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>Pentaerythritol tetranitrate - 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":"29c67c3f-f2f4-4233-9fc4-5b9f2ca4b079","wgCanonicalNamespace":"","wgCanonicalSpecialPageName":false,"wgNamespaceNumber":0,"wgPageName":"Pentaerythritol_tetranitrate","wgTitle":"Pentaerythritol tetranitrate","wgCurRevisionId":1251608019,"wgRevisionId":1251608019,"wgArticleId":42451,"wgIsArticle":true,"wgIsRedirect":false,"wgAction":"view","wgUserName":null,"wgUserGroups":["*"],"wgCategories":["Webarchive template wayback links","CS1 maint: multiple names: authors list","Articles with short description","Short description matches Wikidata","Wikipedia extended-confirmed-protected pages","Use mdy dates from November 2015","Articles without KEGG source","ECHA InfoCard ID from Wikidata","Chembox having GHS data","Articles containing unverified chemical infoboxes","Chembox image size set","Short description is different from Wikidata", "All articles with unsourced statements","Articles with unsourced statements from September 2024","Articles with unsourced statements from November 2010","Articles with unsourced statements from September 2016","Wikipedia articles needing clarification from September 2016","Commons category link is on Wikidata","Antianginals","Explosive chemicals","German inventions","Nitrate esters"],"wgPageViewLanguage":"en","wgPageContentLanguage":"en","wgPageContentModel":"wikitext","wgRelevantPageName":"Pentaerythritol_tetranitrate","wgRelevantArticleId":42451,"wgIsProbablyEditable":false,"wgRelevantPageIsProbablyEditable":false,"wgRestrictionEdit":["extendedconfirmed"],"wgRestrictionMove":["extendedconfirmed"],"wgRedirectedFrom":"Pentaerithrityl_tetranitrate","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":40000,"wgInternalRedirectTargetUrl":"/wiki/Pentaerythritol_tetranitrate","wgRelatedArticlesCompat":[],"wgCentralAuthMobileDomain":false,"wgEditSubmitButtonLabelPublish":true,"wgULSPosition":"interlanguage","wgULSisCompactLinksEnabled":false,"wgVector2022LanguageInHeader":true,"wgULSisLanguageSelectorEmpty":false,"wgWikibaseItemId":"Q189334","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=["mediawiki.action.view.redirect","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/8/88/PETN.svg/1200px-PETN.svg.png"> <meta property="og:image:width" content="1200"> <meta property="og:image:height" content="1023"> <meta property="og:image" content="https://upload.wikimedia.org/wikipedia/commons/thumb/8/88/PETN.svg/800px-PETN.svg.png"> <meta property="og:image:width" content="800"> <meta property="og:image:height" content="682"> <meta property="og:image" content="https://upload.wikimedia.org/wikipedia/commons/thumb/8/88/PETN.svg/640px-PETN.svg.png"> <meta property="og:image:width" content="640"> <meta property="og:image:height" content="546"> <meta name="viewport" content="width=1120"> <meta property="og:title" content="Pentaerythritol tetranitrate - 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/Pentaerythritol_tetranitrate"> <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/Pentaerythritol_tetranitrate"> <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 page-Pentaerythritol_tetranitrate rootpage-Pentaerythritol_tetranitrate 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=Pentaerythritol+tetranitrate" 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=Pentaerythritol+tetranitrate" 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=Pentaerythritol+tetranitrate" 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=Pentaerythritol+tetranitrate" title="You're encouraged to log in; however, it's not mandatory. [o]" accesskey="o"><span class="vector-icon mw-ui-icon-logIn mw-ui-icon-wikimedia-logIn"></span> <span>Log in</span></a></li> </ul> </div> </div> <div id="p-user-menu-anon-editor" class="vector-menu mw-portlet mw-portlet-user-menu-anon-editor" > <div class="vector-menu-heading"> Pages for logged out editors <a href="/wiki/Help:Introduction" aria-label="Learn more about editing"><span>learn more</span></a> </div> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li id="pt-anoncontribs" class="mw-list-item"><a href="/wiki/Special:MyContributions" title="A list of edits made from this IP address [y]" accesskey="y"><span>Contributions</span></a></li><li id="pt-anontalk" class="mw-list-item"><a href="/wiki/Special:MyTalk" title="Discussion about edits from this IP address [n]" accesskey="n"><span>Talk</span></a></li> </ul> </div> </div> </div> </div> </nav> </div> </header> </div> <div class="mw-page-container"> <div class="mw-page-container-inner"> <div class="vector-sitenotice-container"> <div id="siteNotice"></div> </div> <div class="vector-column-start"> <div class="vector-main-menu-container"> <div id="mw-navigation"> <nav id="mw-panel" class="vector-main-menu-landmark" aria-label="Site"> <div id="vector-main-menu-pinned-container" class="vector-pinned-container"> </div> </nav> </div> </div> <div class="vector-sticky-pinned-container"> <nav id="mw-panel-toc" aria-label="Contents" data-event-name="ui.sidebar-toc" class="mw-table-of-contents-container vector-toc-landmark"> <div id="vector-toc-pinned-container" class="vector-pinned-container"> <div id="vector-toc" class="vector-toc vector-pinnable-element"> <div class="vector-pinnable-header vector-toc-pinnable-header vector-pinnable-header-pinned" data-feature-name="toc-pinned" data-pinnable-element-id="vector-toc" > <h2 class="vector-pinnable-header-label">Contents</h2> <button class="vector-pinnable-header-toggle-button vector-pinnable-header-pin-button" data-event-name="pinnable-header.vector-toc.pin">move to sidebar</button> <button class="vector-pinnable-header-toggle-button vector-pinnable-header-unpin-button" data-event-name="pinnable-header.vector-toc.unpin">hide</button> </div> <ul class="vector-toc-contents" id="mw-panel-toc-list"> <li id="toc-mw-content-text" class="vector-toc-list-item vector-toc-level-1"> <a href="#" class="vector-toc-link"> <div class="vector-toc-text">(Top)</div> </a> </li> <li id="toc-History" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#History"> <div class="vector-toc-text"> <span class="vector-toc-numb">1</span> <span>History</span> </div> </a> <ul id="toc-History-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-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">2</span> <span>Properties</span> </div> </a> <ul id="toc-Properties-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Production" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Production"> <div class="vector-toc-text"> <span class="vector-toc-numb">3</span> <span>Production</span> </div> </a> <ul id="toc-Production-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Explosive_use" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Explosive_use"> <div class="vector-toc-text"> <span class="vector-toc-numb">4</span> <span>Explosive use</span> </div> </a> <button aria-controls="toc-Explosive_use-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> <span class="vector-icon mw-ui-icon-wikimedia-expand"></span> <span>Toggle Explosive use subsection</span> </button> <ul id="toc-Explosive_use-sublist" class="vector-toc-list"> <li id="toc-In_mixtures" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#In_mixtures"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.1</span> <span>In mixtures</span> </div> </a> <ul id="toc-In_mixtures-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Terrorist_use" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Terrorist_use"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.2</span> <span>Terrorist use</span> </div> </a> <ul id="toc-Terrorist_use-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Detection" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Detection"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.3</span> <span>Detection</span> </div> </a> <ul id="toc-Detection-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Medical_use" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Medical_use"> <div class="vector-toc-text"> <span class="vector-toc-numb">5</span> <span>Medical use</span> </div> </a> <ul id="toc-Medical_use-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">6</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">7</span> <span>References</span> </div> </a> <ul id="toc-References-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Further_reading" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Further_reading"> <div class="vector-toc-text"> <span class="vector-toc-numb">8</span> <span>Further reading</span> </div> </a> <ul id="toc-Further_reading-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">Pentaerythritol tetranitrate</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 41 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-41" 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">41 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%B1%D8%A8%D8%A7%D8%B9%D9%8A_%D9%86%D8%AA%D8%B1%D8%A7%D8%AA_%D8%AE%D9%85%D8%A7%D8%B3%D9%8A_%D8%A7%D9%8A%D8%B1%D9%8A%D8%AB%D8%B1%D9%8A%D8%AA%D9%88%D9%84" title="رباعي نترات خماسي ايريثريتول – Arabic" lang="ar" hreflang="ar" data-title="رباعي نترات خماسي ايريثريتول" 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%DB%8C%D9%86%D8%AA%D8%B1%DB%8C%D8%AA" title="پینتریت – South Azerbaijani" lang="azb" hreflang="azb" data-title="پینتریت" data-language-autonym="تۆرکجه" data-language-local-name="South Azerbaijani" class="interlanguage-link-target"><span>تۆرکجه</span></a></li><li class="interlanguage-link interwiki-bg mw-list-item"><a href="https://bg.wikipedia.org/wiki/%D0%9F%D0%B5%D0%BD%D1%82%D0%B0%D0%B5%D1%80%D0%B8%D1%82%D1%80%D0%B8%D1%82%D0%BE%D0%BB_%D1%82%D0%B5%D1%82%D1%80%D0%B0%D0%BD%D0%B8%D1%82%D1%80%D0%B0%D1%82" title="Пентаеритритол тетранитрат – Bulgarian" lang="bg" hreflang="bg" data-title="Пентаеритритол тетранитрат" data-language-autonym="Български" data-language-local-name="Bulgarian" class="interlanguage-link-target"><span>Български</span></a></li><li class="interlanguage-link interwiki-ca mw-list-item"><a href="https://ca.wikipedia.org/wiki/Pentaeritritol_tetranitrat" title="Pentaeritritol tetranitrat – Catalan" lang="ca" hreflang="ca" data-title="Pentaeritritol tetranitrat" 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/Pentrit" title="Pentrit – Czech" lang="cs" hreflang="cs" data-title="Pentrit" 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/Pentrit" title="Pentrit – Danish" lang="da" hreflang="da" data-title="Pentrit" 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/Nitropenta" title="Nitropenta – German" lang="de" hreflang="de" data-title="Nitropenta" data-language-autonym="Deutsch" data-language-local-name="German" class="interlanguage-link-target"><span>Deutsch</span></a></li><li class="interlanguage-link interwiki-el mw-list-item"><a href="https://el.wikipedia.org/wiki/PETN" title="PETN – Greek" lang="el" hreflang="el" data-title="PETN" 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/Pent" title="Pent – Spanish" lang="es" hreflang="es" data-title="Pent" 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/PETN" title="PETN – Esperanto" lang="eo" hreflang="eo" data-title="PETN" 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/Pentaeritritol_tetranitrato" title="Pentaeritritol tetranitrato – Basque" lang="eu" hreflang="eu" data-title="Pentaeritritol tetranitrato" 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%DB%8C%D9%86%D8%AA%D8%B1%DB%8C%D8%AA" title="پینتریت – Persian" lang="fa" hreflang="fa" data-title="پینتریت" 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/T%C3%A9tranitrate_de_penta%C3%A9rythritol" title="Tétranitrate de pentaérythritol – French" lang="fr" hreflang="fr" data-title="Tétranitrate de pentaérythritol" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target"><span>Français</span></a></li><li class="interlanguage-link interwiki-ko mw-list-item"><a href="https://ko.wikipedia.org/wiki/PETN" title="PETN – Korean" lang="ko" hreflang="ko" data-title="PETN" data-language-autonym="한국어" data-language-local-name="Korean" class="interlanguage-link-target"><span>한국어</span></a></li><li class="interlanguage-link interwiki-hr mw-list-item"><a href="https://hr.wikipedia.org/wiki/Pentrit" title="Pentrit – Croatian" lang="hr" hreflang="hr" data-title="Pentrit" 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/Pentaeritritol_tetranitrat" title="Pentaeritritol tetranitrat – Indonesian" lang="id" hreflang="id" data-title="Pentaeritritol tetranitrat" 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/Tetranitrato_di_pentaeritrite" title="Tetranitrato di pentaeritrite – Italian" lang="it" hreflang="it" data-title="Tetranitrato di pentaeritrite" 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/PETN" title="PETN – Hebrew" lang="he" hreflang="he" data-title="PETN" data-language-autonym="עברית" data-language-local-name="Hebrew" class="interlanguage-link-target"><span>עברית</span></a></li><li class="interlanguage-link interwiki-kk mw-list-item"><a href="https://kk.wikipedia.org/wiki/%D0%A2%D0%AD%D0%9D" title="ТЭН – Kazakh" lang="kk" hreflang="kk" data-title="ТЭН" data-language-autonym="Қазақша" data-language-local-name="Kazakh" class="interlanguage-link-target"><span>Қазақша</span></a></li><li class="interlanguage-link interwiki-lv mw-list-item"><a href="https://lv.wikipedia.org/wiki/Tetranitropentaeritr%C4%ABts" title="Tetranitropentaeritrīts – Latvian" lang="lv" hreflang="lv" data-title="Tetranitropentaeritrīts" data-language-autonym="Latviešu" data-language-local-name="Latvian" class="interlanguage-link-target"><span>Latviešu</span></a></li><li class="interlanguage-link interwiki-lt mw-list-item"><a href="https://lt.wikipedia.org/wiki/PETN" title="PETN – Lithuanian" lang="lt" hreflang="lt" data-title="PETN" 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/Pentaeritrit-tetranitr%C3%A1t" title="Pentaeritrit-tetranitrát – Hungarian" lang="hu" hreflang="hu" data-title="Pentaeritrit-tetranitrát" data-language-autonym="Magyar" data-language-local-name="Hungarian" class="interlanguage-link-target"><span>Magyar</span></a></li><li class="interlanguage-link interwiki-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/Penta-erytritoltetranitraat" title="Penta-erytritoltetranitraat – Dutch" lang="nl" hreflang="nl" data-title="Penta-erytritoltetranitraat" 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%9A%E3%83%B3%E3%82%B9%E3%83%AA%E3%83%83%E3%83%88" title="ペンスリット – Japanese" lang="ja" hreflang="ja" data-title="ペンスリット" 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/Pentritt" title="Pentritt – Norwegian Bokmål" lang="nb" hreflang="nb" data-title="Pentritt" 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-ps mw-list-item"><a href="https://ps.wikipedia.org/wiki/%D9%BE%DB%8C%D9%86%D9%BC%D8%B1%DB%8C%D9%BC" title="پینټریټ – Pashto" lang="ps" hreflang="ps" data-title="پینټریټ" data-language-autonym="پښتو" data-language-local-name="Pashto" class="interlanguage-link-target"><span>پښتو</span></a></li><li class="interlanguage-link interwiki-pl mw-list-item"><a href="https://pl.wikipedia.org/wiki/Pentryt" title="Pentryt – Polish" lang="pl" hreflang="pl" data-title="Pentryt" 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/Tetranitrato_de_pentaeritrina" title="Tetranitrato de pentaeritrina – Portuguese" lang="pt" hreflang="pt" data-title="Tetranitrato de pentaeritrina" data-language-autonym="Português" data-language-local-name="Portuguese" class="interlanguage-link-target"><span>Português</span></a></li><li class="interlanguage-link interwiki-ru mw-list-item"><a href="https://ru.wikipedia.org/wiki/%D0%9F%D0%B5%D0%BD%D1%82%D0%B0%D1%8D%D1%80%D0%B8%D1%82%D1%80%D0%B8%D1%82%D1%82%D0%B5%D1%82%D1%80%D0%B0%D0%BD%D0%B8%D1%82%D1%80%D0%B0%D1%82" title="Пентаэритриттетранитрат – Russian" lang="ru" hreflang="ru" data-title="Пентаэритриттетранитрат" 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/Pentaerythritol_tetranitrate" title="Pentaerythritol tetranitrate – Simple English" lang="en-simple" hreflang="en-simple" data-title="Pentaerythritol tetranitrate" 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/Pentrit" title="Pentrit – Slovak" lang="sk" hreflang="sk" data-title="Pentrit" 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/Pentrit" title="Pentrit – Slovenian" lang="sl" hreflang="sl" data-title="Pentrit" data-language-autonym="Slovenščina" data-language-local-name="Slovenian" class="interlanguage-link-target"><span>Slovenščina</span></a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/Pentaeritritol_tetranitrat" title="Pentaeritritol tetranitrat – Serbian" lang="sr" hreflang="sr" data-title="Pentaeritritol tetranitrat" 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/Pentaeritritol_tetranitrat" title="Pentaeritritol tetranitrat – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Pentaeritritol tetranitrat" 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/PETN" title="PETN – Finnish" lang="fi" hreflang="fi" data-title="PETN" 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/Pentyl_(spr%C3%A4ng%C3%A4mne)" title="Pentyl (sprängämne) – Swedish" lang="sv" hreflang="sv" data-title="Pentyl (sprängämne)" 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%AF%86%E0%AE%A9%E0%AF%8D%E0%AE%9F%E0%AE%BE%E0%AE%8E%E0%AE%B0%E0%AE%BF%E0%AE%A4%E0%AF%8D%E0%AE%B0%E0%AE%BF%E0%AE%9F%E0%AF%8D%E0%AE%9F%E0%AF%8B%E0%AE%B2%E0%AF%8D_%E0%AE%9F%E0%AF%86%E0%AE%9F%E0%AF%8D%E0%AE%B0%E0%AE%BE%E0%AE%A8%E0%AF%88%E0%AE%9F%E0%AF%8D%E0%AE%B0%E0%AF%87%E0%AE%9F%E0%AF%8D" title="பென்டாஎரித்ரிட்டோல் டெட்ராநைட்ரேட் – Tamil" lang="ta" hreflang="ta" data-title="பென்டாஎரித்ரிட்டோல் டெட்ராநைட்ரேட்" data-language-autonym="தமிழ்" data-language-local-name="Tamil" class="interlanguage-link-target"><span>தமிழ்</span></a></li><li class="interlanguage-link interwiki-tr mw-list-item"><a href="https://tr.wikipedia.org/wiki/Pentaeritritol_tetranitrat" title="Pentaeritritol tetranitrat – Turkish" lang="tr" hreflang="tr" data-title="Pentaeritritol tetranitrat" data-language-autonym="Türkçe" data-language-local-name="Turkish" class="interlanguage-link-target"><span>Türkçe</span></a></li><li class="interlanguage-link interwiki-uk mw-list-item"><a href="https://uk.wikipedia.org/wiki/%D0%A2%D0%B5%D1%82%D1%80%D0%B0%D0%BD%D1%96%D1%82%D1%80%D0%BE%D0%BF%D0%B5%D0%BD%D1%82%D0%B0%D0%B5%D1%80%D0%B8%D1%82%D1%80%D0%B8%D1%82" title="Тетранітропентаеритрит – Ukrainian" lang="uk" hreflang="uk" data-title="Тетранітропентаеритрит" data-language-autonym="Українська" data-language-local-name="Ukrainian" class="interlanguage-link-target"><span>Українська</span></a></li><li class="interlanguage-link interwiki-vi mw-list-item"><a href="https://vi.wikipedia.org/wiki/PETN" title="PETN – Vietnamese" lang="vi" hreflang="vi" data-title="PETN" data-language-autonym="Tiếng Việt" data-language-local-name="Vietnamese" class="interlanguage-link-target"><span>Tiếng Việt</span></a></li><li class="interlanguage-link interwiki-zh mw-list-item"><a href="https://zh.wikipedia.org/wiki/%E5%AD%A3%E6%88%8A%E5%9B%9B%E9%86%87%E5%9B%9B%E7%A1%9D%E9%85%B8%E9%85%AF" title="季戊四醇四硝酸酯 – Chinese" lang="zh" hreflang="zh" data-title="季戊四醇四硝酸酯" 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/Q189334#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/Pentaerythritol_tetranitrate" 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:Pentaerythritol_tetranitrate" 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/Pentaerythritol_tetranitrate"><span>Read</span></a></li><li id="ca-viewsource" class="vector-tab-noicon mw-list-item"><a href="/w/index.php?title=Pentaerythritol_tetranitrate&action=edit" title="This page is protected.
You can view its source [e]" accesskey="e"><span>View source</span></a></li><li id="ca-history" class="vector-tab-noicon mw-list-item"><a href="/w/index.php?title=Pentaerythritol_tetranitrate&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/Pentaerythritol_tetranitrate"><span>Read</span></a></li><li id="ca-more-viewsource" class="vector-more-collapsible-item mw-list-item"><a href="/w/index.php?title=Pentaerythritol_tetranitrate&action=edit"><span>View source</span></a></li><li id="ca-more-history" class="vector-more-collapsible-item mw-list-item"><a href="/w/index.php?title=Pentaerythritol_tetranitrate&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/Pentaerythritol_tetranitrate" 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/Pentaerythritol_tetranitrate" 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=Pentaerythritol_tetranitrate&oldid=1251608019" 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=Pentaerythritol_tetranitrate&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=Pentaerythritol_tetranitrate&id=1251608019&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%2FPentaerythritol_tetranitrate"><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%2FPentaerythritol_tetranitrate"><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=Pentaerythritol_tetranitrate&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=Pentaerythritol_tetranitrate&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:Pentaerythritol_tetranitrate" 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/Q189334" 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 id="mw-indicator-pp-default" class="mw-indicator"><div class="mw-parser-output"><span typeof="mw:File"><a href="/wiki/Wikipedia:Protection_policy#extended" title="This article is extended-protected"><img alt="Extended-protected article" src="//upload.wikimedia.org/wikipedia/en/thumb/8/8c/Extended-protection-shackle.svg/20px-Extended-protection-shackle.svg.png" decoding="async" width="20" height="20" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/8/8c/Extended-protection-shackle.svg/30px-Extended-protection-shackle.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/8/8c/Extended-protection-shackle.svg/40px-Extended-protection-shackle.svg.png 2x" data-file-width="512" data-file-height="512" /></a></span></div></div> </div> <div id="siteSub" class="noprint">From Wikipedia, the free encyclopedia</div> </div> <div id="contentSub"><div id="mw-content-subtitle"><span class="mw-redirectedfrom">(Redirected from <a href="/w/index.php?title=Pentaerithrityl_tetranitrate&redirect=no" class="mw-redirect" title="Pentaerithrityl tetranitrate">Pentaerithrityl tetranitrate</a>)</span></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">Explosive chemical compound</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">"PETN" redirects here. For the wind power station, see <a href="/wiki/Taiba_N%27Diaye_Wind_Power_Station" title="Taiba N'Diaye Wind Power Station">Taiba N'Diaye Wind Power Station</a>.</div> <p> <style data-mw-deduplicate="TemplateStyles:r1084375498">.mw-parser-output .ib-chembox{border-collapse:collapse;text-align:left}.mw-parser-output .ib-chembox td,.mw-parser-output .ib-chembox th{border:1px solid #a2a9b1;width:40%}.mw-parser-output .ib-chembox td+td{width:60%}</style> </p> <table class="infobox ib-chembox"> <caption>Pentaerythritol tetranitrate </caption> <tbody><tr> <td colspan="2" style="text-align:center; padding:2px;"><span typeof="mw:File"><a href="/wiki/File:PETN.svg" class="mw-file-description"><img alt="Skeletal formula" src="//upload.wikimedia.org/wikipedia/commons/thumb/8/88/PETN.svg/220px-PETN.svg.png" decoding="async" width="220" height="188" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/8/88/PETN.svg/330px-PETN.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/8/88/PETN.svg/440px-PETN.svg.png 2x" data-file-width="312" data-file-height="266" /></a></span> </td></tr> <tr> <td colspan="2" style="text-align:center; padding:2px;"><span typeof="mw:File"><a href="/wiki/File:PETN-from-xtal-2006-3D-balls-B.png" class="mw-file-description"><img alt="Ball-and-stick model" src="//upload.wikimedia.org/wikipedia/commons/thumb/6/6c/PETN-from-xtal-2006-3D-balls-B.png/220px-PETN-from-xtal-2006-3D-balls-B.png" decoding="async" width="220" height="166" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/6c/PETN-from-xtal-2006-3D-balls-B.png/330px-PETN-from-xtal-2006-3D-balls-B.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/6c/PETN-from-xtal-2006-3D-balls-B.png/440px-PETN-from-xtal-2006-3D-balls-B.png 2x" data-file-width="2000" data-file-height="1506" /></a></span> </td></tr> <tr> <td colspan="2" style="text-align:center; padding:2px;"><span typeof="mw:File"><a href="/wiki/File:Pentaerythritol_tetranitrate_05.jpg" class="mw-file-description"><img alt="Pentaerythritol tetranitrate after crystalization from acetone" src="//upload.wikimedia.org/wikipedia/commons/thumb/9/93/Pentaerythritol_tetranitrate_05.jpg/235px-Pentaerythritol_tetranitrate_05.jpg" decoding="async" width="235" height="176" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/9/93/Pentaerythritol_tetranitrate_05.jpg/353px-Pentaerythritol_tetranitrate_05.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/9/93/Pentaerythritol_tetranitrate_05.jpg/470px-Pentaerythritol_tetranitrate_05.jpg 2x" data-file-width="4308" data-file-height="3231" /></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/Preferred_IUPAC_name" title="Preferred IUPAC name">Preferred IUPAC name</a> <div style="max-width:22em; word-wrap:break-word; padding-left:1.7em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0; max-width:22em;">2,2-Bis[(nitrooxy)methyl]propane-1,3-diyl dinitrate</div></div> </td></tr> <tr> <td colspan="2" style="text-align:left;">Other names <div style="max-width:22em; word-wrap:break-word; padding-left:1.7em;">[3-Nitrooxy-2,2-bis(nitrooxymethyl)propyl] nitrate</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=78-11-5">78-11-5</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">3D model (<a href="/wiki/JSmol" class="mw-redirect" title="JSmol">JSmol</a>)</div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="chemapps.stolaf.edu (3D interactive model)"><a rel="nofollow" class="external text" href="https://chemapps.stolaf.edu/jmol/jmol.php?model=C%28C%28CO%5BN%2B%5D%28%3DO%29%5BO-%5D%29%28CO%5BN%2B%5D%28%3DO%29%5BO-%5D%29CO%5BN%2B%5D%28%3DO%29%5BO-%5D%29O%5BN%2B%5D%28%3DO%29%5BO-%5D">Interactive image</a></span></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ChEMBL" title="ChEMBL">ChEMBL</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.ebi.ac.uk"><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chembldb/index.php/compound/inspect/ChEMBL466659">ChEMBL466659</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.6271.html">6271</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ECHA_InfoCard" class="mw-redirect" title="ECHA InfoCard"><span title="echa.europa.eu">ECHA InfoCard</span></a> </td> <td><a rel="nofollow" class="external text" href="https://echa.europa.eu/substance-information/-/substanceinfo/100.000.987">100.000.987</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q189334#P2566" title="Edit this at Wikidata"><img alt="Edit this at Wikidata" src="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/10px-OOjs_UI_icon_edit-ltr-progressive.svg.png" decoding="async" width="10" height="10" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/15px-OOjs_UI_icon_edit-ltr-progressive.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/20px-OOjs_UI_icon_edit-ltr-progressive.svg.png 2x" data-file-width="20" data-file-height="20" /></a></span> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/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/6518">6518</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/10L39TRG1Z">10L39TRG1Z</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/DTXSID2023430">DTXSID2023430</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q189334#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/C5H8N4O12/c10-6(11)18-1-5(2-19-7(12)13,3-20-8(14)15)4-21-9(16)17/h1-4H2<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: TZRXHJWUDPFEEY-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=1S/C5H8N4O12/c10-6(11)18-1-5(2-19-7(12)13,3-20-8(14)15)4-21-9(16)17/h1-4H2</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%;">C(C(CO[N+](=O)[O-])(CO[N+](=O)[O-])CO[N+](=O)[O-])O[N+](=O)[O-]</div></li></ul> </div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Properties </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Chemical_formula" title="Chemical formula">Chemical formula</a></div> </td> <td><span title="Carbon">C</span><sub>5</sub><span title="Hydrogen">H</span><sub>8</sub><span title="Nitrogen">N</span><sub>4</sub><span title="Oxygen">O</span><sub>12</sub> </td></tr> <tr> <td><a href="/wiki/Molar_mass" title="Molar mass">Molar mass</a> </td> <td>316.137 g/mol    </td></tr> <tr> <td>Appearance </td> <td>White crystalline solid<sup id="cite_ref-epa1_1-0" class="reference"><a href="#cite_note-epa1-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><a href="/wiki/Density" title="Density">Density</a> </td> <td>1.77 g/cm<sup>3</sup> at 20 °C </td></tr> <tr> <td><a href="/wiki/Melting_point" title="Melting point">Melting point</a> </td> <td>141.3 °C (286.3 °F; 414.4 K) </td></tr> <tr> <td><a href="/wiki/Boiling_point" title="Boiling point">Boiling point</a> </td> <td>180 °C (356 °F; 453 K) (decomposes above 150 °C (302 °F)) </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Explosive data </th></tr> <tr> <td><a href="/wiki/Shock_sensitivity" title="Shock sensitivity">Shock sensitivity</a> </td> <td>Medium </td></tr> <tr> <td><a href="/wiki/Friction_sensitivity" title="Friction sensitivity">Friction sensitivity</a> </td> <td>Medium </td></tr> <tr> <td><a href="/wiki/Detonation_velocity" title="Detonation velocity">Detonation velocity</a> </td> <td>8400 m/s (density 1.7 g/cm<sup>3</sup>) </td></tr> <tr> <td><a href="/wiki/Relative_effectiveness_factor" class="mw-redirect" title="Relative effectiveness factor">RE factor</a> </td> <td>1.66 </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Hazards </th></tr> <tr> <td colspan="2" style="text-align:left; background-color:#eaeaea;"><a href="/wiki/Globally_Harmonized_System_of_Classification_and_Labelling_of_Chemicals" title="Globally Harmonized System of Classification and Labelling of Chemicals"><b>GHS</b> labelling</a>: </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/GHS_hazard_pictograms" title="GHS hazard pictograms">Pictograms</a></div> </td> <td><span typeof="mw:File"><a href="/wiki/File:GHS-pictogram-skull.svg" class="mw-file-description" title="GHS06: Toxic"><img alt="GHS06: Toxic" src="//upload.wikimedia.org/wikipedia/commons/thumb/5/58/GHS-pictogram-skull.svg/50px-GHS-pictogram-skull.svg.png" decoding="async" width="50" height="50" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/5/58/GHS-pictogram-skull.svg/75px-GHS-pictogram-skull.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/5/58/GHS-pictogram-skull.svg/100px-GHS-pictogram-skull.svg.png 2x" data-file-width="724" data-file-height="724" /></a></span> <span typeof="mw:File"><a href="/wiki/File:GHS-pictogram-explos.svg" class="mw-file-description" title="GHS01: Explosive"><img alt="GHS01: Explosive" src="//upload.wikimedia.org/wikipedia/commons/thumb/4/4a/GHS-pictogram-explos.svg/50px-GHS-pictogram-explos.svg.png" decoding="async" width="50" height="50" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/4/4a/GHS-pictogram-explos.svg/75px-GHS-pictogram-explos.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/4/4a/GHS-pictogram-explos.svg/100px-GHS-pictogram-explos.svg.png 2x" data-file-width="724" data-file-height="724" /></a></span> <span typeof="mw:File"><a href="/wiki/File:GHS-pictogram-silhouette.svg" class="mw-file-description" title="GHS08: Health hazard"><img alt="GHS08: Health hazard" src="//upload.wikimedia.org/wikipedia/commons/thumb/2/21/GHS-pictogram-silhouette.svg/50px-GHS-pictogram-silhouette.svg.png" decoding="async" width="50" height="50" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/2/21/GHS-pictogram-silhouette.svg/75px-GHS-pictogram-silhouette.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/2/21/GHS-pictogram-silhouette.svg/100px-GHS-pictogram-silhouette.svg.png 2x" data-file-width="724" data-file-height="724" /></a></span> </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Globally_Harmonized_System_of_Classification_and_Labelling_of_Chemicals#Signal_word" title="Globally Harmonized System of Classification and Labelling of Chemicals">Signal word</a></div> </td> <td><b>Danger</b> </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/GHS_hazard_statements" title="GHS hazard statements">Hazard statements</a></div> </td> <td><abbr class="abbr" title="H201: Explosive: mass explosion hazard">H201</abbr>, <abbr class="abbr" title="H241: Heating may cause a fire or explosion">H241</abbr>, <abbr class="abbr" title="H302: Harmful if swallowed">H302</abbr>, <abbr class="abbr" title="H316: Causes mild skin irritation">H316</abbr>, <abbr class="abbr" title="H370: Causes damage to organs">H370</abbr>, <abbr class="abbr" title="H373: May cause damage to organs through prolonged or repeated exposure">H373</abbr> </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/GHS_precautionary_statements" title="GHS precautionary statements">Precautionary statements</a></div> </td> <td><abbr class="abbr" title="P210: Keep away from heat, hot surfaces, sparks, open flames and other ignition sources. No smoking.">P210</abbr>, <abbr class="abbr" title="P250: Do not subject to grinding/shock/.../friction.">P250</abbr>, <abbr class="abbr" title="P261: Avoid breathing dust/fume/gas/mist/vapours/spray.">P261</abbr>, <abbr class="abbr" title="P264: Wash ... thoroughly after handling.">P264</abbr>, <abbr class="abbr" title="P301+P312: IF SWALLOWED: Call a POISON CENTER or doctor/physician if you feel unwell.">P301+P312</abbr>, <abbr class="abbr" title="P370+P380: In case of fire: Evacuate area.">P370+P380</abbr>, <abbr class="abbr" title="P372: Explosion risk.">P372</abbr>, <abbr class="abbr" title="P401: Store in accordance with ...">P401</abbr>, <abbr class="abbr" title="P501: Dispose of contents/container to ...">P501</abbr> </td></tr> <tr> <td><a href="/wiki/NFPA_704" title="NFPA 704"><b>NFPA 704</b></a> (fire diamond) </td> <td><style data-mw-deduplicate="TemplateStyles:r1170367383">.mw-parser-output .nfpa-704-diamond-ref{float:right;padding:1px;text-align:right}.mw-parser-output .nfpa-704-diamond-container{width:82px;font-family:sans-serif;margin:0 auto}.mw-parser-output .nfpa-704-diamond-container-ref{float:left;margin-left:1em}.mw-parser-output .nfpa-704-diamond-images{float:left;font-size:20px;text-align:center;position:relative;height:80px;width:80px;padding:1px}.mw-parser-output .nfpa-704-diamond-map{position:absolute;height:80px;width:80px}.mw-parser-output .nfpa-704-diamond .noresize{margin:0 auto}.mw-parser-output .nfpa-704-diamond-code{line-height:1em;text-align:center;position:absolute}.mw-parser-output .nfpa-704-diamond-code>a{color:black}.mw-parser-output .nfpa-704-diamond-blue{width:13px;top:31px;left:15px}.mw-parser-output .nfpa-704-diamond-red{width:12px;top:12px;left:35px}.mw-parser-output .nfpa-704-diamond-yellow{width:13px;top:31px;left:54px}.mw-parser-output .nfpa-704-diamond-white-image{position:relative;top:51px;left:0}.mw-parser-output .nfpa-704-diamond-white-text{vertical-align:middle;text-align:center;line-height:80%;position:absolute;top:52px}.mw-parser-output .nfpa-704-diamond-white-text a>span{position:absolute;color:black}.mw-parser-output .nfpa-704-diamond-white-wors{font-size:15px;width:23px;left:29px}.mw-parser-output .nfpa-704-diamond-white-wox{font-size:15px;font-stretch:condensed;width:21px;line-height:80%;top:-4px;left:29px}.mw-parser-output .nfpa-704-diamond-white-abcp{font-size:13.5px;font-stretch:condensed;width:28px;left:26px}.mw-parser-output .nfpa-704-diamond-white-ac{font-size:10px;width:30px;left:25px}.mw-parser-output .nfpa-704-diamond-white-strike{text-decoration:line-through}</style><div class="nfpa-704-diamond notheme"><div class="nfpa-704-diamond-container"><div class="nfpa-704-diamond-images nounderlines"> <div class="nfpa-704-diamond-map"><figure class="noresize" typeof="mw:File"><span><img alt="NFPA 704 four-colored diamond" src="//upload.wikimedia.org/wikipedia/commons/thumb/6/6f/NFPA_704.svg/80px-NFPA_704.svg.png" decoding="async" width="80" height="80" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/6f/NFPA_704.svg/120px-NFPA_704.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/6f/NFPA_704.svg/160px-NFPA_704.svg.png 2x" data-file-width="512" data-file-height="512" usemap="#ImageMap_ecc1c618d934ecb3" /></span><map name="ImageMap_ecc1c618d934ecb3"><area href="/wiki/NFPA_704#Blue" shape="poly" coords="23,23,47,47,23,70,0,47" alt="Health 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroform" title="Health 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroform" /><area href="/wiki/NFPA_704#Red" shape="poly" coords="47,0,70,23,47,47,23,23" alt="Flammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oil" title="Flammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oil" /><area href="/wiki/NFPA_704#Yellow" shape="poly" coords="70,23,94,47,70,70,47,47" alt="Instability 3: Capable of detonation or explosive decomposition but requires a strong initiating source, must be heated under confinement before initiation, reacts explosively with water, or will detonate if severely shocked. E.g. hydrogen peroxide" title="Instability 3: Capable of detonation or explosive decomposition but requires a strong initiating source, must be heated under confinement before initiation, reacts explosively with water, or will detonate if severely shocked. E.g. hydrogen peroxide" /><area href="/wiki/NFPA_704#White" shape="poly" coords="47,47,70,70,47,94,23,70" alt="Special hazards (white): no code" title="Special hazards (white): no code" /></map><figcaption></figcaption></figure></div><div class="nfpa-704-diamond-code nfpa-704-diamond-blue"> <a href="/wiki/NFPA_704#Blue" title="NFPA 704"><span title="Health 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroform" class="notheme mw-no-invert">2</span></a></div><div class="nfpa-704-diamond-code nfpa-704-diamond-red"> <a href="/wiki/NFPA_704#Red" title="NFPA 704"><span title="Flammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oil" class="notheme mw-no-invert">1</span></a></div><div class="nfpa-704-diamond-code nfpa-704-diamond-yellow"> <a href="/wiki/NFPA_704#Yellow" title="NFPA 704"><span title="Instability 3: Capable of detonation or explosive decomposition but requires a strong initiating source, must be heated under confinement before initiation, reacts explosively with water, or will detonate if severely shocked. E.g. hydrogen peroxide" class="notheme mw-no-invert">3</span></a></div></div></div></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Autoignition_temperature" title="Autoignition temperature">Autoignition<br />temperature</a></div> </td> <td>190 °C (374 °F; 463 K) </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Pharmacology </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Anatomical_Therapeutic_Chemical_Classification_System" title="Anatomical Therapeutic Chemical Classification System">ATC code</a></div> </td> <td><a href="/wiki/ATC_code_C01" title="ATC code C01">C01DA05</a> (<span title="www.whocc.no"><a rel="nofollow" class="external text" href="https://www.whocc.no/atc_ddd_index/?code=C01DA05">WHO</a></span>)  </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=477001336&page2=Pentaerythritol+tetranitrate">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>Pentaerythritol tetranitrate</b> (<b>PETN</b>), also known as <b>PENT</b>, <b>pentyl</b>, <b>PENTA</b> (<i><b>ПЕНТА</b></i>, primarily in Russian), <b>TEN</b> (tetraeritrit nitrate), <b>corpent</b>, or <b>penthrite</b> (or, rarely and primarily in German, as <i><b>nitropenta</b></i>), is an <a href="/wiki/Explosive" title="Explosive">explosive</a> material. It is the <a href="/wiki/Nitrate_ester" title="Nitrate ester">nitrate ester</a> of <a href="/wiki/Pentaerythritol" title="Pentaerythritol">pentaerythritol</a>, and is structurally very similar to <a href="/wiki/Nitroglycerin" title="Nitroglycerin">nitroglycerin</a>. <a href="/wiki/Penta-" class="mw-redirect" title="Penta-">Penta</a> refers to the five <a href="/wiki/Carbon_atom" class="mw-redirect" title="Carbon atom">carbon atoms</a> of the <a href="/wiki/Neopentane" title="Neopentane">neopentane</a> skeleton. PETN is a very powerful explosive material with a <a href="/wiki/Relative_effectiveness_factor" class="mw-redirect" title="Relative effectiveness factor">relative effectiveness factor</a> of 1.66.<sup id="cite_ref-urlPETN_[Pentaerythritol_tetranitrate]_2-0" class="reference"><a href="#cite_note-urlPETN_[Pentaerythritol_tetranitrate]-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> When mixed with a <a href="/wiki/Plasticizer" title="Plasticizer">plasticizer</a>, PETN forms a <a href="/wiki/Plastic_explosive" title="Plastic explosive">plastic explosive</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> Along with <a href="/wiki/RDX" title="RDX">RDX</a> it is the main ingredient of <a href="/wiki/Semtex" title="Semtex">Semtex</a>. </p><p>PETN is also used as a <a href="/wiki/Vasodilation" title="Vasodilation">vasodilator</a> drug to treat certain heart conditions, such as for management of <a href="/wiki/Angina" title="Angina">angina</a>.<sup id="cite_ref-newdrugs_4-0" class="reference"><a href="#cite_note-newdrugs-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-ebadi_5-0" class="reference"><a href="#cite_note-ebadi-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="History">History</h2></div> <p>Pentaerythritol tetranitrate was first prepared and patented in 1894 by the explosives manufacturer <a href="/w/index.php?title=RWS_(company)&action=edit&redlink=1" class="new" title="RWS (company) (page does not exist)">Rheinisch-Westfälische Sprengstoff A.G.</a><span class="noprint" style="font-size:85%; font-style: normal;"> [<a href="https://de.wikipedia.org/wiki/RWS_(Unternehmen)" class="extiw" title="de:RWS (Unternehmen)">de</a>]</span> of <a href="/wiki/Cologne" title="Cologne">Cologne, Germany</a>.<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><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><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><sup id="cite_ref-9" class="reference"><a href="#cite_note-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> The production of PETN started in 1912, when the improved method of production was patented by the German government. PETN was used by the German Military in <span class="nowrap"><a href="/wiki/World_War_I" title="World War I">World War I</a></span>.<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-11" class="reference"><a href="#cite_note-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> It was also used in the <a href="/wiki/MG_FF_cannon" title="MG FF cannon">MG FF/M autocannons</a> and many other weapon systems of the <a href="/wiki/Luftwaffe" title="Luftwaffe">Luftwaffe</a> in World War II.<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (September 2024)">citation needed</span></a></i>]</sup> </p> <div class="mw-heading mw-heading2"><h2 id="Properties">Properties</h2></div> <p>PETN is practically <a href="/wiki/Solubility" title="Solubility">insoluble</a> in water (0.01 g/100 mL at 50 °C), weakly soluble in common nonpolar <a href="/wiki/Solvent" title="Solvent">solvents</a> such as <a href="/wiki/Aliphatic_compound" title="Aliphatic compound">aliphatic hydrocarbons</a> (like gasoline) or <a href="/wiki/Carbon_tetrachloride" title="Carbon tetrachloride">tetrachloromethane</a>, but soluble in some other organic solvents, particularly in <a href="/wiki/Acetone" title="Acetone">acetone</a> (about 15 g/100 g of the solution at 20 °C, 55 g/100 g at 60 °C) and <a href="/wiki/Dimethylformamide" title="Dimethylformamide">dimethylformamide</a> (40 g/100 g of the solution at 40 °C, 70 g/100 g at 70 °C). It is a non-planar molecule that crystallizes in the space group <i>P</i><span style="text-decoration:overline;">4</span>2<sub>1</sub><i>c</i>.<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> PETN forms <a href="/wiki/Eutectic_system" title="Eutectic system">eutectic</a> mixtures with some liquid or molten <a href="/wiki/Aromaticity" title="Aromaticity">aromatic</a> <a href="/wiki/Nitro_compound" title="Nitro compound">nitro compounds</a>, <i>e.g.</i> <a href="/wiki/Trinitrotoluene" class="mw-redirect" title="Trinitrotoluene">trinitrotoluene</a> (TNT) or <a href="/wiki/Tetryl" title="Tetryl">tetryl</a>. Due to steric hindrance of the adjacent neopentyl-like moiety, PETN is resistant to attack by many chemical <a href="/wiki/Reagent" title="Reagent">reagents</a>; it does not <a href="/wiki/Hydrolysis" title="Hydrolysis">hydrolyze</a> in water at room temperature or in weaker <a href="/wiki/Alkalinity" title="Alkalinity">alkaline</a> <a href="/wiki/Aqueous_solution" title="Aqueous solution">aqueous solutions</a>. Water at 100 °C or above causes <a href="/wiki/Hydrolysis" title="Hydrolysis">hydrolysis</a> to dinitrate; presence of 0.1% <a href="/wiki/Nitric_acid" title="Nitric acid">nitric acid</a> accelerates the reaction. </p><p>The <a href="/wiki/Chemical_stability" title="Chemical stability">chemical stability</a> of PETN is of interest, because of the presence of PETN in aging weapons.<sup id="cite_ref-13" class="reference"><a href="#cite_note-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup> <a href="/wiki/Neutron_radiation" title="Neutron radiation">Neutron radiation</a> degrades PETN, producing <a href="/wiki/Carbon_dioxide" title="Carbon dioxide">carbon dioxide</a> and some pentaerythritol dinitrate and <a href="/wiki/Nitrate" title="Nitrate">trinitrate</a>. <a href="/wiki/Gamma_radiation" class="mw-redirect" title="Gamma radiation">Gamma radiation</a> increases the <a href="/wiki/Thermal_decomposition" title="Thermal decomposition">thermal decomposition</a> sensitivity of PETN, lowers melting point by few degrees Celsius, and causes swelling of the samples. Like other nitrate esters, the primary <a href="/wiki/Chemical_decomposition" title="Chemical decomposition">degradation</a> mechanism is the loss of <a href="/wiki/Nitrogen_dioxide" title="Nitrogen dioxide">nitrogen dioxide</a>; this reaction is <a href="/wiki/Autocatalytic" class="mw-redirect" title="Autocatalytic">autocatalytic</a>.<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (November 2010)">citation needed</span></a></i>]</sup> Studies were performed on <a href="/wiki/Thermal_decomposition" title="Thermal decomposition">thermal decomposition</a> of PETN.<sup id="cite_ref-14" class="reference"><a href="#cite_note-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup> </p><p>In the environment, PETN undergoes <a href="/wiki/Biodegradation" title="Biodegradation">biodegradation</a>. Some bacteria denitrate PETN to trinitrate and then dinitrate, which is then further degraded.<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> PETN has low <a href="/wiki/Volatility_(chemistry)" title="Volatility (chemistry)">volatility</a> and low solubility in water, and therefore has low <a href="/wiki/Bioavailability" title="Bioavailability">bioavailability</a> for most organisms. Its <a href="/wiki/Toxicity" title="Toxicity">toxicity</a> is relatively low, and its <a href="/wiki/Transdermal" title="Transdermal">transdermal</a> absorption also seems to be low. It poses a threat for aquatic <a href="/wiki/Organism" title="Organism">organisms</a>. It can be degraded to pentaerythritol by <a href="/wiki/Iron" title="Iron">iron</a>.<sup id="cite_ref-16" class="reference"><a href="#cite_note-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Production">Production</h2></div> <p>Production is by the reaction of <a href="/wiki/Pentaerythritol" title="Pentaerythritol">pentaerythritol</a> with concentrated <a href="/wiki/Nitric_acid" title="Nitric acid">nitric acid</a> to form a precipitate which can be recrystallized from acetone to give processable crystals.<sup id="cite_ref-Ullmann_17-0" class="reference"><a href="#cite_note-Ullmann-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup> </p><p>Variations of a method first published in US Patent 2,370,437 by Acken and Vyverberg (1945 to Du Pont) form the basis of all current commercial production.<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (September 2024)">citation needed</span></a></i>]</sup> </p><p>PETN is manufactured by numerous manufacturers as a powder, or together with <a href="/wiki/Nitrocellulose" title="Nitrocellulose">nitrocellulose</a> and <a href="/wiki/Plasticizer" title="Plasticizer">plasticizer</a> as thin plasticized sheets (e.g. <a href="/wiki/Primasheet" title="Primasheet">Primasheet</a> 1000 or <a href="/wiki/Detasheet" title="Detasheet">Detasheet</a>). PETN residues are easily detectable in hair of people handling it.<sup id="cite_ref-18" class="reference"><a href="#cite_note-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup> The highest residue retention is on black hair; some residues remain even after washing.<sup id="cite_ref-19" class="reference"><a href="#cite_note-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-latimes.com_20-0" class="reference"><a href="#cite_note-latimes.com-20"><span class="cite-bracket">[</span>20<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Explosive_use">Explosive use</h2></div> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:Pentryt.jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/5/55/Pentryt.jpg/220px-Pentryt.jpg" decoding="async" width="220" height="140" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/5/55/Pentryt.jpg/330px-Pentryt.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/5/55/Pentryt.jpg/440px-Pentryt.jpg 2x" data-file-width="960" data-file-height="609" /></a><figcaption>Pentaerythritol tetranitrate before crystallization from acetone</figcaption></figure> <p>The most common use of PETN is as an explosive with high <a href="/wiki/Brisance" title="Brisance">brisance</a>. It is a <a href="/wiki/Secondary_explosive" class="mw-redirect" title="Secondary explosive">secondary explosive</a>, meaning it is more difficult to detonate than <a href="/wiki/Primary_explosive" class="mw-redirect" title="Primary explosive">primary explosives</a>, so dropping or igniting it will typically not cause an explosion (at <a href="/wiki/Standard_atmospheric_pressure" class="mw-redirect" title="Standard atmospheric pressure">standard atmospheric pressure</a> it is difficult to ignite and burns vigorously), but is more sensitive to shock and friction than other secondary explosives such as <a href="/wiki/TNT" title="TNT">TNT</a> or <a href="/wiki/Tetryl" title="Tetryl">tetryl</a>.<sup id="cite_ref-Ullmann_17-1" class="reference"><a href="#cite_note-Ullmann-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-nyt_21-0" class="reference"><a href="#cite_note-nyt-21"><span class="cite-bracket">[</span>21<span class="cite-bracket">]</span></a></sup> Under certain conditions a <a href="/wiki/Deflagration_to_detonation_transition" title="Deflagration to detonation transition">deflagration to detonation transition</a> can occur, just like that of <a href="/wiki/Ammonium_nitrate" title="Ammonium nitrate">ammonium nitrate</a>. </p><p>It is rarely used alone in military operations due to its lower stability, but is primarily used in the main charges of plastic explosives (such as <a href="/wiki/C-4_(explosive)" title="C-4 (explosive)">C4</a>) along with other explosives (especially <a href="/wiki/RDX" title="RDX">RDX</a>), <a href="/wiki/Explosive_booster" title="Explosive booster">booster</a> and <a href="/wiki/Burst_charge" title="Burst charge">bursting charges</a> of small <a href="/wiki/Caliber" title="Caliber">caliber</a> <a href="/wiki/Ammunition" title="Ammunition">ammunition</a>, in upper charges of <a href="/wiki/Detonator" title="Detonator">detonators</a> in some <a href="/wiki/Land_mine" title="Land mine">land mines</a> and shells, as the explosive core of <a href="/wiki/Detonation_cord" class="mw-redirect" title="Detonation cord">detonation cord</a>.<sup id="cite_ref-urlwww.dynonobel.com_22-0" class="reference"><a href="#cite_note-urlwww.dynonobel.com-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> PETN is the least stable of the common military explosives, but can be stored without significant deterioration for longer than <a href="/wiki/Nitroglycerin" title="Nitroglycerin">nitroglycerin</a> or <a href="/wiki/Nitrocellulose" title="Nitrocellulose">nitrocellulose</a>.<sup id="cite_ref-24" class="reference"><a href="#cite_note-24"><span class="cite-bracket">[</span>24<span class="cite-bracket">]</span></a></sup> </p><p>During <a href="/wiki/World_War_II" title="World War II">World War II</a>, PETN was most importantly used in <a href="/wiki/Exploding-bridgewire_detonator" title="Exploding-bridgewire detonator">exploding-bridgewire detonators</a> for the atomic bombs. These exploding-bridgewire detonators gave more precise detonation compared to <a href="/wiki/Primacord" title="Primacord">primacord</a>. PETN was used for these detonators because it was safer than primary explosives like <a href="/wiki/Lead_azide" class="mw-redirect" title="Lead azide">lead azide</a>: while it was sensitive, it would not detonate below a threshold amount of energy.<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> Exploding bridgewires containing PETN remain used in current nuclear weapons. In spark detonators, PETN is used to avoid the need for primary explosives; the energy needed for a successful direct initiation of PETN by an <a href="/wiki/Electric_spark" title="Electric spark">electric spark</a> ranges between 10–60 mJ. </p><p>PETN was used in the manufacturing of <a href="/wiki/Pager" title="Pager">pagers</a> provided to <a href="/wiki/Hezbollah" title="Hezbollah">Hezbollah</a>. On September 17, 2024, the pagers <a href="/wiki/2024_Lebanon_pager_explosions" class="mw-redirect" title="2024 Lebanon pager explosions">detonated</a>, killing 12 people and injuring thousands.<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> </p><p>Its basic explosion characteristics are: </p> <ul><li>Explosion energy: 5810 kJ/kg (1390 kcal/kg), so 1 kg of PETN has the energy of 1.24 kg TNT.</li> <li><a href="/wiki/Detonation_velocity" title="Detonation velocity">Detonation velocity</a>: 8350 m/s (1.73 g/cm<sup>3</sup>), 7910 m/s (1.62 g/cm<sup>3</sup>), 7420 m/s (1.5 g/cm<sup>3</sup>), 8500 m/s (pressed in a steel tube)</li> <li>Volume of gases produced: 790 dm<sup>3</sup>/kg (other value: 768 dm<sup>3</sup>/kg)</li> <li>Explosion temperature: 4230 °C</li> <li><a href="/wiki/Oxygen_balance" title="Oxygen balance">Oxygen balance</a>: −6.31 atom -g/kg</li> <li><a href="/wiki/Melting_point" title="Melting point">Melting point</a>: 141.3 °C (pure), 140–141 °C (technical)</li> <li><a href="/wiki/Trauzl_lead_block_test" title="Trauzl lead block test">Trauzl lead block test</a>: 523 cm<sup>3</sup> (other values: 500 cm<sup>3</sup> when sealed with sand, or 560 cm<sup>3</sup> when sealed with water)</li> <li>Critical diameter (minimal diameter of a rod that can sustain detonation propagation): 0.9 mm for PETN at 1 g/cm<sup>3</sup>, smaller for higher densities (other value: 1.5 mm)</li></ul> <div class="mw-heading mw-heading3"><h3 id="In_mixtures">In mixtures</h3></div> <p>PETN is used in a number of compositions. It is a major ingredient of the <a href="/wiki/Semtex" title="Semtex">Semtex</a> <a href="/wiki/Plastic_explosive" title="Plastic explosive">plastic explosive</a>. It is also used as a component of <a href="/wiki/Pentolite" title="Pentolite">pentolite</a>, a 50/50 blend with TNT. The XTX8003 extrudable explosive, used in the <a href="/wiki/W68" title="W68">W68</a> and <a href="/wiki/W76" title="W76">W76</a> nuclear warheads, is a mixture of 80% PETN and 20% of Sylgard 182, a <a href="/wiki/Silicone_rubber" title="Silicone rubber">silicone rubber</a>.<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> It is often <a href="/wiki/Phlegmatized" class="mw-redirect" title="Phlegmatized">phlegmatized</a> by addition of 5–40% of <a href="/wiki/Wax" title="Wax">wax</a>, or by polymers (producing <a href="/wiki/Polymer-bonded_explosive" title="Polymer-bonded explosive">polymer-bonded explosives</a>); in this form it is used in some cannon shells up to <a href="/wiki/30_mm_caliber" title="30 mm caliber">30 mm caliber</a>, though it is unsuitable for higher calibers. It is also used as a component of some gun <a href="/wiki/Propellant" title="Propellant">propellants</a> and <a href="/wiki/Solid_rocket_propellant" class="mw-redirect" title="Solid rocket propellant">solid rocket propellants</a>. Nonphlegmatized PETN is stored and handled with approximately 10% water content. PETN alone cannot be <a href="/wiki/Casting" title="Casting">cast</a> as it explosively decomposes slightly above its melting point,<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (September 2016)">citation needed</span></a></i>]</sup><sup class="noprint Inline-Template" style="margin-left:0.1em; white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Please_clarify" title="Wikipedia:Please clarify"><span title="The text near this tag may need clarification or removal of jargon. (September 2016)">clarification needed</span></a></i>]</sup> but it can be mixed with other explosives to form castable mixtures. </p><p>PETN can be initiated by a <a href="/wiki/Laser" title="Laser">laser</a>.<sup id="cite_ref-28" class="reference"><a href="#cite_note-28"><span class="cite-bracket">[</span>28<span class="cite-bracket">]</span></a></sup> A pulse with duration of 25 nanoseconds and 0.5–4.2 joules of energy from a <a href="/wiki/Q-switching" title="Q-switching">Q-switched</a> <a href="/wiki/Ruby_laser" title="Ruby laser">ruby laser</a> can initiate detonation of a PETN surface coated with a 100 nm thick aluminium layer in less than half of a microsecond.<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (November 2010)">citation needed</span></a></i>]</sup> </p><p>PETN has been replaced in many applications by <a href="/wiki/RDX" title="RDX">RDX</a>, which is thermally more stable and has a longer <a href="/wiki/Shelf_life" title="Shelf life">shelf life</a>.<sup id="cite_ref-29" class="reference"><a href="#cite_note-29"><span class="cite-bracket">[</span>29<span class="cite-bracket">]</span></a></sup> PETN can be used in some <a href="/wiki/Ram_accelerator" title="Ram accelerator">ram accelerator</a> types.<sup id="cite_ref-30" class="reference"><a href="#cite_note-30"><span class="cite-bracket">[</span>30<span class="cite-bracket">]</span></a></sup> Replacement of the central carbon atom with <a href="/wiki/Silicon" title="Silicon">silicon</a> produces Si-PETN, which is extremely sensitive.<sup id="cite_ref-31" class="reference"><a href="#cite_note-31"><span class="cite-bracket">[</span>31<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-32" class="reference"><a href="#cite_note-32"><span class="cite-bracket">[</span>32<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Terrorist_use">Terrorist use</h3></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">Main articles: <a href="/wiki/Shoe_Bomber" class="mw-redirect" title="Shoe Bomber">Shoe Bomber</a>, <a href="/wiki/2009_Christmas_Day_bomb_plot" class="mw-redirect" title="2009 Christmas Day bomb plot">2009 Christmas Day bomb plot</a>, and <a href="/wiki/2010_cargo_plane_bomb_plot" class="mw-redirect" title="2010 cargo plane bomb plot">2010 cargo plane bomb plot</a></div> <p>Ten kilograms of PETN was used in the <a href="/wiki/1980_Paris_synagogue_bombing" title="1980 Paris synagogue bombing">1980 Paris synagogue bombing</a>. </p><p>In 1983, 307 people were killed after a truck bomb filled with PETN was detonated at the <a href="/wiki/1983_Beirut_barracks_bombings" title="1983 Beirut barracks bombings">Beirut barracks</a>. </p><p>In 1983, the "Maison de France" house in Berlin was brought to a near-total collapse by the detonation of 24 kilograms (53 lb) of PETN by terrorist <a href="/wiki/Johannes_Weinrich" title="Johannes Weinrich">Johannes Weinrich</a>.<sup id="cite_ref-33" class="reference"><a href="#cite_note-33"><span class="cite-bracket">[</span>33<span class="cite-bracket">]</span></a></sup> </p><p>On July 17, 1996, <a href="/wiki/TWA_Flight_800#Missile_or_bomb_detonation" title="TWA Flight 800">flight TWA 800</a> exploded and crashed in the Atlantic Ocean. Traces of PETN were found in the wreckage. </p><p>In 1999, <a href="/wiki/Alfred_Heinz_Reumayr" title="Alfred Heinz Reumayr">Alfred Heinz Reumayr</a> used PETN as the main charge for his fourteen <a href="/wiki/Improvised_explosive_device" title="Improvised explosive device">improvised explosive devices</a> that he constructed in a thwarted attempt to damage the <a href="/wiki/Trans-Alaska_Pipeline_System" title="Trans-Alaska Pipeline System">Trans-Alaska Pipeline System</a>. </p><p>In 2001, <a href="/wiki/Al-Qaeda" title="Al-Qaeda">al-Qaeda</a> member <a href="/wiki/Richard_Reid_(shoe_bomber)" class="mw-redirect" title="Richard Reid (shoe bomber)">Richard Reid</a>, the "Shoe Bomber", used PETN in the sole of his shoe in his unsuccessful attempt to blow up <a href="/wiki/2001_American_Airlines_Flight_63_bombing_attempt" class="mw-redirect" title="2001 American Airlines Flight 63 bombing attempt">American Airlines Flight 63</a> from Paris to Miami.<sup id="cite_ref-latimes.com_20-1" class="reference"><a href="#cite_note-latimes.com-20"><span class="cite-bracket">[</span>20<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-urlBBC_News|AMERICAS|Shoe_bomb_suspect_did_not_act_alone_34-0" class="reference"><a href="#cite_note-urlBBC_News|AMERICAS|Shoe_bomb_suspect_did_not_act_alone-34"><span class="cite-bracket">[</span>34<span class="cite-bracket">]</span></a></sup> He had intended to use the solid <a href="/wiki/Triacetone_triperoxide" class="mw-redirect" title="Triacetone triperoxide">triacetone triperoxide</a> (TATP) as a detonator.<sup id="cite_ref-nyt_21-1" class="reference"><a href="#cite_note-nyt-21"><span class="cite-bracket">[</span>21<span class="cite-bracket">]</span></a></sup> </p><p>In 2009, PETN was used in an attempt by <a href="/wiki/Al-Qaeda_in_the_Arabian_Peninsula" title="Al-Qaeda in the Arabian Peninsula">al-Qaeda in the Arabian Peninsula</a> to murder the Saudi Arabian Deputy Minister of Interior Prince <a href="/wiki/Muhammad_bin_Nayef" title="Muhammad bin Nayef">Muhammad bin Nayef</a>, by Saudi <a href="/wiki/Suicide_bomber" class="mw-redirect" title="Suicide bomber">suicide bomber</a> <a href="/wiki/Abdullah_Hassan_Al_Aseery" class="mw-redirect" title="Abdullah Hassan Al Aseery">Abdullah Hassan al Asiri</a>. The target survived and the bomber died in the blast. The PETN was hidden in the bomber's <a href="/wiki/Rectum" title="Rectum">rectum</a>, which security experts described as a novel technique.<sup id="cite_ref-35" class="reference"><a href="#cite_note-35"><span class="cite-bracket">[</span>35<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-36" class="reference"><a href="#cite_note-36"><span class="cite-bracket">[</span>36<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-37" class="reference"><a href="#cite_note-37"><span class="cite-bracket">[</span>37<span class="cite-bracket">]</span></a></sup> </p><p>On 25 December 2009, PETN was found in the underwear of <a href="/wiki/Umar_Farouk_Abdulmutallab" title="Umar Farouk Abdulmutallab">Umar Farouk Abdulmutallab</a>, the "Underwear bomber", a Nigerian with links to al-Qaeda in the Arabian Peninsula.<sup id="cite_ref-38" class="reference"><a href="#cite_note-38"><span class="cite-bracket">[</span>38<span class="cite-bracket">]</span></a></sup> According to US law enforcement officials,<sup id="cite_ref-39" class="reference"><a href="#cite_note-39"><span class="cite-bracket">[</span>39<span class="cite-bracket">]</span></a></sup> he had attempted to blow up <a href="/wiki/Northwest_Airlines_Flight_253" title="Northwest Airlines Flight 253">Northwest Airlines Flight 253</a> while approaching Detroit from Amsterdam.<sup id="cite_ref-urlABC_News|AMERICAS|Investigators:_Northwest_Bomb_Plot_Planned_by_Al-Qaeda_in_Yemen_40-0" class="reference"><a href="#cite_note-urlABC_News|AMERICAS|Investigators:_Northwest_Bomb_Plot_Planned_by_Al-Qaeda_in_Yemen-40"><span class="cite-bracket">[</span>40<span class="cite-bracket">]</span></a></sup> Abdulmutallab had tried, unsuccessfully, to detonate approximately 80 grams (2.8 oz) of PETN sewn into his underwear by adding liquid from a syringe;<sup id="cite_ref-41" class="reference"><a href="#cite_note-41"><span class="cite-bracket">[</span>41<span class="cite-bracket">]</span></a></sup> however, only a small fire resulted.<sup id="cite_ref-nyt_21-2" class="reference"><a href="#cite_note-nyt-21"><span class="cite-bracket">[</span>21<span class="cite-bracket">]</span></a></sup> </p><p>In the al-Qaeda in the Arabian Peninsula October <a href="/wiki/2010_cargo_plane_bomb_plot" class="mw-redirect" title="2010 cargo plane bomb plot">2010 cargo plane bomb plot</a>, two PETN-filled printer cartridges were found at <a href="/wiki/East_Midlands_Airport" title="East Midlands Airport">East Midlands Airport</a> and in <a href="/wiki/Dubai" title="Dubai">Dubai</a> on flights bound for the US on an intelligence tip. Both packages contained sophisticated bombs concealed in computer <a href="/wiki/Toner_cartridge" title="Toner cartridge">printer cartridges</a> filled with PETN.<sup id="cite_ref-scientificamerican1_42-0" class="reference"><a href="#cite_note-scientificamerican1-42"><span class="cite-bracket">[</span>42<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-nytimes4_43-0" class="reference"><a href="#cite_note-nytimes4-43"><span class="cite-bracket">[</span>43<span class="cite-bracket">]</span></a></sup> The bomb found in England contained 400 grams (14 oz) of PETN, and the one found in Dubai contained 300 grams (11 oz) of PETN.<sup id="cite_ref-nytimes4_43-1" class="reference"><a href="#cite_note-nytimes4-43"><span class="cite-bracket">[</span>43<span class="cite-bracket">]</span></a></sup> Hans Michels, professor of <a href="/wiki/Safety_engineering" title="Safety engineering">safety engineering</a> at <a href="/wiki/University_College_London" title="University College London">University College London</a>, told a newspaper that 6 grams (0.21 oz) of PETN—"around 50 times less than was used—would be enough to blast a hole in a metal plate twice the thickness of an aircraft's skin".<sup id="cite_ref-44" class="reference"><a href="#cite_note-44"><span class="cite-bracket">[</span>44<span class="cite-bracket">]</span></a></sup> In contrast, according to an experiment conducted by a BBC documentary team designed to simulate Abdulmutallab's Christmas Day bombing, using a Boeing 747 plane, even 80 grams of PETN was not sufficient to materially damage the fuselage.<sup id="cite_ref-45" class="reference"><a href="#cite_note-45"><span class="cite-bracket">[</span>45<span class="cite-bracket">]</span></a></sup> </p><p>On 12 July 2017, 150 grams of PETN was found in the <a href="/wiki/Uttar_Pradesh_Legislative_Assembly" title="Uttar Pradesh Legislative Assembly">Assembly of Uttar Pradesh</a>,<sup id="cite_ref-46" class="reference"><a href="#cite_note-46"><span class="cite-bracket">[</span>46<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-47" class="reference"><a href="#cite_note-47"><span class="cite-bracket">[</span>47<span class="cite-bracket">]</span></a></sup> India's most populous state.<sup id="cite_ref-48" class="reference"><a href="#cite_note-48"><span class="cite-bracket">[</span>48<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-49" class="reference"><a href="#cite_note-49"><span class="cite-bracket">[</span>49<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Detection">Detection</h3></div> <p>In the wake of terrorist PETN bomb plots, an article in <i><a href="/wiki/Scientific_American" title="Scientific American">Scientific American</a></i> noted PETN is difficult to detect because it does not readily vaporize into the surrounding air.<sup id="cite_ref-scientificamerican1_42-1" class="reference"><a href="#cite_note-scientificamerican1-42"><span class="cite-bracket">[</span>42<span class="cite-bracket">]</span></a></sup> The <i><a href="/wiki/Los_Angeles_Times" title="Los Angeles Times">Los Angeles Times</a></i> noted in November 2010 that PETN's low <a href="/wiki/Vapor_pressure" title="Vapor pressure">vapor pressure</a> makes it difficult for bomb-sniffing dogs to detect.<sup id="cite_ref-latimes.com_20-2" class="reference"><a href="#cite_note-latimes.com-20"><span class="cite-bracket">[</span>20<span class="cite-bracket">]</span></a></sup> </p><p>Many technologies can be used to detect PETN, including chemical sensors, X-rays, infrared, microwaves<sup id="cite_ref-50" class="reference"><a href="#cite_note-50"><span class="cite-bracket">[</span>50<span class="cite-bracket">]</span></a></sup> and terahertz,<sup id="cite_ref-51" class="reference"><a href="#cite_note-51"><span class="cite-bracket">[</span>51<span class="cite-bracket">]</span></a></sup> some of which have been implemented in public screening applications, primarily for air travel. PETN is one of the explosive chemicals typically of interest in that area, and it belongs to a family of common <a href="/wiki/Nitro_compound" title="Nitro compound">nitrate-based explosive chemicals</a> which can often be detected by the same tests. </p><p>One detection system in use at airports involves analysis of swab samples obtained from passengers and their baggage. Whole-body imaging scanners that use radio-frequency <a href="/wiki/Electromagnetic_wave" class="mw-redirect" title="Electromagnetic wave">electromagnetic waves</a>, low-intensity <a href="/wiki/X-rays" class="mw-redirect" title="X-rays">X-rays</a>, or T-rays of terahertz frequency that can detect objects hidden under clothing are not widely used because of cost, concerns about the resulting traveler delays, and privacy concerns.<sup id="cite_ref-52" class="reference"><a href="#cite_note-52"><span class="cite-bracket">[</span>52<span class="cite-bracket">]</span></a></sup> </p><p>Both parcels in the 2010 cargo plane bomb plot were x-rayed without the bombs being spotted.<sup id="cite_ref-spiegel1_53-0" class="reference"><a href="#cite_note-spiegel1-53"><span class="cite-bracket">[</span>53<span class="cite-bracket">]</span></a></sup> <a href="/wiki/Qatar_Airways" title="Qatar Airways">Qatar Airways</a> said the PETN bomb "could not be detected by x-ray screening or trained <a href="/wiki/Sniffer_dog" class="mw-redirect" title="Sniffer dog">sniffer dogs</a>".<sup id="cite_ref-autogenerated1_54-0" class="reference"><a href="#cite_note-autogenerated1-54"><span class="cite-bracket">[</span>54<span class="cite-bracket">]</span></a></sup> The <a href="/wiki/Federal_Criminal_Police_Office_(Germany)" title="Federal Criminal Police Office (Germany)">Bundeskriminalamt</a> received copies of the Dubai x-rays, and an investigator said German staff would not have identified the bomb either.<sup id="cite_ref-spiegel1_53-1" class="reference"><a href="#cite_note-spiegel1-53"><span class="cite-bracket">[</span>53<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-aljazeera1_55-0" class="reference"><a href="#cite_note-aljazeera1-55"><span class="cite-bracket">[</span>55<span class="cite-bracket">]</span></a></sup> New airport security procedures followed in the U.S., largely to protect against PETN.<sup id="cite_ref-latimes.com_20-3" class="reference"><a href="#cite_note-latimes.com-20"><span class="cite-bracket">[</span>20<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Medical_use">Medical use</h2></div> <p>Like <a href="/wiki/Nitroglycerin" title="Nitroglycerin">nitroglycerin</a> (glyceryl trinitrate) and other <a href="/wiki/Nitrate_(pharmacology)" class="mw-redirect" title="Nitrate (pharmacology)">nitrates</a>, PETN is also used medically as a <a href="/wiki/Vasodilator" class="mw-redirect" title="Vasodilator">vasodilator</a> in the treatment of <a href="/wiki/Heart_disease" class="mw-redirect" title="Heart disease">heart conditions</a>.<sup id="cite_ref-newdrugs_4-1" class="reference"><a href="#cite_note-newdrugs-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-ebadi_5-1" class="reference"><a href="#cite_note-ebadi-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> These drugs work by releasing the signaling gas <a href="/wiki/Nitric_oxide" title="Nitric oxide">nitric oxide</a> in the body. The heart medicine <i>Lentonitrat</i> is nearly pure PETN.<sup id="cite_ref-56" class="reference"><a href="#cite_note-56"><span class="cite-bracket">[</span>56<span class="cite-bracket">]</span></a></sup> </p><p>Monitoring of oral usage of the drug by patients has been performed by determination of plasma levels of several of its hydrolysis products, pentaerythritol dinitrate, pentaerythritol mononitrate and pentaerythritol, in plasma using <a href="/wiki/Gas_chromatography-mass_spectrometry" class="mw-redirect" title="Gas chromatography-mass spectrometry">gas chromatography-mass spectrometry</a>.<sup id="cite_ref-57" class="reference"><a href="#cite_note-57"><span class="cite-bracket">[</span>57<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="See_also">See also</h2></div> <ul><li><a href="/wiki/Erythritol_tetranitrate" title="Erythritol tetranitrate">Erythritol tetranitrate</a></li> <li><a href="/wiki/RE_factor" class="mw-redirect" title="RE factor">RE factor</a></li></ul> <div class="mw-heading mw-heading2"><h2 id="References">References</h2></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-epa1-1"><span class="mw-cite-backlink"><b><a href="#cite_ref-epa1_1-0">^</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 class="citation web cs1"><a rel="nofollow" class="external text" href="https://hhpprtv.ornl.gov/issue_papers/PentaerythritoltetranitratePETN.pdf">"Provisional Peer-Reviewed Toxicity Values for Pentaerythritol Tetranitrate (PETN) (CASRN 78-11-5)"</a> <span class="cs1-format">(PDF)</span>. United States Environmental Protection Agency. July 2021. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20240801034435/https://hhpprtv.ornl.gov/issue_papers/PentaerythritoltetranitratePETN.pdf">Archived</a> <span class="cs1-format">(PDF)</span> from the original on August 1, 2024.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=Provisional+Peer-Reviewed+Toxicity+Values+for+Pentaerythritol+Tetranitrate+%28PETN%29+%28CASRN+78-11-5%29&rft.pub=United+States+Environmental+Protection+Agency&rft.date=2021-07&rft_id=https%3A%2F%2Fhhpprtv.ornl.gov%2Fissue_papers%2FPentaerythritoltetranitratePETN.pdf&rfr_id=info%3Asid%2Fen.wikipedia.org%3APentaerythritol+tetranitrate" class="Z3988"></span></span> </li> <li id="cite_note-urlPETN_[Pentaerythritol_tetranitrate]-2"><span class="mw-cite-backlink"><b><a href="#cite_ref-urlPETN_[Pentaerythritol_tetranitrate]_2-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="http://www.globalsecurity.org/military/systems/munitions/explosives-nitrate-petn.htm">"PETN (Pentaerythritol tetranitrate)"</a><span class="reference-accessdate">. Retrieved <span class="nowrap">March 29,</span> 2010</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=PETN+%28Pentaerythritol+tetranitrate%29&rft_id=http%3A%2F%2Fwww.globalsecurity.org%2Fmilitary%2Fsystems%2Fmunitions%2Fexplosives-nitrate-petn.htm&rfr_id=info%3Asid%2Fen.wikipedia.org%3APentaerythritol+tetranitrate" 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="CITEREFChilds1994" class="citation encyclopaedia cs1">Childs, John (1994). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=nEQ7FUAdmc8C&pg=PA231">"Explosives"</a> <span class="cs1-format">(<a href="/wiki/Google_Books" title="Google Books">Google Books</a> extract)</span>. <i>A dictionary of military history and the art of war</i>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-631-16848-5" title="Special:BookSources/978-0-631-16848-5"><bdi>978-0-631-16848-5</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Explosives&rft.btitle=A+dictionary+of+military+history+and+the+art+of+war&rft.date=1994&rft.isbn=978-0-631-16848-5&rft.aulast=Childs&rft.aufirst=John&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DnEQ7FUAdmc8C%26pg%3DPA231&rfr_id=info%3Asid%2Fen.wikipedia.org%3APentaerythritol+tetranitrate" class="Z3988"></span></span> </li> <li id="cite_note-newdrugs-4"><span class="mw-cite-backlink">^ <a href="#cite_ref-newdrugs_4-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-newdrugs_4-1"><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 class="citation journal cs1"><a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1831125">"New Drugs"</a>. <i><a href="/wiki/Can_Med_Assoc_J" class="mw-redirect" title="Can Med Assoc J">Can Med Assoc J</a></i>. <b>80</b> (12): 997–998. 1959. <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/PMC1831125">1831125</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/20325960">20325960</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Can+Med+Assoc+J&rft.atitle=New+Drugs&rft.volume=80&rft.issue=12&rft.pages=997-998&rft.date=1959&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC1831125%23id-name%3DPMC&rft_id=info%3Apmid%2F20325960&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC1831125&rfr_id=info%3Asid%2Fen.wikipedia.org%3APentaerythritol+tetranitrate" class="Z3988"></span></span> </li> <li id="cite_note-ebadi-5"><span class="mw-cite-backlink">^ <a href="#cite_ref-ebadi_5-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-ebadi_5-1"><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="CITEREFEbadi,_Manuchair_S.1998" class="citation book cs1">Ebadi, Manuchair S. (1998). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=-EAxShTKfGAC&pg=PA383"><i>CRC desk reference of clinical pharmacology</i></a> <span class="cs1-format">(<a href="/wiki/Google_Books" title="Google Books">Google Books</a> excerpt)</span>. CRC Press. p. 383. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-8493-9683-0" title="Special:BookSources/978-0-8493-9683-0"><bdi>978-0-8493-9683-0</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=CRC+desk+reference+of+clinical+pharmacology&rft.pages=383&rft.pub=CRC+Press&rft.date=1998&rft.isbn=978-0-8493-9683-0&rft.au=Ebadi%2C+Manuchair+S.&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3D-EAxShTKfGAC%26pg%3DPA383&rfr_id=info%3Asid%2Fen.wikipedia.org%3APentaerythritol+tetranitrate" 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">Deutsches Reichspatent 81,664 (1894)</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">Thieme, Bruno <a rel="nofollow" class="external text" href="http://pdfpiw.uspto.gov/.piw?Docid=00541899&homeurl=http%3A%2F%2Fpatft.uspto.gov%2Fnetacgi%2Fnph-Parser%3FSect1%3DPTO1%2526Sect2%3DHITOFF%2526d%3DPALL%2526p%3D1%2526u%3D%25252Fnetahtml%25252FPTO%25252Fsrchnum.htm%2526r%3D1%2526f%3DG%2526l%3D50%2526s1%3D0541,899.PN.%2526OS%3DPN%2F0541,899%2526RS%3DPN%2F0541,899&PageNum=&Rtype=&SectionNum=&idkey=NONE&Input=View+first+page">"Process of making nitropentaerythrit,"</a> <a rel="nofollow" class="external text" href="https://web.archive.org/web/20210711151323/https://pdfpiw.uspto.gov/.piw?Docid=00541899&homeurl=http%3A%2F%2Fpatft.uspto.gov%2Fnetacgi%2Fnph-Parser%3FSect1%3DPTO1%2526Sect2%3DHITOFF%2526d%3DPALL%2526p%3D1%2526u%3D%25252Fnetahtml%25252FPTO%25252Fsrchnum.htm%2526r%3D1%2526f%3DG%2526l%3D50%2526s1%3D0541%2C899.PN.%2526OS%3DPN%2F0541%2C899%2526RS%3DPN%2F0541%2C899&PageNum=&Rtype=&SectionNum=&idkey=NONE&Input=View+first+page">Archived</a> July 11, 2021, at the <a href="/wiki/Wayback_Machine" title="Wayback Machine">Wayback Machine</a> U.S. patent no. 541,899 (filed: November 13, 1894; issued: July 2, 1895).</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">Krehl, Peter O. K. (2009) <i>History of Shock Waves, Explosions and Impact</i>. Berlin, Germany: Springer-Verlag. <a rel="nofollow" class="external text" href="https://books.google.com/books?id=PmuqCHDC3pwC&pg=PA405">p. 405</a>.</span> </li> <li id="cite_note-9"><span class="mw-cite-backlink"><b><a href="#cite_ref-9">^</a></b></span> <span class="reference-text">Urbański, Tadeusz; Ornaf, Władysław and Laverton, Sylvia (1965) <i>Chemistry and Technology of Explosives</i>, vol. 2 (Oxford, England: Permagon Press. <a rel="nofollow" class="external text" href="https://archive.org/stream/ChemistryAndTechnologyOfExplosives-VolumeIi/ChemistryAndTechnologyOfExplosives-VolumeIi-TadeuszUrbanski#page/n183/mode/2up">p. 175.</a></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">German Patent 265,025 (1912)</span> </li> <li id="cite_note-11"><span class="mw-cite-backlink"><b><a href="#cite_ref-11">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFStettbacher,_Alfred1933" class="citation book cs1">Stettbacher, Alfred (1933). <i>Die Schiess- und Sprengstoffe</i> (2. völlig umgearb. Aufl. ed.). Leipzig: Barth. p. 459.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Die+Schiess-+und+Sprengstoffe&rft.place=Leipzig&rft.pages=459&rft.edition=2.+v%C3%B6llig+umgearb.+Aufl.&rft.pub=Barth&rft.date=1933&rft.au=Stettbacher%2C+Alfred&rfr_id=info%3Asid%2Fen.wikipedia.org%3APentaerythritol+tetranitrate" class="Z3988"></span></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="CITEREFZhurova,_Elizabeth_A.;_Stash,_Adam_I.;_Tsirelson,_Vladimir_G.;_Zhurov,_Vladimir_V.;_Bartashevich,_Ekaterina_V.;_Potemkin,_Vladimir_A.;_Pinkerton,_A._Alan2006" class="citation journal cs1">Zhurova, Elizabeth A.; Stash, Adam I.; Tsirelson, Vladimir G.; Zhurov, Vladimir V.; Bartashevich, Ekaterina V.; Potemkin, Vladimir A.; Pinkerton, A. Alan (2006). "Atoms-in-Molecules Study of Intra- and Intermolecular Bonding in the Pentaerythritol Tetranitrate Crystal". <i>Journal of the American Chemical Society</i>. <b>128</b> (45): 14728–14734. <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%2Fja0658620">10.1021/ja0658620</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/17090061">17090061</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=Atoms-in-Molecules+Study+of+Intra-+and+Intermolecular+Bonding+in+the+Pentaerythritol+Tetranitrate+Crystal&rft.volume=128&rft.issue=45&rft.pages=14728-14734&rft.date=2006&rft_id=info%3Adoi%2F10.1021%2Fja0658620&rft_id=info%3Apmid%2F17090061&rft.au=Zhurova%2C+Elizabeth+A.%3B+Stash%2C+Adam+I.%3B+Tsirelson%2C+Vladimir+G.%3B+Zhurov%2C+Vladimir+V.%3B+Bartashevich%2C+Ekaterina+V.%3B+Potemkin%2C+Vladimir+A.%3B+Pinkerton%2C+A.+Alan&rfr_id=info%3Asid%2Fen.wikipedia.org%3APentaerythritol+tetranitrate" class="Z3988"></span><span class="cs1-maint citation-comment"><code class="cs1-code">{{<a href="/wiki/Template:Cite_journal" title="Template:Cite journal">cite journal</a>}}</code>: CS1 maint: multiple names: authors list (<a href="/wiki/Category:CS1_maint:_multiple_names:_authors_list" title="Category:CS1 maint: multiple names: authors list">link</a>)</span></span> </li> <li id="cite_note-13"><span class="mw-cite-backlink"><b><a href="#cite_ref-13">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFFoltz2009" class="citation techreport cs1">Foltz, M. F. (July 27, 2009). <a rel="nofollow" class="external text" href="https://www.osti.gov/servlets/purl/966904"><i>Aging of Pentaerythritol Tetranitrate (PETN)</i></a> (Technical report). <a href="/wiki/Lawrence_Livermore_National_Laboratory" title="Lawrence Livermore National Laboratory">Lawrence Livermore National Laboratory</a>. <a href="/wiki/OSTI_(identifier)" class="mw-redirect" title="OSTI (identifier)">OSTI</a> <a rel="nofollow" class="external text" href="https://www.osti.gov/biblio/966904">966904</a>. LLNL-TR-415057<span class="reference-accessdate">. Retrieved <span class="nowrap">May 14,</span> 2023</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=report&rft.btitle=Aging+of+Pentaerythritol+Tetranitrate+%28PETN%29&rft.pub=Lawrence+Livermore+National+Laboratory&rft.date=2009-07-27&rft_id=https%3A%2F%2Fwww.osti.gov%2Fbiblio%2F966904%23id-name%3DOSTI&rft.aulast=Foltz&rft.aufirst=M.+F.&rft_id=https%3A%2F%2Fwww.osti.gov%2Fservlets%2Fpurl%2F966904&rfr_id=info%3Asid%2Fen.wikipedia.org%3APentaerythritol+tetranitrate" class="Z3988"></span></span> </li> <li id="cite_note-14"><span class="mw-cite-backlink"><b><a href="#cite_ref-14">^</a></b></span> <span class="reference-text">German, V.N. et al. <a rel="nofollow" class="external text" href="http://www.intdetsymp.org/detsymp2002/PaperSubmit/FinalManuscript/pdf/German-258.pdf">Thermal decomposition of PENT and HMX over a wide temperature range</a> <a rel="nofollow" class="external text" href="https://web.archive.org/web/20200410211224/http://www.intdetsymp.org/detsymp2002/PaperSubmit/FinalManuscript/pdf/German-258.pdf">Archived</a> April 10, 2020, at the <a href="/wiki/Wayback_Machine" title="Wayback Machine">Wayback Machine</a>. Institute of Physics of Explosion, RFNC-VNIIEF, Sarov, Russia</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="CITEREFZhuangGuiGillham2012" class="citation journal cs1">Zhuang, Li; Gui, Lai; Gillham, Robert W. (October 1, 2012). <a rel="nofollow" class="external text" href="http://www.sciencedirect.com/science/article/pii/S0045653512005942">"Biodegradation of pentaerythritol tetranitrate (PETN) by anaerobic consortia from a contaminated site"</a>. <i>Chemosphere</i>. <b>89</b> (7): 810–816. <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/2012Chmsp..89..810Z">2012Chmsp..89..810Z</a>. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2Fj.chemosphere.2012.04.062">10.1016/j.chemosphere.2012.04.062</a>. <a href="/wiki/ISSN_(identifier)" class="mw-redirect" title="ISSN (identifier)">ISSN</a> <a rel="nofollow" class="external text" href="https://search.worldcat.org/issn/0045-6535">0045-6535</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/22647196">22647196</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Chemosphere&rft.atitle=Biodegradation+of+pentaerythritol+tetranitrate+%28PETN%29+by+anaerobic+consortia+from+a+contaminated+site&rft.volume=89&rft.issue=7&rft.pages=810-816&rft.date=2012-10-01&rft_id=info%3Adoi%2F10.1016%2Fj.chemosphere.2012.04.062&rft.issn=0045-6535&rft_id=info%3Apmid%2F22647196&rft_id=info%3Abibcode%2F2012Chmsp..89..810Z&rft.aulast=Zhuang&rft.aufirst=Li&rft.au=Gui%2C+Lai&rft.au=Gillham%2C+Robert+W.&rft_id=http%3A%2F%2Fwww.sciencedirect.com%2Fscience%2Farticle%2Fpii%2FS0045653512005942&rfr_id=info%3Asid%2Fen.wikipedia.org%3APentaerythritol+tetranitrate" 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="CITEREFZhuangGuiGillham2008" class="citation journal cs1">Zhuang, L; Gui, L; Gillham, R. W. (2008). "Degradation of Pentaerythritol Tetranitrate (PETN) by Granular Iron". <i><a href="/wiki/Environ._Sci._Technol." class="mw-redirect" title="Environ. Sci. Technol.">Environ. Sci. Technol.</a></i> <b>42</b> (12): 4534–9. <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/2008EnST...42.4534Z">2008EnST...42.4534Z</a>. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1021%2Fes7029703">10.1021/es7029703</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/18605582">18605582</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Environ.+Sci.+Technol.&rft.atitle=Degradation+of+Pentaerythritol+Tetranitrate+%28PETN%29+by+Granular+Iron&rft.volume=42&rft.issue=12&rft.pages=4534-9&rft.date=2008&rft_id=info%3Apmid%2F18605582&rft_id=info%3Adoi%2F10.1021%2Fes7029703&rft_id=info%3Abibcode%2F2008EnST...42.4534Z&rft.aulast=Zhuang&rft.aufirst=L&rft.au=Gui%2C+L&rft.au=Gillham%2C+R.+W.&rfr_id=info%3Asid%2Fen.wikipedia.org%3APentaerythritol+tetranitrate" class="Z3988"></span></span> </li> <li id="cite_note-Ullmann-17"><span class="mw-cite-backlink">^ <a href="#cite_ref-Ullmann_17-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Ullmann_17-1"><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="CITEREFBoileau,_JacquesFauquignon,_ClaudeHueber,_BernardMeyer,_Hans_H." class="citation encyclopaedia cs1">Boileau, Jacques; Fauquignon, Claude; Hueber, Bernard & Meyer, Hans H. "Explosives". <i><a href="/wiki/Ullmann%27s_Encyclopedia_of_Industrial_Chemistry" title="Ullmann's Encyclopedia of Industrial Chemistry">Ullmann's Encyclopedia of Industrial Chemistry</a></i>. Weinheim: Wiley-VCH. <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%2F14356007.a10_143.pub2">10.1002/14356007.a10_143.pub2</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-3527306732" title="Special:BookSources/978-3527306732"><bdi>978-3527306732</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Explosives&rft.btitle=Ullmann%27s+Encyclopedia+of+Industrial+Chemistry&rft.place=Weinheim&rft.pub=Wiley-VCH&rft_id=info%3Adoi%2F10.1002%2F14356007.a10_143.pub2&rft.isbn=978-3527306732&rft.au=Boileau%2C+Jacques&rft.au=Fauquignon%2C+Claude&rft.au=Hueber%2C+Bernard&rft.au=Meyer%2C+Hans+H.&rfr_id=info%3Asid%2Fen.wikipedia.org%3APentaerythritol+tetranitrate" class="Z3988"></span></span> </li> <li id="cite_note-18"><span class="mw-cite-backlink"><b><a href="#cite_ref-18">^</a></b></span> <span class="reference-text">Winslow, Ron. (December 29, 2009) <a rel="nofollow" class="external text" href="https://www.wsj.com/articles/SB126195987401406861">A Primer in PETN – WSJ.com</a>. <i>The Wall Street Journal</i>. Retrieved 2010-02-08.</span> </li> <li id="cite_note-19"><span class="mw-cite-backlink"><b><a href="#cite_ref-19">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFOxleySmithKirschenbaumShinde2005" class="citation journal cs1">Oxley, Jimmie C.; Smith, James L.; Kirschenbaum, Louis J.; Shinde, Kajal. P.; Marimganti, Suvarna (2005). "Accumulation of Explosives in Hair". <i>Journal of Forensic Sciences</i>. <b>50</b> (4): 826–31. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1520%2FJFS2004545">10.1520/JFS2004545</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/16078483">16078483</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+Forensic+Sciences&rft.atitle=Accumulation+of+Explosives+in+Hair&rft.volume=50&rft.issue=4&rft.pages=826-31&rft.date=2005&rft_id=info%3Adoi%2F10.1520%2FJFS2004545&rft_id=info%3Apmid%2F16078483&rft.aulast=Oxley&rft.aufirst=Jimmie+C.&rft.au=Smith%2C+James+L.&rft.au=Kirschenbaum%2C+Louis+J.&rft.au=Shinde%2C+Kajal.+P.&rft.au=Marimganti%2C+Suvarna&rfr_id=info%3Asid%2Fen.wikipedia.org%3APentaerythritol+tetranitrate" class="Z3988"></span></span> </li> <li id="cite_note-latimes.com-20"><span class="mw-cite-backlink">^ <a href="#cite_ref-latimes.com_20-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-latimes.com_20-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-latimes.com_20-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-latimes.com_20-3"><sup><i><b>d</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFBennett2010" class="citation news cs1">Bennett, Brian (November 24, 2010). <a rel="nofollow" class="external text" href="https://www.latimes.com/archives/la-xpm-2010-nov-24-la-na-petn-20101124-story.html">"PETN: The explosive that airport security is targeting"</a>. <i>Los Angeles Times</i>. Tribune Washington Bureau<span class="reference-accessdate">. Retrieved <span class="nowrap">July 19,</span> 2015</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Los+Angeles+Times&rft.atitle=PETN%3A+The+explosive+that+airport+security+is+targeting&rft.date=2010-11-24&rft.aulast=Bennett&rft.aufirst=Brian&rft_id=https%3A%2F%2Fwww.latimes.com%2Farchives%2Fla-xpm-2010-nov-24-la-na-petn-20101124-story.html&rfr_id=info%3Asid%2Fen.wikipedia.org%3APentaerythritol+tetranitrate" class="Z3988"></span></span> </li> <li id="cite_note-nyt-21"><span class="mw-cite-backlink">^ <a href="#cite_ref-nyt_21-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-nyt_21-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-nyt_21-2"><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="CITEREFChang,_Kenneth2009" class="citation news cs1">Chang, Kenneth (December 27, 2009). <a rel="nofollow" class="external text" href="https://www.nytimes.com/2009/12/28/us/28explosives.html?ref=us">"Explosive on Flight 253 Is Among Most Powerful"</a>. <i>The New York Times</i>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=The+New+York+Times&rft.atitle=Explosive+on+Flight+253+Is+Among+Most+Powerful&rft.date=2009-12-27&rft.au=Chang%2C+Kenneth&rft_id=https%3A%2F%2Fwww.nytimes.com%2F2009%2F12%2F28%2Fus%2F28explosives.html%3Fref%3Dus&rfr_id=info%3Asid%2Fen.wikipedia.org%3APentaerythritol+tetranitrate" class="Z3988"></span></span> </li> <li id="cite_note-urlwww.dynonobel.com-22"><span class="mw-cite-backlink"><b><a href="#cite_ref-urlwww.dynonobel.com_22-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://web.archive.org/web/20110710160725/http://www.dynonobel.com/files/2010/04/Primacord.pdf">"Primacord Technical Information"</a> <span class="cs1-format">(PDF)</span>. Dyno Nobel. Archived from <a rel="nofollow" class="external text" href="http://www.dynonobel.com/files/2010/04/Primacord.pdf">the original</a> <span class="cs1-format">(PDF)</span> on July 10, 2011<span class="reference-accessdate">. Retrieved <span class="nowrap">April 22,</span> 2009</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=Primacord+Technical+Information&rft.pub=Dyno+Nobel&rft_id=http%3A%2F%2Fwww.dynonobel.com%2Ffiles%2F2010%2F04%2FPrimacord.pdf&rfr_id=info%3Asid%2Fen.wikipedia.org%3APentaerythritol+tetranitrate" 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="CITEREFZhangLiHe2020" class="citation journal cs1">Zhang, Y.; Li, Q.; He, Y. (2020). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7675531">"Explosive power of Pentaerythritol Tetranitrate"</a>. <i>ACS Omega</i>. <b>5</b> (45): 28984–28991. <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%2Facsomega.0c03133">10.1021/acsomega.0c03133</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/PMC7675531">7675531</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/33225129">33225129</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=ACS+Omega&rft.atitle=Explosive+power+of+Pentaerythritol+Tetranitrate&rft.volume=5&rft.issue=45&rft.pages=28984-28991&rft.date=2020&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC7675531%23id-name%3DPMC&rft_id=info%3Apmid%2F33225129&rft_id=info%3Adoi%2F10.1021%2Facsomega.0c03133&rft.aulast=Zhang&rft.aufirst=Y.&rft.au=Li%2C+Q.&rft.au=He%2C+Y.&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC7675531&rfr_id=info%3Asid%2Fen.wikipedia.org%3APentaerythritol+tetranitrate" 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"><a rel="nofollow" class="external text" href="http://www.britannica.com/EBchecked/topic/454067/PETN">PETN (chemical compound)</a>. <i>Encyclopædia Britannica</i>. Retrieved February 8, 2010.</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="CITEREFLillian_HoddesonPaul_W._HenriksenRoger_A._MeadeCatherine_L._Westfall2004" class="citation book cs1">Lillian Hoddeson; Paul W. Henriksen; Roger A. Meade; Catherine L. Westfall; Gordon Baym; Richard Hewlett; Alison Kerr; Robert Penneman; Leslie Redman; Robert Seidel (2004). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=KoTve97yYB8C&pg=PA164"><i>A Technical History of Los Alamos During the Oppenheimer Years, 1943–1945</i></a> <span class="cs1-format">(<a href="/wiki/Google_Books" title="Google Books">Google Books</a> excerpt)</span>. Cambridge University Press. pp. 164–173. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-521-54117-6" title="Special:BookSources/978-0-521-54117-6"><bdi>978-0-521-54117-6</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=A+Technical+History+of+Los+Alamos+During+the+Oppenheimer+Years%2C+1943%E2%80%931945&rft.pages=164-173&rft.pub=Cambridge+University+Press&rft.date=2004&rft.isbn=978-0-521-54117-6&rft.au=Lillian+Hoddeson&rft.au=Paul+W.+Henriksen&rft.au=Roger+A.+Meade&rft.au=Catherine+L.+Westfall&rft.au=Gordon+Baym&rft.au=Richard+Hewlett&rft.au=Alison+Kerr&rft.au=Robert+Penneman&rft.au=Leslie+Redman&rft.au=Robert+Seidel&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DKoTve97yYB8C%26pg%3DPA164&rfr_id=info%3Asid%2Fen.wikipedia.org%3APentaerythritol+tetranitrate" 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="CITEREFGebeilyPearsonGauthier-Villars2024" class="citation web cs1">Gebeily, Maya; Pearson, James; Gauthier-Villars, David (October 16, 2024). <a rel="nofollow" class="external text" href="https://www.reuters.com/graphics/ISRAEL-PALESTINIANS/HEZBOLLAH-PAGERS/mopawkkwjpa/">"How Israel's bulky pager fooled Hezbollah"</a>. <a href="/wiki/Reuters" title="Reuters">Reuters</a><span class="reference-accessdate">. Retrieved <span class="nowrap">October 16,</span> 2024</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=How+Israel%27s+bulky+pager+fooled+Hezbollah&rft.pub=Reuters&rft.date=2024-10-16&rft.aulast=Gebeily&rft.aufirst=Maya&rft.au=Pearson%2C+James&rft.au=Gauthier-Villars%2C+David&rft_id=https%3A%2F%2Fwww.reuters.com%2Fgraphics%2FISRAEL-PALESTINIANS%2FHEZBOLLAH-PAGERS%2Fmopawkkwjpa%2F&rfr_id=info%3Asid%2Fen.wikipedia.org%3APentaerythritol+tetranitrate" 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="CITEREFShepoddBehrensAnexMiller1997" class="citation techreport cs1">Shepodd, T; Behrens, R; Anex, D; Miller, D; Anderson, K (July 1, 1997). <a rel="nofollow" class="external text" href="https://www.osti.gov/servlets/purl/650196"><i>Degradation chemistry of PETN and its homologues</i></a> (Technical report). Sandia National Laboratory. <a href="/wiki/OSTI_(identifier)" class="mw-redirect" title="OSTI (identifier)">OSTI</a> <a rel="nofollow" class="external text" href="https://www.osti.gov/biblio/650196">650196</a>. SAND-97-8684C<span class="reference-accessdate">. Retrieved <span class="nowrap">May 14,</span> 2023</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=report&rft.btitle=Degradation+chemistry+of+PETN+and+its+homologues&rft.pub=Sandia+National+Laboratory&rft.date=1997-07-01&rft_id=https%3A%2F%2Fwww.osti.gov%2Fbiblio%2F650196%23id-name%3DOSTI&rft.aulast=Shepodd&rft.aufirst=T&rft.au=Behrens%2C+R&rft.au=Anex%2C+D&rft.au=Miller%2C+D&rft.au=Anderson%2C+K&rft_id=https%3A%2F%2Fwww.osti.gov%2Fservlets%2Fpurl%2F650196&rfr_id=info%3Asid%2Fen.wikipedia.org%3APentaerythritol+tetranitrate" class="Z3988"></span></span> </li> <li id="cite_note-28"><span class="mw-cite-backlink"><b><a href="#cite_ref-28">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFTarzhanovZinchenkoSdobnovTokarev1996" class="citation journal cs1">Tarzhanov, V. I.; Zinchenko, A. D.; Sdobnov, V. I.; Tokarev, B. B.; Pogrebov, A. I.; Volkova, A. A. (1996). "Laser initiation of PETN". <i>Combustion, Explosion, and Shock Waves</i>. <b>32</b> (4): 454. <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%2FBF01998499">10.1007/BF01998499</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:98083192">98083192</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Combustion%2C+Explosion%2C+and+Shock+Waves&rft.atitle=Laser+initiation+of+PETN&rft.volume=32&rft.issue=4&rft.pages=454&rft.date=1996&rft_id=info%3Adoi%2F10.1007%2FBF01998499&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A98083192%23id-name%3DS2CID&rft.aulast=Tarzhanov&rft.aufirst=V.+I.&rft.au=Zinchenko%2C+A.+D.&rft.au=Sdobnov%2C+V.+I.&rft.au=Tokarev%2C+B.+B.&rft.au=Pogrebov%2C+A.+I.&rft.au=Volkova%2C+A.+A.&rfr_id=info%3Asid%2Fen.wikipedia.org%3APentaerythritol+tetranitrate" class="Z3988"></span></span> </li> <li id="cite_note-29"><span class="mw-cite-backlink"><b><a href="#cite_ref-29">^</a></b></span> <span class="reference-text">US Army – Encyclopedia of Explosives and Related Items, vol.8</span> </li> <li id="cite_note-30"><span class="mw-cite-backlink"><b><a href="#cite_ref-30">^</a></b></span> <span class="reference-text"><a rel="nofollow" class="external text" href="http://fluid.ippt.gov.pl/ictam04/CD_ICTAM04/FM3/12843/FM3_12843.pdf">Simulation of ram accelerator with PETN layer</a>, Arkadiusz Kobiera and Piotr Wolanski, XXI ICTAM, August 15–21, 2004, Warsaw, Poland</span> </li> <li id="cite_note-31"><span class="mw-cite-backlink"><b><a href="#cite_ref-31">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFWei-Guang_Liu2009" class="citation journal cs1">Wei-Guang Liu; et al. (2009). <a rel="nofollow" class="external text" href="https://web.archive.org/web/20180321192503/http://www.wag.caltech.edu/publications/sup/pdf/806.pdf">"Explanation of the Colossal Detonation Sensitivity of Silicon Pentaerythritol Tetranitrate (Si-PETN) Explosive"</a> <span class="cs1-format">(PDF)</span>. <i>J. Am. Chem. Soc</i>. <b>131</b> (22): 7490–1. <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%2Fja809725p">10.1021/ja809725p</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/19489634">19489634</a>. Archived from <a rel="nofollow" class="external text" href="http://www.wag.caltech.edu/publications/sup/pdf/806.pdf">the original</a> <span class="cs1-format">(PDF)</span> on March 21, 2018<span class="reference-accessdate">. Retrieved <span class="nowrap">January 3,</span> 2010</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=J.+Am.+Chem.+Soc.&rft.atitle=Explanation+of+the+Colossal+Detonation+Sensitivity+of+Silicon+Pentaerythritol+Tetranitrate+%28Si-PETN%29+Explosive&rft.volume=131&rft.issue=22&rft.pages=7490-1&rft.date=2009&rft_id=info%3Adoi%2F10.1021%2Fja809725p&rft_id=info%3Apmid%2F19489634&rft.au=Wei-Guang+Liu&rft_id=http%3A%2F%2Fwww.wag.caltech.edu%2Fpublications%2Fsup%2Fpdf%2F806.pdf&rfr_id=info%3Asid%2Fen.wikipedia.org%3APentaerythritol+tetranitrate" class="Z3988"></span></span> </li> <li id="cite_note-32"><span class="mw-cite-backlink"><b><a href="#cite_ref-32">^</a></b></span> <span class="reference-text"><a rel="nofollow" class="external text" href="http://comporgchem.com/blog/?p=258">Computational Organic Chemistry » Si-PETN sensitivity explained</a>. Comporgchem.com (July 20, 2009). Retrieved 2010-02-08.</span> </li> <li id="cite_note-33"><span class="mw-cite-backlink"><b><a href="#cite_ref-33">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation news cs1"><a rel="nofollow" class="external text" href="http://www.spiegel.de/panorama/0,1518,56218,00.html">"Article detailing attack on Maison de France in Berlin (German)"</a>. <i>Der Spiegel</i>. December 13, 1999<span class="reference-accessdate">. Retrieved <span class="nowrap">November 4,</span> 2010</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Der+Spiegel&rft.atitle=Article+detailing+attack+on+Maison+de+France+in+Berlin+%28German%29&rft.date=1999-12-13&rft_id=http%3A%2F%2Fwww.spiegel.de%2Fpanorama%2F0%2C1518%2C56218%2C00.html&rfr_id=info%3Asid%2Fen.wikipedia.org%3APentaerythritol+tetranitrate" class="Z3988"></span></span> </li> <li id="cite_note-urlBBC_News|AMERICAS|Shoe_bomb_suspect_did_not_act_alone-34"><span class="mw-cite-backlink"><b><a href="#cite_ref-urlBBC_News|AMERICAS|Shoe_bomb_suspect_did_not_act_alone_34-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation news cs1"><a rel="nofollow" class="external text" href="http://news.bbc.co.uk/2/hi/americas/1783237.stm">"<span class="cs1-kern-left"></span>'Shoe bomb suspect 'did not act alone'<span class="cs1-kern-right"></span>"</a>. <i>BBC News</i>. January 25, 2002<span class="reference-accessdate">. Retrieved <span class="nowrap">April 22,</span> 2009</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=BBC+News&rft.atitle=%27Shoe+bomb+suspect+%27did+not+act+alone%27&rft.date=2002-01-25&rft_id=http%3A%2F%2Fnews.bbc.co.uk%2F2%2Fhi%2Famericas%2F1783237.stm&rfr_id=info%3Asid%2Fen.wikipedia.org%3APentaerythritol+tetranitrate" class="Z3988"></span></span> </li> <li id="cite_note-35"><span class="mw-cite-backlink"><b><a href="#cite_ref-35">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://web.archive.org/web/20091231030044/http://homelandsecuritynewswire.com/saudi-suicide-bomber-hid-ied-his-anal-cavity">"Saudi suicide bomber hid IED in his anal cavity"</a>. <i>Homeland Security Newswire</i>. September 9, 2009. Archived from <a rel="nofollow" class="external text" href="http://homelandsecuritynewswire.com/saudi-suicide-bomber-hid-ied-his-anal-cavity">the original</a> on December 31, 2009<span class="reference-accessdate">. Retrieved <span class="nowrap">December 28,</span> 2009</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=Homeland+Security+Newswire&rft.atitle=Saudi+suicide+bomber+hid+IED+in+his+anal+cavity&rft.date=2009-09-09&rft_id=http%3A%2F%2Fhomelandsecuritynewswire.com%2Fsaudi-suicide-bomber-hid-ied-his-anal-cavity&rfr_id=info%3Asid%2Fen.wikipedia.org%3APentaerythritol+tetranitrate" class="Z3988"></span></span> </li> <li id="cite_note-36"><span class="mw-cite-backlink"><b><a href="#cite_ref-36">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFEngland,_Andrew2010" class="citation web cs1">England, Andrew (November 1, 2010). <span class="id-lock-subscription" title="Paid subscription required"><a rel="nofollow" class="external text" href="https://www.ft.com/content/c2a28a88-e606-11df-9cdd-00144feabdc0">"Bomb clues point to Yemeni terrorists"</a></span>. <i>Financial Times</i>. <a rel="nofollow" class="external text" href="https://ghostarchive.org/archive/20221210/https://www.ft.com/content/c2a28a88-e606-11df-9cdd-00144feabdc0">Archived</a> from the original on December 10, 2022.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=Financial+Times&rft.atitle=Bomb+clues+point+to+Yemeni+terrorists&rft.date=2010-11-01&rft.au=England%2C+Andrew&rft_id=https%3A%2F%2Fwww.ft.com%2Fcontent%2Fc2a28a88-e606-11df-9cdd-00144feabdc0&rfr_id=info%3Asid%2Fen.wikipedia.org%3APentaerythritol+tetranitrate" class="Z3988"></span></span> </li> <li id="cite_note-37"><span class="mw-cite-backlink"><b><a href="#cite_ref-37">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation news cs1"><a rel="nofollow" class="external text" href="https://www.cbsnews.com/news/saudi-bombmaker-key-suspect-in-yemen-plot/">"Saudi Bombmaker Key Suspect in Yemen Plot"</a>. CBS News. November 1, 2010. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20121102214722/http://www.cbsnews.com/stories/2010/11/01/world/main7010288.shtml">Archived</a> from the original on November 2, 2012<span class="reference-accessdate">. Retrieved <span class="nowrap">November 2,</span> 2010</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.atitle=Saudi+Bombmaker+Key+Suspect+in+Yemen+Plot&rft.date=2010-11-01&rft_id=https%3A%2F%2Fwww.cbsnews.com%2Fnews%2Fsaudi-bombmaker-key-suspect-in-yemen-plot%2F&rfr_id=info%3Asid%2Fen.wikipedia.org%3APentaerythritol+tetranitrate" class="Z3988"></span></span> </li> <li id="cite_note-38"><span class="mw-cite-backlink"><b><a href="#cite_ref-38">^</a></b></span> <span class="reference-text"> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation news cs1"><a rel="nofollow" class="external text" href="https://web.archive.org/web/20091231020948/http://www.foxnews.com/story/0,2933,581307,00.html">"Al Qaeda Claims Responsibility for Attempted Bombing of U.S. Plane"</a>. FOX News Network. December 28, 2009. Archived from <a rel="nofollow" class="external text" href="http://www.foxnews.com/story/0,2933,581307,00.html">the original</a> on December 31, 2009<span class="reference-accessdate">. Retrieved <span class="nowrap">December 29,</span> 2009</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.atitle=Al+Qaeda+Claims+Responsibility+for+Attempted+Bombing+of+U.S.+Plane&rft.date=2009-12-28&rft_id=http%3A%2F%2Fwww.foxnews.com%2Fstory%2F0%2C2933%2C581307%2C00.html&rfr_id=info%3Asid%2Fen.wikipedia.org%3APentaerythritol+tetranitrate" class="Z3988"></span></span> </li> <li id="cite_note-39"><span class="mw-cite-backlink"><b><a href="#cite_ref-39">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation news cs1"><a rel="nofollow" class="external text" href="http://big.assets.huffingtonpost.com/AbdumutallabCharges.pdf">"Criminal Complaint"</a> <span class="cs1-format">(PDF)</span>. <i><a href="/wiki/The_Huffington_Post" class="mw-redirect" title="The Huffington Post">The Huffington Post</a></i>. <a rel="nofollow" class="external text" href="https://ghostarchive.org/archive/20221009/http://big.assets.huffingtonpost.com/AbdumutallabCharges.pdf">Archived</a> <span class="cs1-format">(PDF)</span> from the original on October 9, 2022<span class="reference-accessdate">. Retrieved <span class="nowrap">November 4,</span> 2010</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=The+Huffington+Post&rft.atitle=Criminal+Complaint&rft_id=http%3A%2F%2Fbig.assets.huffingtonpost.com%2FAbdumutallabCharges.pdf&rfr_id=info%3Asid%2Fen.wikipedia.org%3APentaerythritol+tetranitrate" class="Z3988"></span></span> </li> <li id="cite_note-urlABC_News|AMERICAS|Investigators:_Northwest_Bomb_Plot_Planned_by_Al-Qaeda_in_Yemen-40"><span class="mw-cite-backlink"><b><a href="#cite_ref-urlABC_News|AMERICAS|Investigators:_Northwest_Bomb_Plot_Planned_by_Al-Qaeda_in_Yemen_40-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://abcnews.go.com/Blotter/northwest-bomb-plot-planned-al-qaeda-yemen/story?id=9426085&page=1">"Investigators: Northwest Bomb Plot Planned by al Qaeda in Yemen"</a>. ABC News. December 26, 2009<span class="reference-accessdate">. Retrieved <span class="nowrap">December 26,</span> 2009</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=Investigators%3A+Northwest+Bomb+Plot+Planned+by+al+Qaeda+in+Yemen&rft.pub=ABC+News&rft.date=2009-12-26&rft_id=https%3A%2F%2Fabcnews.go.com%2FBlotter%2Fnorthwest-bomb-plot-planned-al-qaeda-yemen%2Fstory%3Fid%3D9426085%26page%3D1&rfr_id=info%3Asid%2Fen.wikipedia.org%3APentaerythritol+tetranitrate" class="Z3988"></span></span> </li> <li id="cite_note-41"><span class="mw-cite-backlink"><b><a href="#cite_ref-41">^</a></b></span> <span class="reference-text"><a rel="nofollow" class="external text" href="https://www.washingtonpost.com/wp-dyn/content/article/2009/12/28/AR2009122800582.html">Explosive in Detroit terror case could have blown hole in airplane, sources say</a> <i>The Washington Post</i>. Retrieved February 8, 2010.</span> </li> <li id="cite_note-scientificamerican1-42"><span class="mw-cite-backlink">^ <a href="#cite_ref-scientificamerican1_42-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-scientificamerican1_42-1"><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="CITEREFGreenemeier" class="citation web cs1">Greenemeier, Larry. <a rel="nofollow" class="external text" href="http://www.scientificamerican.com/article.cfm?id=aircraft-cargo-bomb-security">"Exposing the Weakest Link: As Airline Passenger Security Tightens, Bombers Target Cargo Holds"</a>. <i>Scientific American</i><span class="reference-accessdate">. Retrieved <span class="nowrap">November 3,</span> 2010</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=Scientific+American&rft.atitle=Exposing+the+Weakest+Link%3A+As+Airline+Passenger+Security+Tightens%2C+Bombers+Target+Cargo+Holds&rft.aulast=Greenemeier&rft.aufirst=Larry&rft_id=http%3A%2F%2Fwww.scientificamerican.com%2Farticle.cfm%3Fid%3Daircraft-cargo-bomb-security&rfr_id=info%3Asid%2Fen.wikipedia.org%3APentaerythritol+tetranitrate" class="Z3988"></span></span> </li> <li id="cite_note-nytimes4-43"><span class="mw-cite-backlink">^ <a href="#cite_ref-nytimes4_43-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-nytimes4_43-1"><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="CITEREFShaneWorth2010" class="citation news cs1">Shane, Scott; Worth, Robert F. (November 1, 2010). <a rel="nofollow" class="external text" href="https://www.nytimes.com/2010/11/02/world/02terror.html?src=twrhp">"Early Parcels Sent to U.S. Were Eyed as Dry Run"</a>. <i>The New York Times</i>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=The+New+York+Times&rft.atitle=Early+Parcels+Sent+to+U.S.+Were+Eyed+as+Dry+Run&rft.date=2010-11-01&rft.aulast=Shane&rft.aufirst=Scott&rft.au=Worth%2C+Robert+F.&rft_id=https%3A%2F%2Fwww.nytimes.com%2F2010%2F11%2F02%2Fworld%2F02terror.html%3Fsrc%3Dtwrhp&rfr_id=info%3Asid%2Fen.wikipedia.org%3APentaerythritol+tetranitrate" class="Z3988"></span></span> </li> <li id="cite_note-44"><span class="mw-cite-backlink"><b><a href="#cite_ref-44">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation news cs1"><a rel="nofollow" class="external text" href="http://indiatoday.intoday.in/site/Story/118746/World/parcel-bombs-could-rip-50-planes-in-half.html">"Parcel bombs could rip 50 planes in half"</a>. <i><a href="/wiki/India_Today" title="India Today">India Today</a></i><span class="reference-accessdate">. Retrieved <span class="nowrap">November 3,</span> 2010</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=India+Today&rft.atitle=Parcel+bombs+could+rip+50+planes+in+half&rft_id=http%3A%2F%2Findiatoday.intoday.in%2Fsite%2FStory%2F118746%2FWorld%2Fparcel-bombs-could-rip-50-planes-in-half.html&rfr_id=info%3Asid%2Fen.wikipedia.org%3APentaerythritol+tetranitrate" class="Z3988"></span></span> </li> <li id="cite_note-45"><span class="mw-cite-backlink"><b><a href="#cite_ref-45">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://web.archive.org/web/20101013011037/http://news.discovery.com/tech/underwear-bomber-explosion-plane-test.html">"<span class="cs1-kern-left"></span>'Underwear Bomber' Could not have Blown Up Plane"</a>. <a href="/wiki/Discovery_Channel" title="Discovery Channel">Discovery</a>. March 10, 2010. Archived from <a rel="nofollow" class="external text" href="http://news.discovery.com/tech/underwear-bomber-explosion-plane-test.html">the original</a> on October 13, 2010<span class="reference-accessdate">. Retrieved <span class="nowrap">November 16,</span> 2010</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=%27Underwear+Bomber%27+Could+not+have+Blown+Up+Plane&rft.pub=Discovery&rft.date=2010-03-10&rft_id=http%3A%2F%2Fnews.discovery.com%2Ftech%2Funderwear-bomber-explosion-plane-test.html&rfr_id=info%3Asid%2Fen.wikipedia.org%3APentaerythritol+tetranitrate" class="Z3988"></span></span> </li> <li id="cite_note-46"><span class="mw-cite-backlink"><b><a href="#cite_ref-46">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://indianexpress.com/article/what-is/what-is-petn-explsoive-uttar-pradesh-assembly-yogi-adityanath-4750049/">"What is PETN explosive device found in Uttar Pradesh Assembly?"</a>. July 15, 2017.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=What+is+PETN+explosive+device+found+in+Uttar+Pradesh+Assembly%3F&rft.date=2017-07-15&rft_id=https%3A%2F%2Findianexpress.com%2Farticle%2Fwhat-is%2Fwhat-is-petn-explsoive-uttar-pradesh-assembly-yogi-adityanath-4750049%2F&rfr_id=info%3Asid%2Fen.wikipedia.org%3APentaerythritol+tetranitrate" class="Z3988"></span></span> </li> <li id="cite_note-47"><span class="mw-cite-backlink"><b><a href="#cite_ref-47">^</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.firstpost.com/india/highly-explosive-petn-found-in-uttar-pradesh-assembly-yogi-adityanath-chairs-high-level-meet-demands-nia-probe-3812119.html">"Highly explosive PETN found in Uttar Pradesh Assembly: Yogi Adityanath demands NIA probe"</a>. July 14, 2017.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=Highly+explosive+PETN+found+in+Uttar+Pradesh+Assembly%3A+Yogi+Adityanath+demands+NIA+probe&rft.date=2017-07-14&rft_id=http%3A%2F%2Fwww.firstpost.com%2Findia%2Fhighly-explosive-petn-found-in-uttar-pradesh-assembly-yogi-adityanath-chairs-high-level-meet-demands-nia-probe-3812119.html&rfr_id=info%3Asid%2Fen.wikipedia.org%3APentaerythritol+tetranitrate" class="Z3988"></span></span> </li> <li id="cite_note-48"><span class="mw-cite-backlink"><b><a href="#cite_ref-48">^</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.censusindia.gov.in/2011census/PCA/PCA_Highlights/pca_highlights_file/India/Chapter-1.pdf">"Population and decadal change by residence : 2011 (PERSONS)"</a> <span class="cs1-format">(PDF)</span>. Office of the Registrar General & Census Commissioner, India. p. 2. <a rel="nofollow" class="external text" href="https://ghostarchive.org/archive/20221009/http://www.censusindia.gov.in/2011census/PCA/PCA_Highlights/pca_highlights_file/India/Chapter-1.pdf">Archived</a> <span class="cs1-format">(PDF)</span> from the original on October 9, 2022.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=Population+and+decadal+change+by+residence+%3A+2011+%28PERSONS%29&rft.pages=2&rft.pub=Office+of+the+Registrar+General+%26+Census+Commissioner%2C+India&rft_id=http%3A%2F%2Fwww.censusindia.gov.in%2F2011census%2FPCA%2FPCA_Highlights%2Fpca_highlights_file%2FIndia%2FChapter-1.pdf&rfr_id=info%3Asid%2Fen.wikipedia.org%3APentaerythritol+tetranitrate" class="Z3988"></span></span> </li> <li id="cite_note-49"><span class="mw-cite-backlink"><b><a href="#cite_ref-49">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://www.telangana.gov.in/PDFDocuments/Statistical%20Year%20Book%202015.pdf">"Statistical Year Book 2015"</a> <span class="cs1-format">(PDF)</span>. <i>telangana.gov.in</i>. Directorate of Economics and Statistics, Government of Telangana. <a rel="nofollow" class="external text" href="https://ghostarchive.org/archive/20221009/https://www.telangana.gov.in/PDFDocuments/Statistical%20Year%20Book%202015.pdf">Archived</a> <span class="cs1-format">(PDF)</span> from the original on October 9, 2022<span class="reference-accessdate">. Retrieved <span class="nowrap">March 4,</span> 2019</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=telangana.gov.in&rft.atitle=Statistical+Year+Book+2015&rft_id=https%3A%2F%2Fwww.telangana.gov.in%2FPDFDocuments%2FStatistical%2520Year%2520Book%25202015.pdf&rfr_id=info%3Asid%2Fen.wikipedia.org%3APentaerythritol+tetranitrate" class="Z3988"></span></span> </li> <li id="cite_note-50"><span class="mw-cite-backlink"><b><a href="#cite_ref-50">^</a></b></span> <span class="reference-text">Committee on the Review of Existing and Potential Standoff Explosives Detection Techniques, National Research Council (2004) <a rel="nofollow" class="external text" href="http://www.nap.edu/openbook.php?record_id=10998&page=1">Existing and Potential Standoff Explosives Detection Techniques</a>, National Academies Press, Washington, D.C. p. 77.</span> </li> <li id="cite_note-51"><span class="mw-cite-backlink"><b><a href="#cite_ref-51">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFBou-SleimanPerraudBousquetGuillet2015" class="citation book cs1">Bou-Sleiman, J.; Perraud, J.-B.; Bousquet, B.; Guillet, J.-P.; Palka, N.; Mounaix, P. (2015). "Discrimination and identification of RDX/PETN explosives by chemometrics applied to terahertz time-domain spectral imaging". In Salmon, Neil A; Jacobs, Eddie L (eds.). <i>Millimetre Wave and Terahertz Sensors and Technology VIII</i>. Vol. 9651. p. 965109. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1117%2F12.2197442">10.1117/12.2197442</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:137950290">137950290</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Discrimination+and+identification+of+RDX%2FPETN+explosives+by+chemometrics+applied+to+terahertz+time-domain+spectral+imaging&rft.btitle=Millimetre+Wave+and+Terahertz+Sensors+and+Technology+VIII&rft.pages=965109&rft.date=2015&rft_id=info%3Adoi%2F10.1117%2F12.2197442&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A137950290%23id-name%3DS2CID&rft.aulast=Bou-Sleiman&rft.aufirst=J.&rft.au=Perraud%2C+J.-B.&rft.au=Bousquet%2C+B.&rft.au=Guillet%2C+J.-P.&rft.au=Palka%2C+N.&rft.au=Mounaix%2C+P.&rfr_id=info%3Asid%2Fen.wikipedia.org%3APentaerythritol+tetranitrate" class="Z3988"></span></span> </li> <li id="cite_note-52"><span class="mw-cite-backlink"><b><a href="#cite_ref-52">^</a></b></span> <span class="reference-text"><a rel="nofollow" class="external text" href="https://www.washingtonpost.com/wp-dyn/content/article/2009/12/27/AR2009122702021.html">"Equipment to detect explosives is available"</a>. <i><a href="/wiki/The_Washington_Post" title="The Washington Post">The Washington Post</a></i>. Retrieved February 8, 2010.</span> </li> <li id="cite_note-spiegel1-53"><span class="mw-cite-backlink">^ <a href="#cite_ref-spiegel1_53-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-spiegel1_53-1"><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 class="citation news cs1"><a rel="nofollow" class="external text" href="http://www.spiegel.de/international/world/0,1518,726746,00.html">"Foiled Parcel Plot: World Scrambles to Tighten Air Cargo Security"</a>. <i><a href="/wiki/Der_Spiegel" title="Der Spiegel">Der Spiegel</a></i><span class="reference-accessdate">. Retrieved <span class="nowrap">November 2,</span> 2010</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Der+Spiegel&rft.atitle=Foiled+Parcel+Plot%3A+World+Scrambles+to+Tighten+Air+Cargo+Security&rft_id=http%3A%2F%2Fwww.spiegel.de%2Finternational%2Fworld%2F0%2C1518%2C726746%2C00.html&rfr_id=info%3Asid%2Fen.wikipedia.org%3APentaerythritol+tetranitrate" class="Z3988"></span></span> </li> <li id="cite_note-autogenerated1-54"><span class="mw-cite-backlink"><b><a href="#cite_ref-autogenerated1_54-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation news cs1"><a rel="nofollow" class="external text" href="https://www.bbc.co.uk/news/11658452">"Q&A: Air freight bomb plot"</a>. <i><a href="/wiki/BBC_News" title="BBC News">BBC News</a></i>. October 30, 2010<span class="reference-accessdate">. Retrieved <span class="nowrap">November 3,</span> 2010</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=BBC+News&rft.atitle=Q%26A%3A+Air+freight+bomb+plot&rft.date=2010-10-30&rft_id=https%3A%2F%2Fwww.bbc.co.uk%2Fnews%2F11658452&rfr_id=info%3Asid%2Fen.wikipedia.org%3APentaerythritol+tetranitrate" class="Z3988"></span></span> </li> <li id="cite_note-aljazeera1-55"><span class="mw-cite-backlink"><b><a href="#cite_ref-aljazeera1_55-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="http://english.aljazeera.net/news/middleeast/2010/10/20101031144429122829.html">"Passenger jets carried Dubai bomb"</a>. <a href="/wiki/Al_Jazeera_Media_Network" title="Al Jazeera Media Network">Al Jazeera</a>. October 31, 2010.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=Passenger+jets+carried+Dubai+bomb&rft.pub=Al+Jazeera&rft.date=2010-10-31&rft_id=http%3A%2F%2Fenglish.aljazeera.net%2Fnews%2Fmiddleeast%2F2010%2F10%2F20101031144429122829.html&rfr_id=info%3Asid%2Fen.wikipedia.org%3APentaerythritol+tetranitrate" class="Z3988"></span></span> </li> <li id="cite_note-56"><span class="mw-cite-backlink"><b><a href="#cite_ref-56">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFRussek_H._I.1966" class="citation journal cs1">Russek H. I. (1966). "The therapeutic role of coronary vasodilators: glyceryl trinitrate, isosorbide dinitrate, and pentaerythritol tetranitrate". <i>American Journal of the Medical Sciences</i>. <b>252</b> (1): 9–20. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1097%2F00000441-196607000-00002">10.1097/00000441-196607000-00002</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/4957459">4957459</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:30975527">30975527</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=American+Journal+of+the+Medical+Sciences&rft.atitle=The+therapeutic+role+of+coronary+vasodilators%3A+glyceryl+trinitrate%2C+isosorbide+dinitrate%2C+and+pentaerythritol+tetranitrate.&rft.volume=252&rft.issue=1&rft.pages=9-20&rft.date=1966&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A30975527%23id-name%3DS2CID&rft_id=info%3Apmid%2F4957459&rft_id=info%3Adoi%2F10.1097%2F00000441-196607000-00002&rft.au=Russek+H.+I.&rfr_id=info%3Asid%2Fen.wikipedia.org%3APentaerythritol+tetranitrate" class="Z3988"></span></span> </li> <li id="cite_note-57"><span class="mw-cite-backlink"><b><a href="#cite_ref-57">^</a></b></span> <span class="reference-text">Baselt, R. (2008) <i>Disposition of Toxic Drugs and Chemicals in Man</i>, 8th edition, Biomedical Publications, Foster City, CA. pp. 1201–1203. <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/0962652369" title="Special:BookSources/0962652369">0962652369</a>.</span> </li> </ol></div> <div class="mw-heading mw-heading2"><h2 id="Further_reading">Further reading</h2></div> <style data-mw-deduplicate="TemplateStyles:r1235681985">.mw-parser-output .side-box{margin:4px 0;box-sizing:border-box;border:1px solid #aaa;font-size:88%;line-height:1.25em;background-color:var(--background-color-interactive-subtle,#f8f9fa);display:flow-root}.mw-parser-output .side-box-abovebelow,.mw-parser-output .side-box-text{padding:0.25em 0.9em}.mw-parser-output .side-box-image{padding:2px 0 2px 0.9em;text-align:center}.mw-parser-output .side-box-imageright{padding:2px 0.9em 2px 0;text-align:center}@media(min-width:500px){.mw-parser-output .side-box-flex{display:flex;align-items:center}.mw-parser-output .side-box-text{flex:1;min-width:0}}@media(min-width:720px){.mw-parser-output .side-box{width:238px}.mw-parser-output .side-box-right{clear:right;float:right;margin-left:1em}.mw-parser-output .side-box-left{margin-right:1em}}</style><style data-mw-deduplicate="TemplateStyles:r1237033735">@media print{body.ns-0 .mw-parser-output .sistersitebox{display:none!important}}@media screen{html.skin-theme-clientpref-night .mw-parser-output .sistersitebox img[src*="Wiktionary-logo-en-v2.svg"]{background-color:white}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .sistersitebox img[src*="Wiktionary-logo-en-v2.svg"]{background-color:white}}</style><div class="side-box side-box-right plainlinks sistersitebox"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"> <div class="side-box-flex"> <div class="side-box-image"><span class="noviewer" typeof="mw:File"><span><img alt="" src="//upload.wikimedia.org/wikipedia/en/thumb/4/4a/Commons-logo.svg/30px-Commons-logo.svg.png" decoding="async" width="30" height="40" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/4/4a/Commons-logo.svg/45px-Commons-logo.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/4/4a/Commons-logo.svg/59px-Commons-logo.svg.png 2x" data-file-width="1024" data-file-height="1376" /></span></span></div> <div class="side-box-text plainlist">Wikimedia Commons has media related to <span style="font-weight: bold; font-style: italic;"><a href="https://commons.wikimedia.org/wiki/Category:Pentaerythritol_tetranitrate" class="extiw" title="commons:Category:Pentaerythritol tetranitrate">Pentaerythritol tetranitrate</a></span>.</div></div> </div> <ul><li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFCooper,_Paul1997" class="citation book cs1">Cooper, Paul (1997). <i>Explosives Engineering</i>. Weinheim: Wiley-VCH. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-471-18636-6" title="Special:BookSources/978-0-471-18636-6"><bdi>978-0-471-18636-6</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Explosives+Engineering&rft.place=Weinheim&rft.pub=Wiley-VCH&rft.date=1997&rft.isbn=978-0-471-18636-6&rft.au=Cooper%2C+Paul&rfr_id=info%3Asid%2Fen.wikipedia.org%3APentaerythritol+tetranitrate" class="Z3988"></span></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><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"></div><div role="navigation" class="navbox" aria-labelledby="Vasodilators_used_in_cardiac_diseases_(C01D)" 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:Vasodilators_used_in_cardiac_diseases" title="Template:Vasodilators used in cardiac diseases"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Vasodilators_used_in_cardiac_diseases" title="Template talk:Vasodilators used in cardiac diseases"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Vasodilators_used_in_cardiac_diseases" title="Special:EditPage/Template:Vasodilators used in cardiac diseases"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Vasodilators_used_in_cardiac_diseases_(C01D)" style="font-size:114%;margin:0 4em"><a href="/wiki/Vasodilator" class="mw-redirect" title="Vasodilator">Vasodilators</a> used in <a href="/wiki/Cardiac_disease" class="mw-redirect" title="Cardiac disease">cardiac diseases</a> (<a href="/wiki/ATC_code_C01#C01D" title="ATC code C01">C01D</a>)</div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Nitrovasodilator" title="Nitrovasodilator">Nitrovasodilators</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Medical_use_of_nitroglycerin" class="mw-redirect" title="Medical use of nitroglycerin">Nitroglycerin</a> #</li> <li><a href="/wiki/Isosorbide_dinitrate" title="Isosorbide dinitrate">Isosorbide dinitrate</a> #</li> <li><a href="/wiki/Isosorbide_mononitrate" title="Isosorbide mononitrate">Isosorbide mononitrate</a></li> <li><a href="/wiki/Itramin_tosilate" title="Itramin tosilate">Itramin tosilate</a></li> <li><a href="/wiki/Linsidomine" title="Linsidomine">Linsidomine</a></li> <li><a href="/wiki/Molsidomine" title="Molsidomine">Molsidomine</a></li> <li><a href="/wiki/Nicorandil" title="Nicorandil">Nicorandil</a></li> <li><a class="mw-selflink selflink">Pentaerythritol tetranitrate</a></li> <li><a href="/wiki/Propatylnitrate" title="Propatylnitrate">Propatylnitrate</a></li> <li>Tenitramine</li> <li><a href="/wiki/Trolnitrate" title="Trolnitrate">Trolnitrate</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Quinolone" title="Quinolone">Quinolone</a> vasodilators</th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Flosequinan" title="Flosequinan">Flosequinan</a><sup>‡</sup></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Others</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Benziodarone" title="Benziodarone">Benziodarone</a></li> <li><a href="/wiki/Carbocromen" title="Carbocromen">Carbocromen</a></li> <li><a href="/wiki/Cinepazet" title="Cinepazet">Cinepazet</a></li> <li><a href="/wiki/Cloridarol" title="Cloridarol">Cloridarol</a></li> <li><a href="/wiki/Dilazep" title="Dilazep">Dilazep</a></li> <li><a href="/wiki/Efloxate" title="Efloxate">Efloxate</a></li> <li><a href="/wiki/Etafenone" title="Etafenone">Etafenone</a></li> <li><a href="/wiki/Gapicomine" title="Gapicomine">Gapicomine</a></li> <li><a href="/wiki/Heptaminol" title="Heptaminol">Heptaminol</a></li> <li><a href="/wiki/Hexobendine" title="Hexobendine">Hexobendine</a></li> <li><a href="/wiki/Imolamine" title="Imolamine">Imolamine</a></li> <li><a href="/wiki/Levosimendan" title="Levosimendan">Levosimendan</a></li> <li><a href="/wiki/Nesiritide" title="Nesiritide">Nesiritide</a></li> <li><a href="/wiki/Nicorandil" title="Nicorandil">Nicorandil</a></li> <li><a href="/wiki/Oxyfedrine" title="Oxyfedrine">Oxyfedrine</a></li> <li><a href="/wiki/Pimobendan" title="Pimobendan">Pimobendan</a></li> <li><a href="/wiki/Prenylamine" title="Prenylamine">Prenylamine</a></li> <li><a href="/wiki/Serelaxin" title="Serelaxin">Serelaxin</a></li> <li><a href="/wiki/Trapidil" title="Trapidil">Trapidil</a></li> <li><a href="/wiki/Vericiguat" title="Vericiguat">Vericiguat</a></li></ul> </div></td></tr><tr><td class="navbox-abovebelow" colspan="2" style="background: transparent; padding: 0px;"><div><div class="hlist"> <ul><li><sup>#</sup><a href="/wiki/WHO_Model_List_of_Essential_Medicines" title="WHO Model List of Essential Medicines">WHO-EM</a></li> <li><sup>‡</sup><a href="/wiki/List_of_withdrawn_drugs" title="List of withdrawn drugs">Withdrawn</a> from market</li> <li><a href="/wiki/Clinical_trial" title="Clinical trial">Clinical trials</a>: <ul><li><sup>†</sup><a href="/wiki/Phases_of_clinical_research#Phase_III" title="Phases of clinical research">Phase III</a></li> <li><sup>§</sup>Never to phase III</li></ul></li></ul> </div></div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"></div><div role="navigation" class="navbox" aria-labelledby="Nitric_oxide_signaling_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:Nitric_oxide_signaling_modulators" title="Template:Nitric oxide signaling modulators"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Nitric_oxide_signaling_modulators" title="Template talk:Nitric oxide signaling modulators"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Nitric_oxide_signaling_modulators" title="Special:EditPage/Template:Nitric oxide signaling modulators"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Nitric_oxide_signaling_modulators" style="font-size:114%;margin:0 4em"><a href="/wiki/Nitric_oxide" title="Nitric oxide">Nitric oxide</a> <a href="/wiki/Cell_signaling" title="Cell signaling">signaling</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/Nitric_oxide" title="Nitric oxide">Forms</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Nitroxyl" title="Nitroxyl">Nitroxyl anion (NO<sup>−</sup>; oxonitrate(1-), hyponitrite anion)</a></li> <li><a href="/wiki/Nitric_oxide" title="Nitric oxide">Nitric oxide (NO<sup>⋅</sup>; nitrogen monoxide)</a></li> <li><a href="/wiki/Nitrosonium" title="Nitrosonium">Nitrosonium (NO<sup>+</sup>; nitrosyl cation)</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Biological_target" title="Biological target">Targets</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 id="sGC" scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Soluble_guanylate_cyclase" class="mw-redirect" title="Soluble guanylate cyclase">sGC</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><i>Activators/stimulators:</i> <a href="/w/index.php?title=Ataciguat&action=edit&redlink=1" class="new" title="Ataciguat (page does not exist)">Ataciguat</a></li> <li><a href="/w/index.php?title=BAY_41-2272&action=edit&redlink=1" class="new" title="BAY 41-2272 (page does not exist)">BAY 41-2272</a></li> <li><a href="/w/index.php?title=BAY_41-8543&action=edit&redlink=1" class="new" title="BAY 41-8543 (page does not exist)">BAY 41-8543</a></li> <li><a href="/w/index.php?title=BAY_60-4552&action=edit&redlink=1" class="new" title="BAY 60-4552 (page does not exist)">BAY 60-4552</a></li> <li><a href="/w/index.php?title=BI-703704&action=edit&redlink=1" class="new" title="BI-703704 (page does not exist)">BI-703704</a></li> <li><a href="/wiki/Cinaciguat" title="Cinaciguat">Cinaciguat (BAY 58-2667)</a></li> <li><a href="/w/index.php?title=GSK-2181236A&action=edit&redlink=1" class="new" title="GSK-2181236A (page does not exist)">GSK-2181236A</a></li> <li><a href="/w/index.php?title=Praliciguat&action=edit&redlink=1" class="new" title="Praliciguat (page does not exist)">Praliciguat</a></li> <li><a href="/wiki/Riociguat" title="Riociguat">Riociguat</a></li> <li><a href="/wiki/Vericiguat" title="Vericiguat">Vericiguat</a></li></ul> <ul><li><i>Inhibitors:</i> <a href="/w/index.php?title=1H-(1,2,4)Oxadiazolo(4,3-a)quinoxalin-1-one&action=edit&redlink=1" class="new" title="1H-(1,2,4)Oxadiazolo(4,3-a)quinoxalin-1-one (page does not exist)">ODQ</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/NO_donor" class="mw-redirect" title="NO donor">NO donors</a><br /><small>(<a href="/wiki/Prodrug" title="Prodrug">prodrugs</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"> <ul><li><i><a href="/wiki/Nitrate" title="Nitrate">Nitrates</a>:</i> <a href="/wiki/Diethylene_glycol_dinitrate" title="Diethylene glycol dinitrate">Diethylene glycol dinitrate (DEGDN)</a></li> <li><a href="/wiki/Erythritol_tetranitrate" title="Erythritol tetranitrate">Erythritol tetranitrate (ETN)</a></li> <li><a href="/wiki/Ethylene_glycol_dinitrate" title="Ethylene glycol dinitrate">Ethylene glycol dinitrate (EGDN; nitroglycol)</a></li> <li><a href="/wiki/Isosorbide_mononitrate" title="Isosorbide mononitrate">Isosorbide mononitrate (ISMN)</a></li> <li><a href="/wiki/Isosorbide_dinitrate" title="Isosorbide dinitrate">Isosorbide dinitrate (ISDN)</a></li> <li><a href="/wiki/Itramin_tosilate" title="Itramin tosilate">Itramin tosilate</a></li> <li><a href="/wiki/Mannitol_hexanitrate" title="Mannitol hexanitrate">Mannitol hexanitrate</a></li> <li><a href="/wiki/Naproxcinod" title="Naproxcinod">Naproxcinod (nitronaproxen; AZD-3582, HCT-3012)</a></li> <li><a href="/w/index.php?title=NCX-466&action=edit&redlink=1" class="new" title="NCX-466 (page does not exist)">NCX-466</a></li> <li><a href="/w/index.php?title=NCX-2216&action=edit&redlink=1" class="new" title="NCX-2216 (page does not exist)">NCX-2216</a></li> <li><a href="/w/index.php?title=NCX-4016&action=edit&redlink=1" class="new" title="NCX-4016 (page does not exist)">NCX-4016</a></li> <li><a href="/w/index.php?title=NCX_4040&action=edit&redlink=1" class="new" title="NCX 4040 (page does not exist)">NCX 4040</a></li> <li><a href="/w/index.php?title=NCX-4215&action=edit&redlink=1" class="new" title="NCX-4215 (page does not exist)">NCX-4215</a></li> <li><a href="/wiki/Nicorandil" title="Nicorandil">Nicorandil</a></li> <li><a href="/wiki/Nipradilol" title="Nipradilol">Nipradilol (K-351)</a></li> <li><a href="/wiki/Nitrate" title="Nitrate">Nitrate (NO<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1.2em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline">−</sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">3</sub></span></span>)</a></li> <li><a href="/w/index.php?title=Nitroatorvastatin&action=edit&redlink=1" class="new" title="Nitroatorvastatin (page does not exist)">Nitroatorvastatin (NCX-6560)</a></li> <li><a href="/w/index.php?title=Nitroflurbiprofen&action=edit&redlink=1" class="new" title="Nitroflurbiprofen (page does not exist)">Nitroflurbiprofen (HCT-1026)</a></li> <li><a href="/w/index.php?title=Nitrofluvastatin&action=edit&redlink=1" class="new" title="Nitrofluvastatin (page does not exist)">Nitrofluvastatin</a></li> <li><a href="/wiki/Nitroglycerin_(drug)" class="mw-redirect" title="Nitroglycerin (drug)">Nitroglycerin (glyceryl trinitrate (GTN))</a></li> <li><a href="/w/index.php?title=Nitropravastatin&action=edit&redlink=1" class="new" title="Nitropravastatin (page does not exist)">Nitropravastatin (NCX-6550)</a></li> <li><a href="/wiki/Pentaerithrityl_tetranitrate" class="mw-redirect" title="Pentaerithrityl tetranitrate">Pentaerithrityl tetranitrate (PETN)</a></li> <li><a href="/wiki/Propatylnitrate" title="Propatylnitrate">Propatylnitrate</a></li> <li><a href="/wiki/Propylene_glycol_dinitrate" title="Propylene glycol dinitrate">Propylene glycol dinitrate (PGDN)</a></li> <li><a href="/w/index.php?title=Sodium_trioxodinitrate&action=edit&redlink=1" class="new" title="Sodium trioxodinitrate (page does not exist)">Sodium trioxodinitrate (Angeli's salt)</a></li> <li>Tenitramine</li> <li><a href="/wiki/Trolnitrate" title="Trolnitrate">Trolnitrate</a></li></ul> <ul><li><i><a href="/wiki/Nitroso_compound" class="mw-redirect" title="Nitroso compound">Nitroso compounds</a>/<a href="/wiki/Nitrite" title="Nitrite">nitrites</a>:</i> <a href="/wiki/Nitrite" title="Nitrite">Nitrite (NO<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1.2em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline">−</sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">2</sub></span></span>)</a>; <i>O-Nitroso compounds (<a href="/wiki/Alkyl_nitrite" title="Alkyl nitrite">alkyl nitrites</a>):</i> <a href="/wiki/Amyl_nitrite" title="Amyl nitrite">Amyl nitrite (isoamyl nitrite, isopentyl nitrite)</a></li> <li><a href="/wiki/Cyclohexyl_nitrite" title="Cyclohexyl nitrite">Cyclohexyl nitrite</a></li> <li><a href="/wiki/Ethyl_nitrite" title="Ethyl nitrite">Ethyl nitrite</a></li> <li><a href="/wiki/Hexyl_nitrite" title="Hexyl nitrite">Hexyl nitrite</a></li> <li><a href="/wiki/Isobutyl_nitrite" title="Isobutyl nitrite">Isobutyl nitrite (2-methylpropyl nitrite)</a></li> <li><a href="/wiki/Isopropyl_nitrite" title="Isopropyl nitrite">Isopropyl nitrite</a></li> <li><a href="/wiki/Methyl_nitrite" title="Methyl nitrite">Methyl nitrite</a></li> <li><a href="/wiki/Butyl_nitrite" title="Butyl nitrite"><i>n</i>-Butyl nitrite</a></li> <li><a href="/wiki/Pentyl_nitrite" title="Pentyl nitrite">Pentyl nitrite</a></li> <li><a href="/wiki/Tert-Butyl_nitrite" title="Tert-Butyl nitrite"><i>tert</i>-Butyl nitrite</a>; <i><a href="/wiki/S-Nitrosothiol" title="S-Nitrosothiol">S-Nitroso compounds</a> (thionitrites):</i> <a href="/w/index.php?title=LA810&action=edit&redlink=1" class="new" title="LA810 (page does not exist)">LA810</a></li> <li><a href="/w/index.php?title=S-Nitrosoalbumin&action=edit&redlink=1" class="new" title="S-Nitrosoalbumin (page does not exist)">S-Nitrosoalbumin (SNALB)</a></li> <li><a href="/w/index.php?title=S-Nitrosated_AR545C&action=edit&redlink=1" class="new" title="S-Nitrosated AR545C (page does not exist)">S-Nitrosated AR545C</a></li> <li><a href="/w/index.php?title=S-Nitroso-N-acetylcysteine&action=edit&redlink=1" class="new" title="S-Nitroso-N-acetylcysteine (page does not exist)">S-Nitroso-N-acetylcysteine (SNAC)</a></li> <li><a href="/wiki/S-Nitroso-N-acetylpenicillamine" title="S-Nitroso-N-acetylpenicillamine">S-Nitroso-N-acetylpenicillamine (SNAP)</a></li> <li><a href="/w/index.php?title=S-Nitroso-N-valerylpenicillamine&action=edit&redlink=1" class="new" title="S-Nitroso-N-valerylpenicillamine (page does not exist)">S-Nitroso-N-valerylpenicillamine (SNVP)</a></li> <li><a href="/w/index.php?title=S-Nitrosocaptopril&action=edit&redlink=1" class="new" title="S-Nitrosocaptopril (page does not exist)">S-Nitrosocaptopril (SNO-Cap)</a></li> <li><a href="/w/index.php?title=S-Nitrosocysteine&action=edit&redlink=1" class="new" title="S-Nitrosocysteine (page does not exist)">S-Nitrosocysteine (SNC, CysNO, SNO-Cys)</a></li> <li><a href="/w/index.php?title=S-Nitrosodiclofenac&action=edit&redlink=1" class="new" title="S-Nitrosodiclofenac (page does not exist)">S-Nitrosodiclofenac</a></li> <li><a href="/wiki/S-Nitrosoglutathione" title="S-Nitrosoglutathione">S-Nitrosoglutathione (GSNO, SNOG)</a></li> <li><a href="/w/index.php?title=S-Nitrosated_tissue-type_plasminogen_activator&action=edit&redlink=1" class="new" title="S-Nitrosated tissue-type plasminogen activator (page does not exist)">SNO-t-PA</a></li> <li><a href="/w/index.php?title=S-Nitrosated_von_Willebrand_factor&action=edit&redlink=1" class="new" title="S-Nitrosated von Willebrand factor (page does not exist)">SNO-vWF</a>; <i>N-Nitroso compounds (e.g., <a href="/wiki/Nitrosamine" title="Nitrosamine">nitrosamines</a>):</i> <a href="/w/index.php?title=SIN-1A&action=edit&redlink=1" class="new" title="SIN-1A (page does not exist)">SIN-1A</a></li></ul> <ul><li><i>Nitrosyl compounds:</i> <i><a href="/wiki/Metal_nitrosyl_complex" title="Metal nitrosyl complex">Metal nitrosyl complexes</a>:</i> <a href="/wiki/Roussin%27s_black_salt" title="Roussin's black salt">Roussin's black salt</a></li> <li><a href="/wiki/Roussin%27s_red_salt" title="Roussin's red salt">Roussin's red salt</a></li> <li><a href="/wiki/Sodium_nitroprusside" title="Sodium nitroprusside">Sodium nitroprusside (SNP)</a></li></ul> <ul><li><i><a href="/wiki/NONOate" title="NONOate">NONOates</a> (diazeniumdiolates):</i> <a href="/w/index.php?title=Diethylamine/NO&action=edit&redlink=1" class="new" title="Diethylamine/NO (page does not exist)">Diethylamine/NO (DEA/NO)</a></li> <li><a href="/w/index.php?title=Diethylenetriamine/NO&action=edit&redlink=1" class="new" title="Diethylenetriamine/NO (page does not exist)">Diethylenetriamine/NO (DETA/NO)</a></li> <li><a href="/w/index.php?title=GLO/NO&action=edit&redlink=1" class="new" title="GLO/NO (page does not exist)">GLO/NO</a></li> <li><a href="/w/index.php?title=JS-K&action=edit&redlink=1" class="new" title="JS-K (page does not exist)">JS-K</a></li> <li><a href="/w/index.php?title=Methylamine_hexamethylene_methylamine/NO&action=edit&redlink=1" class="new" title="Methylamine hexamethylene methylamine/NO (page does not exist)">Methylamine hexamethylene methylamine/NO (MAHMA/NO)</a></li> <li><a href="/w/index.php?title=PROLI/NO&action=edit&redlink=1" class="new" title="PROLI/NO (page does not exist)">PROLI/NO</a></li> <li><a href="/w/index.php?title=Spermine/NO&action=edit&redlink=1" class="new" title="Spermine/NO (page does not exist)">Spermine/NO (SPER/NO)</a></li> <li><a href="/w/index.php?title=V-PYRRO/NO&action=edit&redlink=1" class="new" title="V-PYRRO/NO (page does not exist)">V-PYRRO/NO</a></li></ul> <ul><li><i>Heterocyclic compounds:</i> <i><a href="/wiki/Furoxan" title="Furoxan">Furoxans</a>:</i> <a href="/wiki/Furoxan" title="Furoxan">Furoxan</a></li> <li><a href="/w/index.php?title=REC15/2739&action=edit&redlink=1" class="new" title="REC15/2739 (page does not exist)">REC15/2739</a>; <i><a href="/w/index.php?title=Sydnonimine&action=edit&redlink=1" class="new" title="Sydnonimine (page does not exist)">Sydnonimines</a>:</i> <a href="/wiki/Feprosidnine" title="Feprosidnine">Feprosidnine</a></li> <li><a href="/wiki/Linsidomine" title="Linsidomine">Linsidomine (SIN-1)</a></li> <li><a href="/wiki/Molsidomine" title="Molsidomine">Molsidomine (SIN-10)</a></li> <li><a href="/w/index.php?title=Sydnonimine&action=edit&redlink=1" class="new" title="Sydnonimine (page does not exist)">Sydnonimine</a></li></ul> <ul><li><i>Unsorted:</i> <a href="/wiki/Cimlanod" title="Cimlanod">Cimlanod</a></li> <li><a href="/w/index.php?title=FK-409&action=edit&redlink=1" class="new" title="FK-409 (page does not exist)">FK-409</a></li> <li><a href="/w/index.php?title=FR144220&action=edit&redlink=1" class="new" title="FR144220 (page does not exist)">FR144220</a></li> <li><a href="/w/index.php?title=FR146881&action=edit&redlink=1" class="new" title="FR146881 (page does not exist)">FR146881</a></li> <li><a href="/w/index.php?title=N-Acetyl-N-acetoxy-4-chlorobenzenesulfonamide&action=edit&redlink=1" class="new" title="N-Acetyl-N-acetoxy-4-chlorobenzenesulfonamide (page does not exist)">N-Acetyl-N-acetoxy-4-chlorobenzenesulfonamide</a></li></ul> </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:1%;text-align:center;"><a href="/wiki/Nitric_oxide_synthase" title="Nitric oxide synthase">NOS</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/NOS1" title="NOS1">nNOS</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="/w/index.php?title=3-Bromo-7-nitroindazole&action=edit&redlink=1" class="new" title="3-Bromo-7-nitroindazole (page does not exist)">3-Bromo-7-nitroindazole</a></li> <li><a href="/w/index.php?title=3-Chloroindazole&action=edit&redlink=1" class="new" title="3-Chloroindazole (page does not exist)">3-Chloroindazole</a></li> <li><a href="/w/index.php?title=3-Chloro-5-nitroindazole&action=edit&redlink=1" class="new" title="3-Chloro-5-nitroindazole (page does not exist)">3-Chloro-5-nitroindazole</a></li> <li><a href="/w/index.php?title=5-Nitroindazole&action=edit&redlink=1" class="new" title="5-Nitroindazole (page does not exist)">5-Nitroindazole</a></li> <li><a href="/w/index.php?title=6-Nitroindazole&action=edit&redlink=1" class="new" title="6-Nitroindazole (page does not exist)">6-Nitroindazole</a></li> <li><a href="/wiki/7-Nitroindazole" title="7-Nitroindazole">7-Nitroindazole</a></li> <li><a href="/w/index.php?title=A-84643&action=edit&redlink=1" class="new" title="A-84643 (page does not exist)">A-84643</a></li> <li><a href="/wiki/Aminoguanidine" class="mw-redirect" title="Aminoguanidine">Aminoguanidine (pimagedine)</a></li> <li><a href="/w/index.php?title=ARL-17477&action=edit&redlink=1" class="new" title="ARL-17477 (page does not exist)">ARL-17477</a></li> <li><a href="/wiki/Indazole" title="Indazole">Indazole</a></li> <li><a href="/w/index.php?title=N5-(1-Iminoethyl)-L-ornithine&action=edit&redlink=1" class="new" title="N5-(1-Iminoethyl)-L-ornithine (page does not exist)">N<sup>5</sup>-(1-Iminoethyl)-L-ornithine (<small>L</small>-NIO)</a></li> <li><a href="/w/index.php?title=N%CF%89-Methyl-L-arginine&action=edit&redlink=1" class="new" title="Nω-Methyl-L-arginine (page does not exist)">N<sup>ω</sup>-Methyl-<small>L</small>-arginine (<small>L</small>-NMA)</a></li> <li><a href="/w/index.php?title=N%CF%89-Propyl-L-arginine&action=edit&redlink=1" class="new" title="Nω-Propyl-L-arginine (page does not exist)">N<sup>ω</sup>-Propyl-<small>L</small>-arginine (<small>L</small>-NPA)</a></li> <li><a href="/wiki/Nitroarginine" title="Nitroarginine">Nitroarginine (NNA, NOARG)</a></li> <li><a href="/wiki/Pentamidine_isethionate" class="mw-redirect" title="Pentamidine isethionate">Pentamidine isethionate</a></li> <li><a href="/w/index.php?title=1-(2-Trifluoromethylphenyl)imidazole&action=edit&redlink=1" class="new" title="1-(2-Trifluoromethylphenyl)imidazole (page does not exist)">TRIM</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Nitric_oxide_synthase_2_(inducible)" title="Nitric oxide synthase 2 (inducible)">iNOS</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="/w/index.php?title=1-Amino-2-hydroxyguanidine&action=edit&redlink=1" class="new" title="1-Amino-2-hydroxyguanidine (page does not exist)">1-Amino-2-hydroxyguanidine</a></li> <li><a href="/w/index.php?title=2-Ethylaminoguanidine&action=edit&redlink=1" class="new" title="2-Ethylaminoguanidine (page does not exist)">2-Ethylaminoguanidine</a></li> <li><a href="/w/index.php?title=2-Iminopiperidine&action=edit&redlink=1" class="new" title="2-Iminopiperidine (page does not exist)">2-Iminopiperidine</a></li> <li><a href="/w/index.php?title=1400W&action=edit&redlink=1" class="new" title="1400W (page does not exist)">1400W</a></li> <li><a href="/w/index.php?title=S-aminoethylisothiourea&action=edit&redlink=1" class="new" title="S-aminoethylisothiourea (page does not exist)">AEITU</a></li> <li><a href="/wiki/Aminoguanidine" class="mw-redirect" title="Aminoguanidine">Aminoguanidine (pimagedine)</a></li> <li><a href="/w/index.php?title=2-Amino-5,6-dihydro-6-methyl-4H-1,3-thiazine&action=edit&redlink=1" class="new" title="2-Amino-5,6-dihydro-6-methyl-4H-1,3-thiazine (page does not exist)">AMT</a></li> <li><a href="/w/index.php?title=AR-C_102222&action=edit&redlink=1" class="new" title="AR-C 102222 (page does not exist)">AR-C 102222</a></li> <li><a href="/w/index.php?title=BYK-191023&action=edit&redlink=1" class="new" title="BYK-191023 (page does not exist)">BYK-191023</a></li> <li><a href="/wiki/Canavanine" title="Canavanine">Canavanine</a></li> <li><a href="/w/index.php?title=Cindunistat&action=edit&redlink=1" class="new" title="Cindunistat (page does not exist)">Cindunistat (SD-6010)</a></li> <li><a href="/w/index.php?title=S-Ethylisothiourea&action=edit&redlink=1" class="new" title="S-Ethylisothiourea (page does not exist)">EITU</a></li> <li><a href="/w/index.php?title=S-Isopropylisothiourea&action=edit&redlink=1" class="new" title="S-Isopropylisothiourea (page does not exist)">IPTU</a></li> <li><a href="/w/index.php?title=S-Methylisothiourea&action=edit&redlink=1" class="new" title="S-Methylisothiourea (page does not exist)">MITU</a></li> <li><a href="/w/index.php?title=N5-(1-Iminoethyl)-L-ornithine&action=edit&redlink=1" class="new" title="N5-(1-Iminoethyl)-L-ornithine (page does not exist)">N<sup>5</sup>-(1-Iminoethyl)-<small>L</small>-ornithine (<small>L</small>-NIO)</a></li> <li><a href="/w/index.php?title=N6-(1-Iminoethyl)-L-lysine&action=edit&redlink=1" class="new" title="N6-(1-Iminoethyl)-L-lysine (page does not exist)">N<sup>6</sup>-(1-Iminoethyl)-<small>L</small>-lysine (<small>L</small>-NIL)</a></li> <li><a href="/w/index.php?title=N%CF%89-Methyl-L-arginine&action=edit&redlink=1" class="new" title="Nω-Methyl-L-arginine (page does not exist)">N<sup>ω</sup>-Methyl-<small>L</small>-arginine (<small>L</small>-NMA)</a></li> <li><a href="/w/index.php?title=Ronopterin&action=edit&redlink=1" class="new" title="Ronopterin (page does not exist)">Ronopterin (VAS-203)</a></li> <li><a href="/w/index.php?title=1-(2-Trifluoromethylphenyl)imidazole&action=edit&redlink=1" class="new" title="1-(2-Trifluoromethylphenyl)imidazole (page does not exist)">TRIM</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Endothelial_NOS" title="Endothelial NOS">eNOS</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/Aminoguanidine" class="mw-redirect" title="Aminoguanidine">Aminoguanidine (pimagedine)</a></li> <li><a href="/w/index.php?title=N5-(1-Iminoethyl)-L-ornithine&action=edit&redlink=1" class="new" title="N5-(1-Iminoethyl)-L-ornithine (page does not exist)">N<sup>5</sup>-(1-Iminoethyl)-<small>L</small>-ornithine (<small>L</small>-NIO)</a></li> <li><a href="/w/index.php?title=N%CF%89-Methyl-L-arginine&action=edit&redlink=1" class="new" title="Nω-Methyl-L-arginine (page does not exist)">N<sup>ω</sup>-Methyl-<small>L</small>-arginine (<small>L</small>-NMA)</a></li> <li><a href="/wiki/Nitroarginine" title="Nitroarginine">Nitroarginine (NNA, NOARG)</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;">Unsorted</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Asymmetric_dimethylarginine" title="Asymmetric dimethylarginine">Asymmetric dimethylarginine (ADMA)</a></li> <li><a href="/w/index.php?title=CKD-712&action=edit&redlink=1" class="new" title="CKD-712 (page does not exist)">CKD-712</a></li> <li><a href="/w/index.php?title=Guanidinoethyldisulfide&action=edit&redlink=1" class="new" title="Guanidinoethyldisulfide (page does not exist)">Guanidinoethyldisulfide (GED)</a></li> <li><a href="/w/index.php?title=GW-273629&action=edit&redlink=1" class="new" title="GW-273629 (page does not exist)">GW-273629</a></li> <li><a href="/wiki/Indospicine" title="Indospicine">Indospicine</a></li> <li><a href="/w/index.php?title=KD-7040&action=edit&redlink=1" class="new" title="KD-7040 (page does not exist)">KD-7040</a></li> <li><a href="/w/index.php?title=Nitroarginine_methyl_ester&action=edit&redlink=1" class="new" title="Nitroarginine methyl ester (page does not exist)">Nitroarginine methyl ester (NAME)</a></li> <li><a href="/w/index.php?title=NCX-456&action=edit&redlink=1" class="new" title="NCX-456 (page does not exist)">NCX-456</a></li> <li><a href="/w/index.php?title=NXN-462&action=edit&redlink=1" class="new" title="NXN-462 (page does not exist)">NXN-462</a></li> <li><a href="/w/index.php?title=ONO-1714&action=edit&redlink=1" class="new" title="ONO-1714 (page does not exist)">ONO-1714</a></li> <li><a href="/w/index.php?title=VAS-2381&action=edit&redlink=1" class="new" title="VAS-2381 (page does not exist)">VAS-2381</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/Arginase" title="Arginase">Arginase</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="/w/index.php?title=2S-Amino-6-boronohexonic_acid&action=edit&redlink=1" class="new" title="2S-Amino-6-boronohexonic acid (page does not exist)">ABH</a></li> <li><a href="/w/index.php?title=N%CF%89-Hydroxy-L-arginine&action=edit&redlink=1" class="new" title="Nω-Hydroxy-L-arginine (page does not exist)">N<sup>ω</sup>-Hydroxy-<small>L</small>-arginine (NOHA)</a></li> <li><a href="/wiki/Chlorogenic_acid" title="Chlorogenic acid">chlorogenic acid</a></li> <li><a href="/wiki/Ginseng" title="Ginseng">ginseng</a></li> <li><a href="/wiki/Epicatechin" class="mw-redirect" title="Epicatechin">epicatechin</a></li> <li><a href="/wiki/Ornithine" title="Ornithine">ornithine</a></li> <li><a href="/wiki/Norvaline" title="Norvaline">norvaline</a></li> <li><a href="/wiki/Lysine" title="Lysine">lysine</a></li> <li><a href="/w/index.php?title=Alpha_aminoacids&action=edit&redlink=1" class="new" title="Alpha aminoacids (page does not exist)">alpha aminoacids</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/CAMK" title="CAMK">CAMK</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="/w/index.php?title=Calmidazolium&action=edit&redlink=1" class="new" title="Calmidazolium (page does not exist)">Calmidazolium</a></li> <li><a href="/w/index.php?title=W-7_(drug)&action=edit&redlink=1" class="new" title="W-7 (drug) (page does not exist)">W-7</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;">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><i>Precursors:</i> <a href="/wiki/Arginine" title="Arginine"><small>L</small>-Arginine</a></li> <li><a href="/w/index.php?title=N%CF%89-Hydroxy-L-arginine&action=edit&redlink=1" class="new" title="Nω-Hydroxy-L-arginine (page does not exist)">N<sup>ω</sup>-Hydroxy-<small>L</small>-arginine (NOHA)</a></li></ul> <ul><li><i>Cofactors:</i> <a href="/wiki/Nicotinamide_adenine_dinucleotide_phosphate" title="Nicotinamide adenine dinucleotide phosphate">NADPH</a></li> <li><a href="/wiki/Flavin_adenine_dinucleotide" title="Flavin adenine dinucleotide">FAD</a></li> <li><a href="/wiki/Flavin_mononucleotide" title="Flavin mononucleotide">FMN</a></li> <li><a href="/wiki/Heme" title="Heme">Heme</a></li> <li><a href="/wiki/Tetrahydrobiopterin" title="Tetrahydrobiopterin">BH<sub>4</sub></a></li> <li><a href="/wiki/Calmodulin" title="Calmodulin">CaM</a></li> <li><a href="/wiki/Oxygen" title="Oxygen">O<sub>2</sub></a></li> <li><a href="/wiki/Calcium" title="Calcium">Ca<sup>2+</sup></a></li></ul> <ul><li><i>Indirect/downstream NO modulators:</i> <a href="/wiki/ACE_inhibitor" title="ACE inhibitor">ACE inhibitors</a>/<a href="/wiki/Angiotensin_II_receptor_antagonist" class="mw-redirect" title="Angiotensin II receptor antagonist">AT-II receptor antagonists</a> (e.g., <a href="/wiki/Captopril" title="Captopril">captopril</a>, <a href="/wiki/Losartan" title="Losartan">losartan</a>)</li> <li><a href="/wiki/Endothelin_receptor_antagonist" title="Endothelin receptor antagonist">ET<sub>B</sub> receptor antagonists</a> (e.g., <a href="/wiki/Bosentan" title="Bosentan">bosentan</a>)</li> <li><a href="/wiki/L-Type_calcium_channel" class="mw-redirect" title="L-Type calcium channel">L-Type calcium channel</a> <a href="/wiki/Calcium_channel_blocker" title="Calcium channel blocker">blockers</a> (e.g., <a href="/wiki/Dihydropyridine" class="mw-redirect" title="Dihydropyridine">dihydropyridines</a>: <a href="/wiki/Nifedipine" title="Nifedipine">nifedipine</a>)</li> <li><a href="/wiki/Nebivolol" title="Nebivolol">Nebivolol</a> (<a href="/wiki/Beta_blocker" title="Beta blocker">beta blocker</a>)</li> <li><a href="/wiki/PDE5_inhibitor" title="PDE5 inhibitor">PDE5 inhibitors</a> (e.g., <a href="/wiki/Sildenafil" title="Sildenafil">sildenafil</a>)</li> <li>non-selective PDE inhibitors (e.g., <a href="/wiki/Caffeine" title="Caffeine">caffeine</a>)</li> <li>PDE9 inhibitors (e.g., <a href="/wiki/Paraxanthine" title="Paraxanthine">paraxanthine</a>)</li> <li>cGMP preferring PDE inhibitors (e.g., sildenafil, paraxanthine, tadalafil)</li> <li><a href="/wiki/Statin" title="Statin">Statins</a> (e.g., <a href="/wiki/Simvastatin" title="Simvastatin">simvastatin</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><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=Pentaerythritol_tetranitrate&oldid=1251608019">https://en.wikipedia.org/w/index.php?title=Pentaerythritol_tetranitrate&oldid=1251608019</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:Antianginals" title="Category:Antianginals">Antianginals</a></li><li><a href="/wiki/Category:Explosive_chemicals" title="Category:Explosive chemicals">Explosive chemicals</a></li><li><a href="/wiki/Category:German_inventions" title="Category:German inventions">German inventions</a></li><li><a href="/wiki/Category:Nitrate_esters" title="Category:Nitrate esters">Nitrate esters</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:Webarchive_template_wayback_links" title="Category:Webarchive template wayback links">Webarchive template wayback links</a></li><li><a href="/wiki/Category:CS1_maint:_multiple_names:_authors_list" title="Category:CS1 maint: multiple names: authors list">CS1 maint: multiple names: authors list</a></li><li><a href="/wiki/Category:Articles_with_short_description" title="Category:Articles with short description">Articles with short description</a></li><li><a href="/wiki/Category:Short_description_matches_Wikidata" title="Category:Short description matches Wikidata">Short description matches Wikidata</a></li><li><a href="/wiki/Category:Wikipedia_extended-confirmed-protected_pages" title="Category:Wikipedia extended-confirmed-protected pages">Wikipedia extended-confirmed-protected pages</a></li><li><a href="/wiki/Category:Use_mdy_dates_from_November_2015" title="Category:Use mdy dates from November 2015">Use mdy dates from November 2015</a></li><li><a href="/wiki/Category:Articles_without_KEGG_source" title="Category:Articles without KEGG source">Articles without KEGG source</a></li><li><a href="/wiki/Category:ECHA_InfoCard_ID_from_Wikidata" title="Category:ECHA InfoCard ID from Wikidata">ECHA InfoCard ID from Wikidata</a></li><li><a href="/wiki/Category:Chembox_having_GHS_data" title="Category:Chembox having GHS data">Chembox having GHS data</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_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:All_articles_with_unsourced_statements" title="Category:All articles with unsourced statements">All articles with unsourced statements</a></li><li><a href="/wiki/Category:Articles_with_unsourced_statements_from_September_2024" title="Category:Articles with unsourced statements from September 2024">Articles with unsourced statements from September 2024</a></li><li><a href="/wiki/Category:Articles_with_unsourced_statements_from_November_2010" title="Category:Articles with unsourced statements from November 2010">Articles with unsourced statements from November 2010</a></li><li><a href="/wiki/Category:Articles_with_unsourced_statements_from_September_2016" title="Category:Articles with unsourced statements from September 2016">Articles with unsourced statements from September 2016</a></li><li><a href="/wiki/Category:Wikipedia_articles_needing_clarification_from_September_2016" title="Category:Wikipedia articles needing clarification from September 2016">Wikipedia articles needing clarification from September 2016</a></li><li><a href="/wiki/Category:Commons_category_link_is_on_Wikidata" title="Category:Commons category link is on Wikidata">Commons category link is on 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 17 October 2024, at 01:05<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=Pentaerythritol_tetranitrate&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-fn5x6","wgBackendResponseTime":165,"wgPageParseReport":{"limitreport":{"cputime":"1.213","walltime":"1.754","ppvisitednodes":{"value":11775,"limit":1000000},"postexpandincludesize":{"value":289739,"limit":2097152},"templateargumentsize":{"value":48957,"limit":2097152},"expansiondepth":{"value":26,"limit":100},"expensivefunctioncount":{"value":15,"limit":500},"unstrip-depth":{"value":1,"limit":20},"unstrip-size":{"value":195981,"limit":5000000},"entityaccesscount":{"value":1,"limit":400},"timingprofile":["100.00% 1549.130 1 -total"," 43.41% 672.499 1 Template:Chembox"," 23.40% 362.536 1 Template:Reflist"," 20.63% 319.624 1 Template:Chembox_Identifiers"," 14.49% 224.444 24 Template:Trim"," 12.57% 194.719 6 Template:Chembox_headerbar"," 10.50% 162.586 23 Template:Main_other"," 8.39% 129.970 14 Template:Cite_web"," 7.79% 120.703 1 Template:Chembox_parametercheck"," 7.30% 113.077 1 Template:Antianginals_(nitrates)"]},"scribunto":{"limitreport-timeusage":{"value":"0.588","limit":"10.000"},"limitreport-memusage":{"value":12397349,"limit":52428800}},"cachereport":{"origin":"mw-web.eqiad.main-5dc468848-8dkhh","timestamp":"20241122140543","ttl":2592000,"transientcontent":false}}});});</script> <script type="application/ld+json">{"@context":"https:\/\/schema.org","@type":"Article","name":"Pentaerythritol tetranitrate","url":"https:\/\/en.wikipedia.org\/wiki\/Pentaerythritol_tetranitrate","sameAs":"http:\/\/www.wikidata.org\/entity\/Q189334","mainEntity":"http:\/\/www.wikidata.org\/entity\/Q189334","author":{"@type":"Organization","name":"Contributors to Wikimedia projects"},"publisher":{"@type":"Organization","name":"Wikimedia Foundation, Inc.","logo":{"@type":"ImageObject","url":"https:\/\/www.wikimedia.org\/static\/images\/wmf-hor-googpub.png"}},"datePublished":"2002-03-02T10:55:27Z","dateModified":"2024-10-17T01:05:09Z","image":"https:\/\/upload.wikimedia.org\/wikipedia\/commons\/8\/88\/PETN.svg","headline":"explosive chemical compound"}</script> </body> </html>