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class="vector-toc-text"> <span class="vector-toc-numb">2</span> <span>Use in biosynthesis of coenzyme A</span> </div> </a> <ul id="toc-Use_in_biosynthesis_of_coenzyme_A-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Dietary_recommendations" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Dietary_recommendations"> <div class="vector-toc-text"> <span class="vector-toc-numb">3</span> <span>Dietary recommendations</span> </div> </a> <button aria-controls="toc-Dietary_recommendations-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 Dietary recommendations subsection</span> </button> <ul id="toc-Dietary_recommendations-sublist" class="vector-toc-list"> <li id="toc-Safety" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Safety"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.1</span> <span>Safety</span> </div> </a> <ul id="toc-Safety-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Labeling_requirements" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Labeling_requirements"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.2</span> <span>Labeling requirements</span> </div> </a> <ul id="toc-Labeling_requirements-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Sources" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Sources"> <div class="vector-toc-text"> <span class="vector-toc-numb">4</span> <span>Sources</span> </div> </a> <button aria-controls="toc-Sources-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 Sources subsection</span> </button> <ul id="toc-Sources-sublist" class="vector-toc-list"> <li id="toc-Dietary" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Dietary"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.1</span> <span>Dietary</span> </div> </a> <ul id="toc-Dietary-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Supplements" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Supplements"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.2</span> <span>Supplements</span> </div> </a> <ul id="toc-Supplements-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Fortification" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Fortification"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.3</span> <span>Fortification</span> </div> </a> <ul id="toc-Fortification-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Absorption,_metabolism_and_excretion" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Absorption,_metabolism_and_excretion"> <div class="vector-toc-text"> <span class="vector-toc-numb">5</span> <span>Absorption, metabolism and excretion</span> </div> </a> <ul id="toc-Absorption,_metabolism_and_excretion-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Deficiency" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Deficiency"> <div class="vector-toc-text"> <span class="vector-toc-numb">6</span> <span>Deficiency</span> </div> </a> <ul id="toc-Deficiency-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Animal_nutrition" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Animal_nutrition"> <div class="vector-toc-text"> <span class="vector-toc-numb">7</span> <span>Animal nutrition</span> </div> </a> <ul id="toc-Animal_nutrition-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Synthesis" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Synthesis"> <div class="vector-toc-text"> <span class="vector-toc-numb">8</span> <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-Biosynthesis" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Biosynthesis"> <div class="vector-toc-text"> <span class="vector-toc-numb">8.1</span> <span>Biosynthesis</span> </div> </a> <ul id="toc-Biosynthesis-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Industrial_synthesis" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Industrial_synthesis"> <div class="vector-toc-text"> <span class="vector-toc-numb">8.2</span> <span>Industrial synthesis</span> </div> </a> <ul id="toc-Industrial_synthesis-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-History" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#History"> <div class="vector-toc-text"> <span class="vector-toc-numb">9</span> <span>History</span> </div> </a> <ul id="toc-History-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">10</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" title="Table of Contents" > <input type="checkbox" id="vector-page-titlebar-toc-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-vector-page-titlebar-toc" class="vector-dropdown-checkbox " aria-label="Toggle the table of contents" > <label id="vector-page-titlebar-toc-label" for="vector-page-titlebar-toc-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--icon-only " aria-hidden="true" ><span class="vector-icon mw-ui-icon-listBullet mw-ui-icon-wikimedia-listBullet"></span> <span class="vector-dropdown-label-text">Toggle the table of contents</span> </label> <div class="vector-dropdown-content"> <div id="vector-page-titlebar-toc-unpinned-container" class="vector-unpinned-container"> </div> </div> </div> </nav> <h1 id="firstHeading" class="firstHeading mw-first-heading"><span class="mw-page-title-main">Pantothenic acid</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 60 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-60" 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">60 languages</span> </label> <div class="vector-dropdown-content"> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li class="interlanguage-link interwiki-af mw-list-item"><a href="https://af.wikipedia.org/wiki/Pantoteensuur" title="Pantoteensuur – Afrikaans" lang="af" hreflang="af" data-title="Pantoteensuur" data-language-autonym="Afrikaans" data-language-local-name="Afrikaans" class="interlanguage-link-target"><span>Afrikaans</span></a></li><li class="interlanguage-link interwiki-ar mw-list-item"><a href="https://ar.wikipedia.org/wiki/%D9%81%D9%8A%D8%AA%D8%A7%D9%85%D9%8A%D9%86_%D8%A8%D9%8A5" title="فيتامين بي5 – Arabic" lang="ar" hreflang="ar" data-title="فيتامين بي5" data-language-autonym="العربية" data-language-local-name="Arabic" class="interlanguage-link-target"><span>العربية</span></a></li><li class="interlanguage-link interwiki-azb mw-list-item"><a href="https://azb.wikipedia.org/wiki/%D9%BE%D8%A7%D9%86%D8%AA%D9%88%D8%AA%D9%86%DB%8C%DA%A9_%D8%A7%D8%B3%DB%8C%D8%AF" title="پانتوتنیک اسید – South Azerbaijani" lang="azb" hreflang="azb" data-title="پانتوتنیک اسید" data-language-autonym="تۆرکجه" data-language-local-name="South Azerbaijani" class="interlanguage-link-target"><span>تۆرکجه</span></a></li><li class="interlanguage-link interwiki-bg mw-list-item"><a href="https://bg.wikipedia.org/wiki/%D0%9F%D0%B0%D0%BD%D1%82%D0%BE%D1%82%D0%B5%D0%BD%D0%BE%D0%B2%D0%B0_%D0%BA%D0%B8%D1%81%D0%B5%D0%BB%D0%B8%D0%BD%D0%B0" title="Пантотенова киселина – Bulgarian" lang="bg" hreflang="bg" data-title="Пантотенова киселина" data-language-autonym="Български" data-language-local-name="Bulgarian" class="interlanguage-link-target"><span>Български</span></a></li><li class="interlanguage-link interwiki-bs mw-list-item"><a href="https://bs.wikipedia.org/wiki/Vitamin_B5" title="Vitamin B5 – Bosnian" lang="bs" hreflang="bs" data-title="Vitamin B5" 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/%C3%80cid_pantot%C3%A8nic" title="Àcid pantotènic – Catalan" lang="ca" hreflang="ca" data-title="Àcid pantotènic" 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/Kyselina_pantothenov%C3%A1" title="Kyselina pantothenová – Czech" lang="cs" hreflang="cs" data-title="Kyselina pantothenová" data-language-autonym="Čeština" data-language-local-name="Czech" class="interlanguage-link-target"><span>Čeština</span></a></li><li class="interlanguage-link interwiki-cy mw-list-item"><a href="https://cy.wikipedia.org/wiki/Asid_pantothenig" title="Asid pantothenig – Welsh" lang="cy" hreflang="cy" data-title="Asid pantothenig" data-language-autonym="Cymraeg" data-language-local-name="Welsh" class="interlanguage-link-target"><span>Cymraeg</span></a></li><li class="interlanguage-link interwiki-de mw-list-item"><a href="https://de.wikipedia.org/wiki/Pantothens%C3%A4ure" title="Pantothensäure – German" lang="de" hreflang="de" data-title="Pantothensäure" data-language-autonym="Deutsch" data-language-local-name="German" class="interlanguage-link-target"><span>Deutsch</span></a></li><li class="interlanguage-link interwiki-dv mw-list-item"><a href="https://dv.wikipedia.org/wiki/%DE%88%DE%A8%DE%93%DE%A6%DE%89%DE%A8%DE%82%DE%B0_%DE%84%DE%A95" title="ވިޓަމިން ބީ5 – Divehi" lang="dv" hreflang="dv" data-title="ވިޓަމިން ބީ5" data-language-autonym="ދިވެހިބަސް" data-language-local-name="Divehi" class="interlanguage-link-target"><span>ދިވެހިބަސް</span></a></li><li class="interlanguage-link interwiki-et mw-list-item"><a href="https://et.wikipedia.org/wiki/B5-vitamiin" title="B5-vitamiin – Estonian" lang="et" hreflang="et" data-title="B5-vitamiin" data-language-autonym="Eesti" data-language-local-name="Estonian" class="interlanguage-link-target"><span>Eesti</span></a></li><li class="interlanguage-link interwiki-el mw-list-item"><a href="https://el.wikipedia.org/wiki/%CE%A0%CE%B1%CE%BD%CF%84%CE%BF%CE%B8%CE%B5%CE%BD%CE%B9%CE%BA%CF%8C_%CE%BF%CE%BE%CF%8D" title="Παντοθενικό οξύ – Greek" lang="el" hreflang="el" data-title="Παντοθενικό οξύ" data-language-autonym="Ελληνικά" data-language-local-name="Greek" class="interlanguage-link-target"><span>Ελληνικά</span></a></li><li class="interlanguage-link interwiki-es mw-list-item"><a href="https://es.wikipedia.org/wiki/Vitamina_B5" title="Vitamina B5 – Spanish" lang="es" hreflang="es" data-title="Vitamina B5" data-language-autonym="Español" data-language-local-name="Spanish" class="interlanguage-link-target"><span>Español</span></a></li><li class="interlanguage-link interwiki-eo mw-list-item"><a href="https://eo.wikipedia.org/wiki/Pantotenata_acido" title="Pantotenata acido – Esperanto" lang="eo" hreflang="eo" data-title="Pantotenata acido" data-language-autonym="Esperanto" data-language-local-name="Esperanto" class="interlanguage-link-target"><span>Esperanto</span></a></li><li class="interlanguage-link interwiki-eu mw-list-item"><a href="https://eu.wikipedia.org/wiki/B5_bitamina" title="B5 bitamina – Basque" lang="eu" hreflang="eu" data-title="B5 bitamina" 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%B3%DB%8C%D8%AF_%D9%BE%D8%A7%D9%86%D8%AA%D9%88%D8%AA%D9%86%DB%8C%DA%A9" title="اسید پانتوتنیک – Persian" lang="fa" hreflang="fa" data-title="اسید پانتوتنیک" data-language-autonym="فارسی" data-language-local-name="Persian" class="interlanguage-link-target"><span>فارسی</span></a></li><li class="interlanguage-link interwiki-fr mw-list-item"><a href="https://fr.wikipedia.org/wiki/Vitamine_B5" title="Vitamine B5 – French" lang="fr" hreflang="fr" data-title="Vitamine B5" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target"><span>Français</span></a></li><li class="interlanguage-link interwiki-ga mw-list-item"><a href="https://ga.wikipedia.org/wiki/Aig%C3%A9ad_pantait%C3%A9ineach" title="Aigéad pantaitéineach – Irish" lang="ga" hreflang="ga" data-title="Aigéad pantaitéineach" data-language-autonym="Gaeilge" data-language-local-name="Irish" class="interlanguage-link-target"><span>Gaeilge</span></a></li><li class="interlanguage-link interwiki-gl mw-list-item"><a href="https://gl.wikipedia.org/wiki/Vitamina_B5" title="Vitamina B5 – Galician" lang="gl" hreflang="gl" data-title="Vitamina B5" data-language-autonym="Galego" data-language-local-name="Galician" class="interlanguage-link-target"><span>Galego</span></a></li><li class="interlanguage-link interwiki-ko mw-list-item"><a href="https://ko.wikipedia.org/wiki/%ED%8C%90%ED%86%A0%ED%85%90%EC%82%B0" title="판토텐산 – Korean" lang="ko" hreflang="ko" data-title="판토텐산" 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%8A%D5%A1%D5%B6%D5%BF%D5%B8%D5%BF%D5%A5%D5%B6%D5%A1%D5%A9%D5%A9%D5%B8%D6%82" title="Պանտոտենաթթու – Armenian" lang="hy" hreflang="hy" data-title="Պանտոտենաթթու" data-language-autonym="Հայերեն" data-language-local-name="Armenian" class="interlanguage-link-target"><span>Հայերեն</span></a></li><li class="interlanguage-link interwiki-hi mw-list-item"><a href="https://hi.wikipedia.org/wiki/%E0%A4%AA%E0%A5%87%E0%A4%A8%E0%A5%8D%E0%A4%9F%E0%A5%8B%E0%A4%A5%E0%A5%87%E0%A4%A8%E0%A4%BF%E0%A4%95_%E0%A4%85%E0%A4%AE%E0%A5%8D%E0%A4%B2" title="पेन्टोथेनिक अम्ल – Hindi" lang="hi" hreflang="hi" data-title="पेन्टोथेनिक अम्ल" data-language-autonym="हिन्दी" data-language-local-name="Hindi" class="interlanguage-link-target"><span>हिन्दी</span></a></li><li class="interlanguage-link interwiki-hr mw-list-item"><a href="https://hr.wikipedia.org/wiki/Vitamin_B5" title="Vitamin B5 – Croatian" lang="hr" hreflang="hr" data-title="Vitamin B5" data-language-autonym="Hrvatski" data-language-local-name="Croatian" class="interlanguage-link-target"><span>Hrvatski</span></a></li><li class="interlanguage-link interwiki-id mw-list-item"><a href="https://id.wikipedia.org/wiki/Asam_pantotenat" title="Asam pantotenat – Indonesian" lang="id" hreflang="id" data-title="Asam pantotenat" data-language-autonym="Bahasa Indonesia" data-language-local-name="Indonesian" class="interlanguage-link-target"><span>Bahasa Indonesia</span></a></li><li class="interlanguage-link interwiki-it mw-list-item"><a href="https://it.wikipedia.org/wiki/Acido_pantotenico" title="Acido pantotenico – Italian" lang="it" hreflang="it" data-title="Acido pantotenico" data-language-autonym="Italiano" data-language-local-name="Italian" class="interlanguage-link-target"><span>Italiano</span></a></li><li class="interlanguage-link interwiki-he mw-list-item"><a href="https://he.wikipedia.org/wiki/%D7%95%D7%99%D7%98%D7%9E%D7%99%D7%9F_B5" title="ויטמין B5 – Hebrew" lang="he" hreflang="he" data-title="ויטמין B5" data-language-autonym="עברית" data-language-local-name="Hebrew" class="interlanguage-link-target"><span>עברית</span></a></li><li class="interlanguage-link interwiki-kk mw-list-item"><a href="https://kk.wikipedia.org/wiki/%D0%9F%D0%B0%D0%BD%D1%82%D0%BE%D1%82%D0%B5%D0%BD_%D2%9B%D1%8B%D1%88%D2%9B%D1%8B%D0%BB%D1%8B" title="Пантотен қышқылы – Kazakh" lang="kk" hreflang="kk" data-title="Пантотен қышқылы" data-language-autonym="Қазақша" data-language-local-name="Kazakh" class="interlanguage-link-target"><span>Қазақша</span></a></li><li class="interlanguage-link interwiki-ky mw-list-item"><a href="https://ky.wikipedia.org/wiki/%D0%9F%D0%B0%D0%BD%D1%82%D0%BE%D1%82%D0%B5%D0%BD_%D0%BA%D1%8B%D1%87%D0%BA%D1%8B%D0%BB%D1%8B" title="Пантотен кычкылы – Kyrgyz" lang="ky" hreflang="ky" data-title="Пантотен кычкылы" data-language-autonym="Кыргызча" data-language-local-name="Kyrgyz" class="interlanguage-link-target"><span>Кыргызча</span></a></li><li class="interlanguage-link interwiki-lv mw-list-item"><a href="https://lv.wikipedia.org/wiki/Pantot%C4%93nsk%C4%81be" title="Pantotēnskābe – Latvian" lang="lv" hreflang="lv" data-title="Pantotēnskābe" data-language-autonym="Latviešu" data-language-local-name="Latvian" class="interlanguage-link-target"><span>Latviešu</span></a></li><li class="interlanguage-link interwiki-lb mw-list-item"><a href="https://lb.wikipedia.org/wiki/Pantothensaier" title="Pantothensaier – Luxembourgish" lang="lb" hreflang="lb" data-title="Pantothensaier" data-language-autonym="Lëtzebuergesch" data-language-local-name="Luxembourgish" class="interlanguage-link-target"><span>Lëtzebuergesch</span></a></li><li class="interlanguage-link interwiki-lt mw-list-item"><a href="https://lt.wikipedia.org/wiki/Pantoteno_r%C5%ABg%C5%A1tis" title="Pantoteno rūgštis – Lithuanian" lang="lt" hreflang="lt" data-title="Pantoteno rūgštis" data-language-autonym="Lietuvių" data-language-local-name="Lithuanian" class="interlanguage-link-target"><span>Lietuvių</span></a></li><li class="interlanguage-link interwiki-hu mw-list-item"><a href="https://hu.wikipedia.org/wiki/Pantot%C3%A9nsav" title="Pantoténsav – Hungarian" lang="hu" hreflang="hu" data-title="Pantoténsav" data-language-autonym="Magyar" data-language-local-name="Hungarian" class="interlanguage-link-target"><span>Magyar</span></a></li><li class="interlanguage-link interwiki-mk mw-list-item"><a href="https://mk.wikipedia.org/wiki/%D0%9F%D0%B0%D0%BD%D1%82%D0%BE%D1%82%D0%B5%D0%BD%D1%81%D0%BA%D0%B0_%D0%BA%D0%B8%D1%81%D0%B5%D0%BB%D0%B8%D0%BD%D0%B0" title="Пантотенска киселина – Macedonian" lang="mk" hreflang="mk" data-title="Пантотенска киселина" data-language-autonym="Македонски" data-language-local-name="Macedonian" class="interlanguage-link-target"><span>Македонски</span></a></li><li class="interlanguage-link interwiki-ml mw-list-item"><a href="https://ml.wikipedia.org/wiki/%E0%B4%AA%E0%B4%BE%E0%B4%A8%E0%B5%8D%E0%B4%B1%E0%B5%8B%E0%B4%A4%E0%B5%8D%E0%B4%A4%E0%B4%BF%E0%B4%A8%E0%B4%BF%E0%B4%95%E0%B5%8D_%E0%B4%86%E0%B4%B8%E0%B4%BF%E0%B4%A1%E0%B5%8D" title="പാന്റോത്തിനിക് ആസിഡ് – Malayalam" lang="ml" hreflang="ml" data-title="പാന്റോത്തിനിക് ആസിഡ്" data-language-autonym="മലയാളം" data-language-local-name="Malayalam" class="interlanguage-link-target"><span>മലയാളം</span></a></li><li class="interlanguage-link interwiki-ms mw-list-item"><a href="https://ms.wikipedia.org/wiki/Asid_pantotenik" title="Asid pantotenik – Malay" lang="ms" hreflang="ms" data-title="Asid pantotenik" data-language-autonym="Bahasa Melayu" data-language-local-name="Malay" class="interlanguage-link-target"><span>Bahasa Melayu</span></a></li><li class="interlanguage-link interwiki-mn mw-list-item"><a href="https://mn.wikipedia.org/wiki/%D0%9F%D0%B0%D0%BD%D1%82%D0%BE%D1%82%D0%B5%D0%BD%D1%8B_%D1%85%D2%AF%D1%87%D0%B8%D0%BB" title="Пантотены хүчил – Mongolian" lang="mn" hreflang="mn" data-title="Пантотены хүчил" data-language-autonym="Монгол" data-language-local-name="Mongolian" class="interlanguage-link-target"><span>Монгол</span></a></li><li class="interlanguage-link interwiki-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/Pantotheenzuur" title="Pantotheenzuur – Dutch" lang="nl" hreflang="nl" data-title="Pantotheenzuur" 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%91%E3%83%B3%E3%83%88%E3%83%86%E3%83%B3%E9%85%B8" title="パントテン酸 – Japanese" lang="ja" hreflang="ja" data-title="パントテン酸" 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/Pantotensyre" title="Pantotensyre – Norwegian Bokmål" lang="nb" hreflang="nb" data-title="Pantotensyre" 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-oc mw-list-item"><a href="https://oc.wikipedia.org/wiki/Vitamina_B5" title="Vitamina B5 – Occitan" lang="oc" hreflang="oc" data-title="Vitamina B5" data-language-autonym="Occitan" data-language-local-name="Occitan" class="interlanguage-link-target"><span>Occitan</span></a></li><li class="interlanguage-link interwiki-pl mw-list-item"><a href="https://pl.wikipedia.org/wiki/Kwas_pantotenowy" title="Kwas pantotenowy – Polish" lang="pl" hreflang="pl" data-title="Kwas pantotenowy" data-language-autonym="Polski" data-language-local-name="Polish" class="interlanguage-link-target"><span>Polski</span></a></li><li class="interlanguage-link interwiki-pt mw-list-item"><a href="https://pt.wikipedia.org/wiki/%C3%81cido_pantot%C3%A9nico" title="Ácido pantoténico – Portuguese" lang="pt" hreflang="pt" data-title="Ácido pantoténico" data-language-autonym="Português" data-language-local-name="Portuguese" class="interlanguage-link-target"><span>Português</span></a></li><li class="interlanguage-link interwiki-ro mw-list-item"><a href="https://ro.wikipedia.org/wiki/Acid_pantotenic" title="Acid pantotenic – Romanian" lang="ro" hreflang="ro" data-title="Acid pantotenic" data-language-autonym="Română" data-language-local-name="Romanian" class="interlanguage-link-target"><span>Română</span></a></li><li class="interlanguage-link interwiki-ru mw-list-item"><a href="https://ru.wikipedia.org/wiki/%D0%9F%D0%B0%D0%BD%D1%82%D0%BE%D1%82%D0%B5%D0%BD%D0%BE%D0%B2%D0%B0%D1%8F_%D0%BA%D0%B8%D1%81%D0%BB%D0%BE%D1%82%D0%B0" title="Пантотеновая кислота – Russian" lang="ru" hreflang="ru" data-title="Пантотеновая кислота" data-language-autonym="Русский" data-language-local-name="Russian" class="interlanguage-link-target"><span>Русский</span></a></li><li class="interlanguage-link interwiki-sah mw-list-item"><a href="https://sah.wikipedia.org/wiki/%D0%9F%D0%B0%D0%BD%D1%82%D0%BE%D1%82%D0%B5%D0%BD%D0%B8%D0%BA_%D0%B0%D1%81%D0%B8%D0%B4" title="Пантотеник асид – Yakut" lang="sah" hreflang="sah" data-title="Пантотеник асид" data-language-autonym="Саха тыла" data-language-local-name="Yakut" class="interlanguage-link-target"><span>Саха тыла</span></a></li><li class="interlanguage-link interwiki-simple mw-list-item"><a href="https://simple.wikipedia.org/wiki/Pantothenic_acid" title="Pantothenic acid – Simple English" lang="en-simple" hreflang="en-simple" data-title="Pantothenic acid" data-language-autonym="Simple English" data-language-local-name="Simple English" class="interlanguage-link-target"><span>Simple English</span></a></li><li class="interlanguage-link interwiki-sk mw-list-item"><a href="https://sk.wikipedia.org/wiki/Kyselina_pantot%C3%A9nov%C3%A1" title="Kyselina pantoténová – Slovak" lang="sk" hreflang="sk" data-title="Kyselina pantoténová" data-language-autonym="Slovenčina" data-language-local-name="Slovak" class="interlanguage-link-target"><span>Slovenčina</span></a></li><li class="interlanguage-link interwiki-sl mw-list-item"><a href="https://sl.wikipedia.org/wiki/Pantotenska_kislina" title="Pantotenska kislina – Slovenian" lang="sl" hreflang="sl" data-title="Pantotenska kislina" data-language-autonym="Slovenščina" data-language-local-name="Slovenian" class="interlanguage-link-target"><span>Slovenščina</span></a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/Pantotenska_kiselina" title="Pantotenska kiselina – Serbian" lang="sr" hreflang="sr" data-title="Pantotenska kiselina" data-language-autonym="Српски / srpski" data-language-local-name="Serbian" class="interlanguage-link-target"><span>Српски / srpski</span></a></li><li class="interlanguage-link interwiki-sh mw-list-item"><a href="https://sh.wikipedia.org/wiki/Vitamin_B5" title="Vitamin B5 – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Vitamin B5" data-language-autonym="Srpskohrvatski / српскохрватски" data-language-local-name="Serbo-Croatian" class="interlanguage-link-target"><span>Srpskohrvatski / српскохрватски</span></a></li><li class="interlanguage-link interwiki-fi mw-list-item"><a href="https://fi.wikipedia.org/wiki/Pantoteenihappo" title="Pantoteenihappo – Finnish" lang="fi" hreflang="fi" data-title="Pantoteenihappo" 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/Pantotensyra" title="Pantotensyra – Swedish" lang="sv" hreflang="sv" data-title="Pantotensyra" data-language-autonym="Svenska" data-language-local-name="Swedish" class="interlanguage-link-target"><span>Svenska</span></a></li><li class="interlanguage-link interwiki-ta mw-list-item"><a href="https://ta.wikipedia.org/wiki/%E0%AE%AA%E0%AE%BE%E0%AE%A9%E0%AF%8D%E0%AE%9F%E0%AF%8B%E0%AE%A4%E0%AF%86%E0%AE%A9%E0%AE%BF%E0%AE%95%E0%AF%8D_%E0%AE%85%E0%AE%AE%E0%AE%BF%E0%AE%B2%E0%AE%AE%E0%AF%8D" title="பான்டோதெனிக் அமிலம் – Tamil" lang="ta" hreflang="ta" data-title="பான்டோதெனிக் அமிலம்" data-language-autonym="தமிழ்" data-language-local-name="Tamil" class="interlanguage-link-target"><span>தமிழ்</span></a></li><li class="interlanguage-link interwiki-th mw-list-item"><a href="https://th.wikipedia.org/wiki/%E0%B8%81%E0%B8%A3%E0%B8%94%E0%B9%81%E0%B8%9E%E0%B8%99%E0%B9%82%E0%B8%97%E0%B9%80%E0%B8%97%E0%B8%99%E0%B8%B4%E0%B8%81" title="กรดแพนโทเทนิก – Thai" lang="th" hreflang="th" data-title="กรดแพนโทเทนิก" data-language-autonym="ไทย" data-language-local-name="Thai" class="interlanguage-link-target"><span>ไทย</span></a></li><li class="interlanguage-link interwiki-tr mw-list-item"><a href="https://tr.wikipedia.org/wiki/Pantotenik_asit" title="Pantotenik asit – Turkish" lang="tr" hreflang="tr" data-title="Pantotenik asit" data-language-autonym="Türkçe" data-language-local-name="Turkish" class="interlanguage-link-target"><span>Türkçe</span></a></li><li class="interlanguage-link interwiki-uk mw-list-item"><a href="https://uk.wikipedia.org/wiki/%D0%9F%D0%B0%D0%BD%D1%82%D0%BE%D1%82%D0%B5%D0%BD%D0%BE%D0%B2%D0%B0_%D0%BA%D0%B8%D1%81%D0%BB%D0%BE%D1%82%D0%B0" title="Пантотенова кислота – Ukrainian" lang="uk" hreflang="uk" data-title="Пантотенова кислота" data-language-autonym="Українська" data-language-local-name="Ukrainian" class="interlanguage-link-target"><span>Українська</span></a></li><li class="interlanguage-link interwiki-ur mw-list-item"><a href="https://ur.wikipedia.org/wiki/%D9%BE%DB%8C%D9%86%D9%B9%D9%88%D8%AA%DA%BE%DB%8C%D9%86%DA%A9_%D8%AA%DB%8C%D8%B2%D8%A7%D8%A8" title="پینٹوتھینک تیزاب – Urdu" lang="ur" hreflang="ur" data-title="پینٹوتھینک تیزاب" data-language-autonym="اردو" data-language-local-name="Urdu" class="interlanguage-link-target"><span>اردو</span></a></li><li class="interlanguage-link interwiki-vi mw-list-item"><a href="https://vi.wikipedia.org/wiki/Acid_pantothenic" title="Acid pantothenic – Vietnamese" lang="vi" hreflang="vi" data-title="Acid pantothenic" 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.hatnote i{font-style:normal}.mw-parser-output .hatnote+link+.hatnote{margin-top:-0.5em}@media print{body.ns-0 .mw-parser-output .hatnote{display:none!important}}</style><div role="note" class="hatnote navigation-not-searchable">Not to be confused with <a href="/wiki/Pantethine" title="Pantethine">pantethine</a>.</div> <p> <style data-mw-deduplicate="TemplateStyles:r1268415487">.mw-parser-output .ib-chembox{border-collapse:collapse;text-align:left}.mw-parser-output .ib-chembox td,.mw-parser-output .ib-chembox th{border:1px solid #a2a9b1;width:40%}.mw-parser-output .ib-chembox td+td{width:60%}@media screen{html.skin-theme-clientpref-night .mw-parser-output .ib-chembox figure:not(.skin-invert-image):not(.skin-invert):not(.bg-transparent){background:var(--background-color-inverted,#f8f9fa)}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .ib-chembox figure:not(.skin-invert-image):not(.skin-invert):not(.bg-transparent){background:var(--background-color-inverted,#f8f9fa)}}</style> </p> <table class="infobox ib-chembox"> <caption>Pantothenic acid </caption> <tbody><tr> <td colspan="2" style="text-align:center; padding:2px;"><figure class="mw-halign-center skin-invert-image" typeof="mw:File"><a href="/wiki/File:(R)-Pantothenic_acid_Formula_V.1.svg" class="mw-file-description" title="Skeletal formula of (R)-pantothenic acid"><img alt="Skeletal formula of (R)-pantothenic acid" src="//upload.wikimedia.org/wikipedia/commons/thumb/0/0b/%28R%29-Pantothenic_acid_Formula_V.1.svg/250px-%28R%29-Pantothenic_acid_Formula_V.1.svg.png" decoding="async" width="220" height="74" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/0/0b/%28R%29-Pantothenic_acid_Formula_V.1.svg/330px-%28R%29-Pantothenic_acid_Formula_V.1.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/0/0b/%28R%29-Pantothenic_acid_Formula_V.1.svg/440px-%28R%29-Pantothenic_acid_Formula_V.1.svg.png 2x" data-file-width="405" data-file-height="136" /></a><figcaption>Skeletal formula of (R)-pantothenic acid</figcaption></figure> </td></tr> <tr> <td colspan="2" style="text-align:center; padding:2px;"><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Pantothenic-acid-based-on-xtal-3D-bs-17.png" class="mw-file-description" title="Pantothenic acid molecule"><img alt="Pantothenic acid molecule" src="//upload.wikimedia.org/wikipedia/commons/thumb/6/67/Pantothenic-acid-based-on-xtal-3D-bs-17.png/220px-Pantothenic-acid-based-on-xtal-3D-bs-17.png" decoding="async" width="220" height="120" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/67/Pantothenic-acid-based-on-xtal-3D-bs-17.png/330px-Pantothenic-acid-based-on-xtal-3D-bs-17.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/67/Pantothenic-acid-based-on-xtal-3D-bs-17.png/440px-Pantothenic-acid-based-on-xtal-3D-bs-17.png 2x" data-file-width="3000" data-file-height="1632" /></a><figcaption>Pantothenic acid molecule</figcaption></figure> </td></tr> <tr> <th colspan="2" style="background: #f8eaba;color:inherit; text-align: center;">Names </th></tr> <tr> <td colspan="2" style="text-align:left;"><a href="/wiki/Preferred_IUPAC_name" title="Preferred IUPAC name">Preferred IUPAC name</a> <div style="max-width:22em; word-wrap:break-word; padding-left:1.7em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0; max-width:22em;">3-[(2<i>R</i>)-2,4-Dihydroxy-3,3-dimethylbutanamido]propanoic acid</div></div> </td></tr> <tr> <td colspan="2" style="text-align:left;"><a href="/wiki/Chemical_nomenclature#Systematic_name" title="Chemical nomenclature">Systematic IUPAC name</a> <div style="max-width:22em; word-wrap:break-word; padding-left:1.7em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0; max-width:22em;">3-[(2<i>R</i>)-(2,4-Dihydroxy-3,3-dimethylbutanoyl)amino]propanoic acid</div></div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba;color:inherit; text-align: center;">Identifiers </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/CAS_Registry_Number" title="CAS Registry Number">CAS Number</a></div> </td> <td><style data-mw-deduplicate="TemplateStyles:r1126788409">.mw-parser-output .plainlist ol,.mw-parser-output .plainlist ul{line-height:inherit;list-style:none;margin:0;padding:0}.mw-parser-output .plainlist ol li,.mw-parser-output .plainlist ul li{margin-bottom:0}</style><div class="plainlist"><ul><li><span title="commonchemistry.cas.org"><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=599-54-2">599-54-2</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li><li><span title="commonchemistry.cas.org"><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=79-83-4">79-83-4</a></span> (<i>R</i>)<sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">3D model (<a href="/wiki/JSmol" class="mw-redirect" title="JSmol">JSmol</a>)</div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><span title="chemapps.stolaf.edu (3D interactive model)"><a rel="nofollow" class="external text" href="https://chemapps.stolaf.edu/jmol/jmol.php?model=CC%28C%29%28CO%29C%28C%28%3DO%29NCCC%28%3DO%29O%29O">Interactive image</a></span></li><li>(<i>R</i>): <span title="chemapps.stolaf.edu (3D interactive model)"><a rel="nofollow" class="external text" href="https://chemapps.stolaf.edu/jmol/jmol.php?model=CC%28C%29%28CO%29%5BC%40H%5D%28C%28%3DO%29NCCC%28%3DO%29O%29O">Interactive image</a></span></li><li>(<i>S</i>): <span title="chemapps.stolaf.edu (3D interactive model)"><a rel="nofollow" class="external text" href="https://chemapps.stolaf.edu/jmol/jmol.php?model=CC%28C%29%28CO%29%5BC%40%40H%5D%28C%28%3DO%29NCCC%28%3DO%29O%29O">Interactive image</a></span></li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Beilstein_database" title="Beilstein database">Beilstein Reference</a></div> </td> <td>1727062, 1727064 (<i>R</i>) </td></tr> <tr> <td><a href="/wiki/ChEBI" title="ChEBI">ChEBI</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><span title="www.ebi.ac.uk"><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chebi/searchId.do?chebiId=7916">CHEBI:7916</a></span><sup> <span typeof="mw:File"><span><img alt="☒" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/7px-X_mark.svg.png" decoding="async" width="7" height="8" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/11px-X_mark.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/14px-X_mark.svg.png 2x" data-file-width="525" data-file-height="600" /></span></span><span style="display:none">N</span></sup></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ChEMBL" title="ChEMBL">ChEMBL</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><span title="www.ebi.ac.uk"><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chembl/explore/compound/ChEMBL1594">ChEMBL1594</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ChemSpider" title="ChemSpider">ChemSpider</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><span title="www.chemspider.com"><a rel="nofollow" class="external text" href="https://www.chemspider.com/Chemical-Structure.963.html">963</a></span><sup> <span typeof="mw:File"><span><img alt="☒" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/7px-X_mark.svg.png" decoding="async" width="7" height="8" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/11px-X_mark.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/14px-X_mark.svg.png 2x" data-file-width="525" data-file-height="600" /></span></span><span style="display:none">N</span></sup></li><li><span title="www.chemspider.com"><a rel="nofollow" class="external text" href="https://www.chemspider.com/Chemical-Structure.6361.html">6361</a></span> (<i>R</i>)<sup> <span typeof="mw:File"><span><img alt="☒" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/7px-X_mark.svg.png" decoding="async" width="7" height="8" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/11px-X_mark.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/14px-X_mark.svg.png 2x" data-file-width="525" data-file-height="600" /></span></span><span style="display:none">N</span></sup></li><li><span title="www.chemspider.com"><a rel="nofollow" class="external text" href="https://www.chemspider.com/Chemical-Structure.4677898.html">4677898</a></span> (<i>S</i>)<sup> <span typeof="mw:File"><span><img alt="☒" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/7px-X_mark.svg.png" decoding="async" width="7" height="8" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/11px-X_mark.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/14px-X_mark.svg.png 2x" data-file-width="525" data-file-height="600" /></span></span><span style="display:none">N</span></sup></li></ul></div> </td></tr> <tr> <td><a href="/wiki/DrugBank" title="DrugBank">DrugBank</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><span title="www.drugbank.ca"><a rel="nofollow" class="external text" href="https://www.drugbank.ca/drugs/DB01783">DB01783</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ECHA_InfoCard" class="mw-redirect" title="ECHA InfoCard"><span title="echa.europa.eu">ECHA InfoCard</span></a> </td> <td><a rel="nofollow" class="external text" href="https://echa.europa.eu/substance-information/-/substanceinfo/100.009.061">100.009.061</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q179894#P2566" title="Edit this at Wikidata"><img alt="Edit this at Wikidata" src="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/10px-OOjs_UI_icon_edit-ltr-progressive.svg.png" decoding="async" width="10" height="10" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/15px-OOjs_UI_icon_edit-ltr-progressive.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/20px-OOjs_UI_icon_edit-ltr-progressive.svg.png 2x" data-file-width="20" data-file-height="20" /></a></span> </td></tr> <tr> <td><a href="/wiki/European_Community_number" title="European Community number"><span title="European Community number (chemical identifier)">EC Number</span></a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li>209-965-4</li></ul></div> </td></tr> <tr> <td><a href="/wiki/KEGG" title="KEGG">KEGG</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><span title="www.kegg.jp"><a rel="nofollow" class="external text" href="https://www.kegg.jp/entry/D07413">D07413</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><a href="/wiki/Medical_Subject_Headings" title="Medical Subject Headings">MeSH</a> </td> <td><span title="www.nlm.nih.gov"><a rel="nofollow" class="external text" href="https://www.nlm.nih.gov/cgi/mesh/2014/MB_cgi?mode=&term=Pantothenic+Acid">Pantothenic+Acid</a></span> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/PubChem" title="PubChem">PubChem</a> <abbr title="Compound ID">CID</abbr></div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><span title="pubchem.ncbi.nlm.nih.gov"><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/988">988</a></span></li><li><span title="pubchem.ncbi.nlm.nih.gov"><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/6613">6613</a></span> (<i>R</i>)</li><li><span title="pubchem.ncbi.nlm.nih.gov"><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/5748353">5748353</a></span> (<i>S</i>)</li></ul></div> </td></tr> <tr> <td><a href="/wiki/RTECS" class="mw-redirect" title="RTECS">RTECS number</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li>RU4729000</li></ul></div> </td></tr> <tr> <td><a href="/wiki/Unique_Ingredient_Identifier" title="Unique Ingredient Identifier">UNII</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><span title="precision.fda.gov"><a rel="nofollow" class="external text" href="https://precision.fda.gov/uniisearch/srs/unii/66Y94D1203">66Y94D1203</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li><li><span title="precision.fda.gov"><a rel="nofollow" class="external text" href="https://precision.fda.gov/uniisearch/srs/unii/19F5HK2737">19F5HK2737</a></span> (<i>R</i>)<sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/CompTox_Chemicals_Dashboard" title="CompTox Chemicals Dashboard">CompTox Dashboard</a> <span style="font-weight:normal">(<abbr title="U.S. Environmental Protection Agency">EPA</abbr>)</span></div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><span title="comptox.epa.gov"><a rel="nofollow" class="external text" href="https://comptox.epa.gov/dashboard/chemical/details/DTXSID7047229">DTXSID7047229</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q179894#P3117" title="Edit this at Wikidata"><img alt="Edit this at Wikidata" src="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/10px-OOjs_UI_icon_edit-ltr-progressive.svg.png" decoding="async" width="10" height="10" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/15px-OOjs_UI_icon_edit-ltr-progressive.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/20px-OOjs_UI_icon_edit-ltr-progressive.svg.png 2x" data-file-width="20" data-file-height="20" /></a></span></span></li></ul></div> </td></tr> <tr> <td colspan="2"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold; text-align:left; font-weight:normal;"><div><a href="/wiki/International_Chemical_Identifier" title="International Chemical Identifier">InChI</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.5em; text-align:left;"><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">InChI=1S/C9H17NO5/c1-9(2,5-11)7(14)8(15)10-4-3-6(12)13/h7,11,14H,3-5H2,1-2H3,(H,10,15)(H,12,13)<sup> <span typeof="mw:File"><span><img alt="☒" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/7px-X_mark.svg.png" decoding="async" width="7" height="8" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/11px-X_mark.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/14px-X_mark.svg.png 2x" data-file-width="525" data-file-height="600" /></span></span><span style="display:none">N</span></sup></div><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">Key: GHOKWGTUZJEAQD-UHFFFAOYSA-N<sup> <span typeof="mw:File"><span><img alt="☒" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/7px-X_mark.svg.png" decoding="async" width="7" height="8" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/11px-X_mark.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/14px-X_mark.svg.png 2x" data-file-width="525" data-file-height="600" /></span></span><span style="display:none">N</span></sup></div></div></li></ul> </div> </td></tr> <tr> <td colspan="2"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold; text-align:left; font-weight:normal;"><div><a href="/wiki/Simplified_molecular-input_line-entry_system" class="mw-redirect" title="Simplified molecular-input line-entry system">SMILES</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.6em; word-wrap:break-word; text-indent:-1.5em; text-align:left; font-size:97%; line-height:120%;">CC(C)(CO)C(C(=O)NCCC(=O)O)O</div></li><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.6em; word-wrap:break-word; text-indent:-1.5em; text-align:left; font-size:97%; line-height:120%;">(<i>R</i>): CC(C)(CO)[C@H](C(=O)NCCC(=O)O)O</div></li><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.6em; word-wrap:break-word; text-indent:-1.5em; text-align:left; font-size:97%; line-height:120%;">(<i>S</i>): CC(C)(CO)[C@@H](C(=O)NCCC(=O)O)O</div></li></ul> </div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba;color:inherit; text-align: center;">Properties </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Chemical_formula" title="Chemical formula">Chemical formula</a></div> </td> <td><span title="Carbon">C</span><sub>9</sub><span title="Hydrogen">H</span><sub>17</sub><span title="Nitrogen">N</span><span title="Oxygen">O</span><sub>5</sub> </td></tr> <tr> <td><a href="/wiki/Molar_mass" title="Molar mass">Molar mass</a> </td> <td><span class="nowrap"><span data-sort-value="7002219237000000000♠"></span>219.237</span> g·mol<sup>−1</sup>   </td></tr> <tr> <td>Appearance </td> <td>Yellow oil<br /> Colorless crystals (Ca<sup>2+</sup> salt) </td></tr> <tr> <td><a href="/wiki/Odor" title="Odor">Odor</a> </td> <td>Odorless </td></tr> <tr> <td><a href="/wiki/Density" title="Density">Density</a> </td> <td>1.266 g/cm<sup>3</sup><br /> 1.32 g/cm<sup>3</sup> (Ca<sup>2+</sup> salt)<sup id="cite_ref-eu_1-0" class="reference"><a href="#cite_note-eu-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><a href="/wiki/Melting_point" title="Melting point">Melting point</a> </td> <td>183.833 °C (362.899 °F; 456.983 K) <br /> 196–200 °C (385–392 °F; 469–473 K)<br /> decomposes (Ca<sup>2+</sup> salt)<sup id="cite_ref-eu_1-2" class="reference"><a href="#cite_note-eu-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-chemicalland_3-1" class="reference"><a href="#cite_note-chemicalland-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-mod_5-2" class="reference"><a href="#cite_note-mod-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Aqueous_solution" title="Aqueous solution">Solubility in water</a></div> </td> <td>Very soluble<sup id="cite_ref-crc_2-0" class="reference"><a href="#cite_note-crc-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup><br /> 2.11 g/mL (Ca<sup>2+</sup> salt)<sup id="cite_ref-eu_1-1" class="reference"><a href="#cite_note-eu-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><a href="/wiki/Solubility" title="Solubility">Solubility</a> </td> <td>Very soluble in <a href="/wiki/Benzene" title="Benzene">C<sub>6</sub>H<sub>6</sub></a>, <a href="/wiki/Diethyl_ether" title="Diethyl ether">ether</a><sup id="cite_ref-crc_2-1" class="reference"><a href="#cite_note-crc-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup><br />Ca<sup>2+</sup> salt:<br />Slightly soluble in <a href="/wiki/Ethanol" title="Ethanol">alcohol</a>, <a href="/wiki/Chloroform" title="Chloroform">CHCl<sub>3</sub></a><sup id="cite_ref-chemicalland_3-0" class="reference"><a href="#cite_note-chemicalland-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><a href="/wiki/Partition_coefficient" title="Partition coefficient">log <i>P</i></a> </td> <td>−1.416<sup id="cite_ref-hmdbsa_4-0" class="reference"><a href="#cite_note-hmdbsa-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><a href="/wiki/Acid_dissociation_constant" title="Acid dissociation constant">Acidity</a> (p<i>K</i><sub>a</sub>) </td> <td>4.41<sup id="cite_ref-mod_5-0" class="reference"><a href="#cite_note-mod-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><a href="/wiki/Acid_dissociation_constant" title="Acid dissociation constant">Basicity</a> (p<i>K</i><sub>b</sub>) </td> <td>9.698 </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Specific_rotation" title="Specific rotation">Chiral rotation</a> ([α]<sub>D</sub>)</div> </td> <td>+37.5°<br /> +24.3° (Ca<sup>2+</sup> salt)<sup id="cite_ref-mod_5-1" class="reference"><a href="#cite_note-mod-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <th colspan="2" style="background: #f8eaba;color:inherit; text-align: center;">Hazards </th></tr> <tr> <td><a href="/wiki/NFPA_704" title="NFPA 704"><b>NFPA 704</b></a> (fire diamond) </td> <td><style data-mw-deduplicate="TemplateStyles:r1170367383">.mw-parser-output .nfpa-704-diamond-ref{float:right;padding:1px;text-align:right}.mw-parser-output .nfpa-704-diamond-container{width:82px;font-family:sans-serif;margin:0 auto}.mw-parser-output .nfpa-704-diamond-container-ref{float:left;margin-left:1em}.mw-parser-output .nfpa-704-diamond-images{float:left;font-size:20px;text-align:center;position:relative;height:80px;width:80px;padding:1px}.mw-parser-output .nfpa-704-diamond-map{position:absolute;height:80px;width:80px}.mw-parser-output .nfpa-704-diamond .noresize{margin:0 auto}.mw-parser-output .nfpa-704-diamond-code{line-height:1em;text-align:center;position:absolute}.mw-parser-output .nfpa-704-diamond-code>a{color:black}.mw-parser-output .nfpa-704-diamond-blue{width:13px;top:31px;left:15px}.mw-parser-output .nfpa-704-diamond-red{width:12px;top:12px;left:35px}.mw-parser-output .nfpa-704-diamond-yellow{width:13px;top:31px;left:54px}.mw-parser-output .nfpa-704-diamond-white-image{position:relative;top:51px;left:0}.mw-parser-output .nfpa-704-diamond-white-text{vertical-align:middle;text-align:center;line-height:80%;position:absolute;top:52px}.mw-parser-output .nfpa-704-diamond-white-text a>span{position:absolute;color:black}.mw-parser-output .nfpa-704-diamond-white-wors{font-size:15px;width:23px;left:29px}.mw-parser-output .nfpa-704-diamond-white-wox{font-size:15px;font-stretch:condensed;width:21px;line-height:80%;top:-4px;left:29px}.mw-parser-output .nfpa-704-diamond-white-abcp{font-size:13.5px;font-stretch:condensed;width:28px;left:26px}.mw-parser-output .nfpa-704-diamond-white-ac{font-size:10px;width:30px;left:25px}.mw-parser-output .nfpa-704-diamond-white-strike{text-decoration:line-through}</style><div class="nfpa-704-diamond notheme"><div class="nfpa-704-diamond-container"><div class="nfpa-704-diamond-images nounderlines"> <div class="nfpa-704-diamond-map"><figure class="noresize" typeof="mw:File"><span><img alt="NFPA 704 four-colored diamond" src="//upload.wikimedia.org/wikipedia/commons/thumb/6/6f/NFPA_704.svg/80px-NFPA_704.svg.png" decoding="async" width="80" height="80" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/6f/NFPA_704.svg/120px-NFPA_704.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/6f/NFPA_704.svg/160px-NFPA_704.svg.png 2x" data-file-width="512" data-file-height="512" usemap="#ImageMap_482e25fdfe95519d" /></span><map name="ImageMap_482e25fdfe95519d"><area href="/wiki/NFPA_704#Blue" shape="poly" coords="23,23,47,47,23,70,0,47" alt="Health 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroform" title="Health 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroform" /><area href="/wiki/NFPA_704#Red" shape="poly" coords="47,0,70,23,47,47,23,23" alt="Flammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oil" title="Flammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oil" /><area href="/wiki/NFPA_704#Yellow" shape="poly" coords="70,23,94,47,70,70,47,47" alt="Instability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogen" title="Instability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogen" /><area href="/wiki/NFPA_704#White" shape="poly" coords="47,47,70,70,47,94,23,70" alt="Special hazards (white): no code" title="Special hazards (white): no code" /></map><figcaption></figcaption></figure></div><div class="nfpa-704-diamond-code nfpa-704-diamond-blue"> <a href="/wiki/NFPA_704#Blue" title="NFPA 704"><span title="Health 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroform" class="notheme mw-no-invert">2</span></a></div><div class="nfpa-704-diamond-code nfpa-704-diamond-red"> <a href="/wiki/NFPA_704#Red" title="NFPA 704"><span title="Flammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oil" class="notheme mw-no-invert">1</span></a></div><div class="nfpa-704-diamond-code nfpa-704-diamond-yellow"> <a href="/wiki/NFPA_704#Yellow" title="NFPA 704"><span title="Instability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogen" class="notheme mw-no-invert">0</span></a></div></div></div></div> </td></tr> <tr> <td colspan="2" style="text-align:left; background-color:#eaeaea;color:inherit;"><b>Lethal dose</b> or concentration (LD, LC): </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">LD<sub>50</sub> (<a href="/wiki/Lethal_dose#LD50" title="Lethal dose">median dose</a>)</div> </td> <td>> 10 mg/g (Ca<sup>2+</sup> salt)<sup id="cite_ref-chemicalland_3-2" class="reference"><a href="#cite_note-chemicalland-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <th colspan="2" style="background: #f8eaba;color:inherit; text-align: center;">Related compounds </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">Related alkanoic acids</div> </td> <td><a href="/wiki/Arginine" title="Arginine">Arginine</a><br /><a href="/wiki/Hopantenic_acid" title="Hopantenic acid">Hopantenic acid</a><br /><a href="/wiki/4-(%CE%B3-Glutamylamino)butanoic_acid" title="4-(γ-Glutamylamino)butanoic acid">4-(γ-Glutamylamino)butanoic acid</a> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">Related compounds</div> </td> <td><a href="/wiki/Panthenol" title="Panthenol">Panthenol</a> </td></tr> <tr> <td colspan="2" style="text-align:left; background:#f8eaba; color:inherit; border:1px solid #a2a9b1;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">Except where otherwise noted, data are given for materials in their <a href="/wiki/Standard_state" title="Standard state">standard state</a> (at 25 °C [77 °F], 100 kPa).</div> <div style="margin-top: 0.3em;"><div style="text-align:center;"><span typeof="mw:File"><span><img alt="☒" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/12px-X_mark.svg.png" decoding="async" width="12" height="14" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/18px-X_mark.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/24px-X_mark.svg.png 2x" data-file-width="525" data-file-height="600" /></span></span><span style="display:none">N</span> <span class="reflink plainlinks nourlexpansion"><a class="external text" href="https://en.wikipedia.org/w/index.php?title=Special:ComparePages&rev1=477003091&page2=Pantothenic+acid">verify</a></span> (<a href="/wiki/Wikipedia:WikiProject_Chemicals/Chembox_validation" title="Wikipedia:WikiProject Chemicals/Chembox validation">what is</a> <sup><span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span><span typeof="mw:File"><span><img alt="☒" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/7px-X_mark.svg.png" decoding="async" width="7" height="8" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/11px-X_mark.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/14px-X_mark.svg.png 2x" data-file-width="525" data-file-height="600" /></span></span><span style="display:none">N</span></sup> ?) </div></div> <div style="margin-top: 0.3em; text-align: center;"><a href="/wiki/Wikipedia:Chemical_infobox#References" title="Wikipedia:Chemical infobox">Infobox references</a></div> </td></tr> </tbody></table><div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Chemical compound</div> <p><b>Pantothenic acid</b> (<b>vitamin B<sub>5</sub></b>) is a <a href="/wiki/B_vitamin" class="mw-redirect" title="B vitamin">B vitamin</a> and an <a href="/wiki/Essential_nutrient" class="mw-redirect" title="Essential nutrient">essential nutrient</a>.<sup id="cite_ref-ods_6-0" class="reference"><a href="#cite_note-ods-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> All animals need pantothenic acid in order to synthesize <a href="/wiki/Coenzyme_A" title="Coenzyme A">coenzyme A</a> (CoA), which is essential for cellular energy production and for the synthesis and degradation of <a href="/wiki/Protein" title="Protein">proteins</a>, <a href="/wiki/Carbohydrate" title="Carbohydrate">carbohydrates</a>, and <a href="/wiki/Fat" title="Fat">fats</a>.<sup id="cite_ref-ods_6-1" class="reference"><a href="#cite_note-ods-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-lpi_7-0" class="reference"><a href="#cite_note-lpi-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> </p><p>Pantothenic acid is the combination of <a href="/wiki/Pantoic_acid" title="Pantoic acid">pantoic acid</a> and <a href="/wiki/Beta-Alanine" class="mw-redirect" title="Beta-Alanine">β-alanine</a>. Its name comes from the <a href="/wiki/Greek_language" title="Greek language">Greek</a> <span title="Ancient Greek (to 1453)-language text"><span lang="grc">πάντοθεν</span></span> <i>pantothen</i>, meaning "from everywhere", because pantothenic acid, at least in small amounts, is in almost all foods.<sup id="cite_ref-ods_6-2" class="reference"><a href="#cite_note-ods-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-usda_8-0" class="reference"><a href="#cite_note-usda-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-lpi_7-1" class="reference"><a href="#cite_note-lpi-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> Deficiency of pantothenic acid is very rare in humans.<sup id="cite_ref-ods_6-3" class="reference"><a href="#cite_note-ods-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-lpi_7-2" class="reference"><a href="#cite_note-lpi-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> In dietary supplements and animal feed, the form commonly used is calcium pantothenate, because chemically it is more stable, and hence makes for longer product shelf-life, than sodium pantothenate and free pantothenic acid.<sup id="cite_ref-eu_1-3" class="reference"><a href="#cite_note-eu-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Definition">Definition</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Pantothenic_acid&action=edit&section=1" title="Edit section: Definition"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure class="mw-halign-left skin-invert-image" typeof="mw:File/Thumb"><a href="/wiki/File:Coenzym_A_beschriftet.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/4/47/Coenzym_A_beschriftet.svg/300px-Coenzym_A_beschriftet.svg.png" decoding="async" width="300" height="122" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/4/47/Coenzym_A_beschriftet.svg/450px-Coenzym_A_beschriftet.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/4/47/Coenzym_A_beschriftet.svg/600px-Coenzym_A_beschriftet.svg.png 2x" data-file-width="845" data-file-height="343" /></a><figcaption>Structure of coenzyme A: 1: 3′-phosphoadenosine. 2: diphosphate, organophosphate anhydride. 3: pantoic acid. 4: β-alanine. 5: cysteamine.</figcaption></figure> <p>Pantothenic acid is a water-soluble <a href="/wiki/Vitamin" title="Vitamin">vitamin</a>, one of the <a href="/wiki/B_vitamin" class="mw-redirect" title="B vitamin">B vitamins</a>. It is synthesized from the amino acid β-alanine and pantoic acid (see <a href="#Biosynthesis">biosynthesis</a> and structure of coenzyme A figures). Unlike <a href="/wiki/Vitamin_E" title="Vitamin E">vitamin E</a> or <a href="/wiki/Vitamin_K" title="Vitamin K">vitamin K</a>, which occurs in several chemically related forms known as <a href="/wiki/Vitamer" title="Vitamer">vitamers</a>, pantothenic acid is only one chemical compound. It is a starting compound in the synthesis of <a href="/wiki/Coenzyme_A" title="Coenzyme A">coenzyme A</a> (CoA), a cofactor for many enzyme processes.<sup id="cite_ref-lpi_7-3" class="reference"><a href="#cite_note-lpi-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-PKIN2012Panto_9-0" class="reference"><a href="#cite_note-PKIN2012Panto-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-DRItext_10-0" class="reference"><a href="#cite_note-DRItext-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Use_in_biosynthesis_of_coenzyme_A">Use in biosynthesis of coenzyme A</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Pantothenic_acid&action=edit&section=2" title="Edit section: Use in biosynthesis of coenzyme A"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure class="mw-default-size mw-halign-left skin-invert-image" typeof="mw:File/Thumb"><a href="/wiki/File:CoA_Biosynthetic_Pathway.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/6/6f/CoA_Biosynthetic_Pathway.png/220px-CoA_Biosynthetic_Pathway.png" decoding="async" width="220" height="245" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/6f/CoA_Biosynthetic_Pathway.png/330px-CoA_Biosynthetic_Pathway.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/6f/CoA_Biosynthetic_Pathway.png/440px-CoA_Biosynthetic_Pathway.png 2x" data-file-width="610" data-file-height="678" /></a><figcaption>Details of the biosynthetic pathway of CoA synthesis from pantothenic acid</figcaption></figure> <p>Pantothenic acid is a precursor to CoA via a five-step process. The biosynthesis requires pantothenic acid, cysteine, and four equivalents of ATP (see figure).<sup id="cite_ref-Leonardi2005_11-0" class="reference"><a href="#cite_note-Leonardi2005-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> </p> <ol><li>Pantothenic acid is <a href="/wiki/Phosphorylation" title="Phosphorylation">phosphorylated</a> to 4′-phosphopantothenate by the enzyme <a href="/wiki/Pantothenate_kinase" title="Pantothenate kinase">pantothenate kinase</a>. This is the committed step in CoA biosynthesis and requires ATP.<sup id="cite_ref-Leonardi2007_12-0" class="reference"><a href="#cite_note-Leonardi2007-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup></li> <li>A <a href="/wiki/Cysteine" title="Cysteine">cysteine</a> is added to 4′-phosphopantothenate by the enzyme <a href="/wiki/Phosphopantothenoylcysteine_synthetase" class="mw-redirect" title="Phosphopantothenoylcysteine synthetase">phosphopantothenoylcysteine synthetase</a> to form 4'-phospho-N-pantothenoylcysteine (PPC). This step is coupled with <a href="/wiki/ATP_hydrolysis" title="ATP hydrolysis">ATP hydrolysis</a>.<sup id="cite_ref-Leonardi2007_12-1" class="reference"><a href="#cite_note-Leonardi2007-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup></li> <li>PPC is <a href="/wiki/Decarboxylation" title="Decarboxylation">decarboxylated</a> to <a href="/wiki/4%27-phosphopantetheine" class="mw-redirect" title="4'-phosphopantetheine">4′-phosphopantetheine</a> by <a href="/wiki/Phosphopantothenoylcysteine_decarboxylase" title="Phosphopantothenoylcysteine decarboxylase">phosphopantothenoylcysteine decarboxylase</a></li> <li>4′-Phosphopantetheine is adenylated (or more properly, <a href="/wiki/Adenylation" class="mw-redirect" title="Adenylation">AMPylated</a>) to form dephospho-CoA by the enzyme <a href="/wiki/Pantetheine-phosphate_adenylyltransferase" title="Pantetheine-phosphate adenylyltransferase">phosphopantetheine adenylyl transferase</a></li> <li>Finally, dephospho-CoA is phosphorylated to coenzyme A by the enzyme <a href="/wiki/Dephospho-CoA_kinase" title="Dephospho-CoA kinase">dephosphocoenzyme A kinase</a>. This final step also requires ATP.<sup id="cite_ref-Leonardi2007_12-2" class="reference"><a href="#cite_note-Leonardi2007-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup></li></ol> <p>This pathway is suppressed by <a href="/wiki/End-product_inhibition" class="mw-redirect" title="End-product inhibition">end-product inhibition</a>, meaning that CoA is a competitive inhibitor of pantothenate kinase, the enzyme responsible for the first step.<sup id="cite_ref-Leonardi2007_12-3" class="reference"><a href="#cite_note-Leonardi2007-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup> </p><p>Coenzyme A is necessary in the reaction mechanism of the <a href="/wiki/Citric_acid_cycle" title="Citric acid cycle">citric acid cycle</a>. This process is the body's primary <a href="/wiki/Catabolism" title="Catabolism">catabolic pathway</a> and is essential in breaking down the building blocks of the cell such as <a href="/wiki/Carbohydrate" title="Carbohydrate">carbohydrates</a>, <a href="/wiki/Amino_acid" title="Amino acid">amino acids</a> and <a href="/wiki/Lipid" title="Lipid">lipids</a>, for fuel.<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> CoA is important in energy metabolism for <a href="/wiki/Pyruvate" class="mw-redirect" title="Pyruvate">pyruvate</a> to enter the <a href="/wiki/Tricarboxylic_acid_cycle" class="mw-redirect" title="Tricarboxylic acid cycle">tricarboxylic acid cycle</a> (TCA cycle) as acetyl-CoA, and for <a href="/wiki/%CE%91-ketoglutarate" class="mw-redirect" title="Α-ketoglutarate">α-ketoglutarate</a> to be transformed to <a href="/wiki/Succinyl-CoA" title="Succinyl-CoA">succinyl-CoA</a> in the cycle.<sup id="cite_ref-Gropper_2009_14-0" class="reference"><a href="#cite_note-Gropper_2009-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup> CoA is also required for acylation and acetylation, which, for example, are involved in <a href="/wiki/Signal_transduction" title="Signal transduction">signal transduction</a>, and various enzyme functions.<sup id="cite_ref-Gropper_2009_14-1" class="reference"><a href="#cite_note-Gropper_2009-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup> In addition to functioning as CoA, this compound can act as an <a href="/wiki/Acyl" class="mw-redirect" title="Acyl">acyl</a> group carrier to form <a href="/wiki/Acetyl-CoA" title="Acetyl-CoA">acetyl-CoA</a> and other related compounds; this is a way to transport <a href="/wiki/Carbon" title="Carbon">carbon</a> atoms within the cell.<sup id="cite_ref-PKIN2012Panto_9-1" class="reference"><a href="#cite_note-PKIN2012Panto-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> CoA is also required in the formation of <a href="/wiki/Acyl_carrier_protein" title="Acyl carrier protein">acyl carrier protein</a> (ACP),<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> which is required for fatty acid synthesis.<sup id="cite_ref-PKIN2012Panto_9-2" class="reference"><a href="#cite_note-PKIN2012Panto-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-16" class="reference"><a href="#cite_note-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup> Its synthesis also connects with other vitamins such as thiamin and folic acid.<sup id="cite_ref-17" class="reference"><a href="#cite_note-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Dietary_recommendations">Dietary recommendations</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Pantothenic_acid&action=edit&section=3" title="Edit section: Dietary recommendations"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The US Institute of Medicine (IOM) updated Estimated Average Requirements (EARs) and Recommended Dietary Allowances (RDAs) for B vitamins in 1998. At that time, there was not sufficient information to establish EARs and RDAs for pantothenic acid. In instances such as this, the Board sets Adequate Intakes (AIs), with the understanding that at some later date, AIs may be replaced by more exact information.<sup id="cite_ref-DRItext_10-1" class="reference"><a href="#cite_note-DRItext-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-DRIExplain_18-0" class="reference"><a href="#cite_note-DRIExplain-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup> </p><p>The current AI for teens and adults ages 14 and up is 5 mg/day. This was based in part on the observation that for a typical diet, urinary excretion was approximately 2.6 mg/day, and that <a href="/wiki/Bioavailability" title="Bioavailability">bioavailability</a> of food-bound pantothenic acid was roughly 50%.<sup id="cite_ref-DRItext_10-2" class="reference"><a href="#cite_note-DRItext-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> AI for pregnancy is 6 mg/day. AI for <a href="/wiki/Lactation" title="Lactation">lactation</a> is 7 mg/day. For infants up to 12 months, the AI is 1.8 mg/day. For children ages 1–13 years, the AI increases with age from 2 to 4 mg/day. Collectively the EARs, RDAs, AIs and ULs are referred to as <a href="/wiki/Dietary_Reference_Intake" title="Dietary Reference Intake">Dietary Reference Intakes</a> (DRIs).<sup id="cite_ref-DRItext_10-3" class="reference"><a href="#cite_note-DRItext-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-DRIExplain_18-1" class="reference"><a href="#cite_note-DRIExplain-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup> </p> <table class="wikitable"> <tbody><tr> <th>Age group </th> <th>Age </th> <th>Adequate intake<sup id="cite_ref-DRItext_10-4" class="reference"><a href="#cite_note-DRItext-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> </th></tr> <tr> <td>Infants </td> <td>0–6 months </td> <td>1.7 mg </td></tr> <tr> <td>Infants </td> <td>7–12 months </td> <td>1.8 mg </td></tr> <tr> <td>Children </td> <td>1–3 years </td> <td>2 mg </td></tr> <tr> <td>Children </td> <td>4–8 years </td> <td>3 mg </td></tr> <tr> <td>Children </td> <td>9–13 years </td> <td>4 mg </td></tr> <tr> <td>Adult men and women </td> <td>14+ years </td> <td>5 mg </td></tr> <tr> <td>Pregnant women </td> <td>(vs. 5) </td> <td>6 mg </td></tr> <tr> <td>Breastfeeding women </td> <td>(vs. 5) </td> <td>7 mg </td></tr></tbody></table> <p>While for many nutrients, the US Department of Agriculture uses food composition data combined with food consumption survey results to estimate average consumption, the surveys and reports do not include pantothenic acid in the analyses.<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> Less formal estimates of adult daily intakes report about 4 to 7 mg/day.<sup id="cite_ref-DRItext_10-5" class="reference"><a href="#cite_note-DRItext-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> </p><p>The <a href="/wiki/European_Food_Safety_Authority" title="European Food Safety Authority">European Food Safety Authority</a> (EFSA) refers to the collective set of information as Dietary Reference Values, with Population Reference Intake (PRI) instead of RDA, and Average Requirement instead of EAR. AI and UL are defined the same as in the US. For women and men over age 11, the Adequate Intake (AI) is set at 5 mg/day. AI for pregnancy is 5 mg/day, for lactation 7 mg/day. For children ages 1–10 years, the AI is 4 mg/day. These AIs are similar to the US AIs.<sup id="cite_ref-20" class="reference"><a href="#cite_note-20"><span class="cite-bracket">[</span>20<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Safety">Safety</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Pantothenic_acid&action=edit&section=4" title="Edit section: Safety"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>As for safety, the IOM sets <a href="/wiki/Tolerable_upper_intake_level" class="mw-redirect" title="Tolerable upper intake level">Tolerable upper intake levels</a> (ULs) for vitamins and minerals when evidence is sufficient. In the case of pantothenic acid, there is no UL, as there is no human data for adverse effects from high doses.<sup id="cite_ref-DRItext_10-6" class="reference"><a href="#cite_note-DRItext-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> The EFSA also reviewed the safety question and reached the same conclusion as in the United States – that there was not sufficient evidence to set a UL for pantothenic acid.<sup id="cite_ref-21" class="reference"><a href="#cite_note-21"><span class="cite-bracket">[</span>21<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Labeling_requirements">Labeling requirements</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Pantothenic_acid&action=edit&section=5" title="Edit section: Labeling requirements"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>For US food and dietary supplement labeling purposes, the amount in a serving is expressed as a percent of Daily Value (%DV). For pantothenic acid labeling purposes, 100% of the Daily Value was 10 mg, but as of May 2016 it was revised to 5 mg to bring it into agreement with the AI.<sup id="cite_ref-FedReg_22-0" class="reference"><a href="#cite_note-FedReg-22"><span class="cite-bracket">[</span>22<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-23" class="reference"><a href="#cite_note-23"><span class="cite-bracket">[</span>23<span class="cite-bracket">]</span></a></sup> Compliance with the updated labeling regulations was required by January 2020 for manufacturers with <a href="/wiki/US$" class="mw-redirect" title="US$">US$</a>10 million or more in annual food sales, and by January 2021 for manufacturers with lower volume food sales.<sup id="cite_ref-FDAdelay_24-0" class="reference"><a href="#cite_note-FDAdelay-24"><span class="cite-bracket">[</span>24<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-25" class="reference"><a href="#cite_note-25"><span class="cite-bracket">[</span>25<span class="cite-bracket">]</span></a></sup> A table of the old and new adult daily values is provided at <a href="/wiki/Reference_Daily_Intake" title="Reference Daily Intake">Reference Daily Intake</a>. </p> <div class="mw-heading mw-heading2"><h2 id="Sources">Sources</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Pantothenic_acid&action=edit&section=6" title="Edit section: Sources"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Dietary">Dietary</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Pantothenic_acid&action=edit&section=7" title="Edit section: Dietary"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Food sources of pantothenic acid include animal-sourced foods, including dairy foods and eggs.<sup id="cite_ref-ods_6-4" class="reference"><a href="#cite_note-ods-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-usda_8-1" class="reference"><a href="#cite_note-usda-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> Potatoes, tomato products, oat-cereals, sunflower seeds, avocado are good plant sources. Mushrooms are good sources, too. Whole grains are another source of the vitamin, but milling to make white rice or white flour removes much of the pantothenic acid, as it is found in the outer layers of whole grains.<sup id="cite_ref-ods_6-5" class="reference"><a href="#cite_note-ods-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-DRItext_10-7" class="reference"><a href="#cite_note-DRItext-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> In animal feeds, the most important sources are alfalfa, cereal, fish meal, peanut meal, molasses, rice bran, wheat bran, and yeasts.<sup id="cite_ref-Combs2007_26-0" class="reference"><a href="#cite_note-Combs2007-26"><span class="cite-bracket">[</span>26<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Supplements">Supplements</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Pantothenic_acid&action=edit&section=8" title="Edit section: Supplements"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><a href="/wiki/Dietary_supplements" class="mw-redirect" title="Dietary supplements">Dietary supplements</a> of pantothenic acid commonly use <a href="/wiki/Pantothenol" class="mw-redirect" title="Pantothenol">pantothenol</a> (or <i>panthenol</i>), a <a href="/wiki/Shelf-stable_food" title="Shelf-stable food">shelf-stable</a> <a href="/wiki/Functional_analog_(chemistry)" title="Functional analog (chemistry)">analog</a>, which is converted to pantothenic acid once consumed.<sup id="cite_ref-lpi_7-4" class="reference"><a href="#cite_note-lpi-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> Calcium pantothenate – a <a href="/wiki/Salt_(chemistry)" title="Salt (chemistry)">salt</a> – may be used in manufacturing because it is more resistant than pantothenic acid to factors that deteriorate stability, such as acid, <a href="/wiki/Alkali" title="Alkali">alkali</a> or heat.<sup id="cite_ref-PKIN2012Panto_9-3" class="reference"><a href="#cite_note-PKIN2012Panto-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Combs2007_26-1" class="reference"><a href="#cite_note-Combs2007-26"><span class="cite-bracket">[</span>26<span class="cite-bracket">]</span></a></sup> The amount of pantothenic acid in dietary supplement products may contain up to 1,000 mg (200 times the Adequate Intake level for adults), without evidence that such large amounts provide any benefit.<sup id="cite_ref-lpi_7-5" class="reference"><a href="#cite_note-lpi-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-ods_6-6" class="reference"><a href="#cite_note-ods-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> According to <a href="/wiki/WebMD" title="WebMD">WebMD</a>, pantothenic acid supplements have a long list of claimed uses, but there is insufficient scientific evidence to support any of them.<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> </p><p>As a dietary supplement, pantothenic acid is not the same as <a href="/wiki/Pantethine" title="Pantethine">pantethine</a>, which is composed of two pantothenic acid molecules linked by a <a href="/wiki/Disulfide" title="Disulfide">disulfide</a> bridge.<sup id="cite_ref-lpi_7-6" class="reference"><a href="#cite_note-lpi-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> Sold as a high-dose supplement (600 mg), pantethine may be effective for lowering blood levels of <a href="/wiki/LDL_cholesterol" class="mw-redirect" title="LDL cholesterol">LDL cholesterol</a> – a <a href="/wiki/Risk_factor_(epidemiology)" class="mw-redirect" title="Risk factor (epidemiology)">risk factor</a> for cardiovascular diseases – but its long-term effects are unknown, so use should be supervised by a physician.<sup id="cite_ref-lpi_7-7" class="reference"><a href="#cite_note-lpi-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> Dietary supplementation with pantothenic acid does not have the cholesterol-lowering effect as pantethine.<sup id="cite_ref-PKIN2012Panto_9-4" class="reference"><a href="#cite_note-PKIN2012Panto-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Fortification">Fortification</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Pantothenic_acid&action=edit&section=9" title="Edit section: Fortification"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>According to the Global Fortification Data Exchange, pantothenic acid deficiency is so rare that no countries require that foods be fortified.<sup id="cite_ref-Map_28-0" class="reference"><a href="#cite_note-Map-28"><span class="cite-bracket">[</span>28<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Absorption,_metabolism_and_excretion"><span id="Absorption.2C_metabolism_and_excretion"></span>Absorption, metabolism and excretion</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Pantothenic_acid&action=edit&section=10" title="Edit section: Absorption, metabolism and excretion"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>When found in foods, most pantothenic acid is in the form of CoA or bound to <a href="/wiki/Acyl_carrier_protein" title="Acyl carrier protein">acyl carrier protein</a> (ACP). For the intestinal cells to absorb this vitamin, it must be converted into free pantothenic acid. Within the <a href="/wiki/Lumen_(anatomy)" title="Lumen (anatomy)">lumen</a> of the intestine, CoA and ACP are <a href="/wiki/Hydrolysis" title="Hydrolysis">hydrolyzed</a> into 4'-phosphopantetheine. The 4'-phosphopantetheine is then <a href="/wiki/Dephosphorylation" title="Dephosphorylation">dephosphorylated</a> into <a href="/wiki/Pantetheine" title="Pantetheine">pantetheine</a>. <a href="/wiki/Pantetheine_hydrolase" title="Pantetheine hydrolase">Pantetheinase</a>, an intestinal enzyme, then hydrolyzes pantetheine into free pantothenic acid.<sup id="cite_ref-Trumbo_29-0" class="reference"><a href="#cite_note-Trumbo-29"><span class="cite-bracket">[</span>29<span class="cite-bracket">]</span></a></sup> Free pantothenic acid is absorbed into intestinal cells via a saturable, sodium-dependent active transport system.<sup id="cite_ref-Gropper_2009_14-2" class="reference"><a href="#cite_note-Gropper_2009-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup> At high levels of intake, when this mechanism is saturated, some pantothenic acid may also be additionally absorbed via passive diffusion.<sup id="cite_ref-Combs2007_26-2" class="reference"><a href="#cite_note-Combs2007-26"><span class="cite-bracket">[</span>26<span class="cite-bracket">]</span></a></sup> As a whole, when intake increases 10-fold, absorption rate decreases to 10%.<sup id="cite_ref-Gropper_2009_14-3" class="reference"><a href="#cite_note-Gropper_2009-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup> </p><p>Pantothenic acid is excreted in urine. This occurs after its release from CoA. Urinary amounts are on the order of 2.6 mg/day, but decreased to negligible amounts when subjects in multi-week experimental situations were fed diets devoid of the vitamin.<sup id="cite_ref-DRItext_10-8" class="reference"><a href="#cite_note-DRItext-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Deficiency">Deficiency</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Pantothenic_acid&action=edit&section=11" title="Edit section: Deficiency"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Pantothenic acid deficiency in humans is very rare and has not been thoroughly studied. In the few cases where deficiency has been seen (prisoners of war during World War II, victims of starvation, or limited volunteer trials), nearly all symptoms were reversed with orally administered pantothenic acid.<sup id="cite_ref-Gropper_2009_14-4" class="reference"><a href="#cite_note-Gropper_2009-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-PKIN2012Panto_9-5" class="reference"><a href="#cite_note-PKIN2012Panto-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> Symptoms of deficiency are similar to other <a href="/wiki/Vitamin_B" class="mw-redirect" title="Vitamin B">vitamin B</a> deficiencies. There is impaired energy production, due to low CoA levels, which could cause symptoms of irritability, <a href="/wiki/Fatigue_(medical)" class="mw-redirect" title="Fatigue (medical)">fatigue</a>, and <a href="/wiki/Apathy" title="Apathy">apathy</a>.<sup id="cite_ref-Gropper_2009_14-5" class="reference"><a href="#cite_note-Gropper_2009-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup> Acetylcholine synthesis is also impaired; therefore, neurological symptoms can also appear in deficiency;<sup id="cite_ref-DRIGuide2006_30-0" class="reference"><a href="#cite_note-DRIGuide2006-30"><span class="cite-bracket">[</span>30<span class="cite-bracket">]</span></a></sup> they include sensation of numbness in hands and feet, <a href="/wiki/Paresthesia" title="Paresthesia">paresthesia</a> and muscle cramps. Additional symptoms could include restlessness, malaise, sleep disturbances, nausea, vomiting and abdominal cramps.<sup id="cite_ref-DRIGuide2006_30-1" class="reference"><a href="#cite_note-DRIGuide2006-30"><span class="cite-bracket">[</span>30<span class="cite-bracket">]</span></a></sup> </p><p>In animals, symptoms include disorders of the nervous, gastrointestinal, and immune systems, reduced growth rate, decreased food intake, skin lesions and changes in hair coat, and alterations in lipid and carbohydrate metabolism.<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> In rodents, there can be loss of hair color, which led to marketing of pantothenic acid as a dietary supplement which could prevent or treat graying of hair in humans (despite the lack of any human trial evidence).<sup id="cite_ref-PKIN2012Panto_9-6" class="reference"><a href="#cite_note-PKIN2012Panto-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> </p><p>Pantothenic acid status can be assessed by measuring either whole blood concentration or 24-hour urinary excretion. In humans, whole blood values less than 1 μmol/L are considered low, as is urinary excretion of less than 4.56 mmol/day.<sup id="cite_ref-PKIN2012Panto_9-7" class="reference"><a href="#cite_note-PKIN2012Panto-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Animal_nutrition">Animal nutrition</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Pantothenic_acid&action=edit&section=12" title="Edit section: Animal nutrition"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Calcium pantothenate and dexpanthenol (D-panthenol) are European Food Safety Authority (EFSA) approved additives to animal feed.<sup id="cite_ref-eu_1-4" class="reference"><a href="#cite_note-eu-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> Supplementation is on the order of 8–20 mg/kg for pigs, 10–15 mg/kg for poultry, 30–50 mg/kg for fish and 8–14 mg/kg feed for pets. These are recommended concentrations, designed to be higher than what are thought to be requirements.<sup id="cite_ref-eu_1-5" class="reference"><a href="#cite_note-eu-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> There is some evidence that feed supplementation increases pantothenic acid concentration in tissues, i.e., meat, consumed by humans, and also for eggs, but this raises no concerns for consumer safety.<sup id="cite_ref-eu_1-6" class="reference"><a href="#cite_note-eu-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> </p><p>No dietary requirement for pantothenic acid has been established in ruminant species. Synthesis of pantothenic acid by <a href="/wiki/Rumen" title="Rumen">ruminal</a> microorganisms appears to be 20 to 30 times more than dietary amounts.<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> Net microbial synthesis of pantothenic acid in the rumen of steer calves has been estimated to be 2.2 mg/kg of digestible organic matter consumed per day. Supplementation of pantothenic acid at 5 to 10 times theoretical requirements did not improve growth performance of feedlot cattle.<sup id="cite_ref-33" class="reference"><a href="#cite_note-33"><span class="cite-bracket">[</span>33<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Synthesis">Synthesis</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Pantothenic_acid&action=edit&section=13" title="Edit section: Synthesis"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Biosynthesis">Biosynthesis</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Pantothenic_acid&action=edit&section=14" title="Edit section: Biosynthesis"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure class="mw-default-size skin-invert-image" typeof="mw:File/Thumb"><a href="/wiki/File:Pantothenic_acid_biosynthesis.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/8/8d/Pantothenic_acid_biosynthesis.svg/220px-Pantothenic_acid_biosynthesis.svg.png" decoding="async" width="220" height="371" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/8/8d/Pantothenic_acid_biosynthesis.svg/330px-Pantothenic_acid_biosynthesis.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/8/8d/Pantothenic_acid_biosynthesis.svg/440px-Pantothenic_acid_biosynthesis.svg.png 2x" data-file-width="480" data-file-height="810" /></a><figcaption>Pantothenic acid biosynthesis</figcaption></figure> <p>Bacteria synthesize pantothenic acid from the amino acids aspartate and a precursor to the amino acid valine. Aspartate is converted to <a href="/wiki/%CE%92-alanine" class="mw-redirect" title="Β-alanine">β-alanine</a>. The amino group of valine is replaced by a keto-<a href="/wiki/Moiety_(chemistry)" title="Moiety (chemistry)">moiety</a> to yield <a href="/wiki/%CE%91-ketoisovalerate" class="mw-redirect" title="Α-ketoisovalerate">α-ketoisovalerate</a>, which, in turn, forms α-ketopantoate following transfer of a methyl group, then D-pantoate (also known as pantoic acid) following reduction. β-alanine and pantoic acid are then condensed to form pantothenic acid (see figure).<sup id="cite_ref-Leonardi2007_12-4" class="reference"><a href="#cite_note-Leonardi2007-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Industrial_synthesis">Industrial synthesis</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Pantothenic_acid&action=edit&section=15" title="Edit section: Industrial synthesis"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The industrial synthesis of pantothenic acid starts with the <a href="/wiki/Aldol_condensation" title="Aldol condensation">aldol condensation</a> of <a href="/wiki/Isobutyraldehyde" title="Isobutyraldehyde">isobutyraldehyde</a> and <a href="/wiki/Formaldehyde" title="Formaldehyde">formaldehyde</a>. The resulting <a href="/wiki/Hydroxypivaldehyde" title="Hydroxypivaldehyde">hydroxypivaldehyde</a> is converted to its <a href="/wiki/Cyanohydrin" title="Cyanohydrin">cyanohydrin</a> derivative. which is cyclised to give <a href="/wiki/Racemic" class="mw-redirect" title="Racemic">racemic</a> pantolactone. This sequence of reactions was first published in 1904.<sup id="cite_ref-34" class="reference"><a href="#cite_note-34"><span class="cite-bracket">[</span>34<span class="cite-bracket">]</span></a></sup> </p> <dl><dd><span class="skin-invert-image" typeof="mw:File"><a href="/wiki/File:Pantothenic_acid_synthesis.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/8/84/Pantothenic_acid_synthesis.svg/650px-Pantothenic_acid_synthesis.svg.png" decoding="async" width="650" height="196" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/8/84/Pantothenic_acid_synthesis.svg/975px-Pantothenic_acid_synthesis.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/8/84/Pantothenic_acid_synthesis.svg/1300px-Pantothenic_acid_synthesis.svg.png 2x" data-file-width="512" data-file-height="154" /></a></span></dd></dl> <p>Synthesis of the vitamin is completed by <a href="/wiki/Chiral_resolution" title="Chiral resolution">resolution</a> of the lactone using <a href="/wiki/Quinine" title="Quinine">quinine</a>, for example, followed by treatment with the calcium or sodium salt of β-alanine.<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> <div class="mw-heading mw-heading2"><h2 id="History">History</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Pantothenic_acid&action=edit&section=16" title="Edit section: History"><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">Further information: <a href="/wiki/Vitamin#History" title="Vitamin">Vitamin § History</a></div> <p>The term <i>vitamin</i> is derived from the word <i>vitamine</i>, which was coined in 1912 by Polish biochemist <a href="/wiki/Casimir_Funk" title="Casimir Funk">Casimir Funk</a>, who isolated a complex of water-soluble micronutrients essential to life, all of which he presumed to be <a href="/wiki/Amine" title="Amine">amines</a>.<sup id="cite_ref-Funk_36-0" class="reference"><a href="#cite_note-Funk-36"><span class="cite-bracket">[</span>36<span class="cite-bracket">]</span></a></sup> When this presumption was later determined not to be true, the "e" was dropped from the name, hence "vitamin".<sup id="cite_ref-Combs2007_26-3" class="reference"><a href="#cite_note-Combs2007-26"><span class="cite-bracket">[</span>26<span class="cite-bracket">]</span></a></sup> Vitamin nomenclature was alphabetical, with <a href="/wiki/Elmer_McCollum" title="Elmer McCollum">Elmer McCollum</a> calling these fat-soluble A and water-soluble B.<sup id="cite_ref-Combs2007_26-4" class="reference"><a href="#cite_note-Combs2007-26"><span class="cite-bracket">[</span>26<span class="cite-bracket">]</span></a></sup> Over time, eight chemically distinct, water-soluble B vitamins were isolated and numbered, with pantothenic acid as vitamin B<sub>5</sub>.<sup id="cite_ref-Combs2007_26-5" class="reference"><a href="#cite_note-Combs2007-26"><span class="cite-bracket">[</span>26<span class="cite-bracket">]</span></a></sup> </p><p>The essential nature of pantothenic acid was discovered by <a href="/wiki/Roger_J._Williams" title="Roger J. Williams">Roger J. Williams</a> in 1933 by showing it was required for the growth of yeast.<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> Three years later Elvehjem and Jukes demonstrated that it was a growth and anti-dermatitis factor in chickens.<sup id="cite_ref-PKIN2012Panto_9-8" class="reference"><a href="#cite_note-PKIN2012Panto-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> Williams dubbed the compound "pantothenic acid", deriving the name from the Greek word <i>pantothen</i>, which translates as "from everywhere". His reason was that he found it to be present in almost every food he tested.<sup id="cite_ref-PKIN2012Panto_9-9" class="reference"><a href="#cite_note-PKIN2012Panto-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> Williams went on to determine the chemical structure in 1940.<sup id="cite_ref-PKIN2012Panto_9-10" class="reference"><a href="#cite_note-PKIN2012Panto-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> In 1953, <a href="/wiki/Fritz_Lipmann" class="mw-redirect" title="Fritz Lipmann">Fritz Lipmann</a> shared the <a href="/wiki/Nobel_Prize_in_Physiology_or_Medicine" title="Nobel Prize in Physiology or Medicine">Nobel Prize in Physiology or Medicine</a> "for his discovery of co-enzyme A and its importance for intermediary metabolism", work he had published in 1946.<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> </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=Pantothenic_acid&action=edit&section=17" 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" style="column-width: 30em;"> <ol class="references"> <li id="cite_note-eu-1"><span class="mw-cite-backlink">^ <a href="#cite_ref-eu_1-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-eu_1-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-eu_1-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-eu_1-3"><sup><i><b>d</b></i></sup></a> <a href="#cite_ref-eu_1-4"><sup><i><b>e</b></i></sup></a> <a href="#cite_ref-eu_1-5"><sup><i><b>f</b></i></sup></a> <a href="#cite_ref-eu_1-6"><sup><i><b>g</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 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A">A</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/%CE%91-Carotene" title="Α-Carotene">α-Carotene</a></li> <li><a href="/wiki/%CE%92-Carotene" title="Β-Carotene">β-Carotene</a></li> <li><a href="/wiki/Retinol" title="Retinol">Retinol</a><sup>#</sup></li> <li><a href="/wiki/Tretinoin" title="Tretinoin">Tretinoin</a><sup>#</sup></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Vitamin_D" title="Vitamin D">D</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>D<sub>2</sub> <ul><li><a href="/wiki/Ergosterol" title="Ergosterol">Ergosterol</a></li> <li><a href="/wiki/Ergocalciferol" title="Ergocalciferol">Ergocalciferol</a><sup>#</sup></li></ul></li> <li>D<sub>3</sub> <ul><li><a href="/wiki/7-Dehydrocholesterol" title="7-Dehydrocholesterol">7-Dehydrocholesterol</a></li> <li><a href="/wiki/Previtamin_D3" title="Previtamin D3">Previtamin D<sub>3</sub></a></li> <li><a href="/wiki/Cholecalciferol" title="Cholecalciferol">Cholecalciferol</a><sup>#</sup></li> <li><a href="/wiki/Calcifediol" title="Calcifediol">25-hydroxycholecalciferol</a></li> <li><a href="/wiki/Calcitriol" title="Calcitriol">Calcitriol (1,25-dihydroxycholecalciferol)</a></li> <li><a href="/wiki/Calcitroic_acid" title="Calcitroic acid">Calcitroic acid</a></li></ul></li> <li>D<sub>4</sub> <ul><li><a href="/wiki/22-Dihydroergocalciferol" title="22-Dihydroergocalciferol">Dihydroergocalciferol</a></li></ul></li> <li><a href="/wiki/Vitamin_D5" title="Vitamin D5">D<sub>5</sub></a></li> <li>D analogues <ul><li><a href="/wiki/Alfacalcidol" title="Alfacalcidol">Alfacalcidol</a></li> <li><a href="/wiki/Dihydrotachysterol" title="Dihydrotachysterol">Dihydrotachysterol</a></li> <li><a href="/wiki/Calcipotriol" title="Calcipotriol">Calcipotriol</a></li> <li><a href="/wiki/Tacalcitol" title="Tacalcitol">Tacalcitol</a></li> <li><a href="/wiki/Paricalcitol" title="Paricalcitol">Paricalcitol</a></li></ul></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Vitamin_E" title="Vitamin E">E</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/Tocopherol" title="Tocopherol">Tocopherol</a> <ul><li><a href="/wiki/%CE%91-Tocopherol" title="Α-Tocopherol">Alpha</a></li> <li><a href="/wiki/%CE%92-Tocopherol" title="Β-Tocopherol">Beta</a></li> <li><a href="/wiki/%CE%93-Tocopherol" title="Γ-Tocopherol">Gamma</a></li> <li><a href="/wiki/%CE%94-Tocopherol" title="Δ-Tocopherol">Delta</a></li></ul></li> <li><a href="/wiki/Tocotrienol" title="Tocotrienol">Tocotrienol</a> <ul><li><a href="/wiki/%CE%91-Tocotrienol" title="Α-Tocotrienol">Alpha</a></li> <li><a href="/wiki/%CE%92-Tocotrienol" title="Β-Tocotrienol">Beta</a></li> <li><a href="/wiki/%CE%93-Tocotrienol" title="Γ-Tocotrienol">Gamma</a></li> <li>Delta</li></ul></li> <li><a href="/wiki/Tocofersolan" title="Tocofersolan">Tocofersolan</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Vitamin_K" title="Vitamin K">K</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/1,4-Naphthoquinone" title="1,4-Naphthoquinone">Naphthoquinone</a></li> <li><a href="/wiki/Phytomenadione" title="Phytomenadione">Phylloquinone (K<sub>1</sub>)</a><sup>#</sup></li> <li><a href="/wiki/Vitamin_K2" title="Vitamin K2">Menaquinones (K<sub>2</sub>)</a></li> <li><a href="/wiki/Menadione" title="Menadione">Menadione (K<sub>3</sub>)</a><sup>‡</sup></li> <li><a href="/wiki/Vitamin_K4" class="mw-redirect" title="Vitamin K4">Various (K<sub>4</sub>)</a></li> <li><a href="/wiki/4-Amino-2-methyl-1-naphthol" title="4-Amino-2-methyl-1-naphthol">4-Amino-2-methyl-1-naphthol (K<sub>5</sub>)</a><sup>‡</sup></li> <li><a href="/wiki/2-Methylnaphthalene-1,4-diamine" title="2-Methylnaphthalene-1,4-diamine">2-Methylnaphthalene-1,4-diamine (K<sub>6</sub>)</a></li> <li><a href="/wiki/4-Amino-3-methyl-1-naphthol" title="4-Amino-3-methyl-1-naphthol">4-Amino-3-methyl-1-naphthol (K<sub>7</sub>)</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Water <br />soluble</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/B_vitamins" title="B vitamins">B</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>B<sub>1</sub> <ul><li><a href="/wiki/Thiamine" title="Thiamine">Thiamine</a><sup>#</sup></li></ul></li> <li><a href="/wiki/Vitamin_B1_analogues" title="Vitamin B1 analogues">B<sub>1</sub> analogues</a> <ul><li><a href="/wiki/Acefurtiamine" title="Acefurtiamine">Acefurtiamine</a></li> <li><a href="/wiki/Allithiamine" title="Allithiamine">Allithiamine</a></li> <li><a href="/wiki/Benfotiamine" title="Benfotiamine">Benfotiamine</a></li> <li><a href="/wiki/Fursultiamine" title="Fursultiamine">Fursultiamine</a></li> <li><a href="/wiki/Octotiamine" title="Octotiamine">Octotiamine</a></li> <li><a href="/wiki/Prosultiamine" title="Prosultiamine">Prosultiamine</a></li> <li><a href="/wiki/Sulbutiamine" title="Sulbutiamine">Sulbutiamine</a></li></ul></li> <li>B<sub>2</sub> <ul><li><a href="/wiki/Riboflavin" title="Riboflavin">Riboflavin</a><sup>#</sup></li></ul></li> <li><a href="/wiki/Vitamin_B3" title="Vitamin B3">B<sub>3</sub></a> <ul><li><a href="/wiki/Nicotinic_acid" title="Nicotinic acid">Nicotinic acid</a></li> <li><a href="/wiki/Nicotinamide" title="Nicotinamide">Nicotinamide</a><sup>#</sup></li></ul></li> <li>B<sub>5</sub> <ul><li><a class="mw-selflink selflink">Pantothenic acid</a></li> <li><a href="/wiki/Panthenol" title="Panthenol">Dexpanthenol</a></li> <li><a href="/wiki/Pantethine" title="Pantethine">Pantethine</a></li></ul></li> <li><a href="/wiki/Vitamin_B6" title="Vitamin B6">B<sub>6</sub></a> <ul><li><a href="/wiki/Pyridoxine" title="Pyridoxine">Pyridoxine</a><sup>#</sup>, <a href="/wiki/Pyridoxal_phosphate" title="Pyridoxal phosphate">Pyridoxal phosphate</a></li> <li><a href="/wiki/Pyridoxamine" title="Pyridoxamine">Pyridoxamine</a></li> <li><a href="/wiki/Pyritinol" title="Pyritinol">Pyritinol</a></li></ul></li> <li>B<sub>7</sub> <ul><li><a href="/wiki/Biotin" title="Biotin">Biotin</a></li></ul></li> <li>B<sub>9</sub> <ul><li><a href="/wiki/Folate" title="Folate">Folic acid</a><sup>#</sup></li> <li><a href="/wiki/Dihydrofolic_acid" title="Dihydrofolic acid">Dihydrofolic acid</a></li> <li><a href="/wiki/Folinic_acid" title="Folinic acid">Folinic acid</a></li> <li><a href="/wiki/Levomefolic_acid" title="Levomefolic acid">Levomefolic acid</a></li></ul></li> <li><a href="/wiki/Vitamin_B12" title="Vitamin B12">B<sub>12</sub></a> <ul><li><a href="/wiki/Adenosylcobalamin" title="Adenosylcobalamin">Adenosylcobalamin</a></li> <li><a href="/wiki/Cyanocobalamin" title="Cyanocobalamin">Cyanocobalamin</a></li> <li><a href="/wiki/Hydroxocobalamin" title="Hydroxocobalamin">Hydroxocobalamin</a><sup>#</sup></li> <li><a href="/wiki/Methylcobalamin" title="Methylcobalamin">Methylcobalamin</a></li></ul></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Vitamin_C" title="Vitamin C">C</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/Vitamin_C" title="Vitamin C">Ascorbic acid</a><sup>#</sup></li> <li><a href="/wiki/Dehydroascorbic_acid" title="Dehydroascorbic acid">Dehydroascorbic acid</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Combinations</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/Multivitamin" title="Multivitamin">Multivitamins</a></li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"><div class="hlist"> <ul><li><sup>#</sup><a href="/wiki/WHO_Model_List_of_Essential_Medicines" title="WHO Model List of Essential Medicines">WHO-EM</a></li> <li><sup>‡</sup><a href="/wiki/List_of_withdrawn_drugs" title="List of withdrawn drugs">Withdrawn</a> from market</li> <li><a href="/wiki/Clinical_trial" title="Clinical trial">Clinical trials</a>: <ul><li><sup>†</sup><a href="/wiki/Phases_of_clinical_research#Phase_III" title="Phases of clinical research">Phase III</a></li> <li><sup>§</sup>Never to phase III</li></ul></li></ul> </div></div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374" /><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235" /></div><div role="navigation" class="navbox" aria-labelledby="Dietary_supplements155" 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:Dietary_supplement" title="Template:Dietary supplement"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Dietary_supplement" title="Template talk:Dietary supplement"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Dietary_supplement" title="Special:EditPage/Template:Dietary supplement"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Dietary_supplements155" style="font-size:114%;margin:0 4em"><a href="/wiki/Dietary_supplement" title="Dietary supplement">Dietary supplements</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%">Types</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/Bodybuilding_supplement" title="Bodybuilding supplement">Bodybuilding supplement</a></li> <li><a href="/wiki/Energy_drink" title="Energy drink">Energy drink</a></li> <li><a href="/wiki/Energy_bar" title="Energy bar">Energy bar</a></li> <li><a href="/wiki/Essential_fatty_acid" title="Essential fatty acid">Fatty acids</a></li> <li><a href="/wiki/Herbal_medicine" title="Herbal medicine">Herbal supplements</a></li> <li><a href="/wiki/Mineral_(nutrient)" title="Mineral (nutrient)">Minerals</a></li> <li><a href="/wiki/Prebiotic_(nutrition)" title="Prebiotic (nutrition)">Prebiotics</a></li> <li><a href="/wiki/Probiotic" title="Probiotic">Probiotics</a> (<a href="/wiki/Lactobacillus" title="Lactobacillus">Lactobacillus</a></li> <li><a href="/wiki/Bifidobacterium" title="Bifidobacterium">Bifidobacterium</a>)</li> <li><a href="/wiki/Protein_supplement" title="Protein supplement">Protein supplements</a></li> <li><a href="/wiki/Vitamin" title="Vitamin">Vitamins</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Vitamin" title="Vitamin">Vitamins</a> and<br /><a href="/wiki/Mineral_(nutrient)" title="Mineral (nutrient)">chemical elements<br /> ("minerals")</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/Vitamin_A" title="Vitamin A">Retinol (Vitamin A)</a></li> <li><a href="/wiki/B_vitamins" title="B vitamins">B vitamins</a> <ul><li><a href="/wiki/Thiamine" title="Thiamine">Thiamine (B<sub>1</sub>)</a></li> <li><a href="/wiki/Riboflavin" title="Riboflavin">Riboflavin (B<sub>2</sub>)</a></li> <li><a href="/wiki/Niacin_(nutrient)" class="mw-redirect" title="Niacin (nutrient)">Niacin (B<sub>3</sub>)</a></li> <li><a class="mw-selflink selflink">Pantothenic acid (B<sub>5</sub>)</a></li> <li><a href="/wiki/Vitamin_B6" title="Vitamin B6">Pyridoxine (B<sub>6</sub>)</a></li> <li><a href="/wiki/Biotin" title="Biotin">Biotin (B<sub>7</sub>)</a></li> <li><a href="/wiki/Folate" title="Folate">Folic acid (B<sub>9</sub>)</a></li> <li><a href="/wiki/Cyanocobalamin" title="Cyanocobalamin">Cyanocobalamin (B<sub>12</sub>)</a></li></ul></li> <li><a href="/wiki/Vitamin_C" title="Vitamin C">Ascorbic acid (Vitamin C)</a></li> <li><a href="/wiki/Vitamin_D" title="Vitamin D">Ergocalciferol and Cholecalciferol (Vitamin D)</a></li> <li><a href="/wiki/Vitamin_E" title="Vitamin E">Tocopherol (Vitamin E)</a></li> <li><a href="/wiki/Vitamin_K" title="Vitamin K">Naphthoquinone (Vitamin K)</a></li></ul> <ul><li><a href="/wiki/Calcium_supplement" title="Calcium supplement">Calcium</a></li> <li><a href="/wiki/Choline" title="Choline">Choline</a></li> <li><a href="/wiki/Chromium" title="Chromium">Chromium</a></li> <li><a href="/wiki/Cobalt" title="Cobalt">Cobalt</a></li> <li><a href="/wiki/Copper" title="Copper">Copper</a></li> <li><a href="/wiki/Fluorine" title="Fluorine">Fluorine</a></li> <li><a href="/wiki/Iodine" title="Iodine">Iodine</a></li> <li><a href="/wiki/Iron" title="Iron">Iron</a></li> <li><a href="/wiki/Magnesium" title="Magnesium">Magnesium</a></li> <li><a href="/wiki/Manganese" title="Manganese">Manganese</a></li> <li><a href="/wiki/Molybdenum" title="Molybdenum">Molybdenum</a></li> <li><a href="/wiki/Phosphorus" title="Phosphorus">Phosphorus</a></li> <li><a href="/wiki/Potassium" title="Potassium">Potassium</a></li> <li><a href="/wiki/Selenium" title="Selenium">Selenium</a></li> <li><a href="/wiki/Sodium" title="Sodium">Sodium</a></li> <li><a href="/wiki/Sulfur" title="Sulfur">Sulfur</a></li> <li><a href="/wiki/Zinc" title="Zinc">Zinc</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Other common <br />ingredients</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/Arginine_alpha-ketoglutarate" title="Arginine alpha-ketoglutarate">AAKG</a></li> <li><a href="/wiki/Beta-Hydroxy_beta-methylbutyric_acid" class="mw-redirect" title="Beta-Hydroxy beta-methylbutyric acid">β-hydroxy β-methylbutyrate</a></li> <li><a href="/wiki/Carnitine" title="Carnitine">Carnitine</a></li> <li><a href="/wiki/Chondroitin_sulfate" title="Chondroitin sulfate">Chondroitin sulfate</a></li> <li><a href="/wiki/Cod_liver_oil" title="Cod liver oil">Cod liver oil</a></li> <li><a href="/wiki/Copper_gluconate" title="Copper gluconate">Copper gluconate</a></li> <li><a href="/wiki/Creatine" title="Creatine">Creatine</a></li> <li><a href="/wiki/Dietary_fiber" title="Dietary fiber">Dietary fiber</a></li> <li><a href="/wiki/Echinacea#Medicinal_effects" title="Echinacea">Echinacea</a></li> <li><a href="/wiki/Ephedra_(medicine)" title="Ephedra (medicine)">Ephedra</a></li> <li><a href="/wiki/Fish_oil" title="Fish oil">Fish oil</a></li> <li><a href="/wiki/Folate" title="Folate">Folic acid</a></li> <li><a href="/wiki/Ginseng" title="Ginseng">Ginseng</a></li> <li><a href="/wiki/Glucosamine" title="Glucosamine">Glucosamine</a></li> <li><a href="/wiki/Glutamine" title="Glutamine">Glutamine</a></li> <li><a href="/wiki/Grape_seed_extract" title="Grape seed extract">Grape seed extract</a></li> <li><a href="/wiki/Guarana" title="Guarana">Guarana</a></li> <li><a href="/wiki/Iron_supplement" title="Iron supplement">Iron supplements</a></li> <li><a href="/wiki/Lonicera_japonica" title="Lonicera japonica">Japanese honeysuckle</a></li> <li><a href="/wiki/Krill_oil" title="Krill oil">Krill oil</a></li> <li><a href="/wiki/Lingzhi_(mushroom)" title="Lingzhi (mushroom)">Lingzhi</a></li> <li><a href="/wiki/Linseed_oil" title="Linseed oil">Linseed oil</a></li> <li><a href="/wiki/Lipoic_acid" title="Lipoic acid">Lipoic acid</a></li> <li><a href="/wiki/Silybum_marianum#Health_benefits" title="Silybum marianum">Milk thistle</a></li> <li><a href="/wiki/Melatonin_(supplement)" class="mw-redirect" title="Melatonin (supplement)">Melatonin</a></li> <li><a href="/wiki/Red_yeast_rice" title="Red yeast rice">Red yeast rice</a></li> <li><a href="/wiki/Royal_jelly" title="Royal jelly">Royal jelly</a></li> <li><a href="/wiki/Saw_palmetto_extract" title="Saw palmetto extract">Saw palmetto</a></li> <li><a href="/wiki/Spirulina_(dietary_supplement)" title="Spirulina (dietary supplement)">Spirulina</a></li> <li><a href="/wiki/Hypericum_perforatum#Medicinal_uses" title="Hypericum perforatum">St John's wort</a></li> <li><a href="/wiki/Taurine" title="Taurine">Taurine</a></li> <li><a href="/wiki/Wheatgrass" title="Wheatgrass">Wheatgrass</a></li> <li><a href="/wiki/Goji" title="Goji">Wolfberry</a></li> <li><a href="/wiki/Yohimbine" title="Yohimbine">Yohimbine</a></li> <li><a href="/wiki/Zinc_gluconate" title="Zinc gluconate">Zinc gluconate</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Related articles</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/Codex_Alimentarius" title="Codex Alimentarius">Codex Alimentarius</a></li> <li><a href="/wiki/Enzyte" title="Enzyte">Enzyte</a></li> <li><a href="/wiki/Hadacol" title="Hadacol">Hadacol</a></li> <li><a href="/wiki/Herbal_tea" title="Herbal tea">Herbal tea</a></li> <li><a href="/wiki/Nutraceutical" title="Nutraceutical">Nutraceutical</a></li> <li><a href="/wiki/Multivitamin" title="Multivitamin">Multivitamin</a></li> <li><a href="/wiki/Nutrition" title="Nutrition">Nutrition</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="Metabolism_of_vitamins,_coenzymes,_and_cofactors146" 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:Metabolism_of_vitamins,_coenzymes,_and_cofactors" title="Template:Metabolism of vitamins, coenzymes, and cofactors"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Metabolism_of_vitamins,_coenzymes,_and_cofactors" title="Template talk:Metabolism of vitamins, coenzymes, and cofactors"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Metabolism_of_vitamins,_coenzymes,_and_cofactors" title="Special:EditPage/Template:Metabolism of vitamins, coenzymes, and cofactors"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Metabolism_of_vitamins,_coenzymes,_and_cofactors146" style="font-size:114%;margin:0 4em"><a href="/wiki/Metabolism" title="Metabolism">Metabolism</a> of <a href="/wiki/Vitamin" title="Vitamin">vitamins</a>, coenzymes, and <a href="/wiki/Cofactor_(biochemistry)" title="Cofactor (biochemistry)">cofactors</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%">Fat soluble vitamins</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Vitamin_A" title="Vitamin A">Vitamin A</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/Retinol_binding_protein" class="mw-redirect" title="Retinol binding protein">Retinol binding protein</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Vitamin_E" title="Vitamin E">Vitamin E</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Alpha-tocopherol_transfer_protein" title="Alpha-tocopherol transfer protein">Alpha-tocopherol transfer protein</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Vitamin_D" title="Vitamin D">Vitamin D</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><i>liver</i> (<a href="/wiki/CYP27A1" title="CYP27A1">Sterol 27-hydroxylase or CYP27A1</a>)</li> <li><i>renal</i> (<a href="/wiki/25-Hydroxyvitamin_D3_1-alpha-hydroxylase" class="mw-redirect" title="25-Hydroxyvitamin D3 1-alpha-hydroxylase">25-Hydroxyvitamin D<sub>3</sub> 1-alpha-hydroxylase or CYP27B1</a>)</li> <li><i>degradation</i> (<a href="/wiki/CYP24A1" title="CYP24A1">1,25-Dihydroxyvitamin D<sub>3</sub> 24-hydroxylase or CYP24A1</a>)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Vitamin_K" title="Vitamin K">Vitamin K</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/Vitamin_K_epoxide_reductase" title="Vitamin K epoxide reductase">Vitamin K epoxide reductase</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Water soluble vitamins</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Thiamine" title="Thiamine">Thiamine</a> (B<sub>1</sub>)</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/Thiamine_diphosphokinase" title="Thiamine diphosphokinase">Thiamine diphosphokinase</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Niacin_(nutrient)" class="mw-redirect" title="Niacin (nutrient)">Niacin</a> (B<sub>3</sub>)</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/Indoleamine_2,3-dioxygenase" title="Indoleamine 2,3-dioxygenase">Indoleamine 2,3-dioxygenase</a></li> <li><a href="/wiki/Formamidase" title="Formamidase">Formamidase</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a class="mw-selflink selflink">Pantothenic acid</a> (B<sub>5</sub>)</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/Pantothenate_kinase" title="Pantothenate kinase">Pantothenate kinase</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Folic_acid" class="mw-redirect" title="Folic acid">Folic acid</a> (B<sub>9</sub>)</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><td colspan="2" class="navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Dihydropteroate_synthase" title="Dihydropteroate synthase">Dihydropteroate synthase</a></li> <li><a href="/wiki/Dihydrofolate_reductase" title="Dihydrofolate reductase">Dihydrofolate reductase</a></li> <li><a href="/wiki/Serine_hydroxymethyltransferase" title="Serine hydroxymethyltransferase">Serine hydroxymethyltransferase</a></li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Methylenetetrahydrofolate_reductase" title="Methylenetetrahydrofolate reductase">Methylenetetrahydrofolate reductase</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Vitamin_B12" title="Vitamin B12">Vitamin B<sub>12</sub></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/MMAA" title="MMAA">MMAA</a></li> <li><a href="/wiki/MMAB" title="MMAB">MMAB</a></li> <li><a href="/wiki/MMACHC" title="MMACHC">MMACHC</a></li> <li><a href="/wiki/MMADHC" title="MMADHC">MMADHC</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Vitamin_C" title="Vitamin C">Vitamin C</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/L-gulonolactone_oxidase" title="L-gulonolactone oxidase">L-gulonolactone oxidase</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Riboflavin" title="Riboflavin">Riboflavin</a> (B<sub>2</sub>)</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/Riboflavin_kinase" title="Riboflavin kinase">Riboflavin kinase</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Nonvitamin cofactors</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th id="Tetrahydrobiopterin40" scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Tetrahydrobiopterin" title="Tetrahydrobiopterin">Tetrahydrobiopterin</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><td colspan="2" class="navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/GTP_cyclohydrolase_I" title="GTP cyclohydrolase I">GTP cyclohydrolase I</a></li> <li><a href="/wiki/6-pyruvoyltetrahydropterin_synthase" class="mw-redirect" title="6-pyruvoyltetrahydropterin synthase">6-pyruvoyltetrahydropterin synthase</a></li> <li><a href="/wiki/Sepiapterin_reductase" title="Sepiapterin reductase">Sepiapterin reductase</a></li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/PCBD1" title="PCBD1">PCBD1</a></li> <li><a href="/wiki/PTS_(gene)" title="PTS (gene)">PTS</a></li> <li><a href="/wiki/QDPR" title="QDPR">QDPR</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Molybdopterin" title="Molybdopterin">Molybdopterin</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/MOCS1" title="MOCS1">MOCS1</a></li> <li><a href="/wiki/MOCS2" title="MOCS2">MOCS2</a></li> <li><a href="/wiki/MOCS3" title="MOCS3">MOCS3</a></li> <li><a href="/wiki/Gephyrin" title="Gephyrin">Gephyrin</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374" /><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235" /></div><div role="navigation" class="navbox" aria-labelledby="Preparations_for_treatment_of_wounds_and_ulcers_(D03)133" 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:Preparations_for_treatment_of_wounds_and_ulcers" title="Template:Preparations for treatment of wounds and ulcers"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Preparations_for_treatment_of_wounds_and_ulcers" title="Template talk:Preparations for treatment of wounds and ulcers"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Preparations_for_treatment_of_wounds_and_ulcers" title="Special:EditPage/Template:Preparations for treatment of wounds and ulcers"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Preparations_for_treatment_of_wounds_and_ulcers_(D03)133" style="font-size:114%;margin:0 4em">Preparations for treatment of <a href="/wiki/Wound" title="Wound">wounds</a> and <a href="/wiki/Ulcer_(dermatology)" title="Ulcer (dermatology)">ulcers</a> (<a href="/wiki/ATC_code_D03" title="ATC code D03">D03</a>)</div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Cicatrizant" class="mw-redirect" title="Cicatrizant">Cicatrizants</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/Epichlorohydrin" title="Epichlorohydrin">epichlorohydrin</a>:</i> <a href="/wiki/Cadexomer_iodine" title="Cadexomer iodine">Cadexomer iodine</a></li> <li><a href="/wiki/Crilanomer" title="Crilanomer">Crilanomer</a></li> <li><a href="/wiki/Dextranomer" title="Dextranomer">Dextranomer</a></li></ul> <ul><li><i><a class="mw-selflink selflink">B5</a>:</i> <a class="mw-selflink selflink">Calcium pantothenate</a></li> <li><a href="/wiki/Panthenol" title="Panthenol">Dexpanthenol</a></li></ul> <ul><li><i><a href="/wiki/Nitrate" title="Nitrate">nitrate</a>:</i> <a href="/wiki/Medical_use_of_nitroglycerin" class="mw-redirect" title="Medical use of nitroglycerin">Nitroglycerin</a></li> <li><a href="/wiki/Isosorbide_dinitrate" title="Isosorbide dinitrate">Isosorbide dinitrate</a></li></ul> <ul><li>other: <a href="/wiki/Becaplermin" title="Becaplermin">Becaplermin</a></li> <li><a href="/wiki/Beremagene_geperpavec" title="Beremagene geperpavec">Beremagene geperpavec</a></li> <li><a href="/wiki/Birch_triterpenes" title="Birch triterpenes">Betulae cortex</a></li> <li><a href="/wiki/Centella_asiatica" title="Centella asiatica">Centella asiatica herba</a></li> <li><a href="/wiki/Enoxolone" title="Enoxolone">Enoxolone</a></li> <li><a href="/wiki/Hyaluronan" class="mw-redirect" title="Hyaluronan">Hyaluronic acid</a></li> <li><a href="/wiki/Ketanserin" title="Ketanserin">Ketanserin</a></li> <li><a href="/wiki/Nepidermin" title="Nepidermin">Nepidermin</a></li> <li><a href="/wiki/Tetrachlorodecaoxide" title="Tetrachlorodecaoxide">Sodium chlorite (tetrachlorodecaoxide)</a></li> <li><a href="/wiki/Trafermin" title="Trafermin">Trafermin</a></li> <li><a href="/wiki/Trolamine" class="mw-redirect" title="Trolamine">Trolamine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Proteolytic enzymes</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/Bromelain_(pharmacology)" title="Bromelain (pharmacology)">Bromelain (anacaulase)</a></li> <li><a href="/wiki/Clostridiopeptidase" class="mw-redirect" title="Clostridiopeptidase">Clostridiopeptidase</a></li> <li><a href="/wiki/Trypsin" title="Trypsin">Trypsin</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_modulators127" 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_modulators127" 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_modulators859" 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_modulators859" 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/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_modulators859" 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_modulators859" 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/Choline_m-bromophenyl_ether" title="Choline m-bromophenyl ether">Choline m-bromophenyl ether</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" class="mw-redirect" 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 class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374" /><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235" /><style 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