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<span>Synthesis</span> </div> </a> <button aria-controls="toc-Synthesis-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 Synthesis subsection</span> </button> <ul id="toc-Synthesis-sublist" class="vector-toc-list"> <li id="toc-Alcoholysis_of_POCl3" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Alcoholysis_of_POCl3"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.1</span> <span>Alcoholysis of <span>POCl<sub>3</sub></span></span> </div> </a> <ul id="toc-Alcoholysis_of_POCl3-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Esterification_of_phosphoric_acid_and_P2O5" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Esterification_of_phosphoric_acid_and_P2O5"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.2</span> <span>Esterification of phosphoric acid and P<sub>2</sub>O<sub>5</sub></span> </div> </a> <ul id="toc-Esterification_of_phosphoric_acid_and_P2O5-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Oxidation_of_phosphite_and_phosphonate_esters" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Oxidation_of_phosphite_and_phosphonate_esters"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.3</span> <span>Oxidation of phosphite and phosphonate esters</span> </div> </a> <ul id="toc-Oxidation_of_phosphite_and_phosphonate_esters-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Phosphorylation" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Phosphorylation"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.4</span> <span>Phosphorylation</span> </div> </a> <ul id="toc-Phosphorylation-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Properties" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Properties"> <div class="vector-toc-text"> <span class="vector-toc-numb">3</span> <span>Properties</span> </div> </a> <button aria-controls="toc-Properties-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 Properties subsection</span> </button> <ul id="toc-Properties-sublist" class="vector-toc-list"> <li id="toc-Bonding" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Bonding"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.1</span> <span>Bonding</span> </div> </a> <ul id="toc-Bonding-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Acidity" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Acidity"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.2</span> <span>Acidity</span> </div> </a> <ul id="toc-Acidity-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Water_solubility" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Water_solubility"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.3</span> <span>Water solubility</span> </div> </a> <ul id="toc-Water_solubility-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Industrial_materials" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Industrial_materials"> <div class="vector-toc-text"> <span class="vector-toc-numb">4</span> <span>Industrial materials</span> </div> </a> <button aria-controls="toc-Industrial_materials-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 Industrial materials subsection</span> </button> <ul id="toc-Industrial_materials-sublist" class="vector-toc-list"> <li id="toc-Pesticides" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Pesticides"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.1</span> <span>Pesticides</span> </div> </a> <ul id="toc-Pesticides-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Flame_retardants" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Flame_retardants"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.2</span> <span>Flame retardants</span> </div> </a> <ul id="toc-Flame_retardants-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Plasticisers" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Plasticisers"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.3</span> <span>Plasticisers</span> </div> </a> <ul id="toc-Plasticisers-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Hydraulic_fluids_and_lubricant_additives" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Hydraulic_fluids_and_lubricant_additives"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.4</span> <span>Hydraulic fluids and lubricant additives</span> </div> </a> <ul id="toc-Hydraulic_fluids_and_lubricant_additives-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Metal_extractants" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Metal_extractants"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.5</span> <span>Metal extractants</span> </div> </a> <ul id="toc-Metal_extractants-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Surfactants" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Surfactants"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.6</span> <span>Surfactants</span> </div> </a> <ul id="toc-Surfactants-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Nerve_agents" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Nerve_agents"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.7</span> <span>Nerve agents</span> </div> </a> <ul id="toc-Nerve_agents-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-In_nature" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#In_nature"> <div class="vector-toc-text"> <span class="vector-toc-numb">5</span> <span>In nature</span> </div> </a> <ul id="toc-In_nature-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">6</span> <span>References</span> </div> </a> <ul id="toc-References-sublist" class="vector-toc-list"> </ul> </li> </ul> </div> </div> </nav> </div> </div> <div class="mw-content-container"> <main id="content" class="mw-body"> <header class="mw-body-header vector-page-titlebar"> <nav aria-label="Contents" class="vector-toc-landmark"> <div id="vector-page-titlebar-toc" class="vector-dropdown vector-page-titlebar-toc vector-button-flush-left" > <input type="checkbox" id="vector-page-titlebar-toc-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-vector-page-titlebar-toc" class="vector-dropdown-checkbox " aria-label="Toggle the table of contents" > <label id="vector-page-titlebar-toc-label" for="vector-page-titlebar-toc-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--icon-only " aria-hidden="true" ><span class="vector-icon mw-ui-icon-listBullet mw-ui-icon-wikimedia-listBullet"></span> <span class="vector-dropdown-label-text">Toggle the table of contents</span> </label> <div class="vector-dropdown-content"> <div id="vector-page-titlebar-toc-unpinned-container" class="vector-unpinned-container"> </div> </div> </div> </nav> <h1 id="firstHeading" class="firstHeading mw-first-heading"><span class="mw-page-title-main">Organophosphate</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 23 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-23" 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">23 languages</span> </label> <div class="vector-dropdown-content"> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li class="interlanguage-link interwiki-ar mw-list-item"><a href="https://ar.wikipedia.org/wiki/%D9%81%D9%88%D8%B3%D9%81%D8%A7%D8%AA_%D8%B9%D8%B6%D9%88%D9%8A" title="فوسفات عضوي – Arabic" lang="ar" hreflang="ar" data-title="فوسفات عضوي" data-language-autonym="العربية" data-language-local-name="Arabic" class="interlanguage-link-target"><span>العربية</span></a></li><li class="interlanguage-link interwiki-bs mw-list-item"><a href="https://bs.wikipedia.org/wiki/Organofosfat" title="Organofosfat – Bosnian" lang="bs" hreflang="bs" data-title="Organofosfat" 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/Organofosfat" title="Organofosfat – Catalan" lang="ca" hreflang="ca" data-title="Organofosfat" 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/Organofosf%C3%A1ty" title="Organofosfáty – Czech" lang="cs" hreflang="cs" data-title="Organofosfáty" data-language-autonym="Čeština" data-language-local-name="Czech" class="interlanguage-link-target"><span>Čeština</span></a></li><li class="interlanguage-link interwiki-de mw-list-item"><a href="https://de.wikipedia.org/wiki/Phosphors%C3%A4ureester" title="Phosphorsäureester – German" lang="de" hreflang="de" data-title="Phosphorsäureester" data-language-autonym="Deutsch" data-language-local-name="German" class="interlanguage-link-target"><span>Deutsch</span></a></li><li class="interlanguage-link interwiki-es mw-list-item"><a href="https://es.wikipedia.org/wiki/Organofosfato" title="Organofosfato – Spanish" lang="es" hreflang="es" data-title="Organofosfato" data-language-autonym="Español" data-language-local-name="Spanish" class="interlanguage-link-target"><span>Español</span></a></li><li class="interlanguage-link interwiki-eu mw-list-item"><a href="https://eu.wikipedia.org/wiki/Organofosfato" title="Organofosfato – Basque" lang="eu" hreflang="eu" data-title="Organofosfato" data-language-autonym="Euskara" data-language-local-name="Basque" class="interlanguage-link-target"><span>Euskara</span></a></li><li class="interlanguage-link interwiki-fa mw-list-item"><a href="https://fa.wikipedia.org/wiki/%D8%A7%D8%B1%DA%AF%D8%A7%D9%86%D9%88%D9%81%D8%B3%D9%81%D8%A7%D8%AA" title="ارگانوفسفات – Persian" lang="fa" hreflang="fa" data-title="ارگانوفسفات" data-language-autonym="فارسی" data-language-local-name="Persian" class="interlanguage-link-target"><span>فارسی</span></a></li><li class="interlanguage-link interwiki-gl mw-list-item"><a href="https://gl.wikipedia.org/wiki/Organofosfato" title="Organofosfato – Galician" lang="gl" hreflang="gl" data-title="Organofosfato" data-language-autonym="Galego" data-language-local-name="Galician" class="interlanguage-link-target"><span>Galego</span></a></li><li class="interlanguage-link interwiki-ko mw-list-item"><a href="https://ko.wikipedia.org/wiki/%EC%9C%A0%EA%B8%B0_%EC%9D%B8%EC%82%B0%EC%97%BC" title="유기 인산염 – Korean" lang="ko" hreflang="ko" data-title="유기 인산염" 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%95%D6%80%D5%A3%D5%A1%D5%B6%D5%A1%D5%AF%D5%A1%D5%B6_%D6%86%D5%B8%D5%BD%D6%86%D5%A1%D5%BF%D5%B6%D5%A5%D6%80" title="Օրգանական ֆոսֆատներ – Armenian" lang="hy" hreflang="hy" data-title="Օրգանական ֆոսֆատներ" data-language-autonym="Հայերեն" data-language-local-name="Armenian" class="interlanguage-link-target"><span>Հայերեն</span></a></li><li class="interlanguage-link interwiki-it mw-list-item"><a href="https://it.wikipedia.org/wiki/Organofosfato" title="Organofosfato – Italian" lang="it" hreflang="it" data-title="Organofosfato" data-language-autonym="Italiano" data-language-local-name="Italian" class="interlanguage-link-target"><span>Italiano</span></a></li><li class="interlanguage-link interwiki-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/Organofosforverbinding" title="Organofosforverbinding – Dutch" lang="nl" hreflang="nl" data-title="Organofosforverbinding" data-language-autonym="Nederlands" data-language-local-name="Dutch" class="interlanguage-link-target"><span>Nederlands</span></a></li><li class="interlanguage-link interwiki-ja mw-list-item"><a href="https://ja.wikipedia.org/wiki/%E3%83%AA%E3%83%B3%E9%85%B8%E3%82%A8%E3%82%B9%E3%83%86%E3%83%AB" title="リン酸エステル – Japanese" lang="ja" hreflang="ja" data-title="リン酸エステル" data-language-autonym="日本語" data-language-local-name="Japanese" class="interlanguage-link-target"><span>日本語</span></a></li><li class="interlanguage-link interwiki-no mw-list-item"><a href="https://no.wikipedia.org/wiki/Organofosfater" title="Organofosfater – Norwegian Bokmål" lang="nb" hreflang="nb" data-title="Organofosfater" 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-pt mw-list-item"><a href="https://pt.wikipedia.org/wiki/%C3%89ster_fosfato" title="Éster fosfato – Portuguese" lang="pt" hreflang="pt" data-title="Éster fosfato" data-language-autonym="Português" data-language-local-name="Portuguese" class="interlanguage-link-target"><span>Português</span></a></li><li class="interlanguage-link interwiki-ru mw-list-item"><a href="https://ru.wikipedia.org/wiki/%D0%9E%D1%80%D0%B3%D0%B0%D0%BD%D0%B8%D1%87%D0%B5%D1%81%D0%BA%D0%B8%D0%B5_%D1%84%D0%BE%D1%81%D1%84%D0%B0%D1%82%D1%8B" title="Органические фосфаты – Russian" lang="ru" hreflang="ru" data-title="Органические фосфаты" data-language-autonym="Русский" data-language-local-name="Russian" class="interlanguage-link-target"><span>Русский</span></a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/Organofosfat" title="Organofosfat – Serbian" lang="sr" hreflang="sr" data-title="Organofosfat" 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-fi mw-list-item"><a href="https://fi.wikipedia.org/wiki/Organofosfaatit" title="Organofosfaatit – Finnish" lang="fi" hreflang="fi" data-title="Organofosfaatit" 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/Organofosfat" title="Organofosfat – Swedish" lang="sv" hreflang="sv" data-title="Organofosfat" data-language-autonym="Svenska" data-language-local-name="Swedish" class="interlanguage-link-target"><span>Svenska</span></a></li><li class="interlanguage-link interwiki-tr mw-list-item"><a href="https://tr.wikipedia.org/wiki/Organofosfat" title="Organofosfat – Turkish" lang="tr" hreflang="tr" data-title="Organofosfat" data-language-autonym="Türkçe" data-language-local-name="Turkish" class="interlanguage-link-target"><span>Türkçe</span></a></li><li class="interlanguage-link interwiki-vi mw-list-item"><a href="https://vi.wikipedia.org/wiki/H%E1%BB%A3p_ch%E1%BA%A5t_c%C6%A1_phospho" title="Hợp chất cơ phospho – Vietnamese" lang="vi" hreflang="vi" data-title="Hợp chất cơ phospho" data-language-autonym="Tiếng Việt" data-language-local-name="Vietnamese" class="interlanguage-link-target"><span>Tiếng Việt</span></a></li><li class="interlanguage-link interwiki-zh mw-list-item"><a href="https://zh.wikipedia.org/wiki/%E7%A3%B7%E9%85%B8%E9%85%AF" title="磷酸酯 – Chinese" lang="zh" hreflang="zh" data-title="磷酸酯" data-language-autonym="中文" data-language-local-name="Chinese" class="interlanguage-link-target"><span>中文</span></a></li> </ul> <div class="after-portlet after-portlet-lang"><span class="wb-langlinks-edit wb-langlinks-link"><a href="https://www.wikidata.org/wiki/Special:EntityPage/Q411097#sitelinks-wikipedia" title="Edit interlanguage links" class="wbc-editpage">Edit links</a></span></div> </div> </div> </div> </header> <div class="vector-page-toolbar"> <div 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searchaux" style="display:none">Organic compounds with the structure O=P(OR)3</div> <style data-mw-deduplicate="TemplateStyles:r1236090951">.mw-parser-output .hatnote{font-style:italic}.mw-parser-output div.hatnote{padding-left:1.6em;margin-bottom:0.5em}.mw-parser-output .hatnote i{font-style:normal}.mw-parser-output .hatnote+link+.hatnote{margin-top:-0.5em}@media print{body.ns-0 .mw-parser-output .hatnote{display:none!important}}</style><div role="note" class="hatnote navigation-not-searchable">This article is about the organic derivatives of the phosphate ion. For the inorganic ion, see <a href="/wiki/Phosphate" title="Phosphate">phosphate</a>. For all organic compound incorporating phosphorus, see <a href="/wiki/Organophosphorus_chemistry" title="Organophosphorus chemistry">organophosphorus chemistry</a>.</div> <figure class="mw-default-size mw-halign-right" typeof="mw:File/Thumb"><a href="/wiki/File:Phosphate_formula.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/e/e9/Phosphate_formula.svg/220px-Phosphate_formula.svg.png" decoding="async" width="220" height="160" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/e9/Phosphate_formula.svg/330px-Phosphate_formula.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/e/e9/Phosphate_formula.svg/440px-Phosphate_formula.svg.png 2x" data-file-width="204" data-file-height="148" /></a><figcaption>General chemical structure of the organophosphate <a href="/wiki/Functional_group" title="Functional group">functional group</a> </figcaption></figure> <p>In <a href="/wiki/Organic_chemistry" title="Organic chemistry">organic chemistry</a>, <b>organophosphates</b> (also known as <b>phosphate esters</b>, or <b>OPEs</b>) are a class of <a href="/wiki/Organophosphorus_compound" class="mw-redirect" title="Organophosphorus compound">organophosphorus compounds</a> with the general structure <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">O=P(OR)<sub class="template-chem2-sub">3</sub></span>, a central phosphate molecule with <a href="/wiki/Alkyl" class="mw-redirect" title="Alkyl">alkyl</a> or <a href="/wiki/Aryl" class="mw-redirect" title="Aryl">aromatic substituents</a>.<sup id="cite_ref-:3_1-0" class="reference"><a href="#cite_note-:3-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> They can be considered as <a href="/wiki/Ester" title="Ester">esters</a> of <a href="/wiki/Phosphoric_acid" title="Phosphoric acid">phosphoric acid</a>. Organophosphates are best known for their use as <a href="/wiki/Pesticide" title="Pesticide">pesticides</a>. </p><p>Like most <a href="/wiki/Functional_group" title="Functional group">functional groups</a>, organophosphates occur in a diverse range of forms,<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> with important examples including key biomolecules such as <a href="/wiki/DNA" title="DNA">DNA</a>, <a href="/wiki/RNA" title="RNA">RNA</a> and <a href="/wiki/Adenosine_triphosphate" title="Adenosine triphosphate">ATP</a>, as well as many <a href="/wiki/Insecticide" title="Insecticide">insecticides</a>, <a href="/wiki/Herbicide" title="Herbicide">herbicides</a>, <a href="/wiki/Nerve_agent" title="Nerve agent">nerve agents</a> and <a href="/wiki/Flame_retardant" title="Flame retardant">flame retardants</a>. OPEs have been widely used in various products as flame retardants, <a href="/wiki/Plasticizer" title="Plasticizer">plasticizers</a>, and performance additives to engine oil. The low cost of production and compatibility to diverse polymers made OPEs to be widely used in industry including textile, furniture, electronics as plasticizers and flame retardants. These compounds are added to the final product physically rather than by chemical bond.<sup id="cite_ref-:5_3-0" class="reference"><a href="#cite_note-:5-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> Due to this, OPEs leak into the environment more readily through volatilization, leaching, and abrasion.<sup id="cite_ref-:6_4-0" class="reference"><a href="#cite_note-:6-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> OPEs have been detected in diverse environmental compartments such as air, dust, water, sediment, soil and biota samples at higher frequency and concentration.<sup id="cite_ref-:3_1-1" class="reference"><a href="#cite_note-:3-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-:6_4-1" class="reference"><a href="#cite_note-:6-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> </p><p>The popularity of OPEs as flame retardants came as a substitution for the highly regulated <a href="/wiki/Brominated_flame_retardant" title="Brominated flame retardant">brominated flame retardants</a>.<sup id="cite_ref-:4_5-0" class="reference"><a href="#cite_note-:4-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Forms">Forms</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Organophosphate&action=edit&section=1" title="Edit section: Forms"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Organophosphates are a class of compounds encompassing a number of distinct but closely related <a href="/wiki/Function_group" class="mw-redirect" title="Function group">function groups</a>. These are primarily the <a href="/wiki/Ester" title="Ester">esters</a> of <a href="/wiki/Phosphoric_acid" title="Phosphoric acid">phosphoric acid</a> and can be mono‑esters, di‑esters or tri‑esters depending on the number of attached <a href="/wiki/Organic_compound" title="Organic compound">organic</a> groups (abbreviated as 'R' in the image below). In general man‑made organophosphates are most often triesters, while biological organophosphates are usually mono- or di-esters. The hydolysis of triesters can form diesters and monoesters.<sup id="cite_ref-6" class="reference"><a href="#cite_note-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> </p><p><span typeof="mw:File"><a href="/wiki/File:Phosphors%C3%A4ureester.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/5/53/Phosphors%C3%A4ureester.png/400px-Phosphors%C3%A4ureester.png" decoding="async" width="400" height="96" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/5/53/Phosphors%C3%A4ureester.png/600px-Phosphors%C3%A4ureester.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/5/53/Phosphors%C3%A4ureester.png/800px-Phosphors%C3%A4ureester.png 2x" data-file-width="1951" data-file-height="469" /></a></span> </p><p>In the context of pesticides, derivatives of organophosphates such as <a href="/wiki/Organothiophosphate" title="Organothiophosphate">organothiophosphates</a> (P=S) or <a href="/wiki/Phosphorodiamidate" class="mw-redirect" title="Phosphorodiamidate">phosphorodiamidates</a> (P-N) are included as being organophosphates. The reason is that these compound are converted into organophosphates biologically. </p><p><span typeof="mw:File"><a href="/wiki/File:Thiophosphors%C3%A4ureester_Dithiophosphors%C3%A4ureester.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/4/4b/Thiophosphors%C3%A4ureester_Dithiophosphors%C3%A4ureester.svg/300px-Thiophosphors%C3%A4ureester_Dithiophosphors%C3%A4ureester.svg.png" decoding="async" width="300" height="104" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/4/4b/Thiophosphors%C3%A4ureester_Dithiophosphors%C3%A4ureester.svg/450px-Thiophosphors%C3%A4ureester_Dithiophosphors%C3%A4ureester.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/4/4b/Thiophosphors%C3%A4ureester_Dithiophosphors%C3%A4ureester.svg/600px-Thiophosphors%C3%A4ureester_Dithiophosphors%C3%A4ureester.svg.png 2x" data-file-width="751" data-file-height="260" /></a></span> </p><p>In biology the esters of <a href="/wiki/Diphosphoric_acid" class="mw-redirect" title="Diphosphoric acid">diphosphoric acid</a> and <a href="/wiki/Triphosphoric_acid" title="Triphosphoric acid">triphosphoric acid</a> are generally included as organophosphates. The reason is again a practical one, as many cellular processes involve the mono- di and tri- phosphates of the same compound. For instance, the phosphates of <a href="/wiki/Adenosine" title="Adenosine">adenosine</a> (<a href="/wiki/Adenosine_monophosphate" title="Adenosine monophosphate">AMP</a>, <a href="/wiki/Adenosine_diphosphate" title="Adenosine diphosphate">ADP</a>, <a href="/wiki/Adenosine_triphosphate" title="Adenosine triphosphate">ATP</a>) play a key role in many metabolic processes. </p><p><span typeof="mw:File"><a href="/wiki/File:Di_u_Triphosphors%C3%A4ureester.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/6/63/Di_u_Triphosphors%C3%A4ureester.png/475px-Di_u_Triphosphors%C3%A4ureester.png" decoding="async" width="475" height="91" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/6/63/Di_u_Triphosphors%C3%A4ureester.png 1.5x" data-file-width="557" data-file-height="107" /></a></span> </p> <div class="mw-heading mw-heading2"><h2 id="Synthesis">Synthesis</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Organophosphate&action=edit&section=2" title="Edit section: Synthesis"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Alcoholysis_of_POCl3">Alcoholysis of <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">POCl<sub class="template-chem2-sub">3</sub></span></h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Organophosphate&action=edit&section=3" title="Edit section: Alcoholysis of POCl3"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><a href="/wiki/Phosphorus_oxychloride" class="mw-redirect" title="Phosphorus oxychloride">Phosphorus oxychloride</a> reacts readily with <a href="/wiki/Alcohols" class="mw-redirect" title="Alcohols">alcohols</a> to give organophosphates. This is the dominant industrial route and is responsible for almost all organophosphate production. </p> <dl><dd><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">O=PCl<sub class="template-chem2-sub">3</sub> + 3 ROH → O=P(OR)<sub class="template-chem2-sub">3</sub> + 3 HCl</span></dd></dl> <p>When aliphatic alcohols are used the HCl by-product can react with the phosphate esters to give <a href="/wiki/Organochloride" class="mw-redirect" title="Organochloride">organochlorides</a> and a lower ester. </p> <dl><dd><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">O=P(OR)<sub class="template-chem2-sub">3</sub> + HCl → O=P(OR)<sub class="template-chem2-sub">2</sub>OH + RCl</span></dd></dl> <p>This reaction is usually undesirable and is exacerbated by high reaction temperatures. It can be inhibited by the use of a base or the removal of HCl through <a href="/wiki/Sparging_(chemistry)" title="Sparging (chemistry)">sparging</a>. </p> <div class="mw-heading mw-heading3"><h3 id="Esterification_of_phosphoric_acid_and_P2O5">Esterification of phosphoric acid and P<sub>2</sub>O<sub>5</sub></h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Organophosphate&action=edit&section=4" title="Edit section: Esterification of phosphoric acid and P2O5"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><a href="/wiki/Esterification" class="mw-redirect" title="Esterification">Esterifications</a> of <a href="/wiki/Phosphoric_acid" title="Phosphoric acid">phosphoric acid</a> with alcohols proceed less readily than the more common <a href="/wiki/Carboxylic_acid" title="Carboxylic acid">carboxylic acid</a> esterifications, with the reactions rarely proceeding much further than the phosphate mono-ester. The reaction requires high temperatures, under which the phosphoric acid can dehydrate to form poly-phosphoric acids. These are exceedingly viscous and their linear polymeric structure renders them less reactive than phosphoric acid.<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> Despite these limitations the reaction does see industrial use for the formation of monoalkyl phosphates, which are used as <a href="/wiki/Surfactant" title="Surfactant">surfactants</a>.<sup id="cite_ref-8" class="reference"><a href="#cite_note-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> A major appeal of this route is the low cost of phosphoric acid compared to phosphorus oxychloride. </p> <dl><dd><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">OP(OH)<sub class="template-chem2-sub">3</sub> + ROH → OP(OH)<sub class="template-chem2-sub">2</sub>(OR) + H<sub class="template-chem2-sub">2</sub>O</span></dd></dl> <p><a href="/wiki/P2O5" class="mw-redirect" title="P2O5">P<sub>2</sub>O<sub>5</sub></a> is the anhydride of phosphoric acid and acts similarly. The reaction yields equimolar amounts of di- and monoesters with no phosphoric acid. The process is mostly limited to primary alcohols, as secondary alcohols are prone to undesirable side reactions such as dehydration.<sup id="cite_ref-9" class="reference"><a href="#cite_note-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Oxidation_of_phosphite_and_phosphonate_esters">Oxidation of phosphite and phosphonate esters</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Organophosphate&action=edit&section=5" title="Edit section: Oxidation of phosphite and phosphonate esters"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><a href="/wiki/Organophosphites" class="mw-redirect" title="Organophosphites">Organophosphites</a> can be easily oxidised to give organophosphates. This is not a common industrial route, however large quantities of organophosphites are manufactured as antioxidant <a href="/wiki/Polymer_stabilizers" class="mw-redirect" title="Polymer stabilizers">stabilisers</a> for plastics. The gradual oxidation these generates organophosphates in the human environment.<sup id="cite_ref-10" class="reference"><a href="#cite_note-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-11" class="reference"><a href="#cite_note-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup><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> </p> <dl><dd><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">P(OR)<sub class="template-chem2-sub">3</sub> + [O] → OP(OR)<sub class="template-chem2-sub">3</sub></span></dd></dl> <p>A more specialised alternative is the <a href="/wiki/Atherton-Todd" class="mw-redirect" title="Atherton-Todd">Atherton-Todd</a> reaction, which converts a <a href="/wiki/Dialkyl_phosphite" class="mw-redirect" title="Dialkyl phosphite">dialkyl phosphite</a> to a phosphoryl chloride. This can then react with an alcohol to give an organophosphate and HCl. </p> <div class="mw-heading mw-heading3"><h3 id="Phosphorylation">Phosphorylation</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Organophosphate&action=edit&section=6" title="Edit section: Phosphorylation"><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/Phosphorylation" title="Phosphorylation">Phosphorylation</a></div> <p>The formation of organophosphates is an important part of biochemistry and living systems achieve this using a variety of <a href="/wiki/Enzyme" title="Enzyme">enzymes</a>. Phosphorylation is essential to the processes of both <a href="/wiki/Anaerobic_respiration" title="Anaerobic respiration">anaerobic</a> and <a href="/wiki/Aerobic_respiration" class="mw-redirect" title="Aerobic respiration">aerobic respiration</a>, which involve the production of <a href="/wiki/Adenosine_triphosphate" title="Adenosine triphosphate">adenosine triphosphate</a> (ATP), the "high-energy" exchange medium in the cell. <a href="/wiki/Protein_phosphorylation" title="Protein phosphorylation">Protein phosphorylation</a> is the most abundant <a href="/wiki/Posttranslational_modification" class="mw-redirect" title="Posttranslational modification">post-translational modification</a> in eukaryotes. Many enzymes and receptors are switched "on" or "off" by phosphorylation and dephosphorylation. </p> <div class="mw-heading mw-heading2"><h2 id="Properties">Properties</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Organophosphate&action=edit&section=7" title="Edit section: Properties"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Bonding">Bonding</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Organophosphate&action=edit&section=8" title="Edit section: Bonding"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The bonding in organophosphates has been a matter of prolonged debate; the phosphorus atom is classically <a href="/wiki/Hypervalent_molecule" title="Hypervalent molecule">hypervalent</a>, as it possesses more bonds than the <a href="/wiki/Octet_rule" title="Octet rule">octet rule</a> should allow.<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> The focus of debate is usually on the nature of the <a href="/wiki/Phosphoryl" class="mw-redirect" title="Phosphoryl">phosphoryl</a> P=O bond, which displays (in spite of the common depiction) non-classical bonding, with a <a href="/wiki/Bond_order" title="Bond order">bond order</a> somewhere between 1 and 2. Early papers explained the hypervalence in terms of d-<a href="/wiki/Orbital_hybridisation" title="Orbital hybridisation">orbital hybridisation</a>, with the energy penalty of promoting electrons into the higher energy orbitals being off-set by the stabilisation of additional bonding.<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> Later advances in <a href="/wiki/Computational_chemistry" title="Computational chemistry">computational chemistry</a> showed that d-orbitals played little significant role in bonding.<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><sup id="cite_ref-Simons_16-0" class="reference"><a href="#cite_note-Simons-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup> Current models rely on either <a href="/wiki/Negative_hyperconjugation" title="Negative hyperconjugation">negative hyperconjugation</a>,<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> or a more complex arraignment with a <a href="/wiki/Coordinate_covalent_bond" title="Coordinate covalent bond">dative</a>-type bond from P to O, combined with back-donation from an oxygen 2p orbital.<sup id="cite_ref-Simons_16-1" class="reference"><a href="#cite_note-Simons-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup><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> These models agree with the experimental observations of the phosphoryl as being shorter than P-OR bonds<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> and much more polarised. It has been argued that a more accurate depiction is dipolar (i.e. (RO)<sub>3</sub>P<sup>+</sup>-O<sup>-</sup>),<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> which is similar to the depiction of <a href="/wiki/Ylide" title="Ylide">phosphorus ylides</a> such as <a href="/wiki/Methylenetriphenylphosphorane" title="Methylenetriphenylphosphorane">methylenetriphenylphosphorane</a>. However in contrast to ylides, the phosphoryl group is unreactive and organophosphates are poor nucleophiles, despite the high concentration of charge on the phosphoryl oxygen. The polarisation accounts in part for the higher melting points of phosphates when compared to their corresponding <a href="/wiki/Phosphite" class="mw-redirect" title="Phosphite">phosphites</a>. The bonding in penta-coordinate <a href="/wiki/Phosphoranes" title="Phosphoranes">phosphoranes</a> (i.e. P(OR)<sub>5</sub>) is entirely different and involves <a href="/wiki/Three-center_four-electron_bond" title="Three-center four-electron bond">three-center four-electron bonds</a>. </p> <div class="mw-heading mw-heading3"><h3 id="Acidity">Acidity</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Organophosphate&action=edit&section=9" title="Edit section: Acidity"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Phosphate esters bearing P-OH groups are <a href="/wiki/Acid" title="Acid">acidic</a>. The pKa of the first OH group is typically between 1-2, while the second OH <a href="/wiki/Deprotonation" title="Deprotonation">deprotonates</a> at a pKa between 6-7.<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> As such, phosphate mono- and di-esters are negatively charged at <a href="/wiki/Intracellular_pH" title="Intracellular pH">physiological pH</a>.<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> This is of great practical importance, as it makes these compounds far more resistant to degradation by hydrolysis or other forms of nucleophilic attack, due to electrostatic repulsion between negative charges.<sup id="cite_ref-why_23-0" class="reference"><a href="#cite_note-why-23"><span class="cite-bracket">[</span>23<span class="cite-bracket">]</span></a></sup> This effects nearly all organophosphate biomolecules, such as DNA and RNA and accounts in-part for their high stability.<sup id="cite_ref-why_23-1" class="reference"><a href="#cite_note-why-23"><span class="cite-bracket">[</span>23<span class="cite-bracket">]</span></a></sup> The presence of this negative charge also makes these compounds much more water soluble. </p> <div class="mw-heading mw-heading3"><h3 id="Water_solubility">Water solubility</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Organophosphate&action=edit&section=10" title="Edit section: Water solubility"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The water solubility of organophosphates is an important factor in biological, industrial and environmental settings. The wide variety of substitutes used in organophosphate esters results in great variations in physical properties. OPEs exhibit a wide range of octanol/water <a href="/wiki/Partition_coefficient" title="Partition coefficient">partition coefficients</a> where log Kow values range from -0.98 up to 10.6.<sup id="cite_ref-:4_5-1" class="reference"><a href="#cite_note-:4-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> Mono- and di- esters are usually water soluble, particularity biomolecules. Tri-esters such as flame retardants and plasticisers have positive log Kow values ranging between 1.44 and 9.49, signifying <a href="/wiki/Hydrophobicity" class="mw-redirect" title="Hydrophobicity">hydrophobicity</a>.<sup id="cite_ref-:4_5-2" class="reference"><a href="#cite_note-:4-5"><span class="cite-bracket">[</span>5<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><sup id="cite_ref-:6_4-2" class="reference"><a href="#cite_note-:6-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-:7_25-0" class="reference"><a href="#cite_note-:7-25"><span class="cite-bracket">[</span>25<span class="cite-bracket">]</span></a></sup> Hydrophobic OPEs are more likely to be bioaccumulated and biomagnified in aquatic ecosystems.<sup id="cite_ref-:5_3-1" class="reference"><a href="#cite_note-:5-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> Halogenated organophosphates tend to be denser than water and sink, causing them to accumulate in sediments.<sup id="cite_ref-26" class="reference"><a href="#cite_note-26"><span class="cite-bracket">[</span>26<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Industrial_materials">Industrial materials</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Organophosphate&action=edit&section=11" title="Edit section: Industrial materials"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Pesticides">Pesticides<span class="anchor" id="Insecticides"></span></h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Organophosphate&action=edit&section=12" title="Edit section: Pesticides"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure class="mw-default-size mw-halign-right" typeof="mw:File/Thumb"><a href="/wiki/File:Malathion.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/0/0c/Malathion.png/220px-Malathion.png" decoding="async" width="220" height="132" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/0/0c/Malathion.png/330px-Malathion.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/0/0c/Malathion.png/440px-Malathion.png 2x" data-file-width="2273" data-file-height="1367" /></a><figcaption><a href="/wiki/Malathion" title="Malathion">Malathion</a>, one of the first organophosphate insecticides. It remains important as a Vector control agent.</figcaption></figure> <p>Organophosphates are best known for their use as pesticides. The vast majority are <a href="/wiki/Insecticides" class="mw-redirect" title="Insecticides">insecticides</a> and are used either to protect crops, or as <a href="/wiki/Vector_control" title="Vector control">vector control</a> agents to reduce the transmission of diseases spread by insects, such as mosquitoes. Health concerns have seen their use significantly decrease since the turn of the century.<sup id="cite_ref-27" class="reference"><a href="#cite_note-27"><span class="cite-bracket">[</span>27<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Vector-trends_28-0" class="reference"><a href="#cite_note-Vector-trends-28"><span class="cite-bracket">[</span>28<span class="cite-bracket">]</span></a></sup> <a href="/wiki/Glyphosate" title="Glyphosate">Glyphosate</a> is sometimes called an organophosphate, but is in-fact a <a href="/wiki/Phosphonate" title="Phosphonate">phosphonate</a>. Its chemistry, mechanism of toxicity and end-use as a herbicide are different from the organophosphate insecticides. </p><p>The development of organophosphate insecticides dates back to the 1930s and is generally credited to <a href="/wiki/Gerhard_Schrader" title="Gerhard Schrader">Gerhard Schrader</a>.<sup id="cite_ref-OPs_at_80_29-0" class="reference"><a href="#cite_note-OPs_at_80-29"><span class="cite-bracket">[</span>29<span class="cite-bracket">]</span></a></sup> At the time pesticides were largely limited to arsenic salts (<a href="/wiki/Calcium_arsenate" title="Calcium arsenate">calcium arsenate</a>, <a href="/wiki/Lead_arsenate" class="mw-redirect" title="Lead arsenate">lead arsenate</a> and <a href="/wiki/Paris_green" title="Paris green">Paris green</a>)<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> or <a href="/wiki/Pyrethrin" title="Pyrethrin">pyrethrin</a> plant extracts, all of which had major problems.<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> Schrader was seeking more effective agents, however while some organophosphates were found to be far more dangerous to insects than higher animals,<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> the potential effectiveness of others as <a href="/wiki/Chemical_weapon" title="Chemical weapon">chemical weapons</a> did not go unnoticed. The development of organophosphate insecticides and the earliest <a href="/wiki/Nerve_agent" title="Nerve agent">nerve agents</a> was conjoined, with Schrader also developing the nerve agents <a href="/wiki/Tabun_(nerve_agent)" title="Tabun (nerve agent)">tabun</a> and <a href="/wiki/Sarin" title="Sarin">sarin</a>. Organophosphate pesticides were not commercialised until after WWII. <a href="/wiki/Parathion" title="Parathion">Parathion</a> was among the first marketed, followed by <a href="/wiki/Malathion" title="Malathion">malathion</a> and <a href="/wiki/Azinphosmethyl" class="mw-redirect" title="Azinphosmethyl">azinphosmethyl</a> . Although organophosphates were used in considerable qualities they were originally less important than <a href="/wiki/Organochlorine" class="mw-redirect" title="Organochlorine">organochlorine</a> insecticides such as <a href="/wiki/DDT" title="DDT">DDT</a>, <a href="/wiki/Dieldrin" title="Dieldrin">dieldrin</a>, and <a href="/wiki/Heptachlor" title="Heptachlor">heptachlor</a>. When many of the organochlorines were banned in the 1970s, following the publishing of <a href="/wiki/Silent_Spring" title="Silent Spring">Silent Spring</a>, organophosphates became the most important class of insecticides globally. Nearly 100 were commercialised, with the following being a varied selection: </p> <style data-mw-deduplicate="TemplateStyles:r1184024115">.mw-parser-output .div-col{margin-top:0.3em;column-width:30em}.mw-parser-output .div-col-small{font-size:90%}.mw-parser-output .div-col-rules{column-rule:1px solid #aaa}.mw-parser-output .div-col dl,.mw-parser-output .div-col ol,.mw-parser-output .div-col ul{margin-top:0}.mw-parser-output .div-col li,.mw-parser-output .div-col dd{page-break-inside:avoid;break-inside:avoid-column}</style><div class="div-col" style="column-width: 18em;"> <ul><li><a href="/wiki/Acephate" title="Acephate">Acephate</a></li> <li><a href="/wiki/Azinphos-methyl" title="Azinphos-methyl">Azinphos-methyl</a></li> <li><a href="/wiki/Bensulide" title="Bensulide">Bensulide</a></li> <li><a href="/wiki/Chlorethoxyfos" title="Chlorethoxyfos">Chlorethoxyfos</a></li> <li><a href="/wiki/Coumaphos" title="Coumaphos">Coumaphos</a></li> <li><a href="/wiki/Diazinon" title="Diazinon">Diazinon</a></li> <li><a href="/wiki/Dichlorvos" title="Dichlorvos">Dichlorvos</a></li> <li><a href="/wiki/Dicrotophos" title="Dicrotophos">Dicrotophos</a></li> <li><a href="/wiki/Dimethoate" title="Dimethoate">Dimethoate</a></li> <li><a href="/wiki/Disulfoton" title="Disulfoton">Disulfoton</a></li> <li><a href="/wiki/Ethion" title="Ethion">Ethion</a></li> <li><a href="/wiki/Ethoprop" class="mw-redirect" title="Ethoprop">Ethoprop</a></li> <li><a href="/wiki/Ethyl_parathion" class="mw-redirect" title="Ethyl parathion">Ethyl parathion</a></li> <li><a href="/wiki/Fenamiphos" title="Fenamiphos">Fenamiphos</a></li> <li><a href="/wiki/Fenitrothion" title="Fenitrothion">Fenitrothion</a></li> <li><a href="/wiki/Fonofos" title="Fonofos">Fonofos</a></li> <li><a href="/wiki/Isoxathion" title="Isoxathion">Isoxathion</a></li> <li><a href="/wiki/Malathion" title="Malathion">Malathion</a></li> <li><a href="/wiki/Methamidophos" title="Methamidophos">Methamidophos</a></li> <li><a href="/wiki/Methidathion" title="Methidathion">Methidathion</a></li> <li><a href="/wiki/Mevinphos" title="Mevinphos">Mevinphos</a></li> <li><a href="/wiki/Naled" title="Naled">Naled</a></li> <li><a href="/wiki/Phosmet" title="Phosmet">Phosmet</a></li> <li><a href="/wiki/Profenofos" title="Profenofos">Profenofos</a></li> <li><a href="/wiki/Propetamphos" title="Propetamphos">Propetamphos</a></li> <li><a href="/wiki/Quinalphos" title="Quinalphos">Quinalphos</a></li> <li><a href="/wiki/Sulfotep" title="Sulfotep">Sulfotep</a></li> <li><a href="/wiki/Tebupirimfos" title="Tebupirimfos">Tebupirimfos</a></li> <li><a href="/wiki/Temephos" class="mw-redirect" title="Temephos">Temephos</a></li> <li><a href="/wiki/Terbufos" title="Terbufos">Terbufos</a></li> <li><a href="/wiki/Tetrachlorvinphos" title="Tetrachlorvinphos">Tetrachlorvinphos</a></li> <li><a href="/wiki/Triazofos" title="Triazofos">Triazofos</a></li></ul> </div> <p>Organophosphate insecticides are <a href="/wiki/Acetylcholinesterase_inhibitor" title="Acetylcholinesterase inhibitor">acetylcholinesterase inhibitors</a>, which disrupt the transmission of nerve signals in exposed organisms, with fatal results. The risk of human death through <a href="/wiki/Organophosphate_poisoning" title="Organophosphate poisoning">organophosphate poisoning</a><sup id="cite_ref-33" class="reference"><a href="#cite_note-33"><span class="cite-bracket">[</span>33<span class="cite-bracket">]</span></a></sup> was obvious from the start and led to efforts to lower toxicity against mammals while not reducing efficacy against insects.<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><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> </p><p>The majority of organophosphate insecticides are <a href="/wiki/Organothiophosphate" title="Organothiophosphate">organothiophosphates</a> (P=S) or <a href="/wiki/Phosphorodiamidate" class="mw-redirect" title="Phosphorodiamidate">phosphorodiamidates</a> (P-N), both of which are significantly weaker acetylcholinesterase inhibitors than the corresponding phosphates (P=O). They are 'activated' biologically by the exposed organism, via oxidative conversion of P=S to P=O,<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> hydroxylation,<sup id="cite_ref-37" class="reference"><a href="#cite_note-37"><span class="cite-bracket">[</span>37<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-38" class="reference"><a href="#cite_note-38"><span class="cite-bracket">[</span>38<span class="cite-bracket">]</span></a></sup> or other related process which see them transformed into organophosphates. In mammals these transformations occur almost exclusively in the liver,<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> while in insects they take place in the gut and <a href="/wiki/Fat_body" title="Fat body">fat body</a>.<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><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><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> As the transformations are handled by different <a href="/wiki/Enzyme" title="Enzyme">enzymes</a> in different classes of organism it is possible to find compounds which activate more rapidly and completely in insects, and thus display more targeted lethal action. </p><p>This selectivity is far from perfect and organophosphate insecticides remain <a href="/wiki/Acute_toxicity" title="Acute toxicity">acutely toxic</a> to humans, with many thousands estimated to be killed each year due to intentional (suicide)<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> or unintentional poisoning. Beyond their acute toxicity, long-term exposure to organophosphates is associated with a number of heath risks, including <a href="/wiki/Organophosphate-induced_delayed_neuropathy" title="Organophosphate-induced delayed neuropathy">organophosphate-induced delayed neuropathy</a> (muscle weakness) and developmental <a href="/wiki/Neurotoxicity" title="Neurotoxicity">neurotoxicity</a>.<sup id="cite_ref-OPs_at_80_29-1" class="reference"><a href="#cite_note-OPs_at_80-29"><span class="cite-bracket">[</span>29<span class="cite-bracket">]</span></a></sup><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> There is limited evidence that certain compounds cause cancer, including <a href="/wiki/Malathion" title="Malathion">malathion</a> and <a href="/wiki/Diazinon" title="Diazinon">diazinon</a>.<sup id="cite_ref-46" class="reference"><a href="#cite_note-46"><span class="cite-bracket">[</span>46<span class="cite-bracket">]</span></a></sup> Children<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> and farmworkers<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> are considered to be at greater risk. </p><p><a href="/wiki/Pesticide_regulation_in_the_United_States" title="Pesticide regulation in the United States">Pesticide regulation in the United States</a> and the <a href="/wiki/Regulation_of_pesticides_in_the_European_Union" title="Regulation of pesticides in the European Union">regulation of pesticides in the European Union</a> have both been increasing restrictions on organophosphate pesticides since the 1990s, particularly when used for crop protection. The use of organophosphates has decreased considerably since that time, having been replaced by <a href="/wiki/Pyrethroid" title="Pyrethroid">pyrethroids</a> and <a href="/wiki/Neonicotinoid" title="Neonicotinoid">neonicotinoids</a>, which are effective a much lower levels.<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> Reported cases of organophosphate poisoning in the US have reduced during this period.<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><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> Regulation in the global south can be less extensive.<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><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>In 2015, only 3 of the 50 most common crop-specific pesticides used in the US were organophosphates (<a href="/wiki/Chlorpyrifos" title="Chlorpyrifos">Chlorpyrifos</a>, <a href="/wiki/Bensulide" title="Bensulide">Bensulide</a>, <a href="/wiki/Acephate" title="Acephate">Acephate</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> of these <a href="/wiki/Chlorpyrifos" title="Chlorpyrifos">Chlorpyrifos</a> was banned in 2021.<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> No new organophosphate pesticides have been commercialised in the 21st century.<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> The situation in <a href="/wiki/Vector_control" title="Vector control">vector control</a> is fairly similar, despite different risk trade-offs,<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> with the global use of organophosphate insecticides falling by nearly half between 2010 and 2019.<sup id="cite_ref-Vector-trends_28-1" class="reference"><a href="#cite_note-Vector-trends-28"><span class="cite-bracket">[</span>28<span class="cite-bracket">]</span></a></sup> <a href="/wiki/Pirimiphos-methyl" title="Pirimiphos-methyl">Pirimiphos-methyl</a>, <a href="/wiki/Malathion" title="Malathion">Malathion</a> and <a href="/wiki/Temefos" title="Temefos">Temefos</a> are still important, primarily for the control of <a href="/wiki/Malaria" title="Malaria">malaria</a> in the Asia-Pacific region.<sup id="cite_ref-Vector-trends_28-2" class="reference"><a href="#cite_note-Vector-trends-28"><span class="cite-bracket">[</span>28<span class="cite-bracket">]</span></a></sup> The continued use of these agents is being challenged by the emergence of <a href="/wiki/Insecticide_resistance" class="mw-redirect" title="Insecticide resistance">insecticide resistance</a>.<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> <div class="mw-heading mw-heading3"><h3 id="Flame_retardants">Flame retardants</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Organophosphate&action=edit&section=13" title="Edit section: Flame retardants"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure class="mw-default-size mw-halign-right" typeof="mw:File/Thumb"><a href="/wiki/File:Bisphenol_A_diphenyl_phosphate.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/d/dc/Bisphenol_A_diphenyl_phosphate.svg/220px-Bisphenol_A_diphenyl_phosphate.svg.png" decoding="async" width="220" height="80" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/d/dc/Bisphenol_A_diphenyl_phosphate.svg/330px-Bisphenol_A_diphenyl_phosphate.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/d/dc/Bisphenol_A_diphenyl_phosphate.svg/440px-Bisphenol_A_diphenyl_phosphate.svg.png 2x" data-file-width="231" data-file-height="84" /></a><figcaption><a href="/wiki/Bisphenol_A_diphenyl_phosphate" class="mw-redirect" title="Bisphenol A diphenyl phosphate">Bisphenol A diphenyl phosphate</a>, a common organophosphate flame retardant </figcaption></figure> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">Main article: <a href="/wiki/Flame_retardants" class="mw-redirect" title="Flame retardants">flame retardants</a></div> <p>Flame retardants are added to materials to prevent combustion and to delay the spread of fire after ignition. Organophosphate flame retardants are part of a wider family of phosphorus-based agents which include organic <a href="/wiki/Phosphonate" title="Phosphonate">phosphonate</a> and <a href="/wiki/Phosphinate" title="Phosphinate">phosphinate</a> esters, in addition to inorganic salts.<sup id="cite_ref-retardants-review_59-0" class="reference"><a href="#cite_note-retardants-review-59"><span class="cite-bracket">[</span>59<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Clariant_60-0" class="reference"><a href="#cite_note-Clariant-60"><span class="cite-bracket">[</span>60<span class="cite-bracket">]</span></a></sup> When some prominent <a href="/wiki/Brominated_flame_retardant" title="Brominated flame retardant">brominated flame retardant</a> were banned in the early 2000s phosphorus-based agents were promoted as safer replacements. This has led to a large increase in their use, with an estimated 1 million tonnes of organophosphate flame retardants produced in 2018.<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> Safety concerns have subsequently been raised about some of these reagents,<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><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> with several under regulatory scrutiny.<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><sup id="cite_ref-ECHA-PFR_65-0" class="reference"><a href="#cite_note-ECHA-PFR-65"><span class="cite-bracket">[</span>65<span class="cite-bracket">]</span></a></sup> </p><p>Organophosphate flame retardants were first developed in the first half of the twentieth century in the from of <a href="/wiki/Triphenyl_phosphate" title="Triphenyl phosphate">triphenyl phosphate</a>, <a href="/wiki/Tricresyl_phosphate" title="Tricresyl phosphate">tricresyl phosphate</a> and <a href="/wiki/Tributyl_phosphate" title="Tributyl phosphate">tributyl phosphate</a> for use in plastics like <a href="/wiki/Cellulose_nitrate" class="mw-redirect" title="Cellulose nitrate">cellulose nitrate</a> and <a href="/wiki/Cellulose_acetate" title="Cellulose acetate">cellulose acetate</a>.<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> Use in cellulose products is still significant, but the largest area of application is now in plasticized vinyl polymers, primarily <a href="/wiki/PVC" class="mw-redirect" title="PVC">PVC</a>. The more modern organophosphate flame retardants come in 2 major types; <a href="/wiki/Chlorinated" class="mw-redirect" title="Chlorinated">chlorinated</a> aliphatic compounds or aromatic diphosphates.<sup id="cite_ref-retardants-review_59-1" class="reference"><a href="#cite_note-retardants-review-59"><span class="cite-bracket">[</span>59<span class="cite-bracket">]</span></a></sup> The chlorinated compounds <a href="/wiki/Tris(1,3-dichloro-2-propyl)phosphate" title="Tris(1,3-dichloro-2-propyl)phosphate">TDCPP</a>, <a href="/wiki/Tris(1-chloro-2-propyl)phosphate" class="mw-redirect" title="Tris(1-chloro-2-propyl)phosphate">TCPP</a> and <a href="/wiki/Tris(2-chloroethyl)_phosphate" title="Tris(2-chloroethyl) phosphate">TCEP</a> are all involatile liquids, of which TCPP is perhaps the most important. They are used in <a href="/wiki/Polyurethane" title="Polyurethane">polyurethane</a> (insulation, soft furnishings), <a href="/wiki/PVC" class="mw-redirect" title="PVC">PVC</a> (wire and cable) <a href="/wiki/Phenolic_resin" class="mw-redirect" title="Phenolic resin">phenolic resins</a> and <a href="/wiki/Epoxy_resins" class="mw-redirect" title="Epoxy resins">epoxy resins</a> (varnishes, coatings and adhesives). The most important of the diphosphates is <a href="/wiki/Bisphenol-A_bis(diphenyl_phosphate)" title="Bisphenol-A bis(diphenyl phosphate)">bisphenol-A bis(diphenyl phosphate)</a>, with related analogues based around <a href="/wiki/Resorcinol" title="Resorcinol">resorcinol</a> and <a href="/wiki/Hydroquinone" title="Hydroquinone">hydroquinone</a>. These are used in <a href="/wiki/Polymer_blend" title="Polymer blend">polymer blends</a> of <a href="/wiki/Engineering_plastic" title="Engineering plastic">engineering plastics</a>, such as <a href="/wiki/Poly(phenylene_oxide)" class="mw-redirect" title="Poly(phenylene oxide)">PPO</a>/<a href="/wiki/High_Impact_Polystyrene" class="mw-redirect" title="High Impact Polystyrene">HIPS</a> and <a href="/wiki/Polycarbonate" title="Polycarbonate">PC</a>/<a href="/wiki/Acrylonitrile_butadiene_styrene" title="Acrylonitrile butadiene styrene">ABS</a>,<sup id="cite_ref-67" class="reference"><a href="#cite_note-67"><span class="cite-bracket">[</span>67<span class="cite-bracket">]</span></a></sup> which are commonly used to make casing for electrical items like TVs, computers and home appliances. </p><p>Organophosphates act multifunctionally to retard fire in both the gas phase and condensed (solid) phase. Halogenated organophosphates are more active overall as their degradation products interfere with combustion directly in the gas phase. All organophosphates have activity in the condensed phase, by forming phosphorus acids which promote <a href="/wiki/Charring" title="Charring">char</a> formation, insulating the surface from heat and air. </p><p>Organophosphates were originally thought to be a safe replacements for brominated flame retardants, however many are now coming under regulatory pressure due to their apparent health risks.<sup id="cite_ref-ECHA-PFR_65-1" class="reference"><a href="#cite_note-ECHA-PFR-65"><span class="cite-bracket">[</span>65<span class="cite-bracket">]</span></a></sup><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><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> The chlorinated organophosphates may be carcinogenic, while others such as <a href="/wiki/Tricresyl_phosphate" title="Tricresyl phosphate">tricresyl phosphate</a> have necrotoxic properties.<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> Bisphenol-A bis(diphenyl phosphate) can hydrolyse to form <a href="/wiki/Bisphenol-A" class="mw-redirect" title="Bisphenol-A">Bisphenol-A</a> which is under significant scrutiny as potential <a href="/wiki/Endocrine-disrupting_chemical" class="mw-redirect" title="Endocrine-disrupting chemical">endocrine-disrupting chemical</a>. Although their names imply that they are a single chemical, some (but not all) are produced as complex mixtures. For instance, commercial grade TCPP can contain 7 different <a href="/wiki/Isomer" title="Isomer">isomers</a>,<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> while <a href="/wiki/Tricresyl_phosphate" title="Tricresyl phosphate">tricresyl phosphate</a> can contain up to 10.<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> This makes their safety profiles harder to ascertain, as material from different producers can have different compositions.<sup id="cite_ref-73" class="reference"><a href="#cite_note-73"><span class="cite-bracket">[</span>73<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Plasticisers">Plasticisers</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Organophosphate&action=edit&section=14" title="Edit section: Plasticisers"><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/Plasticizer" title="Plasticizer">Plasticizer</a></div> <figure class="mw-default-size mw-halign-right" typeof="mw:File/Thumb"><a href="/wiki/File:2-Ethylhexyl_diphenyl_phosphate_Structural_Formula_V2.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/e/e5/2-Ethylhexyl_diphenyl_phosphate_Structural_Formula_V2.svg/220px-2-Ethylhexyl_diphenyl_phosphate_Structural_Formula_V2.svg.png" decoding="async" width="220" height="133" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/e5/2-Ethylhexyl_diphenyl_phosphate_Structural_Formula_V2.svg/330px-2-Ethylhexyl_diphenyl_phosphate_Structural_Formula_V2.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/e/e5/2-Ethylhexyl_diphenyl_phosphate_Structural_Formula_V2.svg/440px-2-Ethylhexyl_diphenyl_phosphate_Structural_Formula_V2.svg.png 2x" data-file-width="378" data-file-height="229" /></a><figcaption><a href="/wiki/2-Ethylhexyl_diphenyl_phosphate" title="2-Ethylhexyl diphenyl phosphate">2-Ethylhexyl diphenyl phosphate</a> an alkyl diaryl organophosphate used as both a plasticizer and flame retardant in PVC</figcaption></figure> <p>Plasticisers are added to polymers and plastics to improve their flexibility and processability, giving a softer more easily deformable material. In this way brittle polymers can be made more durable. The most frequently plasticised polymers are the vinyls (<a href="/wiki/PVC" class="mw-redirect" title="PVC">PVC</a>, <a href="/wiki/Polyvinyl_butyral" title="Polyvinyl butyral">PVB</a>, <a href="/wiki/Poly(vinyl_acetate)" class="mw-redirect" title="Poly(vinyl acetate)">PVA</a> and <a href="/wiki/Polyvinyl_chloride_acetate" title="Polyvinyl chloride acetate">PVCA</a>), as well as cellulose plastics (<a href="/wiki/Cellulose_acetate" title="Cellulose acetate">cellulose acetate</a>, <a href="/wiki/Nitrocellulose" title="Nitrocellulose">nitrocellulose</a> and <a href="/wiki/Cellulose_acetate_butyrate" title="Cellulose acetate butyrate">cellulose acetate butyrate</a>).<sup id="cite_ref-Ullmann's_74-0" class="reference"><a href="#cite_note-Ullmann's-74"><span class="cite-bracket">[</span>74<span class="cite-bracket">]</span></a></sup> PVC dominates the market, consuming 80-90% of global plasticiser production.<sup id="cite_ref-Ullmann's_74-1" class="reference"><a href="#cite_note-Ullmann's-74"><span class="cite-bracket">[</span>74<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Plast-market_75-0" class="reference"><a href="#cite_note-Plast-market-75"><span class="cite-bracket">[</span>75<span class="cite-bracket">]</span></a></sup> PVC can accept large amounts of plasticiser; it is common for products to be 0-50% plasticiser by mass, but loadings can be as high as 70-80% in the case of <a href="/wiki/Plastisol" title="Plastisol">plastisols</a>.<sup id="cite_ref-additives_handbook_76-0" class="reference"><a href="#cite_note-additives_handbook-76"><span class="cite-bracket">[</span>76<span class="cite-bracket">]</span></a></sup> </p><p>Pure PVC is more than 60% chlorine by mass and is difficult to burn, but its flammability increases the more it is plasticised.<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> Organophosphates find use because they are multifunctional; primarily plasticising but also imparting flame resistance. Compounds are typically triaryl or alkyl diaryl phosphates, with <a href="/w/index.php?title=Cresyl_diphenyl_phosphate&action=edit&redlink=1" class="new" title="Cresyl diphenyl phosphate (page does not exist)">cresyl diphenyl phosphate</a> and <a href="/wiki/2-ethylhexyl_diphenyl_phosphate" class="mw-redirect" title="2-ethylhexyl diphenyl phosphate">2-ethylhexyl diphenyl phosphate</a> being important examples respectively.<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> These are both liquids with high boiling points. Organophosphates are more expensive than traditional plasticisers and so tend be used in combination with other plasticisers and flame retardants.<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> </p> <div class="mw-heading mw-heading3"><h3 id="Hydraulic_fluids_and_lubricant_additives">Hydraulic fluids and lubricant additives</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Organophosphate&action=edit&section=15" title="Edit section: Hydraulic fluids and lubricant additives"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Similar to their use as plastisiers, organophosphates are well suited to use as <a href="/wiki/Hydraulic_fluid" title="Hydraulic fluid">hydraulic fluids</a> due to their low freezing points and high boiling points, fire-resistance, non-corrosiveness, excellent boundary lubrication properties and good general chemical stability. The triaryl phosphates are the most important group, with tricresyl phosphate being the first to be commercialised in the 1940s, with <a href="/wiki/Trixylyl_phosphate" title="Trixylyl phosphate">trixylyl phosphate</a> following shortly after. Butylphenyl diphenyl phosphate and propylphenyl diphenyl phosphate became available after 1960.<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><p>In addition to their use as hydraulic base-stock, organophosphates (tricresyl phosphate) and metal organothiophosphates (<a href="/wiki/Zinc_dithiophosphate" title="Zinc dithiophosphate">zinc dithiophosphate</a>) are used as both an <a href="/wiki/Antiwear_additive" title="Antiwear additive">antiwear additives</a> and <a href="/wiki/Extreme_pressure_additive" title="Extreme pressure additive">extreme pressure additives</a> in <a href="/wiki/Lubricant" title="Lubricant">lubricants</a>, where they remain effective even at high temperatures.<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><sup id="cite_ref-82" class="reference"><a href="#cite_note-82"><span class="cite-bracket">[</span>82<span class="cite-bracket">]</span></a></sup><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> </p> <div class="mw-heading mw-heading3"><h3 id="Metal_extractants">Metal extractants</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Organophosphate&action=edit&section=16" title="Edit section: Metal extractants"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Organophosphates have long been used in the field of <a href="/wiki/Extractive_metallurgy" title="Extractive metallurgy">extractive metallurgy</a> to liberate valuable <a href="/wiki/Rare-earth_element" title="Rare-earth element">rare earth metals</a> from their <a href="/wiki/Ore" title="Ore">ores</a>.<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> <a href="/wiki/Di(2-ethylhexyl)phosphoric_acid" title="Di(2-ethylhexyl)phosphoric acid">Di(2-ethylhexyl)phosphoric acid</a> and <a href="/wiki/Tributyl_phosphate" title="Tributyl phosphate">tributyl phosphate</a> are used for the <a href="/wiki/Liquid%E2%80%93liquid_extraction" title="Liquid–liquid extraction">liquid–liquid extraction</a> of these elements from the acidic mixtures form by the <a href="/wiki/Leaching_(metallurgy)" title="Leaching (metallurgy)">leaching</a> of mineral deposits.<sup id="cite_ref-85" class="reference"><a href="#cite_note-85"><span class="cite-bracket">[</span>85<span class="cite-bracket">]</span></a></sup> The same compounds are also used in <a href="/wiki/Nuclear_reprocessing" title="Nuclear reprocessing">nuclear reprocessing</a>, as part of the <a href="/wiki/PUREX" title="PUREX">PUREX</a> process.<sup id="cite_ref-86" class="reference"><a href="#cite_note-86"><span class="cite-bracket">[</span>86<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Surfactants">Surfactants</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Organophosphate&action=edit&section=17" title="Edit section: Surfactants"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Mono- and di- phosphate esters of alcohols (or alcohol <a href="/wiki/Ethoxylate" class="mw-redirect" title="Ethoxylate">ethoxylates</a>) act as <a href="/wiki/Surfactant" title="Surfactant">surfactants</a> (detergents).<sup id="cite_ref-Farn2008_87-0" class="reference"><a href="#cite_note-Farn2008-87"><span class="cite-bracket">[</span>87<span class="cite-bracket">]</span></a></sup> Although they are very common in biology as <a href="/wiki/Phospholipid" title="Phospholipid">phospholipids</a>, their industrial use is largely limited to certain niche areas. Compared to the more common sulfur-based anionic surfactants (such as <a href="/wiki/Alkylbenzene_sulfonates" class="mw-redirect" title="Alkylbenzene sulfonates">LAS</a> or <a href="/wiki/Sodium_laureth_sulfate" title="Sodium laureth sulfate">SLES</a>), phosphate ester surfactants are more expensive and generate less foam.<sup id="cite_ref-Farn2008_87-1" class="reference"><a href="#cite_note-Farn2008-87"><span class="cite-bracket">[</span>87<span class="cite-bracket">]</span></a></sup> Benefits include high stability at extremes of pH, low skin irritation and a high tolerance to dissolved salts.<sup id="cite_ref-88" class="reference"><a href="#cite_note-88"><span class="cite-bracket">[</span>88<span class="cite-bracket">]</span></a></sup> In agricultural settings monoesters of fatty alcohol ethoxylates are used, which are able to disperse poorly miscible or insoluble pesticides into water. As they are low-foaming these mixtures can be sprayed effectively onto fields, while a high salt tolerance allows co-spraying of pesticides and inorganic fertilisers.<sup id="cite_ref-89" class="reference"><a href="#cite_note-89"><span class="cite-bracket">[</span>89<span class="cite-bracket">]</span></a></sup> Low-levels of phosphate mono-esters, such as <a href="/w/index.php?title=Potassium_cetyl_phosphate&action=edit&redlink=1" class="new" title="Potassium cetyl phosphate (page does not exist)">potassium cetyl phosphate</a>, find use in cosmetic creams and lotions.<sup id="cite_ref-90" class="reference"><a href="#cite_note-90"><span class="cite-bracket">[</span>90<span class="cite-bracket">]</span></a></sup> These in oil-in-water formulations are primarily based on non-ionic surfactants, with the anionic phosphate acting as emulsion-stabilisers. Phosphate tri-esters such as <a href="/wiki/Tributyl_phosphate" title="Tributyl phosphate">tributyl phosphate</a> are used as <a href="/wiki/Anti-foaming_agent" class="mw-redirect" title="Anti-foaming agent">anti-foaming agent</a> in paints and concrete. </p> <div class="mw-heading mw-heading3"><h3 id="Nerve_agents">Nerve agents</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Organophosphate&action=edit&section=18" title="Edit section: Nerve agents"><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/Nerve_agents" class="mw-redirect" title="Nerve agents">Nerve agents</a></div> <p>Although the first phosphorus compounds observed to act as cholinesterase inhibitors were organophosphates,<sup id="cite_ref-91" class="reference"><a href="#cite_note-91"><span class="cite-bracket">[</span>91<span class="cite-bracket">]</span></a></sup> the vast majority of nerve agents are instead <a href="/wiki/Phosphonate" title="Phosphonate">phosphonates</a> containing a P-C bond. Only a handful of organophosphate nerve agents were developed between the 1930s and 1960s, including <a href="/wiki/Diisopropylfluorophosphate" class="mw-redirect" title="Diisopropylfluorophosphate">diisopropylfluorophosphate</a>, <a href="/wiki/VG_(nerve_agent)" title="VG (nerve agent)">VG</a> and <a href="/wiki/Neopentylene_fluorophosphate" title="Neopentylene fluorophosphate">NPF</a>. Between 1971 and 1993 the <a href="/wiki/Soviet_Union" title="Soviet Union">Soviet Union</a> developed many new potential nerve agents, commonly known as the <a href="/wiki/Novichok_agents" class="mw-redirect" title="Novichok agents">Novichok agents</a>.<sup id="cite_ref-92" class="reference"><a href="#cite_note-92"><span class="cite-bracket">[</span>92<span class="cite-bracket">]</span></a></sup> Some of these can be considered organophosphates (in a broad sense), being derivatives of <a href="/wiki/Fluorophosphoric_acid" title="Fluorophosphoric acid">fluorophosphoric acid</a>. Examples include <a href="/wiki/A-232" title="A-232">A-232</a>, <a href="/wiki/A-234_(nerve_agent)" title="A-234 (nerve agent)">A-234</a>, <a href="/wiki/A-262" title="A-262">A-262</a>, <a href="/wiki/C01-A035" title="C01-A035">C01-A035</a> and <a href="/wiki/C01-A039" title="C01-A039">C01-A039</a>. The most notable of these is A-234, which was claimed to be responsible for the <a href="/wiki/Poisoning_of_Sergei_and_Yulia_Skripal" title="Poisoning of Sergei and Yulia Skripal">poisoning of Sergei and Yulia Skripal</a> in Salisbury (UK) 2018.<sup id="cite_ref-93" class="reference"><a href="#cite_note-93"><span class="cite-bracket">[</span>93<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="In_nature">In nature</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Organophosphate&action=edit&section=19" title="Edit section: In nature"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The detection of OPEs in the air as far away as Antarctica at concentrations around 1 ng/m<sup>3</sup> suggests their persistence in air, and their potential for long-range transport.<sup id="cite_ref-:7_25-1" class="reference"><a href="#cite_note-:7-25"><span class="cite-bracket">[</span>25<span class="cite-bracket">]</span></a></sup> OPEs were measured in high frequency in air and water and widely distributed in northern hemisphere.<sup id="cite_ref-94" class="reference"><a href="#cite_note-94"><span class="cite-bracket">[</span>94<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-:8_95-0" class="reference"><a href="#cite_note-:8-95"><span class="cite-bracket">[</span>95<span class="cite-bracket">]</span></a></sup> The chlorinated OPEs (TCEP, TCIPP, TDCIPP) in urban sampling sites and non-halogenated like TBOEP in rural areas respectively were frequently measured in the environment across multiple sites. In the Laurentian Great Lakes total OPEs concentrations were found to be 2–3 orders of magnitude higher than concentrations of brominated flame retardants measured in similar air.<sup id="cite_ref-:8_95-1" class="reference"><a href="#cite_note-:8-95"><span class="cite-bracket">[</span>95<span class="cite-bracket">]</span></a></sup> Waters from rivers in Germany, Austria, and Spain have been consistently recorded for TBOEP and TCIPP at highest concentrations.<sup id="cite_ref-:7_25-2" class="reference"><a href="#cite_note-:7-25"><span class="cite-bracket">[</span>25<span class="cite-bracket">]</span></a></sup> From these studies, it is clear that OPE concentrations in both air and water samples are often orders of magnitude higher than other flame retardants, and that concentrations are largely dependent on sampling location, with higher concentrations in more urban, polluted locations. </p> <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=Organophosphate&action=edit&section=20" title="Edit section: References"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1239543626">.mw-parser-output .reflist{margin-bottom:0.5em;list-style-type:decimal}@media screen{.mw-parser-output .reflist{font-size:90%}}.mw-parser-output .reflist .references{font-size:100%;margin-bottom:0;list-style-type:inherit}.mw-parser-output .reflist-columns-2{column-width:30em}.mw-parser-output .reflist-columns-3{column-width:25em}.mw-parser-output .reflist-columns{margin-top:0.3em}.mw-parser-output .reflist-columns ol{margin-top:0}.mw-parser-output .reflist-columns li{page-break-inside:avoid;break-inside:avoid-column}.mw-parser-output .reflist-upper-alpha{list-style-type:upper-alpha}.mw-parser-output .reflist-upper-roman{list-style-type:upper-roman}.mw-parser-output .reflist-lower-alpha{list-style-type:lower-alpha}.mw-parser-output .reflist-lower-greek{list-style-type:lower-greek}.mw-parser-output .reflist-lower-roman{list-style-type:lower-roman}</style><div class="reflist reflist-columns references-column-width reflist-columns-2"> <ol class="references"> <li id="cite_note-:3-1"><span class="mw-cite-backlink">^ <a href="#cite_ref-:3_1-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-:3_1-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><style data-mw-deduplicate="TemplateStyles:r1238218222">.mw-parser-output cite.citation{font-style:inherit;word-wrap:break-word}.mw-parser-output .citation q{quotes:"\"""\"""'""'"}.mw-parser-output .citation:target{background-color:rgba(0,127,255,0.133)}.mw-parser-output .id-lock-free.id-lock-free a{background:url("//upload.wikimedia.org/wikipedia/commons/6/65/Lock-green.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-limited.id-lock-limited a,.mw-parser-output .id-lock-registration.id-lock-registration a{background:url("//upload.wikimedia.org/wikipedia/commons/d/d6/Lock-gray-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-subscription.id-lock-subscription a{background:url("//upload.wikimedia.org/wikipedia/commons/a/aa/Lock-red-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .cs1-ws-icon a{background:url("//upload.wikimedia.org/wikipedia/commons/4/4c/Wikisource-logo.svg")right 0.1em center/12px no-repeat}body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-free a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-limited a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-registration a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-subscription a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .cs1-ws-icon a{background-size:contain;padding:0 1em 0 0}.mw-parser-output .cs1-code{color:inherit;background:inherit;border:none;padding:inherit}.mw-parser-output .cs1-hidden-error{display:none;color:var(--color-error,#d33)}.mw-parser-output .cs1-visible-error{color:var(--color-error,#d33)}.mw-parser-output .cs1-maint{display:none;color:#085;margin-left:0.3em}.mw-parser-output .cs1-kern-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right{padding-right:0.2em}.mw-parser-output .citation .mw-selflink{font-weight:inherit}@media screen{.mw-parser-output .cs1-format{font-size:95%}html.skin-theme-clientpref-night .mw-parser-output .cs1-maint{color:#18911f}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .cs1-maint{color:#18911f}}</style><cite id="CITEREFGreavesLetcherChenMcGoldrick2016" class="citation journal cs1">Greaves, Alana K.; Letcher, Robert J.; Chen, Da; McGoldrick, Daryl J.; Gauthier, Lewis T.; Backus, Sean M. 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.navbar{display:none!important}}</style><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Organophosphorus" title="Template:Organophosphorus"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Organophosphorus" title="Template talk:Organophosphorus"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Organophosphorus" title="Special:EditPage/Template:Organophosphorus"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Organophosphorus" style="font-size:114%;margin:0 4em"><a href="/wiki/Organophosphorus_chemistry" title="Organophosphorus chemistry">Organophosphorus</a></div></th></tr><tr><td colspan="2" class="navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Phosphite_anion" title="Phosphite anion">PO<sub>3</sub>H<sup>2−</sup></a></li> <li><a href="/wiki/Phosphite_ester" title="Phosphite ester">P(O–)<sub>3</sub></a></li> <li><a href="/wiki/Phosphoric_acids_and_phosphates" title="Phosphoric acids and phosphates">P<sub>2</sub>O<sub>5</sub>·<span class="texhtml mvar" style="font-style:italic;">n</span>H<sub>2</sub>O</a></li> <li><a class="mw-selflink selflink">OP(O–)<sub>3</sub></a></li> <li><a href="/w/index.php?title=Organophosphonic_acid&action=edit&redlink=1" class="new" title="Organophosphonic acid (page does not exist)">–P(OH)<sub>2</sub></a></li> <li><a href="/wiki/Phosphonite" title="Phosphonite">–P(O–)<sub>2</sub></a></li> <li><a href="/wiki/Phosphonate" title="Phosphonate">–P(O)(O–)<sub>2</sub></a></li> <li><a href="/wiki/Phosphinite" title="Phosphinite">–OP<</a> <ul><li>free acid <a href="/wiki/Phosphinous_acids" title="Phosphinous acids">HOP(CF<sub>3</sub>)<sub>2</sub></a></li></ul></li> <li><a href="/wiki/Organophosphinic_acid" title="Organophosphinic acid">HOP(O)<</a></li> <li><a href="/wiki/Phosphinate" title="Phosphinate">PO<sub>2</sub>H<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1.2em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline">−</sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">2</sub></span></span></a></li> <li><a href="/wiki/Organophosphine" title="Organophosphine">–P<</a></li> <li><a href="/wiki/Phosphine_oxide" title="Phosphine oxide">–P(O)<</a></li> <li><a href="/wiki/Phosphoramidite" title="Phosphoramidite">(–O)<sub>2</sub>PN<</a> <ul><li>e.g. <a href="/wiki/Nucleoside_phosphoramidite" title="Nucleoside phosphoramidite">Nucleoside phosphoramidite</a></li></ul></li> <li><a href="/wiki/Phosphoramidate" title="Phosphoramidate">(–O)<sub>2</sub>P(O)N<</a> <ul><li>e.g. <a href="/wiki/Phosphocreatine" title="Phosphocreatine">Phosphocreatine</a></li></ul></li> <li><a href="/w/index.php?title=Phosphorodiamidite&action=edit&redlink=1" class="new" title="Phosphorodiamidite (page does not exist)">–OP(N<)<sub>2</sub></a></li> <li><a href="/wiki/Phosphoramidate" title="Phosphoramidate">–OP(O)(N<)<sub>2</sub></a> <ul><li>e.g. <a href="/wiki/Morpholino" title="Morpholino">Morpholino</a></li> <li><a href="/wiki/Cyclophosphamide" title="Cyclophosphamide">Cyclophosphamide</a></li></ul></li> <li><a href="/wiki/Aminophosphine" title="Aminophosphine">P(N<)<sub>3</sub></a> <ul><li>e.g. <a href="/wiki/Tris(dimethylamino)phosphine" title="Tris(dimethylamino)phosphine">P(NMe<sub>2</sub>)<sub>3</sub></a></li></ul></li> <li><a href="/wiki/Phosphoramides" title="Phosphoramides">OP(N<)<sub>3</sub></a> <ul><li>e.g. <a href="/wiki/Hexamethylphosphoramide" title="Hexamethylphosphoramide">Hexamethylphosphoramide</a></li> <li><a href="/wiki/Metepa" title="Metepa">Metepa</a></li></ul></li> <li><a href="/w/index.php?title=Phosphorimide_triamide&action=edit&redlink=1" class="new" title="Phosphorimide triamide (page does not exist)">–NP(N<)<sub>3</sub></a></li> <li><a href="/wiki/Phosphonamidate" class="mw-redirect" title="Phosphonamidate">–P(O)(O–)N<</a></li> <li><a href="/w/index.php?title=Phosphonamide&action=edit&redlink=1" class="new" title="Phosphonamide (page does not exist)">–P(O)(N<)<sub>2</sub></a></li> <li><a href="/w/index.php?title=Phosphinamide&action=edit&redlink=1" class="new" title="Phosphinamide (page does not exist)">>P(O)N<</a></li> <li><a href="/wiki/Thiophosphate" title="Thiophosphate">PS<sub><span class="texhtml mvar" style="font-style:italic;">x</span></sub>O<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1.2em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline">3−</sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline"><span class="texhtml">4-<i>x</i></span></sub></span></span></a></li> <li><a href="/wiki/Organothiophosphate" title="Organothiophosphate">(–O)<sub>3</sub>PS</a></li> <li><a href="/wiki/Cyclophosphines" class="mw-redirect" title="Cyclophosphines">(-P)<sub>5</sub></a></li></ul> </div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"></div><div role="navigation" class="navbox" aria-labelledby="Pest_control:_Insecticides" 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:Insecticides" title="Template:Insecticides"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Insecticides" title="Template talk:Insecticides"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Insecticides" title="Special:EditPage/Template:Insecticides"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Pest_control:_Insecticides" style="font-size:114%;margin:0 4em"><a href="/wiki/Pest_control" title="Pest control">Pest control</a>: <a href="/wiki/Insecticide" title="Insecticide">Insecticides</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%;background:PowderBlue;"><a href="/wiki/Carbamate" title="Carbamate">Carbamates</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/Aldicarb" title="Aldicarb">Aldicarb</a></li> <li><a href="/wiki/Aminocarb" title="Aminocarb">Aminocarb</a></li> <li><a href="/wiki/Bendiocarb" title="Bendiocarb">Bendiocarb</a></li> <li><a href="/wiki/Butocarboxim" title="Butocarboxim">Butocarboxim</a></li> <li><a href="/wiki/Carbaryl" title="Carbaryl">Carbaryl</a></li> <li><a href="/wiki/Carbofuran" title="Carbofuran">Carbofuran</a></li> <li><a href="/wiki/Carbosulfan" title="Carbosulfan">Carbosulfan</a></li> <li><a href="/wiki/M-Cumenyl_methylcarbamate" title="M-Cumenyl methylcarbamate">m-Cumenyl methylcarbamate</a></li> <li><a href="/wiki/Ethienocarb" class="mw-redirect" title="Ethienocarb">Ethienocarb</a></li> <li><a href="/wiki/Fenobucarb" title="Fenobucarb">Fenobucarb</a></li> <li><a href="/w/index.php?title=Isoprocarb&action=edit&redlink=1" class="new" title="Isoprocarb (page does not exist)">Isoprocarb</a></li> <li><a href="/wiki/Methomyl" title="Methomyl">Methomyl</a></li> <li><a href="/wiki/Metolcarb" title="Metolcarb">Metolcarb</a></li> <li><a href="/wiki/Oxamyl" title="Oxamyl">Oxamyl</a></li> <li><a href="/wiki/Promecarb" title="Promecarb">Promecarb</a></li> <li><a href="/wiki/Propoxur" title="Propoxur">Propoxur</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;background:PowderBlue;"><a href="/wiki/Inorganic_compound" title="Inorganic compound">Inorganic compounds</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/Aluminium_phosphide" title="Aluminium phosphide">Aluminium phosphide</a></li> <li><a href="/wiki/Boric_acid" title="Boric acid">Boric acid</a></li> <li><a href="/wiki/Chromated_copper_arsenate" title="Chromated copper arsenate">Chromated copper arsenate</a></li> <li><a href="/wiki/Copper(II)_arsenate" title="Copper(II) arsenate">Copper(II) arsenate</a></li> <li><a href="/wiki/Copper(I)_cyanide" title="Copper(I) cyanide">Copper(I) cyanide</a></li> <li><a href="/wiki/Cryolite" title="Cryolite">Cryolite</a></li> <li><a href="/wiki/Diatomaceous_earth" title="Diatomaceous earth">Diatomaceous earth</a></li> <li><a href="/wiki/Lead_hydrogen_arsenate" title="Lead hydrogen arsenate">Lead hydrogen arsenate</a></li> <li><a href="/wiki/Paris_Green" class="mw-redirect" title="Paris Green">Paris Green</a></li> <li><a href="/wiki/Scheele%27s_Green" class="mw-redirect" title="Scheele's Green">Scheele's Green</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;background:PowderBlue;"><a href="/wiki/Insect_growth_regulator" title="Insect growth regulator">Insect growth regulators</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/Benzoylurea" class="mw-redirect" title="Benzoylurea">Benzoylureas</a></li> <li><a href="/wiki/Diflubenzuron" title="Diflubenzuron">Diflubenzuron</a></li> <li><a href="/wiki/Flufenoxuron" title="Flufenoxuron">Flufenoxuron</a></li> <li><a href="/wiki/Hydroprene" title="Hydroprene">Hydroprene</a></li> <li><a href="/wiki/Lufenuron" title="Lufenuron">Lufenuron</a></li> <li><a href="/wiki/Methoprene" title="Methoprene">Methoprene</a></li> <li><a href="/wiki/Pyriproxyfen" title="Pyriproxyfen">Pyriproxyfen</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;background:PowderBlue;"><a href="/wiki/Neonicotinoid" title="Neonicotinoid">Neonicotinoids</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/Acetamiprid" title="Acetamiprid">Acetamiprid</a></li> <li><a href="/wiki/Clothianidin" title="Clothianidin">Clothianidin</a></li> <li><a href="/wiki/Dinotefuran" title="Dinotefuran">Dinotefuran</a></li> <li><a href="/wiki/Imidacloprid" title="Imidacloprid">Imidacloprid</a></li> <li><a href="/wiki/Imidaclothiz" title="Imidaclothiz">Imidaclothiz</a></li> <li><a href="/wiki/Nitenpyram" title="Nitenpyram">Nitenpyram</a></li> <li><a href="/wiki/Nithiazine" title="Nithiazine">Nithiazine</a></li> <li><a href="/wiki/Paichongding" title="Paichongding">Paichongding</a></li> <li><a href="/wiki/Thiacloprid" title="Thiacloprid">Thiacloprid</a></li> <li><a href="/wiki/Thiamethoxam" title="Thiamethoxam">Thiamethoxam</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;background:PowderBlue;"><a href="/wiki/Organochloride" class="mw-redirect" title="Organochloride">Organochlorides</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/Aldrin" title="Aldrin">Aldrin</a></li> <li><a href="/wiki/Beta-Hexachlorocyclohexane" class="mw-redirect" title="Beta-Hexachlorocyclohexane">Beta-HCH</a></li> <li><a href="/wiki/Carbon_tetrachloride" title="Carbon tetrachloride">Carbon tetrachloride</a></li> <li><a href="/wiki/Chlordane" title="Chlordane">Chlordane</a></li> <li><a href="/wiki/Hexachlorocyclopentadiene" title="Hexachlorocyclopentadiene">Cyclodiene</a></li> <li><a href="/wiki/1,2-Dichlorobenzene" title="1,2-Dichlorobenzene">1,2-DCB</a></li> <li><a href="/wiki/1,4-Dichlorobenzene" title="1,4-Dichlorobenzene">1,4-DCB</a></li> <li><a href="/wiki/1,1-Dichloroethane" title="1,1-Dichloroethane">1,1-DCE</a></li> <li><a href="/wiki/1,2-Dichloroethane" title="1,2-Dichloroethane">1,2-DCE</a></li> <li><a href="/wiki/Dichlorodiphenyldichloroethane" title="Dichlorodiphenyldichloroethane">DDD</a></li> <li><a href="/wiki/Dichlorodiphenyldichloroethylene" title="Dichlorodiphenyldichloroethylene">DDE</a></li> <li><a href="/wiki/DDT" title="DDT">DDT</a></li> <li><a href="/wiki/DFDT" title="DFDT">DFDT</a></li> <li><a href="/wiki/Dicofol" title="Dicofol">Dicofol</a></li> <li><a href="/wiki/Dieldrin" title="Dieldrin">Dieldrin</a></li> <li><a href="/wiki/Endosulfan" title="Endosulfan">Endosulfan</a></li> <li><a href="/wiki/Endrin" title="Endrin">Endrin</a></li> <li><a href="/wiki/Heptachlor" title="Heptachlor">Heptachlor</a></li> <li><a href="/wiki/Kepone" class="mw-redirect" title="Kepone">Kepone</a></li> <li><a href="/wiki/Lindane" title="Lindane">Lindane</a></li> <li><a href="/wiki/Methoxychlor" title="Methoxychlor">Methoxychlor</a></li> <li><a href="/wiki/Mirex" title="Mirex">Mirex</a></li> <li><a href="/wiki/Tetradifon" title="Tetradifon">Tetradifon</a></li> <li><a href="/wiki/Toxaphene" title="Toxaphene">Toxaphene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;background:PowderBlue;"><a href="/wiki/Organophosphorus_compound" class="mw-redirect" title="Organophosphorus compound">Organophosphorus</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/Acephate" title="Acephate">Acephate</a></li> <li><a href="/wiki/Azamethiphos" title="Azamethiphos">Azamethiphos</a></li> <li><a href="/wiki/Azinphos-methyl" title="Azinphos-methyl">Azinphos-methyl</a></li> <li><a href="/wiki/Bensulide" title="Bensulide">Bensulide</a></li> <li><a href="/wiki/Chlorethoxyfos" title="Chlorethoxyfos">Chlorethoxyfos</a></li> <li><a href="/wiki/Chlorfenvinphos" title="Chlorfenvinphos">Chlorfenvinphos</a></li> <li><a href="/wiki/Chlorpyrifos" title="Chlorpyrifos">Chlorpyrifos</a></li> <li><a href="/wiki/Chlorpyrifos-methyl" class="mw-redirect" title="Chlorpyrifos-methyl">Chlorpyrifos-methyl</a></li> <li><a href="/wiki/Coumaphos" title="Coumaphos">Coumaphos</a></li> <li><a href="/wiki/Demeton-S-methyl" title="Demeton-S-methyl">Demeton-S-methyl</a></li> <li><a href="/wiki/Diazinon" title="Diazinon">Diazinon</a></li> <li><a href="/wiki/Dichlorvos" title="Dichlorvos">Dichlorvos</a></li> <li><a href="/wiki/Dicrotophos" title="Dicrotophos">Dicrotophos</a></li> <li><a href="/wiki/Diisopropyl_fluorophosphate" title="Diisopropyl fluorophosphate">Diisopropyl fluorophosphate</a></li> <li><a href="/wiki/Dimefox" title="Dimefox">Dimefox</a></li> <li><a href="/wiki/Dimethoate" title="Dimethoate">Dimethoate</a></li> <li><a href="/wiki/Dioxathion" title="Dioxathion">Dioxathion</a></li> <li><a href="/wiki/Disulfoton" title="Disulfoton">Disulfoton</a></li> <li><a href="/wiki/Ethion" title="Ethion">Ethion</a></li> <li><a href="/wiki/Ethoprop" class="mw-redirect" title="Ethoprop">Ethoprop</a></li> <li><a href="/wiki/Fenamiphos" title="Fenamiphos">Fenamiphos</a></li> <li><a href="/wiki/Fenitrothion" title="Fenitrothion">Fenitrothion</a></li> <li><a href="/wiki/Fenthion" title="Fenthion">Fenthion</a></li> <li><a href="/w/index.php?title=Fosthiazate&action=edit&redlink=1" class="new" title="Fosthiazate (page does not exist)">Fosthiazate</a></li> <li><a href="/wiki/Isoxathion" title="Isoxathion">Isoxathion</a></li> <li><a href="/wiki/Malathion" title="Malathion">Malathion</a></li> <li><a href="/wiki/Methamidophos" title="Methamidophos">Methamidophos</a></li> <li><a href="/wiki/Methidathion" title="Methidathion">Methidathion</a></li> <li><a href="/wiki/Mevinphos" title="Mevinphos">Mevinphos</a></li> <li><a href="/wiki/Mipafox" title="Mipafox">Mipafox</a></li> <li><a href="/wiki/Monocrotophos" title="Monocrotophos">Monocrotophos</a></li> <li><a href="/wiki/Naled" title="Naled">Naled</a></li> <li><a href="/wiki/Omethoate" title="Omethoate">Omethoate</a></li> <li><a href="/wiki/Oxydemeton-methyl" title="Oxydemeton-methyl">Oxydemeton-methyl</a></li> <li><a href="/wiki/Parathion" title="Parathion">Parathion</a></li> <li><a href="/wiki/Parathion-methyl" class="mw-redirect" title="Parathion-methyl">Parathion-methyl</a></li> <li><a href="/wiki/Phenthoate" title="Phenthoate">Phenthoate</a></li> <li><a href="/wiki/Phorate" title="Phorate">Phorate</a></li> <li><a href="/wiki/Phosalone" title="Phosalone">Phosalone</a></li> <li><a href="/wiki/Phosmet" title="Phosmet">Phosmet</a></li> <li><a href="/wiki/Phoxim" title="Phoxim">Phoxim</a></li> <li><a href="/wiki/Pirimiphos-methyl" title="Pirimiphos-methyl">Pirimiphos-methyl</a></li> <li><a href="/wiki/Quinalphos" title="Quinalphos">Quinalphos</a></li> <li><a href="/wiki/R-16661" title="R-16661">R-16661</a></li> <li><a href="/wiki/Schradan" title="Schradan">Schradan</a></li> <li><a href="/wiki/Temefos" title="Temefos">Temefos</a></li> <li><a href="/wiki/Tebupirimfos" title="Tebupirimfos">Tebupirimfos</a></li> <li><a href="/wiki/Terbufos" title="Terbufos">Terbufos</a></li> <li><a href="/wiki/Tetrachlorvinphos" title="Tetrachlorvinphos">Tetrachlorvinphos</a></li> <li><a href="/w/index.php?title=Tribufos&action=edit&redlink=1" class="new" title="Tribufos (page does not exist)">Tribufos</a></li> <li><a href="/wiki/Metrifonate" title="Metrifonate">Trichlorfon</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;background:PowderBlue;"><a href="/wiki/Pyrethroid" title="Pyrethroid">Pyrethroids</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/Acrinathrin" title="Acrinathrin">Acrinathrin</a></li> <li><a href="/wiki/Allethrins" title="Allethrins">Allethrins</a></li> <li><a href="/wiki/Bifenthrin" title="Bifenthrin">Bifenthrin</a></li> <li><a href="/wiki/Bioallethrin" title="Bioallethrin">Bioallethrin</a></li> <li><a href="/wiki/Cyfluthrin" title="Cyfluthrin">Cyfluthrin</a></li> <li><a href="/wiki/Cyhalothrin" title="Cyhalothrin">Cyhalothrin</a></li> <li><a href="/wiki/Cypermethrin" title="Cypermethrin">Cypermethrin</a></li> <li><a href="/wiki/Cyphenothrin" title="Cyphenothrin">Cyphenothrin</a></li> <li><a href="/wiki/Deltamethrin" title="Deltamethrin">Deltamethrin</a></li> <li><a href="/wiki/Empenthrin" title="Empenthrin">Empenthrin</a></li> <li><a href="/wiki/Esfenvalerate" title="Esfenvalerate">Esfenvalerate</a></li> <li><a href="/wiki/Etofenprox" title="Etofenprox">Etofenprox</a></li> <li><a href="/wiki/Fenpropathrin" title="Fenpropathrin">Fenpropathrin</a></li> <li><a href="/wiki/Fenvalerate" title="Fenvalerate">Fenvalerate</a></li> <li><a href="/wiki/Flumethrin" title="Flumethrin">Flumethrin</a></li> <li><a href="/wiki/Fluvalinate" title="Fluvalinate">Fluvalinate</a></li> <li><a href="/wiki/Imiprothrin" title="Imiprothrin">Imiprothrin</a></li> <li><a href="/wiki/Metofluthrin" title="Metofluthrin">Metofluthrin</a></li> <li><a href="/wiki/Permethrin" title="Permethrin">Permethrin</a></li> <li><a href="/wiki/Phenothrin" title="Phenothrin">Phenothrin</a></li> <li><a href="/wiki/Prallethrin" title="Prallethrin">Prallethrin</a></li> <li><a href="/wiki/Pyrethrin" title="Pyrethrin">Pyrethrin</a> (<a href="/wiki/Pyrethrin_I" title="Pyrethrin I">I</a>, <a href="/wiki/Pyrethrin_II" title="Pyrethrin II">II</a>; <a href="/wiki/Chrysanthemic_acid" title="Chrysanthemic acid">chrysanthemic acid</a>)</li> <li><a href="/wiki/Pyrethrum" title="Pyrethrum">Pyrethrum</a></li> <li><a href="/wiki/Resmethrin" title="Resmethrin">Resmethrin</a></li> <li><a href="/wiki/Silafluofen" title="Silafluofen">Silafluofen</a></li> <li><a href="/wiki/Tefluthrin" title="Tefluthrin">Tefluthrin</a></li> <li><a href="/wiki/Tetramethrin" title="Tetramethrin">Tetramethrin</a></li> <li><a href="/wiki/Tralomethrin" title="Tralomethrin">Tralomethrin</a></li> <li><a href="/wiki/Transfluthrin" title="Transfluthrin">Transfluthrin</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;background:PowderBlue;"><a href="/wiki/Diamide_insecticides" title="Diamide insecticides">Diamides</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/Chlorantraniliprole" title="Chlorantraniliprole">Chlorantraniliprole</a></li> <li><a href="/wiki/Cyantraniliprole" title="Cyantraniliprole">Cyantraniliprole</a></li> <li><a href="/wiki/Flubendiamide" title="Flubendiamide">Flubendiamide</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;background:PowderBlue;">Other chemicals</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/Afoxolaner" title="Afoxolaner">Afoxolaner</a></li> <li><a href="/wiki/Amitraz" title="Amitraz">Amitraz</a></li> <li><a href="/wiki/Azadirachtin" title="Azadirachtin">Azadirachtin</a></li> <li><a href="/wiki/Nereistoxin" title="Nereistoxin">Bensultap</a></li> <li><a href="/wiki/Buprofezin" title="Buprofezin">Buprofezin</a></li> <li><a href="/wiki/Nereistoxin" title="Nereistoxin">Cartap</a></li> <li><a href="/wiki/Chlordimeform" title="Chlordimeform">Chlordimeform</a></li> <li><a href="/wiki/Chlorfenapyr" title="Chlorfenapyr">Chlorfenapyr</a></li> <li><a href="/wiki/Cyromazine" title="Cyromazine">Cyromazine</a></li> <li><a href="/w/index.php?title=Fenazaquin&action=edit&redlink=1" class="new" title="Fenazaquin (page does not exist)">Fenazaquin</a></li> <li><a href="/wiki/Fenoxycarb" title="Fenoxycarb">Fenoxycarb</a></li> <li><a href="/wiki/Fipronil" title="Fipronil">Fipronil</a></li> <li><a href="/wiki/Fluralaner" title="Fluralaner">Fluralaner</a></li> <li><a href="/wiki/Hydramethylnon" title="Hydramethylnon">Hydramethylnon</a></li> <li><a href="/wiki/Indoxacarb" title="Indoxacarb">Indoxacarb</a></li> <li><a href="/wiki/Limonene" title="Limonene">Limonene</a></li> <li><a href="/wiki/Lotilaner" title="Lotilaner">Lotilaner</a> (<a href="/wiki/Lotilaner/milbemycin_oxime" class="mw-redirect" title="Lotilaner/milbemycin oxime">+milbemycin oxime</a>)</li> <li><a href="/w/index.php?title=Pyridaben&action=edit&redlink=1" class="new" title="Pyridaben (page does not exist)">Pyridaben</a></li> <li><a href="/wiki/Pyriprole" title="Pyriprole">Pyriprole</a></li> <li><a href="/wiki/Sarolaner" title="Sarolaner">Sarolaner</a></li> <li><a href="/wiki/Adjuvants" class="mw-redirect" title="Adjuvants">Adjuvants</a> (<a href="/wiki/Piperonyl_butoxide" title="Piperonyl butoxide">Piperonyl butoxide</a>, <a href="/wiki/Sesamex" title="Sesamex">Sesamex</a>)</li> <li><a href="/wiki/Spinosad" title="Spinosad">Spinosad</a></li> <li><a href="/wiki/Sulfluramid" title="Sulfluramid">Sulfluramid</a></li> <li><a href="/wiki/Tebufenozide" title="Tebufenozide">Tebufenozide</a></li> <li><a href="/wiki/Tebufenpyrad" title="Tebufenpyrad">Tebufenpyrad</a></li> <li><a href="/wiki/Veracevine" title="Veracevine">Veracevine</a></li> <li><a href="/wiki/Xanthone" title="Xanthone">Xanthone</a></li> <li><a href="/wiki/Metaflumizone" title="Metaflumizone">Metaflumizone</a></li> <li><a href="/wiki/Ryanodine" title="Ryanodine">Ryanodine</a></li> <li><a href="/w/index.php?title=Ryanodol&action=edit&redlink=1" class="new" title="Ryanodol (page does not exist)">Ryanodol</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;background:PowderBlue;"><a href="/wiki/Metabolite" title="Metabolite">Metabolites</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/Oxon_(chemical)" title="Oxon (chemical)">Oxon</a></li> <li><a href="/wiki/Malaoxon" title="Malaoxon">Malaoxon</a></li> <li><a href="/wiki/Paraoxon" title="Paraoxon">Paraoxon</a></li> <li><a href="/wiki/TCPy" title="TCPy">TCPy</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;background:PowderBlue;"><a href="/wiki/Biopesticide" title="Biopesticide">Biopesticides</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><i><a href="/wiki/Bacillus_thuringiensis" title="Bacillus thuringiensis">Bacillus thuringiensis</a></i></li> <li><a href="/wiki/Baculovirus" class="mw-redirect" title="Baculovirus">Baculovirus</a></li> <li><i><a href="/wiki/Beauveria_bassiana" title="Beauveria bassiana">Beauveria bassiana</a></i></li> <li><i><a href="/w/index.php?title=Beauveria_brongniartii&action=edit&redlink=1" class="new" title="Beauveria brongniartii (page does not exist)">Beauveria brongniartii</a></i></li> <li><i><a href="/wiki/Isaria_fumosorosea" title="Isaria fumosorosea">Isaria fumosorosea</a></i></li> <li><i><a href="/wiki/Metarhizium_acridum" title="Metarhizium acridum">Metarhizium acridum</a></i></li> <li><i><a href="/wiki/Metarhizium_anisopliae" title="Metarhizium anisopliae">Metarhizium anisopliae</a></i></li> <li><i><a href="/wiki/Nomuraea_rileyi" class="mw-redirect" title="Nomuraea rileyi">Nomuraea rileyi</a></i></li> <li><i><a href="/wiki/Lecanicillium_lecanii" title="Lecanicillium lecanii">Lecanicillium lecanii</a></i></li> <li><i><a href="/wiki/Paenibacillus_popilliae" class="mw-redirect" title="Paenibacillus popilliae">Paenibacillus popilliae</a></i></li> <li><i><a href="/wiki/Purpureocillium_lilacinum" title="Purpureocillium lilacinum">Purpureocillium lilacinum</a></i></li> <li><a href="/wiki/Spinosad" title="Spinosad">Spinosad</a></li></ul> </div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"></div><div role="navigation" class="navbox" aria-labelledby="Health_issues_of_plastics_and_polyhalogenated_compounds_(PHCs)" 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:Health_issues_of_plastics" title="Template:Health issues of plastics"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Health_issues_of_plastics" title="Template talk:Health issues of plastics"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Health_issues_of_plastics" title="Special:EditPage/Template:Health issues of plastics"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Health_issues_of_plastics_and_polyhalogenated_compounds_(PHCs)" style="font-size:114%;margin:0 4em">Health issues of <a href="/wiki/Plastic" title="Plastic">plastics</a> and <a href="/wiki/Polyhalogenated_compound" title="Polyhalogenated compound">polyhalogenated compounds</a> (PHCs)</div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Plasticizer" title="Plasticizer">Plasticizers</a>: <a href="/wiki/Phthalate" class="mw-redirect" title="Phthalate">Phthalates</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/Diisobutyl_phthalate" title="Diisobutyl phthalate">DIBP</a></li> <li><a href="/wiki/Dibutyl_phthalate" title="Dibutyl phthalate">DBP</a></li> <li><a href="/wiki/Benzyl_butyl_phthalate" title="Benzyl butyl phthalate">BBP</a> (BBzP)</li> <li><a href="/wiki/Diisoheptyl_phthalate" title="Diisoheptyl phthalate">DIHP</a></li> <li><a href="/wiki/Bis(2-ethylhexyl)_phthalate" title="Bis(2-ethylhexyl) phthalate">DEHP</a> (DOP)</li> <li><a href="/wiki/Diisodecyl_phthalate" title="Diisodecyl phthalate">DIDP</a></li> <li><a href="/wiki/Diisononyl_phthalate" title="Diisononyl phthalate">DINP</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Miscellaneous plasticizers</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 class="mw-selflink selflink">Organophosphates</a></li> <li><a href="/wiki/Adipic_acid" title="Adipic acid">Adipates</a> (<a href="/wiki/Bis(2-ethylhexyl)_adipate" title="Bis(2-ethylhexyl) adipate">DEHA</a></li> <li><a href="/wiki/Dioctyl_adipate" title="Dioctyl adipate">DOA</a>)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Monomer" title="Monomer">Monomers</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/Bisphenol_A" title="Bisphenol A">Bisphenol A</a> (BPA, in <a href="/wiki/Polycarbonate" title="Polycarbonate">Polycarbonates</a>)</li> <li><a href="/wiki/Vinyl_chloride" title="Vinyl chloride">Vinyl chloride</a> (in <a href="/wiki/Polyvinyl_chloride" title="Polyvinyl chloride">PVC</a>)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Miscellaneous additives incl. PHCs</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/Polybrominated_diphenyl_ethers" title="Polybrominated diphenyl ethers">PBDEs</a></li> <li><a href="/wiki/Polychlorinated_biphenyl" title="Polychlorinated biphenyl">PCBs</a></li> <li><a href="/wiki/Organotin" class="mw-redirect" title="Organotin">Organotins</a></li> <li><a href="/wiki/Perfluorinated_compounds" class="mw-redirect" title="Perfluorinated compounds">PFCs</a> <ul><li><a href="/wiki/Perfluorooctanoic_acid" title="Perfluorooctanoic acid">Perfluorooctanoic acid</a></li></ul></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Plastic#Toxicity" title="Plastic">Health issues</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/Teratogen" class="mw-redirect" title="Teratogen">Teratogen</a></li> <li><a href="/wiki/Carcinogen" title="Carcinogen">Carcinogen</a></li> <li><a href="/wiki/Endocrine_disruptor" title="Endocrine disruptor">Endocrine disruptor</a></li> <li><a href="/wiki/Diabetes" title="Diabetes">Diabetes</a></li> <li><a href="/wiki/Obesity" title="Obesity">Obesity</a></li> <li><a href="/wiki/Polymer_fume_fever" title="Polymer fume fever">Polymer fume fever</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Pollution</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/Plastic_pollution" title="Plastic pollution">Plastic pollution</a> <ul><li><a href="/wiki/Rubber_pollution" title="Rubber pollution">Rubber pollution</a></li></ul></li> <li><a href="/wiki/Great_Pacific_Garbage_Patch" title="Great Pacific Garbage Patch">Great Pacific Garbage Patch</a></li> <li><a href="/wiki/Persistent_organic_pollutant" title="Persistent organic pollutant">Persistent organic pollutant</a></li> <li><a href="/wiki/Polychlorinated_dibenzodioxins" title="Polychlorinated dibenzodioxins">Dioxins</a></li> <li><a href="/wiki/List_of_environmental_health_hazards" class="mw-redirect" title="List of environmental health hazards">List of environmental health hazards</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Regulations</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/1986_California_Proposition_65" title="1986 California Proposition 65">California Proposition 65</a></li> <li><a href="/wiki/Registration,_Evaluation,_Authorisation_and_Restriction_of_Chemicals" title="Registration, Evaluation, Authorisation and Restriction of Chemicals">European REACH regulation</a></li> <li><a href="/wiki/Kashinhou" title="Kashinhou">Japan Toxic Substances Law</a></li> <li><a href="/wiki/Toxic_Substances_Control_Act_of_1976" title="Toxic Substances Control Act of 1976">Toxic Substances Control Act</a></li></ul> </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="Acetylcholine_receptor_modulators" style="padding:3px"><table class="nowraplinks mw-collapsible mw-collapsed navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2" style="background:#e8e8ff;"><div id="Acetylcholine_receptor_modulators" style="font-size:114%;margin:0 4em"><a href="/wiki/Acetylcholine_receptor" title="Acetylcholine receptor">Acetylcholine receptor</a> <a href="/wiki/Receptor_modulator" title="Receptor modulator">modulators</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="Muscarinic_acetylcholine_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:Muscarinic_acetylcholine_receptor_modulators" title="Template:Muscarinic acetylcholine receptor modulators"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Muscarinic_acetylcholine_receptor_modulators" title="Template talk:Muscarinic acetylcholine receptor modulators"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Muscarinic_acetylcholine_receptor_modulators" title="Special:EditPage/Template:Muscarinic acetylcholine receptor modulators"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Muscarinic_acetylcholine_receptor_modulators" style="font-size:114%;margin:0 4em"><a href="/wiki/Muscarinic_acetylcholine_receptor" title="Muscarinic acetylcholine receptor">Muscarinic acetylcholine 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/Muscarinic_acetylcholine_receptors" class="mw-redirect" title="Muscarinic acetylcholine receptors"><abbr title="Muscarinic acetylcholine receptors">mAChRs</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 Muscarinic acetylcholine receptors</span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Muscarinic_agonist" title="Muscarinic agonist">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/77-LH-28-1" title="77-LH-28-1">77-LH-28-1</a></li> <li><a href="/wiki/AC-42" title="AC-42">AC-42</a></li> <li><a href="/w/index.php?title=AC-260,584&action=edit&redlink=1" class="new" title="AC-260,584 (page does not exist)">AC-260,584</a></li> <li><a href="/wiki/Aceclidine" title="Aceclidine">Aceclidine</a></li> <li><a href="/wiki/Acetylcholine" title="Acetylcholine">Acetylcholine</a></li> <li><a href="/w/index.php?title=AF30&action=edit&redlink=1" class="new" title="AF30 (page does not exist)">AF30</a></li> <li><a href="/w/index.php?title=AF150(S)&action=edit&redlink=1" class="new" title="AF150(S) (page does not exist)">AF150(S)</a></li> <li><a href="/w/index.php?title=AF267B&action=edit&redlink=1" class="new" title="AF267B (page does not exist)">AF267B</a></li> <li><a href="/wiki/Alvameline" title="Alvameline">Alvameline</a></li> <li><a href="/w/index.php?title=AQRA-741&action=edit&redlink=1" class="new" title="AQRA-741 (page does not exist)">AQRA-741</a></li> <li><a href="/wiki/Arecoline" title="Arecoline">Arecoline</a></li> <li><a href="/wiki/Bethanechol" title="Bethanechol">Bethanechol</a></li> <li><a href="/wiki/Butyrylcholine" title="Butyrylcholine">Butyrylcholine</a></li> <li><a href="/wiki/Carbachol" title="Carbachol">Carbachol</a></li> <li><a href="/w/index.php?title=CDD-0034&action=edit&redlink=1" class="new" title="CDD-0034 (page does not exist)">CDD-0034</a></li> <li><a href="/w/index.php?title=CDD-0078&action=edit&redlink=1" class="new" title="CDD-0078 (page does not exist)">CDD-0078</a></li> <li><a href="/w/index.php?title=CDD-0097&action=edit&redlink=1" class="new" title="CDD-0097 (page does not exist)">CDD-0097</a></li> <li><a href="/w/index.php?title=CDD-0098&action=edit&redlink=1" class="new" title="CDD-0098 (page does not exist)">CDD-0098</a></li> <li><a href="/w/index.php?title=CDD-0102&action=edit&redlink=1" class="new" title="CDD-0102 (page does not exist)">CDD-0102</a></li> <li><a href="/wiki/Cevimeline" title="Cevimeline">Cevimeline</a></li> <li><a href="/wiki/Choline" title="Choline">Choline</a></li> <li><a href="/wiki/Cis-Dioxolane" class="mw-redirect" title="Cis-Dioxolane">cis-Dioxolane</a></li> <li><a href="/wiki/Clozapine" title="Clozapine">Clozapine</a></li> <li><a href="/wiki/Desmethylclozapine" title="Desmethylclozapine">Desmethylclozapine (norclozapine)</a></li> <li><a href="/w/index.php?title=Ethoxysebacylcholine&action=edit&redlink=1" class="new" title="Ethoxysebacylcholine (page does not exist)">Ethoxysebacylcholine</a></li> <li><a href="/wiki/Itameline" title="Itameline">Itameline</a></li> <li><a href="/w/index.php?title=LY-593,039&action=edit&redlink=1" class="new" title="LY-593,039 (page does not exist)">LY-593,039</a></li> <li><a href="/w/index.php?title=L-689,660&action=edit&redlink=1" class="new" title="L-689,660 (page does not exist)">L-689,660</a></li> <li><a href="/w/index.php?title=LY-2,033,298&action=edit&redlink=1" class="new" title="LY-2,033,298 (page does not exist)">LY-2,033,298</a></li> <li><a href="/w/index.php?title=McNA343&action=edit&redlink=1" class="new" title="McNA343 (page does not exist)">McNA343</a></li> <li><a href="/wiki/Methacholine" title="Methacholine">Methacholine</a></li> <li><a href="/wiki/Milameline" title="Milameline">Milameline</a></li> <li><a href="/wiki/Muscarine" title="Muscarine">Muscarine</a></li> <li><a href="/w/index.php?title=NGX-267&action=edit&redlink=1" class="new" title="NGX-267 (page does not exist)">NGX-267</a></li> <li><a href="/w/index.php?title=Ocvimeline&action=edit&redlink=1" class="new" title="Ocvimeline (page does not exist)">Ocvimeline</a></li> <li><a href="/wiki/Oxotremorine" title="Oxotremorine">Oxotremorine</a></li> <li><a href="/w/index.php?title=PD-151,832&action=edit&redlink=1" class="new" title="PD-151,832 (page does not exist)">PD-151,832</a></li> <li><a href="/wiki/Pilocarpine" title="Pilocarpine">Pilocarpine</a></li> <li><a href="/w/index.php?title=RS86&action=edit&redlink=1" class="new" title="RS86 (page does not exist)">RS86</a></li> <li><a href="/wiki/Sabcomeline" title="Sabcomeline">Sabcomeline</a></li> <li><a href="/w/index.php?title=SDZ_210-086&action=edit&redlink=1" class="new" title="SDZ 210-086 (page does not exist)">SDZ 210-086</a></li> <li><a href="/w/index.php?title=Sebacylcholine&action=edit&redlink=1" class="new" title="Sebacylcholine (page does not exist)">Sebacylcholine</a></li> <li><a href="/w/index.php?title=Suberyldicholine&action=edit&redlink=1" class="new" title="Suberyldicholine (page does not exist)">Suberyldicholine</a></li> <li><a href="/wiki/Talsaclidine" title="Talsaclidine">Talsaclidine</a></li> <li><a href="/wiki/Tazomeline" title="Tazomeline">Tazomeline</a></li> <li><a href="/w/index.php?title=Thiopilocarpine&action=edit&redlink=1" class="new" title="Thiopilocarpine (page does not exist)">Thiopilocarpine</a></li> <li><a href="/wiki/Vedaclidine" title="Vedaclidine">Vedaclidine</a></li> <li><a href="/w/index.php?title=VU-0029767&action=edit&redlink=1" class="new" title="VU-0029767 (page does not exist)">VU-0029767</a></li> <li><a href="/w/index.php?title=VU-0090157&action=edit&redlink=1" class="new" title="VU-0090157 (page does not exist)">VU-0090157</a></li> <li><a href="/wiki/VU-0152099" title="VU-0152099">VU-0152099</a></li> <li><a href="/wiki/VU-0152100" title="VU-0152100">VU-0152100</a></li> <li><a href="/wiki/VU-0238429" title="VU-0238429">VU-0238429</a></li> <li><a href="/w/index.php?title=WAY-132,983&action=edit&redlink=1" class="new" title="WAY-132,983 (page does not exist)">WAY-132,983</a></li> <li><a href="/wiki/Xanomeline" title="Xanomeline">Xanomeline</a></li> <li><a href="/w/index.php?title=YM-796&action=edit&redlink=1" class="new" title="YM-796 (page does not exist)">YM-796</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Muscarinic_antagonist" title="Muscarinic antagonist">Antagonists</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/3-Quinuclidinyl_benzilate" title="3-Quinuclidinyl benzilate">3-Quinuclidinyl benzilate</a></li> <li><a href="/wiki/4-DAMP" title="4-DAMP">4-DAMP</a></li> <li><a href="/wiki/Aclidinium_bromide" title="Aclidinium bromide">Aclidinium bromide</a> (<a href="/wiki/Aclidinium_bromide/formoterol" title="Aclidinium bromide/formoterol">+formoterol</a>)</li> <li><a href="/wiki/Abediterol" title="Abediterol">Abediterol</a></li> <li><a href="/w/index.php?title=AF-DX_250&action=edit&redlink=1" class="new" title="AF-DX 250 (page does not exist)">AF-DX 250</a></li> <li><a href="/wiki/AFDX-384" title="AFDX-384">AF-DX 384</a></li> <li><a href="/wiki/Ambutonium_bromide" title="Ambutonium bromide">Ambutonium bromide</a></li> <li><a href="/wiki/Anisodamine" title="Anisodamine">Anisodamine</a></li> <li><a href="/wiki/Anisodine" title="Anisodine">Anisodine</a></li> <li><a href="/wiki/First-generation_antihistamine" class="mw-redirect" title="First-generation antihistamine">Antihistamines (first-generation)</a> (e.g., <a href="/wiki/Brompheniramine" title="Brompheniramine">brompheniramine</a>, <a href="/wiki/Buclizine" title="Buclizine">buclizine</a>, <a href="/wiki/Captodiame" title="Captodiame">captodiame</a>, <a href="/wiki/Chlorphenamine" title="Chlorphenamine">chlorphenamine (chlorpheniramine)</a>, <a href="/wiki/Cinnarizine" title="Cinnarizine">cinnarizine</a>, <a href="/wiki/Clemastine" title="Clemastine">clemastine</a>, <a href="/wiki/Cyproheptadine" title="Cyproheptadine">cyproheptadine</a>, <a href="/wiki/Dimenhydrinate" title="Dimenhydrinate">dimenhydrinate</a>, <a href="/wiki/Dimetindene" title="Dimetindene">dimetindene</a>, <a href="/wiki/Diphenhydramine" title="Diphenhydramine">diphenhydramine</a>, <a href="/wiki/Doxylamine" title="Doxylamine">doxylamine</a>, <a href="/wiki/Meclizine" title="Meclizine">meclizine</a>, <a href="/wiki/Mequitazine" title="Mequitazine">mequitazine</a>, <a href="/wiki/Perlapine" title="Perlapine">perlapine</a>, <a href="/wiki/Phenindamine" title="Phenindamine">phenindamine</a>, <a href="/wiki/Pheniramine" title="Pheniramine">pheniramine</a>, <a href="/wiki/Phenyltoloxamine" title="Phenyltoloxamine">phenyltoloxamine</a>, <a href="/wiki/Promethazine" title="Promethazine">promethazine</a>, <a href="/wiki/Propiomazine" title="Propiomazine">propiomazine</a>, <a href="/wiki/Triprolidine" title="Triprolidine">triprolidine</a>)</li> <li><a href="/w/index.php?title=AQ-RA_741&action=edit&redlink=1" class="new" title="AQ-RA 741 (page does not exist)">AQ-RA 741</a></li> <li><a href="/wiki/Atropine" title="Atropine">Atropine</a></li> <li><a href="/wiki/Atropine_methonitrate" class="mw-redirect" title="Atropine methonitrate">Atropine methonitrate</a></li> <li><a href="/wiki/Atypical_antipsychotic" title="Atypical antipsychotic">Atypical antipsychotics</a> (e.g., <a href="/wiki/Clozapine" title="Clozapine">clozapine</a>, <a href="/wiki/Fluperlapine" title="Fluperlapine">fluperlapine</a>, <a href="/wiki/Olanzapine" title="Olanzapine">olanzapine</a> (<a href="/wiki/Olanzapine/fluoxetine" title="Olanzapine/fluoxetine">+fluoxetine</a>), <a href="/w/index.php?title=Rilapine&action=edit&redlink=1" class="new" title="Rilapine (page does not exist)">rilapine</a>, <a href="/wiki/Quetiapine" title="Quetiapine">quetiapine</a>, <a href="/wiki/Tenilapine" title="Tenilapine">tenilapine</a>, <a href="/wiki/Zotepine" title="Zotepine">zotepine</a>)</li> <li><a href="/wiki/Benactyzine" title="Benactyzine">Benactyzine</a></li> <li><a href="/wiki/Benzatropine" title="Benzatropine">Benzatropine (benztropine)</a></li> <li><a href="/wiki/Benzilone" title="Benzilone">Benzilone</a></li> <li><a href="/wiki/Benzilylcholine_mustard" title="Benzilylcholine mustard">Benzilylcholine mustard</a></li> <li><a href="/wiki/Benzydamine" title="Benzydamine">Benzydamine</a></li> <li><a href="/wiki/Bevonium" title="Bevonium">Bevonium</a></li> <li><a href="/w/index.php?title=BIBN_99&action=edit&redlink=1" class="new" title="BIBN 99 (page does not exist)">BIBN 99</a></li> <li><a href="/wiki/Biperiden" title="Biperiden">Biperiden</a></li> <li><a href="/wiki/Bornaprine" title="Bornaprine">Bornaprine</a></li> <li><a href="/wiki/Camylofin" title="Camylofin">Camylofin</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/Caramiphen" title="Caramiphen">Caramiphen</a></li> <li><a href="/wiki/Cimetropium_bromide" title="Cimetropium bromide">Cimetropium bromide</a></li> <li><a href="/wiki/Clidinium_bromide" title="Clidinium bromide">Clidinium bromide</a></li> <li><a href="/wiki/Cloperastine" title="Cloperastine">Cloperastine</a></li> <li><a href="/wiki/CS-27349" title="CS-27349">CS-27349</a></li> <li><a href="/wiki/Cyclobenzaprine" title="Cyclobenzaprine">Cyclobenzaprine</a></li> <li><a href="/wiki/Cyclopentolate" title="Cyclopentolate">Cyclopentolate</a></li> <li><a href="/wiki/Darifenacin" title="Darifenacin">Darifenacin</a></li> <li><a href="/w/index.php?title=DAU-5884&action=edit&redlink=1" class="new" title="DAU-5884 (page does not exist)">DAU-5884</a></li> <li><a href="/wiki/Desfesoterodine" title="Desfesoterodine">Desfesoterodine</a></li> <li><a href="/wiki/Dexetimide" title="Dexetimide">Dexetimide</a></li> <li><a href="/w/index.php?title=DIBD&action=edit&redlink=1" class="new" title="DIBD (page does not exist)">DIBD</a></li> <li><a href="/wiki/Dicycloverine" title="Dicycloverine">Dicycloverine (dicyclomine)</a></li> <li><a href="/wiki/Dihexyverine" title="Dihexyverine">Dihexyverine</a></li> <li><a href="/wiki/Difemerine" title="Difemerine">Difemerine</a></li> <li><a href="/wiki/Diphemanil_metilsulfate" title="Diphemanil metilsulfate">Diphemanil metilsulfate</a></li> <li><a href="/wiki/Ditran" title="Ditran">Ditran</a></li> <li><a href="/wiki/Drofenine" title="Drofenine">Drofenine</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/Emepronium_bromide" title="Emepronium bromide">Emepronium bromide</a></li> <li><a href="/wiki/Etanautine" title="Etanautine">Etanautine</a></li> <li><a href="/wiki/Etybenzatropine" title="Etybenzatropine">Etybenzatropine (ethybenztropine)</a></li> <li><a href="/wiki/Fenpiverinium" title="Fenpiverinium">Fenpiverinium</a></li> <li><a href="/wiki/Fentonium_bromide" title="Fentonium bromide">Fentonium bromide</a></li> <li><a href="/wiki/Fesoterodine" title="Fesoterodine">Fesoterodine</a></li> <li><a href="/wiki/Flavoxate" title="Flavoxate">Flavoxate</a></li> <li><a href="/wiki/Glycopyrronium_bromide" title="Glycopyrronium bromide">Glycopyrronium bromide</a> (<a href="/wiki/Beclometasone/formoterol/glycopyrronium_bromide" title="Beclometasone/formoterol/glycopyrronium bromide">+beclometasone/formoterol</a>, <a href="/wiki/Indacaterol/glycopyrronium_bromide" title="Indacaterol/glycopyrronium bromide">+indacaterol</a>, <a href="/wiki/Neostigmine/glycopyrronium_bromide" title="Neostigmine/glycopyrronium bromide">+neostigmine</a>)</li> <li><a href="/w/index.php?title=Hexahydrodifenidol&action=edit&redlink=1" class="new" title="Hexahydrodifenidol (page does not exist)">Hexahydrodifenidol</a></li> <li><a href="/w/index.php?title=Hexahydrosiladifenidol&action=edit&redlink=1" class="new" title="Hexahydrosiladifenidol (page does not exist)">Hexahydrosiladifenidol</a></li> <li><a href="/w/index.php?title=Hexbutinol&action=edit&redlink=1" class="new" title="Hexbutinol (page does not exist)">Hexbutinol</a></li> <li><a href="/wiki/Hexocyclium" title="Hexocyclium">Hexocyclium</a></li> <li><a href="/wiki/Himbacine" title="Himbacine">Himbacine</a></li> <li><a href="/w/index.php?title=HL-031,120&action=edit&redlink=1" class="new" title="HL-031,120 (page does not exist)">HL-031,120</a></li> <li><a href="/wiki/Homatropine" title="Homatropine">Homatropine</a></li> <li><a href="/wiki/Imidafenacin" title="Imidafenacin">Imidafenacin</a></li> <li><a href="/wiki/Ipratropium_bromide" title="Ipratropium bromide">Ipratropium bromide</a> (<a href="/wiki/Ipratropium_bromide/salbutamol" title="Ipratropium bromide/salbutamol">+salbutamol</a>)</li> <li><a href="/wiki/Isopropamide" title="Isopropamide">Isopropamide</a></li> <li><a href="/w/index.php?title=J-104,129&action=edit&redlink=1" class="new" title="J-104,129 (page does not exist)">J-104,129</a></li> <li><a href="/wiki/Hyoscyamine" title="Hyoscyamine">Hyoscyamine</a></li> <li><a href="/wiki/Mamba#Mamba_toxins" title="Mamba">Mamba toxin 3</a></li> <li><a href="/wiki/Mamba#Mamba_toxins" title="Mamba">Mamba toxin 7</a></li> <li><a href="/wiki/Mazaticol" title="Mazaticol">Mazaticol</a></li> <li><a href="/wiki/Mebeverine" title="Mebeverine">Mebeverine</a></li> <li><a href="/wiki/Meladrazine" title="Meladrazine">Meladrazine</a></li> <li><a href="/wiki/Mepenzolate" title="Mepenzolate">Mepenzolate</a></li> <li><a href="/wiki/Methantheline" title="Methantheline">Methantheline</a></li> <li><a href="/wiki/Methoctramine" title="Methoctramine">Methoctramine</a></li> <li><a href="/wiki/Methylatropine" title="Methylatropine">Methylatropine</a></li> <li><a href="/wiki/Methylhomatropine" class="mw-redirect" title="Methylhomatropine">Methylhomatropine</a></li> <li><a href="/wiki/Methylscopolamine_bromide" title="Methylscopolamine bromide">Methylscopolamine</a></li> <li><a href="/wiki/Metixene" title="Metixene">Metixene</a></li> <li><a href="/wiki/Muscarinic_toxin_7" title="Muscarinic toxin 7">Muscarinic toxin 7</a></li> <li><a href="/wiki/N-Ethyl-3-piperidyl_benzilate" title="N-Ethyl-3-piperidyl benzilate">N-Ethyl-3-piperidyl benzilate</a></li> <li><a href="/wiki/N-Methyl-3-piperidyl_benzilate" title="N-Methyl-3-piperidyl benzilate">N-Methyl-3-piperidyl benzilate</a></li> <li><a href="/wiki/Nefopam" title="Nefopam">Nefopam</a></li> <li><a href="/wiki/Octatropine_methylbromide" title="Octatropine methylbromide">Octatropine methylbromide (anisotropine methylbromide)</a></li> <li><a href="/wiki/Orphenadrine" title="Orphenadrine">Orphenadrine</a></li> <li><a href="/wiki/Otenzepad" title="Otenzepad">Otenzepad (AF-DX 116)</a></li> <li><a href="/wiki/Otilonium_bromide" title="Otilonium bromide">Otilonium bromide</a></li> <li><a href="/wiki/Oxapium_iodide" title="Oxapium iodide">Oxapium iodide</a></li> <li><a href="/wiki/Oxitropium_bromide" title="Oxitropium bromide">Oxitropium bromide</a></li> <li><a href="/wiki/Oxybutynin" title="Oxybutynin">Oxybutynin</a></li> <li><a href="/wiki/Oxyphencyclimine" title="Oxyphencyclimine">Oxyphencyclimine</a></li> <li><a href="/wiki/Oxyphenonium_bromide" title="Oxyphenonium bromide">Oxyphenonium bromide</a></li> <li><a href="/w/index.php?title=PBID&action=edit&redlink=1" class="new" title="PBID (page does not exist)">PBID</a></li> <li><a href="/wiki/PD-102,807" title="PD-102,807">PD-102,807</a></li> <li><a href="/wiki/PD-0298029" title="PD-0298029">PD-0298029</a></li> <li><a href="/wiki/Penthienate" title="Penthienate">Penthienate</a></li> <li><a href="/wiki/Pethidine" title="Pethidine">Pethidine</a></li> <li><a href="/w/index.php?title=PFHHSiD&action=edit&redlink=1" class="new" title="PFHHSiD (page does not exist)">pFHHSiD</a></li> <li><a href="/wiki/Phenglutarimide" title="Phenglutarimide">Phenglutarimide</a></li> <li><a href="/wiki/Phenyltoloxamine" title="Phenyltoloxamine">Phenyltoloxamine</a></li> <li><a href="/wiki/Pipenzolate_bromide" title="Pipenzolate bromide">Pipenzolate bromide</a></li> <li><a href="/wiki/Piperidolate" title="Piperidolate">Piperidolate</a></li> <li><a href="/wiki/Pirenzepine" title="Pirenzepine">Pirenzepine</a></li> <li><a href="/wiki/Piroheptine" title="Piroheptine">Piroheptine</a></li> <li><a href="/wiki/Pizotifen" title="Pizotifen">Pizotifen</a></li> <li><a href="/wiki/Poldine" title="Poldine">Poldine</a></li> <li><a href="/wiki/Pridinol" title="Pridinol">Pridinol</a></li> <li><a href="/wiki/Prifinium_bromide" title="Prifinium bromide">Prifinium bromide</a></li> <li><a href="/wiki/Procyclidine" title="Procyclidine">Procyclidine</a></li> <li><a href="/wiki/Profenamine" title="Profenamine">Profenamine (ethopropazine)</a></li> <li><a href="/wiki/Propantheline_bromide" title="Propantheline bromide">Propantheline bromide</a></li> <li><a href="/wiki/Propiverine" title="Propiverine">Propiverine</a></li> <li><a href="/wiki/Quinidine" title="Quinidine">Quinidine</a></li> <li><a href="/wiki/3-Quinuclidinyl_thiochromane-4-carboxylate" title="3-Quinuclidinyl thiochromane-4-carboxylate">3-Quinuclidinyl thiochromane-4-carboxylate</a></li> <li><a href="/wiki/Revefenacin" title="Revefenacin">Revefenacin</a></li> <li><a href="/wiki/Rociverine" title="Rociverine">Rociverine</a></li> <li><a href="/w/index.php?title=RU-47,213&action=edit&redlink=1" class="new" title="RU-47,213 (page does not exist)">RU-47,213</a></li> <li><a href="/w/index.php?title=SCH-57,790&action=edit&redlink=1" class="new" title="SCH-57,790 (page does not exist)">SCH-57,790</a></li> <li><a href="/w/index.php?title=SCH-72,788&action=edit&redlink=1" class="new" title="SCH-72,788 (page does not exist)">SCH-72,788</a></li> <li><a href="/w/index.php?title=SCH-217,443&action=edit&redlink=1" class="new" title="SCH-217,443 (page does not exist)">SCH-217,443</a></li> <li><a href="/wiki/Hyoscine" class="mw-redirect" title="Hyoscine">Scopolamine (hyoscine)</a></li> <li><a href="/wiki/Hyoscine_butylbromide" title="Hyoscine butylbromide">Scopolamine butylbromide (hyoscine butylbromide)</a></li> <li><a href="/w/index.php?title=Silahexacyclium&action=edit&redlink=1" class="new" title="Silahexacyclium (page does not exist)">Silahexacyclium</a></li> <li><a href="/wiki/Sofpironium_bromide" title="Sofpironium bromide">Sofpironium bromide</a></li> <li><a href="/wiki/Solifenacin" title="Solifenacin">Solifenacin</a></li> <li><a href="/wiki/Selective_serotonin_reuptake_inhibitors" class="mw-redirect" title="Selective serotonin reuptake inhibitors"><abbr title="Selective serotonin reuptake inhibitors">SSRIs</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 Selective serotonin reuptake inhibitors</span> (e.g., <a href="/wiki/Femoxetine" title="Femoxetine">femoxetine</a>, <a href="/wiki/Paroxetine" title="Paroxetine">paroxetine</a>)</li> <li><a href="/wiki/Telenzepine" title="Telenzepine">Telenzepine</a></li> <li><a href="/wiki/Terodiline" title="Terodiline">Terodiline</a></li> <li><a href="/wiki/Tetracyclic_antidepressant" title="Tetracyclic antidepressant">Tetracyclic antidepressants</a> (e.g., <a href="/wiki/Amoxapine" title="Amoxapine">amoxapine</a>, <a href="/wiki/Maprotiline" title="Maprotiline">maprotiline</a>, <a href="/wiki/Mianserin" title="Mianserin">mianserin</a>, <a href="/wiki/Mirtazapine" title="Mirtazapine">mirtazapine</a>)</li> <li><a href="/wiki/Tiemonium_iodide" title="Tiemonium iodide">Tiemonium iodide</a></li> <li><a href="/wiki/Timepidium_bromide" title="Timepidium bromide">Timepidium bromide</a></li> <li><a href="/wiki/Tiotropium_bromide" title="Tiotropium bromide">Tiotropium bromide</a></li> <li><a href="/w/index.php?title=Tiquizium_bromide&action=edit&redlink=1" class="new" title="Tiquizium bromide (page does not exist)">Tiquizium bromide</a></li> <li><a href="/wiki/Tofenacin" title="Tofenacin">Tofenacin</a></li> <li><a href="/wiki/Tolterodine" title="Tolterodine">Tolterodine</a></li> <li><a href="/wiki/Tricyclic_antidepressant" title="Tricyclic antidepressant">Tricyclic antidepressants</a> (e.g., <a href="/wiki/Amitriptyline" title="Amitriptyline">amitriptyline</a> (<a href="/wiki/Amitriptyline/perphenazine" title="Amitriptyline/perphenazine">+perphenazine</a>), <a href="/wiki/Amitriptylinoxide" title="Amitriptylinoxide">amitriptylinoxide</a>, <a href="/wiki/Butriptyline" title="Butriptyline">butriptyline</a>, <a href="/wiki/Cidoxepin" title="Cidoxepin">cidoxepin</a>, <a href="/wiki/Clomipramine" title="Clomipramine">clomipramine</a>, <a href="/wiki/Desipramine" title="Desipramine">desipramine</a>, <a href="/w/index.php?title=Desmethyldesipramine&action=edit&redlink=1" class="new" title="Desmethyldesipramine (page does not exist)">desmethyldesipramine</a>, <a href="/wiki/Dibenzepin" title="Dibenzepin">dibenzepin</a>, <a href="/wiki/Dosulepin" title="Dosulepin">dosulepin (dothiepin)</a>, <a href="/wiki/Doxepin" title="Doxepin">doxepin</a>, <a href="/wiki/Imipramine" title="Imipramine">imipramine</a>, <a href="/wiki/Lofepramine" title="Lofepramine">lofepramine</a>, <a href="/wiki/Nitroxazepine" title="Nitroxazepine">nitroxazepine</a>, <a href="/wiki/Northiaden" title="Northiaden">northiaden (desmethyldosulepin)</a>, <a href="/wiki/Nortriptyline" title="Nortriptyline">nortriptyline</a>, <a href="/wiki/Protriptyline" title="Protriptyline">protriptyline</a>, <a href="/wiki/Quinupramine" title="Quinupramine">quinupramine</a>, <a href="/wiki/Trimipramine" title="Trimipramine">trimipramine</a>)</li> <li><a href="/wiki/Tridihexethyl" title="Tridihexethyl">Tridihexethyl</a></li> <li><a href="/wiki/Trihexyphenidyl" title="Trihexyphenidyl">Trihexyphenidyl</a></li> <li><a href="/wiki/Trimebutine" title="Trimebutine">Trimebutine</a></li> <li><a href="/wiki/Tripitamine" class="mw-redirect" title="Tripitamine">Tripitamine (tripitramine)</a></li> <li><a href="/w/index.php?title=Tropacine&action=edit&redlink=1" class="new" title="Tropacine (page does not exist)">Tropacine</a></li> <li><a href="/wiki/Tropatepine" title="Tropatepine">Tropatepine</a></li> <li><a href="/wiki/Tropicamide" title="Tropicamide">Tropicamide</a></li> <li><a href="/wiki/Trospium_chloride" title="Trospium chloride">Trospium chloride</a></li> <li><a href="/wiki/Typical_antipsychotic" title="Typical antipsychotic">Typical antipsychotics</a> (e.g., <a href="/wiki/Chlorpromazine" title="Chlorpromazine">chlorpromazine</a>, <a href="/wiki/Chlorprothixene" title="Chlorprothixene">chlorprothixene</a>, <a href="/wiki/Cyamemazine" title="Cyamemazine">cyamemazine (cyamepromazine)</a>, <a href="/wiki/Loxapine" title="Loxapine">loxapine</a>, <a href="/wiki/Mesoridazine" title="Mesoridazine">mesoridazine</a>, <a href="/wiki/Thioridazine" title="Thioridazine">thioridazine</a>)</li> <li><a href="/wiki/Umeclidinium_bromide" title="Umeclidinium bromide">Umeclidinium bromide</a> (<a href="/wiki/Umeclidinium_bromide/vilanterol" title="Umeclidinium bromide/vilanterol">+vilanterol</a>)</li> <li><a href="/wiki/WIN-2299" title="WIN-2299">WIN-2299</a></li> <li><a href="/wiki/Xanomeline" title="Xanomeline">Xanomeline</a></li> <li><a href="/w/index.php?title=Zamifenacin&action=edit&redlink=1" class="new" title="Zamifenacin (page does not exist)">Zamifenacin</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Precursor_(chemistry)" title="Precursor (chemistry)">Precursors</a><br /><small>(and <a href="/wiki/Prodrug" title="Prodrug">prodrugs</a>)</small></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/Acetyl-coA" class="mw-redirect" title="Acetyl-coA">Acetyl-coA</a></li> <li><a href="/wiki/Adafenoxate" title="Adafenoxate">Adafenoxate</a></li> <li><a href="/wiki/Choline" title="Choline">Choline</a> (<a href="/wiki/Lecithin" title="Lecithin">lecithin</a>)</li> <li><a href="/wiki/Citicoline" title="Citicoline">Citicoline</a></li> <li><a href="/wiki/Cyprodenate" title="Cyprodenate">Cyprodenate</a></li> <li><a href="/wiki/Dimethylethanolamine" title="Dimethylethanolamine">Dimethylethanolamine</a></li> <li><a href="/wiki/Glycerophosphocholine" class="mw-redirect" title="Glycerophosphocholine">Glycerophosphocholine</a></li> <li><a href="/wiki/Meclofenoxate" title="Meclofenoxate">Meclofenoxate (centrophenoxine)</a></li> <li><a href="/wiki/Phosphatidylcholine" title="Phosphatidylcholine">Phosphatidylcholine</a></li> <li><a href="/wiki/Phosphatidylethanolamine" title="Phosphatidylethanolamine">Phosphatidylethanolamine</a></li> <li><a href="/wiki/Phosphorylcholine" title="Phosphorylcholine">Phosphorylcholine</a></li> <li><a href="/wiki/Pirisudanol" title="Pirisudanol">Pirisudanol</a></li></ul> </div></td></tr><tr><td class="navbox-abovebelow" colspan="2"><div> <dl><dt>See also</dt> <dd><a href="/wiki/Template:Receptor_modulators" title="Template:Receptor modulators">Receptor/signaling modulators</a></dd> <dd><a href="/wiki/Template:Nicotinic_acetylcholine_receptor_modulators" title="Template:Nicotinic acetylcholine receptor modulators">Nicotinic acetylcholine receptor modulators</a></dd> <dd><a href="/wiki/Template:Acetylcholine_metabolism_and_transport_modulators" title="Template:Acetylcholine metabolism and transport modulators">Acetylcholine metabolism/transport modulators</a></dd></dl> </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="Nicotinic_acetylcholine_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:Nicotinic_acetylcholine_receptor_modulators" title="Template:Nicotinic acetylcholine receptor modulators"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Nicotinic_acetylcholine_receptor_modulators" title="Template talk:Nicotinic acetylcholine receptor modulators"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Nicotinic_acetylcholine_receptor_modulators" title="Special:EditPage/Template:Nicotinic acetylcholine receptor modulators"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Nicotinic_acetylcholine_receptor_modulators" style="font-size:114%;margin:0 4em"><a href="/wiki/Nicotinic_acetylcholine_receptor" title="Nicotinic acetylcholine receptor">Nicotinic acetylcholine 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/Nicotinic_acetylcholine_receptors" class="mw-redirect" title="Nicotinic acetylcholine receptors"><abbr title="Nicotinic acetylcholine receptors">nAChRs</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 Nicotinic acetylcholine receptors</span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Receptor_agonist" class="mw-redirect" title="Receptor agonist">Agonists</a><br />(and <a href="/wiki/Positive_allosteric_modulators" class="mw-redirect" title="Positive allosteric modulators"><abbr title="positive allosteric modulators">PAMs</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 positive allosteric modulators</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><a href="/wiki/5-Hydroxyindoleacetic_acid" title="5-Hydroxyindoleacetic acid">5-HIAA</a></li> <li><a href="/wiki/6-Chloronicotine" title="6-Chloronicotine">6-Chloronicotine</a></li> <li><a href="/wiki/A-84,543" title="A-84,543">A-84,543</a></li> <li><a href="/wiki/A-366,833" title="A-366,833">A-366,833</a></li> <li><a href="/w/index.php?title=A-582,941&action=edit&redlink=1" class="new" title="A-582,941 (page does not exist)">A-582,941</a></li> <li><a href="/w/index.php?title=A-867,744&action=edit&redlink=1" class="new" title="A-867,744 (page does not exist)">A-867,744</a></li> <li><a href="/wiki/ABT-202" title="ABT-202">ABT-202</a></li> <li><a href="/wiki/ABT-418" title="ABT-418">ABT-418</a></li> <li><a href="/w/index.php?title=ABT-560&action=edit&redlink=1" class="new" title="ABT-560 (page does not exist)">ABT-560</a></li> <li><a href="/w/index.php?title=ABT-894&action=edit&redlink=1" class="new" title="ABT-894 (page does not exist)">ABT-894</a></li> <li><a href="/wiki/Acetylcholine" title="Acetylcholine">Acetylcholine</a></li> <li><a href="/wiki/Altinicline" title="Altinicline">Altinicline</a></li> <li><a href="/wiki/Anabasine" title="Anabasine">Anabasine</a></li> <li><a href="/wiki/Anatabine" title="Anatabine">Anatabine</a></li> <li><a href="/wiki/Anatoxin-a" title="Anatoxin-a">Anatoxin-a</a></li> <li><a href="/wiki/AR-R17779" title="AR-R17779">AR-R17779</a></li> <li><a href="/wiki/Bephenium_hydroxynaphthoate" title="Bephenium hydroxynaphthoate">Bephenium hydroxynaphthoate</a></li> <li><a href="/wiki/Butinoline" title="Butinoline">Butinoline</a></li> <li><a href="/wiki/Butyrylcholine" title="Butyrylcholine">Butyrylcholine</a></li> <li><a href="/wiki/Carbachol" title="Carbachol">Carbachol</a></li> <li><a href="/wiki/Choline" title="Choline">Choline</a></li> <li><a href="/wiki/Cotinine" title="Cotinine">Cotinine</a></li> <li><a href="/wiki/Cytisine" title="Cytisine">Cytisine</a></li> <li><a href="/wiki/Decamethonium" title="Decamethonium">Decamethonium</a></li> <li><a href="/wiki/Desformylflustrabromine" title="Desformylflustrabromine">Desformylflustrabromine</a></li> <li><a href="/wiki/Dianicline" title="Dianicline">Dianicline</a></li> <li><a href="/wiki/Dimethylphenylpiperazinium" title="Dimethylphenylpiperazinium">Dimethylphenylpiperazinium</a></li> <li><a href="/wiki/Epibatidine" title="Epibatidine">Epibatidine</a></li> <li><a href="/wiki/Epiboxidine" title="Epiboxidine">Epiboxidine</a></li> <li><a href="/wiki/Alcohol_(drug)" title="Alcohol (drug)">Ethanol (alcohol)</a></li> <li><a href="/w/index.php?title=Ethoxysebacylcholine&action=edit&redlink=1" class="new" title="Ethoxysebacylcholine (page does not exist)">Ethoxysebacylcholine</a></li> <li><a href="/w/index.php?title=EVP-4473&action=edit&redlink=1" class="new" title="EVP-4473 (page does not exist)">EVP-4473</a></li> <li><a href="/wiki/EVP-6124" class="mw-redirect" title="EVP-6124">EVP-6124</a></li> <li><a href="/wiki/Galantamine" title="Galantamine">Galantamine</a></li> <li><a href="/wiki/GTS-21" title="GTS-21">GTS-21</a></li> <li><a href="/wiki/Ispronicline" title="Ispronicline">Ispronicline</a></li> <li><a href="/wiki/Ivermectin" title="Ivermectin">Ivermectin</a></li> <li><a href="/wiki/JNJ-39393406" title="JNJ-39393406">JNJ-39393406</a></li> <li><a href="/wiki/Levamisole" title="Levamisole">Levamisole</a></li> <li><a href="/wiki/Lobeline" title="Lobeline">Lobeline</a></li> <li><a href="/w/index.php?title=MEM-63,908&action=edit&redlink=1" class="new" title="MEM-63,908 (page does not exist)">MEM-63,908 (RG-3487)</a></li> <li><a href="/wiki/Morantel" title="Morantel">Morantel</a></li> <li><a href="/wiki/Nicotine" title="Nicotine">Nicotine</a> (<a href="/wiki/Tobacco" title="Tobacco">tobacco</a>)</li> <li><a href="/w/index.php?title=NS-1738&action=edit&redlink=1" class="new" title="NS-1738 (page does not exist)">NS-1738</a></li> <li><a href="/wiki/PHA-543,613" title="PHA-543,613">PHA-543,613</a></li> <li><a href="/w/index.php?title=PHA-709,829&action=edit&redlink=1" class="new" title="PHA-709,829 (page does not exist)">PHA-709,829</a></li> <li><a href="/wiki/PNU-120,596" title="PNU-120,596">PNU-120,596</a></li> <li><a href="/wiki/PNU-282,987" title="PNU-282,987">PNU-282,987</a></li> <li><a href="/wiki/Pozanicline" title="Pozanicline">Pozanicline</a></li> <li><a href="/wiki/Pyrantel" title="Pyrantel">Pyrantel</a></li> <li><a href="/wiki/Rivanicline" title="Rivanicline">Rivanicline</a></li> <li><a href="/wiki/RJR-2429" title="RJR-2429">RJR-2429</a></li> <li><a href="/wiki/Sazetidine_A" title="Sazetidine A">Sazetidine A</a></li> <li><a href="/wiki/SB-206553" title="SB-206553">SB-206553</a></li> <li><a href="/w/index.php?title=Sebacylcholine&action=edit&redlink=1" class="new" title="Sebacylcholine (page does not exist)">Sebacylcholine</a></li> <li><a href="/wiki/SIB-1508Y" class="mw-redirect" title="SIB-1508Y">SIB-1508Y</a></li> <li><a href="/wiki/SIB-1553A" title="SIB-1553A">SIB-1553A</a></li> <li><a href="/wiki/SSR-180,711" title="SSR-180,711">SSR-180,711</a></li> <li><a href="/w/index.php?title=Suberyldicholine&action=edit&redlink=1" class="new" title="Suberyldicholine (page does not exist)">Suberyldicholine</a></li> <li><a href="/wiki/Suxamethonium" class="mw-redirect" title="Suxamethonium">Suxamethonium (succinylcholine)</a></li> <li><a href="/wiki/Suxethonium_chloride" title="Suxethonium chloride">Suxethonium (succinyldicholine)</a></li> <li><a href="/wiki/TC-1698" title="TC-1698">TC-1698</a></li> <li><a href="/w/index.php?title=TC-1734&action=edit&redlink=1" class="new" title="TC-1734 (page does not exist)">TC-1734</a></li> <li><a href="/wiki/TC-1827" title="TC-1827">TC-1827</a></li> <li><a href="/wiki/TC-2216" title="TC-2216">TC-2216</a></li> <li><a href="/wiki/TC-5214" class="mw-redirect" title="TC-5214">TC-5214</a></li> <li><a href="/wiki/TC-5619" class="mw-redirect" title="TC-5619">TC-5619</a></li> <li><a href="/w/index.php?title=TC-6683&action=edit&redlink=1" class="new" title="TC-6683 (page does not exist)">TC-6683</a></li> <li><a href="/wiki/Tebanicline" title="Tebanicline">Tebanicline</a></li> <li><a href="/wiki/Tribendimidine" title="Tribendimidine">Tribendimidine</a></li> <li><a href="/wiki/Tropisetron" title="Tropisetron">Tropisetron</a></li> <li><a href="/wiki/UB-165" title="UB-165">UB-165</a></li> <li><a href="/wiki/Varenicline" title="Varenicline">Varenicline</a></li> <li><a href="/wiki/WAY-317,538" class="mw-redirect" title="WAY-317,538">WAY-317,538</a></li> <li><a href="/w/index.php?title=XY-4083&action=edit&redlink=1" class="new" title="XY-4083 (page does not exist)">XY-4083</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Receptor_antagonist" title="Receptor antagonist">Antagonists</a><br />(and <a href="/wiki/Negative_allosteric_modulators" class="mw-redirect" title="Negative allosteric modulators"><abbr title="negative allosteric modulators">NAMs</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 negative allosteric modulators</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><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/%CE%91-Neurotoxin" title="Α-Neurotoxin">α-Neurotoxins</a> (e.g., <a href="/wiki/%CE%91-bungarotoxin" class="mw-redirect" title="Α-bungarotoxin">α-bungarotoxin</a>, <a href="/wiki/%CE%91-cobratoxin" class="mw-redirect" title="Α-cobratoxin">α-cobratoxin</a>, <a href="/wiki/%CE%91-conotoxin" class="mw-redirect" title="Α-conotoxin">α-conotoxin</a>, many others)</li> <li><a href="/w/index.php?title=ABT-126&action=edit&redlink=1" class="new" title="ABT-126 (page does not exist)">ABT-126</a></li> <li><a href="/wiki/Alcuronium" class="mw-redirect" title="Alcuronium">Alcuronium</a></li> <li><a href="/wiki/Allopregnanolone" title="Allopregnanolone">Allopregnanolone</a></li> <li><a href="/wiki/Amantadine" title="Amantadine">Amantadine</a></li> <li><a href="/w/index.php?title=Anatruxonium&action=edit&redlink=1" class="new" title="Anatruxonium (page does not exist)">Anatruxonium</a></li> <li><a href="/w/index.php?title=AQW051&action=edit&redlink=1" class="new" title="AQW051 (page does not exist)">AQW051</a></li> <li><a href="/wiki/Atracurium" class="mw-redirect" title="Atracurium">Atracurium</a></li> <li><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/BNC-210" title="BNC-210">BNC-210</a></li> <li><a href="/wiki/Bungarotoxin" title="Bungarotoxin">Bungarotoxins</a> (e.g., <a href="/wiki/%CE%91-bungarotoxin" class="mw-redirect" title="Α-bungarotoxin">α-bungarotoxin</a>, <a href="/wiki/%CE%9A-bungarotoxin" class="mw-redirect" title="Κ-bungarotoxin">κ-bungarotoxin</a>)</li> <li><a href="/wiki/Bupropion" title="Bupropion">Bupropion</a></li> <li><a href="/wiki/BW284C51" title="BW284C51">BW284C51</a></li> <li><a href="/wiki/BW-A444" title="BW-A444">BW-A444</a></li> <li><a href="/wiki/Candocuronium_iodide" title="Candocuronium iodide">Candocuronium iodide (chandonium iodide)</a></li> <li><a href="/wiki/Chlorisondamine" title="Chlorisondamine">Chlorisondamine</a></li> <li><a href="/wiki/Cisatracurium" class="mw-redirect" title="Cisatracurium">Cisatracurium</a></li> <li><a href="/wiki/Coclaurine" title="Coclaurine">Coclaurine</a></li> <li><a href="/wiki/Coronaridine" title="Coronaridine">Coronaridine</a></li> <li><a href="/wiki/Curare" title="Curare">Curare</a></li> <li><a href="/wiki/Cyclopropane" title="Cyclopropane">Cyclopropane</a></li> <li><a href="/wiki/Dacuronium_bromide" title="Dacuronium bromide">Dacuronium bromide</a></li> <li><a href="/wiki/Decamethonium" title="Decamethonium">Decamethonium</a></li> <li><a href="/wiki/Dehydronorketamine" title="Dehydronorketamine">Dehydronorketamine</a></li> <li><a href="/wiki/Desflurane" title="Desflurane">Desflurane</a></li> <li><a href="/wiki/Dextromethorphan" title="Dextromethorphan">Dextromethorphan</a></li> <li><a href="/wiki/Dextropropoxyphene" title="Dextropropoxyphene">Dextropropoxyphene</a></li> <li><a href="/wiki/Dextrorphan" title="Dextrorphan">Dextrorphan</a></li> <li><a href="/w/index.php?title=Diadonium&action=edit&redlink=1" class="new" title="Diadonium (page does not exist)">Diadonium</a></li> <li><a href="/w/index.php?title=Dihydro-beta-erythroidine&action=edit&redlink=1" class="new" title="Dihydro-beta-erythroidine (page does not exist)">DHβE</a></li> <li><a href="/wiki/Dihydrochandonium" title="Dihydrochandonium">Dihydrochandonium</a></li> <li><a href="/wiki/Dimethyltubocurarine" class="mw-redirect" title="Dimethyltubocurarine">Dimethyltubocurarine (metocurine)</a></li> <li><a href="/wiki/Dioscorine" title="Dioscorine">Dioscorine</a></li> <li><a href="/wiki/Dipyrandium" title="Dipyrandium">Dipyrandium</a></li> <li><a href="/wiki/Dizocilpine" title="Dizocilpine">Dizocilpine (MK-801)</a></li> <li><a href="/wiki/Doxacurium" class="mw-redirect" title="Doxacurium">Doxacurium</a></li> <li><a href="/wiki/Encenicline" title="Encenicline">Encenicline</a></li> <li><a href="/wiki/Enflurane" title="Enflurane">Enflurane</a></li> <li><a href="/wiki/Erythravine" title="Erythravine">Erythravine</a></li> <li><a href="/wiki/Esketamine" title="Esketamine">Esketamine</a></li> <li><a href="/wiki/Fazadinium" class="mw-redirect" title="Fazadinium">Fazadinium</a></li> <li><a href="/wiki/Gallamine" class="mw-redirect" title="Gallamine">Gallamine</a></li> <li><a href="/wiki/Gantacurium_chloride" title="Gantacurium chloride">Gantacurium chloride</a></li> <li><a href="/wiki/Halothane" title="Halothane">Halothane</a></li> <li><a href="/wiki/Hexafluronium" class="mw-redirect" title="Hexafluronium">Hexafluronium</a></li> <li><a href="/wiki/Hexamethonium" title="Hexamethonium">Hexamethonium (benzohexonium)</a></li> <li><a href="/wiki/Hydroxybupropion" title="Hydroxybupropion">Hydroxybupropion</a></li> <li><a href="/wiki/Hydroxynorketamine" title="Hydroxynorketamine">Hydroxynorketamine</a></li> <li><a href="/wiki/Ibogaine" title="Ibogaine">Ibogaine</a></li> <li><a href="/wiki/Isoflurane" title="Isoflurane">Isoflurane</a></li> <li><a href="/wiki/Ketamine" title="Ketamine">Ketamine</a></li> <li><a href="/wiki/Kynurenic_acid" title="Kynurenic acid">Kynurenic acid</a></li> <li><a href="/wiki/Laudanosine" title="Laudanosine">Laudanosine</a></li> <li><a href="/wiki/Laudexium" class="mw-redirect" title="Laudexium">Laudexium (laudolissin)</a></li> <li><a href="/wiki/Levacetylmethadol" title="Levacetylmethadol">Levacetylmethadol</a></li> <li><a href="/wiki/Levomethadone" title="Levomethadone">Levomethadone</a></li> <li><a href="/wiki/Malouetine" title="Malouetine">Malouetine</a></li> <li><a href="/wiki/2-Methoxyethyl-18-methoxycoronaridinate" title="2-Methoxyethyl-18-methoxycoronaridinate">ME-18-MC</a></li> <li><a href="/wiki/Mecamylamine" title="Mecamylamine">Mecamylamine</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 (racemethorphan)</a></li> <li><a href="/wiki/Methyllycaconitine" title="Methyllycaconitine">Methyllycaconitine</a></li> <li><a href="/wiki/Metocurine" title="Metocurine">Metocurine</a></li> <li><a href="/wiki/Mivacurium" class="mw-redirect" title="Mivacurium">Mivacurium</a></li> <li><a href="/wiki/Morphanol" class="mw-redirect" title="Morphanol">Morphanol (racemorphan)</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/Norketamine" title="Norketamine">Norketamine</a></li> <li><a href="/wiki/Pancuronium_bromide" title="Pancuronium bromide">Pancuronium bromide</a></li> <li><a href="/wiki/Pempidine" title="Pempidine">Pempidine</a></li> <li><a href="/wiki/Pentamine" title="Pentamine">Pentamine</a></li> <li><a href="/wiki/Pentolinium" title="Pentolinium">Pentolinium</a></li> <li><a href="/wiki/Phencyclidine" title="Phencyclidine">Phencyclidine</a></li> <li><a href="/wiki/Pipecuronium_bromide" title="Pipecuronium bromide">Pipecuronium bromide</a></li> <li><a href="/wiki/Progesterone" title="Progesterone">Progesterone</a></li> <li><a href="/wiki/Promegestone" title="Promegestone">Promegestone</a></li> <li><a href="/wiki/Radafaxine" title="Radafaxine">Radafaxine</a></li> <li><a href="/wiki/Rapacuronium_bromide" title="Rapacuronium bromide">Rapacuronium bromide</a></li> <li><a href="/wiki/Reboxetine" title="Reboxetine">Reboxetine</a></li> <li><a href="/wiki/Rocuronium_bromide" title="Rocuronium bromide">Rocuronium bromide</a></li> <li><a href="/wiki/Sevoflurane" title="Sevoflurane">Sevoflurane</a></li> <li><a href="/wiki/Stercuronium_iodide" title="Stercuronium iodide">Stercuronium iodide</a></li> <li><a href="/wiki/Surugatoxin" title="Surugatoxin">Surugatoxin</a></li> <li><a href="/wiki/Thiocolchicoside" title="Thiocolchicoside">Thiocolchicoside</a></li> <li><a href="/wiki/Threohydrobupropion" title="Threohydrobupropion">Threohydrobupropion</a></li> <li><a href="/wiki/Toxiferine" title="Toxiferine">Toxiferine</a></li> <li><a href="/wiki/Tramadol" title="Tramadol">Tramadol</a></li> <li><a href="/wiki/Trimetaphan_camsilate" title="Trimetaphan camsilate">Trimetaphan camsilate (trimethaphan camsylate)</a></li> <li><a href="/w/index.php?title=Tropeinium&action=edit&redlink=1" class="new" title="Tropeinium (page does not exist)">Tropeinium</a></li> <li><a href="/wiki/Tubocurarine" class="mw-redirect" title="Tubocurarine">Tubocurarine</a></li> <li><a href="/wiki/Vanoxerine" title="Vanoxerine">Vanoxerine</a></li> <li><a href="/wiki/Vecuronium_bromide" title="Vecuronium bromide">Vecuronium bromide</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%;text-align:center;"><a href="/wiki/Precursor_(chemistry)" title="Precursor (chemistry)">Precursors</a><br /><small>(and <a href="/wiki/Prodrug" title="Prodrug">prodrugs</a>)</small></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/Acetyl-coA" class="mw-redirect" title="Acetyl-coA">Acetyl-coA</a></li> <li><a href="/wiki/Adafenoxate" title="Adafenoxate">Adafenoxate</a></li> <li><a href="/wiki/Choline" title="Choline">Choline</a> (<a href="/wiki/Lecithin" title="Lecithin">lecithin</a>)</li> <li><a href="/wiki/Citicoline" title="Citicoline">Citicoline</a></li> <li><a href="/wiki/Cyprodenate" title="Cyprodenate">Cyprodenate</a></li> <li><a href="/wiki/Dimethylethanolamine" title="Dimethylethanolamine">Dimethylethanolamine</a></li> <li><a href="/wiki/Glycerophosphocholine" class="mw-redirect" title="Glycerophosphocholine">Glycerophosphocholine</a></li> <li><a href="/wiki/Meclofenoxate" title="Meclofenoxate">Meclofenoxate (centrophenoxine)</a></li> <li><a href="/wiki/Phosphatidylcholine" title="Phosphatidylcholine">Phosphatidylcholine</a></li> <li><a href="/wiki/Phosphatidylethanolamine" title="Phosphatidylethanolamine">Phosphatidylethanolamine</a></li> <li><a href="/wiki/Phosphorylcholine" title="Phosphorylcholine">Phosphorylcholine</a></li> <li><a href="/wiki/Pirisudanol" title="Pirisudanol">Pirisudanol</a></li></ul> </div></td></tr><tr><td class="navbox-abovebelow" colspan="2"><div> <dl><dt>See also</dt> <dd><a href="/wiki/Template:Receptor_modulators" title="Template:Receptor modulators">Receptor/signaling modulators</a></dd> <dd><a href="/wiki/Template:Muscarinic_acetylcholine_receptor_modulators" title="Template:Muscarinic acetylcholine receptor modulators">Muscarinic acetylcholine receptor modulators</a></dd> <dd><a href="/wiki/Template:Acetylcholine_metabolism_and_transport_modulators" title="Template:Acetylcholine metabolism and transport modulators">Acetylcholine metabolism/transport modulators</a></dd></dl> </div></td></tr></tbody></table></div> </div></td></tr></tbody></table></div>    </div><noscript><img src="https://login.wikimedia.org/wiki/Special:CentralAutoLogin/start?type=1x1" alt="" width="1" height="1" style="border: none; position: absolute;"></noscript> <div class="printfooter" data-nosnippet="">Retrieved from "<a dir="ltr" href="https://en.wikipedia.org/w/index.php?title=Organophosphate&oldid=1256978316">https://en.wikipedia.org/w/index.php?title=Organophosphate&oldid=1256978316</a>"</div></div> <div id="catlinks" class="catlinks" data-mw="interface"><div id="mw-normal-catlinks" class="mw-normal-catlinks"><a href="/wiki/Help:Category" title="Help:Category">Categories</a>: <ul><li><a href="/wiki/Category:Organophosphates" title="Category:Organophosphates">Organophosphates</a></li><li><a href="/wiki/Category:Phosphorus(V)_compounds" title="Category:Phosphorus(V) compounds">Phosphorus(V) compounds</a></li><li><a href="/wiki/Category:Anticholinesterases" 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