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class="vector-toc-numb">5</span> <span>List of plants that contain thymol</span> </div> </a> <ul id="toc-List_of_plants_that_contain_thymol-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Toxicology_and_environmental_impacts" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Toxicology_and_environmental_impacts"> <div class="vector-toc-text"> <span class="vector-toc-numb">6</span> <span>Toxicology and environmental impacts</span> </div> </a> <button aria-controls="toc-Toxicology_and_environmental_impacts-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 Toxicology and environmental impacts subsection</span> </button> <ul id="toc-Toxicology_and_environmental_impacts-sublist" class="vector-toc-list"> <li id="toc-Environmental_breakdown_and_use_as_a_pesticide" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Environmental_breakdown_and_use_as_a_pesticide"> <div class="vector-toc-text"> <span class="vector-toc-numb">6.1</span> <span>Environmental breakdown and use as a pesticide</span> </div> </a> <ul id="toc-Environmental_breakdown_and_use_as_a_pesticide-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Compendial_status" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Compendial_status"> <div class="vector-toc-text"> <span class="vector-toc-numb">7</span> <span>Compendial status</span> </div> </a> <ul id="toc-Compendial_status-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-See_also" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#See_also"> <div class="vector-toc-text"> <span class="vector-toc-numb">8</span> <span>See also</span> </div> </a> <ul id="toc-See_also-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Notes_and_references" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Notes_and_references"> <div class="vector-toc-text"> <span class="vector-toc-numb">9</span> <span>Notes and references</span> </div> </a> <ul id="toc-Notes_and_references-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-External_links" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#External_links"> <div class="vector-toc-text"> <span class="vector-toc-numb">10</span> <span>External links</span> </div> </a> <ul id="toc-External_links-sublist" class="vector-toc-list"> </ul> </li> </ul> </div> </div> </nav> </div> </div> <div class="mw-content-container"> <main id="content" class="mw-body"> <header class="mw-body-header vector-page-titlebar"> <nav aria-label="Contents" class="vector-toc-landmark"> <div id="vector-page-titlebar-toc" class="vector-dropdown vector-page-titlebar-toc vector-button-flush-left" title="Table of Contents" > <input type="checkbox" id="vector-page-titlebar-toc-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-vector-page-titlebar-toc" class="vector-dropdown-checkbox " aria-label="Toggle the table of contents" > <label id="vector-page-titlebar-toc-label" for="vector-page-titlebar-toc-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--icon-only " aria-hidden="true" ><span class="vector-icon mw-ui-icon-listBullet mw-ui-icon-wikimedia-listBullet"></span> <span class="vector-dropdown-label-text">Toggle the table of contents</span> </label> <div class="vector-dropdown-content"> <div id="vector-page-titlebar-toc-unpinned-container" class="vector-unpinned-container"> </div> </div> </div> </nav> <h1 id="firstHeading" class="firstHeading mw-first-heading"><span class="mw-page-title-main">Thymol</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 35 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-35" 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">35 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%AB%D9%8A%D9%85%D9%88%D9%84" title="ثيمول – Arabic" lang="ar" hreflang="ar" data-title="ثيمول" data-language-autonym="العربية" data-language-local-name="Arabic" class="interlanguage-link-target"><span>العربية</span></a></li><li class="interlanguage-link interwiki-azb mw-list-item"><a href="https://azb.wikipedia.org/wiki/%D8%AA%DB%8C%D9%88%D9%85%D9%88%D9%84" title="تیومول – South Azerbaijani" lang="azb" hreflang="azb" data-title="تیومول" 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%A2%D1%8B%D0%BC%D0%BE%D0%BB" title="Тымол – Belarusian" lang="be" hreflang="be" data-title="Тымол" data-language-autonym="Беларуская" data-language-local-name="Belarusian" class="interlanguage-link-target"><span>Беларуская</span></a></li><li class="interlanguage-link interwiki-bg mw-list-item"><a href="https://bg.wikipedia.org/wiki/%D0%A2%D0%B8%D0%BC%D0%BE%D0%BB" title="Тимол – Bulgarian" lang="bg" hreflang="bg" data-title="Тимол" data-language-autonym="Български" data-language-local-name="Bulgarian" class="interlanguage-link-target"><span>Български</span></a></li><li class="interlanguage-link interwiki-ca mw-list-item"><a href="https://ca.wikipedia.org/wiki/Timol" title="Timol – Catalan" lang="ca" hreflang="ca" data-title="Timol" 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/Thymol" title="Thymol – Czech" lang="cs" hreflang="cs" data-title="Thymol" 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/Thymol" title="Thymol – German" lang="de" hreflang="de" data-title="Thymol" data-language-autonym="Deutsch" data-language-local-name="German" class="interlanguage-link-target"><span>Deutsch</span></a></li><li class="interlanguage-link interwiki-el mw-list-item"><a href="https://el.wikipedia.org/wiki/%CE%98%CF%85%CE%BC%CF%8C%CE%BB%CE%B7" title="Θυμόλη – Greek" lang="el" hreflang="el" data-title="Θυμόλη" 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/Timol" title="Timol – Spanish" lang="es" hreflang="es" data-title="Timol" 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/Timolo" title="Timolo – Esperanto" lang="eo" hreflang="eo" data-title="Timolo" data-language-autonym="Esperanto" data-language-local-name="Esperanto" class="interlanguage-link-target"><span>Esperanto</span></a></li><li class="interlanguage-link interwiki-fa mw-list-item"><a href="https://fa.wikipedia.org/wiki/%D8%AA%DB%8C%D9%85%D9%88%D9%84" title="تیمول – Persian" lang="fa" hreflang="fa" data-title="تیمول" 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/Thymol" title="Thymol – French" lang="fr" hreflang="fr" data-title="Thymol" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target"><span>Français</span></a></li><li class="interlanguage-link interwiki-ko mw-list-item"><a href="https://ko.wikipedia.org/wiki/%ED%8B%B0%EB%AA%B0_(%ED%99%94%ED%95%A9%EB%AC%BC)" title="티몰 (화합물) – Korean" lang="ko" hreflang="ko" data-title="티몰 (화합물)" 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%B9%D5%AB%D5%B4%D5%B8%D5%AC" title="Թիմոլ – Armenian" lang="hy" hreflang="hy" data-title="Թիմոլ" 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%A5%E0%A4%BE%E0%A4%87%E0%A4%AE%E0%A5%8B%E0%A4%B2" title="थाइमोल – Hindi" lang="hi" hreflang="hi" data-title="थाइमोल" 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/Timol" title="Timol – Indonesian" lang="id" hreflang="id" data-title="Timol" 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/Timolo" title="Timolo – Italian" lang="it" hreflang="it" data-title="Timolo" 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%AA%D7%99%D7%9E%D7%95%D7%9C" title="תימול – Hebrew" lang="he" hreflang="he" data-title="תימול" data-language-autonym="עברית" data-language-local-name="Hebrew" class="interlanguage-link-target"><span>עברית</span></a></li><li class="interlanguage-link interwiki-ky mw-list-item"><a href="https://ky.wikipedia.org/wiki/%D0%A2%D0%B8%D0%BC%D0%BE%D0%BB" title="Тимол – Kyrgyz" lang="ky" hreflang="ky" data-title="Тимол" 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/Timols" title="Timols – Latvian" lang="lv" hreflang="lv" data-title="Timols" data-language-autonym="Latviešu" data-language-local-name="Latvian" class="interlanguage-link-target"><span>Latviešu</span></a></li><li class="interlanguage-link interwiki-hu mw-list-item"><a href="https://hu.wikipedia.org/wiki/Timol" title="Timol – Hungarian" lang="hu" hreflang="hu" data-title="Timol" 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%A4%E0%B5%88%E0%B4%AE%E0%B5%8B%E0%B5%BE" title="തൈമോൾ – Malayalam" lang="ml" hreflang="ml" data-title="തൈമോൾ" data-language-autonym="മലയാളം" data-language-local-name="Malayalam" class="interlanguage-link-target"><span>മലയാളം</span></a></li><li class="interlanguage-link interwiki-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/Thymol" title="Thymol – Dutch" lang="nl" hreflang="nl" data-title="Thymol" data-language-autonym="Nederlands" data-language-local-name="Dutch" class="interlanguage-link-target"><span>Nederlands</span></a></li><li class="interlanguage-link interwiki-ja mw-list-item"><a href="https://ja.wikipedia.org/wiki/%E3%83%81%E3%83%A2%E3%83%BC%E3%83%AB" title="チモール – Japanese" lang="ja" hreflang="ja" data-title="チモール" 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-pl mw-list-item"><a href="https://pl.wikipedia.org/wiki/Tymol" title="Tymol – Polish" lang="pl" hreflang="pl" data-title="Tymol" 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/Timol" title="Timol – Portuguese" lang="pt" hreflang="pt" data-title="Timol" 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/Timol" title="Timol – Romanian" lang="ro" hreflang="ro" data-title="Timol" data-language-autonym="Română" data-language-local-name="Romanian" class="interlanguage-link-target"><span>Română</span></a></li><li class="interlanguage-link interwiki-ru mw-list-item"><a href="https://ru.wikipedia.org/wiki/%D0%A2%D0%B8%D0%BC%D0%BE%D0%BB" title="Тимол – Russian" lang="ru" hreflang="ru" data-title="Тимол" data-language-autonym="Русский" data-language-local-name="Russian" class="interlanguage-link-target"><span>Русский</span></a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/Timol" title="Timol – Serbian" lang="sr" hreflang="sr" data-title="Timol" 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/Timol" title="Timol – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Timol" data-language-autonym="Srpskohrvatski / српскохрватски" data-language-local-name="Serbo-Croatian" class="interlanguage-link-target"><span>Srpskohrvatski / српскохрватски</span></a></li><li class="interlanguage-link interwiki-fi mw-list-item"><a href="https://fi.wikipedia.org/wiki/Tymoli" title="Tymoli – Finnish" lang="fi" hreflang="fi" data-title="Tymoli" 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/Tymol" title="Tymol – Swedish" lang="sv" hreflang="sv" data-title="Tymol" data-language-autonym="Svenska" data-language-local-name="Swedish" class="interlanguage-link-target"><span>Svenska</span></a></li><li class="interlanguage-link interwiki-uk mw-list-item"><a href="https://uk.wikipedia.org/wiki/%D0%A2%D0%B8%D0%BC%D0%BE%D0%BB" title="Тимол – Ukrainian" lang="uk" hreflang="uk" data-title="Тимол" data-language-autonym="Українська" data-language-local-name="Ukrainian" class="interlanguage-link-target"><span>Українська</span></a></li><li class="interlanguage-link interwiki-vi mw-list-item"><a href="https://vi.wikipedia.org/wiki/Thymol" title="Thymol – Vietnamese" lang="vi" hreflang="vi" data-title="Thymol" data-language-autonym="Tiếng Việt" data-language-local-name="Vietnamese" class="interlanguage-link-target"><span>Tiếng Việt</span></a></li><li class="interlanguage-link interwiki-zh mw-list-item"><a href="https://zh.wikipedia.org/wiki/%E7%99%BE%E9%87%8C%E9%85%9A" title="百里酚 – Chinese" lang="zh" hreflang="zh" data-title="百里酚" data-language-autonym="中文" data-language-local-name="Chinese" 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class="vector-pinnable-header-label">Appearance</div> <button class="vector-pinnable-header-toggle-button vector-pinnable-header-pin-button" data-event-name="pinnable-header.vector-appearance.pin">move to sidebar</button> <button class="vector-pinnable-header-toggle-button vector-pinnable-header-unpin-button" data-event-name="pinnable-header.vector-appearance.unpin">hide</button> </div> </div> </div> </nav> </div> </div> <div id="bodyContent" class="vector-body" aria-labelledby="firstHeading" data-mw-ve-target-container> <div class="vector-body-before-content"> <div class="mw-indicators"> </div> <div id="siteSub" class="noprint">From Wikipedia, the free encyclopedia</div> </div> <div id="contentSub"><div id="mw-content-subtitle"></div></div> <div id="mw-content-text" class="mw-body-content"><div class="mw-content-ltr mw-parser-output" lang="en" dir="ltr"><div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Chemical compound found in plants including thyme</div> <style data-mw-deduplicate="TemplateStyles:r1236090951">.mw-parser-output .hatnote{font-style:italic}.mw-parser-output div.hatnote{padding-left:1.6em;margin-bottom:0.5em}.mw-parser-output .hatnote i{font-style:normal}.mw-parser-output .hatnote+link+.hatnote{margin-top:-0.5em}@media print{body.ns-0 .mw-parser-output .hatnote{display:none!important}}</style><div role="note" class="hatnote navigation-not-searchable">Not to be confused with <a href="/wiki/Melitracen" title="Melitracen">Thymeol</a>, <a href="/wiki/Thymine" title="Thymine">Thymine</a>, or <a href="/wiki/Thiamine" title="Thiamine">Thiamine</a>.</div> <p> <style data-mw-deduplicate="TemplateStyles:r1268415487">.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%}@media screen{html.skin-theme-clientpref-night .mw-parser-output .ib-chembox figure:not(.skin-invert-image):not(.skin-invert):not(.bg-transparent){background:var(--background-color-inverted,#f8f9fa)}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .ib-chembox figure:not(.skin-invert-image):not(.skin-invert):not(.bg-transparent){background:var(--background-color-inverted,#f8f9fa)}}</style> </p> <table class="infobox ib-chembox"> <caption>Thymol </caption> <tbody><tr> <td colspan="2" style="text-align:center; padding:2px;"><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Thymol2.svg" class="mw-file-description" title="Thymol"><img alt="Thymol" src="//upload.wikimedia.org/wikipedia/commons/thumb/5/5d/Thymol2.svg/150px-Thymol2.svg.png" decoding="async" width="150" height="185" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/5/5d/Thymol2.svg/225px-Thymol2.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/5/5d/Thymol2.svg/300px-Thymol2.svg.png 2x" data-file-width="163" data-file-height="201" /></a><figcaption>Thymol</figcaption></figure> </td></tr> <tr> <td colspan="2" style="text-align:center; padding:2px;"><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Thymol3D.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/9/90/Thymol3D.png/220px-Thymol3D.png" decoding="async" width="220" height="138" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/9/90/Thymol3D.png/330px-Thymol3D.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/9/90/Thymol3D.png/440px-Thymol3D.png 2x" data-file-width="1920" data-file-height="1200" /></a><figcaption></figcaption></figure> </td></tr> <tr> <th colspan="2" style="background: #f8eaba;color:inherit; 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;">5-Methyl-2-(propan-2-yl)phenol<sup id="cite_ref-iupac2013_1-0" class="reference"><a href="#cite_note-iupac2013-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup></div></div> </td></tr> <tr> <td colspan="2" style="text-align:left;"><a href="/wiki/Chemical_nomenclature#Systematic_name" title="Chemical nomenclature">Systematic IUPAC name</a> <div style="max-width:22em; word-wrap:break-word; padding-left:1.7em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0; max-width:22em;">5-Methyl-2-(propan-2-yl)benzenol</div></div> </td></tr> <tr> <td colspan="2" style="text-align:left;">Other names <div style="max-width:22em; word-wrap:break-word; padding-left:1.7em;">2-Isopropyl-5-methylphenol, isopropyl-<i>m</i>-cresol, 1-methyl-3-hydroxy-4-isopropylbenzene, 3-methyl-6-isopropylphenol, 5-methyl-2-(1-methylethyl)phenol, 5-methyl-2-isopropyl-1-phenol, 5-methyl-2-isopropylphenol, 6-isopropyl-3-methylphenol, 6-isopropyl-<i>m</i>-cresol, Apiguard, NSC 11215, NSC 47821, NSC 49142, thyme camphor, <i>m</i>-thymol, and <i>p</i>-cymen-3-ol</div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba;color:inherit; 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=89-83-8">89-83-8</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=CC%28C%29c1ccc%28C%29cc1O">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=27607">CHEBI:27607</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/chembl/explore/compound/ChEMBL29411">ChEMBL29411</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.21105998.html">21105998</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><a href="/wiki/DrugBank" title="DrugBank">DrugBank</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><span title="www.drugbank.ca"><a rel="nofollow" class="external text" href="https://www.drugbank.ca/drugs/DB02513">DB02513</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/100.001.768">100.001.768</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q408883#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>201-944-8</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=2499">2499</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/D01039">D01039</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/6989">6989</a></span></li></ul></div> </td></tr> <tr> <td><a href="/wiki/Unique_Ingredient_Identifier" title="Unique Ingredient Identifier">UNII</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><span title="precision.fda.gov"><a rel="nofollow" class="external text" href="https://precision.fda.gov/uniisearch/srs/unii/3J50XA376E">3J50XA376E</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/CompTox_Chemicals_Dashboard" title="CompTox Chemicals Dashboard">CompTox Dashboard</a> <span style="font-weight:normal">(<abbr title="U.S. Environmental Protection Agency">EPA</abbr>)</span></div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><span title="comptox.epa.gov"><a rel="nofollow" class="external text" href="https://comptox.epa.gov/dashboard/chemical/details/DTXSID6034972">DTXSID6034972</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q408883#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;"><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/C10H14O/c1-7(2)9-5-4-8(3)6-10(9)11/h4-7,11H,1-3H3<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: MGSRCZKZVOBKFT-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/C10H14O/c1-7(2)9-5-4-8(3)6-10(9)11/h4-7,11H,1-3H3</div><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">Key: MGSRCZKZVOBKFT-UHFFFAOYAS</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;"><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%;">CC(C)c1ccc(C)cc1O</div></li></ul> </div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba;color:inherit; 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>10</sub><span title="Hydrogen">H</span><sub>14</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="7002150221000000000♠"></span>150.221</span> g·mol<sup>−1</sup>   </td></tr> <tr> <td><a href="/wiki/Density" title="Density">Density</a> </td> <td>0.96 g/cm<sup>3</sup> </td></tr> <tr> <td><a href="/wiki/Melting_point" title="Melting point">Melting point</a> </td> <td>49 to 51 °C (120 to 124 °F; 322 to 324 K) </td></tr> <tr> <td><a href="/wiki/Boiling_point" title="Boiling point">Boiling point</a> </td> <td>232 °C (450 °F; 505 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>0.9 g/L (20 °C)<sup id="cite_ref-2" class="reference"><a href="#cite_note-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Refractive_index" title="Refractive index">Refractive index</a> (<i>n</i><sub>D</sub>)</div> </td> <td>1.5208<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> </td></tr> <tr> <th colspan="2" style="background: #f8eaba;color:inherit; text-align: center;">Pharmacology </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Anatomical_Therapeutic_Chemical_Classification_System#ATCvet" title="Anatomical Therapeutic Chemical Classification System">ATCvet code</a></div> </td> <td><a href="/wiki/ATC_code_P53" class="mw-redirect" title="ATC code P53">QP53AX22</a> (<span title="www.whocc.no/atcvet"><a rel="nofollow" class="external text" href="https://www.whocc.no/atcvet/atcvet_index/?code=QP53AX22">WHO</a></span>)  </td></tr> <tr> <th colspan="2" style="background: #f8eaba;color:inherit; text-align: center;">Hazards </th></tr> <tr> <td colspan="2" style="text-align:left; background-color:#eaeaea;color:inherit;"><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-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-exclam.svg" class="mw-file-description" title="GHS07: Exclamation mark"><img alt="GHS07: Exclamation mark" src="//upload.wikimedia.org/wikipedia/commons/thumb/c/c3/GHS-pictogram-exclam.svg/50px-GHS-pictogram-exclam.svg.png" decoding="async" width="50" height="50" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/c/c3/GHS-pictogram-exclam.svg/75px-GHS-pictogram-exclam.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/c/c3/GHS-pictogram-exclam.svg/100px-GHS-pictogram-exclam.svg.png 2x" data-file-width="512" data-file-height="512" /></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>Warning</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="H302: Harmful if swallowed">H302</abbr>, <abbr class="abbr" title="H314: Causes severe skin burns and eye damage">H314</abbr>, <abbr class="abbr" title="H411: Toxic to aquatic life with long lasting effects">H411</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="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="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="P301+P312: IF SWALLOWED: Call a POISON CENTER or doctor/physician if you feel unwell.">P301+P312</abbr>, <abbr class="abbr" title="P301+P330+P331: IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.">P301+P330+P331</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="P321: Specific treatment (see ... on this label).">P321</abbr>, <abbr class="abbr" title="P330: Rinse mouth.">P330</abbr>, <abbr class="abbr" title="P363: Wash contaminated clothing before reuse.">P363</abbr>, <abbr class="abbr" title="P391: Collect spillage.">P391</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 colspan="2" style="text-align:left; background:#f8eaba; color:inherit; 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=470609679&page2=Thymol">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>Thymol</b> (also known as <b>2-isopropyl-5-methylphenol</b>, IPMP), <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">C<sub class="template-chem2-sub">10</sub>H<sub class="template-chem2-sub">14</sub>O</span>, is a natural <a href="/wiki/Monoterpene" title="Monoterpene">monoterpenoid</a> <a href="/wiki/Phenols" title="Phenols">phenol</a> derivative of <a href="/wiki/P-Cymene" title="P-Cymene"><i>p</i>-Cymene</a>, <a href="/wiki/Isomer" title="Isomer">isomeric</a> with <a href="/wiki/Carvacrol" title="Carvacrol">carvacrol</a>. It occurs naturally in the oil of <a href="/wiki/Thyme" title="Thyme">thyme</a>, and it is <a href="/wiki/Liquid%E2%80%93liquid_extraction" title="Liquid–liquid extraction">extracted</a> from <i><a href="/wiki/Thymus_vulgaris" title="Thymus vulgaris">Thymus vulgaris</a></i> (common thyme), <a href="/wiki/Ajwain" title="Ajwain">ajwain</a>,<sup id="cite_ref-4" class="reference"><a href="#cite_note-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> and various other plants as a white <a href="/wiki/Crystal" title="Crystal">crystalline</a> substance of a pleasant <a href="/wiki/Aromaticity" title="Aromaticity">aromatic</a> <a href="/wiki/Odor" title="Odor">odor</a> and strong <a href="/wiki/Antiseptic" title="Antiseptic">antiseptic</a> <a href="/wiki/Property" title="Property">properties</a>. Thymol also provides the distinctive, strong flavor of the <a href="/wiki/Herb" title="Herb">culinary herb</a> thyme, also produced from <i>T. vulgaris</i>. Thymol is only slightly <a href="/wiki/Solubility" title="Solubility">soluble</a> in water at neutral <a href="/wiki/PH" title="PH">pH</a>, but it is extremely soluble in <a href="/wiki/Alcohol_(chemistry)" title="Alcohol (chemistry)">alcohols</a> and other organic solvents. It is also soluble in strongly <a href="/wiki/Alkali" title="Alkali">alkaline</a> aqueous solutions due to <a href="/wiki/Deprotonation" title="Deprotonation">deprotonation</a> of the <a href="/wiki/Phenol" title="Phenol">phenol</a>. Its dissociation constant (<a href="/wiki/PKa" class="mw-redirect" title="PKa">p<i>K</i><sub>a</sub></a>) is <span class="nowrap"><span data-sort-value="7001105900000000000♠"></span>10.59<span style="margin-left:0.3em;margin-right:0.15em;">±</span>0.10</span>.<sup id="cite_ref-5" class="reference"><a href="#cite_note-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> Thymol absorbs maximum <a href="/wiki/Ultraviolet" title="Ultraviolet">UV</a> radiation at 274 nm.<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> </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Chemical_synthesis">Chemical synthesis</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Thymol&action=edit&section=1" title="Edit section: Chemical synthesis"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Thymol is produced by the <a href="/wiki/Alkylation" title="Alkylation">alkylation</a> of <a href="/wiki/M-Cresol" title="M-Cresol"><i>m</i>-cresol</a> and <a href="/wiki/Propene" class="mw-redirect" title="Propene">propene</a>:<sup id="cite_ref-7" class="reference"><a href="#cite_note-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-8" class="reference"><a href="#cite_note-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> </p> <dl><dd><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410" /><span class="chemf nowrap">CH<sub class="template-chem2-sub">3</sub>C<sub class="template-chem2-sub">6</sub>H<sub class="template-chem2-sub">4</sub>OH + CH<sub class="template-chem2-sub">2</sub>CHCH<sub class="template-chem2-sub">3</sub> → ((CH<sub class="template-chem2-sub">3</sub>)<sub class="template-chem2-sub">2</sub>CH)CH<sub class="template-chem2-sub">3</sub>C<sub class="template-chem2-sub">6</sub>H<sub class="template-chem2-sub">3</sub>OH</span></dd></dl> <p>A predicted method of biosynthesis of thymol in thyme and oregano begins with the cyclization of geranyl diphosphate by TvTPS2 to γ-terpinene. Oxidation by a <a href="/wiki/Cytochrome_P450" title="Cytochrome P450">cytochrome P450</a> in the CYP71D subfamily creates a <a href="/wiki/Dienol" class="mw-redirect" title="Dienol">dienol</a> intermediate, which is then converted into a ketone by short-chain dehydrogenase. Lastly, <a href="/wiki/Keto-enol_tautomerization" class="mw-redirect" title="Keto-enol tautomerization">keto-enol tautomerization</a> gives thymol. </p> <figure class="mw-halign-center" typeof="mw:File/Thumb"><a href="/wiki/File:Thymol_biosynthesis.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/f/f7/Thymol_biosynthesis.svg/800px-Thymol_biosynthesis.svg.png" decoding="async" width="800" height="99" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/f/f7/Thymol_biosynthesis.svg/1200px-Thymol_biosynthesis.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/f/f7/Thymol_biosynthesis.svg/1600px-Thymol_biosynthesis.svg.png 2x" data-file-width="1060" data-file-height="131" /></a><figcaption>Predicted biosynthesis of thymol in thyme and oregano. Reconstruction of figure 4 in Krause et. al. (2021).<sup id="cite_ref-r505_9-0" class="reference"><a href="#cite_note-r505-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup></figcaption></figure> <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=Thymol&action=edit&section=2" title="Edit section: History"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><a href="/wiki/Ancient_Egypt" title="Ancient Egypt">Ancient Egyptians</a> used thyme for <a href="/wiki/Embalming" title="Embalming">embalming</a>.<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> The <a href="/wiki/Ancient_Greece" title="Ancient Greece">ancient Greeks</a> used it in their baths and burned it as <a href="/wiki/Incense" title="Incense">incense</a> in their temples, believing it was a source of <a href="/wiki/Courage" title="Courage">courage</a>. The spread of thyme throughout Europe was thought to be due to the <a href="/wiki/Ancient_Rome" title="Ancient Rome">Romans</a>, as they used it to purify their rooms and to "give an aromatic flavour to cheese and liqueurs".<sup id="cite_ref-Maud_11-0" class="reference"><a href="#cite_note-Maud-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> In the European <a href="/wiki/Middle_Ages" title="Middle Ages">Middle Ages</a>, the herb was placed beneath pillows to aid sleep and ward off nightmares.<sup id="cite_ref-Huxley_12-0" class="reference"><a href="#cite_note-Huxley-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup> In this period, women also often gave <a href="/wiki/Knight" title="Knight">knights</a> and warriors gifts that included thyme leaves, because it was believed to bring courage to the bearer. Thyme was also used as incense and placed on <a href="/wiki/Coffin" title="Coffin">coffins</a> during <a href="/wiki/Funerals" class="mw-redirect" title="Funerals">funerals</a>, because it was supposed to ensure passage into the next life.<sup id="cite_ref-13" class="reference"><a href="#cite_note-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup> </p><p>The bee balms <i><a href="/wiki/Monarda_fistulosa" title="Monarda fistulosa">Monarda fistulosa</a></i> and <i><a href="/wiki/Monarda_didyma" title="Monarda didyma">Monarda didyma</a></i>, North American wildflowers, are natural sources of thymol. The <a href="/wiki/Blackfoot" class="mw-redirect" title="Blackfoot">Blackfoot</a> Native Americans recognized these plants' strong <a href="/wiki/Antiseptic" title="Antiseptic">antiseptic</a> action and used <a href="/wiki/Poultice" title="Poultice">poultices</a> of the plants for skin <a href="/wiki/Infection" title="Infection">infections</a> and minor <a href="/wiki/Wound" title="Wound">wounds</a>. A <a href="/wiki/Tisane" class="mw-redirect" title="Tisane">tisane</a> made from them was also used to treat mouth and throat <a href="/wiki/Infection" title="Infection">infections</a> caused by dental <a href="/wiki/Caries" class="mw-redirect" title="Caries">caries</a> and <a href="/wiki/Gingivitis" title="Gingivitis">gingivitis</a>.<sup id="cite_ref-14" class="reference"><a href="#cite_note-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup> </p><p>Thymol was first isolated by German chemist <a href="/wiki/Caspar_Neumann_(chemist)" title="Caspar Neumann (chemist)">Caspar Neumann</a> in 1719.<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> In 1853, French chemist Alexandre Lallemand<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> (1816-1886) named thymol and determined its empirical formula.<sup id="cite_ref-17" class="reference"><a href="#cite_note-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup> <a href="/wiki/Antiseptic" title="Antiseptic">Antiseptic</a> properties of thymol were discovered in 1875,<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> and it was first synthesized by Swedish chemist Oskar Widman<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> (1852-1930) in 1882.<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> </p> <div class="mw-heading mw-heading2"><h2 id="Extraction">Extraction</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Thymol&action=edit&section=3" title="Edit section: Extraction"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The conventional method of <a href="/wiki/Extract" title="Extract">extracting</a> is <a href="/wiki/Hydrodistillation" class="mw-redirect" title="Hydrodistillation">hydro-distillation</a> (HD), but can also be extracted with <a href="/wiki/Solvent" title="Solvent">solvent</a>-free <a href="/wiki/Microwave" title="Microwave">microwave</a> extraction (SFME). In 30 minutes, SFME yields similar amounts of thymol with more oxygenated compounds than 4.5 hours of hydro-distillation at atmospheric pressures without the need for solvent.<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> </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=Thymol&action=edit&section=4" title="Edit section: Uses"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure class="mw-default-size mw-halign-right" typeof="mw:File/Thumb"><a href="/wiki/File:Thymolum_by_Danny_S._-_001.JPG" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/6/6c/Thymolum_by_Danny_S._-_001.JPG/250px-Thymolum_by_Danny_S._-_001.JPG" decoding="async" width="220" height="165" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/6c/Thymolum_by_Danny_S._-_001.JPG/330px-Thymolum_by_Danny_S._-_001.JPG 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/6c/Thymolum_by_Danny_S._-_001.JPG/500px-Thymolum_by_Danny_S._-_001.JPG 2x" data-file-width="1280" data-file-height="960" /></a><figcaption>Thymol</figcaption></figure> <p>Thymol during the 1910s was the treatment of choice for <a href="/wiki/Hookworm_infection" title="Hookworm infection">hookworm infection</a> in the United States.<sup id="cite_ref-22" class="reference"><a href="#cite_note-22"><span class="cite-bracket">[</span>22<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Rosenau1913_23-0" class="reference"><a href="#cite_note-Rosenau1913-23"><span class="cite-bracket">[</span>23<span class="cite-bracket">]</span></a></sup> People of the Middle East continue to use <a href="/wiki/Za%27atar" title="Za'atar">za'atar</a>, a delicacy made with large amounts of thyme, to reduce and eliminate internal parasites.<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> It is also used as a <a href="/wiki/Preservative" title="Preservative">preservative</a> in <a href="/wiki/Halothane" title="Halothane">halothane</a>, an <a href="/wiki/Anaesthetic" class="mw-redirect" title="Anaesthetic">anaesthetic</a>, and as an antiseptic in mouthwash. When used to reduce plaque and gingivitis, thymol has been found to be more effective when used in combination with <a href="/wiki/Chlorhexidine" title="Chlorhexidine">chlorhexidine</a> than when used purely by itself.<sup id="cite_ref-25" class="reference"><a href="#cite_note-25"><span class="cite-bracket">[</span>25<span class="cite-bracket">]</span></a></sup> Thymol is also the active antiseptic ingredient in some toothpastes, such as <a href="/wiki/Johnson_%26_Johnson" title="Johnson & Johnson">Johnson & Johnson</a>'s <a href="/wiki/Euthymol" title="Euthymol">Euthymol</a>. Thymol has been used to successfully control <a href="/wiki/Varroa_mite" class="mw-redirect" title="Varroa mite">varroa mites</a> and prevent fermentation and the growth of <a href="/wiki/Mold_(fungus)" class="mw-redirect" title="Mold (fungus)">mold</a> in <a href="/wiki/Bees" class="mw-redirect" title="Bees">bee colonies</a>.<sup id="cite_ref-bees_26-0" class="reference"><a href="#cite_note-bees-26"><span class="cite-bracket">[</span>26<span class="cite-bracket">]</span></a></sup> Thymol is also used as a rapidly degrading, non-persisting <a href="/wiki/Pesticide" title="Pesticide">pesticides</a><sup id="cite_ref-J._Coats_2008_27-0" class="reference"><a href="#cite_note-J._Coats_2008-27"><span class="cite-bracket">[</span>27<span class="cite-bracket">]</span></a></sup> such as insecticides and fungicides which are leveraged in plant care products, where its environmentally friendly, rapid degradation ensures it doesn’t leave persistent residues while effectively controlling pests and fungal issues.<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> Thymol can also be used as a medical disinfectant and general purpose <a href="/wiki/Disinfectant" title="Disinfectant">disinfectant</a>.<sup id="cite_ref-29" class="reference"><a href="#cite_note-29"><span class="cite-bracket">[</span>29<span class="cite-bracket">]</span></a></sup> Thymol is also used in the production of <a href="/wiki/Menthol" title="Menthol">menthol</a> through the hydrogenation of the aromatic ring.<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> </p> <div class="mw-heading mw-heading2"><h2 id="List_of_plants_that_contain_thymol">List of plants that contain thymol</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Thymol&action=edit&section=5" title="Edit section: List of plants that contain thymol"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><i><a href="/wiki/Illicium_verum" title="Illicium verum">Illicium verum</a></i></li> <li><i><a href="/wiki/Euphrasia_rostkoviana" class="mw-redirect" title="Euphrasia rostkoviana">Euphrasia rostkoviana</a></i><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></li> <li><i><a href="/wiki/Lagoecia_cuminoides" class="mw-redirect" title="Lagoecia cuminoides">Lagoecia cuminoides</a></i><sup id="cite_ref-32" class="reference"><a href="#cite_note-32"><span class="cite-bracket">[</span>32<span class="cite-bracket">]</span></a></sup></li> <li><i><a href="/wiki/Monarda_didyma" title="Monarda didyma">Monarda didyma</a></i><sup id="cite_ref-33" class="reference"><a href="#cite_note-33"><span class="cite-bracket">[</span>33<span class="cite-bracket">]</span></a></sup></li> <li><i><a href="/wiki/Monarda_fistulosa" title="Monarda fistulosa">Monarda fistulosa</a></i><sup id="cite_ref-34" class="reference"><a href="#cite_note-34"><span class="cite-bracket">[</span>34<span class="cite-bracket">]</span></a></sup></li> <li><i><a href="/wiki/Mosla" title="Mosla">Mosla chinensis</a></i></li> <li><a href="/wiki/Ocimum_gratissimum" title="Ocimum gratissimum"><i>Ocimum gratissimum</i> L</a>.<sup id="cite_ref-35" class="reference"><a href="#cite_note-35"><span class="cite-bracket">[</span>35<span class="cite-bracket">]</span></a></sup></li> <li><i><a href="/w/index.php?title=Origanum_compactum&action=edit&redlink=1" class="new" title="Origanum compactum (page does not exist)">Origanum compactum</a></i><sup id="cite_ref-ccaa_36-0" class="reference"><a href="#cite_note-ccaa-36"><span class="cite-bracket">[</span>36<span class="cite-bracket">]</span></a></sup></li> <li><i><a href="/wiki/Origanum_dictamnus" title="Origanum dictamnus">Origanum dictamnus</a></i><sup id="cite_ref-lict_37-0" class="reference"><a href="#cite_note-lict-37"><span class="cite-bracket">[</span>37<span class="cite-bracket">]</span></a></sup></li> <li><i><a href="/wiki/Origanum_onites" title="Origanum onites">Origanum onites</a></i><sup id="cite_ref-ihte_38-0" class="reference"><a href="#cite_note-ihte-38"><span class="cite-bracket">[</span>38<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-caae_39-0" class="reference"><a href="#cite_note-caae-39"><span class="cite-bracket">[</span>39<span class="cite-bracket">]</span></a></sup></li> <li><i><a href="/wiki/Origanum_vulgare" class="mw-redirect" title="Origanum vulgare">Origanum vulgare</a></i><sup id="cite_ref-teeo_40-0" class="reference"><a href="#cite_note-teeo-40"><span class="cite-bracket">[</span>40<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-coeo_41-0" class="reference"><a href="#cite_note-coeo-41"><span class="cite-bracket">[</span>41<span class="cite-bracket">]</span></a></sup></li> <li><i><a href="/wiki/Satureja_hortensis" class="mw-redirect" title="Satureja hortensis">Satureja hortensis</a></i></li> <li><i><a href="/wiki/Satureja_thymbra" title="Satureja thymbra">Satureja thymbra</a></i></li> <li><i><a href="/w/index.php?title=Thymus_glandulosus&action=edit&redlink=1" class="new" title="Thymus glandulosus (page does not exist)">Thymus glandulosus</a></i><sup id="cite_ref-ccaa_36-1" class="reference"><a href="#cite_note-ccaa-36"><span class="cite-bracket">[</span>36<span class="cite-bracket">]</span></a></sup></li> <li><i><a href="/wiki/Thymus_hyemalis" title="Thymus hyemalis">Thymus hyemalis</a></i><sup id="cite_ref-apth_42-0" class="reference"><a href="#cite_note-apth-42"><span class="cite-bracket">[</span>42<span class="cite-bracket">]</span></a></sup></li> <li><i><a href="/wiki/Thymus_serpyllum" title="Thymus serpyllum">Thymus serpyllum</a></i></li> <li><i><a href="/wiki/Thymus_praecox" title="Thymus praecox">Thymus praecox</a></i></li> <li><i><a href="/wiki/Thymus_vulgaris" title="Thymus vulgaris">Thymus vulgaris</a></i><sup id="cite_ref-apth_42-1" class="reference"><a href="#cite_note-apth-42"><span class="cite-bracket">[</span>42<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-ivcb_43-0" class="reference"><a href="#cite_note-ivcb-43"><span class="cite-bracket">[</span>43<span class="cite-bracket">]</span></a></sup></li> <li><i><a href="/wiki/Thymus_zygis" title="Thymus zygis">Thymus zygis</a></i><sup id="cite_ref-scet_44-0" class="reference"><a href="#cite_note-scet-44"><span class="cite-bracket">[</span>44<span class="cite-bracket">]</span></a></sup></li> <li><i><a href="/wiki/Trachyspermum_ammi" class="mw-redirect" title="Trachyspermum ammi">Trachyspermum ammi</a></i></li></ul> <div class="mw-heading mw-heading2"><h2 id="Toxicology_and_environmental_impacts">Toxicology and environmental impacts</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Thymol&action=edit&section=6" title="Edit section: Toxicology and environmental impacts"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>In 2009, the <a href="/wiki/United_States_Environmental_Protection_Agency" title="United States Environmental Protection Agency">U.S. Environmental Protection Agency (EPA)</a> reviewed the research literature on the toxicology and environmental impact of thymol and concluded that "thymol has minimal potential toxicity and poses minimal risk".<sup id="cite_ref-45" class="reference"><a href="#cite_note-45"><span class="cite-bracket">[</span>45<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Environmental_breakdown_and_use_as_a_pesticide">Environmental breakdown and use as a pesticide</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Thymol&action=edit&section=7" title="Edit section: Environmental breakdown and use as a pesticide"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Studies have shown that hydrocarbon <a href="/wiki/Monoterpenes" class="mw-redirect" title="Monoterpenes">monoterpenes</a> and thymol in particular degrade rapidly (DT<sub>50</sub> 16 days in water, 5 days in soil<sup id="cite_ref-J._Coats_2008_27-1" class="reference"><a href="#cite_note-J._Coats_2008-27"><span class="cite-bracket">[</span>27<span class="cite-bracket">]</span></a></sup>) in the environment and are, thus, low risks because of rapid dissipation and low bound residues,<sup id="cite_ref-J._Coats_2008_27-2" class="reference"><a href="#cite_note-J._Coats_2008-27"><span class="cite-bracket">[</span>27<span class="cite-bracket">]</span></a></sup> supporting the use of thymol as a pesticide agent that offers a safe alternative to other more persistent chemical pesticides that can be dispersed in runoff and produce subsequent contamination. Though, there has been recent research into sustained released systems for botanically derived pesticides, such as using natural <a href="/wiki/Polysaccharide" title="Polysaccharide">polysaccharides</a> which would be biodegradable and biocompatible.<sup id="cite_ref-46" class="reference"><a href="#cite_note-46"><span class="cite-bracket">[</span>46<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Compendial_status">Compendial status</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Thymol&action=edit&section=8" title="Edit section: Compendial status"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a href="/wiki/British_Pharmacopoeia" title="British Pharmacopoeia">British Pharmacopoeia</a><sup id="cite_ref-ib29_47-0" class="reference"><a href="#cite_note-ib29-47"><span class="cite-bracket">[</span>47<span class="cite-bracket">]</span></a></sup></li> <li><a href="/wiki/Japanese_Pharmacopoeia" title="Japanese Pharmacopoeia">Japanese Pharmacopoeia</a><sup id="cite_ref-jp15_48-0" class="reference"><a href="#cite_note-jp15-48"><span class="cite-bracket">[</span>48<span class="cite-bracket">]</span></a></sup></li></ul> <div class="mw-heading mw-heading2"><h2 id="See_also">See also</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Thymol&action=edit&section=9" title="Edit section: See also"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a href="/wiki/Thymoquinone" title="Thymoquinone">Thymoquinone</a></li> <li><i><a href="/wiki/Nigella_sativa" title="Nigella sativa">Nigella sativa</a></i></li> <li><a href="/wiki/Bromothymol" class="mw-redirect" title="Bromothymol">Bromothymol</a></li></ul> <div class="mw-heading mw-heading2"><h2 id="Notes_and_references">Notes and references</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Thymol&action=edit&section=10" title="Edit section: Notes and references"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1239543626">.mw-parser-output .reflist{margin-bottom:0.5em;list-style-type:decimal}@media screen{.mw-parser-output .reflist{font-size:90%}}.mw-parser-output .reflist .references{font-size:100%;margin-bottom:0;list-style-type:inherit}.mw-parser-output .reflist-columns-2{column-width:30em}.mw-parser-output .reflist-columns-3{column-width:25em}.mw-parser-output .reflist-columns{margin-top:0.3em}.mw-parser-output .reflist-columns ol{margin-top:0}.mw-parser-output .reflist-columns li{page-break-inside:avoid;break-inside:avoid-column}.mw-parser-output .reflist-upper-alpha{list-style-type:upper-alpha}.mw-parser-output .reflist-upper-roman{list-style-type:upper-roman}.mw-parser-output .reflist-lower-alpha{list-style-type:lower-alpha}.mw-parser-output .reflist-lower-greek{list-style-type:lower-greek}.mw-parser-output .reflist-lower-roman{list-style-type:lower-roman}</style><div class="reflist reflist-columns references-column-width" style="column-width: 30em;"> <ol class="references"> <li id="cite_note-iupac2013-1"><span class="mw-cite-backlink"><b><a href="#cite_ref-iupac2013_1-0">^</a></b></span> <span class="reference-text"><style data-mw-deduplicate="TemplateStyles:r1238218222">.mw-parser-output cite.citation{font-style:inherit;word-wrap:break-word}.mw-parser-output .citation q{quotes:"\"""\"""'""'"}.mw-parser-output .citation:target{background-color:rgba(0,127,255,0.133)}.mw-parser-output .id-lock-free.id-lock-free a{background:url("//upload.wikimedia.org/wikipedia/commons/6/65/Lock-green.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-limited.id-lock-limited a,.mw-parser-output .id-lock-registration.id-lock-registration a{background:url("//upload.wikimedia.org/wikipedia/commons/d/d6/Lock-gray-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-subscription.id-lock-subscription a{background:url("//upload.wikimedia.org/wikipedia/commons/a/aa/Lock-red-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .cs1-ws-icon a{background:url("//upload.wikimedia.org/wikipedia/commons/4/4c/Wikisource-logo.svg")right 0.1em center/12px no-repeat}body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-free a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-limited a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-registration a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-subscription a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .cs1-ws-icon a{background-size:contain;padding:0 1em 0 0}.mw-parser-output .cs1-code{color:inherit;background:inherit;border:none;padding:inherit}.mw-parser-output .cs1-hidden-error{display:none;color:var(--color-error,#d33)}.mw-parser-output .cs1-visible-error{color:var(--color-error,#d33)}.mw-parser-output .cs1-maint{display:none;color:#085;margin-left:0.3em}.mw-parser-output .cs1-kern-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right{padding-right:0.2em}.mw-parser-output .citation .mw-selflink{font-weight:inherit}@media screen{.mw-parser-output .cs1-format{font-size:95%}html.skin-theme-clientpref-night .mw-parser-output .cs1-maint{color:#18911f}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .cs1-maint{color:#18911f}}</style><cite class="citation book cs1">"Front Matter". <i>Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book)</i>. Cambridge: The <a href="/wiki/Royal_Society_of_Chemistry" title="Royal Society of Chemistry">Royal Society of Chemistry</a>. 2014. p. 691. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1039%2F9781849733069-FP001">10.1039/9781849733069-FP001</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-85404-182-4" title="Special:BookSources/978-0-85404-182-4"><bdi>978-0-85404-182-4</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Front+Matter&rft.btitle=Nomenclature+of+Organic+Chemistry+%3A+IUPAC+Recommendations+and+Preferred+Names+2013+%28Blue+Book%29&rft.place=Cambridge&rft.pages=691&rft.pub=The+Royal+Society+of+Chemistry&rft.date=2014&rft_id=info%3Adoi%2F10.1039%2F9781849733069-FP001&rft.isbn=978-0-85404-182-4&rfr_id=info%3Asid%2Fen.wikipedia.org%3AThymol" class="Z3988"></span></span> </li> <li id="cite_note-2"><span class="mw-cite-backlink"><b><a href="#cite_ref-2">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/thymol#section=Solubility">"Thymol"</a>. PubChem<span class="reference-accessdate">. Retrieved <span class="nowrap">1 April</span> 2016</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=Thymol&rft.pub=PubChem&rft_id=https%3A%2F%2Fpubchem.ncbi.nlm.nih.gov%2Fcompound%2Fthymol%23section%3DSolubility&rfr_id=info%3Asid%2Fen.wikipedia.org%3AThymol" class="Z3988"></span></span> </li> <li id="cite_note-3"><span class="mw-cite-backlink"><b><a href="#cite_ref-3">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFMndzhoyan1940" class="citation journal cs1">Mndzhoyan, A. L. (1940). "Thymol from <i>Thymus kotschyanus</i>". <i>Sbornik Trudov Armyanskogo Filial. Akad. Nauk</i>. <b>1940</b>: <span class="nowrap">25–</span>28.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Sbornik+Trudov+Armyanskogo+Filial.+Akad.+Nauk.&rft.atitle=Thymol+from+Thymus+kotschyanus.&rft.volume=1940&rft.pages=%3Cspan+class%3D%22nowrap%22%3E25-%3C%2Fspan%3E28&rft.date=1940&rft.aulast=Mndzhoyan&rft.aufirst=A.+L.&rfr_id=info%3Asid%2Fen.wikipedia.org%3AThymol" class="Z3988"></span></span> </li> <li id="cite_note-4"><span class="mw-cite-backlink"><b><a href="#cite_ref-4">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFO'Connell,_John2019" class="citation book cs1">O'Connell, John (27 August 2019). <i>The book of spice : from anise to zedoary</i>. New York: Pegasus. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1681774459" title="Special:BookSources/978-1681774459"><bdi>978-1681774459</bdi></a>. <a href="/wiki/OCLC_(identifier)" class="mw-redirect" title="OCLC (identifier)">OCLC</a> <a rel="nofollow" class="external text" href="https://search.worldcat.org/oclc/959875923">959875923</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=The+book+of+spice+%3A+from+anise+to+zedoary&rft.place=New+York&rft.pub=Pegasus&rft.date=2019-08-27&rft_id=info%3Aoclcnum%2F959875923&rft.isbn=978-1681774459&rft.au=O%27Connell%2C+John&rfr_id=info%3Asid%2Fen.wikipedia.org%3AThymol" class="Z3988"></span></span> </li> <li id="cite_note-5"><span class="mw-cite-backlink"><b><a href="#cite_ref-5">^</a></b></span> <span class="reference-text">CAS Registry: Data obtained from SciFinder<sup class="noprint Inline-Template" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citing_sources#What_information_to_include" title="Wikipedia:Citing sources"><span title="A complete citation is needed. (August 2017)">full citation needed</span></a></i>]</sup></span> </li> <li id="cite_note-6"><span class="mw-cite-backlink"><b><a href="#cite_ref-6">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFNorwitzNataroKeliher1986" class="citation journal cs1">Norwitz, G.; Nataro, N.; Keliher, P. N. (1986). "Study of the Steam Distillation of Phenolic Compounds Using Ultraviolent Spectrometry". <i>Anal. Chem</i>. <b>58</b> (<span class="nowrap">639–</span>640): 641. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1021%2Fac00294a034">10.1021/ac00294a034</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Anal.+Chem.&rft.atitle=Study+of+the+Steam+Distillation+of+Phenolic+Compounds+Using+Ultraviolent+Spectrometry&rft.volume=58&rft.issue=%3Cspan+class%3D%22nowrap%22%3E639%E2%80%93%3C%2Fspan%3E640&rft.pages=641&rft.date=1986&rft_id=info%3Adoi%2F10.1021%2Fac00294a034&rft.aulast=Norwitz&rft.aufirst=G.&rft.au=Nataro%2C+N.&rft.au=Keliher%2C+P.+N.&rfr_id=info%3Asid%2Fen.wikipedia.org%3AThymol" class="Z3988"></span></span> </li> <li id="cite_note-7"><span class="mw-cite-backlink"><b><a href="#cite_ref-7">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFStrohSydelHahn1963" class="citation book cs1">Stroh, R.; Sydel, R.; Hahn, W. (1963). Foerst, Wilhelm (ed.). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=LG2J6i1sUAMC&pg=PA344"><i>Newer Methods of Preparative Organic Chemistry, Volume 2</i></a> (1st ed.). New York: Academic Press. p. 344. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/9780323150422" title="Special:BookSources/9780323150422"><bdi>9780323150422</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Newer+Methods+of+Preparative+Organic+Chemistry%2C+Volume+2&rft.place=New+York&rft.pages=344&rft.edition=1st&rft.pub=Academic+Press&rft.date=1963&rft.isbn=9780323150422&rft.aulast=Stroh&rft.aufirst=R.&rft.au=Sydel%2C+R.&rft.au=Hahn%2C+W.&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DLG2J6i1sUAMC%26pg%3DPA344&rfr_id=info%3Asid%2Fen.wikipedia.org%3AThymol" class="Z3988"></span></span> </li> <li id="cite_note-8"><span class="mw-cite-backlink"><b><a href="#cite_ref-8">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFFiegeVogesHamamotoUmemura2000" class="citation encyclopaedia cs1">Fiege, Helmut; Voges, Heinz-Werner; Hamamoto, Toshikazu; Umemura, Sumio; Iwata, Tadao; Miki, Hisaya; Fujita, Yasuhiro; Buysch, Hans-Josef; Garbe, Dorothea; Paulus, Wilfried (2000). "Phenol Derivatives". <i><a href="/wiki/Ullmann%27s_Encyclopedia_of_Industrial_Chemistry" title="Ullmann's Encyclopedia of Industrial Chemistry">Ullmann's Encyclopedia of Industrial Chemistry</a></i>. Weinheim: Wiley-VCH. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2F14356007.a19_313">10.1002/14356007.a19_313</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/3527306730" title="Special:BookSources/3527306730"><bdi>3527306730</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Phenol+Derivatives&rft.btitle=Ullmann%27s+Encyclopedia+of+Industrial+Chemistry&rft.place=Weinheim&rft.pub=Wiley-VCH&rft.date=2000&rft_id=info%3Adoi%2F10.1002%2F14356007.a19_313&rft.isbn=3527306730&rft.aulast=Fiege&rft.aufirst=Helmut&rft.au=Voges%2C+Heinz-Werner&rft.au=Hamamoto%2C+Toshikazu&rft.au=Umemura%2C+Sumio&rft.au=Iwata%2C+Tadao&rft.au=Miki%2C+Hisaya&rft.au=Fujita%2C+Yasuhiro&rft.au=Buysch%2C+Hans-Josef&rft.au=Garbe%2C+Dorothea&rft.au=Paulus%2C+Wilfried&rfr_id=info%3Asid%2Fen.wikipedia.org%3AThymol" class="Z3988"></span></span> </li> <li id="cite_note-r505-9"><span class="mw-cite-backlink"><b><a href="#cite_ref-r505_9-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFKrauseLiaoCrocollBoachon2021" class="citation journal cs1">Krause, Sandra T.; Liao, Pan; Crocoll, Christoph; Boachon, Benoît; Förster, Christiane; Leidecker, Franziska; Wiese, Natalie; Zhao, Dongyan; Wood, Joshua C.; Buell, C. Robin; Gershenzon, Jonathan; Dudareva, Natalia; Degenhardt, Jörg (28 December 2021). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8719858">"The biosynthesis of thymol, carvacrol, and thymohydroquinone in Lamiaceae proceeds via cytochrome P450s and a short-chain dehydrogenase"</a>. <i>Proceedings of the National Academy of Sciences</i>. <b>118</b> (52). <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1073%2Fpnas.2110092118">10.1073/pnas.2110092118</a>. <a href="/wiki/ISSN_(identifier)" class="mw-redirect" title="ISSN (identifier)">ISSN</a> <a rel="nofollow" class="external text" href="https://search.worldcat.org/issn/0027-8424">0027-8424</a>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8719858">8719858</a></span>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/34930840">34930840</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Proceedings+of+the+National+Academy+of+Sciences&rft.atitle=The+biosynthesis+of+thymol%2C+carvacrol%2C+and+thymohydroquinone+in+Lamiaceae+proceeds+via+cytochrome+P450s+and+a+short-chain+dehydrogenase&rft.volume=118&rft.issue=52&rft.date=2021-12-28&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC8719858%23id-name%3DPMC&rft.issn=0027-8424&rft_id=info%3Apmid%2F34930840&rft_id=info%3Adoi%2F10.1073%2Fpnas.2110092118&rft.aulast=Krause&rft.aufirst=Sandra+T.&rft.au=Liao%2C+Pan&rft.au=Crocoll%2C+Christoph&rft.au=Boachon%2C+Beno%C3%AEt&rft.au=F%C3%B6rster%2C+Christiane&rft.au=Leidecker%2C+Franziska&rft.au=Wiese%2C+Natalie&rft.au=Zhao%2C+Dongyan&rft.au=Wood%2C+Joshua+C.&rft.au=Buell%2C+C.+Robin&rft.au=Gershenzon%2C+Jonathan&rft.au=Dudareva%2C+Natalia&rft.au=Degenhardt%2C+J%C3%B6rg&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC8719858&rfr_id=info%3Asid%2Fen.wikipedia.org%3AThymol" class="Z3988"></span></span> </li> <li id="cite_note-10"><span class="mw-cite-backlink"><b><a href="#cite_ref-10">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite class="citation web cs1"><a rel="nofollow" class="external text" href="http://www.history.com/news/hungry-history/a-brief-history-of-thyme">"A Brief History of Thyme - Hungry History"</a>. <i>HISTORY.com</i>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20160613081647/http://www.history.com/news/hungry-history/a-brief-history-of-thyme">Archived</a> from the original on 13 June 2016<span class="reference-accessdate">. Retrieved <span class="nowrap">9 June</span> 2016</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=HISTORY.com&rft.atitle=A+Brief+History+of+Thyme+-+Hungry+History&rft_id=http%3A%2F%2Fwww.history.com%2Fnews%2Fhungry-history%2Fa-brief-history-of-thyme&rfr_id=info%3Asid%2Fen.wikipedia.org%3AThymol" class="Z3988"></span></span> </li> <li id="cite_note-Maud-11"><span class="mw-cite-backlink"><b><a href="#cite_ref-Maud_11-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFGrieve" class="citation web cs1">Grieve, Mrs. Maud. <a rel="nofollow" class="external text" href="http://botanical.com/botanical/mgmh/t/thygar16.html">"Thyme. A Modern Herbal"</a>. <i>botanical.com</i> (Hypertext version of the 1931 ed.). <a rel="nofollow" class="external text" href="http://archive.wikiwix.com/cache/20110223130247/http://botanical.com/botanical/mgmh/t/thygar16.html">Archived</a> from the original on 23 February 2011<span class="reference-accessdate">. Retrieved <span class="nowrap">9 February</span> 2008</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=botanical.com&rft.atitle=Thyme.+A+Modern+Herbal&rft.aulast=Grieve&rft.aufirst=Mrs.+Maud&rft_id=http%3A%2F%2Fbotanical.com%2Fbotanical%2Fmgmh%2Ft%2Fthygar16.html&rfr_id=info%3Asid%2Fen.wikipedia.org%3AThymol" class="Z3988"></span></span> </li> <li id="cite_note-Huxley-12"><span class="mw-cite-backlink"><b><a href="#cite_ref-Huxley_12-0">^</a></b></span> <span class="reference-text">Huxley, A., ed. (1992). <i>New RHS Dictionary of Gardening</i>. Macmillan.</span> </li> <li id="cite_note-13"><span class="mw-cite-backlink"><b><a href="#cite_ref-13">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite class="citation web cs1"><a rel="nofollow" class="external text" href="http://www.englishplants.co.uk/thyme.html">"Thyme (thymus)"</a>. <i>englishplants.co.uk</i>. The English Cottage Garden Nursery. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20060927050614/http://www.englishplants.co.uk/thyme.html">Archived</a> from the original on 27 September 2006.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=englishplants.co.uk&rft.atitle=Thyme+%28thymus%29&rft_id=http%3A%2F%2Fwww.englishplants.co.uk%2Fthyme.html&rfr_id=info%3Asid%2Fen.wikipedia.org%3AThymol" class="Z3988"></span></span> </li> <li id="cite_note-14"><span class="mw-cite-backlink"><b><a href="#cite_ref-14">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFTilford1997" class="citation book cs1">Tilford, Gregory L. (1997). <i>Edible and Medicinal Plants of the West</i>. Missoula, MT: Mountain Press Publishing. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-87842-359-0" title="Special:BookSources/978-0-87842-359-0"><bdi>978-0-87842-359-0</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Edible+and+Medicinal+Plants+of+the+West&rft.place=Missoula%2C+MT&rft.pub=Mountain+Press+Publishing&rft.date=1997&rft.isbn=978-0-87842-359-0&rft.aulast=Tilford&rft.aufirst=Gregory+L.&rfr_id=info%3Asid%2Fen.wikipedia.org%3AThymol" class="Z3988"></span></span> </li> <li id="cite_note-15"><span class="mw-cite-backlink"><b><a href="#cite_ref-15">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFNeuman1724" class="citation journal cs1">Neuman, Carolo (1724). <a rel="nofollow" class="external text" href="http://rstl.royalsocietypublishing.org/content/33/381-391/321.full.pdf+html">"De Camphora"</a>. <i>Philosophical Transactions of the Royal Society of London</i>. <b>33</b> (389): <span class="nowrap">321–</span>332. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://doi.org/10.1098%2Frstl.1724.0061">10.1098/rstl.1724.0061</a></span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Philosophical+Transactions+of+the+Royal+Society+of+London&rft.atitle=De+Camphora&rft.volume=33&rft.issue=389&rft.pages=%3Cspan+class%3D%22nowrap%22%3E321-%3C%2Fspan%3E332&rft.date=1724&rft_id=info%3Adoi%2F10.1098%2Frstl.1724.0061&rft.aulast=Neuman&rft.aufirst=Carolo&rft_id=http%3A%2F%2Frstl.royalsocietypublishing.org%2Fcontent%2F33%2F381-391%2F321.full.pdf%2Bhtml&rfr_id=info%3Asid%2Fen.wikipedia.org%3AThymol" class="Z3988"></span> On page 324, Neumann mentions that in 1719 he distilled some essential oils from various herbs. On page 326, he mentions that during these experiments, he obtained a crystalline substance from thyme oil, which he called "<i>Camphora Thymi</i>" (<a href="/wiki/Camphor" title="Camphor">camphor</a> of thyme). (Neumann gave the name "camphor" not only to the specific substance that today is called camphor but to any crystalline substance that precipitated from a volatile, fragrant oil from some plant.)</span> </li> <li id="cite_note-16"><span class="mw-cite-backlink"><b><a href="#cite_ref-16">^</a></b></span> <span class="reference-text">Marie-Étienne-Alexandre Lallemand (December 25, 1816 - March 16, 1886)</span> </li> <li id="cite_note-17"><span class="mw-cite-backlink"><b><a href="#cite_ref-17">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFLallemand1853" class="citation journal cs1 cs1-prop-foreign-lang-source">Lallemand, A. 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aria-labelledby="GABAA_receptor_positive_modulators746" style="padding:3px"><table class="nowraplinks mw-collapsible mw-collapsed navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374" /><style data-mw-deduplicate="TemplateStyles:r1239400231">.mw-parser-output .navbar{display:inline;font-size:88%;font-weight:normal}.mw-parser-output .navbar-collapse{float:left;text-align:left}.mw-parser-output .navbar-boxtext{word-spacing:0}.mw-parser-output .navbar ul{display:inline-block;white-space:nowrap;line-height:inherit}.mw-parser-output .navbar-brackets::before{margin-right:-0.125em;content:"[ "}.mw-parser-output .navbar-brackets::after{margin-left:-0.125em;content:" ]"}.mw-parser-output .navbar li{word-spacing:-0.125em}.mw-parser-output .navbar a>span,.mw-parser-output .navbar a>abbr{text-decoration:inherit}.mw-parser-output .navbar-mini abbr{font-variant:small-caps;border-bottom:none;text-decoration:none;cursor:inherit}.mw-parser-output .navbar-ct-full{font-size:114%;margin:0 7em}.mw-parser-output .navbar-ct-mini{font-size:114%;margin:0 4em}html.skin-theme-clientpref-night .mw-parser-output .navbar li a abbr{color:var(--color-base)!important}@media(prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .navbar li a abbr{color:var(--color-base)!important}}@media print{.mw-parser-output .navbar{display:none!important}}</style><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:GABAA_receptor_positive_modulators" title="Template:GABAA receptor positive modulators"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:GABAA_receptor_positive_modulators" title="Template talk:GABAA receptor positive modulators"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:GABAA_receptor_positive_modulators" title="Special:EditPage/Template:GABAA receptor positive modulators"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="GABAA_receptor_positive_modulators746" style="font-size:114%;margin:0 4em"><a href="/wiki/GABAA_receptor_positive_allosteric_modulator" title="GABAA receptor positive allosteric modulator"><abbr title="γ-Aminobutyric acid">GABA</abbr><sub>A</sub> receptor positive modulators</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align: center;"><a href="/wiki/Alcohol_(chemistry)" title="Alcohol (chemistry)">Alcohols</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/w/index.php?title=Brometone&action=edit&redlink=1" class="new" title="Brometone (page does not exist)">Brometone</a></li> <li><a href="/wiki/1-Butanol" title="1-Butanol">Butanol</a></li> <li><a href="/wiki/Chloralodol" title="Chloralodol">Chloralodol</a></li> <li><a href="/wiki/Chlorobutanol" title="Chlorobutanol">Chlorobutanol (cloretone)</a></li> <li><a href="/wiki/Alcohol_(drug)" title="Alcohol (drug)">Ethanol (alcohol)</a> (<a href="/wiki/Alcoholic_drink" class="mw-redirect" title="Alcoholic drink">alcoholic drink</a>)</li> <li><a href="/wiki/Ethchlorvynol" title="Ethchlorvynol">Ethchlorvynol</a></li> <li><a href="/wiki/Isobutanol" title="Isobutanol">Isobutanol</a></li> <li><a href="/wiki/Isopropanol" class="mw-redirect" title="Isopropanol">Isopropanol</a></li> <li><a href="/wiki/Menthol" title="Menthol">Menthol</a></li> <li><a href="/wiki/Methanol" title="Methanol">Methanol</a></li> <li><a href="/wiki/Methylpentynol" title="Methylpentynol">Methylpentynol</a></li> <li><a href="/wiki/1-Pentanol" title="1-Pentanol">Pentanol</a></li> <li><a href="/wiki/Petrichloral" title="Petrichloral">Petrichloral</a></li> <li><a href="/wiki/1-Propanol" title="1-Propanol">Propanol</a></li> <li><a href="/wiki/Tert-Butanol" class="mw-redirect" title="Tert-Butanol"><i>tert</i>-Butanol (2M2P)</a></li> <li><a href="/wiki/Tert-Pentanol" class="mw-redirect" title="Tert-Pentanol"><i>tert</i>-Pentanol (2M2B)</a></li> <li><a href="/wiki/Tribromoethanol" title="Tribromoethanol">Tribromoethanol</a></li> <li><a href="/wiki/Trichloroethanol" class="mw-redirect" title="Trichloroethanol">Trichloroethanol</a></li> <li><a href="/wiki/Triclofos" title="Triclofos">Triclofos</a></li> <li><a href="/wiki/Trifluoroethanol" class="mw-redirect" title="Trifluoroethanol">Trifluoroethanol</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align: center;"><a href="/wiki/Barbiturate" title="Barbiturate">Barbiturates</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/(-)-5-(1,3-Dimethylbutyl)-5-ethylbarbituric_acid" class="mw-redirect" title="(-)-5-(1,3-Dimethylbutyl)-5-ethylbarbituric acid">(-)-DMBB</a></li> <li><a href="/wiki/Allobarbital" title="Allobarbital">Allobarbital</a></li> <li><a href="/wiki/Alphenal" title="Alphenal">Alphenal</a></li> <li><a href="/wiki/Amobarbital" title="Amobarbital">Amobarbital</a></li> <li><a href="/wiki/Aprobarbital" title="Aprobarbital">Aprobarbital</a></li> <li><a href="/wiki/Barbexaclone" title="Barbexaclone">Barbexaclone</a></li> <li><a href="/wiki/Barbital" title="Barbital">Barbital</a></li> <li><a href="/wiki/Benzobarbital" title="Benzobarbital">Benzobarbital</a></li> <li><a href="/wiki/Benzylbutylbarbiturate" title="Benzylbutylbarbiturate">Benzylbutylbarbiturate</a></li> <li><a href="/wiki/Brallobarbital" title="Brallobarbital">Brallobarbital</a></li> <li><a href="/wiki/Brophebarbital" title="Brophebarbital">Brophebarbital</a></li> <li><a href="/wiki/Butabarbital" title="Butabarbital">Butabarbital/Secbutabarbital</a></li> <li><a href="/wiki/Butalbital" title="Butalbital">Butalbital</a></li> <li><a href="/wiki/Buthalital" title="Buthalital">Buthalital</a></li> <li><a href="/wiki/Butobarbital" title="Butobarbital">Butobarbital</a></li> <li><a href="/wiki/Butallylonal" title="Butallylonal">Butallylonal</a></li> <li><a href="/wiki/Carbubarb" title="Carbubarb">Carbubarb</a></li> <li><a href="/wiki/Crotylbarbital" title="Crotylbarbital">Crotylbarbital</a></li> <li><a href="/wiki/Cyclobarbital" title="Cyclobarbital">Cyclobarbital</a></li> <li><a href="/wiki/Cyclopentobarbital" title="Cyclopentobarbital">Cyclopentobarbital</a></li> <li><a href="/wiki/Difebarbamate" title="Difebarbamate">Difebarbamate</a></li> <li><a href="/wiki/Enallylpropymal" title="Enallylpropymal">Enallylpropymal</a></li> <li><a href="/wiki/Ethallobarbital" title="Ethallobarbital">Ethallobarbital</a></li> <li><a href="/wiki/Eterobarb" title="Eterobarb">Eterobarb</a></li> <li><a href="/wiki/Febarbamate" title="Febarbamate">Febarbamate</a></li> <li><a href="/wiki/Heptabarb" title="Heptabarb">Heptabarb</a></li> <li><a href="/wiki/Heptobarbital" title="Heptobarbital">Heptobarbital</a></li> <li><a href="/wiki/Hexethal" title="Hexethal">Hexethal</a></li> <li><a href="/wiki/Hexobarbital" title="Hexobarbital">Hexobarbital</a></li> <li><a href="/wiki/Metharbital" title="Metharbital">Metharbital</a></li> <li><a href="/wiki/Methitural" title="Methitural">Methitural</a></li> <li><a href="/wiki/Methohexital" title="Methohexital">Methohexital</a></li> <li><a href="/wiki/Methylphenobarbital" title="Methylphenobarbital">Methylphenobarbital</a></li> <li><a href="/wiki/Narcobarbital" title="Narcobarbital">Narcobarbital</a></li> <li><a href="/wiki/Nealbarbital" title="Nealbarbital">Nealbarbital</a></li> <li><a href="/wiki/Pentobarbital" title="Pentobarbital">Pentobarbital</a></li> <li><a href="/wiki/Phenallymal" class="mw-redirect" title="Phenallymal">Phenallymal</a></li> <li><a href="/wiki/Phenobarbital" title="Phenobarbital">Phenobarbital</a></li> <li><a href="/wiki/Phetharbital" title="Phetharbital">Phetharbital</a></li> <li><a href="/wiki/Primidone" title="Primidone">Primidone</a></li> <li><a href="/wiki/Probarbital" title="Probarbital">Probarbital</a></li> <li><a href="/wiki/Propallylonal" title="Propallylonal">Propallylonal</a></li> <li><a href="/wiki/Propylbarbital" title="Propylbarbital">Propylbarbital</a></li> <li><a href="/wiki/Proxibarbital" title="Proxibarbital">Proxibarbital</a></li> <li><a href="/wiki/Reposal" title="Reposal">Reposal</a></li> <li><a href="/wiki/Secobarbital" title="Secobarbital">Secobarbital</a></li> <li><a href="/wiki/Sigmodal" title="Sigmodal">Sigmodal</a></li> <li><a href="/wiki/Spirobarbital" title="Spirobarbital">Spirobarbital</a></li> <li><a href="/wiki/Talbutal" title="Talbutal">Talbutal</a></li> <li><a href="/wiki/Tetrabamate" title="Tetrabamate">Tetrabamate</a></li> <li><a href="/wiki/Tetrabarbital" title="Tetrabarbital">Tetrabarbital</a></li> <li><a href="/wiki/Thialbarbital" title="Thialbarbital">Thialbarbital</a></li> <li><a href="/wiki/Thiamylal" title="Thiamylal">Thiamylal</a></li> <li><a href="/wiki/Thiobarbital" title="Thiobarbital">Thiobarbital</a></li> <li><a href="/wiki/Thiobutabarbital" title="Thiobutabarbital">Thiobutabarbital</a></li> <li><a href="/wiki/Sodium_thiopental" title="Sodium thiopental">Thiopental</a></li> <li><a href="/wiki/Thiotetrabarbital" title="Thiotetrabarbital">Thiotetrabarbital</a></li> <li><a href="/wiki/Valofane" title="Valofane">Valofane</a></li> <li><a href="/wiki/Vinbarbital" title="Vinbarbital">Vinbarbital</a></li> <li><a href="/wiki/Vinylbital" title="Vinylbital">Vinylbital</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align: center;"><a href="/wiki/Benzodiazepine" title="Benzodiazepine">Benzodiazepines</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/2-Oxoquazepam" title="2-Oxoquazepam">2-Oxoquazepam</a></li> <li><a href="/wiki/3-Hydroxyphenazepam" title="3-Hydroxyphenazepam">3-Hydroxyphenazepam</a></li> <li><a href="/wiki/Adinazolam" title="Adinazolam">Adinazolam</a></li> <li><a href="/wiki/Alprazolam" title="Alprazolam">Alprazolam</a></li> <li><a href="/wiki/Arfendazam" title="Arfendazam">Arfendazam</a></li> <li><a href="/wiki/Avizafone" title="Avizafone">Avizafone</a></li> <li><a href="/wiki/Bentazepam" title="Bentazepam">Bentazepam</a></li> <li><a href="/wiki/Bretazenil" title="Bretazenil">Bretazenil</a></li> <li><a href="/wiki/Bromazepam" title="Bromazepam">Bromazepam</a></li> <li><a href="/wiki/Bromazolam" title="Bromazolam">Bromazolam</a></li> <li><a href="/wiki/Brotizolam" title="Brotizolam">Brotizolam</a></li> <li><a href="/wiki/Camazepam" title="Camazepam">Camazepam</a></li> <li><a href="/wiki/Carburazepam" title="Carburazepam">Carburazepam</a></li> <li><a href="/wiki/Chlordiazepoxide" title="Chlordiazepoxide">Chlordiazepoxide</a></li> <li><a href="/wiki/Ciclotizolam" title="Ciclotizolam">Ciclotizolam</a></li> <li><a href="/wiki/Cinazepam" title="Cinazepam">Cinazepam</a></li> <li><a href="/wiki/Cinolazepam" title="Cinolazepam">Cinolazepam</a></li> <li><a href="/wiki/Clazolam" title="Clazolam">Clazolam</a></li> <li><a href="/wiki/Climazolam" title="Climazolam">Climazolam</a></li> <li><a href="/wiki/Clobazam" title="Clobazam">Clobazam</a></li> <li><a href="/wiki/Clonazepam" title="Clonazepam">Clonazepam</a></li> <li><a href="/wiki/Clonazolam" title="Clonazolam">Clonazolam</a></li> <li><a href="/wiki/Cloniprazepam" title="Cloniprazepam">Cloniprazepam</a></li> <li><a href="/wiki/Clorazepate" title="Clorazepate">Clorazepate</a></li> <li><a href="/wiki/Clotiazepam" title="Clotiazepam">Clotiazepam</a></li> <li><a href="/wiki/Cloxazolam" title="Cloxazolam">Cloxazolam</a></li> <li><a href="/wiki/CP-1414S" title="CP-1414S">CP-1414S</a></li> <li><a href="/wiki/Cyprazepam" title="Cyprazepam">Cyprazepam</a></li> <li><a href="/wiki/Delorazepam" title="Delorazepam">Delorazepam</a></li> <li><a href="/wiki/Demoxepam" title="Demoxepam">Demoxepam</a></li> <li><a href="/wiki/Diazepam" title="Diazepam">Diazepam</a></li> <li><a href="/wiki/Diclazepam" title="Diclazepam">Diclazepam</a></li> <li><a href="/wiki/Dimdazenil" title="Dimdazenil">Dimdazenil</a></li> <li><a href="/wiki/Doxefazepam" title="Doxefazepam">Doxefazepam</a></li> <li><a href="/wiki/Elfazepam" title="Elfazepam">Elfazepam</a></li> <li><a href="/wiki/Estazolam" title="Estazolam">Estazolam</a></li> <li><a href="/wiki/Ethyl_carfluzepate" title="Ethyl carfluzepate">Ethyl carfluzepate</a></li> <li><a href="/wiki/Ethyl_dirazepate" title="Ethyl dirazepate">Ethyl dirazepate</a></li> <li><a href="/wiki/Ethyl_loflazepate" title="Ethyl loflazepate">Ethyl loflazepate</a></li> <li><a href="/wiki/Etizolam" title="Etizolam">Etizolam</a></li> <li><a href="/wiki/FG-8205" title="FG-8205">FG-8205</a></li> <li><a href="/wiki/Fletazepam" title="Fletazepam">Fletazepam</a></li> <li><a href="/wiki/Flubromazepam" title="Flubromazepam">Flubromazepam</a></li> <li><a href="/wiki/Flubromazolam" title="Flubromazolam">Flubromazolam</a></li> <li><a href="/wiki/Fludiazepam" title="Fludiazepam">Fludiazepam</a></li> <li><a href="/wiki/Flunitrazepam" title="Flunitrazepam">Flunitrazepam</a></li> <li><a href="/wiki/Flunitrazolam" title="Flunitrazolam">Flunitrazolam</a></li> <li><a href="/wiki/Flurazepam" title="Flurazepam">Flurazepam</a></li> <li><a href="/wiki/Flutazolam" title="Flutazolam">Flutazolam</a></li> <li><a href="/wiki/Flutemazepam" title="Flutemazepam">Flutemazepam</a></li> <li><a href="/wiki/Flutoprazepam" title="Flutoprazepam">Flutoprazepam</a></li> <li><a href="/wiki/Fosazepam" title="Fosazepam">Fosazepam</a></li> <li><a href="/wiki/Gidazepam" title="Gidazepam">Gidazepam</a></li> <li><a href="/wiki/Halazepam" title="Halazepam">Halazepam</a></li> <li><a href="/wiki/Haloxazolam" title="Haloxazolam">Haloxazolam</a></li> <li><a href="/wiki/Iclazepam" title="Iclazepam">Iclazepam</a></li> <li><a href="/wiki/Imidazenil" title="Imidazenil">Imidazenil</a></li> <li><a href="/wiki/Irazepine" title="Irazepine">Irazepine</a></li> <li><a href="/wiki/Ketazolam" title="Ketazolam">Ketazolam</a></li> <li><a href="/wiki/Lofendazam" title="Lofendazam">Lofendazam</a></li> <li><a href="/wiki/Lopirazepam" title="Lopirazepam">Lopirazepam</a></li> <li><a href="/wiki/Loprazolam" title="Loprazolam">Loprazolam</a></li> <li><a href="/wiki/Lorazepam" title="Lorazepam">Lorazepam</a></li> <li><a href="/wiki/Lormetazepam" title="Lormetazepam">Lormetazepam</a></li> <li><a href="/wiki/Meclonazepam" title="Meclonazepam">Meclonazepam</a></li> <li><a href="/wiki/Medazepam" title="Medazepam">Medazepam</a></li> <li><a href="/wiki/Menitrazepam" title="Menitrazepam">Menitrazepam</a></li> <li><a href="/wiki/Metaclazepam" title="Metaclazepam">Metaclazepam</a></li> <li><a href="/wiki/Mexazolam" title="Mexazolam">Mexazolam</a></li> <li><a href="/wiki/Midazolam" title="Midazolam">Midazolam</a></li> <li><a href="/wiki/Motrazepam" title="Motrazepam">Motrazepam</a></li> <li><a href="/wiki/N-Desalkylflurazepam" title="N-Desalkylflurazepam">N-Desalkylflurazepam</a></li> <li><a href="/wiki/Nifoxipam" title="Nifoxipam">Nifoxipam</a></li> <li><a href="/wiki/Nimetazepam" title="Nimetazepam">Nimetazepam</a></li> <li><a href="/wiki/Nitrazepam" title="Nitrazepam">Nitrazepam</a></li> <li><a href="/wiki/Nitrazepate" title="Nitrazepate">Nitrazepate</a></li> <li><a href="/wiki/Nitrazolam" title="Nitrazolam">Nitrazolam</a></li> <li><a href="/wiki/Nordazepam" title="Nordazepam">Nordazepam</a></li> <li><a href="/wiki/Nortetrazepam" title="Nortetrazepam">Nortetrazepam</a></li> <li><a href="/wiki/Oxazepam" title="Oxazepam">Oxazepam</a></li> <li><a href="/wiki/Oxazolam" title="Oxazolam">Oxazolam</a></li> <li><a href="/wiki/Phenazepam" title="Phenazepam">Phenazepam</a></li> <li><a href="/wiki/Pinazepam" title="Pinazepam">Pinazepam</a></li> <li><a href="/wiki/Pivoxazepam" title="Pivoxazepam">Pivoxazepam</a></li> <li><a href="/wiki/Prazepam" title="Prazepam">Prazepam</a></li> <li><a href="/wiki/Premazepam" title="Premazepam">Premazepam</a></li> <li><a href="/wiki/Proflazepam" title="Proflazepam">Proflazepam</a></li> <li><a href="/wiki/Pyrazolam" title="Pyrazolam">Pyrazolam</a></li> <li><a href="/wiki/QH-II-66" title="QH-II-66">QH-II-66</a></li> <li><a href="/wiki/Quazepam" title="Quazepam">Quazepam</a></li> <li><a href="/wiki/Reclazepam" title="Reclazepam">Reclazepam</a></li> <li><a href="/wiki/Remimazolam" title="Remimazolam">Remimazolam</a></li> <li><a href="/wiki/Rilmazafone" title="Rilmazafone">Rilmazafone</a></li> <li><a href="/wiki/Ripazepam" title="Ripazepam">Ripazepam</a></li> <li><a href="/wiki/Ro48-6791" title="Ro48-6791">Ro48-6791</a></li> <li><a href="/wiki/Ro48-8684" title="Ro48-8684">Ro48-8684</a></li> <li><a href="/wiki/SH-053-R-CH3-2%E2%80%B2F" title="SH-053-R-CH3-2′F">SH-053-R-CH3-2′F</a></li> <li><a href="/wiki/Sulazepam" title="Sulazepam">Sulazepam</a></li> <li><a href="/wiki/Temazepam" title="Temazepam">Temazepam</a></li> <li><a href="/wiki/Tetrazepam" title="Tetrazepam">Tetrazepam</a></li> <li><a href="/wiki/Tolufazepam" class="mw-redirect" title="Tolufazepam">Tolufazepam</a></li> <li><a href="/wiki/Triazolam" title="Triazolam">Triazolam</a></li> <li><a href="/wiki/Triflubazam" title="Triflubazam">Triflubazam</a></li> <li><a href="/wiki/Triflunordazepam" title="Triflunordazepam">Triflunordazepam (Ro5-2904)</a></li> <li><a href="/wiki/Tuclazepam" title="Tuclazepam">Tuclazepam</a></li> <li><a href="/wiki/Uldazepam" title="Uldazepam">Uldazepam</a></li> <li><a href="/wiki/Zapizolam" title="Zapizolam">Zapizolam</a></li> <li><a href="/wiki/Zolazepam" title="Zolazepam">Zolazepam</a></li> <li><a href="/wiki/Zomebazam" title="Zomebazam">Zomebazam</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align: center;"><a href="/wiki/Carbamate" title="Carbamate">Carbamates</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Carisbamate" title="Carisbamate">Carisbamate</a></li> <li><a href="/wiki/Carisoprodol" title="Carisoprodol">Carisoprodol</a></li> <li><a href="/wiki/Clocental" title="Clocental">Clocental</a></li> <li><a href="/wiki/Cyclarbamate" title="Cyclarbamate">Cyclarbamate</a></li> <li><a href="/wiki/Difebarbamate" title="Difebarbamate">Difebarbamate</a></li> <li><a href="/wiki/Emylcamate" title="Emylcamate">Emylcamate</a></li> <li><a href="/wiki/Ethinamate" title="Ethinamate">Ethinamate</a></li> <li><a href="/wiki/Febarbamate" title="Febarbamate">Febarbamate</a></li> <li><a href="/wiki/Felbamate" title="Felbamate">Felbamate</a></li> <li><a href="/wiki/Hexapropymate" title="Hexapropymate">Hexapropymate</a></li> <li><a href="/wiki/Hydroxyphenamate" title="Hydroxyphenamate">Hydroxyphenamate</a></li> <li><a href="/wiki/Lorbamate" title="Lorbamate">Lorbamate</a></li> <li><a href="/wiki/Mebutamate" title="Mebutamate">Mebutamate</a></li> <li><a href="/wiki/Meprobamate" title="Meprobamate">Meprobamate</a></li> <li><a href="/wiki/Nisobamate" title="Nisobamate">Nisobamate</a></li> <li><a href="/wiki/Pentabamate" title="Pentabamate">Pentabamate</a></li> <li><a href="/wiki/Phenprobamate" title="Phenprobamate">Phenprobamate</a></li> <li><a href="/wiki/Procymate" title="Procymate">Procymate</a></li> <li><a href="/wiki/Styramate" title="Styramate">Styramate</a></li> <li><a href="/wiki/Tetrabamate" title="Tetrabamate">Tetrabamate</a></li> <li><a href="/wiki/Tybamate" title="Tybamate">Tybamate</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align: center;"><a href="/wiki/Flavonoid" title="Flavonoid">Flavonoids</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/6-Methylapigenin" title="6-Methylapigenin">6-Methylapigenin</a></li> <li><a href="/wiki/Ampelopsin" title="Ampelopsin">Ampelopsin (dihydromyricetin)</a></li> <li><a href="/wiki/Apigenin" title="Apigenin">Apigenin</a></li> <li><a href="/wiki/Baicalein" title="Baicalein">Baicalein</a></li> <li><a href="/wiki/Baicalin" title="Baicalin">Baicalin</a></li> <li><a href="/wiki/Catechin" title="Catechin">Catechin</a></li> <li><a href="/wiki/Epigallocatechin" class="mw-redirect" title="Epigallocatechin">EGC</a></li> <li><a href="/wiki/Epigallocatechin_gallate" title="Epigallocatechin gallate">EGCG</a></li> <li><a href="/wiki/Hispidulin" title="Hispidulin">Hispidulin</a></li> <li><a href="/w/index.php?title=Linarin&action=edit&redlink=1" class="new" title="Linarin (page does not exist)">Linarin</a></li> <li><a href="/wiki/Luteolin" title="Luteolin">Luteolin</a></li> <li><a href="/w/index.php?title=Trans-6,4%E2%80%B2-dimethoxyretrochalcone&action=edit&redlink=1" class="new" title="Trans-6,4′-dimethoxyretrochalcone (page does not exist)">Rc-OMe</a></li> <li><a href="/wiki/Scutellaria" title="Scutellaria">Skullcap</a> constituents (e.g., <a href="/wiki/Baicalin" title="Baicalin">baicalin</a>)</li> <li><a href="/wiki/Wogonin" title="Wogonin">Wogonin</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align: center;"><a href="/wiki/Imidazole" title="Imidazole">Imidazoles</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Etomidate" title="Etomidate">Etomidate</a></li> <li><a href="/wiki/Metomidate" title="Metomidate">Metomidate</a></li> <li><a href="/wiki/Propoxate" title="Propoxate">Propoxate</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align: center;"><a href="/wiki/Kava" title="Kava">Kava</a> constituents</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/w/index.php?title=10-Methoxyyangonin&action=edit&redlink=1" class="new" title="10-Methoxyyangonin (page does not exist)">10-Methoxyyangonin</a></li> <li><a href="/w/index.php?title=11-Methoxyyangonin&action=edit&redlink=1" class="new" title="11-Methoxyyangonin (page does not exist)">11-Methoxyyangonin</a></li> <li><a href="/w/index.php?title=11-Hydroxyyangonin&action=edit&redlink=1" class="new" title="11-Hydroxyyangonin (page does not exist)">11-Hydroxyyangonin</a></li> <li><a href="/wiki/Desmethoxyyangonin" title="Desmethoxyyangonin">Desmethoxyyangonin</a></li> <li><a href="/w/index.php?title=11-Methoxy-12-hydroxydehydrokavain&action=edit&redlink=1" class="new" title="11-Methoxy-12-hydroxydehydrokavain (page does not exist)">11-Methoxy-12-hydroxydehydrokavain</a></li> <li><a href="/w/index.php?title=7,8-Dihydroyangonin&action=edit&redlink=1" class="new" title="7,8-Dihydroyangonin (page does not exist)">7,8-Dihydroyangonin</a></li> <li><a href="/wiki/Kavain" title="Kavain">Kavain</a></li> <li><a href="/w/index.php?title=5-Hydroxykavain&action=edit&redlink=1" class="new" title="5-Hydroxykavain (page does not exist)">5-Hydroxykavain</a></li> <li><a href="/w/index.php?title=5,6-Dihydroyangonin&action=edit&redlink=1" class="new" title="5,6-Dihydroyangonin (page does not exist)">5,6-Dihydroyangonin</a></li> <li><a href="/w/index.php?title=7,8-Dihydrokavain&action=edit&redlink=1" class="new" title="7,8-Dihydrokavain (page does not exist)">7,8-Dihydrokavain</a></li> <li><a href="/w/index.php?title=5,6,7,8-Tetrahydroyangonin&action=edit&redlink=1" class="new" title="5,6,7,8-Tetrahydroyangonin (page does not exist)">5,6,7,8-Tetrahydroyangonin</a></li> <li><a href="/w/index.php?title=5,6-Dehydromethysticin&action=edit&redlink=1" class="new" title="5,6-Dehydromethysticin (page does not exist)">5,6-Dehydromethysticin</a></li> <li><a href="/wiki/Methysticin" title="Methysticin">Methysticin</a></li> <li><a href="/w/index.php?title=7,8-Dihydromethysticin&action=edit&redlink=1" class="new" title="7,8-Dihydromethysticin (page does not exist)">7,8-Dihydromethysticin</a></li> <li><a href="/wiki/Yangonin" title="Yangonin">Yangonin</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align: center;"><a href="/wiki/Monoureide" class="mw-redirect" title="Monoureide">Monoureides</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Acecarbromal" title="Acecarbromal">Acecarbromal</a></li> <li><a href="/wiki/Apronal" title="Apronal">Apronal (apronalide)</a></li> <li><a href="/wiki/Bromisoval" title="Bromisoval">Bromisoval</a></li> <li><a href="/wiki/Carbromal" title="Carbromal">Carbromal</a></li> <li><a href="/w/index.php?title=Capuride&action=edit&redlink=1" class="new" title="Capuride (page does not exist)">Capuride</a></li> <li><a href="/w/index.php?title=Ectylurea&action=edit&redlink=1" class="new" title="Ectylurea (page does not exist)">Ectylurea</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align: center;"><a href="/wiki/Neuroactive_steroid" class="mw-redirect" title="Neuroactive steroid">Neuroactive steroids</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Acebrochol" title="Acebrochol">Acebrochol</a></li> <li><a href="/wiki/Allopregnanolone" title="Allopregnanolone">Allopregnanolone (brexanolone)</a></li> <li><a href="/wiki/Alfadolone" title="Alfadolone">Alfadolone</a></li> <li><a href="/wiki/Alfaxalone" title="Alfaxalone">Alfaxalone</a></li> <li><a href="/wiki/3%CE%B1-Androstanediol" title="3α-Androstanediol">3α-Androstanediol</a></li> <li><a href="/wiki/Androstenol" title="Androstenol">Androstenol</a></li> <li><a href="/wiki/Androsterone" title="Androsterone">Androsterone</a></li> <li>Certain <a href="/wiki/Anabolic-androgenic_steroid" class="mw-redirect" title="Anabolic-androgenic steroid">anabolic-androgenic steroids</a></li> <li><a href="/wiki/Cholesterol" title="Cholesterol">Cholesterol</a></li> <li><a href="/wiki/Dihydrodeoxycorticosterone" title="Dihydrodeoxycorticosterone">DHDOC</a></li> <li><a href="/wiki/3%CE%B1-Dihydroprogesterone" title="3α-Dihydroprogesterone">3α-DHP</a></li> <li><a href="/wiki/5%CE%B1-Dihydroprogesterone" title="5α-Dihydroprogesterone">5α-DHP</a></li> <li><a href="/wiki/5%CE%B2-Dihydroprogesterone" title="5β-Dihydroprogesterone">5β-DHP</a></li> <li><a href="/wiki/Dihydrotestosterone" title="Dihydrotestosterone">DHT</a></li> <li><a href="/wiki/Etiocholanolone" title="Etiocholanolone">Etiocholanolone</a></li> <li><a href="/wiki/Ganaxolone" title="Ganaxolone">Ganaxolone</a></li> <li><a href="/wiki/Hydroxydione" title="Hydroxydione">Hydroxydione</a></li> <li><a href="/wiki/Minaxolone" title="Minaxolone">Minaxolone</a></li> <li><a href="/wiki/ORG-20599" title="ORG-20599">ORG-20599</a></li> <li><a href="/wiki/ORG-21465" title="ORG-21465">ORG-21465</a></li> <li><a href="/wiki/P1-185" title="P1-185">P1-185</a></li> <li><a href="/wiki/Posovolone" title="Posovolone">Posovolone</a></li> <li><a href="/wiki/Pregnanolone" title="Pregnanolone">Pregnanolone (eltanolone)</a></li> <li><a href="/wiki/Progesterone" title="Progesterone">Progesterone</a></li> <li><a href="/wiki/Renanolone" title="Renanolone">Renanolone</a></li> <li><a href="/w/index.php?title=SAGE-105&action=edit&redlink=1" class="new" title="SAGE-105 (page does not exist)">SAGE-105</a></li> <li><a href="/wiki/SAGE-324" title="SAGE-324">SAGE-324</a></li> <li><a href="/w/index.php?title=SAGE-516&action=edit&redlink=1" class="new" title="SAGE-516 (page does not exist)">SAGE-516</a></li> <li><a href="/w/index.php?title=SAGE-689&action=edit&redlink=1" class="new" title="SAGE-689 (page does not exist)">SAGE-689</a></li> <li><a href="/w/index.php?title=SAGE-872&action=edit&redlink=1" class="new" title="SAGE-872 (page does not exist)">SAGE-872</a></li> <li><a href="/wiki/Testosterone" title="Testosterone">Testosterone</a></li> <li><a href="/wiki/Tetrahydrodeoxycorticosterone" title="Tetrahydrodeoxycorticosterone">THDOC</a></li> <li><a href="/wiki/Zuranolone" title="Zuranolone">Zuranolone</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align: center;"><a href="/wiki/Nonbenzodiazepine" title="Nonbenzodiazepine">Nonbenzodiazepines</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i><a href="/wiki/Cyclopyrrolone" class="mw-redirect" title="Cyclopyrrolone">Cyclopyrrolones</a></i>: <a href="/wiki/Eszopiclone" title="Eszopiclone">Eszopiclone</a></li> <li><a href="/wiki/Pagoclone" title="Pagoclone">Pagoclone</a></li> <li><a href="/wiki/Pazinaclone" title="Pazinaclone">Pazinaclone</a></li> <li><a href="/wiki/Suproclone" title="Suproclone">Suproclone</a></li> <li><a href="/wiki/Suriclone" title="Suriclone">Suriclone</a></li> <li><a href="/wiki/Zopiclone" title="Zopiclone">Zopiclone</a></li></ul> <ul><li><i><a href="/wiki/Imidazopyridine" title="Imidazopyridine">Imidazopyridines</a></i>: <a href="/wiki/Alpidem" title="Alpidem">Alpidem</a></li> <li><a href="/wiki/DS-1_(drug)" title="DS-1 (drug)">DS-1</a></li> <li><a href="/wiki/Necopidem" title="Necopidem">Necopidem</a></li> <li><a href="/wiki/Saripidem" title="Saripidem">Saripidem</a></li> <li><a href="/wiki/Zolpidem" title="Zolpidem">Zolpidem</a></li></ul> <ul><li><i><a href="/wiki/Pyrazolopyrimidine" title="Pyrazolopyrimidine">Pyrazolopyrimidines</a></i>: <a href="/wiki/Divaplon" title="Divaplon">Divaplon</a></li> <li><a href="/wiki/Fasiplon" title="Fasiplon">Fasiplon</a></li> <li><a href="/wiki/Indiplon" title="Indiplon">Indiplon</a></li> <li><a href="/wiki/Lorediplon" title="Lorediplon">Lorediplon</a></li> <li><a href="/wiki/Ocinaplon" title="Ocinaplon">Ocinaplon</a></li> <li><a href="/wiki/Panadiplon" title="Panadiplon">Panadiplon</a></li> <li><a href="/wiki/Taniplon" title="Taniplon">Taniplon</a></li> <li><a href="/wiki/Zaleplon" title="Zaleplon">Zaleplon</a></li></ul> <ul><li><i>Others</i>: <a href="/wiki/Adipiplon" title="Adipiplon">Adipiplon</a></li> <li><a href="/wiki/CGS-8216" title="CGS-8216">CGS-8216</a></li> <li><a href="/wiki/CGS-9896" title="CGS-9896">CGS-9896</a></li> <li><a href="/wiki/CGS-13767" title="CGS-13767">CGS-13767</a></li> <li><a href="/wiki/CGS-20625" title="CGS-20625">CGS-20625</a></li> <li><a href="/wiki/CL-218,872" title="CL-218,872">CL-218,872</a></li> <li><a href="/wiki/CP-615,003" title="CP-615,003">CP-615,003</a></li> <li><a href="/w/index.php?title=CTP-354&action=edit&redlink=1" class="new" title="CTP-354 (page does not exist)">CTP-354</a></li> <li><a href="/wiki/ELB-139" title="ELB-139">ELB-139</a></li> <li><a href="/wiki/GBLD-345" title="GBLD-345">GBLD-345</a></li> <li><a href="/wiki/Imepitoin" title="Imepitoin">Imepitoin</a></li> <li><a href="/wiki/JM-1232" title="JM-1232">JM-1232</a></li> <li><a href="/wiki/L-838,417" title="L-838,417">L-838,417</a></li> <li><a href="/wiki/Lirequinil" title="Lirequinil">Lirequinil (Ro41-3696)</a></li> <li><a href="/wiki/NS-2664" title="NS-2664">NS-2664</a></li> <li><a href="/wiki/NS-2710" title="NS-2710">NS-2710</a></li> <li><a href="/wiki/NS-11394" title="NS-11394">NS-11394</a></li> <li><a href="/wiki/Pipequaline" title="Pipequaline">Pipequaline</a></li> <li><a href="/wiki/ROD-188" title="ROD-188">ROD-188</a></li> <li><a href="/wiki/RWJ-51204" title="RWJ-51204">RWJ-51204</a></li> <li><a href="/wiki/SB-205,384" class="mw-redirect" title="SB-205,384">SB-205,384</a></li> <li><a href="/wiki/SX-3228" title="SX-3228">SX-3228</a></li> <li><a href="/w/index.php?title=TGSC01AA&action=edit&redlink=1" class="new" title="TGSC01AA (page does not exist)">TGSC01AA</a></li> <li><a href="/wiki/TP-003" title="TP-003">TP-003</a></li> <li><a href="/wiki/TPA-023" title="TPA-023">TPA-023</a></li> <li><a href="/wiki/TP-13" title="TP-13">TP-13</a></li> <li><a href="/wiki/U-89843A" title="U-89843A">U-89843A</a></li> <li><a href="/wiki/U-90042" title="U-90042">U-90042</a></li> <li><a href="/wiki/Viqualine" title="Viqualine">Viqualine</a></li> <li><a href="/wiki/Y-23684" title="Y-23684">Y-23684</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align: center;"><a href="/wiki/Phenol" title="Phenol">Phenols</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Fospropofol" title="Fospropofol">Fospropofol</a></li> <li><a href="/wiki/Propofol" title="Propofol">Propofol</a></li> <li><a class="mw-selflink selflink">Thymol</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align: center;"><a href="/wiki/Piperidinedione" class="mw-redirect" title="Piperidinedione">Piperidinediones</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Glutethimide" title="Glutethimide">Glutethimide</a></li> <li><a href="/wiki/Methyprylon" title="Methyprylon">Methyprylon</a></li> <li><a href="/wiki/Piperidione" title="Piperidione">Piperidione</a></li> <li><a href="/wiki/Pyrithyldione" title="Pyrithyldione">Pyrithyldione</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align: center;"><a href="/wiki/Pyrazolopyridine" class="mw-redirect" title="Pyrazolopyridine">Pyrazolopyridines</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Cartazolate" title="Cartazolate">Cartazolate</a></li> <li><a href="/wiki/Etazolate" title="Etazolate">Etazolate</a></li> <li><a href="/wiki/ICI-190,622" title="ICI-190,622">ICI-190,622</a></li> <li><a href="/wiki/Tracazolate" title="Tracazolate">Tracazolate</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align: center;"><a href="/wiki/Quinazolinone" title="Quinazolinone">Quinazolinones</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Afloqualone" title="Afloqualone">Afloqualone</a></li> <li><a href="/wiki/Cloroqualone" title="Cloroqualone">Cloroqualone</a></li> <li><a href="/wiki/Diproqualone" title="Diproqualone">Diproqualone</a></li> <li><a href="/wiki/Etaqualone" title="Etaqualone">Etaqualone</a></li> <li><a href="/wiki/Mebroqualone" title="Mebroqualone">Mebroqualone</a></li> <li><a href="/wiki/Mecloqualone" title="Mecloqualone">Mecloqualone</a></li> <li><a href="/wiki/Methaqualone" title="Methaqualone">Methaqualone</a></li> <li><a href="/wiki/Methylmethaqualone" title="Methylmethaqualone">Methylmethaqualone</a></li> <li><a href="/wiki/Nitromethaqualone" title="Nitromethaqualone">Nitromethaqualone</a></li> <li><a href="/wiki/SL-164" title="SL-164">SL-164</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align: center;"><a href="/wiki/Inhalational_anaesthetic" class="mw-redirect" title="Inhalational anaesthetic">Volatiles</a>/<a href="/wiki/Inhalational_anaesthetic" class="mw-redirect" title="Inhalational anaesthetic">gases</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Acetone" title="Acetone">Acetone</a></li> <li><a href="/wiki/Acetophenone" title="Acetophenone">Acetophenone</a></li> <li><a href="/wiki/Acetylglycinamide_chloral_hydrate" title="Acetylglycinamide chloral hydrate">Acetylglycinamide chloral hydrate</a></li> <li><a href="/wiki/Aliflurane" title="Aliflurane">Aliflurane</a></li> <li><a href="/wiki/Benzene" title="Benzene">Benzene</a></li> <li><a href="/wiki/Butane" title="Butane">Butane</a></li> <li><a href="/wiki/Butylene" class="mw-redirect" title="Butylene">Butylene</a></li> <li><a href="/wiki/Centalun" title="Centalun">Centalun</a></li> <li><a href="/wiki/Chloral" title="Chloral">Chloral</a></li> <li><a href="/wiki/Chloral_betaine" title="Chloral betaine">Chloral betaine</a></li> <li><a href="/wiki/Chloral_hydrate" title="Chloral hydrate">Chloral hydrate</a></li> <li><a href="/wiki/Chloroform" title="Chloroform">Chloroform</a></li> <li><a href="/wiki/Cryofluorane" class="mw-redirect" title="Cryofluorane">Cryofluorane</a></li> <li><a href="/wiki/Desflurane" title="Desflurane">Desflurane</a></li> <li><a href="/wiki/Dichloralphenazone" title="Dichloralphenazone">Dichloralphenazone</a></li> <li><a href="/wiki/Dichloromethane" title="Dichloromethane">Dichloromethane</a></li> <li><a href="/wiki/Diethyl_ether" title="Diethyl ether">Diethyl ether</a></li> <li><a href="/wiki/Enflurane" title="Enflurane">Enflurane</a></li> <li><a href="/wiki/Chloroethane" title="Chloroethane">Ethyl chloride</a></li> <li><a href="/wiki/Ethylene" title="Ethylene">Ethylene</a></li> <li><a href="/wiki/Fluroxene" title="Fluroxene">Fluroxene</a></li> <li><a href="/wiki/Gasoline" title="Gasoline">Gasoline</a></li> <li><a href="/wiki/Halopropane" title="Halopropane">Halopropane</a></li> <li><a href="/wiki/Halothane" title="Halothane">Halothane</a></li> <li><a href="/wiki/Isoflurane" title="Isoflurane">Isoflurane</a></li> <li><a href="/wiki/Kerosene" title="Kerosene">Kerosine</a></li> <li><a href="/wiki/Methoxyflurane" title="Methoxyflurane">Methoxyflurane</a></li> <li><a href="/wiki/Methoxypropane" title="Methoxypropane">Methoxypropane</a></li> <li><a href="/wiki/Nitric_oxide" title="Nitric oxide">Nitric oxide</a></li> <li><a href="/wiki/Nitrogen" title="Nitrogen">Nitrogen</a></li> <li><a href="/wiki/Nitrous_oxide" title="Nitrous oxide">Nitrous oxide</a></li> <li><a href="/wiki/Norflurane" class="mw-redirect" title="Norflurane">Norflurane</a></li> <li><a href="/wiki/Paraldehyde" title="Paraldehyde">Paraldehyde</a></li> <li><a href="/wiki/Propane" title="Propane">Propane</a></li> <li><a href="/wiki/Propene" class="mw-redirect" title="Propene">Propylene</a></li> <li><a href="/wiki/Roflurane" title="Roflurane">Roflurane</a></li> <li><a href="/wiki/Sevoflurane" title="Sevoflurane">Sevoflurane</a></li> <li><a href="/wiki/Synthane" title="Synthane">Synthane</a></li> <li><a href="/wiki/Teflurane" title="Teflurane">Teflurane</a></li> <li><a href="/wiki/Toluene" title="Toluene">Toluene</a></li> <li><a href="/wiki/1,1,1-Trichloroethane" title="1,1,1-Trichloroethane">Trichloroethane (methyl chloroform)</a></li> <li><a href="/wiki/Trichloroethylene" title="Trichloroethylene">Trichloroethylene</a></li> <li><a href="/wiki/Divinyl_ether" title="Divinyl ether">Vinyl ether</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align: center;">Others/unsorted</th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/3-Hydroxybutanal" title="3-Hydroxybutanal">3-Hydroxybutanal</a></li> <li><a href="/w/index.php?title=%CE%91-Ethyl-%CE%B1-methylthiobutyrolactone&action=edit&redlink=1" class="new" title="Α-Ethyl-α-methylthiobutyrolactone (page does not exist)">α-EMTBL</a></li> <li><a href="/w/index.php?title=AA-29504&action=edit&redlink=1" class="new" title="AA-29504 (page does not exist)">AA-29504</a></li> <li><a href="/wiki/Alogabat" title="Alogabat">Alogabat</a></li> <li><a href="/wiki/Avermectin" title="Avermectin">Avermectins</a> (e.g., <a href="/wiki/Ivermectin" title="Ivermectin">ivermectin</a>)</li> <li><a href="/wiki/Bromide" title="Bromide">Bromide</a> compounds (e.g., <a href="/wiki/Lithium_bromide" title="Lithium bromide">lithium bromide</a>, <a href="/wiki/Potassium_bromide" title="Potassium bromide">potassium bromide</a>, <a href="/wiki/Sodium_bromide" title="Sodium bromide">sodium bromide</a>)</li> <li><a href="/wiki/Carbamazepine" title="Carbamazepine">Carbamazepine</a></li> <li><a href="/wiki/Chloralose" title="Chloralose">Chloralose</a></li> <li><a href="/wiki/Chlormezanone" title="Chlormezanone">Chlormezanone</a></li> <li><a href="/wiki/Clomethiazole" title="Clomethiazole">Clomethiazole</a></li> <li><a href="/wiki/Darigabat" title="Darigabat">Darigabat</a></li> <li><a href="/wiki/3,3-Diethyl-2-pyrrolidinone" title="3,3-Diethyl-2-pyrrolidinone">DEABL</a></li> <li><a href="/wiki/Deuterated_etifoxine" title="Deuterated etifoxine">Deuterated etifoxine</a></li> <li><a href="/wiki/Dihydroergoline" class="mw-redirect" title="Dihydroergoline">Dihydroergolines</a> (e.g., <a href="/wiki/Dihydroergocryptine" title="Dihydroergocryptine">dihydroergocryptine</a>, <a href="/w/index.php?title=Dihydroergosine&action=edit&redlink=1" class="new" title="Dihydroergosine (page does not exist)">dihydroergosine</a>, <a href="/wiki/Dihydroergotamine" title="Dihydroergotamine">dihydroergotamine</a>, <a href="/wiki/Ergoloid" title="Ergoloid">ergoloid (dihydroergotoxine)</a>)</li> <li><a href="/w/index.php?title=4-Chloro-N-(2-(2-thienyl)imidazo(1,2-a)pyridin-3-yl)benzamide&action=edit&redlink=1" class="new" title="4-Chloro-N-(2-(2-thienyl)imidazo(1,2-a)pyridin-3-yl)benzamide (page does not exist)">DS2</a></li> <li><a href="/wiki/Efavirenz" title="Efavirenz">Efavirenz</a></li> <li><a href="/wiki/Etazepine" title="Etazepine">Etazepine</a></li> <li><a href="/wiki/Etifoxine" title="Etifoxine">Etifoxine</a></li> <li><a href="/wiki/Fenamate" class="mw-redirect" title="Fenamate">Fenamates</a> (e.g., <a href="/wiki/Flufenamic_acid" title="Flufenamic acid">flufenamic acid</a>, <a href="/wiki/Mefenamic_acid" title="Mefenamic acid">mefenamic acid</a>, <a href="/wiki/Niflumic_acid" title="Niflumic acid">niflumic acid</a>, <a href="/wiki/Tolfenamic_acid" title="Tolfenamic acid">tolfenamic acid</a>)</li> <li><a href="/wiki/Fluoxetine" title="Fluoxetine">Fluoxetine</a></li> <li><a href="/wiki/Flupirtine" title="Flupirtine">Flupirtine</a></li> <li><a href="/wiki/Hopantenic_acid" title="Hopantenic acid">Hopantenic acid</a></li> <li><a href="/wiki/KRM-II-81" title="KRM-II-81">KRM-II-81</a></li> <li><a href="/wiki/Lanthanum" title="Lanthanum">Lanthanum</a></li> <li><a href="/wiki/Lavender_oil" title="Lavender oil">Lavender oil</a></li> <li><a href="/wiki/Lignan" title="Lignan">Lignans</a> (e.g., <a href="/wiki/4-O-methylhonokiol" class="mw-redirect" title="4-O-methylhonokiol">4-O-methylhonokiol</a>, <a href="/wiki/Honokiol" title="Honokiol">honokiol</a>, <a href="/wiki/Magnolol" title="Magnolol">magnolol</a>, <a href="/wiki/Obovatol" title="Obovatol">obovatol</a>)</li> <li><a href="/wiki/Loreclezole" title="Loreclezole">Loreclezole</a></li> <li><a href="/wiki/Menthyl_isovalerate" title="Menthyl isovalerate">Menthyl isovalerate (validolum)</a></li> <li><a href="/wiki/Monastrol" title="Monastrol">Monastrol</a></li> <li><a href="/wiki/Nicotinic_acid" title="Nicotinic acid">Nicotinic acid</a></li> <li><a href="/wiki/Nicotinamide" title="Nicotinamide">Nicotinamide</a></li> <li><a href="/wiki/Org_25435" class="mw-redirect" title="Org 25435">Org 25,435</a></li> <li><a href="/wiki/Phenytoin" title="Phenytoin">Phenytoin</a></li> <li><a href="/wiki/Propanidid" title="Propanidid">Propanidid</a></li> <li><a href="/wiki/Retigabine" title="Retigabine">Retigabine (ezogabine)</a></li> <li><a href="/wiki/Safranal" title="Safranal">Safranal</a></li> <li><a href="/wiki/Seproxetine" title="Seproxetine">Seproxetine</a></li> <li><a href="/wiki/Stiripentol" title="Stiripentol">Stiripentol</a></li> <li><a href="/w/index.php?title=Sulfonylalkane&action=edit&redlink=1" class="new" title="Sulfonylalkane (page does not exist)">Sulfonylalkanes</a> (e.g., <a href="/wiki/Sulfonmethane" title="Sulfonmethane">sulfonmethane (sulfonal)</a>, <a href="/wiki/Tetronal" title="Tetronal">tetronal</a>, <a href="/wiki/Trional" title="Trional">trional</a>)</li> <li><a href="/wiki/Terpenoid" title="Terpenoid">Terpenoids</a> (e.g., <a href="/wiki/Borneol" title="Borneol">borneol</a>)</li> <li><a href="/wiki/Topiramate" title="Topiramate">Topiramate</a></li> <li><a href="/wiki/Valerian_(herb)" title="Valerian (herb)">Valerian</a> constituents (e.g., <a href="/wiki/3-methylbutanoic_acid" class="mw-redirect" title="3-methylbutanoic acid">isovaleric acid</a>, <a href="/wiki/Isovaleramide" title="Isovaleramide">isovaleramide</a>, <a href="/wiki/Valerenic_acid" title="Valerenic acid">valerenic acid</a>, <a href="/w/index.php?title=Valerenol&action=edit&redlink=1" class="new" title="Valerenol (page does not exist)">valerenol</a>)</li></ul> <ul><li><i>Unsorted benzodiazepine site positive modulators:</i> <a href="/wiki/%CE%91-Pinene" title="Α-Pinene">α-Pinene</a></li> <li><a href="/wiki/MRK-409_(MK-0343)" class="mw-redirect" title="MRK-409 (MK-0343)">MRK-409 (MK-0343)</a></li> <li><a href="/w/index.php?title=TCS-1105&action=edit&redlink=1" class="new" title="TCS-1105 (page does not exist)">TCS-1105</a></li> <li><a href="/wiki/TCS-1205" title="TCS-1205">TCS-1205</a></li></ul> </div></td></tr><tr><td class="navbox-abovebelow" colspan="2"><div><i><b>See also:</b> <a href="/wiki/Template:Receptor_modulators" title="Template:Receptor modulators">Receptor/signaling modulators</a> • <a href="/wiki/Template:GABA_receptor_modulators" title="Template:GABA receptor modulators">GABA receptor modulators</a> • <a href="/wiki/Template:GABA_metabolism_and_transport_modulators" title="Template:GABA metabolism and transport modulators">GABA metabolism/transport 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" /></div><div role="navigation" class="navbox" aria-labelledby="TRP_channel_modulators711" 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_modulators711" 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">5,6-EET</a></li> <li><a href="/wiki/12-Hydroxyeicosatetraenoic_acid" title="12-Hydroxyeicosatetraenoic 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-%CE%B1-sanshool" title="Hydroxy-α-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/Acrolein" title="Acrolein">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/12-Hydroxyeicosatetraenoic_acid" title="12-Hydroxyeicosatetraenoic acid">12S-HETE</a></li> <li><a href="/wiki/12-Hydroxyeicosatetraenoic_acid" title="12-Hydroxyeicosatetraenoic 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-%CE%B1-sanshool" title="Hydroxy-α-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 class="mw-selflink selflink">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" /></div><div role="navigation" class="navbox" aria-labelledby="Types_of_terpenes_and_terpenoids_(#_of_isoprene_units)435" 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:Terpenoids" title="Template:Terpenoids"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Terpenoids" title="Template talk:Terpenoids"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Terpenoids" title="Special:EditPage/Template:Terpenoids"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Types_of_terpenes_and_terpenoids_(#_of_isoprene_units)435" style="font-size:114%;margin:0 4em">Types of <a href="/wiki/Terpene" title="Terpene">terpenes</a> and <a href="/wiki/Terpenoid" title="Terpenoid">terpenoids</a> (# of <a href="/wiki/Isoprene" title="Isoprene">isoprene</a> units)</div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%">Basic forms:</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li>Acyclic (linear, <i>cis</i> and <i>trans</i> forms)</li> <li>Monocyclic (single ring)</li> <li>Bicyclic (2 rings)</li> <li><a href="/wiki/Iridoid" title="Iridoid">Iridoids</a> (cyclopentane ring)</li> <li>Iridoid glycosides (iridoids bound to a sugar)</li> <li><a href="/wiki/Steroid" title="Steroid">Steroids</a> (4 rings)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Hemiterpenoid" class="mw-redirect" title="Hemiterpenoid">Hemiterpenoids</a> (1)</th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Isoprene" title="Isoprene">Isoprene</a> (C<sub>5</sub>H<sub>8</sub>)</li> <li><a href="/wiki/Prenol" title="Prenol">Prenol</a></li> <li><a href="/wiki/Isovaleric_acid" title="Isovaleric acid">Isovaleric acid</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Monoterpene" title="Monoterpene">Monoterpenes</a> <br />(C<sub>10</sub>H<sub>16</sub>)(2)</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%">Acyclic</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/Ocimene" title="Ocimene">Ocimene</a></li> <li><a href="/wiki/Myrcene" title="Myrcene">Myrcenes</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Monocyclic</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/Limonene" title="Limonene">Limonene</a></li> <li><a href="/wiki/Terpinene" title="Terpinene">Terpinene</a></li> <li><a href="/wiki/Phellandrene" title="Phellandrene">Phellandrene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Bicyclic</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/Pinene" title="Pinene">Pinene</a> (<a href="/wiki/Alpha-Pinene" class="mw-redirect" title="Alpha-Pinene">α</a> and <a href="/wiki/Beta-Pinene" class="mw-redirect" title="Beta-Pinene">β</a>)</li> <li><a href="/wiki/Camphene" title="Camphene">Camphene</a></li> <li><a href="/wiki/Thujene" title="Thujene">Thujene</a></li> <li><a href="/wiki/Sabinene" title="Sabinene">Sabinene</a></li> <li><a href="/wiki/Carene" class="mw-redirect" title="Carene">Carene</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Monoterpenoids <br />(2,modified)</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%">Acyclic</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/Citronellal" title="Citronellal">Citronellal</a></li> <li><a href="/wiki/Citral" title="Citral">Citral</a></li> <li><a href="/wiki/Citronellol" title="Citronellol">Citronellol</a></li> <li><a href="/wiki/Geraniol" title="Geraniol">Geraniol</a></li> <li><a href="/wiki/Geranyl_pyrophosphate" title="Geranyl pyrophosphate">Geranyl pyrophosphate</a></li> <li><a href="/wiki/Halomon" title="Halomon">Halomon</a></li> <li><a href="/wiki/Linalool" title="Linalool">Linalool</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Monocyclic</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/Grapefruit_mercaptan" title="Grapefruit mercaptan">Grapefruit mercaptan</a></li> <li><a href="/wiki/Menthol" title="Menthol">Menthol</a></li> <li><a href="/wiki/P-Cymene" title="P-Cymene">p-Cymene</a></li> <li><a href="/wiki/Thujaplicin" title="Thujaplicin">Thujaplicins</a> (<a href="/wiki/Hinokitiol" title="Hinokitiol">Hinokitiol</a>)</li> <li><a class="mw-selflink selflink">Thymol</a></li> <li><a href="/wiki/Perillyl_alcohol" title="Perillyl alcohol">Perillyl alcohol</a></li> <li><a href="/wiki/Carvacrol" title="Carvacrol">Carvacrol</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Bicyclic</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/Camphor" title="Camphor">Camphor</a></li> <li><a href="/wiki/Borneol" title="Borneol">Borneol</a></li> <li><a href="/wiki/Bornyl_acetate" title="Bornyl acetate">Bornyl acetate</a></li> <li><a href="/wiki/Eucalyptol" title="Eucalyptol">Eucalyptol</a></li> <li><a href="/wiki/Ascaridole" title="Ascaridole">Ascaridole</a></li> <li><a href="/wiki/Umbellulone" title="Umbellulone">Umbellulone</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/Sesquiterpenoids" class="mw-redirect" title="Sesquiterpenoids">Sesquiterpenoids</a> (3)</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Artemisinin" title="Artemisinin">Artemisinin</a></li> <li><a href="/wiki/Bisabolol" title="Bisabolol">Bisabolol</a></li> <li><a href="/wiki/Cadinene" class="mw-redirect" title="Cadinene">Cadinene</a></li> <li><a href="/wiki/Cadinol" title="Cadinol">Cadinol</a></li> <li><a href="/wiki/Cedrene" title="Cedrene">Cedrene</a></li> <li>Chanootin</li> <li><a href="/wiki/Farnesyl_pyrophosphate" title="Farnesyl pyrophosphate">Farnesyl pyrophosphate</a></li> <li>Juniperol</li> <li><a href="/wiki/Longifolene" title="Longifolene">Longifolene</a></li> <li>Muurolene</li> <li>Nootkatin</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Terpenoid" title="Terpenoid">Diterpenoids</a> (4)</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%">Acyclic</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/Phytol" title="Phytol">Phytol</a></li> <li><a href="/wiki/Geranylgeranyl_pyrophosphate" title="Geranylgeranyl pyrophosphate">Geranylgeranyl pyrophosphate</a></li> <li>Geranyl-linalool</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Monocyclic</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/Retinol" title="Retinol">Retinol</a></li> <li><a href="/wiki/Retinal" title="Retinal">Retinal</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Bicyclic</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i>cis</i>-Abienol</li> <li>Epimanool</li> <li><a href="/wiki/Salvinorin_A" title="Salvinorin A">Salvinorin A</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Tricyclic</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/Cembrene" class="mw-redirect" title="Cembrene">Cembrene</a></li> <li><a href="/wiki/Forskolin" title="Forskolin">Forskolin</a></li> <li>Manoyl oxide</li> <li>Pimaral</li> <li>Pimarol</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Tetracyclic</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/Aphidicolin" title="Aphidicolin">Aphidicolin</a></li> <li><a href="/wiki/Gibberellin" title="Gibberellin">Gibberellin</a></li> <li><a href="/wiki/Paclitaxel" title="Paclitaxel">Paclitaxel</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Resin_acid" title="Resin acid">Resin acids</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/Abietic_acid" title="Abietic acid">Abietic acid</a></li> <li>Communic acid</li> <li>Dehydroabietic acid</li> <li><a href="/wiki/Isopimaric_acid" title="Isopimaric acid">Isopimaric acid</a></li> <li>Lambertianic acid</li> <li><a href="/wiki/Levopimaric_acid" title="Levopimaric acid">Levopimaric acid</a></li> <li>Mercusic acid</li> <li>Neoabietic acid</li> <li><a href="/wiki/Pimaric_acid" title="Pimaric acid">Pimaric acid</a></li> <li>Sandaracopimaric acid</li> <li>Secodehydroabietic acid</li> <li>Palustric acid</li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Sesterterpenoid" class="mw-redirect" title="Sesterterpenoid">Sesterterpenoids</a> (5)</th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li>Geranylfarnesol</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Triterpenoid" class="mw-redirect" title="Triterpenoid">Triterpenoids</a> (6)</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Steroid" title="Steroid">Steroids</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/Phytosterol" title="Phytosterol">Phytosterols</a> <ul><li><a href="/wiki/Campesterol" title="Campesterol">Campesterol</a></li> <li>Citrostadienol</li> <li><a href="/wiki/Cycloartenol" title="Cycloartenol">Cycloartenol</a></li> <li><a href="/wiki/Sitostanol" class="mw-redirect" title="Sitostanol">Sitostanol</a></li> <li><a href="/wiki/Sitosterol" class="mw-redirect" title="Sitosterol">Sitosterol</a></li> <li><a href="/wiki/Stigmasterol" title="Stigmasterol">Stigmasterol</a></li></ul></li> <li><a href="/wiki/Tocopherol" title="Tocopherol">Tocopherols</a></li> <li><a href="/wiki/Cholesterol" title="Cholesterol">Cholesterol</a></li> <li><a href="/wiki/Testosterone" title="Testosterone">Testosterone</a></li> <li><a href="/wiki/Cholecalciferol" title="Cholecalciferol">Cholecalciferol</a></li> <li><a href="/wiki/Ecdysone" title="Ecdysone">Ecdysones</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/Betulin" title="Betulin">Betulin</a></li> <li><a href="/wiki/Lanosterol" title="Lanosterol">Lanosterol</a></li> <li><a href="/wiki/Saponin" title="Saponin">Saponins</a></li> <li>Serratenediol</li> <li><a href="/wiki/Squalane" title="Squalane">Squalane</a></li> <li>Acids <ul><li><a href="/wiki/Oleanolic_acid" title="Oleanolic acid">Oleanolic acid</a></li> <li><a href="/wiki/Ursolic_acid" title="Ursolic acid">Ursolic acid</a></li> <li><a href="/wiki/Betulinic_acid" title="Betulinic acid">Betulinic acid</a></li> <li><a href="/wiki/Moronic_acid" title="Moronic acid">Moronic acid</a></li></ul></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Sesquarterpenes/oids (7)</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li>Ferrugicadiol</li> <li>Tetraprenylcurcumene</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Tetraterpenoid" class="mw-redirect" title="Tetraterpenoid">Tetraterpenoids</a><br />(<a href="/wiki/Carotenoid" title="Carotenoid">Carotenoids</a>) (8)</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Carotene" title="Carotene">Carotenes</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Alpha-Carotene" class="mw-redirect" title="Alpha-Carotene">Alpha-Carotene</a></li> <li><a href="/wiki/Beta-Carotene" class="mw-redirect" title="Beta-Carotene">Beta-Carotene</a></li> <li><a href="/wiki/Gamma-Carotene" class="mw-redirect" title="Gamma-Carotene">Gamma-Carotene</a></li> <li><a href="/wiki/Delta-Carotene" class="mw-redirect" title="Delta-Carotene">Delta-Carotene</a></li> <li><a href="/wiki/Lycopene" title="Lycopene">Lycopene</a></li> <li><a href="/wiki/Neurosporene" title="Neurosporene">Neurosporene</a></li> <li><a href="/wiki/Phytofluene" title="Phytofluene">Phytofluene</a></li> <li><a href="/wiki/Phytoene" title="Phytoene">Phytoene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Xanthophyll" title="Xanthophyll">Xanthophylls</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/Canthaxanthin" title="Canthaxanthin">Canthaxanthin</a></li> <li><a href="/wiki/Cryptoxanthin" class="mw-redirect" title="Cryptoxanthin">Cryptoxanthin</a></li> <li><a href="/wiki/Zeaxanthin" title="Zeaxanthin">Zeaxanthin</a></li> <li><a href="/wiki/Astaxanthin" title="Astaxanthin">Astaxanthin</a></li> <li><a href="/wiki/Lutein" title="Lutein">Lutein</a></li> <li><a href="/wiki/Rubixanthin" title="Rubixanthin">Rubixanthin</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/Polyterpenoid" class="mw-redirect" title="Polyterpenoid">Polyterpenoids</a> (many)</th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Natural_rubber" title="Natural rubber">Natural rubber</a></li> <li><a href="/wiki/Gutta_percha" class="mw-redirect" title="Gutta percha">Gutta percha</a></li> <li>Gutta-balatá</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Norisoprenoids (modified)</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li>3-oxo-α-ionol</li> <li>7,8-dihydroionone</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Synthesis</th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li>Terpene synthase enzymes (many), having in common a <a href="/wiki/Terpene_synthase_N_terminal_domain" title="Terpene synthase N terminal domain">terpene synthase N terminal domain</a> (<a href="/wiki/Protein_domain" title="Protein domain">protein domain</a>)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Activated isoprene forms</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Isopentenyl_pyrophosphate" title="Isopentenyl pyrophosphate">Isopentenyl pyrophosphate</a> (IPP)</li> <li><a href="/wiki/Dimethylallyl_pyrophosphate" title="Dimethylallyl pyrophosphate">Dimethylallyl pyrophosphate</a> (DMAPP)</li></ul> </div></td></tr></tbody></table></div>    </div><noscript><img src="https://login.wikimedia.org/wiki/Special:CentralAutoLogin/start?useformat=desktop&type=1x1&usesul3=0" alt="" width="1" height="1" style="border: none; position: absolute;"></noscript> <div class="printfooter" data-nosnippet="">Retrieved from "<a dir="ltr" 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