In vitro</a></i> studies seem to suggest that epibatidine is hardly, if at all, metabolized in the human body.<sup id="cite_ref-pmid11093658_31-0" class="reference"><a href="#cite_note-pmid11093658-31"><span class="cite-bracket">[</span>31<span class="cite-bracket">]</span></a></sup> </p><p>Also there is currently little information on the path of clearance from the body. Maximum concentration in the brain is reached at about 30 minutes after entering the body.<sup id="cite_ref-Traynor_10-3" class="reference"><a href="#cite_note-Traynor-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Potential_medical_uses">Potential medical uses</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Epibatidine&action=edit&section=9" title="Edit section: Potential medical uses"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Epibatidine has a high analgesic potency, as stated above. Studies show it has a potency at least 200 times that of <a href="/wiki/Morphine" title="Morphine">morphine</a>.<sup id="cite_ref-Traynor_10-4" class="reference"><a href="#cite_note-Traynor-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> As the compound was not addictive nor did it cause <a href="/wiki/Habituation#Neurobiology_of_Habituation" title="Habituation">habituation</a>,<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (March 2014)">citation needed</span></a></i>]</sup>, it was initially thought to be very promising to replace morphine as a painkiller. However, the therapeutic concentration is very close to the toxic concentration. This means that even at a therapeutic dose (5 μg/kg<sup id="cite_ref-Daly_28-1" class="reference"><a href="#cite_note-Daly-28"><span class="cite-bracket">[</span>28<span class="cite-bracket">]</span></a></sup>), some epibatidine might bind to the <a href="/wiki/Muscarinic_acetylcholine_receptors" class="mw-redirect" title="Muscarinic acetylcholine receptors">muscarinic acetylcholine receptors</a> and cause adverse effects, such as <a href="/wiki/Hypertension" title="Hypertension">hypertension</a>, <a href="/wiki/Bradycardia" title="Bradycardia">bradycardia</a> and muscular <a href="/wiki/Paresis" title="Paresis">paresis</a>.<sup id="cite_ref-M._Fisher_23-2" class="reference"><a href="#cite_note-M._Fisher-23"><span class="cite-bracket">[</span>23<span class="cite-bracket">]</span></a></sup> </p><p>Compared to the gold standard in pain management, <a href="/wiki/Morphine" title="Morphine">morphine</a>, epibatidine needed only 2.5 μg/kg (11.98 nmol/kg) to initiate a pain-relieving effect whilst the same effect required approximately 10 mg/kg (35.05 μmol/kg) of morphine (approx. 2,900 times the efficacy.) Currently, only rudimentary research into epibatidine's effects has yet been performed; the drug has been administered only to <a href="/wiki/Rodents" class="mw-redirect" title="Rodents">rodents</a> for analysis at this time.<sup id="cite_ref-Broka_12-1" class="reference"><a href="#cite_note-Broka-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Antidote">Antidote</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Epibatidine&action=edit&section=10" title="Edit section: Antidote"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The antidote to epibatidine is <a href="/wiki/Mecamylamine" title="Mecamylamine">mecamylamine</a>,<sup id="cite_ref-Damaj_32-0" class="reference"><a href="#cite_note-Damaj-32"><span class="cite-bracket">[</span>32<span class="cite-bracket">]</span></a></sup> a nicotinic acetylcholine receptor antagonist that is non-selective and non-competitive.<sup id="cite_ref-Bacher_33-0" class="reference"><a href="#cite_note-Bacher-33"><span class="cite-bracket">[</span>33<span class="cite-bracket">]</span></a></sup> Both the (+) and the (-) enantiomers of mecamylamine were seen to be efficient and both have the same affinity for nicotinic acetylcholine receptors.<sup id="cite_ref-34" class="reference"><a href="#cite_note-34"><span class="cite-bracket">[</span>34<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="See_also">See also</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Epibatidine&action=edit&section=11" title="Edit section: See also"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a href="/wiki/6-Chloronicotine" title="6-Chloronicotine">6-Chloronicotine</a></li> <li><a href="/wiki/Arrow_poison" title="Arrow poison">Arrow poison</a></li> <li><a href="/wiki/Batrachotoxin" title="Batrachotoxin">Batrachotoxin</a> (and closely related <a href="/wiki/Homobatrachotoxin" class="mw-redirect" title="Homobatrachotoxin">homobatrachotoxin</a>)</li> <li><a href="/wiki/Nemertelline" title="Nemertelline">Nemertelline</a>, neurotoxin closely related to <a href="/wiki/Nicotelline" title="Nicotelline">nicotelline</a></li> <li><a href="/wiki/Phantasmidine" title="Phantasmidine">Phantasmidine</a></li> <li><a href="/wiki/Tetrodotoxin" title="Tetrodotoxin">Tetrodotoxin</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=Epibatidine&action=edit&section=12" title="Edit section: References"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1239543626">.mw-parser-output .reflist{margin-bottom:0.5em;list-style-type:decimal}@media screen{.mw-parser-output .reflist{font-size:90%}}.mw-parser-output .reflist .references{font-size:100%;margin-bottom:0;list-style-type:inherit}.mw-parser-output .reflist-columns-2{column-width:30em}.mw-parser-output .reflist-columns-3{column-width:25em}.mw-parser-output .reflist-columns{margin-top:0.3em}.mw-parser-output .reflist-columns ol{margin-top:0}.mw-parser-output .reflist-columns li{page-break-inside:avoid;break-inside:avoid-column}.mw-parser-output .reflist-upper-alpha{list-style-type:upper-alpha}.mw-parser-output .reflist-upper-roman{list-style-type:upper-roman}.mw-parser-output .reflist-lower-alpha{list-style-type:lower-alpha}.mw-parser-output .reflist-lower-greek{list-style-type:lower-greek}.mw-parser-output .reflist-lower-roman{list-style-type:lower-roman}</style><div class="reflist reflist-columns references-column-width reflist-columns-2"> <ol class="references"> <li id="cite_note-1"><span class="mw-cite-backlink"><b><a href="#cite_ref-1">^</a></b></span> <span class="reference-text"><style data-mw-deduplicate="TemplateStyles:r1238218222">.mw-parser-output cite.citation{font-style:inherit;word-wrap:break-word}.mw-parser-output .citation q{quotes:"\"""\"""'""'"}.mw-parser-output .citation:target{background-color:rgba(0,127,255,0.133)}.mw-parser-output .id-lock-free.id-lock-free a{background:url("//upload.wikimedia.org/wikipedia/commons/6/65/Lock-green.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-limited.id-lock-limited a,.mw-parser-output .id-lock-registration.id-lock-registration a{background:url("//upload.wikimedia.org/wikipedia/commons/d/d6/Lock-gray-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-subscription.id-lock-subscription a{background:url("//upload.wikimedia.org/wikipedia/commons/a/aa/Lock-red-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .cs1-ws-icon a{background:url("//upload.wikimedia.org/wikipedia/commons/4/4c/Wikisource-logo.svg")right 0.1em center/12px no-repeat}body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-free a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-limited a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-registration a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-subscription a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .cs1-ws-icon a{background-size:contain;padding:0 1em 0 0}.mw-parser-output .cs1-code{color:inherit;background:inherit;border:none;padding:inherit}.mw-parser-output .cs1-hidden-error{display:none;color:var(--color-error,#d33)}.mw-parser-output .cs1-visible-error{color:var(--color-error,#d33)}.mw-parser-output .cs1-maint{display:none;color:#085;margin-left:0.3em}.mw-parser-output .cs1-kern-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right{padding-right:0.2em}.mw-parser-output .citation .mw-selflink{font-weight:inherit}@media screen{.mw-parser-output .cs1-format{font-size:95%}html.skin-theme-clientpref-night .mw-parser-output .cs1-maint{color:#18911f}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .cs1-maint{color:#18911f}}</style><cite id="CITEREFFitchSpandeGarraffoYeh2010" class="citation journal cs1">Fitch RW, Spande TF, Garraffo HM, Yeh HJ, Daly JW (March 2010). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2866194">"Phantasmidine: an epibatidine congener from the ecuadorian poison frog Epipedobates anthonyi"</a>. <i>Journal of Natural Products</i>. <b>73</b> (3): <span class="nowrap">331–</span>337. <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%2Fnp900727e">10.1021/np900727e</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/PMC2866194">2866194</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/20337496">20337496</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+Natural+Products&rft.atitle=Phantasmidine%3A+an+epibatidine+congener+from+the+ecuadorian+poison+frog+Epipedobates+anthonyi&rft.volume=73&rft.issue=3&rft.pages=%3Cspan+class%3D%22nowrap%22%3E331-%3C%2Fspan%3E337&rft.date=2010-03&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC2866194%23id-name%3DPMC&rft_id=info%3Apmid%2F20337496&rft_id=info%3Adoi%2F10.1021%2Fnp900727e&rft.aulast=Fitch&rft.aufirst=RW&rft.au=Spande%2C+TF&rft.au=Garraffo%2C+HM&rft.au=Yeh%2C+HJ&rft.au=Daly%2C+JW&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC2866194&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEpibatidine" class="Z3988"></span></span> </li> <li id="cite_note-H.M._Garraffo_(2009)-2"><span class="mw-cite-backlink">^ <a href="#cite_ref-H.M._Garraffo_(2009)_2-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-H.M._Garraffo_(2009)_2-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-H.M._Garraffo_(2009)_2-2"><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="CITEREFGarraffoSpandeWilliams2009" class="citation journal cs1">Garraffo HM, Spande TF, Williams M (April 2009). <a rel="nofollow" class="external text" href="http://www.chm.bris.ac.uk/sillymolecules/epibatidine.pdf">"Epibatidine: from frog alkaloid to analgesic clinical candidates: a testimonial to" true grit"!"</a> <span class="cs1-format">(PDF)</span>. <i>Heterocycles</i>. <b>79</b> (1): <span class="nowrap">207–</span>217. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.3987%2FREV-08-SR%28D%295">10.3987/REV-08-SR(D)5</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Heterocycles&rft.atitle=Epibatidine%3A+from+frog+alkaloid+to+analgesic+clinical+candidates%3A+a+testimonial+to%22+true+grit%22%21.&rft.volume=79&rft.issue=1&rft.pages=%3Cspan+class%3D%22nowrap%22%3E207-%3C%2Fspan%3E217&rft.date=2009-04&rft_id=info%3Adoi%2F10.3987%2FREV-08-SR%28D%295&rft.aulast=Garraffo&rft.aufirst=HM&rft.au=Spande%2C+TF&rft.au=Williams%2C+M&rft_id=http%3A%2F%2Fwww.chm.bris.ac.uk%2Fsillymolecules%2Fepibatidine.pdf&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEpibatidine" class="Z3988"></span></span> </li> <li id="cite_note-Schwarcz,_Joe-3"><span class="mw-cite-backlink"><b><a href="#cite_ref-Schwarcz,_Joe_3-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFSchwarcz2012" class="citation book cs1">Schwarcz J (2012). <i>The Right Chemistry</i>. Random House.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=The+Right+Chemistry&rft.pub=Random+House&rft.date=2012&rft.aulast=Schwarcz&rft.aufirst=J&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEpibatidine" class="Z3988"></span></span> </li> <li id="cite_note-Epipedobates_anthonyi-4"><span class="mw-cite-backlink"><b><a href="#cite_ref-Epipedobates_anthonyi_4-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFMaxonWhittaker2009" class="citation web cs1">Maxon J, Whittaker K (March 2009). <a rel="nofollow" class="external text" href="http://amphibiaweb.org/cgi/amphib_query?where-genus=Epipedobates&where-species=anthonyi">"<i>Epipedobates anthonyi</i>"</a>. Berkeley, CA, USA: University of California<span class="reference-accessdate">. Retrieved <span class="nowrap">2015-05-06</span></span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=Epipedobates+anthonyi&rft.place=Berkeley%2C+CA%2C+USA&rft.pub=University+of+California&rft.date=2009-03&rft.aulast=Maxon&rft.aufirst=J&rft.au=Whittaker%2C+K&rft_id=http%3A%2F%2Famphibiaweb.org%2Fcgi%2Famphib_query%3Fwhere-genus%3DEpipedobates%26where-species%3Danthonyi&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEpibatidine" class="Z3988"></span></span> </li> <li id="cite_note-J.W._Daly_(2000)-5"><span class="mw-cite-backlink">^ <a href="#cite_ref-J.W._Daly_(2000)_5-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-J.W._Daly_(2000)_5-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-J.W._Daly_(2000)_5-2"><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="CITEREFDalyGarraffoSpandeDecker2000" class="citation journal cs1">Daly JW, Garraffo HM, Spande TF, Decker MW, Sullivan JP, Williams M (April 2000). <a rel="nofollow" class="external text" href="https://zenodo.org/record/1229984">"Alkaloids from frog skin: the discovery of epibatidine and the potential for developing novel non-opioid analgesics"</a>. <i>Natural Product Reports</i>. <b>17</b> (2): <span class="nowrap">131–</span>135. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1039%2Fa900728h">10.1039/a900728h</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/10821107">10821107</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Natural+Product+Reports&rft.atitle=Alkaloids+from+frog+skin%3A+the+discovery+of+epibatidine+and+the+potential+for+developing+novel+non-opioid+analgesics&rft.volume=17&rft.issue=2&rft.pages=%3Cspan+class%3D%22nowrap%22%3E131-%3C%2Fspan%3E135&rft.date=2000-04&rft_id=info%3Adoi%2F10.1039%2Fa900728h&rft_id=info%3Apmid%2F10821107&rft.aulast=Daly&rft.aufirst=JW&rft.au=Garraffo%2C+HM&rft.au=Spande%2C+TF&rft.au=Decker%2C+MW&rft.au=Sullivan%2C+JP&rft.au=Williams%2C+M&rft_id=https%3A%2F%2Fzenodo.org%2Frecord%2F1229984&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEpibatidine" class="Z3988"></span></span> </li> <li id="cite_note-E.N._Lasley_(1999)-6"><span class="mw-cite-backlink"><b><a href="#cite_ref-E.N._Lasley_(1999)_6-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFLasley1999" class="citation journal cs1">Lasley EN (December 1999). <a rel="nofollow" class="external text" href="https://doi.org/10.1525%2Fbisi.1999.49.12.945">"Having Their Toxins and Eating Them Too Study of the natural sources of many animals' chemical defenses is providing new insights into nature's medicine chest"</a>. <i>BioScience</i>. <b>45</b> (12). Oxford Journals: <span class="nowrap">945–</span>950. <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/10.1525%2Fbisi.1999.49.12.945">10.1525/bisi.1999.49.12.945</a></span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=BioScience&rft.atitle=Having+Their+Toxins+and+Eating+Them+Too+Study+of+the+natural+sources+of+many+animals%27+chemical+defenses+is+providing+new+insights+into+nature%27s+medicine+chest&rft.volume=45&rft.issue=12&rft.pages=%3Cspan+class%3D%22nowrap%22%3E945-%3C%2Fspan%3E950&rft.date=1999-12&rft_id=info%3Adoi%2F10.1525%2Fbisi.1999.49.12.945&rft.aulast=Lasley&rft.aufirst=EN&rft_id=https%3A%2F%2Fdoi.org%2F10.1525%252Fbisi.1999.49.12.945&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEpibatidine" class="Z3988"></span></span> </li> <li id="cite_note-7"><span class="mw-cite-backlink"><b><a href="#cite_ref-7">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFDalyGarraffoSpandeDecker2000" class="citation journal cs1">Daly JW, Garraffo HM, Spande TF, Decker MW, Sullivan JP, Williams M (April 2000). <a rel="nofollow" class="external text" href="https://zenodo.org/record/1229984">"Alkaloids from frog skin: the discovery of epibatidine and the potential for developing novel non-opioid analgesics"</a>. <i>Natural Product Reports</i>. <b>17</b> (2): <span class="nowrap">131–</span>135. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1039%2FA900728H">10.1039/A900728H</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/10821107">10821107</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Natural+Product+Reports&rft.atitle=Alkaloids+from+frog+skin%3A+the+discovery+of+epibatidine+and+the+potential+for+developing+novel+non-opioid+analgesics&rft.volume=17&rft.issue=2&rft.pages=%3Cspan+class%3D%22nowrap%22%3E131-%3C%2Fspan%3E135&rft.date=2000-04&rft_id=info%3Adoi%2F10.1039%2FA900728H&rft_id=info%3Apmid%2F10821107&rft.aulast=Daly&rft.aufirst=JW&rft.au=Garraffo%2C+HM&rft.au=Spande%2C+TF&rft.au=Decker%2C+MW&rft.au=Sullivan%2C+JP&rft.au=Williams%2C+M&rft_id=https%3A%2F%2Fzenodo.org%2Frecord%2F1229984&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEpibatidine" class="Z3988"></span></span> </li> <li id="cite_note-Donnelly-Roberts-8"><span class="mw-cite-backlink"><b><a href="#cite_ref-Donnelly-Roberts_8-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFDonnelly-RobertsPuttfarckenKuntzweilerBriggs1998" class="citation journal cs1">Donnelly-Roberts DL, Puttfarcken PS, Kuntzweiler TA, Briggs CA, Anderson DJ, Campbell JE, et al. (May 1998). <a rel="nofollow" class="external text" href="http://jpet.aspetjournals.org/content/285/2/777.short">"ABT-594 [(R)-5-(2-azetidinylmethoxy)-2-chloropyridine]: a novel, orally effective analgesic acting via neuronal nicotinic acetylcholine receptors: I. In vitro characterization"</a>. <i>The Journal of Pharmacology and Experimental Therapeutics</i>. <b>285</b> (2): <span class="nowrap">777–</span>786. <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/9580626">9580626</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+Pharmacology+and+Experimental+Therapeutics&rft.atitle=ABT-594+%5B%28R%29-5-%282-azetidinylmethoxy%29-2-chloropyridine%5D%3A+a+novel%2C+orally+effective+analgesic+acting+via+neuronal+nicotinic+acetylcholine+receptors%3A+I.+In+vitro+characterization&rft.volume=285&rft.issue=2&rft.pages=%3Cspan+class%3D%22nowrap%22%3E777-%3C%2Fspan%3E786&rft.date=1998-05&rft_id=info%3Apmid%2F9580626&rft.aulast=Donnelly-Roberts&rft.aufirst=DL&rft.au=Puttfarcken%2C+PS&rft.au=Kuntzweiler%2C+TA&rft.au=Briggs%2C+CA&rft.au=Anderson%2C+DJ&rft.au=Campbell%2C+JE&rft.au=Piattoni-Kaplan%2C+M&rft.au=McKenna%2C+DG&rft.au=Wasicak%2C+JT&rft.au=Holladay%2C+MW&rft.au=Williams%2C+M&rft.au=Arneric%2C+SP&rft_id=http%3A%2F%2Fjpet.aspetjournals.org%2Fcontent%2F285%2F2%2F777.short&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEpibatidine" class="Z3988"></span></span> </li> <li id="cite_note-9"><span class="mw-cite-backlink"><b><a href="#cite_ref-9">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFOlivoHemenway2002" class="citation journal cs1">Olivo HF, Hemenway MS (2002). "Recent syntheses of epibatidine. A review". <i>Organic Preparations and Procedures International</i>. <b>34</b> (1): <span class="nowrap">1–</span>26. <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%2F00304940209355744">10.1080/00304940209355744</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:98696766">98696766</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Organic+Preparations+and+Procedures+International&rft.atitle=Recent+syntheses+of+epibatidine.+A+review&rft.volume=34&rft.issue=1&rft.pages=%3Cspan+class%3D%22nowrap%22%3E1-%3C%2Fspan%3E26&rft.date=2002&rft_id=info%3Adoi%2F10.1080%2F00304940209355744&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A98696766%23id-name%3DS2CID&rft.aulast=Olivo&rft.aufirst=HF&rft.au=Hemenway%2C+MS&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEpibatidine" class="Z3988"></span></span> </li> <li id="cite_note-Traynor-10"><span class="mw-cite-backlink">^ <a href="#cite_ref-Traynor_10-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Traynor_10-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-Traynor_10-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-Traynor_10-3"><sup><i><b>d</b></i></sup></a> <a href="#cite_ref-Traynor_10-4"><sup><i><b>e</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFTraynor1998" class="citation journal cs1">Traynor JR (July 1998). <a rel="nofollow" class="external text" href="https://doi.org/10.1093%2Fbja%2F81.1.69">"Epibatidine and pain"</a>. <i>British Journal of Anaesthesia</i>. <b>81</b> (1): <span class="nowrap">69–</span>76. <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%2Fbja%2F81.1.69">10.1093/bja/81.1.69</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/9771274">9771274</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=British+Journal+of+Anaesthesia&rft.atitle=Epibatidine+and+pain&rft.volume=81&rft.issue=1&rft.pages=%3Cspan+class%3D%22nowrap%22%3E69-%3C%2Fspan%3E76&rft.date=1998-07&rft_id=info%3Adoi%2F10.1093%2Fbja%2F81.1.69&rft_id=info%3Apmid%2F9771274&rft.aulast=Traynor&rft.aufirst=JR&rft_id=https%3A%2F%2Fdoi.org%2F10.1093%252Fbja%252F81.1.69&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEpibatidine" class="Z3988"></span></span> </li> <li id="cite_note-car-11"><span class="mw-cite-backlink">^ <a href="#cite_ref-car_11-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-car_11-1"><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="CITEREFClaytonRegan1993" class="citation journal cs1">Clayton SC, Regan AC (1993). "A total synthesis of (±)-epibatidine". <i>Tetrahedron Letters</i>. <b>34</b> (46): <span class="nowrap">7493–</span>7496. <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%2FS0040-4039%2800%2960162-4">10.1016/S0040-4039(00)60162-4</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Tetrahedron+Letters&rft.atitle=A+total+synthesis+of+%28%C2%B1%29-epibatidine&rft.volume=34&rft.issue=46&rft.pages=%3Cspan+class%3D%22nowrap%22%3E7493-%3C%2Fspan%3E7496&rft.date=1993&rft_id=info%3Adoi%2F10.1016%2FS0040-4039%2800%2960162-4&rft.aulast=Clayton&rft.aufirst=SC&rft.au=Regan%2C+AC&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEpibatidine" class="Z3988"></span></span> </li> <li id="cite_note-Broka-12"><span class="mw-cite-backlink">^ <a href="#cite_ref-Broka_12-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Broka_12-1"><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="CITEREFBroka1994" class="citation journal cs1">Broka CA (1994). "Synthetic approaches to epibatidine". <i>Medicinal Chemistry Research</i>. <b>4</b> (7): <span class="nowrap">449–</span>460.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Medicinal+Chemistry+Research&rft.atitle=Synthetic+approaches+to+epibatidine.&rft.volume=4&rft.issue=7&rft.pages=%3Cspan+class%3D%22nowrap%22%3E449-%3C%2Fspan%3E460&rft.date=1994&rft.aulast=Broka&rft.aufirst=CA&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEpibatidine" class="Z3988"></span></span> </li> <li id="cite_note-13"><span class="mw-cite-backlink"><b><a href="#cite_ref-13">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFBroka1993" class="citation journal cs1">Broka CA (1993). "Total synthesis of epibatidine". <i>Tetrahedron Lett</i>. <b>34</b> (20): <span class="nowrap">3251–</span>3254. <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%2Fs0040-4039%2800%2973674-4">10.1016/s0040-4039(00)73674-4</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Tetrahedron+Lett&rft.atitle=Total+synthesis+of+epibatidine&rft.volume=34&rft.issue=20&rft.pages=%3Cspan+class%3D%22nowrap%22%3E3251-%3C%2Fspan%3E3254&rft.date=1993&rft_id=info%3Adoi%2F10.1016%2Fs0040-4039%2800%2973674-4&rft.aulast=Broka&rft.aufirst=CA&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEpibatidine" class="Z3988"></span></span> </li> <li id="cite_note-14"><span class="mw-cite-backlink"><b><a href="#cite_ref-14">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFHuangShen1993" class="citation journal cs1">Huang DF, Shen TY (1993). "A versatile total synthesis of epibatidine and analogs". <i>Tetrahedron Lett</i>. <b>34</b> (28): <span class="nowrap">4477–</span>4480. <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%2F0040-4039%2893%2988063-o">10.1016/0040-4039(93)88063-o</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Tetrahedron+Lett&rft.atitle=A+versatile+total+synthesis+of+epibatidine+and+analogs&rft.volume=34&rft.issue=28&rft.pages=%3Cspan+class%3D%22nowrap%22%3E4477-%3C%2Fspan%3E4480&rft.date=1993&rft_id=info%3Adoi%2F10.1016%2F0040-4039%2893%2988063-o&rft.aulast=Huang&rft.aufirst=DF&rft.au=Shen%2C+TY&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEpibatidine" class="Z3988"></span></span> </li> <li id="cite_note-Dowd-15"><span class="mw-cite-backlink">^ <a href="#cite_ref-Dowd_15-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Dowd_15-1"><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="CITEREFDowd" class="citation web cs1">Dowd MJ. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20101205015705/http://www.pharmacy.vcu.edu/medchem/articles/epi/index.html">"Epibatidine"</a>. <i>Department of Medicinal Chemistry</i>. Virginia Commonwealth University. Archived from <a rel="nofollow" class="external text" href="http://www.pharmacy.vcu.edu/medchem/articles/epi/index.html">the original</a> on December 5, 2010.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=Department+of+Medicinal+Chemistry&rft.atitle=Epibatidine&rft.aulast=Dowd&rft.aufirst=MJ&rft_id=http%3A%2F%2Fwww.pharmacy.vcu.edu%2Fmedchem%2Farticles%2Fepi%2Findex.html&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEpibatidine" 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 class="citation web cs1"><a rel="nofollow" class="external text" href="http://www.mongabay.com/05epidatidine.htm">"Deriving a non-opiate painkiller [ABT-594] from Epipedobates tricolor"</a>. Mongabay.com<span class="reference-accessdate">. Retrieved <span class="nowrap">2014-03-12</span></span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=Deriving+a+non-opiate+painkiller+%5BABT-594%26%2393%3B+from+Epipedobates+tricolor&rft.pub=Mongabay.com&rft_id=http%3A%2F%2Fwww.mongabay.com%2F05epidatidine.htm&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEpibatidine" class="Z3988"></span></span> </li> <li id="cite_note-17"><span class="mw-cite-backlink"><b><a href="#cite_ref-17">^</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.chm.bris.ac.uk/webprojects2002/jjones/Content/Epibatidine.htm">"Epibatidine"</a>. <i>School of Chemistry</i>. University of Bristol<span class="reference-accessdate">. Retrieved <span class="nowrap">2021-11-12</span></span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=School+of+Chemistry&rft.atitle=Epibatidine&rft_id=http%3A%2F%2Fwww.chm.bris.ac.uk%2Fwebprojects2002%2Fjjones%2FContent%2FEpibatidine.htm&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEpibatidine" class="Z3988"></span></span> </li> <li id="cite_note-18"><span class="mw-cite-backlink"><b><a href="#cite_ref-18">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFRizziDallanoceMateraMagrone2008" class="citation journal cs1">Rizzi L, Dallanoce C, Matera C, Magrone P, Pucci L, Gotti C, et al. (August 2008). "Epiboxidine and novel-related analogues: a convenient synthetic approach and estimation of their affinity at neuronal nicotinic acetylcholine receptor subtypes". <i>Bioorganic & Medicinal Chemistry Letters</i>. <b>18</b> (16): <span class="nowrap">4651–</span>4654. <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.bmcl.2008.07.016">10.1016/j.bmcl.2008.07.016</a>. <a href="/wiki/Hdl_(identifier)" class="mw-redirect" title="Hdl (identifier)">hdl</a>:<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://hdl.handle.net/2434%2F59291">2434/59291</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/18644719">18644719</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Bioorganic+%26+Medicinal+Chemistry+Letters&rft.atitle=Epiboxidine+and+novel-related+analogues%3A+a+convenient+synthetic+approach+and+estimation+of+their+affinity+at+neuronal+nicotinic+acetylcholine+receptor+subtypes&rft.volume=18&rft.issue=16&rft.pages=%3Cspan+class%3D%22nowrap%22%3E4651-%3C%2Fspan%3E4654&rft.date=2008-08&rft_id=info%3Ahdl%2F2434%2F59291&rft_id=info%3Apmid%2F18644719&rft_id=info%3Adoi%2F10.1016%2Fj.bmcl.2008.07.016&rft.aulast=Rizzi&rft.aufirst=L&rft.au=Dallanoce%2C+C&rft.au=Matera%2C+C&rft.au=Magrone%2C+P&rft.au=Pucci%2C+L&rft.au=Gotti%2C+C&rft.au=Clementi%2C+F&rft.au=De+Amici%2C+M&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEpibatidine" class="Z3988"></span></span> </li> <li id="cite_note-19"><span class="mw-cite-backlink"><b><a href="#cite_ref-19">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFDallanoceMateraDe_AmiciRizzi2012" class="citation journal cs1">Dallanoce C, Matera C, De Amici M, Rizzi L, Pucci L, Gotti C, et al. (July 2012). "The enantiomers of epiboxidine and of two related analogs: synthesis and estimation of their binding affinity at α4β2 and α7 neuronal nicotinic acetylcholine receptors". <i>Chirality</i>. <b>24</b> (7): <span class="nowrap">543–</span>551. <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%2Fchir.22052">10.1002/chir.22052</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/22566097">22566097</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Chirality&rft.atitle=The+enantiomers+of+epiboxidine+and+of+two+related+analogs%3A+synthesis+and+estimation+of+their+binding+affinity+at+%CE%B14%CE%B22+and+%CE%B17+neuronal+nicotinic+acetylcholine+receptors&rft.volume=24&rft.issue=7&rft.pages=%3Cspan+class%3D%22nowrap%22%3E543-%3C%2Fspan%3E551&rft.date=2012-07&rft_id=info%3Adoi%2F10.1002%2Fchir.22052&rft_id=info%3Apmid%2F22566097&rft.aulast=Dallanoce&rft.aufirst=C&rft.au=Matera%2C+C&rft.au=De+Amici%2C+M&rft.au=Rizzi%2C+L&rft.au=Pucci%2C+L&rft.au=Gotti%2C+C&rft.au=Clementi%2C+F&rft.au=De+Micheli%2C+C&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEpibatidine" class="Z3988"></span></span> </li> <li id="cite_note-20"><span class="mw-cite-backlink"><b><a href="#cite_ref-20">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFDallanoceMateraPucciGotti2012" class="citation journal cs1">Dallanoce C, Matera C, Pucci L, Gotti C, Clementi F, Amici MD, Micheli CD (January 2012). "Synthesis and binding affinity at α4β2 and α7 nicotinic acetylcholine receptors of new analogs of epibatidine and epiboxidine containing the 7-azabicyclo[2.2.1]hept-2-ene ring system". <i>Bioorganic & Medicinal Chemistry Letters</i>. <b>22</b> (2): <span class="nowrap">829–</span>832. <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.bmcl.2011.12.052">10.1016/j.bmcl.2011.12.052</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/22222032">22222032</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Bioorganic+%26+Medicinal+Chemistry+Letters&rft.atitle=Synthesis+and+binding+affinity+at+%CE%B14%CE%B22+and+%CE%B17+nicotinic+acetylcholine+receptors+of+new+analogs+of+epibatidine+and+epiboxidine+containing+the+7-azabicyclo%5B2.2.1%5Dhept-2-ene+ring+system&rft.volume=22&rft.issue=2&rft.pages=%3Cspan+class%3D%22nowrap%22%3E829-%3C%2Fspan%3E832&rft.date=2012-01&rft_id=info%3Adoi%2F10.1016%2Fj.bmcl.2011.12.052&rft_id=info%3Apmid%2F22222032&rft.aulast=Dallanoce&rft.aufirst=C&rft.au=Matera%2C+C&rft.au=Pucci%2C+L&rft.au=Gotti%2C+C&rft.au=Clementi%2C+F&rft.au=Amici%2C+MD&rft.au=Micheli%2C+CD&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEpibatidine" class="Z3988"></span></span> </li> <li id="cite_note-21"><span class="mw-cite-backlink"><b><a href="#cite_ref-21">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFDallanoceMagroneMateraLo_Presti2010" class="citation journal cs1">Dallanoce C, Magrone P, Matera C, Lo Presti L, De Amici M, Riganti L, et al. (December 2010). "Synthesis of novel chiral Δ2-isoxazoline derivatives related to ABT-418 and estimation of their affinity at neuronal nicotinic acetylcholine receptor subtypes". <i>European Journal of Medicinal Chemistry</i>. <b>45</b> (12): <span class="nowrap">5594–</span>5601. <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.ejmech.2010.09.009">10.1016/j.ejmech.2010.09.009</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/20932609">20932609</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+Medicinal+Chemistry&rft.atitle=Synthesis+of+novel+chiral+%CE%942-isoxazoline+derivatives+related+to+ABT-418+and+estimation+of+their+affinity+at+neuronal+nicotinic+acetylcholine+receptor+subtypes&rft.volume=45&rft.issue=12&rft.pages=%3Cspan+class%3D%22nowrap%22%3E5594-%3C%2Fspan%3E5601&rft.date=2010-12&rft_id=info%3Adoi%2F10.1016%2Fj.ejmech.2010.09.009&rft_id=info%3Apmid%2F20932609&rft.aulast=Dallanoce&rft.aufirst=C&rft.au=Magrone%2C+P&rft.au=Matera%2C+C&rft.au=Lo+Presti%2C+L&rft.au=De+Amici%2C+M&rft.au=Riganti%2C+L&rft.au=Clementi%2C+F&rft.au=Gotti%2C+C&rft.au=De+Micheli%2C+C&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEpibatidine" class="Z3988"></span></span> </li> <li id="cite_note-22"><span class="mw-cite-backlink"><b><a href="#cite_ref-22">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFOlivoHemenway1999" class="citation journal cs1">Olivo HF, Hemenway MS (November 1999). "Total Synthesis of (+/-)-Epibatidine Using a Biocatalytic Approach". <i>The Journal of Organic Chemistry</i>. <b>64</b> (24): <span class="nowrap">8968–</span>8969. <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%2Fjo991141q">10.1021/jo991141q</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/11674810">11674810</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+Organic+Chemistry&rft.atitle=Total+Synthesis+of+%28%2B%2F-%29-Epibatidine+Using+a+Biocatalytic+Approach&rft.volume=64&rft.issue=24&rft.pages=%3Cspan+class%3D%22nowrap%22%3E8968-%3C%2Fspan%3E8969&rft.date=1999-11&rft_id=info%3Adoi%2F10.1021%2Fjo991141q&rft_id=info%3Apmid%2F11674810&rft.aulast=Olivo&rft.aufirst=HF&rft.au=Hemenway%2C+MS&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEpibatidine" class="Z3988"></span></span> </li> <li id="cite_note-M._Fisher-23"><span class="mw-cite-backlink">^ <a href="#cite_ref-M._Fisher_23-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-M._Fisher_23-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-M._Fisher_23-2"><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="CITEREFFisherHuangfuShenGuyenet1994" class="citation journal cs1">Fisher M, Huangfu D, Shen TY, Guyenet PG (August 1994). <a rel="nofollow" class="external text" href="http://jpet.aspetjournals.org/content/270/2/702.abstract">"Epibatidine, an alkaloid from the poison frog Epipedobates tricolor, is a powerful ganglionic depolarizing agent"</a>. <i>The Journal of Pharmacology and Experimental Therapeutics</i>. <b>270</b> (2): <span class="nowrap">702–</span>707. <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/8071862">8071862</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+Pharmacology+and+Experimental+Therapeutics&rft.atitle=Epibatidine%2C+an+alkaloid+from+the+poison+frog+Epipedobates+tricolor%2C+is+a+powerful+ganglionic+depolarizing+agent&rft.volume=270&rft.issue=2&rft.pages=%3Cspan+class%3D%22nowrap%22%3E702-%3C%2Fspan%3E707&rft.date=1994-08&rft_id=info%3Apmid%2F8071862&rft.aulast=Fisher&rft.aufirst=M&rft.au=Huangfu%2C+D&rft.au=Shen%2C+TY&rft.au=Guyenet%2C+PG&rft_id=http%3A%2F%2Fjpet.aspetjournals.org%2Fcontent%2F270%2F2%2F702.abstract&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEpibatidine" class="Z3988"></span></span> </li> <li id="cite_note-24"><span class="mw-cite-backlink"><b><a href="#cite_ref-24">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFTraynor1998" class="citation journal cs1">Traynor JR (July 1998). <a rel="nofollow" class="external text" href="https://doi.org/10.1093%2Fbja%2F81.1.69">"Epibatidine and pain"</a>. <i>British Journal of Anaesthesia</i>. <b>81</b> (1): <span class="nowrap">69–</span>76. <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%2Fbja%2F81.1.69">10.1093/bja/81.1.69</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/9771274">9771274</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=British+Journal+of+Anaesthesia&rft.atitle=Epibatidine+and+pain&rft.volume=81&rft.issue=1&rft.pages=%3Cspan+class%3D%22nowrap%22%3E69-%3C%2Fspan%3E76&rft.date=1998-07&rft_id=info%3Adoi%2F10.1093%2Fbja%2F81.1.69&rft_id=info%3Apmid%2F9771274&rft.aulast=Traynor&rft.aufirst=JR&rft_id=https%3A%2F%2Fdoi.org%2F10.1093%252Fbja%252F81.1.69&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEpibatidine" class="Z3988"></span></span> </li> <li id="cite_note-25"><span class="mw-cite-backlink"><b><a href="#cite_ref-25">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFPrinceSine1998" class="citation journal cs1">Prince RJ, Sine SM (April 1998). <a rel="nofollow" class="external text" href="https://doi.org/10.1074%2Fjbc.273.14.7843">"Epibatidine binds with unique site and state selectivity to muscle nicotinic acetylcholine receptors"</a>. <i>The Journal of Biological Chemistry</i>. <b>273</b> (14): <span class="nowrap">7843–</span>7849. <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.273.14.7843">10.1074/jbc.273.14.7843</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/9525877">9525877</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=Epibatidine+binds+with+unique+site+and+state+selectivity+to+muscle+nicotinic+acetylcholine+receptors&rft.volume=273&rft.issue=14&rft.pages=%3Cspan+class%3D%22nowrap%22%3E7843-%3C%2Fspan%3E7849&rft.date=1998-04&rft_id=info%3Adoi%2F10.1074%2Fjbc.273.14.7843&rft_id=info%3Apmid%2F9525877&rft.aulast=Prince&rft.aufirst=RJ&rft.au=Sine%2C+SM&rft_id=https%3A%2F%2Fdoi.org%2F10.1074%252Fjbc.273.14.7843&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEpibatidine" class="Z3988"></span></span> </li> <li id="cite_note-26"><span class="mw-cite-backlink"><b><a href="#cite_ref-26">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFHoggRaggenbassBertrand2003" class="citation journal cs1">Hogg RC, Raggenbass M, Bertrand D (2003). "Nicotinic acetylcholine receptors: from structure to brain function". <i>Reviews of Physiology, Biochemistry and Pharmacology</i>. <b>147</b>: <span class="nowrap">1–</span>46. <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%2Fs10254-003-0005-1">10.1007/s10254-003-0005-1</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-3-540-01365-5" title="Special:BookSources/978-3-540-01365-5"><bdi>978-3-540-01365-5</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/12783266">12783266</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Reviews+of+Physiology%2C+Biochemistry+and+Pharmacology&rft.atitle=Nicotinic+acetylcholine+receptors%3A+from+structure+to+brain+function&rft.volume=147&rft.pages=%3Cspan+class%3D%22nowrap%22%3E1-%3C%2Fspan%3E46&rft.date=2003&rft_id=info%3Apmid%2F12783266&rft_id=info%3Adoi%2F10.1007%2Fs10254-003-0005-1&rft.isbn=978-3-540-01365-5&rft.aulast=Hogg&rft.aufirst=RC&rft.au=Raggenbass%2C+M&rft.au=Bertrand%2C+D&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEpibatidine" class="Z3988"></span></span> </li> <li id="cite_note-27"><span class="mw-cite-backlink"><b><a href="#cite_ref-27">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFOlena2017" class="citation web cs1">Olena A (September 21, 2017). <a rel="nofollow" class="external text" href="http://www.the-scientist.com/?articles.view/articleNo/50409/title/How-Poison-Frogs-Avoid-Poisoning-Themselves/">"How Poison Frogs Avoid Poisoning Themselves"</a>. <i>The Scientist</i>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=The+Scientist&rft.atitle=How+Poison+Frogs+Avoid+Poisoning+Themselves.&rft.date=2017-09-21&rft.aulast=Olena&rft.aufirst=A&rft_id=http%3A%2F%2Fwww.the-scientist.com%2F%3Farticles.view%2FarticleNo%2F50409%2Ftitle%2FHow-Poison-Frogs-Avoid-Poisoning-Themselves%2F&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEpibatidine" class="Z3988"></span></span> </li> <li id="cite_note-Daly-28"><span class="mw-cite-backlink">^ <a href="#cite_ref-Daly_28-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Daly_28-1"><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="CITEREFBadioDaly1994" class="citation journal cs1">Badio B, Daly JW (April 1994). "Epibatidine, a potent analgetic and nicotinic agonist". <i>Molecular Pharmacology</i>. <b>45</b> (4): <span class="nowrap">563–</span>9. <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/8183234">8183234</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Molecular+Pharmacology&rft.atitle=Epibatidine%2C+a+potent+analgetic+and+nicotinic+agonist&rft.volume=45&rft.issue=4&rft.pages=%3Cspan+class%3D%22nowrap%22%3E563-%3C%2Fspan%3E9&rft.date=1994-04&rft_id=info%3Apmid%2F8183234&rft.aulast=Badio&rft.aufirst=B&rft.au=Daly%2C+JW&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEpibatidine" class="Z3988"></span></span> </li> <li id="cite_note-29"><span class="mw-cite-backlink"><b><a href="#cite_ref-29">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFSihverLångströmNordberg2002" class="citation journal cs1">Sihver W, Långström B, Nordberg A (2002). <a rel="nofollow" class="external text" href="https://doi.org/10.1034%2Fj.1600-0404.2000.00304.x">"Ligands for in vivo imaging of nicotinic receptor subtypes in Alzheimer brain"</a>. <i>Acta Neurologica Scandinavica. Supplementum</i>. <b>176</b>: <span class="nowrap">27–</span>33. <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/10.1034%2Fj.1600-0404.2000.00304.x">10.1034/j.1600-0404.2000.00304.x</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/11261802">11261802</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:23541883">23541883</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Acta+Neurologica+Scandinavica.+Supplementum&rft.atitle=Ligands+for+in+vivo+imaging+of+nicotinic+receptor+subtypes+in+Alzheimer+brain&rft.volume=176&rft.pages=%3Cspan+class%3D%22nowrap%22%3E27-%3C%2Fspan%3E33&rft.date=2002&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A23541883%23id-name%3DS2CID&rft_id=info%3Apmid%2F11261802&rft_id=info%3Adoi%2F10.1034%2Fj.1600-0404.2000.00304.x&rft.aulast=Sihver&rft.aufirst=W&rft.au=L%C3%A5ngstr%C3%B6m%2C+B&rft.au=Nordberg%2C+A&rft_id=https%3A%2F%2Fdoi.org%2F10.1034%252Fj.1600-0404.2000.00304.x&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEpibatidine" class="Z3988"></span></span> </li> <li id="cite_note-Sullivan-30"><span class="mw-cite-backlink"><b><a href="#cite_ref-Sullivan_30-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFSullivanBannon1996" class="citation journal cs1">Sullivan JP, Bannon AW (1996). "Epibatidine: Pharmacological Properties of a Novel Nicotinic Acetylcholine Receptor Agonist and Analgesic Agent". <i>CNS Drug Reviews</i>. <b>2</b> (1): <span class="nowrap">21–</span>39. <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.1527-3458.1996.tb00288.x">10.1111/j.1527-3458.1996.tb00288.x</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=CNS+Drug+Reviews&rft.atitle=Epibatidine%3A+Pharmacological+Properties+of+a+Novel+Nicotinic+Acetylcholine+Receptor+Agonist+and+Analgesic+Agent&rft.volume=2&rft.issue=1&rft.pages=%3Cspan+class%3D%22nowrap%22%3E21-%3C%2Fspan%3E39&rft.date=1996&rft_id=info%3Adoi%2F10.1111%2Fj.1527-3458.1996.tb00288.x&rft.aulast=Sullivan&rft.aufirst=JP&rft.au=Bannon%2C+AW&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEpibatidine" class="Z3988"></span></span> </li> <li id="cite_note-pmid11093658-31"><span class="mw-cite-backlink"><b><a href="#cite_ref-pmid11093658_31-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFWattHitzelMorrisonLocker2000" class="citation journal cs1">Watt AP, Hitzel L, Morrison D, Locker KL (October 2000). "Determination of the in vitro metabolism of (+)- and (-)-epibatidine". <i>Journal of Chromatography A</i>. <b>896</b> (<span class="nowrap">1–</span>2): <span class="nowrap">229–</span>38. <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%2Fs0021-9673%2800%2900597-5">10.1016/s0021-9673(00)00597-5</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/11093658">11093658</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+Chromatography+A&rft.atitle=Determination+of+the+in+vitro+metabolism+of+%28%2B%29-+and+%28-%29-epibatidine&rft.volume=896&rft.issue=%3Cspan+class%3D%22nowrap%22%3E1%E2%80%93%3C%2Fspan%3E2&rft.pages=%3Cspan+class%3D%22nowrap%22%3E229-%3C%2Fspan%3E38&rft.date=2000-10&rft_id=info%3Adoi%2F10.1016%2Fs0021-9673%2800%2900597-5&rft_id=info%3Apmid%2F11093658&rft.aulast=Watt&rft.aufirst=AP&rft.au=Hitzel%2C+L&rft.au=Morrison%2C+D&rft.au=Locker%2C+KL&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEpibatidine" class="Z3988"></span></span> </li> <li id="cite_note-Damaj-32"><span class="mw-cite-backlink"><b><a href="#cite_ref-Damaj_32-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFDamajCreasyGroveRosecrans1994" class="citation journal cs1">Damaj MI, Creasy KR, Grove AD, Rosecrans JA, Martin BR (November 1994). "Pharmacological effects of epibatidine optical enantiomers". <i>Brain Research</i>. <b>664</b> (<span class="nowrap">1–</span>2): <span class="nowrap">34–</span>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%2F0006-8993%2894%2991950-x">10.1016/0006-8993(94)91950-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/7895043">7895043</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:46489298">46489298</a>.</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=Pharmacological+effects+of+epibatidine+optical+enantiomers&rft.volume=664&rft.issue=%3Cspan+class%3D%22nowrap%22%3E1%E2%80%93%3C%2Fspan%3E2&rft.pages=%3Cspan+class%3D%22nowrap%22%3E34-%3C%2Fspan%3E40&rft.date=1994-11&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A46489298%23id-name%3DS2CID&rft_id=info%3Apmid%2F7895043&rft_id=info%3Adoi%2F10.1016%2F0006-8993%2894%2991950-x&rft.aulast=Damaj&rft.aufirst=MI&rft.au=Creasy%2C+KR&rft.au=Grove%2C+AD&rft.au=Rosecrans%2C+JA&rft.au=Martin%2C+BR&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEpibatidine" class="Z3988"></span></span> </li> <li id="cite_note-Bacher-33"><span class="mw-cite-backlink"><b><a href="#cite_ref-Bacher_33-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFBacherWuShytleGeorge2009" class="citation journal cs1">Bacher I, Wu B, Shytle DR, George TP (November 2009). "Mecamylamine - a nicotinic acetylcholine receptor antagonist with potential for the treatment of neuropsychiatric disorders". <i>Expert Opinion on Pharmacotherapy</i>. <b>10</b> (16): <span class="nowrap">2709–</span>2721. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1517%2F14656560903329102">10.1517/14656560903329102</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/19874251">19874251</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:25690407">25690407</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Expert+Opinion+on+Pharmacotherapy&rft.atitle=Mecamylamine+-+a+nicotinic+acetylcholine+receptor+antagonist+with+potential+for+the+treatment+of+neuropsychiatric+disorders&rft.volume=10&rft.issue=16&rft.pages=%3Cspan+class%3D%22nowrap%22%3E2709-%3C%2Fspan%3E2721&rft.date=2009-11&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A25690407%23id-name%3DS2CID&rft_id=info%3Apmid%2F19874251&rft_id=info%3Adoi%2F10.1517%2F14656560903329102&rft.aulast=Bacher&rft.aufirst=I&rft.au=Wu%2C+B&rft.au=Shytle%2C+DR&rft.au=George%2C+TP&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEpibatidine" class="Z3988"></span></span> </li> <li id="cite_note-34"><span class="mw-cite-backlink"><b><a href="#cite_ref-34">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFNickellGrinevichSiripurapuSmith2013" class="citation journal cs1">Nickell JR, Grinevich VP, Siripurapu KB, Smith AM, Dwoskin LP (July 2013). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3690754">"Potential therapeutic uses of mecamylamine and its stereoisomers"</a>. <i>Pharmacology, Biochemistry, and Behavior</i>. <b>108</b>: <span class="nowrap">28–</span>43. <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.pbb.2013.04.005">10.1016/j.pbb.2013.04.005</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/PMC3690754">3690754</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/23603417">23603417</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Pharmacology%2C+Biochemistry%2C+and+Behavior&rft.atitle=Potential+therapeutic+uses+of+mecamylamine+and+its+stereoisomers&rft.volume=108&rft.pages=%3Cspan+class%3D%22nowrap%22%3E28-%3C%2Fspan%3E43&rft.date=2013-07&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC3690754%23id-name%3DPMC&rft_id=info%3Apmid%2F23603417&rft_id=info%3Adoi%2F10.1016%2Fj.pbb.2013.04.005&rft.aulast=Nickell&rft.aufirst=JR&rft.au=Grinevich%2C+VP&rft.au=Siripurapu%2C+KB&rft.au=Smith%2C+AM&rft.au=Dwoskin%2C+LP&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC3690754&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEpibatidine" class="Z3988"></span></span> </li> </ol></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=Epibatidine&action=edit&section=13" title="Edit section: External links"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a rel="nofollow" class="external text" href="https://web.archive.org/web/20090106012913/http://www.chemsoc.org/ExemplarChem/entries/2004/icl_Pan/index.html">Epibatidine at chemsoc.org</a></li></ul> <div class="navbox-styles"><style data-mw-deduplicate="TemplateStyles:r1129693374">.mw-parser-output .hlist dl,.mw-parser-output .hlist ol,.mw-parser-output .hlist ul{margin:0;padding:0}.mw-parser-output .hlist dd,.mw-parser-output .hlist dt,.mw-parser-output .hlist li{margin:0;display:inline}.mw-parser-output .hlist.inline,.mw-parser-output .hlist.inline dl,.mw-parser-output .hlist.inline ol,.mw-parser-output .hlist.inline ul,.mw-parser-output .hlist dl dl,.mw-parser-output .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: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></div><div role="navigation" class="navbox" aria-labelledby="Stimulants535" 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" /><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:Stimulants" title="Template:Stimulants"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Stimulants" title="Template talk:Stimulants"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Stimulants" title="Special:EditPage/Template:Stimulants"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Stimulants535" style="font-size:114%;margin:0 4em"><a href="/wiki/Stimulant" title="Stimulant">Stimulants</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Adamantane" title="Adamantane">Adamantanes</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/Adapromine" title="Adapromine">Adapromine</a></li> <li><a href="/wiki/Amantadine" title="Amantadine">Amantadine</a></li> <li><a href="/wiki/Bromantane" title="Bromantane">Bromantane</a></li> <li><a href="/wiki/Memantine" title="Memantine">Memantine</a></li> <li><a href="/wiki/Rimantadine" title="Rimantadine">Rimantadine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Adenosine_receptor" title="Adenosine receptor">Adenosine antagonists</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/8-Chlorotheophylline" title="8-Chlorotheophylline">8-Chlorotheophylline</a></li> <li><a href="/wiki/8-Cyclopentyl-1,3-dimethylxanthine" title="8-Cyclopentyl-1,3-dimethylxanthine">8-Cyclopentyltheophylline</a></li> <li><a href="/wiki/8-Phenyltheophylline" title="8-Phenyltheophylline">8-Phenyltheophylline</a></li> <li><a href="/wiki/Aminophylline" title="Aminophylline">Aminophylline</a></li> <li><a href="/wiki/Caffeine" title="Caffeine">Caffeine</a></li> <li><a href="/wiki/CGS-15943" title="CGS-15943">CGS-15943</a></li> <li><a href="/wiki/Dimethazan" title="Dimethazan">Dimethazan</a></li> <li><a href="/wiki/Istradefylline" title="Istradefylline">Istradefylline</a></li> <li><a href="/wiki/Paraxanthine" title="Paraxanthine">Paraxanthine</a></li> <li><a href="/wiki/SCH-58261" title="SCH-58261">SCH-58261</a></li> <li><a href="/wiki/Theobromine" title="Theobromine">Theobromine</a></li> <li><a href="/wiki/Theophylline" title="Theophylline">Theophylline</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Psychotropic_alkylamines" title="Psychotropic alkylamines">Alkylamines</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/Cyclopentamine" title="Cyclopentamine">Cyclopentamine</a></li> <li><a href="/wiki/Cypenamine" title="Cypenamine">Cypenamine</a></li> <li><a href="/wiki/Cyprodenate" title="Cyprodenate">Cyprodenate</a></li> <li><a href="/wiki/Heptaminol" title="Heptaminol">Heptaminol</a></li> <li><a href="/wiki/Isometheptene" title="Isometheptene">Isometheptene</a></li> <li><a href="/wiki/Methylhexanamine" title="Methylhexanamine">Methylhexaneamine</a></li> <li><a href="/wiki/Octodrine" title="Octodrine">Octodrine</a></li> <li><a href="/wiki/Propylhexedrine" title="Propylhexedrine">Propylhexedrine</a></li> <li><a href="/wiki/Tuaminoheptane" title="Tuaminoheptane">Tuaminoheptane</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Ampakine" title="Ampakine">Ampakines</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/CX-516" title="CX-516">CX-516</a></li> <li><a href="/wiki/CX-546" title="CX-546">CX-546</a></li> <li><a href="/wiki/CX-614" class="mw-redirect" title="CX-614">CX-614</a></li> <li><a href="/wiki/Farampator" title="Farampator">CX-691</a></li> <li><a href="/wiki/CX717" title="CX717">CX-717</a></li> <li><a href="/wiki/IDRA-21" title="IDRA-21">IDRA-21</a></li> <li><a href="/wiki/LY-404,187" class="mw-redirect" title="LY-404,187">LY-404,187</a></li> <li><a href="/wiki/LY-503,430" class="mw-redirect" title="LY-503,430">LY-503,430</a></li> <li><a href="/wiki/Nooglutyl" title="Nooglutyl">Nooglutyl</a></li> <li><a href="/wiki/Org_26576" class="mw-redirect" title="Org 26576">Org 26576</a></li> <li><a href="/wiki/PEPA_(drug)" title="PEPA (drug)">PEPA</a></li> <li><a href="/wiki/S-18986" title="S-18986">S-18986</a></li> <li><a href="/wiki/Sunifiram" title="Sunifiram">Sunifiram</a></li> <li><a href="/wiki/Unifiram" title="Unifiram">Unifiram</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Arylcyclohexylamine" title="Arylcyclohexylamine">Arylcyclohexylamines</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/Benocyclidine" title="Benocyclidine">Benocyclidine</a></li> <li><a href="/wiki/Dieticyclidine" title="Dieticyclidine">Dieticyclidine</a></li> <li><a href="/wiki/Esketamine" title="Esketamine">Esketamine</a></li> <li><a href="/wiki/Eticyclidine" title="Eticyclidine">Eticyclidine</a></li> <li><a href="/wiki/Gacyclidine" title="Gacyclidine">Gacyclidine</a></li> <li><a href="/wiki/Ketamine" title="Ketamine">Ketamine</a></li> <li><a href="/wiki/Phencyclamine" class="mw-redirect" title="Phencyclamine">Phencyclamine</a></li> <li><a href="/wiki/Phencyclidine" title="Phencyclidine">Phencyclidine</a></li> <li><a href="/wiki/Rolicyclidine" title="Rolicyclidine">Rolicyclidine</a></li> <li><a href="/wiki/Tenocyclidine" title="Tenocyclidine">Tenocyclidine</a></li> <li><a href="/wiki/Tiletamine" title="Tiletamine">Tiletamine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Benzazepine" title="Benzazepine">Benzazepines</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/6-Br-APB" title="6-Br-APB">6-Br-APB</a></li> <li><a href="/wiki/SKF-77434" class="mw-redirect" title="SKF-77434">SKF-77434</a></li> <li><a href="/wiki/SKF-81297" class="mw-redirect" title="SKF-81297">SKF-81297</a></li> <li><a href="/wiki/SKF-82958" class="mw-redirect" title="SKF-82958">SKF-82958</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Substituted_cathinone" title="Substituted cathinone">Cathinones</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/3-FMC" class="mw-redirect" title="3-FMC">3-FMC</a></li> <li><a href="/wiki/3-MMC" class="mw-redirect" title="3-MMC">3-MMC</a></li> <li><a href="/wiki/3,4-Dimethylmethcathinone" title="3,4-Dimethylmethcathinone">3,4-DMMC</a></li> <li><a href="/wiki/4-Bromomethcathinone" title="4-Bromomethcathinone">4-BMC</a></li> <li><a href="/wiki/4-Chloromethcathinone" title="4-Chloromethcathinone">4-CMC</a></li> <li><a href="/wiki/4-Methylbuphedrone" title="4-Methylbuphedrone">4-Methylbuphedrone</a></li> <li><a href="/wiki/4-Methylcathinone" title="4-Methylcathinone">4-Methylcathinone</a></li> <li><a href="/wiki/4-Methyl-%CE%B1-ethylaminopentiophenone" title="4-Methyl-α-ethylaminopentiophenone">4-MEAP</a></li> <li><a href="/wiki/4-Methylpentedrone" title="4-Methylpentedrone">4-Methylpentedrone</a></li> <li><a href="/wiki/Amfepramone" title="Amfepramone">Amfepramone</a></li> <li><a href="/wiki/Benzedrone" title="Benzedrone">Benzedrone</a></li> <li><a href="/wiki/Buphedrone" title="Buphedrone">Buphedrone</a></li> <li><a href="/wiki/Bupropion" title="Bupropion">Bupropion</a></li> <li><a href="/wiki/Butylone" title="Butylone">Butylone</a></li> <li><a href="/wiki/Cathinone" title="Cathinone">Cathinone</a></li> <li><a href="/wiki/Dimethylcathinone" title="Dimethylcathinone">Dimethylcathinone</a></li> <li><a href="/wiki/Ethcathinone" title="Ethcathinone">Ethcathinone</a></li> <li><a href="/wiki/Ethylone" title="Ethylone">Ethylone</a></li> <li><a href="/wiki/Flephedrone" title="Flephedrone">Flephedrone</a></li> <li><a href="/wiki/Hexedrone" title="Hexedrone">Hexedrone</a></li> <li><a href="/wiki/Isoethcathinone" title="Isoethcathinone">Isoethcathinone</a></li> <li><a href="/wiki/Mephedrone" title="Mephedrone">Mephedrone</a></li> <li><a href="/wiki/Methcathinone" title="Methcathinone">Methcathinone</a></li> <li><a href="/wiki/Methedrone" title="Methedrone">Methedrone</a></li> <li><a href="/wiki/Methylenedioxycathinone" title="Methylenedioxycathinone">Methylenedioxycathinone</a></li> <li><a href="/wiki/Methylone" title="Methylone">Methylone</a></li> <li><a href="/wiki/Mexedrone" title="Mexedrone">Mexedrone</a></li> <li><a href="/wiki/N-Ethylbuphedrone" title="N-Ethylbuphedrone">N-Ethylbuphedrone</a></li> <li><a href="/wiki/N-Ethylhexedrone" title="N-Ethylhexedrone">N-Ethylhexedrone</a></li> <li><a href="/wiki/Pentedrone" title="Pentedrone">Pentedrone</a></li> <li><a href="/wiki/Pentylone" title="Pentylone">Pentylone</a></li> <li><a href="/wiki/Phthalimidopropiophenone" title="Phthalimidopropiophenone">Phthalimidopropiophenone</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Acetylcholine" title="Acetylcholine">Cholinergics</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/A-84,543" title="A-84,543">A-84,543</a></li> <li><a href="/wiki/A-366,833" title="A-366,833">A-366,833</a></li> <li><a href="/wiki/ABT-202" title="ABT-202">ABT-202</a></li> <li><a href="/wiki/ABT-418" title="ABT-418">ABT-418</a></li> <li><a href="/wiki/AR-R17779" title="AR-R17779">AR-R17779</a></li> <li><a href="/wiki/Altinicline" title="Altinicline">Altinicline</a></li> <li><a href="/wiki/Anabasine" title="Anabasine">Anabasine</a></li> <li><a href="/wiki/Arecoline" title="Arecoline">Arecoline</a></li> <li><a href="/wiki/Bradanicline" title="Bradanicline">Bradanicline</a></li> <li><a href="/wiki/Cotinine" title="Cotinine">Cotinine</a></li> <li><a href="/wiki/Cytisine" title="Cytisine">Cytisine</a></li> <li><a href="/wiki/Dianicline" title="Dianicline">Dianicline</a></li> <li><a class="mw-selflink selflink">Epibatidine</a></li> <li><a href="/wiki/Epiboxidine" title="Epiboxidine">Epiboxidine</a></li> <li><a href="/wiki/GTS-21" title="GTS-21">GTS-21</a></li> <li><a href="/wiki/Ispronicline" title="Ispronicline">Ispronicline</a></li> <li><a href="/wiki/Nicotine" title="Nicotine">Nicotine</a></li> <li><a href="/wiki/PHA-543,613" title="PHA-543,613">PHA-543,613</a></li> <li><a href="/wiki/PNU-120,596" title="PNU-120,596">PNU-120,596</a></li> <li><a href="/wiki/PNU-282,987" title="PNU-282,987">PNU-282,987</a></li> <li><a href="/wiki/Pozanicline" title="Pozanicline">Pozanicline</a></li> <li><a href="/wiki/Rivanicline" title="Rivanicline">Rivanicline</a></li> <li><a href="/wiki/Sazetidine_A" title="Sazetidine A">Sazetidine A</a></li> <li><a href="/wiki/SIB-1553A" title="SIB-1553A">SIB-1553A</a></li> <li><a href="/wiki/SSR-180,711" title="SSR-180,711">SSR-180,711</a></li> <li><a href="/wiki/TC-1698" title="TC-1698">TC-1698</a></li> <li><a href="/wiki/TC-1827" title="TC-1827">TC-1827</a></li> <li><a href="/wiki/TC-2216" title="TC-2216">TC-2216</a></li> <li><a href="/wiki/Tebanicline" title="Tebanicline">Tebanicline</a></li> <li><a href="/wiki/UB-165" title="UB-165">UB-165</a></li> <li><a href="/wiki/Varenicline" title="Varenicline">Varenicline</a></li> <li><a href="/wiki/WAY-317,538" class="mw-redirect" title="WAY-317,538">WAY-317,538</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Convulsion" title="Convulsion">Convulsants</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/Anatoxin-a" title="Anatoxin-a">Anatoxin-a</a></li> <li><a href="/wiki/Bicuculline" title="Bicuculline">Bicuculline</a></li> <li><a href="/wiki/DMCM" title="DMCM">DMCM</a></li> <li><a href="/wiki/Flurothyl" title="Flurothyl">Flurothyl</a></li> <li><a href="/wiki/Gabazine" title="Gabazine">Gabazine</a></li> <li><a href="/wiki/Pentylenetetrazol" title="Pentylenetetrazol">Pentetrazol</a></li> <li><a href="/wiki/Picrotoxin" title="Picrotoxin">Picrotoxin</a></li> <li><a href="/wiki/Strychnine" title="Strychnine">Strychnine</a></li> <li><a href="/wiki/Thujone" title="Thujone">Thujone</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Eugeroic" title="Eugeroic">Eugeroics</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/Adrafinil" title="Adrafinil">Adrafinil</a></li> <li><a href="/wiki/Armodafinil" title="Armodafinil">Armodafinil</a></li> <li><a href="/wiki/CRL-40,940" class="mw-redirect" title="CRL-40,940">CRL-40,940</a></li> <li><a href="/wiki/CRL-40,941" class="mw-redirect" title="CRL-40,941">CRL-40,941</a></li> <li><a href="/wiki/Fluorenol" title="Fluorenol">Fluorenol</a></li> <li><a href="/wiki/Modafinil" title="Modafinil">Modafinil</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Oxazoline" title="Oxazoline">Oxazolines</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/4-Methylaminorex" title="4-Methylaminorex">4-Methylaminorex</a></li> <li><a href="/wiki/Aminorex" title="Aminorex">Aminorex</a></li> <li><a href="/wiki/Clominorex" title="Clominorex">Clominorex</a></li> <li><a href="/wiki/Cyclazodone" title="Cyclazodone">Cyclazodone</a></li> <li><a href="/wiki/Fenozolone" title="Fenozolone">Fenozolone</a></li> <li><a href="/wiki/Fluminorex" title="Fluminorex">Fluminorex</a></li> <li><a href="/wiki/Pemoline" title="Pemoline">Pemoline</a></li> <li><a href="/wiki/Thozalinone" title="Thozalinone">Thozalinone</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Substituted_phenethylamine" title="Substituted phenethylamine">Phenethylamines</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/4-Methylphenylisobutylamine" title="4-Methylphenylisobutylamine">1-(4-Methylphenyl)-2-aminobutane</a></li> <li><a href="/wiki/1-Methylamino-1-(3,4-methylenedioxyphenyl)propane" title="1-Methylamino-1-(3,4-methylenedioxyphenyl)propane">1-Methylamino-1-(3,4-methylenedioxyphenyl)propane</a></li> <li><a href="/wiki/2-Fluoroamphetamine" title="2-Fluoroamphetamine">2-Fluoroamphetamine</a></li> <li><a href="/wiki/2-FMA" class="mw-redirect" title="2-FMA">2-Fluoromethamphetamine</a></li> <li><a href="/wiki/2-Hydroxyphenethylamine" class="mw-redirect" title="2-Hydroxyphenethylamine">2-OH-PEA</a></li> <li><a href="/wiki/2-Phenyl-3-aminobutane" title="2-Phenyl-3-aminobutane">2-Phenyl-3-aminobutane</a></li> <li><a href="/wiki/2,3-Methylenedioxyamphetamine" title="2,3-Methylenedioxyamphetamine">2,3-MDA</a></li> <li><a href="/wiki/3-FA" class="mw-redirect" title="3-FA">3-Fluoroamphetamine</a></li> <li><a href="/wiki/3-Fluoroethamphetamine" title="3-Fluoroethamphetamine">3-Fluoroethamphetamine</a></li> <li><a href="/wiki/3-Methoxyamphetamine" title="3-Methoxyamphetamine">3-Methoxyamphetamine</a></li> <li><a href="/wiki/3-Methylamphetamine" title="3-Methylamphetamine">3-Methylamphetamine</a></li> <li><a href="/wiki/4-FA" class="mw-redirect" title="4-FA">4-Fluoroamphetamine</a></li> <li><a href="/wiki/4-FMA" class="mw-redirect" title="4-FMA">4-Fluoromethamphetamine</a></li> <li><a href="/wiki/4-Methylamphetamine" title="4-Methylamphetamine">4-MA</a></li> <li><a href="/wiki/4-Methylmethamphetamine" title="4-Methylmethamphetamine">4-MMA</a></li> <li><a href="/wiki/4-Methylthioamphetamine" title="4-Methylthioamphetamine">4-MTA</a></li> <li><a href="/wiki/6-Fluoronorepinephrine" title="6-Fluoronorepinephrine">6-FNE</a></li> <li><a href="/wiki/AL-1095" title="AL-1095">AL-1095</a></li> <li><a href="/wiki/Alfetamine" title="Alfetamine">Alfetamine</a></li> <li><a href="/wiki/Alpha-Ethylphenethylamine" class="mw-redirect" title="Alpha-Ethylphenethylamine">a-Ethylphenethylamine</a></li> <li><a href="/wiki/Amfecloral" title="Amfecloral">Amfecloral</a></li> <li><a href="/wiki/Amfepentorex" title="Amfepentorex">Amfepentorex</a></li> <li><a href="/wiki/Amidephrine" title="Amidephrine">Amidephrine</a></li> <li><a href="/wiki/2-Amino-1,2-dihydronaphthalene" title="2-Amino-1,2-dihydronaphthalene">2-Amino-1,2-dihydronaphthalene</a></li> <li><a href="/wiki/2-Aminoindane" title="2-Aminoindane">2-Aminoindane</a></li> <li><a href="/wiki/5-(2-Aminopropyl)indole" title="5-(2-Aminopropyl)indole">5-(2-Aminopropyl)indole</a></li> <li><a href="/wiki/2-Aminotetralin" title="2-Aminotetralin">2-Aminotetralin</a></li> <li><a href="/wiki/Acridorex" title="Acridorex">Acridorex</a></li> <li><a href="/wiki/Amphetamine" title="Amphetamine">Amphetamine</a> (<a href="/wiki/Dextroamphetamine" title="Dextroamphetamine">Dextroamphetamine</a>, <a href="/wiki/Levoamphetamine" title="Levoamphetamine">Levoamphetamine</a>)</li> <li><a href="/wiki/Amphetaminil" class="mw-redirect" title="Amphetaminil">Amphetaminil</a></li> <li><a href="/wiki/Arbutamine" title="Arbutamine">Arbutamine</a></li> <li><a href="/wiki/%CE%92-Methylphenethylamine" title="Β-Methylphenethylamine">β-Methylphenethylamine</a></li> <li><a href="/wiki/%CE%92-Phenylmethamphetamine" title="Β-Phenylmethamphetamine">β-Phenylmethamphetamine</a></li> <li><a href="/wiki/Benfluorex" title="Benfluorex">Benfluorex</a></li> <li><a href="/wiki/Benzphetamine" title="Benzphetamine">Benzphetamine</a></li> <li><a href="/wiki/Benzodioxolylbutanamine" class="mw-redirect" title="Benzodioxolylbutanamine">BDB</a></li> <li><a href="/wiki/BOH_(drug)" title="BOH (drug)">BOH</a></li> <li><a href="/wiki/3-Benzhydrylmorpholine" title="3-Benzhydrylmorpholine">3-Benzhydrylmorpholine</a></li> <li><a href="/wiki/Benzofuranylpropylaminopentane" title="Benzofuranylpropylaminopentane">BPAP</a></li> <li><a href="/wiki/Camfetamine" title="Camfetamine">Camfetamine</a></li> <li><a href="/wiki/Cathine" title="Cathine">Cathine</a></li> <li><a href="/wiki/Chlorphentermine" title="Chlorphentermine">Chlorphentermine</a></li> <li><a href="/wiki/Cilobamine" title="Cilobamine">Cilobamine</a></li> <li><a href="/wiki/Cinnamedrine" title="Cinnamedrine">Cinnamedrine</a></li> <li><a href="/wiki/Clenbuterol" title="Clenbuterol">Clenbuterol</a></li> <li><a href="/wiki/Clobenzorex" title="Clobenzorex">Clobenzorex</a></li> <li><a href="/wiki/Cloforex" title="Cloforex">Cloforex</a></li> <li><a href="/wiki/Clortermine" title="Clortermine">Clortermine</a></li> <li><a href="/wiki/Cypenamine" title="Cypenamine">Cypenamine</a></li> <li><a href="/wiki/D-Deprenyl" title="D-Deprenyl"><small>D</small>-Deprenyl</a></li> <li><a href="/wiki/Denopamine" title="Denopamine">Denopamine</a></li> <li><a href="/wiki/Dimethoxyamphetamine" title="Dimethoxyamphetamine">Dimethoxyamphetamine</a></li> <li><a href="/wiki/Dimethylamphetamine" title="Dimethylamphetamine">Dimethylamphetamine</a></li> <li><a href="/wiki/Dobutamine" title="Dobutamine">Dobutamine</a></li> <li><a href="/wiki/L-DOPA" title="L-DOPA">DOPA</a> (<a href="/wiki/D-DOPA" title="D-DOPA">Dextrodopa</a>, <a href="/wiki/L-DOPA" title="L-DOPA">Levodopa</a>)</li> <li><a href="/wiki/Dopamine" title="Dopamine">Dopamine</a></li> <li><a href="/wiki/Dopexamine" title="Dopexamine">Dopexamine</a></li> <li><a href="/wiki/L-DOPS" class="mw-redirect" title="L-DOPS">Droxidopa</a></li> <li><a href="/wiki/Ethylbenzodioxolylbutanamine" class="mw-redirect" title="Ethylbenzodioxolylbutanamine">EBDB</a></li> <li><a href="/wiki/Ephedrine" title="Ephedrine">Ephedrine</a></li> <li><a href="/wiki/Epinephrine" class="mw-redirect" title="Epinephrine">Epinephrine</a></li> <li><a href="/wiki/Epinine" class="mw-redirect" title="Epinine">Epinine</a></li> <li><a href="/wiki/Etafedrine" title="Etafedrine">Etafedrine</a></li> <li><a href="/wiki/Ethylnorepinephrine" title="Ethylnorepinephrine">Ethylnorepinephrine</a></li> <li><a href="/wiki/Etilamfetamine" title="Etilamfetamine">Etilamfetamine</a></li> <li><a href="/wiki/Etilefrine" title="Etilefrine">Etilefrine</a></li> <li><a href="/wiki/Famprofazone" title="Famprofazone">Famprofazone</a></li> <li><a href="/wiki/Fencamfamin" title="Fencamfamin">Fencamfamin</a></li> <li><a href="/wiki/Fencamine" title="Fencamine">Fencamine</a></li> <li><a href="/wiki/Fenethylline" title="Fenethylline">Fenethylline</a></li> <li><a href="/wiki/Fenfluramine" title="Fenfluramine">Fenfluramine</a> (<a href="/wiki/Dexfenfluramine" title="Dexfenfluramine">Dexfenfluramine</a>, <a href="/wiki/Levofenfluramine" title="Levofenfluramine">Levofenfluramine</a>)</li> <li><a href="/wiki/Fenproporex" title="Fenproporex">Fenproporex</a></li> <li><a href="/wiki/Feprosidnine" title="Feprosidnine">Feprosidnine</a></li> <li><a href="/wiki/Fludorex" title="Fludorex">Fludorex</a></li> <li><a href="/wiki/Formetorex" title="Formetorex">Formetorex</a></li> <li><a href="/wiki/Furfenorex" title="Furfenorex">Furfenorex</a></li> <li><a href="/wiki/Gepefrine" title="Gepefrine">Gepefrine</a></li> <li><a href="/wiki/Hexapradol" title="Hexapradol">Hexapradol</a></li> <li><a href="/wiki/4-Hydroxy-3-methoxymethamphetamine" title="4-Hydroxy-3-methoxymethamphetamine">HMMA</a></li> <li><a href="/wiki/Hordenine" title="Hordenine">Hordenine</a></li> <li><a href="/wiki/4-Hydroxyamphetamine" title="4-Hydroxyamphetamine">4-Hydroxyamphetamine</a></li> <li><a href="/wiki/5-IAI" title="5-IAI">5-Iodo-2-aminoindane</a></li> <li><a href="/wiki/Ibopamine" title="Ibopamine">Ibopamine</a></li> <li><a href="/wiki/Indanylaminopropane" class="mw-redirect" title="Indanylaminopropane">Indanylamphetamine</a></li> <li><a href="/wiki/Iofetamine" class="mw-redirect" title="Iofetamine">Iofetamine</a></li> <li><a href="/wiki/Isoetarine" title="Isoetarine">Isoetarine</a></li> <li><a href="/wiki/Isoprenaline" title="Isoprenaline">Isoprenaline</a></li> <li><a href="/wiki/Selegiline" title="Selegiline"><small>L</small>-Deprenyl</a> (Selegiline)</li> <li><a href="/wiki/Lefetamine" title="Lefetamine">Lefetamine</a></li> <li><a href="/wiki/Lisdexamfetamine" title="Lisdexamfetamine">Lisdexamfetamine</a></li> <li><a href="/wiki/Lophophine" title="Lophophine">Lophophine</a></li> <li><a href="/wiki/Methylbenzodioxolylbutanamine" class="mw-redirect" title="Methylbenzodioxolylbutanamine">MBDB</a></li> <li><a href="/wiki/3,4-Methylenedioxyamphetamine" title="3,4-Methylenedioxyamphetamine">MDA (tenamfetamine)</a></li> <li><a href="/wiki/Methylenedioxybutylamphetamine" title="Methylenedioxybutylamphetamine">MDBU</a></li> <li><a href="/wiki/Methylenedioxyethylamphetamine" class="mw-redirect" title="Methylenedioxyethylamphetamine">MDEA</a></li> <li><a href="/wiki/MDMA" title="MDMA">MDMA (midomafetamine)</a></li> <li><a href="/wiki/Methylenedioxymethylphenethylamine" class="mw-redirect" title="Methylenedioxymethylphenethylamine">MDMPEA</a></li> <li><a href="/wiki/Methylenedioxyhydroxyamphetamine" class="mw-redirect" title="Methylenedioxyhydroxyamphetamine">MDOH</a></li> <li><a href="/wiki/Methylenedioxypropylamphetamine" class="mw-redirect" title="Methylenedioxypropylamphetamine">MDPR</a></li> <li><a href="/wiki/Methylenedioxyphenethylamine" class="mw-redirect" title="Methylenedioxyphenethylamine">MDPEA</a></li> <li><a href="/wiki/Mefenorex" title="Mefenorex">Mefenorex</a></li> <li><a href="/wiki/Mephentermine" title="Mephentermine">Mephentermine</a></li> <li><a href="/wiki/Metanephrine" title="Metanephrine">Metanephrine</a></li> <li><a href="/wiki/Metaraminol" title="Metaraminol">Metaraminol</a></li> <li><a href="/wiki/Mesocarb" title="Mesocarb">Mesocarb</a></li> <li><a href="/wiki/Methamphetamine" title="Methamphetamine">Methamphetamine</a> (<a href="/wiki/Methamphetamine" title="Methamphetamine">Dextromethamphetamine</a>, <a href="/wiki/Levomethamphetamine" title="Levomethamphetamine">Levomethamphetamine</a>)</li> <li><a href="/wiki/Methoxamine" title="Methoxamine">Methoxamine</a></li> <li><a href="/wiki/Methoxyphenamine" title="Methoxyphenamine">Methoxyphenamine</a></li> <li><a href="/wiki/3-Methoxy-4-methylamphetamine" title="3-Methoxy-4-methylamphetamine">MMA</a></li> <li><a href="/wiki/Methoxyphenamine" title="Methoxyphenamine">Methoxyphenamine</a></li> <li><a href="/wiki/MMDA_(drug)" title="MMDA (drug)">MMDA</a></li> <li><a href="/wiki/MMDMA" title="MMDMA">MMDMA</a></li> <li><a href="/wiki/3-Methoxymethamphetamine" title="3-Methoxymethamphetamine">MMMA</a></li> <li><a href="/wiki/Morforex" title="Morforex">Morforex</a></li> <li><a href="/wiki/N,alpha-Diethylphenylethylamine" class="mw-redirect" title="N,alpha-Diethylphenylethylamine">N,alpha-Diethylphenylethylamine</a></li> <li><a href="/wiki/N,N-Dimethylphenethylamine" title="N,N-Dimethylphenethylamine">N,N-Dimethylphenethylamine</a></li> <li><a href="/wiki/Naphthylaminopropane" title="Naphthylaminopropane">Naphthylamphetamine</a></li> <li><a href="/wiki/Nisoxetine" title="Nisoxetine">Nisoxetine</a></li> <li><a href="/wiki/Norepinephrine" title="Norepinephrine">Norepinephrine</a></li> <li><a href="/wiki/Norfenefrine" title="Norfenefrine">Norfenefrine</a></li> <li><a href="/wiki/Norfenfluramine" title="Norfenfluramine">Norfenfluramine</a></li> <li><a href="/wiki/Normetanephrine" title="Normetanephrine">Normetanephrine</a></li> <li><a href="/wiki/L-Norpseudoephedrine" title="L-Norpseudoephedrine"><small>L</small>-Norpseudoephedrine</a></li> <li><a href="/wiki/Octopamine" title="Octopamine">Octopamine</a></li> <li><a href="/wiki/Orciprenaline" title="Orciprenaline">Orciprenaline</a></li> <li><a href="/wiki/Ortetamine" title="Ortetamine">Ortetamine</a></li> <li><a href="/wiki/Oxifentorex" title="Oxifentorex">Oxifentorex</a></li> <li><a href="/wiki/Oxilofrine" title="Oxilofrine">Oxilofrine</a></li> <li><a href="/wiki/Para-Bromoamphetamine" title="Para-Bromoamphetamine">PBA</a></li> <li><a href="/wiki/Para-Chloroamphetamine" title="Para-Chloroamphetamine">PCA</a></li> <li><a href="/wiki/Para-Chloromethamphetamine" title="Para-Chloromethamphetamine">PCMA</a></li> <li><a href="/wiki/Norpholedrine" class="mw-redirect" title="Norpholedrine">PHA</a></li> <li><a href="/wiki/Pentorex" title="Pentorex">Pentorex</a></li> <li><a href="/wiki/Phenatine" title="Phenatine">Phenatine</a></li> <li><a href="/wiki/Phenpromethamine" title="Phenpromethamine">Phenpromethamine</a></li> <li><a href="/wiki/Phentermine" title="Phentermine">Phentermine</a></li> <li><a href="/wiki/Phenylalanine" title="Phenylalanine">Phenylalanine</a></li> <li><a href="/wiki/Phenylephrine" title="Phenylephrine">Phenylephrine</a></li> <li><a href="/wiki/Phenylpropanolamine" title="Phenylpropanolamine">Phenylpropanolamine</a></li> <li><a href="/wiki/Pholedrine" title="Pholedrine">Pholedrine</a></li> <li><a href="/wiki/Para-Iodoamphetamine" title="Para-Iodoamphetamine">PIA</a></li> <li><a href="/wiki/Para-Methoxyamphetamine" title="Para-Methoxyamphetamine">PMA</a></li> <li><a href="/wiki/Para-Methoxyethylamphetamine" class="mw-redirect" title="Para-Methoxyethylamphetamine">PMEA</a></li> <li><a href="/wiki/Para-Methoxymethamphetamine" title="Para-Methoxymethamphetamine">PMMA</a></li> <li><a href="/wiki/Phenylpropylaminopentane" title="Phenylpropylaminopentane">PPAP</a></li> <li><a href="/wiki/Prenylamine" title="Prenylamine">Prenylamine</a></li> <li><a href="/wiki/Propylamphetamine" title="Propylamphetamine">Propylamphetamine</a></li> <li><a href="/wiki/Pseudoephedrine" title="Pseudoephedrine">Pseudoephedrine</a></li> <li><a href="/wiki/Ropinirole" title="Ropinirole">Ropinirole</a></li> <li><a href="/wiki/Salbutamol" title="Salbutamol">Salbutamol</a> (<a href="/wiki/Levosalbutamol" title="Levosalbutamol">Levosalbutamol</a>)</li> <li><a href="/wiki/Sibutramine" title="Sibutramine">Sibutramine</a></li> <li><a href="/wiki/Solriamfetol" title="Solriamfetol">Solriamfetol</a></li> <li><a href="/wiki/Synephrine" title="Synephrine">Synephrine</a></li> <li><a href="/wiki/Theodrenaline" title="Theodrenaline">Theodrenaline</a></li> <li><a href="/wiki/Tiflorex" title="Tiflorex">Tiflorex</a></li> <li><a href="/wiki/Tranylcypromine" title="Tranylcypromine">Tranylcypromine</a></li> <li><a href="/wiki/Tyramine" title="Tyramine">Tyramine</a></li> <li><a href="/wiki/Tyrosine" title="Tyrosine">Tyrosine</a></li> <li><a href="/wiki/Xylopropamine" title="Xylopropamine">Xylopropamine</a></li> <li><a href="/wiki/Zylofuramine" title="Zylofuramine">Zylofuramine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Substituted_phenylmorpholine" title="Substituted phenylmorpholine">Phenylmorpholines</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/3-Fluorophenmetrazine" title="3-Fluorophenmetrazine">3-Fluorophenmetrazine</a></li> <li><a href="/wiki/Fenbutrazate" title="Fenbutrazate">Fenbutrazate</a></li> <li><a href="/wiki/Fenmetramide" title="Fenmetramide">Fenmetramide</a></li> <li><a href="/wiki/G-130" title="G-130">G-130</a></li> <li><a href="/wiki/Manifaxine" title="Manifaxine">Manifaxine</a></li> <li><a href="/wiki/Morazone" title="Morazone">Morazone</a></li> <li><a href="/wiki/Morforex" title="Morforex">Morforex</a></li> <li><a href="/wiki/Oxaflozane" title="Oxaflozane">Oxaflozane</a></li> <li><a href="/wiki/PD-128,907" title="PD-128,907">PD-128,907</a></li> <li><a href="/wiki/Phendimetrazine" title="Phendimetrazine">Phendimetrazine</a></li> <li><a href="/wiki/Phenmetrazine" title="Phenmetrazine">Phenmetrazine</a></li> <li><a href="/wiki/2-Phenyl-3,6-dimethylmorpholine" title="2-Phenyl-3,6-dimethylmorpholine">2-Phenyl-3,6-dimethylmorpholine</a></li> <li><a href="/wiki/Pseudophenmetrazine" title="Pseudophenmetrazine">Pseudophenmetrazine</a></li> <li><a href="/wiki/Radafaxine" title="Radafaxine">Radafaxine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Piperazine" title="Piperazine">Piperazines</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/2C-B-BZP" title="2C-B-BZP">2C-B-BZP</a></li> <li><a href="/wiki/1-(3-chlorophenyl)-4-(2-phenylethyl)piperazine" class="mw-redirect" title="1-(3-chlorophenyl)-4-(2-phenylethyl)piperazine">3C-PEP</a></li> <li><a href="/wiki/Benzylpiperazine" title="Benzylpiperazine">BZP</a></li> <li><a href="/wiki/CM156" title="CM156">CM156</a></li> <li><a href="/wiki/DBL-583" title="DBL-583">DBL-583</a></li> <li><a href="/wiki/GBR-12783" title="GBR-12783">GBR-12783</a></li> <li><a href="/wiki/GBR-12935" title="GBR-12935">GBR-12935</a></li> <li><a href="/wiki/GBR-13069" title="GBR-13069">GBR-13069</a></li> <li><a href="/wiki/GBR-13098" title="GBR-13098">GBR-13098</a></li> <li><a href="/wiki/GBR-13119" title="GBR-13119">GBR-13119</a></li> <li><a href="/wiki/JJC8-088" title="JJC8-088">JJC8-088</a></li> <li><a href="/wiki/Para-Methoxyphenylpiperazine" title="Para-Methoxyphenylpiperazine">MeOPP</a></li> <li><a href="/wiki/Methylbenzylpiperazine" title="Methylbenzylpiperazine">MBZP</a></li> <li><a href="/wiki/Ortho-Methylphenylpiperazine" title="Ortho-Methylphenylpiperazine">oMPP</a></li> <li><a href="/wiki/Vanoxerine" title="Vanoxerine">Vanoxerine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Piperidine" title="Piperidine">Piperidines</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-Benzyl-4-(2-(diphenylmethoxy)ethyl)piperidine" title="1-Benzyl-4-(2-(diphenylmethoxy)ethyl)piperidine">1-Benzyl-4-(2-(diphenylmethoxy)ethyl)piperidine</a></li> <li><a href="/wiki/2-Benzylpiperidine" title="2-Benzylpiperidine">2-Benzylpiperidine</a></li> <li><a href="/wiki/2-Methyl-3-phenylpiperidine" title="2-Methyl-3-phenylpiperidine">2-Methyl-3-phenylpiperidine</a></li> <li><a href="/wiki/3,4-Dichloromethylphenidate" title="3,4-Dichloromethylphenidate">3,4-Dichloromethylphenidate</a></li> <li><a href="/wiki/4-Benzylpiperidine" title="4-Benzylpiperidine">4-Benzylpiperidine</a></li> <li><a href="/wiki/4-Fluoromethylphenidate" title="4-Fluoromethylphenidate">4-Fluoromethylphenidate</a></li> <li><a href="/wiki/4-Methylmethylphenidate" title="4-Methylmethylphenidate">4-Methylmethylphenidate</a></li> <li><a href="/wiki/Desoxypipradrol" title="Desoxypipradrol">Desoxypipradrol</a></li> <li><a href="/wiki/Difemetorex" title="Difemetorex">Difemetorex</a></li> <li><a href="/wiki/Diphenylpyraline" title="Diphenylpyraline">Diphenylpyraline</a></li> <li><a href="/wiki/HDEP-28" title="HDEP-28">Ethylnaphthidate</a></li> <li><a href="/wiki/Ethylphenidate" title="Ethylphenidate">Ethylphenidate</a></li> <li><a href="/wiki/HDMP-28" title="HDMP-28">Methylnaphthidate</a></li> <li><a href="/wiki/Isopropylphenidate" title="Isopropylphenidate">Isopropylphenidate</a></li> <li><a href="/wiki/JZ-IV-10" title="JZ-IV-10">JZ-IV-10</a></li> <li><a href="/wiki/Methylphenidate" title="Methylphenidate">Methylphenidate</a> (<a href="/wiki/Dexmethylphenidate" title="Dexmethylphenidate">Dexmethylphenidate</a>)</li> <li><a href="/wiki/(%2B)-CPCA" title="(+)-CPCA">Nocaine</a></li> <li><a href="/wiki/Levophacetoperane" title="Levophacetoperane">Phacetoperane</a></li> <li><a href="/wiki/Pipradrol" title="Pipradrol">Pipradrol</a></li> <li><a href="/wiki/Propylphenidate" title="Propylphenidate">Propylphenidate</a></li> <li><a href="/wiki/Serdexmethylphenidate" title="Serdexmethylphenidate">Serdexmethylphenidate</a></li> <li><a href="/wiki/SCH-5472" title="SCH-5472">SCH-5472</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Pyrrolidine" title="Pyrrolidine">Pyrrolidines</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-Diphenylmethylpyrrolidine" title="2-Diphenylmethylpyrrolidine">2-Diphenylmethylpyrrolidine</a></li> <li><a href="/wiki/4-Chloro-alpha-pyrrolidinovalerophenone" class="mw-redirect" title="4-Chloro-alpha-pyrrolidinovalerophenone">4-Cl-PVP</a></li> <li><a href="/wiki/5-DBFPV" title="5-DBFPV">5-DBFPV</a></li> <li><a href="/wiki/Alpha-Pyrrolidinopropiophenone" class="mw-redirect" title="Alpha-Pyrrolidinopropiophenone">α-PPP</a></li> <li><a href="/wiki/Alpha-Pyrrolidinobutiophenone" class="mw-redirect" title="Alpha-Pyrrolidinobutiophenone">α-PBP</a></li> <li><a href="/wiki/%CE%91-PCYP" title="Α-PCYP">α-PCYP</a></li> <li><a href="/wiki/%CE%91-PHiP" title="Α-PHiP">α-PHiP</a></li> <li><a href="/wiki/Alpha-Pyrrolidinohexiophenone" class="mw-redirect" title="Alpha-Pyrrolidinohexiophenone">α-PHP</a></li> <li><a href="/wiki/%CE%91-Pyrrolidinoheptaphenone" title="Α-Pyrrolidinoheptaphenone">α-PHPP</a></li> <li><a href="/wiki/Alpha-Pyrrolidinopentiophenone" class="mw-redirect" title="Alpha-Pyrrolidinopentiophenone">α-PVP</a></li> <li><a href="/wiki/Alpha-Pyrrolidinopentiothiophenone" class="mw-redirect" title="Alpha-Pyrrolidinopentiothiophenone">α-PVT</a></li> <li><a href="/wiki/Diphenylprolinol" title="Diphenylprolinol">Diphenylprolinol</a></li> <li><a href="/wiki/3%27,4%27-Dimethoxy-%CE%B1-Pyrrolidinopentiophenone" class="mw-redirect" title="3',4'-Dimethoxy-α-Pyrrolidinopentiophenone">DMPVP</a></li> <li><a href="/wiki/4%27-Fluoro-%CE%B1-Pyrrolidinooctanophenone" class="mw-redirect" title="4'-Fluoro-α-Pyrrolidinooctanophenone">FPOP</a></li> <li><a href="/wiki/4%27-Fluoro-%CE%B1-Pyrrolidinopentiophenone" class="mw-redirect" title="4'-Fluoro-α-Pyrrolidinopentiophenone">FPVP</a></li> <li><a href="/wiki/3%27,4%27-Methylenedioxy-%CE%B1-pyrrolidinopropiophenone" title="3',4'-Methylenedioxy-α-pyrrolidinopropiophenone">MDPPP</a></li> <li><a href="/wiki/3%27,4%27-Methylenedioxy-%CE%B1-pyrrolidinobutiophenone" title="3',4'-Methylenedioxy-α-pyrrolidinobutiophenone">MDPBP</a></li> <li><a href="/wiki/4%27-Methyl-a-pyrrolidinobutiophenone" class="mw-redirect" title="4'-Methyl-a-pyrrolidinobutiophenone">MPBP</a></li> <li><a href="/wiki/4%27-Methyl-%CE%B1-pyrrolidinohexiophenone" title="4'-Methyl-α-pyrrolidinohexiophenone">MPHP</a></li> <li><a href="/wiki/4%27-Methyl-%CE%B1-pyrrolidinopropiophenone" title="4'-Methyl-α-pyrrolidinopropiophenone">MPPP</a></li> <li><a href="/wiki/4%27-Methoxy-%CE%B1-Pyrrolidinopentiophenone" class="mw-redirect" title="4'-Methoxy-α-Pyrrolidinopentiophenone">MOPVP</a></li> <li><a href="/wiki/4%27-Methoxy-%CE%B1-pyrrolidinopropiophenone" title="4'-Methoxy-α-pyrrolidinopropiophenone">MOPPP</a></li> <li><a href="/wiki/Indapyrophenidone" title="Indapyrophenidone">Indapyrophenidone</a></li> <li><a href="/wiki/Methylenedioxypyrovalerone" title="Methylenedioxypyrovalerone">MDPV</a></li> <li><a href="/wiki/Naphyrone" title="Naphyrone">Naphyrone</a></li> <li><a href="/wiki/Phenylethylpyrrolidine" title="Phenylethylpyrrolidine">PEP</a></li> <li><a href="/wiki/Picilorex" title="Picilorex">Picilorex</a></li> <li><a href="/wiki/Prolintane" title="Prolintane">Prolintane</a></li> <li><a href="/wiki/Pyrovalerone" title="Pyrovalerone">Pyrovalerone</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Racetam" title="Racetam">Racetams</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/Oxiracetam" title="Oxiracetam">Oxiracetam</a></li> <li><a href="/wiki/Phenylpiracetam" title="Phenylpiracetam">Phenylpiracetam</a></li> <li><a href="/wiki/Phenylpiracetam_hydrazide" title="Phenylpiracetam hydrazide">Phenylpiracetam hydrazide</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Tropane" title="Tropane">Tropanes</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/4-fluorotropacocaine" class="mw-redirect" title="4-fluorotropacocaine">4-fluorotropacocaine</a></li> <li><a href="/wiki/4%27-Fluorococaine" class="mw-redirect" title="4'-Fluorococaine">4'-Fluorococaine</a></li> <li><a href="/wiki/Altropane" title="Altropane">Altropane (IACFT)</a></li> <li><a href="/wiki/Brasofensine" title="Brasofensine">Brasofensine</a></li> <li><a href="/wiki/WIN_35428" class="mw-redirect" title="WIN 35428">CFT (WIN 35,428)</a></li> <li><a href="/wiki/RTI-55" title="RTI-55">β-CIT (RTI-55)</a></li> <li><a href="/wiki/Cocaethylene" title="Cocaethylene">Cocaethylene</a></li> <li><a href="/wiki/Cocaine" title="Cocaine">Cocaine</a></li> <li><a href="/wiki/Dichloropane" title="Dichloropane">Dichloropane (RTI-111)</a></li> <li><a href="/wiki/Difluoropine" title="Difluoropine">Difluoropine</a></li> <li><a href="/wiki/FE-%CE%B2-CPPIT" title="FE-β-CPPIT">FE-β-CPPIT</a></li> <li><a href="/wiki/FP-%CE%B2-CPPIT" title="FP-β-CPPIT">FP-β-CPPIT</a></li> <li><a href="/wiki/Ioflupane_(123I)" title="Ioflupane (123I)">Ioflupane (<sup>123</sup>I)</a></li> <li><a href="/wiki/Norcocaine" title="Norcocaine">Norcocaine</a></li> <li><a href="/wiki/2-Propanoyl-3-(4-isopropylphenyl)-tropane" title="2-Propanoyl-3-(4-isopropylphenyl)-tropane">PIT</a></li> <li><a href="/wiki/2%CE%B2-Propanoyl-3%CE%B2-(4-tolyl)-tropane" title="2β-Propanoyl-3β-(4-tolyl)-tropane">PTT</a></li> <li><a href="/wiki/RTI-31" title="RTI-31">RTI-31</a></li> <li><a href="/wiki/RTI-32" title="RTI-32">RTI-32</a></li> <li><a href="/wiki/RTI-51" title="RTI-51">RTI-51</a></li> <li><a href="/wiki/RTI-112" title="RTI-112">RTI-112</a></li> <li><a href="/wiki/RTI-113" title="RTI-113">RTI-113</a></li> <li><a href="/wiki/RTI-120" title="RTI-120">RTI-120</a></li> <li><a href="/wiki/RTI-121" title="RTI-121">RTI-121 (IPCIT)</a></li> <li><a href="/wiki/RTI-126" title="RTI-126">RTI-126</a></li> <li><a href="/wiki/RTI-150" title="RTI-150">RTI-150</a></li> <li><a href="/wiki/RTI-177" title="RTI-177">RTI-177</a></li> <li><a href="/wiki/RTI-229" title="RTI-229">RTI-229</a></li> <li><a href="/wiki/(-)-2%CE%B2-(3-(4-Methylphenyl)isoxazol-5-yl)-3%CE%B2-(4-chlorophenyl)tropane" class="mw-redirect" title="(-)-2β-(3-(4-Methylphenyl)isoxazol-5-yl)-3β-(4-chlorophenyl)tropane">RTI-336</a></li> <li><a href="/wiki/RTI-354" class="mw-redirect" title="RTI-354">RTI-354</a></li> <li><a href="/wiki/RTI-371" title="RTI-371">RTI-371</a></li> <li><a href="/wiki/RTI-386" class="mw-redirect" title="RTI-386">RTI-386</a></li> <li><a href="/wiki/Salicylmethylecgonine" title="Salicylmethylecgonine">Salicylmethylecgonine</a></li> <li><a href="/wiki/Tesofensine" title="Tesofensine">Tesofensine</a></li> <li><a href="/wiki/Troparil" title="Troparil">Troparil (β-CPT, WIN 35,065-2)</a></li> <li><a href="/wiki/Tropoxane" title="Tropoxane">Tropoxane</a></li> <li><a href="/wiki/2%CE%B2-Propanoyl-3%CE%B2-(2-naphthyl)-tropane" title="2β-Propanoyl-3β-(2-naphthyl)-tropane">WF-23</a></li> <li><a href="/wiki/2%CE%B1-(Propanoyl)-3%CE%B2-(2-(6-methoxynaphthyl))-tropane" title="2α-(Propanoyl)-3β-(2-(6-methoxynaphthyl))-tropane">WF-33</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><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/4-HO-%CE%B1MT" title="4-HO-αMT">4-HO-αMT</a></li> <li><a href="/wiki/4-Methyl-%CE%B1ET" class="mw-redirect" title="4-Methyl-αET">4-Methyl-αET</a></li> <li><a href="/wiki/4-Methyl-%CE%B1MT" class="mw-redirect" title="4-Methyl-αMT">4-Methyl-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-Fluoro-%CE%B1MT" class="mw-redirect" title="5-Fluoro-αMT">5-Fluoro-αMT</a></li> <li><a href="/wiki/5-MeO-%CE%B1ET" class="mw-redirect" title="5-MeO-αET">5-MeO-αET</a></li> <li><a href="/wiki/5-MeO-%CE%B1MT" class="mw-redirect" title="5-MeO-αMT">5-MeO-αMT</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/6-Fluoro-%CE%B1MT" class="mw-redirect" title="6-Fluoro-αMT">6-Fluoro-αMT</a></li> <li><a href="/wiki/7-Methyl-%CE%B1ET" class="mw-redirect" title="7-Methyl-αET">7-Methyl-αET</a></li> <li><a href="/wiki/%CE%91-Ethyltryptamine" title="Α-Ethyltryptamine">αET</a></li> <li><a href="/wiki/%CE%91-Methyltryptamine" title="Α-Methyltryptamine">αMT</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Others</th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/2-MDP" title="2-MDP">2-MDP</a></li> <li><a href="/wiki/3,3-Diphenylcyclobutanamine" title="3,3-Diphenylcyclobutanamine">3,3-Diphenylcyclobutanamine</a></li> <li><a href="/wiki/Amfonelic_acid" title="Amfonelic acid">Amfonelic acid</a></li> <li><a href="/wiki/Amineptine" title="Amineptine">Amineptine</a></li> <li><a href="/wiki/Amiphenazole" title="Amiphenazole">Amiphenazole</a></li> <li><a href="/wiki/Atipamezole" title="Atipamezole">Atipamezole</a></li> <li><a href="/wiki/Atomoxetine" title="Atomoxetine">Atomoxetine</a></li> <li><a href="/wiki/Bemegride" title="Bemegride">Bemegride</a></li> <li><a href="/wiki/Benzydamine" title="Benzydamine">Benzydamine</a></li> <li><a href="/wiki/Butyltolylquinuclidine" title="Butyltolylquinuclidine">BTQ</a></li> <li><a href="/wiki/BTS_74,398" title="BTS 74,398">BTS 74,398</a></li> <li><a href="/wiki/Centanafadine" title="Centanafadine">Centanafadine</a></li> <li><a href="/wiki/Ciclazindol" title="Ciclazindol">Ciclazindol</a></li> <li><a href="/wiki/Clofenciclan" title="Clofenciclan">Clofenciclan</a></li> <li><a href="/wiki/Cropropamide" class="mw-redirect" title="Cropropamide">Cropropamide</a></li> <li><a href="/wiki/Crotetamide" class="mw-redirect" title="Crotetamide">Crotetamide</a></li> <li><a href="/wiki/D-161" title="D-161">D-161</a></li> <li><a href="/wiki/Desipramine" title="Desipramine">Desipramine</a></li> <li><a href="/wiki/Diclofensine" title="Diclofensine">Diclofensine</a></li> <li><a href="/wiki/Dimethocaine" title="Dimethocaine">Dimethocaine</a></li> <li><a href="/wiki/Efaroxan" title="Efaroxan">Efaroxan</a></li> <li><a href="/wiki/Etamivan" title="Etamivan">Etamivan</a></li> <li><a href="/wiki/Fenisorex" title="Fenisorex">Fenisorex</a></li> <li><a href="/wiki/Fenpentadiol" title="Fenpentadiol">Fenpentadiol</a></li> <li><a href="/wiki/Gamfexine" title="Gamfexine">Gamfexine</a></li> <li><a href="/wiki/Gilutensin" class="mw-redirect" title="Gilutensin">Gilutensin</a></li> <li><a href="/wiki/GSK1360707F" title="GSK1360707F">GSK1360707F</a></li> <li><a href="/wiki/GYKI-52895" class="mw-redirect" title="GYKI-52895">GYKI-52895</a></li> <li><a href="/wiki/Hexacyclonate" title="Hexacyclonate">Hexacyclonate</a></li> <li><a href="/wiki/Idazoxan" title="Idazoxan">Idazoxan</a></li> <li><a href="/wiki/Indanorex" title="Indanorex">Indanorex</a></li> <li><a href="/wiki/Indatraline" title="Indatraline">Indatraline</a></li> <li><a href="/wiki/JNJ-7925476" title="JNJ-7925476">JNJ-7925476</a></li> <li><a href="/wiki/Lazabemide" title="Lazabemide">Lazabemide</a></li> <li><a href="/wiki/Leptacline" title="Leptacline">Leptacline</a></li> <li><a href="/wiki/Lomevactone" title="Lomevactone">Lomevactone</a></li> <li><a href="/wiki/LR-5182" title="LR-5182">LR-5182</a></li> <li><a href="/wiki/Mazindol" title="Mazindol">Mazindol</a></li> <li><a href="/wiki/Meclofenoxate" title="Meclofenoxate">Meclofenoxate</a></li> <li><a href="/wiki/Medifoxamine" title="Medifoxamine">Medifoxamine</a></li> <li><a href="/wiki/Mefexamide" title="Mefexamide">Mefexamide</a></li> <li><a href="/wiki/Methamnetamine" title="Methamnetamine">Methamnetamine</a></li> <li><a href="/wiki/Methastyridone" title="Methastyridone">Methastyridone</a></li> <li><a href="/wiki/Methiopropamine" title="Methiopropamine">Methiopropamine</a></li> <li><a href="/wiki/Naphthylaminopropane" title="Naphthylaminopropane">Naphthylaminopropane</a></li> <li><a href="/wiki/Nefopam" title="Nefopam">Nefopam</a></li> <li><a href="/wiki/Nikethamide" title="Nikethamide">Nikethamide</a></li> <li><a href="/wiki/Nomifensine" title="Nomifensine">Nomifensine</a></li> <li><a href="/wiki/O-2172" title="O-2172">O-2172</a></li> <li><a href="/wiki/Oxaprotiline" title="Oxaprotiline">Oxaprotiline</a></li> <li><a href="/wiki/PNU-99,194" title="PNU-99,194">PNU-99,194</a></li> <li><a href="/wiki/PRC200" class="mw-redirect" title="PRC200">PRC200-SS</a></li> <li><a href="/wiki/Rasagiline" title="Rasagiline">Rasagiline</a></li> <li><a href="/wiki/Rauwolscine" title="Rauwolscine">Rauwolscine</a></li> <li><a href="/wiki/Rubidium_chloride" title="Rubidium chloride">Rubidium chloride</a></li> <li><a href="/wiki/Setazindol" title="Setazindol">Setazindol</a></li> <li><a href="/wiki/Tametraline" title="Tametraline">Tametraline</a></li> <li><a href="/wiki/Tandamine" title="Tandamine">Tandamine</a></li> <li><a href="/wiki/Thiopropamine" title="Thiopropamine">Thiopropamine</a></li> <li><a href="/wiki/Thiothinone" title="Thiothinone">Thiothinone</a></li> <li><a href="/wiki/Trazium" title="Trazium">Trazium</a></li> <li><a href="/wiki/UH-232" title="UH-232">UH-232</a></li> <li><a href="/wiki/Yohimbine" title="Yohimbine">Yohimbine</a></li></ul> </div></td></tr><tr><td class="navbox-abovebelow" colspan="2" style="font-style:italic"><div><a href="/wiki/ATC_code" class="mw-redirect" title="ATC code">ATC code</a>: <a href="/wiki/ATC_code_N06#N06B" title="ATC code N06">N06B</a></div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374" /><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235" /><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374" /></div><div role="navigation" class="navbox" aria-labelledby="Analgesics_(N02A,_N02B)251" 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:Analgesics" title="Template:Analgesics"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Analgesics" title="Template talk:Analgesics"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Analgesics" title="Special:EditPage/Template:Analgesics"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Analgesics_(N02A,_N02B)251" style="font-size:114%;margin:0 4em"><a href="/wiki/Analgesic" title="Analgesic">Analgesics</a> (<a href="/wiki/ATC_code_N02#N02A" title="ATC code N02">N02A</a>, <a href="/wiki/ATC_code_N02#N02B" title="ATC code N02">N02B</a>)</div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Opioid" title="Opioid">Opioids</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/Opiate" title="Opiate">Opiates</a>/<a href="/wiki/Opium" title="Opium">opium</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/Codeine" title="Codeine">Codeine</a><sup>#</sup> <ul><li><a href="/wiki/Codeine/aspirin" class="mw-redirect" title="Codeine/aspirin">+aspirin</a></li> <li><a href="/wiki/Codeine/paracetamol" title="Codeine/paracetamol">+paracetamol</a></li></ul></li> <li><a href="/wiki/Morphine" title="Morphine">Morphine</a><sup>#</sup> (<a href="/wiki/Morphine/naltrexone" title="Morphine/naltrexone">+naltrexone</a>)</li> <li><a href="/wiki/Opium" title="Opium">Opium</a></li> <li><a href="/wiki/Laudanum" title="Laudanum">Laudanum</a></li> <li><a href="/wiki/Paregoric" title="Paregoric">Paregoric</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Semisynthetic</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/Acetyldihydrocodeine" title="Acetyldihydrocodeine">Acetyldihydrocodeine</a></li> <li><a href="/wiki/Benzylmorphine" title="Benzylmorphine">Benzylmorphine</a></li> <li><a href="/wiki/Buprenorphine" title="Buprenorphine">Buprenorphine</a><span class="nowrap"> </span>(<a href="/wiki/Buprenorphine/naloxone" title="Buprenorphine/naloxone">+naloxone</a>)</li> <li><a href="/wiki/Butorphanol" title="Butorphanol">Butorphanol</a></li> <li><a href="/wiki/Desomorphine" title="Desomorphine">Desomorphine</a></li> <li><a href="/wiki/Heroin" title="Heroin">Diamorphine (heroin)</a></li> <li><a href="/wiki/Dihydrocodeine" title="Dihydrocodeine">Dihydrocodeine</a><span class="nowrap"> </span>(<a href="/wiki/Co-dydramol" title="Co-dydramol">+paracetamol</a>)</li> <li><a href="/wiki/Dihydromorphine" title="Dihydromorphine">Dihydromorphine</a></li> <li><a href="/wiki/Etorphine" title="Etorphine">Etorphine</a></li> <li><a href="/wiki/Ethylmorphine" title="Ethylmorphine">Ethylmorphine</a></li> <li><a href="/wiki/Hydrocodone" title="Hydrocodone">Hydrocodone</a><span class="nowrap"> </span>(<a href="/wiki/Hydrocodone/paracetamol" title="Hydrocodone/paracetamol">+paracetamol</a>, <a href="/wiki/Hydrocodone/ibuprofen" title="Hydrocodone/ibuprofen">+ibuprofen</a>, <a href="/wiki/Hydrocodone/aspirin" title="Hydrocodone/aspirin">+aspirin</a>)</li> <li><a href="/wiki/Hydromorphinol" title="Hydromorphinol">Hydromorphinol</a></li> <li><a href="/wiki/Hydromorphone" title="Hydromorphone">Hydromorphone</a></li> <li><a href="/wiki/Levorphanol" title="Levorphanol">Levorphanol</a></li> <li><a href="/wiki/Metopon" title="Metopon">Metopon</a></li> <li><a href="/wiki/Nalbuphine" title="Nalbuphine">Nalbuphine</a></li> <li><a href="/wiki/Nicocodeine" title="Nicocodeine">Nicocodeine</a></li> <li><a href="/wiki/Nicodicodine" title="Nicodicodine">Nicodicodine</a></li> <li><a href="/wiki/Nicomorphine" title="Nicomorphine">Nicomorphine</a></li> <li><a href="/wiki/Oxycodone" title="Oxycodone">Oxycodone</a><span class="nowrap"> </span>(<a href="/wiki/Oxycodone/paracetamol" title="Oxycodone/paracetamol">+paracetamol</a>, <a href="/wiki/Oxycodone/aspirin" title="Oxycodone/aspirin">+aspirin</a>, <a href="/wiki/Oxycodone/ibuprofen" title="Oxycodone/ibuprofen">+ibuprofen</a>, <a href="/wiki/Oxycodone/naloxone" title="Oxycodone/naloxone">+naloxone</a>, <a href="/w/index.php?title=Oxycodone/naltrexone&action=edit&redlink=1" class="new" title="Oxycodone/naltrexone (page does not exist)">+naltrexone</a>)</li> <li><a href="/wiki/Oxymorphone" title="Oxymorphone">Oxymorphone</a></li> <li><a href="/wiki/Papaveretum" title="Papaveretum">Papaveretum</a></li> <li><a href="/wiki/Thebacon" title="Thebacon">Thebacon</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Synthetic</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/Alfentanil" title="Alfentanil">Alfentanil</a></li> <li><a href="/wiki/Prodine" title="Prodine">Alphaprodine</a></li> <li><a href="/wiki/Anileridine" title="Anileridine">Anileridine</a></li> <li><a href="/wiki/Bezitramide" title="Bezitramide">Bezitramide</a></li> <li><a href="/wiki/Carfentanil" title="Carfentanil">Carfentanil</a></li> <li><a href="/wiki/Dextromoramide" title="Dextromoramide">Dextromoramide</a></li> <li><a href="/wiki/Dextropropoxyphene" title="Dextropropoxyphene">Dextropropoxyphene</a></li> <li><a href="/wiki/Dezocine" title="Dezocine">Dezocine</a></li> <li><a href="/wiki/Dimenoxadol" title="Dimenoxadol">Dimenoxadol</a></li> <li><a href="/wiki/Dipipanone" title="Dipipanone">Dipipanone</a></li> <li><a href="/wiki/Ethoheptazine" title="Ethoheptazine">Ethoheptazine</a></li> <li><a href="/wiki/Fentanyl" title="Fentanyl">Fentanyl</a><sup>#</sup> (<a href="/wiki/Fentanyl/fluanisone" title="Fentanyl/fluanisone">+fluanisone</a>)</li> <li><a href="/wiki/Ketobemidone" title="Ketobemidone">Ketobemidone</a></li> <li><a href="/wiki/Lofentanil" title="Lofentanil">Lofentanil</a></li> <li><a href="/wiki/Meptazinol" title="Meptazinol">Meptazinol</a></li> <li><a href="/wiki/Methadone" title="Methadone">Methadone</a><sup>#</sup></li> <li><a href="/wiki/NFEPP" title="NFEPP">NFEPP</a></li> <li><a href="/wiki/Norpipanone" title="Norpipanone">Norpipanone</a></li> <li><a href="/wiki/Oliceridine" title="Oliceridine">Oliceridine</a></li> <li><a href="/wiki/Pentazocine" title="Pentazocine">Pentazocine</a></li> <li><a href="/wiki/Pethidine" title="Pethidine">Pethidine (meperidine)</a></li> <li><a href="/wiki/Phenadoxone" title="Phenadoxone">Phenadoxone</a></li> <li><a href="/wiki/Phenazocine" title="Phenazocine">Phenazocine</a></li> <li><a href="/wiki/Phenoperidine" title="Phenoperidine">Phenoperidine</a></li> <li><a href="/wiki/Piminodine" title="Piminodine">Piminodine</a></li> <li><a href="/wiki/Piritramide" title="Piritramide">Piritramide</a></li> <li><a href="/wiki/Proheptazine" title="Proheptazine">Proheptazine</a></li> <li><a href="/wiki/Propiram" title="Propiram">Propiram</a></li> <li><a href="/wiki/Remifentanil" title="Remifentanil">Remifentanil</a></li> <li><a href="/wiki/Sufentanil" title="Sufentanil">Sufentanil</a></li> <li><a href="/wiki/Tapentadol" title="Tapentadol">Tapentadol</a></li> <li><a href="/wiki/Tilidine" title="Tilidine">Tilidine</a></li> <li><a href="/wiki/Tramadol" title="Tramadol">Tramadol</a><span class="nowrap"> </span>(<a href="/wiki/Celecoxib/tramadol" title="Celecoxib/tramadol">+celecoxib</a>, <a href="/wiki/Tramadol/paracetamol" title="Tramadol/paracetamol">+paracetamol</a>)</li> <li><a href="/wiki/Viminol" title="Viminol">Viminol</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/Paracetamol" title="Paracetamol">Paracetamol</a>-type</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/Acetanilide" title="Acetanilide">Acetanilide</a><sup>‡</sup></li> <li><a href="/wiki/Bucetin" title="Bucetin">Bucetin</a><sup>‡</sup></li> <li><a href="/w/index.php?title=Butacetin&action=edit&redlink=1" class="new" title="Butacetin (page does not exist)">Butacetin</a><sup>‡</sup></li> <li><a href="/wiki/Paracetamol" title="Paracetamol">Paracetamol (acetaminophen)</a><sup>#</sup> <ul><li><a href="/wiki/Aspirin/paracetamol/caffeine" title="Aspirin/paracetamol/caffeine">+aspirin/caffeine</a></li> <li><a href="/wiki/Codeine/paracetamol" title="Codeine/paracetamol">+codeine</a></li> <li><a href="/wiki/Hydrocodone/paracetamol" title="Hydrocodone/paracetamol">+hydrocodone</a></li> <li><a href="/wiki/Ibuprofen/paracetamol" title="Ibuprofen/paracetamol">+ibuprofen</a></li> <li><a href="/wiki/Paracetamol/metoclopramide" title="Paracetamol/metoclopramide">+metoclopramide</a></li> <li><a href="/wiki/Oxycodone/paracetamol" title="Oxycodone/paracetamol">+oxycodone</a></li> <li><a href="/wiki/Propyphenazone/paracetamol/caffeine" title="Propyphenazone/paracetamol/caffeine">+propyphenazone/caffeine</a></li> <li><a href="/wiki/Tramadol/paracetamol" title="Tramadol/paracetamol">+tramadol</a></li></ul></li> <li><a href="/w/index.php?title=Parapropamol&action=edit&redlink=1" class="new" title="Parapropamol (page does not exist)">Parapropamol</a><sup>‡</sup></li> <li><a href="/wiki/Phenacetin" title="Phenacetin">Phenacetin</a><sup>‡</sup></li> <li><a href="/wiki/Propacetamol" title="Propacetamol">Propacetamol</a><sup>‡</sup></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Nonsteroidal_anti-inflammatory_drug" title="Nonsteroidal anti-inflammatory drug">NSAIDs</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%">Propionates</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/Benoxaprofen" title="Benoxaprofen">Benoxaprofen</a> <sup>‡</sup></li> <li><a href="/wiki/Fenoprofen" title="Fenoprofen">Fenoprofen</a></li> <li><a href="/wiki/Flurbiprofen" title="Flurbiprofen">Flurbiprofen</a></li> <li><a href="/wiki/Ibuprofen" title="Ibuprofen">Ibuprofen</a><sup>#</sup><span class="nowrap"> </span>(<a href="/wiki/Dexibuprofen" title="Dexibuprofen">Dexibuprofen</a>)<span class="nowrap"> </span>(<a href="/wiki/Ibuprofen/paracetamol" title="Ibuprofen/paracetamol">+paracetamol</a>)</li> <li><a href="/wiki/Ketoprofen" title="Ketoprofen">Ketoprofen</a><span class="nowrap"> </span>(<a href="/wiki/Dexketoprofen" title="Dexketoprofen">Dexketoprofen</a>)</li> <li><a href="/wiki/Loxoprofen" title="Loxoprofen">Loxoprofen</a></li> <li><a href="/wiki/Naproxen" title="Naproxen">Naproxen</a></li> <li><a href="/wiki/Oxaprozin" title="Oxaprozin">Oxaprozin</a></li> <li><a href="/wiki/Suprofen" title="Suprofen">Suprofen</a></li> <li><a href="/wiki/Tiaprofenic_acid" title="Tiaprofenic acid">Tiaprofenic acid</a></li> <li><a href="/wiki/Zaltoprofen" title="Zaltoprofen">Zaltoprofen</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Oxicams</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/Isoxicam" title="Isoxicam">Isoxicam</a></li> <li><a href="/wiki/Lornoxicam" title="Lornoxicam">Lornoxicam</a></li> <li><a href="/wiki/Meloxicam" title="Meloxicam">Meloxicam</a></li> <li><a href="/wiki/Piroxicam" title="Piroxicam">Piroxicam</a></li> <li><a href="/wiki/Tenoxicam" title="Tenoxicam">Tenoxicam</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Acetates</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/Acemetacin" title="Acemetacin">Acemetacin</a></li> <li><a href="/wiki/Bromfenac" title="Bromfenac">Bromfenac</a></li> <li><a href="/wiki/Diclofenac" title="Diclofenac">Diclofenac</a></li> <li><a href="/wiki/Etodolac" title="Etodolac">Etodolac</a></li> <li><a href="/wiki/Indometacin" title="Indometacin">Indometacin</a><span class="nowrap"> </span>(<a href="/wiki/Indometacin_farnesil" title="Indometacin farnesil">Indometacin farnesil</a>)</li> <li><a href="/wiki/Ketorolac" title="Ketorolac">Ketorolac</a></li> <li><a href="/wiki/Sulindac" title="Sulindac">Sulindac</a></li> <li><a href="/wiki/Tolmetin" title="Tolmetin">Tolmetin</a></li> <li><a href="/wiki/Zomepirac" title="Zomepirac">Zomepirac</a> <sup>‡</sup></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/COX-2_inhibitor" class="mw-redirect" title="COX-2 inhibitor">COX-2 inhibitors</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/Celecoxib" title="Celecoxib">Celecoxib</a><span class="nowrap"> </span>(<a href="/wiki/Celecoxib/tramadol" title="Celecoxib/tramadol">+tramadol</a>)</li> <li><a href="/wiki/Etoricoxib" title="Etoricoxib">Etoricoxib</a></li> <li><a href="/wiki/Lumiracoxib" title="Lumiracoxib">Lumiracoxib</a> <sup>‡</sup></li> <li><a href="/wiki/Parecoxib" title="Parecoxib">Parecoxib</a></li> <li><a href="/wiki/Rofecoxib" title="Rofecoxib">Rofecoxib</a> <sup>‡</sup></li> <li><a href="/wiki/Valdecoxib" title="Valdecoxib">Valdecoxib</a> <sup>‡</sup></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Fenamic_acid" title="Fenamic acid">Fenamates</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/Flufenamic_acid" title="Flufenamic acid">Flufenamic acid</a></li> <li><a href="/wiki/Meclofenamic_acid" title="Meclofenamic acid">Meclofenamic acid</a></li> <li><a href="/wiki/Mefenamic_acid" title="Mefenamic acid">Mefenamic acid</a></li> <li><a href="/wiki/Tolfenamic_acid" title="Tolfenamic acid">Tolfenamic acid</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Salicylic_acid" title="Salicylic acid">Salicylates</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/Aspirin" title="Aspirin">Aspirin (acetylsalicylic acid)</a><sup>#</sup> (<a href="/wiki/Aspirin/paracetamol/caffeine" title="Aspirin/paracetamol/caffeine">+paracetamol/caffeine</a>)</li> <li><a href="/wiki/Aloxiprin" title="Aloxiprin">Aloxiprin</a></li> <li><a href="/wiki/Benorilate" title="Benorilate">Benorylate</a></li> <li><a href="/wiki/Carbasalate_calcium" title="Carbasalate calcium">Carbasalate calcium</a></li> <li><a href="/wiki/Choline_salicylate" class="mw-redirect" title="Choline salicylate">Choline salicylate</a></li> <li><a href="/wiki/Diflunisal" title="Diflunisal">Diflunisal</a></li> <li><a href="/wiki/Dipyrocetyl" title="Dipyrocetyl">Dipyrocetyl</a></li> <li><a href="/wiki/Ethenzamide" title="Ethenzamide">Ethenzamide</a></li> <li><a href="/wiki/Guacetisal" title="Guacetisal">Guacetisal</a></li> <li><a href="/wiki/Imidazole_salicylate" title="Imidazole salicylate">Imidazole salicylate</a></li> <li><a href="/wiki/Magnesium_salicylate" title="Magnesium salicylate">Magnesium salicylate</a></li> <li><a href="/wiki/Morpholine_salicylate" title="Morpholine salicylate">Morpholine salicylate</a></li> <li><a href="/wiki/Potassium_salicylate" title="Potassium salicylate">Potassium salicylate</a></li> <li><a href="/wiki/Salicin" title="Salicin">Salicin</a></li> <li><a href="/wiki/Salicylamide" title="Salicylamide">Salicylamide</a></li> <li><a href="/wiki/Salsalate" title="Salsalate">Salsalate</a></li> <li><a href="/wiki/Sodium_salicylate" title="Sodium salicylate">Sodium salicylate</a></li> <li><a href="/wiki/Wintergreen" title="Wintergreen">Wintergreen</a><span class="nowrap"> </span>(<a href="/wiki/Methyl_salicylate" title="Methyl salicylate">methyl salicylate</a>)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Pyrazolone" title="Pyrazolone">Pyrazolones</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/Aminophenazone" title="Aminophenazone">Aminophenazone</a><sup>‡</sup></li> <li><a href="/wiki/Ampyrone" title="Ampyrone">Ampyrone</a></li> <li><a href="/wiki/Metamizole" title="Metamizole">Metamizole (dipyrone)</a></li> <li><a href="/wiki/Nifenazone" title="Nifenazone">Nifenazone</a></li> <li><a href="/wiki/Phenazone" title="Phenazone">Phenazone</a></li> <li><a href="/wiki/Propyphenazone" title="Propyphenazone">Propyphenazone</a><span class="nowrap"> </span>(<a href="/wiki/Propyphenazone/paracetamol/caffeine" title="Propyphenazone/paracetamol/caffeine">+paracetamol/caffeine</a>)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Others</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Benzydamine" title="Benzydamine">Benzydamine</a></li> <li><a href="/wiki/Floctafenine" title="Floctafenine">Floctafenine</a></li> <li><a href="/wiki/Glafenine" title="Glafenine">Glafenine</a></li> <li><a href="/wiki/Nabumetone" title="Nabumetone">Nabumetone</a></li> <li><a href="/wiki/Nimesulide" title="Nimesulide">Nimesulide</a></li> <li><a href="/wiki/Proquazone" title="Proquazone">Proquazone</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/Cannabinoid" title="Cannabinoid">Cannabinoids</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/Cannabidiol" title="Cannabidiol">Cannabidiol</a></li> <li><a href="/wiki/Cannabis_(drug)" title="Cannabis (drug)">Cannabis</a></li> <li><a href="/wiki/Nabilone" title="Nabilone">Nabilone</a></li> <li><a href="/wiki/Nabiximols" title="Nabiximols">Nabiximols</a></li> <li><a href="/wiki/Tetrahydrocannabinol" title="Tetrahydrocannabinol">Tetrahydrocannabinol (dronabinol)</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Channel_modulator" title="Channel modulator">Ion channel<br />modulators</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Calcium_channel_blocker" title="Calcium channel blocker">Calcium blockers</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/Alcohol_(drug)" title="Alcohol (drug)">Alcohol (ethanol)</a></li> <li><a href="/wiki/Gabapentin" title="Gabapentin">Gabapentin</a></li> <li><a href="/wiki/Gabapentin_enacarbil" title="Gabapentin enacarbil">Gabapentin enacarbil</a></li> <li><a href="/wiki/Leconotide" title="Leconotide">Leconotide</a></li> <li><a href="/wiki/Mirogabalin" title="Mirogabalin">Mirogabalin</a></li> <li><a href="/wiki/Pregabalin" title="Pregabalin">Pregabalin</a></li> <li><a href="/wiki/Ziconotide" title="Ziconotide">Ziconotide</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Sodium_channel_blocker" title="Sodium channel blocker">Sodium blockers</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Carbamazepine" title="Carbamazepine">Carbamazepine</a></li> <li><a href="/wiki/Lacosamide" title="Lacosamide">Lacosamide</a></li> <li><a href="/wiki/Local_anesthetic" title="Local anesthetic">Local anesthetics</a> (e.g., <a href="/wiki/Cocaine" title="Cocaine">cocaine</a>, <a href="/wiki/Lidocaine" title="Lidocaine">lidocaine</a>)</li> <li><a href="/wiki/Mexiletine" title="Mexiletine">Mexiletine</a></li> <li><a href="/wiki/Nefopam" title="Nefopam">Nefopam</a></li> <li><a href="/wiki/Tricyclic_antidepressant" title="Tricyclic antidepressant">Tricyclic antidepressants</a> (e.g., <a href="/wiki/Amitriptyline" title="Amitriptyline">amitriptyline</a><sup>#</sup>)</li></ul> <ul><li><i>Na<sub>v</sub>1.7/1.8-selective:</i> <a href="/wiki/DSP-2230" title="DSP-2230">DSP-2230</a><sup>§</sup></li> <li><a href="/wiki/Funapide" title="Funapide">Funapide</a><sup>§</sup></li> <li><a href="/wiki/PF-05089771" title="PF-05089771">PF-05089771</a><sup>§</sup></li> <li><a href="/wiki/Suzetrigine" title="Suzetrigine">Suzetrigine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Potassium_channel_opener" title="Potassium channel opener">Potassium openers</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/Flupirtine" title="Flupirtine">Flupirtine</a><sup>‡</sup></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Muscle_relaxant" title="Muscle relaxant">Myorelaxants</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/Carisoprodol" title="Carisoprodol">Carisoprodol</a></li> <li><a href="/wiki/Chlorzoxazone" title="Chlorzoxazone">Chlorzoxazone</a></li> <li><a href="/wiki/Cyclobenzaprine" title="Cyclobenzaprine">Cyclobenzaprine</a></li> <li><a href="/wiki/Mephenoxalone" title="Mephenoxalone">Mephenoxalone</a></li> <li><a href="/wiki/Methocarbamol" title="Methocarbamol">Methocarbamol</a></li> <li><a href="/wiki/Orphenadrine" title="Orphenadrine">Orphenadrine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Others</th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Analgecine" title="Analgecine">Analgecine</a></li> <li><a href="/wiki/Analgesic_adjuvant" title="Analgesic adjuvant">Analgesic adjuvant</a></li> <li><a href="/wiki/Bedinvetmab" title="Bedinvetmab">Bedinvetmab</a></li> <li><a href="/wiki/Camphor" title="Camphor">Camphor</a></li> <li><a href="/wiki/Capsaicin" title="Capsaicin">Capsaicin</a></li> <li><a href="/wiki/Clonidine" title="Clonidine">Clonidine</a></li> <li><a href="/wiki/Frunevetmab" title="Frunevetmab">Frunevetmab</a></li> <li><a href="/wiki/Ketamine" title="Ketamine">Ketamine</a></li> <li><a href="/wiki/Menthol" title="Menthol">Menthol</a></li> <li><a href="/wiki/Methoxyflurane" title="Methoxyflurane">Methoxyflurane</a></li> <li><a href="/wiki/Phenazopyridine" title="Phenazopyridine">Phenazopyridine</a></li> <li><a href="/wiki/Proglumide" title="Proglumide">Proglumide</a></li> <li><a href="/wiki/Rimazolium" title="Rimazolium">Rimazolium</a></li> <li><a href="/wiki/Tanezumab" title="Tanezumab">Tanezumab</a></li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"><div class="hlist"> <ul><li><sup>#</sup><a href="/wiki/WHO_Model_List_of_Essential_Medicines" title="WHO Model List of Essential Medicines">WHO-EM</a></li> <li><sup>‡</sup><a href="/wiki/List_of_withdrawn_drugs" title="List of withdrawn drugs">Withdrawn</a> from market</li> <li><a href="/wiki/Clinical_trial" title="Clinical trial">Clinical trials</a>: <ul><li><sup>†</sup><a href="/wiki/Phases_of_clinical_research#Phase_III" title="Phases of clinical research">Phase III</a></li> <li><sup>§</sup>Never to phase III</li></ul></li></ul> </div></div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374" /><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235" /></div><div role="navigation" class="navbox" aria-labelledby="*_Toxins_**_cardiotoxin_**_cytotoxin_**_enterotoxin_**_hemotoxin_**_hepatotoxin_**_neurotoxin_**_phototoxin403" 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:Toxins" title="Template:Toxins"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Toxins" title="Template talk:Toxins"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Toxins" title="Special:EditPage/Template:Toxins"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="*_Toxins_**_cardiotoxin_**_cytotoxin_**_enterotoxin_**_hemotoxin_**_hepatotoxin_**_neurotoxin_**_phototoxin403" style="font-size:114%;margin:0 4em"> <ul><li><a href="/wiki/Toxin" title="Toxin">Toxins</a> <ul><li><a href="/wiki/Cardiotoxicity" title="Cardiotoxicity">cardiotoxin</a></li> <li><a href="/wiki/Cytotoxicity" title="Cytotoxicity">cytotoxin</a></li> <li><a href="/wiki/Enterotoxin" title="Enterotoxin">enterotoxin</a></li> <li><a href="/wiki/Hemotoxin" title="Hemotoxin">hemotoxin</a></li> <li><a href="/wiki/Hepatotoxin" title="Hepatotoxin">hepatotoxin</a></li> <li><a href="/wiki/Neurotoxin" title="Neurotoxin">neurotoxin</a></li> <li><a href="/wiki/Phototoxin" title="Phototoxin">phototoxin</a></li></ul></li></ul> </div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Microbial_toxin" title="Microbial toxin">Bacterial<br /> toxins</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/Exotoxin" title="Exotoxin">Exotoxin</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="Gram_positive119" scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Gram-positive_bacteria" title="Gram-positive bacteria">Gram<br /> positive</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/Bacilli" title="Bacilli">Bacilli</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%"><span class="nobold"><a href="/wiki/Clostridium" title="Clostridium">Clostridium</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><i><a href="/wiki/Clostridium_tetani" title="Clostridium tetani">tetani</a></i> <ul><li><a href="/wiki/Tetanospasmin" class="mw-redirect" title="Tetanospasmin">Tetanospasmin</a></li> <li><a href="/wiki/Tetanolysin" title="Tetanolysin">Tetanolysin</a></li></ul></li> <li><i><a href="/wiki/Clostridium_perfringens" title="Clostridium perfringens">perfringens</a></i> <ul><li><a href="/wiki/Clostridium_perfringens_alpha_toxin" title="Clostridium perfringens alpha toxin">Alpha toxin</a></li> <li><a href="/wiki/Clostridium_enterotoxin" title="Clostridium enterotoxin">Enterotoxin</a></li></ul></li> <li><i><a href="/wiki/Clostridium_difficile_(bacteria)" class="mw-redirect" title="Clostridium difficile (bacteria)">difficile</a></i> <ul><li><a href="/wiki/Clostridioides_difficile_toxin_A" title="Clostridioides difficile toxin A">A</a></li> <li><a href="/wiki/Clostridioides_difficile_toxin_B" title="Clostridioides difficile toxin B">B</a></li></ul></li> <li><i><a href="/wiki/Clostridium_botulinum" title="Clostridium botulinum">botulinum</a></i> <ul><li><a href="/wiki/Botulinum_toxin" title="Botulinum toxin">Botox</a></li></ul></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><span class="nobold">Other:</span></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Anthrax_toxin" title="Anthrax toxin">Anthrax toxin</a></li> <li><a href="/wiki/Listeriolysin_O" title="Listeriolysin O">Listeriolysin O</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/Coccus" class="mw-redirect" title="Coccus">Cocci</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><a href="/wiki/Streptolysin" title="Streptolysin">Streptolysin</a></li> <li><a href="/wiki/Leukocidin" title="Leukocidin">Leukocidin</a> <ul><li><a href="/wiki/Panton%E2%80%93Valentine_leukocidin" title="Panton–Valentine leukocidin">Panton–Valentine leukocidin</a></li></ul></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><span class="nobold"><a href="/wiki/Staphylococcus" title="Staphylococcus">Staphylococcus</a></span></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Staphylococcus_aureus_alpha_toxin" title="Staphylococcus aureus alpha toxin">Staphylococcus aureus alpha</a>/<a href="/wiki/Staphylococcus_aureus_beta_toxin" title="Staphylococcus aureus beta toxin">beta</a>/<a href="/wiki/Staphylococcus_aureus_delta_toxin" title="Staphylococcus aureus delta toxin">delta</a></li> <li><a href="/wiki/Exfoliatin" title="Exfoliatin">Exfoliatin</a></li> <li><a href="/wiki/Toxic_shock_syndrome_toxin-1" title="Toxic shock syndrome toxin-1">Toxic shock syndrome toxin</a></li> <li><a href="/wiki/Enterotoxin_type_B" title="Enterotoxin type B">Staphylococcal Enterotoxin B (SEB)</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/Actinomycetota" title="Actinomycetota">Actinomycetota</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/Cord_factor" title="Cord factor">Cord factor</a></li> <li><a href="/wiki/Diphtheria_toxin" title="Diphtheria toxin">Diphtheria toxin</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/Gram-negative_bacteria" title="Gram-negative bacteria">Gram<br /> negative</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/Shiga_toxin" title="Shiga toxin">Shiga toxin</a>/Verotoxin</li> <li><a href="/wiki/Heat-stable_enterotoxin" title="Heat-stable enterotoxin"><i>E. coli</i> heat-stable enterotoxin</a></li> <li><a href="/wiki/Cholera_toxin" title="Cholera toxin">Cholera toxin</a>/<a href="/wiki/Heat-labile_enterotoxin" class="mw-redirect" title="Heat-labile enterotoxin">Heat-labile enterotoxin</a></li> <li><a href="/wiki/Pertussis_toxin" title="Pertussis toxin">Pertussis toxin</a></li> <li><a href="/wiki/Pseudomonas_exotoxin" title="Pseudomonas exotoxin">Pseudomonas exotoxin</a></li> <li><a href="/wiki/Extracellular_adenylate_cyclase" title="Extracellular adenylate cyclase">Extracellular adenylate cyclase</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Exotoxin#Types" title="Exotoxin">Mechanisms</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/Exotoxin#Type_I:_cell_surface-active" title="Exotoxin">type I</a></i> <ul><li><a href="/wiki/Superantigen" title="Superantigen">Superantigen</a></li></ul></li> <li><i><a href="/wiki/Exotoxin#Type_II:_membrane_damaging" title="Exotoxin">type II</a></i> <ul><li><a href="/wiki/Pore-forming_toxin" title="Pore-forming toxin">Pore-forming toxin</a></li></ul></li> <li><i><a href="/wiki/Exotoxin#Type_III:_intracellular" title="Exotoxin">type III</a></i> <ul><li><a href="/wiki/AB_toxin" title="AB toxin">AB toxin</a>/<a href="/wiki/AB5_toxin" title="AB5 toxin">AB5</a></li></ul></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Endotoxin" class="mw-redirect" title="Endotoxin">Endotoxin</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/Lipopolysaccharide" title="Lipopolysaccharide">Lipopolysaccharide</a> <ul><li><a href="/wiki/Lipid_A" title="Lipid A">Lipid A</a></li></ul></li> <li><a href="/wiki/Delta_endotoxins" title="Delta endotoxins"><i>Bacillus thuringiensis</i> delta endotoxin</a> <ul><li><a href="/wiki/Cry1Ac" title="Cry1Ac">Cry1Ac</a></li> <li><a href="/wiki/Cry3Bb1" class="mw-redirect" title="Cry3Bb1">Cry3Bb1</a></li></ul></li> <li>Other <i>B. thuringiensis</i> toxins <ul><li><a href="/wiki/Cry6Aa" title="Cry6Aa">Cry6Aa</a></li> <li><a href="/wiki/Cry34Ab1" title="Cry34Ab1">Cry34Ab1</a></li></ul></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Virulence_factor" title="Virulence factor">Virulence<br /> factor</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/Clumping_factor_A" title="Clumping factor A">Clumping factor A</a></li> <li><a href="/wiki/Fibronectin_binding_protein_A" title="Fibronectin binding protein A">Fibronectin binding protein A</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/Mycotoxin" title="Mycotoxin">Mycotoxins</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/Aflatoxin" title="Aflatoxin">Aflatoxin</a></li> <li><a href="/wiki/Amatoxin" title="Amatoxin">Amatoxin</a> (<a href="/wiki/%CE%91-Amanitin" title="Α-Amanitin">alpha-amanitin</a>, <a href="/wiki/%CE%92-Amanitin" title="Β-Amanitin">beta-amanitin</a>, <a href="/wiki/%CE%93-Amanitin" title="Γ-Amanitin">gamma-amanitin</a>, <a href="/wiki/%CE%95-Amanitin" title="Ε-Amanitin">epsilon-amanitin</a>)</li> <li><a href="/wiki/3-Nitropropionic_acid" title="3-Nitropropionic acid">beta-Nitropropionic acid</a></li> <li><a href="/wiki/Citrinin" title="Citrinin">Citrinin</a></li> <li><a href="/wiki/Cytochalasin" title="Cytochalasin">Cytochalasin</a></li> <li><a href="/wiki/Ergotamine" title="Ergotamine">Ergotamine</a></li> <li><a href="/wiki/Fumonisin" title="Fumonisin">Fumonisin</a> (<a href="/wiki/Fumonisin_B1" title="Fumonisin B1">Fumonisin B1</a>, <a href="/wiki/Fumonisin_B2" title="Fumonisin B2">Fumonisin B2</a>, Fumonisin B3, <a href="/wiki/Fumonisin_B4" title="Fumonisin B4">Fumonisin B4</a>)</li> <li><a href="/wiki/Gliotoxin" title="Gliotoxin">Gliotoxin</a></li> <li><a href="/wiki/Ibotenic_acid" title="Ibotenic acid">Ibotenic acid</a></li> <li><a href="/wiki/Lolitrem_B" title="Lolitrem B">Lolitrem B</a></li> <li><a href="/wiki/Muscimol" title="Muscimol">Muscimol</a></li> <li><a href="/wiki/Orellanine" title="Orellanine">Orellanine</a></li> <li><a href="/wiki/Ochratoxin" title="Ochratoxin">Ochratoxin</a></li> <li><a href="/wiki/Patulin" title="Patulin">Patulin</a></li> <li><a href="/wiki/Phalloidin" title="Phalloidin">Phalloidin</a></li> <li><a href="/wiki/Sterigmatocystin" title="Sterigmatocystin">Sterigmatocystin</a></li> <li><a href="/wiki/Trichothecene" title="Trichothecene">Trichothecene</a></li> <li><a href="/wiki/Vomitoxin" title="Vomitoxin">Vomitoxin</a></li> <li><a href="/wiki/Zeranol" title="Zeranol">Zeranol</a></li> <li><a href="/wiki/Zearalenone" title="Zearalenone">Zearalenone</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Plant" title="Plant">Plant</a> toxins</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/Amygdalin" title="Amygdalin">Amygdalin</a></li> <li><a href="/wiki/Anisatin" title="Anisatin">Anisatin</a></li> <li><a href="/wiki/Antiarin" title="Antiarin">Antiarin</a></li> <li><a href="/wiki/Brucine" title="Brucine">Brucine</a></li> <li><a href="/wiki/Chaconine" title="Chaconine">Chaconine</a></li> <li><a href="/wiki/Cicutoxin" title="Cicutoxin">Cicutoxin</a></li> <li><a href="/wiki/Coniine" title="Coniine">Coniine</a></li> <li><a href="/wiki/Daphnin" title="Daphnin">Daphnin</a></li> <li><a href="/wiki/Delphinine" title="Delphinine">Delphinine</a></li> <li><a href="/wiki/Divicine" title="Divicine">Divicine</a></li> <li><a href="/wiki/Djenkolic_acid" title="Djenkolic acid">Djenkolic acid</a></li> <li><a href="/wiki/Falcarinol" title="Falcarinol">Falcarinol</a></li> <li><a href="/wiki/Gossypol" title="Gossypol">Gossypol</a></li> <li><a href="/wiki/Helenalin" title="Helenalin">Helenalin</a></li> <li><a href="/wiki/Ledol" title="Ledol">Ledol</a></li> <li><a href="/wiki/Linamarin" title="Linamarin">Linamarin</a></li> <li><a href="/wiki/Lotaustralin" title="Lotaustralin">Lotaustralin</a></li> <li><a href="/wiki/Mimosine" title="Mimosine">Mimosine</a></li> <li><a href="/wiki/Oenanthotoxin" title="Oenanthotoxin">Oenanthotoxin</a></li> <li><a href="/wiki/Oleandrin" title="Oleandrin">Oleandrin</a></li> <li><a href="/wiki/Persin" title="Persin">Persin</a></li> <li><a href="/wiki/Protoanemonin" title="Protoanemonin">Protoanemonin</a></li> <li><a href="/wiki/Pseudaconitine" title="Pseudaconitine">Pseudaconitine</a></li> <li><a href="/wiki/Retronecine" title="Retronecine">Retronecine</a></li> <li><a href="/wiki/Resiniferatoxin" title="Resiniferatoxin">Resiniferatoxin</a></li> <li><a href="/wiki/Hyoscine_hydrobromide" class="mw-redirect" title="Hyoscine hydrobromide">Scopolamine</a></li> <li><a href="/wiki/Solamargine" title="Solamargine">Solamargine</a></li> <li><a href="/wiki/Solanidine" title="Solanidine">Solanidine</a></li> <li><a href="/wiki/Solanine" title="Solanine">Solanine</a></li> <li><a href="/wiki/Solasodamine" class="mw-redirect" title="Solasodamine">Solasodamine</a></li> <li><a href="/wiki/Solasodine" title="Solasodine">Solasodine</a></li> <li><a href="/wiki/Solasonine" title="Solasonine">Solasonine</a></li> <li><a href="/wiki/Solauricidine" class="mw-redirect" title="Solauricidine">Solauricidine</a></li> <li><a href="/wiki/Solauricine" class="mw-redirect" title="Solauricine">Solauricine</a></li> <li><a href="/wiki/Strychnine" title="Strychnine">Strychnine</a></li> <li><a href="/wiki/Swainsonine" title="Swainsonine">Swainsonine</a></li> <li><a href="/wiki/Tagetitoxin" title="Tagetitoxin">Tagetitoxin</a></li> <li><a href="/wiki/Tinyatoxin" title="Tinyatoxin">Tinyatoxin</a></li> <li><a href="/wiki/Tomatine" title="Tomatine">Tomatine</a></li> <li><a href="/wiki/Toxalbumin" title="Toxalbumin">Toxalbumin</a> <ul><li><a href="/wiki/Abrin" title="Abrin">Abrin</a></li> <li><a href="/wiki/Ricin" title="Ricin">Ricin</a></li></ul></li> <li><a href="/wiki/Tutin_(toxin)" title="Tutin (toxin)">Tutin</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Invertebrate" title="Invertebrate">Invertebrate</a> <br />toxins</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%"><span class="nobold"><a href="/wiki/Scorpion" title="Scorpion">Scorpion</a>:</span></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Androctonus_australis_hector_insect_toxin" title="Androctonus australis hector insect toxin">Androctonus australis hector insect toxin</a></li> <li><a href="/wiki/Charybdotoxin" title="Charybdotoxin">Charybdotoxin</a></li> <li><a href="/wiki/Maurotoxin" title="Maurotoxin">Maurotoxin</a></li> <li><a href="/wiki/Agitoxin" title="Agitoxin">Agitoxin</a></li> <li><a href="/wiki/Margatoxin" title="Margatoxin">Margatoxin</a></li> <li><a href="/wiki/Slotoxin" title="Slotoxin">Slotoxin</a></li> <li><a href="/wiki/Scyllatoxin" title="Scyllatoxin">Scyllatoxin</a></li> <li><a href="/wiki/Hefutoxin" title="Hefutoxin">Hefutoxin</a></li> <li><a href="/wiki/HgeTx1" title="HgeTx1">HgeTx1</a></li> <li><a href="/wiki/HsTx1" title="HsTx1">HsTx1</a></li> <li><a href="/wiki/Kaliotoxin" title="Kaliotoxin">Kaliotoxin</a></li> <li><a href="/wiki/Lq2" title="Lq2">Lq2</a></li> <li><a href="/wiki/Birtoxin" title="Birtoxin">Birtoxin</a></li> <li><a href="/wiki/Bestoxin" title="Bestoxin">Bestoxin</a></li> <li><a href="/wiki/BmKAEP" title="BmKAEP">BmKAEP</a></li> <li><a href="/wiki/Phaiodotoxin" title="Phaiodotoxin">Phaiodotoxin</a></li> <li><a href="/wiki/Imperatoxin" title="Imperatoxin">Imperatoxin</a></li> <li><a href="/wiki/Pandinus_imperator_(Pi3)_toxin" title="Pandinus imperator (Pi3) toxin">Pi3</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><span class="nobold"><a href="/wiki/Spider" title="Spider">Spider</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><a href="/wiki/Latrotoxin" title="Latrotoxin">Latrotoxin</a> <ul><li><a href="/wiki/Alpha-Latrotoxin" class="mw-redirect" title="Alpha-Latrotoxin">Alpha-latrotoxin</a></li></ul></li> <li><a href="/wiki/CSTX" title="CSTX">CSTX</a></li> <li><a href="/wiki/Cupiennin" title="Cupiennin">Cupiennins</a></li> <li><a href="/wiki/Phoneutria_nigriventer_toxin-3" title="Phoneutria nigriventer toxin-3">PhTx3</a></li> <li><a href="/wiki/Stromatoxin" title="Stromatoxin">Stromatoxin</a></li> <li><a href="/wiki/Vanillotoxin" title="Vanillotoxin">Vanillotoxin</a></li> <li><a href="/wiki/Huwentoxin" title="Huwentoxin">Huwentoxin</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><span class="nobold"><a href="/wiki/Mollusca" title="Mollusca">Mollusca</a>:</span></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Conotoxin" title="Conotoxin">Conotoxin</a></li> <li><a href="/wiki/Eledoisin" title="Eledoisin">Eledoisin</a></li> <li><a href="/wiki/Onchidal" title="Onchidal">Onchidal</a></li> <li><a href="/wiki/Saxitoxin" title="Saxitoxin">Saxitoxin</a></li> <li><a href="/wiki/Tetrodotoxin" title="Tetrodotoxin">Tetrodotoxin</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/Vertebrate" title="Vertebrate">Vertebrate</a> <br />toxins</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%"><span class="nobold"><a href="/wiki/Fish" title="Fish">Fish</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><a href="/wiki/Ciguatoxin" title="Ciguatoxin">Ciguatoxin</a></li> <li><a href="/wiki/Tetrodotoxin" title="Tetrodotoxin">Tetrodotoxin</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><span class="nobold"><a href="/wiki/Amphibian" title="Amphibian">Amphibian</a>:</span></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Allopumiliotoxin_267A" title="Allopumiliotoxin 267A">(+)-Allopumiliotoxin 267A</a></li> <li><a href="/wiki/Batrachotoxin" title="Batrachotoxin">Batrachotoxin</a></li> <li><a href="/wiki/Bufotoxin" title="Bufotoxin">Bufotoxins</a> <ul><li><a href="/wiki/Arenobufagin" title="Arenobufagin">Arenobufagin</a></li> <li><a href="/wiki/Bufotalin" title="Bufotalin">Bufotalin</a></li> <li><a href="/wiki/Bufotenin" title="Bufotenin">Bufotenin</a></li> <li><a href="/wiki/Cinobufagin" title="Cinobufagin">Cinobufagin</a></li> <li><a href="/wiki/Marinobufagenin" title="Marinobufagenin">Marinobufagin</a></li></ul></li> <li><a class="mw-selflink selflink">Epibatidine</a></li> <li><a href="/wiki/Histrionicotoxin" class="mw-redirect" title="Histrionicotoxin">Histrionicotoxin</a></li> <li><a href="/wiki/Pumiliotoxin_251D" title="Pumiliotoxin 251D">Pumiliotoxin 251D</a></li> <li><a href="/wiki/Samandarin" title="Samandarin">Samandarin</a></li> <li><a href="/wiki/Samandaridine" title="Samandaridine">Samandaridine</a></li> <li><a href="/wiki/Tetrodotoxin" title="Tetrodotoxin">Tarichatoxin</a></li> <li><a href="/wiki/Zetekitoxin_AB" title="Zetekitoxin AB">Zetekitoxin AB</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><span class="nobold"><a href="/wiki/Reptile" title="Reptile">Reptile</a>/<br /><a href="/wiki/Snake_venom" title="Snake venom">Snake venom</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><a href="/wiki/Bungarotoxin" title="Bungarotoxin">Bungarotoxin</a> <ul><li><a href="/wiki/%CE%91-Bungarotoxin" title="Α-Bungarotoxin">α-Bungarotoxin</a></li> <li><a href="/wiki/%CE%92-Bungarotoxin" title="Β-Bungarotoxin">β-Bungarotoxin</a></li></ul></li> <li><a href="/wiki/Calciseptine" title="Calciseptine">Calciseptine</a></li> <li><a href="/wiki/Taicatoxin" title="Taicatoxin">Taicatoxin</a></li> <li><a href="/wiki/Calcicludine" title="Calcicludine">Calcicludine</a></li> <li><a href="/wiki/Cardiotoxin_III" title="Cardiotoxin III">Cardiotoxin III</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><td colspan="2" class="navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i>note: some toxins are produced by lower species and pass through intermediate species</i></li></ul> </div></td></tr><tr><td class="navbox-abovebelow" colspan="2"><div> <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> <a href="/wiki/Category:Toxicology" title="Category:Toxicology">Category</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="Nicotinic_acetylcholine_receptor_modulators859" 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:Nicotinic_acetylcholine_receptor_modulators" title="Template:Nicotinic acetylcholine receptor modulators"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Nicotinic_acetylcholine_receptor_modulators" title="Template talk:Nicotinic acetylcholine receptor modulators"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Nicotinic_acetylcholine_receptor_modulators" title="Special:EditPage/Template:Nicotinic acetylcholine receptor modulators"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Nicotinic_acetylcholine_receptor_modulators859" style="font-size:114%;margin:0 4em"><a href="/wiki/Nicotinic_acetylcholine_receptor" title="Nicotinic acetylcholine receptor">Nicotinic acetylcholine 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/Nicotinic_acetylcholine_receptors" class="mw-redirect" title="Nicotinic acetylcholine receptors"><abbr title="Nicotinic acetylcholine receptors">nAChRs</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Nicotinic acetylcholine receptors</span></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/Receptor_agonist" class="mw-redirect" title="Receptor agonist">Agonists</a><br />(and <a href="/wiki/Positive_allosteric_modulators" class="mw-redirect" title="Positive allosteric modulators"><abbr title="positive allosteric modulators">PAMs</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip positive allosteric modulators</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><a href="/wiki/5-Hydroxyindoleacetic_acid" title="5-Hydroxyindoleacetic acid">5-HIAA</a></li> <li><a href="/wiki/6-Chloronicotine" title="6-Chloronicotine">6-Chloronicotine</a></li> <li><a href="/wiki/A-84,543" title="A-84,543">A-84,543</a></li> <li><a href="/wiki/A-366,833" title="A-366,833">A-366,833</a></li> <li><a href="/w/index.php?title=A-582,941&action=edit&redlink=1" class="new" title="A-582,941 (page does not exist)">A-582,941</a></li> <li><a href="/w/index.php?title=A-867,744&action=edit&redlink=1" class="new" title="A-867,744 (page does not exist)">A-867,744</a></li> <li><a href="/wiki/ABT-202" title="ABT-202">ABT-202</a></li> <li><a href="/wiki/ABT-418" title="ABT-418">ABT-418</a></li> <li><a href="/w/index.php?title=ABT-560&action=edit&redlink=1" class="new" title="ABT-560 (page does not exist)">ABT-560</a></li> <li><a href="/w/index.php?title=ABT-894&action=edit&redlink=1" class="new" title="ABT-894 (page does not exist)">ABT-894</a></li> <li><a href="/wiki/Acetylcholine" title="Acetylcholine">Acetylcholine</a></li> <li><a href="/wiki/Altinicline" title="Altinicline">Altinicline</a></li> <li><a href="/wiki/Anabasine" title="Anabasine">Anabasine</a></li> <li><a href="/wiki/Anatabine" title="Anatabine">Anatabine</a></li> <li><a href="/wiki/Anatoxin-a" title="Anatoxin-a">Anatoxin-a</a></li> <li><a href="/wiki/AR-R17779" title="AR-R17779">AR-R17779</a></li> <li><a href="/wiki/Bephenium_hydroxynaphthoate" title="Bephenium hydroxynaphthoate">Bephenium hydroxynaphthoate</a></li> <li><a href="/wiki/Butinoline" title="Butinoline">Butinoline</a></li> <li><a href="/wiki/Butyrylcholine" title="Butyrylcholine">Butyrylcholine</a></li> <li><a href="/wiki/Carbachol" title="Carbachol">Carbachol</a></li> <li><a href="/wiki/Choline" title="Choline">Choline</a></li> <li><a href="/wiki/Choline_m-bromophenyl_ether" title="Choline m-bromophenyl ether">Choline m-bromophenyl ether</a></li> <li><a href="/wiki/Cotinine" title="Cotinine">Cotinine</a></li> <li><a href="/wiki/Cytisine" title="Cytisine">Cytisine</a></li> <li><a href="/wiki/Decamethonium" title="Decamethonium">Decamethonium</a></li> <li><a href="/wiki/Desformylflustrabromine" title="Desformylflustrabromine">Desformylflustrabromine</a></li> <li><a href="/wiki/Dianicline" title="Dianicline">Dianicline</a></li> <li><a href="/wiki/Dimethylphenylpiperazinium" title="Dimethylphenylpiperazinium">Dimethylphenylpiperazinium</a></li> <li><a class="mw-selflink selflink">Epibatidine</a></li> <li><a href="/wiki/Epiboxidine" title="Epiboxidine">Epiboxidine</a></li> <li><a href="/wiki/Alcohol_(drug)" title="Alcohol (drug)">Ethanol (alcohol)</a></li> <li><a href="/w/index.php?title=Ethoxysebacylcholine&action=edit&redlink=1" class="new" title="Ethoxysebacylcholine (page does not exist)">Ethoxysebacylcholine</a></li> <li><a href="/w/index.php?title=EVP-4473&action=edit&redlink=1" class="new" title="EVP-4473 (page does not exist)">EVP-4473</a></li> <li><a href="/wiki/EVP-6124" class="mw-redirect" title="EVP-6124">EVP-6124</a></li> <li><a href="/wiki/Galantamine" title="Galantamine">Galantamine</a></li> <li><a href="/wiki/GTS-21" title="GTS-21">GTS-21</a></li> <li><a href="/wiki/Ispronicline" title="Ispronicline">Ispronicline</a></li> <li><a href="/wiki/Ivermectin" title="Ivermectin">Ivermectin</a></li> <li><a href="/wiki/JNJ-39393406" title="JNJ-39393406">JNJ-39393406</a></li> <li><a href="/wiki/Levamisole" title="Levamisole">Levamisole</a></li> <li><a href="/wiki/Lobeline" title="Lobeline">Lobeline</a></li> <li><a href="/w/index.php?title=MEM-63,908&action=edit&redlink=1" class="new" title="MEM-63,908 (page does not exist)">MEM-63,908 (RG-3487)</a></li> <li><a href="/wiki/Morantel" title="Morantel">Morantel</a></li> <li><a href="/wiki/Nicotine" title="Nicotine">Nicotine</a> (<a href="/wiki/Tobacco" title="Tobacco">tobacco</a>)</li> <li><a href="/w/index.php?title=NS-1738&action=edit&redlink=1" class="new" title="NS-1738 (page does not exist)">NS-1738</a></li> <li><a href="/wiki/PHA-543,613" title="PHA-543,613">PHA-543,613</a></li> <li><a href="/w/index.php?title=PHA-709,829&action=edit&redlink=1" class="new" title="PHA-709,829 (page does not exist)">PHA-709,829</a></li> <li><a href="/wiki/PNU-120,596" title="PNU-120,596">PNU-120,596</a></li> <li><a href="/wiki/PNU-282,987" title="PNU-282,987">PNU-282,987</a></li> <li><a href="/wiki/Pozanicline" title="Pozanicline">Pozanicline</a></li> <li><a href="/wiki/Pyrantel" title="Pyrantel">Pyrantel</a></li> <li><a href="/wiki/Rivanicline" title="Rivanicline">Rivanicline</a></li> <li><a href="/wiki/RJR-2429" title="RJR-2429">RJR-2429</a></li> <li><a href="/wiki/Sazetidine_A" title="Sazetidine A">Sazetidine A</a></li> <li><a href="/wiki/SB-206553" title="SB-206553">SB-206553</a></li> <li><a href="/w/index.php?title=Sebacylcholine&action=edit&redlink=1" class="new" title="Sebacylcholine (page does not exist)">Sebacylcholine</a></li> <li><a href="/wiki/SIB-1508Y" class="mw-redirect" title="SIB-1508Y">SIB-1508Y</a></li> <li><a href="/wiki/SIB-1553A" title="SIB-1553A">SIB-1553A</a></li> <li><a href="/wiki/SSR-180,711" title="SSR-180,711">SSR-180,711</a></li> <li><a href="/w/index.php?title=Suberyldicholine&action=edit&redlink=1" class="new" title="Suberyldicholine (page does not exist)">Suberyldicholine</a></li> <li><a href="/wiki/Suxamethonium" class="mw-redirect" title="Suxamethonium">Suxamethonium (succinylcholine)</a></li> <li><a href="/wiki/Suxethonium_chloride" title="Suxethonium chloride">Suxethonium (succinyldicholine)</a></li> <li><a href="/wiki/TC-1698" title="TC-1698">TC-1698</a></li> <li><a href="/w/index.php?title=TC-1734&action=edit&redlink=1" class="new" title="TC-1734 (page does not exist)">TC-1734</a></li> <li><a href="/wiki/TC-1827" title="TC-1827">TC-1827</a></li> <li><a href="/wiki/TC-2216" title="TC-2216">TC-2216</a></li> <li><a href="/wiki/TC-5214" class="mw-redirect" title="TC-5214">TC-5214</a></li> <li><a href="/wiki/TC-5619" class="mw-redirect" title="TC-5619">TC-5619</a></li> <li><a href="/w/index.php?title=TC-6683&action=edit&redlink=1" class="new" title="TC-6683 (page does not exist)">TC-6683</a></li> <li><a href="/wiki/Tebanicline" title="Tebanicline">Tebanicline</a></li> <li><a href="/wiki/Tribendimidine" title="Tribendimidine">Tribendimidine</a></li> <li><a href="/wiki/Tropisetron" title="Tropisetron">Tropisetron</a></li> <li><a href="/wiki/UB-165" title="UB-165">UB-165</a></li> <li><a href="/wiki/Varenicline" title="Varenicline">Varenicline</a></li> <li><a href="/wiki/WAY-317,538" class="mw-redirect" title="WAY-317,538">WAY-317,538</a></li> <li><a href="/w/index.php?title=XY-4083&action=edit&redlink=1" class="new" title="XY-4083 (page does not exist)">XY-4083</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Receptor_antagonist" title="Receptor antagonist">Antagonists</a><br />(and <a href="/wiki/Negative_allosteric_modulators" class="mw-redirect" title="Negative allosteric modulators"><abbr title="negative allosteric modulators">NAMs</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip negative allosteric modulators</span>)</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/18-Methylaminocoronaridine" title="18-Methylaminocoronaridine">18-MAC</a></li> <li><a href="/wiki/18-Methoxycoronaridine" title="18-Methoxycoronaridine">18-MC</a></li> <li><a href="/wiki/%CE%91-Neurotoxin" title="Α-Neurotoxin">α-Neurotoxins</a> (e.g., <a href="/wiki/%CE%91-bungarotoxin" class="mw-redirect" title="Α-bungarotoxin">α-bungarotoxin</a>, <a href="/wiki/%CE%91-cobratoxin" class="mw-redirect" title="Α-cobratoxin">α-cobratoxin</a>, <a href="/wiki/%CE%91-conotoxin" class="mw-redirect" title="Α-conotoxin">α-conotoxin</a>, many others)</li> <li><a href="/w/index.php?title=ABT-126&action=edit&redlink=1" class="new" title="ABT-126 (page does not exist)">ABT-126</a></li> <li><a href="/wiki/Alcuronium" class="mw-redirect" title="Alcuronium">Alcuronium</a></li> <li><a href="/wiki/Allopregnanolone" title="Allopregnanolone">Allopregnanolone</a></li> <li><a href="/wiki/Amantadine" title="Amantadine">Amantadine</a></li> <li><a href="/w/index.php?title=Anatruxonium&action=edit&redlink=1" class="new" title="Anatruxonium (page does not exist)">Anatruxonium</a></li> <li><a href="/w/index.php?title=AQW051&action=edit&redlink=1" class="new" title="AQW051 (page does not exist)">AQW051</a></li> <li><a href="/wiki/Atracurium" class="mw-redirect" title="Atracurium">Atracurium</a></li> <li><a href="/wiki/Barbiturates" class="mw-redirect" title="Barbiturates">Barbiturates</a> (e.g., <a href="/wiki/Pentobarbital" title="Pentobarbital">pentobarbital</a>, <a href="/wiki/Sodium_thiopental" title="Sodium thiopental">sodium thiopental</a>)</li> <li><a href="/wiki/BNC-210" class="mw-redirect" title="BNC-210">BNC-210</a></li> <li><a href="/wiki/Bungarotoxin" title="Bungarotoxin">Bungarotoxins</a> (e.g., <a href="/wiki/%CE%91-bungarotoxin" class="mw-redirect" title="Α-bungarotoxin">α-bungarotoxin</a>, <a href="/wiki/%CE%9A-bungarotoxin" class="mw-redirect" title="Κ-bungarotoxin">κ-bungarotoxin</a>)</li> <li><a href="/wiki/Bupropion" title="Bupropion">Bupropion</a></li> <li><a href="/wiki/BW284C51" title="BW284C51">BW284C51</a></li> <li><a href="/wiki/BW-A444" title="BW-A444">BW-A444</a></li> <li><a href="/wiki/Candocuronium_iodide" title="Candocuronium iodide">Candocuronium iodide (chandonium iodide)</a></li> <li><a href="/wiki/Chlorisondamine" title="Chlorisondamine">Chlorisondamine</a></li> <li><a href="/wiki/Cisatracurium" class="mw-redirect" title="Cisatracurium">Cisatracurium</a></li> <li><a href="/wiki/Coclaurine" title="Coclaurine">Coclaurine</a></li> <li><a href="/wiki/Coronaridine" title="Coronaridine">Coronaridine</a></li> <li><a href="/wiki/Curare" title="Curare">Curare</a></li> <li><a href="/wiki/Cyclopropane" title="Cyclopropane">Cyclopropane</a></li> <li><a href="/wiki/Dacuronium_bromide" title="Dacuronium bromide">Dacuronium bromide</a></li> <li><a href="/wiki/Decamethonium" title="Decamethonium">Decamethonium</a></li> <li><a href="/wiki/Dehydronorketamine" title="Dehydronorketamine">Dehydronorketamine</a></li> <li><a href="/wiki/Desflurane" title="Desflurane">Desflurane</a></li> <li><a href="/wiki/Dextromethorphan" title="Dextromethorphan">Dextromethorphan</a></li> <li><a href="/wiki/Dextropropoxyphene" title="Dextropropoxyphene">Dextropropoxyphene</a></li> <li><a href="/wiki/Dextrorphan" title="Dextrorphan">Dextrorphan</a></li> <li><a href="/w/index.php?title=Diadonium&action=edit&redlink=1" class="new" title="Diadonium (page does not exist)">Diadonium</a></li> <li><a href="/w/index.php?title=Dihydro-beta-erythroidine&action=edit&redlink=1" class="new" title="Dihydro-beta-erythroidine (page does not exist)">DHβE</a></li> <li><a href="/wiki/Dihydrochandonium" title="Dihydrochandonium">Dihydrochandonium</a></li> <li><a href="/wiki/Dimethyltubocurarine" class="mw-redirect" title="Dimethyltubocurarine">Dimethyltubocurarine (metocurine)</a></li> <li><a href="/wiki/Dioscorine" title="Dioscorine">Dioscorine</a></li> <li><a href="/wiki/Dipyrandium" title="Dipyrandium">Dipyrandium</a></li> <li><a href="/wiki/Dizocilpine" title="Dizocilpine">Dizocilpine (MK-801)</a></li> <li><a href="/wiki/Doxacurium" class="mw-redirect" title="Doxacurium">Doxacurium</a></li> <li><a href="/wiki/Encenicline" title="Encenicline">Encenicline</a></li> <li><a href="/wiki/Enflurane" title="Enflurane">Enflurane</a></li> <li><a href="/wiki/Erythravine" title="Erythravine">Erythravine</a></li> <li><a href="/wiki/Esketamine" title="Esketamine">Esketamine</a></li> <li><a href="/wiki/Fazadinium" class="mw-redirect" title="Fazadinium">Fazadinium</a></li> <li><a href="/wiki/Gallamine" class="mw-redirect" title="Gallamine">Gallamine</a></li> <li><a href="/wiki/Gantacurium_chloride" title="Gantacurium chloride">Gantacurium chloride</a></li> <li><a href="/wiki/Halothane" title="Halothane">Halothane</a></li> <li><a href="/wiki/Hexafluronium" class="mw-redirect" title="Hexafluronium">Hexafluronium</a></li> <li><a href="/wiki/Hexamethonium" title="Hexamethonium">Hexamethonium (benzohexonium)</a></li> <li><a href="/wiki/Hydroxybupropion" title="Hydroxybupropion">Hydroxybupropion</a></li> <li><a href="/wiki/Hydroxynorketamine" title="Hydroxynorketamine">Hydroxynorketamine</a></li> <li><a href="/wiki/Ibogaine" title="Ibogaine">Ibogaine</a></li> <li><a href="/wiki/Isoflurane" title="Isoflurane">Isoflurane</a></li> <li><a href="/wiki/Ketamine" title="Ketamine">Ketamine</a></li> <li><a href="/wiki/Kynurenic_acid" title="Kynurenic acid">Kynurenic acid</a></li> <li><a href="/wiki/Laudanosine" title="Laudanosine">Laudanosine</a></li> <li><a href="/wiki/Laudexium" class="mw-redirect" title="Laudexium">Laudexium (laudolissin)</a></li> <li><a href="/wiki/Levacetylmethadol" title="Levacetylmethadol">Levacetylmethadol</a></li> <li><a href="/wiki/Levomethadone" title="Levomethadone">Levomethadone</a></li> <li><a href="/wiki/Malouetine" title="Malouetine">Malouetine</a></li> <li><a href="/wiki/2-Methoxyethyl-18-methoxycoronaridinate" title="2-Methoxyethyl-18-methoxycoronaridinate">ME-18-MC</a></li> <li><a href="/wiki/Mecamylamine" title="Mecamylamine">Mecamylamine</a></li> <li><a href="/wiki/Memantine" title="Memantine">Memantine</a></li> <li><a href="/wiki/Methadone" title="Methadone">Methadone</a></li> <li><a href="/wiki/Methorphan" title="Methorphan">Methorphan (racemethorphan)</a></li> <li><a href="/wiki/Methyllycaconitine" title="Methyllycaconitine">Methyllycaconitine</a></li> <li><a href="/wiki/Metocurine" title="Metocurine">Metocurine</a></li> <li><a href="/wiki/Mivacurium" class="mw-redirect" title="Mivacurium">Mivacurium</a></li> <li><a href="/wiki/Morphanol" class="mw-redirect" title="Morphanol">Morphanol (racemorphan)</a></li> <li><a href="/wiki/Neramexane" title="Neramexane">Neramexane</a></li> <li><a href="/wiki/Nitrous_oxide" title="Nitrous oxide">Nitrous oxide</a></li> <li><a href="/wiki/Norketamine" title="Norketamine">Norketamine</a></li> <li><a href="/wiki/Pancuronium_bromide" title="Pancuronium bromide">Pancuronium bromide</a></li> <li><a href="/wiki/Pempidine" title="Pempidine">Pempidine</a></li> <li><a href="/wiki/Pentamine" title="Pentamine">Pentamine</a></li> <li><a href="/wiki/Pentolinium" title="Pentolinium">Pentolinium</a></li> <li><a href="/wiki/Phencyclidine" title="Phencyclidine">Phencyclidine</a></li> <li><a href="/wiki/Pipecuronium_bromide" title="Pipecuronium bromide">Pipecuronium bromide</a></li> <li><a href="/wiki/Progesterone" title="Progesterone">Progesterone</a></li> <li><a href="/wiki/Promegestone" title="Promegestone">Promegestone</a></li> <li><a href="/wiki/Radafaxine" title="Radafaxine">Radafaxine</a></li> <li><a href="/wiki/Rapacuronium_bromide" title="Rapacuronium bromide">Rapacuronium bromide</a></li> <li><a href="/wiki/Reboxetine" title="Reboxetine">Reboxetine</a></li> <li><a href="/wiki/Rocuronium_bromide" title="Rocuronium bromide">Rocuronium bromide</a></li> <li><a href="/wiki/Sevoflurane" title="Sevoflurane">Sevoflurane</a></li> <li><a href="/wiki/Stercuronium_iodide" title="Stercuronium iodide">Stercuronium iodide</a></li> <li><a href="/wiki/Surugatoxin" title="Surugatoxin">Surugatoxin</a></li> <li><a href="/wiki/Thiocolchicoside" title="Thiocolchicoside">Thiocolchicoside</a></li> <li><a href="/wiki/Threohydrobupropion" title="Threohydrobupropion">Threohydrobupropion</a></li> <li><a href="/wiki/Toxiferine" title="Toxiferine">Toxiferine</a></li> <li><a href="/wiki/Tramadol" title="Tramadol">Tramadol</a></li> <li><a href="/wiki/Trimetaphan_camsilate" title="Trimetaphan camsilate">Trimetaphan camsilate (trimethaphan camsylate)</a></li> <li><a href="/w/index.php?title=Tropeinium&action=edit&redlink=1" class="new" title="Tropeinium (page does not exist)">Tropeinium</a></li> <li><a href="/wiki/Tubocurarine" class="mw-redirect" title="Tubocurarine">Tubocurarine</a></li> <li><a href="/wiki/Vanoxerine" title="Vanoxerine">Vanoxerine</a></li> <li><a href="/wiki/Vecuronium_bromide" title="Vecuronium bromide">Vecuronium bromide</a></li> <li><a href="/wiki/Xenon" title="Xenon">Xenon</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/Precursor_(chemistry)" title="Precursor (chemistry)">Precursors</a><br /><small>(and <a href="/wiki/Prodrug" title="Prodrug">prodrugs</a>)</small></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/Acetyl-coA" class="mw-redirect" title="Acetyl-coA">Acetyl-coA</a></li> <li><a href="/wiki/Adafenoxate" title="Adafenoxate">Adafenoxate</a></li> <li><a href="/wiki/Choline" title="Choline">Choline</a> (<a href="/wiki/Lecithin" title="Lecithin">lecithin</a>)</li> <li><a href="/wiki/Citicoline" title="Citicoline">Citicoline</a></li> <li><a href="/wiki/Cyprodenate" title="Cyprodenate">Cyprodenate</a></li> <li><a href="/wiki/Dimethylethanolamine" title="Dimethylethanolamine">Dimethylethanolamine</a></li> <li><a href="/wiki/Glycerophosphocholine" class="mw-redirect" title="Glycerophosphocholine">Glycerophosphocholine</a></li> <li><a href="/wiki/Meclofenoxate" title="Meclofenoxate">Meclofenoxate (centrophenoxine)</a></li> <li><a href="/wiki/Phosphatidylcholine" title="Phosphatidylcholine">Phosphatidylcholine</a></li> <li><a href="/wiki/Phosphatidylethanolamine" title="Phosphatidylethanolamine">Phosphatidylethanolamine</a></li> <li><a href="/wiki/Phosphorylcholine" title="Phosphorylcholine">Phosphorylcholine</a></li> <li><a href="/wiki/Pirisudanol" title="Pirisudanol">Pirisudanol</a></li></ul> </div></td></tr><tr><td class="navbox-abovebelow" colspan="2"><div> <dl><dt>See also</dt> <dd><a href="/wiki/Template:Receptor_modulators" title="Template:Receptor modulators">Receptor/signaling modulators</a></dd> <dd><a href="/wiki/Template:Muscarinic_acetylcholine_receptor_modulators" title="Template:Muscarinic acetylcholine receptor modulators">Muscarinic acetylcholine receptor modulators</a></dd> <dd><a href="/wiki/Template:Acetylcholine_metabolism_and_transport_modulators" title="Template:Acetylcholine metabolism and transport modulators">Acetylcholine metabolism/transport modulators</a></dd></dl> </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="Neurotoxins205" style="padding:3px"><table class="nowraplinks hlist mw-collapsible autocollapse navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374" /><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231" /><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Neurotoxins" title="Template:Neurotoxins"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Neurotoxins" title="Template talk:Neurotoxins"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Neurotoxins" title="Special:EditPage/Template:Neurotoxins"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Neurotoxins205" style="font-size:114%;margin:0 4em"><a href="/wiki/Neurotoxin" title="Neurotoxin">Neurotoxins</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%">Animal toxins</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/Batrachotoxin" title="Batrachotoxin">Batrachotoxin</a></li> <li><a href="/wiki/Bestoxin" title="Bestoxin">Bestoxin</a></li> <li><a href="/wiki/Birtoxin" title="Birtoxin">Birtoxin</a></li> <li><a href="/wiki/Bungarotoxin" title="Bungarotoxin">Bungarotoxin</a></li> <li><a href="/wiki/Charybdotoxin" title="Charybdotoxin">Charybdotoxin</a></li> <li><a href="/wiki/Conotoxin" title="Conotoxin">Conotoxin</a></li> <li><a href="/wiki/Fasciculin" title="Fasciculin">Fasciculin</a></li> <li><a href="/wiki/Huwentoxin" title="Huwentoxin">Huwentoxin</a></li> <li><a href="/wiki/Poneratoxin" title="Poneratoxin">Poneratoxin</a></li> <li><a href="/wiki/Saxitoxin" title="Saxitoxin">Saxitoxin</a></li> <li><a href="/wiki/Tetrodotoxin" title="Tetrodotoxin">Tetrodotoxin</a></li> <li><a href="/wiki/Vanillotoxin" title="Vanillotoxin">Vanillotoxin</a></li> <li><a href="/wiki/Ssm_spooky_toxin" title="Ssm spooky toxin">Spooky toxin (SsTx)</a></li> <li><a class="mw-selflink selflink">Epibatidine</a></li> <li><a href="/wiki/Zetekitoxin_AB" title="Zetekitoxin AB">Zetekitoxin AB</a></li> <li><a href="/wiki/Dendrotoxin" title="Dendrotoxin">Dendrotoxin</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Bacterial_toxin" class="mw-redirect" title="Bacterial toxin">Bacterial</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/Botulinum_toxin" title="Botulinum toxin">Botulinum toxin</a></li> <li><a href="/wiki/Tetanospasmin" class="mw-redirect" title="Tetanospasmin">Tetanospasmin</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Cyanotoxin" title="Cyanotoxin">Cyanotoxins</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/Anatoxin-a" title="Anatoxin-a">Anatoxin-a</a></li> <li><a href="/wiki/Guanitoxin" title="Guanitoxin">Guanitoxin</a></li> <li><a href="/wiki/Beta-Methylamino-L-alanine" class="mw-redirect" title="Beta-Methylamino-L-alanine">BMAA</a></li> <li><a href="/wiki/Saxitoxin" title="Saxitoxin">Saxitoxin</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Plant_toxin" class="mw-redirect" title="Plant toxin">Plant toxins</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/Aconitine" title="Aconitine">Aconitine</a></li> <li><a href="/wiki/Bicuculline" title="Bicuculline">Bicuculline</a></li> <li><a href="/wiki/Penitrem_A" title="Penitrem A">Penitrem A</a></li> <li><a href="/wiki/Picrotoxin" title="Picrotoxin">Picrotoxin</a></li> <li><a href="/wiki/Strychnine" title="Strychnine">Strychnine</a></li> <li><a href="/wiki/Tutin_(toxin)" title="Tutin (toxin)">Tutin</a></li> <li><a href="/wiki/Rotenone" title="Rotenone">Rotenone</a></li> <li><a href="/wiki/Ginkgotoxin" title="Ginkgotoxin">Ginkgotoxin</a></li> <li><a href="/wiki/Cicutoxin" title="Cicutoxin">Cicutoxin</a></li> <li><a href="/wiki/Oenanthotoxin" title="Oenanthotoxin">Oenanthotoxin</a></li> <li><a href="/wiki/Thujone" title="Thujone">Thujone</a></li> <li><a href="/wiki/Volkensin" title="Volkensin">Volkensin</a></li> <li><a href="/wiki/Veratridine" title="Veratridine">Veratridine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Mycotoxin" title="Mycotoxin">Mycotoxins</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/Ibotenic_acid" title="Ibotenic acid">Ibotenic acid</a></li> <li><a href="/wiki/Muscarine" title="Muscarine">Muscarine</a></li> <li><a href="/wiki/Muscimol" title="Muscimol">Muscimol</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Pesticide" title="Pesticide">Pesticides</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/Fenpropathrin" title="Fenpropathrin">Fenpropathrin</a></li> <li><a href="/wiki/Tetramethylenedisulfotetramine" title="Tetramethylenedisulfotetramine">Tetramethylenedisulfotetramine</a></li> <li><a href="/wiki/Bromethalin" title="Bromethalin">Bromethalin</a></li> <li><a href="/wiki/Crimidine" title="Crimidine">Crimidine</a></li> <li><a href="/wiki/Methamidophos" title="Methamidophos">Methamidophos</a></li> <li><a href="/wiki/Endosulfan" title="Endosulfan">Endosulfan</a></li> <li><a href="/wiki/Fipronil" title="Fipronil">Fipronil</a></li> <li><a href="/wiki/Phenylsilatrane" title="Phenylsilatrane">Phenylsilatrane</a></li> <li><a href="/wiki/Chlorophenylsilatrane" title="Chlorophenylsilatrane">Chlorophenylsilatrane</a></li> <li><a href="/wiki/Sulfuryl_fluoride" title="Sulfuryl fluoride">Sulfuryl fluoride</a></li> <li><a href="/wiki/Mipafox" title="Mipafox">Mipafox</a></li> <li><a href="/wiki/Schradan" title="Schradan">Schradan</a></li> <li><a href="/wiki/Dimefox" title="Dimefox">Dimefox</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Nerve_agent" title="Nerve agent">Nerve agents</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/Cyclosarin" title="Cyclosarin">Cyclosarin</a></li> <li><a href="/wiki/EA-3148" title="EA-3148">EA-3148</a></li> <li><a href="/wiki/Novichok_agent" class="mw-redirect" title="Novichok agent">Novichok agent</a></li> <li><a href="/wiki/Sarin" title="Sarin">Sarin</a></li> <li><a href="/wiki/Soman" title="Soman">Soman</a></li> <li><a href="/wiki/Tabun_(nerve_agent)" title="Tabun (nerve agent)">Tabun</a></li> <li><a href="/wiki/VE_(nerve_agent)" title="VE (nerve agent)">VE</a></li> <li><a href="/wiki/VG_(nerve_agent)" title="VG (nerve agent)">VG</a></li> <li><a href="/wiki/VM_(nerve_agent)" title="VM (nerve agent)">VM</a></li> <li><a href="/wiki/VP_(nerve_agent)" class="mw-redirect" title="VP (nerve agent)">VP</a></li> <li><a href="/wiki/VR_(nerve_agent)" title="VR (nerve agent)">VR</a></li> <li><a href="/wiki/VX_(nerve_agent)" title="VX (nerve agent)">VX</a></li> <li><a href="/wiki/GV_(nerve_agent)" title="GV (nerve agent)">GV</a></li> <li><a href="/wiki/EA-3990" title="EA-3990">EA-3990</a></li> <li><a href="/wiki/EA-4056" title="EA-4056">EA-4056</a></li> <li><a href="/wiki/T-1123" title="T-1123">T-1123</a></li> <li><a href="/wiki/Octamethylene-bis(5-dimethylcarbamoxyisoquinolinium_bromide)" title="Octamethylene-bis(5-dimethylcarbamoxyisoquinolinium bromide)">Octamethylene-bis(5-dimethylcarbamoxyisoquinolinium bromide)</a></li> <li><a href="/wiki/Fluorotabun" title="Fluorotabun">Fluorotabun</a></li> <li><a href="/wiki/Chinese_VX" title="Chinese VX">Chinese VX</a></li> <li><a href="/wiki/EA-2192" title="EA-2192">EA-2192</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Bicyclic_phosphate" title="Bicyclic phosphate">Bicyclic phosphates</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/TBPS" title="TBPS">TBPS</a></li> <li><a href="/wiki/TBPO" title="TBPO">TBPO</a></li> <li><a href="/wiki/IPTBO" title="IPTBO">IPTBO</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Cholinergic neurotoxins</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="/w/index.php?title=Acetylcholine_mustard&action=edit&redlink=1" class="new" title="Acetylcholine mustard (page does not exist)">Acetylcholine mustard</a></li> <li><a href="/w/index.php?title=Catecholine&action=edit&redlink=1" class="new" title="Catecholine (page does not exist)">Catecholine</a></li> <li><a href="/w/index.php?title=Choline_mustard&action=edit&redlink=1" class="new" title="Choline mustard (page does not exist)">Choline mustard</a></li> <li><a href="/wiki/Ethylcholine_mustard" title="Ethylcholine mustard">Ethylcholine mustard</a></li> <li><a href="/w/index.php?title=Hemicholinium_mustard&action=edit&redlink=1" class="new" title="Hemicholinium mustard (page does not exist)">Hemicholinium mustard</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Psychoactive_drug" title="Psychoactive drug">Psychoactive drugs</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/Alcohol_(drug)" title="Alcohol (drug)">Alcohol</a></li> <li><a href="/wiki/Nitrous_oxide" title="Nitrous oxide">Nitrous oxide</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-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Dimethylcadmium" title="Dimethylcadmium">Dimethylcadmium</a></li> <li><a href="/wiki/Dimethylmercury" title="Dimethylmercury">Dimethylmercury</a></li> <li><a href="/wiki/Toxopyrimidine" title="Toxopyrimidine">Toxopyrimidine</a></li> <li><a href="/wiki/IDPN_(chemical)" title="IDPN (chemical)">IDPN</a></li> <li><a href="/wiki/Tetraethyllead" title="Tetraethyllead">Tetraethyllead</a></li></ul> </div></td></tr></tbody></table></div>    </div><noscript><img src="https://auth.wikimedia.org/loginwiki/wiki/Special:CentralAutoLogin/start?useformat=desktop&type=1x1&usesul3=1" 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=Epibatidine&oldid=1268918875">https://en.wikipedia.org/w/index.php?title=Epibatidine&oldid=1268918875</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:Analgesics" title="Category:Analgesics">Analgesics</a></li><li><a href="/wiki/Category:Nicotinic_agonists" title="Category:Nicotinic agonists">Nicotinic agonists</a></li><li><a href="/wiki/Category:Amphibian_toxins" title="Category:Amphibian toxins">Amphibian toxins</a></li><li><a href="/wiki/Category:Pyridine_alkaloids" title="Category:Pyridine alkaloids">Pyridine alkaloids</a></li><li><a href="/wiki/Category:Halogen-containing_alkaloids" title="Category:Halogen-containing alkaloids">Halogen-containing alkaloids</a></li><li><a href="/wiki/Category:Chloropyridines" title="Category:Chloropyridines">Chloropyridines</a></li><li><a href="/wiki/Category:Neurotoxins" title="Category:Neurotoxins">Neurotoxins</a></li><li><a href="/wiki/Category:Halogen-containing_natural_products" title="Category:Halogen-containing natural products">Halogen-containing natural products</a></li><li><a href="/wiki/Category:Chlorine-containing_natural_products" title="Category:Chlorine-containing natural products">Chlorine-containing natural products</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:Articles_with_short_description" title="Category:Articles with short description">Articles with short description</a></li><li><a href="/wiki/Category:Short_description_is_different_from_Wikidata" title="Category:Short description is different from Wikidata">Short description is different from Wikidata</a></li><li><a href="/wiki/Category:Articles_with_changed_KEGG_identifier" title="Category:Articles with changed KEGG identifier">Articles with changed KEGG identifier</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:Drugs_missing_an_ATC_code" title="Category:Drugs missing an ATC code">Drugs missing an ATC code</a></li><li><a href="/wiki/Category:Drugs_with_no_legal_status" title="Category:Drugs with no legal status">Drugs with no legal status</a></li><li><a href="/wiki/Category:Drugboxes_which_contain_changes_to_verified_fields" title="Category:Drugboxes which contain changes to verified fields">Drugboxes which contain changes to verified fields</a></li><li><a href="/wiki/Category:Drugboxes_which_contain_changes_to_watched_fields" title="Category:Drugboxes which contain changes to watched fields">Drugboxes which contain changes to watched fields</a></li><li><a href="/wiki/Category:All_articles_with_unsourced_statements" title="Category:All articles with unsourced statements">All articles with unsourced statements</a></li><li><a href="/wiki/Category:Articles_with_unsourced_statements_from_May_2018" title="Category:Articles with unsourced statements from May 2018">Articles with unsourced statements from May 2018</a></li><li><a href="/wiki/Category:Articles_with_unsourced_statements_from_March_2014" title="Category:Articles with unsourced statements from March 2014">Articles with unsourced statements from March 2014</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 12 January 2025, at 04:40<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=Epibatidine&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://www.wikimedia.org/" class="cdx-button cdx-button--fake-button cdx-button--size-large cdx-button--fake-button--enabled"><picture><source media="(min-width: 500px)" srcset="/static/images/footer/wikimedia-button.svg" width="84" height="29"><img src="/static/images/footer/wikimedia.svg" width="25" height="25" alt="Wikimedia Foundation" lang="en" loading="lazy"></picture></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"><picture><source media="(min-width: 500px)" srcset="/w/resources/assets/poweredby_mediawiki.svg" width="88" height="31"><img src="/w/resources/assets/mediawiki_compact.svg" alt="Powered by MediaWiki" lang="en" width="25" height="25" loading="lazy"></picture></a></li> </ul> </footer> </div> </div> </div> <div class="vector-header-container vector-sticky-header-container"> <div id="vector-sticky-header" class="vector-sticky-header"> <div class="vector-sticky-header-start"> <div class="vector-sticky-header-icon-start vector-button-flush-left vector-button-flush-right" aria-hidden="true"> <button class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-sticky-header-search-toggle" tabindex="-1" data-event-name="ui.vector-sticky-search-form.icon"><span class="vector-icon mw-ui-icon-search mw-ui-icon-wikimedia-search"></span> <span>Search</span> </button> </div> <div role="search" class="vector-search-box-vue vector-search-box-show-thumbnail vector-search-box"> <div class="vector-typeahead-search-container"> <div class="cdx-typeahead-search cdx-typeahead-search--show-thumbnail"> <form action="/w/index.php" id="vector-sticky-search-form" class="cdx-search-input cdx-search-input--has-end-button"> <div 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"> <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> <div class="vector-sticky-header-context-bar"> <nav aria-label="Contents" class="vector-toc-landmark"> <div id="vector-sticky-header-toc" class="vector-dropdown mw-portlet mw-portlet-sticky-header-toc vector-sticky-header-toc vector-button-flush-left" > <input type="checkbox" id="vector-sticky-header-toc-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-vector-sticky-header-toc" class="vector-dropdown-checkbox " aria-label="Toggle the table of contents" > <label id="vector-sticky-header-toc-label" for="vector-sticky-header-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-sticky-header-toc-unpinned-container" class="vector-unpinned-container"> </div> </div> </div> </nav> <div class="vector-sticky-header-context-bar-primary" aria-hidden="true" ><span class="mw-page-title-main">Epibatidine</span></div> </div> </div> <div class="vector-sticky-header-end" aria-hidden="true"> <div class="vector-sticky-header-icons"> <a href="#" class="cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--icon-only" id="ca-talk-sticky-header" tabindex="-1" data-event-name="talk-sticky-header"><span class="vector-icon mw-ui-icon-speechBubbles mw-ui-icon-wikimedia-speechBubbles"></span> <span></span> </a> <a href="#" class="cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--icon-only" id="ca-subject-sticky-header" tabindex="-1" data-event-name="subject-sticky-header"><span class="vector-icon mw-ui-icon-article mw-ui-icon-wikimedia-article"></span> <span></span> </a> <a href="#" class="cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--icon-only" id="ca-history-sticky-header" tabindex="-1" data-event-name="history-sticky-header"><span class="vector-icon mw-ui-icon-wikimedia-history mw-ui-icon-wikimedia-wikimedia-history"></span> <span></span> </a> <a href="#" class="cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--icon-only mw-watchlink" id="ca-watchstar-sticky-header" tabindex="-1" data-event-name="watch-sticky-header"><span class="vector-icon mw-ui-icon-wikimedia-star mw-ui-icon-wikimedia-wikimedia-star"></span> <span></span> </a> <a href="#" class="cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--icon-only" id="ca-edit-sticky-header" tabindex="-1" data-event-name="wikitext-edit-sticky-header"><span class="vector-icon mw-ui-icon-wikimedia-wikiText mw-ui-icon-wikimedia-wikimedia-wikiText"></span> <span></span> </a> <a href="#" class="cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--icon-only" id="ca-ve-edit-sticky-header" tabindex="-1" data-event-name="ve-edit-sticky-header"><span class="vector-icon mw-ui-icon-wikimedia-edit mw-ui-icon-wikimedia-wikimedia-edit"></span> <span></span> </a> <a href="#" class="cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--icon-only" id="ca-viewsource-sticky-header" tabindex="-1" data-event-name="ve-edit-protected-sticky-header"><span class="vector-icon mw-ui-icon-wikimedia-editLock mw-ui-icon-wikimedia-wikimedia-editLock"></span> <span></span> </a> </div> <div class="vector-sticky-header-buttons"> <button class="cdx-button cdx-button--weight-quiet mw-interlanguage-selector" id="p-lang-btn-sticky-header" tabindex="-1" data-event-name="ui.dropdown-p-lang-btn-sticky-header"><span class="vector-icon mw-ui-icon-wikimedia-language mw-ui-icon-wikimedia-wikimedia-language"></span> <span>12 languages</span> </button> <a href="#" class="cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--action-progressive" id="ca-addsection-sticky-header" tabindex="-1" data-event-name="addsection-sticky-header"><span class="vector-icon mw-ui-icon-speechBubbleAdd-progressive mw-ui-icon-wikimedia-speechBubbleAdd-progressive"></span> <span>Add topic</span> </a> </div> <div class="vector-sticky-header-icon-end"> <div class="vector-user-links"> </div> </div> </div> </div> </div> <div class="mw-portlet mw-portlet-dock-bottom emptyPortlet" id="p-dock-bottom"> <ul> </ul> </div> <script>(RLQ=window.RLQ||[]).push(function(){mw.config.set({"wgHostname":"mw-web.codfw.main-7ccc697c5f-mvnpf","wgBackendResponseTime":205,"wgPageParseReport":{"limitreport":{"cputime":"1.267","walltime":"1.580","ppvisitednodes":{"value":7948,"limit":1000000},"postexpandincludesize":{"value":323685,"limit":2097152},"templateargumentsize":{"value":7469,"limit":2097152},"expansiondepth":{"value":18,"limit":100},"expensivefunctioncount":{"value":5,"limit":500},"unstrip-depth":{"value":1,"limit":20},"unstrip-size":{"value":182109,"limit":5000000},"entityaccesscount":{"value":1,"limit":400},"timingprofile":["100.00% 1109.575 1 -total"," 32.32% 358.664 1 Template:Reflist"," 32.16% 356.864 1 Template:Infobox_drug"," 26.04% 288.914 28 Template:Cite_journal"," 25.71% 285.325 1 Template:Infobox"," 17.23% 191.174 9 Template:Navbox"," 8.62% 95.640 17 Template:Unbulleted_list"," 8.35% 92.662 1 Template:Stimulants"," 7.81% 86.690 2 Template:Short_description"," 5.58% 61.940 1 Template:Poison_frog_alkaloids"]},"scribunto":{"limitreport-timeusage":{"value":"0.605","limit":"10.000"},"limitreport-memusage":{"value":9302342,"limit":52428800}},"cachereport":{"origin":"mw-web.eqiad.main-6df8dbf59d-h69nl","timestamp":"20250331031820","ttl":2592000,"transientcontent":false}}});});</script> <script type="application/ld+json">{"@context":"https:\/\/schema.org","@type":"Article","name":"Epibatidine","url":"https:\/\/en.wikipedia.org\/wiki\/Epibatidine","sameAs":"http:\/\/www.wikidata.org\/entity\/Q423783","mainEntity":"http:\/\/www.wikidata.org\/entity\/Q423783","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":"2005-06-23T22:15:29Z","dateModified":"2025-01-12T04:40:42Z","image":"https:\/\/upload.wikimedia.org\/wikipedia\/commons\/e\/e0\/Epibatidine_molecule_ball.png","headline":"Epibatidine"}</script> </body> </html>