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<ul id="toc-Production-sublist" class="vector-toc-list"> <li id="toc-Deuterochloroform" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Deuterochloroform"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.1</span> <span>Deuterochloroform</span> </div> </a> <ul id="toc-Deuterochloroform-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Inadvertent_formation_of_chloroform" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Inadvertent_formation_of_chloroform"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.2</span> <span>Inadvertent formation of chloroform</span> </div> </a> <ul id="toc-Inadvertent_formation_of_chloroform-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Uses" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Uses"> <div class="vector-toc-text"> <span class="vector-toc-numb">5</span> <span>Uses</span> </div> </a> <button aria-controls="toc-Uses-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 Uses subsection</span> </button> <ul id="toc-Uses-sublist" class="vector-toc-list"> <li id="toc-Solvent" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Solvent"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.1</span> <span>Solvent</span> </div> </a> <ul id="toc-Solvent-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Refrigerant" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Refrigerant"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.2</span> <span>Refrigerant</span> </div> </a> <ul id="toc-Refrigerant-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Lewis_acid" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Lewis_acid"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.3</span> <span>Lewis acid</span> </div> </a> <ul id="toc-Lewis_acid-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Reagent" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Reagent"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.4</span> <span>Reagent</span> </div> </a> <ul id="toc-Reagent-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Anaesthetic" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Anaesthetic"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.5</span> <span>Anaesthetic</span> </div> </a> <ul id="toc-Anaesthetic-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Criminal_use" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Criminal_use"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.6</span> <span>Criminal use</span> </div> </a> <ul id="toc-Criminal_use-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Safety" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Safety"> <div class="vector-toc-text"> <span class="vector-toc-numb">6</span> <span>Safety</span> </div> </a> <button aria-controls="toc-Safety-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 Safety subsection</span> </button> <ul id="toc-Safety-sublist" class="vector-toc-list"> <li id="toc-Exposure" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Exposure"> <div class="vector-toc-text"> <span class="vector-toc-numb">6.1</span> <span>Exposure</span> </div> </a> <ul id="toc-Exposure-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Pharmacology" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Pharmacology"> <div class="vector-toc-text"> <span class="vector-toc-numb">6.2</span> <span>Pharmacology</span> </div> </a> <ul id="toc-Pharmacology-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Conversion_to_phosgene" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Conversion_to_phosgene"> <div class="vector-toc-text"> <span class="vector-toc-numb">6.3</span> <span>Conversion to phosgene</span> </div> </a> <ul id="toc-Conversion_to_phosgene-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Regulation" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Regulation"> <div class="vector-toc-text"> <span class="vector-toc-numb">6.4</span> <span>Regulation</span> </div> </a> <ul id="toc-Regulation-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Bioremediation_of_chloroform" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Bioremediation_of_chloroform"> <div class="vector-toc-text"> <span class="vector-toc-numb">7</span> <span>Bioremediation of chloroform</span> </div> </a> <ul id="toc-Bioremediation_of_chloroform-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Gallery" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Gallery"> <div class="vector-toc-text"> <span class="vector-toc-numb">8</span> <span>Gallery</span> </div> </a> <ul id="toc-Gallery-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-References" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#References"> <div class="vector-toc-text"> <span class="vector-toc-numb">9</span> <span>References</span> </div> </a> <ul id="toc-References-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-External_links" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#External_links"> <div class="vector-toc-text"> <span class="vector-toc-numb">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" > <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">Chloroform</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 65 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-65" 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">65 languages</span> </label> <div class="vector-dropdown-content"> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li class="interlanguage-link interwiki-af mw-list-item"><a href="https://af.wikipedia.org/wiki/Chloroform" title="Chloroform – Afrikaans" lang="af" hreflang="af" data-title="Chloroform" data-language-autonym="Afrikaans" data-language-local-name="Afrikaans" class="interlanguage-link-target"><span>Afrikaans</span></a></li><li class="interlanguage-link interwiki-ar mw-list-item"><a href="https://ar.wikipedia.org/wiki/%D9%83%D9%84%D9%88%D8%B1%D9%88%D9%81%D9%88%D8%B1%D9%85" title="كلوروفورم – Arabic" lang="ar" hreflang="ar" data-title="كلوروفورم" data-language-autonym="العربية" data-language-local-name="Arabic" class="interlanguage-link-target"><span>العربية</span></a></li><li class="interlanguage-link interwiki-az mw-list-item"><a href="https://az.wikipedia.org/wiki/Xloroform" title="Xloroform – Azerbaijani" lang="az" hreflang="az" data-title="Xloroform" data-language-autonym="Azərbaycanca" data-language-local-name="Azerbaijani" class="interlanguage-link-target"><span>Azərbaycanca</span></a></li><li class="interlanguage-link interwiki-azb mw-list-item"><a href="https://azb.wikipedia.org/wiki/%DA%A9%D9%88%D9%84%D9%88%D8%B1%D9%88%D9%81%D8%B1%D9%85" title="کولوروفرم – South Azerbaijani" lang="azb" hreflang="azb" data-title="کولوروفرم" data-language-autonym="تۆرکجه" data-language-local-name="South Azerbaijani" class="interlanguage-link-target"><span>تۆرکجه</span></a></li><li class="interlanguage-link interwiki-bn mw-list-item"><a href="https://bn.wikipedia.org/wiki/%E0%A6%95%E0%A7%8D%E0%A6%B2%E0%A7%8B%E0%A6%B0%E0%A7%8B%E0%A6%AB%E0%A6%B0%E0%A6%AE" title="ক্লোরোফরম – Bangla" lang="bn" hreflang="bn" data-title="ক্লোরোফরম" data-language-autonym="বাংলা" data-language-local-name="Bangla" class="interlanguage-link-target"><span>বাংলা</span></a></li><li class="interlanguage-link interwiki-be mw-list-item"><a href="https://be.wikipedia.org/wiki/%D0%A5%D0%BB%D0%B0%D1%80%D0%B0%D1%84%D0%BE%D1%80%D0%BC" title="Хлараформ – Belarusian" lang="be" hreflang="be" data-title="Хлараформ" data-language-autonym="Беларуская" data-language-local-name="Belarusian" class="interlanguage-link-target"><span>Беларуская</span></a></li><li class="interlanguage-link interwiki-be-x-old mw-list-item"><a href="https://be-tarask.wikipedia.org/wiki/%D0%A5%D0%BB%D1%8F%D1%80%D0%B0%D1%84%D0%BE%D1%80%D0%BC" title="Хляраформ – Belarusian (Taraškievica orthography)" lang="be-tarask" hreflang="be-tarask" data-title="Хляраформ" data-language-autonym="Беларуская (тарашкевіца)" data-language-local-name="Belarusian (Taraškievica orthography)" class="interlanguage-link-target"><span>Беларуская (тарашкевіца)</span></a></li><li class="interlanguage-link interwiki-bg mw-list-item"><a href="https://bg.wikipedia.org/wiki/%D0%A5%D0%BB%D0%BE%D1%80%D0%BE%D1%84%D0%BE%D1%80%D0%BC" title="Хлороформ – Bulgarian" lang="bg" hreflang="bg" data-title="Хлороформ" data-language-autonym="Български" data-language-local-name="Bulgarian" class="interlanguage-link-target"><span>Български</span></a></li><li class="interlanguage-link interwiki-bs mw-list-item"><a href="https://bs.wikipedia.org/wiki/Hloroform" title="Hloroform – Bosnian" lang="bs" hreflang="bs" data-title="Hloroform" data-language-autonym="Bosanski" data-language-local-name="Bosnian" class="interlanguage-link-target"><span>Bosanski</span></a></li><li class="interlanguage-link interwiki-ca mw-list-item"><a href="https://ca.wikipedia.org/wiki/Cloroform" title="Cloroform – Catalan" lang="ca" hreflang="ca" data-title="Cloroform" 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/Chloroform" title="Chloroform – Czech" lang="cs" hreflang="cs" data-title="Chloroform" data-language-autonym="Čeština" data-language-local-name="Czech" class="interlanguage-link-target"><span>Čeština</span></a></li><li class="interlanguage-link interwiki-da mw-list-item"><a href="https://da.wikipedia.org/wiki/Kloroform" title="Kloroform – Danish" lang="da" hreflang="da" data-title="Kloroform" data-language-autonym="Dansk" data-language-local-name="Danish" class="interlanguage-link-target"><span>Dansk</span></a></li><li class="interlanguage-link interwiki-de mw-list-item"><a href="https://de.wikipedia.org/wiki/Chloroform" title="Chloroform – German" lang="de" hreflang="de" data-title="Chloroform" data-language-autonym="Deutsch" data-language-local-name="German" class="interlanguage-link-target"><span>Deutsch</span></a></li><li class="interlanguage-link interwiki-et mw-list-item"><a href="https://et.wikipedia.org/wiki/Kloroform" title="Kloroform – Estonian" lang="et" hreflang="et" data-title="Kloroform" data-language-autonym="Eesti" data-language-local-name="Estonian" class="interlanguage-link-target"><span>Eesti</span></a></li><li class="interlanguage-link interwiki-el mw-list-item"><a href="https://el.wikipedia.org/wiki/%CE%A7%CE%BB%CF%89%CF%81%CE%BF%CF%86%CF%8C%CF%81%CE%BC%CE%B9%CE%BF" title="Χλωροφόρμιο – Greek" lang="el" hreflang="el" data-title="Χλωροφόρμιο" 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/Cloroformo" title="Cloroformo – Spanish" lang="es" hreflang="es" data-title="Cloroformo" 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/Kloroformo" title="Kloroformo – Esperanto" lang="eo" hreflang="eo" data-title="Kloroformo" data-language-autonym="Esperanto" data-language-local-name="Esperanto" class="interlanguage-link-target"><span>Esperanto</span></a></li><li class="interlanguage-link interwiki-eu mw-list-item"><a href="https://eu.wikipedia.org/wiki/Kloroformo" title="Kloroformo – Basque" lang="eu" hreflang="eu" data-title="Kloroformo" data-language-autonym="Euskara" data-language-local-name="Basque" class="interlanguage-link-target"><span>Euskara</span></a></li><li class="interlanguage-link interwiki-fa mw-list-item"><a href="https://fa.wikipedia.org/wiki/%DA%A9%D9%84%D8%B1%D9%88%D9%81%D8%B1%D9%85" title="کلروفرم – Persian" lang="fa" hreflang="fa" data-title="کلروفرم" 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/Chloroforme" title="Chloroforme – French" lang="fr" hreflang="fr" data-title="Chloroforme" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target"><span>Français</span></a></li><li class="interlanguage-link interwiki-ga mw-list-item"><a href="https://ga.wikipedia.org/wiki/Cl%C3%B3raform" title="Clóraform – Irish" lang="ga" hreflang="ga" data-title="Clóraform" data-language-autonym="Gaeilge" data-language-local-name="Irish" class="interlanguage-link-target"><span>Gaeilge</span></a></li><li class="interlanguage-link interwiki-gl mw-list-item"><a href="https://gl.wikipedia.org/wiki/Cloroformo" title="Cloroformo – Galician" lang="gl" hreflang="gl" data-title="Cloroformo" data-language-autonym="Galego" data-language-local-name="Galician" class="interlanguage-link-target"><span>Galego</span></a></li><li class="interlanguage-link interwiki-ko mw-list-item"><a href="https://ko.wikipedia.org/wiki/%ED%81%B4%EB%A1%9C%EB%A1%9C%ED%8F%AC%EB%A6%84" title="클로로포름 – Korean" lang="ko" hreflang="ko" data-title="클로로포름" data-language-autonym="한국어" data-language-local-name="Korean" class="interlanguage-link-target"><span>한국어</span></a></li><li class="interlanguage-link interwiki-hy mw-list-item"><a href="https://hy.wikipedia.org/wiki/%D5%94%D5%AC%D5%B8%D6%80%D5%B8%D6%86%D5%B8%D6%80%D5%B4" title="Քլորոֆորմ – Armenian" lang="hy" hreflang="hy" data-title="Քլորոֆորմ" 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%95%E0%A5%8D%E0%A4%B2%E0%A5%8B%E0%A4%B0%E0%A5%8B%E0%A4%AB%E0%A5%89%E0%A4%B0%E0%A5%8D%E0%A4%AE" title="क्लोरोफॉर्म – Hindi" lang="hi" hreflang="hi" data-title="क्लोरोफॉर्म" data-language-autonym="हिन्दी" data-language-local-name="Hindi" class="interlanguage-link-target"><span>हिन्दी</span></a></li><li class="interlanguage-link interwiki-hr mw-list-item"><a href="https://hr.wikipedia.org/wiki/Kloroform" title="Kloroform – Croatian" lang="hr" hreflang="hr" data-title="Kloroform" data-language-autonym="Hrvatski" data-language-local-name="Croatian" class="interlanguage-link-target"><span>Hrvatski</span></a></li><li class="interlanguage-link interwiki-io mw-list-item"><a href="https://io.wikipedia.org/wiki/Kloroformo" title="Kloroformo – Ido" lang="io" hreflang="io" data-title="Kloroformo" data-language-autonym="Ido" data-language-local-name="Ido" class="interlanguage-link-target"><span>Ido</span></a></li><li class="interlanguage-link interwiki-id mw-list-item"><a href="https://id.wikipedia.org/wiki/Kloroform" title="Kloroform – Indonesian" lang="id" hreflang="id" data-title="Kloroform" 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/Cloroformio" title="Cloroformio – Italian" lang="it" hreflang="it" data-title="Cloroformio" 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%9B%D7%9C%D7%95%D7%A8%D7%95%D7%A4%D7%95%D7%A8%D7%9D" title="כלורופורם – Hebrew" lang="he" hreflang="he" data-title="כלורופורם" data-language-autonym="עברית" data-language-local-name="Hebrew" class="interlanguage-link-target"><span>עברית</span></a></li><li class="interlanguage-link interwiki-kk mw-list-item"><a href="https://kk.wikipedia.org/wiki/%D0%A5%D0%BB%D0%BE%D1%80%D0%BE%D1%84%D0%BE%D1%80%D0%BC" title="Хлороформ – Kazakh" lang="kk" hreflang="kk" data-title="Хлороформ" data-language-autonym="Қазақша" data-language-local-name="Kazakh" class="interlanguage-link-target"><span>Қазақша</span></a></li><li class="interlanguage-link interwiki-ku mw-list-item"><a href="https://ku.wikipedia.org/wiki/Kloroform" title="Kloroform – Kurdish" lang="ku" hreflang="ku" data-title="Kloroform" data-language-autonym="Kurdî" data-language-local-name="Kurdish" class="interlanguage-link-target"><span>Kurdî</span></a></li><li class="interlanguage-link interwiki-ky mw-list-item"><a href="https://ky.wikipedia.org/wiki/%D0%A5%D0%BB%D0%BE%D1%80%D0%BE%D1%84%D0%BE%D1%80%D0%BC" title="Хлороформ – Kyrgyz" lang="ky" hreflang="ky" data-title="Хлороформ" 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/Hloroforms" title="Hloroforms – Latvian" lang="lv" hreflang="lv" data-title="Hloroforms" data-language-autonym="Latviešu" data-language-local-name="Latvian" class="interlanguage-link-target"><span>Latviešu</span></a></li><li class="interlanguage-link interwiki-lb mw-list-item"><a href="https://lb.wikipedia.org/wiki/Chloroform" title="Chloroform – Luxembourgish" lang="lb" hreflang="lb" data-title="Chloroform" data-language-autonym="Lëtzebuergesch" data-language-local-name="Luxembourgish" class="interlanguage-link-target"><span>Lëtzebuergesch</span></a></li><li class="interlanguage-link interwiki-hu mw-list-item"><a href="https://hu.wikipedia.org/wiki/Kloroform" title="Kloroform – Hungarian" lang="hu" hreflang="hu" data-title="Kloroform" data-language-autonym="Magyar" data-language-local-name="Hungarian" class="interlanguage-link-target"><span>Magyar</span></a></li><li class="interlanguage-link interwiki-mk mw-list-item"><a href="https://mk.wikipedia.org/wiki/%D0%A5%D0%BB%D0%BE%D1%80%D0%BE%D1%84%D0%BE%D1%80%D0%BC" title="Хлороформ – Macedonian" lang="mk" hreflang="mk" data-title="Хлороформ" data-language-autonym="Македонски" data-language-local-name="Macedonian" class="interlanguage-link-target"><span>Македонски</span></a></li><li class="interlanguage-link interwiki-ms mw-list-item"><a href="https://ms.wikipedia.org/wiki/Kloroform" title="Kloroform – Malay" lang="ms" hreflang="ms" data-title="Kloroform" data-language-autonym="Bahasa Melayu" data-language-local-name="Malay" class="interlanguage-link-target"><span>Bahasa Melayu</span></a></li><li class="interlanguage-link interwiki-my mw-list-item"><a href="https://my.wikipedia.org/wiki/%E1%80%80%E1%80%9C%E1%80%AD%E1%80%AF%E1%80%9B%E1%80%AD%E1%80%AF%E1%80%96%E1%80%B1%E1%80%AC%E1%80%84%E1%80%BA%E1%80%B8" title="ကလိုရိုဖောင်း – Burmese" lang="my" hreflang="my" data-title="ကလိုရိုဖောင်း" data-language-autonym="မြန်မာဘာသာ" data-language-local-name="Burmese" class="interlanguage-link-target"><span>မြန်မာဘာသာ</span></a></li><li class="interlanguage-link interwiki-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/Chloroform" title="Chloroform – Dutch" lang="nl" hreflang="nl" data-title="Chloroform" data-language-autonym="Nederlands" data-language-local-name="Dutch" class="interlanguage-link-target"><span>Nederlands</span></a></li><li class="interlanguage-link interwiki-ja mw-list-item"><a href="https://ja.wikipedia.org/wiki/%E3%82%AF%E3%83%AD%E3%83%AD%E3%83%9B%E3%83%AB%E3%83%A0" title="クロロホルム – Japanese" lang="ja" hreflang="ja" data-title="クロロホルム" data-language-autonym="日本語" data-language-local-name="Japanese" class="interlanguage-link-target"><span>日本語</span></a></li><li class="interlanguage-link interwiki-no mw-list-item"><a href="https://no.wikipedia.org/wiki/Kloroform" title="Kloroform – Norwegian Bokmål" lang="nb" hreflang="nb" data-title="Kloroform" data-language-autonym="Norsk bokmål" data-language-local-name="Norwegian Bokmål" class="interlanguage-link-target"><span>Norsk bokmål</span></a></li><li class="interlanguage-link interwiki-uz mw-list-item"><a href="https://uz.wikipedia.org/wiki/Xloroform" title="Xloroform – Uzbek" lang="uz" hreflang="uz" data-title="Xloroform" data-language-autonym="Oʻzbekcha / ўзбекча" data-language-local-name="Uzbek" class="interlanguage-link-target"><span>Oʻzbekcha / ўзбекча</span></a></li><li class="interlanguage-link interwiki-blk mw-list-item"><a href="https://blk.wikipedia.org/wiki/%E1%80%80%E1%80%9C%E1%80%AD%E1%80%AF%E1%80%9B%E1%80%AD%E1%80%AF%E1%80%96%E1%80%B1%E1%80%AC%E1%80%84%E1%80%BA%E1%80%B8" title="ကလိုရိုဖောင်း – Pa'O" lang="blk" hreflang="blk" data-title="ကလိုရိုဖောင်း" data-language-autonym="ပအိုဝ်ႏဘာႏသာႏ" data-language-local-name="Pa'O" class="interlanguage-link-target"><span>ပအိုဝ်ႏဘာႏသာႏ</span></a></li><li class="interlanguage-link interwiki-pl mw-list-item"><a href="https://pl.wikipedia.org/wiki/Chloroform" title="Chloroform – Polish" lang="pl" hreflang="pl" data-title="Chloroform" 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/Clorof%C3%B3rmio" title="Clorofórmio – Portuguese" lang="pt" hreflang="pt" data-title="Clorofórmio" 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/Cloroform" title="Cloroform – Romanian" lang="ro" hreflang="ro" data-title="Cloroform" 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%A5%D0%BB%D0%BE%D1%80%D0%BE%D1%84%D0%BE%D1%80%D0%BC" title="Хлороформ – Russian" lang="ru" hreflang="ru" data-title="Хлороформ" data-language-autonym="Русский" data-language-local-name="Russian" class="interlanguage-link-target"><span>Русский</span></a></li><li class="interlanguage-link interwiki-sq mw-list-item"><a href="https://sq.wikipedia.org/wiki/Kloroformi" title="Kloroformi – Albanian" lang="sq" hreflang="sq" data-title="Kloroformi" data-language-autonym="Shqip" data-language-local-name="Albanian" class="interlanguage-link-target"><span>Shqip</span></a></li><li class="interlanguage-link interwiki-simple mw-list-item"><a href="https://simple.wikipedia.org/wiki/Chloroform" title="Chloroform – Simple English" lang="en-simple" hreflang="en-simple" data-title="Chloroform" data-language-autonym="Simple English" data-language-local-name="Simple English" class="interlanguage-link-target"><span>Simple English</span></a></li><li class="interlanguage-link interwiki-sk mw-list-item"><a href="https://sk.wikipedia.org/wiki/Trichl%C3%B3rmet%C3%A1n" title="Trichlórmetán – Slovak" lang="sk" hreflang="sk" data-title="Trichlórmetán" data-language-autonym="Slovenčina" data-language-local-name="Slovak" class="interlanguage-link-target"><span>Slovenčina</span></a></li><li class="interlanguage-link interwiki-sl mw-list-item"><a href="https://sl.wikipedia.org/wiki/Kloroform" title="Kloroform – Slovenian" lang="sl" hreflang="sl" data-title="Kloroform" data-language-autonym="Slovenščina" data-language-local-name="Slovenian" class="interlanguage-link-target"><span>Slovenščina</span></a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/%D0%A5%D0%BB%D0%BE%D1%80%D0%BE%D1%84%D0%BE%D1%80%D0%BC" title="Хлороформ – Serbian" lang="sr" hreflang="sr" data-title="Хлороформ" 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/Kloroform" title="Kloroform – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Kloroform" 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/Kloroformi" title="Kloroformi – Finnish" lang="fi" hreflang="fi" data-title="Kloroformi" 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/Kloroform" title="Kloroform – Swedish" lang="sv" hreflang="sv" data-title="Kloroform" data-language-autonym="Svenska" data-language-local-name="Swedish" class="interlanguage-link-target"><span>Svenska</span></a></li><li class="interlanguage-link interwiki-ta mw-list-item"><a href="https://ta.wikipedia.org/wiki/%E0%AE%95%E0%AF%81%E0%AE%B3%E0%AF%8B%E0%AE%B0%E0%AF%8B%E0%AE%AA%E0%AE%BE%E0%AE%B0%E0%AE%AE%E0%AF%8D" title="குளோரோபாரம் – Tamil" lang="ta" hreflang="ta" data-title="குளோரோபாரம்" data-language-autonym="தமிழ்" data-language-local-name="Tamil" class="interlanguage-link-target"><span>தமிழ்</span></a></li><li class="interlanguage-link interwiki-te mw-list-item"><a href="https://te.wikipedia.org/wiki/%E0%B0%95%E0%B1%8D%E0%B0%B2%E0%B1%8B%E0%B0%B0%E0%B1%8B%E0%B0%AB%E0%B0%BE%E0%B0%AE%E0%B1%8D" title="క్లోరోఫామ్ – Telugu" lang="te" hreflang="te" data-title="క్లోరోఫామ్" data-language-autonym="తెలుగు" data-language-local-name="Telugu" class="interlanguage-link-target"><span>తెలుగు</span></a></li><li class="interlanguage-link interwiki-th mw-list-item"><a href="https://th.wikipedia.org/wiki/%E0%B8%84%E0%B8%A5%E0%B8%AD%E0%B9%82%E0%B8%A3%E0%B8%9F%E0%B8%AD%E0%B8%A3%E0%B9%8C%E0%B8%A1" title="คลอโรฟอร์ม – Thai" lang="th" hreflang="th" data-title="คลอโรฟอร์ม" data-language-autonym="ไทย" data-language-local-name="Thai" class="interlanguage-link-target"><span>ไทย</span></a></li><li class="interlanguage-link interwiki-tr badge-Q17437796 badge-featuredarticle mw-list-item" title="featured article badge"><a href="https://tr.wikipedia.org/wiki/Kloroform" title="Kloroform – Turkish" lang="tr" hreflang="tr" data-title="Kloroform" data-language-autonym="Türkçe" data-language-local-name="Turkish" class="interlanguage-link-target"><span>Türkçe</span></a></li><li class="interlanguage-link interwiki-uk mw-list-item"><a href="https://uk.wikipedia.org/wiki/%D0%A5%D0%BB%D0%BE%D1%80%D0%BE%D1%84%D0%BE%D1%80%D0%BC" title="Хлороформ – Ukrainian" lang="uk" hreflang="uk" data-title="Хлороформ" data-language-autonym="Українська" data-language-local-name="Ukrainian" class="interlanguage-link-target"><span>Українська</span></a></li><li class="interlanguage-link interwiki-ur mw-list-item"><a href="https://ur.wikipedia.org/wiki/%DA%A9%D9%84%D9%88%D8%B1%D9%88%D9%81%D8%A7%D9%85" title="کلوروفام – Urdu" lang="ur" hreflang="ur" data-title="کلوروفام" data-language-autonym="اردو" data-language-local-name="Urdu" class="interlanguage-link-target"><span>اردو</span></a></li><li class="interlanguage-link interwiki-vi mw-list-item"><a href="https://vi.wikipedia.org/wiki/Chloroform" title="Chloroform – Vietnamese" lang="vi" hreflang="vi" data-title="Chloroform" data-language-autonym="Tiếng Việt" data-language-local-name="Vietnamese" class="interlanguage-link-target"><span>Tiếng Việt</span></a></li><li class="interlanguage-link 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.ambox{display:none!important}}</style><table class="box-Expand_language plainlinks metadata ambox ambox-notice skin-invert-image" role="presentation"><tbody><tr><td class="mbox-image"><div class="mbox-image-div"><span typeof="mw:File"><span><img alt="" src="//upload.wikimedia.org/wikipedia/commons/thumb/8/8a/Translation_to_english_arrow.svg/50px-Translation_to_english_arrow.svg.png" decoding="async" width="50" height="17" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/8/8a/Translation_to_english_arrow.svg/75px-Translation_to_english_arrow.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/8/8a/Translation_to_english_arrow.svg/100px-Translation_to_english_arrow.svg.png 2x" data-file-width="60" data-file-height="20" /></span></span></div></td><td class="mbox-text"><div class="mbox-text-span"><style data-mw-deduplicate="TemplateStyles:r1214851843">.mw-parser-output .hidden-begin{box-sizing:border-box;width:100%;padding:5px;border:none;font-size:95%}.mw-parser-output .hidden-title{font-weight:bold;line-height:1.6;text-align:left}.mw-parser-output .hidden-content{text-align:left}@media all and (max-width:500px){.mw-parser-output .hidden-begin{width:auto!important;clear:none!important;float:none!important}}</style><div class="hidden-begin mw-collapsible mw-collapsed" style="font-size:100%; padding: 0px;"><div class="hidden-title skin-nightmode-reset-color" style="text-align:center; padding-right: 3em; font-weight: normal; text-align: left">You can help <b>expand this article with text translated from <a href="https://tr.wikipedia.org/wiki/Kloroform" class="extiw" title="tr:Kloroform">the corresponding article</a> in Turkish</b>.  <i><small>(September 2024)</small></i> <small>Click [show] for important translation instructions.</small></div><div class="hidden-content mw-collapsible-content" style=""> <ul><li><a rel="nofollow" class="external text" href="https://translate.google.com/translate?&u=https%3A%2F%2Ftr.wikipedia.org%2Fwiki%2FKloroform&sl=tr&tl=en&prev=_t&hl=en">View</a> a machine-translated version of the Turkish article.</li> <li>Machine translation, like <a rel="nofollow" class="external text" href="https://deepl.com">DeepL</a> or <a rel="nofollow" class="external text" href="https://translate.google.com/">Google Translate</a>, is a useful starting point for translations, but translators must revise errors as necessary and confirm that the translation is accurate, rather than simply copy-pasting machine-translated text into the English Wikipedia.</li> <li>Do not translate text that appears unreliable or low-quality. If possible, verify the text with references provided in the foreign-language article.</li> <li>You <b>must</b> provide <a href="/wiki/Wikipedia:Copying_within_Wikipedia" title="Wikipedia:Copying within Wikipedia">copyright attribution</a> in the <a href="/wiki/Help:Edit_summary" title="Help:Edit summary">edit summary</a> accompanying your translation by providing an <a href="/wiki/Help:Interlanguage_links" title="Help:Interlanguage links">interlanguage link</a> to the source of your translation. A model attribution edit summary is <code>Content in this edit is translated from the existing Turkish Wikipedia article at [[:tr:Kloroform]]; see its history for attribution.</code></li> <li>You may also add the template <code>{{Translated|tr|Kloroform}}</code> to the <a href="/wiki/Talk:Chloroform" title="Talk:Chloroform">talk page</a>.</li> <li>For more guidance, see <a href="/wiki/Wikipedia:Translation" title="Wikipedia:Translation">Wikipedia:Translation</a>.</li></ul></div></div></div></td></tr></tbody></table> <style data-mw-deduplicate="TemplateStyles:r1084375498">.mw-parser-output .ib-chembox{border-collapse:collapse;text-align:left}.mw-parser-output .ib-chembox td,.mw-parser-output .ib-chembox th{border:1px solid #a2a9b1;width:40%}.mw-parser-output .ib-chembox td+td{width:60%}</style> <table class="infobox ib-chembox"> <caption>Chloroform </caption> <tbody><tr> <td colspan="2" class="borderless" style="text-align:center"> <table border="0" style="width:100%;display:inline-table;"> <tbody><tr> <td style="border-right:1px solid #aaa; width:50%;"><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Chloroform_displayed.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/9/9f/Chloroform_displayed.svg/110px-Chloroform_displayed.svg.png" decoding="async" width="110" height="103" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/9/9f/Chloroform_displayed.svg/165px-Chloroform_displayed.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/9/9f/Chloroform_displayed.svg/220px-Chloroform_displayed.svg.png 2x" data-file-width="640" data-file-height="600" /></a><figcaption></figcaption></figure> </td> <td style="width:50%;"><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Chloroform-3D-balls.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/2/25/Chloroform-3D-balls.png/110px-Chloroform-3D-balls.png" decoding="async" width="110" height="109" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/2/25/Chloroform-3D-balls.png/165px-Chloroform-3D-balls.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/2/25/Chloroform-3D-balls.png/220px-Chloroform-3D-balls.png 2x" data-file-width="1100" data-file-height="1091" /></a><figcaption></figcaption></figure> </td></tr></tbody></table> </td></tr> <tr> <td colspan="2" style="text-align:center; padding:2px;"><span typeof="mw:File"><a href="/wiki/File:Chloroform_by_Danny_S._-_002.JPG" class="mw-file-description" title="Chloroform in its liquid state shown in a test tube"><img alt="Chloroform in its liquid state shown in a test tube" src="//upload.wikimedia.org/wikipedia/commons/thumb/5/55/Chloroform_by_Danny_S._-_002.JPG/100px-Chloroform_by_Danny_S._-_002.JPG" decoding="async" width="100" height="150" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/5/55/Chloroform_by_Danny_S._-_002.JPG/150px-Chloroform_by_Danny_S._-_002.JPG 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/5/55/Chloroform_by_Danny_S._-_002.JPG/200px-Chloroform_by_Danny_S._-_002.JPG 2x" data-file-width="1116" data-file-height="1678" /></a></span> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Names </th></tr> <tr> <td colspan="2" style="text-align:left;"><a href="/wiki/Preferred_IUPAC_name" title="Preferred IUPAC name">Preferred IUPAC name</a> <div style="max-width:22em; word-wrap:break-word; padding-left:1.7em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0; max-width:22em;">Trichloromethane</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;"><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><i>Chloroformium</i></li><li>Freon 20</li><li>Methane trichloride</li><li>Methyl trichloride</li><li>Methenyl trichloride</li><li>Methenyl chloride</li><li>Refrigerant-20</li><li>terchloride/perchloride of formyle<sup id="cite_ref-1" class="reference"><a href="#cite_note-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup><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> <i>(archaic)</i></li><li><i>Trichloretum Formylicum</i> (<a href="/wiki/Latin" title="Latin">Latin</a>)</li></ul></div></div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Identifiers </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/CAS_Registry_Number" title="CAS Registry Number">CAS Number</a></div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="commonchemistry.cas.org"><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=67-66-3">67-66-3</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=ClC%28Cl%29Cl">Interactive image</a></span></li></ul></div> </td></tr> <tr> <td>Abbreviations </td> <td>R-20, TCM </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=35255">CHEBI:35255</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ChEMBL" title="ChEMBL">ChEMBL</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.ebi.ac.uk"><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chembldb/index.php/compound/inspect/ChEMBL44618">ChEMBL44618</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.5977.html">5977</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ECHA_InfoCard" class="mw-redirect" title="ECHA InfoCard"><span title="echa.europa.eu">ECHA InfoCard</span></a> </td> <td><a rel="nofollow" class="external text" href="https://echa.europa.eu/substance-information/-/substanceinfo/100.000.603">100.000.603</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q172275#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>200-663-8</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/C13827">C13827</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/6212">6212</a></span></li></ul></div> </td></tr> <tr> <td><a href="/wiki/RTECS" class="mw-redirect" title="RTECS">RTECS number</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li>FS9100000</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/7V31YC746X">7V31YC746X</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><a href="/wiki/UN_number" title="UN number">UN number</a> </td> <td>1888 </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/DTXSID1020306">DTXSID1020306</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q172275#P3117" title="Edit this at Wikidata"><img alt="Edit this at Wikidata" src="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/10px-OOjs_UI_icon_edit-ltr-progressive.svg.png" decoding="async" width="10" height="10" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/15px-OOjs_UI_icon_edit-ltr-progressive.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/20px-OOjs_UI_icon_edit-ltr-progressive.svg.png 2x" data-file-width="20" data-file-height="20" /></a></span></span></li></ul></div> </td></tr> <tr> <td colspan="2"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold; text-align:left; font-weight:normal; background:transparent;"><div><a href="/wiki/International_Chemical_Identifier" title="International Chemical Identifier">InChI</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.5em; text-align:left;"><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">InChI=1S/CHCl3/c2-1(3)4/h1H<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: HEDRZPFGACZZDS-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/CHCl3/c2-1(3)4/h1H</div><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">Key: HEDRZPFGACZZDS-UHFFFAOYAG</div></div></li></ul> </div> </td></tr> <tr> <td colspan="2"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold; text-align:left; font-weight:normal; background:transparent;"><div><a href="/wiki/Simplified_molecular-input_line-entry_system" class="mw-redirect" title="Simplified molecular-input line-entry system">SMILES</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.6em; word-wrap:break-word; text-indent:-1.5em; text-align:left; font-size:97%; line-height:120%;">ClC(Cl)Cl</div></li></ul> </div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Properties </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Chemical_formula" title="Chemical formula">Chemical formula</a></div> </td> <td><span title="Carbon">C</span><span title="Hydrogen">H</span><span title="Chlorine">Cl</span><sub>3</sub> </td></tr> <tr> <td><a href="/wiki/Molar_mass" title="Molar mass">Molar mass</a> </td> <td><span class="nowrap"><span data-sort-value="7002119370000000000♠"></span>119.37</span> g·mol<sup>−1</sup>   </td></tr> <tr> <td>Appearance </td> <td>Highly refractive colorless liquid </td></tr> <tr> <td><a href="/wiki/Odor" title="Odor">Odor</a> </td> <td>Sweet, minty, pleasant </td></tr> <tr> <td><a href="/wiki/Density" title="Density">Density</a> </td> <td>1.564 g/cm<sup>3</sup> (−20 °C)<br /> 1.489 g/cm<sup>3</sup> (25 °C)<br /> 1.394 g/cm<sup>3</sup> (60 °C) </td></tr> <tr> <td><a href="/wiki/Melting_point" title="Melting point">Melting point</a> </td> <td>−63.5 °C (−82.3 °F; 209.7 K) </td></tr> <tr> <td><a href="/wiki/Boiling_point" title="Boiling point">Boiling point</a> </td> <td>61.15 °C (142.07 °F; 334.30 K) <br /> decomposes at 450 °C </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>10.62 g/L (0 °C)<br /> 8.09 g/L (20 °C)<br /> 7.32 g/L (60 °C) </td></tr> <tr> <td><a href="/wiki/Solubility" title="Solubility">Solubility</a> </td> <td>Soluble in <a href="/wiki/Benzene" title="Benzene">benzene</a><br /> Miscible in <a href="/wiki/Diethyl_ether" title="Diethyl ether">diethyl ether</a>, <a href="/wiki/Oil" title="Oil">oils</a>, <a href="/wiki/Ligroin" title="Ligroin">ligroin</a>, <a href="/wiki/Ethanol" title="Ethanol">alcohol</a>, <a href="/wiki/Carbon_tetrachloride" title="Carbon tetrachloride">CCl<sub>4</sub></a>, <a href="/wiki/Carbon_disulfide" title="Carbon disulfide">CS<sub>2</sub></a> </td></tr> <tr> <td><a href="/wiki/Solubility" title="Solubility">Solubility</a> in <a href="/wiki/Acetone" title="Acetone">acetone</a> </td> <td>≥ 100 g/L (19 °C) </td></tr> <tr> <td><a href="/wiki/Solubility" title="Solubility">Solubility</a> in <a href="/wiki/Dimethyl_sulfoxide" title="Dimethyl sulfoxide">dimethyl sulfoxide</a> </td> <td>≥ 100 g/L (19 °C) </td></tr> <tr> <td><a href="/wiki/Vapor_pressure" title="Vapor pressure">Vapor pressure</a> </td> <td>0.62 kPa (−40 °C)<br /> 7.89 kPa (0 °C)<br /> 25.9 kPa (25 °C)<br /> 313 kPa (100 °C)<br /> 2.26 MPa (200 °C) </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Henry%27s_law" title="Henry's law">Henry's law<br />constant</a> (<i>k</i><sub>H</sub>)</div> </td> <td>3.67 L·atm/mol (24 °C) </td></tr> <tr> <td><a href="/wiki/Acid_dissociation_constant" title="Acid dissociation constant">Acidity</a> (p<i>K</i><sub>a</sub>) </td> <td>15.7 (20 °C) </td></tr> <tr> <td><a href="/wiki/Ultraviolet%E2%80%93visible_spectroscopy" title="Ultraviolet–visible spectroscopy">UV-vis</a> (λ<sub>max</sub>) </td> <td>250 nm, 260 nm, 280 nm </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Magnetic_susceptibility" title="Magnetic susceptibility">Magnetic susceptibility</a> (χ)</div> </td> <td>−59.30·10<sup>−6</sup> cm<sup>3</sup>/mol </td></tr> <tr> <td><a href="/wiki/Thermal_conductivity" class="mw-redirect" title="Thermal conductivity">Thermal conductivity</a> </td> <td>0.13 W/(m·K) (20 °C) </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>1.4459 (20 °C) </td></tr> <tr> <td><a href="/wiki/Viscosity" title="Viscosity">Viscosity</a> </td> <td>0.563 cP (20 °C) </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Structure </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Molecular_geometry" title="Molecular geometry">Molecular shape</a></div> </td> <td>Tetrahedral </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Dipole#Molecular_dipoles" title="Dipole">Dipole moment</a></div> </td> <td>1.15 D </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Thermochemistry </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Heat_capacity" title="Heat capacity">Heat capacity</a> <span style="font-size:112%;">(<i>C</i>)</span></div> </td> <td>114.25 J/(mol·K) </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Standard_molar_entropy" title="Standard molar entropy">Std molar<br />entropy</a> <span style="font-size:112%;">(<i>S</i><sup>⦵</sup><sub>298</sub>)</span></div> </td> <td>202.9 J/(mol·K) </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Standard_enthalpy_change_of_formation" class="mw-redirect" title="Standard enthalpy change of formation">Std enthalpy of<br />formation</a> <span style="font-size:112%;">(Δ<sub>f</sub><i>H</i><sup>⦵</sup><sub>298</sub>)</span></div> </td> <td>−134.3 kJ/mol </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Gibbs_free_energy#Standard_energy_change_of_formation" title="Gibbs free energy">Gibbs free energy</a> <span style="font-size:112%;">(Δ<sub>f</sub><i>G</i><sup>⦵</sup>)</span></div> </td> <td>−71.1 kJ/mol </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Standard_enthalpy_change_of_combustion" class="mw-redirect" title="Standard enthalpy change of combustion">Std enthalpy of<br />combustion</a> <span style="font-size:112%;">(Δ<sub>c</sub><i>H</i><sup>⦵</sup><sub>298</sub>)</span></div> </td> <td>473.21 kJ/mol </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Pharmacology </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Anatomical_Therapeutic_Chemical_Classification_System" title="Anatomical Therapeutic Chemical Classification System">ATC code</a></div> </td> <td><a href="/wiki/ATC_code_N01" title="ATC code N01">N01AB02</a> (<span title="www.whocc.no"><a rel="nofollow" class="external text" href="https://www.whocc.no/atc_ddd_index/?code=N01AB02">WHO</a></span>)  </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Hazards<sup id="cite_ref-PubChem_9-0" class="reference"><a href="#cite_note-PubChem-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> </th></tr> <tr> <td colspan="2" style="text-align:left; background-color:#eaeaea;"><b><a href="/wiki/Occupational_safety_and_health" title="Occupational safety and health">Occupational safety and health</a></b> (OHS/OSH): </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">Main hazards</div> </td> <td>Decomposes to extremely toxic <a href="/wiki/Phosgene" title="Phosgene">phosgene</a> and <a href="/wiki/Hydrogen_chloride" title="Hydrogen chloride">hydrogen chloride</a> in presence of light – possibly carcinogenic – <a href="/wiki/Reproductive_toxicity" title="Reproductive toxicity">Reproductive toxicity</a> – hepatotoxic<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><sup id="cite_ref-PGCH_4-0" class="reference"><a href="#cite_note-PGCH-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-:1_5-0" class="reference"><a href="#cite_note-:1-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td colspan="2" style="text-align:left; background-color:#eaeaea;"><a href="/wiki/Globally_Harmonized_System_of_Classification_and_Labelling_of_Chemicals" title="Globally Harmonized System of Classification and Labelling of Chemicals"><b>GHS</b> labelling</a>: </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/GHS_hazard_pictograms" title="GHS hazard pictograms">Pictograms</a></div> </td> <td><span typeof="mw:File"><a href="/wiki/File:GHS-pictogram-skull.svg" class="mw-file-description" title="GHS06: Toxic"><img alt="GHS06: Toxic" src="//upload.wikimedia.org/wikipedia/commons/thumb/5/58/GHS-pictogram-skull.svg/50px-GHS-pictogram-skull.svg.png" decoding="async" width="50" height="50" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/5/58/GHS-pictogram-skull.svg/75px-GHS-pictogram-skull.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/5/58/GHS-pictogram-skull.svg/100px-GHS-pictogram-skull.svg.png 2x" data-file-width="724" data-file-height="724" /></a></span> <span typeof="mw:File"><a href="/wiki/File:GHS-pictogram-silhouette.svg" class="mw-file-description" title="GHS08: Health hazard"><img alt="GHS08: Health hazard" src="//upload.wikimedia.org/wikipedia/commons/thumb/2/21/GHS-pictogram-silhouette.svg/50px-GHS-pictogram-silhouette.svg.png" decoding="async" width="50" height="50" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/2/21/GHS-pictogram-silhouette.svg/75px-GHS-pictogram-silhouette.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/2/21/GHS-pictogram-silhouette.svg/100px-GHS-pictogram-silhouette.svg.png 2x" data-file-width="724" data-file-height="724" /></a></span> <span typeof="mw:File"><a href="/wiki/File:GHS-pictogram-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> </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Globally_Harmonized_System_of_Classification_and_Labelling_of_Chemicals#Signal_word" title="Globally Harmonized System of Classification and Labelling of Chemicals">Signal word</a></div> </td> <td><b>Danger</b> </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/GHS_hazard_statements" title="GHS hazard statements">Hazard statements</a></div> </td> <td><abbr class="abbr" title="H302: Harmful if swallowed">H302</abbr>, <abbr class="abbr" title="H315: Causes skin irritation">H315</abbr>, <abbr class="abbr" title="H319: Causes serious eye irritation">H319</abbr>, <abbr class="abbr" title="H331: Toxic if inhaled">H331</abbr>, <abbr class="abbr" title="H336: May cause drowsiness or dizziness">H336</abbr>, <abbr class="abbr" title="H351: Suspected of causing cancer">H351</abbr>, <abbr class="abbr" title="H361d: Suspected of damaging the unborn child">H361d</abbr>, <abbr class="abbr" title="H372: Causes damage to organs through prolonged or repeated exposure">H372</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="P201: Obtain special instructions before use.">P201</abbr>, <abbr class="abbr" title="P202: Do not handle until all safety precautions have been read and understood.">P202</abbr>, <abbr class="abbr" title="P235: Keep cool.">P235</abbr>, <abbr class="abbr" title="P260: Do not breathe dust/fume/gas/mist/vapours/spray.">P260</abbr>, <abbr class="abbr" title="P264: Wash ... thoroughly after handling.">P264</abbr>, <abbr class="abbr" title="P270: Do not eat, drink or smoke when using this product.">P270</abbr>, <abbr class="abbr" title="P271: Use only outdoors or in a well-ventilated area.">P271</abbr>, <abbr class="abbr" title="P280: Wear protective gloves/protective clothing/eye protection/face protection.">P280</abbr>, <abbr class="abbr" title="P281: Use personal protective equipment as required.">P281</abbr>, <abbr class="abbr" title="P301+P330+P331: IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.">P301+P330+P331</abbr>, <abbr class="abbr" title="P302+P352: IF ON SKIN: Wash with soap and water.">P302+P352</abbr>, <abbr class="abbr" title="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="P308+P313: IF exposed or concerned: Get medical advice/attention.">P308+P313</abbr>, <abbr class="abbr" title="P310: Immediately call a POISON CENTER or doctor/physician.">P310</abbr>, <abbr class="abbr" title="P311: Call a POISON CENTER or doctor/physician.">P311</abbr>, <abbr class="abbr" title="P314: Get Medical advice/attention if you feel unwell.">P314</abbr>, <abbr class="abbr" title="P332+P313: If skin irritation occurs: Get medical advice/attention.">P332+P313</abbr>, <abbr class="abbr" title="P337+P313: If eye irritation persists: Get medical advice/attention.">P337+P313</abbr>, <abbr class="abbr" title="P362: Take off contaminated clothing.">P362</abbr>, <abbr class="abbr" title="P403+P233: Store in a well ventilated place. Keep container tightly closed.">P403+P233</abbr>, <abbr class="abbr" title="P405: Store locked up.">P405</abbr>, <abbr class="abbr" title="P501: Dispose of contents/container to ...">P501</abbr> </td></tr> <tr> <td><a href="/wiki/NFPA_704" title="NFPA 704"><b>NFPA 704</b></a> (fire diamond) </td> <td><style data-mw-deduplicate="TemplateStyles:r1170367383">.mw-parser-output .nfpa-704-diamond-ref{float:right;padding:1px;text-align:right}.mw-parser-output .nfpa-704-diamond-container{width:82px;font-family:sans-serif;margin:0 auto}.mw-parser-output .nfpa-704-diamond-container-ref{float:left;margin-left:1em}.mw-parser-output .nfpa-704-diamond-images{float:left;font-size:20px;text-align:center;position:relative;height:80px;width:80px;padding:1px}.mw-parser-output .nfpa-704-diamond-map{position:absolute;height:80px;width:80px}.mw-parser-output .nfpa-704-diamond .noresize{margin:0 auto}.mw-parser-output .nfpa-704-diamond-code{line-height:1em;text-align:center;position:absolute}.mw-parser-output .nfpa-704-diamond-code>a{color:black}.mw-parser-output .nfpa-704-diamond-blue{width:13px;top:31px;left:15px}.mw-parser-output .nfpa-704-diamond-red{width:12px;top:12px;left:35px}.mw-parser-output .nfpa-704-diamond-yellow{width:13px;top:31px;left:54px}.mw-parser-output .nfpa-704-diamond-white-image{position:relative;top:51px;left:0}.mw-parser-output .nfpa-704-diamond-white-text{vertical-align:middle;text-align:center;line-height:80%;position:absolute;top:52px}.mw-parser-output .nfpa-704-diamond-white-text a>span{position:absolute;color:black}.mw-parser-output .nfpa-704-diamond-white-wors{font-size:15px;width:23px;left:29px}.mw-parser-output .nfpa-704-diamond-white-wox{font-size:15px;font-stretch:condensed;width:21px;line-height:80%;top:-4px;left:29px}.mw-parser-output .nfpa-704-diamond-white-abcp{font-size:13.5px;font-stretch:condensed;width:28px;left:26px}.mw-parser-output .nfpa-704-diamond-white-ac{font-size:10px;width:30px;left:25px}.mw-parser-output .nfpa-704-diamond-white-strike{text-decoration:line-through}</style><div class="nfpa-704-diamond notheme"><div class="nfpa-704-diamond-container"><div class="nfpa-704-diamond-images nounderlines"> <div class="nfpa-704-diamond-map"><figure class="noresize" typeof="mw:File"><span><img alt="NFPA 704 four-colored diamond" src="//upload.wikimedia.org/wikipedia/commons/thumb/6/6f/NFPA_704.svg/80px-NFPA_704.svg.png" decoding="async" width="80" height="80" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/6f/NFPA_704.svg/120px-NFPA_704.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/6f/NFPA_704.svg/160px-NFPA_704.svg.png 2x" data-file-width="512" data-file-height="512" usemap="#ImageMap_d27e9ea14ebdeff9" /></span><map name="ImageMap_d27e9ea14ebdeff9"><area href="/wiki/NFPA_704#Blue" shape="poly" coords="23,23,47,47,23,70,0,47" alt="Health 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroform" title="Health 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroform" /><area href="/wiki/NFPA_704#Red" shape="poly" coords="47,0,70,23,47,47,23,23" alt="Flammability 0: Will not burn. E.g. water" title="Flammability 0: Will not burn. E.g. water" /><area href="/wiki/NFPA_704#Yellow" shape="poly" coords="70,23,94,47,70,70,47,47" alt="Instability 1: Normally stable, but can become unstable at elevated temperatures and pressures. E.g. calcium" title="Instability 1: Normally stable, but can become unstable at elevated temperatures and pressures. E.g. calcium" /><area href="/wiki/NFPA_704#White" shape="poly" coords="47,47,70,70,47,94,23,70" alt="Special hazards (white): no code" title="Special hazards (white): no code" /></map><figcaption></figcaption></figure></div><div class="nfpa-704-diamond-code nfpa-704-diamond-blue"> <a href="/wiki/NFPA_704#Blue" title="NFPA 704"><span title="Health 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroform" class="notheme mw-no-invert">2</span></a></div><div class="nfpa-704-diamond-code nfpa-704-diamond-red"> <a href="/wiki/NFPA_704#Red" title="NFPA 704"><span title="Flammability 0: Will not burn. E.g. water" class="notheme mw-no-invert">0</span></a></div><div class="nfpa-704-diamond-code nfpa-704-diamond-yellow"> <a href="/wiki/NFPA_704#Yellow" title="NFPA 704"><span title="Instability 1: Normally stable, but can become unstable at elevated temperatures and pressures. E.g. calcium" class="notheme mw-no-invert">1</span></a></div></div></div></div> </td></tr> <tr> <td><a href="/wiki/Flash_point" title="Flash point">Flash point</a> </td> <td>Nonflammable </td></tr> <tr> <td colspan="2" style="text-align:left; background-color:#eaeaea;"><b>Lethal dose</b> or concentration (LD, LC): </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">LD<sub>50</sub> (<a href="/wiki/Lethal_dose#LD50" title="Lethal dose">median dose</a>)</div> </td> <td>704 mg/kg (mouse, dermal)<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> </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">LC<sub>50</sub> (<a href="/wiki/Lethal_dose#LC50" title="Lethal dose">median concentration</a>)</div> </td> <td>47,702 mg/m<sup>3</sup> (rat, 4 hr)<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> </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">LC<sub>Lo</sub> (<a href="/wiki/Lethal_dose#LCLo" title="Lethal dose">lowest published</a>)</div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li>20,000 ppm (guinea pig, 2 hr)</li><li>7,056 ppm (cat, 4 hr)</li><li>25,000 ppm (human, 5 min)</li></ul></div><sup id="cite_ref-IDLH_8-0" class="reference"><a href="#cite_note-IDLH-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup><sup class="noprint Inline-Template" style="margin-left:0.1em; white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Please_clarify" title="Wikipedia:Please clarify"><span title="What is "ppm"??? Is it a mass/mass fraction, volume/volume fraction, mole/mole fraction, mass/volume fraction, and who knows what else??? Using ambiguous units like "ppm" without unambiguous explanation what that unit stands for irritates readers who are not experts in this field, and the readers have no power to read the writer's mind! (June 2023)">clarification needed</span></a></i>]</sup> </td></tr> <tr> <td colspan="2" style="text-align:left; background-color:#eaeaea;"><a href="/wiki/National_Institute_for_Occupational_Safety_and_Health" title="National Institute for Occupational Safety and Health"><b>NIOSH</b></a> (US health exposure limits): </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Permissible_exposure_limit" title="Permissible exposure limit">PEL</a> (Permissible)</div> </td> <td>50 ppm (240 mg/m<sup>3</sup>)<sup id="cite_ref-PGCH_4-1" class="reference"><a href="#cite_note-PGCH-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Recommended_exposure_limit" title="Recommended exposure limit">REL</a> (Recommended)</div> </td> <td>Ca ST 2 ppm (9.78 mg/m<sup>3</sup>) [60-minute]<sup id="cite_ref-PGCH_4-2" class="reference"><a href="#cite_note-PGCH-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/IDLH" class="mw-redirect" title="IDLH">IDLH</a> (Immediate danger)</div> </td> <td>500 ppm<sup id="cite_ref-PGCH_4-3" class="reference"><a href="#cite_note-PGCH-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup><sup class="noprint Inline-Template" style="margin-left:0.1em; white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Please_clarify" title="Wikipedia:Please clarify"><span title="What is "ppm"??? Is it a mass/mass fraction, volume/volume fraction, mole/mole fraction, mass/volume fraction, and who knows what else??? Using ambiguous units like "ppm" without unambiguous explanation what that unit stands for irritates readers who are not experts in this field, and the readers have no power to read the writer's mind! (June 2023)">clarification needed</span></a></i>]</sup> </td></tr> <tr> <td><a href="/wiki/Safety_data_sheet" title="Safety data sheet">Safety data sheet</a> (SDS) </td> <td><a rel="nofollow" class="external autonumber" href="https://www.merckmillipore.com/Web-IE-Site/en_US/-/EUR/ShowDocument-File?ProductSKU=MDA_CHEM-107024&DocumentType=MSD&DocumentId=107024_SDS_GB_EN.PDF&DocumentUID=370414&Language=EN&Country=GB&Origin=PDP&Display=inline">[1]</a> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Related compounds </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">Related compounds</div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><a href="/wiki/Deuterated_chloroform" title="Deuterated chloroform">Deuterated chloroform</a> <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">CDCl<sub class="template-chem2-sub">3</sub></span></li><li><a href="/wiki/Chloromethane" title="Chloromethane">Chloromethane</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">CH<sub class="template-chem2-sub">3</sub>Cl</span></li><li><a href="/wiki/Dichloromethane" title="Dichloromethane">Dichloromethane</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">CH<sub class="template-chem2-sub">2</sub>Cl<sub class="template-chem2-sub">2</sub></span></li><li><a href="/wiki/Tetrachloromethane" class="mw-redirect" title="Tetrachloromethane">Tetrachloromethane</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">CCl<sub class="template-chem2-sub">4</sub></span></li><li><a href="/wiki/Fluoroform" title="Fluoroform">Fluoroform</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">CHF<sub class="template-chem2-sub">3</sub></span></li><li><a href="/wiki/Bromoform" title="Bromoform">Bromoform</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">CHBr<sub class="template-chem2-sub">3</sub></span></li><li><a href="/wiki/Iodoform" title="Iodoform">Iodoform</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">CHI<sub class="template-chem2-sub">3</sub></span></li><li><a href="/wiki/Chlorodifluoromethane" title="Chlorodifluoromethane">Chlorodifluoromethane</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">CHF<sub class="template-chem2-sub">2</sub>Cl</span></li><li><a href="/wiki/Dichlorofluoromethane" title="Dichlorofluoromethane">Dichlorofluoromethane</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">CHFCl<sub class="template-chem2-sub">2</sub></span></li><li><a href="/wiki/Bromodichloromethane" title="Bromodichloromethane">Bromodichloromethane</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">CHCl<sub class="template-chem2-sub">2</sub>Br</span></li><li><a href="/wiki/Dibromochloromethane" title="Dibromochloromethane">Dibromochloromethane</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">CHClBr<sub class="template-chem2-sub">2</sub></span></li><li><a href="/wiki/Bromodifluoromethane" title="Bromodifluoromethane">Bromodifluoromethane</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">CHF<sub class="template-chem2-sub">2</sub>Br</span></li><li><a href="/wiki/Dibromofluoromethane" title="Dibromofluoromethane">Dibromofluoromethane</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">CHFBr<sub class="template-chem2-sub">2</sub></span></li></ul></div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Supplementary data page </th></tr> <tr> <td colspan="2" style="text-align:center"><a href="/wiki/Chloroform_(data_page)" title="Chloroform (data page)">Chloroform (data page)</a> </td></tr> <tr> <td colspan="2" style="text-align:left; background:#f8eaba; border:1px solid #a2a9b1;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">Except where otherwise noted, data are given for materials in their <a href="/wiki/Standard_state" title="Standard state">standard state</a> (at 25 °C [77 °F], 100 kPa).</div> <div style="margin-top: 0.3em;"><div style="text-align:center;"><span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/12px-Yes_check.svg.png" decoding="async" width="12" height="12" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/18px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/24px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span> <span class="reflink plainlinks nourlexpansion"><a class="external text" href="https://en.wikipedia.org/w/index.php?title=Special:ComparePages&rev1=407464807&page2=Chloroform">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>Chloroform</b>,<sup id="cite_ref-iupac2013_10-0" class="reference"><a href="#cite_note-iupac2013-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> or <b>trichloromethane</b> (often abbreviated as <b>TCM</b>), is an <a href="/wiki/Organochloride" class="mw-redirect" title="Organochloride">organochloride</a> with the <a href="/wiki/Chemical_formula" title="Chemical formula">formula</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap"><a href="/wiki/Carbon" title="Carbon">C</a><a href="/wiki/Hydrogen" title="Hydrogen">H</a><a href="/wiki/Chlorine" title="Chlorine">Cl</a><sub class="template-chem2-sub">3</sub></span> and a common <a href="/wiki/Solvent" title="Solvent">solvent</a>. It is a volatile, colorless, sweet-smelling, dense liquid produced on a large scale as a precursor to <a href="/wiki/Refrigerant" title="Refrigerant">refrigerants</a> and <a href="/wiki/PTFE" class="mw-redirect" title="PTFE">PTFE</a>.<sup id="cite_ref-Ullmann_11-0" class="reference"><a href="#cite_note-Ullmann-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> Chloroform was once used as an <a href="/wiki/Inhalational_anesthetic" title="Inhalational anesthetic">inhalational anesthetic</a> between the 19th century and the first half of the 20th century.<sup id="cite_ref-12" class="reference"><a href="#cite_note-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup><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> It is miscible with many solvents but it is only very slightly soluble in water (only 8 g/L at 20°C). </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Structure_and_name">Structure and name</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Chloroform&action=edit&section=1" title="Edit section: Structure and name"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The molecule adopts a <a href="/wiki/Tetrahedral_molecular_geometry" title="Tetrahedral molecular geometry">tetrahedral molecular geometry</a> with C<sub>3v</sub> <a href="/wiki/Symmetry_group" title="Symmetry group">symmetry</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> The chloroform molecule can be viewed as a <a href="/wiki/Methane" title="Methane">methane</a> molecule with three hydrogen atoms replaced with three chlorine atoms, leaving a single hydrogen atom. </p><p>The name "chloroform" is a <a href="/wiki/Portmanteau" class="mw-redirect" title="Portmanteau">portmanteau</a> of <i>terchloride</i> (tertiary chloride, a trichloride) and <i>formyle</i>, an obsolete name for the <a href="/wiki/Methylylidene" class="mw-redirect" title="Methylylidene">methylylidene</a> radical (CH) derived from <a href="/wiki/Formic_acid" title="Formic acid">formic acid</a>. </p> <div class="mw-heading mw-heading2"><h2 id="Natural_occurrence">Natural occurrence</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Chloroform&action=edit&section=2" title="Edit section: Natural occurrence"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Many kinds of <a href="/wiki/Seaweed" title="Seaweed">seaweed</a> produce chloroform, and <a href="/wiki/Fungi" class="mw-redirect" title="Fungi">fungi</a> are believed to produce chloroform in soil.<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> Abiotic processes are also believed to contribute to natural chloroform productions in soils, although the mechanism is still unclear.<sup id="cite_ref-16" class="reference"><a href="#cite_note-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup> </p><p>Chloroform is a volatile organic compound.<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> </p> <div class="mw-heading mw-heading2"><h2 id="History">History</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Chloroform&action=edit&section=3" title="Edit section: History"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Chloroform was synthesized independently by several investigators <abbr title="circa">c.</abbr><span style="white-space:nowrap;"> 1831</span>: </p> <ul><li>Moldenhawer, a German pharmacist from <a href="/wiki/Frankfurt_an_der_Oder" class="mw-redirect" title="Frankfurt an der Oder">Frankfurt an der Oder</a>, appears to have produced chloroform in 1830 by mixing <a href="/wiki/Chlorinated_lime#Chlorine-based_bleaches" class="mw-redirect" title="Chlorinated lime">chlorinated lime</a> with <a href="/wiki/Ethanol" title="Ethanol">ethanol</a>; however, he mistook it for <i>Chloräther</i> (chloric ether, <a href="/wiki/1,2-dichloroethane" class="mw-redirect" title="1,2-dichloroethane">1,2-dichloroethane</a>).<sup id="cite_ref-18" class="reference"><a href="#cite_note-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup><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></li> <li><a href="/wiki/Samuel_Guthrie_(physician)" title="Samuel Guthrie (physician)">Samuel Guthrie</a>, a U.S. physician from <a href="/wiki/Sackets_Harbor,_New_York" title="Sackets Harbor, New York">Sackets Harbor, New York</a>, also appears to have produced chloroform in 1831 by reacting chlorinated lime with ethanol, and noted its <a href="/wiki/Anesthetic" title="Anesthetic">anaesthetic</a> properties; however, he also believed that he had prepared chloric ether.<sup id="cite_ref-20" class="reference"><a href="#cite_note-20"><span class="cite-bracket">[</span>20<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-21" class="reference"><a href="#cite_note-21"><span class="cite-bracket">[</span>21<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-22" class="reference"><a href="#cite_note-22"><span class="cite-bracket">[</span>22<span class="cite-bracket">]</span></a></sup></li> <li><a href="/wiki/Justus_von_Liebig" title="Justus von Liebig">Justus von Liebig</a> carried out the <a href="/wiki/Bond_cleavage" title="Bond cleavage">alkaline cleavage</a> of <a href="/wiki/Chloral" title="Chloral">chloral</a>. Liebig incorrectly states that the <a href="/wiki/Empirical_formula" title="Empirical formula">empirical formula</a> of chloroform was <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">C<sub class="template-chem2-sub">2</sub>Cl<sub class="template-chem2-sub">5</sub></span> and named it "<i>Chlorkohlenstoff</i>" ("carbon chloride").<sup id="cite_ref-23" class="reference"><a href="#cite_note-23"><span class="cite-bracket">[</span>23<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-24" class="reference"><a href="#cite_note-24"><span class="cite-bracket">[</span>24<span class="cite-bracket">]</span></a></sup></li> <li><a href="/wiki/Eug%C3%A8ne_Soubeiran" title="Eugène Soubeiran">Eugène Soubeiran</a> obtained the compound by the action of <a href="/wiki/Chlorine_bleach" class="mw-redirect" title="Chlorine bleach">chlorine bleach</a> on both <a href="/wiki/Ethanol" title="Ethanol">ethanol</a> and <a href="/wiki/Acetone" title="Acetone">acetone</a>.<sup id="cite_ref-25" class="reference"><a href="#cite_note-25"><span class="cite-bracket">[</span>25<span class="cite-bracket">]</span></a></sup></li></ul> <p>In 1834, French chemist <a href="/wiki/Jean-Baptiste_Dumas" title="Jean-Baptiste Dumas">Jean-Baptiste Dumas</a> determined chloroform's empirical formula and named it:<sup id="cite_ref-26" class="reference"><a href="#cite_note-26"><span class="cite-bracket">[</span>26<span class="cite-bracket">]</span></a></sup> "<i>Es scheint mir also erweisen, dass die von mir analysirte Substanz, … zur Formel hat: C<sub>2</sub>H<sub>2</sub>Cl<sub>6</sub>.</i>" (Thus it seems to me to show that the substance I analyzed … has as [its empirical] formula: C<sub>2</sub>H<sub>2</sub>Cl<sub>6</sub>.). [Note: The coefficients of his empirical formula should be halved.] ... "<i>Diess hat mich veranlasst diese Substanz mit dem Namen 'Chloroform' zu belegen.</i>" (This had caused me to impose the name "chloroform" upon this substance [i.e., formyl chloride or chloride of formic acid].) </p><p>In 1835, Dumas prepared the substance by alkaline cleavage of <a href="/wiki/Trichloroacetic_acid" title="Trichloroacetic acid">trichloroacetic acid</a>. </p><p>In 1842, <a href="/wiki/Robert_Mortimer_Glover" title="Robert Mortimer Glover">Robert Mortimer Glover</a> in London discovered the anaesthetic qualities of chloroform on laboratory animals.<sup id="cite_ref-pdf1_27-0" class="reference"><a href="#cite_note-pdf1-27"><span class="cite-bracket">[</span>27<span class="cite-bracket">]</span></a></sup> </p><p>In 1847, Scottish obstetrician <a href="/wiki/James_Y._Simpson" class="mw-redirect" title="James Y. Simpson">James Y. Simpson</a> was the first to demonstrate the anaesthetic properties of chloroform in humans, provided by local pharmacist <a href="/wiki/William_Flockhart" title="William Flockhart">William Flockhart</a> of Duncan, Flockhart and company,<sup id="cite_ref-Gordon2002_28-0" class="reference"><a href="#cite_note-Gordon2002-28"><span class="cite-bracket">[</span>28<span class="cite-bracket">]</span></a></sup> and helped to popularize the drug for use in medicine.<sup id="cite_ref-eb_29-0" class="reference"><a href="#cite_note-eb-29"><span class="cite-bracket">[</span>29<span class="cite-bracket">]</span></a></sup> </p><p>By the 1850s, chloroform was being produced on a commercial basis. In Britain, about 750,000 doses a week were being produced by 1895,<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> using the Liebig procedure, which retained its importance until the 1960s. Today, chloroform – along with <a href="/wiki/Dichloromethane" title="Dichloromethane">dichloromethane</a> – is prepared exclusively and on a massive scale by the chlorination of methane and chloromethane.<sup id="cite_ref-Ullmann_11-1" class="reference"><a href="#cite_note-Ullmann-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Production">Production</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Chloroform&action=edit&section=4" title="Edit section: Production"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Industrially, chloroform is produced by heating a mixture of <a href="/wiki/Chlorine" title="Chlorine">chlorine</a> and either <a href="/wiki/Methyl_chloride" class="mw-redirect" title="Methyl chloride">methyl chloride</a> (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">CH<sub class="template-chem2-sub">3</sub>Cl</span>) or <a href="/wiki/Methane" title="Methane">methane</a> (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">CH<sub class="template-chem2-sub">4</sub></span>).<sup id="cite_ref-Ullmann_11-2" class="reference"><a href="#cite_note-Ullmann-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> At 400–500 °C, <a href="/wiki/Free_radical_halogenation" class="mw-redirect" title="Free radical halogenation">free radical halogenation</a> occurs, converting these precursors to progressively more chlorinated compounds: </p> <dl><dd><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">CH<sub class="template-chem2-sub">4</sub> + <a href="/wiki/Chlorine" title="Chlorine">Cl<sub class="template-chem2-sub">2</sub></a> → CH<sub class="template-chem2-sub">3</sub>Cl + <a href="/wiki/Hydrogen_chloride" title="Hydrogen chloride">HCl</a></span></dd> <dd><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">CH<sub class="template-chem2-sub">3</sub>Cl + Cl<sub class="template-chem2-sub">2</sub> → <a href="/wiki/Dichloromethane" title="Dichloromethane">CH<sub class="template-chem2-sub">2</sub>Cl<sub class="template-chem2-sub">2</sub></a> + HCl</span></dd> <dd><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">CH<sub class="template-chem2-sub">2</sub>Cl<sub class="template-chem2-sub">2</sub> + Cl<sub class="template-chem2-sub">2</sub> → CHCl<sub class="template-chem2-sub">3</sub> + HCl</span></dd></dl> <p>Chloroform undergoes further chlorination to yield <a href="/wiki/Carbon_tetrachloride" title="Carbon tetrachloride">carbon tetrachloride</a> (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">CCl<sub class="template-chem2-sub">4</sub></span>): </p> <dl><dd><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">CHCl<sub class="template-chem2-sub">3</sub> + Cl<sub class="template-chem2-sub">2</sub> → CCl<sub class="template-chem2-sub">4</sub> + HCl</span></dd></dl> <p>The output of this process is a mixture of the four chloromethanes: <a href="/wiki/Chloromethane" title="Chloromethane">chloromethane</a>, <a href="/wiki/Methylene_chloride" class="mw-redirect" title="Methylene chloride">methylene chloride</a> (dichloromethane), trichloromethane (chloroform), and tetrachloromethane (carbon tetrachloride). These can then be separated by <a href="/wiki/Distillation" title="Distillation">distillation</a>.<sup id="cite_ref-Ullmann_11-3" class="reference"><a href="#cite_note-Ullmann-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> </p><p>Chloroform may also be produced on a small scale via the <a href="/wiki/Haloform_reaction" title="Haloform reaction">haloform reaction</a> between <a href="/wiki/Acetone" title="Acetone">acetone</a> and <a href="/wiki/Sodium_hypochlorite" title="Sodium hypochlorite">sodium hypochlorite</a>: :<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">3 NaOCl + (CH<sub class="template-chem2-sub">3</sub>)<sub class="template-chem2-sub">2</sub>CO → CHCl<sub class="template-chem2-sub">3</sub> + 2 <a href="/wiki/Sodium_hydroxide" title="Sodium hydroxide">NaOH</a> + <a href="/wiki/Sodium_acetate" title="Sodium acetate">CH<sub class="template-chem2-sub">3</sub>COONa</a></span> </p> <div class="mw-heading mw-heading3"><h3 id="Deuterochloroform">Deuterochloroform</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Chloroform&action=edit&section=5" title="Edit section: Deuterochloroform"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">Main article: <a href="/wiki/Deuterated_chloroform" title="Deuterated chloroform">Deuterated chloroform</a></div> <p><a href="/wiki/Deuterated_chloroform" title="Deuterated chloroform">Deuterated chloroform</a> is an <a href="/wiki/Isotopologue" title="Isotopologue">isotopologue</a> of chloroform with a single <a href="/wiki/Deuterium" title="Deuterium">deuterium</a> atom. <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">CDCl<sub class="template-chem2-sub">3</sub></span> is a common solvent used in <a href="/wiki/NMR_spectroscopy" class="mw-redirect" title="NMR spectroscopy">NMR spectroscopy</a>. Deuterochloroform is produced by the reaction of <a href="/wiki/Hexachloroacetone" title="Hexachloroacetone">hexachloroacetone</a> with <a href="/wiki/Heavy_water" title="Heavy water">heavy water</a>.<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> The haloform process is now obsolete for production of ordinary chloroform. Deuterochloroform can also be prepared by reacting <a href="/wiki/Sodium_deuteroxide" title="Sodium deuteroxide">sodium deuteroxide</a> with <a href="/wiki/Chloral_hydrate" title="Chloral hydrate">chloral hydrate</a>.<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><sup id="cite_ref-33" class="reference"><a href="#cite_note-33"><span class="cite-bracket">[</span>33<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Inadvertent_formation_of_chloroform">Inadvertent formation of chloroform</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Chloroform&action=edit&section=6" title="Edit section: Inadvertent formation of chloroform"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The haloform reaction can also occur inadvertently in domestic settings. Sodium hypochlorite solution (<a href="/wiki/Chlorine_bleach" class="mw-redirect" title="Chlorine bleach">chlorine bleach</a>) mixed with common household liquids such as <a href="/wiki/Acetone" title="Acetone">acetone</a>, <a href="/wiki/Methyl_ethyl_ketone" class="mw-redirect" title="Methyl ethyl ketone">methyl ethyl ketone</a>, <a href="/wiki/Ethanol" title="Ethanol">ethanol</a>, or <a href="/wiki/Isopropyl_alcohol" title="Isopropyl alcohol">isopropyl alcohol</a> can produce some chloroform, in addition to other compounds, such as <a href="/wiki/Chloroacetone" title="Chloroacetone">chloroacetone</a> or <a href="/wiki/Dichloroacetone" class="mw-redirect" title="Dichloroacetone">dichloroacetone</a>.<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (November 2020)">citation needed</span></a></i>]</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=Chloroform&action=edit&section=7" title="Edit section: Uses"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>In terms of scale, the most important reaction of chloroform is with <a href="/wiki/Hydrogen_fluoride" title="Hydrogen fluoride">hydrogen fluoride</a> to give <a href="/wiki/Monochlorodifluoromethane" class="mw-redirect" title="Monochlorodifluoromethane">monochlorodifluoromethane</a> (HCFC-22), a precursor in the production of polytetrafluoroethylene (<a href="/wiki/Teflon" class="mw-redirect" title="Teflon">Teflon</a>) and other fluoropolymers:<sup id="cite_ref-Ullmann_11-4" class="reference"><a href="#cite_note-Ullmann-11"><span class="cite-bracket">[</span>11<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">CHCl<sub class="template-chem2-sub">3</sub> + 2 HF → CHClF<sub class="template-chem2-sub">2</sub> + 2 HCl</span></dd></dl> <p>The reaction is conducted in the presence of a <a href="/wiki/Catalysis" title="Catalysis">catalytic</a> amount of <a href="/wiki/Antimony_trifluoride#Applications" title="Antimony trifluoride">mixed antimony halides</a>. Chlorodifluoromethane is then converted to <a href="/wiki/Tetrafluoroethylene" title="Tetrafluoroethylene">tetrafluoroethylene</a>, the main precursor of <a href="/wiki/Teflon" class="mw-redirect" title="Teflon">Teflon</a>.<sup id="cite_ref-34" class="reference"><a href="#cite_note-34"><span class="cite-bracket">[</span>34<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Solvent">Solvent</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Chloroform&action=edit&section=8" title="Edit section: Solvent"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The <a href="/wiki/Hydrogen" title="Hydrogen">hydrogen</a> attached to <a href="/wiki/Carbon" title="Carbon">carbon</a> in chloroform participates in hydrogen bonding,<sup id="cite_ref-35" class="reference"><a href="#cite_note-35"><span class="cite-bracket">[</span>35<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-36" class="reference"><a href="#cite_note-36"><span class="cite-bracket">[</span>36<span class="cite-bracket">]</span></a></sup> making it a good solvent for many materials. </p><p>Worldwide, chloroform is also used in pesticide formulations, as a <a href="/wiki/Solvent" title="Solvent">solvent</a> for <a href="/wiki/Lipids" class="mw-redirect" title="Lipids">lipids</a>, <a href="/wiki/Rubber" class="mw-redirect" title="Rubber">rubber</a>, <a href="/wiki/Alkaloid" title="Alkaloid">alkaloids</a>, <a href="/wiki/Wax" title="Wax">waxes</a>, <a href="/wiki/Gutta-percha" title="Gutta-percha">gutta-percha</a>, and <a href="/wiki/Resin" title="Resin">resins</a>, as a cleaning agent, as a grain <a href="/wiki/Fumigant" class="mw-redirect" title="Fumigant">fumigant</a>, in <a href="/wiki/Fire_extinguishers" class="mw-redirect" title="Fire extinguishers">fire extinguishers</a>, and in the rubber industry.<sup id="cite_ref-cicad_37-0" class="reference"><a href="#cite_note-cicad-37"><span class="cite-bracket">[</span>37<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-pth_38-0" class="reference"><a href="#cite_note-pth-38"><span class="cite-bracket">[</span>38<span class="cite-bracket">]</span></a></sup> <a href="/wiki/Deuterated_chloroform" title="Deuterated chloroform"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">CDCl<sub class="template-chem2-sub">3</sub></span></a> is a common solvent used in <a href="/wiki/NMR_spectroscopy" class="mw-redirect" title="NMR spectroscopy">NMR spectroscopy</a>.<sup id="cite_ref-39" class="reference"><a href="#cite_note-39"><span class="cite-bracket">[</span>39<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Refrigerant">Refrigerant</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Chloroform&action=edit&section=9" title="Edit section: Refrigerant"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Chloroform is used as a precursor to make R-22 (chlorodifluoromethane). This is done by reacting it with a solution of <a href="/wiki/Hydrofluoric_acid" title="Hydrofluoric acid">hydrofluoric acid</a> (HF) which fluorinates the <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">CHCl<sub class="template-chem2-sub">3</sub></span> molecule and releases hydrochloric acid as a byproduct.<sup id="cite_ref-40" class="reference"><a href="#cite_note-40"><span class="cite-bracket">[</span>40<span class="cite-bracket">]</span></a></sup> Before the <a href="/wiki/Montreal_Protocol" title="Montreal Protocol">Montreal Protocol</a> was enforced, most of the chloroform produced in the United States was used in the production of <a href="/wiki/Chlorodifluoromethane" title="Chlorodifluoromethane">chlorodifluoromethane</a>. However, its production remains high, as it is a key precursor of PTFE.<sup id="cite_ref-41" class="reference"><a href="#cite_note-41"><span class="cite-bracket">[</span>41<span class="cite-bracket">]</span></a></sup> </p><p>Although chloroform has properties such as a low boiling point, and a low global warming potential of only 31 (compared to the 1760 of R-22), which are appealing properties for a refrigerant, there is little information to suggest that it has seen widespread use as a refrigerant in any consumer products.<sup id="cite_ref-42" class="reference"><a href="#cite_note-42"><span class="cite-bracket">[</span>42<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Lewis_acid">Lewis acid</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Chloroform&action=edit&section=10" title="Edit section: Lewis acid"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>In solvents such as <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">CCl<sub class="template-chem2-sub">4</sub></span> and alkanes, chloroform hydrogen bonds to a variety of Lewis bases. <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">HCCl<sub class="template-chem2-sub">3</sub></span> is classified as a <a href="/wiki/HSAB" class="mw-redirect" title="HSAB">hard acid</a>, and the <a href="/wiki/ECW_model" title="ECW model">ECW model</a> lists its acid parameters as E<sub>A</sub> = 1.56 and C<sub>A</sub> = 0.44. </p> <div class="mw-heading mw-heading3"><h3 id="Reagent">Reagent</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Chloroform&action=edit&section=11" title="Edit section: Reagent"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>As a <a href="/wiki/Reagent" title="Reagent">reagent</a>, chloroform serves as a source of the <a href="/wiki/Dichlorocarbene" title="Dichlorocarbene">dichlorocarbene</a> intermediate <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">CCl<sub class="template-chem2-sub">2</sub></span>.<sup id="cite_ref-43" class="reference"><a href="#cite_note-43"><span class="cite-bracket">[</span>43<span class="cite-bracket">]</span></a></sup> It reacts with aqueous <a href="/wiki/Sodium_hydroxide" title="Sodium hydroxide">sodium hydroxide</a>, usually in the presence of a <a href="/wiki/Phase_transfer_catalyst" class="mw-redirect" title="Phase transfer catalyst">phase transfer catalyst</a>, to produce <a href="/wiki/Dichlorocarbene" title="Dichlorocarbene">dichlorocarbene</a>, <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">CCl<sub class="template-chem2-sub">2</sub></span>.<sup id="cite_ref-44" class="reference"><a href="#cite_note-44"><span class="cite-bracket">[</span>44<span class="cite-bracket">]</span></a></sup><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> This reagent effects ortho-formylation of activated <a href="/wiki/Aromatic_rings" class="mw-redirect" title="Aromatic rings">aromatic rings</a>, such as <a href="/wiki/Phenols" title="Phenols">phenols</a>, producing aryl <a href="/wiki/Aldehyde" title="Aldehyde">aldehydes</a> in a reaction known as the <a href="/wiki/Reimer%E2%80%93Tiemann_reaction" title="Reimer–Tiemann reaction">Reimer–Tiemann reaction</a>. Alternatively, the <a href="/wiki/Carbene" title="Carbene">carbene</a> can be trapped by an <a href="/wiki/Alkene" title="Alkene">alkene</a> to form a <a href="/wiki/Cyclopropane" title="Cyclopropane">cyclopropane</a> derivative. In the <a href="/wiki/Kharasch_addition" title="Kharasch addition">Kharasch addition</a>, chloroform forms the <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">•CHCl<sub class="template-chem2-sub">2</sub></span> free radical which adds to alkenes.<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (November 2020)">citation needed</span></a></i>]</sup> </p> <div class="mw-heading mw-heading3"><h3 id="Anaesthetic">Anaesthetic</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Chloroform&action=edit&section=12" title="Edit section: Anaesthetic"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:Chickamauga_2009,_Chloroform.jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/4/4f/Chickamauga_2009%2C_Chloroform.jpg/220px-Chickamauga_2009%2C_Chloroform.jpg" decoding="async" width="220" height="162" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/4/4f/Chickamauga_2009%2C_Chloroform.jpg/330px-Chickamauga_2009%2C_Chloroform.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/4/4f/Chickamauga_2009%2C_Chloroform.jpg/440px-Chickamauga_2009%2C_Chloroform.jpg 2x" data-file-width="3335" data-file-height="2449" /></a><figcaption>Antique bottles of chloroform</figcaption></figure> <p>Chloroform is a powerful <a href="/wiki/General_anesthetic" class="mw-redirect" title="General anesthetic">general anesthetic</a>, <a href="/wiki/Euphoriant" class="mw-redirect" title="Euphoriant">euphoriant</a>, <a href="/wiki/Anxiolytic" title="Anxiolytic">anxiolytic</a>, and <a href="/wiki/Sedative" title="Sedative">sedative</a> when inhaled or ingested. The <a href="/wiki/Anaesthetic" class="mw-redirect" title="Anaesthetic">anaesthetic</a> qualities of chloroform were first described in 1842 in a thesis by <a href="/wiki/Robert_Mortimer_Glover" title="Robert Mortimer Glover">Robert Mortimer Glover</a>, which won the Gold Medal of the <a href="/wiki/Harveian_Society" class="mw-redirect" title="Harveian Society">Harveian Society</a> for that year.<sup id="cite_ref-46" class="reference"><a href="#cite_note-46"><span class="cite-bracket">[</span>46<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-47" class="reference"><a href="#cite_note-47"><span class="cite-bracket">[</span>47<span class="cite-bracket">]</span></a></sup> Glover also undertook practical experiments on dogs to prove his theories, refined his theories, and presented them in his doctoral thesis at the <a href="/wiki/University_of_Edinburgh" title="University of Edinburgh">University of Edinburgh</a> in the summer of 1847, identifying anaesthetizing halogenous compounds as a "new order of poisonous substances".<sup id="cite_ref-48" class="reference"><a href="#cite_note-48"><span class="cite-bracket">[</span>48<span class="cite-bracket">]</span></a></sup> </p><p>The Scottish <a href="/wiki/Obstetrics" title="Obstetrics">obstetrician</a> <a href="/wiki/James_Young_Simpson" title="James Young Simpson">James Young Simpson</a> was one of those examiners required to read the thesis, but later claimed to have never read it and to have come to his own conclusions independently. <sup id="cite_ref-49" class="reference"><a href="#cite_note-49"><span class="cite-bracket">[</span>49<span class="cite-bracket">]</span></a></sup> Perkins-McVey, among others, have raised doubts about the credibility of Simpson's claim, noting that Simpson's publications on the subject in 1847 explicitly echo Glover's and, being one of the thesis examiners, Simpson was likely aware of the content of Glover's study, even if he skirted his duties as an examiner. <sup id="cite_ref-50" class="reference"><a href="#cite_note-50"><span class="cite-bracket">[</span>50<span class="cite-bracket">]</span></a></sup> In 1847 and 1848, Glover would pen a series of heated letters accusing Simpson of stealing his discovery, which had already earned Simpson considerably notoriety. <sup id="cite_ref-51" class="reference"><a href="#cite_note-51"><span class="cite-bracket">[</span>51<span class="cite-bracket">]</span></a></sup> Whatever the source of his inspiration, on 4 November 1847, Simpson argued that he had discovered the anaesthetic qualities of chloroform in humans. He and two colleagues entertained themselves by trying the effects of various substances, and thus revealed the potential for chloroform in medical procedures.<sup id="cite_ref-Gordon2002_28-1" class="reference"><a href="#cite_note-Gordon2002-28"><span class="cite-bracket">[</span>28<span class="cite-bracket">]</span></a></sup> </p> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:James_Young_Simpson_chloroform.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/0/06/James_Young_Simpson_chloroform.png/220px-James_Young_Simpson_chloroform.png" decoding="async" width="220" height="304" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/0/06/James_Young_Simpson_chloroform.png/330px-James_Young_Simpson_chloroform.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/0/06/James_Young_Simpson_chloroform.png/440px-James_Young_Simpson_chloroform.png 2x" data-file-width="1507" data-file-height="2080" /></a><figcaption>An illustration depicting James Young Simpson and his friends found unconscious.</figcaption></figure> <p>A few days later, during the course of a dental procedure in <a href="/wiki/Edinburgh" title="Edinburgh">Edinburgh</a>, <a href="/wiki/Francis_Brodie_Imlach" title="Francis Brodie Imlach">Francis Brodie Imlach</a> became the first person to use chloroform on a patient in a clinical context.<sup id="cite_ref-52" class="reference"><a href="#cite_note-52"><span class="cite-bracket">[</span>52<span class="cite-bracket">]</span></a></sup> </p><p>In May 1848, <a href="/wiki/Robert_Halliday_Gunning" title="Robert Halliday Gunning">Robert Halliday Gunning</a> made a presentation to the Medico-Chirurgical Society of Edinburgh following a series of laboratory <a href="/wiki/Domestic_rabbit#Experimentation" title="Domestic rabbit">experiments on rabbits</a> that confirmed Glover's findings and also refuted Simpson's claims of originality. The laboratory experiments that proved the dangers of chloroform were largely ignored.<sup id="cite_ref-53" class="reference"><a href="#cite_note-53"><span class="cite-bracket">[</span>53<span class="cite-bracket">]</span></a></sup> </p><p>The use of chloroform during <a href="/wiki/Surgery" title="Surgery">surgery</a> expanded rapidly in Europe; for instance in the 1850s chloroform was used by the physician <a href="/wiki/John_Snow" title="John Snow">John Snow</a> during the births of <a href="/wiki/Queen_Victoria" title="Queen Victoria">Queen Victoria</a>'s last two children <a href="/wiki/Prince_Leopold,_Duke_of_Albany" title="Prince Leopold, Duke of Albany">Leopold</a> and <a href="/wiki/Princess_Beatrice_of_the_United_Kingdom" title="Princess Beatrice of the United Kingdom">Beatrice</a>.<sup id="cite_ref-54" class="reference"><a href="#cite_note-54"><span class="cite-bracket">[</span>54<span class="cite-bracket">]</span></a></sup> In the United States, chloroform began to replace <a href="/wiki/Diethyl_ether" title="Diethyl ether">ether</a> as an anesthetic at the beginning of the 20th century;<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (February 2023)">citation needed</span></a></i>]</sup> it was abandoned in favor of ether on discovery of its toxicity, especially its tendency to cause fatal <a href="/wiki/Cardiac_arrhythmia" class="mw-redirect" title="Cardiac arrhythmia">cardiac arrhythmias</a> analogous to what is now termed "<a href="/wiki/Intoxicative_inhalant#Sudden_sniffing_death_syndrome" class="mw-redirect" title="Intoxicative inhalant">sudden sniffer's death</a>". Some people used chloroform as a recreational drug or to attempt suicide.<sup id="cite_ref-55" class="reference"><a href="#cite_note-55"><span class="cite-bracket">[</span>55<span class="cite-bracket">]</span></a></sup> One possible mechanism of action of chloroform is that it increases the movement of <a href="/wiki/Potassium" title="Potassium">potassium</a> ions through certain types of <a href="/wiki/Potassium_channel" title="Potassium channel">potassium channels</a> in <a href="/wiki/Nerve_cells" class="mw-redirect" title="Nerve cells">nerve cells</a>.<sup id="cite_ref-56" class="reference"><a href="#cite_note-56"><span class="cite-bracket">[</span>56<span class="cite-bracket">]</span></a></sup> Chloroform could also be mixed with other anaesthetic agents such as ether to make C.E. mixture, or ether and <a href="/wiki/Ethanol" title="Ethanol">alcohol</a> to make <a href="/wiki/A.C.E._mixture" class="mw-redirect" title="A.C.E. mixture">A.C.E. mixture</a>.<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (November 2020)">citation needed</span></a></i>]</sup> </p><p>In 1848, Hannah Greener, a 15-year-old girl who was having an infected toenail removed, died after being given the anaesthetic.<sup id="cite_ref-57" class="reference"><a href="#cite_note-57"><span class="cite-bracket">[</span>57<span class="cite-bracket">]</span></a></sup> Her autopsy establishing the cause of death was undertaken by <a href="/wiki/John_Fife_(surgeon)" title="John Fife (surgeon)">John Fife</a> assisted by <a href="/wiki/Robert_Mortimer_Glover" title="Robert Mortimer Glover">Robert Mortimer Glover</a>.<sup id="cite_ref-pdf1_27-1" class="reference"><a href="#cite_note-pdf1-27"><span class="cite-bracket">[</span>27<span class="cite-bracket">]</span></a></sup> A number of physically fit patients died after inhaling it. In 1848, however, John Snow developed an inhaler that regulated the dosage and so successfully reduced the number of deaths.<sup id="cite_ref-58" class="reference"><a href="#cite_note-58"><span class="cite-bracket">[</span>58<span class="cite-bracket">]</span></a></sup> </p><p>The opponents and supporters of chloroform disagreed on the question of whether the medical complications were due to respiratory disturbance or whether chloroform had a specific effect on the heart. Between 1864 and 1910, numerous commissions in Britain studied chloroform but failed to come to any clear conclusions. It was only in 1911 that Levy proved in experiments with animals that chloroform can cause ventricular fibrillation.<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (March 2023)">citation needed</span></a></i>]</sup> Despite this, between 1865 and 1920, chloroform was used in 80 to 95% of all narcoses performed in the UK and German-speaking countries. In Germany, comprehensive surveys of the fatality rate during anaesthesia were made by Gurlt between 1890 and 1897.<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (March 2023)">citation needed</span></a></i>]</sup> At the same time in the UK the medical journal <i><a href="/wiki/The_Lancet" title="The Lancet">The Lancet</a></i> carried out a questionnaire survey<sup id="cite_ref-59" class="reference"><a href="#cite_note-59"><span class="cite-bracket">[</span>59<span class="cite-bracket">]</span></a></sup> and compiled a report detailing numerous adverse reactions to anesthetics, including chloroform.<sup id="cite_ref-60" class="reference"><a href="#cite_note-60"><span class="cite-bracket">[</span>60<span class="cite-bracket">]</span></a></sup> In 1934, Killian gathered all the statistics compiled until then and found that the chances of suffering fatal complications under ether were between 1:14,000 and 1:28,000, whereas with chloroform the chances were between 1:3,000 and 1:6,000.<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (March 2023)">citation needed</span></a></i>]</sup> The rise of gas anaesthesia using <a href="/wiki/Nitrous_oxide" title="Nitrous oxide">nitrous oxide</a>, improved equipment for administering anesthetics, and the discovery of <a href="/wiki/Hexobarbital" title="Hexobarbital">hexobarbital</a> in 1932 led to the gradual decline of chloroform narcosis.<sup id="cite_ref-61" class="reference"><a href="#cite_note-61"><span class="cite-bracket">[</span>61<span class="cite-bracket">]</span></a></sup> </p><p>The latest reported anaesthetic use of chloroform in the Western world dates to 1987, when the last doctor who used it retired, about 140 years after its first use.<sup id="cite_ref-62" class="reference"><a href="#cite_note-62"><span class="cite-bracket">[</span>62<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Criminal_use">Criminal use</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Chloroform&action=edit&section=13" title="Edit section: Criminal use"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Chloroform has been used by criminals to knock out, daze, or murder victims. Joseph Harris was charged in 1894 with using chloroform to rob people.<sup id="cite_ref-63" class="reference"><a href="#cite_note-63"><span class="cite-bracket">[</span>63<span class="cite-bracket">]</span></a></sup> <a href="/wiki/Serial_killer" title="Serial killer">Serial killer</a> <a href="/wiki/H._H._Holmes" title="H. H. Holmes">H. H. Holmes</a> used chloroform overdoses to kill his female victims. In September 1900, chloroform was implicated in the murder of the U.S. businessman <a href="/wiki/William_Marsh_Rice" title="William Marsh Rice">William Marsh Rice</a>. Chloroform was deemed a factor in the alleged murder of a woman in 1991, when she was asphyxiated while asleep.<sup id="cite_ref-64" class="reference"><a href="#cite_note-64"><span class="cite-bracket">[</span>64<span class="cite-bracket">]</span></a></sup> In 2002, 13-year-old <a href="/wiki/Murder_of_Kacie_Woody" title="Murder of Kacie Woody">Kacie Woody</a> was sedated with chloroform when she was abducted by David Fuller and during the time that he had her, before he shot and killed her.<sup id="cite_ref-65" class="reference"><a href="#cite_note-65"><span class="cite-bracket">[</span>65<span class="cite-bracket">]</span></a></sup> In a 2007 plea bargain, a man confessed to using <a href="/wiki/Electroshock_weapon" title="Electroshock weapon">stun guns</a> and chloroform to sexually assault minors.<sup id="cite_ref-66" class="reference"><a href="#cite_note-66"><span class="cite-bracket">[</span>66<span class="cite-bracket">]</span></a></sup> </p><p>The use of chloroform as an <a href="/wiki/Incapacitating_agent" title="Incapacitating agent">incapacitating agent</a> has become widely recognized, bordering on <a href="/wiki/Clich%C3%A9" title="Cliché">cliché</a>, through the adoption by <a href="/wiki/Crime_fiction" title="Crime fiction">crime fiction</a> authors of plots involving criminals' use of chloroform-soaked rags to render victims unconscious. However, it is nearly impossible to incapacitate someone using chloroform in this way.<sup id="cite_ref-Anaesthesia_67-0" class="reference"><a href="#cite_note-Anaesthesia-67"><span class="cite-bracket">[</span>67<span class="cite-bracket">]</span></a></sup> It takes at least five minutes of inhalation of chloroform to render a person unconscious. Most criminal cases involving chloroform involve co-administration of another drug, such as <a href="/wiki/Ethanol" title="Ethanol">alcohol</a> or <a href="/wiki/Diazepam" title="Diazepam">diazepam</a>, or the victim being complicit in its administration. After a person has lost consciousness owing to chloroform inhalation, a continuous volume must be administered, and the chin must be supported to keep the tongue from obstructing the airway, a difficult procedure, typically requiring the skills of an <a href="/wiki/Anesthesiologist" class="mw-redirect" title="Anesthesiologist">anesthesiologist</a>. In 1865, as a direct result of the criminal reputation chloroform had gained, the medical journal <i><a href="/wiki/The_Lancet" title="The Lancet">The Lancet</a></i> offered a "permanent scientific reputation" to anyone who could demonstrate "instantaneous insensibility", i.e. loss of consciousness, using chloroform.<sup id="cite_ref-68" class="reference"><a href="#cite_note-68"><span class="cite-bracket">[</span>68<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Safety">Safety</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Chloroform&action=edit&section=14" title="Edit section: Safety"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Exposure">Exposure</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Chloroform&action=edit&section=15" title="Edit section: Exposure"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Chloroform is formed as a by-product of <a href="/wiki/Water_chlorination" title="Water chlorination">water chlorination</a>, along with a range of other <a href="/wiki/Disinfection_by-product" title="Disinfection by-product">disinfection by-products</a>, and it is therefore often present in municipal tap water and swimming pools. Reported ranges vary considerably, but are generally below the current health standard for total <a href="/wiki/Trihalomethanes" class="mw-redirect" title="Trihalomethanes">trihalomethanes</a> (THMs) of 100 μg/L.<sup id="cite_ref-69" class="reference"><a href="#cite_note-69"><span class="cite-bracket">[</span>69<span class="cite-bracket">]</span></a></sup> However, when considered in combination with other trihalomethanes often present in drinking water, the concentration of THMs often exceeds the recommended limit of exposure.<sup id="cite_ref-70" class="reference"><a href="#cite_note-70"><span class="cite-bracket">[</span>70<span class="cite-bracket">]</span></a></sup> </p><p>While few studies have assessed the risks posed by chloroform exposure through drinking water in isolation from other THMs, many studies have shown that exposure to the general category of THMs, including chloroform, is associated with an increased risk of cancer of the bladder or lower GI tract.<sup id="cite_ref-71" class="reference"><a href="#cite_note-71"><span class="cite-bracket">[</span>71<span class="cite-bracket">]</span></a></sup> </p><p>Historically, chloroform exposure may well have been higher, owing to its common use as an anesthetic, as an ingredient in cough syrups, and as a constituent of <a href="/wiki/Tobacco_smoke" title="Tobacco smoke">tobacco smoke</a>, where <a href="/wiki/DDT" title="DDT">DDT</a> had previously been used as a <a href="/wiki/Fumigant" class="mw-redirect" title="Fumigant">fumigant</a>.<sup id="cite_ref-72" class="reference"><a href="#cite_note-72"><span class="cite-bracket">[</span>72<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Pharmacology">Pharmacology</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Chloroform&action=edit&section=16" title="Edit section: Pharmacology"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Chloroform is well absorbed, metabolized, and eliminated rapidly by mammals after oral, inhalation, or dermal exposure. Accidental splashing into the eyes has caused irritation.<sup id="cite_ref-cicad_37-1" class="reference"><a href="#cite_note-cicad-37"><span class="cite-bracket">[</span>37<span class="cite-bracket">]</span></a></sup> Prolonged dermal exposure can result in the development of sores as a result of <a href="/wiki/Defatting_(medical)" title="Defatting (medical)">defatting</a>. Elimination is primarily through the lungs as chloroform and carbon dioxide; less than 1% is excreted in the urine.<sup id="cite_ref-pth_38-1" class="reference"><a href="#cite_note-pth-38"><span class="cite-bracket">[</span>38<span class="cite-bracket">]</span></a></sup> </p><p>Chloroform is metabolized in the liver by the <a href="/wiki/Cytochrome_P-450" class="mw-redirect" title="Cytochrome P-450">cytochrome P-450</a> enzymes, by oxidation to trichloromethanol and by reduction to the dichloromethyl <a href="/wiki/Free_radical" class="mw-redirect" title="Free radical">free radical</a>. Other metabolites of chloroform include <a href="/wiki/Hydrochloric_acid" title="Hydrochloric acid">hydrochloric acid</a> and diglutathionyl dithiocarbonate, with <a href="/wiki/Carbon_dioxide" title="Carbon dioxide">carbon dioxide</a> as the predominant end-product of metabolism.<sup id="cite_ref-eot_73-0" class="reference"><a href="#cite_note-eot-73"><span class="cite-bracket">[</span>73<span class="cite-bracket">]</span></a></sup> </p><p>Like most other general anesthetics and sedative-hypnotic drugs, chloroform is a <a href="/wiki/Allosteric_modulator" title="Allosteric modulator">positive allosteric modulator</a> at <a href="/wiki/GABAA_receptor" title="GABAA receptor">GABA<sub>A</sub> receptors</a>.<sup id="cite_ref-74" class="reference"><a href="#cite_note-74"><span class="cite-bracket">[</span>74<span class="cite-bracket">]</span></a></sup> Chloroform causes depression of the <a href="/wiki/Central_nervous_system" title="Central nervous system">central nervous system</a> (CNS), ultimately producing deep <a href="/wiki/Coma" title="Coma">coma</a> and respiratory center depression.<sup id="cite_ref-eot_73-1" class="reference"><a href="#cite_note-eot-73"><span class="cite-bracket">[</span>73<span class="cite-bracket">]</span></a></sup> When ingested, chloroform causes symptoms similar to those seen after inhalation. Serious illness has followed ingestion of 7.5 g (0.26 oz). The mean lethal oral dose in an adult is estimated at 45 g (1.6 oz).<sup id="cite_ref-cicad_37-2" class="reference"><a href="#cite_note-cicad-37"><span class="cite-bracket">[</span>37<span class="cite-bracket">]</span></a></sup> </p><p>The anesthetic use of chloroform has been discontinued, because it caused deaths from respiratory failure and cardiac arrhythmias. Following chloroform-induced anesthesia, some patients suffered <a href="/wiki/Nausea" title="Nausea">nausea</a>, <a href="/wiki/Vomiting" title="Vomiting">vomiting</a>, <a href="/wiki/Hyperthermia" title="Hyperthermia">hyperthermia</a>, <a href="/wiki/Jaundice" title="Jaundice">jaundice</a>, and coma owing to <a href="/wiki/Hepatic_dysfunction" class="mw-redirect" title="Hepatic dysfunction">hepatic dysfunction</a>. At autopsy, liver <a href="/wiki/Necrosis" title="Necrosis">necrosis</a> and degeneration have been observed.<sup id="cite_ref-cicad_37-3" class="reference"><a href="#cite_note-cicad-37"><span class="cite-bracket">[</span>37<span class="cite-bracket">]</span></a></sup> The hepatotoxicity and nephrotoxicity of chloroform is thought to be due largely to <a href="/wiki/Phosgene" title="Phosgene">phosgene</a>, one of its metabolites.<sup id="cite_ref-eot_73-2" class="reference"><a href="#cite_note-eot-73"><span class="cite-bracket">[</span>73<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Conversion_to_phosgene">Conversion to phosgene</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Chloroform&action=edit&section=17" title="Edit section: Conversion to phosgene"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Chloroform converts slowly in the presence of UV light and air to the extremely poisonous gas, <a href="/wiki/Phosgene" title="Phosgene">phosgene</a> (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">COCl<sub class="template-chem2-sub">2</sub></span>), releasing <a href="/wiki/HCl" class="mw-redirect" title="HCl">HCl</a> in the process.<sup id="cite_ref-earlham_75-0" class="reference"><a href="#cite_note-earlham-75"><span class="cite-bracket">[</span>75<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">2 CHCl<sub class="template-chem2-sub">3</sub> + O<sub class="template-chem2-sub">2</sub> → 2 COCl<sub class="template-chem2-sub">2</sub> + 2 HCl</span></dd></dl> <p>To prevent accidents, commercial chloroform is stabilized with <a href="/wiki/Ethanol" title="Ethanol">ethanol</a> or <a href="/wiki/Pentene" title="Pentene">amylene</a>, but samples that have been recovered or dried no longer contain any stabilizer. Amylene has been found to be ineffective, and the phosgene can affect analytes in samples, lipids, and nucleic acids dissolved in or extracted with chloroform.<sup id="cite_ref-76" class="reference"><a href="#cite_note-76"><span class="cite-bracket">[</span>76<span class="cite-bracket">]</span></a></sup> When ethanol is used as a stabiliser for chloroform, it reacts with phosgene (which is soluble in chloroform) to form the relatively harmless <a href="/wiki/Diethyl_carbonate" title="Diethyl carbonate">diethyl carbonate</a> ester: </p> <dl><dd>2 CH<sub>3</sub>CH<sub>2</sub>OH + COCl<sub>2</sub> → CO<sub>3</sub>(CH<sub>2</sub>CH<sub>3</sub>)<sub>2</sub> + 2 HCl</dd></dl> <p>Phosgene and HCl can be removed from chloroform by washing with saturated aqueous <a href="/wiki/Carbonate" title="Carbonate">carbonate</a> solutions, such as <a href="/wiki/Sodium_bicarbonate" title="Sodium bicarbonate">sodium bicarbonate</a>. This procedure is simple and results in harmless products. Phosgene reacts with water to form <a href="/wiki/Carbon_dioxide" title="Carbon dioxide">carbon dioxide</a> and HCl,<sup id="cite_ref-77" class="reference"><a href="#cite_note-77"><span class="cite-bracket">[</span>77<span class="cite-bracket">]</span></a></sup> and the carbonate salt <a href="/wiki/Neutralization_(chemistry)" title="Neutralization (chemistry)">neutralizes</a> the resulting acid.<sup id="cite_ref-78" class="reference"><a href="#cite_note-78"><span class="cite-bracket">[</span>78<span class="cite-bracket">]</span></a></sup> </p><p>Suspected samples can be tested for phosgene using filter paper which when treated with 5% <a href="/wiki/Diphenylamine" title="Diphenylamine">diphenylamine</a>, 5% <a href="/wiki/Dimethylaminobenzaldehyde" class="mw-redirect" title="Dimethylaminobenzaldehyde">dimethylaminobenzaldehyde</a> in <a href="/wiki/Ethanol" title="Ethanol">ethanol</a>, and then dried, turns yellow in the presence of phosgene vapour.<sup id="cite_ref-79" class="reference"><a href="#cite_note-79"><span class="cite-bracket">[</span>79<span class="cite-bracket">]</span></a></sup> There are several <a href="/wiki/Colorimetry" title="Colorimetry">colorimetric</a> and <a href="/wiki/Fluorometry" class="mw-redirect" title="Fluorometry">fluorometric</a> reagents for phosgene, and it can also be quantified using <a href="/wiki/Mass_spectrometry" title="Mass spectrometry">mass spectrometry</a>.<sup id="cite_ref-80" class="reference"><a href="#cite_note-80"><span class="cite-bracket">[</span>80<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Regulation">Regulation</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Chloroform&action=edit&section=18" title="Edit section: Regulation"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Chloroform is suspected of causing <a href="/wiki/Cancer" title="Cancer">cancer</a> (i.e. it is possibly <a href="/wiki/Carcinogen" title="Carcinogen">carcinogenic</a>, <a href="/wiki/IARC_Group_2B" class="mw-redirect" title="IARC Group 2B">IARC Group 2B</a>) as per the <a href="/wiki/International_Agency_for_Research_on_Cancer" title="International Agency for Research on Cancer">International Agency for Research on Cancer</a> (IARC) Monographs.<sup id="cite_ref-81" class="reference"><a href="#cite_note-81"><span class="cite-bracket">[</span>81<span class="cite-bracket">]</span></a></sup> </p><p>It is classified as an <a href="/wiki/List_of_extremely_hazardous_substances" class="mw-redirect" title="List of extremely hazardous substances">extremely hazardous substance</a> in the United States, as defined in Section 302 of the US <a href="/wiki/Emergency_Planning_and_Community_Right-to-Know_Act" title="Emergency Planning and Community Right-to-Know Act">Emergency Planning and Community Right-to-Know Act</a> (42 U.S.C. 11002), and is subject to strict reporting requirements by facilities that produce, store, or use it in significant quantities.<sup id="cite_ref-gov-right-know_82-0" class="reference"><a href="#cite_note-gov-right-know-82"><span class="cite-bracket">[</span>82<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Bioremediation_of_chloroform">Bioremediation of chloroform</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Chloroform&action=edit&section=19" title="Edit section: Bioremediation of chloroform"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Some <a href="/wiki/Anaerobic_organism" title="Anaerobic organism">anaerobic bacteria</a> use chloroform for respiration, termed <a href="/wiki/Halorespiration" title="Halorespiration">organohalide respiration</a>, converting it to <a href="/wiki/Dichloromethane" title="Dichloromethane">dichloromethane</a>.<sup id="cite_ref-83" class="reference"><a href="#cite_note-83"><span class="cite-bracket">[</span>83<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-84" class="reference"><a href="#cite_note-84"><span class="cite-bracket">[</span>84<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Gallery">Gallery</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Chloroform&action=edit&section=20" title="Edit section: Gallery"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul class="gallery mw-gallery-traditional"> <li class="gallerybox" style="width: 155px"> <div class="thumb" style="width: 150px; height: 150px;"><span typeof="mw:File"><a href="/wiki/File:CHCl3_mm.png" class="mw-file-description" title="CHCl3 measured by the Advanced Global Atmospheric Gases Experiment (AGAGE) in the lower atmosphere (troposphere) at stations around the world. Abundances are given as pollution free monthly mean mole fractions in parts-per-trillion (ppt)."><img alt="CHCl3 measured by the Advanced Global Atmospheric Gases Experiment (AGAGE) in the lower atmosphere (troposphere) at stations around the world. Abundances are given as pollution free monthly mean mole fractions in parts-per-trillion (ppt)." src="//upload.wikimedia.org/wikipedia/commons/thumb/6/67/CHCl3_mm.png/120px-CHCl3_mm.png" decoding="async" width="120" height="68" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/67/CHCl3_mm.png/180px-CHCl3_mm.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/67/CHCl3_mm.png/240px-CHCl3_mm.png 2x" data-file-width="3503" data-file-height="1977" /></a></span></div> <div class="gallerytext"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">CHCl<sub class="template-chem2-sub">3</sub></span> measured by the Advanced Global Atmospheric Gases Experiment (<a rel="nofollow" class="external text" href="http://agage.mit.edu/">AGAGE</a>) in the lower atmosphere (<a href="/wiki/Troposphere" title="Troposphere">troposphere</a>) at stations around the world. Abundances are given as pollution free monthly mean mole fractions in <a href="/wiki/Parts-per_notation" title="Parts-per notation">parts-per-trillion</a> (ppt).</div> </li> </ul> <div class="mw-heading mw-heading2"><h2 id="References">References</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Chloroform&action=edit&section=21" title="Edit section: References"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1239543626">.mw-parser-output .reflist{margin-bottom:0.5em;list-style-type:decimal}@media screen{.mw-parser-output .reflist{font-size:90%}}.mw-parser-output .reflist .references{font-size:100%;margin-bottom:0;list-style-type:inherit}.mw-parser-output .reflist-columns-2{column-width:30em}.mw-parser-output .reflist-columns-3{column-width:25em}.mw-parser-output .reflist-columns{margin-top:0.3em}.mw-parser-output .reflist-columns ol{margin-top:0}.mw-parser-output .reflist-columns li{page-break-inside:avoid;break-inside:avoid-column}.mw-parser-output .reflist-upper-alpha{list-style-type:upper-alpha}.mw-parser-output .reflist-upper-roman{list-style-type:upper-roman}.mw-parser-output .reflist-lower-alpha{list-style-type:lower-alpha}.mw-parser-output .reflist-lower-greek{list-style-type:lower-greek}.mw-parser-output .reflist-lower-roman{list-style-type:lower-roman}</style><div class="reflist"> <div class="mw-references-wrap mw-references-columns"><ol class="references"> <li id="cite_note-1"><span class="mw-cite-backlink"><b><a href="#cite_ref-1">^</a></b></span> <span class="reference-text">Gregory, William, A Handbook of Organic Chemistry (Third edition corrected and much extended), 1852, page 177</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">Daniel Pereira Gardner, Medicinal Chemistry for the Use of Students and the Profession: Being a Manual of the Science, with Its Applications to Toxicology, Physiology, Therapeutics, Hygiene, Etc (1848), page 271</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"><style data-mw-deduplicate="TemplateStyles:r1238218222">.mw-parser-output cite.citation{font-style:inherit;word-wrap:break-word}.mw-parser-output .citation q{quotes:"\"""\"""'""'"}.mw-parser-output .citation:target{background-color:rgba(0,127,255,0.133)}.mw-parser-output .id-lock-free.id-lock-free a{background:url("//upload.wikimedia.org/wikipedia/commons/6/65/Lock-green.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-limited.id-lock-limited a,.mw-parser-output .id-lock-registration.id-lock-registration a{background:url("//upload.wikimedia.org/wikipedia/commons/d/d6/Lock-gray-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-subscription.id-lock-subscription a{background:url("//upload.wikimedia.org/wikipedia/commons/a/aa/Lock-red-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .cs1-ws-icon a{background:url("//upload.wikimedia.org/wikipedia/commons/4/4c/Wikisource-logo.svg")right 0.1em center/12px no-repeat}body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-free a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-limited a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-registration a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-subscription a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .cs1-ws-icon a{background-size:contain;padding:0 1em 0 0}.mw-parser-output .cs1-code{color:inherit;background:inherit;border:none;padding:inherit}.mw-parser-output .cs1-hidden-error{display:none;color:var(--color-error,#d33)}.mw-parser-output .cs1-visible-error{color:var(--color-error,#d33)}.mw-parser-output .cs1-maint{display:none;color:#085;margin-left:0.3em}.mw-parser-output .cs1-kern-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right{padding-right:0.2em}.mw-parser-output .citation .mw-selflink{font-weight:inherit}@media screen{.mw-parser-output .cs1-format{font-size:95%}html.skin-theme-clientpref-night .mw-parser-output .cs1-maint{color:#18911f}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .cs1-maint{color:#18911f}}</style><cite class="citation web cs1"><a rel="nofollow" class="external text" href="http://www.unece.org/fileadmin/DAM/trans/danger/publi/ghs/ghs_rev02/English/03e_part3.pdf">"Part 3 Health Hazards"</a> <span class="cs1-format">(PDF)</span>. <i>Globally Harmonized System of Classification and Labelling of Chemicals (GHS)</i>. Second revised edition. United Nations. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20190304062207/http://www.unece.org/fileadmin/DAM/trans/danger/publi/ghs/ghs_rev02/English/03e_part3.pdf">Archived</a> <span class="cs1-format">(PDF)</span> from the original on 4 March 2019<span class="reference-accessdate">. Retrieved <span class="nowrap">30 September</span> 2017</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=Globally+Harmonized+System+of+Classification+and+Labelling+of+Chemicals+%28GHS%29&rft.atitle=Part+3+Health+Hazards&rft_id=http%3A%2F%2Fwww.unece.org%2Ffileadmin%2FDAM%2Ftrans%2Fdanger%2Fpubli%2Fghs%2Fghs_rev02%2FEnglish%2F03e_part3.pdf&rfr_id=info%3Asid%2Fen.wikipedia.org%3AChloroform" class="Z3988"></span></span> </li> <li id="cite_note-PGCH-4"><span class="mw-cite-backlink">^ <a href="#cite_ref-PGCH_4-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-PGCH_4-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-PGCH_4-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-PGCH_4-3"><sup><i><b>d</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFNIOSH_Pocket_Guide_to_Chemical_Hazards" class="citation web cs1">NIOSH Pocket Guide to Chemical Hazards. <a rel="nofollow" class="external text" href="https://www.cdc.gov/niosh/npg/npgd0127.html">"#0127"</a>. <a href="/wiki/National_Institute_for_Occupational_Safety_and_Health" title="National Institute for Occupational Safety and Health">National Institute for Occupational Safety and Health</a> (NIOSH).</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=%230127&rft.pub=National+Institute+for+Occupational+Safety+and+Health+%28NIOSH%29&rft.au=NIOSH+Pocket+Guide+to+Chemical+Hazards&rft_id=https%3A%2F%2Fwww.cdc.gov%2Fniosh%2Fnpg%2Fnpgd0127.html&rfr_id=info%3Asid%2Fen.wikipedia.org%3AChloroform" class="Z3988"></span></span> </li> <li id="cite_note-:1-5"><span class="mw-cite-backlink"><b><a href="#cite_ref-:1_5-0">^</a></b></span> <span class="reference-text">Toxicity on <a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/6212#section=Toxicity">PubChem</a> <a rel="nofollow" class="external text" href="https://web.archive.org/web/20180817125017/https://pubchem.ncbi.nlm.nih.gov/compound/6212#section=Toxicity">Archived</a> 17 August 2018 at the <a href="/wiki/Wayback_Machine" title="Wayback Machine">Wayback Machine</a></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="CITEREFLewis2012" class="citation book cs1">Lewis, Richard J. (2012). <i>Sax's Dangerous Properties of Industrial Materials</i> (12th ed.). Wiley. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-470-62325-1" title="Special:BookSources/978-0-470-62325-1"><bdi>978-0-470-62325-1</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Sax%27s+Dangerous+Properties+of+Industrial+Materials&rft.edition=12th&rft.pub=Wiley&rft.date=2012&rft.isbn=978-0-470-62325-1&rft.aulast=Lewis&rft.aufirst=Richard+J.&rfr_id=info%3Asid%2Fen.wikipedia.org%3AChloroform" 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 class="citation web cs1"><a rel="nofollow" class="external text" href="https://www.epa.gov/sites/default/files/2016-09/documents/chloroform.pdf">"Chloroform"</a> <span class="cs1-format">(PDF)</span>. <i>Environmental Protection Agency</i>. 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Retrieved <span class="nowrap">19 February</span> 2024</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=Environmental+Protection+Agency&rft.atitle=Chloroform&rft.date=2016-09&rft_id=https%3A%2F%2Fwww.epa.gov%2Fsites%2Fdefault%2Ffiles%2F2016-09%2Fdocuments%2Fchloroform.pdf&rfr_id=info%3Asid%2Fen.wikipedia.org%3AChloroform" class="Z3988"></span></span> </li> <li id="cite_note-IDLH-8"><span class="mw-cite-backlink"><b><a href="#cite_ref-IDLH_8-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://www.cdc.gov/niosh/idlh/67663.html">"Chloroform"</a>. <i>Immediately Dangerous to Life or Health Concentrations (IDLH)</i>. <a href="/wiki/National_Institute_for_Occupational_Safety_and_Health" title="National Institute for Occupational Safety and Health">National Institute for Occupational Safety and Health</a> (NIOSH).</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=Immediately+Dangerous+to+Life+or+Health+Concentrations+%28IDLH%29&rft.atitle=Chloroform&rft_id=https%3A%2F%2Fwww.cdc.gov%2Fniosh%2Fidlh%2F67663.html&rfr_id=info%3Asid%2Fen.wikipedia.org%3AChloroform" class="Z3988"></span></span> </li> <li id="cite_note-PubChem-9"><span class="mw-cite-backlink"><b><a href="#cite_ref-PubChem_9-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/6212#section=Safety-and-Hazards">"PubChem: Safety and Hazards – GHS Classification"</a>. 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Retrieved <span class="nowrap">17 August</span> 2018</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=PubChem%3A+Safety+and+Hazards+%E2%80%93+GHS+Classification&rft.pub=National+Center+for+Biotechnology+Information%2C+U.S.+National+Library+of+Medicine&rft_id=https%3A%2F%2Fpubchem.ncbi.nlm.nih.gov%2Fcompound%2F6212%23section%3DSafety-and-Hazards&rfr_id=info%3Asid%2Fen.wikipedia.org%3AChloroform" class="Z3988"></span></span> </li> <li id="cite_note-iupac2013-10"><span class="mw-cite-backlink"><b><a href="#cite_ref-iupac2013_10-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation book cs1">"Front Matter". <i>Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013 (Blue Book)</i>. Cambridge: <a href="/wiki/Royal_Society_of_Chemistry" title="Royal Society of Chemistry">The Royal Society of Chemistry</a>. 2014. p. 661. <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>. <q>The retained names 'bromoform' for HCBr<sub>3</sub>, 'chloroform' for HCCl<sub>3</sub>, and 'iodoform' for HCI<sub>3</sub> are acceptable in general nomenclature. Preferred IUPAC names are substitutive names.</q></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=661&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%3AChloroform" class="Z3988"></span></span> </li> <li id="cite_note-Ullmann-11"><span class="mw-cite-backlink">^ <a href="#cite_ref-Ullmann_11-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Ullmann_11-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-Ullmann_11-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-Ullmann_11-3"><sup><i><b>d</b></i></sup></a> <a href="#cite_ref-Ullmann_11-4"><sup><i><b>e</b></i></sup></a></span> <span class="reference-text"> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFRossberg" class="citation encyclopaedia cs1">Rossberg, M.; et al. 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"Halocarbon Emissions from a Degraded Forested Wetland in Coastal South Carolina Impacted by Sea Level Rise". <i>ACS Earth and Space Chemistry</i>. <b>2</b> (10): 955–967. <a href="/wiki/Bibcode_(identifier)" class="mw-redirect" title="Bibcode (identifier)">Bibcode</a>:<a rel="nofollow" class="external text" href="https://ui.adsabs.harvard.edu/abs/2018ESC.....2..955J">2018ESC.....2..955J</a>. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1021%2Facsearthspacechem.8b00044">10.1021/acsearthspacechem.8b00044</a>. <a href="/wiki/S2CID_(identifier)" class="mw-redirect" title="S2CID (identifier)">S2CID</a> <a rel="nofollow" class="external text" href="https://api.semanticscholar.org/CorpusID:134649348">134649348</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=ACS+Earth+and+Space+Chemistry&rft.atitle=Halocarbon+Emissions+from+a+Degraded+Forested+Wetland+in+Coastal+South+Carolina+Impacted+by+Sea+Level+Rise&rft.volume=2&rft.issue=10&rft.pages=955-967&rft.date=2018&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A134649348%23id-name%3DS2CID&rft_id=info%3Adoi%2F10.1021%2Facsearthspacechem.8b00044&rft_id=info%3Abibcode%2F2018ESC.....2..955J&rft.aulast=Jiao&rft.aufirst=Yi&rfr_id=info%3Asid%2Fen.wikipedia.org%3AChloroform" class="Z3988"></span></span> </li> <li id="cite_note-17"><span class="mw-cite-backlink"><b><a href="#cite_ref-17">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="http://aqt-vru.com/emissions/complete-list-of-vocs/">"Complete list of VOC's"</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=Complete+list+of+VOC%27s&rft_id=http%3A%2F%2Faqt-vru.com%2Femissions%2Fcomplete-list-of-vocs%2F&rfr_id=info%3Asid%2Fen.wikipedia.org%3AChloroform" class="Z3988"></span></span> </li> <li id="cite_note-18"><span class="mw-cite-backlink"><b><a href="#cite_ref-18">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFMoldenhawer1830" class="citation journal cs1">Moldenhawer (1830). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=a_E3AAAAMAAJ&pg=PA222">"Verfahren den Spiritus von dem Fuselöl auf leichte Weise zu befreien"</a> [Procedure for freeing ethanol of fusel oil in an easy way]. <i>Magazin für Pharmacie</i>. <b>8</b> (31): 222–227. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20200729120000/https://books.google.com/books?id=a_E3AAAAMAAJ&pg=PA222">Archived</a> from the original on 29 July 2020<span class="reference-accessdate">. Retrieved <span class="nowrap">6 May</span> 2016</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Magazin+f%C3%BCr+Pharmacie&rft.atitle=Verfahren+den+Spiritus+von+dem+Fusel%C3%B6l+auf+leichte+Weise+zu+befreien&rft.volume=8&rft.issue=31&rft.pages=222-227&rft.date=1830&rft.au=Moldenhawer&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3Da_E3AAAAMAAJ%26pg%3DPA222&rfr_id=info%3Asid%2Fen.wikipedia.org%3AChloroform" class="Z3988"></span></span> </li> <li id="cite_note-19"><span class="mw-cite-backlink"><b><a href="#cite_ref-19">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFDefalqueWright2000" class="citation journal cs1">Defalque, Ray J.; Wright, A. J. (2000). <a rel="nofollow" class="external text" href="https://doi.org/10.1097%2F00000542-200001000-00060">"Was chloroform produced before 1831?"</a>. <i>Anesthesiology</i>. <b>92</b> (1): 290–291. <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/10.1097%2F00000542-200001000-00060">10.1097/00000542-200001000-00060</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/10638939">10638939</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Anesthesiology&rft.atitle=Was+chloroform+produced+before+1831%3F&rft.volume=92&rft.issue=1&rft.pages=290-291&rft.date=2000&rft_id=info%3Adoi%2F10.1097%2F00000542-200001000-00060&rft_id=info%3Apmid%2F10638939&rft.aulast=Defalque&rft.aufirst=Ray+J.&rft.au=Wright%2C+A.+J.&rft_id=https%3A%2F%2Fdoi.org%2F10.1097%252F00000542-200001000-00060&rfr_id=info%3Asid%2Fen.wikipedia.org%3AChloroform" class="Z3988"></span></span> </li> <li id="cite_note-20"><span class="mw-cite-backlink"><b><a href="#cite_ref-20">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFGuthrie1832" class="citation journal cs1">Guthrie, Samuel (1832). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=iuzRAAAAMAAJ&pg=PA64">"New mode of preparing a spirituous solution of chloric ether"</a>. <i>The American Journal of Science and Arts</i>. <b>21</b>: 64–65 and 405–408. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20200729135541/https://books.google.com/books?id=iuzRAAAAMAAJ&pg=PA64">Archived</a> from the original on 29 July 2020<span class="reference-accessdate">. Retrieved <span class="nowrap">6 May</span> 2016</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=The+American+Journal+of+Science+and+Arts&rft.atitle=New+mode+of+preparing+a+spirituous+solution+of+chloric+ether&rft.volume=21&rft.pages=64-65+and+405-408&rft.date=1832&rft.aulast=Guthrie&rft.aufirst=Samuel&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DiuzRAAAAMAAJ%26pg%3DPA64&rfr_id=info%3Asid%2Fen.wikipedia.org%3AChloroform" class="Z3988"></span></span> </li> <li id="cite_note-21"><span class="mw-cite-backlink"><b><a href="#cite_ref-21">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFGuthrie1887" class="citation book cs1">Guthrie, Ossian (1887). <a rel="nofollow" class="external text" href="https://archive.org/details/39002011125375.med.yale.edu"><i>Memoirs of Dr. Samuel Guthrie, and the History of the Discovery of Chloroform</i></a>. Chicago: George K. Hazlitt & Co. p. <a rel="nofollow" class="external text" href="https://archive.org/details/39002011125375.med.yale.edu/page/n43">1</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Memoirs+of+Dr.+Samuel+Guthrie%2C+and+the+History+of+the+Discovery+of+Chloroform&rft.place=Chicago&rft.pages=1&rft.pub=George+K.+Hazlitt+%26+Co.&rft.date=1887&rft.aulast=Guthrie&rft.aufirst=Ossian&rft_id=https%3A%2F%2Farchive.org%2Fdetails%2F39002011125375.med.yale.edu&rfr_id=info%3Asid%2Fen.wikipedia.org%3AChloroform" class="Z3988"></span></span> </li> <li id="cite_note-22"><span class="mw-cite-backlink"><b><a href="#cite_ref-22">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFStratmann2003" class="citation book cs1">Stratmann, Linda (2003). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=VvA7AwAAQBAJ&pg=PT30">"Chapter 2"</a>. <i>Chloroform: The Quest for Oblivion</i>. Stroud: Sutton Publishing. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-7524-9931-4" title="Special:BookSources/978-0-7524-9931-4"><bdi>978-0-7524-9931-4</bdi></a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20200729120316/https://books.google.com/books?id=VvA7AwAAQBAJ&pg=PT30">Archived</a> from the original on 29 July 2020<span class="reference-accessdate">. Retrieved <span class="nowrap">6 May</span> 2016</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Chapter+2&rft.btitle=Chloroform%3A+The+Quest+for+Oblivion&rft.place=Stroud&rft.pub=Sutton+Publishing&rft.date=2003&rft.isbn=978-0-7524-9931-4&rft.aulast=Stratmann&rft.aufirst=Linda&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DVvA7AwAAQBAJ%26pg%3DPT30&rfr_id=info%3Asid%2Fen.wikipedia.org%3AChloroform" class="Z3988"></span></span> </li> <li id="cite_note-23"><span class="mw-cite-backlink"><b><a href="#cite_ref-23">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFLiebig1831" class="citation journal cs1">Liebig, Justus von (1831). <a rel="nofollow" class="external text" href="https://babel.hathitrust.org/cgi/pt?id=uc1.a0002753747;view=1up;seq=462">"Ueber die Zersetzung des Alkohols durch Chlor"</a> [On the decomposition of alcohol by chlorine]. <i>Annalen der Physik und Chemie</i>. <b>99</b> (11): 444. <a href="/wiki/Bibcode_(identifier)" class="mw-redirect" title="Bibcode (identifier)">Bibcode</a>:<a rel="nofollow" class="external text" href="https://ui.adsabs.harvard.edu/abs/1831AnP....99..444L">1831AnP....99..444L</a>. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2Fandp.18310991111">10.1002/andp.18310991111</a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20170510154137/https://babel.hathitrust.org/cgi/pt?id=uc1.a0002753747;view=1up;seq=462">Archived</a> from the original on 10 May 2017<span class="reference-accessdate">. Retrieved <span class="nowrap">6 May</span> 2016</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Annalen+der+Physik+und+Chemie&rft.atitle=Ueber+die+Zersetzung+des+Alkohols+durch+Chlor&rft.volume=99&rft.issue=11&rft.pages=444&rft.date=1831&rft_id=info%3Adoi%2F10.1002%2Fandp.18310991111&rft_id=info%3Abibcode%2F1831AnP....99..444L&rft.aulast=Liebig&rft.aufirst=Justus+von&rft_id=https%3A%2F%2Fbabel.hathitrust.org%2Fcgi%2Fpt%3Fid%3Duc1.a0002753747%3Bview%3D1up%3Bseq%3D462&rfr_id=info%3Asid%2Fen.wikipedia.org%3AChloroform" class="Z3988"></span></span> </li> <li id="cite_note-24"><span class="mw-cite-backlink"><b><a href="#cite_ref-24">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFLiebig1832" class="citation journal cs1">Liebig, Justus von (1832). <a rel="nofollow" class="external text" href="https://babel.hathitrust.org/cgi/pt?id=wu.89048351662&view=1up&seq=861">"Ueber die Verbindungen, welche durch die Einwirkung des Chlors auf Alkohol, Aether, ölbildendes Gas und Essiggeist entstehen"</a> [On the compounds which arise by the reaction of chlorine with alcohol [ethanol], ether [diethyl ether], oil-forming gas [ethylene], and spirit of vinegar [acetone]]. <i>Annalen der Physik und Chemie</i>. <b>100</b> (2): 243–295. <a href="/wiki/Bibcode_(identifier)" class="mw-redirect" title="Bibcode (identifier)">Bibcode</a>:<a rel="nofollow" class="external text" href="https://ui.adsabs.harvard.edu/abs/1832AnP...100..243L">1832AnP...100..243L</a>. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2Fandp.18321000206">10.1002/andp.18321000206</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Annalen+der+Physik+und+Chemie&rft.atitle=Ueber+die+Verbindungen%2C+welche+durch+die+Einwirkung+des+Chlors+auf+Alkohol%2C+Aether%2C+%C3%B6lbildendes+Gas+und+Essiggeist+entstehen&rft.volume=100&rft.issue=2&rft.pages=243-295&rft.date=1832&rft_id=info%3Adoi%2F10.1002%2Fandp.18321000206&rft_id=info%3Abibcode%2F1832AnP...100..243L&rft.aulast=Liebig&rft.aufirst=Justus+von&rft_id=https%3A%2F%2Fbabel.hathitrust.org%2Fcgi%2Fpt%3Fid%3Dwu.89048351662%26view%3D1up%26seq%3D861&rfr_id=info%3Asid%2Fen.wikipedia.org%3AChloroform" class="Z3988"></span><br />On pages 259–265, Liebig describes <i>Chlorkohlenstoff</i> ("carbon chloride", chloroform), but on p. 264, Liebig incorrectly states that the <a href="/wiki/Empirical_formula" title="Empirical formula">empirical formula</a> of chloroform is C<sub>2</sub>Cl<sub>5</sub>.</span> </li> <li id="cite_note-25"><span class="mw-cite-backlink"><b><a href="#cite_ref-25">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFSoubeiran1831" class="citation journal cs1">Soubeiran, Eugène (1831). <a rel="nofollow" class="external text" href="https://babel.hathitrust.org/cgi/pt?id=ien.35556014127963;view=1up;seq=115">"Recherches sur quelques combinaisons du chlore"</a> [Investigations into some compounds of chlorine]. <i>Annales de Chimie et de Physique</i>. Série 2. <b>48</b>: 113–157. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20170510154147/https://babel.hathitrust.org/cgi/pt?id=ien.35556014127963;view=1up;seq=115">Archived</a> from the original on 10 May 2017<span class="reference-accessdate">. Retrieved <span class="nowrap">6 May</span> 2016</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Annales+de+Chimie+et+de+Physique&rft.atitle=Recherches+sur+quelques+combinaisons+du+chlore&rft.volume=48&rft.pages=113-157&rft.date=1831&rft.aulast=Soubeiran&rft.aufirst=Eug%C3%A8ne&rft_id=https%3A%2F%2Fbabel.hathitrust.org%2Fcgi%2Fpt%3Fid%3Dien.35556014127963%3Bview%3D1up%3Bseq%3D115&rfr_id=info%3Asid%2Fen.wikipedia.org%3AChloroform" class="Z3988"></span> <ul><li>Reprinted in <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFSoubeiran1831" class="citation journal cs1">Soubeiran, Eugène (1831). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=QP1BAAAAcAAJ&pg=PA657">"Recherches sur quelques combinaisons du chlore"</a> [Investigations on some compounds of chlorine]. <i>Journal de Pharmacie et des Sciences Accessoires</i>. <b>17</b>: 657–672. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20200729112744/https://books.google.com/books?id=QP1BAAAAcAAJ&pg=PA657">Archived</a> from the original on 29 July 2020<span class="reference-accessdate">. Retrieved <span class="nowrap">6 May</span> 2016</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Journal+de+Pharmacie+et+des+Sciences+Accessoires&rft.atitle=Recherches+sur+quelques+combinaisons+du+chlore&rft.volume=17&rft.pages=657-672&rft.date=1831&rft.aulast=Soubeiran&rft.aufirst=Eug%C3%A8ne&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DQP1BAAAAcAAJ%26pg%3DPA657&rfr_id=info%3Asid%2Fen.wikipedia.org%3AChloroform" class="Z3988"></span></li> <li>Reprinted in <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFSoubeiran1832" class="citation journal cs1">Soubeiran, Eugène (1832). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=aBZJAQAAMAAJ&pg=PA1">"Suite des recherches sur quelques combinaisons du chlore"</a> [Continuation of investigations on some compounds of chlorine]. <i>Journal de Pharmacie et des Sciences Accessoires</i>. <b>18</b>: 1–24. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20200729121309/https://books.google.com/books?id=aBZJAQAAMAAJ&pg=PA1">Archived</a> from the original on 29 July 2020<span class="reference-accessdate">. Retrieved <span class="nowrap">6 May</span> 2016</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Journal+de+Pharmacie+et+des+Sciences+Accessoires&rft.atitle=Suite+des+recherches+sur+quelques+combinaisons+du+chlore&rft.volume=18&rft.pages=1-24&rft.date=1832&rft.aulast=Soubeiran&rft.aufirst=Eug%C3%A8ne&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DaBZJAQAAMAAJ%26pg%3DPA1&rfr_id=info%3Asid%2Fen.wikipedia.org%3AChloroform" class="Z3988"></span></li></ul> </span></li> <li id="cite_note-26"><span class="mw-cite-backlink"><b><a href="#cite_ref-26">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFDumas1834" class="citation journal cs1">Dumas, J.-B. (1834). "Récherches rélative à l'action du chlore sur l'alcool" [Experiments regarding the action of chlorine on alcohol]. <i>L'Institut, Journal Général des Sociétés et Travaux Scientifiques de la France et de l'Étranger</i>. <b>2</b>: 106–108 and 112–115.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=L%27Institut%2C+Journal+G%C3%A9n%C3%A9ral+des+Soci%C3%A9t%C3%A9s+et+Travaux+Scientifiques+de+la+France+et+de+l%27%C3%89tranger&rft.atitle=R%C3%A9cherches+r%C3%A9lative+%C3%A0+l%27action+du+chlore+sur+l%27alcool&rft.volume=2&rft.pages=106-108+and+112-115&rft.date=1834&rft.aulast=Dumas&rft.aufirst=J.-B.&rfr_id=info%3Asid%2Fen.wikipedia.org%3AChloroform" class="Z3988"></span> <ul><li>Reprinted in <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFDumas1834" class="citation journal cs1">Dumas, J.-B. (1834). <a rel="nofollow" class="external text" href="https://babel.hathitrust.org/cgi/pt?id=umn.31951d00316736l;view=1up;seq=668">"Untersuchung über die Wirkung des Chlors auf den Alkohol"</a> [Investigation of the action of chlorine on alcohol]. <i>Annalen der Physik und Chemie</i>. <b>107</b> (42): 657–673. <a href="/wiki/Bibcode_(identifier)" class="mw-redirect" title="Bibcode (identifier)">Bibcode</a>:<a rel="nofollow" class="external text" href="https://ui.adsabs.harvard.edu/abs/1834AnP...107..657D">1834AnP...107..657D</a>. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2Fandp.18341074202">10.1002/andp.18341074202</a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20170510152609/https://babel.hathitrust.org/cgi/pt?id=umn.31951d00316736l;view=1up;seq=668">Archived</a> from the original on 10 May 2017<span class="reference-accessdate">. Retrieved <span class="nowrap">12 May</span> 2016</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Annalen+der+Physik+und+Chemie&rft.atitle=Untersuchung+%C3%BCber+die+Wirkung+des+Chlors+auf+den+Alkohol&rft.volume=107&rft.issue=42&rft.pages=657-673&rft.date=1834&rft_id=info%3Adoi%2F10.1002%2Fandp.18341074202&rft_id=info%3Abibcode%2F1834AnP...107..657D&rft.aulast=Dumas&rft.aufirst=J.-B.&rft_id=https%3A%2F%2Fbabel.hathitrust.org%2Fcgi%2Fpt%3Fid%3Dumn.31951d00316736l%3Bview%3D1up%3Bseq%3D668&rfr_id=info%3Asid%2Fen.wikipedia.org%3AChloroform" class="Z3988"></span><br />On p. 653, Dumas states chloroform's empirical formula:</li></ul> <dl><dd><dl><dd><i>"Es scheint mir also erweisen, dass die von mir analysirte Substance, … zur Formel hat: <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">C<sub class="template-chem2-sub">2</sub>H<sub class="template-chem2-sub">2</sub>Cl<sub class="template-chem2-sub">6</sub></span>."</i> (Thus it seems to me to show that the substance [that was] analyzed by me … has as [its empirical] formula: <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">C<sub class="template-chem2-sub">2</sub>H<sub class="template-chem2-sub">2</sub>Cl<sub class="template-chem2-sub">6</sub></span>.) [Note: The coefficients of his empirical formula must be halved.]</dd></dl></dd> <dd>Dumas then notes that chloroform's simple <a href="/wiki/Empirical_formula" title="Empirical formula">empirical formula</a> resembles that of <a href="/wiki/Formic_acid" title="Formic acid">formic acid</a>. Furthermore, if chloroform is boiled with <a href="/wiki/Potassium_hydroxide" title="Potassium hydroxide">potassium hydroxide</a>, one of the products is <a href="/wiki/Potassium_formate" title="Potassium formate">potassium formate</a>. On p. 654, Dumas names chloroform: <dl><dd><i>"Diess hat mich veranlasst diese Substanz mit dem Namen 'Chloroform' zu belegen."</i> (This caused me to bestow this substance with the name "chloroform" [i.e., formyl chloride or chloride of formic acid].)</dd></dl></dd></dl> <ul><li>Reprinted in <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFDumas1835" class="citation journal cs1">Dumas, J.-B. (1835). <a rel="nofollow" class="external text" href="https://babel.hathitrust.org/cgi/pt?id=uva.x002457902;view=1up;seq=542">"Ueber die Wirkung des Chlors auf den Alkohol"</a> [On the action of chlorine on alcohol]. <i>Annalen der Pharmacie</i>. <b>16</b> (2): 164–171. <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%2Fjlac.18350160213">10.1002/jlac.18350160213</a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20170510152601/https://babel.hathitrust.org/cgi/pt?id=uva.x002457902;view=1up;seq=542">Archived</a> from the original on 10 May 2017<span class="reference-accessdate">. Retrieved <span class="nowrap">12 May</span> 2016</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Annalen+der+Pharmacie&rft.atitle=Ueber+die+Wirkung+des+Chlors+auf+den+Alkohol&rft.volume=16&rft.issue=2&rft.pages=164-171&rft.date=1835&rft_id=info%3Adoi%2F10.1002%2Fjlac.18350160213&rft.aulast=Dumas&rft.aufirst=J.-B.&rft_id=https%3A%2F%2Fbabel.hathitrust.org%2Fcgi%2Fpt%3Fid%3Duva.x002457902%3Bview%3D1up%3Bseq%3D542&rfr_id=info%3Asid%2Fen.wikipedia.org%3AChloroform" class="Z3988"></span></li></ul> </span></li> <li id="cite_note-pdf1-27"><span class="mw-cite-backlink">^ <a href="#cite_ref-pdf1_27-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-pdf1_27-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFDefalqueWright2004" class="citation journal cs1">Defalque, R. J.; Wright, A. J. (2004). <a rel="nofollow" class="external text" href="http://www.ph.ucla.edu/epi/snow/anaesthesia59_394_400_2004.pdf">"The short, tragic life of Robert M. Glover"</a> <span class="cs1-format">(PDF)</span>. <i>Anaesthesia</i>. <b>59</b> (4): 394–400. <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/10.1111%2Fj.1365-2044.2004.03671.x">10.1111/j.1365-2044.2004.03671.x</a></span>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/15023112">15023112</a>. <a href="/wiki/S2CID_(identifier)" class="mw-redirect" title="S2CID (identifier)">S2CID</a> <a rel="nofollow" class="external text" href="https://api.semanticscholar.org/CorpusID:46428403">46428403</a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20160309080158/http://www.ph.ucla.edu/epi/snow/anaesthesia59_394_400_2004.pdf">Archived</a> <span class="cs1-format">(PDF)</span> from the original on 9 March 2016.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Anaesthesia&rft.atitle=The+short%2C+tragic+life+of+Robert+M.+Glover&rft.volume=59&rft.issue=4&rft.pages=394-400&rft.date=2004&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A46428403%23id-name%3DS2CID&rft_id=info%3Apmid%2F15023112&rft_id=info%3Adoi%2F10.1111%2Fj.1365-2044.2004.03671.x&rft.aulast=Defalque&rft.aufirst=R.+J.&rft.au=Wright%2C+A.+J.&rft_id=http%3A%2F%2Fwww.ph.ucla.edu%2Fepi%2Fsnow%2Fanaesthesia59_394_400_2004.pdf&rfr_id=info%3Asid%2Fen.wikipedia.org%3AChloroform" class="Z3988"></span></span> </li> <li id="cite_note-Gordon2002-28"><span class="mw-cite-backlink">^ <a href="#cite_ref-Gordon2002_28-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Gordon2002_28-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFGordon2002" class="citation book cs1">Gordon, H. Laing (November 2002). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=pYer05UwKBYC&pg=PA106"><i>Sir James Young Simpson and Chloroform (1811–1870)</i></a>. Minerva Group. pp. 106–109. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1-4102-0291-8" title="Special:BookSources/978-1-4102-0291-8"><bdi>978-1-4102-0291-8</bdi></a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20160506214333/https://books.google.com/books?id=pYer05UwKBYC&pg=PA106">Archived</a> from the original on 6 May 2016<span class="reference-accessdate">. Retrieved <span class="nowrap">5 January</span> 2016</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Sir+James+Young+Simpson+and+Chloroform+%281811%E2%80%931870%29&rft.pages=106-109&rft.pub=Minerva+Group&rft.date=2002-11&rft.isbn=978-1-4102-0291-8&rft.aulast=Gordon&rft.aufirst=H.+Laing&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DpYer05UwKBYC%26pg%3DPA106&rfr_id=info%3Asid%2Fen.wikipedia.org%3AChloroform" class="Z3988"></span></span> </li> <li id="cite_note-eb-29"><span class="mw-cite-backlink"><b><a href="#cite_ref-eb_29-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation encyclopaedia cs1"><a rel="nofollow" class="external text" href="https://www.britannica.com/EBchecked/topic/545447/Sir-James-Young-Simpson-1st-Baronet">"Sir James Young Simpson"</a>. <i>Encyclopædia Britannica</i>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20130727130133/https://www.britannica.com/EBchecked/topic/545447/Sir-James-Young-Simpson-1st-Baronet">Archived</a> from the original on 27 July 2013<span class="reference-accessdate">. Retrieved <span class="nowrap">23 August</span> 2013</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Sir+James+Young+Simpson&rft.btitle=Encyclop%C3%A6dia+Britannica&rft_id=https%3A%2F%2Fwww.britannica.com%2FEBchecked%2Ftopic%2F545447%2FSir-James-Young-Simpson-1st-Baronet&rfr_id=info%3Asid%2Fen.wikipedia.org%3AChloroform" class="Z3988"></span></span> </li> <li id="cite_note-30"><span class="mw-cite-backlink"><b><a href="#cite_ref-30">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFWorling1998" class="citation journal cs1">Worling, P.M. (1998). 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Edwards (2013). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3638459">"Identification of Dehalobacter reductive dehalogenases that catalyse dechlorination of chloroform, 1,1,1-trichloroethane and 1,1-dichloroethane"</a>. <i>Philos Trans R Soc Lond B Biol Sci</i>. <b>368</b> (1616): 20120318. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1098%2Frstb.2012.0318">10.1098/rstb.2012.0318</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/PMC3638459">3638459</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/23479748">23479748</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Philos+Trans+R+Soc+Lond+B+Biol+Sci&rft.atitle=Identification+of+Dehalobacter+reductive+dehalogenases+that+catalyse+dechlorination+of+chloroform%2C+1%2C1%2C1-trichloroethane+and+1%2C1-dichloroethane&rft.volume=368&rft.issue=1616&rft.pages=20120318&rft.date=2013&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC3638459%23id-name%3DPMC&rft_id=info%3Apmid%2F23479748&rft_id=info%3Adoi%2F10.1098%2Frstb.2012.0318&rft.au=Shuiquan+Tang&rft.au=Elizabeth+A.+Edwards&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC3638459&rfr_id=info%3Asid%2Fen.wikipedia.org%3AChloroform" class="Z3988"></span></span> </li> <li id="cite_note-84"><span class="mw-cite-backlink"><b><a href="#cite_ref-84">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFJugderErtanWongBraidy2016" class="citation journal cs1">Jugder, Bat-Erdene; Ertan, Haluk; Wong, Yie Kuan; Braidy, Nady; Manefield, Michael; Marquis, Christopher P.; Lee, Matthew (10 August 2016). "Genomic, transcriptomic and proteomic analyses of Dehalobacter UNSWDHB in response to chloroform". <i>Environmental Microbiology Reports</i>. <b>8</b> (5): 814–824. <a href="/wiki/Bibcode_(identifier)" class="mw-redirect" title="Bibcode (identifier)">Bibcode</a>:<a rel="nofollow" class="external text" href="https://ui.adsabs.harvard.edu/abs/2016EnvMR...8..814J">2016EnvMR...8..814J</a>. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1111%2F1758-2229.12444">10.1111/1758-2229.12444</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/1758-2229">1758-2229</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/27452500">27452500</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Environmental+Microbiology+Reports&rft.atitle=Genomic%2C+transcriptomic+and+proteomic+analyses+of+Dehalobacter+UNSWDHB+in+response+to+chloroform&rft.volume=8&rft.issue=5&rft.pages=814-824&rft.date=2016-08-10&rft_id=info%3Adoi%2F10.1111%2F1758-2229.12444&rft.issn=1758-2229&rft_id=info%3Apmid%2F27452500&rft_id=info%3Abibcode%2F2016EnvMR...8..814J&rft.aulast=Jugder&rft.aufirst=Bat-Erdene&rft.au=Ertan%2C+Haluk&rft.au=Wong%2C+Yie+Kuan&rft.au=Braidy%2C+Nady&rft.au=Manefield%2C+Michael&rft.au=Marquis%2C+Christopher+P.&rft.au=Lee%2C+Matthew&rfr_id=info%3Asid%2Fen.wikipedia.org%3AChloroform" class="Z3988"></span></span> </li> </ol></div></div> <div class="mw-heading mw-heading2"><h2 id="External_links">External links</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Chloroform&action=edit&section=22" title="Edit section: External links"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1235681985">.mw-parser-output .side-box{margin:4px 0;box-sizing:border-box;border:1px solid #aaa;font-size:88%;line-height:1.25em;background-color:var(--background-color-interactive-subtle,#f8f9fa);display:flow-root}.mw-parser-output .side-box-abovebelow,.mw-parser-output .side-box-text{padding:0.25em 0.9em}.mw-parser-output .side-box-image{padding:2px 0 2px 0.9em;text-align:center}.mw-parser-output .side-box-imageright{padding:2px 0.9em 2px 0;text-align:center}@media(min-width:500px){.mw-parser-output .side-box-flex{display:flex;align-items:center}.mw-parser-output .side-box-text{flex:1;min-width:0}}@media(min-width:720px){.mw-parser-output .side-box{width:238px}.mw-parser-output .side-box-right{clear:right;float:right;margin-left:1em}.mw-parser-output .side-box-left{margin-right:1em}}</style><style data-mw-deduplicate="TemplateStyles:r1237033735">@media print{body.ns-0 .mw-parser-output .sistersitebox{display:none!important}}@media screen{html.skin-theme-clientpref-night .mw-parser-output .sistersitebox img[src*="Wiktionary-logo-en-v2.svg"]{background-color:white}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .sistersitebox img[src*="Wiktionary-logo-en-v2.svg"]{background-color:white}}</style><div class="side-box side-box-right plainlinks sistersitebox"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"> <div class="side-box-flex"> <div class="side-box-image"><span class="noviewer" typeof="mw:File"><span><img alt="" src="//upload.wikimedia.org/wikipedia/en/thumb/4/4a/Commons-logo.svg/30px-Commons-logo.svg.png" decoding="async" width="30" height="40" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/4/4a/Commons-logo.svg/45px-Commons-logo.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/4/4a/Commons-logo.svg/59px-Commons-logo.svg.png 2x" data-file-width="1024" data-file-height="1376" /></span></span></div> <div class="side-box-text plainlist">Wikimedia Commons has media related to <span style="font-weight: bold; font-style: italic;"><a href="https://commons.wikimedia.org/wiki/Category:Chloroform" class="extiw" title="commons:Category:Chloroform">Chloroform</a></span>.</div></div> </div> <ul><li><a rel="nofollow" class="external text" href="http://www.chm.bris.ac.uk/motm/chloroform/chloroformv.htm">Chloroform "The Molecular Lifesaver"</a> – An article at Oxford University providing facts about chloroform.</li> <li><a rel="nofollow" class="external text" href="https://archive.org/details/0055-0000-7637-0000-0-0000-0000-0">Chloroform Administration</a> – a short film of anaesthetic chloroform application, filmed in the 1930s</li> <li><a rel="nofollow" class="external text" href="http://www.inchem.org/documents/cicads/cicads/cicad58.htm">Concise International Chemical Assessment Document 58</a></li> <li>IARC Summaries & Evaluations: <a rel="nofollow" class="external text" href="http://www.inchem.org/documents/iarc/vol01/chloroform.html">Vol. 1 (1972)</a>, <a rel="nofollow" class="external text" href="http://www.inchem.org/documents/iarc/vol20/chloroform.html">Vol. 20 (1979)</a>, <a rel="nofollow" class="external text" href="http://www.inchem.org/documents/iarc/suppl7/chloroform.html">Suppl. 7 (1987)</a>, <a rel="nofollow" class="external text" href="http://www.inchem.org/documents/iarc/vol73/73-05.html">Vol. 73 (1999)</a></li> <li><a rel="nofollow" class="external text" href="https://www.ilo.org/dyn/icsc/showcard.display?p_lang=en&p_card_id=0027&p_version=2">International Chemical Safety Card 0027</a></li> <li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFNIOSH_Pocket_Guide_to_Chemical_Hazards" class="citation web cs1">NIOSH Pocket Guide to Chemical Hazards. <a rel="nofollow" class="external text" href="https://www.cdc.gov/niosh/npg/npgd0127.html">"#0127"</a>. <a href="/wiki/National_Institute_for_Occupational_Safety_and_Health" title="National Institute for Occupational Safety and Health">National Institute for Occupational Safety and Health</a> (NIOSH).</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=%230127&rft.pub=National+Institute+for+Occupational+Safety+and+Health+%28NIOSH%29&rft.au=NIOSH+Pocket+Guide+to+Chemical+Hazards&rft_id=https%3A%2F%2Fwww.cdc.gov%2Fniosh%2Fnpg%2Fnpgd0127.html&rfr_id=info%3Asid%2Fen.wikipedia.org%3AChloroform" class="Z3988"></span></li> <li><a rel="nofollow" class="external text" href="http://webbook.nist.gov/cgi/cbook.cgi?ID=67-66-3&Units=SI&cTG=on&cTC=on&cTP=on">NIST Standard Reference Database</a></li></ul> <div class="navbox-styles"><style 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.navbox-odd{background-color:transparent}.mw-parser-output .navbox .hlist td dl,.mw-parser-output .navbox .hlist td ol,.mw-parser-output .navbox .hlist td ul,.mw-parser-output .navbox td.hlist dl,.mw-parser-output .navbox td.hlist ol,.mw-parser-output .navbox td.hlist ul{padding:0.125em 0}.mw-parser-output .navbox .navbar{display:block;font-size:100%}.mw-parser-output .navbox-title .navbar{float:left;text-align:left;margin-right:0.5em}body.skin--responsive .mw-parser-output .navbox-image img{max-width:none!important}@media print{body.ns-0 .mw-parser-output .navbox{display:none!important}}</style></div><div role="navigation" class="navbox" aria-labelledby="Halomethanes" style="padding:3px"><table class="nowraplinks mw-collapsible autocollapse navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><style 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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:Halomethanes" title="Template:Halomethanes"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Halomethanes" title="Template talk:Halomethanes"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Halomethanes" title="Special:EditPage/Template:Halomethanes"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Halomethanes" style="font-size:114%;margin:0 4em"><a href="/wiki/Halomethane" title="Halomethane">Halomethanes</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Methane" title="Methane">Unsubstituted</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/Methane" title="Methane">CH<sub>4</sub></a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Monohalomethane" title="Monohalomethane">Monosubstituted</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/Fluoromethane" title="Fluoromethane">CH<sub>3</sub>F</a></li> <li><a href="/wiki/Chloromethane" title="Chloromethane">CH<sub>3</sub>Cl</a></li> <li><a href="/wiki/Bromomethane" title="Bromomethane">CH<sub>3</sub>Br</a></li> <li><a href="/wiki/Iodomethane" title="Iodomethane">CH<sub>3</sub>I</a></li> <li><a href="/w/index.php?title=Methyl_astatide&action=edit&redlink=1" class="new" title="Methyl astatide (page does not exist)">CH<sub>3</sub>At</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Dihalomethane" title="Dihalomethane">Disubstituted</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/Difluoromethane" title="Difluoromethane">CH<sub>2</sub>F<sub>2</sub></a></li> <li><a href="/wiki/Chlorofluoromethane" title="Chlorofluoromethane">CH<sub>2</sub>ClF</a></li> <li><a href="/wiki/Bromofluoromethane" title="Bromofluoromethane">CH<sub>2</sub>BrF</a></li> <li><a href="/wiki/Fluoroiodomethane" title="Fluoroiodomethane">CH<sub>2</sub>FI</a></li> <li><a href="/wiki/Dichloromethane" title="Dichloromethane">CH<sub>2</sub>Cl<sub>2</sub></a></li> <li><a href="/wiki/Bromochloromethane" title="Bromochloromethane">CH<sub>2</sub>BrCl</a></li> <li><a href="/wiki/Chloroiodomethane" title="Chloroiodomethane">CH<sub>2</sub>ClI</a></li> <li><a href="/wiki/Dibromomethane" title="Dibromomethane">CH<sub>2</sub>Br<sub>2</sub></a></li> <li><a href="/wiki/Bromoiodomethane" title="Bromoiodomethane">CH<sub>2</sub>BrI</a></li> <li><a href="/wiki/Diiodomethane" title="Diiodomethane">CH<sub>2</sub>I<sub>2</sub></a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Trihalomethane" title="Trihalomethane">Trisubstituted</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/Fluoroform" title="Fluoroform">CHF<sub>3</sub></a></li> <li><a href="/wiki/Chlorodifluoromethane" title="Chlorodifluoromethane">CHClF<sub>2</sub></a></li> <li><a href="/wiki/Bromodifluoromethane" title="Bromodifluoromethane">CHBrF<sub>2</sub></a></li> <li><a href="/w/index.php?title=Difluoroiodomethane&action=edit&redlink=1" class="new" title="Difluoroiodomethane (page does not exist)">CHF<sub>2</sub>I</a></li> <li><a href="/wiki/Dichlorofluoromethane" title="Dichlorofluoromethane">CHCl<sub>2</sub>F</a></li> <li><a href="/wiki/Bromochlorofluoromethane" title="Bromochlorofluoromethane">C*HBrClF</a></li> <li><a href="/w/index.php?title=Chlorofluoroiodomethane&action=edit&redlink=1" class="new" title="Chlorofluoroiodomethane (page does not exist)">C*HClFI</a></li> <li><a href="/wiki/Dibromofluoromethane" title="Dibromofluoromethane">CHBr<sub>2</sub>F</a></li> <li><a href="/w/index.php?title=Bromofluoroiodomethane&action=edit&redlink=1" class="new" title="Bromofluoroiodomethane (page does not exist)">C*HBrFI</a></li> <li><a href="/w/index.php?title=Fluorodiiodomethane&action=edit&redlink=1" class="new" title="Fluorodiiodomethane (page does not exist)">CHFI<sub>2</sub></a></li> <li><a class="mw-selflink selflink">CHCl<sub>3</sub></a></li> <li><a href="/wiki/Bromodichloromethane" title="Bromodichloromethane">CHBrCl<sub>2</sub></a></li> <li><a href="/wiki/Dichloroiodomethane" title="Dichloroiodomethane">CHCl<sub>2</sub>I</a></li> <li><a href="/wiki/Dibromochloromethane" title="Dibromochloromethane">CHBr<sub>2</sub>Cl</a></li> <li><a href="/w/index.php?title=Bromochloroiodomethane&action=edit&redlink=1" class="new" title="Bromochloroiodomethane (page does not exist)">C*HBrClI</a></li> <li><a href="/w/index.php?title=Chlorodiiodomethane&action=edit&redlink=1" class="new" title="Chlorodiiodomethane (page does not exist)">CHClI<sub>2</sub></a></li> <li><a href="/wiki/Bromoform" title="Bromoform">CHBr<sub>3</sub></a></li> <li><a href="/w/index.php?title=Dibromoiodomethane&action=edit&redlink=1" class="new" title="Dibromoiodomethane (page does not exist)">CHBr<sub>2</sub>I</a></li> <li><a href="/w/index.php?title=Bromodiiodomethane&action=edit&redlink=1" class="new" title="Bromodiiodomethane (page does not exist)">CHBrI<sub>2</sub></a></li> <li><a href="/wiki/Iodoform" title="Iodoform">CHI<sub>3</sub></a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Tetrahalomethane" title="Tetrahalomethane">Tetrasubstituted</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/Tetrafluoromethane" class="mw-redirect" title="Tetrafluoromethane">CF<sub>4</sub></a></li> <li><a href="/wiki/Chlorotrifluoromethane" title="Chlorotrifluoromethane">CClF<sub>3</sub></a></li> <li><a href="/wiki/Bromotrifluoromethane" title="Bromotrifluoromethane">CBrF<sub>3</sub></a></li> <li><a href="/wiki/Trifluoroiodomethane" title="Trifluoroiodomethane">CF<sub>3</sub>I</a></li> <li><a href="/wiki/Dichlorodifluoromethane" title="Dichlorodifluoromethane">CCl<sub>2</sub>F<sub>2</sub></a></li> <li><a href="/wiki/Bromochlorodifluoromethane" title="Bromochlorodifluoromethane">CBrClF<sub>2</sub></a></li> <li><a href="/w/index.php?title=Chlorodifluoroiodomethane&action=edit&redlink=1" class="new" title="Chlorodifluoroiodomethane (page does not exist)">CClF<sub>2</sub>I</a></li> <li><a href="/wiki/Dibromodifluoromethane" title="Dibromodifluoromethane">CBr<sub>2</sub>F<sub>2</sub></a></li> <li><a href="/w/index.php?title=Bromodifluoroiodomethane&action=edit&redlink=1" class="new" title="Bromodifluoroiodomethane (page does not exist)">CBrF<sub>2</sub>I</a></li> <li><a href="/w/index.php?title=Difluorodiiodomethane&action=edit&redlink=1" class="new" title="Difluorodiiodomethane (page does not exist)">CF<sub>2</sub>I<sub>2</sub></a></li> <li><a href="/wiki/Trichlorofluoromethane" title="Trichlorofluoromethane">CCl<sub>3</sub>F</a></li> <li><a href="/w/index.php?title=Bromodichlorofluoromethane&action=edit&redlink=1" class="new" title="Bromodichlorofluoromethane (page does not exist)">CBrCl<sub>2</sub>F</a></li> <li><a href="/w/index.php?title=Dichlorofluoroiodomethane&action=edit&redlink=1" class="new" title="Dichlorofluoroiodomethane (page does not exist)">CCl<sub>2</sub>FI</a></li> <li><a href="/w/index.php?title=Dibromochlorofluoromethane&action=edit&redlink=1" class="new" title="Dibromochlorofluoromethane (page does not exist)">CBr<sub>2</sub>ClF</a></li> <li><a href="/wiki/Bromochlorofluoroiodomethane" title="Bromochlorofluoroiodomethane">C*BrClFI</a></li> <li><a href="/w/index.php?title=Chlorofluorodiiodomethane&action=edit&redlink=1" class="new" title="Chlorofluorodiiodomethane (page does not exist)">CClFI<sub>2</sub></a></li> <li><a href="/wiki/Tribromofluoromethane" title="Tribromofluoromethane">CBr<sub>3</sub>F</a></li> <li><a href="/w/index.php?title=Dibromofluoroiodomethane&action=edit&redlink=1" class="new" title="Dibromofluoroiodomethane (page does not exist)">CBr<sub>2</sub>FI</a></li> <li><a href="/w/index.php?title=Bromofluorodiiodomethane&action=edit&redlink=1" class="new" title="Bromofluorodiiodomethane (page does not exist)">CBrFI<sub>2</sub></a></li> <li><a href="/wiki/Fluorotriiodomethane" title="Fluorotriiodomethane">CFI<sub>3</sub></a></li> <li><a href="/wiki/Carbon_tetrachloride" title="Carbon tetrachloride">CCl<sub>4</sub></a></li> <li><a href="/w/index.php?title=Bromotrichloromethane&action=edit&redlink=1" class="new" title="Bromotrichloromethane (page does not exist)">CBrCl<sub>3</sub></a></li> <li><a href="/w/index.php?title=Trichloroiodomethane&action=edit&redlink=1" class="new" title="Trichloroiodomethane (page does not exist)">CCl<sub>3</sub>I</a></li> <li><a href="/w/index.php?title=Dibromodichloromethane&action=edit&redlink=1" class="new" title="Dibromodichloromethane (page does not exist)">CBr<sub>2</sub>Cl<sub>2</sub></a></li> <li><a href="/w/index.php?title=Bromodichloroiodomethane&action=edit&redlink=1" class="new" title="Bromodichloroiodomethane (page does not exist)">CBrCl<sub>2</sub>I</a></li> <li><a href="/w/index.php?title=Dichlorodiiodomethane&action=edit&redlink=1" class="new" title="Dichlorodiiodomethane (page does not exist)">CCl<sub>2</sub>I<sub>2</sub></a></li> <li><a href="/w/index.php?title=Tribromochloromethane&action=edit&redlink=1" class="new" title="Tribromochloromethane (page does not exist)">CBr<sub>3</sub>Cl</a></li> <li><a href="/w/index.php?title=Dibromochloroiodomethane&action=edit&redlink=1" class="new" title="Dibromochloroiodomethane (page does not exist)">CBr<sub>2</sub>ClI</a></li> <li><a href="/w/index.php?title=Bromochlorodiiodomethane&action=edit&redlink=1" class="new" title="Bromochlorodiiodomethane (page does not exist)">CBrClI<sub>2</sub></a></li> <li><a href="/w/index.php?title=Chlorotriiodomethane&action=edit&redlink=1" class="new" title="Chlorotriiodomethane (page does not exist)">CClI<sub>3</sub></a></li> <li><a href="/wiki/Tetrabromomethane" class="mw-redirect" title="Tetrabromomethane">CBr<sub>4</sub></a></li> <li><a href="/w/index.php?title=Tribromoiodomethane&action=edit&redlink=1" class="new" title="Tribromoiodomethane (page does not exist)">CBr<sub>3</sub>I</a></li> <li><a href="/w/index.php?title=Dibromodiiodomethane&action=edit&redlink=1" class="new" title="Dibromodiiodomethane (page does not exist)">CBr<sub>2</sub>I<sub>2</sub></a></li> <li><a href="/w/index.php?title=Bromotriiodomethane&action=edit&redlink=1" class="new" title="Bromotriiodomethane (page does not exist)">CBrI<sub>3</sub></a></li> <li><a href="/wiki/Carbon_tetraiodide" title="Carbon tetraiodide">CI<sub>4</sub></a></li></ul> </div></td></tr><tr><td class="navbox-abovebelow" colspan="2"><div>* <a href="/wiki/Chirality_(chemistry)" title="Chirality (chemistry)">Chiral</a> compound.</div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"></div><div role="navigation" class="navbox" aria-labelledby="General_anesthetics_(N01A)" style="padding:3px"><table class="nowraplinks mw-collapsible autocollapse navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><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:General_anesthetics" title="Template:General anesthetics"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:General_anesthetics" title="Template talk:General anesthetics"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:General_anesthetics" title="Special:EditPage/Template:General anesthetics"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="General_anesthetics_(N01A)" style="font-size:114%;margin:0 4em"><a href="/wiki/General_anaesthetic" title="General anaesthetic">General anesthetics</a> (<a href="/wiki/ATC_code_N01#N01A" title="ATC code N01">N01A</a>)</div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Inhalational_anesthetic" title="Inhalational anesthetic">Inhalational</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a class="mw-selflink selflink">Chloroform</a><sup>‡</sup></li> <li><a href="/wiki/Cyclopropane" title="Cyclopropane">Cyclopropane</a><sup>‡</sup></li> <li><a href="/wiki/Desflurane" title="Desflurane">Desflurane</a></li> <li><a href="/wiki/Diethyl_ether" title="Diethyl ether">Diethyl ether</a><sup>‡</sup></li> <li><a href="/wiki/Enflurane" title="Enflurane">Enflurane</a></li> <li><a href="/wiki/Ethylene" title="Ethylene">Ethylene</a><sup>‡</sup></li> <li><a href="/wiki/Fluroxene" title="Fluroxene">Fluroxene</a><sup>‡</sup></li> <li><a href="/wiki/Halothane" title="Halothane">Halothane</a><sup>#</sup></li> <li><a href="/wiki/Isoflurane" title="Isoflurane">Isoflurane</a><sup>#</sup></li> <li><a href="/wiki/Methoxyflurane" title="Methoxyflurane">Methoxyflurane</a></li> <li><a href="/wiki/Methoxypropane" title="Methoxypropane">Methoxypropane</a><sup>‡</sup></li> <li><a href="/wiki/Nitrous_oxide" title="Nitrous oxide">Nitrous oxide</a><sup>#</sup></li> <li><a href="/wiki/Sevoflurane" title="Sevoflurane">Sevoflurane</a></li> <li><a href="/wiki/Trichloroethylene" title="Trichloroethylene">Trichloroethylene</a><sup>‡</sup></li> <li><a href="/wiki/Divinyl_ether" title="Divinyl ether">Vinyl ether</a><sup>‡</sup></li> <li><a href="/wiki/Xenon" title="Xenon">Xenon</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/General_anaesthetic#Injection" title="General anaesthetic">Injection</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Phenols" title="Phenols">Phenols</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/Ciprofol" title="Ciprofol">Ciprofol</a><sup>†</sup></li> <li><a href="/wiki/Fospropofol" title="Fospropofol">Fospropofol</a></li> <li><a href="/wiki/Propofol" title="Propofol">Propofol</a><sup>#</sup></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Barbiturate" title="Barbiturate">Barbiturates</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/Amobarbital" title="Amobarbital">Amobarbital</a></li> <li><a href="/wiki/Hexobarbital" title="Hexobarbital">Hexobarbital</a></li> <li><a href="/wiki/Methohexital" title="Methohexital">Methohexital</a></li> <li><a href="/wiki/Narcobarbital" title="Narcobarbital">Narcobarbital</a></li> <li><a href="/wiki/Thiamylal" title="Thiamylal">Thiamylal</a></li> <li><a href="/wiki/Sodium_thiopental" title="Sodium thiopental">Thiopental</a><sup>#</sup></li> <li><a href="/wiki/Thiotetrabarbital" title="Thiotetrabarbital">Thiotetrabarbital</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Benzodiazepine" title="Benzodiazepine">Benzodiazepines</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/Midazolam" title="Midazolam">Midazolam</a><sup>#</sup></li> <li><a href="/wiki/Diazepam" title="Diazepam">Diazepam</a><sup>#</sup></li> <li><a href="/wiki/Lorazepam" title="Lorazepam">Lorazepam</a><sup>#</sup></li> <li><a href="/wiki/Remimazolam" title="Remimazolam">Remimazolam</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Opioid" title="Opioid">Opioids</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Morphine" title="Morphine">Morphine</a><sup>#</sup></li> <li><a href="/wiki/Oxycodone" title="Oxycodone">Oxycodone</a></li> <li><a href="/wiki/Anileridine" title="Anileridine">Anileridine</a><sup>‡</sup></li> <li><a href="/wiki/Embutramide" title="Embutramide">Embutramide</a><sup>‡</sup></li> <li><a href="/wiki/Fentanyl" title="Fentanyl">Fentanyl</a><sup>#</sup></li> <li><a href="/wiki/Alfentanil" title="Alfentanil">Alfentanil</a></li> <li><a href="/wiki/Phenoperidine" title="Phenoperidine">Phenoperidine</a></li> <li><a href="/wiki/Remifentanil" title="Remifentanil">Remifentanil</a>÷</li> <li><a href="/wiki/Sufentanil" title="Sufentanil">Sufentanil</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Arylcyclohexylamine" title="Arylcyclohexylamine">Arylcyclohexylamines</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Esketamine" title="Esketamine">Esketamine</a></li> <li><a href="/wiki/Ketamine" title="Ketamine">Ketamine</a><sup>#</sup></li> <li><a href="/wiki/Phencyclidine" title="Phencyclidine">Phencyclidine</a><sup>‡</sup></li> <li><a href="/wiki/Tiletamine" title="Tiletamine">Tiletamine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Neurosteroid" title="Neurosteroid">Neuroactive 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/Alfadolone" title="Alfadolone">Alfadolone</a></li> <li><a href="/wiki/Alfaxalone" title="Alfaxalone">Alfaxalone</a></li> <li><a href="/wiki/Hydroxydione" title="Hydroxydione">Hydroxydione</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Others</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Etomidate" title="Etomidate">Etomidate</a></li> <li><a href="/wiki/Propanidid" title="Propanidid">Propanidid</a><sup>‡</sup></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><td colspan="2" class="navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"><div class="hlist"> <ul><li><sup>#</sup><a href="/wiki/WHO_Model_List_of_Essential_Medicines" title="WHO Model List of Essential Medicines">WHO-EM</a></li> <li><sup>‡</sup><a href="/wiki/List_of_withdrawn_drugs" title="List of withdrawn drugs">Withdrawn</a> from market</li> <li><a href="/wiki/Clinical_trial" title="Clinical trial">Clinical trials</a>: <ul><li><sup>†</sup><a href="/wiki/Phases_of_clinical_research#Phase_III" title="Phases of clinical research">Phase III</a></li> <li><sup>§</sup>Never to phase III</li></ul></li></ul> </div></div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"></div><div role="navigation" class="navbox" aria-labelledby="Hallucinogens" 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:Hallucinogens" title="Template:Hallucinogens"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Hallucinogens" title="Template talk:Hallucinogens"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Hallucinogens" title="Special:EditPage/Template:Hallucinogens"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Hallucinogens" style="font-size:114%;margin:0 4em"><a href="/wiki/Hallucinogen" title="Hallucinogen">Hallucinogens</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Psychedelic_drug" title="Psychedelic drug">Psychedelics</a><br /><small>(<a href="/wiki/5-HT2A_receptor" title="5-HT2A receptor">5-HT<sub>2A</sub></a><br />agonists)</small></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Substituted_benzofuran" title="Substituted benzofuran">Benzofurans</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/2C-B-FLY" title="2C-B-FLY">2C-B-FLY</a></li> <li><a href="/wiki/2CBFly-NBOMe" title="2CBFly-NBOMe">2CBFly-NBOMe</a></li> <li><a href="/wiki/5-MeO-BFE" class="mw-redirect" title="5-MeO-BFE">5-MeO-BFE</a></li> <li><a href="/wiki/5-MeO-DiBF" title="5-MeO-DiBF">5-MeO-DiBF</a></li> <li><a href="/wiki/Bromo-DragonFLY" title="Bromo-DragonFLY">Bromo-DragonFLY</a></li> <li><a href="/wiki/F-2_(drug)" title="F-2 (drug)">F-2</a></li> <li><a href="/wiki/F-22_(psychedelic)" title="F-22 (psychedelic)">F-22</a></li> <li><a href="/wiki/TFMFly" title="TFMFly">TFMFly</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Lysergamides" title="Lysergamides">Lyserg‐<br />amides</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/1B-LSD" title="1B-LSD">1B-LSD</a></li> <li><a href="/wiki/1cP-LSD" title="1cP-LSD">1cP-LSD</a></li> <li><a href="/wiki/1P-ETH-LAD" title="1P-ETH-LAD">1P-ETH-LAD</a></li> <li><a href="/wiki/1P-LSD" title="1P-LSD">1P-LSD</a></li> <li><a href="/wiki/1cP-AL-LAD" title="1cP-AL-LAD">1cP-AL-LAD</a></li> <li><a href="/w/index.php?title=1cP-MiPLA&action=edit&redlink=1" class="new" title="1cP-MiPLA (page does not exist)">1cP-MiPLA</a></li> <li><a href="/wiki/1V-LSD" title="1V-LSD">1V-LSD</a></li> <li><a href="/wiki/Lysergic_acid_2-butyl_amide" title="Lysergic acid 2-butyl amide">2-Butyllysergamide</a></li> <li><a href="/wiki/Lysergic_acid_3-pentyl_amide" title="Lysergic acid 3-pentyl amide">3-Pentyllysergamide</a></li> <li><a href="/wiki/AL-LAD" title="AL-LAD">AL-LAD</a></li> <li><a href="/wiki/ALD-52" title="ALD-52">ALD-52</a></li> <li><a href="/wiki/BU-LAD" title="BU-LAD">BU-LAD</a></li> <li><a href="/wiki/Diallyllysergamide" title="Diallyllysergamide">Diallyllysergamide</a></li> <li><a href="/wiki/Dimethyllysergamide" title="Dimethyllysergamide">Dimethyllysergamide</a></li> <li><a href="/wiki/ECPLA" title="ECPLA">ECPLA</a></li> <li><a href="/wiki/Ergometrine" title="Ergometrine">Ergometrine</a></li> <li><a href="/wiki/ETH-LAD" title="ETH-LAD">ETH-LAD</a></li> <li><a href="/wiki/IP-LAD" class="mw-redirect" title="IP-LAD">IP-LAD</a></li> <li><a href="/wiki/LAE-32" title="LAE-32">LAE-32</a></li> <li><a href="/wiki/LAMPA" title="LAMPA">LAMPA</a></li> <li><a href="/wiki/LPD-824" title="LPD-824">LPD-824</a></li> <li><a href="/wiki/Ergine" title="Ergine">LSA</a></li> <li><a href="/wiki/LSD" title="LSD">LSD</a></li> <li><a href="/wiki/LSD-Pip" title="LSD-Pip">LSD-Pip</a></li> <li><a href="/wiki/Lysergic_acid_hydroxyethylamide" title="Lysergic acid hydroxyethylamide">LSH</a></li> <li><a href="/wiki/LSM-775" title="LSM-775">LSM-775</a></li> <li><a href="/wiki/Lysergic_acid_2,4-dimethylazetidide" title="Lysergic acid 2,4-dimethylazetidide">LSZ</a></li> <li><a href="/wiki/Methylergometrine" title="Methylergometrine">Methylergometrine</a></li> <li><a href="/wiki/Methylisopropyllysergamide" title="Methylisopropyllysergamide">MIPLA</a></li> <li><a href="/wiki/Methysergide" title="Methysergide">Methysergide</a></li> <li><a href="/wiki/N1-Methyl-lysergic_acid_diethylamide" title="N1-Methyl-lysergic acid diethylamide">MLD-41</a></li> <li><a href="/wiki/PARGY-LAD" title="PARGY-LAD">PARGY-LAD</a></li> <li><a href="/wiki/PRO-LAD" title="PRO-LAD">PRO-LAD</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Substituted_phenethylamine" title="Substituted phenethylamine">Phenethyl‐<br />amines</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th id="2C-x" scope="row" class="navbox-group" style="width:1%"><a href="/wiki/2C_(psychedelics)" title="2C (psychedelics)">2C-<i>x</i></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/2C-B" title="2C-B">2C-B</a></li> <li><a href="/w/index.php?title=2C-B-AN&action=edit&redlink=1" class="new" title="2C-B-AN (page does not exist)">2C-B-AN</a></li> <li><a href="/w/index.php?title=2C-Bn&action=edit&redlink=1" class="new" title="2C-Bn (page does not exist)">2C-Bn</a></li> <li><a href="/w/index.php?title=2C-Bu&action=edit&redlink=1" class="new" title="2C-Bu (page does not exist)">2C-Bu</a></li> <li><a href="/wiki/2C-C" title="2C-C">2C-C</a></li> <li><a href="/w/index.php?title=2C-CN&action=edit&redlink=1" class="new" title="2C-CN (page does not exist)">2C-CN</a></li> <li><a href="/wiki/2C-CP" title="2C-CP">2C-CP</a></li> <li><a href="/wiki/2C-D" title="2C-D">2C-D</a></li> <li><a href="/wiki/2C-E" title="2C-E">2C-E</a></li> <li><a href="/wiki/2C-EF" title="2C-EF">2C-EF</a></li> <li><a href="/wiki/2C-F" title="2C-F">2C-F</a></li> <li><a href="/wiki/2C-G" title="2C-G">2C-G</a></li> <li><a href="/wiki/2C-G-1" class="mw-redirect" title="2C-G-1">2C-G-1</a></li> <li><a href="/wiki/2C-G-2" class="mw-redirect" title="2C-G-2">2C-G-2</a></li> <li><a href="/wiki/2C-G-3" class="mw-redirect" title="2C-G-3">2C-G-3</a></li> <li><a href="/wiki/2C-G-4" class="mw-redirect" title="2C-G-4">2C-G-4</a></li> <li><a href="/wiki/2C-G-5" class="mw-redirect" title="2C-G-5">2C-G-5</a></li> <li><a href="/wiki/2C-G-6" class="mw-redirect" title="2C-G-6">2C-G-6</a></li> <li><a href="/wiki/2C-G-N" class="mw-redirect" title="2C-G-N">2C-G-N</a></li> <li><a href="/wiki/2C-H" title="2C-H">2C-H</a></li> <li><a href="/wiki/2C-I" title="2C-I">2C-I</a></li> <li><a href="/wiki/2C-iP" title="2C-iP">2C-iP</a></li> <li><a href="/wiki/2C-N" title="2C-N">2C-N</a></li> <li><a href="/w/index.php?title=2C-NH2&action=edit&redlink=1" class="new" title="2C-NH2 (page does not exist)">2C-NH2</a></li> <li><a href="/wiki/2C-O" class="mw-redirect" title="2C-O">2C-O</a></li> <li><a href="/wiki/2C-O-4" title="2C-O-4">2C-O-4</a></li> <li><a href="/wiki/2C-P" title="2C-P">2C-P</a></li> <li><a href="/w/index.php?title=2C-Ph&action=edit&redlink=1" class="new" title="2C-Ph (page does not exist)">2C-Ph</a></li> <li><a href="/wiki/2C-SE" class="mw-redirect" title="2C-SE">2C-SE</a></li> <li><a href="/wiki/2C-T" title="2C-T">2C-T</a></li> <li><a href="/wiki/2C-T-2" title="2C-T-2">2C-T-2</a></li> <li><a href="/wiki/2C-T-3" title="2C-T-3">2C-T-3</a></li> <li><a href="/wiki/2C-T-4" title="2C-T-4">2C-T-4</a></li> <li><a href="/w/index.php?title=2C-T-5&action=edit&redlink=1" class="new" title="2C-T-5 (page does not exist)">2C-T-5</a></li> <li><a href="/w/index.php?title=2C-T-6&action=edit&redlink=1" class="new" title="2C-T-6 (page does not exist)">2C-T-6</a></li> <li><a href="/wiki/2C-T-7" title="2C-T-7">2C-T-7</a></li> <li><a href="/wiki/2C-T-8" title="2C-T-8">2C-T-8</a></li> <li><a href="/wiki/2C-T-9" class="mw-redirect" title="2C-T-9">2C-T-9</a></li> <li><a href="/w/index.php?title=2C-T-10&action=edit&redlink=1" class="new" title="2C-T-10 (page does not exist)">2C-T-10</a></li> <li><a href="/w/index.php?title=2C-T-11&action=edit&redlink=1" class="new" title="2C-T-11 (page does not exist)">2C-T-11</a></li> <li><a href="/w/index.php?title=2C-T-12&action=edit&redlink=1" class="new" title="2C-T-12 (page does not exist)">2C-T-12</a></li> <li><a href="/wiki/2C-T-13" title="2C-T-13">2C-T-13</a></li> <li><a href="/w/index.php?title=2C-T-14&action=edit&redlink=1" class="new" title="2C-T-14 (page does not exist)">2C-T-14</a></li> <li><a href="/wiki/2C-T-15" title="2C-T-15">2C-T-15</a></li> <li><a href="/wiki/2C-T-16" title="2C-T-16">2C-T-16</a></li> <li><a href="/wiki/2C-T-17" title="2C-T-17">2C-T-17</a></li> <li><a href="/w/index.php?title=2C-T-18&action=edit&redlink=1" class="new" title="2C-T-18 (page does not exist)">2C-T-18</a></li> <li><a href="/wiki/2C-T-19" title="2C-T-19">2C-T-19</a></li> <li><a href="/w/index.php?title=2C-T-20&action=edit&redlink=1" class="new" title="2C-T-20 (page does not exist)">2C-T-20</a></li> <li><a href="/wiki/2C-T-21" title="2C-T-21">2C-T-21</a></li> <li><a href="/w/index.php?title=2C-T-22&action=edit&redlink=1" class="new" title="2C-T-22 (page does not exist)">2C-T-22</a></li> <li><a href="/w/index.php?title=2C-T-22.5&action=edit&redlink=1" class="new" title="2C-T-22.5 (page does not exist)">2C-T-22.5</a></li> <li><a href="/w/index.php?title=2C-T-23&action=edit&redlink=1" class="new" title="2C-T-23 (page does not exist)">2C-T-23</a></li> <li><a href="/w/index.php?title=2C-T-24&action=edit&redlink=1" class="new" title="2C-T-24 (page does not exist)">2C-T-24</a></li> <li><a href="/w/index.php?title=2C-T-25&action=edit&redlink=1" class="new" title="2C-T-25 (page does not exist)">2C-T-25</a></li> <li><a href="/w/index.php?title=2C-T-27&action=edit&redlink=1" class="new" title="2C-T-27 (page does not exist)">2C-T-27</a></li> <li><a href="/wiki/2C-T-28" title="2C-T-28">2C-T-28</a></li> <li><a href="/w/index.php?title=2C-T-30&action=edit&redlink=1" class="new" title="2C-T-30 (page does not exist)">2C-T-30</a></li> <li><a href="/w/index.php?title=2C-T-31&action=edit&redlink=1" class="new" title="2C-T-31 (page does not exist)">2C-T-31</a></li> <li><a href="/w/index.php?title=2C-T-32&action=edit&redlink=1" class="new" title="2C-T-32 (page does not exist)">2C-T-32</a></li> <li><a href="/w/index.php?title=2C-T-33&action=edit&redlink=1" class="new" title="2C-T-33 (page does not exist)">2C-T-33</a></li> <li><a href="/wiki/2C-TFE" title="2C-TFE">2C-TFE</a></li> <li><a href="/wiki/2C-TFM" title="2C-TFM">2C-TFM</a></li> <li><a href="/wiki/2C-YN" title="2C-YN">2C-YN</a></li> <li><a href="/wiki/2C-V" title="2C-V">2C-V</a></li></ul> </div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/25-NB" title="25-NB">25<i>x</i>-NB<i>x</i></a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%">25<i>x</i>-<abbr title="NB: N-benzyl">NB</abbr></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/25B-NB" class="mw-redirect" title="25B-NB">25B-NB</a></li> <li><a href="/w/index.php?title=25C-NB&action=edit&redlink=1" class="new" title="25C-NB (page does not exist)">25C-NB</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">25<i>x</i>-<abbr title="NB: N-benzyl; 3OMe: 3-methoxy">NB3OMe</abbr></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=25B-NB3OMe&action=edit&redlink=1" class="new" title="25B-NB3OMe (page does not exist)">25B-NB3OMe</a></li> <li><a href="/wiki/25C-NB3OMe" title="25C-NB3OMe">25C-NB3OMe</a></li> <li><a href="/w/index.php?title=25D-NB3OMe&action=edit&redlink=1" class="new" title="25D-NB3OMe (page does not exist)">25D-NB3OMe</a></li> <li><a href="/w/index.php?title=25E-NB3OMe&action=edit&redlink=1" class="new" title="25E-NB3OMe (page does not exist)">25E-NB3OMe</a></li> <li><a href="/w/index.php?title=25H-NB3OMe&action=edit&redlink=1" class="new" title="25H-NB3OMe (page does not exist)">25H-NB3OMe</a></li> <li><a href="/wiki/25I-NB3OMe" title="25I-NB3OMe">25I-NB3OMe</a></li> <li><a href="/w/index.php?title=25N-NB3OMe&action=edit&redlink=1" class="new" title="25N-NB3OMe (page does not exist)">25N-NB3OMe</a></li> <li><a href="/w/index.php?title=25P-NB3OMe&action=edit&redlink=1" class="new" title="25P-NB3OMe (page does not exist)">25P-NB3OMe</a></li> <li><a href="/w/index.php?title=25T2-NB3OMe&action=edit&redlink=1" class="new" title="25T2-NB3OMe (page does not exist)">25T2-NB3OMe</a></li> <li><a href="/w/index.php?title=25T4-NB3OMe&action=edit&redlink=1" class="new" title="25T4-NB3OMe (page does not exist)">25T4-NB3OMe</a></li> <li><a href="/w/index.php?title=25T7-NB3OMe&action=edit&redlink=1" class="new" title="25T7-NB3OMe (page does not exist)">25T7-NB3OMe</a></li> <li><a href="/w/index.php?title=25TFM-NB3OMe&action=edit&redlink=1" class="new" title="25TFM-NB3OMe (page does not exist)">25TFM-NB3OMe</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">25<i>x</i>-<abbr title="NB: N-benzyl; 4OMe: 4-methoxy">NB4OMe</abbr></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=25B-NB4OMe&action=edit&redlink=1" class="new" title="25B-NB4OMe (page does not exist)">25B-NB4OMe</a></li> <li><a href="/wiki/25C-NB4OMe" title="25C-NB4OMe">25C-NB4OMe</a></li> <li><a href="/w/index.php?title=25D-NB4OMe&action=edit&redlink=1" class="new" title="25D-NB4OMe (page does not exist)">25D-NB4OMe</a></li> <li><a href="/w/index.php?title=25E-NB4OMe&action=edit&redlink=1" class="new" title="25E-NB4OMe (page does not exist)">25E-NB4OMe</a></li> <li><a href="/w/index.php?title=25H-NB4OMe&action=edit&redlink=1" class="new" title="25H-NB4OMe (page does not exist)">25H-NB4OMe</a></li> <li><a href="/wiki/25I-NB4OMe" title="25I-NB4OMe">25I-NB4OMe</a></li> <li><a href="/w/index.php?title=25N-NB4OMe&action=edit&redlink=1" class="new" title="25N-NB4OMe (page does not exist)">25N-NB4OMe</a></li> <li><a href="/w/index.php?title=25P-NB4OMe&action=edit&redlink=1" class="new" title="25P-NB4OMe (page does not exist)">25P-NB4OMe</a></li> <li><a href="/w/index.php?title=25T2-NB4OMe&action=edit&redlink=1" class="new" title="25T2-NB4OMe (page does not exist)">25T2-NB4OMe</a></li> <li><a href="/w/index.php?title=25T4-NB4OMe&action=edit&redlink=1" class="new" title="25T4-NB4OMe (page does not exist)">25T4-NB4OMe</a></li> <li><a href="/w/index.php?title=25T7-NB4OMe&action=edit&redlink=1" class="new" title="25T7-NB4OMe (page does not exist)">25T7-NB4OMe</a></li> <li><a href="/w/index.php?title=25TFM-NB4OMe&action=edit&redlink=1" class="new" title="25TFM-NB4OMe (page does not exist)">25TFM-NB4OMe</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">25<i>x</i>-<abbr title="NB: N-benzyl; F: fluoro">NBF</abbr></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/25B-NBF" title="25B-NBF">25B-NBF</a></li> <li><a href="/wiki/25C-NBF" title="25C-NBF">25C-NBF</a></li> <li><a href="/w/index.php?title=25D-NBF&action=edit&redlink=1" class="new" title="25D-NBF (page does not exist)">25D-NBF</a></li> <li><a href="/w/index.php?title=25E-NBF&action=edit&redlink=1" class="new" title="25E-NBF (page does not exist)">25E-NBF</a></li> <li><a href="/w/index.php?title=25H-NBF&action=edit&redlink=1" class="new" title="25H-NBF (page does not exist)">25H-NBF</a></li> <li><a href="/wiki/25I-NBF" title="25I-NBF">25I-NBF</a></li> <li><a href="/w/index.php?title=25P-NBF&action=edit&redlink=1" class="new" title="25P-NBF (page does not exist)">25P-NBF</a></li> <li><a href="/w/index.php?title=25T2-NBF&action=edit&redlink=1" class="new" title="25T2-NBF (page does not exist)">25T2-NBF</a></li> <li><a href="/w/index.php?title=25T7-NBF&action=edit&redlink=1" class="new" title="25T7-NBF (page does not exist)">25T7-NBF</a></li> <li><a href="/w/index.php?title=25TFM-NBF&action=edit&redlink=1" class="new" title="25TFM-NBF (page does not exist)">25TFM-NBF</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">25<i>x</i>-<abbr title="NB: N-benzyl; MD: methylenedioxy">NBMD</abbr></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=25B-NBMD&action=edit&redlink=1" class="new" title="25B-NBMD (page does not exist)">25B-NBMD</a></li> <li><a href="/w/index.php?title=25C-NBMD&action=edit&redlink=1" class="new" title="25C-NBMD (page does not exist)">25C-NBMD</a></li> <li><a href="/w/index.php?title=25D-NBMD&action=edit&redlink=1" class="new" title="25D-NBMD (page does not exist)">25D-NBMD</a></li> <li><a href="/w/index.php?title=25E-NBMD&action=edit&redlink=1" class="new" title="25E-NBMD (page does not exist)">25E-NBMD</a></li> <li><a href="/w/index.php?title=25F-NBMD&action=edit&redlink=1" class="new" title="25F-NBMD (page does not exist)">25F-NBMD</a></li> <li><a href="/w/index.php?title=25H-NBMD&action=edit&redlink=1" class="new" title="25H-NBMD (page does not exist)">25H-NBMD</a></li> <li><a href="/wiki/25I-NBMD" title="25I-NBMD">25I-NBMD</a></li> <li><a href="/w/index.php?title=25P-NBMD&action=edit&redlink=1" class="new" title="25P-NBMD (page does not exist)">25P-NBMD</a></li> <li><a href="/w/index.php?title=25T2-NBMD&action=edit&redlink=1" class="new" title="25T2-NBMD (page does not exist)">25T2-NBMD</a></li> <li><a href="/w/index.php?title=25T7-NBMD&action=edit&redlink=1" class="new" title="25T7-NBMD (page does not exist)">25T7-NBMD</a></li> <li><a href="/w/index.php?title=25TFM-NBMD&action=edit&redlink=1" class="new" title="25TFM-NBMD (page does not exist)">25TFM-NBMD</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">25<i>x</i>-<abbr title="NB: N-benzyl; OH: hydroxy">NBOH</abbr></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/25B-NBOH" title="25B-NBOH">25B-NBOH</a></li> <li><a href="/wiki/25C-NBOH" title="25C-NBOH">25C-NBOH</a></li> <li><a href="/wiki/25CN-NBOH" title="25CN-NBOH">25CN-NBOH</a></li> <li><a href="/w/index.php?title=25D-NBOH&action=edit&redlink=1" class="new" title="25D-NBOH (page does not exist)">25D-NBOH</a></li> <li><a href="/wiki/25E-NBOH" title="25E-NBOH">25E-NBOH</a></li> <li><a href="/w/index.php?title=25F-NBOH&action=edit&redlink=1" class="new" title="25F-NBOH (page does not exist)">25F-NBOH</a></li> <li><a href="/w/index.php?title=25H-NBOH&action=edit&redlink=1" class="new" title="25H-NBOH (page does not exist)">25H-NBOH</a></li> <li><a href="/wiki/25I-NBOH" title="25I-NBOH">25I-NBOH</a></li> <li><a href="/w/index.php?title=25P-NBOH&action=edit&redlink=1" class="new" title="25P-NBOH (page does not exist)">25P-NBOH</a></li> <li><a href="/w/index.php?title=25T2-NBOH&action=edit&redlink=1" class="new" title="25T2-NBOH (page does not exist)">25T2-NBOH</a></li> <li><a href="/w/index.php?title=25T7-NBOH&action=edit&redlink=1" class="new" title="25T7-NBOH (page does not exist)">25T7-NBOH</a></li> <li><a href="/w/index.php?title=25TFM-NBOH&action=edit&redlink=1" class="new" title="25TFM-NBOH (page does not exist)">25TFM-NBOH</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">25<i>x</i>-<abbr title="NB: N-benzyl; OMe: methoxy">NBOMe</abbr></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/25B-NBOMe" title="25B-NBOMe">25B-NBOMe</a></li> <li><a href="/wiki/25C-NBOMe" title="25C-NBOMe">25C-NBOMe</a></li> <li><a href="/wiki/25CN-NBOMe" title="25CN-NBOMe">25CN-NBOMe</a></li> <li><a href="/wiki/25D-NBOMe" title="25D-NBOMe">25D-NBOMe</a></li> <li><a href="/wiki/25E-NBOMe" title="25E-NBOMe">25E-NBOMe</a></li> <li><a href="/w/index.php?title=25F-NBOMe&action=edit&redlink=1" class="new" title="25F-NBOMe (page does not exist)">25F-NBOMe</a></li> <li><a href="/wiki/25G-NBOMe" title="25G-NBOMe">25G-NBOMe</a></li> <li><a href="/wiki/25H-NBOMe" title="25H-NBOMe">25H-NBOMe</a></li> <li><a href="/wiki/25I-NBOMe" title="25I-NBOMe">25I-NBOMe</a></li> <li><a href="/wiki/25iP-NBOMe" title="25iP-NBOMe">25iP-NBOMe</a></li> <li><a href="/wiki/25N-NBOMe" title="25N-NBOMe">25N-NBOMe</a></li> <li><a href="/wiki/25P-NBOMe" title="25P-NBOMe">25P-NBOMe</a></li> <li><a href="/w/index.php?title=25T-NBOMe&action=edit&redlink=1" class="new" title="25T-NBOMe (page does not exist)">25T-NBOMe</a></li> <li><a href="/w/index.php?title=25T2-NBOMe&action=edit&redlink=1" class="new" title="25T2-NBOMe (page does not exist)">25T2-NBOMe</a></li> <li><a href="/w/index.php?title=25T4-NBOMe&action=edit&redlink=1" class="new" title="25T4-NBOMe (page does not exist)">25T4-NBOMe</a></li> <li><a href="/wiki/25T7-NBOMe" title="25T7-NBOMe">25T7-NBOMe</a></li> <li><a href="/wiki/25TFM-NBOMe" title="25TFM-NBOMe">25TFM-NBOMe</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Atypical structures</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=25B-N1POMe&action=edit&redlink=1" class="new" title="25B-N1POMe (page does not exist)">25B-N1POMe</a></li> <li><a href="/w/index.php?title=25B-NAcPip&action=edit&redlink=1" class="new" title="25B-NAcPip (page does not exist)">25B-NAcPip</a></li> <li><a href="/w/index.php?title=25B-NB23DM&action=edit&redlink=1" class="new" title="25B-NB23DM (page does not exist)">25B-NB23DM</a></li> <li><a href="/w/index.php?title=25B-NB25DM&action=edit&redlink=1" class="new" title="25B-NB25DM (page does not exist)">25B-NB25DM</a></li> <li><a href="/w/index.php?title=25C-NBCl&action=edit&redlink=1" class="new" title="25C-NBCl (page does not exist)">25C-NBCl</a></li> <li><a href="/w/index.php?title=25C-NBOEt&action=edit&redlink=1" class="new" title="25C-NBOEt (page does not exist)">25C-NBOEt</a></li> <li><a href="/w/index.php?title=25C-NBOiPr&action=edit&redlink=1" class="new" title="25C-NBOiPr (page does not exist)">25C-NBOiPr</a></li> <li><a href="/w/index.php?title=25I-N2Nap1OH&action=edit&redlink=1" class="new" title="25I-N2Nap1OH (page does not exist)">25I-N2Nap1OH</a></li> <li><a href="/w/index.php?title=25I-N3MT2M&action=edit&redlink=1" class="new" title="25I-N3MT2M (page does not exist)">25I-N3MT2M</a></li> <li><a href="/w/index.php?title=25I-N4MT3M&action=edit&redlink=1" class="new" title="25I-N4MT3M (page does not exist)">25I-N4MT3M</a></li> <li><a href="/wiki/25I-NB34MD" title="25I-NB34MD">25I-NB34MD</a></li> <li><a href="/w/index.php?title=25I-NBAm&action=edit&redlink=1" class="new" title="25I-NBAm (page does not exist)">25I-NBAm</a></li> <li><a href="/w/index.php?title=25I-NBBr&action=edit&redlink=1" class="new" title="25I-NBBr (page does not exist)">25I-NBBr</a></li> <li><a href="/w/index.php?title=25I-NBMeOH&action=edit&redlink=1" class="new" title="25I-NBMeOH (page does not exist)">25I-NBMeOH</a></li> <li><a href="/w/index.php?title=25I-NBTFM&action=edit&redlink=1" class="new" title="25I-NBTFM (page does not exist)">25I-NBTFM</a></li> <li><a href="/wiki/2CBCB-NBOMe" title="2CBCB-NBOMe">2CBCB-NBOMe</a></li> <li><a href="/wiki/2CBFly-NBOMe" title="2CBFly-NBOMe">2CBFly-NBOMe</a></li> <li><a href="/wiki/4-EA-NBOMe" title="4-EA-NBOMe">4-EA-NBOMe</a></li> <li><a href="/w/index.php?title=5-APB-NBOMe&action=edit&redlink=1" class="new" title="5-APB-NBOMe (page does not exist)">5-APB-NBOMe</a></li> <li><a href="/w/index.php?title=5MT-NBOMe&action=edit&redlink=1" class="new" title="5MT-NBOMe (page does not exist)">5MT-NBOMe</a></li> <li><a href="/w/index.php?title=C30-NBOMe&action=edit&redlink=1" class="new" title="C30-NBOMe (page does not exist)">C30-NBOMe</a></li> <li><a href="/w/index.php?title=DOB-NBOMe&action=edit&redlink=1" class="new" title="DOB-NBOMe (page does not exist)">DOB-NBOMe</a></li> <li><a href="/w/index.php?title=DOI-NBOMe&action=edit&redlink=1" class="new" title="DOI-NBOMe (page does not exist)">DOI-NBOMe</a></li> <li><a href="/w/index.php?title=FECIMBI-36&action=edit&redlink=1" class="new" title="FECIMBI-36 (page does not exist)">FECIMBI-36</a></li> <li><a href="/w/index.php?title=MDPEA-NBOMe&action=edit&redlink=1" class="new" title="MDPEA-NBOMe (page does not exist)">MDPEA-NBOMe</a></li> <li><a href="/wiki/N-Ethyl-2C-B" title="N-Ethyl-2C-B">N-Ethyl-2C-B</a></li> <li><a href="/w/index.php?title=NBOMe-escaline&action=edit&redlink=1" class="new" title="NBOMe-escaline (page does not exist)">NBOMe-escaline</a></li> <li><a href="/wiki/NBOMe-mescaline" title="NBOMe-mescaline">NBOMe-mescaline</a></li> <li><a href="/wiki/ZDCM-04" title="ZDCM-04">ZDCM-04</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">25<i>x</i>-NM<i>x</i></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=25B-NMe7BF&action=edit&redlink=1" class="new" title="25B-NMe7BF (page does not exist)">25B-NMe7BF</a></li> <li><a href="/w/index.php?title=25B-NMe7BT&action=edit&redlink=1" class="new" title="25B-NMe7BT (page does not exist)">25B-NMe7BT</a></li> <li><a href="/w/index.php?title=25B-NMe7Bim&action=edit&redlink=1" class="new" title="25B-NMe7Bim (page does not exist)">25B-NMe7Bim</a></li> <li><a href="/w/index.php?title=25B-NMe7Box&action=edit&redlink=1" class="new" title="25B-NMe7Box (page does not exist)">25B-NMe7Box</a></li> <li><a href="/w/index.php?title=25B-NMe7DHBF&action=edit&redlink=1" class="new" title="25B-NMe7DHBF (page does not exist)">25B-NMe7DHBF</a></li> <li><a href="/w/index.php?title=25B-NMe7Ind&action=edit&redlink=1" class="new" title="25B-NMe7Ind (page does not exist)">25B-NMe7Ind</a></li> <li><a href="/w/index.php?title=25B-NMe7Indz&action=edit&redlink=1" class="new" title="25B-NMe7Indz (page does not exist)">25B-NMe7Indz</a></li> <li><a href="/w/index.php?title=25B-NMePyr&action=edit&redlink=1" class="new" title="25B-NMePyr (page does not exist)">25B-NMePyr</a></li> <li><a href="/w/index.php?title=25I-NMe7DHBF&action=edit&redlink=1" class="new" title="25I-NMe7DHBF (page does not exist)">25I-NMe7DHBF</a></li> <li><a href="/w/index.php?title=25I-NMeFur&action=edit&redlink=1" class="new" title="25I-NMeFur (page does not exist)">25I-NMeFur</a></li> <li><a href="/w/index.php?title=25I-NMeTHF&action=edit&redlink=1" class="new" title="25I-NMeTHF (page does not exist)">25I-NMeTHF</a></li> <li><a href="/w/index.php?title=25I-NMeTh&action=edit&redlink=1" class="new" title="25I-NMeTh (page does not exist)">25I-NMeTh</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/N-(2C)-fentanyl" class="mw-redirect" title="N-(2C)-fentanyl">N-(2C)-fentanyl</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/w/index.php?title=N-(2C-B)_fentanyl&action=edit&redlink=1" class="new" title="N-(2C-B) fentanyl (page does not exist)">N-(2C-B) fentanyl</a></li> <li><a href="/w/index.php?title=N-(2C-C)_fentanyl&action=edit&redlink=1" class="new" title="N-(2C-C) fentanyl (page does not exist)">N-(2C-C) fentanyl</a></li> <li><a href="/w/index.php?title=N-(2C-D)_fentanyl&action=edit&redlink=1" class="new" title="N-(2C-D) fentanyl (page does not exist)">N-(2C-D) fentanyl</a></li> <li><a href="/w/index.php?title=N-(2C-E)_fentanyl&action=edit&redlink=1" class="new" title="N-(2C-E) fentanyl (page does not exist)">N-(2C-E) fentanyl</a></li> <li><a href="/w/index.php?title=N-(2C-G)_fentanyl&action=edit&redlink=1" class="new" title="N-(2C-G) fentanyl (page does not exist)">N-(2C-G) fentanyl</a></li> <li><a href="/w/index.php?title=N-(2C-H)_fentanyl&action=edit&redlink=1" class="new" title="N-(2C-H) fentanyl (page does not exist)">N-(2C-H) fentanyl</a></li> <li><a href="/w/index.php?title=N-(2C-I)_fentanyl&action=edit&redlink=1" class="new" title="N-(2C-I) fentanyl (page does not exist)">N-(2C-I) fentanyl</a></li> <li><a href="/w/index.php?title=N-(2C-IP)_fentanyl&action=edit&redlink=1" class="new" title="N-(2C-IP) fentanyl (page does not exist)">N-(2C-IP) fentanyl</a></li> <li><a href="/w/index.php?title=N-(2C-N)_fentanyl&action=edit&redlink=1" class="new" title="N-(2C-N) fentanyl (page does not exist)">N-(2C-N) fentanyl</a></li> <li><a href="/w/index.php?title=N-(2C-P)_fentanyl&action=edit&redlink=1" class="new" title="N-(2C-P) fentanyl (page does not exist)">N-(2C-P) fentanyl</a></li> <li><a href="/w/index.php?title=N-(2C-T)_fentanyl&action=edit&redlink=1" class="new" title="N-(2C-T) fentanyl (page does not exist)">N-(2C-T) fentanyl</a></li> <li><a href="/w/index.php?title=N-(2C-T-2)_fentanyl&action=edit&redlink=1" class="new" title="N-(2C-T-2) fentanyl (page does not exist)">N-(2C-T-2) fentanyl</a></li> <li><a href="/w/index.php?title=N-(2C-T-4)_fentanyl&action=edit&redlink=1" class="new" title="N-(2C-T-4) fentanyl (page does not exist)">N-(2C-T-4) fentanyl</a></li> <li><a href="/w/index.php?title=N-(2C-T-7)_fentanyl&action=edit&redlink=1" class="new" title="N-(2C-T-7) fentanyl (page does not exist)">N-(2C-T-7) fentanyl</a></li> <li><a href="/w/index.php?title=N-(2C-TFM)_fentanyl&action=edit&redlink=1" class="new" title="N-(2C-TFM) fentanyl (page does not exist)">N-(2C-TFM) fentanyl</a></li></ul> </div></td></tr></tbody></table><div> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">3C-<i>x</i></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/3C-AL" title="3C-AL">3C-AL</a></li> <li><a href="/wiki/3C-BZ" title="3C-BZ">3C-BZ</a></li> <li><a href="/wiki/3C-DFE" title="3C-DFE">3C-DFE</a></li> <li><a href="/wiki/3C-E" title="3C-E">3C-E</a></li> <li><a href="/wiki/3C-MAL" title="3C-MAL">3C-MAL</a></li> <li><a href="/wiki/3C-P" title="3C-P">3C-P</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">4C-<i>x</i></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/4C-B" title="4C-B">4C-B</a></li> <li><a href="/w/index.php?title=4C-C&action=edit&redlink=1" class="new" title="4C-C (page does not exist)">4C-C</a></li> <li><a href="/wiki/4C-D" class="mw-redirect" title="4C-D">4C-D</a></li> <li><a href="/w/index.php?title=4C-E&action=edit&redlink=1" class="new" title="4C-E (page does not exist)">4C-E</a></li> <li><a href="/w/index.php?title=4C-I&action=edit&redlink=1" class="new" title="4C-I (page does not exist)">4C-I</a></li> <li><a href="/w/index.php?title=4C-N&action=edit&redlink=1" class="new" title="4C-N (page does not exist)">4C-N</a></li> <li><a href="/w/index.php?title=4C-P&action=edit&redlink=1" class="new" title="4C-P (page does not exist)">4C-P</a></li> <li><a href="/wiki/4C-T-2" title="4C-T-2">4C-T-2</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/DOx" title="DOx">DO<i>x</i></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/Aleph_(psychedelic)" title="Aleph (psychedelic)">DOT</a></li> <li><a href="/wiki/2,5-Dimethoxy-4-bromoamphetamine" title="2,5-Dimethoxy-4-bromoamphetamine">DOB</a></li> <li><a href="/wiki/2,5-Dimethoxy-4-chloroamphetamine" title="2,5-Dimethoxy-4-chloroamphetamine">DOC</a></li> <li><a href="/wiki/2,5-Dimethoxy-4-(2-fluoroethyl)amphetamine" title="2,5-Dimethoxy-4-(2-fluoroethyl)amphetamine">DOEF</a></li> <li><a href="/wiki/2,5-Dimethoxy-4-ethylamphetamine" title="2,5-Dimethoxy-4-ethylamphetamine">DOET</a></li> <li><a href="/wiki/2,5-Dimethoxy-4-fluoroamphetamine" title="2,5-Dimethoxy-4-fluoroamphetamine">DOF</a></li> <li><a href="/wiki/2,5-Dimethoxy-4-iodoamphetamine" title="2,5-Dimethoxy-4-iodoamphetamine">DOI</a></li> <li><a href="/wiki/2,5-Dimethoxy-4-isopropylamphetamine" title="2,5-Dimethoxy-4-isopropylamphetamine">DOiPR</a></li> <li><a href="/wiki/2,5-Dimethoxy-4-methylamphetamine" title="2,5-Dimethoxy-4-methylamphetamine">DOM</a></li> <li><a href="/wiki/2,5-Dimethoxy-4-nitroamphetamine" title="2,5-Dimethoxy-4-nitroamphetamine">DON</a></li> <li><a href="/wiki/2,5-Dimethoxy-4-propylamphetamine" title="2,5-Dimethoxy-4-propylamphetamine">DOPR</a></li> <li><a href="/wiki/2,5-Dimethoxy-4-trifluoromethylamphetamine" title="2,5-Dimethoxy-4-trifluoromethylamphetamine">DOTFM</a></li> <li><a href="/wiki/2,5-Dimethoxy-4-ethoxyamphetamine" title="2,5-Dimethoxy-4-ethoxyamphetamine">MEM</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">HOT-<i>x</i></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/HOT-2" title="HOT-2">HOT-2</a></li> <li><a href="/wiki/HOT-7" title="HOT-7">HOT-7</a></li> <li><a href="/wiki/HOT-17" title="HOT-17">HOT-17</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Substituted_methylenedioxyphenethylamine" title="Substituted methylenedioxyphenethylamine">MD<em>xx</em></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/DMMDA" title="DMMDA">DMMDA</a></li> <li><a href="/wiki/2,3-Dimethoxy-4,5-methylenedioxyamphetamine" class="mw-redirect" title="2,3-Dimethoxy-4,5-methylenedioxyamphetamine">DMMDA-2</a></li> <li><a href="/wiki/Lophophine" title="Lophophine">Lophophine</a></li> <li><a href="/wiki/3,4-Methylenedioxyamphetamine" title="3,4-Methylenedioxyamphetamine">MDA</a></li> <li><a href="/wiki/MDAI" title="MDAI">MDAI</a></li> <li><a href="/wiki/MDBZ" class="mw-redirect" title="MDBZ">MDBZ</a></li> <li><a href="/wiki/MDMA" title="MDMA">MDMA</a></li> <li><a href="/wiki/MMDA_(drug)" title="MMDA (drug)">MMDA</a></li> <li><a href="/wiki/MMDA-2" title="MMDA-2">MMDA-2</a></li> <li><a href="/wiki/MMDA-3a" class="mw-redirect" title="MMDA-3a">MMDA-3a</a></li> <li><a href="/wiki/MMDMA" title="MMDMA">MMDMA</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Mescaline (subst.)</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-Bromomescaline" title="2-Bromomescaline">2-Bromomescaline</a></li> <li><a href="/wiki/Thioescaline" title="Thioescaline">3-TE</a></li> <li><a href="/wiki/Thioescaline" title="Thioescaline">4-TE</a></li> <li><a href="/wiki/Thiomescaline" title="Thiomescaline">3-TM</a></li> <li><a href="/wiki/Thiomescaline" title="Thiomescaline">4-TM</a></li> <li><a href="/wiki/Allylescaline" title="Allylescaline">Allylescaline</a></li> <li><a href="/wiki/Asymbescaline" title="Asymbescaline">Asymbescaline</a></li> <li><a href="/wiki/Buscaline" title="Buscaline">Buscaline</a></li> <li><a href="/wiki/Cyclopropylmescaline" title="Cyclopropylmescaline">Cyclopropylmescaline</a></li> <li><a href="/w/index.php?title=Difluoromescaline&action=edit&redlink=1" class="new" title="Difluoromescaline (page does not exist)">Difluoromescaline</a></li> <li><a href="/w/index.php?title=Difluoroescaline&action=edit&redlink=1" class="new" title="Difluoroescaline (page does not exist)">Difluoroescaline</a></li> <li><a href="/wiki/Escaline" title="Escaline">Escaline</a></li> <li><a href="/w/index.php?title=Fluoroproscaline&action=edit&redlink=1" class="new" title="Fluoroproscaline (page does not exist)">Fluoroproscaline</a></li> <li><a href="/w/index.php?title=Isobuscaline&action=edit&redlink=1" class="new" title="Isobuscaline (page does not exist)">Isobuscaline</a></li> <li><a href="/wiki/Isoproscaline" title="Isoproscaline">Isoproscaline</a></li> <li><a href="/wiki/Jimscaline" title="Jimscaline">Jimscaline</a></li> <li><a href="/wiki/Mescaline" title="Mescaline">Mescaline</a></li> <li><a href="/wiki/Metaescaline" title="Metaescaline">Metaescaline</a></li> <li><a href="/wiki/Methallylescaline" title="Methallylescaline">Methallylescaline</a></li> <li><a href="/wiki/Proscaline" title="Proscaline">Proscaline</a></li> <li><a href="/wiki/Thioproscaline" title="Thioproscaline">Thioproscaline</a></li> <li><a href="/w/index.php?title=Trifluoroescaline&action=edit&redlink=1" class="new" title="Trifluoroescaline (page does not exist)">Trifluoroescaline</a></li> <li><a href="/wiki/Trifluoromescaline" title="Trifluoromescaline">Trifluoromescaline</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Trimethoxyamphetamine" title="Trimethoxyamphetamine">TMAs</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>TMA</li> <li>TMA-2</li> <li>TMA-3</li> <li>TMA-4</li> <li>TMA-5</li> <li>TMA-6</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Others</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/2C-B-BUTTERFLY" title="2C-B-BUTTERFLY">2C-B-BUTTERFLY</a></li> <li><a href="/w/index.php?title=2C-B-DragonFLY&action=edit&redlink=1" class="new" title="2C-B-DragonFLY (page does not exist)">2C-B-DragonFLY</a></li> <li><a href="/w/index.php?title=2C-B-DragonFLY-NBOH&action=edit&redlink=1" class="new" title="2C-B-DragonFLY-NBOH (page does not exist)">2C-B-DragonFLY-NBOH</a></li> <li><a href="/w/index.php?title=2C-B-FLY-NB2EtO5Cl&action=edit&redlink=1" class="new" title="2C-B-FLY-NB2EtO5Cl (page does not exist)">2C-B-FLY-NB2EtO5Cl</a></li> <li><a href="/w/index.php?title=2CB-5-hemifly&action=edit&redlink=1" class="new" title="2CB-5-hemifly (page does not exist)">2CB-5-hemifly</a></li> <li><a href="/wiki/2CB-Ind" title="2CB-Ind">2CB-Ind</a></li> <li><a href="/wiki/2CD-5EtO" title="2CD-5EtO">2CD-5EtO</a></li> <li><a href="/wiki/TOET_(psychedelic)#2-TOET" title="TOET (psychedelic)">2-TOET</a></li> <li><a href="/wiki/TOET_(psychedelic)#5-TOET" title="TOET (psychedelic)">5-TOET</a></li> <li><a href="/wiki/TOM_(psychedelic)" title="TOM (psychedelic)">2-TOM</a></li> <li><a href="/wiki/TOM_(psychedelic)" title="TOM (psychedelic)">5-TOM</a></li> <li><a href="/wiki/BOB_(psychedelic)" title="BOB (psychedelic)">BOB</a></li> <li><a href="/wiki/BOD_(psychedelic)" title="BOD (psychedelic)">BOD</a></li> <li><a href="/wiki/%CE%92k-2C-B" title="Βk-2C-B">βk-2C-B</a></li> <li><a href="/w/index.php?title=%CE%92k-2C-I&action=edit&redlink=1" class="new" title="Βk-2C-I (page does not exist)">βk-2C-I</a></li> <li><a href="/wiki/DESOXY" title="DESOXY">DESOXY</a></li> <li><a href="/wiki/2,5-Dimethoxy-4-methylphenylcyclopropylamine" title="2,5-Dimethoxy-4-methylphenylcyclopropylamine">DMCPA</a></li> <li><a href="/wiki/DMBMPP" title="DMBMPP">DMBMPP</a></li> <li><a href="/wiki/DOB-FLY" title="DOB-FLY">DOB-FLY</a></li> <li><a href="/wiki/Fenfluramine" title="Fenfluramine">Fenfluramine</a></li> <li><a href="/wiki/Ganesha_(psychedelic)" title="Ganesha (psychedelic)">Ganesha</a></li> <li><a href="/wiki/Macromerine" title="Macromerine">Macromerine</a></li> <li><a href="/wiki/3-Methoxy-4-methylamphetamine" title="3-Methoxy-4-methylamphetamine">MMA</a></li> <li><a href="/wiki/TCB-2" title="TCB-2">TCB-2</a></li> <li><a href="/wiki/TOMSO" title="TOMSO">TOMSO</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/Substituted_piperazine" title="Substituted piperazine">Piperazines</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/2C-B-PP" title="2C-B-PP">2C-B-PP</a></li> <li><a href="/wiki/Benzylpiperazine" title="Benzylpiperazine">BZP</a></li> <li><a href="/wiki/Para-Fluorophenylpiperazine" title="Para-Fluorophenylpiperazine">pFPP</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Substituted_tryptamine" title="Substituted tryptamine">Tryptamines</a></th><td class="navbox-list-with-group navbox-list navbox-odd" 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/Substituted_alpha-alkyltryptamine" class="mw-redirect" title="Substituted alpha-alkyltryptamine"><i>alpha</i>-alkyltryptamines</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/AL-37350A" title="AL-37350A">4,5-DHP-α-MT</a></li> <li><a href="/wiki/5-MeO-AET" title="5-MeO-AET">5-MeO-α-ET</a></li> <li><a href="/wiki/5-MeO-aMT" title="5-MeO-aMT">5-MeO-α-MT</a></li> <li><a href="/wiki/Alpha-Ethyltryptamine" class="mw-redirect" title="Alpha-Ethyltryptamine">α-ET</a></li> <li><a href="/wiki/Alpha-Methyltryptamine" class="mw-redirect" title="Alpha-Methyltryptamine">α-MT</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><i>x</i>-<abbr title="N,N-Diallyltryptamine">DALT</abbr></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=4-HO-DALT&action=edit&redlink=1" class="new" title="4-HO-DALT (page does not exist)">(Daltocin) 4-HO-DALT</a></li> <li><a href="/wiki/4-AcO-DALT" title="4-AcO-DALT">(Daltacetin) 4-AcO-DALT</a></li> <li><a href="/wiki/5-MeO-DALT" title="5-MeO-DALT">5-MeO-DALT</a></li> <li><a href="/wiki/DALT" title="DALT">DALT</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><i>x</i>-<abbr title="N,N-Diethyltryptamine">DET</abbr></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-Acetoxy-DET" class="mw-redirect" title="4-Acetoxy-DET">(Ethacetin) 4-AcO-DET</a></li> <li><a href="/wiki/4-HO-DET" title="4-HO-DET">(Ethocin) 4-HO-DET</a></li> <li><a href="/wiki/5-MeO-DET" title="5-MeO-DET">5-MeO-DET</a></li> <li><a href="/wiki/Diethyltryptamine" title="Diethyltryptamine">(T-9) DET</a></li> <li><a href="/wiki/Ethocybin" title="Ethocybin">(Ethocybin) 4-PO-DET</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><i>x</i>-<abbr title="N,N-Diisopropyltryptamine">DiPT</abbr></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/4-Acetoxy-DiPT" title="4-Acetoxy-DiPT">(Ipracetin) 4-AcO-DiPT</a></li> <li><a href="/wiki/4-HO-DiPT" title="4-HO-DiPT">(Iprocin) 4-HO-DiPT</a></li> <li><a href="/wiki/5-Methoxy-N,N-diisopropyltryptamine" class="mw-redirect" title="5-Methoxy-N,N-diisopropyltryptamine">5-MeO-DiPT</a></li> <li><a href="/wiki/Diisopropyltryptamine" class="mw-redirect" title="Diisopropyltryptamine">DiPT</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><i>x</i>-<abbr title="N,N-Dimethyltryptamine">DMT</abbr></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/1-(2-Dimethylaminoethyl)dihydropyrano(3,2-e)indole" class="mw-redirect" title="1-(2-Dimethylaminoethyl)dihydropyrano(3,2-e)indole">4,5-DHP-DMT</a></li> <li><a href="/wiki/2,N,N-TMT" title="2,N,N-TMT">2,N,N-TMT</a></li> <li><a href="/wiki/O-Acetylpsilocin" title="O-Acetylpsilocin">4-AcO-DMT</a></li> <li><a href="/wiki/4-Hydroxy-5-methoxydimethyltryptamine" title="4-Hydroxy-5-methoxydimethyltryptamine">4-HO-5-MeO-DMT</a></li> <li><a href="/w/index.php?title=4,N,N-TMT&action=edit&redlink=1" class="new" title="4,N,N-TMT (page does not exist)">4,N,N-TMT</a></li> <li><a href="/wiki/4-Propionyloxy-DMT" class="mw-redirect" title="4-Propionyloxy-DMT">4-Propionyloxy-DMT</a></li> <li><a href="/w/index.php?title=5,6-diBr-DMT&action=edit&redlink=1" class="new" title="5,6-diBr-DMT (page does not exist)">5,6-diBr-DMT</a></li> <li><a href="/wiki/5-AcO-DMT" class="mw-redirect" title="5-AcO-DMT">5-AcO-DMT</a></li> <li><a href="/wiki/5-Bromo-DMT" title="5-Bromo-DMT">5-Bromo-DMT</a></li> <li><a href="/w/index.php?title=(Indapex)_5-MeO-2-TMT&action=edit&redlink=1" class="new" title="(Indapex) 5-MeO-2-TMT (page does not exist)">5-MeO-2,<i>N</i>,<i>N</i>-TMT</a></li> <li><a href="/w/index.php?title=5-MeO-4,N,N-TMT&action=edit&redlink=1" class="new" title="5-MeO-4,N,N-TMT (page does not exist)">5-MeO-4,<i>N</i>,<i>N</i>-TMT</a></li> <li><a href="/w/index.php?title=5-MeO-%CE%B1,N,N-TMT&action=edit&redlink=1" class="new" title="5-MeO-α,N,N-TMT (page does not exist)">5-MeO-α,N,N-TMT</a></li> <li><a href="/wiki/5-MeO-DMT" title="5-MeO-DMT">5-MeO-DMT</a></li> <li><a href="/wiki/5,N,N-TMT" title="5,N,N-TMT">5-<i>N</i>,<i>N</i>-TMT</a></li> <li><a href="/wiki/7,N,N-TMT" title="7,N,N-TMT">7,N,N-TMT</a></li> <li><a href="/wiki/Alpha-N,N-Trimethyltryptamine" class="mw-redirect" title="Alpha-N,N-Trimethyltryptamine">α,N,N-TMT</a></li> <li><a href="/wiki/Bufotenin" title="Bufotenin">(Bufotenin) 5-HO-DMT</a></li> <li><a href="/wiki/N,N-Dimethyltryptamine" title="N,N-Dimethyltryptamine">DMT</a></li> <li><a href="/wiki/Norbaeocystin" title="Norbaeocystin">Norbaeocystin</a></li> <li><a href="/wiki/Psilocin" title="Psilocin">(Psilocin) 4-HO-DMT</a></li> <li><a href="/wiki/Psilocybin" title="Psilocybin">(Psilocybin) 4-PO-DMT</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><i>x</i>-<abbr title="N,N-Dipropyltryptamine">DPT</abbr></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=4-Acetoxy-DPT&action=edit&redlink=1" class="new" title="4-Acetoxy-DPT (page does not exist)">(Depracetin) 4-AcO-DPT</a></li> <li><a href="/wiki/4-HO-DPT" title="4-HO-DPT">(Deprocin) 4-HO-DPT</a></li> <li><a href="/wiki/5-MeO-DPT" title="5-MeO-DPT">5-MeO-DPT</a></li> <li><a href="/wiki/Dipropyltryptamine" title="Dipropyltryptamine">(The Light) DPT</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Ibogaine-related</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/18-Methylaminocoronaridine" title="18-Methylaminocoronaridine">18-MAC</a></li> <li><a href="/wiki/18-Methoxycoronaridine" title="18-Methoxycoronaridine">18-MC</a></li> <li><a href="/wiki/Coronaridine" title="Coronaridine">Coronaridine</a></li> <li><a href="/wiki/Ibogaine" title="Ibogaine">Ibogaine</a></li> <li><a href="/wiki/Ibogamine" title="Ibogamine">Ibogamine</a></li> <li><a href="/wiki/2-Methoxyethyl-18-methoxycoronaridinate" title="2-Methoxyethyl-18-methoxycoronaridinate">ME-18-MC</a></li> <li><a href="/wiki/Noribogaine" title="Noribogaine">Noribogaine</a></li> <li><a href="/wiki/Tabernanthine" title="Tabernanthine">Tabernanthine</a></li> <li><a href="/wiki/Voacangine" title="Voacangine">Voacangine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><i>x</i>-<abbr title="N-Methyl-N-ethyltryptamine">MET</abbr></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/4-HO-MET" title="4-HO-MET">(Metocin) 4-HO-MET</a></li> <li><a href="/wiki/4-AcO-MET" title="4-AcO-MET">(Metocetin) 4-AcO-MET</a></li> <li><a href="/wiki/5-MeO-MET" title="5-MeO-MET">5-MeO-MET</a></li> <li><a href="/wiki/N-Methyl-N-ethyltryptamine" title="N-Methyl-N-ethyltryptamine">MET</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><i>x</i>-<abbr title="N-Methyl-N-isopropyltryptamine">MiPT</abbr></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-Acetoxy-MiPT" class="mw-redirect" title="4-Acetoxy-MiPT">(Mipracetin) 4-AcO-MiPT</a></li> <li><a href="/wiki/4-HO-MiPT" title="4-HO-MiPT">(Miprocin) 4-HO-MiPT</a></li> <li><a href="/wiki/5,N-Dimethyl-N-isopropyltryptamine" class="mw-redirect" title="5,N-Dimethyl-N-isopropyltryptamine">5-Me-MiPT</a></li> <li><a href="/wiki/5-MeO-MiPT" title="5-MeO-MiPT">(Moxy) 5-MeO-MiPT</a></li> <li><a href="/wiki/Methylisopropyltryptamine" class="mw-redirect" title="Methylisopropyltryptamine">MiPT</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Others</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/4-HO-DBT" title="4-HO-DBT">4-HO-DBT</a></li> <li><a href="/wiki/4-HO-EPT" title="4-HO-EPT">4-HO-EPT</a></li> <li><a href="/wiki/4-HO-McPT" title="4-HO-McPT">4-HO-McPT</a></li> <li><a href="/wiki/4-HO-MPMI" title="4-HO-MPMI">(Lucigenol) 4-HO-MPMI</a></li> <li><a href="/wiki/4-HO-MPT" title="4-HO-MPT">(Meprocin) 4-HO-MPT</a></li> <li><a href="/wiki/5-MeO-EiPT" title="5-MeO-EiPT">5-MeO-EiPT</a></li> <li><a href="/wiki/5-MeO-MALT" title="5-MeO-MALT">5-MeO-MALT</a></li> <li><a href="/wiki/5-MeO-MPMI" title="5-MeO-MPMI">5-MeO-MPMI</a></li> <li><a href="/wiki/Aeruginascin" title="Aeruginascin">Aeruginascin</a></li> <li><a href="/wiki/Baeocystin" title="Baeocystin">Baeocystin</a></li> <li><a href="/wiki/Dibutyltryptamine" title="Dibutyltryptamine">DBT</a></li> <li><a href="/w/index.php?title=Dicyclopropyltryptamine&action=edit&redlink=1" class="new" title="Dicyclopropyltryptamine (page does not exist)">DCPT</a></li> <li><a href="/wiki/Ethylisopropyltryptamine" title="Ethylisopropyltryptamine">EiPT</a></li> <li><a href="/wiki/Ethylpropyltryptamine" title="Ethylpropyltryptamine">EPT</a></li> <li><a href="/wiki/Methylpropyltryptamine" title="Methylpropyltryptamine">MPT</a></li> <li><a href="/wiki/Propylisopropyltryptamine" title="Propylisopropyltryptamine">PiPT</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Others</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/AL-38022A" title="AL-38022A">AL-38022A</a></li> <li><a href="/wiki/ALPHA_(psychedelic)" title="ALPHA (psychedelic)">ALPHA</a></li> <li><a href="/wiki/Dimemebfe" title="Dimemebfe">Dimemebfe</a></li> <li><a href="/wiki/Efavirenz" title="Efavirenz">Efavirenz</a></li> <li><a href="/wiki/Glaucine" title="Glaucine">Glaucine</a></li> <li><a href="/wiki/Lorcaserin" title="Lorcaserin">Lorcaserin</a></li> <li><a href="/wiki/M-ALPHA" class="mw-redirect" title="M-ALPHA">M-ALPHA</a></li> <li><a href="/wiki/RH-34" title="RH-34">RH-34</a><br /><small>Also <a href="/wiki/Empathogen-entactogen" class="mw-redirect" title="Empathogen-entactogen">empathogens</a> in general (e. g.: <a href="/wiki/5-APB" title="5-APB">5-APB</a>, <a href="/wiki/5-MAPB" title="5-MAPB">5-MAPB</a>, <a href="/wiki/6-APB" title="6-APB">6-APB</a> and other <a href="/wiki/Substituted_benzofuran" title="Substituted benzofuran">substituted benzofurans</a>).</small></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Dissociative" title="Dissociative">Dissociatives</a><br /><small>(<a href="/wiki/NMDA_receptor" title="NMDA receptor">NMDAR</a><br /><a href="/wiki/NMDA_receptor_antagonist" title="NMDA receptor antagonist">antagonists</a>)</small></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Arylcyclohexylamine" title="Arylcyclohexylamine">Arylcyclo‐<br />hexylamines</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%">Ketamine-related</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/2-Fluorodeschloroketamine" title="2-Fluorodeschloroketamine">2-Fluorodeschloroketamine</a></li> <li><a href="/wiki/Arketamine" title="Arketamine">Arketamine</a> ((R)-ketamine)</li> <li><a href="/wiki/Deschloroketamine" title="Deschloroketamine">Deschloroketamine</a></li> <li><a href="/wiki/Ethketamine" class="mw-redirect" title="Ethketamine">Ethketamine</a> (N-Ethylnorketamine)</li> <li><a href="/wiki/Esketamine" title="Esketamine">Esketamine</a> ((S)-ketamine)</li> <li><a href="/wiki/Ketamine" title="Ketamine">Ketamine</a></li> <li><a href="/wiki/Methoxetamine" title="Methoxetamine">Methoxetamine</a></li> <li><a href="/wiki/Methoxmetamine" title="Methoxmetamine">Methoxmetamine</a></li> <li><a href="/wiki/Methoxyketamine" title="Methoxyketamine">Methoxyketamine</a></li> <li><a href="/wiki/MXiPr" class="mw-redirect" title="MXiPr">MXiPr</a></li> <li><a href="/wiki/Norketamine" title="Norketamine">Norketamine</a></li> <li><a href="/wiki/Tiletamine" title="Tiletamine">Tiletamine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">PCP-related</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%27-Oxo-PCE" class="mw-redirect" title="2'-Oxo-PCE">2'-Oxo-PCE</a></li> <li><a href="/w/index.php?title=3-HO-PCE&action=edit&redlink=1" class="new" title="3-HO-PCE (page does not exist)">3-HO-PCE</a></li> <li><a href="/wiki/3-HO-PCP" title="3-HO-PCP">3-HO-PCP</a></li> <li><a href="/wiki/3-MeO-PCE" title="3-MeO-PCE">3-MeO-PCE</a></li> <li><a href="/wiki/3-MeO-PCMo" title="3-MeO-PCMo">3-MeO-PCMo</a></li> <li><a href="/wiki/3-MeO-PCP" title="3-MeO-PCP">3-MeO-PCP</a></li> <li><a href="/w/index.php?title=3-MeO-PCPr&action=edit&redlink=1" class="new" title="3-MeO-PCPr (page does not exist)">3-MeO-PCPr</a></li> <li><a href="/w/index.php?title=3-MeO-PCPy&action=edit&redlink=1" class="new" title="3-MeO-PCPy (page does not exist)">3-MeO-PCPy</a></li> <li><a href="/wiki/4-MeO-PCP" title="4-MeO-PCP">4-MeO-PCP</a></li> <li><a href="/wiki/BDPC" title="BDPC">BDPC</a></li> <li><a href="/wiki/Dieticyclidine" title="Dieticyclidine">Dieticyclidine</a> (PCDE)</li> <li><a href="/wiki/Eticyclidine" title="Eticyclidine">Eticyclidine</a> (PCE)</li> <li><a href="/wiki/PCPr" title="PCPr">PCPr</a></li> <li><a href="/wiki/Phencyclidine" title="Phencyclidine">Phencyclidine</a> (PCP)</li> <li><a href="/wiki/Rolicyclidine" title="Rolicyclidine">Rolicyclidine</a> (PCPy)</li> <li><a href="/wiki/Tenocyclidine" title="Tenocyclidine">Tenocyclidine</a> (TCP)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Others</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/BTCP" class="mw-redirect" title="BTCP">BTCP</a></li> <li><a href="/wiki/Gacyclidine" title="Gacyclidine">Gacyclidine</a></li> <li><a href="/wiki/PRE-084" title="PRE-084">PRE-084</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/Adamantane" title="Adamantane">Adamantanes</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/Amantadine" title="Amantadine">Amantadine</a></li> <li><a href="/wiki/Memantine" title="Memantine">Memantine</a></li> <li><a href="/wiki/Rimantadine" title="Rimantadine">Rimantadine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Diarylethylamines</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/Diphenidine" title="Diphenidine">Diphenidine</a></li> <li><a href="/wiki/Ephenidine" title="Ephenidine">Ephenidine</a></li> <li><a href="/wiki/Fluorolintane" title="Fluorolintane">Fluorolintane</a></li> <li><a href="/wiki/Methoxphenidine" title="Methoxphenidine">Methoxphenidine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Morphinan" title="Morphinan">Morphinans</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/Dextrallorphan" title="Dextrallorphan">Dextrallorphan</a></li> <li><a href="/wiki/Dextromethorphan" title="Dextromethorphan">Dextromethorphan</a></li> <li><a href="/wiki/Dextrorphan" title="Dextrorphan">Dextrorphan</a></li> <li><a href="/wiki/Racemethorphan" class="mw-redirect" title="Racemethorphan">Racemethorphan</a></li> <li><a href="/wiki/Racemorphan" title="Racemorphan">Racemorphan</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Others</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/2-EMSB" class="mw-redirect" title="2-EMSB">2-EMSB</a></li> <li><a href="/wiki/2-MDP" title="2-MDP">2-MDP</a></li> <li><a href="/wiki/8A-PDHQ" title="8A-PDHQ">8A-PDHQ</a></li> <li><a href="/wiki/Aptiganel" title="Aptiganel">Aptiganel</a></li> <li><a href="/wiki/Budipine" title="Budipine">Budipine</a></li> <li><a href="/wiki/Delucemine" title="Delucemine">Delucemine</a></li> <li><a href="/wiki/Dexoxadrol" title="Dexoxadrol">Dexoxadrol</a></li> <li><a href="/wiki/Dizocilpine" title="Dizocilpine">Dizocilpine</a></li> <li><a href="/wiki/Etoxadrol" title="Etoxadrol">Etoxadrol</a></li> <li><a href="/wiki/Herkinorin" title="Herkinorin">Herkinorin</a></li> <li><a href="/wiki/Ibogaine" title="Ibogaine">Ibogaine</a></li> <li><a href="/wiki/Midafotel" title="Midafotel">Midafotel</a></li> <li><a href="/wiki/NEFA_(drug)" title="NEFA (drug)">NEFA</a></li> <li><a href="/wiki/Neramexane" title="Neramexane">Neramexane</a></li> <li><a href="/wiki/Nitrous_oxide" title="Nitrous oxide">Nitrous oxide</a></li> <li><a href="/wiki/Noribogaine" title="Noribogaine">Noribogaine</a></li> <li><a href="/wiki/Perzinfotel" title="Perzinfotel">Perzinfotel</a></li> <li><a href="/wiki/RB-64" title="RB-64">RB-64</a></li> <li><a href="/wiki/Remacemide" title="Remacemide">Remacemide</a></li> <li><a href="/wiki/Selfotel" title="Selfotel">Selfotel</a></li> <li><a href="/wiki/Xenon" title="Xenon">Xenon</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Deliriant" title="Deliriant">Deliriants</a><br /><small>(<a href="/wiki/Muscarinic_acetylcholine_receptor" title="Muscarinic acetylcholine receptor">mAChR</a><br /><a href="/wiki/Anticholinergic" title="Anticholinergic">antagonists</a>)</small></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Atropine" title="Atropine">Atropine</a></li> <li><a href="/wiki/Benactyzine" title="Benactyzine">Benactyzine</a></li> <li><a href="/wiki/Benzatropine" title="Benzatropine">Benzatropine</a></li> <li><a href="/wiki/Benzydamine" title="Benzydamine">Benzydamine</a></li> <li><a href="/wiki/Biperiden" title="Biperiden">Biperiden</a></li> <li><a href="/w/index.php?title=BRN-1484501&action=edit&redlink=1" class="new" title="BRN-1484501 (page does not exist)">BRN-1484501</a></li> <li><a href="/wiki/Brompheniramine" title="Brompheniramine">Brompheniramine</a></li> <li><a href="/wiki/3-Quinuclidinyl_benzilate" title="3-Quinuclidinyl benzilate">BZ</a></li> <li><a href="/wiki/CAR-226,086" title="CAR-226,086">CAR-226,086</a></li> <li><a href="/wiki/CAR-301,060" title="CAR-301,060">CAR-301,060</a></li> <li><a href="/wiki/CAR-302,196" title="CAR-302,196">CAR-302,196</a></li> <li><a href="/wiki/CAR-302,282" title="CAR-302,282">CAR-302,282</a></li> <li><a href="/w/index.php?title=CAR-302,368&action=edit&redlink=1" class="new" title="CAR-302,368 (page does not exist)">CAR-302,368</a></li> <li><a href="/w/index.php?title=CAR-302,537&action=edit&redlink=1" class="new" title="CAR-302,537 (page does not exist)">CAR-302,537</a></li> <li><a href="/wiki/CAR-302,668" title="CAR-302,668">CAR-302,668</a></li> <li><a href="/wiki/Chloropyramine" title="Chloropyramine">Chloropyramine</a></li> <li><a href="/wiki/Chlorphenamine" title="Chlorphenamine">Chlorphenamine</a></li> <li><a href="/wiki/Clemastine" title="Clemastine">Clemastine</a></li> <li><a href="/wiki/CS-27349" title="CS-27349">CS-27349</a></li> <li><a href="/wiki/Cyclizine" title="Cyclizine">Cyclizine</a></li> <li><a href="/wiki/Cyproheptadine" title="Cyproheptadine">Cyproheptadine</a></li> <li><a href="/wiki/Dicycloverine" title="Dicycloverine">Dicycloverine</a></li> <li><a href="/wiki/Dimenhydrinate" title="Dimenhydrinate">Dimenhydrinate</a></li> <li><a href="/wiki/Diphenhydramine" title="Diphenhydramine">Diphenhydramine</a></li> <li><a href="/wiki/Ditran" title="Ditran">Ditran</a></li> <li><a href="/wiki/Doxylamine" title="Doxylamine">Doxylamine</a></li> <li><a href="/wiki/EA-3167" title="EA-3167">EA-3167</a></li> <li><a href="/wiki/EA-3443" title="EA-3443">EA-3443</a></li> <li><a href="/wiki/EA-3580" title="EA-3580">EA-3580</a></li> <li><a href="/wiki/EA-3834" title="EA-3834">EA-3834</a></li> <li><a href="/wiki/Flavoxate" title="Flavoxate">Flavoxate</a></li> <li><a href="/wiki/Hyoscyamine" title="Hyoscyamine">Hyoscyamine</a></li> <li><a href="/wiki/N-Ethyl-3-piperidyl_benzilate" title="N-Ethyl-3-piperidyl benzilate">JB-318</a></li> <li><a href="/wiki/N-Methyl-3-piperidyl_benzilate" title="N-Methyl-3-piperidyl benzilate">JB-336</a></li> <li><a href="/wiki/Meclozine" class="mw-redirect" title="Meclozine">Meclozine</a></li> <li><a href="/wiki/Mepyramine" title="Mepyramine">Mepyramine</a></li> <li><a href="/wiki/Orphenadrine" title="Orphenadrine">Orphenadrine</a></li> <li><a href="/wiki/Oxybutynin" title="Oxybutynin">Oxybutynin</a></li> <li><a href="/wiki/Pheniramine" title="Pheniramine">Pheniramine</a></li> <li><a href="/wiki/Phenyltoloxamine" title="Phenyltoloxamine">Phenyltoloxamine</a></li> <li><a href="/wiki/Procyclidine" title="Procyclidine">Procyclidine</a></li> <li><a href="/wiki/Promethazine" title="Promethazine">Promethazine</a></li> <li><a href="/wiki/Scopolamine" title="Scopolamine">Scopolamine</a></li> <li><a href="/wiki/Tolterodine" title="Tolterodine">Tolterodine</a></li> <li><a href="/wiki/Trihexyphenidyl" title="Trihexyphenidyl">Trihexyphenidyl</a></li> <li><a href="/wiki/Tripelennamine" title="Tripelennamine">Tripelennamine</a></li> <li><a href="/wiki/Triprolidine" title="Triprolidine">Triprolidine</a></li> <li><a href="/wiki/WIN-2299" title="WIN-2299">WIN-2299</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Others</th><td class="navbox-list-with-group navbox-list navbox-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/Cannabinoid" title="Cannabinoid">Cannabinoids</a><br /><small>(<a href="/wiki/Cannabinoid_receptor_type_1" class="mw-redirect" title="Cannabinoid receptor type 1">CB<sub>1</sub></a> agonists)</small></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Phytocannabinoids" class="mw-redirect" title="Phytocannabinoids">Natural</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/Salvinorin_A" title="Salvinorin A">Salvinorin A</a></li> <li><a href="/wiki/Tetrahydrocannabinol" title="Tetrahydrocannabinol">THC (Dronabinol)</a></li> <li><a href="/wiki/THCV" class="mw-redirect" title="THCV">THCV</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Synthetic_cannabinoids" title="Synthetic cannabinoids">Synthetic</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/List_of_AM_cannabinoids" title="List of AM cannabinoids">AM-<i>x</i></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/AM-087" title="AM-087">AM-087</a></li> <li><a href="/wiki/AM251" class="mw-redirect" title="AM251">AM-251</a></li> <li><a href="/w/index.php?title=AM-279_(disambiguation)&action=edit&redlink=1" class="new" title="AM-279 (disambiguation) (page does not exist)">AM-279</a></li> <li><a href="/w/index.php?title=AM-281_(disambiguation)&action=edit&redlink=1" class="new" title="AM-281 (disambiguation) (page does not exist)">AM-281</a></li> <li><a href="/w/index.php?title=AM-356_(disambiguation)&action=edit&redlink=1" class="new" title="AM-356 (disambiguation) (page does not exist)">AM-356</a></li> <li><a href="/w/index.php?title=AM-374_(disambiguation)&action=edit&redlink=1" class="new" title="AM-374 (disambiguation) (page does not exist)">AM-374</a></li> <li><a href="/w/index.php?title=AM-381_(disambiguation)&action=edit&redlink=1" class="new" title="AM-381 (disambiguation) (page does not exist)">AM-381</a></li> <li><a href="/wiki/AM-404" class="mw-redirect" title="AM-404">AM-404</a></li> <li><a href="/wiki/AM-411" title="AM-411">AM-411</a></li> <li><a href="/wiki/AM-630" title="AM-630">AM-630</a></li> <li><a href="/w/index.php?title=AM-661&action=edit&redlink=1" class="new" title="AM-661 (page does not exist)">AM-661</a></li> <li><a href="/wiki/AM-678" class="mw-redirect" title="AM-678">AM-678</a></li> <li><a href="/wiki/AM-679_(cannabinoid)" title="AM-679 (cannabinoid)">AM-679</a></li> <li><a href="/wiki/AM-694" title="AM-694">AM-694</a></li> <li><a href="/w/index.php?title=AM-735&action=edit&redlink=1" class="new" title="AM-735 (page does not exist)">AM-735</a></li> <li><a href="/wiki/AM-855" title="AM-855">AM-855</a></li> <li><a href="/w/index.php?title=AM-881&action=edit&redlink=1" class="new" title="AM-881 (page does not exist)">AM-881</a></li> <li><a href="/wiki/AM-883" class="mw-redirect" title="AM-883">AM-883</a></li> <li><a href="/wiki/AM-905" title="AM-905">AM-905</a></li> <li><a href="/wiki/AM-906" title="AM-906">AM-906</a></li> <li><a href="/wiki/AM-919" title="AM-919">AM-919</a></li> <li><a href="/wiki/AM-926" class="mw-redirect" title="AM-926">AM-926</a></li> <li><a href="/wiki/AM-938" title="AM-938">AM-938</a></li> <li><a href="/w/index.php?title=AM-1116&action=edit&redlink=1" class="new" title="AM-1116 (page does not exist)">AM-1116</a></li> <li><a href="/w/index.php?title=AM-1172&action=edit&redlink=1" class="new" title="AM-1172 (page does not exist)">AM-1172</a></li> <li><a href="/wiki/AM-1220" title="AM-1220">AM-1220</a></li> <li><a href="/wiki/AM-1221" title="AM-1221">AM-1221</a></li> <li><a href="/wiki/AM-1235" title="AM-1235">AM-1235</a></li> <li><a href="/wiki/AM-1241" title="AM-1241">AM-1241</a></li> <li><a href="/wiki/AM-1248" title="AM-1248">AM-1248</a></li> <li><a href="/w/index.php?title=AM-1710&action=edit&redlink=1" class="new" title="AM-1710 (page does not exist)">AM-1710</a></li> <li><a href="/wiki/AM-1714" title="AM-1714">AM-1714</a></li> <li><a href="/w/index.php?title=AM-1902&action=edit&redlink=1" class="new" title="AM-1902 (page does not exist)">AM-1902</a></li> <li><a href="/wiki/AM-2201" title="AM-2201">AM-2201</a></li> <li><a href="/w/index.php?title=AM-2212&action=edit&redlink=1" class="new" title="AM-2212 (page does not exist)">AM-2212</a></li> <li><a href="/w/index.php?title=AM-2213&action=edit&redlink=1" class="new" title="AM-2213 (page does not exist)">AM-2213</a></li> <li><a href="/wiki/AM-2232" title="AM-2232">AM-2232</a></li> <li><a href="/wiki/AM-2233" title="AM-2233">AM-2233</a></li> <li><a href="/wiki/AM-2389" title="AM-2389">AM-2389</a></li> <li><a href="/w/index.php?title=AM-3102&action=edit&redlink=1" class="new" title="AM-3102 (page does not exist)">AM-3102</a></li> <li><a href="/wiki/AM-4030" title="AM-4030">AM-4030</a></li> <li><a href="/w/index.php?title=AM-4054&action=edit&redlink=1" class="new" title="AM-4054 (page does not exist)">AM-4054</a></li> <li><a href="/wiki/AM-4056" class="mw-redirect" title="AM-4056">AM-4056</a></li> <li><a href="/wiki/AM-4113" class="mw-redirect" title="AM-4113">AM-4113</a></li> <li><a href="/wiki/AM-6545" title="AM-6545">AM-6545</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/List_of_CP_cannabinoids" title="List of CP cannabinoids">CP <i>x</i></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/CP_47,497" title="CP 47,497">CP 47,497</a></li> <li><a href="/wiki/CP_55,244" title="CP 55,244">CP 55,244</a></li> <li><a href="/wiki/CP_55,940" title="CP 55,940">CP 55,940</a></li> <li><a href="/w/index.php?title=(%C2%B1)-CP_55,940&action=edit&redlink=1" class="new" title="(±)-CP 55,940 (page does not exist)">(±)-CP 55,940</a></li> <li><a href="/w/index.php?title=(%2B)-CP_55,940&action=edit&redlink=1" class="new" title="(+)-CP 55,940 (page does not exist)">(+)-CP 55,940</a></li> <li><a href="/w/index.php?title=(-)-CP_55,940&action=edit&redlink=1" class="new" title="(-)-CP 55,940 (page does not exist)">(-)-CP 55,940</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/List_of_HU_cannabinoids" title="List of HU cannabinoids">HU-<i>x</i></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/HU-210" title="HU-210">HU-210</a></li> <li><a href="/wiki/HU-211" class="mw-redirect" title="HU-211">HU-211</a></li> <li><a href="/wiki/HU-239" class="mw-redirect" title="HU-239">HU-239</a></li> <li><a href="/wiki/HU-243" title="HU-243">HU-243</a></li> <li><a href="/wiki/HU-308" class="mw-redirect" title="HU-308">HU-308</a></li> <li><a href="/wiki/HU-320" title="HU-320">HU-320</a></li> <li><a href="/wiki/HU-331" title="HU-331">HU-331</a></li> <li><a href="/wiki/HU-336" title="HU-336">HU-336</a></li> <li><a href="/wiki/HU-345" title="HU-345">HU-345</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/List_of_JWH_cannabinoids" title="List of JWH cannabinoids">JWH-<i>x</i></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/JWH-007" title="JWH-007">JWH-007</a></li> <li><a href="/wiki/JWH-015" title="JWH-015">JWH-015</a></li> <li><a href="/wiki/JWH-018" title="JWH-018">JWH-018</a></li> <li><a href="/wiki/JWH-019" title="JWH-019">JWH-019</a></li> <li><a href="/wiki/JWH-030" title="JWH-030">JWH-030</a></li> <li><a href="/wiki/JWH-047" title="JWH-047">JWH-047</a></li> <li><a href="/wiki/JWH-048" title="JWH-048">JWH-048</a></li> <li><a href="/wiki/JWH-051" title="JWH-051">JWH-051</a></li> <li><a href="/wiki/JWH-057" title="JWH-057">JWH-057</a></li> <li><a href="/wiki/JWH-073" title="JWH-073">JWH-073</a></li> <li><a href="/wiki/JWH-081" title="JWH-081">JWH-081</a></li> <li><a href="/wiki/JWH-098" title="JWH-098">JWH-098</a></li> <li><a href="/wiki/JWH-116" title="JWH-116">JWH-116</a></li> <li><a href="/wiki/JWH-120" title="JWH-120">JWH-120</a></li> <li><a href="/wiki/JWH-122" title="JWH-122">JWH-122</a></li> <li><a href="/wiki/JWH-133" title="JWH-133">JWH-133</a></li> <li><a href="/w/index.php?title=JWH-139&action=edit&redlink=1" class="new" title="JWH-139 (page does not exist)">JWH-139</a></li> <li><a href="/wiki/JWH-147" title="JWH-147">JWH-147</a></li> <li><a href="/wiki/JWH-148" title="JWH-148">JWH-148</a></li> <li><a href="/wiki/JWH-149" title="JWH-149">JWH-149</a></li> <li><a href="/wiki/JWH-149" title="JWH-149">JWH-149</a></li> <li><a href="/wiki/JWH-161" title="JWH-161">JWH-161</a></li> <li><a href="/wiki/JWH-164" title="JWH-164">JWH-164</a></li> <li><a href="/w/index.php?title=JWH-166&action=edit&redlink=1" class="new" title="JWH-166 (page does not exist)">JWH-166</a></li> <li><a href="/wiki/JWH-167" title="JWH-167">JWH-167</a></li> <li><a href="/wiki/JWH-171" class="mw-redirect" title="JWH-171">JWH-171</a></li> <li><a href="/wiki/JWH-175" title="JWH-175">JWH-175</a></li> <li><a href="/wiki/JWH-176" title="JWH-176">JWH-176</a></li> <li><a href="/w/index.php?title=JWH-181&action=edit&redlink=1" class="new" title="JWH-181 (page does not exist)">JWH-181</a></li> <li><a href="/wiki/JWH-182" class="mw-redirect" title="JWH-182">JWH-182</a></li> <li><a href="/wiki/JWH-184" title="JWH-184">JWH-184</a></li> <li><a href="/wiki/JWH-185" title="JWH-185">JWH-185</a></li> <li><a href="/w/index.php?title=JWH-192&action=edit&redlink=1" class="new" title="JWH-192 (page does not exist)">JWH-192</a></li> <li><a href="/wiki/JWH-193" title="JWH-193">JWH-193</a></li> <li><a href="/w/index.php?title=JWH-194&action=edit&redlink=1" class="new" title="JWH-194 (page does not exist)">JWH-194</a></li> <li><a href="/w/index.php?title=JWH-195&action=edit&redlink=1" class="new" title="JWH-195 (page does not exist)">JWH-195</a></li> <li><a href="/wiki/JWH-196" title="JWH-196">JWH-196</a></li> <li><a href="/w/index.php?title=JWH-197&action=edit&redlink=1" class="new" title="JWH-197 (page does not exist)">JWH-197</a></li> <li><a href="/wiki/JWH-198" title="JWH-198">JWH-198</a></li> <li><a href="/w/index.php?title=JWH-199&action=edit&redlink=1" class="new" title="JWH-199 (page does not exist)">JWH-199</a></li> <li><a href="/wiki/JWH-200" title="JWH-200">JWH-200</a></li> <li><a href="/wiki/JWH-203" title="JWH-203">JWH-203</a></li> <li><a href="/w/index.php?title=JWH-205&action=edit&redlink=1" class="new" title="JWH-205 (page does not exist)">JWH-205</a></li> <li><a href="/wiki/JWH-210" title="JWH-210">JWH-210</a></li> <li><a href="/wiki/JWH-210" title="JWH-210">JWH-210</a></li> <li><a href="/w/index.php?title=JWH-213&action=edit&redlink=1" class="new" title="JWH-213 (page does not exist)">JWH-213</a></li> <li><a href="/w/index.php?title=JWH-220&action=edit&redlink=1" class="new" title="JWH-220 (page does not exist)">JWH-220</a></li> <li><a href="/w/index.php?title=JWH-229&action=edit&redlink=1" class="new" title="JWH-229 (page does not exist)">JWH-229</a></li> <li><a href="/w/index.php?title=JWH-234&action=edit&redlink=1" class="new" title="JWH-234 (page does not exist)">JWH-234</a></li> <li><a href="/wiki/JWH-249" title="JWH-249">JWH-249</a></li> <li><a href="/wiki/JWH-250" title="JWH-250">JWH-250</a></li> <li><a href="/wiki/JWH-251" title="JWH-251">JWH-251</a></li> <li><a href="/w/index.php?title=JWH-253&action=edit&redlink=1" class="new" title="JWH-253 (page does not exist)">JWH-253</a></li> <li><a href="/w/index.php?title=JWH-258&action=edit&redlink=1" class="new" title="JWH-258 (page does not exist)">JWH-258</a></li> <li><a href="/w/index.php?title=JWH-300&action=edit&redlink=1" class="new" title="JWH-300 (page does not exist)">JWH-300</a></li> <li><a href="/wiki/JWH-302" title="JWH-302">JWH-302</a></li> <li><a href="/wiki/JWH-307" title="JWH-307">JWH-307</a></li> <li><a href="/w/index.php?title=JWH-336&action=edit&redlink=1" class="new" title="JWH-336 (page does not exist)">JWH-336</a></li> <li><a href="/w/index.php?title=JWH-350&action=edit&redlink=1" class="new" title="JWH-350 (page does not exist)">JWH-350</a></li> <li><a href="/wiki/JWH-359" title="JWH-359">JWH-359</a></li> <li><a href="/w/index.php?title=JWH-387&action=edit&redlink=1" class="new" title="JWH-387 (page does not exist)">JWH-387</a></li> <li><a href="/wiki/JWH-398" title="JWH-398">JWH-398</a></li> <li><a href="/wiki/JWH-424" title="JWH-424">JWH-424</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/List_of_miscellaneous_designer_cannabinoids" title="List of miscellaneous designer cannabinoids">Misc. designer cannabinoids</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/4-HTMPIPO" title="4-HTMPIPO">4-HTMPIPO</a></li> <li><a href="/wiki/5F-AB-FUPPYCA" title="5F-AB-FUPPYCA">5F-AB-FUPPYCA</a></li> <li><a href="/wiki/5F-AB-PINACA" title="5F-AB-PINACA">5F-AB-PINACA</a></li> <li><a href="/wiki/5F-ADB" title="5F-ADB">5F-ADB</a></li> <li><a href="/wiki/5F-ADB-PINACA" title="5F-ADB-PINACA">5F-ADB-PINACA</a></li> <li><a href="/wiki/5F-ADBICA" title="5F-ADBICA">5F-ADBICA</a></li> <li><a href="/wiki/5F-AMB" title="5F-AMB">5F-AMB</a></li> <li><a href="/wiki/5F-APINACA" title="5F-APINACA">5F-APINACA</a></li> <li><a href="/wiki/5F-CUMYL-PINACA" title="5F-CUMYL-PINACA">5F-CUMYL-PINACA</a></li> <li><a href="/wiki/5F-NNE1" title="5F-NNE1">5F-NNE1</a></li> <li><a href="/wiki/5F-PB-22" title="5F-PB-22">5F-PB-22</a></li> <li><a href="/wiki/5F-SDB-006" title="5F-SDB-006">5F-SDB-006</a></li> <li><a href="/wiki/A-796,260" title="A-796,260">A-796,260</a></li> <li><a href="/wiki/A-836,339" title="A-836,339">A-836,339</a></li> <li><a href="/wiki/AB-001" title="AB-001">AB-001</a></li> <li><a href="/wiki/AB-005" title="AB-005">AB-005</a></li> <li><a href="/wiki/AB-CHFUPYCA" title="AB-CHFUPYCA">AB-CHFUPYCA</a></li> <li><a href="/wiki/AB-CHMINACA" title="AB-CHMINACA">AB-CHMINACA</a></li> <li><a href="/wiki/AB-FUBINACA" title="AB-FUBINACA">AB-FUBINACA</a></li> <li><a href="/wiki/AB-PINACA" title="AB-PINACA">AB-PINACA</a></li> <li><a href="/wiki/ADAMANTYL-THPINACA" class="mw-redirect" title="ADAMANTYL-THPINACA">ADAMANTYL-THPINACA</a></li> <li><a href="/wiki/ADB-CHMINACA" title="ADB-CHMINACA">ADB-CHMINACA</a></li> <li><a href="/wiki/ADB-FUBINACA" title="ADB-FUBINACA">ADB-FUBINACA</a></li> <li><a href="/wiki/ADB-PINACA" title="ADB-PINACA">ADB-PINACA</a></li> <li><a href="/wiki/ADBICA" title="ADBICA">ADBICA</a></li> <li><a href="/wiki/ADSB-FUB-187" title="ADSB-FUB-187">ADSB-FUB-187</a></li> <li><a href="/wiki/AMB-FUBINACA" title="AMB-FUBINACA">AMB-FUBINACA</a></li> <li><a href="/wiki/APICA_(synthetic_cannabinoid_drug)" title="APICA (synthetic cannabinoid drug)">APICA</a></li> <li><a href="/wiki/APINACA" title="APINACA">APINACA</a></li> <li><a href="/wiki/APP-FUBINACA" title="APP-FUBINACA">APP-FUBINACA</a></li> <li><a href="/wiki/CB-13" title="CB-13">CB-13</a></li> <li><a href="/wiki/CUMYL-PICA" title="CUMYL-PICA">CUMYL-PICA</a></li> <li><a href="/wiki/CUMYL-PINACA" title="CUMYL-PINACA">CUMYL-PINACA</a></li> <li><a href="/wiki/CUMYL-THPINACA" title="CUMYL-THPINACA">CUMYL-THPINACA</a></li> <li><a href="/wiki/Dimethylheptylpyran" title="Dimethylheptylpyran">DMHP</a></li> <li><a href="/wiki/EAM-2201" title="EAM-2201">EAM-2201</a></li> <li><a href="/wiki/FAB-144" title="FAB-144">FAB-144</a></li> <li><a href="/wiki/FDU-PB-22" title="FDU-PB-22">FDU-PB-22</a></li> <li><a href="/wiki/FUB-144" title="FUB-144">FUB-144</a></li> <li><a href="/wiki/FUB-APINACA" title="FUB-APINACA">FUB-APINACA</a></li> <li><a href="/wiki/FUB-JWH-018" title="FUB-JWH-018">FUB-JWH-018</a></li> <li><a href="/wiki/FUB-PB-22" title="FUB-PB-22">FUB-PB-22</a></li> <li><a href="/wiki/FUBIMINA" title="FUBIMINA">FUBIMINA</a></li> <li><a href="/wiki/JTE_7-31" title="JTE 7-31">JTE 7-31</a></li> <li><a href="/wiki/JTE-907" title="JTE-907">JTE-907</a></li> <li><a href="/wiki/Levonantradol" title="Levonantradol">Levonantradol</a></li> <li><a href="/wiki/MDMB-CHMICA" title="MDMB-CHMICA">MDMB-CHMICA</a></li> <li><a href="/wiki/MDMB-CHMINACA" title="MDMB-CHMINACA">MDMB-CHMINACA</a></li> <li><a href="/wiki/MDMB-FUBINACA" title="MDMB-FUBINACA">MDMB-FUBINACA</a></li> <li><a href="/wiki/MEPIRAPIM" class="mw-redirect" title="MEPIRAPIM">MEPIRAPIM</a></li> <li><a href="/wiki/MAM-2201" title="MAM-2201">MAM-2201</a></li> <li><a href="/wiki/MDA-19" title="MDA-19">MDA-19</a></li> <li><a href="/wiki/MN-18" title="MN-18">MN-18</a></li> <li><a href="/wiki/MN-25" title="MN-25">MN-25</a></li> <li><a href="/wiki/NESS-0327" title="NESS-0327">NESS-0327</a></li> <li><a href="/wiki/NESS-040C5" title="NESS-040C5">NESS-040C5</a></li> <li><a href="/wiki/Nabilone" title="Nabilone">Nabilone</a></li> <li><a href="/wiki/Nabitan" title="Nabitan">Nabitan</a></li> <li><a href="/wiki/NM-2201" title="NM-2201">NM-2201</a></li> <li><a href="/wiki/NNE1" title="NNE1">NNE1</a></li> <li><a href="/wiki/Org_28611" title="Org 28611">Org 28611</a></li> <li><a href="/wiki/Parahexyl" title="Parahexyl">Parahexyl</a></li> <li><a href="/wiki/PTI-1" title="PTI-1">PTI-1</a></li> <li><a href="/wiki/PTI-2" title="PTI-2">PTI-2</a></li> <li><a href="/wiki/PX-1" title="PX-1">PX-1</a></li> <li><a href="/wiki/PX-2" title="PX-2">PX-2</a></li> <li><a href="/wiki/PX-3" title="PX-3">PX-3</a></li> <li><a href="/wiki/QUCHIC" title="QUCHIC">QUCHIC</a></li> <li><a href="/wiki/QUPIC" class="mw-redirect" title="QUPIC">QUPIC</a></li> <li><a href="/wiki/RCS-4" title="RCS-4">RCS-4</a></li> <li><a href="/wiki/RCS-8" title="RCS-8">RCS-8</a></li> <li><a href="/wiki/SDB-005" title="SDB-005">SDB-005</a></li> <li><a href="/wiki/SDB-006" title="SDB-006">SDB-006</a></li> <li><a href="/wiki/STS-135_(drug)" title="STS-135 (drug)">STS-135</a></li> <li><a href="/wiki/THC-O-acetate" title="THC-O-acetate">THC-O-acetate</a></li> <li><a href="/wiki/THC-O-phosphate" title="THC-O-phosphate">THC-O-phosphate</a></li> <li><a href="/wiki/THJ-018" title="THJ-018">THJ-018</a></li> <li><a href="/wiki/THJ-2201" title="THJ-2201">THJ-2201</a></li> <li><a href="/wiki/UR-144" title="UR-144">UR-144</a></li> <li><a href="/wiki/WIN_55,212-2" title="WIN 55,212-2">WIN 55,212-2</a></li> <li><a href="/wiki/XLR-11" title="XLR-11">XLR-11</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Dopamine_receptor_D2" title="Dopamine receptor D2">D<sub>2</sub></a> <a href="/wiki/Dopamine_agonist" title="Dopamine agonist">agonists</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/Apomorphine" title="Apomorphine">Apomorphine</a></li> <li><a href="/wiki/Aporphine" title="Aporphine">Aporphine</a></li> <li><a href="/wiki/Bromocriptine" title="Bromocriptine">Bromocriptine</a></li> <li><a href="/wiki/Cabergoline" title="Cabergoline">Cabergoline</a></li> <li><a href="/wiki/Lisuride" title="Lisuride">Lisuride</a></li> <li><a href="/wiki/LSD" title="LSD">LSD</a></li> <li><a href="/wiki/Memantine" title="Memantine">Memantine</a></li> <li><a href="/wiki/Nuciferine" title="Nuciferine">Nuciferine</a></li> <li><a href="/wiki/Pergolide" title="Pergolide">Pergolide</a></li> <li><a href="/wiki/Phenethylamine" title="Phenethylamine">Phenethylamine</a></li> <li><a href="/wiki/Piribedil" title="Piribedil">Piribedil</a></li> <li><a href="/wiki/Pramipexole" title="Pramipexole">Pramipexole</a></li> <li><a href="/wiki/Ropinirole" title="Ropinirole">Ropinirole</a></li> <li><a href="/wiki/Rotigotine" title="Rotigotine">Rotigotine</a></li> <li><a href="/wiki/Salvinorin_A" title="Salvinorin A">Salvinorin A</a><br /><small>Also indirect D<sub>2</sub> agonists, such as <a href="/wiki/Dopamine_reuptake_inhibitor" title="Dopamine reuptake inhibitor">dopamine reuptake inhibitors</a> (<a href="/wiki/Cocaine" title="Cocaine">cocaine</a>, <a href="/wiki/Methylphenidate" title="Methylphenidate">methylphenidate</a>), <a href="/wiki/Releasing_agent" class="mw-redirect" title="Releasing agent">releasing agents</a> (<a href="/wiki/Amphetamine" title="Amphetamine">amphetamine</a>, <a href="/wiki/Methamphetamine" title="Methamphetamine">methamphetamine</a>), and <a href="/wiki/Precursor_(chemistry)" title="Precursor (chemistry)">precursors</a> (<a href="/wiki/L-DOPA" title="L-DOPA">levodopa</a>).</small></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/GABAA_receptor" title="GABAA receptor">GABA<sub>A</sub></a><br />enhancers</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/CI-966" title="CI-966">CI-966</a></li> <li><a href="/wiki/Eszopiclone" title="Eszopiclone">Eszopiclone</a></li> <li><a href="/wiki/Ibotenic_acid" title="Ibotenic acid">Ibotenic acid</a></li> <li><a href="/wiki/Muscimol" title="Muscimol">Muscimol</a> (<i><a href="/wiki/Amanita_muscaria" title="Amanita muscaria">Amanita muscaria</a></i>)</li> <li><a href="/wiki/Zaleplon" title="Zaleplon">Zaleplon</a></li> <li><a href="/wiki/Zolpidem" title="Zolpidem">Zolpidem</a></li> <li><a href="/wiki/Zopiclone" title="Zopiclone">Zopiclone</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Inhalant" title="Inhalant">Inhalants</a><br /><small>(Mixed <a href="/wiki/Mechanism_of_action" title="Mechanism of action">MOA</a>)</small></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/Aliphatic_hydrocarbons" class="mw-redirect" title="Aliphatic hydrocarbons">Aliphatic hydrocarbons</a> <ul><li><a href="/wiki/Butane" title="Butane">Butane</a></li> <li><a href="/wiki/Gasoline" title="Gasoline">Gasoline</a></li> <li><a href="/wiki/Kerosene" title="Kerosene">Kerosene</a></li> <li><a href="/wiki/Propane" title="Propane">Propane</a></li></ul></li> <li><a href="/wiki/Aromatic_hydrocarbon" class="mw-redirect" title="Aromatic hydrocarbon">Aromatic hydrocarbons</a> <ul><li><a href="/wiki/Toluene" title="Toluene">Toluene</a></li></ul></li> <li><a href="/wiki/Ether" title="Ether">Ethers</a> <ul><li><a href="/wiki/Diethyl_ether" title="Diethyl ether">Diethyl ether</a></li> <li><a href="/wiki/Enflurane" title="Enflurane">Enflurane</a></li></ul></li> <li><a href="/wiki/Haloalkane" title="Haloalkane">Haloalkanes</a> <ul><li><a href="/wiki/Chlorofluorocarbon" title="Chlorofluorocarbon">Chlorofluorocarbons</a></li> <li><a class="mw-selflink selflink">Chloroform</a></li></ul></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/%CE%9A-opioid_receptor" title="Κ-opioid receptor">κOR</a> <a href="/wiki/Opioid" title="Opioid">agonists</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/Salvinorin_B_ethoxymethyl_ether" class="mw-redirect" title="Salvinorin B ethoxymethyl ether">2-EMSB</a></li> <li><a href="/wiki/Alazocine" title="Alazocine">Alazocine</a></li> <li><a href="/wiki/Bremazocine" title="Bremazocine">Bremazocine</a></li> <li><a href="/wiki/Butorphan" class="mw-redirect" title="Butorphan">Butorphan</a></li> <li><a href="/wiki/Butorphanol" title="Butorphanol">Butorphanol</a></li> <li><a href="/wiki/Cyclazocine" title="Cyclazocine">Cyclazocine</a></li> <li><a href="/wiki/Cyclorphan" title="Cyclorphan">Cyclorphan</a></li> <li><a href="/wiki/Cyprenorphine" title="Cyprenorphine">Cyprenorphine</a></li> <li><a href="/wiki/Diprenorphine" title="Diprenorphine">Diprenorphine</a></li> <li><a href="/wiki/Enadoline" title="Enadoline">Enadoline</a></li> <li><a href="/wiki/Herkinorin" title="Herkinorin">Herkinorin</a></li> <li><a href="/wiki/Heroin" title="Heroin">Heroin</a></li> <li><a href="/wiki/HZ-2" title="HZ-2">HZ-2</a></li> <li><a href="/wiki/Ibogaine" title="Ibogaine">Ibogaine</a></li> <li><a href="/wiki/Ketazocine" title="Ketazocine">Ketazocine</a></li> <li><a href="/wiki/Levallorphan" title="Levallorphan">Levallorphan</a></li> <li><a href="/wiki/Levomethorphan" title="Levomethorphan">Levomethorphan</a></li> <li><a href="/wiki/Levorphanol" title="Levorphanol">Levorphanol</a></li> <li><a href="/wiki/LPK-26" title="LPK-26">LPK-26</a></li> <li><a href="/wiki/Metazocine" title="Metazocine">Metazocine</a></li> <li><a href="/wiki/Morphine" title="Morphine">Morphine</a></li> <li><a href="/wiki/Nalbuphine" title="Nalbuphine">Nalbuphine</a></li> <li><a href="/wiki/Nalmefene" title="Nalmefene">Nalmefene</a></li> <li><a href="/wiki/Nalorphine" title="Nalorphine">Nalorphine</a></li> <li><a href="/wiki/Noribogaine" title="Noribogaine">Noribogaine</a></li> <li><a href="/wiki/Oxilorphan" title="Oxilorphan">Oxilorphan</a></li> <li><a href="/wiki/Pentazocine" title="Pentazocine">Pentazocine</a></li> <li><a href="/wiki/Phenazocine" title="Phenazocine">Phenazocine</a></li> <li><a href="/wiki/Proxorphan" title="Proxorphan">Proxorphan</a></li> <li><a href="/wiki/Racemethorphan" class="mw-redirect" title="Racemethorphan">Racemethorphan</a></li> <li><a href="/wiki/Racemorphan" title="Racemorphan">Racemorphan</a></li> <li><a href="/wiki/Salvinorin_A" title="Salvinorin A">Salvinorin A</a></li> <li><a href="/wiki/Spiradoline" title="Spiradoline">Spiradoline</a></li> <li><a href="/wiki/Tifluadom" title="Tifluadom">Tifluadom</a></li> <li><a href="/wiki/U-50488" title="U-50488">U-50488</a></li> <li><a href="/wiki/U-69,593" title="U-69,593">U-69,593</a></li> <li><a href="/wiki/Xorphanol" title="Xorphanol">Xorphanol</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Oneirogen" title="Oneirogen">Oneirogens</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/Calea_ternifolia" title="Calea ternifolia">Calea zacatechichi</a></li> <li><a href="/wiki/Silene_undulata" title="Silene undulata">Silene capensis</a></li> <li><a href="/wiki/Galantamine" title="Galantamine">Galantamine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Others</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Glaucine" title="Glaucine">Glaucine</a></li> <li><a href="/wiki/Isoaminile" title="Isoaminile">Isoaminile</a></li> <li><a href="/wiki/Noscapine" title="Noscapine">Noscapine</a></li> <li><a href="/wiki/Prenoxdiazine" title="Prenoxdiazine">Prenoxdiazine</a></li> <li><a href="/wiki/Pukateine" title="Pukateine">Pukateine</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"></div><div role="navigation" class="navbox" aria-labelledby="Pharmacodynamics" 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" style="background:#e8e8ff;background:#ccccff"><div id="Pharmacodynamics" style="font-size:114%;margin:0 4em"><a href="/wiki/Pharmacodynamics" title="Pharmacodynamics">Pharmacodynamics</a></div></th></tr><tr><td colspan="2" class="navbox-list navbox-odd" style="width:100%;padding:0;font-size:114%"><div style="padding:0px"> <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="GABAA_receptor_positive_modulators" style="padding:3px"><table class="nowraplinks mw-collapsible mw-collapsed navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template: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_modulators" 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 href="/wiki/Thymol" title="Thymol">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 class="mw-selflink selflink">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/Niacin" title="Niacin">Niacin</a></li> <li><a href="/wiki/Niacinamide" class="mw-redirect" title="Niacinamide">Niacinamide</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="Ionotropic_glutamate_receptor_modulators" style="padding:3px"><table class="nowraplinks hlist mw-collapsible mw-collapsed navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Ionotropic_glutamate_receptor_modulators" title="Template:Ionotropic glutamate receptor modulators"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Ionotropic_glutamate_receptor_modulators" title="Template talk:Ionotropic glutamate receptor modulators"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Ionotropic_glutamate_receptor_modulators" title="Special:EditPage/Template:Ionotropic glutamate receptor modulators"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Ionotropic_glutamate_receptor_modulators" style="font-size:114%;margin:0 4em"><a href="/wiki/Ionotropic_glutamate_receptor" title="Ionotropic glutamate receptor">Ionotropic glutamate receptor</a> <a href="/wiki/Receptor_modulator" title="Receptor modulator">modulators</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/%CE%91-Amino-3-hydroxy-5-methyl-4-isoxazolepropionic_acid_receptor" class="mw-redirect" title="Α-Amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid receptor"><abbr title="α-Amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid receptor">AMPAR</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip α-Amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid receptor</span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><b>Agonists:</b> <i>Main site agonists:</i> <a href="/wiki/5-Fluorowillardiine" title="5-Fluorowillardiine">5-Fluorowillardiine</a></li> <li><a href="/wiki/Acromelic_acid_A" title="Acromelic acid A">Acromelic acid (acromelate)</a></li> <li><a href="/wiki/AMPA" title="AMPA">AMPA</a></li> <li><a href="/w/index.php?title=%CE%92-N-Oxalylamino-L-Alanine&action=edit&redlink=1" class="new" title="Β-N-Oxalylamino-L-Alanine (page does not exist)">BOAA</a></li> <li><a href="/wiki/Domoic_acid" title="Domoic acid">Domoic acid</a></li> <li><a href="/wiki/Glutamate" class="mw-redirect" title="Glutamate">Glutamate</a></li> <li><a href="/wiki/Ibotenic_acid" title="Ibotenic acid">Ibotenic acid</a></li> <li><a href="/wiki/Proline" title="Proline">Proline</a></li> <li><a href="/wiki/Quisqualic_acid" title="Quisqualic acid">Quisqualic acid</a></li> <li><a href="/wiki/Willardiine" title="Willardiine">Willardiine</a>; <i>Positive allosteric modulators:</i> <a href="/wiki/Aniracetam" title="Aniracetam">Aniracetam</a></li> <li><a href="/wiki/Cyclothiazide" title="Cyclothiazide">Cyclothiazide</a></li> <li><a href="/wiki/CX-516" title="CX-516">CX-516</a></li> <li><a href="/wiki/CX-546" title="CX-546">CX-546</a></li> <li><a href="/wiki/CX614" title="CX614">CX-614</a></li> <li><a href="/wiki/Farampator" title="Farampator">Farampator (CX-691, ORG-24448)</a></li> <li><a href="/wiki/CX717" title="CX717">CX-717</a></li> <li><a href="/wiki/CX-1739" class="mw-redirect" title="CX-1739">CX-1739</a></li> <li><a href="/w/index.php?title=CX-1942&action=edit&redlink=1" class="new" title="CX-1942 (page does not exist)">CX-1942</a></li> <li><a href="/wiki/Diazoxide" title="Diazoxide">Diazoxide</a></li> <li><a href="/wiki/Hydrochlorothiazide" title="Hydrochlorothiazide">Hydrochlorothiazide (HCTZ)</a></li> <li><a href="/wiki/IDRA-21" title="IDRA-21">IDRA-21</a></li> <li><a href="/w/index.php?title=LY-392098&action=edit&redlink=1" class="new" title="LY-392098 (page does not exist)">LY-392098</a></li> <li><a href="/w/index.php?title=LY-395153&action=edit&redlink=1" class="new" title="LY-395153 (page does not exist)">LY-395153</a></li> <li><a href="/wiki/LY-404187" title="LY-404187">LY-404187</a></li> <li><a href="/w/index.php?title=LY-451646&action=edit&redlink=1" class="new" title="LY-451646 (page does not exist)">LY-451646</a></li> <li><a href="/wiki/LY-503430" title="LY-503430">LY-503430</a></li> <li><a href="/wiki/Mibampator" title="Mibampator">Mibampator (LY-451395)</a></li> <li><a href="/wiki/Nooglutyl" title="Nooglutyl">Nooglutyl</a></li> <li><a href="/wiki/ORG-26576" title="ORG-26576">ORG-26576</a></li> <li><a href="/wiki/Oxiracetam" title="Oxiracetam">Oxiracetam</a></li> <li><a href="/wiki/PEPA_(drug)" title="PEPA (drug)">PEPA</a></li> <li><a href="/wiki/Pesampator" title="Pesampator">Pesampator (BIIB-104, PF-04958242)</a></li> <li><a href="/wiki/Piracetam" title="Piracetam">Piracetam</a></li> <li><a href="/wiki/Pramiracetam" title="Pramiracetam">Pramiracetam</a></li> <li><a href="/wiki/S-18986" title="S-18986">S-18986</a></li> <li><a href="/wiki/Tulrampator" title="Tulrampator">Tulrampator (S-47445, CX-1632)</a></li></ul> <ul><li><b>Antagonists:</b> <a href="/w/index.php?title=ACEA-1011&action=edit&redlink=1" class="new" title="ACEA-1011 (page does not exist)">ACEA-1011</a></li> <li><a href="/w/index.php?title=ATPO&action=edit&redlink=1" class="new" title="ATPO (page does not exist)">ATPO</a></li> <li><a href="/wiki/Becampanel" title="Becampanel">Becampanel</a></li> <li><a href="/wiki/Caroverine" title="Caroverine">Caroverine</a></li> <li><a href="/wiki/CNQX" title="CNQX">CNQX</a></li> <li><a href="/wiki/Dasolampanel" title="Dasolampanel">Dasolampanel</a></li> <li><a href="/wiki/DNQX" title="DNQX">DNQX</a></li> <li><a href="/wiki/Fanapanel" title="Fanapanel">Fanapanel (MPQX)</a></li> <li><a href="/w/index.php?title=Gamma-D-Glutamylaminomethylsulfonic_acid&action=edit&redlink=1" class="new" title="Gamma-D-Glutamylaminomethylsulfonic acid (page does not exist)">GAMS</a></li> <li><a href="/wiki/Kaitocephalin" title="Kaitocephalin">Kaitocephalin</a></li> <li><a href="/wiki/Kynurenic_acid" title="Kynurenic acid">Kynurenic acid</a></li> <li><a href="/wiki/Kynurenine" title="Kynurenine">Kynurenine</a></li> <li><a href="/wiki/Licostinel" title="Licostinel">Licostinel (ACEA-1021)</a></li> <li><a href="/wiki/NBQX" title="NBQX">NBQX</a></li> <li><a href="/w/index.php?title=PNQX&action=edit&redlink=1" class="new" title="PNQX (page does not exist)">PNQX</a></li> <li><a href="/wiki/Selurampanel" title="Selurampanel">Selurampanel</a></li> <li><a href="/wiki/Tezampanel" title="Tezampanel">Tezampanel</a></li> <li><a href="/wiki/Theanine" title="Theanine">Theanine</a></li> <li><a href="/wiki/Topiramate" title="Topiramate">Topiramate</a></li> <li><a href="/w/index.php?title=YM90K&action=edit&redlink=1" class="new" title="YM90K (page does not exist)">YM90K</a></li> <li><a href="/wiki/Zonampanel" title="Zonampanel">Zonampanel</a>; <i>Negative allosteric modulators:</i> <a href="/wiki/Barbiturates" class="mw-redirect" title="Barbiturates">Barbiturates</a> (e.g., <a href="/wiki/Pentobarbital" title="Pentobarbital">pentobarbital</a>, <a href="/wiki/Sodium_thiopental" title="Sodium thiopental">sodium thiopental</a>)</li> <li><a href="/wiki/Cyclopropane" title="Cyclopropane">Cyclopropane</a></li> <li><a href="/wiki/Enflurane" title="Enflurane">Enflurane</a></li> <li><a href="/wiki/Alcohol_(drug)" title="Alcohol (drug)">Ethanol (alcohol)</a></li> <li><a href="/wiki/Evans_blue_(dye)" title="Evans blue (dye)">Evans blue</a></li> <li><a href="/wiki/GYKI_52466" title="GYKI 52466">GYKI-52466</a></li> <li><a href="/w/index.php?title=GYKI-53655&action=edit&redlink=1" class="new" title="GYKI-53655 (page does not exist)">GYKI-53655</a></li> <li><a href="/wiki/Halothane" title="Halothane">Halothane</a></li> <li><a href="/wiki/Irampanel" title="Irampanel">Irampanel</a></li> <li><a href="/wiki/Isoflurane" title="Isoflurane">Isoflurane</a></li> <li><a href="/wiki/Perampanel" title="Perampanel">Perampanel</a></li> <li><a href="/wiki/Pregnenolone_sulfate" title="Pregnenolone sulfate">Pregnenolone sulfate</a></li> <li><a href="/wiki/Sevoflurane" title="Sevoflurane">Sevoflurane</a></li> <li><a href="/wiki/Talampanel" title="Talampanel">Talampanel</a>; <i>Unknown/unsorted antagonists:</i> <a href="/wiki/Minocycline" title="Minocycline">Minocycline</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Kainate_receptor" title="Kainate receptor"><abbr title="Kainate receptor">KAR</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Kainate receptor</span></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><b>Agonists:</b> <i>Main site agonists:</i> <a href="/w/index.php?title=5-Bromowillardiine&action=edit&redlink=1" class="new" title="5-Bromowillardiine (page does not exist)">5-Bromowillardiine</a></li> <li><a href="/wiki/5-Iodowillardiine" title="5-Iodowillardiine">5-Iodowillardiine</a></li> <li><a href="/w/index.php?title=Acromelic_acid&action=edit&redlink=1" class="new" title="Acromelic acid (page does not exist)">Acromelic acid (acromelate)</a></li> <li><a href="/wiki/AMPA" title="AMPA">AMPA</a></li> <li><a href="/w/index.php?title=ATPA&action=edit&redlink=1" class="new" title="ATPA (page does not exist)">ATPA</a></li> <li><a href="/wiki/Domoic_acid" title="Domoic acid">Domoic acid</a></li> <li><a href="/wiki/Glutamate" class="mw-redirect" title="Glutamate">Glutamate</a></li> <li><a href="/wiki/Ibotenic_acid" title="Ibotenic acid">Ibotenic acid</a></li> <li><a href="/wiki/Kainic_acid" title="Kainic acid">Kainic acid</a></li> <li><a href="/w/index.php?title=LY-339434&action=edit&redlink=1" class="new" title="LY-339434 (page does not exist)">LY-339434</a></li> <li><a href="/wiki/Proline" title="Proline">Proline</a></li> <li><a href="/wiki/Quisqualic_acid" title="Quisqualic acid">Quisqualic acid</a></li> <li><a href="/wiki/SYM-2081" title="SYM-2081">SYM-2081</a>; <i>Positive allosteric modulators:</i> <a href="/wiki/Cyclothiazide" title="Cyclothiazide">Cyclothiazide</a></li> <li><a href="/wiki/Diazoxide" title="Diazoxide">Diazoxide</a></li> <li><a href="/wiki/Enflurane" title="Enflurane">Enflurane</a></li> <li><a href="/wiki/Halothane" title="Halothane">Halothane</a></li> <li><a href="/wiki/Isoflurane" title="Isoflurane">Isoflurane</a></li></ul> <ul><li><b>Antagonists:</b> <a href="/w/index.php?title=ACEA-1011&action=edit&redlink=1" class="new" title="ACEA-1011 (page does not exist)">ACEA-1011</a></li> <li><a href="/wiki/CNQX" title="CNQX">CNQX</a></li> <li><a href="/wiki/Dasolampanel" title="Dasolampanel">Dasolampanel</a></li> <li><a href="/wiki/DNQX" title="DNQX">DNQX</a></li> <li><a href="/w/index.php?title=Gamma-D-Glutamylaminomethylsulfonic_acid&action=edit&redlink=1" class="new" title="Gamma-D-Glutamylaminomethylsulfonic acid (page does not exist)">GAMS</a></li> <li><a href="/wiki/Kaitocephalin" title="Kaitocephalin">Kaitocephalin</a></li> <li><a href="/wiki/Kynurenic_acid" title="Kynurenic acid">Kynurenic acid</a></li> <li><a href="/wiki/Licostinel" title="Licostinel">Licostinel (ACEA-1021)</a></li> <li><a href="/w/index.php?title=LY-382884&action=edit&redlink=1" class="new" title="LY-382884 (page does not exist)">LY-382884</a></li> <li><a href="/wiki/NBQX" title="NBQX">NBQX</a></li> <li><a href="/wiki/NS102" title="NS102">NS102</a></li> <li><a href="/wiki/Selurampanel" title="Selurampanel">Selurampanel</a></li> <li><a href="/wiki/Tezampanel" title="Tezampanel">Tezampanel</a></li> <li><a href="/wiki/Theanine" title="Theanine">Theanine</a></li> <li><a href="/wiki/Topiramate" title="Topiramate">Topiramate</a></li> <li><a href="/wiki/UBP-302" title="UBP-302">UBP-302</a>; <i>Negative allosteric modulators:</i> <a href="/wiki/Barbiturates" class="mw-redirect" title="Barbiturates">Barbiturates</a> (e.g., <a href="/wiki/Pentobarbital" title="Pentobarbital">pentobarbital</a>, <a href="/wiki/Sodium_thiopental" title="Sodium thiopental">sodium thiopental</a>)</li> <li><a href="/wiki/Enflurane" title="Enflurane">Enflurane</a></li> <li><a href="/wiki/Alcohol_(drug)" title="Alcohol (drug)">Ethanol (alcohol)</a></li> <li><a href="/wiki/Evans_blue_(dye)" title="Evans blue (dye)">Evans blue</a></li> <li><a href="/w/index.php?title=NS-3763&action=edit&redlink=1" class="new" title="NS-3763 (page does not exist)">NS-3763</a></li> <li><a href="/wiki/Pregnenolone_sulfate" title="Pregnenolone sulfate">Pregnenolone sulfate</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/N-Methyl-D-aspartate_receptor" class="mw-redirect" title="N-Methyl-D-aspartate receptor"><abbr title="N-Methyl-D-aspartate receptor">NMDAR</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip N-Methyl-D-aspartate receptor</span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><b>Agonists:</b> <i>Main site agonists:</i> <a href="/w/index.php?title=2-Amino-2-(3-hydroxy-5-methylisoxazol-4-yl)acetic_acid&action=edit&redlink=1" class="new" title="2-Amino-2-(3-hydroxy-5-methylisoxazol-4-yl)acetic acid (page does not exist)">AMAA</a></li> <li><a href="/wiki/Aspartate" class="mw-redirect" title="Aspartate">Aspartate</a></li> <li><a href="/wiki/Glutamate" class="mw-redirect" title="Glutamate">Glutamate</a></li> <li><a href="/wiki/Homocysteic_acid" title="Homocysteic acid">Homocysteic acid (<small>L</small>-HCA)</a></li> <li><a href="/wiki/Homoquinolinic_acid" title="Homoquinolinic acid">Homoquinolinic acid</a></li> <li><a href="/wiki/Ibotenic_acid" title="Ibotenic acid">Ibotenic acid</a></li> <li><a href="/wiki/N-Methyl-D-aspartic_acid" title="N-Methyl-D-aspartic acid">NMDA</a></li> <li><a href="/wiki/Proline" title="Proline">Proline</a></li> <li><a href="/wiki/Quinolinic_acid" title="Quinolinic acid">Quinolinic acid</a></li> <li><a href="/wiki/Tetrazolylglycine" title="Tetrazolylglycine">Tetrazolylglycine</a></li> <li><a href="/wiki/Theanine" title="Theanine">Theanine</a>; <i>Glycine site agonists:</i> <a href="/w/index.php?title=%CE%92-Fluoro-D-alanine&action=edit&redlink=1" class="new" title="Β-Fluoro-D-alanine (page does not exist)">β-Fluoro-<small>D</small>-alanine</a></li> <li><a href="/w/index.php?title=ACBD_(drug)&action=edit&redlink=1" class="new" title="ACBD (drug) (page does not exist)">ACBD</a></li> <li><a href="/wiki/1-Aminocyclopropanecarboxylic_acid" class="mw-redirect" title="1-Aminocyclopropanecarboxylic acid">ACC (ACPC)</a></li> <li><a href="/wiki/ACPD" title="ACPD">ACPD</a></li> <li><a href="/w/index.php?title=AK-51_(drug)&action=edit&redlink=1" class="new" title="AK-51 (drug) (page does not exist)">AK-51</a></li> <li><a href="/wiki/Apimostinel" title="Apimostinel">Apimostinel (NRX-1074)</a></li> <li><a href="/wiki/B6B21" class="mw-redirect" title="B6B21">B6B21</a></li> <li><a href="/w/index.php?title=Carboxycyclopropylglycine&action=edit&redlink=1" class="new" title="Carboxycyclopropylglycine (page does not exist)">CCG</a></li> <li><a href="/wiki/Alanine" title="Alanine"><small>D</small>-Alanine</a></li> <li><a href="/wiki/Cycloserine" title="Cycloserine"><small>D</small>-Cycloserine</a></li> <li><a href="/wiki/Serine" title="Serine"><small>D</small>-Serine</a></li> <li><a href="/w/index.php?title=N-(3,3-Diphenylpropyl)glycinamide&action=edit&redlink=1" class="new" title="N-(3,3-Diphenylpropyl)glycinamide (page does not exist)">DHPG</a></li> <li><a href="/wiki/Dimethylglycine" title="Dimethylglycine">Dimethylglycine</a></li> <li><a href="/wiki/Glycine" title="Glycine">Glycine</a></li> <li><a href="/wiki/HA-966" title="HA-966">HA-966</a></li> <li><a href="/w/index.php?title=L-687414&action=edit&redlink=1" class="new" title="L-687414 (page does not exist)">L-687414</a></li> <li><a href="/wiki/Alanine" title="Alanine"><small>L</small>-Alanine</a></li> <li><a href="/wiki/Serine" title="Serine"><small>L</small>-Serine</a></li> <li><a href="/wiki/Milacemide" title="Milacemide">Milacemide</a></li> <li><a href="/wiki/Neboglamine" title="Neboglamine">Neboglamine (nebostinel)</a></li> <li><a href="/wiki/Rapastinel" title="Rapastinel">Rapastinel (GLYX-13)</a></li> <li><a href="/wiki/Sarcosine" title="Sarcosine">Sarcosine</a>; <i>Polyamine site agonists:</i> <a href="/wiki/Neomycin" title="Neomycin">Neomycin</a></li> <li><a href="/wiki/Spermidine" title="Spermidine">Spermidine</a></li> <li><a href="/wiki/Spermine" title="Spermine">Spermine</a>; <i>Other positive allosteric modulators:</i> <a href="/wiki/24S-Hydroxycholesterol" title="24S-Hydroxycholesterol">24<i>S</i>-Hydroxycholesterol</a></li> <li><a href="/wiki/Dehydroepiandrosterone" title="Dehydroepiandrosterone"><abbr title="Dehydroepiandrosterone">DHEA</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Dehydroepiandrosterone</span> (<a href="/wiki/Prasterone" title="Prasterone">prasterone</a>)</li> <li><a href="/wiki/Dehydroepiandrosterone_sulfate" title="Dehydroepiandrosterone sulfate"><abbr title="Dehydroepiandrosterone">DHEA</abbr> sulfate</a> (<a href="/wiki/Prasterone_sulfate" title="Prasterone sulfate">prasterone sulfate</a>)</li> <li><a href="/w/index.php?title=Epipregnanolone_sulfate&action=edit&redlink=1" class="new" title="Epipregnanolone sulfate (page does not exist)">Epipregnanolone sulfate</a></li> <li><a href="/w/index.php?title=Plazinemdor&action=edit&redlink=1" class="new" title="Plazinemdor (page does not exist)">Plazinemdor</a></li> <li><a href="/wiki/Pregnenolone_sulfate" title="Pregnenolone sulfate">Pregnenolone sulfate</a></li> <li><a href="/w/index.php?title=SAGE-201&action=edit&redlink=1" class="new" title="SAGE-201 (page does not exist)">SAGE-201</a></li> <li><a href="/w/index.php?title=SAGE-301&action=edit&redlink=1" class="new" title="SAGE-301 (page does not exist)">SAGE-301</a></li> <li><a href="/wiki/SAGE-718" class="mw-redirect" title="SAGE-718">SAGE-718</a></li></ul> <ul><li><b>Antagonists:</b> <i>Competitive antagonists:</i> <a href="/wiki/AP5" title="AP5">AP5 (APV)</a></li> <li><a href="/wiki/AP-7_(drug)" title="AP-7 (drug)">AP7</a></li> <li><a href="/wiki/CGP-37849" title="CGP-37849">CGP-37849</a></li> <li><a href="/wiki/CGP-39551" title="CGP-39551">CGP-39551</a></li> <li><a href="/w/index.php?title=CGP-39653&action=edit&redlink=1" class="new" title="CGP-39653 (page does not exist)">CGP-39653</a></li> <li><a href="/w/index.php?title=CGP-40116&action=edit&redlink=1" class="new" title="CGP-40116 (page does not exist)">CGP-40116</a></li> <li><a href="/wiki/CGS-19755" class="mw-redirect" title="CGS-19755">CGS-19755</a></li> <li><a href="/w/index.php?title=3-(2-carboxypiperazin-4-yl)propyl-1-phosphonic_acid&action=edit&redlink=1" class="new" title="3-(2-carboxypiperazin-4-yl)propyl-1-phosphonic acid (page does not exist)">CPP</a></li> <li><a href="/wiki/Kaitocephalin" title="Kaitocephalin">Kaitocephalin</a></li> <li><a href="/w/index.php?title=LY-233053&action=edit&redlink=1" class="new" title="LY-233053 (page does not exist)">LY-233053</a></li> <li><a href="/wiki/LY-235959" title="LY-235959">LY-235959</a></li> <li><a href="/w/index.php?title=LY-274614&action=edit&redlink=1" class="new" title="LY-274614 (page does not exist)">LY-274614</a></li> <li><a href="/w/index.php?title=MDL-100453&action=edit&redlink=1" class="new" title="MDL-100453 (page does not exist)">MDL-100453</a></li> <li><a href="/wiki/Midafotel" title="Midafotel">Midafotel (d-CPPene)</a></li> <li><a href="/w/index.php?title=NPC-12626&action=edit&redlink=1" class="new" title="NPC-12626 (page does not exist)">NPC-12626</a></li> <li><a href="/w/index.php?title=NPC-17742&action=edit&redlink=1" class="new" title="NPC-17742 (page does not exist)">NPC-17742</a></li> <li><a href="/w/index.php?title=PBPD&action=edit&redlink=1" class="new" title="PBPD (page does not exist)">PBPD</a></li> <li><a href="/wiki/PEAQX" title="PEAQX">PEAQX</a></li> <li><a href="/wiki/Perzinfotel" title="Perzinfotel">Perzinfotel</a></li> <li><a href="/w/index.php?title=Cis-1-(phenanthrene-2-carbonyl)piperazine-2,3-dicarboxylic_acid&action=edit&redlink=1" class="new" title="Cis-1-(phenanthrene-2-carbonyl)piperazine-2,3-dicarboxylic acid (page does not exist)">PPDA</a></li> <li><a href="/w/index.php?title=SDZ-220581&action=edit&redlink=1" class="new" title="SDZ-220581 (page does not exist)">SDZ-220581</a></li> <li><a href="/wiki/Selfotel" title="Selfotel">Selfotel</a>; <i>Glycine site antagonists:</i> <a href="/wiki/4-Chlorokynurenine" title="4-Chlorokynurenine">4-Cl-KYN (AV-101)</a></li> <li><a href="/wiki/5,7-Dichlorokynurenic_acid" title="5,7-Dichlorokynurenic acid">5,7-DCKA</a></li> <li><a href="/wiki/7-Chlorokynurenic_acid" title="7-Chlorokynurenic acid">7-CKA</a></li> <li><a href="/wiki/1-Aminocyclopropane-1-carboxylic_acid" title="1-Aminocyclopropane-1-carboxylic acid">ACC</a></li> <li><a href="/w/index.php?title=ACEA-1011&action=edit&redlink=1" class="new" title="ACEA-1011 (page does not exist)">ACEA-1011</a></li> <li><a href="/w/index.php?title=ACEA-1328&action=edit&redlink=1" class="new" title="ACEA-1328 (page does not exist)">ACEA-1328</a></li> <li><a href="/wiki/Apimostinel" title="Apimostinel">Apimostinel (NRX-1074)</a></li> <li><a href="/wiki/AV-101" class="mw-redirect" title="AV-101">AV-101</a></li> <li><a href="/wiki/Carisoprodol" title="Carisoprodol">Carisoprodol</a></li> <li><a href="/w/index.php?title=CGP-39653&action=edit&redlink=1" class="new" title="CGP-39653 (page does not exist)">CGP-39653</a></li> <li><a href="/wiki/CNQX" title="CNQX">CNQX</a></li> <li><a href="/wiki/Cycloserine" title="Cycloserine"><small>D</small>-Cycloserine</a></li> <li><a href="/wiki/DNQX" title="DNQX">DNQX</a></li> <li><a href="/wiki/Felbamate" title="Felbamate">Felbamate</a></li> <li><a href="/wiki/Gavestinel" title="Gavestinel">Gavestinel</a></li> <li><a href="/w/index.php?title=GV-196771&action=edit&redlink=1" class="new" title="GV-196771 (page does not exist)">GV-196771</a></li> <li><a href="/w/index.php?title=Harkoseride&action=edit&redlink=1" class="new" title="Harkoseride (page does not exist)">Harkoseride</a></li> <li><a href="/wiki/Kynurenic_acid" title="Kynurenic acid">Kynurenic acid</a></li> <li><a href="/wiki/Kynurenine" title="Kynurenine">Kynurenine</a></li> <li><a href="/w/index.php?title=L-689560&action=edit&redlink=1" class="new" title="L-689560 (page does not exist)">L-689560</a></li> <li><a href="/wiki/L-701324" title="L-701324">L-701324</a></li> <li><a href="/wiki/Licostinel" title="Licostinel">Licostinel (ACEA-1021)</a></li> <li><a href="/w/index.php?title=LU-73068&action=edit&redlink=1" class="new" title="LU-73068 (page does not exist)">LU-73068</a></li> <li><a href="/w/index.php?title=MDL-105519&action=edit&redlink=1" class="new" title="MDL-105519 (page does not exist)">MDL-105519</a></li> <li><a href="/wiki/Meprobamate" title="Meprobamate">Meprobamate</a></li> <li><a href="/w/index.php?title=MRZ_2/576&action=edit&redlink=1" class="new" title="MRZ 2/576 (page does not exist)">MRZ 2/576</a></li> <li><a href="/w/index.php?title=PNQX&action=edit&redlink=1" class="new" title="PNQX (page does not exist)">PNQX</a></li> <li><a href="/wiki/Rapastinel" title="Rapastinel">Rapastinel (GLYX-13)</a></li> <li><a href="/wiki/ZD-9379" title="ZD-9379">ZD-9379</a>; <i>Polyamine site antagonists:</i> <a href="/w/index.php?title=Arcaine&action=edit&redlink=1" class="new" title="Arcaine (page does not exist)">Arcaine</a></li> <li><a href="/w/index.php?title=Co_101676&action=edit&redlink=1" class="new" title="Co 101676 (page does not exist)">Co 101676</a></li> <li><a href="/wiki/1,3-Diaminopropane" title="1,3-Diaminopropane">Diaminopropane</a></li> <li><a href="/wiki/Diethylenetriamine" title="Diethylenetriamine">Diethylenetriamine</a></li> <li><a href="/wiki/Huperzine_A" title="Huperzine A">Huperzine A</a></li> <li><a href="/wiki/Putrescine" title="Putrescine">Putrescine</a>; <i>Uncompetitive pore blockers (mostly dizocilpine site):</i> <a href="/wiki/2-MDP" title="2-MDP">2-MDP</a></li> <li><a href="/wiki/3-HO-PCP" title="3-HO-PCP">3-HO-PCP</a></li> <li><a href="/wiki/3-MeO-PCE" title="3-MeO-PCE">3-MeO-PCE</a></li> <li><a href="/wiki/3-MeO-PCMo" title="3-MeO-PCMo">3-MeO-PCMo</a></li> <li><a href="/wiki/3-MeO-PCP" title="3-MeO-PCP">3-MeO-PCP</a></li> <li><a href="/wiki/4-MeO-PCP" title="4-MeO-PCP">4-MeO-PCP</a></li> <li><a href="/wiki/8a-Phenyldecahydroquinoline" class="mw-redirect" title="8a-Phenyldecahydroquinoline">8A-PDHQ</a></li> <li><a href="/wiki/18-Methoxycoronaridine" title="18-Methoxycoronaridine">18-MC</a></li> <li><a href="/wiki/Alpha-Endopsychosin" class="mw-redirect" title="Alpha-Endopsychosin">α-Endopsychosin</a></li> <li><a href="/wiki/Alaproclate" title="Alaproclate">Alaproclate</a></li> <li><a href="/wiki/Alazocine" title="Alazocine">Alazocine (SKF-10047)</a></li> <li><a href="/wiki/Amantadine" title="Amantadine">Amantadine</a></li> <li><a href="/wiki/Aptiganel" title="Aptiganel">Aptiganel</a></li> <li><a href="/w/index.php?title=Argiotoxin-636&action=edit&redlink=1" class="new" title="Argiotoxin-636 (page does not exist)">Argiotoxin-636</a></li> <li><a href="/wiki/Arketamine" title="Arketamine">Arketamine</a></li> <li><a href="/w/index.php?title=ARL-12495&action=edit&redlink=1" class="new" title="ARL-12495 (page does not exist)">ARL-12495</a></li> <li><a href="/wiki/ARL-15896-AR" class="mw-redirect" title="ARL-15896-AR">ARL-15896-AR</a></li> <li><a href="/wiki/ARL-16247" class="mw-redirect" title="ARL-16247">ARL-16247</a></li> <li><a href="/wiki/Budipine" title="Budipine">Budipine</a></li> <li><a href="/wiki/Coronaridine" title="Coronaridine">Coronaridine</a></li> <li><a href="/wiki/Delucemine" title="Delucemine">Delucemine (NPS-1506)</a></li> <li><a href="/wiki/Dexoxadrol" title="Dexoxadrol">Dexoxadrol</a></li> <li><a href="/wiki/Dextrallorphan" title="Dextrallorphan">Dextrallorphan</a></li> <li><a href="/wiki/Dextromethadone" class="mw-redirect" title="Dextromethadone">Dextromethadone</a></li> <li><a href="/wiki/Dextromethorphan" title="Dextromethorphan">Dextromethorphan</a></li> <li><a href="/wiki/Dextrorphan" title="Dextrorphan">Dextrorphan</a></li> <li><a href="/wiki/Dieticyclidine" title="Dieticyclidine">Dieticyclidine</a></li> <li><a href="/wiki/Diphenidine" title="Diphenidine">Diphenidine</a></li> <li><a href="/wiki/Dizocilpine" title="Dizocilpine">Dizocilpine</a></li> <li><a href="/wiki/Ephenidine" title="Ephenidine">Ephenidine</a></li> <li><a href="/wiki/Esketamine" title="Esketamine">Esketamine</a></li> <li><a href="/wiki/Etoxadrol" title="Etoxadrol">Etoxadrol</a></li> <li><a href="/wiki/Eticyclidine" title="Eticyclidine">Eticyclidine</a></li> <li><a href="/wiki/Fluorolintane" title="Fluorolintane">Fluorolintane</a></li> <li><a href="/wiki/Gacyclidine" title="Gacyclidine">Gacyclidine</a></li> <li><a href="/wiki/Ibogaine" title="Ibogaine">Ibogaine</a></li> <li><a href="/wiki/Ibogamine" title="Ibogamine">Ibogamine</a></li> <li><a href="/wiki/Indantadol" title="Indantadol">Indantadol</a></li> <li><a href="/wiki/Ketamine" title="Ketamine">Ketamine</a></li> <li><a href="/wiki/Ketobemidone" title="Ketobemidone">Ketobemidone</a></li> <li><a href="/wiki/Lanicemine" title="Lanicemine">Lanicemine</a></li> <li><a href="/wiki/Levomethadone" title="Levomethadone">Levomethadone</a></li> <li><a href="/wiki/Levomethorphan" title="Levomethorphan">Levomethorphan</a></li> <li><a href="/wiki/Levomilnacipran" title="Levomilnacipran">Levomilnacipran</a></li> <li><a href="/wiki/Levorphanol" title="Levorphanol">Levorphanol</a></li> <li><a href="/wiki/Loperamide" title="Loperamide">Loperamide</a></li> <li><a href="/wiki/Memantine" title="Memantine">Memantine</a></li> <li><a href="/wiki/Methadone" title="Methadone">Methadone</a></li> <li><a href="/wiki/Methorphan" title="Methorphan">Methorphan</a></li> <li><a href="/wiki/Methoxetamine" title="Methoxetamine">Methoxetamine</a></li> <li><a href="/wiki/Methoxphenidine" title="Methoxphenidine">Methoxphenidine</a></li> <li><a href="/wiki/Milnacipran" title="Milnacipran">Milnacipran</a></li> <li><a href="/wiki/Morphanol" class="mw-redirect" title="Morphanol">Morphanol</a></li> <li><a href="/wiki/NEFA_(drug)" title="NEFA (drug)">NEFA</a></li> <li><a href="/wiki/Neramexane" title="Neramexane">Neramexane</a></li> <li><a href="/wiki/Nitromemantine" title="Nitromemantine">Nitromemantine</a></li> <li><a href="/wiki/Noribogaine" title="Noribogaine">Noribogaine</a></li> <li><a href="/wiki/Norketamine" title="Norketamine">Norketamine</a></li> <li><a href="/wiki/Orphenadrine" title="Orphenadrine">Orphenadrine</a></li> <li><a href="/wiki/PCPr" title="PCPr">PCPr</a></li> <li><a href="/wiki/PD-137889" title="PD-137889">PD-137889</a></li> <li><a href="/wiki/Pethidine" title="Pethidine">Pethidine (meperidine)</a></li> <li><a href="/wiki/Phencyclamine" class="mw-redirect" title="Phencyclamine">Phencyclamine</a></li> <li><a href="/wiki/Phencyclidine" title="Phencyclidine">Phencyclidine</a></li> <li><a href="/wiki/Propoxyphene" class="mw-redirect" title="Propoxyphene">Propoxyphene</a></li> <li><a href="/wiki/Remacemide" title="Remacemide">Remacemide</a></li> <li><a href="/wiki/Rhynchophylline" title="Rhynchophylline">Rhynchophylline</a></li> <li><a href="/wiki/Rimantadine" title="Rimantadine">Rimantadine</a></li> <li><a href="/wiki/Rolicyclidine" title="Rolicyclidine">Rolicyclidine</a></li> <li><a href="/wiki/Sabeluzole" title="Sabeluzole">Sabeluzole</a></li> <li><a href="/wiki/Tabernanthine" title="Tabernanthine">Tabernanthine</a></li> <li><a href="/wiki/Tenocyclidine" title="Tenocyclidine">Tenocyclidine</a></li> <li><a href="/wiki/Tiletamine" title="Tiletamine">Tiletamine</a></li> <li><a href="/wiki/Tramadol" title="Tramadol">Tramadol</a>; <i>Ifenprodil (NR2B) site antagonists:</i></li> <li><a href="/wiki/Besonprodil" title="Besonprodil">Besonprodil</a></li> <li><a href="/wiki/Buphenine" title="Buphenine">Buphenine (nylidrin)</a></li> <li><a href="/w/index.php?title=CO-101244&action=edit&redlink=1" class="new" title="CO-101244 (page does not exist)">CO-101244 (PD-174494)</a></li> <li><a href="/wiki/Eliprodil" title="Eliprodil">Eliprodil</a></li> <li><a href="/wiki/Haloperidol" title="Haloperidol">Haloperidol</a></li> <li><a href="/wiki/Isoxsuprine" title="Isoxsuprine">Isoxsuprine</a></li> <li><a href="/w/index.php?title=Radiprodil&action=edit&redlink=1" class="new" title="Radiprodil (page does not exist)">Radiprodil (RGH-896)</a></li> <li><a href="/wiki/Rislenemdaz" title="Rislenemdaz">Rislenemdaz (CERC-301, MK-0657)</a></li> <li><a href="/w/index.php?title=Ro_8-4304&action=edit&redlink=1" class="new" title="Ro 8-4304 (page does not exist)">Ro 8-4304</a></li> <li><a href="/w/index.php?title=Ro_25-6981&action=edit&redlink=1" class="new" title="Ro 25-6981 (page does not exist)">Ro 25-6981</a></li> <li><a href="/wiki/Safaprodil" class="mw-redirect" title="Safaprodil">Safaprodil</a></li> <li><a href="/wiki/Traxoprodil" title="Traxoprodil">Traxoprodil (CP-101606)</a>; <i>NR2A-selective antagonists:</i> <a href="/w/index.php?title=MPX-004&action=edit&redlink=1" class="new" title="MPX-004 (page does not exist)">MPX-004</a></li> <li><a href="/w/index.php?title=MPX-007&action=edit&redlink=1" class="new" title="MPX-007 (page does not exist)">MPX-007</a></li> <li><a href="/w/index.php?title=TCN-201&action=edit&redlink=1" class="new" title="TCN-201 (page does not exist)">TCN-201</a></li> <li><a href="/w/index.php?title=TCN-213&action=edit&redlink=1" class="new" title="TCN-213 (page does not exist)">TCN-213</a>; <i>Cations:</i> <a href="/wiki/Hydrogen" title="Hydrogen">Hydrogen</a></li> <li><a href="/wiki/Magnesium" title="Magnesium">Magnesium</a></li> <li><a href="/wiki/Zinc" title="Zinc">Zinc</a>; <i>Alcohols/volatile anesthetics/related:</i> <a href="/wiki/Benzene" title="Benzene">Benzene</a></li> <li><a href="/wiki/Butane" title="Butane">Butane</a></li> <li><a class="mw-selflink selflink">Chloroform</a></li> <li><a href="/wiki/Cyclopropane" title="Cyclopropane">Cyclopropane</a></li> <li><a href="/wiki/Desflurane" title="Desflurane">Desflurane</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/Alcohol_(drug)" title="Alcohol (drug)">Ethanol (alcohol)</a></li> <li><a href="/wiki/Halothane" title="Halothane">Halothane</a></li> <li><a href="/wiki/Hexanol" title="Hexanol">Hexanol</a></li> <li><a href="/wiki/Isoflurane" title="Isoflurane">Isoflurane</a></li> <li><a href="/wiki/Methoxyflurane" title="Methoxyflurane">Methoxyflurane</a></li> <li><a href="/wiki/Nitrous_oxide" title="Nitrous oxide">Nitrous oxide</a></li> <li><a href="/wiki/Octanol" title="Octanol">Octanol</a></li> <li><a href="/wiki/Sevoflurane" title="Sevoflurane">Sevoflurane</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</a></li> <li><a href="/wiki/2,2,2-Trichloroethanol" title="2,2,2-Trichloroethanol">Trichloroethanol</a></li> <li><a href="/wiki/Trichloroethylene" title="Trichloroethylene">Trichloroethylene</a></li> <li><a href="/wiki/Ethyl_carbamate" title="Ethyl carbamate">Urethane</a></li> <li><a href="/wiki/Xenon" title="Xenon">Xenon</a></li> <li><a href="/wiki/Xylene" title="Xylene">Xylene</a>; <i>Unknown/unsorted antagonists:</i> <a href="/w/index.php?title=ARR-15896&action=edit&redlink=1" class="new" title="ARR-15896 (page does not exist)">ARR-15896</a></li> <li><a href="/wiki/Bumetanide" title="Bumetanide">Bumetanide</a></li> <li><a href="/wiki/Caroverine" title="Caroverine">Caroverine</a></li> <li><a href="/wiki/Conantokin" title="Conantokin">Conantokin</a></li> <li><a href="/wiki/D-%CE%B1-Aminoadipate" class="mw-redirect" title="D-α-Aminoadipate"><small>D</small>-αAA</a></li> <li><a href="/wiki/Dexanabinol" title="Dexanabinol">Dexanabinol</a></li> <li><a href="/wiki/Flufenamic_acid" title="Flufenamic acid">Flufenamic acid</a></li> <li><a href="/wiki/Flupirtine" title="Flupirtine">Flupirtine</a></li> <li><a href="/w/index.php?title=FPL-12495&action=edit&redlink=1" class="new" title="FPL-12495 (page does not exist)">FPL-12495</a></li> <li><a href="/w/index.php?title=FR-115427&action=edit&redlink=1" class="new" title="FR-115427 (page does not exist)">FR-115427</a></li> <li><a href="/wiki/Furosemide" title="Furosemide">Furosemide</a></li> <li><a href="/wiki/Hodgkinsine" title="Hodgkinsine">Hodgkinsine</a></li> <li><a href="/w/index.php?title=Ipenoxazone&action=edit&redlink=1" class="new" title="Ipenoxazone (page does not exist)">Ipenoxazone (MLV-6976)</a></li> <li><a href="/w/index.php?title=MDL-27266&action=edit&redlink=1" class="new" title="MDL-27266 (page does not exist)">MDL-27266</a></li> <li><a href="/wiki/Metaphit" title="Metaphit">Metaphit</a></li> <li><a href="/wiki/Minocycline" title="Minocycline">Minocycline</a></li> <li><a href="/wiki/2-Methyl-6-(phenylethynyl)pyridine" title="2-Methyl-6-(phenylethynyl)pyridine">MPEP</a></li> <li><a href="/wiki/Niflumic_acid" title="Niflumic acid">Niflumic acid</a></li> <li><a href="/wiki/Pentamidine" title="Pentamidine">Pentamidine</a></li> <li><a href="/wiki/Pentamidine_isethionate" class="mw-redirect" title="Pentamidine isethionate">Pentamidine isethionate</a></li> <li><a href="/wiki/Piretanide" title="Piretanide">Piretanide</a></li> <li><a href="/wiki/Psychotridine" title="Psychotridine">Psychotridine</a></li> <li><a href="/wiki/Transcrocetin" class="mw-redirect" title="Transcrocetin">Transcrocetin</a> (<a href="/wiki/Saffron" title="Saffron">saffron</a>)</li></ul> <ul><li><b>Unsorted:</b> <i>Allosteric modulators:</i> <a href="/wiki/AGN-241751" class="mw-redirect" title="AGN-241751">AGN-241751</a></li></ul> </div></td></tr><tr><td class="navbox-abovebelow" colspan="2"><div> <ul><li><i><b>See also:</b> <a href="/wiki/Template:Receptor_modulators" title="Template:Receptor modulators">Receptor/signaling modulators</a></i></li> <li><i><a href="/wiki/Template:Metabotropic_glutamate_receptor_modulators" title="Template:Metabotropic glutamate receptor modulators">Metabotropic glutamate receptor modulators</a></i></li> <li><i><a href="/wiki/Template:Glutamate_metabolism_and_transport_modulators" title="Template:Glutamate metabolism and transport modulators">Glutamate metabolism/transport modulators</a></i></li></ul> </div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"></div><div role="navigation" class="navbox" aria-labelledby="Glycine_receptor_modulators" style="padding:3px"><table class="nowraplinks hlist mw-collapsible mw-collapsed navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Glycine_receptor_modulators" title="Template:Glycine receptor modulators"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Glycine_receptor_modulators" title="Template talk:Glycine receptor modulators"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Glycine_receptor_modulators" title="Special:EditPage/Template:Glycine receptor modulators"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Glycine_receptor_modulators" style="font-size:114%;margin:0 4em"><a href="/wiki/Glycine_receptor" title="Glycine receptor">Glycine receptor</a> <a href="/wiki/Receptor_modulator" title="Receptor modulator">modulators</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Receptor_(biochemistry)" title="Receptor (biochemistry)">Receptor</a><br /><small>(<a href="/wiki/Ligand_(biochemistry)" title="Ligand (biochemistry)">ligands</a>)</small></th><td class="navbox-list-with-group navbox-list navbox-odd" 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:4em;;text-align:center;"><a href="/wiki/Glycine_receptor" title="Glycine receptor"><abbr title="Glycine receptor">GlyR</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Glycine receptor</span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><b>Agonists:</b> <a href="/wiki/%CE%92-Alanine" title="Β-Alanine">β-Alanine</a></li> <li><a href="/wiki/Beta-Aminobutyric_acid" class="mw-redirect" title="Beta-Aminobutyric acid">β-ABA (BABA)</a></li> <li><a href="/w/index.php?title=%CE%92-Aminoisobutyric_acid&action=edit&redlink=1" class="new" title="Β-Aminoisobutyric acid (page does not exist)">β-AIBA</a></li> <li><a href="/wiki/Caesium" title="Caesium">Caesium</a></li> <li><a href="/wiki/Alanine" title="Alanine"><small>D</small>-Alanine</a></li> <li><a href="/wiki/Serine" title="Serine"><small>D</small>-Serine</a></li> <li><a href="/wiki/Gamma-Aminobutyric_acid" class="mw-redirect" title="Gamma-Aminobutyric acid">GABA</a></li> <li><a href="/wiki/Glycine" title="Glycine">Glycine</a></li> <li><a href="/wiki/Hypotaurine" title="Hypotaurine">Hypotaurine</a></li> <li><a href="/wiki/Ivermectin" title="Ivermectin">Ivermectin</a></li> <li><a href="/wiki/Alanine" title="Alanine"><small>L</small>-Alanine</a></li> <li><a href="/wiki/Proline" title="Proline"><small>L</small>-Proline</a></li> <li><a href="/wiki/Serine" title="Serine"><small>L</small>-Serine</a></li> <li><a href="/wiki/Threonine" title="Threonine"><small>L</small>-Threonine</a></li> <li><a href="/w/index.php?title=MDL-27531&action=edit&redlink=1" class="new" title="MDL-27531 (page does not exist)">MDL-27531</a></li> <li><a href="/wiki/Milacemide" title="Milacemide">Milacemide</a></li> <li><a href="/wiki/Picolinic_acid" title="Picolinic acid">Picolinic acid</a></li> <li><a href="/wiki/Propofol" title="Propofol">Propofol</a></li> <li><a href="/wiki/Quisqualamine" title="Quisqualamine">Quisqualamine</a></li> <li><a href="/wiki/Sarcosine" title="Sarcosine">Sarcosine</a></li> <li><a href="/wiki/Taurine" title="Taurine">Taurine</a></li></ul> <ul><li><b>Positive modulators:</b> <a href="/wiki/Alcohol_(chemistry)" title="Alcohol (chemistry)">Alcohols</a> (e.g., <a href="/w/index.php?title=Brometone&action=edit&redlink=1" class="new" title="Brometone (page does not exist)">brometone</a>, <a href="/wiki/Chlorobutanol" title="Chlorobutanol">chlorobutanol (chloretone)</a>, <a href="/wiki/Alcohol_(drug)" title="Alcohol (drug)">ethanol (alcohol)</a>, <a href="/wiki/Tert-Butyl_alcohol" title="Tert-Butyl alcohol"><i>tert</i>-butanol (2M2P)</a>, <a href="/wiki/Tribromoethanol" title="Tribromoethanol">tribromoethanol</a>, <a href="/wiki/Trichloroethanol" class="mw-redirect" title="Trichloroethanol">trichloroethanol</a>, <a href="/wiki/Trifluoroethanol" class="mw-redirect" title="Trifluoroethanol">trifluoroethanol</a>)</li> <li><a href="/wiki/Alkylbenzene_sulfonate" title="Alkylbenzene sulfonate">Alkylbenzene sulfonate</a></li> <li><a href="/wiki/Anandamide" title="Anandamide">Anandamide</a></li> <li><a href="/wiki/Barbiturate" title="Barbiturate">Barbiturates</a> (e.g., <a href="/wiki/Pentobarbital" title="Pentobarbital">pentobarbital</a>, <a href="/wiki/Sodium_thiopental" title="Sodium thiopental">sodium thiopental</a>)</li> <li><a href="/wiki/Chlormethiazole" class="mw-redirect" title="Chlormethiazole">Chlormethiazole</a></li> <li><a href="/w/index.php?title=D12-116&action=edit&redlink=1" class="new" title="D12-116 (page does not exist)">D12-116</a></li> <li><a href="/wiki/Dihydropyridine" class="mw-redirect" title="Dihydropyridine">Dihydropyridines</a> (e.g., <a href="/wiki/Nicardipine" title="Nicardipine">nicardipine</a>)</li> <li><a href="/wiki/Etomidate" title="Etomidate">Etomidate</a></li> <li><a href="/wiki/Ginseng" title="Ginseng">Ginseng</a> constituents (e.g., <a href="/wiki/Ginsenoside" title="Ginsenoside">ginsenosides</a> (e.g., <a href="/w/index.php?title=Ginsenoside-Rf&action=edit&redlink=1" class="new" title="Ginsenoside-Rf (page does not exist)">ginsenoside-Rf</a>))</li> <li><a href="/wiki/Glutamic_acid" title="Glutamic acid">Glutamic acid (glutamate)</a></li> <li><a href="/wiki/Ivermectin" title="Ivermectin">Ivermectin</a></li> <li><a href="/wiki/Ketamine" title="Ketamine">Ketamine</a></li> <li><a href="/wiki/Neuroactive_steroid" class="mw-redirect" title="Neuroactive steroid">Neuroactive steroids</a> (e.g., <a href="/wiki/Alfaxolone" class="mw-redirect" title="Alfaxolone">alfaxolone</a>, <a href="/wiki/Pregnenolone" title="Pregnenolone">pregnenolone (eltanolone)</a>, <a href="/wiki/Pregnenolone_acetate" title="Pregnenolone acetate">pregnenolone acetate</a>, <a href="/wiki/Minaxolone" title="Minaxolone">minaxolone</a>, <a href="/wiki/ORG-20599" title="ORG-20599">ORG-20599</a>)</li> <li><a href="/wiki/Nitrous_oxide" title="Nitrous oxide">Nitrous oxide</a></li> <li><a href="/wiki/Penicillin_G" class="mw-redirect" title="Penicillin G">Penicillin G</a></li> <li><a href="/wiki/Propofol" title="Propofol">Propofol</a></li> <li><a href="/wiki/Tamoxifen" title="Tamoxifen">Tamoxifen</a></li> <li><a href="/wiki/Tetrahydrocannabinol" title="Tetrahydrocannabinol">Tetrahydrocannabinol</a></li> <li><a href="/wiki/Triclofos" title="Triclofos">Triclofos</a></li> <li><a href="/w/index.php?title=Tropeine&action=edit&redlink=1" class="new" title="Tropeine (page does not exist)">Tropeines</a> (e.g., <a href="/wiki/Atropine" title="Atropine">atropine</a>, <a href="/wiki/Bemesetron" title="Bemesetron">bemesetron</a>, <a href="/wiki/Cocaine" title="Cocaine">cocaine</a>, <a href="/w/index.php?title=LY-278584&action=edit&redlink=1" class="new" title="LY-278584 (page does not exist)">LY-278584</a>, <a href="/wiki/Tropisetron" title="Tropisetron">tropisetron</a>, <a href="/wiki/Zatosetron" title="Zatosetron">zatosetron</a>)</li> <li><a href="/wiki/Volatility_(chemistry)" title="Volatility (chemistry)">Volatiles</a>/<a href="/wiki/Gas" title="Gas">gases</a> (e.g., <a href="/wiki/Chloral_hydrate" title="Chloral hydrate">chloral hydrate</a>, <a class="mw-selflink selflink">chloroform</a>, <a href="/wiki/Desflurane" title="Desflurane">desflurane</a>, <a href="/wiki/Diethyl_ether" title="Diethyl ether">diethyl ether (ether)</a>, <a href="/wiki/Enflurane" title="Enflurane">enflurane</a>, <a href="/wiki/Halothane" title="Halothane">halothane</a>, <a href="/wiki/Isoflurane" title="Isoflurane">isoflurane</a>, <a href="/wiki/Methoxyflurane" title="Methoxyflurane">methoxyflurane</a>, <a href="/wiki/Sevoflurane" title="Sevoflurane">sevoflurane</a>, <a href="/wiki/Toluene" title="Toluene">toluene</a>, <a href="/wiki/1,1,1-trichloroethane" class="mw-redirect" title="1,1,1-trichloroethane">trichloroethane (methyl chloroform)</a>, <a href="/wiki/Trichloroethylene" title="Trichloroethylene">trichloroethylene</a>)</li> <li><a href="/wiki/Xenon" title="Xenon">Xenon</a></li> <li><a href="/wiki/Zinc" title="Zinc">Zinc</a></li></ul> <ul><li><b>Antagonists:</b> <a href="/w/index.php?title=2-Aminostrychnine&action=edit&redlink=1" class="new" title="2-Aminostrychnine (page does not exist)">2-Aminostrychnine</a></li> <li><a href="/w/index.php?title=2-Nitrostrychnine&action=edit&redlink=1" class="new" title="2-Nitrostrychnine (page does not exist)">2-Nitrostrychnine</a></li> <li><a href="/w/index.php?title=4-Phenyl-4-formyl-N-methylpiperidine&action=edit&redlink=1" class="new" title="4-Phenyl-4-formyl-N-methylpiperidine (page does not exist)">4-Phenyl-4-formyl-N-methylpiperidine</a></li> <li><a href="/w/index.php?title=%CE%91-Ethyl-%CE%B1-methyl-%CE%B3-thiobutyrolactone&action=edit&redlink=1" class="new" title="Α-Ethyl-α-methyl-γ-thiobutyrolactone (page does not exist)">αEMBTL</a></li> <li><a href="/wiki/Bicuculline" title="Bicuculline">Bicuculline</a></li> <li><a href="/wiki/Brucine" title="Brucine">Brucine</a></li> <li><a href="/wiki/Cacotheline" title="Cacotheline">Cacotheline</a></li> <li><a href="/wiki/Caffeine" title="Caffeine">Caffeine</a></li> <li><a href="/wiki/Colchicine" title="Colchicine">Colchicine</a></li> <li><a href="/wiki/Colubrine" class="mw-redirect" title="Colubrine">Colubrine</a></li> <li><a href="/w/index.php?title=Cyanotriphenylborate&action=edit&redlink=1" class="new" title="Cyanotriphenylborate (page does not exist)">Cyanotriphenylborate</a></li> <li><a href="/wiki/Dendrobine" title="Dendrobine">Dendrobine</a></li> <li><a href="/w/index.php?title=Diaboline&action=edit&redlink=1" class="new" title="Diaboline (page does not exist)">Diaboline</a></li> <li><a href="/wiki/Endocannabinoid" class="mw-redirect" title="Endocannabinoid">Endocannabinoids</a> (e.g., <a href="/wiki/2-arachidonylglycerol" class="mw-redirect" title="2-arachidonylglycerol">2-AG</a>, <a href="/wiki/Anandamide" title="Anandamide">anandamide (AEA)</a>)</li> <li><a href="/wiki/Gaboxadol" title="Gaboxadol">Gaboxadol (THIP)</a></li> <li><a href="/wiki/Gelsemine" title="Gelsemine">Gelsemine</a></li> <li><a href="/w/index.php?title=Iso-THAZ&action=edit&redlink=1" class="new" title="Iso-THAZ (page does not exist)">iso-THAZ</a></li> <li><a href="/wiki/Isobutyric_acid" title="Isobutyric acid">Isobutyric acid</a></li> <li><a href="/wiki/Isonipecotic_acid" title="Isonipecotic acid">Isonipecotic acid</a></li> <li><a href="/w/index.php?title=Isostrychnine&action=edit&redlink=1" class="new" title="Isostrychnine (page does not exist)">Isostrychnine</a></li> <li><a href="/wiki/Laudanosine" title="Laudanosine">Laudanosine</a></li> <li><a href="/w/index.php?title=N-Methylbicuculline&action=edit&redlink=1" class="new" title="N-Methylbicuculline (page does not exist)">N-Methylbicuculline</a></li> <li><a href="/w/index.php?title=N-Methylstrychnine&action=edit&redlink=1" class="new" title="N-Methylstrychnine (page does not exist)">N-Methylstrychnine</a></li> <li><a href="/w/index.php?title=N,N-Dimethylmuscimol&action=edit&redlink=1" class="new" title="N,N-Dimethylmuscimol (page does not exist)">N,N-Dimethylmuscimol</a></li> <li><a href="/wiki/Nipecotic_acid" title="Nipecotic acid">Nipecotic acid</a></li> <li><a href="/wiki/Pitrazepin" title="Pitrazepin">Pitrazepin</a></li> <li><a href="/w/index.php?title=Pseudostrychnine&action=edit&redlink=1" class="new" title="Pseudostrychnine (page does not exist)">Pseudostrychnine</a></li> <li><a href="/wiki/Quinoline" title="Quinoline">Quinolines</a> (e.g., <a href="/w/index.php?title=4-hydroxyquinoline&action=edit&redlink=1" class="new" title="4-hydroxyquinoline (page does not exist)">4-hydroxyquinoline</a>, <a href="/w/index.php?title=4-hydroxyquinoline-3-carboxylic_acid&action=edit&redlink=1" class="new" title="4-hydroxyquinoline-3-carboxylic acid (page does not exist)">4-hydroxyquinoline-3-carboxylic acid</a>, <a href="/w/index.php?title=5,7-dichloro-4-hydroxyquinoline-3-carboxylic_acid&action=edit&redlink=1" class="new" title="5,7-dichloro-4-hydroxyquinoline-3-carboxylic acid (page does not exist)">5,7-CIQA</a>, <a href="/w/index.php?title=7-chloro-4-hydroxyquinoline&action=edit&redlink=1" class="new" title="7-chloro-4-hydroxyquinoline (page does not exist)">7-CIQ</a>, <a href="/w/index.php?title=7-trifluoromethyl-4-hydroxyquinoline&action=edit&redlink=1" class="new" title="7-trifluoromethyl-4-hydroxyquinoline (page does not exist)">7-TFQ</a>, <a href="/w/index.php?title=7-trifluoromethyl-4-hydroxyquinoline-3-carboxylic_acid&action=edit&redlink=1" class="new" title="7-trifluoromethyl-4-hydroxyquinoline-3-carboxylic acid (page does not exist)">7-TFQA</a>)</li> <li><a href="/w/index.php?title=RU-5135&action=edit&redlink=1" class="new" title="RU-5135 (page does not exist)">RU-5135</a></li> <li><a href="/wiki/Sinomenine" title="Sinomenine">Sinomenine</a></li> <li><a href="/wiki/Strychnine" title="Strychnine">Strychnine</a></li> <li><a href="/wiki/Thiocolchicoside" title="Thiocolchicoside">Thiocolchicoside</a></li> <li><a href="/wiki/Tutin_(toxin)" title="Tutin (toxin)">Tutin</a></li></ul> <ul><li><b>Negative modulators:</b> <a href="/wiki/Amiloride" title="Amiloride">Amiloride</a></li> <li><a href="/wiki/Benzodiazepine" title="Benzodiazepine">Benzodiazepines</a> (e.g., <a href="/wiki/Bromazepam" title="Bromazepam">bromazepam</a>, <a href="/wiki/Clonazepam" title="Clonazepam">clonazepam</a>, <a href="/wiki/Diazepam" title="Diazepam">diazepam</a>, <a href="/wiki/Flunitrazepam" title="Flunitrazepam">flunitrazepam</a>, <a href="/wiki/Flurazepam" title="Flurazepam">flurazepam</a>)</li> <li><a href="/wiki/Corymine" title="Corymine">Corymine</a></li> <li><a href="/w/index.php?title=Cyanotriphenylborate&action=edit&redlink=1" class="new" title="Cyanotriphenylborate (page does not exist)">Cyanotriphenylborate</a></li> <li><a href="/wiki/Daidzein" title="Daidzein">Daidzein</a></li> <li><a href="/wiki/Dihydropyridine" class="mw-redirect" title="Dihydropyridine">Dihydropyridines</a> (e.g., <a href="/wiki/Nicardipine" title="Nicardipine">nicardipine</a>, <a href="/wiki/Nifedipine" title="Nifedipine">nifedipine</a>, <a href="/wiki/Nitrendipine" title="Nitrendipine">nitrendipine</a>)</li> <li><a href="/wiki/Furosemide" title="Furosemide">Furosemide</a></li> <li><a href="/wiki/Genistein" title="Genistein">Genistein</a></li> <li><a href="/wiki/Ginkgo_biloba" title="Ginkgo biloba">Ginkgo</a> constituents (e.g., <a href="/wiki/Bilobalide" title="Bilobalide">bilobalide</a>, <a href="/wiki/Ginkgolide" title="Ginkgolide">ginkgolides</a> (e.g., <a href="/w/index.php?title=Ginkgolide_A&action=edit&redlink=1" class="new" title="Ginkgolide A (page does not exist)">ginkgolide A</a>, <a href="/wiki/Ginkgolide_B" class="mw-redirect" title="Ginkgolide B">ginkgolide B</a>, <a href="/w/index.php?title=Ginkgolide_C&action=edit&redlink=1" class="new" title="Ginkgolide C (page does not exist)">ginkgolide C</a>, <a href="/w/index.php?title=Ginkgolide_J&action=edit&redlink=1" class="new" title="Ginkgolide J (page does not exist)">ginkgolide J</a>, <a href="/w/index.php?title=Ginkgolide_M&action=edit&redlink=1" class="new" title="Ginkgolide M (page does not exist)">ginkgolide M</a>))</li> <li><a href="/wiki/Imipramine" title="Imipramine">Imipramine</a></li> <li><a href="/wiki/NBQX" title="NBQX">NBQX</a></li> <li><a href="/wiki/Neuroactive_steroid" class="mw-redirect" title="Neuroactive steroid">Neuroactive steroids</a> (e.g., <a href="/wiki/3%CE%B1-androsterone_sulfate" class="mw-redirect" title="3α-androsterone sulfate">3α-androsterone sulfate</a>, <a href="/w/index.php?title=3%CE%B2-androsterone_sulfate&action=edit&redlink=1" class="new" title="3β-androsterone sulfate (page does not exist)">3β-androsterone sulfate</a>, <a href="/wiki/11-deoxycorticosterone" class="mw-redirect" title="11-deoxycorticosterone">deoxycorticosterone</a>, <a href="/wiki/DHEA_sulfate" class="mw-redirect" title="DHEA sulfate">DHEA sulfate</a>, <a href="/wiki/Pregnenolone_sulfate" title="Pregnenolone sulfate">pregnenolone sulfate</a>, <a href="/wiki/Progesterone" title="Progesterone">progesterone</a>)</li> <li><a href="/wiki/Opioid" title="Opioid">Opioids</a> (e.g., <a href="/wiki/Codeine" title="Codeine">codeine</a>, <a href="/wiki/Dextromethorphan" title="Dextromethorphan">dextromethorphan</a>, <a href="/wiki/Dextrorphan" title="Dextrorphan">dextrorphan</a>, <a href="/wiki/Levomethadone" title="Levomethadone">levomethadone</a>, <a href="/wiki/Levorphanol" title="Levorphanol">levorphanol</a>, <a href="/wiki/Morphine" title="Morphine">morphine</a>, <a href="/wiki/Oripavine" title="Oripavine">oripavine</a>, <a href="/wiki/Pethidine" title="Pethidine">pethidine</a>, <a href="/wiki/Thebaine" title="Thebaine">thebaine</a>)</li> <li><a href="/wiki/Picrotoxin" title="Picrotoxin">Picrotoxin</a> (i.e., <a href="/wiki/Picrotin" class="mw-redirect" title="Picrotin">picrotin</a> and <a href="/wiki/Picrotoxinin" class="mw-redirect" title="Picrotoxinin">picrotoxinin</a>)</li> <li><a href="/w/index.php?title=Phenylbenzene_%CF%89-phosphono-%CE%B1-amino_acid&action=edit&redlink=1" class="new" title="Phenylbenzene ω-phosphono-α-amino acid (page does not exist)">PMBA</a></li> <li><a href="/wiki/Riluzole" title="Riluzole">Riluzole</a></li> <li><a href="/w/index.php?title=Tropeine&action=edit&redlink=1" class="new" title="Tropeine (page does not exist)">Tropeines</a> (e.g., <a href="/wiki/Bemesetron" title="Bemesetron">bemesetron</a>, <a href="/w/index.php?title=LY-278584&action=edit&redlink=1" class="new" title="LY-278584 (page does not exist)">LY-278584</a>, <a href="/wiki/Tropisetron" title="Tropisetron">tropisetron</a>, <a href="/wiki/Zatosetron" title="Zatosetron">zatosetron</a>)</li> <li><a href="/wiki/Verapamil" title="Verapamil">Verapamil</a></li> <li><a href="/wiki/Zinc" title="Zinc">Zinc</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:4em;;text-align:center;"><a href="/wiki/N-Methyl-D-aspartate_receptor" class="mw-redirect" title="N-Methyl-D-aspartate receptor"><abbr title="N-Methyl-D-aspartate receptor">NMDAR</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip N-Methyl-D-aspartate receptor</span></th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li>See <a href="/wiki/Template:Ionotropic_glutamate_receptor_modulators" title="Template:Ionotropic glutamate receptor modulators">here</a> instead.</li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Neurotransmitter_transporter" title="Neurotransmitter transporter">Transporter</a><br /><small>(<a href="/wiki/Reuptake_inhibitor" title="Reuptake inhibitor">blockers</a>)</small></th><td class="navbox-list-with-group navbox-list navbox-odd" 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:4em;;text-align:center;"><a href="/wiki/Glycine_transporter_1" class="mw-redirect" title="Glycine transporter 1"><abbr title="Glycine transporter 1">GlyT1</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Glycine transporter 1</span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/w/index.php?title=ACPPB&action=edit&redlink=1" class="new" title="ACPPB (page does not exist)">ACPPB</a></li> <li><a href="/w/index.php?title=ALX-5407&action=edit&redlink=1" class="new" title="ALX-5407 (page does not exist)">ALX-5407 (NFPS)</a></li> <li><a href="/wiki/ASP2535" title="ASP2535">ASP2535</a></li> <li><a href="/wiki/Bitopertin" title="Bitopertin">Bitopertin (RG1678/RO4917838)</a></li> <li><a href="/w/index.php?title=CP-802079&action=edit&redlink=1" class="new" title="CP-802079 (page does not exist)">CP-802079</a></li> <li><a href="/wiki/Alcohol_(drug)" title="Alcohol (drug)">Ethanol (alcohol)</a></li> <li><a href="/w/index.php?title=Glycyldodecylamide&action=edit&redlink=1" class="new" title="Glycyldodecylamide (page does not exist)">Glycyldodecylamide</a></li> <li><a href="/w/index.php?title=GSK1018921&action=edit&redlink=1" class="new" title="GSK1018921 (page does not exist)">GSK1018921</a></li> <li><a href="/wiki/Iclepertin" title="Iclepertin">Iclepertin</a></li> <li><a href="/wiki/LY-2365109" title="LY-2365109">LY-2365109</a></li> <li><a href="/wiki/Mardepodect" title="Mardepodect">Mardepodect</a></li> <li><a href="/wiki/ORG-24598" title="ORG-24598">ORG-24598</a></li> <li><a href="/wiki/ORG-25935" title="ORG-25935">ORG-25935 (SCH-900435)</a></li> <li><a href="/wiki/Pesampator" title="Pesampator">Pesampator (BIIB-104, PF-04958242)</a></li> <li><a href="/w/index.php?title=PF-03463275&action=edit&redlink=1" class="new" title="PF-03463275 (page does not exist)">PF-03463275</a></li> <li><a href="/wiki/Sarcosine" title="Sarcosine">Sarcosine</a></li> <li><a href="/wiki/SNG-12" title="SNG-12">SNG-12 (Synapsinae)</a></li> <li><a href="/w/index.php?title=SSR-103,800&action=edit&redlink=1" class="new" title="SSR-103,800 (page does not exist)">SSR-103,800</a></li> <li><a href="/w/index.php?title=SSR-504,734&action=edit&redlink=1" class="new" title="SSR-504,734 (page does not exist)">SSR-504,734</a></li> <li><a href="/wiki/Tilapertin" title="Tilapertin">Tilapertin</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:4em;;text-align:center;"><a href="/wiki/Glycine_transporter_2" class="mw-redirect" title="Glycine transporter 2"><abbr title="Glycine transporter 2">GlyT2</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Glycine transporter 2</span></th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/ALX-1393" title="ALX-1393">ALX-1393</a></li> <li><a href="/wiki/Amoxapine" title="Amoxapine">Amoxapine</a></li> <li><a href="/wiki/Alcohol_(drug)" title="Alcohol (drug)">Ethanol (alcohol)</a></li> <li><a href="/wiki/N-Arachidonylglycine" title="N-Arachidonylglycine">NAGly</a></li> <li><a href="/wiki/Opiranserin" title="Opiranserin">Opiranserin (VVZ-149)</a></li> <li><a href="/w/index.php?title=ORG-25543&action=edit&redlink=1" class="new" title="ORG-25543 (page does not exist)">ORG-25543</a></li> <li><a href="/w/index.php?title=VVZ-368&action=edit&redlink=1" class="new" title="VVZ-368 (page does not exist)">VVZ-368</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><td class="navbox-abovebelow" colspan="2"><div> <dl><dt>See also</dt> <dd><i><a href="/wiki/Template:Receptor_modulators" title="Template:Receptor modulators">Receptor/signaling modulators</a></i></dd> <dd><i><a href="/wiki/Template:GABA_receptor_modulators" title="Template:GABA receptor modulators">GABA receptor modulators</a></i></dd> <dd><i><a href="/wiki/Template:GABAA_receptor_positive_modulators" title="Template:GABAA receptor positive modulators">GABA<sub>A</sub> receptor positive modulators</a></i></dd> <dd><i><a href="/wiki/Template:Ionotropic_glutamate_receptor_modulators" title="Template:Ionotropic glutamate receptor modulators">Ionotropic glutamate receptor modulators</a></i></dd></dl> </div></td></tr></tbody></table></div></div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"></div><div role="navigation" class="navbox" aria-labelledby="Chloroform_committees_and_commissions" 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="3"><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:Chloroform_committees_and_commissions" title="Template:Chloroform committees and commissions"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Chloroform_committees_and_commissions" title="Template talk:Chloroform committees and commissions"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Chloroform_committees_and_commissions" title="Special:EditPage/Template:Chloroform committees and commissions"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Chloroform_committees_and_commissions" style="font-size:114%;margin:0 4em">Chloroform committees and commissions</div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%">1847</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em">(Chloroform first used)</div></td><td class="noviewer navbox-image" rowspan="9" style="width:1px;padding:0 0 0 2px"><div><figure typeof="mw:File/Thumb"><a href="/wiki/File:Chickamauga_2009,_Chloroform.jpg" class="mw-file-description"><img alt="Antique Chloroform Bottles" src="//upload.wikimedia.org/wikipedia/commons/thumb/4/4f/Chickamauga_2009%2C_Chloroform.jpg/100px-Chickamauga_2009%2C_Chloroform.jpg" decoding="async" width="100" height="73" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/4/4f/Chickamauga_2009%2C_Chloroform.jpg/150px-Chickamauga_2009%2C_Chloroform.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/4/4f/Chickamauga_2009%2C_Chloroform.jpg/200px-Chickamauga_2009%2C_Chloroform.jpg 2x" data-file-width="3335" data-file-height="2449" /></a><figcaption>Antique bottles of <a class="mw-selflink selflink">chloroform</a></figcaption></figure></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">1864</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/Chloroform_Committee" title="Chloroform Committee">Chloroform Committee</a> <ul><li><a href="/wiki/Medical_and_Chirurgical_Society_of_London" title="Medical and Chirurgical Society of London">Royal Medico-Chirurgical Society</a></li></ul></li> <li><i>See also: <a href="/wiki/Clover_bag" class="mw-redirect" title="Clover bag">Clover bag</a></i></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">1877</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/The_Glasgow_Committee_on_An%C3%A6sthetics" class="mw-redirect" title="The Glasgow Committee on Anæsthetics">The Glasgow Committee on Anæsthetics</a> <ul><li><a href="/wiki/British_Medical_Association" title="British Medical Association">British Medical Association</a></li></ul></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">1888</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="/w/index.php?title=First_Hyderabad_Commission&action=edit&redlink=1" class="new" title="First Hyderabad Commission (page does not exist)">First Hyderabad Commissions</a> <ul><li><span class="wrap">Surgeon-Major Lawrie of the <a href="/wiki/Bengal_Medical_Service" class="mw-redirect" title="Bengal Medical Service">Bengal Medical Service</a> appointed by the <a href="/wiki/Nizam_of_Hyderabad" title="Nizam of Hyderabad">Nizam</a>: <a href="/wiki/Mahbub_Ali_Khan,_Asaf_Jah_VI" class="mw-redirect" title="Mahbub Ali Khan, Asaf Jah VI">Mahbub Ali Khan, Asaf Jah VI</a></span></li></ul></li> <li><i>See also: <a href="/w/index.php?title=Lawrie%27s_Apparatus&action=edit&redlink=1" class="new" title="Lawrie's Apparatus (page does not exist)">Lawrie's Apparatus</a></i></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">1889</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><span class="wrap"><a href="/w/index.php?title=Second_Hyderabad_Commission&action=edit&redlink=1" class="new" title="Second Hyderabad Commission (page does not exist)">Second Hyderabad Commission</a> (Surgeon-Major Lawrie with T. Lauder Brunton FRS of St. Bartholomew's Hospital)</span></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">1891</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="/w/index.php?title=British_Medical_Association_An%C3%A6sthetics_Committee&action=edit&redlink=1" class="new" title="British Medical Association Anæsthetics Committee (page does not exist)">British Medical Association Anæsthetics Committee</a> <ul><li><a href="/wiki/British_Medical_Association" title="British Medical Association">British Medical Association</a></li></ul></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">1893</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><span class="wrap"><a href="/wiki/The_Lancet" title="The Lancet">The Lancet</a> commissioned Dudley Buxton to implement a questionnaire to report deaths, the method of induction and the clinical stance of chloroform.</span></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">1901</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/The_Special_Chloroform_Committee_of_the_British_Medical_Association" class="mw-redirect" title="The Special Chloroform Committee of the British Medical Association">The Special Chloroform Committee of the British Medical Association</a> <ul><li><a href="/wiki/British_Medical_Association" title="British Medical Association">British Medical Association</a></li></ul></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">1912</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=American_Medical_Association_Committee_on_An%C3%A6sthesia&action=edit&redlink=1" class="new" title="American Medical Association Committee on Anæsthesia (page does not exist)">American Medical Association Committee on Anæsthesia</a> (<a href="/wiki/American_Medical_Association" title="American Medical Association">American Medical Association</a>) - ban chloroform</li></ul> </div></td></tr><tr><td class="navbox-abovebelow" colspan="3"><div>The list shown in this table is referenced.to view its references see: <a href="/wiki/Template:Chloroform_committees_and_commissions" title="Template:Chloroform committees and commissions">Template:Chloroform committees and commissions</a>.</div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"><style 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tooltip-dotted" title="Chloroforme"><a rel="nofollow" class="external text" href="https://catalogue.bnf.fr/ark:/12148/cb12430403w">France</a></span></span></li><li><span class="uid"><span class="rt-commentedText tooltip tooltip-dotted" title="Chloroforme"><a rel="nofollow" class="external text" href="https://data.bnf.fr/ark:/12148/cb12430403w">BnF data</a></span></span></li><li><span class="uid"><span class="rt-commentedText tooltip tooltip-dotted" title="chloroform"><a rel="nofollow" class="external text" href="https://aleph.nkp.cz/F/?func=find-c&local_base=aut&ccl_term=ica=ph273307&CON_LNG=ENG">Czech Republic</a></span></span></li><li><span class="uid"><a rel="nofollow" class="external text" href="http://olduli.nli.org.il/F/?func=find-b&local_base=NLX10&find_code=UID&request=987007285616305171">Israel</a></span></li></ul></div></td></tr></tbody></table></div>    </div><noscript><img src="https://login.wikimedia.org/wiki/Special:CentralAutoLogin/start?type=1x1" alt="" width="1" 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