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<span>Production</span> </div> </a> <button aria-controls="toc-Production-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 Production subsection</span> </button> <ul id="toc-Production-sublist" class="vector-toc-list"> <li id="toc-Niche_or_laboratory_methods" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Niche_or_laboratory_methods"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.1</span> <span>Niche or laboratory methods</span> </div> </a> <ul id="toc-Niche_or_laboratory_methods-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Reactions" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Reactions"> <div class="vector-toc-text"> <span class="vector-toc-numb">3</span> <span>Reactions</span> </div> </a> <ul id="toc-Reactions-sublist" 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class="vector-toc-text"> <span class="vector-toc-numb">4.2</span> <span>Biocide</span> </div> </a> <ul id="toc-Biocide-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Chemical_precursor" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Chemical_precursor"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.3</span> <span>Chemical precursor</span> </div> </a> <ul id="toc-Chemical_precursor-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Health_risks" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Health_risks"> <div class="vector-toc-text"> <span class="vector-toc-numb">5</span> <span>Health risks</span> </div> </a> <button aria-controls="toc-Health_risks-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 Health risks subsection</span> </button> <ul id="toc-Health_risks-sublist" class="vector-toc-list"> <li id="toc-Cigarette_smoke" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Cigarette_smoke"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.1</span> <span>Cigarette smoke</span> </div> </a> <ul id="toc-Cigarette_smoke-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Chemotherapy_metabolite" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Chemotherapy_metabolite"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.2</span> <span>Chemotherapy metabolite</span> </div> </a> <ul id="toc-Chemotherapy_metabolite-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Endogenous_production" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Endogenous_production"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.3</span> <span>Endogenous production</span> </div> </a> <ul id="toc-Endogenous_production-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Analytical_methods" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Analytical_methods"> <div class="vector-toc-text"> <span class="vector-toc-numb">6</span> <span>Analytical methods</span> </div> </a> <ul id="toc-Analytical_methods-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> </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">Acrolein</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 46 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-46" 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">46 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%A3%D9%83%D8%B1%D9%88%D9%84%D9%8A%D9%86" title="أكرولين – Arabic" lang="ar" hreflang="ar" data-title="أكرولين" data-language-autonym="العربية" data-language-local-name="Arabic" class="interlanguage-link-target"><span>العربية</span></a></li><li class="interlanguage-link interwiki-az mw-list-item"><a href="https://az.wikipedia.org/wiki/Akrolein" title="Akrolein – Azerbaijani" lang="az" hreflang="az" data-title="Akrolein" data-language-autonym="Azərbaycanca" data-language-local-name="Azerbaijani" class="interlanguage-link-target"><span>Azərbaycanca</span></a></li><li class="interlanguage-link interwiki-azb mw-list-item"><a href="https://azb.wikipedia.org/wiki/%D8%A7%DA%A9%D8%B1%D9%88%D9%84%DB%8C%D9%86" title="اکرولین – South Azerbaijani" lang="azb" hreflang="azb" data-title="اکرولین" data-language-autonym="تۆرکجه" data-language-local-name="South Azerbaijani" class="interlanguage-link-target"><span>تۆرکجه</span></a></li><li class="interlanguage-link interwiki-be mw-list-item"><a href="https://be.wikipedia.org/wiki/%D0%90%D0%BA%D1%80%D0%B0%D0%BB%D0%B5%D1%96%D0%BD" title="Акралеін – Belarusian" lang="be" hreflang="be" data-title="Акралеін" data-language-autonym="Беларуская" data-language-local-name="Belarusian" class="interlanguage-link-target"><span>Беларуская</span></a></li><li class="interlanguage-link interwiki-ca mw-list-item"><a href="https://ca.wikipedia.org/wiki/Acrole%C3%AFna" title="Acroleïna – Catalan" lang="ca" hreflang="ca" data-title="Acroleïna" 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/Akrolein" title="Akrolein – Czech" lang="cs" hreflang="cs" data-title="Akrolein" data-language-autonym="Čeština" data-language-local-name="Czech" class="interlanguage-link-target"><span>Čeština</span></a></li><li class="interlanguage-link interwiki-de mw-list-item"><a href="https://de.wikipedia.org/wiki/Acrolein" title="Acrolein – German" lang="de" hreflang="de" data-title="Acrolein" data-language-autonym="Deutsch" data-language-local-name="German" class="interlanguage-link-target"><span>Deutsch</span></a></li><li class="interlanguage-link interwiki-et mw-list-item"><a href="https://et.wikipedia.org/wiki/Akroleiin" title="Akroleiin – Estonian" lang="et" hreflang="et" data-title="Akroleiin" data-language-autonym="Eesti" data-language-local-name="Estonian" class="interlanguage-link-target"><span>Eesti</span></a></li><li class="interlanguage-link interwiki-el mw-list-item"><a href="https://el.wikipedia.org/wiki/%CE%A0%CF%81%CE%BF%CF%80%CE%B5%CE%BD%CE%AC%CE%BB%CE%B7" title="Προπενάλη – Greek" lang="el" hreflang="el" data-title="Προπενάλη" 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/Acrole%C3%ADna" title="Acroleína – Spanish" lang="es" hreflang="es" data-title="Acroleína" 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/Akroleino" title="Akroleino – Esperanto" lang="eo" hreflang="eo" data-title="Akroleino" 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/Akroleina" title="Akroleina – Basque" lang="eu" hreflang="eu" data-title="Akroleina" data-language-autonym="Euskara" data-language-local-name="Basque" class="interlanguage-link-target"><span>Euskara</span></a></li><li class="interlanguage-link interwiki-fa mw-list-item"><a href="https://fa.wikipedia.org/wiki/%D8%A2%DA%A9%D8%B1%D9%88%D9%84%D8%A6%DB%8C%D9%86" title="آکرولئین – Persian" lang="fa" hreflang="fa" data-title="آکرولئین" 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/Acrol%C3%A9ine" title="Acroléine – French" lang="fr" hreflang="fr" data-title="Acroléine" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target"><span>Français</span></a></li><li class="interlanguage-link interwiki-gl mw-list-item"><a href="https://gl.wikipedia.org/wiki/Acrole%C3%ADna" title="Acroleína – Galician" lang="gl" hreflang="gl" data-title="Acroleína" data-language-autonym="Galego" data-language-local-name="Galician" class="interlanguage-link-target"><span>Galego</span></a></li><li class="interlanguage-link interwiki-ko mw-list-item"><a href="https://ko.wikipedia.org/wiki/%EC%95%84%ED%81%AC%EB%A1%A4%EB%A0%88%EC%9D%B8" title="아크롤레인 – Korean" lang="ko" hreflang="ko" data-title="아크롤레인" data-language-autonym="한국어" data-language-local-name="Korean" class="interlanguage-link-target"><span>한국어</span></a></li><li class="interlanguage-link interwiki-hy mw-list-item"><a href="https://hy.wikipedia.org/wiki/%D4%B1%D5%AF%D6%80%D5%B8%D5%AC%D5%A5%D5%AB%D5%B6" title="Ակրոլեին – Armenian" lang="hy" hreflang="hy" data-title="Ակրոլեին" data-language-autonym="Հայերեն" data-language-local-name="Armenian" class="interlanguage-link-target"><span>Հայերեն</span></a></li><li class="interlanguage-link interwiki-hi mw-list-item"><a href="https://hi.wikipedia.org/wiki/%E0%A4%8F%E0%A4%95%E0%A5%8D%E0%A4%B0%E0%A5%8B%E0%A4%B2%E0%A4%BF%E0%A4%A8" title="एक्रोलिन – Hindi" lang="hi" hreflang="hi" data-title="एक्रोलिन" data-language-autonym="हिन्दी" data-language-local-name="Hindi" class="interlanguage-link-target"><span>हिन्दी</span></a></li><li class="interlanguage-link interwiki-id mw-list-item"><a href="https://id.wikipedia.org/wiki/Akrolein" title="Akrolein – Indonesian" lang="id" hreflang="id" data-title="Akrolein" 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/Acroleina" title="Acroleina – Italian" lang="it" hreflang="it" data-title="Acroleina" data-language-autonym="Italiano" data-language-local-name="Italian" class="interlanguage-link-target"><span>Italiano</span></a></li><li class="interlanguage-link interwiki-he mw-list-item"><a href="https://he.wikipedia.org/wiki/%D7%90%D7%A7%D7%A8%D7%95%D7%9C%D7%99%D7%99%D7%9F" title="אקרוליין – Hebrew" lang="he" hreflang="he" data-title="אקרוליין" data-language-autonym="עברית" data-language-local-name="Hebrew" class="interlanguage-link-target"><span>עברית</span></a></li><li class="interlanguage-link interwiki-ka mw-list-item"><a href="https://ka.wikipedia.org/wiki/%E1%83%90%E1%83%99%E1%83%A0%E1%83%9D%E1%83%9A%E1%83%94%E1%83%98%E1%83%9C%E1%83%98" title="აკროლეინი – Georgian" lang="ka" hreflang="ka" data-title="აკროლეინი" data-language-autonym="ქართული" data-language-local-name="Georgian" class="interlanguage-link-target"><span>ქართული</span></a></li><li class="interlanguage-link interwiki-kk mw-list-item"><a href="https://kk.wikipedia.org/wiki/%D0%90%D0%BA%D1%80%D0%BE%D0%BB%D0%B5%D0%B8%D0%BD" title="Акролеин – Kazakh" lang="kk" hreflang="kk" data-title="Акролеин" data-language-autonym="Қазақша" data-language-local-name="Kazakh" class="interlanguage-link-target"><span>Қазақша</span></a></li><li class="interlanguage-link interwiki-ky mw-list-item"><a href="https://ky.wikipedia.org/wiki/%D0%90%D0%BA%D1%80%D0%BE%D0%BB%D0%B5%D0%B8%D0%BD" title="Акролеин – Kyrgyz" lang="ky" hreflang="ky" data-title="Акролеин" data-language-autonym="Кыргызча" data-language-local-name="Kyrgyz" class="interlanguage-link-target"><span>Кыргызча</span></a></li><li class="interlanguage-link interwiki-lv mw-list-item"><a href="https://lv.wikipedia.org/wiki/Akrole%C4%ABns" title="Akroleīns – Latvian" lang="lv" hreflang="lv" data-title="Akroleīns" 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/Akroleinas" title="Akroleinas – Lithuanian" lang="lt" hreflang="lt" data-title="Akroleinas" 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/Akrolein" title="Akrolein – Hungarian" lang="hu" hreflang="hu" data-title="Akrolein" data-language-autonym="Magyar" data-language-local-name="Hungarian" class="interlanguage-link-target"><span>Magyar</span></a></li><li class="interlanguage-link interwiki-ml mw-list-item"><a href="https://ml.wikipedia.org/wiki/%E0%B4%85%E0%B4%95%E0%B5%8D%E0%B4%B0%E0%B5%8B%E0%B4%B2%E0%B4%BF%E0%B5%BB" title="അക്രോലിൻ – Malayalam" lang="ml" hreflang="ml" data-title="അക്രോലിൻ" data-language-autonym="മലയാളം" data-language-local-name="Malayalam" class="interlanguage-link-target"><span>മലയാളം</span></a></li><li class="interlanguage-link interwiki-ms mw-list-item"><a href="https://ms.wikipedia.org/wiki/Akrolein" title="Akrolein – Malay" lang="ms" hreflang="ms" data-title="Akrolein" data-language-autonym="Bahasa Melayu" data-language-local-name="Malay" class="interlanguage-link-target"><span>Bahasa Melayu</span></a></li><li class="interlanguage-link interwiki-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/Acrole%C3%AFne" title="Acroleïne – Dutch" lang="nl" hreflang="nl" data-title="Acroleïne" 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%82%A2%E3%82%AF%E3%83%AD%E3%83%AC%E3%82%A4%E3%83%B3" title="アクロレイン – Japanese" lang="ja" hreflang="ja" data-title="アクロレイン" data-language-autonym="日本語" data-language-local-name="Japanese" class="interlanguage-link-target"><span>日本語</span></a></li><li class="interlanguage-link interwiki-uz mw-list-item"><a href="https://uz.wikipedia.org/wiki/Akrolein" title="Akrolein – Uzbek" lang="uz" hreflang="uz" data-title="Akrolein" data-language-autonym="Oʻzbekcha / ўзбекча" data-language-local-name="Uzbek" class="interlanguage-link-target"><span>Oʻzbekcha / ўзбекча</span></a></li><li class="interlanguage-link interwiki-pl mw-list-item"><a href="https://pl.wikipedia.org/wiki/Akroleina" title="Akroleina – Polish" lang="pl" hreflang="pl" data-title="Akroleina" 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/Acrole%C3%ADna" title="Acroleína – Portuguese" lang="pt" hreflang="pt" data-title="Acroleína" data-language-autonym="Português" data-language-local-name="Portuguese" class="interlanguage-link-target"><span>Português</span></a></li><li class="interlanguage-link interwiki-ro mw-list-item"><a href="https://ro.wikipedia.org/wiki/Acrolein%C4%83" title="Acroleină – Romanian" lang="ro" hreflang="ro" data-title="Acroleină" data-language-autonym="Română" data-language-local-name="Romanian" class="interlanguage-link-target"><span>Română</span></a></li><li class="interlanguage-link interwiki-ru mw-list-item"><a href="https://ru.wikipedia.org/wiki/%D0%90%D0%BA%D1%80%D0%BE%D0%BB%D0%B5%D0%B8%D0%BD" title="Акролеин – Russian" lang="ru" hreflang="ru" data-title="Акролеин" data-language-autonym="Русский" data-language-local-name="Russian" class="interlanguage-link-target"><span>Русский</span></a></li><li class="interlanguage-link interwiki-sl mw-list-item"><a href="https://sl.wikipedia.org/wiki/Akrolein" title="Akrolein – Slovenian" lang="sl" hreflang="sl" data-title="Akrolein" 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/Akrolein" title="Akrolein – Serbian" lang="sr" hreflang="sr" data-title="Akrolein" 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/Akrolein" title="Akrolein – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Akrolein" 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 badge-Q17559452 badge-recommendedarticle mw-list-item" title="recommended article"><a href="https://fi.wikipedia.org/wiki/Akroleiini" title="Akroleiini – Finnish" lang="fi" hreflang="fi" data-title="Akroleiini" 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/Akrolein" title="Akrolein – Swedish" lang="sv" hreflang="sv" data-title="Akrolein" data-language-autonym="Svenska" data-language-local-name="Swedish" class="interlanguage-link-target"><span>Svenska</span></a></li><li class="interlanguage-link interwiki-tg mw-list-item"><a href="https://tg.wikipedia.org/wiki/%D0%90%D0%BA%D1%80%D0%BE%D0%BB%D0%B5%D0%B8%D0%BD" title="Акролеин – Tajik" lang="tg" hreflang="tg" data-title="Акролеин" data-language-autonym="Тоҷикӣ" data-language-local-name="Tajik" class="interlanguage-link-target"><span>Тоҷикӣ</span></a></li><li class="interlanguage-link interwiki-tr mw-list-item"><a href="https://tr.wikipedia.org/wiki/Akrolein" title="Akrolein – Turkish" lang="tr" hreflang="tr" 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id="siteSub" class="noprint">From Wikipedia, the free encyclopedia</div> </div> <div id="contentSub"><div id="mw-content-subtitle"></div></div> <div id="mw-content-text" class="mw-body-content"><div class="mw-content-ltr mw-parser-output" lang="en" dir="ltr"><style data-mw-deduplicate="TemplateStyles:r1236090951">.mw-parser-output .hatnote{font-style:italic}.mw-parser-output div.hatnote{padding-left:1.6em;margin-bottom:0.5em}.mw-parser-output .hatnote i{font-style:normal}.mw-parser-output .hatnote+link+.hatnote{margin-top:-0.5em}@media print{body.ns-0 .mw-parser-output .hatnote{display:none!important}}</style><div role="note" class="hatnote navigation-not-searchable">Not to be confused with <a href="/wiki/Propanol" title="Propanol">Propanol</a>, <a href="/wiki/Acyloin" title="Acyloin">Acyloin</a>, or <a href="/wiki/Propanal" class="mw-redirect" title="Propanal">Propanal</a>.</div> <style data-mw-deduplicate="TemplateStyles:r1084375498">.mw-parser-output .ib-chembox{border-collapse:collapse;text-align:left}.mw-parser-output .ib-chembox td,.mw-parser-output .ib-chembox th{border:1px solid #a2a9b1;width:40%}.mw-parser-output .ib-chembox td+td{width:60%}</style> <table class="infobox ib-chembox"> <caption>Acrolein </caption> <tbody><tr> <td colspan="2" class="borderless" style="text-align:center"> <table border="0" style="width:100%;display:inline-table;"> <tbody><tr> <td style="border-right:1px solid #aaa; width:50%;"><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Acrolein-s-trans-2D-w.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/7/70/Acrolein-s-trans-2D-w.png/110px-Acrolein-s-trans-2D-w.png" decoding="async" width="110" height="88" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/7/70/Acrolein-s-trans-2D-w.png/165px-Acrolein-s-trans-2D-w.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/7/70/Acrolein-s-trans-2D-w.png/220px-Acrolein-s-trans-2D-w.png 2x" data-file-width="1100" data-file-height="875" /></a><figcaption></figcaption></figure> </td> <td style="width:50%;"><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Acrolein-s-trans-2D-skeletal.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/8/89/Acrolein-s-trans-2D-skeletal.png/110px-Acrolein-s-trans-2D-skeletal.png" decoding="async" width="110" height="44" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/8/89/Acrolein-s-trans-2D-skeletal.png/165px-Acrolein-s-trans-2D-skeletal.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/8/89/Acrolein-s-trans-2D-skeletal.png/220px-Acrolein-s-trans-2D-skeletal.png 2x" data-file-width="1219" data-file-height="493" /></a><figcaption></figcaption></figure> </td></tr></tbody></table> </td></tr> <tr> <td colspan="2" class="borderless" style="text-align:center"> <table border="0" style="width:100%;display:inline-table;"> <tbody><tr> <td style="border-right:1px solid #aaa; width:50%;"><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Acrolein-s-trans-GED-MW-3D-bs-17.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/6/6e/Acrolein-s-trans-GED-MW-3D-bs-17.png/110px-Acrolein-s-trans-GED-MW-3D-bs-17.png" decoding="async" width="110" height="77" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/6e/Acrolein-s-trans-GED-MW-3D-bs-17.png/165px-Acrolein-s-trans-GED-MW-3D-bs-17.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/6e/Acrolein-s-trans-GED-MW-3D-bs-17.png/220px-Acrolein-s-trans-GED-MW-3D-bs-17.png 2x" data-file-width="3000" data-file-height="2087" /></a><figcaption></figcaption></figure> </td> <td style="width:50%;"><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Acrolein-s-trans-GED-MW-3D-sf.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/c/c8/Acrolein-s-trans-GED-MW-3D-sf.png/120px-Acrolein-s-trans-GED-MW-3D-sf.png" decoding="async" width="120" height="91" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/c/c8/Acrolein-s-trans-GED-MW-3D-sf.png/180px-Acrolein-s-trans-GED-MW-3D-sf.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/c/c8/Acrolein-s-trans-GED-MW-3D-sf.png/240px-Acrolein-s-trans-GED-MW-3D-sf.png 2x" data-file-width="2913" data-file-height="2208" /></a><figcaption></figcaption></figure> </td></tr></tbody></table> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Names </th></tr> <tr> <td colspan="2" style="text-align:left;"><a href="/wiki/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;">Prop-2-enal</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;">Acraldehyde<sup id="cite_ref-NIOSH_1-0" class="reference"><a href="#cite_note-NIOSH-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup><br />Acrylic aldehyde<sup id="cite_ref-NIOSH_1-1" class="reference"><a href="#cite_note-NIOSH-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup><br />Allyl aldehyde<sup id="cite_ref-NIOSH_1-2" class="reference"><a href="#cite_note-NIOSH-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup><br />Ethylene aldehyde<br /> Acrylaldehyde<sup id="cite_ref-NIOSH_1-3" class="reference"><a href="#cite_note-NIOSH-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup></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=107-02-8">107-02-8</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=O%3DCC%3DC">Interactive image</a></span></li><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%3DCC%3DO">Interactive image</a></span></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ChEBI" title="ChEBI">ChEBI</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.ebi.ac.uk"><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chebi/searchId.do?chebiId=15368">CHEBI:15368</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ChEMBL" title="ChEMBL">ChEMBL</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.ebi.ac.uk"><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chembldb/index.php/compound/inspect/ChEMBL721">ChEMBL721</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.7559.html">7559</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/100.003.141">100.003.141</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q342790#P2566" title="Edit this at Wikidata"><img alt="Edit this at Wikidata" src="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/10px-OOjs_UI_icon_edit-ltr-progressive.svg.png" decoding="async" width="10" height="10" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/15px-OOjs_UI_icon_edit-ltr-progressive.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/20px-OOjs_UI_icon_edit-ltr-progressive.svg.png 2x" data-file-width="20" data-file-height="20" /></a></span> </td></tr> <tr> <td><a href="/wiki/European_Community_number" title="European Community number"><span title="European Community number (chemical identifier)">EC Number</span></a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li>203-453-4</li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/IUPHAR/BPS" class="mw-redirect" title="IUPHAR/BPS">IUPHAR/BPS</a></div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.guidetopharmacology.org"><a rel="nofollow" class="external text" href="http://www.guidetopharmacology.org/GRAC/LigandDisplayForward?tab=summary&ligandId=2418">2418</a></span></li></ul></div> </td></tr> <tr> <td><a href="/wiki/KEGG" title="KEGG">KEGG</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.kegg.jp"><a rel="nofollow" class="external text" href="https://www.kegg.jp/entry/C01471">C01471</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/PubChem" title="PubChem">PubChem</a> <abbr title="Compound ID">CID</abbr></div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="pubchem.ncbi.nlm.nih.gov"><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/7847">7847</a></span></li></ul></div> </td></tr> <tr> <td><a href="/wiki/RTECS" class="mw-redirect" title="RTECS">RTECS number</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li>AS1050000</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/7864XYD3JJ">7864XYD3JJ</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/UN_number" title="UN number">UN number</a> </td> <td>1092 </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/DTXSID5020023">DTXSID5020023</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q342790#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/C3H4O/c1-2-3-4/h2-3H,1H2<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: HGINCPLSRVDWNT-UHFFFAOYSA-N<sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></div></div></li><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.5em; text-align:left;"><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">InChI=1/C3H4O/c1-2-3-4/h2-3H,1H2</div><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">Key: HGINCPLSRVDWNT-UHFFFAOYAQ</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%;">O=CC=C</div></li><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.6em; word-wrap:break-word; text-indent:-1.5em; text-align:left; font-size:97%; line-height:120%;">C=CC=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>3</sub><span title="Hydrogen">H</span><sub>4</sub><span title="Oxygen">O</span> </td></tr> <tr> <td><a href="/wiki/Molar_mass" title="Molar mass">Molar mass</a> </td> <td><span class="nowrap"><span data-sort-value="7001560640000000000♠"></span>56.064</span> g·mol<sup>−1</sup>   </td></tr> <tr> <td>Appearance </td> <td>Colorless to yellow liquid. Colorless gas in smoke. </td></tr> <tr> <td><a href="/wiki/Odor" title="Odor">Odor</a> </td> <td>Acrid, Foul, Irritating </td></tr> <tr> <td><a href="/wiki/Density" title="Density">Density</a> </td> <td>0.839 g/mL </td></tr> <tr> <td><a href="/wiki/Melting_point" title="Melting point">Melting point</a> </td> <td>−88 °C (−126 °F; 185 K) </td></tr> <tr> <td><a href="/wiki/Boiling_point" title="Boiling point">Boiling point</a> </td> <td>53 °C (127 °F; 326 K) </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Aqueous_solution" title="Aqueous solution">Solubility in water</a></div> </td> <td>Appreciable (> 10%) </td></tr> <tr> <td><a href="/wiki/Vapor_pressure" title="Vapor pressure">Vapor pressure</a> </td> <td>210 mmHg<sup id="cite_ref-NIOSH_1-4" class="reference"><a href="#cite_note-NIOSH-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Hazards<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> </th></tr> <tr> <td colspan="2" style="text-align:left; background-color:#eaeaea;"><b><a href="/wiki/Occupational_safety_and_health" title="Occupational safety and health">Occupational safety and health</a></b> (OHS/OSH): </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">Main hazards</div> </td> <td>Highly poisonous. Causes severe irritation to exposed membranes. Extremely flammable liquid and vapor. </td></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-flamme.svg" class="mw-file-description" title="GHS02: Flammable"><img alt="GHS02: Flammable" src="//upload.wikimedia.org/wikipedia/commons/thumb/6/6d/GHS-pictogram-flamme.svg/50px-GHS-pictogram-flamme.svg.png" decoding="async" width="50" height="50" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/6d/GHS-pictogram-flamme.svg/75px-GHS-pictogram-flamme.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/6d/GHS-pictogram-flamme.svg/100px-GHS-pictogram-flamme.svg.png 2x" data-file-width="512" data-file-height="512" /></a></span> <span typeof="mw:File"><a href="/wiki/File:GHS-pictogram-acid.svg" class="mw-file-description" title="GHS05: Corrosive"><img alt="GHS05: Corrosive" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a1/GHS-pictogram-acid.svg/50px-GHS-pictogram-acid.svg.png" decoding="async" width="50" height="50" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a1/GHS-pictogram-acid.svg/75px-GHS-pictogram-acid.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a1/GHS-pictogram-acid.svg/100px-GHS-pictogram-acid.svg.png 2x" data-file-width="724" data-file-height="724" /></a></span> <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-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> <span typeof="mw:File"><a href="/wiki/File:GHS-pictogram-pollu.svg" class="mw-file-description" title="GHS09: Environmental hazard"><img alt="GHS09: Environmental hazard" src="//upload.wikimedia.org/wikipedia/commons/thumb/b/b9/GHS-pictogram-pollu.svg/50px-GHS-pictogram-pollu.svg.png" decoding="async" width="50" height="50" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/b/b9/GHS-pictogram-pollu.svg/75px-GHS-pictogram-pollu.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/b/b9/GHS-pictogram-pollu.svg/100px-GHS-pictogram-pollu.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="H225: Highly flammable liquid and vapour">H225</abbr>, <abbr class="abbr" title="H300: Fatal if swallowed">H300</abbr>, <abbr class="abbr" title="H311: Toxic in contact with skin">H311</abbr>, <abbr class="abbr" title="H314: Causes severe skin burns and eye damage">H314</abbr>, <abbr class="abbr" title="H330: Fatal if inhaled">H330</abbr>, <abbr class="abbr" title="H410: Very toxic to aquatic life with long lasting effects">H410</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="P233: Keep container tightly closed.">P233</abbr>, <abbr class="abbr" title="P240: Ground and bond container and receiving equipment.">P240</abbr>, <abbr class="abbr" title="P241: Use explosion-proof electrical/ventilating/light/.../equipment.">P241</abbr>, <abbr class="abbr" title="P242: Use only non-sparking tools.">P242</abbr>, <abbr class="abbr" title="P243: Take precautionary measures to prevent static discharges.">P243</abbr>, <abbr class="abbr" title="P260: Do not breathe dust/fume/gas/mist/vapours/spray.">P260</abbr>, <abbr class="abbr" title="P264: Wash ... thoroughly after handling.">P264</abbr>, <abbr class="abbr" title="P270: Do not eat, drink or smoke when using this product.">P270</abbr>, <abbr class="abbr" title="P271: Use only outdoors or in a well-ventilated area.">P271</abbr>, <abbr class="abbr" title="P273: Avoid release to the environment.">P273</abbr>, <abbr class="abbr" title="P280: Wear protective gloves/protective clothing/eye protection/face protection.">P280</abbr>, <abbr class="abbr" title="P284: Wear respiratory protection.">P284</abbr>, <abbr class="abbr" title="P301+P310: IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.">P301+P310</abbr>, <abbr class="abbr" title="P301+P330+P331: IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.">P301+P330+P331</abbr>, <abbr class="abbr" title="P302+P352: IF ON SKIN: Wash with soap and water.">P302+P352</abbr>, <abbr class="abbr" title="P303+P361+P353: IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water [or shower].">P303+P361+P353</abbr>, <abbr class="abbr" title="P304+P340: IF INHALED: Remove victim to fresh air and keep at rest in a position comfortable for breathing.">P304+P340</abbr>, <abbr class="abbr" title="P305+P351+P338: IF IN EYES: Rinse continuously with water for several minutes. Remove contact lenses if present and easy to do. Continue rinsing.">P305+P351+P338</abbr>, <abbr class="abbr" title="P310: Immediately call a POISON CENTER or doctor/physician.">P310</abbr>, <abbr class="abbr" title="P312: Call a POISON CENTER or doctor/physician if you feel unwell.">P312</abbr>, <abbr class="abbr" title="P320: Specific treatment is urgent (see ... on this label).">P320</abbr>, <abbr class="abbr" title="P321: Specific treatment (see ... on this label).">P321</abbr>, <abbr class="abbr" title="P322: Specific measures (see ... on this label).">P322</abbr>, <abbr class="abbr" title="P330: Rinse mouth.">P330</abbr>, <abbr class="abbr" title="P361: Remove/Take off immediately all contaminated clothing.">P361</abbr>, <abbr class="abbr" title="P363: Wash contaminated clothing before reuse.">P363</abbr>, <abbr class="abbr" title="P370+P378: In case of fire: Use ... to extinguish.">P370+P378</abbr>, <abbr class="abbr" title="P391: Collect spillage.">P391</abbr>, <abbr class="abbr" title="P403+P233: Store in a well ventilated place. Keep container tightly closed.">P403+P233</abbr>, <abbr class="abbr" title="P403+P235: Store in a well ventilated place. Keep cool.">P403+P235</abbr>, <abbr class="abbr" title="P405: Store locked up.">P405</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_0654ab5114f989e7" /></span><map name="ImageMap_0654ab5114f989e7"><area href="/wiki/NFPA_704#Blue" shape="poly" coords="23,23,47,47,23,70,0,47" alt="Health 4: Very short exposure could cause death or major residual injury. E.g. VX gas" title="Health 4: Very short exposure could cause death or major residual injury. E.g. VX gas" /><area href="/wiki/NFPA_704#Red" shape="poly" coords="47,0,70,23,47,47,23,23" alt="Flammability 3: Liquids and solids that can be ignited under almost all ambient temperature conditions. Flash point between 23 and 38 °C (73 and 100 °F). E.g. gasoline" title="Flammability 3: Liquids and solids that can be ignited under almost all ambient temperature conditions. Flash point between 23 and 38 °C (73 and 100 °F). E.g. gasoline" /><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 4: Very short exposure could cause death or major residual injury. E.g. VX gas" class="notheme mw-no-invert">4</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 3: Liquids and solids that can be ignited under almost all ambient temperature conditions. Flash point between 23 and 38 °C (73 and 100 °F). E.g. gasoline" class="notheme mw-no-invert">3</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><a href="/wiki/Flash_point" title="Flash point">Flash point</a> </td> <td>−26 °C (−15 °F; 247 K) </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>278 °C (532 °F; 551 K) </td></tr> <tr> <td><a href="/wiki/Explosive_limit" class="mw-redirect" title="Explosive limit">Explosive limits</a> </td> <td>2.8-31%<sup id="cite_ref-NIOSH_1-5" class="reference"><a href="#cite_note-NIOSH-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td colspan="2" style="text-align:left; background-color:#eaeaea;"><b>Lethal dose</b> or concentration (LD, LC): </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">LC<sub>50</sub> (<a href="/wiki/Lethal_dose#LC50" title="Lethal dose">median concentration</a>)</div> </td> <td>875 ppm (mouse, 1 min)<br />175 ppm (mouse, 10 min)<br />150 ppm (dog, 30 min)<br />8 ppm (rat, 4 hr)<br />375 ppm (rat, 10 min)<br />25.4 ppm (hamster, 4 hr)<br />131 ppm (rat, 30 min)<sup id="cite_ref-IDLH_2-0" class="reference"><a href="#cite_note-IDLH-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">LC<sub>Lo</sub> (<a href="/wiki/Lethal_dose#LCLo" title="Lethal dose">lowest published</a>)</div> </td> <td>674 ppm (cat, 2 hr)<sup id="cite_ref-IDLH_2-1" class="reference"><a href="#cite_note-IDLH-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td colspan="2" style="text-align:left; background-color:#eaeaea;"><a href="/wiki/National_Institute_for_Occupational_Safety_and_Health" title="National Institute for Occupational Safety and Health"><b>NIOSH</b></a> (US health exposure limits): </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Permissible_exposure_limit" title="Permissible exposure limit">PEL</a> (Permissible)</div> </td> <td>TWA 0.1 ppm (0.25 mg/m<sup>3</sup>)<sup id="cite_ref-NIOSH_1-6" class="reference"><a href="#cite_note-NIOSH-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Recommended_exposure_limit" title="Recommended exposure limit">REL</a> (Recommended)</div> </td> <td>TWA 0.1 ppm (0.25 mg/m<sup>3</sup>) ST 0.3 ppm (0.8 mg/m<sup>3</sup>)<sup id="cite_ref-NIOSH_1-7" class="reference"><a href="#cite_note-NIOSH-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/IDLH" class="mw-redirect" title="IDLH">IDLH</a> (Immediate danger)</div> </td> <td>2 ppm<sup id="cite_ref-NIOSH_1-8" class="reference"><a href="#cite_note-NIOSH-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><a href="/wiki/Safety_data_sheet" title="Safety data sheet">Safety data sheet</a> (SDS) </td> <td><a rel="nofollow" class="external text" href="https://www.sigmaaldrich.com/GB/en/sds/aldrich/110221">Sigma-Aldrich SDS</a> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Related compounds </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">Related alkenals</div> </td> <td><a href="/wiki/Crotonaldehyde" title="Crotonaldehyde">Crotonaldehyde</a><br /> <p><a href="/wiki/Cis-3-hexenal" class="mw-redirect" title="Cis-3-hexenal"><i>cis</i>-3-Hexenal</a><br /> <a href="/wiki/(E,E)-2,4-decadienal" class="mw-redirect" title="(E,E)-2,4-decadienal">(<i>E</i>,<i>E</i>)-2,4-Decadienal</a> </p> </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=477241293&page2=Acrolein">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>Acrolein</b> (systematic name: <b>propenal</b>) is the simplest <a href="/wiki/Alpha-beta_Unsaturated_carbonyl_compounds" class="mw-redirect" title="Alpha-beta Unsaturated carbonyl compounds">unsaturated aldehyde</a>. It is a colorless liquid with a foul and acrid aroma. The smell of burnt fat (as when <a href="/wiki/Cooking_oil" title="Cooking oil">cooking oil</a> is heated to its <a href="/wiki/Smoke_point" title="Smoke point">smoke point</a>) is caused by <a href="/wiki/Glycerol" title="Glycerol">glycerol</a> in the burning fat breaking down into acrolein. It is produced industrially from <a href="/wiki/Propene" class="mw-redirect" title="Propene">propene</a> and mainly used as a <a href="/wiki/Biocide" title="Biocide">biocide</a> and a building block to other chemical compounds, such as the <a href="/wiki/Amino_acid" title="Amino acid">amino acid</a> <a href="/wiki/Methionine" title="Methionine">methionine</a>. </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="History">History</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Acrolein&action=edit&section=1" title="Edit section: History"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Acrolein was first named and characterized as an aldehyde by the Swedish chemist <a href="/wiki/J%C3%B6ns_Jacob_Berzelius" title="Jöns Jacob Berzelius">Jöns Jacob Berzelius</a> in 1839. He had been working with it as a thermal degradation product of <a href="/wiki/Glycerol" title="Glycerol">glycerol</a>, a material used in the manufacture of soap. The name is a contraction of 'acrid' (referring to its pungent smell) and 'oleum' (referring to its oil-like consistency). In the 20th century, acrolein became an important intermediate for the industrial production of <a href="/wiki/Acrylic_acid" title="Acrylic acid">acrylic acid</a> and acrylic plastics.<sup id="cite_ref-4" class="reference"><a href="#cite_note-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Production">Production</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Acrolein&action=edit&section=2" title="Edit section: Production"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Acrolein is prepared industrially by oxidation of <a href="/wiki/Propene" class="mw-redirect" title="Propene">propene</a>. The process uses air as the source of oxygen and requires <a href="/wiki/Metal_oxide" class="mw-redirect" title="Metal oxide">metal oxides</a> as <a href="/wiki/Heterogeneous_catalyst" class="mw-redirect" title="Heterogeneous catalyst">heterogeneous catalysts</a>:<sup id="cite_ref-Ullmann_5-0" class="reference"><a href="#cite_note-Ullmann-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> </p> <dl><dd><style data-mw-deduplicate="TemplateStyles:r1123817410">.mw-parser-output .template-chem2-su{display:inline-block;font-size:80%;line-height:1;vertical-align:-0.35em}.mw-parser-output .template-chem2-su>span{display:block;text-align:left}.mw-parser-output sub.template-chem2-sub{font-size:80%;vertical-align:-0.35em}.mw-parser-output sup.template-chem2-sup{font-size:80%;vertical-align:0.65em}</style><span class="chemf nowrap">CH<sub class="template-chem2-sub">3</sub>CH=CH<sub class="template-chem2-sub">2</sub> + O<sub class="template-chem2-sub">2</sub> → CH<sub class="template-chem2-sub">2</sub>=CHCHO + H<sub class="template-chem2-sub">2</sub>O</span></dd></dl> <p>About 500,000 tons of acrolein are produced in this way annually in North America, Europe, and Japan. Additionally, all <a href="/wiki/Acrylic_acid" title="Acrylic acid">acrylic acid</a> is produced via the transient formation of acrolein. </p><p><a href="/wiki/Propane" title="Propane">Propane</a> represents a promising but challenging feedstock for the synthesis of acrolein (and acrylic acid).The main challenge is in fact the overoxidation to this acid. </p><p>When <a href="/wiki/Glycerol" title="Glycerol">glycerol</a> (also called glycerin) is heated to 280 °C, it decomposes into acrolein: </p> <dl><dd>(CH<sub>2</sub>OH)<sub>2</sub>CHOH → CH<sub>2</sub>=CHCHO + 2 H<sub>2</sub>O</dd></dl> <p>This route is attractive when glycerol is co-generated in the production of biodiesel from vegetable oils or animal fats. The dehydration of glycerol has been demonstrated but has not proven competitive with the route from <a href="/wiki/Petrochemical" title="Petrochemical">petrochemicals</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> </p> <div class="mw-heading mw-heading3"><h3 id="Niche_or_laboratory_methods">Niche or laboratory methods</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Acrolein&action=edit&section=3" title="Edit section: Niche or laboratory methods"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The original industrial route to acrolein, developed by Degussa, involves <a href="/wiki/Aldol_condensation" title="Aldol condensation">aldol condensation</a> of <a href="/wiki/Formaldehyde" title="Formaldehyde">formaldehyde</a> and <a href="/wiki/Acetaldehyde" title="Acetaldehyde">acetaldehyde</a>: </p> <dl><dd>HCHO + CH<sub>3</sub>CHO → CH<sub>2</sub>=CHCHO + H<sub>2</sub>O</dd></dl> <p>Acrolein may also be produced on lab scale by the action of <a href="/wiki/Potassium_bisulfate" title="Potassium bisulfate">potassium bisulfate</a> on glycerol (glycerine).<sup id="cite_ref-8" class="reference"><a href="#cite_note-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Reactions">Reactions</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Acrolein&action=edit&section=4" title="Edit section: Reactions"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Acrolein is a relatively <a href="/wiki/Electrophile" title="Electrophile">electrophilic</a> compound and a reactive one, hence its high toxicity. It is a good <a href="/wiki/Michael_acceptor" class="mw-redirect" title="Michael acceptor">Michael acceptor</a>, hence its useful reaction with thiols. It forms <a href="/wiki/Acetal" title="Acetal">acetals</a> readily, a prominent one being the <a href="/wiki/Spirocycle" class="mw-redirect" title="Spirocycle">spirocycle</a> derived from <a href="/wiki/Pentaerythritol" title="Pentaerythritol">pentaerythritol</a>, diallylidene pentaerythritol. Acrolein participates in many <a href="/wiki/Diels-Alder_reaction" class="mw-redirect" title="Diels-Alder reaction">Diels-Alder reactions</a>, even with itself. Via Diels-Alder reactions, it is a precursor to some commercial fragrances, including <a href="/wiki/Myrac_aldehyde" class="mw-redirect" title="Myrac aldehyde">myrac aldehyde ("lyral")</a> and <a href="/wiki/Norbornene" title="Norbornene">norbornene</a>-2-carboxaldehyde.<sup id="cite_ref-Ullmann_5-1" class="reference"><a href="#cite_note-Ullmann-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> The monomer <a href="/wiki/3,4-epoxycyclohexylmethyl-3%27,4%27-epoxycyclohexane_carboxylate" class="mw-redirect" title="3,4-epoxycyclohexylmethyl-3',4'-epoxycyclohexane carboxylate">3,4-epoxycyclohexylmethyl-3',4'-epoxycyclohexane carboxylate</a> is also produced from acrolein via the intermediacy of <a href="/wiki/Tetrahydrobenzaldehyde" title="Tetrahydrobenzaldehyde">tetrahydrobenzaldehyde</a>. </p> <div class="mw-heading mw-heading2"><h2 id="Uses">Uses</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Acrolein&action=edit&section=5" title="Edit section: Uses"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Military_uses">Military uses</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Acrolein&action=edit&section=6" title="Edit section: Military uses"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Acrolein was used in warfare due to its irritant and blistering properties. The French used the chemical in their hand grenades and artillery shells<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> during <a href="/wiki/World_War_I" title="World War I">World War I</a> under the name "Papite".<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> </p> <div class="mw-heading mw-heading3"><h3 id="Biocide">Biocide</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Acrolein&action=edit&section=7" title="Edit section: Biocide"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Acrolein is mainly used as a <a href="/wiki/Contact_herbicide" class="mw-redirect" title="Contact herbicide">contact herbicide</a> to control submersed and floating weeds, as well as algae, in <a href="/wiki/Irrigation_canal" class="mw-redirect" title="Irrigation canal">irrigation canals</a>. It is used at a level of 10 ppm in irrigation and recirculating waters. In the <a href="/wiki/Oil_and_gas_industry" class="mw-redirect" title="Oil and gas industry">oil and gas industry</a>, it is used as a <a href="/wiki/Biocide" title="Biocide">biocide</a> in <a href="/wiki/Drilling_water" class="mw-redirect" title="Drilling water">drilling waters</a>, as well as a scavenger for <a href="/wiki/Hydrogen_sulfide" title="Hydrogen sulfide">hydrogen sulfide</a> and <a href="/wiki/Thiol" title="Thiol">mercaptans</a>.<sup id="cite_ref-Ullmann_5-2" class="reference"><a href="#cite_note-Ullmann-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Chemical_precursor">Chemical precursor</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Acrolein&action=edit&section=8" title="Edit section: Chemical precursor"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>A number of useful compounds are made from acrolein, exploiting its bifunctionality. The amino acid <a href="/wiki/Methionine" title="Methionine">methionine</a> is produced by addition of <a href="/wiki/Methanethiol" title="Methanethiol">methanethiol</a> followed by the <a href="/wiki/Strecker_synthesis" class="mw-redirect" title="Strecker synthesis">Strecker synthesis</a>. Acrolein condenses with acetaldehyde and amines to give <a href="/wiki/Methylpyridine" class="mw-redirect" title="Methylpyridine">methylpyridines</a>.<sup id="cite_ref-ul_11-0" class="reference"><a href="#cite_note-ul-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> It is also an intermediate in the <a href="/wiki/Skraup_reaction" title="Skraup reaction">Skraup synthesis</a> of <a href="/wiki/Quinoline" title="Quinoline">quinolines</a>. </p><p>Acrolein will polymerize in the presence of oxygen and in water at concentrations above 22%. The color and texture of the polymer depends on the conditions. The polymer is a clear, yellow solid. In water, it will form a hard, porous plastic.<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (March 2020)">citation needed</span></a></i>]</sup> </p><p>Acrolein has been used as a fixative in preparation of biological specimens for <a href="/wiki/Electron_microscopy" class="mw-redirect" title="Electron microscopy">electron microscopy</a>.<sup id="cite_ref-Dykstra_12-0" class="reference"><a href="#cite_note-Dykstra-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Health_risks">Health risks</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Acrolein&action=edit&section=9" title="Edit section: Health risks"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Acrolein is toxic and is a strong irritant for the skin, eyes, and nasal passages.<sup id="cite_ref-Ullmann_5-3" class="reference"><a href="#cite_note-Ullmann-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> The main metabolic pathway for acrolein is the <a href="/wiki/Alkylation" title="Alkylation">alkylation</a> of <a href="/wiki/Glutathione" title="Glutathione">glutathione</a>. The <a href="/wiki/World_Health_Organization" title="World Health Organization">WHO</a> suggests a "tolerable oral acrolein intake" of 7.5 μg per day per kg of body weight. Although acrolein occurs in <a href="/wiki/French_fries" title="French fries">French fries</a> (and other fried foods), the levels are only a few μg per kg.<sup id="cite_ref-ToxRev_13-0" class="reference"><a href="#cite_note-ToxRev-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup> In response to occupational exposures to acrolein, the US <a href="/wiki/Occupational_Safety_and_Health_Administration" title="Occupational Safety and Health Administration">Occupational Safety and Health Administration</a> has set a <a href="/wiki/Permissible_exposure_limit" title="Permissible exposure limit">permissible exposure limit</a> at 0.1 ppm (0.25 mg/m<sup>3</sup>) at an eight-hour time-weighted average.<sup id="cite_ref-cdc_14-0" class="reference"><a href="#cite_note-cdc-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup> Acrolein acts in an immunosuppressive manner and may promote regulatory cells,<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> thereby preventing the generation of allergies on the one hand, but also increasing the risk of cancer. </p><p>Acrolein was identified as one of the chemicals involved in the <a href="/wiki/2019_Kim_Kim_River_toxic_pollution" title="2019 Kim Kim River toxic pollution">2019 Kim Kim River toxic pollution</a> incident.<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-heading3"><h3 id="Cigarette_smoke">Cigarette smoke</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Acrolein&action=edit&section=10" title="Edit section: Cigarette smoke"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Connections exist between acrolein gas in the smoke from <a href="/wiki/Tobacco_smoking" title="Tobacco smoking">tobacco cigarettes</a> and the risk of <a href="/wiki/Lung_cancer" title="Lung cancer">lung cancer</a>.<sup id="cite_ref-Feng_17-0" class="reference"><a href="#cite_note-Feng-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup> Acrolein is one of seven <a href="/wiki/Toxicant" title="Toxicant">toxicants</a> in <a href="/wiki/Cigarette" title="Cigarette">cigarette</a> smoke that are most associated with <a href="/wiki/Respiratory_tract" title="Respiratory tract">respiratory tract</a> <a href="/wiki/Carcinogenesis" title="Carcinogenesis">carcinogenesis</a>.<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 mechanism of action of acrolein appears to involve induction of increased <a href="/wiki/Reactive_oxygen_species" title="Reactive oxygen species">reactive oxygen species</a> and <a href="/wiki/DNA_damage_(naturally_occurring)" title="DNA damage (naturally occurring)">DNA damage</a> related to <a href="/wiki/Oxidative_stress" title="Oxidative stress">oxidative stress</a>.<sup id="cite_ref-19" class="reference"><a href="#cite_note-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup> </p><p>In terms of the "noncarcinogenic health quotient"<sup class="noprint Inline-Template" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Manual_of_Style#Technical_language" title="Wikipedia:Manual of Style"><span title="The material near this tag may be using jargon that limits the article's accessibility. (January 2023)">jargon</span></a></i>]</sup> for components in cigarette smoke, acrolein dominates, contributing 40 times more than the next component, <a href="/wiki/Hydrogen_cyanide" title="Hydrogen cyanide">hydrogen cyanide</a>.<sup id="cite_ref-20" class="reference"><a href="#cite_note-20"><span class="cite-bracket">[</span>20<span class="cite-bracket">]</span></a></sup> The acrolein content in cigarette smoke depends on the type of cigarette and added <a href="/wiki/Glycerin" class="mw-redirect" title="Glycerin">glycerin</a>, making up to 220 μg acrolein per cigarette.<sup id="cite_ref-21" class="reference"><a href="#cite_note-21"><span class="cite-bracket">[</span>21<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-22" class="reference"><a href="#cite_note-22"><span class="cite-bracket">[</span>22<span class="cite-bracket">]</span></a></sup> Importantly, while the concentration of the constituents in mainstream smoke can be reduced by filters, this has no significant effect on the composition of the side-stream smoke where acrolein usually resides, and which is inhaled by <a href="/wiki/Passive_smoking" title="Passive smoking">passive smoking</a>.<sup id="cite_ref-23" class="reference"><a href="#cite_note-23"><span class="cite-bracket">[</span>23<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-24" class="reference"><a href="#cite_note-24"><span class="cite-bracket">[</span>24<span class="cite-bracket">]</span></a></sup> <a href="/wiki/E-cigarette" class="mw-redirect" title="E-cigarette">E-cigarettes</a>, used normally, only generate "negligible" levels of acrolein (less than 10 μg "per puff").<sup id="cite_ref-McNeill2015_25-0" class="reference"><a href="#cite_note-McNeill2015-25"><span class="cite-bracket">[</span>25<span class="cite-bracket">]</span></a></sup><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> <div class="mw-heading mw-heading3"><h3 id="Chemotherapy_metabolite">Chemotherapy metabolite</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Acrolein&action=edit&section=11" title="Edit section: Chemotherapy metabolite"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><a href="/wiki/Cyclophosphamide" title="Cyclophosphamide">Cyclophosphamide</a> and <a href="/wiki/Ifosfamide" title="Ifosfamide">ifosfamide</a> treatment results in the production of acrolein.<sup id="cite_ref-Paci_27-0" class="reference"><a href="#cite_note-Paci-27"><span class="cite-bracket">[</span>27<span class="cite-bracket">]</span></a></sup> Acrolein produced during cyclophosphamide treatment collects in the urinary bladder and if untreated can cause hemorrhagic cystitis. </p> <div class="mw-heading mw-heading3"><h3 id="Endogenous_production">Endogenous production</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Acrolein&action=edit&section=12" title="Edit section: Endogenous production"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Acrolein is a component of <a href="/wiki/Reuterin" title="Reuterin">reuterin</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> Reuterin can be produced by gut microbes when glycerol is present. Microbe-produced reuterin is a potential resource of acrolein.<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> </p> <div class="mw-heading mw-heading2"><h2 id="Analytical_methods">Analytical methods</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Acrolein&action=edit&section=13" title="Edit section: Analytical methods"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The "acrolein test" is for the presence of <a href="/wiki/Glycerin" class="mw-redirect" title="Glycerin">glycerin</a> or <a href="/wiki/Fat" title="Fat">fats</a>. A sample is heated with <a href="/wiki/Potassium_bisulfate" title="Potassium bisulfate">potassium bisulfate</a>, and acrolein is released if the test is positive. When a fat is heated strongly in the presence of a dehydrating agent such as potassium bisulfate (<span class="chemf nowrap">KHSO<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline"></sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">4</sub></span></span></span>), the glycerol portion of the molecule is dehydrated to form the unsaturated <a href="/wiki/Aldehyde" title="Aldehyde">aldehyde</a>, acrolein (CH<sub>2</sub>=CH–CHO), which has the odor peculiar to burnt cooking grease. More modern methods exist.<sup id="cite_ref-ToxRev_13-1" class="reference"><a href="#cite_note-ToxRev-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup> </p><p>In the US, EPA methods 603 and 624.1 are designed to measure acrolein in industrial and municipal <a href="/wiki/Wastewater" title="Wastewater">wastewater</a> streams.<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><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> </p> <div style="clear:both;" class=""></div> <div class="mw-heading mw-heading2"><h2 id="References">References</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Acrolein&action=edit&section=14" title="Edit section: References"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1239543626">.mw-parser-output .reflist{margin-bottom:0.5em;list-style-type:decimal}@media screen{.mw-parser-output .reflist{font-size:90%}}.mw-parser-output .reflist .references{font-size:100%;margin-bottom:0;list-style-type:inherit}.mw-parser-output .reflist-columns-2{column-width:30em}.mw-parser-output .reflist-columns-3{column-width:25em}.mw-parser-output .reflist-columns{margin-top:0.3em}.mw-parser-output .reflist-columns ol{margin-top:0}.mw-parser-output .reflist-columns li{page-break-inside:avoid;break-inside:avoid-column}.mw-parser-output .reflist-upper-alpha{list-style-type:upper-alpha}.mw-parser-output .reflist-upper-roman{list-style-type:upper-roman}.mw-parser-output .reflist-lower-alpha{list-style-type:lower-alpha}.mw-parser-output .reflist-lower-greek{list-style-type:lower-greek}.mw-parser-output .reflist-lower-roman{list-style-type:lower-roman}</style><div class="reflist"> <div class="mw-references-wrap mw-references-columns"><ol class="references"> <li id="cite_note-NIOSH-1"><span class="mw-cite-backlink">^ <a href="#cite_ref-NIOSH_1-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-NIOSH_1-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-NIOSH_1-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-NIOSH_1-3"><sup><i><b>d</b></i></sup></a> <a href="#cite_ref-NIOSH_1-4"><sup><i><b>e</b></i></sup></a> <a href="#cite_ref-NIOSH_1-5"><sup><i><b>f</b></i></sup></a> <a href="#cite_ref-NIOSH_1-6"><sup><i><b>g</b></i></sup></a> <a href="#cite_ref-NIOSH_1-7"><sup><i><b>h</b></i></sup></a> <a href="#cite_ref-NIOSH_1-8"><sup><i><b>i</b></i></sup></a></span> <span class="reference-text"><style data-mw-deduplicate="TemplateStyles:r1238218222">.mw-parser-output cite.citation{font-style:inherit;word-wrap:break-word}.mw-parser-output .citation q{quotes:"\"""\"""'""'"}.mw-parser-output .citation:target{background-color:rgba(0,127,255,0.133)}.mw-parser-output .id-lock-free.id-lock-free a{background:url("//upload.wikimedia.org/wikipedia/commons/6/65/Lock-green.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-limited.id-lock-limited a,.mw-parser-output .id-lock-registration.id-lock-registration a{background:url("//upload.wikimedia.org/wikipedia/commons/d/d6/Lock-gray-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-subscription.id-lock-subscription a{background:url("//upload.wikimedia.org/wikipedia/commons/a/aa/Lock-red-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .cs1-ws-icon a{background:url("//upload.wikimedia.org/wikipedia/commons/4/4c/Wikisource-logo.svg")right 0.1em center/12px no-repeat}body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-free a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-limited a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-registration a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-subscription a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .cs1-ws-icon a{background-size:contain;padding:0 1em 0 0}.mw-parser-output .cs1-code{color:inherit;background:inherit;border:none;padding:inherit}.mw-parser-output .cs1-hidden-error{display:none;color:var(--color-error,#d33)}.mw-parser-output .cs1-visible-error{color:var(--color-error,#d33)}.mw-parser-output .cs1-maint{display:none;color:#085;margin-left:0.3em}.mw-parser-output .cs1-kern-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right{padding-right:0.2em}.mw-parser-output .citation .mw-selflink{font-weight:inherit}@media screen{.mw-parser-output .cs1-format{font-size:95%}html.skin-theme-clientpref-night .mw-parser-output .cs1-maint{color:#18911f}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .cs1-maint{color:#18911f}}</style><cite id="CITEREFNIOSH_Pocket_Guide_to_Chemical_Hazards" class="citation web cs1">NIOSH Pocket Guide to Chemical Hazards. <a rel="nofollow" class="external text" href="https://www.cdc.gov/niosh/npg/npgd0011.html">"#0011"</a>. <a href="/wiki/National_Institute_for_Occupational_Safety_and_Health" title="National Institute for Occupational Safety and Health">National Institute for Occupational Safety and Health</a> (NIOSH).</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=%230011&rft.pub=National+Institute+for+Occupational+Safety+and+Health+%28NIOSH%29&rft.au=NIOSH+Pocket+Guide+to+Chemical+Hazards&rft_id=https%3A%2F%2Fwww.cdc.gov%2Fniosh%2Fnpg%2Fnpgd0011.html&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAcrolein" class="Z3988"></span></span> </li> <li id="cite_note-IDLH-2"><span class="mw-cite-backlink">^ <a href="#cite_ref-IDLH_2-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-IDLH_2-1"><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 web cs1"><a rel="nofollow" class="external text" href="https://www.cdc.gov/niosh/idlh/107028.html">"Acrolein"</a>. <i>Immediately Dangerous to Life or Health Concentrations (IDLH)</i>. <a href="/wiki/National_Institute_for_Occupational_Safety_and_Health" title="National Institute for Occupational Safety and Health">National Institute for Occupational Safety and Health</a> (NIOSH).</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=Immediately+Dangerous+to+Life+or+Health+Concentrations+%28IDLH%29&rft.atitle=Acrolein&rft_id=https%3A%2F%2Fwww.cdc.gov%2Fniosh%2Fidlh%2F107028.html&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAcrolein" 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 class="citation web cs1"><a rel="nofollow" class="external text" href="https://web.archive.org/web/20150402091414/http://www.nmsu.edu/safety/programs/chem_safety/NFPA-ratingA-C.htm">"Archived copy"</a>. Archived from <a rel="nofollow" class="external text" href="http://www.nmsu.edu/safety/programs/chem_safety/NFPA-ratingA-C.htm">the original</a> on 2015-04-02<span class="reference-accessdate">. Retrieved <span class="nowrap">2015-03-26</span></span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=Archived+copy&rft_id=http%3A%2F%2Fwww.nmsu.edu%2Fsafety%2Fprograms%2Fchem_safety%2FNFPA-ratingA-C.htm&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAcrolein" class="Z3988"></span><span class="cs1-maint citation-comment"><code class="cs1-code">{{<a href="/wiki/Template:Cite_web" title="Template:Cite web">cite web</a>}}</code>: CS1 maint: archived copy as title (<a href="/wiki/Category:CS1_maint:_archived_copy_as_title" title="Category:CS1 maint: archived copy as title">link</a>)</span></span> </li> <li id="cite_note-4"><span class="mw-cite-backlink"><b><a href="#cite_ref-4">^</a></b></span> <span class="reference-text">Jan F. 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href="https://web.archive.org/web/20081121222220/http://www.accustandard.com/asi/pdfs/epa_methods/603.pdf">Appendix A To Part 136 Methods For Organic Chemical Analysis of Municipal and Industrial Wastewater, Method 603—Acrolein And Acrylonitrile> </a></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"><a rel="nofollow" class="external text" href="https://www.epa.gov/sites/production/files/2017-08/documents/method_624-1_2016.pdf">Method 624.1 — Purgables by GC-MS> </a></span> </li> </ol></div></div> <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 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navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Chemical_agents" title="Template:Chemical agents"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Chemical_agents" title="Template talk:Chemical agents"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Chemical_agents" title="Special:EditPage/Template:Chemical agents"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Agents_used_in_chemical_warfareincapacitationriot_control" style="font-size:114%;margin:0 4em"><div class="hlist"><ul><li>Agents used in <a href="/wiki/Chemical_warfare" title="Chemical warfare">chemical warfare</a></li><li><a href="/wiki/Incapacitating_agent" title="Incapacitating agent">incapacitation</a></li><li><a href="/wiki/Riot_control" title="Riot control">riot control</a></li></ul></div></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Blood_agent" title="Blood agent">Blood agents</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Cyanogen" title="Cyanogen">Cyanogen</a></li> <li><a href="/wiki/Cyanogen_bromide" title="Cyanogen bromide">Cyanogen bromide</a></li> <li><a href="/wiki/Cyanogen_chloride" title="Cyanogen chloride">Cyanogen chloride</a> (CK)</li> <li><a href="/wiki/Hydrogen_cyanide" title="Hydrogen cyanide">Hydrogen cyanide</a> (AC)</li> <li><a href="/wiki/Arsine" title="Arsine">Arsine</a></li> <li><a href="/wiki/Cacodyl_cyanide" title="Cacodyl cyanide">Cacodyl cyanide</a></li> <li><a href="/wiki/Cacodyl_oxide" title="Cacodyl oxide">Cacodyl oxide</a></li> <li><a href="/wiki/Hydrogen_sulfide" title="Hydrogen sulfide">Hydrogen sulfide</a></li> <li><a href="/wiki/Phosphine" title="Phosphine">Phosphine</a></li> <li><a href="/wiki/Carbon_monoxide" title="Carbon monoxide">Carbon monoxide</a></li> <li><a href="/wiki/Phosphorus_trifluoride" title="Phosphorus trifluoride">Phosphorus trifluoride</a></li> <li><a href="/wiki/Methyl_cyanoformate" title="Methyl cyanoformate">Methyl cyanoformate</a></li> <li><a href="/wiki/Iron_pentacarbonyl" title="Iron pentacarbonyl">Iron pentacarbonyl</a></li> <li><a href="/wiki/Nickel_tetracarbonyl" title="Nickel tetracarbonyl">Nickel tetracarbonyl</a></li> <li><a href="/wiki/2,3,7,8-Tetrachlorodibenzodioxin" title="2,3,7,8-Tetrachlorodibenzodioxin">2,3,7,8-Tetrachlorodibenzodioxin</a></li> <li><a href="/wiki/Glycolonitrile" title="Glycolonitrile">Glycolonitrile</a></li> <li><a href="/wiki/Lactonitrile" title="Lactonitrile">Lactonitrile</a></li> <li><a href="/wiki/Acetone_cyanohydrin" title="Acetone cyanohydrin">Acetone cyanohydrin</a></li> <li><a href="/wiki/Stibine" title="Stibine">Stibine</a></li> <li><a href="/wiki/Chloral_cyanohydrin" title="Chloral cyanohydrin">Chloral cyanohydrin</a></li></ul></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Blister_agent" title="Blister agent">Blister agents</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Arsenical" title="Arsenical">Arsenicals</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <li><a href="/wiki/Ethyldichloroarsine" title="Ethyldichloroarsine">Ethyldichloroarsine</a> (ED)</li> <li><a href="/wiki/Methyldichloroarsine" title="Methyldichloroarsine">Methyldichloroarsine</a> (MD)</li> <li><a href="/wiki/Phenyldichloroarsine" title="Phenyldichloroarsine">Phenyldichloroarsine</a> (PD)</li> <li><a href="/wiki/Lewisite" title="Lewisite">Lewisite</a> (L)</li> <li><a href="/wiki/Lewisite_2" title="Lewisite 2">Lewisite 2</a> (L2)</li> <li><a href="/wiki/Lewisite_3" title="Lewisite 3">Lewisite 3</a> (L3)</li> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Sulfur_mustard" class="mw-redirect" title="Sulfur mustard">Sulfur mustards</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Mustard_gas" title="Mustard gas">Levinstein mustard</a> (EA-229)</li> <li><a href="/wiki/O-Mustard" class="mw-redirect" title="O-Mustard">T</a></li> <li><a href="/wiki/Sesquimustard" title="Sesquimustard">Q</a></li> <li><a href="/wiki/2-Chloroethyl_ethyl_sulfide" title="2-Chloroethyl ethyl sulfide">CEES</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Nitrogen_mustard" title="Nitrogen mustard">Nitrogen mustards</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/HN1_(nitrogen_mustard)" title="HN1 (nitrogen mustard)">HN1</a></li> <li><a href="/wiki/Chlormethine" title="Chlormethine">HN2</a></li> <li><a href="/wiki/HN3_(nitrogen_mustard)" title="HN3 (nitrogen mustard)">HN3</a></li> <li><a href="/wiki/TL-301" title="TL-301">TL-301</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Nettle_agent" title="Nettle agent">Nettle agents</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Phosgene_oxime" title="Phosgene oxime">Phosgene oxime</a> (CX)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Other</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/KB-16" title="KB-16">KB-16</a></li> <li><a href="/wiki/Dibutylchloromethyltin_chloride" title="Dibutylchloromethyltin chloride">Dibutylchloromethyltin chloride</a></li> <li><a href="/wiki/Selenium_oxychloride" class="mw-redirect" title="Selenium oxychloride">Selenium oxychloride</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Nerve_agent" title="Nerve agent">Nerve agents</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Nerve_agent#G-Series" title="Nerve agent">G-agents</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Tabun_(nerve_agent)" title="Tabun (nerve agent)">Tabun</a> (GA)</li> <li><a href="/wiki/Sarin" title="Sarin">Sarin (GB)</a></li> <li><a href="/wiki/Chlorosarin" title="Chlorosarin">Chlorosarin</a> (ClGB)</li> <li><a href="/wiki/Thiosarin" title="Thiosarin">Thiosarin</a> (SGB)</li> <li><a href="/wiki/Soman" title="Soman">Soman</a> (GD)</li> <li><a href="/wiki/Chlorosoman" title="Chlorosoman">Chlorosoman</a> (ClGD)</li> <li><a href="/wiki/Ethylsarin" title="Ethylsarin">Ethylsarin</a> (GE)</li> <li><a href="/wiki/GH_(nerve_agent)" title="GH (nerve agent)">GH</a></li> <li><a href="/wiki/Cyclosarin" title="Cyclosarin">Cyclosarin</a> (GF)</li> <li><a href="/wiki/GP_(nerve_agent)" title="GP (nerve agent)">GP</a></li> <li><a href="/wiki/Fluorotabun" title="Fluorotabun">Fluorotabun</a></li> <li><a href="/wiki/EA-1356" title="EA-1356">EA-1356</a></li> <li><a href="/wiki/EA-4352" title="EA-4352">EA-4352</a></li> <li><a href="/wiki/Crotylsarin" title="Crotylsarin">Crotylsarin</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Nerve_agent#V-Series" title="Nerve agent">V-agents</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/EA-2192" title="EA-2192">EA-2192</a></li> <li><a href="/wiki/EA-3148" title="EA-3148">EA-3148</a></li> <li><a href="/wiki/VE_(nerve_agent)" title="VE (nerve agent)">VE</a></li> <li><a href="/wiki/VG_(nerve_agent)" title="VG (nerve agent)">VG</a></li> <li><a href="/wiki/VM_(nerve_agent)" title="VM (nerve agent)">VM</a></li> <li><a href="/wiki/3,3,5-Trimethylcyclohexyl_3-pyridyl_methylphosphonate" title="3,3,5-Trimethylcyclohexyl 3-pyridyl methylphosphonate">VP</a></li> <li><a href="/wiki/VR_(nerve_agent)" title="VR (nerve agent)">VR</a></li> <li><a href="/wiki/VS_(nerve_agent)" title="VS (nerve agent)">VS</a></li> <li><a href="/wiki/VX_(nerve_agent)" title="VX (nerve agent)">VX</a></li> <li><a href="/wiki/EA-1763" title="EA-1763">EA-1763</a></li> <li><a href="/wiki/Chinese_VX" title="Chinese VX">Chinese VX</a></li> <li><a href="/wiki/V-sub_x" title="V-sub x">V-sub x (GD-7)</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">GV agents</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/GV_(nerve_agent)" title="GV (nerve agent)">GV (EA-5365)</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Novichok_agent" class="mw-redirect" title="Novichok agent">Novichok agents</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/VR_(nerve_agent)" title="VR (nerve agent)">A-208</a></li> <li><a href="/wiki/A-232" title="A-232">A-232</a></li> <li><a href="/wiki/A-234_(nerve_agent)" title="A-234 (nerve agent)">A-234</a></li> <li><a href="/wiki/A-242" title="A-242">A-242</a></li> <li><a href="/wiki/A-262" title="A-262">A-262</a></li> <li><a href="/wiki/C01-A035" title="C01-A035">C01-A035</a></li> <li><a href="/wiki/C01-A039" title="C01-A039">C01-A039</a></li> <li><a href="/wiki/C01-A042" title="C01-A042">C01-A042</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Carbamate" title="Carbamate">Carbamates</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Dimethylcarbamoyl_fluoride" title="Dimethylcarbamoyl fluoride">Dimethylcarbamoyl fluoride</a></li> <li><a href="/wiki/EA-3887" title="EA-3887">EA-3887</a></li> <li><a href="/wiki/EA-3887A" class="mw-redirect" title="EA-3887A">EA-3887A</a></li> <li><a href="/wiki/EA-3966" title="EA-3966">EA-3966</a></li> <li><a href="/wiki/EA-3990" title="EA-3990">EA-3990</a></li> <li><a href="/wiki/EA-4056" title="EA-4056">EA-4056</a></li> <li><a href="/wiki/T-1123" title="T-1123">T-1123</a></li> <li><a href="/wiki/T-1152" title="T-1152">T-1152</a></li> <li><a href="/wiki/T-1194" title="T-1194">T-1194</a></li> <li><a href="/wiki/Octamethylene-bis(5-dimethylcarbamoxyisoquinolinium_bromide)" title="Octamethylene-bis(5-dimethylcarbamoxyisoquinolinium bromide)">Octamethylene-bis(5-dimethylcarbamoxyisoquinolinium bromide)</a></li> <li><a href="/wiki/TL-599" title="TL-599">TL-599</a></li> <li><a href="/wiki/TL-1238" title="TL-1238">TL-1238</a></li> <li><a href="/wiki/TL-1299" class="mw-redirect" title="TL-1299">TL-1299</a></li> <li><a href="/wiki/TL-1317" class="mw-redirect" title="TL-1317">TL-1317</a></li> <li><a href="/wiki/Miotine" title="Miotine">Miotine (AR-28/T-1843)</a></li> <li><a href="/wiki/3152_CT" title="3152 CT">3152 CT</a></li> <li><a href="/wiki/4-686-293-01" title="4-686-293-01">4-686-293-01 (Agent 1-10)</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Other</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Diisopropyl_fluorophosphate" title="Diisopropyl fluorophosphate">Diisopropyl fluorophosphate</a></li> <li><a href="/wiki/Dicyclohexyl_phosphorofluoridate" title="Dicyclohexyl phosphorofluoridate">Dicyclohexyl phosphorofluoridate</a></li> <li><a href="/wiki/EA-2012" title="EA-2012">EA-2012</a></li> <li><a href="/wiki/EA-2054" title="EA-2054">EA-2054</a></li> <li><a href="/wiki/EA-2098" title="EA-2098">EA-2098</a></li> <li><a href="/wiki/EA-2613" title="EA-2613">EA-2613</a></li> <li><a href="/wiki/2-Ethoxycarbonyl-1-methylvinyl_cyclohexyl_methylphosphonate" title="2-Ethoxycarbonyl-1-methylvinyl cyclohexyl methylphosphonate">2-Ethoxycarbonyl-1-methylvinyl cyclohexyl methylphosphonate</a></li> <li><a href="/wiki/Neopentylene_fluorophosphate" title="Neopentylene fluorophosphate">Neopentylene fluorophosphate</a></li> <li><a href="/wiki/Selenophos" title="Selenophos">Selenophos</a></li> <li><a href="/wiki/Phospholine" class="mw-redirect" title="Phospholine">Phospholine</a></li> <li><a href="/wiki/R-16661" title="R-16661">R-16661</a></li> <li><a href="/wiki/Ro_3-0422" title="Ro 3-0422">Ro 3-0422</a></li> <li><a href="/wiki/Methanesulfonyl_fluoride" title="Methanesulfonyl fluoride">Methanesulfonyl fluoride</a></li> <li><a href="/wiki/Dimefox" title="Dimefox">Dimefox (TL-792)</a></li> <li><a href="/wiki/MSPI_(nerve_agent)" title="MSPI (nerve agent)">MSPI</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Precursors</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/Acetonitrile" title="Acetonitrile">Acetonitrile</a></li> <li><a href="/wiki/Arsenic_trichloride" title="Arsenic trichloride">AT</a></li> <li><a href="/wiki/Arsenic_trioxide" title="Arsenic trioxide">ATO</a></li> <li><a href="/wiki/Aluminium_phosphide" title="Aluminium phosphide">AlP</a></li> <li><a href="/wiki/Kinnear%E2%80%93Perren_reaction" title="Kinnear–Perren reaction">A.P.C. complex</a></li> <li><a href="/wiki/Chlorosarin" title="Chlorosarin">Chlorosarin</a></li> <li><a href="/wiki/Chlorosoman" title="Chlorosoman">Chlorosoman</a></li> <li><a href="/wiki/Cyclohexanol" title="Cyclohexanol">Cyclohexanol</a></li> <li><a href="/wiki/1,8-Dibromooctane" title="1,8-Dibromooctane">1,8-Dibromooctane</a></li> <li><a href="/wiki/N,N-Diisopropylaminoethanol" title="N,N-Diisopropylaminoethanol">N,N-Diisopropylaminoethanol</a> (KB)</li> <li><a href="/wiki/Diisopropyl_methylphosphonate" title="Diisopropyl methylphosphonate">EA-1250</a></li> <li><a href="/wiki/Diisopropylphosphite" title="Diisopropylphosphite">DIHP</a></li> <li><a href="/wiki/Ethanol" title="Ethanol">ZS</a></li> <li><a href="/wiki/Diethylphosphite" title="Diethylphosphite">DEHP</a></li> <li><a href="/wiki/Dimethyl_methylphosphonate" title="Dimethyl methylphosphonate">EA-1224</a></li> <li><a href="/wiki/Dimethylamidophosphoric_dichloride" title="Dimethylamidophosphoric dichloride">Dimethylamidophosphoric dichloride</a></li> <li><a href="/wiki/Dimethylamidophosphoric_dicyanide" title="Dimethylamidophosphoric dicyanide">Dimethylamidophosphoric dicyanide</a></li> <li><a href="/wiki/Dimethylphosphite" title="Dimethylphosphite">DMHP</a></li> <li><a href="/wiki/Ethylphosphonoselenoic_dichloride" title="Ethylphosphonoselenoic dichloride">Ethylphosphonoselenoic dichloride</a></li> <li><a href="/wiki/Formaldoxime" title="Formaldoxime">Formaldoxime</a></li> <li><a href="/wiki/Fulminic_acid" title="Fulminic acid">Nital</a></li> <li><a href="/wiki/4-Hydroxycoumarin" title="4-Hydroxycoumarin">4-Hydroxycoumarin</a></li> <li><a href="/wiki/Isopropyl_alcohol" title="Isopropyl alcohol">Isopropyl alcohol</a> (TB)</li> <li><a href="/wiki/Methyldichlorophosphine" title="Methyldichlorophosphine">Methyldichlorophosphine</a> (SW)</li> <li><a href="/wiki/Methylphosphonyl_difluoride" title="Methylphosphonyl difluoride">Methylphosphonyl difluoride (difluoro)</a> (DF)</li> <li><a href="/wiki/Methylphosphonyl_dichloride" title="Methylphosphonyl dichloride">Methylphosphonyl dichloride (dichloro)</a></li> <li><a href="/wiki/Nitromethane" title="Nitromethane">Nitromethane</a></li> <li><a href="/wiki/OPA_mixture" title="OPA mixture">OPA mixture</a></li> <li><a href="/wiki/Phosphoryl_chloride" title="Phosphoryl chloride">Phosphoryl chloride</a></li> <li><a href="/wiki/Phosphorus_pentachloride" title="Phosphorus pentachloride">Phosphorus pentachloride</a></li> <li><a href="/wiki/Phosphorus_trichloride" title="Phosphorus trichloride">Phosphorus trichloride</a> (TH)</li> <li><a href="/wiki/Pinacolone" title="Pinacolone">Pinacolone</a></li> <li><a href="/wiki/Pinacolyl_alcohol" title="Pinacolyl alcohol">Pinacolyl alcohol</a></li> <li><a href="/wiki/Phenacyl_chloride" title="Phenacyl chloride">Phenacyl chloride</a></li> <li><a href="/wiki/QL_(chemical)" title="QL (chemical)">QL</a></li> <li><a href="/wiki/2,4,5-Trichlorophenol" title="2,4,5-Trichlorophenol">2,4,5-Trichlorophenol</a></li> <li><a href="/wiki/3,3,5-Trimethylcyclohexanol" title="3,3,5-Trimethylcyclohexanol">3,3,5-Trimethylcyclohexanol</a></li> <li><a href="/wiki/Triethyl_phosphite" title="Triethyl phosphite">Triethyl phosphite</a></li> <li><a href="/wiki/Trimethyl_phosphite" title="Trimethyl phosphite">Trimethyl phosphite</a></li> <li><a href="/wiki/Thionyl_chloride" title="Thionyl chloride">TC</a></li> <li><a href="/wiki/Thiodiglycol" title="Thiodiglycol">TG</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Neurotoxin" title="Neurotoxin">Neurotoxins</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/Anatoxin-a" title="Anatoxin-a">Anatoxin-a</a></li> <li><a href="/wiki/Saxitoxin" title="Saxitoxin">Saxitoxin</a> (TZ)</li> <li><a href="/wiki/Bungarotoxin" title="Bungarotoxin">Bungarotoxin</a></li> <li><a href="/wiki/Botulinum_toxin" title="Botulinum toxin">Botulinum toxin</a> (BTX)</li> <li><a href="/wiki/Tetanospasmin" class="mw-redirect" title="Tetanospasmin">Tetanospasmin</a> (TeNT)</li> <li><a href="/wiki/Ryanodine" title="Ryanodine">Ryanodine</a></li> <li><a href="/wiki/Ciguatoxin" title="Ciguatoxin">Ciguatoxin</a> (CTX)</li> <li><a href="/wiki/Guanitoxin" title="Guanitoxin">Guanitoxin</a> (GTX)</li> <li><a href="/wiki/Chlorophenylsilatrane" title="Chlorophenylsilatrane">Chlorophenylsilatrane</a></li> <li><a href="/wiki/Palytoxin" title="Palytoxin">Palytoxin</a> (PTX)</li> <li><a href="/wiki/Maitotoxin" title="Maitotoxin">Maitotoxin</a> (MTX)</li> <li><a href="/wiki/Tetrodotoxin" title="Tetrodotoxin">Tetrodotoxin</a></li> <li><a href="/wiki/Aconitine" title="Aconitine">Aconitine</a></li> <li><a href="/wiki/Brevetoxin" title="Brevetoxin">Brevetoxin</a> (PbTX)</li> <li><a href="/wiki/Strychnine" title="Strychnine">Strychnine</a></li> <li><a href="/wiki/Antillatoxin" title="Antillatoxin">Antillatoxin</a> (ATX)</li> <li><a href="/wiki/Tetraethyllead" title="Tetraethyllead">Tetraethyllead</a></li> <li><a href="/wiki/Dimethylmercury" title="Dimethylmercury">Dimethylmercury</a></li> <li><a href="/wiki/HN1_(nitrogen_mustard)" title="HN1 (nitrogen mustard)">HN1 hydrochloride</a></li> <li><a href="/wiki/HN2" class="mw-redirect" title="HN2">HN2 hydrochloride</a></li> <li><a href="/wiki/Tris(2-chloroethyl)amine" class="mw-redirect" title="Tris(2-chloroethyl)amine">HN3 hydrochloride</a></li> <li><a href="/wiki/IDPN_(chemical)" title="IDPN (chemical)">A-8564</a></li> <li><a href="/wiki/Picrotoxin" title="Picrotoxin">Picrotoxin</a></li> <li><a href="/wiki/Sulfuryl_fluoride" title="Sulfuryl fluoride">Sulfuryl fluoride</a></li> <li><a href="/wiki/Tremorine" title="Tremorine">Tremorine</a></li> <li><a href="/wiki/Oxotremorine" title="Oxotremorine">Oxotremorine</a></li> <li><a href="/wiki/Batrachotoxin" title="Batrachotoxin">Batrachotoxin</a></li> <li><a href="/wiki/Tetramethylenedisulfotetramine" title="Tetramethylenedisulfotetramine">Tetramethylenedisulfotetramine (TETS)</a></li> <li><a href="/wiki/Bicyclic_phosphate" title="Bicyclic phosphate">Bicyclic phosphates</a> <ul><li><a href="/wiki/IPTBO" title="IPTBO">IPTBO</a></li> <li><a href="/wiki/TBPO" title="TBPO">TBPO</a></li> <li><a href="/wiki/TBPS" title="TBPS">TBPS</a></li></ul></li> <li><a href="/wiki/Cloflubicyne" title="Cloflubicyne">Cloflubicyne</a></li> <li><a href="/wiki/Trimethylolpropane_phosphite" title="Trimethylolpropane phosphite">Trimethylolpropane phosphite</a></li> <li><a href="/wiki/Domoic_acid" title="Domoic acid">Domoic acid</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Pulmonary_agent" title="Pulmonary agent">Pulmonary/<br />choking agents</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Chlorine" title="Chlorine">Chlorine</a></li> <li><a href="/wiki/Bromine" title="Bromine">Bromine</a></li> <li><a href="/wiki/Phosgene" title="Phosgene">Phosgene</a> (CG)</li> <li><a href="/wiki/Fluorine" title="Fluorine">Fluorine</a></li> <li><a href="/wiki/Perfluoroisobutene" title="Perfluoroisobutene">Perfluoroisobutene</a></li> <li><a href="/wiki/Chloropicrin" title="Chloropicrin">Chloropicrin</a> (PS)</li> <li><a href="/wiki/Dimethyl(trifluoromethylthio)arsine" title="Dimethyl(trifluoromethylthio)arsine">Dimethyl(trifluoromethylthio)arsine</a></li> <li><a href="/wiki/Diphosgene" title="Diphosgene">Diphosgene</a> (DP)</li> <li><a href="/wiki/Disulfur_decafluoride" title="Disulfur decafluoride">Disulfur decafluoride</a> (Z)</li> <li><a class="mw-selflink selflink">Acrolein</a></li> <li><a href="/wiki/Ethyl_bromoacetate" title="Ethyl bromoacetate">Ethyl bromoacetate</a></li> <li><a href="/wiki/Perchloromethyl_mercaptan" title="Perchloromethyl mercaptan">Perchloromethyl mercaptan</a></li> <li><a href="/wiki/Phenylcarbylamine_chloride" title="Phenylcarbylamine chloride">Phenylcarbylamine chloride</a></li> <li><a href="/wiki/Tetranitromethane" title="Tetranitromethane">Tetranitromethane</a></li> <li><a href="/wiki/Tetrachlorodinitroethane" title="Tetrachlorodinitroethane">Tetrachlorodinitroethane</a></li> <li><a href="/wiki/Chlorine_trifluoride" title="Chlorine trifluoride">Chlorine trifluoride</a></li> <li><a href="/wiki/Perchloryl_fluoride" title="Perchloryl fluoride">Perchloryl fluoride</a></li> <li><a href="/wiki/Cadmium_oxide" title="Cadmium oxide">Cadmium oxide</a></li> <li><a href="/wiki/Cadmium_chloride" title="Cadmium chloride">Cadmium chloride</a></li> <li><a href="/wiki/Mercury(II)_chloride" title="Mercury(II) chloride">Mercuric chloride</a></li> <li><a href="/wiki/Selenium_dioxide" title="Selenium dioxide">Selenium dioxide</a></li> <li><a href="/wiki/Selenoyl_fluoride" title="Selenoyl fluoride">Selenoyl fluoride</a></li> <li><a href="/wiki/Trifluoronitrosomethane" title="Trifluoronitrosomethane">Trifluoronitrosomethane</a></li> <li><a href="/wiki/Trichloronitrosomethane" title="Trichloronitrosomethane">Trichloronitrosomethane</a></li> <li><a href="/wiki/Nitric_oxide" title="Nitric oxide">Nitric oxide</a></li> <li><a href="/wiki/Nitrogen_dioxide" title="Nitrogen dioxide">Nitrogen dioxide</a></li> <li><a href="/wiki/Dinitrogen_tetroxide" title="Dinitrogen tetroxide">Dinitrogen tetroxide</a></li> <li><a href="/wiki/Sulfur_dioxide" title="Sulfur dioxide">Sulfur dioxide</a></li> <li><a href="/wiki/Phosphorus_trichloride" title="Phosphorus trichloride">Phosphorus trichloride</a></li> <li><a href="/wiki/Methyl_isocyanate" title="Methyl isocyanate">Methyl isocyanate</a></li> <li><a href="/wiki/Ethenone" title="Ethenone">Ethenone</a></li> <li><a href="/wiki/Methyl_vinyl_ketone" title="Methyl vinyl ketone">Methyl vinyl ketone</a></li> <li><a href="/wiki/Trifluoroacetyl_chloride" title="Trifluoroacetyl chloride">Trifluoroacetyl chloride</a></li> <li><a href="/wiki/Salcomine" title="Salcomine">Salcomine</a></li> <li><a href="/wiki/Fluomine" title="Fluomine">Fluomine</a></li> <li><a href="/wiki/Uranium_hexafluoride" title="Uranium hexafluoride">Uranium hexafluoride</a></li> <li><a href="/wiki/Diborane" title="Diborane">Diborane</a></li> <li><a href="/wiki/Green_Cross_(chemical_warfare)" title="Green Cross (chemical warfare)">Green Cross</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Vomiting_agent" title="Vomiting agent">Vomiting agents</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/Adamsite" title="Adamsite">Adamsite</a> (DM)</li> <li><a href="/wiki/Chloropicrin" title="Chloropicrin">Chloropicrin</a></li> <li><a href="/wiki/Litharge" title="Litharge">Litharge</a>-<a href="/wiki/Glycerine" class="mw-redirect" title="Glycerine">glycerine</a></li> <li><a href="/wiki/Diphenylchlorarsine" title="Diphenylchlorarsine">Diphenylchlorarsine</a></li> <li><a href="/wiki/Diphenylcyanoarsine" title="Diphenylcyanoarsine">Diphenylcyanoarsine</a></li> <li><a href="/wiki/Cacodyl_cyanide" title="Cacodyl cyanide">Cacodyl cyanide</a></li> <li><a href="/wiki/O-Dianisidine" title="O-Dianisidine">o-Dianisidine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Incapacitating_agent" title="Incapacitating agent">Incapacitating<br />agents</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/3-Quinuclidinyl_benzilate" title="3-Quinuclidinyl benzilate">BZ</a> (CS-4030)</li> <li><a href="/wiki/Apomorphine" title="Apomorphine">Apomorphine</a></li> <li><a href="/wiki/Butyrophenone" title="Butyrophenone">Butyrophenone</a></li> <li><a href="/wiki/Etonitazene" title="Etonitazene">EA-4941</a> (CS-4640)</li> <li><a href="/wiki/Etorphine" title="Etorphine">Etorphine</a></li> <li><a href="/wiki/Benactyzine" title="Benactyzine">EA-2092</a></li> <li><a href="/wiki/Ditran" title="Ditran">CS-4297</a></li> <li><a href="/wiki/Etoxadrol" title="Etoxadrol">Etoxadrol</a></li> <li><a href="/wiki/Dimethylheptylpyran" title="Dimethylheptylpyran">Dimethylheptylpyran</a> (DMHP)</li> <li><a href="/wiki/Phencyclidine" title="Phencyclidine">EA-2148</a></li> <li><a href="/wiki/EA-3167" title="EA-3167">EA-3167</a></li> <li><a href="/wiki/EA-3443" title="EA-3443">EA-3443</a></li> <li><a href="/wiki/Pethidine" title="Pethidine">Pethidine</a></li> <li><a href="/wiki/EA-3580" title="EA-3580">EA-3580</a></li> <li><a href="/wiki/Ibogaine" title="Ibogaine">Ibogaine</a></li> <li><a href="/wiki/EA-3834" title="EA-3834">EA-3834</a></li> <li><a href="/wiki/Kolokol-1" title="Kolokol-1">Kolokol-1</a></li> <li><a href="/wiki/LSD" title="LSD">LSD-25</a></li> <li><a href="/wiki/PAVA_spray" title="PAVA spray">PAVA spray</a></li> <li><a href="/wiki/Psilocybin" title="Psilocybin">Psilocybin</a></li> <li><a href="/wiki/Incapacitating_agent#Sleeping_gas" title="Incapacitating agent">Sleeping gas</a></li> <li><a href="/wiki/Carfentanil" title="Carfentanil">Carfentanil</a></li> <li><a href="/wiki/N-Ethyl-3-piperidyl_benzilate" title="N-Ethyl-3-piperidyl benzilate">JB-318</a></li> <li><a href="/wiki/N-Methyl-3-piperidyl_benzilate" title="N-Methyl-3-piperidyl benzilate">JB-336</a></li> <li><a href="/wiki/CS-27349" title="CS-27349">CS-27349</a></li> <li><a href="/wiki/CAR-226,086" title="CAR-226,086">CAR-226,086</a></li> <li><a href="/wiki/CAR-301,060" title="CAR-301,060">CAR-301,060</a></li> <li><a href="/wiki/CAR-302,196" title="CAR-302,196">CAR-302,196</a></li> <li><a href="/wiki/CAR-302,282" title="CAR-302,282">CAR-302,282</a></li> <li><a href="/wiki/CAR-302,668" title="CAR-302,668">CAR-302,668</a></li> <li><a href="/wiki/Benperidol" title="Benperidol">Benperidol</a></li> <li><a href="/wiki/Desflurane" title="Desflurane">Desflurane</a></li> <li><a href="/wiki/Enflurane" title="Enflurane">Enflurane</a></li> <li><a href="/wiki/Bufotenin" title="Bufotenin">Bufotenin</a></li> <li><a href="/wiki/Isoflurane" title="Isoflurane">Isoflurane</a></li> <li><a href="/wiki/Halothane" title="Halothane">Halothane</a></li> <li><a href="/wiki/Sevoflurane" title="Sevoflurane">Sevoflurane</a></li> <li><a href="/wiki/Pentazocine" title="Pentazocine">Pentazocine</a></li> <li><a href="/wiki/Procarbazine" title="Procarbazine">Procarbazine</a></li> <li><a href="/wiki/Fluphenazine" title="Fluphenazine">Fluphenazine</a></li> <li><a href="/wiki/Chlorpromazine" title="Chlorpromazine">Chlorpromazine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Tear_gas" title="Tear gas">Lachrymatory<br />agents</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/Xylyl_bromide" title="Xylyl bromide">Xylyl bromide</a></li> <li><a href="/wiki/Pepper_spray" title="Pepper spray">Pepper spray</a> (OC)</li> <li><a href="/wiki/Mace_(spray)" title="Mace (spray)">Mace (spray)</a></li> <li><a href="/wiki/Phenacyl_chloride" title="Phenacyl chloride">CN</a></li> <li><a href="/wiki/CS_gas" title="CS gas">CS</a></li> <li><a href="/wiki/CR_gas" title="CR gas">CR</a></li> <li><a href="/wiki/CNS_(chemical_weapon)" title="CNS (chemical weapon)">CNS</a></li> <li><a href="/wiki/Benzyl_chloride" title="Benzyl chloride">Benzyl chloride</a></li> <li><a href="/wiki/Benzyl_bromide" title="Benzyl bromide">Benzyl bromide</a></li> <li><a href="/wiki/Benzyl_iodide" title="Benzyl iodide">Benzyl iodide</a></li> <li><a href="/wiki/Bromobenzyl_cyanide" title="Bromobenzyl cyanide">Bromobenzyl cyanide</a></li> <li><a href="/wiki/Thiophosgene" title="Thiophosgene">Thiophosgene</a></li> <li><a href="/wiki/Chloroacetone" title="Chloroacetone">Chloroacetone</a></li> <li><a href="/wiki/Bromoacetone" title="Bromoacetone">Bromoacetone</a></li> <li><a href="/wiki/Bromomethyl_ethyl_ketone" title="Bromomethyl ethyl ketone">Bromomethyl ethyl ketone</a></li> <li><a class="mw-selflink selflink">Acrolein</a></li> <li><a href="/wiki/Phenacyl_bromide" title="Phenacyl bromide">Phenacyl bromide</a></li> <li><a href="/wiki/Chloroacetophenone_oxime" title="Chloroacetophenone oxime">Chloroacetophenone oxime</a></li> <li><a href="/wiki/Ethyl_bromoacetate" title="Ethyl bromoacetate">Ethyl bromoacetate</a></li> <li><a href="/wiki/Ethyl_iodoacetate" title="Ethyl iodoacetate">Ethyl iodoacetate</a></li> <li><a href="/wiki/Iodoacetone" title="Iodoacetone">Iodoacetone</a></li> <li><a href="/wiki/Allyl_isothiocyanate" title="Allyl isothiocyanate">Allyl isothiocyanate</a></li> <li><a href="/wiki/Hexamethylene_diisocyanate" title="Hexamethylene diisocyanate">Hexamethylene diisocyanate</a></li> <li><a href="/wiki/Crotonaldehyde" title="Crotonaldehyde">Crotonaldehyde</a></li> <li><a href="/wiki/DRC-5593" title="DRC-5593">DRC-5593</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Malodorant" title="Malodorant">Malodorant</a> agents</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/Thioacetone" title="Thioacetone">Thioacetone</a></li> <li><a href="/wiki/Allicin" title="Allicin">Allicin</a></li> <li><a href="/wiki/Skatole" title="Skatole">Skatole</a></li> <li><a href="/wiki/Cadaverine" title="Cadaverine">Cadaverine</a></li> <li><a href="/wiki/Putrescine" title="Putrescine">Putrescine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Cornea-clouding agents</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/Lewisite" title="Lewisite">Lewisite</a></li> <li><a href="/wiki/Phosgene_oxime" title="Phosgene oxime">CX</a></li> <li><a href="/wiki/KB-16" title="KB-16">KB-16</a></li> <li><a href="/wiki/Methyl_cyanoacrylate" title="Methyl cyanoacrylate">Methyl cyanoacrylate</a></li> <li><a href="/wiki/N-Methylmorpholine" title="N-Methylmorpholine">N-Methylmorpholine</a></li> <li><a href="/wiki/Allyl_alcohol" title="Allyl alcohol">Allyl alcohol</a></li> <li><a href="/wiki/Osmium_tetroxide" title="Osmium tetroxide">Osmium tetroxide</a></li> <li><a class="mw-selflink selflink">Acrolein</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Biological toxins</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Abrin" title="Abrin">Abrin</a></li> <li><a href="/wiki/Aconitine" title="Aconitine">Aconitine</a></li> <li><a href="/wiki/Cyclopiazonic_acid" title="Cyclopiazonic acid">Cyclopiazonic acid</a></li> <li><a href="/wiki/Histrionicotoxins" title="Histrionicotoxins">Histrionicotoxins</a></li> <li><a href="/wiki/Aflatoxins" class="mw-redirect" title="Aflatoxins">Aflatoxins</a></li> <li><a href="/wiki/Anatoxin-a" title="Anatoxin-a">Anatoxin-a</a></li> <li><a href="/wiki/Batrachotoxin" title="Batrachotoxin">Batrachotoxin</a></li> <li><a href="/wiki/Botulinum_toxin" title="Botulinum toxin">Botulinum toxin</a></li> <li><a href="/wiki/Brevetoxin" title="Brevetoxin">Brevetoxin</a></li> <li><a href="/wiki/Ciguatoxin" title="Ciguatoxin">Ciguatoxin</a></li> <li><a href="/wiki/Domoic_acid" title="Domoic acid">Domoic acid</a></li> <li><a href="/wiki/Enterotoxin_type_B" title="Enterotoxin type B">Enterotoxin type B</a></li> <li><a href="/wiki/Grayanotoxin" title="Grayanotoxin">Grayanotoxin</a></li> <li><a href="/wiki/Guanitoxin" title="Guanitoxin">Guanitoxin</a></li> <li><a href="/wiki/Maitotoxin" title="Maitotoxin">Maitotoxin</a></li> <li><a href="/wiki/Modeccin" title="Modeccin">Modeccin</a></li> <li><a href="/wiki/Palytoxin" title="Palytoxin">Palytoxin</a></li> <li><a href="/wiki/Ricin" title="Ricin">Ricin</a></li> <li><a href="/wiki/Saxitoxin" title="Saxitoxin">Saxitoxin</a></li> <li><a href="/wiki/Shiga_toxin" title="Shiga toxin">Shiga toxin</a></li> <li><a href="/wiki/T-2_mycotoxin" title="T-2 mycotoxin">T-2 mycotoxin</a></li> <li><a href="/wiki/Tetanospasmin" class="mw-redirect" title="Tetanospasmin">Tetanospasmin</a></li> <li><a href="/wiki/Tetrodotoxin" title="Tetrodotoxin">Tetrodotoxin</a></li> <li><a href="/wiki/Volkensin" title="Volkensin">Volkensin</a></li> <li><a href="/wiki/Veratridine" title="Veratridine">Veratridine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Other</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Methyl_fluoroacetate" title="Methyl fluoroacetate">Methyl fluoroacetate</a></li> <li><a href="/wiki/Napalm" title="Napalm">Napalm</a> (variants and mixtures)</li> <li><a href="/wiki/Fluoroethyl_fluoroacetate" title="Fluoroethyl fluoroacetate">Fluoroethyl fluoroacetate</a></li> <li><a href="/wiki/Depleted_uranium" title="Depleted uranium">Depleted uranium</a> <ul><li>post-combustion <a href="/wiki/Uranium_oxide" title="Uranium oxide">uranium oxides</a></li></ul></li> <li><a href="/wiki/Plutonium" title="Plutonium">Plutonium</a> and <a href="/wiki/Plutonium_compounds" title="Plutonium compounds">its compounds</a></li> <li><a href="/wiki/Polonium" title="Polonium">Polonium</a></li> <li><a href="/wiki/White_phosphorus_munitions" class="mw-redirect" title="White phosphorus munitions">White phosphorus</a></li></ul> </div></td></tr><tr><td class="navbox-abovebelow" colspan="2"><div> <ul><li><a href="/wiki/List_of_chemical_warfare_agents" title="List of chemical warfare agents">List of chemical warfare agents</a></li> <li><a href="/wiki/CB_military_symbol" title="CB military symbol">CB military symbol</a></li></ul> </div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"></div><div role="navigation" class="navbox" aria-labelledby="Molecules_detected_in_outer_space" style="padding:3px"><table class="nowraplinks hlist mw-collapsible mw-collapsed navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Molecules_detected_in_outer_space" title="Template:Molecules detected in outer space"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Molecules_detected_in_outer_space" title="Template talk:Molecules detected in outer space"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Molecules_detected_in_outer_space" title="Special:EditPage/Template:Molecules detected in outer space"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Molecules_detected_in_outer_space" style="font-size:114%;margin:0 4em"><a href="/wiki/List_of_interstellar_and_circumstellar_molecules" title="List of interstellar and circumstellar molecules">Molecules detected in outer space</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Molecule" title="Molecule">Molecules</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Diatomic_molecule" title="Diatomic molecule">Diatomic</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Aluminium_monochloride" title="Aluminium monochloride">Aluminium monochloride</a></li> <li><a href="/wiki/Aluminium_monofluoride" title="Aluminium monofluoride">Aluminium monofluoride</a></li> <li><a href="/wiki/Aluminium(II)_oxide" title="Aluminium(II) oxide">Aluminium(II) oxide</a></li> <li><a href="/wiki/Argonium" title="Argonium">Argonium</a></li> <li><a href="/wiki/Carbon_cation" class="mw-redirect" title="Carbon cation">Carbon cation</a></li> <li><a href="/wiki/Carbon_monophosphide" title="Carbon monophosphide">Carbon monophosphide</a></li> <li><a href="/wiki/Carbon_monosulfide" title="Carbon monosulfide">Carbon monosulfide</a></li> <li><a href="/wiki/Carbon_monoxide" title="Carbon monoxide">Carbon monoxide</a></li> <li><a href="/wiki/Cyano_radical" title="Cyano radical">Cyano radical</a></li> <li><a href="/wiki/Diatomic_carbon" title="Diatomic carbon">Diatomic carbon</a></li> <li><a href="/w/index.php?title=Fluoromethylidynium&action=edit&redlink=1" class="new" title="Fluoromethylidynium (page does not exist)">Fluoromethylidynium</a></li> <li><a href="/wiki/Helium_hydride_ion" title="Helium hydride ion">Helium hydride ion</a></li> <li><a href="/wiki/Hydrogen_chloride" title="Hydrogen chloride">Hydrogen chloride</a></li> <li><a href="/wiki/Hydrogen_fluoride" title="Hydrogen fluoride">Hydrogen fluoride</a></li> <li><a href="/wiki/Hydrogen" title="Hydrogen">Hydrogen</a> (molecular)</li> <li><a href="/wiki/Hydroxyl_radical" title="Hydroxyl radical">Hydroxyl radical</a></li> <li><a href="/wiki/Iron(II)_oxide" title="Iron(II) oxide">Iron(II) oxide</a></li> <li><a href="/wiki/Magnesium_monohydride" title="Magnesium monohydride">Magnesium monohydride</a></li> <li><a href="/wiki/Methylidyne_radical" title="Methylidyne radical">Methylidyne radical</a></li> <li><a href="/wiki/Nitric_oxide" title="Nitric oxide">Nitric oxide</a></li> <li><a href="/wiki/Nitrogen" title="Nitrogen">Nitrogen</a> (molecular)</li> <li><a href="/wiki/Imidogen" title="Imidogen">Imidogen</a></li> <li><a href="/wiki/Sulfur_mononitride" title="Sulfur mononitride">Sulfur mononitride</a></li> <li><a href="/wiki/Oxygen" title="Oxygen">Oxygen</a> (molecular)</li> <li><a href="/wiki/Phosphorus_monoxide" title="Phosphorus monoxide">Phosphorus monoxide</a></li> <li><a href="/wiki/Phosphorus_mononitride" title="Phosphorus mononitride">Phosphorus mononitride</a></li> <li><a href="/wiki/Potassium_chloride" title="Potassium chloride">Potassium chloride</a></li> <li><a href="/wiki/Silicon_carbide" title="Silicon carbide">Silicon carbide</a></li> <li><a href="/wiki/Silicon_monoxide" title="Silicon monoxide">Silicon monoxide</a></li> <li><a href="/wiki/Silicon_monosulfide" title="Silicon monosulfide">Silicon monosulfide</a></li> <li><a href="/wiki/Sodium_chloride" title="Sodium chloride">Sodium chloride</a></li> <li><a href="/wiki/Sodium_iodide" title="Sodium iodide">Sodium iodide</a></li> <li><a href="/wiki/Sulfanyl" title="Sulfanyl">Sulfanyl</a></li> <li><a href="/wiki/Sulfur_monoxide" title="Sulfur monoxide">Sulfur monoxide</a></li> <li><a href="/wiki/Titanium(II)_oxide" title="Titanium(II) oxide">Titanium(II) oxide</a></li></ul> </div></td><td class="noviewer navbox-image" rowspan="9" style="width:1px;padding:0 0 0 2px"><div><span typeof="mw:File"><a href="/wiki/Nitrous_oxide" title="Nitrous oxide"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/9/93/Nitrous-oxide-3D-balls.png/60px-Nitrous-oxide-3D-balls.png" decoding="async" width="60" height="24" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/9/93/Nitrous-oxide-3D-balls.png/90px-Nitrous-oxide-3D-balls.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/9/93/Nitrous-oxide-3D-balls.png/120px-Nitrous-oxide-3D-balls.png 2x" data-file-width="1100" data-file-height="441" /></a></span> <br /><br /><br /><br /> <span typeof="mw:File"><a href="/wiki/Ethanol" title="Ethanol"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/b/b0/Ethanol-3D-balls.png/60px-Ethanol-3D-balls.png" decoding="async" width="60" height="41" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/b/b0/Ethanol-3D-balls.png/90px-Ethanol-3D-balls.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/b/b0/Ethanol-3D-balls.png/120px-Ethanol-3D-balls.png 2x" data-file-width="1100" data-file-height="754" /></a></span> <br /><br /><br /><br /> <span typeof="mw:File"><a href="/wiki/Buckminsterfullerene" title="Buckminsterfullerene"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/0/0f/Buckminsterfullerene-perspective-3D-balls.png/60px-Buckminsterfullerene-perspective-3D-balls.png" decoding="async" width="60" height="63" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/0/0f/Buckminsterfullerene-perspective-3D-balls.png/90px-Buckminsterfullerene-perspective-3D-balls.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/0/0f/Buckminsterfullerene-perspective-3D-balls.png/120px-Buckminsterfullerene-perspective-3D-balls.png 2x" data-file-width="1056" data-file-height="1100" /></a></span></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Triatomic_molecule" title="Triatomic molecule">Triatomic</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/Aluminium(I)_hydroxide" class="mw-redirect" title="Aluminium(I) hydroxide">Aluminium(I) hydroxide</a></li> <li><a href="/w/index.php?title=Aluminium_isocyanide&action=edit&redlink=1" class="new" title="Aluminium isocyanide (page does not exist)">Aluminium isocyanide</a></li> <li><a href="/wiki/Amino_radical" title="Amino radical">Amino radical</a></li> <li><a href="/wiki/Carbon_dioxide" title="Carbon dioxide">Carbon dioxide</a></li> <li><a href="/wiki/Carbonyl_sulfide" title="Carbonyl sulfide">Carbonyl sulfide</a></li> <li><a href="/w/index.php?title=CCP_radical&action=edit&redlink=1" class="new" title="CCP radical (page does not exist)">CCP radical</a></li> <li><a href="/wiki/Halonium_ion" title="Halonium ion">Chloronium</a></li> <li><a href="/wiki/Diazenylium" title="Diazenylium">Diazenylium</a></li> <li><a href="/wiki/Dicarbon_monoxide" title="Dicarbon monoxide">Dicarbon monoxide</a></li> <li><a href="/w/index.php?title=Disilicon_carbide&action=edit&redlink=1" class="new" title="Disilicon carbide (page does not exist)">Disilicon carbide</a></li> <li><a href="/wiki/Ethynyl_radical" title="Ethynyl radical">Ethynyl radical</a></li> <li><a href="/w/index.php?title=Formyl_radical&action=edit&redlink=1" class="new" title="Formyl radical (page does not exist)">Formyl radical</a></li> <li><a href="/wiki/Hydrogen_cyanide" title="Hydrogen cyanide">Hydrogen cyanide</a> (HCN)</li> <li><a href="/wiki/Hydrogen_isocyanide" title="Hydrogen isocyanide">Hydrogen isocyanide</a> (HNC)</li> <li><a href="/wiki/Hydrogen_sulfide" title="Hydrogen sulfide">Hydrogen sulfide</a></li> <li><a href="/wiki/Hydroperoxyl" title="Hydroperoxyl">Hydroperoxyl</a></li> <li><a href="/w/index.php?title=Iron_cyanide&action=edit&redlink=1" class="new" title="Iron cyanide (page does not exist)">Iron cyanide</a></li> <li><a href="/w/index.php?title=Isoformyl&action=edit&redlink=1" class="new" title="Isoformyl (page does not exist)">Isoformyl</a></li> <li><a href="/wiki/Magnesium_cyanide" title="Magnesium cyanide">Magnesium cyanide</a></li> <li><a href="/w/index.php?title=Magnesium_isocyanide&action=edit&redlink=1" class="new" title="Magnesium isocyanide (page does not exist)">Magnesium isocyanide</a></li> <li><a href="/wiki/Methylene_(compound)" title="Methylene (compound)">Methylene</a></li> <li><a href="/wiki/Diazenylium" title="Diazenylium">N<sub>2</sub>H<sup>+</sup></a></li> <li><a href="/wiki/Nitrous_oxide" title="Nitrous oxide">Nitrous oxide</a></li> <li><a href="/wiki/Nitroxyl" title="Nitroxyl">Nitroxyl</a></li> <li><a href="/wiki/Ozone" title="Ozone">Ozone</a></li> <li><a href="/wiki/Methylidynephosphane" title="Methylidynephosphane">Methylidynephosphane</a></li> <li><a href="/wiki/Potassium_cyanide" title="Potassium cyanide">Potassium cyanide</a></li> <li><a href="/wiki/Trihydrogen_cation" title="Trihydrogen cation">Trihydrogen cation</a></li> <li><a href="/wiki/Sodium_cyanide" title="Sodium cyanide">Sodium cyanide</a></li> <li><a href="/wiki/Sodium_hydroxide" title="Sodium hydroxide">Sodium hydroxide</a></li> <li><a href="/w/index.php?title=Silicon_carbonitride&action=edit&redlink=1" class="new" title="Silicon carbonitride (page does not exist)">Silicon carbonitride</a></li> <li><a href="/w/index.php?title=C-Silicon_dicarbide&action=edit&redlink=1" class="new" title="C-Silicon dicarbide (page does not exist)">c-Silicon dicarbide</a></li> <li><a href="/w/index.php?title=SiNC&action=edit&redlink=1" class="new" title="SiNC (page does not exist)">SiNC</a></li> <li><a href="/wiki/Sulfur_dioxide" title="Sulfur dioxide">Sulfur dioxide</a></li> <li><a href="/w/index.php?title=Thioformyl&action=edit&redlink=1" class="new" title="Thioformyl (page does not exist)">Thioformyl</a></li> <li><a href="/wiki/Thioxoethenylidene" title="Thioxoethenylidene">Thioxoethenylidene</a></li> <li><a href="/wiki/Titanium_dioxide" title="Titanium dioxide">Titanium dioxide</a></li> <li><a href="/wiki/Tricarbon" title="Tricarbon">Tricarbon</a></li> <li><a href="/wiki/Water" title="Water">Water</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/List_of_interstellar_and_circumstellar_molecules#Molecules" title="List of interstellar and circumstellar molecules">Four<br />atoms</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Acetylene" title="Acetylene">Acetylene</a></li> <li><a href="/wiki/Ammonia" title="Ammonia">Ammonia</a></li> <li><a href="/wiki/Isocyanic_acid" title="Isocyanic acid">Isocyanic acid</a></li> <li><a href="/wiki/Polyyne" title="Polyyne">Cyanoethynyl</a></li> <li><a href="/wiki/Interstellar_formaldehyde" title="Interstellar formaldehyde">Formaldehyde</a></li> <li><a href="/wiki/Fulminic_acid" title="Fulminic acid">Fulminic acid</a></li> <li><a href="/w/index.php?title=HCCN&action=edit&redlink=1" class="new" title="HCCN (page does not exist)">HCCN</a></li> <li><a href="/wiki/Hydrogen_peroxide" title="Hydrogen peroxide">Hydrogen peroxide</a></li> <li><a href="/w/index.php?title=Hydromagnesium_isocyanide&action=edit&redlink=1" class="new" title="Hydromagnesium isocyanide (page does not exist)">Hydromagnesium isocyanide</a></li> <li><a href="/wiki/Isocyanic_acid" title="Isocyanic acid">Isocyanic acid</a></li> <li><a href="/wiki/Thiocyanic_acid" title="Thiocyanic acid">Isothiocyanic acid</a></li> <li><a href="/w/index.php?title=Ketenyl&action=edit&redlink=1" class="new" title="Ketenyl (page does not exist)">Ketenyl</a></li> <li><a href="/w/index.php?title=Methylene_amidogen&action=edit&redlink=1" class="new" title="Methylene amidogen (page does not exist)">Methylene amidogen</a></li> <li><a href="/wiki/Methyl_cation" class="mw-redirect" title="Methyl cation">Methyl cation</a></li> <li><a href="/wiki/Methyl_radical" title="Methyl radical">Methyl radical</a></li> <li><a href="/wiki/Propynylidyne" title="Propynylidyne">Propynylidyne</a></li> <li><a href="/w/index.php?title=Protonated_carbon_dioxide&action=edit&redlink=1" class="new" title="Protonated carbon dioxide (page does not exist)">Protonated carbon dioxide</a></li> <li><a href="/wiki/Protonated_hydrogen_cyanide" title="Protonated hydrogen cyanide">Protonated hydrogen cyanide</a></li> <li><a href="/w/index.php?title=Silicon_tricarbide&action=edit&redlink=1" class="new" title="Silicon tricarbide (page does not exist)">Silicon tricarbide</a></li> <li><a href="/wiki/Thioformaldehyde" title="Thioformaldehyde">Thioformaldehyde</a></li> <li><a href="/wiki/Tricarbon_monoxide" title="Tricarbon monoxide">Tricarbon monoxide</a></li> <li><a href="/wiki/Tricarbon_monosulfide" title="Tricarbon monosulfide">Tricarbon monosulfide</a></li> <li><a href="/wiki/Thiocyanic_acid" title="Thiocyanic acid">Thiocyanic acid</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/List_of_interstellar_and_circumstellar_molecules#Molecules" title="List of interstellar and circumstellar molecules">Five<br />atoms</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/Ammonium" title="Ammonium">Ammonium</a> ion</li> <li><a href="/wiki/Polyyne" title="Polyyne">Butadiynyl</a></li> <li><a href="/wiki/Carbodiimide" title="Carbodiimide">Carbodiimide</a></li> <li><a href="/wiki/Cyanamide" title="Cyanamide">Cyanamide</a></li> <li><a href="/wiki/Cyanoacetylene" title="Cyanoacetylene">Cyanoacetylene</a></li> <li><a href="/w/index.php?title=Cyanoformaldehyde&action=edit&redlink=1" class="new" title="Cyanoformaldehyde (page does not exist)">Cyanoformaldehyde</a></li> <li><a href="/wiki/Cyanomethyl" title="Cyanomethyl">Cyanomethyl</a></li> <li><a href="/wiki/Cyclopropenylidene" title="Cyclopropenylidene">Cyclopropenylidene</a></li> <li><a href="/wiki/Formic_acid" title="Formic acid">Formic acid</a></li> <li><a href="/w/index.php?title=Isocyanoacetylene&action=edit&redlink=1" class="new" title="Isocyanoacetylene (page does not exist)">Isocyanoacetylene</a></li> <li><a href="/wiki/Ketene" title="Ketene">Ketene</a></li> <li><a href="/wiki/Methane" title="Methane">Methane</a></li> <li><a href="/wiki/Methoxy" class="mw-redirect" title="Methoxy">Methoxy radical</a></li> <li><a href="/w/index.php?title=Methylenimine&action=edit&redlink=1" class="new" title="Methylenimine (page does not exist)">Methylenimine</a></li> <li><a href="/w/index.php?title=Propadienylidene&action=edit&redlink=1" class="new" title="Propadienylidene (page does not exist)">Propadienylidene</a></li> <li><a href="/w/index.php?title=Protonated_formaldehyde&action=edit&redlink=1" class="new" title="Protonated formaldehyde (page does not exist)">Protonated formaldehyde</a></li> <li><a href="/wiki/Silane" title="Silane">Silane</a></li> <li><a href="/w/index.php?title=Silicon-carbide_cluster&action=edit&redlink=1" class="new" title="Silicon-carbide cluster (page does not exist)">Silicon-carbide cluster</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/List_of_interstellar_and_circumstellar_molecules#Molecules" title="List of interstellar and circumstellar molecules">Six<br />atoms</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Acetonitrile" title="Acetonitrile">Acetonitrile</a></li> <li><a href="/w/index.php?title=Cyanobutadiynyl_radical&action=edit&redlink=1" class="new" title="Cyanobutadiynyl radical (page does not exist)">Cyanobutadiynyl radical</a></li> <li><a href="/w/index.php?title=E-Cyanomethanimine&action=edit&redlink=1" class="new" title="E-Cyanomethanimine (page does not exist)">E-Cyanomethanimine</a></li> <li><a href="/wiki/Cyclopropenone" title="Cyclopropenone">Cyclopropenone</a></li> <li><a href="/wiki/Diacetylene" title="Diacetylene">Diacetylene</a></li> <li><a href="/wiki/Ethylene" title="Ethylene">Ethylene</a></li> <li><a href="/wiki/Formamide" title="Formamide">Formamide</a></li> <li><a href="/w/index.php?title=HC4N&action=edit&redlink=1" class="new" title="HC4N (page does not exist)">HC<sub>4</sub>N</a></li> <li><a href="/wiki/Ketenimine" class="mw-redirect" title="Ketenimine">Ketenimine</a></li> <li><a href="/wiki/Methanethiol" title="Methanethiol">Methanethiol</a></li> <li><a href="/wiki/Methanol" title="Methanol">Methanol</a></li> <li><a href="/wiki/Methyl_isocyanide" title="Methyl isocyanide">Methyl isocyanide</a></li> <li><a href="/wiki/Polyyne" title="Polyyne">Pentynylidyne</a></li> <li><a href="/wiki/Propynal" class="mw-redirect" title="Propynal">Propynal</a></li> <li><a href="/w/index.php?title=Protonated_cyanoacetylene&action=edit&redlink=1" class="new" title="Protonated cyanoacetylene (page does not exist)">Protonated cyanoacetylene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/List_of_interstellar_and_circumstellar_molecules#Molecules" title="List of interstellar and circumstellar molecules">Seven<br />atoms</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/Acetaldehyde" title="Acetaldehyde">Acetaldehyde</a></li> <li><a href="/wiki/Acrylonitrile" title="Acrylonitrile">Acrylonitrile</a> <ul><li><a href="/wiki/Vinyl_cyanide" class="mw-redirect" title="Vinyl cyanide">Vinyl cyanide</a></li></ul></li> <li><a href="/wiki/Cyanopolyyne" title="Cyanopolyyne">Cyanodiacetylene</a></li> <li><a href="/wiki/Ethylene_oxide" title="Ethylene oxide">Ethylene oxide</a></li> <li><a href="/wiki/Glycolonitrile" title="Glycolonitrile">Glycolonitrile</a></li> <li><a href="/wiki/Hexatriynyl_radical" title="Hexatriynyl radical">Hexatriynyl radical</a></li> <li><a href="/wiki/Propyne" title="Propyne">Propyne</a></li> <li><a href="/wiki/Methylamine" title="Methylamine">Methylamine</a></li> <li><a href="/wiki/Methyl_isocyanate" title="Methyl isocyanate">Methyl isocyanate</a></li> <li><a href="/wiki/Vinyl_alcohol" title="Vinyl alcohol">Vinyl alcohol</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/List_of_interstellar_and_circumstellar_molecules#Molecules" title="List of interstellar and circumstellar molecules">Eight<br />atoms</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Acetic_acid" title="Acetic acid">Acetic acid</a></li> <li><a href="/wiki/Aminoacetonitrile" title="Aminoacetonitrile">Aminoacetonitrile</a></li> <li><a href="/w/index.php?title=Cyanoallene&action=edit&redlink=1" class="new" title="Cyanoallene (page does not exist)">Cyanoallene</a></li> <li><a href="/wiki/Ethanimine" title="Ethanimine">Ethanimine</a></li> <li><a href="/wiki/Glycolaldehyde" title="Glycolaldehyde">Glycolaldehyde</a></li> <li><a href="/wiki/Polyyne" title="Polyyne">Hexapentaenylidene</a></li> <li><a href="/wiki/Polyyne" title="Polyyne">Methylcyanoacetylene</a></li> <li><a href="/wiki/Methyl_formate" title="Methyl formate">Methyl formate</a></li> <li><a class="mw-selflink selflink">Acrolein</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/List_of_interstellar_and_circumstellar_molecules#Molecules" title="List of interstellar and circumstellar molecules">Nine<br />atoms</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/Acetamide" title="Acetamide">Acetamide</a></li> <li><a href="/wiki/Cyanopolyyne" title="Cyanopolyyne">Cyanohexatriyne</a></li> <li><a href="/wiki/Dimethyl_ether" title="Dimethyl ether">Dimethyl ether</a></li> <li><a href="/wiki/Ethanol" title="Ethanol">Ethanol</a></li> <li><a href="/wiki/Polyyne" title="Polyyne">Methyldiacetylene</a></li> <li><a href="/wiki/Octatetraynyl_radical" title="Octatetraynyl radical">Octatetraynyl radical</a></li> <li><a href="/wiki/Propene" class="mw-redirect" title="Propene">Propene</a></li> <li><a href="/wiki/Ethanethiol" title="Ethanethiol">Ethanethiol</a></li> <li><a href="/wiki/Propionitrile" title="Propionitrile">Propionitrile</a></li> <li><a href="/wiki/N-Methylformamide" title="N-Methylformamide">N-Methylformamide</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/List_of_interstellar_and_circumstellar_molecules#Molecules" title="List of interstellar and circumstellar molecules">Ten<br />atoms<br />or more</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Acetone" title="Acetone">Acetone</a></li> <li><a href="/wiki/Benzene" title="Benzene">Benzene</a></li> <li><a href="/wiki/Benzonitrile" title="Benzonitrile">Benzonitrile</a></li> <li><a href="/wiki/Buckminsterfullerene" title="Buckminsterfullerene">Buckminsterfullerene</a> (C<sub>60</sub>, C<sub>60</sub><sup>+</sup>, fullerene, buckyball)</li> <li><a href="/wiki/C70_fullerene" title="C70 fullerene">C<sub>70</sub> fullerene</a></li> <li><a href="/wiki/Cyanopolyyne" title="Cyanopolyyne">Cyanodecapentayne</a></li> <li><a href="/wiki/Ethylene_glycol" title="Ethylene glycol">Ethylene glycol</a></li> <li><a href="/wiki/Ethyl_formate" title="Ethyl formate">Ethyl formate</a></li> <li><a href="/wiki/Methyl_acetate" title="Methyl acetate">Methyl acetate</a></li> <li><a href="/wiki/Cyanopolyyne" title="Cyanopolyyne">Methyl-cyano-diacetylene</a></li> <li><a href="/wiki/Polyyne" title="Polyyne">Methyltriacetylene</a></li> <li><a href="/wiki/Propionaldehyde" title="Propionaldehyde">Propionaldehyde</a></li> <li><a href="/wiki/Butyronitrile" title="Butyronitrile">Butyronitrile</a></li> <li><a href="/wiki/Pyrimidine" title="Pyrimidine">Pyrimidine</a></li> <li><a href="/w/index.php?title=Heptatrienyl_radical&action=edit&redlink=1" class="new" title="Heptatrienyl radical (page does not exist)">Heptatrienyl radical</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Deuterium" title="Deuterium">Deuterated</a><br />molecules</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/Ammonia" title="Ammonia">Ammonia</a></li> <li><a href="/wiki/Ammonium" title="Ammonium">Ammonium</a> ion</li> <li><a href="/wiki/Formaldehyde" title="Formaldehyde">Formaldehyde</a></li> <li><a href="/wiki/Interstellar_formaldehyde#Interstellar_reactions" title="Interstellar formaldehyde">Formyl radical</a></li> <li><a href="/wiki/Heavy_water" title="Heavy water">Heavy water</a></li> <li><a href="/wiki/Hydrogen_cyanide" title="Hydrogen cyanide">Hydrogen cyanide</a></li> <li><a href="/wiki/Hydrogen_deuteride" title="Hydrogen deuteride">Hydrogen deuteride</a></li> <li><a href="/wiki/Hydrogen_isocyanide" title="Hydrogen isocyanide">Hydrogen isocyanide</a></li> <li><a href="/wiki/Propyne" title="Propyne">Propyne</a></li> <li><a href="/wiki/Diazenylium" title="Diazenylium">N<sub>2</sub>D<sup>+</sup></a></li> <li><a href="/wiki/Trihydrogen_cation" title="Trihydrogen cation">Trihydrogen cation</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/List_of_interstellar_and_circumstellar_molecules#Molecules" title="List of interstellar and circumstellar molecules">Unconfirmed</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Anthracene" title="Anthracene">Anthracene</a></li> <li><a href="/wiki/Dihydroxyacetone" title="Dihydroxyacetone">Dihydroxyacetone</a></li> <li><a href="/wiki/Methoxyethane" title="Methoxyethane">Methoxyethane</a></li> <li><a href="/wiki/Glycine" title="Glycine">Glycine</a></li> <li><a href="/wiki/Graphene" title="Graphene">Graphene</a></li> <li><a href="/wiki/Hemolithin" title="Hemolithin">Hemolithin</a></li> <li><a href="/w/index.php?title=H2NCO%2B&action=edit&redlink=1" class="new" title="H2NCO+ (page does not exist)">H<sub>2</sub>NCO<sup>+</sup></a></li> <li><a href="/wiki/Carbon" title="Carbon">Linear C<sub>5</sub></a></li> <li><a href="/wiki/Naphthalene" title="Naphthalene">Naphthalene cation</a></li> <li><a href="/wiki/Phosphine" title="Phosphine">Phosphine</a></li> <li><a href="/wiki/Pyrene" title="Pyrene">Pyrene</a></li> <li><a href="/wiki/Silylidyne" title="Silylidyne">Silylidyne</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/List_of_interstellar_and_circumstellar_molecules#See_also" title="List of interstellar and circumstellar molecules">Related</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/Abiogenesis" title="Abiogenesis">Abiogenesis</a></li> <li><a href="/wiki/Astrobiology" title="Astrobiology">Astrobiology</a></li> <li><a href="/wiki/Astrochemistry" title="Astrochemistry">Astrochemistry</a></li> <li><a href="/wiki/Atomic_and_molecular_astrophysics" title="Atomic and molecular astrophysics">Atomic and molecular astrophysics</a></li> <li><a href="/wiki/Chemical_formula" title="Chemical formula">Chemical formula</a></li> <li><a href="/wiki/Circumstellar_dust" title="Circumstellar dust">Circumstellar dust</a></li> <li><a href="/wiki/Circumstellar_envelope" title="Circumstellar envelope">Circumstellar envelope</a></li> <li><a href="/wiki/Cosmic_dust" title="Cosmic dust">Cosmic dust</a></li> <li><a href="/wiki/Cosmic_ray" title="Cosmic ray">Cosmic ray</a></li> <li><a href="/wiki/Cosmochemistry" title="Cosmochemistry">Cosmochemistry</a></li> <li><a href="/wiki/Diffuse_interstellar_band" class="mw-redirect" title="Diffuse interstellar band">Diffuse interstellar band</a></li> <li><a href="/wiki/Earliest_known_life_forms" title="Earliest known life forms">Earliest known life forms</a></li> <li><a href="/wiki/Extraterrestrial_life" title="Extraterrestrial life">Extraterrestrial life</a></li> <li><a href="/wiki/Extraterrestrial_liquid_water" title="Extraterrestrial liquid water">Extraterrestrial liquid water</a></li> <li><a href="/wiki/Forbidden_mechanism" title="Forbidden mechanism">Forbidden mechanism</a></li> <li><a href="/wiki/Homochirality" title="Homochirality">Homochirality</a></li> <li><a href="/wiki/Intergalactic_dust" title="Intergalactic dust">Intergalactic dust</a></li> <li><a href="/wiki/Interplanetary_medium" title="Interplanetary medium">Interplanetary medium</a></li> <li><a href="/wiki/Interstellar_medium" title="Interstellar medium">Interstellar medium</a></li> <li><a href="/wiki/Photodissociation_region" title="Photodissociation region">Photodissociation region</a></li> <li><a href="/wiki/Iron%E2%80%93sulfur_world_theory" class="mw-redirect" title="Iron–sulfur world theory">Iron–sulfur world theory</a></li> <li><a href="/wiki/Kerogen" title="Kerogen">Kerogen</a></li> <li><a href="/wiki/Molecules_in_stars" title="Molecules in stars">Molecules in stars</a></li> <li><a href="/wiki/Nexus_for_Exoplanet_System_Science" title="Nexus for Exoplanet System Science">Nexus for Exoplanet System Science</a></li> <li><a href="/wiki/Organic_compound" title="Organic compound">Organic compound</a></li> <li><a href="/wiki/Outer_space" title="Outer space">Outer space</a></li> <li><a href="/wiki/PAH_world_hypothesis" title="PAH world hypothesis">PAH world hypothesis</a></li> <li><a href="/wiki/Pseudo-panspermia" title="Pseudo-panspermia">Pseudo-panspermia</a></li> <li><a href="/wiki/Polycyclic_aromatic_hydrocarbon" title="Polycyclic aromatic hydrocarbon">Polycyclic aromatic hydrocarbon</a> (PAH)</li> <li><a href="/wiki/RNA_world_hypothesis" class="mw-redirect" title="RNA world hypothesis">RNA world hypothesis</a></li> <li><a href="/wiki/Spectroscopy" title="Spectroscopy">Spectroscopy</a></li> <li><a href="/wiki/Tholin" title="Tholin">Tholin</a></li></ul> </div></td></tr><tr><td class="navbox-abovebelow" colspan="2" style="font-weight: bold;"><div> <ul><li><b><span class="noviewer" typeof="mw:File"><span title="Category"><img alt="" src="//upload.wikimedia.org/wikipedia/en/thumb/9/96/Symbol_category_class.svg/16px-Symbol_category_class.svg.png" decoding="async" width="16" height="16" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/9/96/Symbol_category_class.svg/23px-Symbol_category_class.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/9/96/Symbol_category_class.svg/31px-Symbol_category_class.svg.png 2x" data-file-width="180" data-file-height="185" /></span></span> <a href="/wiki/Category:Astrochemistry" title="Category:Astrochemistry">Category:Astrochemistry</a></b></li> <li><span class="nowrap"><span class="noviewer" typeof="mw:File"><span><img alt="" src="//upload.wikimedia.org/wikipedia/commons/thumb/5/5c/Earth-moon.jpg/16px-Earth-moon.jpg" decoding="async" width="16" height="13" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/5/5c/Earth-moon.jpg/24px-Earth-moon.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/5/5c/Earth-moon.jpg/32px-Earth-moon.jpg 2x" data-file-width="3000" data-file-height="2400" /></span></span> </span><a href="/wiki/Portal:Outer_space" title="Portal:Outer space">Outer space portal</a></li> <li><span class="nowrap"><span class="noviewer" typeof="mw:File"><span><img alt="" src="//upload.wikimedia.org/wikipedia/commons/thumb/0/00/Crab_Nebula.jpg/16px-Crab_Nebula.jpg" decoding="async" width="16" height="16" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/0/00/Crab_Nebula.jpg/24px-Crab_Nebula.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/0/00/Crab_Nebula.jpg/32px-Crab_Nebula.jpg 2x" data-file-width="3864" data-file-height="3864" /></span></span> </span><a href="/wiki/Portal:Astronomy" title="Portal:Astronomy">Astronomy portal</a></li> <li><span class="nowrap"><span class="noviewer" typeof="mw:File"><span><img alt="" src="//upload.wikimedia.org/wikipedia/commons/thumb/e/ed/Papapishu-Lab-icon-6.svg/16px-Papapishu-Lab-icon-6.svg.png" decoding="async" width="16" height="16" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/ed/Papapishu-Lab-icon-6.svg/24px-Papapishu-Lab-icon-6.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/e/ed/Papapishu-Lab-icon-6.svg/32px-Papapishu-Lab-icon-6.svg.png 2x" data-file-width="512" data-file-height="512" /></span></span> </span><a href="/wiki/Portal:Chemistry" title="Portal:Chemistry">Chemistry portal</a></li></ul> </div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"></div><div role="navigation" class="navbox" aria-labelledby="TRP_channel_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:Transient_receptor_potential_channel_modulators" title="Template:Transient receptor potential channel modulators"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Transient_receptor_potential_channel_modulators" title="Template talk:Transient receptor potential channel modulators"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Transient_receptor_potential_channel_modulators" title="Special:EditPage/Template:Transient receptor potential channel modulators"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="TRP_channel_modulators" style="font-size:114%;margin:0 4em"><a href="/wiki/Transient_receptor_potential_channel" title="Transient receptor potential channel"><abbr title="Transient receptor potential">TRP</abbr> channel</a> <a href="/wiki/Channel_modulator" title="Channel modulator">modulators</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><abbr title="Transient receptor potential ankyrin channel"><a href="/wiki/TRPA_(ion_channel)" title="TRPA (ion channel)">TRPA</a></abbr></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;">Activators</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/4-Hydroxynonenal" title="4-Hydroxynonenal">4-Hydroxynonenal</a></li> <li><a href="/wiki/4-Oxo-2-nonenal" title="4-Oxo-2-nonenal">4-Oxo-2-nonenal</a></li> <li><a href="/wiki/Epoxyeicosatrienoic_acid" title="Epoxyeicosatrienoic acid">4,5-EET</a></li> <li><a href="/wiki/Epoxyeicosatrienoic_acid" title="Epoxyeicosatrienoic acid">12S-HpETE</a></li> <li><a href="/wiki/Cyclopentenone_prostaglandins" title="Cyclopentenone prostaglandins">15-Deoxy-Δ<sup>12,14</sup>-prostaglandin J2</a></li> <li><a href="/wiki/Hydroxy_alpha_sanshool" class="mw-redirect" title="Hydroxy alpha sanshool">α-Sanshool</a> (<a href="/wiki/Ginger" title="Ginger">ginger</a>, <a href="/wiki/Sichuan_pepper" title="Sichuan pepper">Sichuan</a> and <a href="/wiki/Grains_of_paradise" title="Grains of paradise">melegueta peppers</a>)</li> <li><a class="mw-selflink selflink">Acrolein</a></li> <li><a href="/wiki/Allicin" title="Allicin">Allicin</a> (<a href="/wiki/Garlic" title="Garlic">garlic</a>)</li> <li><a href="/wiki/Allyl_isothiocyanate" title="Allyl isothiocyanate">Allyl isothiocyanate</a> (<a href="/wiki/Mustard_plant" title="Mustard plant">mustard</a>, <a href="/wiki/Radish" title="Radish">radish</a>, <a href="/wiki/Horseradish" title="Horseradish">horseradish</a>, <a href="/wiki/Wasabi" title="Wasabi">wasabi</a>)</li> <li><a href="/wiki/AM404" title="AM404">AM404</a></li> <li><a href="/wiki/ASP-7663" title="ASP-7663">ASP-7663</a></li> <li><a href="/wiki/Bradykinin" title="Bradykinin">Bradykinin</a></li> <li><a href="/wiki/Cannabichromene" title="Cannabichromene">Cannabichromene</a> (<a href="/wiki/Cannabis" title="Cannabis">cannabis</a>)</li> <li><a href="/wiki/Cannabidiol" title="Cannabidiol">Cannabidiol</a> (<a href="/wiki/Cannabis" title="Cannabis">cannabis</a>)</li> <li><a href="/wiki/Cannabigerol" title="Cannabigerol">Cannabigerol</a> (<a href="/wiki/Cannabis" title="Cannabis">cannabis</a>)</li> <li><a href="/wiki/Cinnamaldehyde" title="Cinnamaldehyde">Cinnamaldehyde</a> (<a href="/wiki/Cinnamon" title="Cinnamon">cinnamon</a>)</li> <li><a href="/wiki/CR_gas" title="CR gas">CR gas (dibenzoxazepine; DBO)</a></li> <li><a href="/wiki/CS_gas" title="CS gas">CS gas (2-chlorobenzal malononitrile)</a></li> <li><a href="/wiki/Cuminaldehyde" title="Cuminaldehyde">Cuminaldehyde</a> (<a href="/wiki/Cumin" title="Cumin">cumin</a>)</li> <li><a href="/wiki/Curcumin" title="Curcumin">Curcumin</a> (<a href="/wiki/Turmeric" title="Turmeric">turmeric</a>)</li> <li><a href="/w/index.php?title=Dehydroligustilide&action=edit&redlink=1" class="new" title="Dehydroligustilide (page does not exist)">Dehydroligustilide</a> (<a href="/wiki/Celery" title="Celery">celery</a>)</li> <li><a href="/wiki/Diallyl_disulfide" title="Diallyl disulfide">Diallyl disulfide</a></li> <li><a href="/wiki/Dicentrine" title="Dicentrine">Dicentrine</a> (<i><a href="/wiki/Lindera" title="Lindera">Lindera</a></i> spp.)</li> <li><a href="/w/index.php?title=Farnesyl_thiosalicylic_acid&action=edit&redlink=1" class="new" title="Farnesyl thiosalicylic acid (page does not exist)">Farnesyl thiosalicylic acid</a></li> <li><a href="/wiki/Formalin" class="mw-redirect" title="Formalin">Formalin</a></li> <li><a href="/wiki/Gingerol" title="Gingerol">Gingerols</a> (<a href="/wiki/Ginger" title="Ginger">ginger</a>)</li> <li><a href="/wiki/Hepoxilin_A3" class="mw-redirect" title="Hepoxilin A3">Hepoxilin A3</a></li> <li><a href="/wiki/Hepoxilin_B3" class="mw-redirect" title="Hepoxilin B3">Hepoxilin B3</a></li> <li><a href="/wiki/Hydrogen_peroxide" title="Hydrogen peroxide">Hydrogen peroxide</a></li> <li><a href="/wiki/Icilin" title="Icilin">Icilin</a></li> <li><a href="/wiki/Isothiocyanate" title="Isothiocyanate">Isothiocyanate</a></li> <li><a href="/wiki/JT-010" title="JT-010">JT-010</a></li> <li><a href="/wiki/Ligustilide" title="Ligustilide">Ligustilide</a> (<a href="/wiki/Celery" title="Celery">celery</a>, <i><a href="/wiki/Angelica_acutiloba" title="Angelica acutiloba">Angelica acutiloba</a></i>)</li> <li><a href="/wiki/Linalool" title="Linalool">Linalool</a> (<a href="/wiki/Sichuan_pepper" title="Sichuan pepper">Sichuan pepper</a>, <a href="/wiki/Thyme" title="Thyme">thyme</a>)</li> <li><a href="/wiki/Methylglyoxal" title="Methylglyoxal">Methylglyoxal</a></li> <li><a href="/wiki/Methyl_salicylate" title="Methyl salicylate">Methyl salicylate</a> (<a href="/wiki/Wintergreen" title="Wintergreen">wintergreen</a>)</li> <li><a href="/wiki/N-Methylmaleimide" title="N-Methylmaleimide">N-Methylmaleimide</a></li> <li><a href="/wiki/Nicotine" title="Nicotine">Nicotine</a> (<a href="/wiki/Tobacco" title="Tobacco">tobacco</a>)</li> <li><a href="/wiki/Oleocanthal" title="Oleocanthal">Oleocanthal</a> (<a href="/wiki/Olive_oil" title="Olive oil">olive oil</a>)</li> <li><a href="/wiki/Paclitaxel" title="Paclitaxel">Paclitaxel</a> (<a href="/wiki/Taxus_brevifolia" title="Taxus brevifolia">Pacific yew</a>)</li> <li><a href="/wiki/Paracetamol" title="Paracetamol">Paracetamol (acetaminophen)</a></li> <li><a href="/wiki/PF-4840154" title="PF-4840154">PF-4840154</a></li> <li><a href="/wiki/Phenacyl_chloride" title="Phenacyl chloride">Phenacyl chloride</a></li> <li><a href="/wiki/Polygodial" title="Polygodial">Polygodial</a> (<a href="/wiki/Tasmannia_stipitata" title="Tasmannia stipitata">Dorrigo pepper</a>)</li> <li><a href="/wiki/Shogaol" title="Shogaol">Shogaols</a> (<a href="/wiki/Ginger" title="Ginger">ginger</a>, <a href="/wiki/Sichuan_pepper" title="Sichuan pepper">Sichuan</a> and <a href="/wiki/Grains_of_paradise" title="Grains of paradise">melegueta peppers</a>)</li> <li><a href="/wiki/Tear_gas" title="Tear gas">Tear gases</a></li> <li><a href="/wiki/Tetrahydrocannabinol" title="Tetrahydrocannabinol">Tetrahydrocannabinol</a> (<a href="/wiki/Cannabis" title="Cannabis">cannabis</a>)</li> <li><a href="/wiki/Tetrahydrocannabiorcol" title="Tetrahydrocannabiorcol">Tetrahydrocannabiorcol</a></li> <li><a href="/wiki/Syn-Propanethial-S-oxide" title="Syn-Propanethial-S-oxide">Thiopropanal S-oxide</a> (<a href="/wiki/Onion" title="Onion">onion</a>)</li> <li><a href="/wiki/Umbellulone" title="Umbellulone">Umbellulone</a> (<i>Umbellularia californica</i>)</li> <li><a href="/wiki/WIN_55,212-2" title="WIN 55,212-2">WIN 55,212-2</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;">Blockers</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/A-967079" title="A-967079">A-967079</a></li> <li><a href="/wiki/AM-0902" title="AM-0902">AM-0902</a></li> <li><a href="/w/index.php?title=Dehydroligustilide&action=edit&redlink=1" class="new" title="Dehydroligustilide (page does not exist)">Dehydroligustilide</a> (<a href="/wiki/Celery" title="Celery">celery</a>)</li> <li><a href="/wiki/HC-030031" title="HC-030031">HC-030031</a></li> <li><a href="/wiki/Nicotine" title="Nicotine">Nicotine</a> (<a href="/wiki/Tobacco" title="Tobacco">tobacco</a>)</li> <li><a href="/wiki/PF-04745637" title="PF-04745637">PF-04745637</a></li> <li><a href="/wiki/Ruthenium_red" title="Ruthenium red">Ruthenium red</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;"><abbr title="Transient receptor potential canonical channel"><a href="/wiki/TRPC" title="TRPC">TRPC</a></abbr></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;">Activators</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/Adhyperforin" title="Adhyperforin">Adhyperforin</a> (<a href="/wiki/Hypericum_perforatum" title="Hypericum perforatum">St John's wort</a>)</li> <li><a href="/wiki/Diglyceride" title="Diglyceride">Diacyl glycerol</a></li> <li><a href="/wiki/GSK1702934A" title="GSK1702934A">GSK1702934A</a></li> <li><a href="/wiki/Hyperforin" title="Hyperforin">Hyperforin</a> (<a href="/wiki/Hypericum_perforatum" title="Hypericum perforatum">St John's wort</a>)</li> <li><a href="/wiki/Substance_P" title="Substance P">Substance P</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;">Blockers</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%E2%80%B2-5-Dichlorodiphenylamine-2-carboxylic_acid&action=edit&redlink=1" class="new" title="3′-5-Dichlorodiphenylamine-2-carboxylic acid (page does not exist)">DCDPC</a></li> <li><a href="/wiki/Dehydroepiandrosterone_sulfate" title="Dehydroepiandrosterone sulfate">DHEA-S</a></li> <li><a href="/wiki/Flufenamic_acid" title="Flufenamic acid">Flufenamic acid</a></li> <li><a href="/wiki/GSK417651A" title="GSK417651A">GSK417651A</a></li> <li><a href="/w/index.php?title=GSK2293017A&action=edit&redlink=1" class="new" title="GSK2293017A (page does not exist)">GSK2293017A</a></li> <li><a href="/wiki/Meclofenamic_acid" title="Meclofenamic acid">Meclofenamic acid</a></li> <li><a href="/wiki/N-(p-Amylcinnamoyl)anthranilic_acid" title="N-(p-Amylcinnamoyl)anthranilic acid">N-(p-Amylcinnamoyl)anthranilic acid</a></li> <li><a href="/wiki/Niflumic_acid" title="Niflumic acid">Niflumic acid</a></li> <li><a href="/wiki/Pregnenolone_sulfate" title="Pregnenolone sulfate">Pregnenolone sulfate</a></li> <li><a href="/wiki/Progesterone" title="Progesterone">Progesterone</a></li> <li><a href="/w/index.php?title=Pyr3&action=edit&redlink=1" class="new" title="Pyr3 (page does not exist)">Pyr3</a></li> <li><a href="/wiki/Tolfenamic_acid" title="Tolfenamic acid">Tolfenamic acid</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;"><abbr title="Transient receptor potential melastatin channel"><a href="/wiki/TRPM" title="TRPM">TRPM</a></abbr></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;">Activators</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/Adenosine_diphosphate_ribose" title="Adenosine diphosphate ribose">ADP-ribose</a></li> <li><a href="/w/index.php?title=BCTC_(drug)&action=edit&redlink=1" class="new" title="BCTC (drug) (page does not exist)">BCTC</a></li> <li><a href="/wiki/Calcium" title="Calcium">Calcium</a> (intracellular)</li> <li><a href="/wiki/CIM-0216" title="CIM-0216">CIM-0216</a></li> <li><a href="/wiki/Cold" title="Cold">Cold</a></li> <li><a href="/w/index.php?title=Coolact_P&action=edit&redlink=1" class="new" title="Coolact P (page does not exist)">Coolact P</a></li> <li><a href="/wiki/Cooling_Agent_10" class="mw-redirect" title="Cooling Agent 10">Cooling Agent 10</a></li> <li><a href="/wiki/Eucalyptol" title="Eucalyptol">Eucalyptol</a> (<a href="/wiki/Eucalyptus" title="Eucalyptus">eucalyptus</a>)</li> <li><a href="/w/index.php?title=Frescolat_MGA&action=edit&redlink=1" class="new" title="Frescolat MGA (page does not exist)">Frescolat MGA</a></li> <li><a href="/w/index.php?title=Frescolat_ML&action=edit&redlink=1" class="new" title="Frescolat ML (page does not exist)">Frescolat ML</a></li> <li><a href="/wiki/Geraniol" title="Geraniol">Geraniol</a></li> <li><a href="/wiki/Hydroxycitronellal" title="Hydroxycitronellal">Hydroxycitronellal</a></li> <li><a href="/wiki/Icilin" title="Icilin">Icilin</a></li> <li><a href="/wiki/Linalool" title="Linalool">Linalool</a></li> <li><a href="/wiki/Menthol" title="Menthol">Menthol</a> (<a href="/wiki/Mentha" title="Mentha">mint</a>)</li> <li><a href="/w/index.php?title=PMD_38&action=edit&redlink=1" class="new" title="PMD 38 (page does not exist)">PMD 38</a></li> <li><a href="/wiki/Pregnenolone_sulfate" title="Pregnenolone sulfate">Pregnenolone sulfate</a></li> <li><a href="/w/index.php?title=Rutamarin&action=edit&redlink=1" class="new" title="Rutamarin (page does not exist)">Rutamarin</a> (<i><a href="/wiki/Ruta_graveolens" title="Ruta graveolens">Ruta graveolens</a></i>)</li> <li><a href="/wiki/Steviol_glycoside" title="Steviol glycoside">Steviol glycosides</a> (e.g., <a href="/wiki/Stevioside" title="Stevioside">stevioside</a>) (<i><a href="/wiki/Stevia_rebaudiana" title="Stevia rebaudiana">Stevia rebaudiana</a></i>)</li> <li>Sweet <a href="/wiki/Taste" title="Taste">tastants</a> (e.g., <a href="/wiki/Glucose" title="Glucose">glucose</a>, <a href="/wiki/Fructose" title="Fructose">fructose</a>, <a href="/wiki/Sucrose" title="Sucrose">sucrose</a>; indirectly)</li> <li><a href="/w/index.php?title=Thio-BCTC&action=edit&redlink=1" class="new" title="Thio-BCTC (page does not exist)">Thio-BCTC</a></li> <li><a href="/wiki/WS-12" class="mw-redirect" title="WS-12">WS-12</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;">Blockers</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/AMG-333" title="AMG-333">AMG-333</a></li> <li><a href="/wiki/Capsazepine" title="Capsazepine">Capsazepine</a></li> <li><a href="/wiki/Clotrimazole" title="Clotrimazole">Clotrimazole</a></li> <li><a href="/w/index.php?title=3%E2%80%B2-5-Dichlorodiphenylamine-2-carboxylic_acid&action=edit&redlink=1" class="new" title="3′-5-Dichlorodiphenylamine-2-carboxylic acid (page does not exist)">DCDPC</a></li> <li><a href="/w/index.php?title=Elismetrep&action=edit&redlink=1" class="new" title="Elismetrep (page does not exist)">Elismetrep</a></li> <li><a href="/wiki/Flufenamic_acid" title="Flufenamic acid">Flufenamic acid</a></li> <li><a href="/wiki/Meclofenamic_acid" title="Meclofenamic acid">Meclofenamic acid</a></li> <li><a href="/wiki/Mefenamic_acid" title="Mefenamic acid">Mefenamic acid</a></li> <li><a href="/wiki/N-(p-Amylcinnamoyl)anthranilic_acid" title="N-(p-Amylcinnamoyl)anthranilic acid">N-(p-Amylcinnamoyl)anthranilic acid</a></li> <li><a href="/wiki/Nicotine" title="Nicotine">Nicotine</a> (<a href="/wiki/Tobacco" title="Tobacco">tobacco</a>)</li> <li><a href="/wiki/Niflumic_acid" title="Niflumic acid">Niflumic acid</a></li> <li><a href="/wiki/Ononetin" title="Ononetin">Ononetin</a></li> <li><a href="/wiki/PF-05105679" title="PF-05105679">PF-05105679</a></li> <li><a href="/wiki/RQ-00203078" title="RQ-00203078">RQ-00203078</a></li> <li><a href="/wiki/Ruthenium_red" title="Ruthenium red">Ruthenium red</a></li> <li><a href="/w/index.php?title=Rutamarin&action=edit&redlink=1" class="new" title="Rutamarin (page does not exist)">Rutamarin</a> (<i><a href="/wiki/Ruta_graveolens" title="Ruta graveolens">Ruta graveolens</a></i>)</li> <li><a href="/wiki/Tolfenamic_acid" title="Tolfenamic acid">Tolfenamic acid</a></li> <li><a href="/wiki/Triphenylphosphine_oxide" title="Triphenylphosphine oxide">TPPO</a></li> <li><a href="/wiki/TRPM4-IN-5" title="TRPM4-IN-5">TRPM4-IN-5</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;"><abbr title="Transient receptor potential mucolipin channel"><a href="/wiki/TRPML" title="TRPML">TRPML</a></abbr></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;">Activators</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=EVP21&action=edit&redlink=1" class="new" title="EVP21 (page does not exist)">EVP21</a></li> <li><a href="/wiki/MK6-83" title="MK6-83">MK6-83</a></li> <li><a href="/wiki/ML-SA1" title="ML-SA1">ML-SA1</a></li> <li><a href="/wiki/ML2-SA1" title="ML2-SA1">ML2-SA1</a></li> <li><a href="/wiki/Phosphatidylinositol_3,5-bisphosphate" title="Phosphatidylinositol 3,5-bisphosphate">PI(3,5)P<sub>2</sub></a></li> <li><a href="/w/index.php?title=SF-22&action=edit&redlink=1" class="new" title="SF-22 (page does not exist)">SF-22</a></li> <li><a href="/wiki/SN-2" title="SN-2">SN-2</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;">Blockers</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/ML-SI3" title="ML-SI3">ML-SI3</a></li> <li><a href="/wiki/Phosphatidylinositol_4,5-bisphosphate" title="Phosphatidylinositol 4,5-bisphosphate">PI(4,5)P<sub>2</sub></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;"><abbr title="Transient receptor potential polycystin channel"><a href="/wiki/TRPP" title="TRPP">TRPP</a></abbr></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;">Activators</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/Triptolide" title="Triptolide">Triptolide</a> (<i><a href="/wiki/Tripterygium_wilfordii" title="Tripterygium wilfordii">Tripterygium wilfordii</a></i>)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;">Blockers</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/Ruthenium_red" title="Ruthenium red">Ruthenium red</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;"><abbr title="Transient receptor potential vanilloid channel"><a href="/wiki/TRPV" title="TRPV">TRPV</a></abbr></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;">Activators</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/2-Aminoethoxydiphenyl_borate" title="2-Aminoethoxydiphenyl borate">2-APB</a></li> <li><a href="/wiki/Epoxyeicosatrienoic_acid" title="Epoxyeicosatrienoic acid">5',6'-EET</a></li> <li><a href="/wiki/9-Hydroxyoctadecadienoic_acid" title="9-Hydroxyoctadecadienoic acid">9-HODE</a></li> <li><a href="/wiki/9-Hydroxyoctadecadienoic_acid" title="9-Hydroxyoctadecadienoic acid">9-oxoODE</a></li> <li><a href="/wiki/Epoxyeicosatrienoic_acid" title="Epoxyeicosatrienoic acid">12S-HETE</a></li> <li><a href="/wiki/Epoxyeicosatrienoic_acid" title="Epoxyeicosatrienoic acid">12S-HpETE</a></li> <li><a href="/wiki/13-Hydroxyoctadecadienoic_acid" title="13-Hydroxyoctadecadienoic acid">13-HODE</a></li> <li><a href="/wiki/13-Hydroxyoctadecadienoic_acid" title="13-Hydroxyoctadecadienoic acid">13-oxoODE</a></li> <li><a href="/wiki/20-Hydroxyeicosatetraenoic_acid" title="20-Hydroxyeicosatetraenoic acid">20-HETE</a></li> <li><a href="/wiki/Hydroxy_alpha_sanshool" class="mw-redirect" title="Hydroxy alpha sanshool">α-Sanshool</a> (<a href="/wiki/Ginger" title="Ginger">ginger</a>, <a href="/wiki/Sichuan_pepper" title="Sichuan pepper">Sichuan</a> and <a href="/wiki/Grains_of_paradise" title="Grains of paradise">melegueta peppers</a>)</li> <li><a href="/wiki/Allicin" title="Allicin">Allicin</a> (<a href="/wiki/Garlic" title="Garlic">garlic</a>)</li> <li><a href="/wiki/AM404" title="AM404">AM404</a></li> <li><a href="/wiki/Anandamide" title="Anandamide">Anandamide</a></li> <li><a href="/w/index.php?title=Bisandrographolide&action=edit&redlink=1" class="new" title="Bisandrographolide (page does not exist)">Bisandrographolide</a> (<i><a href="/wiki/Andrographis_paniculata" title="Andrographis paniculata">Andrographis paniculata</a></i>)</li> <li><a href="/wiki/Camphor" title="Camphor">Camphor</a> (<a href="/wiki/Cinnamomum_camphora" class="mw-redirect" title="Cinnamomum camphora">camphor laurel</a>, <a href="/wiki/Rosemary" title="Rosemary">rosemary</a>, <a href="/wiki/Camphorweed" title="Camphorweed">camphorweed</a>, <a href="/wiki/African_blue_basil" title="African blue basil">African blue basil</a>, <a href="/wiki/Ocimum_kilimandscharicum" title="Ocimum kilimandscharicum">camphor basil</a>)</li> <li><a href="/wiki/Cannabidiol" title="Cannabidiol">Cannabidiol</a> (<a href="/wiki/Cannabis" title="Cannabis">cannabis</a>)</li> <li><a href="/wiki/Cannabidivarin" title="Cannabidivarin">Cannabidivarin</a> (<a href="/wiki/Cannabis" title="Cannabis">cannabis</a>)</li> <li><a href="/wiki/Capsaicin" title="Capsaicin">Capsaicin</a> (<a href="/wiki/Chili_pepper" title="Chili pepper">chili pepper</a>)</li> <li><a href="/wiki/Carvacrol" title="Carvacrol">Carvacrol</a> (<a href="/wiki/Oregano" title="Oregano">oregano</a>, <a href="/wiki/Thyme" title="Thyme">thyme</a>, <a href="/wiki/Lepidium" title="Lepidium">pepperwort</a>, <a href="/wiki/Monarda_fistulosa" title="Monarda fistulosa">wild bergamot</a>, others)</li> <li><a href="/wiki/Dehydroepiandrosterone" title="Dehydroepiandrosterone">DHEA</a></li> <li><a href="/wiki/Diglyceride" title="Diglyceride">Diacyl glycerol</a></li> <li><a href="/wiki/Dihydrocapsaicin" title="Dihydrocapsaicin">Dihydrocapsaicin</a> (<a href="/wiki/Chili_pepper" title="Chili pepper">chili pepper</a>)</li> <li><a href="/wiki/Estradiol" title="Estradiol">Estradiol</a></li> <li><a href="/wiki/Eugenol" title="Eugenol">Eugenol</a> (<a href="/wiki/Basil" title="Basil">basil</a>, <a href="/wiki/Clove" title="Clove">clove</a>)</li> <li><a href="/wiki/Evodiamine" title="Evodiamine">Evodiamine</a> (<i><a href="/wiki/Tetradium_ruticarpum" title="Tetradium ruticarpum">Euodia ruticarpa</a></i>)</li> <li><a href="/wiki/Gingerol" title="Gingerol">Gingerols</a> (<a href="/wiki/Ginger" title="Ginger">ginger</a>)</li> <li><a href="/wiki/GSK1016790A" title="GSK1016790A">GSK1016790A</a></li> <li><a href="/wiki/Heat" title="Heat">Heat</a></li> <li><a href="/wiki/Hepoxilin_A3" class="mw-redirect" title="Hepoxilin A3">Hepoxilin A3</a></li> <li><a href="/wiki/Hepoxilin_B3" class="mw-redirect" title="Hepoxilin B3">Hepoxilin B3</a></li> <li><a href="/wiki/Homocapsaicin" title="Homocapsaicin">Homocapsaicin</a> (<a href="/wiki/Chili_pepper" title="Chili pepper">chili pepper</a>)</li> <li><a href="/wiki/Homodihydrocapsaicin" title="Homodihydrocapsaicin">Homodihydrocapsaicin</a> (<a href="/wiki/Chili_pepper" title="Chili pepper">chili pepper</a>)</li> <li><a href="/wiki/Incensole" title="Incensole">Incensole</a> (<a href="/wiki/Incense" title="Incense">incense</a>)</li> <li><a href="/wiki/Lysophosphatidic_acid" title="Lysophosphatidic acid">Lysophosphatidic acid</a></li> <li>Low <a href="/wiki/PH" title="PH">pH</a> (acidic conditions)</li> <li><a href="/wiki/Menthol" title="Menthol">Menthol</a> (<a href="/wiki/Mentha" title="Mentha">mint</a>)</li> <li><a href="/wiki/N-Arachidonoyl_dopamine" title="N-Arachidonoyl dopamine">N-Arachidonoyl dopamine</a></li> <li><a href="/w/index.php?title=N-Oleoyldopamine&action=edit&redlink=1" class="new" title="N-Oleoyldopamine (page does not exist)">N-Oleoyldopamine</a></li> <li><a href="/wiki/Oleoylethanolamide" title="Oleoylethanolamide">N-Oleoylethanolamide</a></li> <li><a href="/wiki/Nonivamide" title="Nonivamide">Nonivamide (PAVA)</a> (<a href="/wiki/PAVA_spray" title="PAVA spray">PAVA spray</a>)</li> <li><a href="/wiki/Nordihydrocapsaicin" title="Nordihydrocapsaicin">Nordihydrocapsaicin</a> (<a href="/wiki/Chili_pepper" title="Chili pepper">chili pepper</a>)</li> <li><a href="/wiki/Paclitaxel" title="Paclitaxel">Paclitaxel</a> (<a href="/wiki/Taxus_brevifolia" title="Taxus brevifolia">Pacific yew</a>)</li> <li><a href="/wiki/Paracetamol" title="Paracetamol">Paracetamol (acetaminophen)</a></li> <li><a href="/wiki/Phenylacetylrinvanil" title="Phenylacetylrinvanil">Phenylacetylrinvanil</a></li> <li><a href="/wiki/Phorbol_esters" title="Phorbol esters">Phorbol esters</a> (e.g., <a href="/w/index.php?title=4%CE%B1-phorbol_12,13-didecanoate&action=edit&redlink=1" class="new" title="4α-phorbol 12,13-didecanoate (page does not exist)">4α-PDD</a>)</li> <li><a href="/wiki/Piperine" title="Piperine">Piperine</a> (<a href="/wiki/Black_pepper" title="Black pepper">black pepper</a>, <a href="/wiki/Long_pepper" title="Long pepper">long pepper</a>)</li> <li><a href="/wiki/Polygodial" title="Polygodial">Polygodial</a> (<a href="/wiki/Tasmannia_stipitata" title="Tasmannia stipitata">Dorrigo pepper</a>)</li> <li><a href="/wiki/Probenecid" title="Probenecid">Probenecid</a></li> <li><a href="/wiki/Proton" title="Proton">Protons</a></li> <li><a href="/wiki/RhTx" title="RhTx">RhTx</a></li> <li><a href="/w/index.php?title=Rutamarin&action=edit&redlink=1" class="new" title="Rutamarin (page does not exist)">Rutamarin</a> (<i><a href="/wiki/Ruta_graveolens" title="Ruta graveolens">Ruta graveolens</a></i>)</li> <li><a href="/wiki/Resiniferatoxin" title="Resiniferatoxin">Resiniferatoxin</a> (RTX) (<i><a href="/wiki/Euphorbia_resinifera" title="Euphorbia resinifera">Euphorbia resinifera</a>/<a href="/wiki/Euphorbia_poissonii" title="Euphorbia poissonii">pooissonii</a></i>)</li> <li><a href="/wiki/Shogaol" title="Shogaol">Shogaols</a> (<a href="/wiki/Ginger" title="Ginger">ginger</a>, <a href="/wiki/Sichuan_pepper" title="Sichuan pepper">Sichuan</a> and <a href="/wiki/Grains_of_paradise" title="Grains of paradise">melegueta peppers</a>)</li> <li><a href="/wiki/Tetrahydrocannabivarin" title="Tetrahydrocannabivarin">Tetrahydrocannabivarin</a> (<a href="/wiki/Cannabis" title="Cannabis">cannabis</a>)</li> <li><a href="/wiki/Thymol" title="Thymol">Thymol</a> (<a href="/wiki/Thyme" title="Thyme">thyme</a>, <a href="/wiki/Oregano" title="Oregano">oregano</a>)</li> <li><a href="/wiki/Tinyatoxin" title="Tinyatoxin">Tinyatoxin</a> (<i><a href="/wiki/Euphorbia_resinifera" title="Euphorbia resinifera">Euphorbia resinifera</a>/<a href="/wiki/Euphorbia_poissonii" title="Euphorbia poissonii">pooissonii</a></i>)</li> <li><a href="/wiki/Tramadol" title="Tramadol">Tramadol</a></li> <li><a href="/wiki/Vanillin" title="Vanillin">Vanillin</a> (<a href="/wiki/Vanilla" title="Vanilla">vanilla</a>)</li> <li><a href="/wiki/Zucapsaicin" title="Zucapsaicin">Zucapsaicin</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;">Blockers</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/Spinasterol" title="Spinasterol">α-Spinasterol</a> (<i><a href="/wiki/Vernonia" title="Vernonia">Vernonia tweediana</a></i>)</li> <li><a href="/wiki/AMG-517" title="AMG-517">AMG-517</a></li> <li><a href="/wiki/AMG-9810" title="AMG-9810">AMG-9810</a></li> <li><a href="/w/index.php?title=Asivatrep&action=edit&redlink=1" class="new" title="Asivatrep (page does not exist)">Asivatrep</a></li> <li><a href="/w/index.php?title=BCTC_(drug)&action=edit&redlink=1" class="new" title="BCTC (drug) (page does not exist)">BCTC</a></li> <li><a href="/wiki/Cannabigerol" title="Cannabigerol">Cannabigerol</a> (<a href="/wiki/Cannabis" title="Cannabis">cannabis</a>)</li> <li><a href="/wiki/Cannabigerolic_acid" title="Cannabigerolic acid">Cannabigerolic acid</a> (<a href="/wiki/Cannabis" title="Cannabis">cannabis</a>)</li> <li><a href="/wiki/Cannabigerovarin" title="Cannabigerovarin">Cannabigerovarin</a> (<a href="/wiki/Cannabis" title="Cannabis">cannabis</a>)</li> <li><a href="/wiki/Cannabinol" title="Cannabinol">Cannabinol</a> (<a href="/wiki/Cannabis" title="Cannabis">cannabis</a>)</li> <li><a href="/wiki/Capsazepine" title="Capsazepine">Capsazepine</a></li> <li><a href="/w/index.php?title=3%E2%80%B2-5-Dichlorodiphenylamine-2-carboxylic_acid&action=edit&redlink=1" class="new" title="3′-5-Dichlorodiphenylamine-2-carboxylic acid (page does not exist)">DCDPC</a></li> <li><a href="/wiki/Dehydroepiandrosterone" title="Dehydroepiandrosterone">DHEA</a></li> <li><a href="/wiki/Dehydroepiandrosterone_sulfate" title="Dehydroepiandrosterone sulfate">DHEA-S</a></li> <li><a href="/wiki/Flufenamic_acid" title="Flufenamic acid">Flufenamic acid</a></li> <li><a href="/wiki/GRC-6211" title="GRC-6211">GRC-6211</a></li> <li><a href="/wiki/HC-067047" title="HC-067047">HC-067047</a></li> <li><a href="/wiki/Lanthanum" title="Lanthanum">Lanthanum</a></li> <li><a href="/wiki/Mavatrep" title="Mavatrep">Mavatrep</a></li> <li><a href="/wiki/Meclofenamic_acid" title="Meclofenamic acid">Meclofenamic acid</a></li> <li><a href="/wiki/N-(p-Amylcinnamoyl)anthranilic_acid" title="N-(p-Amylcinnamoyl)anthranilic acid">N-(p-Amylcinnamoyl)anthranilic acid</a></li> <li><a href="/w/index.php?title=NGD-8243&action=edit&redlink=1" class="new" title="NGD-8243 (page does not exist)">NGD-8243</a></li> <li><a href="/wiki/Niflumic_acid" title="Niflumic acid">Niflumic acid</a></li> <li><a href="/wiki/Pregnenolone_sulfate" title="Pregnenolone sulfate">Pregnenolone sulfate</a></li> <li><a href="/w/index.php?title=RN-1734&action=edit&redlink=1" class="new" title="RN-1734 (page does not exist)">RN-1734</a></li> <li><a href="/wiki/RN-9893" title="RN-9893">RN-9893</a></li> <li><a href="/wiki/Ruthenium_red" title="Ruthenium red">Ruthenium red</a></li> <li><a href="/wiki/SB-366791" title="SB-366791">SB-366791</a></li> <li><a href="/wiki/SB-705498" title="SB-705498">SB-705498</a></li> <li><a href="/w/index.php?title=Tivanisiran&action=edit&redlink=1" class="new" title="Tivanisiran (page does not exist)">Tivanisiran</a></li> <li><a href="/wiki/Tolfenamic_acid" title="Tolfenamic acid">Tolfenamic acid</a></li> <li><a href="/wiki/TRPV3-74a" title="TRPV3-74a">TRPV3-74a</a></li></ul> </div></td></tr></tbody></table><div></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> • <a href="/wiki/Template:Ion_channel_modulators" title="Template:Ion channel modulators">Ion channel modulators</a></i></div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"><style data-mw-deduplicate="TemplateStyles:r1038841319">.mw-parser-output .tooltip-dotted{border-bottom:1px dotted;cursor:help}</style><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1038841319"></div><div role="navigation" class="navbox authority-control" aria-label="Navbox" 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