CINXE.COM

<!DOCTYPE html> <html class="client-nojs vector-feature-language-in-header-enabled vector-feature-language-in-main-page-header-disabled vector-feature-sticky-header-disabled vector-feature-page-tools-pinned-disabled vector-feature-toc-pinned-clientpref-1 vector-feature-main-menu-pinned-disabled vector-feature-limited-width-clientpref-1 vector-feature-limited-width-content-enabled vector-feature-custom-font-size-clientpref-1 vector-feature-appearance-pinned-clientpref-1 vector-feature-night-mode-enabled skin-theme-clientpref-day vector-toc-available" lang="en" dir="ltr"> <head> <meta charset="UTF-8"> <title>Purine - Wikipedia</title> <script>(function(){var className="client-js vector-feature-language-in-header-enabled vector-feature-language-in-main-page-header-disabled vector-feature-sticky-header-disabled vector-feature-page-tools-pinned-disabled vector-feature-toc-pinned-clientpref-1 vector-feature-main-menu-pinned-disabled vector-feature-limited-width-clientpref-1 vector-feature-limited-width-content-enabled vector-feature-custom-font-size-clientpref-1 vector-feature-appearance-pinned-clientpref-1 vector-feature-night-mode-enabled skin-theme-clientpref-day vector-toc-available";var cookie=document.cookie.match(/(?:^|; )enwikimwclientpreferences=([^;]+)/);if(cookie){cookie[1].split('%2C').forEach(function(pref){className=className.replace(new RegExp('(^| )'+pref.replace(/-clientpref-\w+$|[^\w-]+/g,'')+'-clientpref-\\w+( |$)'),'$1'+pref+'$2');});}document.documentElement.className=className;}());RLCONF={"wgBreakFrames":false,"wgSeparatorTransformTable":["",""],"wgDigitTransformTable":["",""],"wgDefaultDateFormat":"dmy", "wgMonthNames":["","January","February","March","April","May","June","July","August","September","October","November","December"],"wgRequestId":"30f74181-66cf-46dc-a5a0-90cd974f0718","wgCanonicalNamespace":"","wgCanonicalSpecialPageName":false,"wgNamespaceNumber":0,"wgPageName":"Purine","wgTitle":"Purine","wgCurRevisionId":1251551236,"wgRevisionId":1251551236,"wgArticleId":23652,"wgIsArticle":true,"wgIsRedirect":false,"wgAction":"view","wgUserName":null,"wgUserGroups":["*"],"wgCategories":["CS1: long volume value","Webarchive template wayback links","Articles with short description","Short description is different from Wikidata","ECHA InfoCard ID from Wikidata","Articles containing unverified chemical infoboxes","Chembox image size set","Short description matches Wikidata","Purines","Simple aromatic rings","1898 in science","Emil Fischer","Substances discovered in the 19th century"],"wgPageViewLanguage":"en","wgPageContentLanguage":"en","wgPageContentModel":"wikitext", "wgRelevantPageName":"Purine","wgRelevantArticleId":23652,"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":20000,"wgRelatedArticlesCompat":[],"wgCentralAuthMobileDomain":false,"wgEditSubmitButtonLabelPublish":true,"wgULSPosition":"interlanguage","wgULSisCompactLinksEnabled":false,"wgVector2022LanguageInHeader":true,"wgULSisLanguageSelectorEmpty":false,"wgWikibaseItemId":"Q188261","wgCheckUserClientHintsHeadersJsApi":["brands","architecture","bitness","fullVersionList", "mobile","model","platform","platformVersion"],"GEHomepageSuggestedEditsEnableTopics":true,"wgGETopicsMatchModeEnabled":false,"wgGEStructuredTaskRejectionReasonTextInputEnabled":false,"wgGELevelingUpEnabledForUser":false};RLSTATE={"ext.globalCssJs.user.styles":"ready","site.styles":"ready","user.styles":"ready","ext.globalCssJs.user":"ready","user":"ready","user.options":"loading","ext.cite.styles":"ready","skins.vector.search.codex.styles":"ready","skins.vector.styles":"ready","skins.vector.icons":"ready","jquery.makeCollapsible.styles":"ready","ext.wikimediamessages.styles":"ready","ext.visualEditor.desktopArticleTarget.noscript":"ready","ext.uls.interlanguage":"ready","wikibase.client.init":"ready","ext.wikimediaBadges":"ready"};RLPAGEMODULES=["ext.cite.ux-enhancements","mediawiki.page.media","site","mediawiki.page.ready","jquery.makeCollapsible","mediawiki.toc","skins.vector.js","ext.centralNotice.geoIP","ext.centralNotice.startUp","ext.gadget.ReferenceTooltips", "ext.gadget.switcher","ext.urlShortener.toolbar","ext.centralauth.centralautologin","mmv.bootstrap","ext.popups","ext.visualEditor.desktopArticleTarget.init","ext.visualEditor.targetLoader","ext.echo.centralauth","ext.eventLogging","ext.wikimediaEvents","ext.navigationTiming","ext.uls.interface","ext.cx.eventlogging.campaigns","ext.cx.uls.quick.actions","wikibase.client.vector-2022","ext.checkUser.clientHints","ext.growthExperiments.SuggestedEditSession","wikibase.sidebar.tracking"];</script> <script>(RLQ=window.RLQ||[]).push(function(){mw.loader.impl(function(){return["user.options@12s5i",function($,jQuery,require,module){mw.user.tokens.set({"patrolToken":"+\\","watchToken":"+\\","csrfToken":"+\\"}); }];});});</script> <link rel="stylesheet" href="/w/load.php?lang=en&modules=ext.cite.styles%7Cext.uls.interlanguage%7Cext.visualEditor.desktopArticleTarget.noscript%7Cext.wikimediaBadges%7Cext.wikimediamessages.styles%7Cjquery.makeCollapsible.styles%7Cskins.vector.icons%2Cstyles%7Cskins.vector.search.codex.styles%7Cwikibase.client.init&only=styles&skin=vector-2022"> <script async="" src="/w/load.php?lang=en&modules=startup&only=scripts&raw=1&skin=vector-2022"></script> <meta name="ResourceLoaderDynamicStyles" content=""> <link rel="stylesheet" href="/w/load.php?lang=en&modules=site.styles&only=styles&skin=vector-2022"> <meta name="generator" content="MediaWiki 1.44.0-wmf.4"> <meta name="referrer" content="origin"> <meta name="referrer" content="origin-when-cross-origin"> <meta name="robots" content="max-image-preview:standard"> <meta name="format-detection" content="telephone=no"> <meta property="og:image" content="https://upload.wikimedia.org/wikipedia/commons/thumb/d/d6/Purin_num2.svg/1200px-Purin_num2.svg.png"> <meta property="og:image:width" content="1200"> <meta property="og:image:height" content="944"> <meta property="og:image" content="https://upload.wikimedia.org/wikipedia/commons/thumb/d/d6/Purin_num2.svg/800px-Purin_num2.svg.png"> <meta property="og:image:width" content="800"> <meta property="og:image:height" content="630"> <meta property="og:image" content="https://upload.wikimedia.org/wikipedia/commons/thumb/d/d6/Purin_num2.svg/640px-Purin_num2.svg.png"> <meta property="og:image:width" content="640"> <meta property="og:image:height" content="504"> <meta name="viewport" content="width=1120"> <meta property="og:title" content="Purine - 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/Purine"> <link rel="alternate" type="application/x-wiki" title="Edit this page" href="/w/index.php?title=Purine&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/Purine"> <link rel="license" href="https://creativecommons.org/licenses/by-sa/4.0/deed.en"> <link rel="alternate" type="application/atom+xml" title="Wikipedia Atom feed" href="/w/index.php?title=Special:RecentChanges&feed=atom"> <link rel="dns-prefetch" href="//meta.wikimedia.org" /> <link rel="dns-prefetch" href="//login.wikimedia.org"> </head> <body class="skin--responsive skin-vector skin-vector-search-vue mediawiki ltr sitedir-ltr mw-hide-empty-elt ns-0 ns-subject mw-editable page-Purine rootpage-Purine skin-vector-2022 action-view"><a class="mw-jump-link" href="#bodyContent">Jump to content</a> <div class="vector-header-container"> <header class="vector-header mw-header"> <div class="vector-header-start"> <nav class="vector-main-menu-landmark" aria-label="Site"> <div id="vector-main-menu-dropdown" class="vector-dropdown vector-main-menu-dropdown vector-button-flush-left vector-button-flush-right" > <input type="checkbox" id="vector-main-menu-dropdown-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-vector-main-menu-dropdown" class="vector-dropdown-checkbox " aria-label="Main menu" > <label id="vector-main-menu-dropdown-label" for="vector-main-menu-dropdown-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--icon-only " aria-hidden="true" ><span class="vector-icon mw-ui-icon-menu mw-ui-icon-wikimedia-menu"></span> <span class="vector-dropdown-label-text">Main menu</span> </label> <div class="vector-dropdown-content"> <div id="vector-main-menu-unpinned-container" class="vector-unpinned-container"> <div id="vector-main-menu" class="vector-main-menu vector-pinnable-element"> <div class="vector-pinnable-header vector-main-menu-pinnable-header vector-pinnable-header-unpinned" data-feature-name="main-menu-pinned" data-pinnable-element-id="vector-main-menu" data-pinned-container-id="vector-main-menu-pinned-container" data-unpinned-container-id="vector-main-menu-unpinned-container" > <div class="vector-pinnable-header-label">Main menu</div> <button class="vector-pinnable-header-toggle-button vector-pinnable-header-pin-button" data-event-name="pinnable-header.vector-main-menu.pin">move to sidebar</button> <button class="vector-pinnable-header-toggle-button vector-pinnable-header-unpin-button" data-event-name="pinnable-header.vector-main-menu.unpin">hide</button> </div> <div id="p-navigation" class="vector-menu mw-portlet mw-portlet-navigation" > <div class="vector-menu-heading"> Navigation </div> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li id="n-mainpage-description" class="mw-list-item"><a href="/wiki/Main_Page" title="Visit the main page [z]" accesskey="z"><span>Main page</span></a></li><li id="n-contents" class="mw-list-item"><a href="/wiki/Wikipedia:Contents" title="Guides to browsing Wikipedia"><span>Contents</span></a></li><li id="n-currentevents" class="mw-list-item"><a href="/wiki/Portal:Current_events" title="Articles related to current events"><span>Current events</span></a></li><li id="n-randompage" class="mw-list-item"><a href="/wiki/Special:Random" title="Visit a randomly selected article [x]" accesskey="x"><span>Random article</span></a></li><li id="n-aboutsite" class="mw-list-item"><a href="/wiki/Wikipedia:About" title="Learn about Wikipedia and how it works"><span>About Wikipedia</span></a></li><li id="n-contactpage" class="mw-list-item"><a href="//en.wikipedia.org/wiki/Wikipedia:Contact_us" title="How to contact Wikipedia"><span>Contact us</span></a></li> </ul> </div> </div> <div id="p-interaction" class="vector-menu mw-portlet mw-portlet-interaction" > <div class="vector-menu-heading"> Contribute </div> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li id="n-help" class="mw-list-item"><a href="/wiki/Help:Contents" title="Guidance on how to use and edit Wikipedia"><span>Help</span></a></li><li id="n-introduction" class="mw-list-item"><a href="/wiki/Help:Introduction" title="Learn how to edit Wikipedia"><span>Learn to edit</span></a></li><li id="n-portal" class="mw-list-item"><a href="/wiki/Wikipedia:Community_portal" title="The hub for editors"><span>Community portal</span></a></li><li id="n-recentchanges" class="mw-list-item"><a href="/wiki/Special:RecentChanges" title="A list of recent changes to Wikipedia [r]" accesskey="r"><span>Recent changes</span></a></li><li id="n-upload" class="mw-list-item"><a href="/wiki/Wikipedia:File_upload_wizard" title="Add images or other media for use on Wikipedia"><span>Upload file</span></a></li> </ul> </div> </div> </div> </div> </div> </div> </nav> <a href="/wiki/Main_Page" class="mw-logo"> <img class="mw-logo-icon" src="/static/images/icons/wikipedia.png" alt="" aria-hidden="true" height="50" width="50"> <span class="mw-logo-container skin-invert"> <img class="mw-logo-wordmark" alt="Wikipedia" src="/static/images/mobile/copyright/wikipedia-wordmark-en.svg" style="width: 7.5em; height: 1.125em;"> <img class="mw-logo-tagline" alt="The Free Encyclopedia" src="/static/images/mobile/copyright/wikipedia-tagline-en.svg" width="117" height="13" style="width: 7.3125em; height: 0.8125em;"> </span> </a> </div> <div class="vector-header-end"> <div id="p-search" role="search" class="vector-search-box-vue vector-search-box-collapses vector-search-box-show-thumbnail vector-search-box-auto-expand-width vector-search-box"> <a href="/wiki/Special:Search" class="cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--icon-only search-toggle" title="Search Wikipedia [f]" accesskey="f"><span class="vector-icon mw-ui-icon-search mw-ui-icon-wikimedia-search"></span> <span>Search</span> </a> <div class="vector-typeahead-search-container"> <div class="cdx-typeahead-search cdx-typeahead-search--show-thumbnail cdx-typeahead-search--auto-expand-width"> <form action="/w/index.php" id="searchform" class="cdx-search-input cdx-search-input--has-end-button"> <div id="simpleSearch" class="cdx-search-input__input-wrapper" data-search-loc="header-moved"> <div class="cdx-text-input cdx-text-input--has-start-icon"> <input class="cdx-text-input__input" type="search" name="search" placeholder="Search Wikipedia" aria-label="Search Wikipedia" autocapitalize="sentences" title="Search Wikipedia [f]" accesskey="f" id="searchInput" > <span class="cdx-text-input__icon cdx-text-input__start-icon"></span> </div> <input type="hidden" name="title" value="Special:Search"> </div> <button class="cdx-button cdx-search-input__end-button">Search</button> </form> </div> </div> </div> <nav class="vector-user-links vector-user-links-wide" aria-label="Personal tools"> <div class="vector-user-links-main"> <div id="p-vector-user-menu-preferences" class="vector-menu mw-portlet emptyPortlet" > <div class="vector-menu-content"> <ul class="vector-menu-content-list"> </ul> </div> </div> <div id="p-vector-user-menu-userpage" class="vector-menu mw-portlet emptyPortlet" > <div class="vector-menu-content"> <ul class="vector-menu-content-list"> </ul> </div> </div> <nav class="vector-appearance-landmark" aria-label="Appearance"> <div id="vector-appearance-dropdown" class="vector-dropdown " title="Change the appearance of the page's font size, width, and color" > <input type="checkbox" id="vector-appearance-dropdown-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-vector-appearance-dropdown" class="vector-dropdown-checkbox " aria-label="Appearance" > <label id="vector-appearance-dropdown-label" for="vector-appearance-dropdown-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--icon-only " aria-hidden="true" ><span class="vector-icon mw-ui-icon-appearance mw-ui-icon-wikimedia-appearance"></span> <span class="vector-dropdown-label-text">Appearance</span> </label> <div class="vector-dropdown-content"> <div id="vector-appearance-unpinned-container" class="vector-unpinned-container"> </div> </div> </div> </nav> <div id="p-vector-user-menu-notifications" class="vector-menu mw-portlet emptyPortlet" > <div class="vector-menu-content"> <ul class="vector-menu-content-list"> </ul> </div> </div> <div id="p-vector-user-menu-overflow" class="vector-menu mw-portlet" > <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li id="pt-sitesupport-2" class="user-links-collapsible-item mw-list-item user-links-collapsible-item"><a data-mw="interface" href="https://donate.wikimedia.org/wiki/Special:FundraiserRedirector?utm_source=donate&utm_medium=sidebar&utm_campaign=C13_en.wikipedia.org&uselang=en" class=""><span>Donate</span></a> </li> <li id="pt-createaccount-2" class="user-links-collapsible-item mw-list-item user-links-collapsible-item"><a data-mw="interface" href="/w/index.php?title=Special:CreateAccount&returnto=Purine" 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=Purine" title="You're encouraged to log in; however, it's not mandatory. [o]" accesskey="o" class=""><span>Log in</span></a> </li> </ul> </div> </div> </div> <div id="vector-user-links-dropdown" class="vector-dropdown vector-user-menu vector-button-flush-right vector-user-menu-logged-out" title="Log in and more options" > <input type="checkbox" id="vector-user-links-dropdown-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-vector-user-links-dropdown" class="vector-dropdown-checkbox " aria-label="Personal tools" > <label id="vector-user-links-dropdown-label" for="vector-user-links-dropdown-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--icon-only " aria-hidden="true" ><span class="vector-icon mw-ui-icon-ellipsis mw-ui-icon-wikimedia-ellipsis"></span> <span class="vector-dropdown-label-text">Personal tools</span> </label> <div class="vector-dropdown-content"> <div id="p-personal" class="vector-menu mw-portlet mw-portlet-personal user-links-collapsible-item" title="User menu" > <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li id="pt-sitesupport" class="user-links-collapsible-item mw-list-item"><a href="https://donate.wikimedia.org/wiki/Special:FundraiserRedirector?utm_source=donate&utm_medium=sidebar&utm_campaign=C13_en.wikipedia.org&uselang=en"><span>Donate</span></a></li><li id="pt-createaccount" class="user-links-collapsible-item mw-list-item"><a href="/w/index.php?title=Special:CreateAccount&returnto=Purine" 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=Purine" 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-Dietary_sources" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Dietary_sources"> <div class="vector-toc-text"> <span class="vector-toc-numb">1</span> <span>Dietary sources</span> </div> </a> <ul id="toc-Dietary_sources-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Biochemistry" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Biochemistry"> <div class="vector-toc-text"> <span class="vector-toc-numb">2</span> <span>Biochemistry</span> </div> </a> <ul id="toc-Biochemistry-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Properties" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Properties"> <div class="vector-toc-text"> <span class="vector-toc-numb">3</span> <span>Properties</span> </div> </a> <ul id="toc-Properties-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Notable_purines" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Notable_purines"> <div class="vector-toc-text"> <span class="vector-toc-numb">4</span> <span>Notable purines</span> </div> </a> <ul id="toc-Notable_purines-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Functions" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Functions"> <div class="vector-toc-text"> <span class="vector-toc-numb">5</span> <span>Functions</span> </div> </a> <ul id="toc-Functions-sublist" class="vector-toc-list"> </ul> </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">6</span> <span>History</span> </div> </a> <ul id="toc-History-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Metabolism" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Metabolism"> <div class="vector-toc-text"> <span class="vector-toc-numb">7</span> <span>Metabolism</span> </div> </a> <button aria-controls="toc-Metabolism-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 Metabolism subsection</span> </button> <ul id="toc-Metabolism-sublist" class="vector-toc-list"> <li id="toc-Purine_biosynthesis_in_the_three_domains_of_life" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Purine_biosynthesis_in_the_three_domains_of_life"> <div class="vector-toc-text"> <span class="vector-toc-numb">7.1</span> <span>Purine biosynthesis in the three domains of life</span> </div> </a> <ul id="toc-Purine_biosynthesis_in_the_three_domains_of_life-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Relationship_with_gout" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Relationship_with_gout"> <div class="vector-toc-text"> <span class="vector-toc-numb">7.2</span> <span>Relationship with gout</span> </div> </a> <ul id="toc-Relationship_with_gout-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Laboratory_synthesis" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Laboratory_synthesis"> <div class="vector-toc-text"> <span class="vector-toc-numb">8</span> <span>Laboratory synthesis</span> </div> </a> <ul id="toc-Laboratory_synthesis-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Prebiotic_synthesis_of_purine_ribonucleosides" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Prebiotic_synthesis_of_purine_ribonucleosides"> <div class="vector-toc-text"> <span class="vector-toc-numb">9</span> <span>Prebiotic synthesis of purine ribonucleosides</span> </div> </a> <ul id="toc-Prebiotic_synthesis_of_purine_ribonucleosides-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-See_also" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#See_also"> <div class="vector-toc-text"> <span class="vector-toc-numb">10</span> <span>See also</span> </div> </a> <ul id="toc-See_also-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-References" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#References"> <div class="vector-toc-text"> <span class="vector-toc-numb">11</span> <span>References</span> </div> </a> <ul id="toc-References-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-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">12</span> <span>External links</span> </div> </a> <ul id="toc-External_links-sublist" class="vector-toc-list"> </ul> </li> </ul> </div> </div> </nav> </div> </div> <div class="mw-content-container"> <main id="content" class="mw-body"> <header class="mw-body-header vector-page-titlebar"> <nav aria-label="Contents" class="vector-toc-landmark"> <div id="vector-page-titlebar-toc" class="vector-dropdown vector-page-titlebar-toc vector-button-flush-left" > <input type="checkbox" id="vector-page-titlebar-toc-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-vector-page-titlebar-toc" class="vector-dropdown-checkbox " aria-label="Toggle the table of contents" > <label id="vector-page-titlebar-toc-label" for="vector-page-titlebar-toc-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--icon-only " aria-hidden="true" ><span class="vector-icon mw-ui-icon-listBullet mw-ui-icon-wikimedia-listBullet"></span> <span class="vector-dropdown-label-text">Toggle the table of contents</span> </label> <div class="vector-dropdown-content"> <div id="vector-page-titlebar-toc-unpinned-container" class="vector-unpinned-container"> </div> </div> </div> </nav> <h1 id="firstHeading" class="firstHeading mw-first-heading"><span class="mw-page-title-main">Purine</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 61 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-61" 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">61 languages</span> </label> <div class="vector-dropdown-content"> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li class="interlanguage-link interwiki-ar mw-list-item"><a href="https://ar.wikipedia.org/wiki/%D8%A8%D9%8A%D9%88%D8%B1%D9%8A%D9%86" title="بيورين – Arabic" lang="ar" hreflang="ar" data-title="بيورين" data-language-autonym="العربية" data-language-local-name="Arabic" class="interlanguage-link-target"><span>العربية</span></a></li><li class="interlanguage-link interwiki-azb mw-list-item"><a href="https://azb.wikipedia.org/wiki/%D9%BE%D9%88%D8%B1%DB%8C%D9%86" title="پورین – South Azerbaijani" lang="azb" hreflang="azb" data-title="پورین" data-language-autonym="تۆرکجه" data-language-local-name="South Azerbaijani" class="interlanguage-link-target"><span>تۆرکجه</span></a></li><li class="interlanguage-link interwiki-bn mw-list-item"><a href="https://bn.wikipedia.org/wiki/%E0%A6%AA%E0%A6%BF%E0%A6%89%E0%A6%B0%E0%A6%BF%E0%A6%A8" title="পিউরিন – Bangla" lang="bn" hreflang="bn" data-title="পিউরিন" data-language-autonym="বাংলা" data-language-local-name="Bangla" class="interlanguage-link-target"><span>বাংলা</span></a></li><li class="interlanguage-link interwiki-be mw-list-item"><a href="https://be.wikipedia.org/wiki/%D0%9F%D1%83%D1%80%D1%8B%D0%BD" title="Пурын – Belarusian" lang="be" hreflang="be" data-title="Пурын" data-language-autonym="Беларуская" data-language-local-name="Belarusian" class="interlanguage-link-target"><span>Беларуская</span></a></li><li class="interlanguage-link interwiki-bg mw-list-item"><a href="https://bg.wikipedia.org/wiki/%D0%9F%D1%83%D1%80%D0%B8%D0%BD" title="Пурин – Bulgarian" lang="bg" hreflang="bg" data-title="Пурин" data-language-autonym="Български" data-language-local-name="Bulgarian" class="interlanguage-link-target"><span>Български</span></a></li><li class="interlanguage-link interwiki-bs mw-list-item"><a href="https://bs.wikipedia.org/wiki/Purin" title="Purin – Bosnian" lang="bs" hreflang="bs" data-title="Purin" data-language-autonym="Bosanski" data-language-local-name="Bosnian" class="interlanguage-link-target"><span>Bosanski</span></a></li><li class="interlanguage-link interwiki-ca mw-list-item"><a href="https://ca.wikipedia.org/wiki/Purina" title="Purina – Catalan" lang="ca" hreflang="ca" data-title="Purina" data-language-autonym="Català" data-language-local-name="Catalan" class="interlanguage-link-target"><span>Català</span></a></li><li class="interlanguage-link interwiki-cs mw-list-item"><a href="https://cs.wikipedia.org/wiki/Purin" title="Purin – Czech" lang="cs" hreflang="cs" data-title="Purin" data-language-autonym="Čeština" data-language-local-name="Czech" class="interlanguage-link-target"><span>Čeština</span></a></li><li class="interlanguage-link interwiki-da mw-list-item"><a href="https://da.wikipedia.org/wiki/Purin" title="Purin – Danish" lang="da" hreflang="da" data-title="Purin" 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/Purin" title="Purin – German" lang="de" hreflang="de" data-title="Purin" data-language-autonym="Deutsch" data-language-local-name="German" class="interlanguage-link-target"><span>Deutsch</span></a></li><li class="interlanguage-link interwiki-et mw-list-item"><a href="https://et.wikipedia.org/wiki/Puriin" title="Puriin – Estonian" lang="et" hreflang="et" data-title="Puriin" data-language-autonym="Eesti" data-language-local-name="Estonian" class="interlanguage-link-target"><span>Eesti</span></a></li><li class="interlanguage-link interwiki-el mw-list-item"><a href="https://el.wikipedia.org/wiki/%CE%A0%CE%BF%CF%85%CF%81%CE%AF%CE%BD%CE%B7" title="Πουρίνη – Greek" lang="el" hreflang="el" data-title="Πουρίνη" data-language-autonym="Ελληνικά" data-language-local-name="Greek" class="interlanguage-link-target"><span>Ελληνικά</span></a></li><li class="interlanguage-link interwiki-es mw-list-item"><a href="https://es.wikipedia.org/wiki/Purina" title="Purina – Spanish" lang="es" hreflang="es" data-title="Purina" data-language-autonym="Español" data-language-local-name="Spanish" class="interlanguage-link-target"><span>Español</span></a></li><li class="interlanguage-link interwiki-eo mw-list-item"><a href="https://eo.wikipedia.org/wiki/Purino" title="Purino – Esperanto" lang="eo" hreflang="eo" data-title="Purino" data-language-autonym="Esperanto" data-language-local-name="Esperanto" class="interlanguage-link-target"><span>Esperanto</span></a></li><li class="interlanguage-link interwiki-eu mw-list-item"><a href="https://eu.wikipedia.org/wiki/Purina" title="Purina – Basque" lang="eu" hreflang="eu" data-title="Purina" data-language-autonym="Euskara" data-language-local-name="Basque" class="interlanguage-link-target"><span>Euskara</span></a></li><li class="interlanguage-link interwiki-fa mw-list-item"><a href="https://fa.wikipedia.org/wiki/%D9%BE%D9%88%D8%B1%DB%8C%D9%86" title="پورین – Persian" lang="fa" hreflang="fa" data-title="پورین" data-language-autonym="فارسی" data-language-local-name="Persian" class="interlanguage-link-target"><span>فارسی</span></a></li><li class="interlanguage-link interwiki-fr mw-list-item"><a href="https://fr.wikipedia.org/wiki/Purine" title="Purine – French" lang="fr" hreflang="fr" data-title="Purine" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target"><span>Français</span></a></li><li class="interlanguage-link interwiki-ga mw-list-item"><a href="https://ga.wikipedia.org/wiki/P%C3%BAir%C3%ADn%C3%AD" title="Púiríní – Irish" lang="ga" hreflang="ga" data-title="Púiríní" data-language-autonym="Gaeilge" data-language-local-name="Irish" class="interlanguage-link-target"><span>Gaeilge</span></a></li><li class="interlanguage-link interwiki-gl mw-list-item"><a href="https://gl.wikipedia.org/wiki/Purina" title="Purina – Galician" lang="gl" hreflang="gl" data-title="Purina" data-language-autonym="Galego" data-language-local-name="Galician" class="interlanguage-link-target"><span>Galego</span></a></li><li class="interlanguage-link interwiki-ko mw-list-item"><a href="https://ko.wikipedia.org/wiki/%ED%93%A8%EB%A6%B0" title="퓨린 – Korean" lang="ko" hreflang="ko" data-title="퓨린" data-language-autonym="한국어" data-language-local-name="Korean" class="interlanguage-link-target"><span>한국어</span></a></li><li class="interlanguage-link interwiki-hy mw-list-item"><a href="https://hy.wikipedia.org/wiki/%D5%8A%D5%B8%D6%82%D6%80%D5%AB%D5%B6" title="Պուրին – Armenian" lang="hy" hreflang="hy" data-title="Պուրին" data-language-autonym="Հայերեն" data-language-local-name="Armenian" class="interlanguage-link-target"><span>Հայերեն</span></a></li><li class="interlanguage-link interwiki-hi mw-list-item"><a href="https://hi.wikipedia.org/wiki/%E0%A4%AA%E0%A5%8D%E0%A4%AF%E0%A5%82%E0%A4%B0%E0%A4%BF%E0%A4%A8" title="प्यूरिन – Hindi" lang="hi" hreflang="hi" data-title="प्यूरिन" data-language-autonym="हिन्दी" data-language-local-name="Hindi" class="interlanguage-link-target"><span>हिन्दी</span></a></li><li class="interlanguage-link interwiki-hr mw-list-item"><a href="https://hr.wikipedia.org/wiki/Purin" title="Purin – Croatian" lang="hr" hreflang="hr" data-title="Purin" data-language-autonym="Hrvatski" data-language-local-name="Croatian" class="interlanguage-link-target"><span>Hrvatski</span></a></li><li class="interlanguage-link interwiki-id mw-list-item"><a href="https://id.wikipedia.org/wiki/Purina" title="Purina – Indonesian" lang="id" hreflang="id" data-title="Purina" data-language-autonym="Bahasa Indonesia" data-language-local-name="Indonesian" class="interlanguage-link-target"><span>Bahasa Indonesia</span></a></li><li class="interlanguage-link interwiki-it mw-list-item"><a href="https://it.wikipedia.org/wiki/Purina" title="Purina – Italian" lang="it" hreflang="it" data-title="Purina" data-language-autonym="Italiano" data-language-local-name="Italian" class="interlanguage-link-target"><span>Italiano</span></a></li><li class="interlanguage-link interwiki-he mw-list-item"><a href="https://he.wikipedia.org/wiki/%D7%A4%D7%95%D7%A8%D7%99%D7%9F_(%D7%AA%D7%A8%D7%9B%D7%95%D7%91%D7%AA_%D7%90%D7%95%D7%A8%D7%92%D7%A0%D7%99%D7%AA)" title="פורין (תרכובת אורגנית) – Hebrew" lang="he" hreflang="he" data-title="פורין (תרכובת אורגנית)" data-language-autonym="עברית" data-language-local-name="Hebrew" class="interlanguage-link-target"><span>עברית</span></a></li><li class="interlanguage-link interwiki-ka mw-list-item"><a href="https://ka.wikipedia.org/wiki/%E1%83%9E%E1%83%A3%E1%83%A0%E1%83%98%E1%83%9C%E1%83%98" title="პურინი – Georgian" lang="ka" hreflang="ka" data-title="პურინი" data-language-autonym="ქართული" data-language-local-name="Georgian" class="interlanguage-link-target"><span>ქართული</span></a></li><li class="interlanguage-link interwiki-kk mw-list-item"><a href="https://kk.wikipedia.org/wiki/%D0%9F%D1%83%D1%80%D0%B8%D0%BD" title="Пурин – Kazakh" lang="kk" hreflang="kk" data-title="Пурин" data-language-autonym="Қазақша" data-language-local-name="Kazakh" class="interlanguage-link-target"><span>Қазақша</span></a></li><li class="interlanguage-link interwiki-ky mw-list-item"><a href="https://ky.wikipedia.org/wiki/%D0%9F%D1%83%D1%80%D0%B8%D0%BD" title="Пурин – Kyrgyz" lang="ky" hreflang="ky" data-title="Пурин" data-language-autonym="Кыргызча" data-language-local-name="Kyrgyz" class="interlanguage-link-target"><span>Кыргызча</span></a></li><li class="interlanguage-link interwiki-la mw-list-item"><a href="https://la.wikipedia.org/wiki/Purinum" title="Purinum – Latin" lang="la" hreflang="la" data-title="Purinum" data-language-autonym="Latina" data-language-local-name="Latin" class="interlanguage-link-target"><span>Latina</span></a></li><li class="interlanguage-link interwiki-lt mw-list-item"><a href="https://lt.wikipedia.org/wiki/Purinas" title="Purinas – Lithuanian" lang="lt" hreflang="lt" data-title="Purinas" data-language-autonym="Lietuvių" data-language-local-name="Lithuanian" class="interlanguage-link-target"><span>Lietuvių</span></a></li><li class="interlanguage-link interwiki-hu mw-list-item"><a href="https://hu.wikipedia.org/wiki/Purin" title="Purin – Hungarian" lang="hu" hreflang="hu" data-title="Purin" data-language-autonym="Magyar" data-language-local-name="Hungarian" class="interlanguage-link-target"><span>Magyar</span></a></li><li class="interlanguage-link interwiki-mk mw-list-item"><a href="https://mk.wikipedia.org/wiki/%D0%9F%D1%83%D1%80%D0%B8%D0%BD" title="Пурин – Macedonian" lang="mk" hreflang="mk" data-title="Пурин" data-language-autonym="Македонски" data-language-local-name="Macedonian" class="interlanguage-link-target"><span>Македонски</span></a></li><li class="interlanguage-link interwiki-ml mw-list-item"><a href="https://ml.wikipedia.org/wiki/%E0%B4%AA%E0%B5%8D%E0%B4%AF%E0%B5%82%E0%B4%B0%E0%B4%BF%E0%B5%BB" title="പ്യൂരിൻ – Malayalam" lang="ml" hreflang="ml" data-title="പ്യൂരിൻ" data-language-autonym="മലയാളം" data-language-local-name="Malayalam" class="interlanguage-link-target"><span>മലയാളം</span></a></li><li class="interlanguage-link interwiki-ms mw-list-item"><a href="https://ms.wikipedia.org/wiki/Purina" title="Purina – Malay" lang="ms" hreflang="ms" data-title="Purina" data-language-autonym="Bahasa Melayu" data-language-local-name="Malay" class="interlanguage-link-target"><span>Bahasa Melayu</span></a></li><li class="interlanguage-link interwiki-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/Purine" title="Purine – Dutch" lang="nl" hreflang="nl" data-title="Purine" data-language-autonym="Nederlands" data-language-local-name="Dutch" class="interlanguage-link-target"><span>Nederlands</span></a></li><li class="interlanguage-link interwiki-ja mw-list-item"><a href="https://ja.wikipedia.org/wiki/%E3%83%97%E3%83%AA%E3%83%B3_(%E5%8C%96%E5%AD%A6)" title="プリン (化学) – Japanese" lang="ja" hreflang="ja" data-title="プリン (化学)" data-language-autonym="日本語" data-language-local-name="Japanese" class="interlanguage-link-target"><span>日本語</span></a></li><li class="interlanguage-link interwiki-no mw-list-item"><a href="https://no.wikipedia.org/wiki/Purin" title="Purin – Norwegian Bokmål" lang="nb" hreflang="nb" data-title="Purin" data-language-autonym="Norsk bokmål" data-language-local-name="Norwegian Bokmål" class="interlanguage-link-target"><span>Norsk bokmål</span></a></li><li class="interlanguage-link interwiki-nn mw-list-item"><a href="https://nn.wikipedia.org/wiki/Purin" title="Purin – Norwegian Nynorsk" lang="nn" hreflang="nn" data-title="Purin" data-language-autonym="Norsk nynorsk" data-language-local-name="Norwegian Nynorsk" class="interlanguage-link-target"><span>Norsk nynorsk</span></a></li><li class="interlanguage-link interwiki-oc mw-list-item"><a href="https://oc.wikipedia.org/wiki/Purina" title="Purina – Occitan" lang="oc" hreflang="oc" data-title="Purina" data-language-autonym="Occitan" data-language-local-name="Occitan" class="interlanguage-link-target"><span>Occitan</span></a></li><li class="interlanguage-link interwiki-uz mw-list-item"><a href="https://uz.wikipedia.org/wiki/Purin" title="Purin – Uzbek" lang="uz" hreflang="uz" data-title="Purin" data-language-autonym="Oʻzbekcha / ўзбекча" data-language-local-name="Uzbek" class="interlanguage-link-target"><span>Oʻzbekcha / ўзбекча</span></a></li><li class="interlanguage-link interwiki-pl mw-list-item"><a href="https://pl.wikipedia.org/wiki/Puryna" title="Puryna – Polish" lang="pl" hreflang="pl" data-title="Puryna" 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/Purina" title="Purina – Portuguese" lang="pt" hreflang="pt" data-title="Purina" data-language-autonym="Português" data-language-local-name="Portuguese" class="interlanguage-link-target"><span>Português</span></a></li><li class="interlanguage-link interwiki-ro mw-list-item"><a href="https://ro.wikipedia.org/wiki/Purin%C4%83" title="Purină – Romanian" lang="ro" hreflang="ro" data-title="Purină" data-language-autonym="Română" data-language-local-name="Romanian" class="interlanguage-link-target"><span>Română</span></a></li><li class="interlanguage-link interwiki-ru mw-list-item"><a href="https://ru.wikipedia.org/wiki/%D0%9F%D1%83%D1%80%D0%B8%D0%BD" title="Пурин – Russian" lang="ru" hreflang="ru" data-title="Пурин" data-language-autonym="Русский" data-language-local-name="Russian" class="interlanguage-link-target"><span>Русский</span></a></li><li class="interlanguage-link interwiki-simple mw-list-item"><a href="https://simple.wikipedia.org/wiki/Purine" title="Purine – Simple English" lang="en-simple" hreflang="en-simple" data-title="Purine" data-language-autonym="Simple English" data-language-local-name="Simple English" class="interlanguage-link-target"><span>Simple English</span></a></li><li class="interlanguage-link interwiki-sk mw-list-item"><a href="https://sk.wikipedia.org/wiki/Pur%C3%ADn" title="Purín – Slovak" lang="sk" hreflang="sk" data-title="Purín" data-language-autonym="Slovenčina" data-language-local-name="Slovak" class="interlanguage-link-target"><span>Slovenčina</span></a></li><li class="interlanguage-link interwiki-sl mw-list-item"><a href="https://sl.wikipedia.org/wiki/Purin" title="Purin – Slovenian" lang="sl" hreflang="sl" data-title="Purin" data-language-autonym="Slovenščina" data-language-local-name="Slovenian" class="interlanguage-link-target"><span>Slovenščina</span></a></li><li class="interlanguage-link interwiki-ckb mw-list-item"><a href="https://ckb.wikipedia.org/wiki/%D9%BE%DB%8C%D9%88%D8%B1%DB%8C%D9%86" title="پیورین – Central Kurdish" lang="ckb" hreflang="ckb" data-title="پیورین" data-language-autonym="کوردی" data-language-local-name="Central Kurdish" class="interlanguage-link-target"><span>کوردی</span></a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/%D0%9F%D1%83%D1%80%D0%B8%D0%BD" title="Пурин – Serbian" lang="sr" hreflang="sr" data-title="Пурин" 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/Purin" title="Purin – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Purin" 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/Puriini" title="Puriini – Finnish" lang="fi" hreflang="fi" data-title="Puriini" data-language-autonym="Suomi" data-language-local-name="Finnish" class="interlanguage-link-target"><span>Suomi</span></a></li><li class="interlanguage-link interwiki-sv mw-list-item"><a href="https://sv.wikipedia.org/wiki/Puriner" title="Puriner – Swedish" lang="sv" hreflang="sv" data-title="Puriner" data-language-autonym="Svenska" data-language-local-name="Swedish" class="interlanguage-link-target"><span>Svenska</span></a></li><li class="interlanguage-link interwiki-ta mw-list-item"><a href="https://ta.wikipedia.org/wiki/%E0%AE%AA%E0%AE%BF%E0%AE%AF%E0%AF%82%E0%AE%B0%E0%AE%BF%E0%AE%A9%E0%AF%8D" title="பியூரின் – Tamil" lang="ta" hreflang="ta" data-title="பியூரின்" data-language-autonym="தமிழ்" data-language-local-name="Tamil" class="interlanguage-link-target"><span>தமிழ்</span></a></li><li class="interlanguage-link interwiki-th mw-list-item"><a href="https://th.wikipedia.org/wiki/%E0%B8%9E%E0%B8%B4%E0%B8%A7%E0%B8%A3%E0%B8%B5%E0%B8%99" title="พิวรีน – Thai" lang="th" hreflang="th" data-title="พิวรีน" data-language-autonym="ไทย" data-language-local-name="Thai" class="interlanguage-link-target"><span>ไทย</span></a></li><li class="interlanguage-link interwiki-tr mw-list-item"><a href="https://tr.wikipedia.org/wiki/P%C3%BCrin" title="Pürin – Turkish" lang="tr" hreflang="tr" data-title="Pürin" data-language-autonym="Türkçe" data-language-local-name="Turkish" class="interlanguage-link-target"><span>Türkçe</span></a></li><li class="interlanguage-link interwiki-uk mw-list-item"><a href="https://uk.wikipedia.org/wiki/%D0%9F%D1%83%D1%80%D0%B8%D0%BD" title="Пурин – Ukrainian" lang="uk" hreflang="uk" data-title="Пурин" data-language-autonym="Українська" data-language-local-name="Ukrainian" class="interlanguage-link-target"><span>Українська</span></a></li><li class="interlanguage-link interwiki-ur mw-list-item"><a href="https://ur.wikipedia.org/wiki/%D9%BE%DB%8C%D9%88%D8%B1%DB%8C%D9%86" title="پیورین – Urdu" lang="ur" hreflang="ur" data-title="پیورین" data-language-autonym="اردو" data-language-local-name="Urdu" class="interlanguage-link-target"><span>اردو</span></a></li><li class="interlanguage-link interwiki-wuu mw-list-item"><a href="https://wuu.wikipedia.org/wiki/%E5%98%8C%E5%91%A4" title="嘌呤 – Wu" lang="wuu" hreflang="wuu" data-title="嘌呤" data-language-autonym="吴语" data-language-local-name="Wu" class="interlanguage-link-target"><span>吴语</span></a></li><li class="interlanguage-link interwiki-zh-yue mw-list-item"><a href="https://zh-yue.wikipedia.org/wiki/%E5%98%8C%E5%91%A4" title="嘌呤 – Cantonese" lang="yue" hreflang="yue" data-title="嘌呤" data-language-autonym="粵語" data-language-local-name="Cantonese" class="interlanguage-link-target"><span>粵語</span></a></li><li class="interlanguage-link interwiki-zh mw-list-item"><a href="https://zh.wikipedia.org/wiki/%E5%98%8C%E5%91%A4" title="嘌呤 – Chinese" lang="zh" hreflang="zh" data-title="嘌呤" data-language-autonym="中文" data-language-local-name="Chinese" class="interlanguage-link-target"><span>中文</span></a></li> </ul> <div class="after-portlet after-portlet-lang"><span class="wb-langlinks-edit wb-langlinks-link"><a href="https://www.wikidata.org/wiki/Special:EntityPage/Q188261#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/Purine" 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:Purine" 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/Purine"><span>Read</span></a></li><li id="ca-edit" class="vector-tab-noicon mw-list-item"><a href="/w/index.php?title=Purine&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=Purine&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/Purine"><span>Read</span></a></li><li id="ca-more-edit" class="vector-more-collapsible-item mw-list-item"><a href="/w/index.php?title=Purine&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=Purine&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/Purine" 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/Purine" rel="nofollow" title="Recent changes in pages linked from this page [k]" accesskey="k"><span>Related changes</span></a></li><li id="t-upload" class="mw-list-item"><a href="/wiki/Wikipedia:File_Upload_Wizard" title="Upload files [u]" accesskey="u"><span>Upload file</span></a></li><li id="t-specialpages" class="mw-list-item"><a href="/wiki/Special:SpecialPages" title="A list of all special pages [q]" accesskey="q"><span>Special pages</span></a></li><li id="t-permalink" class="mw-list-item"><a href="/w/index.php?title=Purine&oldid=1251551236" 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=Purine&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=Purine&id=1251551236&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%2FPurine"><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%2FPurine"><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=Purine&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=Purine&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:Purine" 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/Q188261" 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">Heterocyclic aromatic organic compound</div> <style data-mw-deduplicate="TemplateStyles:r1084375498">.mw-parser-output .ib-chembox{border-collapse:collapse;text-align:left}.mw-parser-output .ib-chembox td,.mw-parser-output .ib-chembox th{border:1px solid #a2a9b1;width:40%}.mw-parser-output .ib-chembox td+td{width:60%}</style> <table class="infobox ib-chembox"> <caption>Purine </caption> <tbody><tr> <td colspan="2" style="text-align:center; padding:2px;"><span typeof="mw:File"><a href="/wiki/File:Purin_num2.svg" class="mw-file-description"><img alt="Skeletal formula with numbering convention" src="//upload.wikimedia.org/wikipedia/commons/thumb/d/d6/Purin_num2.svg/150px-Purin_num2.svg.png" decoding="async" width="150" height="118" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/d/d6/Purin_num2.svg/225px-Purin_num2.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/d/d6/Purin_num2.svg/300px-Purin_num2.svg.png 2x" data-file-width="169" data-file-height="133" /></a></span> </td></tr> <tr> <td colspan="2" style="text-align:center; padding:2px;"><span typeof="mw:File"><a href="/wiki/File:Purine-3D-balls.png" class="mw-file-description"><img alt="Ball-and-stick molecular model" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/Purine-3D-balls.png/160px-Purine-3D-balls.png" decoding="async" width="160" height="119" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/Purine-3D-balls.png/240px-Purine-3D-balls.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a2/Purine-3D-balls.png/320px-Purine-3D-balls.png 2x" data-file-width="2000" data-file-height="1487" /></a></span> </td></tr> <tr> <td colspan="2" style="text-align:center; padding:2px;"><span typeof="mw:File"><a href="/wiki/File:Purine-3D-spacefill.png" class="mw-file-description"><img alt="Space-filling molecular model" src="//upload.wikimedia.org/wikipedia/commons/thumb/7/70/Purine-3D-spacefill.png/150px-Purine-3D-spacefill.png" decoding="async" width="150" height="121" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/7/70/Purine-3D-spacefill.png/225px-Purine-3D-spacefill.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/7/70/Purine-3D-spacefill.png/300px-Purine-3D-spacefill.png 2x" data-file-width="2000" data-file-height="1610" /></a></span> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Names </th></tr> <tr> <td colspan="2" style="text-align:left;"><a href="/wiki/Chemical_nomenclature" title="Chemical nomenclature">IUPAC name</a> <div style="max-width:22em; word-wrap:break-word; padding-left:1.7em;">9<i>H</i>-purine</div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Identifiers </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/CAS_Registry_Number" title="CAS Registry Number">CAS Number</a></div> </td> <td><style data-mw-deduplicate="TemplateStyles:r1126788409">.mw-parser-output .plainlist ol,.mw-parser-output .plainlist ul{line-height:inherit;list-style:none;margin:0;padding:0}.mw-parser-output .plainlist ol li,.mw-parser-output .plainlist ul li{margin-bottom:0}</style><div class="plainlist"><ul><li><span title="commonchemistry.cas.org"><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=120-73-0">120-73-0</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> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">3D model (<a href="/wiki/JSmol" class="mw-redirect" title="JSmol">JSmol</a>)</div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="chemapps.stolaf.edu (3D interactive model)"><a rel="nofollow" class="external text" href="https://chemapps.stolaf.edu/jmol/jmol.php?model=c1c2c%28nc%5BnH%5D2%29ncn1">Interactive image</a></span></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ChEBI" title="ChEBI">ChEBI</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.ebi.ac.uk"><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chebi/searchId.do?chebiId=17257">CHEBI:17257</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ChEMBL" title="ChEMBL">ChEMBL</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.ebi.ac.uk"><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chembldb/index.php/compound/inspect/ChEMBL302239">ChEMBL302239</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ChemSpider" title="ChemSpider">ChemSpider</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.chemspider.com"><a rel="nofollow" class="external text" href="https://www.chemspider.com/Chemical-Structure.1015.html">1015</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ECHA_InfoCard" class="mw-redirect" title="ECHA InfoCard"><span title="echa.europa.eu">ECHA InfoCard</span></a> </td> <td><a rel="nofollow" class="external text" href="https://echa.europa.eu/substance-information/-/substanceinfo/100.004.020">100.004.020</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q188261#P2566" title="Edit this at Wikidata"><img alt="Edit this at Wikidata" src="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/10px-OOjs_UI_icon_edit-ltr-progressive.svg.png" decoding="async" width="10" height="10" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/15px-OOjs_UI_icon_edit-ltr-progressive.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/20px-OOjs_UI_icon_edit-ltr-progressive.svg.png 2x" data-file-width="20" data-file-height="20" /></a></span> </td></tr> <tr> <td><a href="/wiki/KEGG" title="KEGG">KEGG</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.kegg.jp"><a rel="nofollow" class="external text" href="https://www.kegg.jp/entry/C15587">C15587</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><a href="/wiki/Medical_Subject_Headings" title="Medical Subject Headings">MeSH</a> </td> <td><span title="www.nlm.nih.gov"><a rel="nofollow" class="external text" href="https://www.nlm.nih.gov/cgi/mesh/2014/MB_cgi?mode=&term=Purine">Purine</a></span> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/PubChem" title="PubChem">PubChem</a> <abbr title="Compound ID">CID</abbr></div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="pubchem.ncbi.nlm.nih.gov"><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/1044">1044</a></span></li></ul></div> </td></tr> <tr> <td><a href="/wiki/Unique_Ingredient_Identifier" title="Unique Ingredient Identifier">UNII</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="precision.fda.gov"><a rel="nofollow" class="external text" href="https://precision.fda.gov/uniisearch/srs/unii/W60KTZ3IZY">W60KTZ3IZY</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/CompTox_Chemicals_Dashboard" title="CompTox Chemicals Dashboard">CompTox Dashboard</a> <span style="font-weight:normal">(<abbr title="U.S. Environmental Protection Agency">EPA</abbr>)</span></div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="comptox.epa.gov"><a rel="nofollow" class="external text" href="https://comptox.epa.gov/dashboard/chemical/details/DTXSID5074470">DTXSID5074470</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q188261#P3117" title="Edit this at Wikidata"><img alt="Edit this at Wikidata" src="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/10px-OOjs_UI_icon_edit-ltr-progressive.svg.png" decoding="async" width="10" height="10" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/15px-OOjs_UI_icon_edit-ltr-progressive.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/20px-OOjs_UI_icon_edit-ltr-progressive.svg.png 2x" data-file-width="20" data-file-height="20" /></a></span></span></li></ul></div> </td></tr> <tr> <td colspan="2"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold; text-align:left; font-weight:normal; background:transparent;"><div><a href="/wiki/International_Chemical_Identifier" title="International Chemical Identifier">InChI</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.5em; text-align:left;"><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">InChI=1S/C5H4N4/c1-4-5(8-2-6-1)9-3-7-4/h1-3H,(H,6,7,8,9)<sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></div><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">Key: KDCGOANMDULRCW-UHFFFAOYSA-N<sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></div></div></li><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.5em; text-align:left;"><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">InChI=1/C5H4N4/c1-4-5(8-2-6-1)9-3-7-4/h1-3H,(H,6,7,8,9)</div><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">Key: KDCGOANMDULRCW-UHFFFAOYAO</div></div></li></ul> </div> </td></tr> <tr> <td colspan="2"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold; text-align:left; font-weight:normal; background:transparent;"><div><a href="/wiki/Simplified_molecular-input_line-entry_system" class="mw-redirect" title="Simplified molecular-input line-entry system">SMILES</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.6em; word-wrap:break-word; text-indent:-1.5em; text-align:left; font-size:97%; line-height:120%;">c1c2c(nc[nH]2)ncn1</div></li></ul> </div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Properties </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Chemical_formula" title="Chemical formula">Chemical formula</a></div> </td> <td><span title="Carbon">C</span><sub>5</sub><span title="Hydrogen">H</span><sub>4</sub><span title="Nitrogen">N</span><sub>4</sub> </td></tr> <tr> <td><a href="/wiki/Molar_mass" title="Molar mass">Molar mass</a> </td> <td><span class="nowrap"><span data-sort-value="7002120115000000000♠"></span>120.115</span> g·mol<sup>−1</sup>   </td></tr> <tr> <td><a href="/wiki/Melting_point" title="Melting point">Melting point</a> </td> <td>214 °C (417 °F; 487 K) </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Aqueous_solution" title="Aqueous solution">Solubility in water</a></div> </td> <td>500 g/L (RT) </td></tr> <tr> <td colspan="2" style="text-align:left; background:#f8eaba; border:1px solid #a2a9b1;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">Except where otherwise noted, data are given for materials in their <a href="/wiki/Standard_state" title="Standard state">standard state</a> (at 25 °C [77 °F], 100 kPa).</div> <div style="margin-top: 0.3em;"><div style="text-align:center;"><span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/12px-Yes_check.svg.png" decoding="async" width="12" height="12" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/18px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/24px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span> <span class="reflink plainlinks nourlexpansion"><a class="external text" href="https://en.wikipedia.org/w/index.php?title=Special:ComparePages&rev1=464376451&page2=Purine">verify</a></span> (<a href="/wiki/Wikipedia:WikiProject_Chemicals/Chembox_validation" title="Wikipedia:WikiProject Chemicals/Chembox validation">what is</a> <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><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> ?) </div></div> <div style="margin-top: 0.3em; text-align: center;"><a href="/wiki/Wikipedia:Chemical_infobox#References" title="Wikipedia:Chemical infobox">Infobox references</a></div> </td></tr> </tbody></table><div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Chemical compound</div> <p><b>Purine</b> is a <a href="/wiki/Heterocyclic_compound" title="Heterocyclic compound">heterocyclic</a> <a href="/wiki/Aromatic" class="mw-redirect" title="Aromatic">aromatic</a> <a href="/wiki/Organic_compound" title="Organic compound">organic compound</a> that consists of two rings (<a href="/wiki/Pyrimidine" title="Pyrimidine">pyrimidine</a> and <a href="/wiki/Imidazole" title="Imidazole">imidazole</a>) fused together. It is <a href="/wiki/Water" title="Water">water</a>-soluble. Purine also gives its name to the wider class of <a href="/wiki/Molecule" title="Molecule">molecules</a>, <b>purines</b>, which include substituted purines and their <a href="/wiki/Tautomer" title="Tautomer">tautomers</a>. They are the most widely occurring <a href="/wiki/Nitrogen" title="Nitrogen">nitrogen</a>-containing heterocycles in nature.<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> </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Dietary_sources">Dietary sources</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Purine&action=edit&section=1" title="Edit section: Dietary sources"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Purines are found in high concentration in meat and meat products, especially internal organs such as <a href="/wiki/Liver" title="Liver">liver</a> and <a href="/wiki/Kidney" title="Kidney">kidney</a>. In general, plant-based diets are low in purines.<sup id="cite_ref-2" class="reference"><a href="#cite_note-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> High-purine plants and algae include some legumes (<a href="/wiki/Lentil" title="Lentil">lentils</a>, <a href="/wiki/Soybeans" class="mw-redirect" title="Soybeans">soybeans</a>, and <a href="/wiki/Black-eyed_pea" title="Black-eyed pea">black-eyed peas</a>) and <a href="/wiki/Spirulina_(dietary_supplement)" title="Spirulina (dietary supplement)">spirulina</a>. Examples of high-purine sources include: <a href="/wiki/Sweetbread" title="Sweetbread">sweetbreads</a>, <a href="/wiki/Anchovies_as_food" title="Anchovies as food">anchovies</a>, <a href="/wiki/Sardines_as_food" title="Sardines as food">sardines</a>, liver, <a href="/wiki/Beef" title="Beef">beef</a> kidneys, <a href="/wiki/Brain_as_food" title="Brain as food">brains</a>, <a href="/wiki/Meat_extract" title="Meat extract">meat extracts</a> (e.g., <a href="/wiki/Oxo_(food)" title="Oxo (food)">Oxo</a>, <a href="/wiki/Bovril" title="Bovril">Bovril</a>), <a href="/wiki/Herring" title="Herring">herring</a>, <a href="/wiki/Mackerel" title="Mackerel">mackerel</a>, <a href="/wiki/Scallop" title="Scallop">scallops</a>, <a href="/wiki/Game_meat" class="mw-redirect" title="Game meat">game meats</a>, <a href="/wiki/Yeast" title="Yeast">yeast</a> (<a href="/wiki/Beer" title="Beer">beer</a>, <a href="/wiki/Yeast_extract" title="Yeast extract">yeast extract</a>, <a href="/wiki/Nutritional_yeast" title="Nutritional yeast">nutritional yeast</a>) and <a href="/wiki/Gravy" title="Gravy">gravy</a>.<sup id="cite_ref-3" class="reference"><a href="#cite_note-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> </p><p>A moderate amount of purine is also contained in red meat, <a href="/wiki/Beef" title="Beef">beef</a>, <a href="/wiki/Pork" title="Pork">pork</a>, <a href="/wiki/Poultry" title="Poultry">poultry</a>, fish and <a href="/wiki/Seafood" title="Seafood">seafood</a>, <a href="/wiki/Asparagus" title="Asparagus">asparagus</a>, <a href="/wiki/Cauliflower" title="Cauliflower">cauliflower</a>, <a href="/wiki/Spinach" title="Spinach">spinach</a>, <a href="/wiki/Edible_mushroom" title="Edible mushroom">mushrooms</a>, <a href="/wiki/Green_pea" class="mw-redirect" title="Green pea">green peas</a>, <a href="/wiki/Lentil" title="Lentil">lentils</a>, dried peas, <a href="/wiki/Bean" title="Bean">beans</a>, <a href="/wiki/Oatmeal" title="Oatmeal">oatmeal</a>, <a href="/wiki/Wheat_bran" class="mw-redirect" title="Wheat bran">wheat bran</a>, <a href="/wiki/Wheat_germ" class="mw-redirect" title="Wheat germ">wheat germ</a>, and <a href="/wiki/Crataegus_monogyna#Edible_"berries",_petals,_and_leaves" title="Crataegus monogyna">haws</a>.<sup id="cite_ref-4" class="reference"><a href="#cite_note-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Biochemistry">Biochemistry</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Purine&action=edit&section=2" title="Edit section: Biochemistry"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Purines and pyrimidines make up the two groups of <a href="/wiki/Nitrogenous_base" class="mw-redirect" title="Nitrogenous base">nitrogenous bases</a>, including the two groups of <a href="/wiki/Nucleotide_bases" class="mw-redirect" title="Nucleotide bases">nucleotide bases</a>. The purine bases are <a href="/wiki/Guanine" title="Guanine">guanine</a> (G) and <a href="/wiki/Adenine" title="Adenine">adenine</a> (A) which form corresponding nucleosides-<a href="/wiki/Deoxyribonucleoside" class="mw-redirect" title="Deoxyribonucleoside">deoxyribonucleosides</a> (<a href="/wiki/Deoxyguanosine" title="Deoxyguanosine">deoxyguanosine</a> and <a href="/wiki/Deoxyadenosine" title="Deoxyadenosine">deoxyadenosine</a>) with deoxyribose moiety and <a href="/wiki/Ribonucleoside" title="Ribonucleoside">ribonucleosides</a> (<a href="/wiki/Guanosine" title="Guanosine">guanosine</a>, <a href="/wiki/Adenosine" title="Adenosine">adenosine</a>) with ribose moiety. These nucleosides with phosphoric acid form corresponding nucleotides (deoxyguanylate, deoxyadenylate and guanylate, adenylate) which are the building blocks of <a href="/wiki/DNA" title="DNA">DNA</a> and <a href="/wiki/RNA" title="RNA">RNA</a>, respectively. Purine bases also play an essential role in many metabolic and signalling processes within the compounds <a href="/wiki/Guanosine_monophosphate" title="Guanosine monophosphate">guanosine monophosphate</a> (GMP) and <a href="/wiki/Adenosine_monophosphate" title="Adenosine monophosphate">adenosine monophosphate</a> (AMP). </p><p>In order to perform these essential cellular processes, both purines and pyrimidines are needed by the <a href="/wiki/Cell_(biology)" title="Cell (biology)">cell</a>, and in similar quantities. Both purine and pyrimidine are self-<a href="/wiki/Enzyme_inhibitor" title="Enzyme inhibitor">inhibiting</a> and <a href="/wiki/Enzyme_activator" title="Enzyme activator">activating</a>. When purines are formed, they <a href="/wiki/Enzyme_inhibition" class="mw-redirect" title="Enzyme inhibition">inhibit</a> the <a href="/wiki/Enzyme" title="Enzyme">enzymes</a> required for more purine formation. This self-inhibition occurs as they also activate the enzymes needed for pyrimidine formation. Pyrimidine simultaneously self-inhibits and activates purine in a similar manner. Because of this, there is nearly an equal amount of both substances in the cell at all times.<sup id="cite_ref-5" class="reference"><a href="#cite_note-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Properties">Properties</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Purine&action=edit&section=3" title="Edit section: Properties"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Purine is both a very weak acid (<a href="/wiki/Acid_dissociation_constant" title="Acid dissociation constant">pK<sub>a</sub></a> 8.93) and an even weaker base (<a href="/wiki/Acid_dissociation_constant" title="Acid dissociation constant">pK<sub>a</sub></a> 2.39).<sup id="cite_ref-6" class="reference"><a href="#cite_note-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> If dissolved in pure water, the <a href="/wiki/PH" title="PH">pH</a> is halfway between these two pKa values. </p><p>Purine is <a href="/wiki/Aromaticity" title="Aromaticity">aromatic</a>, having four <a href="/wiki/Tautomer" title="Tautomer">tautomers</a> each with a hydrogen bonded to a different one of the four nitrogen atoms. These are identified as 1-H, 3-H, 7-H, and 9-H (see image of numbered ring). The common crystalline form favours the 7-H tautomer, while in polar solvents both the 9-H and 7-H tautomers predominate.<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> Substituents to the rings and interactions with other molecules can shift the equilibrium of these tautomers.<sup id="cite_ref-8" class="reference"><a href="#cite_note-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Notable_purines">Notable purines</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Purine&action=edit&section=4" title="Edit section: Notable purines"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>There are many naturally occurring purines. They include the <a href="/wiki/Nucleotide_base" title="Nucleotide base">nucleotide bases</a> <a href="/wiki/Adenine" title="Adenine">adenine</a> and <a href="/wiki/Guanine" title="Guanine">guanine</a>. In <a href="/wiki/DNA" title="DNA">DNA</a>, these bases form <a href="/wiki/Hydrogen_bond" title="Hydrogen bond">hydrogen bonds</a> with their <a href="/wiki/Complementarity_(molecular_biology)" title="Complementarity (molecular biology)">complementary</a> pyrimidines, <a href="/wiki/Thymine" title="Thymine">thymine</a> and <a href="/wiki/Cytosine" title="Cytosine">cytosine</a>, respectively. This is called complementary base pairing. In <a href="/wiki/RNA" title="RNA">RNA</a>, the complement of adenine is <a href="/wiki/Uracil" title="Uracil">uracil</a> instead of thymine. </p><p>Other notable purines are <a href="/wiki/Hypoxanthine" title="Hypoxanthine">hypoxanthine</a>, <a href="/wiki/Xanthine" title="Xanthine">xanthine</a>, <a href="/wiki/Theophylline" title="Theophylline">theophylline</a>, <a href="/wiki/Theobromine" title="Theobromine">theobromine</a>, <a href="/wiki/Caffeine" title="Caffeine">caffeine</a>, <a href="/wiki/Uric_acid" title="Uric acid">uric acid</a> and <a href="/wiki/Isoguanine" title="Isoguanine">isoguanine</a>. </p> <dl><dd><span typeof="mw:File"><a href="/wiki/File:Purines.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/1/1f/Purines.svg/550px-Purines.svg.png" decoding="async" width="550" height="308" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/1/1f/Purines.svg/825px-Purines.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/1/1f/Purines.svg/1100px-Purines.svg.png 2x" data-file-width="803" data-file-height="449" /></a></span><div style="clear:left;" class=""></div></dd></dl> <div class="mw-heading mw-heading2"><h2 id="Functions">Functions</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Purine&action=edit&section=5" title="Edit section: Functions"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Aside from the crucial roles of purines (adenine and guanine) in DNA and RNA, purines are also significant components in a number of other important biomolecules, such as <a href="/wiki/Adenosine_triphosphate" title="Adenosine triphosphate">ATP</a>, <a href="/wiki/Guanosine_triphosphate" title="Guanosine triphosphate">GTP</a>, <a href="/wiki/Cyclic_AMP" class="mw-redirect" title="Cyclic AMP">cyclic AMP</a>, <a href="/wiki/NADH" class="mw-redirect" title="NADH">NADH</a>, and <a href="/wiki/Coenzyme_A" title="Coenzyme A">coenzyme A</a>. Purine (<b>1</b>) itself, has not been found in nature, but it can be produced by <a href="/wiki/Organic_synthesis" title="Organic synthesis">organic synthesis</a>. </p><p>They may also function directly as <a href="/wiki/Neurotransmitters" class="mw-redirect" title="Neurotransmitters">neurotransmitters</a>, acting upon <a href="/wiki/Purinergic_receptors" class="mw-redirect" title="Purinergic receptors">purinergic receptors</a>. Adenosine activates <a href="/wiki/Adenosine_receptor" title="Adenosine receptor">adenosine receptors</a>. </p> <div class="mw-heading mw-heading2"><h2 id="History">History</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Purine&action=edit&section=6" title="Edit section: History"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The word <i>purine</i> (<i>pure urine</i>)<sup id="cite_ref-McGuigan_9-0" class="reference"><a href="#cite_note-McGuigan-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> was coined by the <a href="/wiki/Germany" title="Germany">German</a> <a href="/wiki/Chemist" title="Chemist">chemist</a> <a href="/wiki/Emil_Fischer" title="Emil Fischer">Emil Fischer</a> in 1884.<sup id="cite_ref-10" class="reference"><a href="#cite_note-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Fischer1898_11-0" class="reference"><a href="#cite_note-Fischer1898-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> He synthesized it for the first time in 1898.<sup id="cite_ref-Fischer1898_11-1" class="reference"><a href="#cite_note-Fischer1898-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> The starting material for the reaction sequence was <a href="/wiki/Uric_acid" title="Uric acid">uric acid</a> (<b>8</b>), which had been isolated from <a href="/wiki/Kidney_stone" class="mw-redirect" title="Kidney stone">kidney stones</a> by <a href="/wiki/Carl_Wilhelm_Scheele" title="Carl Wilhelm Scheele">Carl Wilhelm Scheele</a> in 1776.<sup id="cite_ref-12" class="reference"><a href="#cite_note-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup> Uric acid was reacted with <a href="/wiki/Phosphorus_pentachloride" title="Phosphorus pentachloride">PCl<sub>5</sub></a> to give 2,6,8-trichloropurine, which was converted with <a href="/wiki/Hydrogen_iodide" title="Hydrogen iodide">HI</a> and <a href="/wiki/Phosphonium_iodide" title="Phosphonium iodide">PH<sub>4</sub>I</a> to give 2,6-diiodopurine. The product was reduced to purine using <a href="/wiki/Zinc" title="Zinc">zinc</a> dust. </p> <dl><dd><figure class="mw-halign-left" typeof="mw:File/Thumb"><a href="/wiki/File:FischerPurineSynthesis-crop.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/7/78/FischerPurineSynthesis-crop.svg/500px-FischerPurineSynthesis-crop.svg.png" decoding="async" width="500" height="83" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/7/78/FischerPurineSynthesis-crop.svg/750px-FischerPurineSynthesis-crop.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/7/78/FischerPurineSynthesis-crop.svg/1000px-FischerPurineSynthesis-crop.svg.png 2x" data-file-width="786" data-file-height="130" /></a><figcaption>Conversion of uric acid (left) to purine (right) via 2,6,8-trichloropurine and 2,6-diiodopurine intermediates</figcaption></figure><div style="clear:left;" class=""></div></dd></dl> <div class="mw-heading mw-heading2"><h2 id="Metabolism">Metabolism</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Purine&action=edit&section=7" title="Edit section: Metabolism"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></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">Main article: <a href="/wiki/Purine_metabolism" title="Purine metabolism">Purine metabolism</a></div> <p>Many organisms have <a href="/wiki/Metabolic_pathway" title="Metabolic pathway">metabolic pathways</a> to synthesize and break down purines. </p><p>Purines are biologically synthesized as <a href="/wiki/Nucleoside" title="Nucleoside">nucleosides</a> (bases attached to <a href="/wiki/Ribose" title="Ribose">ribose</a>). </p><p>Accumulation of modified purine nucleotides is defective to various cellular processes, especially those involving <a href="/wiki/DNA" title="DNA">DNA</a> and <a href="/wiki/RNA" title="RNA">RNA</a>. To be viable, organisms possess a number of deoxypurine phosphohydrolases, which <a href="/wiki/Hydrolyze" class="mw-redirect" title="Hydrolyze">hydrolyze</a> these purine derivatives removing them from the active <a href="/wiki/Nucleoside_triphosphate" title="Nucleoside triphosphate">NTP</a> and <a href="/wiki/Deoxynucleoside_triphosphate" class="mw-redirect" title="Deoxynucleoside triphosphate">dNTP</a> pools. Deamination of purine bases can result in accumulation of such nucleotides as <a href="/wiki/Inosine_triphosphate" title="Inosine triphosphate">ITP</a>, <a href="/w/index.php?title=Deoxyinosine_triphosphate&action=edit&redlink=1" class="new" title="Deoxyinosine triphosphate (page does not exist)">dITP</a>, <a href="/wiki/Xanthosine_triphosphate" title="Xanthosine triphosphate">XTP</a> and <a href="/w/index.php?title=Deoxyxanthosine_triphosphate&action=edit&redlink=1" class="new" title="Deoxyxanthosine triphosphate (page does not exist)">dXTP</a>.<sup id="cite_ref-pmid_22531138_13-0" class="reference"><a href="#cite_note-pmid_22531138-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup> </p><p>Defects in enzymes that control purine production and breakdown can severely alter a cell's DNA sequences, which may explain why people who carry certain genetic variants of purine metabolic enzymes have a higher risk for some types of <a href="/wiki/Cancer" title="Cancer">cancer</a>. </p> <div class="mw-heading mw-heading3"><h3 id="Purine_biosynthesis_in_the_three_domains_of_life">Purine biosynthesis in the three domains of life</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Purine&action=edit&section=8" title="Edit section: Purine biosynthesis in the three domains of life"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Organisms in all three domains of life, <a href="/wiki/Eukaryote" title="Eukaryote">eukaryotes</a>, <a href="/wiki/Bacteria" title="Bacteria">bacteria</a> and <a href="/wiki/Archaea" title="Archaea">archaea</a>, are able to carry out de novo <a href="/wiki/Purine_metabolism" title="Purine metabolism">biosynthesis of purines</a>. This ability reflects the essentiality of purines for life. The biochemical pathway of synthesis is very similar in eukaryotes and bacterial species, but is more variable among archaeal species.<sup id="cite_ref-Brown2011_14-0" class="reference"><a href="#cite_note-Brown2011-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup> A nearly complete, or complete, set of genes required for purine biosynthesis was determined to be present in 58 of the 65 archaeal species studied.<sup id="cite_ref-Brown2011_14-1" class="reference"><a href="#cite_note-Brown2011-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup> However, also identified were seven archaeal species with entirely, or nearly entirely, absent purine encoding genes. Apparently the archaeal species unable to synthesize purines are able to acquire exogenous purines for growth.,<sup id="cite_ref-Brown2011_14-2" class="reference"><a href="#cite_note-Brown2011-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup> and are thus analogous to purine mutants of eukaryotes, e.g. purine mutants of the Ascomycete fungus <i>Neurospora crassa</i>,<sup id="cite_ref-15" class="reference"><a href="#cite_note-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup> that also require exogenous purines for growth. </p> <div class="mw-heading mw-heading3"><h3 id="Relationship_with_gout">Relationship with gout</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Purine&action=edit&section=9" title="Edit section: Relationship with gout"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">See also: <a href="/wiki/Gout#Cause" title="Gout">Gout § Cause</a></div> <p>Higher levels of <a href="/wiki/Meat" title="Meat">meat</a> and <a href="/wiki/Seafood" title="Seafood">seafood</a> consumption are associated with an increased risk of <a href="/wiki/Gout" title="Gout">gout</a>, whereas a higher level of consumption of <a href="/wiki/Dairy_product" title="Dairy product">dairy products</a> is associated with a decreased risk. Moderate intake of purine-rich vegetables or protein is not associated with an increased risk of gout.<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> Similar results have been found with the risk of <a href="/wiki/Hyperuricemia#Increased_production_of_uric_acid" title="Hyperuricemia">hyperuricemia</a>. </p> <div class="mw-heading mw-heading2"><h2 id="Laboratory_synthesis">Laboratory synthesis</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Purine&action=edit&section=10" title="Edit section: Laboratory synthesis"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>In addition to <i><a href="/wiki/In_vivo" title="In vivo">in vivo</a></i> synthesis of purines in <a href="/wiki/Purine_metabolism" title="Purine metabolism">purine metabolism</a>, purine can also be synthesized artificially. </p><p>Purine is obtained in good yield when <a href="/wiki/Formamide" title="Formamide">formamide</a> is heated in an open vessel at 170 °C for 28 hours.<sup id="cite_ref-Yamada_17-0" class="reference"><a href="#cite_note-Yamada-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup> </p> <dl><dd><span typeof="mw:File"><a href="/wiki/File:Purinesynthesis-en.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/5/5a/Purinesynthesis-en.svg/250px-Purinesynthesis-en.svg.png" decoding="async" width="250" height="99" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/5/5a/Purinesynthesis-en.svg/375px-Purinesynthesis-en.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/5/5a/Purinesynthesis-en.svg/500px-Purinesynthesis-en.svg.png 2x" data-file-width="737" data-file-height="291" /></a></span></dd></dl> <p>This remarkable reaction and others like it have been discussed in the context of <a href="/wiki/Abiogenesis" title="Abiogenesis">the origin of life</a>.<sup id="cite_ref-Saladino_18-0" class="reference"><a href="#cite_note-Saladino-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup> </p><p>Patented August 20, 1968, the current recognized method of industrial-scale production of adenine is a modified form of the formamide method. This method heats up formamide under 120 °C conditions within a sealed flask for 5 hours to form adenine. The reaction is heavily increased  in quantity by using a phosphorus oxychloride (phosphoryl chloride) or phosphorus pentachloride as an acid catalyst and sunlight or ultraviolet conditions. After the 5 hours have passed and the formamide-phosphorus oxychloride-adenine solution cools down, water is put into the flask containing the formamide and now-formed adenine. The water-formamide-adenine solution is then poured through a filtering column of activated charcoal. The water and formamide molecules, being small molecules, will pass through the charcoal and into the waste flask; the large adenine molecules, however, will attach or “adsorb” to the charcoal due to the van der waals forces that interact between the adenine and the carbon in the charcoal. Because charcoal has a large surface area, it's able to capture the majority of molecules that pass a certain size (greater than water and formamide) through it. To extract the adenine from the charcoal-adsorbed adenine, ammonia gas dissolved in water (aqua ammonia) is poured onto the activated charcoal-adenine structure to liberate the adenine into the ammonia-water solution. The solution containing water, ammonia, and adenine is then left to air dry, with the adenine losing solubility due to the loss of ammonia gas that previously made the solution basic and capable of dissolving adenine, thus causing it to crystallize into a pure white powder that can be stored.<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> </p><p>Oro and Kamat (1961) and Orgel co-workers (1966, 1967) have shown that four molecules of <a href="/wiki/Hydrogen_cyanide" title="Hydrogen cyanide">HCN</a> tetramerize to form <a href="/wiki/Diaminomaleonitrile" title="Diaminomaleonitrile">diaminomaleodinitrile</a> (<b>12</b>), which can be converted into almost all naturally occurring purines.<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><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><sup id="cite_ref-23" class="reference"><a href="#cite_note-23"><span class="cite-bracket">[</span>23<span class="cite-bracket">]</span></a></sup><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> For example, five molecules of HCN condense in an exothermic reaction to make <a href="/wiki/Adenine" title="Adenine">adenine</a>, especially in the presence of ammonia. </p> <dl><dd><span class="mw-default-size" typeof="mw:File"><a href="/wiki/File:Basicpurines.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/3/3b/Basicpurines.png" decoding="async" width="648" height="529" class="mw-file-element" data-file-width="648" data-file-height="529" /></a></span></dd></dl> <p><span class="anchor" id="Traube_purine_synthesis"></span> The <b>Traube purine synthesis</b> (1900) is a classic reaction (named after <a href="/wiki/Wilhelm_Traube" title="Wilhelm Traube">Wilhelm Traube</a>) between an <a href="/wiki/Amine" title="Amine">amine</a>-substituted <a href="/wiki/Pyrimidine" title="Pyrimidine">pyrimidine</a> and <a href="/wiki/Formic_acid" title="Formic acid">formic acid</a>.<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> <dl><dd><span class="mw-default-size" typeof="mw:File"><a href="/wiki/File:TraubePurineSynthesis.svg" class="mw-file-description" title="Traube purine synthesis"><img alt="Traube purine synthesis" src="//upload.wikimedia.org/wikipedia/commons/thumb/6/6b/TraubePurineSynthesis.svg/386px-TraubePurineSynthesis.svg.png" decoding="async" width="386" height="129" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/6b/TraubePurineSynthesis.svg/579px-TraubePurineSynthesis.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/6b/TraubePurineSynthesis.svg/772px-TraubePurineSynthesis.svg.png 2x" data-file-width="386" data-file-height="129" /></a></span></dd></dl> <div class="mw-heading mw-heading2"><h2 id="Prebiotic_synthesis_of_purine_ribonucleosides">Prebiotic synthesis of purine ribonucleosides</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Purine&action=edit&section=11" title="Edit section: Prebiotic synthesis of purine ribonucleosides"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>In order to understand how <a href="/wiki/Life" title="Life">life</a> arose, knowledge is required of the chemical pathways that permit formation of the key building blocks of life under plausible <a href="/wiki/Abiogenesis" title="Abiogenesis">prebiotic conditions</a>. Nam et al. (2018)<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> demonstrated the direct condensation of purine and pyrimidine nucleobases with ribose to give ribonucleosides in aqueous microdroplets, a key step leading to RNA formation. Also, a plausible prebiotic process for synthesizing purine ribonucleosides was presented by Becker <i>et al</i>. in 2016.<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-heading2"><h2 id="See_also">See also</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Purine&action=edit&section=12" title="Edit section: See also"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a href="/wiki/Purinones" title="Purinones">Purinones</a></li> <li><a href="/wiki/Pyrimidine" title="Pyrimidine">Pyrimidine</a></li> <li><a href="/wiki/Simple_aromatic_ring" title="Simple aromatic ring">Simple aromatic rings</a></li> <li><a href="/wiki/Transition_(genetics)" title="Transition (genetics)">Transition</a></li> <li><a href="/wiki/Transversion" title="Transversion">Transversion</a></li> <li><a href="/wiki/Gout" title="Gout">Gout</a>, a disorder of purine metabolism</li> <li><a href="/wiki/Adenine" title="Adenine">Adenine</a></li> <li><a href="/wiki/Guanine" title="Guanine">Guanine</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=Purine&action=edit&section=13" 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" style="column-width: 30em;"> <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="CITEREFRosemeyer2004" class="citation journal cs1">Rosemeyer H (March 2004). "The chemodiversity of purine as a constituent of natural products". <i>Chemistry & Biodiversity</i>. <b>1</b> (3): 361–401. <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%2Fcbdv.200490033">10.1002/cbdv.200490033</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/17191854">17191854</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:12416667">12416667</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Chemistry+%26+Biodiversity&rft.atitle=The+chemodiversity+of+purine+as+a+constituent+of+natural+products&rft.volume=1&rft.issue=3&rft.pages=361-401&rft.date=2004-03&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A12416667%23id-name%3DS2CID&rft_id=info%3Apmid%2F17191854&rft_id=info%3Adoi%2F10.1002%2Fcbdv.200490033&rft.aulast=Rosemeyer&rft.aufirst=H&rfr_id=info%3Asid%2Fen.wikipedia.org%3APurine" class="Z3988"></span></span> </li> <li id="cite_note-2"><span class="mw-cite-backlink"><b><a href="#cite_ref-2">^</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.dietaryfiberfood.com/purine-food.php">"Gout: List of Foods High and Low in Purine Content"</a>. <i>Dietaryfiberfood.com</i>. 2016-04-08. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20111112133438/http://www.dietaryfiberfood.com/purine-food.php">Archived</a> from the original on 2011-11-12<span class="reference-accessdate">. Retrieved <span class="nowrap">2016-07-16</span></span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=Dietaryfiberfood.com&rft.atitle=Gout%3A+List+of+Foods+High+and+Low+in+Purine+Content&rft.date=2016-04-08&rft_id=http%3A%2F%2Fwww.dietaryfiberfood.com%2Fpurine-food.php&rfr_id=info%3Asid%2Fen.wikipedia.org%3APurine" class="Z3988"></span></span> </li> <li id="cite_note-3"><span class="mw-cite-backlink"><b><a href="#cite_ref-3">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFKanekoAoyagiFukuuchiInazawa2014" class="citation journal cs1">Kaneko K, Aoyagi Y, Fukuuchi T, Inazawa K, Yamaoka N (2014). <a rel="nofollow" class="external text" href="https://doi.org/10.1248%2Fbpb.b13-00967">"Total purine and purine base content of common foodstuffs for facilitating nutritional therapy for gout and hyperuricemia"</a>. <i>Biological & Pharmaceutical Bulletin</i>. <b>37</b> (5): 709–721. <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/10.1248%2Fbpb.b13-00967">10.1248/bpb.b13-00967</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/24553148">24553148</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Biological+%26+Pharmaceutical+Bulletin&rft.atitle=Total+purine+and+purine+base+content+of+common+foodstuffs+for+facilitating+nutritional+therapy+for+gout+and+hyperuricemia&rft.volume=37&rft.issue=5&rft.pages=709-721&rft.date=2014&rft_id=info%3Adoi%2F10.1248%2Fbpb.b13-00967&rft_id=info%3Apmid%2F24553148&rft.aulast=Kaneko&rft.aufirst=K&rft.au=Aoyagi%2C+Y&rft.au=Fukuuchi%2C+T&rft.au=Inazawa%2C+K&rft.au=Yamaoka%2C+N&rft_id=https%3A%2F%2Fdoi.org%2F10.1248%252Fbpb.b13-00967&rfr_id=info%3Asid%2Fen.wikipedia.org%3APurine" class="Z3988"></span></span> </li> <li id="cite_note-4"><span class="mw-cite-backlink"><b><a href="#cite_ref-4">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="http://www.healthcastle.com/gout.shtml">"Gout Diet: What Foods To Avoid"</a>. <i>Healthcastle.com</i>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20170814152322/http://www.healthcastle.com/gout.shtml">Archived</a> from the original on 2017-08-14<span class="reference-accessdate">. Retrieved <span class="nowrap">2016-07-16</span></span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=Healthcastle.com&rft.atitle=Gout+Diet%3A+What+Foods+To+Avoid&rft_id=http%3A%2F%2Fwww.healthcastle.com%2Fgout.shtml&rfr_id=info%3Asid%2Fen.wikipedia.org%3APurine" class="Z3988"></span></span> </li> <li id="cite_note-5"><span class="mw-cite-backlink"><b><a href="#cite_ref-5">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFGuyton2006" class="citation book cs1">Guyton AC (2006). <span class="id-lock-limited" title="Free access subject to limited trial, subscription normally required"><a rel="nofollow" class="external text" href="https://archive.org/details/textbookmedicalp00acgu"><i>Textbook of Medical Physiology</i></a></span>. Elsevier. p. <a rel="nofollow" class="external text" href="https://archive.org/details/textbookmedicalp00acgu/page/n71">37</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-7216-0240-0" title="Special:BookSources/978-0-7216-0240-0"><bdi>978-0-7216-0240-0</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Textbook+of+Medical+Physiology&rft.pages=37&rft.pub=Elsevier&rft.date=2006&rft.isbn=978-0-7216-0240-0&rft.aulast=Guyton&rft.aufirst=AC&rft_id=https%3A%2F%2Farchive.org%2Fdetails%2Ftextbookmedicalp00acgu&rfr_id=info%3Asid%2Fen.wikipedia.org%3APurine" class="Z3988"></span></span> </li> <li id="cite_note-6"><span class="mw-cite-backlink"><b><a href="#cite_ref-6">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFSeela2014" class="citation book cs1 cs1-prop-long-vol">Seela F, et al. (2014). "Hetarenes III (Six-Membered Rings and Larger Hetero-Rings with Maximum Unsaturation) — Part 2b". In Schaumann E (ed.). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=wy2GAwAAQBAJ&pg=PA310"><i>Houben-Weyl Methods of Organic Chemistry</i></a>. Vol. E 9b/2 (4th Supplement ed.). Thieme. p. 310. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-3-13-181504-0" title="Special:BookSources/978-3-13-181504-0"><bdi>978-3-13-181504-0</bdi></a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20220217094219/https://books.google.com/books?id=wy2GAwAAQBAJ&pg=PA310">Archived</a> from the original on 2022-02-17<span class="reference-accessdate">. Retrieved <span class="nowrap">2020-05-15</span></span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Hetarenes+III+%28Six-Membered+Rings+and+Larger+Hetero-Rings+with+Maximum+Unsaturation%29+%E2%80%94+Part+2b&rft.btitle=Houben-Weyl+Methods+of+Organic+Chemistry&rft.pages=310&rft.edition=4th+Supplement&rft.pub=Thieme&rft.date=2014&rft.isbn=978-3-13-181504-0&rft.aulast=Seela&rft.aufirst=F&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3Dwy2GAwAAQBAJ%26pg%3DPA310&rfr_id=info%3Asid%2Fen.wikipedia.org%3APurine" 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="CITEREFRaczyńskaGalMariaKamińska2020" class="citation journal cs1">Raczyńska ED, Gal JF, Maria PC, Kamińska B, Igielska M, Kurpiewski J, Juras W (April 2020). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7256107">"Purine tautomeric preferences and bond-length alternation in relation with protonation-deprotonation and alkali metal cationization"</a>. <i>Journal of Molecular Modeling</i>. <b>26</b> (5): 93. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1007%2Fs00894-020-4343-6">10.1007/s00894-020-4343-6</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/PMC7256107">7256107</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/32248379">32248379</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+Molecular+Modeling&rft.atitle=Purine+tautomeric+preferences+and+bond-length+alternation+in+relation+with+protonation-deprotonation+and+alkali+metal+cationization&rft.volume=26&rft.issue=5&rft.pages=93&rft.date=2020-04&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC7256107%23id-name%3DPMC&rft_id=info%3Apmid%2F32248379&rft_id=info%3Adoi%2F10.1007%2Fs00894-020-4343-6&rft.aulast=Raczy%C5%84ska&rft.aufirst=ED&rft.au=Gal%2C+JF&rft.au=Maria%2C+PC&rft.au=Kami%C5%84ska%2C+B&rft.au=Igielska%2C+M&rft.au=Kurpiewski%2C+J&rft.au=Juras%2C+W&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC7256107&rfr_id=info%3Asid%2Fen.wikipedia.org%3APurine" class="Z3988"></span></span> </li> <li id="cite_note-8"><span class="mw-cite-backlink"><b><a href="#cite_ref-8">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFStasyukSzatyłowiczKrygowski2012" class="citation journal cs1">Stasyuk OA, Szatyłowicz H, Krygowski TM (April 2012). "Effect of the H-bonding on aromaticity of purine tautomers". <i>The Journal of Organic Chemistry</i>. <b>77</b> (8): 4035–45. <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%2Fjo300406r">10.1021/jo300406r</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/22448684">22448684</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=Effect+of+the+H-bonding+on+aromaticity+of+purine+tautomers&rft.volume=77&rft.issue=8&rft.pages=4035-45&rft.date=2012-04&rft_id=info%3Adoi%2F10.1021%2Fjo300406r&rft_id=info%3Apmid%2F22448684&rft.aulast=Stasyuk&rft.aufirst=OA&rft.au=Szaty%C5%82owicz%2C+H&rft.au=Krygowski%2C+TM&rfr_id=info%3Asid%2Fen.wikipedia.org%3APurine" class="Z3988"></span></span> </li> <li id="cite_note-McGuigan-9"><span class="mw-cite-backlink"><b><a href="#cite_ref-McGuigan_9-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFMcGuigan1921" class="citation book cs1">McGuigan H (1921). <a rel="nofollow" class="external text" href="http://www.ebooksread.com/authors-eng/hugh-mcguigan/an-introduction-to-chemical-pharmacology-pharmacodynamics-in-relation-to--goo/page-20-an-introduction-to-chemical-pharmacology-pharmacodynamics-in-relation-to--goo.shtml"><i>An Introduction To Chemical Pharmacology</i></a>. P. Blakiston's Sons & Co. p. 283. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20200416132051/http://www.ebooksread.com/authors-eng/hugh-mcguigan/an-introduction-to-chemical-pharmacology-pharmacodynamics-in-relation-to--goo/page-20-an-introduction-to-chemical-pharmacology-pharmacodynamics-in-relation-to--goo.shtml">Archived</a> from the original on April 16, 2020<span class="reference-accessdate">. Retrieved <span class="nowrap">July 18,</span> 2012</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=An+Introduction+To+Chemical+Pharmacology&rft.pages=283&rft.pub=P.+Blakiston%27s+Sons+%26+Co.&rft.date=1921&rft.aulast=McGuigan&rft.aufirst=H&rft_id=http%3A%2F%2Fwww.ebooksread.com%2Fauthors-eng%2Fhugh-mcguigan%2Fan-introduction-to-chemical-pharmacology-pharmacodynamics-in-relation-to--goo%2Fpage-20-an-introduction-to-chemical-pharmacology-pharmacodynamics-in-relation-to--goo.shtml&rfr_id=info%3Asid%2Fen.wikipedia.org%3APurine" class="Z3988"></span></span> </li> <li id="cite_note-10"><span class="mw-cite-backlink"><b><a href="#cite_ref-10">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFFischer1884" class="citation journal cs1">Fischer E (1884). <a rel="nofollow" class="external text" href="https://zenodo.org/record/1425341/files/article.pdf">"Ueber die Harnsäure. I."</a> [On uric acid. I.] <span class="cs1-format">(PDF)</span>. <i>Berichte der Deutschen Chemischen Gesellschaft</i>. <b>17</b>: 328–338. <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%2Fcber.18840170196">10.1002/cber.18840170196</a><span class="reference-accessdate">. Retrieved <span class="nowrap">2016-04-20</span></span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Berichte+der+Deutschen+Chemischen+Gesellschaft&rft.atitle=Ueber+die+Harns%C3%A4ure.+I.&rft.volume=17&rft.pages=328-338&rft.date=1884&rft_id=info%3Adoi%2F10.1002%2Fcber.18840170196&rft.aulast=Fischer&rft.aufirst=E&rft_id=https%3A%2F%2Fzenodo.org%2Frecord%2F1425341%2Ffiles%2Farticle.pdf&rfr_id=info%3Asid%2Fen.wikipedia.org%3APurine" class="Z3988"></span> <span style="position:relative; top: -2px;"><span typeof="mw:File"><a href="/wiki/Open_access" title="open access publication – free to read"><img alt="Open access icon" src="//upload.wikimedia.org/wikipedia/commons/thumb/7/77/Open_Access_logo_PLoS_transparent.svg/9px-Open_Access_logo_PLoS_transparent.svg.png" decoding="async" width="9" height="14" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/7/77/Open_Access_logo_PLoS_transparent.svg/14px-Open_Access_logo_PLoS_transparent.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/7/77/Open_Access_logo_PLoS_transparent.svg/18px-Open_Access_logo_PLoS_transparent.svg.png 2x" data-file-width="640" data-file-height="1000" /></a></span></span><br /><a rel="nofollow" class="external text" href="https://babel.hathitrust.org/cgi/pt?id=uiug.30112025692879;view=1up;seq=343">From p. 329</a> <a rel="nofollow" class="external text" href="https://web.archive.org/web/20220217094238/https://babel.hathitrust.org/cgi/pt?id=uiug.30112025692879;view=1up;seq=343;a=zoom:1">Archived</a> 2022-02-17 at the <a href="/wiki/Wayback_Machine" title="Wayback Machine">Wayback Machine</a>: <i>"Um eine rationelle Nomenklatur der so entstehenden zahlreichen Substanzen zu ermöglichen, betrachte ich dieselben als Abkömmlinge der noch unbekannten Wasserstoffverbindung CH<sub>3</sub>.C<sub>5</sub>N<sub>4</sub>H<sub>3</sub> and nenne die letztere Methylpurin."</i> (In order to make possible a rational nomenclature for the numerous existing substances, I regarded them as derivatives of a still unknown hydrogen compound, CH<sub>3</sub>.C<sub>5</sub>N<sub>4</sub>H<sub>3</sub>, and call the latter "methylpurine".)</span> </li> <li id="cite_note-Fischer1898-11"><span class="mw-cite-backlink">^ <a href="#cite_ref-Fischer1898_11-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Fischer1898_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="CITEREFFischer1898" class="citation journal cs1">Fischer E (1898). <a rel="nofollow" class="external text" href="https://zenodo.org/record/1425916/files/article.pdf">"Ueber das Purin und seine Methylderivate"</a> [On purine and its methyl derivatives] <span class="cs1-format">(PDF)</span>. <i>Berichte der Deutschen Chemischen Gesellschaft</i>. <b>31</b> (3): 2550–74. <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%2Fcber.18980310304">10.1002/cber.18980310304</a><span class="reference-accessdate">. Retrieved <span class="nowrap">2016-04-20</span></span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Berichte+der+Deutschen+Chemischen+Gesellschaft&rft.atitle=Ueber+das+Purin+und+seine+Methylderivate&rft.volume=31&rft.issue=3&rft.pages=2550-74&rft.date=1898&rft_id=info%3Adoi%2F10.1002%2Fcber.18980310304&rft.aulast=Fischer&rft.aufirst=E&rft_id=https%3A%2F%2Fzenodo.org%2Frecord%2F1425916%2Ffiles%2Farticle.pdf&rfr_id=info%3Asid%2Fen.wikipedia.org%3APurine" class="Z3988"></span> <span style="position:relative; top: -2px;"><span typeof="mw:File"><a href="/wiki/Open_access" title="open access publication – free to read"><img alt="Open access icon" src="//upload.wikimedia.org/wikipedia/commons/thumb/7/77/Open_Access_logo_PLoS_transparent.svg/9px-Open_Access_logo_PLoS_transparent.svg.png" decoding="async" width="9" height="14" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/7/77/Open_Access_logo_PLoS_transparent.svg/14px-Open_Access_logo_PLoS_transparent.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/7/77/Open_Access_logo_PLoS_transparent.svg/18px-Open_Access_logo_PLoS_transparent.svg.png 2x" data-file-width="640" data-file-height="1000" /></a></span></span><br /><a rel="nofollow" class="external text" href="https://babel.hathitrust.org/cgi/pt?id=hvd.cl1i1u;view=1up;seq=14">From p. 2550</a> <a rel="nofollow" class="external text" href="https://web.archive.org/web/20201018131621/https://babel.hathitrust.org/cgi/pt?id=hvd.cl1i1u;view=1up;seq=14">Archived</a> 2020-10-18 at the <a href="/wiki/Wayback_Machine" title="Wayback Machine">Wayback Machine</a>: <i>"…hielt ich es für zweckmäßig, alle diese Produkte ebenso wie die Harnsäure als Derivate der sauerstofffreien Verbindung C<sub>5</sub>H<sub>4</sub>N<sub>4</sub> zu betrachten, und wählte für diese den Namen Purin, welcher aus den Wörtern purum und uricum kombiniert war."</i> (…I regarded it as expedient to consider all of these products, just like uric acid, as derivatives of the oxygen-free compound C<sub>5</sub>H<sub>4</sub>N<sub>4</sub>, and chose for them the name "purine", which was formed from the [Latin] words <i>purum</i> and <i>uricum</i>.)</span> </li> <li id="cite_note-12"><span class="mw-cite-backlink"><b><a href="#cite_ref-12">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFScheele1776" class="citation journal cs1">Scheele CW (1776). "Examen chemicum calculi urinari" [A chemical examination of kidney stones]. <i>Opuscula</i>. <b>2</b>: 73.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Opuscula&rft.atitle=Examen+chemicum+calculi+urinari&rft.volume=2&rft.pages=73&rft.date=1776&rft.aulast=Scheele&rft.aufirst=CW&rfr_id=info%3Asid%2Fen.wikipedia.org%3APurine" class="Z3988"></span></span> </li> <li id="cite_note-pmid_22531138-13"><span class="mw-cite-backlink"><b><a href="#cite_ref-pmid_22531138_13-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFDaviesMendesSmallboneMalys2012" class="citation journal cs1">Davies O, Mendes P, Smallbone K, Malys N (April 2012). <a rel="nofollow" class="external text" href="https://doi.org/10.5483%2FBMBRep.2012.45.4.259">"Characterisation of multiple substrate-specific (d)ITP/(d)XTPase and modelling of deaminated purine nucleotide metabolism"</a>. <i>BMB Reports</i>. <b>45</b> (4): 259–264. <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/10.5483%2FBMBRep.2012.45.4.259">10.5483/BMBRep.2012.45.4.259</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/22531138">22531138</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=BMB+Reports&rft.atitle=Characterisation+of+multiple+substrate-specific+%28d%29ITP%2F%28d%29XTPase+and+modelling+of+deaminated+purine+nucleotide+metabolism&rft.volume=45&rft.issue=4&rft.pages=259-264&rft.date=2012-04&rft_id=info%3Adoi%2F10.5483%2FBMBRep.2012.45.4.259&rft_id=info%3Apmid%2F22531138&rft.aulast=Davies&rft.aufirst=O&rft.au=Mendes%2C+P&rft.au=Smallbone%2C+K&rft.au=Malys%2C+N&rft_id=https%3A%2F%2Fdoi.org%2F10.5483%252FBMBRep.2012.45.4.259&rfr_id=info%3Asid%2Fen.wikipedia.org%3APurine" class="Z3988"></span></span> </li> <li id="cite_note-Brown2011-14"><span class="mw-cite-backlink">^ <a href="#cite_ref-Brown2011_14-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Brown2011_14-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-Brown2011_14-2"><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="CITEREFBrownHoopesWhiteSarisky2011" class="citation journal cs1">Brown, Anne M.; Hoopes, Samantha L.; White, Robert H.; Sarisky, Catherine A. (2011). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3261824">"Purine biosynthesis in archaea: Variations on a theme"</a>. <i>Biology Direct</i>. <b>6</b>: 63. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://doi.org/10.1186%2F1745-6150-6-63">10.1186/1745-6150-6-63</a></span>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3261824">3261824</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/22168471">22168471</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Biology+Direct&rft.atitle=Purine+biosynthesis+in+archaea%3A+Variations+on+a+theme&rft.volume=6&rft.pages=63&rft.date=2011&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC3261824%23id-name%3DPMC&rft_id=info%3Apmid%2F22168471&rft_id=info%3Adoi%2F10.1186%2F1745-6150-6-63&rft.aulast=Brown&rft.aufirst=Anne+M.&rft.au=Hoopes%2C+Samantha+L.&rft.au=White%2C+Robert+H.&rft.au=Sarisky%2C+Catherine+A.&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC3261824&rfr_id=info%3Asid%2Fen.wikipedia.org%3APurine" class="Z3988"></span></span> </li> <li id="cite_note-15"><span class="mw-cite-backlink"><b><a href="#cite_ref-15">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFBernstein1961" class="citation journal cs1">Bernstein, H. (1961). <a rel="nofollow" class="external text" href="https://doi.org/10.1099%2F00221287-25-1-41">"Imidazole Compounds Accumulated by Purine Mutants of Neurospora crassa"</a>. <i>Journal of General Microbiology</i>. <b>25</b>: 41–46. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://doi.org/10.1099%2F00221287-25-1-41">10.1099/00221287-25-1-41</a></span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Journal+of+General+Microbiology&rft.atitle=Imidazole+Compounds+Accumulated+by+Purine+Mutants+of+Neurospora+crassa&rft.volume=25&rft.pages=41-46&rft.date=1961&rft_id=info%3Adoi%2F10.1099%2F00221287-25-1-41&rft.aulast=Bernstein&rft.aufirst=H.&rft_id=https%3A%2F%2Fdoi.org%2F10.1099%252F00221287-25-1-41&rfr_id=info%3Asid%2Fen.wikipedia.org%3APurine" class="Z3988"></span></span> </li> <li id="cite_note-16"><span class="mw-cite-backlink"><b><a href="#cite_ref-16">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFChoiAtkinsonKarlsonWillett2004" class="citation journal cs1">Choi HK, Atkinson K, Karlson EW, Willett W, Curhan G (March 2004). <a rel="nofollow" class="external text" href="https://doi.org/10.1056%2FNEJMoa035700">"Purine-rich foods, dairy and protein intake, and the risk of gout in men"</a>. <i>The New England Journal of Medicine</i>. <b>350</b> (11): 1093–1103. <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/10.1056%2FNEJMoa035700">10.1056/NEJMoa035700</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/15014182">15014182</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=The+New+England+Journal+of+Medicine&rft.atitle=Purine-rich+foods%2C+dairy+and+protein+intake%2C+and+the+risk+of+gout+in+men&rft.volume=350&rft.issue=11&rft.pages=1093-1103&rft.date=2004-03&rft_id=info%3Adoi%2F10.1056%2FNEJMoa035700&rft_id=info%3Apmid%2F15014182&rft.aulast=Choi&rft.aufirst=HK&rft.au=Atkinson%2C+K&rft.au=Karlson%2C+EW&rft.au=Willett%2C+W&rft.au=Curhan%2C+G&rft_id=https%3A%2F%2Fdoi.org%2F10.1056%252FNEJMoa035700&rfr_id=info%3Asid%2Fen.wikipedia.org%3APurine" class="Z3988"></span></span> </li> <li id="cite_note-Yamada-17"><span class="mw-cite-backlink"><b><a href="#cite_ref-Yamada_17-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFYamadaOkamoto1972" class="citation journal cs1">Yamada H, Okamoto T (1972). <a rel="nofollow" class="external text" href="https://www.jstage.jst.go.jp/article/cpb1958/20/3/20_3_623/_article">"A One-step Synthesis of Purine Ring from Formamide"</a>. <i>Chemical & Pharmaceutical Bulletin</i>. <b>20</b> (3): 623. <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/10.1248%2Fcpb.20.623">10.1248/cpb.20.623</a></span>. <a rel="nofollow" class="external text" href="http://arquivo.pt/wayback/20160516170519/http://www.journalarchive.jst.go.jp/english/jnlabstract_en.php?cdjournal=cpb1958&cdvol=20&noissue=3&startpage=623">Archived</a> from the original on 2016-05-16.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Chemical+%26+Pharmaceutical+Bulletin&rft.atitle=A+One-step+Synthesis+of+Purine+Ring+from+Formamide&rft.volume=20&rft.issue=3&rft.pages=623&rft.date=1972&rft_id=info%3Adoi%2F10.1248%2Fcpb.20.623&rft.aulast=Yamada&rft.aufirst=H&rft.au=Okamoto%2C+T&rft_id=https%3A%2F%2Fwww.jstage.jst.go.jp%2Farticle%2Fcpb1958%2F20%2F3%2F20_3_623%2F_article&rfr_id=info%3Asid%2Fen.wikipedia.org%3APurine" class="Z3988"></span></span> </li> <li id="cite_note-Saladino-18"><span class="mw-cite-backlink"><b><a href="#cite_ref-Saladino_18-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFSaladinoCrestiniCicirielloCostanzo2006" class="citation journal cs1">Saladino R, Crestini C, Ciciriello F, Costanzo G, Di Mauro E (December 2006). "About a formamide-based origin of informational polymers: syntheses of nucleobases and favourable thermodynamic niches for early polymers". <i>Origins of Life and Evolution of the Biosphere</i>. <b>36</b> (5–6): 523–531. <a href="/wiki/Bibcode_(identifier)" class="mw-redirect" title="Bibcode (identifier)">Bibcode</a>:<a rel="nofollow" class="external text" href="https://ui.adsabs.harvard.edu/abs/2006OLEB...36..523S">2006OLEB...36..523S</a>. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1007%2Fs11084-006-9053-2">10.1007/s11084-006-9053-2</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/17136429">17136429</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:36278915">36278915</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Origins+of+Life+and+Evolution+of+the+Biosphere&rft.atitle=About+a+formamide-based+origin+of+informational+polymers%3A+syntheses+of+nucleobases+and+favourable+thermodynamic+niches+for+early+polymers&rft.volume=36&rft.issue=5%E2%80%936&rft.pages=523-531&rft.date=2006-12&rft_id=info%3Adoi%2F10.1007%2Fs11084-006-9053-2&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A36278915%23id-name%3DS2CID&rft_id=info%3Apmid%2F17136429&rft_id=info%3Abibcode%2F2006OLEB...36..523S&rft.aulast=Saladino&rft.aufirst=R&rft.au=Crestini%2C+C&rft.au=Ciciriello%2C+F&rft.au=Costanzo%2C+G&rft.au=Di+Mauro%2C+E&rfr_id=info%3Asid%2Fen.wikipedia.org%3APurine" 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"><style data-mw-deduplicate="TemplateStyles:r1041539562">.mw-parser-output .citation{word-wrap:break-word}.mw-parser-output .citation:target{background-color:rgba(0,127,255,0.133)}</style><span class="citation patent"><a rel="nofollow" class="external autonumber" href="https://patents.google.com/patent/US3398149A/en">[1]</a>, "Process for preparing adenine", issued 1966-11-10</span><span class="Z3988" title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Apatent&rft.number=&rft.cc=&rft.title=Process+for+preparing+adenine&rft.date=1966-11-10"><span style="display: none;"> </span></span> <a rel="nofollow" class="external text" href="https://web.archive.org/web/20210526024518/https://patents.google.com/patent/US3398149A/en">Archived</a> 2021-05-26 at the <a href="/wiki/Wayback_Machine" title="Wayback Machine">Wayback Machine</a></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="CITEREFSanchezFerrisOrgel1967" class="citation journal cs1">Sanchez RA, Ferris JP, Orgel LE (December 1967). "Studies in prebiotic synthesis. II. Synthesis of purine precursors and amino acids from aqueous hydrogen cyanide". <i>Journal of Molecular Biology</i>. <b>30</b> (2): 223–253. <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%2FS0022-2836%2867%2980037-8">10.1016/S0022-2836(67)80037-8</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/4297187">4297187</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+Molecular+Biology&rft.atitle=Studies+in+prebiotic+synthesis.+II.+Synthesis+of+purine+precursors+and+amino+acids+from+aqueous+hydrogen+cyanide&rft.volume=30&rft.issue=2&rft.pages=223-253&rft.date=1967-12&rft_id=info%3Adoi%2F10.1016%2FS0022-2836%2867%2980037-8&rft_id=info%3Apmid%2F4297187&rft.aulast=Sanchez&rft.aufirst=RA&rft.au=Ferris%2C+JP&rft.au=Orgel%2C+LE&rfr_id=info%3Asid%2Fen.wikipedia.org%3APurine" 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="CITEREFFerrisOrgel1966" class="citation journal cs1">Ferris JP, Orgel LE (March 1966). "An Unusual Photochemical Rearrangement in the Synthesis of Adenine from Hydrogen Cyanide". <i>Journal of the American Chemical Society</i>. <b>88</b> (5): 1074. <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%2Fja00957a050">10.1021/ja00957a050</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+the+American+Chemical+Society&rft.atitle=An+Unusual+Photochemical+Rearrangement+in+the+Synthesis+of+Adenine+from+Hydrogen+Cyanide&rft.volume=88&rft.issue=5&rft.pages=1074&rft.date=1966-03&rft_id=info%3Adoi%2F10.1021%2Fja00957a050&rft.aulast=Ferris&rft.aufirst=JP&rft.au=Orgel%2C+LE&rfr_id=info%3Asid%2Fen.wikipedia.org%3APurine" 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="CITEREFFerrisKuderCatalano1969" class="citation journal cs1">Ferris JP, Kuder JE, Catalano AW (November 1969). "Photochemical reactions and the chemical evolution of purines and nicotinamide derivatives". <i>Science</i>. <b>166</b> (3906): 765–6. <a href="/wiki/Bibcode_(identifier)" class="mw-redirect" title="Bibcode (identifier)">Bibcode</a>:<a rel="nofollow" class="external text" href="https://ui.adsabs.harvard.edu/abs/1969Sci...166..765F">1969Sci...166..765F</a>. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1126%2Fscience.166.3906.765">10.1126/science.166.3906.765</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/4241847">4241847</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:695243">695243</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Science&rft.atitle=Photochemical+reactions+and+the+chemical+evolution+of+purines+and+nicotinamide+derivatives&rft.volume=166&rft.issue=3906&rft.pages=765-6&rft.date=1969-11&rft_id=info%3Adoi%2F10.1126%2Fscience.166.3906.765&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A695243%23id-name%3DS2CID&rft_id=info%3Apmid%2F4241847&rft_id=info%3Abibcode%2F1969Sci...166..765F&rft.aulast=Ferris&rft.aufirst=JP&rft.au=Kuder%2C+JE&rft.au=Catalano%2C+AW&rfr_id=info%3Asid%2Fen.wikipedia.org%3APurine" class="Z3988"></span></span> </li> <li id="cite_note-23"><span class="mw-cite-backlink"><b><a href="#cite_ref-23">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFOroKamat1961" class="citation journal cs1">Oro J, Kamat SS (April 1961). "Amino-acid synthesis from hydrogen cyanide under possible primitive earth conditions". <i>Nature</i>. <b>190</b> (4774): 442–3. <a href="/wiki/Bibcode_(identifier)" class="mw-redirect" title="Bibcode (identifier)">Bibcode</a>:<a rel="nofollow" class="external text" href="https://ui.adsabs.harvard.edu/abs/1961Natur.190..442O">1961Natur.190..442O</a>. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1038%2F190442a0">10.1038/190442a0</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/13731262">13731262</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:4219284">4219284</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Nature&rft.atitle=Amino-acid+synthesis+from+hydrogen+cyanide+under+possible+primitive+earth+conditions&rft.volume=190&rft.issue=4774&rft.pages=442-3&rft.date=1961-04&rft_id=info%3Adoi%2F10.1038%2F190442a0&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A4219284%23id-name%3DS2CID&rft_id=info%3Apmid%2F13731262&rft_id=info%3Abibcode%2F1961Natur.190..442O&rft.aulast=Oro&rft.aufirst=J&rft.au=Kamat%2C+SS&rfr_id=info%3Asid%2Fen.wikipedia.org%3APurine" 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="CITEREFBauer1985" class="citation book cs1">Bauer W (1985). <i>Houben-Weyl Methods of Organic Chemistry</i>. Vol. E 5 (4th Supplement ed.). Thieme Georg Verlag. p. 1547. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-3-13-181154-7" title="Special:BookSources/978-3-13-181154-7"><bdi>978-3-13-181154-7</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Houben-Weyl+Methods+of+Organic+Chemistry&rft.pages=1547&rft.edition=4th+Supplement&rft.pub=Thieme+Georg+Verlag&rft.date=1985&rft.isbn=978-3-13-181154-7&rft.aulast=Bauer&rft.aufirst=W&rfr_id=info%3Asid%2Fen.wikipedia.org%3APurine" 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="CITEREFHassnerStumer2002" class="citation book cs1">Hassner A, Stumer C (2002). <i>Organic Syntheses Based on Name Reactions</i> (2nd ed.). Elsevier. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/0-08-043259-X" title="Special:BookSources/0-08-043259-X"><bdi>0-08-043259-X</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Organic+Syntheses+Based+on+Name+Reactions&rft.edition=2nd&rft.pub=Elsevier&rft.date=2002&rft.isbn=0-08-043259-X&rft.aulast=Hassner&rft.aufirst=A&rft.au=Stumer%2C+C&rfr_id=info%3Asid%2Fen.wikipedia.org%3APurine" 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="CITEREFNamNamZare2018" class="citation journal cs1">Nam I, Nam HG, Zare RN (January 2018). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5776833">"Abiotic synthesis of purine and pyrimidine ribonucleosides in aqueous microdroplets"</a>. <i>Proc Natl Acad Sci U S A</i>. <b>115</b> (1): 36–40. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1073%2Fpnas.1718559115">10.1073/pnas.1718559115</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/PMC5776833">5776833</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/29255025">29255025</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Proc+Natl+Acad+Sci+U+S+A&rft.atitle=Abiotic+synthesis+of+purine+and+pyrimidine+ribonucleosides+in+aqueous+microdroplets&rft.volume=115&rft.issue=1&rft.pages=36-40&rft.date=2018-01&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC5776833%23id-name%3DPMC&rft_id=info%3Apmid%2F29255025&rft_id=info%3Adoi%2F10.1073%2Fpnas.1718559115&rft.aulast=Nam&rft.aufirst=I&rft.au=Nam%2C+HG&rft.au=Zare%2C+RN&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC5776833&rfr_id=info%3Asid%2Fen.wikipedia.org%3APurine" 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="CITEREFBeckerThomaDeutschGehrke2016" class="citation journal cs1">Becker S, Thoma I, Deutsch A, Gehrke T, Mayer P, Zipse H, Carell T (May 2016). "A high-yielding, strictly regioselective prebiotic purine nucleoside formation pathway". <i>Science</i>. <b>352</b> (6287): 833–6. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1126%2Fscience.aad2808">10.1126/science.aad2808</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/27174989">27174989</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Science&rft.atitle=A+high-yielding%2C+strictly+regioselective+prebiotic+purine+nucleoside+formation+pathway&rft.volume=352&rft.issue=6287&rft.pages=833-6&rft.date=2016-05&rft_id=info%3Adoi%2F10.1126%2Fscience.aad2808&rft_id=info%3Apmid%2F27174989&rft.aulast=Becker&rft.aufirst=S&rft.au=Thoma%2C+I&rft.au=Deutsch%2C+A&rft.au=Gehrke%2C+T&rft.au=Mayer%2C+P&rft.au=Zipse%2C+H&rft.au=Carell%2C+T&rfr_id=info%3Asid%2Fen.wikipedia.org%3APurine" 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=Purine&action=edit&section=14" 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="http://www.dietaryfiberfood.com/purine-food.php">Purine Content in Food</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="Nucleic_acid_constituents" style="padding:3px"><table class="nowraplinks mw-collapsible autocollapse navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><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:Nucleobases,_nucleosides,_and_nucleotides" title="Template:Nucleobases, nucleosides, and nucleotides"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Nucleobases,_nucleosides,_and_nucleotides" title="Template talk:Nucleobases, nucleosides, and nucleotides"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Nucleobases,_nucleosides,_and_nucleotides" title="Special:EditPage/Template:Nucleobases, nucleosides, and nucleotides"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Nucleic_acid_constituents" style="font-size:114%;margin:0 4em"><a href="/wiki/Nucleic_acid" title="Nucleic acid">Nucleic acid</a> constituents</div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Nucleobase" class="mw-redirect" title="Nucleobase">Nucleobase</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 class="mw-selflink selflink">Purine</a> <ul><li><a href="/wiki/Adenine" title="Adenine">Adenine</a></li> <li><a href="/wiki/Guanine" title="Guanine">Guanine</a></li> <li><a href="/wiki/Hypoxanthine" title="Hypoxanthine">Hypoxanthine</a></li> <li><a href="/wiki/Xanthine" title="Xanthine">Xanthine</a></li> <li><a href="/wiki/Purine_analogue" title="Purine analogue">Purine analogue</a></li></ul></li> <li><a href="/wiki/Pyrimidine" title="Pyrimidine">Pyrimidine</a> <ul><li><a href="/wiki/Uracil" title="Uracil">Uracil</a></li> <li><a href="/wiki/Thymine" title="Thymine">Thymine</a></li> <li><a href="/wiki/Cytosine" title="Cytosine">Cytosine</a></li> <li><a href="/wiki/Pyrimidine_analogue" title="Pyrimidine analogue">Pyrimidine analogue</a></li></ul></li> <li><a href="/wiki/Base_pair#Unnatural_base_pair_(UBP)" title="Base pair">Unnatural base pair (UBP)</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Nucleoside" title="Nucleoside">Nucleoside</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/Ribonucleoside" title="Ribonucleoside">Ribonucleoside</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/Adenosine" title="Adenosine">Adenosine</a></li> <li><a href="/wiki/Guanosine" title="Guanosine">Guanosine</a></li> <li><a href="/wiki/5-Methyluridine" title="5-Methyluridine">5-Methyluridine</a></li> <li><a href="/wiki/Uridine" title="Uridine">Uridine</a></li> <li><a href="/wiki/5-Methylcytidine" title="5-Methylcytidine">5-Methylcytidine</a></li> <li><a href="/wiki/Cytidine" title="Cytidine">Cytidine</a></li> <li><a href="/wiki/Pseudouridine" title="Pseudouridine">Pseudouridine</a></li> <li><a href="/wiki/Inosine" title="Inosine">Inosine</a></li> <li><a href="/wiki/N6-Methyladenosine" title="N6-Methyladenosine"><i>N</i><sup>6</sup>-Methyladenosine</a></li> <li><a href="/wiki/Xanthosine" title="Xanthosine">Xanthosine</a></li> <li><a href="/wiki/Wybutosine" title="Wybutosine">Wybutosine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Deoxyribonucleoside" class="mw-redirect" title="Deoxyribonucleoside">Deoxyribonucleoside</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/Deoxyadenosine" title="Deoxyadenosine">Deoxyadenosine</a></li> <li><a href="/wiki/Deoxyguanosine" title="Deoxyguanosine">Deoxyguanosine</a></li> <li><a href="/wiki/Thymidine" title="Thymidine">Thymidine</a></li> <li><a href="/wiki/Deoxyuridine" title="Deoxyuridine">Deoxyuridine</a></li> <li><a href="/wiki/Deoxycytidine" title="Deoxycytidine">Deoxycytidine</a></li> <li><a href="/w/index.php?title=Deoxyinosine&action=edit&redlink=1" class="new" title="Deoxyinosine (page does not exist)">Deoxyinosine</a></li> <li><a href="/w/index.php?title=Deoxyxanthosine&action=edit&redlink=1" class="new" title="Deoxyxanthosine (page does not exist)">Deoxyxanthosine</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/Nucleotide" title="Nucleotide">Nucleotide</a><br />(Nucleoside monophosphate)</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/Ribonucleotide" title="Ribonucleotide">Ribonucleotide</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/Adenosine_monophosphate" title="Adenosine monophosphate">AMP</a></li> <li><a href="/wiki/Guanosine_monophosphate" title="Guanosine monophosphate">GMP</a></li> <li><a href="/w/index.php?title=5-Methyluridine_monophosphate&action=edit&redlink=1" class="new" title="5-Methyluridine monophosphate (page does not exist)">m<sup>5</sup>UMP</a></li> <li><a href="/wiki/Uridine_monophosphate" title="Uridine monophosphate">UMP</a></li> <li><a href="/wiki/Cytidine_monophosphate" title="Cytidine monophosphate">CMP</a></li> <li><a href="/wiki/Inosinic_acid" title="Inosinic acid">IMP</a></li> <li><a href="/wiki/Xanthosine_monophosphate" title="Xanthosine monophosphate">XMP</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Deoxyribonucleotide" title="Deoxyribonucleotide">Deoxyribonucleotide</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/Deoxyadenosine_monophosphate" title="Deoxyadenosine monophosphate">dAMP</a></li> <li><a href="/wiki/Deoxyguanosine_monophosphate" title="Deoxyguanosine monophosphate">dGMP</a></li> <li><a href="/wiki/Thymidine_monophosphate" title="Thymidine monophosphate">dTMP</a></li> <li><a href="/wiki/Deoxyuridine_monophosphate" title="Deoxyuridine monophosphate">dUMP</a></li> <li><a href="/wiki/Deoxycytidine_monophosphate" title="Deoxycytidine monophosphate">dCMP</a></li> <li><a href="/wiki/Deoxyinosine_monophosphate" title="Deoxyinosine monophosphate">dIMP</a></li> <li><a href="/w/index.php?title=Deoxyxanthosine_monophosphate&action=edit&redlink=1" class="new" title="Deoxyxanthosine monophosphate (page does not exist)">dXMP</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Cyclic_nucleotide" title="Cyclic nucleotide">Cyclic nucleotide</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/Cyclic_adenosine_monophosphate" title="Cyclic adenosine monophosphate">cAMP</a></li> <li><a href="/wiki/Cyclic_guanosine_monophosphate" title="Cyclic guanosine monophosphate">cGMP</a></li> <li><a href="/wiki/Cyclic_di-GMP" title="Cyclic di-GMP">c-di-GMP</a></li> <li><a href="/wiki/Cyclic_di-AMP" title="Cyclic di-AMP">c-di-AMP</a></li> <li><a href="/wiki/Cyclic_ADP-ribose" title="Cyclic ADP-ribose">cADPR</a></li> <li><a href="/wiki/Cyclic_guanosine_monophosphate%E2%80%93adenosine_monophosphate" title="Cyclic guanosine monophosphate–adenosine monophosphate">cGAMP</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Nucleoside diphosphate</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><td colspan="2" class="navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Adenosine_diphosphate" title="Adenosine diphosphate">ADP</a></li> <li><a href="/wiki/Guanosine_diphosphate" title="Guanosine diphosphate">GDP</a></li> <li><a href="/w/index.php?title=5-Methyluridine_diphosphate&action=edit&redlink=1" class="new" title="5-Methyluridine diphosphate (page does not exist)">m<sup>5</sup>UDP</a></li> <li><a href="/wiki/Uridine_diphosphate" title="Uridine diphosphate">UDP</a></li> <li><a href="/wiki/Cytidine_diphosphate" title="Cytidine diphosphate">CDP</a></li> <li><a href="/w/index.php?title=Xanthosine_diphosphate&action=edit&redlink=1" class="new" title="Xanthosine diphosphate (page does not exist)">Xanthosine diphosphate</a></li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Deoxyadenosine_diphosphate" title="Deoxyadenosine diphosphate">dADP</a></li> <li><a href="/wiki/Deoxyguanosine_diphosphate" title="Deoxyguanosine diphosphate">dGDP</a></li> <li><a href="/wiki/Thymidine_diphosphate" title="Thymidine diphosphate">dTDP</a></li> <li><a href="/w/index.php?title=Deoxyuridine_diphosphate&action=edit&redlink=1" class="new" title="Deoxyuridine diphosphate (page does not exist)">dUDP</a></li> <li><a href="/wiki/Deoxycytidine_diphosphate" title="Deoxycytidine diphosphate">dCDP</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/Nucleoside_triphosphate" title="Nucleoside triphosphate">Nucleoside triphosphate</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><td colspan="2" class="navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Adenosine_triphosphate" title="Adenosine triphosphate">ATP</a></li> <li><a href="/wiki/Guanosine_triphosphate" title="Guanosine triphosphate">GTP</a></li> <li><a href="/wiki/5-Methyluridine_triphosphate" title="5-Methyluridine triphosphate">m<sup>5</sup>UTP</a></li> <li><a href="/wiki/Uridine_triphosphate" title="Uridine triphosphate">UTP</a></li> <li><a href="/wiki/Cytidine_triphosphate" title="Cytidine triphosphate">CTP</a></li> <li><a href="/wiki/Inosine_triphosphate" title="Inosine triphosphate">ITP</a></li> <li><a href="/wiki/Xanthosine_triphosphate" title="Xanthosine triphosphate">XTP</a></li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Deoxyadenosine_triphosphate" title="Deoxyadenosine triphosphate">dATP</a></li> <li><a href="/wiki/Deoxyguanosine_triphosphate" title="Deoxyguanosine triphosphate">dGTP</a></li> <li><a href="/wiki/Thymidine_triphosphate" title="Thymidine triphosphate">dTTP</a></li> <li><a href="/w/index.php?title=Deoxyuridine_triphosphate&action=edit&redlink=1" class="new" title="Deoxyuridine triphosphate (page does not exist)">dUTP</a></li> <li><a href="/wiki/Deoxycytidine_triphosphate" title="Deoxycytidine triphosphate">dCTP</a></li> <li><a href="/w/index.php?title=Deoxyinosine_triphosphate&action=edit&redlink=1" class="new" title="Deoxyinosine triphosphate (page does not exist)">dITP</a></li> <li><a href="/w/index.php?title=Deoxyxanthosine_triphosphate&action=edit&redlink=1" class="new" title="Deoxyxanthosine triphosphate (page does not exist)">dXTP</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"></div><div role="navigation" class="navbox" aria-labelledby="Purine_receptor_modulators" 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:Purine_receptor_modulators" title="Template:Purine receptor modulators"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Purine_receptor_modulators" title="Template talk:Purine receptor modulators"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Purine_receptor_modulators" title="Special:EditPage/Template:Purine receptor modulators"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Purine_receptor_modulators" style="font-size:114%;margin:0 4em"><a href="/wiki/Purine_receptor" class="mw-redirect" title="Purine receptor">Purine 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/Receptor_(biochemistry)" title="Receptor (biochemistry)">Receptor</a><br /><small>(<a href="/wiki/Ligand_(biochemistry)" title="Ligand (biochemistry)">ligands</a>)</small></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:6em;;text-align:center;"><a href="/wiki/P0_receptor" class="mw-redirect" title="P0 receptor">P0</a> (<a href="/wiki/Adenine" title="Adenine">adenine</a>)</th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><b>Agonists:</b> <a href="/w/index.php?title=8-Aminoadenine&action=edit&redlink=1" class="new" title="8-Aminoadenine (page does not exist)">8-Aminoadenine</a></li> <li><a href="/wiki/Adenine" title="Adenine">Adenine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:6em;;text-align:center;"><a href="/wiki/Adenosine_receptor" title="Adenosine receptor">P1</a><br />(<a href="/wiki/Adenosine" title="Adenosine">adenosine</a>)</th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><b>Agonists:</b> <a href="/w/index.php?title=2-(1-Hexynyl)-N-methyladenosine&action=edit&redlink=1" class="new" title="2-(1-Hexynyl)-N-methyladenosine (page does not exist)">2-(1-Hexynyl)-<i>N</i>-methyladenosine</a></li> <li><a href="/w/index.php?title=2-Cl-IB-MECA&action=edit&redlink=1" class="new" title="2-Cl-IB-MECA (page does not exist)">2-Cl-IB-MECA</a></li> <li><a href="/w/index.php?title=2-Chloroadenosine&action=edit&redlink=1" class="new" title="2-Chloroadenosine (page does not exist)">2-Chloroadenosine</a></li> <li><a href="/w/index.php?title=2%27-MeCCPA&action=edit&redlink=1" class="new" title="2'-MeCCPA (page does not exist)">2'-MeCCPA</a></li> <li><a href="/w/index.php?title=4%27-O-%CE%B2-D-Glucosyl-9-O-(6%27-deoxysaccharosyl)olivil&action=edit&redlink=1" class="new" title="4'-O-β-D-Glucosyl-9-O-(6'-deoxysaccharosyl)olivil (page does not exist)">4'-O-β-D-Glucosyl-9-O-(6''-deoxysaccharosyl)olivil</a></li> <li><a href="/w/index.php?title=5%27-N-ethylcarboxamidoadenosine&action=edit&redlink=1" class="new" title="5'-N-ethylcarboxamidoadenosine (page does not exist)">5'-<i>N</i>-ethylcarboxamidoadenosine</a></li> <li><a href="/wiki/Adenosine" title="Adenosine">Adenosine</a></li> <li><a href="/wiki/Adenosine_diphosphate" title="Adenosine diphosphate">ADP</a></li> <li><a href="/wiki/Adenosine_monophosphate" title="Adenosine monophosphate">AMP</a></li> <li><a href="/w/index.php?title=Apadenoson&action=edit&redlink=1" class="new" title="Apadenoson (page does not exist)">Apadenoson</a></li> <li><a href="/wiki/ATL-146e" class="mw-redirect" title="ATL-146e">ATL-146e</a></li> <li><a href="/wiki/Adenosine_triphosphate" title="Adenosine triphosphate">ATP</a></li> <li><a href="/wiki/BAY_60%E2%80%936583" title="BAY 60–6583">BAY 60–6583</a></li> <li><a href="/w/index.php?title=Binodenoson&action=edit&redlink=1" class="new" title="Binodenoson (page does not exist)">Binodenoson</a></li> <li><a href="/w/index.php?title=Capadenoson&action=edit&redlink=1" class="new" title="Capadenoson (page does not exist)">Capadenoson</a></li> <li><a href="/wiki/CCPA_(biochemistry)" title="CCPA (biochemistry)">CCPA</a></li> <li><a href="/wiki/CGS-21680" title="CGS-21680">CGS-21680</a></li> <li><a href="/wiki/CP-532,903" title="CP-532,903">CP-532,903</a></li> <li><a href="/w/index.php?title=CV-1808&action=edit&redlink=1" class="new" title="CV-1808 (page does not exist)">CV-1808</a></li> <li><a href="/w/index.php?title=Evodenoson&action=edit&redlink=1" class="new" title="Evodenoson (page does not exist)">Evodenoson</a></li> <li><a href="/w/index.php?title=GR_79236&action=edit&redlink=1" class="new" title="GR 79236 (page does not exist)">GR 79236</a></li> <li><a href="/w/index.php?title=HENECA&action=edit&redlink=1" class="new" title="HENECA (page does not exist)">HENECA</a></li> <li><a href="/w/index.php?title=LUF-5835&action=edit&redlink=1" class="new" title="LUF-5835 (page does not exist)">LUF-5835</a></li> <li><a href="/w/index.php?title=LUF-5845&action=edit&redlink=1" class="new" title="LUF-5845 (page does not exist)">LUF-5845</a></li> <li><a href="/wiki/N6-Cyclopentyladenosine" title="N6-Cyclopentyladenosine"><i>N</i><sup>6</sup>-Cyclopentyladenosine</a></li> <li><a href="/wiki/Namodenoson" title="Namodenoson">Namodenoson</a></li> <li><a href="/w/index.php?title=NECA_(drug)&action=edit&redlink=1" class="new" title="NECA (drug) (page does not exist)">NECA</a></li> <li><a href="/w/index.php?title=Neladenoson_dalanate&action=edit&redlink=1" class="new" title="Neladenoson dalanate (page does not exist)">Neladenoson dalanate</a></li> <li><a href="/w/index.php?title=Piclidenoson&action=edit&redlink=1" class="new" title="Piclidenoson (page does not exist)">Piclidenoson</a></li> <li><a href="/wiki/Regadenoson" title="Regadenoson">Regadenoson</a></li> <li><a href="/w/index.php?title=SDZ_WAG_994&action=edit&redlink=1" class="new" title="SDZ WAG 994 (page does not exist)">SDZ WAG 994</a></li> <li><a href="/w/index.php?title=Selodenoson&action=edit&redlink=1" class="new" title="Selodenoson (page does not exist)">Selodenoson</a></li> <li><a href="/w/index.php?title=Sonedenoson&action=edit&redlink=1" class="new" title="Sonedenoson (page does not exist)">Sonedenoson</a></li> <li><a href="/w/index.php?title=Tecadenoson&action=edit&redlink=1" class="new" title="Tecadenoson (page does not exist)">Tecadenoson</a></li> <li><a href="/w/index.php?title=Trabodenoson&action=edit&redlink=1" class="new" title="Trabodenoson (page does not exist)">Trabodenoson</a></li> <li><a href="/wiki/UK-432,097" title="UK-432,097">UK-432,097</a></li></ul> <ul><li><b>Antagonists:</b> <a href="/wiki/3-Chlorostyrylcaffeine" title="3-Chlorostyrylcaffeine">3-Chlorostyrylcaffeine (CSC)</a></li> <li><a href="/wiki/7-Methylxanthine" title="7-Methylxanthine">7-Methylxanthine</a></li> <li><a href="/wiki/8-Chlorotheophylline" title="8-Chlorotheophylline">8-Chlorotheophylline</a></li> <li><a href="/w/index.php?title=8-Phenyl-1,3-dipropylxanthine&action=edit&redlink=1" class="new" title="8-Phenyl-1,3-dipropylxanthine (page does not exist)">8-Phenyl-1,3-dipropylxanthine</a></li> <li><a href="/wiki/8-Phenyltheophylline" title="8-Phenyltheophylline">8-Phenyltheophylline</a></li> <li><a href="/wiki/Acefylline" title="Acefylline">Acefylline</a></li> <li><a href="/wiki/Aminophylline" title="Aminophylline">Aminophylline</a></li> <li><a href="/wiki/ATL-444" title="ATL-444">ATL-444</a></li> <li><a href="/w/index.php?title=AZD-4635&action=edit&redlink=1" class="new" title="AZD-4635 (page does not exist)">AZD-4635</a></li> <li><a href="/wiki/Bamifylline" title="Bamifylline">Bamifylline</a></li> <li><a href="/wiki/Cafedrine" title="Cafedrine">Cafedrine</a></li> <li><a href="/wiki/Caffeine" title="Caffeine">Caffeine</a></li> <li><a href="/wiki/Caffeine_citrate" title="Caffeine citrate">Caffeine citrate</a></li> <li><a href="/wiki/Cartazolate" title="Cartazolate">Cartazolate</a></li> <li><a href="/w/index.php?title=CGH-2466&action=edit&redlink=1" class="new" title="CGH-2466 (page does not exist)">CGH-2466</a></li> <li><a href="/wiki/CGS-15943" title="CGS-15943">CGS-15943</a></li> <li><a href="/wiki/Choline_theophyllinate" title="Choline theophyllinate">Choline theophyllinate</a></li> <li><a href="/w/index.php?title=Ciforadenant&action=edit&redlink=1" class="new" title="Ciforadenant (page does not exist)">Ciforadenant</a></li> <li><a href="/wiki/8-Cyclopentyl-1,3-dimethylxanthine" title="8-Cyclopentyl-1,3-dimethylxanthine">CPX</a></li> <li><a href="/w/index.php?title=CVT-6883&action=edit&redlink=1" class="new" title="CVT-6883 (page does not exist)">CVT-6883</a></li> <li><a href="/wiki/Dimethazan" title="Dimethazan">Dimethazan</a></li> <li><a href="/wiki/DMPX" title="DMPX">DMPX</a></li> <li><a href="/wiki/8-Cyclopentyl-1,3-dipropylxanthine" class="mw-redirect" title="8-Cyclopentyl-1,3-dipropylxanthine">DPCPX</a></li> <li><a href="/wiki/Dyphylline" class="mw-redirect" title="Dyphylline">Dyphylline</a></li> <li><a href="/wiki/Enprofylline" title="Enprofylline">Enprofylline</a></li> <li><a href="/wiki/Etazolate" title="Etazolate">Etazolate</a></li> <li><a href="/w/index.php?title=Etrumadenant&action=edit&redlink=1" class="new" title="Etrumadenant (page does not exist)">Etrumadenant</a></li> <li><a href="/wiki/Fenethylline" title="Fenethylline">Fenethylline</a></li> <li><a href="/wiki/IBMX" title="IBMX">IBMX</a></li> <li><a href="/w/index.php?title=Imaradenant&action=edit&redlink=1" class="new" title="Imaradenant (page does not exist)">Imaradenant</a></li> <li><a href="/w/index.php?title=Inupadenant&action=edit&redlink=1" class="new" title="Inupadenant (page does not exist)">Inupadenant</a></li> <li><a href="/wiki/ISAM-140" title="ISAM-140">ISAM-140</a></li> <li><a href="/w/index.php?title=ISAM-R316&action=edit&redlink=1" class="new" title="ISAM-R316 (page does not exist)">ISAM-R316</a></li> <li><a href="/wiki/Isovaleric_acid" title="Isovaleric acid">Isovaleric acid</a></li> <li><a href="/wiki/Istradefylline" title="Istradefylline">Istradefylline</a></li> <li><a href="/wiki/KF-26777" title="KF-26777">KF-26777</a></li> <li><a href="/wiki/Lu_AA41063" title="Lu AA41063">Lu AA41063</a></li> <li><a href="/wiki/Lu_AA47070" title="Lu AA47070">Lu AA47070</a></li> <li><a href="/wiki/MRE3008F20" class="mw-redirect" title="MRE3008F20">MRE3008F20</a></li> <li><a href="/wiki/MRS-1191" class="mw-redirect" title="MRS-1191">MRS-1191</a></li> <li><a href="/w/index.php?title=MRS-1220&action=edit&redlink=1" class="new" title="MRS-1220 (page does not exist)">MRS-1220</a></li> <li><a href="/w/index.php?title=MRS-1334&action=edit&redlink=1" class="new" title="MRS-1334 (page does not exist)">MRS-1334</a></li> <li><a href="/wiki/MRS-1523" class="mw-redirect" title="MRS-1523">MRS-1523</a></li> <li><a href="/wiki/MRS-1706" title="MRS-1706">MRS-1706</a></li> <li><a href="/w/index.php?title=MRS-1754&action=edit&redlink=1" class="new" title="MRS-1754 (page does not exist)">MRS-1754</a></li> <li><a href="/w/index.php?title=MRS-3777&action=edit&redlink=1" class="new" title="MRS-3777 (page does not exist)">MRS-3777</a></li> <li><a href="/wiki/MSX-2" title="MSX-2">MSX-2</a></li> <li><a href="/wiki/MSX-3" title="MSX-3">MSX-3</a></li> <li><a href="/wiki/MSX-4" title="MSX-4">MSX-4</a></li> <li><a href="/w/index.php?title=Muvadenant&action=edit&redlink=1" class="new" title="Muvadenant (page does not exist)">Muvadenant</a></li> <li><a href="/wiki/Paraxanthine" title="Paraxanthine">Paraxanthine</a></li> <li><a href="/wiki/Pentoxifylline" title="Pentoxifylline">Pentoxifylline</a></li> <li><a href="/wiki/Preladenant" title="Preladenant">Preladenant</a></li> <li><a href="/wiki/Propentofylline" title="Propentofylline">Propentofylline</a></li> <li><a href="/wiki/Proxyphylline" title="Proxyphylline">Proxyphylline</a></li> <li><a href="/wiki/PSB-10" title="PSB-10">PSB-10</a></li> <li><a href="/w/index.php?title=PSB-11&action=edit&redlink=1" class="new" title="PSB-11 (page does not exist)">PSB-11</a></li> <li><a href="/w/index.php?title=PSB-36&action=edit&redlink=1" class="new" title="PSB-36 (page does not exist)">PSB-36</a></li> <li><a href="/w/index.php?title=PSB-603&action=edit&redlink=1" class="new" title="PSB-603 (page does not exist)">PSB-603</a></li> <li><a href="/w/index.php?title=PSB-788&action=edit&redlink=1" class="new" title="PSB-788 (page does not exist)">PSB-788</a></li> <li><a href="/w/index.php?title=PSB-1115&action=edit&redlink=1" class="new" title="PSB-1115 (page does not exist)">PSB-1115</a></li> <li><a href="/w/index.php?title=PSB-1901&action=edit&redlink=1" class="new" title="PSB-1901 (page does not exist)">PSB-1901</a></li> <li><a href="/wiki/Reversine" title="Reversine">Reversine</a></li> <li><a href="/wiki/Rolofylline" title="Rolofylline">Rolofylline</a></li> <li><a href="/wiki/SCH-442,416" title="SCH-442,416">SCH-442,416</a></li> <li><a href="/wiki/SCH-58261" title="SCH-58261">SCH-58261</a></li> <li><a href="/w/index.php?title=Sipagladenant&action=edit&redlink=1" class="new" title="Sipagladenant (page does not exist)">Sipagladenant</a></li> <li><a href="/w/index.php?title=Taminadenant&action=edit&redlink=1" class="new" title="Taminadenant (page does not exist)">Taminadenant</a></li> <li><a href="/wiki/Theacrine" title="Theacrine">Theacrine</a></li> <li><a href="/wiki/Theobromine" title="Theobromine">Theobromine</a></li> <li><a href="/wiki/Theodrenaline" title="Theodrenaline">Theodrenaline</a></li> <li><a href="/wiki/Theophylline" title="Theophylline">Theophylline</a></li> <li><a href="/w/index.php?title=Tozadenant&action=edit&redlink=1" class="new" title="Tozadenant (page does not exist)">Tozadenant</a></li> <li><a href="/wiki/Tracazolate" title="Tracazolate">Tracazolate</a></li> <li><a href="/w/index.php?title=Vipadenant&action=edit&redlink=1" class="new" title="Vipadenant (page does not exist)">Vipadenant</a></li> <li><a href="/w/index.php?title=VUF-5574&action=edit&redlink=1" class="new" title="VUF-5574 (page does not exist)">VUF-5574</a></li> <li><a href="/wiki/ZM-241,385" title="ZM-241,385">ZM-241,385</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:6em;;text-align:center;"><a href="/wiki/P2_receptor" title="P2 receptor">P2</a><br />(<a href="/wiki/Nucleotide" title="Nucleotide">nucleotide</a>)</th><td class="navbox-list-with-group navbox-list navbox-odd" style="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:3em;;text-align:center;"><a href="/wiki/P2X_purinoreceptor" title="P2X purinoreceptor">P2X</a><br />(<a href="/wiki/Adenosine_triphosphate" title="Adenosine triphosphate"><abbr title="Adenosine triphosphate">ATP</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 Adenosine triphosphate</span>)</th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><b>Agonists:</b> <a href="/w/index.php?title=2-Methylthio-ATP&action=edit&redlink=1" class="new" title="2-Methylthio-ATP (page does not exist)">2-Me-SATP</a></li> <li><a href="/w/index.php?title=%CE%91,%CE%B2-Methylene-ATP&action=edit&redlink=1" class="new" title="Α,β-Methylene-ATP (page does not exist)">α,β-Me-ATP</a></li> <li><a href="/wiki/Adenosine" title="Adenosine">Adenosine</a></li> <li><a href="/wiki/Adenosine_diphosphate" title="Adenosine diphosphate">ADP</a></li> <li><a href="/wiki/Adenosine_monophosphate" title="Adenosine monophosphate">AMP</a></li> <li><a href="/wiki/Diadenosine_tetraphosphate" class="mw-redirect" title="Diadenosine tetraphosphate">Ap4A</a></li> <li><a href="/w/index.php?title=Diadenosine_pentaphosphate&action=edit&redlink=1" class="new" title="Diadenosine pentaphosphate (page does not exist)">Ap5A</a></li> <li><a href="/wiki/Adenosine_triphosphate" title="Adenosine triphosphate">ATP</a></li> <li><a href="/w/index.php?title=Adenosine-5%27-(%CE%B3-thio)-triphosphate&action=edit&redlink=1" class="new" title="Adenosine-5'-(γ-thio)-triphosphate (page does not exist)">ATPγS</a></li> <li><a href="/w/index.php?title=BzATP&action=edit&redlink=1" class="new" title="BzATP (page does not exist)">BzATP</a></li> <li><a href="/w/index.php?title=Cibacron_blue&action=edit&redlink=1" class="new" title="Cibacron blue (page does not exist)">Cibacron blue</a></li> <li><a href="/wiki/Cytidine_triphosphate" title="Cytidine triphosphate">CTP</a></li> <li><a href="/w/index.php?title=D-%CE%B2,%CE%B3-Me-ATP&action=edit&redlink=1" class="new" title="D-β,γ-Me-ATP (page does not exist)">D-β,γ-Me-ATP</a></li> <li><a href="/wiki/Guanosine_triphosphate" title="Guanosine triphosphate">GTP</a></li> <li><a href="/w/index.php?title=HT-AMP&action=edit&redlink=1" class="new" title="HT-AMP (page does not exist)">HT-AMP</a></li> <li><a href="/wiki/Ivermectin" title="Ivermectin">Ivermectin</a></li> <li><a href="/w/index.php?title=L-%CE%B2,%CE%B3-Me-ATP&action=edit&redlink=1" class="new" title="L-β,γ-Me-ATP (page does not exist)">L-β,γ-Me-ATP</a></li> <li><a href="/w/index.php?title=MRS-2219&action=edit&redlink=1" class="new" title="MRS-2219 (page does not exist)">MRS-2219</a></li> <li><a href="/w/index.php?title=PAPET-ATP&action=edit&redlink=1" class="new" title="PAPET-ATP (page does not exist)">PAPET-ATP</a></li> <li><a href="/wiki/Uridine_triphosphate" title="Uridine triphosphate">UTP</a></li> <li><a href="/wiki/Zinc" title="Zinc">Zinc</a></li></ul> <ul><li><b>Antagonists:</b> <a href="/w/index.php?title=5-BDBD&action=edit&redlink=1" class="new" title="5-BDBD (page does not exist)">5-BDBD</a></li> <li><a href="/w/index.php?title=A-317491&action=edit&redlink=1" class="new" title="A-317491 (page does not exist)">A-317491</a></li> <li><a href="/w/index.php?title=A-438079&action=edit&redlink=1" class="new" title="A-438079 (page does not exist)">A-438079</a></li> <li><a href="/w/index.php?title=A-740003&action=edit&redlink=1" class="new" title="A-740003 (page does not exist)">A-740003</a></li> <li><a href="/w/index.php?title=A-804598&action=edit&redlink=1" class="new" title="A-804598 (page does not exist)">A-804598</a></li> <li><a href="/w/index.php?title=A-839977&action=edit&redlink=1" class="new" title="A-839977 (page does not exist)">A-839977</a></li> <li><a href="/wiki/AF-353" title="AF-353">AF-353</a></li> <li><a href="/w/index.php?title=AZ-10606120&action=edit&redlink=1" class="new" title="AZ-10606120 (page does not exist)">AZ-10606120</a></li> <li><a href="/w/index.php?title=AZ-11645373&action=edit&redlink=1" class="new" title="AZ-11645373 (page does not exist)">AZ-11645373</a></li> <li><a href="/wiki/Brilliant_Blue_G" class="mw-redirect" title="Brilliant Blue G">BBG</a></li> <li><a href="/wiki/Calcium" title="Calcium">Calcium</a></li> <li><a href="/w/index.php?title=Calmidazolium&action=edit&redlink=1" class="new" title="Calmidazolium (page does not exist)">Calmidazolium</a></li> <li><a href="/wiki/Chelerythrine" title="Chelerythrine">Chelerythrine</a></li> <li><a href="/wiki/Copper" title="Copper">Copper</a></li> <li><a href="/wiki/Emodin" title="Emodin">Emodin</a> (<i><a href="/wiki/Rheum_officinale" title="Rheum officinale">Rheum officinale</a></i>)</li> <li><a href="/wiki/Evans_blue_(dye)" title="Evans blue (dye)">Evans blue</a></li> <li><a href="/wiki/Gefapixant" title="Gefapixant">Gefapixant</a></li> <li><a href="/w/index.php?title=GW-791343&action=edit&redlink=1" class="new" title="GW-791343 (page does not exist)">GW-791343</a></li> <li><a href="/w/index.php?title=5-(N,N-Hexamethylene)amiloride&action=edit&redlink=1" class="new" title="5-(N,N-Hexamethylene)amiloride (page does not exist)">HMA</a></li> <li><a href="/w/index.php?title=Diinosine_pentaphosphate&action=edit&redlink=1" class="new" title="Diinosine pentaphosphate (page does not exist)">Ip5I</a></li> <li><a href="/w/index.php?title=IsoPPADS&action=edit&redlink=1" class="new" title="IsoPPADS (page does not exist)">isoPPADS</a></li> <li><a href="/w/index.php?title=JNJ-47965567&action=edit&redlink=1" class="new" title="JNJ-47965567 (page does not exist)">JNJ-47965567</a></li> <li><a href="/w/index.php?title=KN-04&action=edit&redlink=1" class="new" title="KN-04 (page does not exist)">KN-04</a></li> <li><a href="/wiki/KN-62" title="KN-62">KN-62</a></li> <li><a href="/wiki/Magnesium" title="Magnesium">Magnesium</a></li> <li><a href="/w/index.php?title=MRS-2159&action=edit&redlink=1" class="new" title="MRS-2159 (page does not exist)">MRS-2159</a></li> <li><a href="/w/index.php?title=NF-023&action=edit&redlink=1" class="new" title="NF-023 (page does not exist)">NF-023</a></li> <li><a href="/w/index.php?title=NF-110&action=edit&redlink=1" class="new" title="NF-110 (page does not exist)">NF-110</a></li> <li><a href="/w/index.php?title=NF-157&action=edit&redlink=1" class="new" title="NF-157 (page does not exist)">NF-157</a></li> <li><a href="/w/index.php?title=NF-279&action=edit&redlink=1" class="new" title="NF-279 (page does not exist)">NF-279</a></li> <li><a href="/w/index.php?title=NF-449&action=edit&redlink=1" class="new" title="NF-449 (page does not exist)">NF-449</a></li> <li><a href="/wiki/Opiranserin" title="Opiranserin">Opiranserin (VVZ-149)</a></li> <li><a href="/w/index.php?title=Oxidized-ATP&action=edit&redlink=1" class="new" title="Oxidized-ATP (page does not exist)">Oxidized-ATP</a></li> <li><a href="/wiki/Phenol_Red" class="mw-redirect" title="Phenol Red">Phenol Red</a></li> <li><a href="/wiki/Phenolphthalein" title="Phenolphthalein">Phenolphthalein</a></li> <li><a href="/wiki/PPADS" title="PPADS">PPADS</a></li> <li><a href="/w/index.php?title=PPNDS&action=edit&redlink=1" class="new" title="PPNDS (page does not exist)">PPNDS</a></li> <li><a href="/w/index.php?title=PSB-12062&action=edit&redlink=1" class="new" title="PSB-12062 (page does not exist)">PSB-12062</a></li> <li><a href="/wiki/Puerarin" title="Puerarin">Puerarin</a> (<i><a href="/wiki/Radix_puerariae" class="mw-redirect" title="Radix puerariae">Radix puerariae</a></i>)</li> <li><a href="/w/index.php?title=Purotoxin_1&action=edit&redlink=1" class="new" title="Purotoxin 1 (page does not exist)">Purotoxin 1</a></li> <li><a href="/w/index.php?title=Reactive_Blue_2&action=edit&redlink=1" class="new" title="Reactive Blue 2 (page does not exist)">RB-2</a></li> <li><a href="/w/index.php?title=Ro_0437626&action=edit&redlink=1" class="new" title="Ro 0437626 (page does not exist)">Ro 0437626</a></li> <li><a href="/w/index.php?title=Ro_51&action=edit&redlink=1" class="new" title="Ro 51 (page does not exist)">Ro 51</a></li> <li><a href="/w/index.php?title=RO-3&action=edit&redlink=1" class="new" title="RO-3 (page does not exist)">RO-3</a></li> <li><a href="/wiki/Sodium_ferulate" title="Sodium ferulate">Sodium ferulate</a> (<i><a href="/wiki/Angelica_sinensis" title="Angelica sinensis">Angelica sinensis</a></i>, <i><a href="/wiki/Ligusticum_wallichii" class="mw-redirect" title="Ligusticum wallichii">Ligusticum wallichii</a></i>)</li> <li><a href="/wiki/Suramin" title="Suramin">Suramin</a></li> <li><a href="/w/index.php?title=TC-P_262&action=edit&redlink=1" class="new" title="TC-P 262 (page does not exist)">TC-P 262</a></li> <li><a href="/wiki/Tetramethylpyrazine" title="Tetramethylpyrazine">Tetramethylpyrazine (ligustrazine)</a> (<i><a href="/wiki/Ligusticum_wallichii" class="mw-redirect" title="Ligusticum wallichii">Ligusticum wallichii</a></i>)</li> <li><a href="/wiki/TNP-ATP" title="TNP-ATP">TNP-ATP</a></li> <li><a href="/wiki/Zinc" title="Zinc">Zinc</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:3em;;text-align:center;"><a href="/wiki/P2Y_receptor" title="P2Y receptor">P2Y</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><b>Agonists:</b> <a href="/w/index.php?title=2-Methylthioladenosine_diphosphate&action=edit&redlink=1" class="new" title="2-Methylthioladenosine diphosphate (page does not exist)">2-Me-SADP</a></li> <li><a href="/w/index.php?title=2-Methylthioadenosine_triphosphate&action=edit&redlink=1" class="new" title="2-Methylthioadenosine triphosphate (page does not exist)">2-Me-SATP</a></li> <li><a href="/w/index.php?title=2-Thio-UTP&action=edit&redlink=1" class="new" title="2-Thio-UTP (page does not exist)">2-Thio-UTP</a></li> <li><a href="/w/index.php?title=5-Bromouridine_5%E2%80%B2-diphosphate&action=edit&redlink=1" class="new" title="5-Bromouridine 5′-diphosphate (page does not exist)">5-Br-UDP</a></li> <li><a href="/w/index.php?title=5-OMe-UDP&action=edit&redlink=1" class="new" title="5-OMe-UDP (page does not exist)">5-OMe-UDP</a></li> <li><a href="/w/index.php?title=%CE%91,%CE%B2-Methylene-ATP&action=edit&redlink=1" class="new" title="Α,β-Methylene-ATP (page does not exist)">α,β-Me-ATP</a></li> <li><a href="/wiki/Adenosine" title="Adenosine">Adenosine</a></li> <li><a href="/wiki/Adenosine_diphosphate" title="Adenosine diphosphate">ADP</a></li> <li><a href="/w/index.php?title=Adenosine-5%27-(%CE%B2-thio)-diphosphate&action=edit&redlink=1" class="new" title="Adenosine-5'-(β-thio)-diphosphate (page does not exist)">ADPβS</a></li> <li><a href="/w/index.php?title=Diadenosine_triphosphate&action=edit&redlink=1" class="new" title="Diadenosine triphosphate (page does not exist)">Ap3A</a></li> <li><a href="/w/index.php?title=AR-C_67085MX&action=edit&redlink=1" class="new" title="AR-C 67085MX (page does not exist)">AR-C 67085MX</a></li> <li><a href="/wiki/Adenosine_triphosphate" title="Adenosine triphosphate">ATP</a></li> <li><a href="/w/index.php?title=Adenosine-5%27-(%CE%B3-thio)-triphosphate&action=edit&redlink=1" class="new" title="Adenosine-5'-(γ-thio)-triphosphate (page does not exist)">ATPγS</a></li> <li><a href="/wiki/Cytidine_triphosphate" title="Cytidine triphosphate">CTP</a></li> <li><a href="/wiki/Deoxyadenosine_triphosphate" title="Deoxyadenosine triphosphate">dATP</a></li> <li><a href="/wiki/Denufosol" title="Denufosol">Denufosol</a></li> <li><a href="/wiki/Diquafosol" title="Diquafosol">Diquafosol</a></li> <li><a href="/w/index.php?title=Inosine_diphosphate&action=edit&redlink=1" class="new" title="Inosine diphosphate (page does not exist)">IDP</a></li> <li><a href="/wiki/Inosine_triphosphate" title="Inosine triphosphate">ITP</a></li> <li><a href="/wiki/INS-365" class="mw-redirect" title="INS-365">INS-365</a></li> <li><a href="/w/index.php?title=INS-37217&action=edit&redlink=1" class="new" title="INS-37217 (page does not exist)">INS-37217</a></li> <li><a href="/w/index.php?title=MRS-2365&action=edit&redlink=1" class="new" title="MRS-2365 (page does not exist)">MRS-2365</a></li> <li><a href="/w/index.php?title=MRS-2690&action=edit&redlink=1" class="new" title="MRS-2690 (page does not exist)">MRS-2690</a></li> <li><a href="/w/index.php?title=MRS-2693&action=edit&redlink=1" class="new" title="MRS-2693 (page does not exist)">MRS-2693</a></li> <li><a href="/w/index.php?title=MRS-2768&action=edit&redlink=1" class="new" title="MRS-2768 (page does not exist)">MRS-2768</a></li> <li><a href="/w/index.php?title=MRS-2957&action=edit&redlink=1" class="new" title="MRS-2957 (page does not exist)">MRS-2957</a></li> <li><a href="/w/index.php?title=MRS-4062&action=edit&redlink=1" class="new" title="MRS-4062 (page does not exist)">MRS-4062</a></li> <li><a href="/w/index.php?title=NF-546&action=edit&redlink=1" class="new" title="NF-546 (page does not exist)">NF-546</a></li> <li><a href="/w/index.php?title=PAPET-ATP&action=edit&redlink=1" class="new" title="PAPET-ATP (page does not exist)">PAPET-ATP</a></li> <li><a href="/w/index.php?title=PSB-0474&action=edit&redlink=1" class="new" title="PSB-0474 (page does not exist)">PSB-0474</a></li> <li><a href="/w/index.php?title=PSB-1114&action=edit&redlink=1" class="new" title="PSB-1114 (page does not exist)">PSB-1114</a></li> <li><a href="/wiki/Uridine_diphosphate" title="Uridine diphosphate">UDP</a></li> <li><a href="/w/index.php?title=Uridine_5%C2%B4-(%CE%B2-thio)-diphosphate&action=edit&redlink=1" class="new" title="Uridine 5´-(β-thio)-diphosphate (page does not exist)">UDPβS</a></li> <li><a href="/wiki/Uridine_diphosphate_galactose" title="Uridine diphosphate galactose">UDP-galactose</a></li> <li><a href="/wiki/Uridine_diphosphate_glucose" title="Uridine diphosphate glucose">UDP-glucose</a></li> <li><a href="/wiki/Uridine_diphosphate_N-acetylglucosamine" title="Uridine diphosphate N-acetylglucosamine">UDP-N-acetylglucosamine</a></li> <li><a href="/w/index.php?title=Diuridine_triphosphate&action=edit&redlink=1" class="new" title="Diuridine triphosphate (page does not exist)">Up3U</a></li> <li><a href="/wiki/Uridine_triphosphate" title="Uridine triphosphate">UTP</a></li> <li><a href="/w/index.php?title=Uridine-5%27-(%CE%B3-thio)-triphosphate&action=edit&redlink=1" class="new" title="Uridine-5'-(γ-thio)-triphosphate (page does not exist)">UTPγS</a></li></ul> <ul><li><b>Antagonists:</b> <a href="/w/index.php?title=2-Methylthioladenosine_monophosphate&action=edit&redlink=1" class="new" title="2-Methylthioladenosine monophosphate (page does not exist)">2-Me-SAMP</a></li> <li><a href="/w/index.php?title=A3P5PS&action=edit&redlink=1" class="new" title="A3P5PS (page does not exist)">A3P5PS</a></li> <li><a href="/w/index.php?title=AMP%CE%B1S&action=edit&redlink=1" class="new" title="AMPαS (page does not exist)">AMPαS</a></li> <li><a href="/wiki/Diadenosine_tetraphosphate" class="mw-redirect" title="Diadenosine tetraphosphate">Ap4A</a></li> <li><a href="/w/index.php?title=AR-C_66096&action=edit&redlink=1" class="new" title="AR-C 66096 (page does not exist)">AR-C 66096</a></li> <li><a href="/w/index.php?title=AR-C_67085MX&action=edit&redlink=1" class="new" title="AR-C 67085MX (page does not exist)">AR-C 67085MX</a></li> <li><a href="/w/index.php?title=AR-C_69931MX&action=edit&redlink=1" class="new" title="AR-C 69931MX (page does not exist)">AR-C 69931MX</a></li> <li><a href="/w/index.php?title=AR-C_118925XX&action=edit&redlink=1" class="new" title="AR-C 118925XX (page does not exist)">AR-C 118925XX</a></li> <li><a href="/wiki/Adenosine_triphosphate" title="Adenosine triphosphate">ATP</a></li> <li><a href="/w/index.php?title=BzATP&action=edit&redlink=1" class="new" title="BzATP (page does not exist)">BzATP</a></li> <li><a href="/w/index.php?title=C1330-7&action=edit&redlink=1" class="new" title="C1330-7 (page does not exist)">C1330-7</a></li> <li><a href="/wiki/Cangrelor" title="Cangrelor">Cangrelor</a></li> <li><a href="/wiki/Clopidogrel" title="Clopidogrel">Clopidogrel</a></li> <li><a href="/wiki/Elinogrel" title="Elinogrel">Elinogrel</a></li> <li><a href="/w/index.php?title=Diinosine_pentaphosphate&action=edit&redlink=1" class="new" title="Diinosine pentaphosphate (page does not exist)">Ip5I</a></li> <li><a href="/w/index.php?title=MRS-2179&action=edit&redlink=1" class="new" title="MRS-2179 (page does not exist)">MRS-2179</a></li> <li><a href="/w/index.php?title=MRS-2211&action=edit&redlink=1" class="new" title="MRS-2211 (page does not exist)">MRS-2211</a></li> <li><a href="/w/index.php?title=MRS-2279&action=edit&redlink=1" class="new" title="MRS-2279 (page does not exist)">MRS-2279</a></li> <li><a href="/w/index.php?title=MRS-2395&action=edit&redlink=1" class="new" title="MRS-2395 (page does not exist)">MRS-2395</a></li> <li><a href="/w/index.php?title=MRS-2500&action=edit&redlink=1" class="new" title="MRS-2500 (page does not exist)">MRS-2500</a></li> <li><a href="/w/index.php?title=MRS-2578&action=edit&redlink=1" class="new" title="MRS-2578 (page does not exist)">MRS-2578</a></li> <li><a href="/w/index.php?title=NF-157&action=edit&redlink=1" class="new" title="NF-157 (page does not exist)">NF-157</a></li> <li><a href="/w/index.php?title=NF-340&action=edit&redlink=1" class="new" title="NF-340 (page does not exist)">NF-340</a></li> <li><a href="/w/index.php?title=2,2%27-Pyridylisatogen_tosylate&action=edit&redlink=1" class="new" title="2,2'-Pyridylisatogen tosylate (page does not exist)">PIT</a></li> <li><a href="/wiki/PPADS" title="PPADS">PPADS</a></li> <li><a href="/wiki/Prasugrel" title="Prasugrel">Prasugrel</a></li> <li><a href="/w/index.php?title=PSB-0739&action=edit&redlink=1" class="new" title="PSB-0739 (page does not exist)">PSB-0739</a></li> <li><a href="/w/index.php?title=Reactive_Blue_2&action=edit&redlink=1" class="new" title="Reactive Blue 2 (page does not exist)">RB-2</a></li> <li><a href="/wiki/Regrelor" title="Regrelor">Regrelor</a></li> <li><a href="/wiki/Suramin" title="Suramin">Suramin</a></li> <li><a href="/wiki/Ticagrelor" title="Ticagrelor">Ticagrelor</a></li> <li><a href="/wiki/Ticlopidine" title="Ticlopidine">Ticlopidine</a></li> <li><a href="/wiki/Uridine_diphosphate" title="Uridine diphosphate">UDP</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Membrane_transport_protein" title="Membrane transport protein">Transporter</a><br /><small>(<a href="/wiki/Reuptake_inhibitor" title="Reuptake inhibitor">blockers</a>)</small></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:6em;;text-align:center;"><a href="/wiki/Concentrative_nucleoside_transporters" class="mw-redirect" title="Concentrative nucleoside transporters"><abbr title="Concentrative nucleoside transporters">CNTs</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 Concentrative nucleoside transporters</span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/w/index.php?title=6-Hydroxy-7-methoxyflavone&action=edit&redlink=1" class="new" title="6-Hydroxy-7-methoxyflavone (page does not exist)">6-Hydroxy-7-methoxyflavone</a></li> <li><a href="/wiki/Adenosine" title="Adenosine">Adenosine</a></li> <li><a href="/w/index.php?title=DMeThPmR&action=edit&redlink=1" class="new" title="DMeThPmR (page does not exist)">dMeThPmR</a></li> <li><a href="/wiki/Estradiol" title="Estradiol">Estradiol</a></li> <li><a href="/w/index.php?title=KGO-2142&action=edit&redlink=1" class="new" title="KGO-2142 (page does not exist)">KGO-2142</a></li> <li><a href="/w/index.php?title=KGO-2173&action=edit&redlink=1" class="new" title="KGO-2173 (page does not exist)">KGO-2173</a></li> <li><a href="/w/index.php?title=MeThPmR&action=edit&redlink=1" class="new" title="MeThPmR (page does not exist)">MeThPmR</a></li> <li><a href="/wiki/Phloridzin" class="mw-redirect" title="Phloridzin">Phloridzin</a></li> <li><a href="/wiki/Progesterone" title="Progesterone">Progesterone</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:6em;;text-align:center;"><a href="/wiki/Equilibrative_nucleoside_transporters" class="mw-redirect" title="Equilibrative nucleoside transporters"><abbr title="Equilibrative nucleoside transporters">ENTs</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 Equilibrative nucleoside transporters</span></th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Barbiturate" title="Barbiturate">Barbiturates</a></li> <li><a href="/wiki/Benzodiazepine" title="Benzodiazepine">Benzodiazepines</a></li> <li><a href="/wiki/Cilostazol" title="Cilostazol">Cilostazol</a></li> <li><a href="/wiki/Dilazep" title="Dilazep">Dilazep</a></li> <li><a href="/wiki/Dipyridamole" title="Dipyridamole">Dipyridamole</a></li> <li><a href="/wiki/Estradiol" title="Estradiol">Estradiol</a></li> <li><a href="/wiki/Ethanol" title="Ethanol">Ethanol</a></li> <li><a href="/wiki/Hexobendine" title="Hexobendine">Hexobendine</a></li> <li><a href="/w/index.php?title=6-S-((4-Nitrophenyl)methyl)-6-thioinosine&action=edit&redlink=1" class="new" title="6-S-((4-Nitrophenyl)methyl)-6-thioinosine (page does not exist)">NBMPR</a></li> <li><a href="/wiki/Pentoxifylline" title="Pentoxifylline">Pentoxifylline</a></li> <li><a href="/wiki/Progesterone" title="Progesterone">Progesterone</a></li> <li><a href="/wiki/Propentofylline" title="Propentofylline">Propentofylline</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:6em;;text-align:center;"><a href="/wiki/Plasma_membrane_monoamine_transporter" title="Plasma membrane monoamine transporter"><abbr title="Plasma membrane monoamine transporter">PMAT</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 Plasma membrane monoamine transporter</span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Decynium-22" title="Decynium-22">Decynium-22</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/Enzyme" title="Enzyme">Enzyme</a><br /><small>(<a href="/wiki/Enzyme_inhibitor" title="Enzyme inhibitor">inhibitors</a>)</small></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:6em;;text-align:center;"><a href="/wiki/Xanthine_oxidase" title="Xanthine oxidase"><abbr title="Xanthine oxidase">XO</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 Xanthine oxidase</span></th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Allopurinol" title="Allopurinol">Allopurinol</a></li> <li><a href="/wiki/Amflutizole" title="Amflutizole">Amflutizole</a></li> <li><a href="/wiki/Benzbromarone" title="Benzbromarone">Benzbromarone</a></li> <li><a href="/wiki/Caffeic_acid" title="Caffeic acid">Caffeic acid</a></li> <li><a href="/wiki/Cinnamaldehyde" title="Cinnamaldehyde">Cinnamaldehyde</a></li> <li><i><a href="/wiki/Cinnamomum_osmophloeum" title="Cinnamomum osmophloeum">Cinnamomum osmophloeum</a></i></li> <li><a href="/wiki/Febuxostat" title="Febuxostat">Febuxostat</a></li> <li><a href="/wiki/Myo-inositol" class="mw-redirect" title="Myo-inositol">Myo-inositol</a></li> <li><a href="/wiki/Kaempferol" title="Kaempferol">Kaempferol</a></li> <li><a href="/wiki/Myricetin" title="Myricetin">Myricetin</a></li> <li><a href="/w/index.php?title=Niraxostat&action=edit&redlink=1" class="new" title="Niraxostat (page does not exist)">Niraxostat</a></li> <li><a href="/wiki/Oxipurinol" title="Oxipurinol">Oxipurinol</a></li> <li><a href="/wiki/Phytic_acid" title="Phytic acid">Phytic acid</a></li> <li><i><a href="/wiki/Pistacia_integerrima" title="Pistacia integerrima">Pistacia integerrima</a></i></li> <li><a href="/wiki/Propolis" title="Propolis">Propolis</a></li> <li><a href="/wiki/Quercetin" title="Quercetin">Quercetin</a></li> <li><a href="/wiki/Tisopurine" title="Tisopurine">Tisopurine</a></li> <li><a href="/wiki/Topiroxostat" title="Topiroxostat">Topiroxostat</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:6em;;text-align:center;">Others</th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Aminopterin" title="Aminopterin">Aminopterin</a></li> <li><a href="/wiki/Azathioprine" title="Azathioprine">Azathioprine</a></li> <li><a href="/wiki/Methotrexate" title="Methotrexate">Methotrexate</a></li> <li><a href="/wiki/Mycophenolic_acid" title="Mycophenolic acid">Mycophenolic acid</a></li> <li><a href="/wiki/Pemetrexed" title="Pemetrexed">Pemetrexed</a></li> <li><a href="/wiki/Pralatrexate" title="Pralatrexate">Pralatrexate</a></li> <li><i>Many others</i></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;">Others</th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><b>Precursors:</b> <a href="/wiki/Adenine" title="Adenine">Adenine</a></li> <li><a href="/wiki/Adenosine" title="Adenosine">Adenosine</a></li> <li><a href="/wiki/Adenosine_monophosphate" title="Adenosine monophosphate">AMP</a></li> <li><a href="/wiki/Adenosine_diphosphate" title="Adenosine diphosphate">ADP</a></li> <li><a href="/wiki/Adenosine_triphosphate" title="Adenosine triphosphate">ATP</a></li> <li><a href="/wiki/Cytosine" title="Cytosine">Cytosine</a></li> <li><a href="/wiki/Cytidine" title="Cytidine">Cytidine</a></li> <li><a href="/wiki/Cytidine_monophosphate" title="Cytidine monophosphate">CMP</a></li> <li><a href="/wiki/Cytidine_diphosphate" title="Cytidine diphosphate">CDP</a></li> <li><a href="/wiki/Cytidine_triphosphate" title="Cytidine triphosphate">CTP</a></li> <li><a href="/wiki/Guanine" title="Guanine">Guanine</a></li> <li><a href="/wiki/Guanosine" title="Guanosine">Guanosine</a></li> <li><a href="/wiki/Guanosine_monophosphate" title="Guanosine monophosphate">GMP</a></li> <li><a href="/wiki/Guanosine_diphosphate" title="Guanosine diphosphate">GDP</a></li> <li><a href="/wiki/Guanosine_triphosphate" title="Guanosine triphosphate">GTP</a></li> <li><a href="/wiki/Hypoxanthine" title="Hypoxanthine">Hypoxanthine</a></li> <li><a href="/wiki/Inosine" title="Inosine">Inosine</a></li> <li><a href="/wiki/Inosine_monophosphate" class="mw-redirect" title="Inosine monophosphate">IMP</a></li> <li><a href="/w/index.php?title=Inosine_diphosphate&action=edit&redlink=1" class="new" title="Inosine diphosphate (page does not exist)">IDP</a></li> <li><a href="/wiki/Inosine_triphosphate" title="Inosine triphosphate">ITP</a></li> <li><a href="/wiki/Ribose" title="Ribose">Ribose</a></li> <li><a href="/wiki/Uracil" title="Uracil">Uracil</a></li> <li><a href="/wiki/Uridine" title="Uridine">Uridine</a></li> <li><a href="/wiki/Uridine_monophosphate" title="Uridine monophosphate">UMP</a></li> <li><a href="/wiki/Uridine_diphosphate" title="Uridine diphosphate">UDP</a></li> <li><a href="/wiki/Uridine_triphosphate" title="Uridine triphosphate">UTP</a></li></ul> <ul><li><b>Others:</b> <a href="/wiki/Chrysophanol" title="Chrysophanol">Chrysophanol</a> (<a href="/wiki/Rhubarb" title="Rhubarb">rhubarb</a>)</li></ul> </div></td></tr><tr><td class="navbox-abovebelow" colspan="2"><div><i><b>See also:</b> <a href="/wiki/Template:Receptor_modulators" title="Template:Receptor modulators">Receptor/signaling modulators</a></i></div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"><style data-mw-deduplicate="TemplateStyles:r1038841319">.mw-parser-output .tooltip-dotted{border-bottom:1px dotted;cursor:help}</style></div><div role="navigation" class="navbox authority-control" aria-label="Navbox" style="padding:3px"><table class="nowraplinks hlist navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Help:Authority_control" title="Help:Authority control">Authority control databases</a>: National <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q188261#identifiers" title="Edit this at Wikidata"><img alt="Edit this at Wikidata" src="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/10px-OOjs_UI_icon_edit-ltr-progressive.svg.png" decoding="async" width="10" height="10" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/15px-OOjs_UI_icon_edit-ltr-progressive.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/20px-OOjs_UI_icon_edit-ltr-progressive.svg.png 2x" data-file-width="20" data-file-height="20" /></a></span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"><ul><li><span class="uid"><a rel="nofollow" class="external text" href="https://id.ndl.go.jp/auth/ndlna/00569220">Japan</a></span></li><li><span class="uid"><span class="rt-commentedText tooltip tooltip-dotted" title="puriny"><a rel="nofollow" class="external text" href="https://aleph.nkp.cz/F/?func=find-c&local_base=aut&ccl_term=ica=ph390000&CON_LNG=ENG">Czech Republic</a></span></span></li></ul></div></td></tr></tbody></table></div>    </div><noscript><img src="https://login.wikimedia.org/wiki/Special:CentralAutoLogin/start?type=1x1" alt="" width="1" height="1" style="border: none; position: absolute;"></noscript> <div class="printfooter" data-nosnippet="">Retrieved from "<a dir="ltr" href="https://en.wikipedia.org/w/index.php?title=Purine&oldid=1251551236">https://en.wikipedia.org/w/index.php?title=Purine&oldid=1251551236</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:Purines" title="Category:Purines">Purines</a></li><li><a href="/wiki/Category:Simple_aromatic_rings" title="Category:Simple aromatic rings">Simple aromatic rings</a></li><li><a href="/wiki/Category:1898_in_science" title="Category:1898 in science">1898 in science</a></li><li><a href="/wiki/Category:Emil_Fischer" title="Category:Emil Fischer">Emil Fischer</a></li><li><a href="/wiki/Category:Substances_discovered_in_the_19th_century" title="Category:Substances discovered in the 19th century">Substances discovered in the 19th century</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:CS1:_long_volume_value" title="Category:CS1: long volume value">CS1: long volume value</a></li><li><a href="/wiki/Category:Webarchive_template_wayback_links" title="Category:Webarchive template wayback links">Webarchive template wayback links</a></li><li><a href="/wiki/Category:Articles_with_short_description" title="Category:Articles with short description">Articles with short description</a></li><li><a href="/wiki/Category:Short_description_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:ECHA_InfoCard_ID_from_Wikidata" title="Category:ECHA InfoCard ID from Wikidata">ECHA InfoCard ID from Wikidata</a></li><li><a href="/wiki/Category:Articles_containing_unverified_chemical_infoboxes" title="Category:Articles containing unverified chemical infoboxes">Articles containing unverified chemical infoboxes</a></li><li><a href="/wiki/Category:Chembox_image_size_set" title="Category:Chembox image size set">Chembox image size set</a></li><li><a href="/wiki/Category:Short_description_matches_Wikidata" title="Category:Short description matches Wikidata">Short description matches Wikidata</a></li></ul></div></div> </div> </main> </div> <div class="mw-footer-container"> <footer id="footer" class="mw-footer" > <ul id="footer-info"> <li id="footer-info-lastmod"> This page was last edited on 16 October 2024, at 18:55<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=Purine&mobileaction=toggle_view_mobile" class="noprint stopMobileRedirectToggle">Mobile view</a></li> </ul> <ul id="footer-icons" class="noprint"> <li id="footer-copyrightico"><a href="https://wikimediafoundation.org/" class="cdx-button cdx-button--fake-button cdx-button--size-large cdx-button--fake-button--enabled"><img src="/static/images/footer/wikimedia-button.svg" width="84" height="29" alt="Wikimedia Foundation" loading="lazy"></a></li> <li id="footer-poweredbyico"><a href="https://www.mediawiki.org/" class="cdx-button cdx-button--fake-button cdx-button--size-large cdx-button--fake-button--enabled"><img src="/w/resources/assets/poweredby_mediawiki.svg" alt="Powered by MediaWiki" width="88" height="31" loading="lazy"></a></li> </ul> </footer> </div> </div> </div> <div class="vector-settings" id="p-dock-bottom"> <ul></ul> </div><script>(RLQ=window.RLQ||[]).push(function(){mw.config.set({"wgHostname":"mw-web.codfw.main-f69cdc8f6-mkx9z","wgBackendResponseTime":143,"wgPageParseReport":{"limitreport":{"cputime":"1.202","walltime":"1.485","ppvisitednodes":{"value":9341,"limit":1000000},"postexpandincludesize":{"value":212526,"limit":2097152},"templateargumentsize":{"value":24728,"limit":2097152},"expansiondepth":{"value":25,"limit":100},"expensivefunctioncount":{"value":4,"limit":500},"unstrip-depth":{"value":1,"limit":20},"unstrip-size":{"value":129897,"limit":5000000},"entityaccesscount":{"value":1,"limit":400},"timingprofile":["100.00% 1248.765 1 -total"," 42.11% 525.844 1 Template:Chembox"," 29.69% 370.800 1 Template:Reflist"," 24.00% 299.688 1 Template:Chembox_Identifiers"," 19.97% 249.327 19 Template:Cite_journal"," 12.93% 161.414 3 Template:Chembox_headerbar"," 12.92% 161.296 10 Template:Trim"," 10.15% 126.803 13 Template:Main_other"," 10.14% 126.623 5 Template:Navbox"," 9.88% 123.371 1 Template:Nucleobases,_nucleosides,_and_nucleotides"]},"scribunto":{"limitreport-timeusage":{"value":"0.610","limit":"10.000"},"limitreport-memusage":{"value":9893093,"limit":52428800}},"cachereport":{"origin":"mw-web.codfw.main-f69cdc8f6-rlhbk","timestamp":"20241122142505","ttl":2592000,"transientcontent":false}}});});</script> <script type="application/ld+json">{"@context":"https:\/\/schema.org","@type":"Article","name":"Purine","url":"https:\/\/en.wikipedia.org\/wiki\/Purine","sameAs":"http:\/\/www.wikidata.org\/entity\/Q188261","mainEntity":"http:\/\/www.wikidata.org\/entity\/Q188261","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":"2001-07-30T16:38:33Z","dateModified":"2024-10-16T18:55:18Z","image":"https:\/\/upload.wikimedia.org\/wikipedia\/commons\/d\/d6\/Purin_num2.svg","headline":"chemical compound"}</script> </body> </html>