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</a> <ul id="toc-Choline_as_a_nutrient-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Metabolism" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Metabolism"> <div class="vector-toc-text"> <span class="vector-toc-numb">3</span> <span>Metabolism</span> </div> </a> <button aria-controls="toc-Metabolism-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 Metabolism subsection</span> </button> <ul id="toc-Metabolism-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">3.1</span> <span>Biosynthesis</span> </div> </a> <ul id="toc-Biosynthesis-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Absorption" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Absorption"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.2</span> <span>Absorption</span> </div> </a> <ul id="toc-Absorption-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Transport" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Transport"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.3</span> <span>Transport</span> </div> </a> <ul id="toc-Transport-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Storage" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Storage"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.4</span> <span>Storage</span> </div> </a> <ul id="toc-Storage-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Excretion" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Excretion"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.5</span> <span>Excretion</span> </div> </a> <ul id="toc-Excretion-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Function" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Function"> <div class="vector-toc-text"> <span class="vector-toc-numb">4</span> <span>Function</span> </div> </a> <button aria-controls="toc-Function-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 Function subsection</span> </button> <ul id="toc-Function-sublist" class="vector-toc-list"> <li id="toc-Phospholipid_precursor" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Phospholipid_precursor"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.1</span> <span>Phospholipid precursor</span> </div> </a> <ul id="toc-Phospholipid_precursor-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Acetylcholine_synthesis" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Acetylcholine_synthesis"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.2</span> <span>Acetylcholine synthesis</span> </div> </a> <ul id="toc-Acetylcholine_synthesis-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Source_of_trimethylglycine" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Source_of_trimethylglycine"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.3</span> <span>Source of trimethylglycine</span> </div> </a> <ul id="toc-Source_of_trimethylglycine-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Content_in_foods" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Content_in_foods"> <div class="vector-toc-text"> <span class="vector-toc-numb">5</span> <span>Content in foods</span> </div> </a> <button aria-controls="toc-Content_in_foods-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 Content in foods subsection</span> </button> <ul id="toc-Content_in_foods-sublist" class="vector-toc-list"> <li id="toc-Daily_values" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Daily_values"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.1</span> <span>Daily values</span> </div> </a> <ul id="toc-Daily_values-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Dietary_recommendations" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Dietary_recommendations"> <div class="vector-toc-text"> <span class="vector-toc-numb">6</span> <span>Dietary recommendations</span> </div> </a> <ul id="toc-Dietary_recommendations-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Intake_in_populations" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Intake_in_populations"> <div class="vector-toc-text"> <span class="vector-toc-numb">7</span> <span>Intake in populations</span> </div> </a> <ul id="toc-Intake_in_populations-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Deficiency" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Deficiency"> <div class="vector-toc-text"> <span class="vector-toc-numb">8</span> <span>Deficiency</span> </div> </a> <button aria-controls="toc-Deficiency-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 Deficiency subsection</span> </button> <ul id="toc-Deficiency-sublist" class="vector-toc-list"> <li id="toc-Signs_and_symptoms" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Signs_and_symptoms"> <div class="vector-toc-text"> <span class="vector-toc-numb">8.1</span> <span>Signs and symptoms</span> </div> </a> <ul id="toc-Signs_and_symptoms-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Causes_and_mechanisms" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Causes_and_mechanisms"> <div class="vector-toc-text"> <span class="vector-toc-numb">8.2</span> <span>Causes and mechanisms</span> </div> </a> <ul id="toc-Causes_and_mechanisms-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Excess_intake" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Excess_intake"> <div class="vector-toc-text"> <span class="vector-toc-numb">9</span> <span>Excess intake</span> </div> </a> <ul id="toc-Excess_intake-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Health_effects" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Health_effects"> <div class="vector-toc-text"> <span class="vector-toc-numb">10</span> <span>Health effects</span> </div> </a> <button aria-controls="toc-Health_effects-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> <span class="vector-icon mw-ui-icon-wikimedia-expand"></span> <span>Toggle Health effects subsection</span> </button> <ul id="toc-Health_effects-sublist" class="vector-toc-list"> <li id="toc-Neural_tube_closure" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Neural_tube_closure"> <div class="vector-toc-text"> <span class="vector-toc-numb">10.1</span> <span>Neural tube closure</span> </div> </a> <ul id="toc-Neural_tube_closure-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Cardiovascular_diseases_and_cancer" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Cardiovascular_diseases_and_cancer"> <div class="vector-toc-text"> <span class="vector-toc-numb">10.2</span> <span>Cardiovascular diseases and cancer</span> </div> </a> <ul id="toc-Cardiovascular_diseases_and_cancer-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Cognition" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Cognition"> <div class="vector-toc-text"> <span class="vector-toc-numb">10.3</span> <span>Cognition</span> </div> </a> <ul id="toc-Cognition-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Perinatal_development" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Perinatal_development"> <div class="vector-toc-text"> <span class="vector-toc-numb">11</span> <span>Perinatal development</span> </div> </a> <button aria-controls="toc-Perinatal_development-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 Perinatal development subsection</span> </button> <ul id="toc-Perinatal_development-sublist" class="vector-toc-list"> <li id="toc-Functions_in_the_fetus" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Functions_in_the_fetus"> <div class="vector-toc-text"> <span class="vector-toc-numb">11.1</span> <span>Functions in the fetus</span> </div> </a> <ul id="toc-Functions_in_the_fetus-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Uses" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Uses"> <div class="vector-toc-text"> <span class="vector-toc-numb">12</span> <span>Uses</span> </div> </a> <ul id="toc-Uses-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-History" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#History"> <div class="vector-toc-text"> <span class="vector-toc-numb">13</span> <span>History</span> </div> </a> <button aria-controls="toc-History-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 History subsection</span> </button> <ul id="toc-History-sublist" class="vector-toc-list"> <li id="toc-Discovery" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Discovery"> <div class="vector-toc-text"> <span class="vector-toc-numb">13.1</span> <span>Discovery</span> </div> </a> <ul id="toc-Discovery-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Discovery_as_a_nutrient" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Discovery_as_a_nutrient"> <div class="vector-toc-text"> <span class="vector-toc-numb">13.2</span> <span>Discovery as a nutrient</span> </div> </a> <ul id="toc-Discovery_as_a_nutrient-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-References" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#References"> <div class="vector-toc-text"> <span class="vector-toc-numb">14</span> <span>References</span> </div> </a> <ul id="toc-References-sublist" class="vector-toc-list"> </ul> </li> </ul> </div> </div> </nav> </div> </div> <div class="mw-content-container"> <main id="content" class="mw-body"> <header class="mw-body-header vector-page-titlebar"> <nav aria-label="Contents" class="vector-toc-landmark"> <div id="vector-page-titlebar-toc" class="vector-dropdown vector-page-titlebar-toc vector-button-flush-left" > <input type="checkbox" id="vector-page-titlebar-toc-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-vector-page-titlebar-toc" class="vector-dropdown-checkbox " aria-label="Toggle the table of contents" > <label id="vector-page-titlebar-toc-label" for="vector-page-titlebar-toc-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--icon-only " aria-hidden="true" ><span class="vector-icon mw-ui-icon-listBullet mw-ui-icon-wikimedia-listBullet"></span> <span class="vector-dropdown-label-text">Toggle the table of contents</span> </label> <div class="vector-dropdown-content"> <div id="vector-page-titlebar-toc-unpinned-container" class="vector-unpinned-container"> </div> </div> </div> </nav> <h1 id="firstHeading" class="firstHeading mw-first-heading"><span class="mw-page-title-main">Choline</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 50 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-50" 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">50 languages</span> </label> <div class="vector-dropdown-content"> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li class="interlanguage-link interwiki-ar mw-list-item"><a href="https://ar.wikipedia.org/wiki/%D9%83%D9%88%D9%84%D9%8A%D9%86_(%D9%85%D8%B1%D9%83%D8%A8_%D9%83%D9%8A%D9%85%D9%8A%D8%A7%D8%A6%D9%8A)" title="كولين (مركب كيميائي) – Arabic" lang="ar" hreflang="ar" data-title="كولين (مركب كيميائي)" 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/%DA%A9%D9%88%D9%84%DB%8C%D9%86" title="کولین – South Azerbaijani" lang="azb" hreflang="azb" data-title="کولین" 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%A5%D0%BE%D0%BB%D0%B8%D0%BD" title="Холин – Bulgarian" lang="bg" hreflang="bg" data-title="Холин" 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/Holin" title="Holin – Bosnian" lang="bs" hreflang="bs" data-title="Holin" 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/Colina" title="Colina – Catalan" lang="ca" hreflang="ca" data-title="Colina" 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/Cholin" title="Cholin – Czech" lang="cs" hreflang="cs" data-title="Cholin" 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/Colin" title="Colin – Welsh" lang="cy" hreflang="cy" data-title="Colin" data-language-autonym="Cymraeg" data-language-local-name="Welsh" class="interlanguage-link-target"><span>Cymraeg</span></a></li><li class="interlanguage-link interwiki-da mw-list-item"><a href="https://da.wikipedia.org/wiki/Cholin" title="Cholin – Danish" lang="da" hreflang="da" data-title="Cholin" data-language-autonym="Dansk" data-language-local-name="Danish" class="interlanguage-link-target"><span>Dansk</span></a></li><li class="interlanguage-link interwiki-de mw-list-item"><a href="https://de.wikipedia.org/wiki/Cholin" title="Cholin – German" lang="de" hreflang="de" data-title="Cholin" data-language-autonym="Deutsch" data-language-local-name="German" class="interlanguage-link-target"><span>Deutsch</span></a></li><li class="interlanguage-link interwiki-et mw-list-item"><a href="https://et.wikipedia.org/wiki/B4-vitamiin" title="B4-vitamiin – Estonian" lang="et" hreflang="et" data-title="B4-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%A7%CE%BF%CE%BB%CE%AF%CE%BD%CE%B7" title="Χολίνη – Greek" lang="el" hreflang="el" data-title="Χολίνη" 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/Colina_(qu%C3%ADmica)" title="Colina (química) – Spanish" lang="es" hreflang="es" data-title="Colina (química)" 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/Kolino" title="Kolino – Esperanto" lang="eo" hreflang="eo" data-title="Kolino" 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/Kolina" title="Kolina – Basque" lang="eu" hreflang="eu" data-title="Kolina" data-language-autonym="Euskara" data-language-local-name="Basque" class="interlanguage-link-target"><span>Euskara</span></a></li><li class="interlanguage-link interwiki-fa mw-list-item"><a href="https://fa.wikipedia.org/wiki/%DA%A9%D9%88%D9%84%DB%8C%D9%86" title="کولین – Persian" lang="fa" hreflang="fa" data-title="کولین" 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/Choline" title="Choline – French" lang="fr" hreflang="fr" data-title="Choline" 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/Coil%C3%ADn" title="Coilín – Irish" lang="ga" hreflang="ga" data-title="Coilín" 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/Colina" title="Colina – Galician" lang="gl" hreflang="gl" data-title="Colina" data-language-autonym="Galego" data-language-local-name="Galician" class="interlanguage-link-target"><span>Galego</span></a></li><li class="interlanguage-link interwiki-ko mw-list-item"><a href="https://ko.wikipedia.org/wiki/%EC%BD%9C%EB%A6%B0_(%ED%99%94%ED%95%A9%EB%AC%BC)" title="콜린 (화합물) – Korean" lang="ko" hreflang="ko" data-title="콜린 (화합물)" data-language-autonym="한국어" data-language-local-name="Korean" class="interlanguage-link-target"><span>한국어</span></a></li><li class="interlanguage-link interwiki-hr mw-list-item"><a href="https://hr.wikipedia.org/wiki/Kolin" title="Kolin – Croatian" lang="hr" hreflang="hr" data-title="Kolin" 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/Kolina" title="Kolina – Indonesian" lang="id" hreflang="id" data-title="Kolina" 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/Colina" title="Colina – Italian" lang="it" hreflang="it" data-title="Colina" data-language-autonym="Italiano" data-language-local-name="Italian" class="interlanguage-link-target"><span>Italiano</span></a></li><li class="interlanguage-link interwiki-he mw-list-item"><a href="https://he.wikipedia.org/wiki/%D7%9B%D7%95%D7%9C%D7%99%D7%9F" title="כולין – Hebrew" lang="he" hreflang="he" data-title="כולין" data-language-autonym="עברית" data-language-local-name="Hebrew" class="interlanguage-link-target"><span>עברית</span></a></li><li class="interlanguage-link interwiki-kk mw-list-item"><a href="https://kk.wikipedia.org/wiki/%D0%A5%D0%BE%D0%BB%D0%B8%D0%BD" title="Холин – Kazakh" lang="kk" hreflang="kk" data-title="Холин" 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%A5%D0%BE%D0%BB%D0%B8%D0%BD" title="Холин – Kyrgyz" lang="ky" hreflang="ky" data-title="Холин" data-language-autonym="Кыргызча" data-language-local-name="Kyrgyz" class="interlanguage-link-target"><span>Кыргызча</span></a></li><li class="interlanguage-link interwiki-lt mw-list-item"><a href="https://lt.wikipedia.org/wiki/Cholinas" title="Cholinas – Lithuanian" lang="lt" hreflang="lt" data-title="Cholinas" 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/Kolin_(vegy%C3%BClet)" title="Kolin (vegyület) – Hungarian" lang="hu" hreflang="hu" data-title="Kolin (vegyület)" data-language-autonym="Magyar" data-language-local-name="Hungarian" class="interlanguage-link-target"><span>Magyar</span></a></li><li class="interlanguage-link interwiki-ms mw-list-item"><a href="https://ms.wikipedia.org/wiki/Kolina" title="Kolina – Malay" lang="ms" hreflang="ms" data-title="Kolina" data-language-autonym="Bahasa Melayu" data-language-local-name="Malay" class="interlanguage-link-target"><span>Bahasa Melayu</span></a></li><li class="interlanguage-link interwiki-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/Choline" title="Choline – Dutch" lang="nl" hreflang="nl" data-title="Choline" data-language-autonym="Nederlands" data-language-local-name="Dutch" class="interlanguage-link-target"><span>Nederlands</span></a></li><li class="interlanguage-link interwiki-ja mw-list-item"><a href="https://ja.wikipedia.org/wiki/%E3%82%B3%E3%83%AA%E3%83%B3_(%E6%A0%84%E9%A4%8A%E7%B4%A0)" title="コリン (栄養素) – Japanese" lang="ja" hreflang="ja" data-title="コリン (栄養素)" data-language-autonym="日本語" data-language-local-name="Japanese" class="interlanguage-link-target"><span>日本語</span></a></li><li class="interlanguage-link interwiki-pl mw-list-item"><a href="https://pl.wikipedia.org/wiki/Cholina" title="Cholina – Polish" lang="pl" hreflang="pl" data-title="Cholina" 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/Colina_(vitamina)" title="Colina (vitamina) – Portuguese" lang="pt" hreflang="pt" data-title="Colina (vitamina)" 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/Colin%C4%83_(compus)" title="Colină (compus) – Romanian" lang="ro" hreflang="ro" data-title="Colină (compus)" data-language-autonym="Română" data-language-local-name="Romanian" class="interlanguage-link-target"><span>Română</span></a></li><li class="interlanguage-link interwiki-ru mw-list-item"><a href="https://ru.wikipedia.org/wiki/%D0%A5%D0%BE%D0%BB%D0%B8%D0%BD" title="Холин – Russian" lang="ru" hreflang="ru" data-title="Холин" 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%A5%D0%BE%D0%BB%D0%B8%D0%BD" title="Холин – Yakut" lang="sah" hreflang="sah" data-title="Холин" 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-sco mw-list-item"><a href="https://sco.wikipedia.org/wiki/Choline" title="Choline – Scots" lang="sco" hreflang="sco" data-title="Choline" data-language-autonym="Scots" data-language-local-name="Scots" class="interlanguage-link-target"><span>Scots</span></a></li><li class="interlanguage-link interwiki-simple mw-list-item"><a href="https://simple.wikipedia.org/wiki/Choline" title="Choline – Simple English" lang="en-simple" hreflang="en-simple" data-title="Choline" 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/Chol%C3%ADn" title="Cholín – Slovak" lang="sk" hreflang="sk" data-title="Cholín" 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/Holin" title="Holin – Slovenian" lang="sl" hreflang="sl" data-title="Holin" 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/Holin" title="Holin – Serbian" lang="sr" hreflang="sr" data-title="Holin" 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/Holin" title="Holin – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Holin" 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/Koliini" title="Koliini – Finnish" lang="fi" hreflang="fi" data-title="Koliini" 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/Kolin" title="Kolin – Swedish" lang="sv" hreflang="sv" data-title="Kolin" data-language-autonym="Svenska" data-language-local-name="Swedish" class="interlanguage-link-target"><span>Svenska</span></a></li><li class="interlanguage-link interwiki-ta mw-list-item"><a href="https://ta.wikipedia.org/wiki/%E0%AE%95%E0%AF%8B%E0%AE%B2%E0%AE%BF%E0%AE%A9%E0%AF%8D" title="கோலின் – Tamil" lang="ta" hreflang="ta" data-title="கோலின்" data-language-autonym="தமிழ்" data-language-local-name="Tamil" class="interlanguage-link-target"><span>தமிழ்</span></a></li><li class="interlanguage-link interwiki-tr mw-list-item"><a href="https://tr.wikipedia.org/wiki/Kolin" title="Kolin – Turkish" lang="tr" hreflang="tr" data-title="Kolin" data-language-autonym="Türkçe" data-language-local-name="Turkish" class="interlanguage-link-target"><span>Türkçe</span></a></li><li class="interlanguage-link interwiki-tyv mw-list-item"><a href="https://tyv.wikipedia.org/wiki/%D0%A5%D0%BE%D0%BB%D0%B8%D0%BD" title="Холин – Tuvinian" lang="tyv" hreflang="tyv" data-title="Холин" data-language-autonym="Тыва дыл" data-language-local-name="Tuvinian" class="interlanguage-link-target"><span>Тыва дыл</span></a></li><li class="interlanguage-link interwiki-uk mw-list-item"><a href="https://uk.wikipedia.org/wiki/%D0%A5%D0%BE%D0%BB%D1%96%D0%BD" title="Холін – Ukrainian" lang="uk" hreflang="uk" data-title="Холін" data-language-autonym="Українська" data-language-local-name="Ukrainian" class="interlanguage-link-target"><span>Українська</span></a></li><li class="interlanguage-link interwiki-vi mw-list-item"><a href="https://vi.wikipedia.org/wiki/Choline" title="Choline – Vietnamese" lang="vi" hreflang="vi" data-title="Choline" data-language-autonym="Tiếng Việt" data-language-local-name="Vietnamese" class="interlanguage-link-target"><span>Tiếng Việt</span></a></li><li class="interlanguage-link interwiki-zh-yue mw-list-item"><a href="https://zh-yue.wikipedia.org/wiki/%E8%86%BD%E9%B9%BC" title="膽鹼 – Cantonese" lang="yue" hreflang="yue" data-title="膽鹼" data-language-autonym="粵語" data-language-local-name="Cantonese" class="interlanguage-link-target"><span>粵語</span></a></li><li class="interlanguage-link interwiki-zh mw-list-item"><a href="https://zh.wikipedia.org/wiki/%E8%83%86%E7%A2%B1" title="胆碱 – Chinese" lang="zh" hreflang="zh" data-title="胆碱" data-language-autonym="中文" data-language-local-name="Chinese" class="interlanguage-link-target"><span>中文</span></a></li> </ul> 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class="vector-menu-heading"> General </div> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li id="t-whatlinkshere" class="mw-list-item"><a href="/wiki/Special:WhatLinksHere/Choline" title="List of all English Wikipedia pages containing links to this page [j]" accesskey="j"><span>What links here</span></a></li><li id="t-recentchangeslinked" class="mw-list-item"><a href="/wiki/Special:RecentChangesLinked/Choline" rel="nofollow" title="Recent changes in pages linked from this page [k]" accesskey="k"><span>Related changes</span></a></li><li id="t-upload" class="mw-list-item"><a href="/wiki/Wikipedia:File_Upload_Wizard" title="Upload files [u]" accesskey="u"><span>Upload file</span></a></li><li id="t-specialpages" class="mw-list-item"><a href="/wiki/Special:SpecialPages" title="A list of all special pages [q]" accesskey="q"><span>Special pages</span></a></li><li id="t-permalink" class="mw-list-item"><a href="/w/index.php?title=Choline&oldid=1254695733" title="Permanent link to this revision of this page"><span>Permanent link</span></a></li><li id="t-info" class="mw-list-item"><a href="/w/index.php?title=Choline&action=info" title="More information about this page"><span>Page information</span></a></li><li id="t-cite" class="mw-list-item"><a href="/w/index.php?title=Special:CiteThisPage&page=Choline&id=1254695733&wpFormIdentifier=titleform" title="Information on how to cite this page"><span>Cite this page</span></a></li><li id="t-urlshortener" class="mw-list-item"><a href="/w/index.php?title=Special:UrlShortener&url=https%3A%2F%2Fen.wikipedia.org%2Fwiki%2FCholine"><span>Get shortened URL</span></a></li><li id="t-urlshortener-qrcode" class="mw-list-item"><a href="/w/index.php?title=Special:QrCode&url=https%3A%2F%2Fen.wikipedia.org%2Fwiki%2FCholine"><span>Download QR code</span></a></li> </ul> </div> </div> <div id="p-coll-print_export" class="vector-menu mw-portlet mw-portlet-coll-print_export" > <div class="vector-menu-heading"> 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dir="ltr"><div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Chemical compound and essential nutrient</div> <style data-mw-deduplicate="TemplateStyles:r1236090951">.mw-parser-output .hatnote{font-style:italic}.mw-parser-output div.hatnote{padding-left:1.6em;margin-bottom:0.5em}.mw-parser-output .hatnote i{font-style:normal}.mw-parser-output .hatnote+link+.hatnote{margin-top:-0.5em}@media print{body.ns-0 .mw-parser-output .hatnote{display:none!important}}</style><div role="note" class="hatnote navigation-not-searchable">Not to be confused with <a href="/wiki/Chlorine" title="Chlorine">chlorine</a>.</div> <p> <style data-mw-deduplicate="TemplateStyles:r1084375498">.mw-parser-output .ib-chembox{border-collapse:collapse;text-align:left}.mw-parser-output .ib-chembox td,.mw-parser-output .ib-chembox th{border:1px solid #a2a9b1;width:40%}.mw-parser-output .ib-chembox td+td{width:60%}</style> </p> <table class="infobox ib-chembox"> <caption>Choline </caption> <tbody><tr> <td colspan="2" style="text-align:center; padding:2px;"><span class="skin-invert-image" typeof="mw:File"><a href="/wiki/File:Choline_cation.png" class="mw-file-description" title="Choline cation skeletal formula"><img alt="Choline cation skeletal formula" src="//upload.wikimedia.org/wikipedia/commons/thumb/2/2e/Choline_cation.png/220px-Choline_cation.png" decoding="async" width="220" height="126" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/2/2e/Choline_cation.png/330px-Choline_cation.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/2/2e/Choline_cation.png/440px-Choline_cation.png 2x" data-file-width="666" data-file-height="382" /></a></span> </td></tr> <tr> <td colspan="2" style="text-align:center; padding:2px;"><span typeof="mw:File"><a href="/wiki/File:Choline-cation-3D-balls.png" class="mw-file-description"><img alt="Ball-and-stick model" src="//upload.wikimedia.org/wikipedia/commons/thumb/c/ca/Choline-cation-3D-balls.png/180px-Choline-cation-3D-balls.png" decoding="async" width="180" height="109" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/c/ca/Choline-cation-3D-balls.png/270px-Choline-cation-3D-balls.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/c/ca/Choline-cation-3D-balls.png/360px-Choline-cation-3D-balls.png 2x" data-file-width="2000" data-file-height="1213" /></a></span> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Names </th></tr> <tr> <td colspan="2" style="text-align:left;"><a href="/wiki/Chemical_nomenclature" title="Chemical nomenclature">IUPAC name</a> <div style="max-width:22em; word-wrap:break-word; padding-left:1.7em;">2-Hydroxyethyl(trimethyl)azanium<sup id="cite_ref-pubchem_1-0" class="reference"><a href="#cite_note-pubchem-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup></div> </td></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;">2-Hydroxy-<i>N</i>,<i>N</i>,<i>N</i>-trimethylethan-1-aminium</div></div> </td></tr> <tr> <td colspan="2" style="text-align:left;">Other names <div style="max-width:22em; word-wrap:break-word; padding-left:1.7em;"><style data-mw-deduplicate="TemplateStyles:r1126788409">.mw-parser-output .plainlist ol,.mw-parser-output .plainlist ul{line-height:inherit;list-style:none;margin:0;padding:0}.mw-parser-output .plainlist ol li,.mw-parser-output .plainlist ul li{margin-bottom:0}</style><div class="plainlist"><ul><li>Bilineurine</li><li>(2-Hydroxyethyl)trimethylammonium</li><li>2-Hydroxy-<i>N</i>,<i>N</i>,<i>N</i>-trimethylethanaminium</li></ul></div></div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Identifiers </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/CAS_Registry_Number" title="CAS Registry Number">CAS Number</a></div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="commonchemistry.cas.org"><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=62-49-7">62-49-7</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">3D model (<a href="/wiki/JSmol" class="mw-redirect" title="JSmol">JSmol</a>)</div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="chemapps.stolaf.edu (3D interactive model)"><a rel="nofollow" class="external text" href="https://chemapps.stolaf.edu/jmol/jmol.php?model=C%5BN%2B%5D%28C%29%28C%29CCO">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>1736748 </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=15354">CHEBI:15354</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ChEMBL" title="ChEMBL">ChEMBL</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.ebi.ac.uk"><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chembldb/index.php/compound/inspect/ChEMBL920">ChEMBL920</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.299.html">299</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><a href="/wiki/DrugBank" title="DrugBank">DrugBank</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.drugbank.ca"><a rel="nofollow" class="external text" href="https://www.drugbank.ca/drugs/DB00122">DB00122</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ECHA_InfoCard" class="mw-redirect" title="ECHA InfoCard"><span title="echa.europa.eu">ECHA InfoCard</span></a> </td> <td><a rel="nofollow" class="external text" href="https://echa.europa.eu/substance-information/-/substanceinfo/100.000.487">100.000.487</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q193166#P2566" title="Edit this at Wikidata"><img alt="Edit this at Wikidata" src="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/10px-OOjs_UI_icon_edit-ltr-progressive.svg.png" decoding="async" width="10" height="10" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/15px-OOjs_UI_icon_edit-ltr-progressive.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/20px-OOjs_UI_icon_edit-ltr-progressive.svg.png 2x" data-file-width="20" data-file-height="20" /></a></span> </td></tr> <tr> <td><a href="/wiki/European_Community_number" title="European Community number"><span title="European Community number (chemical identifier)">EC Number</span></a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li>200-535-1</li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Gmelin_database" title="Gmelin database">Gmelin Reference</a></div> </td> <td>324597 </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/IUPHAR/BPS" class="mw-redirect" title="IUPHAR/BPS">IUPHAR/BPS</a></div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.guidetopharmacology.org"><a rel="nofollow" class="external text" href="http://www.guidetopharmacology.org/GRAC/LigandDisplayForward?tab=summary&ligandId=4551">4551</a></span></li></ul></div> </td></tr> <tr> <td><a href="/wiki/KEGG" title="KEGG">KEGG</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.kegg.jp"><a rel="nofollow" class="external text" href="https://www.kegg.jp/entry/C00114">C00114</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/PubChem" title="PubChem">PubChem</a> <abbr title="Compound ID">CID</abbr></div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="pubchem.ncbi.nlm.nih.gov"><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/305">305</a></span></li></ul></div> </td></tr> <tr> <td><a href="/wiki/Unique_Ingredient_Identifier" title="Unique Ingredient Identifier">UNII</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="precision.fda.gov"><a rel="nofollow" class="external text" href="https://precision.fda.gov/uniisearch/srs/unii/N91BDP6H0X">N91BDP6H0X</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/CompTox_Chemicals_Dashboard" title="CompTox Chemicals Dashboard">CompTox Dashboard</a> <span style="font-weight:normal">(<abbr title="U.S. Environmental Protection Agency">EPA</abbr>)</span></div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="comptox.epa.gov"><a rel="nofollow" class="external text" href="https://comptox.epa.gov/dashboard/chemical/details/DTXSID8043789">DTXSID8043789</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q193166#P3117" title="Edit this at Wikidata"><img alt="Edit this at Wikidata" src="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/10px-OOjs_UI_icon_edit-ltr-progressive.svg.png" decoding="async" width="10" height="10" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/15px-OOjs_UI_icon_edit-ltr-progressive.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/20px-OOjs_UI_icon_edit-ltr-progressive.svg.png 2x" data-file-width="20" data-file-height="20" /></a></span></span></li></ul></div> </td></tr> <tr> <td colspan="2"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold; text-align:left; font-weight:normal; background:transparent;"><div><a href="/wiki/International_Chemical_Identifier" title="International Chemical Identifier">InChI</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.5em; text-align:left;"><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">InChI=1S/C5H14NO/c1-6(2,3)4-5-7/h7H,4-5H2,1-3H3/q+1<sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></div><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">Key: OEYIOHPDSNJKLS-UHFFFAOYSA-N<sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></div></div></li></ul> </div> </td></tr> <tr> <td colspan="2"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold; text-align:left; font-weight:normal; background:transparent;"><div><a href="/wiki/Simplified_molecular-input_line-entry_system" class="mw-redirect" title="Simplified molecular-input line-entry system">SMILES</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.6em; word-wrap:break-word; text-indent:-1.5em; text-align:left; font-size:97%; line-height:120%;">C[N+](C)(C)CCO</div></li></ul> </div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Properties </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Chemical_formula" title="Chemical formula">Chemical formula</a></div> </td> <td><style data-mw-deduplicate="TemplateStyles:r1123817410">.mw-parser-output .template-chem2-su{display:inline-block;font-size:80%;line-height:1;vertical-align:-0.35em}.mw-parser-output .template-chem2-su>span{display:block;text-align:left}.mw-parser-output sub.template-chem2-sub{font-size:80%;vertical-align:-0.35em}.mw-parser-output sup.template-chem2-sup{font-size:80%;vertical-align:0.65em}</style><span class="chemf nowrap">[(CH<sub class="template-chem2-sub">3</sub>)<sub class="template-chem2-sub">3</sub>NCH<sub class="template-chem2-sub">2</sub>CH<sub class="template-chem2-sub">2</sub>OH]<sup class="template-chem2-sup">+</sup></span>  </td></tr> <tr> <td><a href="/wiki/Molar_mass" title="Molar mass">Molar mass</a> </td> <td><span class="nowrap"><span data-sort-value="7002104173000000000♠"></span>104.173</span> g·mol<sup>−1</sup>   </td></tr> <tr> <td>Appearance </td> <td>Viscous colorless deliquescent liquid (choline hydroxide)<sup id="cite_ref-Kirk_2000_2-0" class="reference"><a href="#cite_note-Kirk_2000-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Aqueous_solution" title="Aqueous solution">Solubility in water</a></div> </td> <td>Very soluble (choline hydroxide)<sup id="cite_ref-Kirk_2000_2-1" class="reference"><a href="#cite_note-Kirk_2000-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><a href="/wiki/Solubility" title="Solubility">Solubility</a> </td> <td>soluble in <a href="/wiki/Ethanol" title="Ethanol">ethanol</a>,<sup id="cite_ref-Kirk_2000_2-2" class="reference"><a href="#cite_note-Kirk_2000-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> insoluble in <a href="/wiki/Diethylether" class="mw-redirect" title="Diethylether">diethylether</a> and <a href="/wiki/Chloroform" title="Chloroform">chloroform</a><sup id="cite_ref-ze_3-0" class="reference"><a href="#cite_note-ze-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> (choline hydroxide) </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Structure </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Coordination_geometry" title="Coordination geometry">Coordination geometry</a></div> </td> <td><a href="/wiki/Tetrahedral_molecular_geometry" title="Tetrahedral molecular geometry">Tetrahedral</a> at the <a href="/wiki/Nitrogen" title="Nitrogen">nitrogen</a> atom </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Hazards </th></tr> <tr> <td colspan="2" style="text-align:left; background-color:#eaeaea;"><b><a href="/wiki/Occupational_safety_and_health" title="Occupational safety and health">Occupational safety and health</a></b> (OHS/OSH): </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">Main hazards</div> </td> <td><a href="/wiki/Corrosive" class="mw-redirect" title="Corrosive">Corrosive</a> </td></tr> <tr> <td colspan="2" style="text-align:left; background-color:#eaeaea;"><a href="/wiki/Globally_Harmonized_System_of_Classification_and_Labelling_of_Chemicals" title="Globally Harmonized System of Classification and Labelling of Chemicals"><b>GHS</b> labelling</a>: </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/GHS_hazard_pictograms" title="GHS hazard pictograms">Pictograms</a></div> </td> <td><span typeof="mw:File"><a href="/wiki/File:GHS-pictogram-acid.svg" class="mw-file-description" title="GHS05: Corrosive"><img alt="GHS05: Corrosive" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a1/GHS-pictogram-acid.svg/50px-GHS-pictogram-acid.svg.png" decoding="async" width="50" height="50" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a1/GHS-pictogram-acid.svg/75px-GHS-pictogram-acid.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a1/GHS-pictogram-acid.svg/100px-GHS-pictogram-acid.svg.png 2x" data-file-width="724" data-file-height="724" /></a></span> </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Globally_Harmonized_System_of_Classification_and_Labelling_of_Chemicals#Signal_word" title="Globally Harmonized System of Classification and Labelling of Chemicals">Signal word</a></div> </td> <td><b>Danger</b> </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/GHS_hazard_statements" title="GHS hazard statements">Hazard statements</a></div> </td> <td><abbr class="abbr" title="H314: Causes severe skin burns and eye damage">H314</abbr> </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/GHS_precautionary_statements" title="GHS precautionary statements">Precautionary statements</a></div> </td> <td><abbr class="abbr" title="P260: Do not breathe dust/fume/gas/mist/vapours/spray.">P260</abbr>, <abbr class="abbr" title="P264: Wash ... thoroughly after handling.">P264</abbr>, <abbr class="abbr" title="P280: Wear protective gloves/protective clothing/eye protection/face protection.">P280</abbr>, <abbr class="abbr" title="P301+P330+P331: IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.">P301+P330+P331</abbr>, <abbr class="abbr" title="P303+P361+P353: IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water [or shower].">P303+P361+P353</abbr>, <abbr class="abbr" title="P304+P340: IF INHALED: Remove victim to fresh air and keep at rest in a position comfortable for breathing.">P304+P340</abbr>, <abbr class="abbr" title="P305+P351+P338: IF IN EYES: Rinse continuously with water for several minutes. Remove contact lenses if present and easy to do. Continue rinsing.">P305+P351+P338</abbr>, <abbr class="abbr" title="P310: Immediately call a POISON CENTER or doctor/physician.">P310</abbr>, <abbr class="abbr" title="P321: Specific treatment (see ... on this label).">P321</abbr>, <abbr class="abbr" title="P363: Wash contaminated clothing before reuse.">P363</abbr>, <abbr class="abbr" title="P405: Store locked up.">P405</abbr>, <abbr class="abbr" title="P501: Dispose of contents/container to ...">P501</abbr> </td></tr> <tr> <td><a href="/wiki/NFPA_704" title="NFPA 704"><b>NFPA 704</b></a> (fire diamond) </td> <td><style data-mw-deduplicate="TemplateStyles:r1170367383">.mw-parser-output .nfpa-704-diamond-ref{float:right;padding:1px;text-align:right}.mw-parser-output .nfpa-704-diamond-container{width:82px;font-family:sans-serif;margin:0 auto}.mw-parser-output .nfpa-704-diamond-container-ref{float:left;margin-left:1em}.mw-parser-output .nfpa-704-diamond-images{float:left;font-size:20px;text-align:center;position:relative;height:80px;width:80px;padding:1px}.mw-parser-output .nfpa-704-diamond-map{position:absolute;height:80px;width:80px}.mw-parser-output .nfpa-704-diamond .noresize{margin:0 auto}.mw-parser-output .nfpa-704-diamond-code{line-height:1em;text-align:center;position:absolute}.mw-parser-output .nfpa-704-diamond-code>a{color:black}.mw-parser-output .nfpa-704-diamond-blue{width:13px;top:31px;left:15px}.mw-parser-output .nfpa-704-diamond-red{width:12px;top:12px;left:35px}.mw-parser-output .nfpa-704-diamond-yellow{width:13px;top:31px;left:54px}.mw-parser-output .nfpa-704-diamond-white-image{position:relative;top:51px;left:0}.mw-parser-output .nfpa-704-diamond-white-text{vertical-align:middle;text-align:center;line-height:80%;position:absolute;top:52px}.mw-parser-output .nfpa-704-diamond-white-text a>span{position:absolute;color:black}.mw-parser-output .nfpa-704-diamond-white-wors{font-size:15px;width:23px;left:29px}.mw-parser-output .nfpa-704-diamond-white-wox{font-size:15px;font-stretch:condensed;width:21px;line-height:80%;top:-4px;left:29px}.mw-parser-output .nfpa-704-diamond-white-abcp{font-size:13.5px;font-stretch:condensed;width:28px;left:26px}.mw-parser-output .nfpa-704-diamond-white-ac{font-size:10px;width:30px;left:25px}.mw-parser-output .nfpa-704-diamond-white-strike{text-decoration:line-through}</style><div class="nfpa-704-diamond notheme"><div class="nfpa-704-diamond-container"><div class="nfpa-704-diamond-images nounderlines"> <div class="nfpa-704-diamond-map"><figure class="noresize" typeof="mw:File"><span><img alt="NFPA 704 four-colored diamond" src="//upload.wikimedia.org/wikipedia/commons/thumb/6/6f/NFPA_704.svg/80px-NFPA_704.svg.png" decoding="async" width="80" height="80" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/6f/NFPA_704.svg/120px-NFPA_704.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/6f/NFPA_704.svg/160px-NFPA_704.svg.png 2x" data-file-width="512" data-file-height="512" usemap="#ImageMap_b2ec7847c5245446" /></span><map name="ImageMap_b2ec7847c5245446"><area href="/wiki/NFPA_704#Blue" shape="poly" coords="23,23,47,47,23,70,0,47" alt="Health (blue): no hazard code" title="Health (blue): no hazard code" /><area href="/wiki/NFPA_704#Red" shape="poly" coords="47,0,70,23,47,47,23,23" alt="Flammability (red): no hazard code" title="Flammability (red): no hazard code" /><area href="/wiki/NFPA_704#Yellow" shape="poly" coords="70,23,94,47,70,70,47,47" alt="Instability (yellow): no hazard code" title="Instability (yellow): no hazard code" /><area href="/wiki/NFPA_704#White" shape="poly" coords="47,47,70,70,47,94,23,70" alt="Special hazard COR: Corrosive; strong acid or base. E.g. sulfuric acid, potassium hydroxide" title="Special hazard COR: Corrosive; strong acid or base. E.g. sulfuric acid, potassium hydroxide" /></map><figcaption></figcaption></figure></div><div class="nfpa-704-diamond-code nfpa-704-diamond-blue"> </div><div class="nfpa-704-diamond-code nfpa-704-diamond-red"> </div><div class="nfpa-704-diamond-code nfpa-704-diamond-yellow"> </div><div class="nfpa-704-diamond-white-text mw-no-invert"><a href="/wiki/NFPA_704#White" title="NFPA 704"><span class="nfpa-704-diamond-white-abcp" title="Special hazard COR: Corrosive; strong acid or base. E.g. sulfuric acid, potassium hydroxide">COR</span></a></div></div></div></div> </td></tr> <tr> <td colspan="2" style="text-align:left; background-color:#eaeaea;"><b>Lethal dose</b> or concentration (LD, LC): </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">LD<sub>50</sub> (<a href="/wiki/Lethal_dose#LD50" title="Lethal dose">median dose</a>)</div> </td> <td>3–6 g/kg (rat, oral)<sup id="cite_ref-Kirk_2000_2-3" class="reference"><a href="#cite_note-Kirk_2000-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><a href="/wiki/Safety_data_sheet" title="Safety data sheet">Safety data sheet</a> (SDS) </td> <td>4 </td></tr> <tr> <td colspan="2" style="text-align:left; background:#f8eaba; border:1px solid #a2a9b1;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">Except where otherwise noted, data are given for materials in their <a href="/wiki/Standard_state" title="Standard state">standard state</a> (at 25 °C [77 °F], 100 kPa).</div> <div style="margin-top: 0.3em;"><div style="text-align:center;"><span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/12px-Yes_check.svg.png" decoding="async" width="12" height="12" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/18px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/24px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span> <span class="reflink plainlinks nourlexpansion"><a class="external text" href="https://en.wikipedia.org/w/index.php?title=Special:ComparePages&rev1=477165756&page2=Choline">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>Choline</b> is a <a href="/wiki/Cation" class="mw-redirect" title="Cation">cation</a> with the <a href="/wiki/Chemical_formula" title="Chemical formula">chemical formula</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">[(CH<sub class="template-chem2-sub">3</sub>)<sub class="template-chem2-sub">3</sub>NCH<sub class="template-chem2-sub">2</sub>CH<sub class="template-chem2-sub">2</sub>OH]<sup class="template-chem2-sup">+</sup></span>.<sup id="cite_ref-pubchem_1-1" class="reference"><a href="#cite_note-pubchem-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-lpi_4-0" class="reference"><a href="#cite_note-lpi-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-ods_5-0" class="reference"><a href="#cite_note-ods-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> Choline forms various <a href="/wiki/Salt_(chemistry)" title="Salt (chemistry)">salts</a>, such as <a href="/wiki/Choline_chloride" title="Choline chloride">choline chloride</a> and <a href="/wiki/Choline_bitartrate" title="Choline bitartrate">choline bitartrate</a>. It is an <a href="/wiki/Essential_nutrient" class="mw-redirect" title="Essential nutrient">essential nutrient</a> for humans and many other animals, and is a structural part of <a href="/wiki/Phospholipid" title="Phospholipid">phospholipids</a> and <a href="/wiki/Cell_membrane" title="Cell membrane">cell membranes</a>.<sup id="cite_ref-lpi_4-1" class="reference"><a href="#cite_note-lpi-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-ods_5-1" class="reference"><a href="#cite_note-ods-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> </p><p>Choline is used to synthesize <a href="/wiki/Acetylcholine" title="Acetylcholine">acetylcholine</a>, a <a href="/wiki/Neurotransmitter" title="Neurotransmitter">neurotransmitter</a> involved in muscle control and numerous functions of the nervous system.<sup id="cite_ref-lpi_4-2" class="reference"><a href="#cite_note-lpi-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-ods_5-2" class="reference"><a href="#cite_note-ods-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> Choline is involved in early development of the brain, <a href="/wiki/Gene_expression" title="Gene expression">gene expression</a>, cell membrane <a href="/wiki/Signaling_peptide_receptor" title="Signaling peptide receptor">signaling</a>, and brain metabolism.<sup id="cite_ref-ods_5-3" class="reference"><a href="#cite_note-ods-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> </p><p>Although humans synthesize choline in the <a href="/wiki/Liver" title="Liver">liver</a>, the amount produced naturally is insufficient to meet cellular functions, requiring that some choline be obtained from foods or <a href="/wiki/Dietary_supplement" title="Dietary supplement">dietary supplements</a>.<sup id="cite_ref-ods_5-4" class="reference"><a href="#cite_note-ods-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> Foods rich in choline include meats, poultry, eggs, and other animal-based products, <a href="/wiki/Cruciferous_vegetables" title="Cruciferous vegetables">cruciferous vegetables</a>, beans, nuts, and <a href="/wiki/Whole_grain" title="Whole grain">whole grains</a>.<sup id="cite_ref-ods_5-5" class="reference"><a href="#cite_note-ods-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> Choline is present in breast milk and is commonly added as an <a href="/wiki/Food_additive" title="Food additive">ingredient</a> to <a href="/wiki/Baby_food" title="Baby food">baby foods</a>.<sup id="cite_ref-ods_5-6" class="reference"><a href="#cite_note-ods-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Chemistry">Chemistry</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Choline&action=edit&section=1" title="Edit section: Chemistry"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Choline is a <a href="/wiki/Quaternary_ammonium_cation" title="Quaternary ammonium cation">quaternary ammonium cation</a>. The cholines are a family of water-soluble <a href="/wiki/Quaternary_ammonium_compound" class="mw-redirect" title="Quaternary ammonium compound">quaternary ammonium compounds</a>.<sup id="cite_ref-lpi_4-3" class="reference"><a href="#cite_note-lpi-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> Choline is the parent compound of the cholines class, consisting of <a href="/wiki/Ethanolamine" title="Ethanolamine">ethanolamine</a> residue having three <a href="/wiki/Methyl" class="mw-redirect" title="Methyl">methyl</a> groups attached to the same <a href="/wiki/Nitrogen" title="Nitrogen">nitrogen</a> atom.<sup id="cite_ref-pubchem_1-2" class="reference"><a href="#cite_note-pubchem-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-lpi_4-4" class="reference"><a href="#cite_note-lpi-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> <a href="/wiki/Choline_hydroxide" title="Choline hydroxide">Choline hydroxide</a> is known as choline base. It is <a href="/wiki/Hygroscopic" class="mw-redirect" title="Hygroscopic">hygroscopic</a> and thus often encountered as a colorless <a href="/wiki/Viscous" class="mw-redirect" title="Viscous">viscous</a> hydrated syrup that smells of <a href="/wiki/Trimethylamine" title="Trimethylamine">trimethylamine</a> (TMA). Aqueous solutions of choline are stable, but the compound slowly breaks down to <a href="/wiki/Ethylene_glycol" title="Ethylene glycol">ethylene glycol</a>, <a href="/wiki/Polyethylene_glycol" title="Polyethylene glycol">polyethylene glycols</a>, and TMA.<sup id="cite_ref-Kirk_2000_2-4" class="reference"><a href="#cite_note-Kirk_2000-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> </p><p>Choline chloride can be made by treating TMA with <a href="/wiki/2-chloroethanol" class="mw-redirect" title="2-chloroethanol">2-chloroethanol</a>:<sup id="cite_ref-Kirk_2000_2-5" class="reference"><a href="#cite_note-Kirk_2000-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> </p> <dl><dd><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">(CH<sub class="template-chem2-sub">3</sub>)<sub class="template-chem2-sub">3</sub>N + ClCH<sub class="template-chem2-sub">2</sub>CH<sub class="template-chem2-sub">2</sub>OH → [(CH<sub class="template-chem2-sub">3</sub>)<sub class="template-chem2-sub">3</sub>NCH<sub class="template-chem2-sub">2</sub>CH<sub class="template-chem2-sub">2</sub>OH]<sup class="template-chem2-sup">+</sup>Cl<sup class="template-chem2-sup">−</sup></span></dd></dl> <p>Choline has historically been produced from natural sources, such as via <a href="/wiki/Hydrolysis" title="Hydrolysis">hydrolysis</a> of <a href="/wiki/Lecithin" title="Lecithin">lecithin</a>.<sup id="cite_ref-Kirk_2000_2-6" class="reference"><a href="#cite_note-Kirk_2000-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Choline_as_a_nutrient">Choline as a nutrient</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Choline&action=edit&section=2" title="Edit section: Choline as a nutrient"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Choline is widespread in living beings. In most animals, choline phospholipids are necessary components in <a href="/wiki/Cell_membrane" title="Cell membrane">cell membranes</a>, in the membranes of cell <a href="/wiki/Organelle" title="Organelle">organelles</a>, and in <a href="/wiki/Very_low-density_lipoprotein" title="Very low-density lipoprotein">very low-density lipoproteins</a>.<sup id="cite_ref-lpi_4-5" class="reference"><a href="#cite_note-lpi-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> </p><p>Choline is an <a href="/wiki/Essential_nutrient" class="mw-redirect" title="Essential nutrient">essential nutrient</a> for humans and many other animals.<sup id="cite_ref-lpi_4-6" class="reference"><a href="#cite_note-lpi-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> Humans are capable of some <a href="/wiki/De_novo_synthesis" title="De novo synthesis"><i>de novo</i> synthesis</a> of choline but require additional choline in the diet to maintain health. Dietary requirements can be met by choline by itself or in the form of choline <a href="/wiki/Phospholipid" title="Phospholipid">phospholipids</a>, such as <a href="/wiki/Phosphatidylcholine" title="Phosphatidylcholine">phosphatidylcholine</a>.<sup id="cite_ref-lpi_4-7" class="reference"><a href="#cite_note-lpi-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> Choline is not formally classified as a <a href="/wiki/Vitamin" title="Vitamin">vitamin</a> despite being an essential nutrient with an <a href="/wiki/Amino_acid" title="Amino acid">amino acid</a>–like structure and metabolism.<sup id="cite_ref-ze_3-1" class="reference"><a href="#cite_note-ze-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> </p><p>Choline is required to produce <a href="/wiki/Acetylcholine" title="Acetylcholine">acetylcholine</a> – a <a href="/wiki/Neurotransmitter" title="Neurotransmitter">neurotransmitter</a> – and <a href="/wiki/S-adenosyl_methionine" class="mw-redirect" title="S-adenosyl methionine"><i>S</i>-adenosylmethionine</a> (SAM), a universal <a href="/wiki/Methyl" class="mw-redirect" title="Methyl">methyl</a> donor. Upon methylation SAM is transformed into <a href="/wiki/S-adenosyl_homocysteine" class="mw-redirect" title="S-adenosyl homocysteine">S-adenosyl homocysteine</a>.<sup id="cite_ref-lpi_4-8" class="reference"><a href="#cite_note-lpi-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> </p><p>Symptomatic choline deficiency causes <a href="/wiki/Non-alcoholic_fatty_liver_disease" class="mw-redirect" title="Non-alcoholic fatty liver disease">non-alcoholic fatty liver disease</a> and muscle damage.<sup id="cite_ref-lpi_4-9" class="reference"><a href="#cite_note-lpi-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> Excessive consumption of choline (greater than 7.5 grams per day) can cause <a href="/wiki/Low_blood_pressure" class="mw-redirect" title="Low blood pressure">low blood pressure</a>, <a href="/wiki/Sweating" class="mw-redirect" title="Sweating">sweating</a>, <a href="/wiki/Diarrhea" title="Diarrhea">diarrhea</a>, and <a href="/wiki/Fish-odor_disease" class="mw-redirect" title="Fish-odor disease">fish-like body smell</a> due to <a href="/wiki/Trimethylamine" title="Trimethylamine">trimethylamine</a>, which forms in the metabolism of choline.<sup id="cite_ref-lpi_4-10" class="reference"><a href="#cite_note-lpi-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-eu_6-0" class="reference"><a href="#cite_note-eu-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> Rich dietary sources of choline and choline phospholipids include <a href="/wiki/Organ_meats" class="mw-redirect" title="Organ meats">organ meats</a>, <a href="/wiki/Egg_yolks" class="mw-redirect" title="Egg yolks">egg yolks</a>, <a href="/wiki/Dairy_products" class="mw-redirect" title="Dairy products">dairy products</a>, <a href="/wiki/Peanut" title="Peanut">peanuts</a>, certain <a href="/wiki/Beans" class="mw-redirect" title="Beans">beans</a>, <a href="/wiki/Nut_(fruit)" title="Nut (fruit)">nuts</a> and <a href="/wiki/Seeds" class="mw-redirect" title="Seeds">seeds</a>. <a href="/wiki/Vegetables" class="mw-redirect" title="Vegetables">Vegetables</a> with <a href="/wiki/Pasta" title="Pasta">pasta</a> and <a href="/wiki/Rice" title="Rice">rice</a> also contribute to choline intake in the <a href="/wiki/American_diet" class="mw-redirect" title="American diet">American diet</a>.<sup id="cite_ref-lpi_4-11" class="reference"><a href="#cite_note-lpi-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-ods_5-7" class="reference"><a href="#cite_note-ods-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Metabolism">Metabolism</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Choline&action=edit&section=3" title="Edit section: Metabolism"><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=Choline&action=edit&section=4" title="Edit section: Biosynthesis"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure class="skin-invert-image" typeof="mw:File/Thumb"><a href="/wiki/File:Choline_biosynthesis.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/f/f4/Choline_biosynthesis.svg/450px-Choline_biosynthesis.svg.png" decoding="async" width="450" height="94" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/f/f4/Choline_biosynthesis.svg/675px-Choline_biosynthesis.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/f/f4/Choline_biosynthesis.svg/900px-Choline_biosynthesis.svg.png 2x" data-file-width="1029" data-file-height="216" /></a><figcaption><a href="/wiki/Biosynthesis" title="Biosynthesis">Biosynthesis</a> of choline in plants</figcaption></figure> <p>In plants, the first step in <a href="/wiki/De_novo_synthesis" title="De novo synthesis"><i>de novo</i> biosynthesis</a> of choline is the <a href="/wiki/Decarboxylation" title="Decarboxylation">decarboxylation</a> of <a href="/wiki/Serine" title="Serine">serine</a> into <a href="/wiki/Ethanolamine" title="Ethanolamine">ethanolamine</a>, which is catalyzed by a <a href="/wiki/Decarboxylase" class="mw-redirect" title="Decarboxylase">serine decarboxylase</a>.<sup id="cite_ref-pmid11461929_7-0" class="reference"><a href="#cite_note-pmid11461929-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> The synthesis of choline from ethanolamine may take place in three parallel pathways, where three consecutive <i>N</i>-methylation steps catalyzed by a <a href="/wiki/Methyl_transferase" class="mw-redirect" title="Methyl transferase">methyl transferase</a> are carried out on either the free-base,<sup id="cite_ref-pmid16653153_8-0" class="reference"><a href="#cite_note-pmid16653153-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> phospho-bases,<sup id="cite_ref-pmid10799484_9-0" class="reference"><a href="#cite_note-pmid10799484-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> or phosphatidyl-bases.<sup id="cite_ref-pmid11481443_10-0" class="reference"><a href="#cite_note-pmid11481443-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> The source of the methyl group is <a href="/wiki/S-adenosyl-L-methionine" class="mw-redirect" title="S-adenosyl-L-methionine"><i>S</i>-adenosyl-<span class="smallcaps"><span style="font-variant: small-caps; text-transform: lowercase;">L</span></span>-methionine</a> and <a href="/wiki/S-adenosyl-L-homocysteine" class="mw-redirect" title="S-adenosyl-L-homocysteine"><i>S</i>-adenosyl-<span class="smallcaps"><span style="font-variant: small-caps; text-transform: lowercase;">L</span></span>-homocysteine</a> is generated as a side product.<sup id="cite_ref-11" class="reference"><a href="#cite_note-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> </p> <figure class="skin-invert-image" typeof="mw:File/Thumb"><a href="/wiki/File:Choline_metabolism.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/4/41/Choline_metabolism.svg/300px-Choline_metabolism.svg.png" decoding="async" width="300" height="318" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/4/41/Choline_metabolism.svg/450px-Choline_metabolism.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/4/41/Choline_metabolism.svg/600px-Choline_metabolism.svg.png 2x" data-file-width="650" data-file-height="690" /></a><figcaption>Main pathways of choline (Chol) metabolism, synthesis and excretion. Click for details. Some of the abbreviations are used in this section.</figcaption></figure> <p>In humans and most other animals, de novo synthesis of choline proceeds via the <a href="/wiki/Phosphatidylethanolamine_N-methyltransferase" title="Phosphatidylethanolamine N-methyltransferase">phosphatidylethanolamine N-methyltransferase</a> (PEMT) pathway,<sup id="cite_ref-eu_6-1" class="reference"><a href="#cite_note-eu-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> but biosynthesis is not enough to meet human requirements.<sup id="cite_ref-his_12-0" class="reference"><a href="#cite_note-his-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup> In the hepatic PEMT route, <a href="/wiki/3-phosphoglycerate" class="mw-redirect" title="3-phosphoglycerate">3-phosphoglycerate</a> (3PG) receives 2 <a href="/wiki/Acyl_group" title="Acyl group">acyl groups</a> from <a href="/wiki/Acyl-CoA" title="Acyl-CoA">acyl-CoA</a> forming a <a href="/wiki/Phosphatidic_acid" title="Phosphatidic acid">phosphatidic acid</a>. It reacts with <a href="/wiki/Cytidine_triphosphate" title="Cytidine triphosphate">cytidine triphosphate</a> to form cytidine diphosphate-diacylglycerol. Its <a href="/wiki/Hydroxyl_group" class="mw-redirect" title="Hydroxyl group">hydroxyl group</a> reacts with serine to form <a href="/wiki/Phosphatidylserine" title="Phosphatidylserine">phosphatidylserine</a> which <a href="/wiki/Decarboxylate" class="mw-redirect" title="Decarboxylate">decarboxylates</a> to ethanolamine and <a href="/wiki/Phosphatidylethanolamine" title="Phosphatidylethanolamine">phosphatidylethanolamine</a> (PE) forms. A PEMT enzyme moves three <a href="/wiki/Methyl" class="mw-redirect" title="Methyl">methyl</a> groups from three <a href="/wiki/S-adenosyl_methionine" class="mw-redirect" title="S-adenosyl methionine"><i>S</i>-adenosyl methionines</a> (SAM) donors to the ethanolamine group of the phosphatidylethanolamine to form choline in the form of a phosphatidylcholine. Three <a href="/wiki/S-adenosyl_homocysteine" class="mw-redirect" title="S-adenosyl homocysteine"><i>S</i>-adenosylhomocysteines</a> (SAHs) are formed as a byproduct.<sup id="cite_ref-eu_6-2" class="reference"><a href="#cite_note-eu-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> </p><p>Choline can also be released from more complex precursors. For example, <a href="/wiki/Phosphatidylcholine" title="Phosphatidylcholine">phosphatidylcholines</a> (PC) can be hydrolyzed to choline (Chol) in most cell types. Choline can also be produced by the CDP-choline route, <a href="/wiki/Cytosolic" class="mw-redirect" title="Cytosolic">cytosolic</a> <a href="/wiki/Choline_kinase" title="Choline kinase">choline kinases</a> (CK) phosphorylate choline with <a href="/wiki/Adenosine_triphosphate" title="Adenosine triphosphate">ATP</a> to <a href="/wiki/Phosphocholine" title="Phosphocholine">phosphocholine</a> (PChol).<sup id="cite_ref-ze_3-2" class="reference"><a href="#cite_note-ze-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> This happens in some cell types like liver and kidney. <a href="/wiki/Choline-phosphate_cytidylyltransferase" title="Choline-phosphate cytidylyltransferase">Choline-phosphate cytidylyltransferases</a> (CPCT) transform PChol to <a href="/wiki/CDP-choline" class="mw-redirect" title="CDP-choline">CDP-choline</a> (CDP-Chol) with cytidine triphosphate (CTP). CDP-choline and <a href="/wiki/Diglyceride" title="Diglyceride">diglyceride</a> are transformed to PC by <a href="/wiki/Diacylglycerol_cholinephosphotransferase" title="Diacylglycerol cholinephosphotransferase">diacylglycerol cholinephosphotransferase</a> (CPT).<sup id="cite_ref-eu_6-3" class="reference"><a href="#cite_note-eu-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> </p><p>In humans, certain PEMT-enzyme <a href="/wiki/Mutation" title="Mutation">mutations</a> and <a href="/wiki/Estrogen_deficiency" class="mw-redirect" title="Estrogen deficiency">estrogen deficiency</a> (often due to <a href="/wiki/Menopause" title="Menopause">menopause</a>) increase the dietary need for choline. In rodents, 70% of phosphatidylcholines are formed via the PEMT route and only 30% via the CDP-choline route.<sup id="cite_ref-eu_6-4" class="reference"><a href="#cite_note-eu-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> In <a href="/wiki/Knockout_mice" class="mw-redirect" title="Knockout mice">knockout mice</a>, PEMT inactivation makes them completely dependent on dietary choline.<sup id="cite_ref-ze_3-3" class="reference"><a href="#cite_note-ze-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Absorption">Absorption</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Choline&action=edit&section=5" title="Edit section: Absorption"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>In humans, choline is absorbed from the <a href="/wiki/Intestine" class="mw-redirect" title="Intestine">intestines</a> via the <a href="/wiki/SLC44A1" class="mw-redirect" title="SLC44A1">SLC44A1</a> (CTL1) <a href="/wiki/Membrane_protein" title="Membrane protein">membrane protein</a> via <a href="/wiki/Facilitated_diffusion" title="Facilitated diffusion">facilitated diffusion</a> governed by the choline concentration gradient and the electrical potential across the <a href="/wiki/Enterocyte" title="Enterocyte">enterocyte</a> membranes. SLC44A1 has limited ability to transport choline: at high concentrations part of it is left unabsorbed. Absorbed choline leaves the enterocytes via the <a href="/wiki/Portal_vein" title="Portal vein">portal vein</a>, passes the liver and enters <a href="/wiki/Systemic_circulation" class="mw-redirect" title="Systemic circulation">systemic circulation</a>. <a href="/wiki/Gut_microbe" class="mw-redirect" title="Gut microbe">Gut microbes</a> degrade the unabsorbed choline to trimethylamine, which is oxidized in the liver to <a href="/wiki/Trimethylamine_N-oxide" title="Trimethylamine N-oxide">trimethylamine <i>N</i>-oxide</a>.<sup id="cite_ref-eu_6-5" class="reference"><a href="#cite_note-eu-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> </p><p>Phosphocholine and <a href="/wiki/Glycerophosphocholine" class="mw-redirect" title="Glycerophosphocholine">glycerophosphocholines</a> are hydrolyzed via <a href="/wiki/Phospholipase" title="Phospholipase">phospholipases</a> to choline, which enters the portal vein. Due to their water solubility, some of them escape unchanged to the portal vein. Fat-soluble choline-containing compounds (phosphatidylcholines and <a href="/wiki/Sphingomyelin" title="Sphingomyelin">sphingomyelins</a>) are either hydrolyzed by phospholipases or enter the <a href="/wiki/Lymph" title="Lymph">lymph</a> incorporated into <a href="/wiki/Chylomicron" title="Chylomicron">chylomicrons</a>.<sup id="cite_ref-eu_6-6" class="reference"><a href="#cite_note-eu-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Transport">Transport</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Choline&action=edit&section=6" title="Edit section: Transport"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>In humans, choline is transported as a free ion in blood. Choline–containing <a href="/wiki/Phospholipid" title="Phospholipid">phospholipids</a> and other substances, like glycerophosphocholines, are transported in blood <a href="/wiki/Lipoprotein" title="Lipoprotein">lipoproteins</a>. <a href="/wiki/Blood_plasma" title="Blood plasma">Blood plasma</a> choline levels in healthy <a href="/wiki/Fasting" title="Fasting">fasting</a> adults is 7–20 <a href="/wiki/Micromoles" class="mw-redirect" title="Micromoles">micromoles</a> per liter (μmol/L) and 10 μmol/L on average. Levels are regulated, but choline intake and deficiency alters these levels. Levels are elevated for about 3 hours after choline consumption. Phosphatidylcholine levels in the plasma of fasting adults is 1.5–2.5 mmol/L. Its consumption elevates the free choline levels for about 8–12 hours, but does not affect phosphatidylcholine levels significantly.<sup id="cite_ref-eu_6-7" class="reference"><a href="#cite_note-eu-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> </p><p>Choline is a water-soluble <a href="/wiki/Ion" title="Ion">ion</a> and thus requires transporters to pass through fat-soluble <a href="/wiki/Cell_membrane" title="Cell membrane">cell membranes</a>. Three types of choline transporters are known:<sup id="cite_ref-Inazu_2019_13-0" class="reference"><a href="#cite_note-Inazu_2019-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup> </p> <ul><li><a href="/wiki/SLC5A7" class="mw-redirect" title="SLC5A7">SLC5A7</a></li> <li>CTLs: CTL1 (<a href="/wiki/SLC44A1" class="mw-redirect" title="SLC44A1">SLC44A1</a>), CTL2 (<a href="/wiki/SLC44A2" class="mw-redirect" title="SLC44A2">SLC44A2</a>) and CTL4 (<a href="/wiki/SLC44A4" class="mw-redirect" title="SLC44A4">SLC44A4</a>)</li> <li>OCTs: OCT1 (<a href="/wiki/SLC22A1" title="SLC22A1">SLC22A1</a>) and OCT2 (<a href="/wiki/SLC22A2" title="SLC22A2">SLC22A2</a>)</li></ul> <p>SLC5A7s are <a href="/wiki/Sodium" title="Sodium">sodium</a>- (Na<sup>+</sup>) and ATP-dependent transporters.<sup id="cite_ref-Inazu_2019_13-1" class="reference"><a href="#cite_note-Inazu_2019-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-eu_6-8" class="reference"><a href="#cite_note-eu-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> They have high <a href="/wiki/Binding_affinity" class="mw-redirect" title="Binding affinity">binding affinity</a> for choline, transport it primarily to <a href="/wiki/Neuron" title="Neuron">neurons</a> and are indirectly associated with the <a href="/wiki/Acetylcholine" title="Acetylcholine">acetylcholine</a> production.<sup id="cite_ref-eu_6-9" class="reference"><a href="#cite_note-eu-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> Their deficient function causes <a href="/wiki/Hereditary" class="mw-redirect" title="Hereditary">hereditary</a> weakness in the pulmonary and other muscles in humans via acetylcholine deficiency. In <a href="/wiki/Knockout_mice" class="mw-redirect" title="Knockout mice">knockout mice</a>, their dysfunction results easily in death with <a href="/wiki/Cyanosis" title="Cyanosis">cyanosis</a> and <a href="/wiki/Paralysis" title="Paralysis">paralysis</a>.<sup id="cite_ref-14" class="reference"><a href="#cite_note-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup> </p><p>CTL1s have moderate affinity for choline and transport it in almost all tissues, including the intestines, liver, kidneys, <a href="/wiki/Placenta" title="Placenta">placenta</a> and <a href="/wiki/Mitochondria" class="mw-redirect" title="Mitochondria">mitochondria</a>. CTL1s supply choline for phosphatidylcholine and <a href="/wiki/Trimethylglycine" title="Trimethylglycine">trimethylglycine</a> production.<sup id="cite_ref-eu_6-10" class="reference"><a href="#cite_note-eu-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> CTL2s occur especially in the mitochondria in the tongue, kidneys, muscles and heart. They are associated with the mitochondrial <a href="/wiki/Oxidation" class="mw-redirect" title="Oxidation">oxidation</a> of choline to trimethylglycine. CTL1s and CTL2s are not associated with the acetylcholine production, but transport choline together via the <a href="/wiki/Blood%E2%80%93brain_barrier" title="Blood–brain barrier">blood–brain barrier</a>. Only CTL2s occur on the brain side of the barrier. They also remove excess choline from the neurons back to blood. CTL1s occur only on the blood side of the barrier, but also on the membranes of <a href="/wiki/Astrocyte" title="Astrocyte">astrocytes</a> and neurons.<sup id="cite_ref-Inazu_2019_13-2" class="reference"><a href="#cite_note-Inazu_2019-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup> </p><p>OCT1s and OCT2s are not associated with the acetylcholine production.<sup id="cite_ref-eu_6-11" class="reference"><a href="#cite_note-eu-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> They transport choline with low affinity. OCT1s transport choline primarily in the liver and kidneys; OCT2s in kidneys and the brain.<sup id="cite_ref-Inazu_2019_13-3" class="reference"><a href="#cite_note-Inazu_2019-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Storage">Storage</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Choline&action=edit&section=7" title="Edit section: Storage"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Choline is stored in the cell membranes and <a href="/wiki/Organelle" title="Organelle">organelles</a> as phospholipids, and inside cells as phosphatidylcholines and glycerophosphocholines.<sup id="cite_ref-eu_6-12" class="reference"><a href="#cite_note-eu-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Excretion">Excretion</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Choline&action=edit&section=8" title="Edit section: Excretion"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Even at choline doses of 2–8 g, little choline is excreted into urine in humans. Excretion happens via transporters that occur within kidneys (see <a class="mw-selflink-fragment" href="#Transport">transport</a>). Trimethylglycine is demethylated in the liver and kidneys to <a href="/wiki/Dimethylglycine" title="Dimethylglycine">dimethylglycine</a> (<a href="/wiki/Tetrahydrofolate" class="mw-redirect" title="Tetrahydrofolate">tetrahydrofolate</a> receives one of the methyl groups). <a href="/wiki/Methylglycine" class="mw-redirect" title="Methylglycine">Methylglycine</a> forms, is excreted into urine, or is demethylated to <a href="/wiki/Glycine" title="Glycine">glycine</a>.<sup id="cite_ref-eu_6-13" class="reference"><a href="#cite_note-eu-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Function">Function</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Choline&action=edit&section=9" title="Edit section: Function"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Choline and its derivatives have many biological functions. Notably choline serves as a precursor for other essential cell components and signaling molecules, such as phospholipids that form cell membranes, the <a href="/wiki/Neurotransmitter" title="Neurotransmitter">neurotransmitter</a> acetylcholine, and the <a href="/wiki/Osmoregulator" class="mw-redirect" title="Osmoregulator">osmoregulator</a> <a href="/wiki/Trimethylglycine" title="Trimethylglycine">trimethylglycine</a> (<a href="/wiki/Betaine" title="Betaine">betaine</a>). Trimethylglycine in turn serves as a source of <a href="/wiki/Methyl_group" title="Methyl group">methyl groups</a> by participating in the biosynthesis of <a href="/wiki/S-adenosylmethionine" class="mw-redirect" title="S-adenosylmethionine"><i>S</i>-adenosylmethionine</a>.<sup id="cite_ref-15" class="reference"><a href="#cite_note-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-pmid8333583_16-0" class="reference"><a href="#cite_note-pmid8333583-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Phospholipid_precursor">Phospholipid precursor</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Choline&action=edit&section=10" title="Edit section: Phospholipid precursor"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Choline is transformed to diverse phospholipids, like phosphatidylcholines and sphingomyelins.<sup id="cite_ref-lpi_4-12" class="reference"><a href="#cite_note-lpi-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-ods_5-8" class="reference"><a href="#cite_note-ods-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> These are found in all cell membranes and the membranes of most cell organelles.<sup id="cite_ref-ze_3-4" class="reference"><a href="#cite_note-ze-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> Phosphatidylcholines are structurally important part of the cell membranes. In humans, 40–50% of their phospholipids are phosphatidylcholines.<sup id="cite_ref-eu_6-14" class="reference"><a href="#cite_note-eu-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> </p><p>Choline phospholipids also form <a href="/wiki/Lipid_rafts" class="mw-redirect" title="Lipid rafts">lipid rafts</a> in the cell membranes along with <a href="/wiki/Cholesterol" title="Cholesterol">cholesterol</a>.<sup id="cite_ref-lpi_4-13" class="reference"><a href="#cite_note-lpi-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> The rafts are centers, for example for <a href="/wiki/Cholinergic" title="Cholinergic">cholinergic</a> <a href="/wiki/Receptor_(biochemistry)" title="Receptor (biochemistry)">receptors</a> and receptor <a href="/wiki/Signal_transduction" title="Signal transduction">signal transduction</a> enzymes.<sup id="cite_ref-lpi_4-14" class="reference"><a href="#cite_note-lpi-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-ze_3-5" class="reference"><a href="#cite_note-ze-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> </p><p>Phosphatidylcholines are needed for the synthesis of <a href="/wiki/VLDL" class="mw-redirect" title="VLDL">VLDLs</a>: 70–95% of their phospholipids are phosphatidylcholines in humans.<sup id="cite_ref-eu_6-15" class="reference"><a href="#cite_note-eu-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> </p><p>Choline is also needed for the synthesis of <a href="/wiki/Pulmonary_surfactant" title="Pulmonary surfactant">pulmonary surfactant</a>, which is a mixture consisting mostly of phosphatidylcholines. The surfactant is responsible for lung elasticity, that is for lung tissue's ability to contract and expand. For example, deficiency of phosphatidylcholines in the lung tissues has been linked to <a href="/wiki/Acute_respiratory_distress_syndrome" title="Acute respiratory distress syndrome">acute respiratory distress syndrome</a>.<sup id="cite_ref-17" class="reference"><a href="#cite_note-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup> </p><p>Phosphatidylcholines are excreted into <a href="/wiki/Bile" title="Bile">bile</a> and work together with <a href="/wiki/Bile_acid" title="Bile acid">bile acid</a> salts as <a href="/wiki/Surfactant" title="Surfactant">surfactants</a> in it, thus helping with the <a href="/wiki/Intestinal" class="mw-redirect" title="Intestinal">intestinal</a> absorption of <a href="/wiki/Lipid" title="Lipid">lipids</a>.<sup id="cite_ref-ze_3-6" class="reference"><a href="#cite_note-ze-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Acetylcholine_synthesis">Acetylcholine synthesis</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Choline&action=edit&section=11" title="Edit section: Acetylcholine synthesis"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Choline is a precursor to <a href="/wiki/Acetylcholine" title="Acetylcholine">acetylcholine</a>, a neurotransmitter that plays a necessary role in <a href="/wiki/Muscle_contraction" title="Muscle contraction">muscle contraction</a>, memory and <a href="/wiki/Neural_development" class="mw-redirect" title="Neural development">neural development</a>.<sup id="cite_ref-lpi_4-15" class="reference"><a href="#cite_note-lpi-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-ods_5-9" class="reference"><a href="#cite_note-ods-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-eu_6-16" class="reference"><a href="#cite_note-eu-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> Nonetheless, there is little acetylcholine in the human body relative to other forms of choline.<sup id="cite_ref-ze_3-7" class="reference"><a href="#cite_note-ze-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> Neurons also store choline in the form of phospholipids to their cell membranes for the production of acetylcholine.<sup id="cite_ref-eu_6-17" class="reference"><a href="#cite_note-eu-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Source_of_trimethylglycine">Source of trimethylglycine</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Choline&action=edit&section=12" title="Edit section: Source of trimethylglycine"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>In humans, choline is <a href="/wiki/Oxidized" class="mw-redirect" title="Oxidized">oxidized</a> irreversibly in liver mitochondria to <a href="/wiki/Glycine_betaine_aldehyde" title="Glycine betaine aldehyde">glycine betaine aldehyde</a> by <a href="/wiki/Choline_oxidase" title="Choline oxidase">choline oxidases</a>. This is oxidized by mitochondrial or cytosolic <a href="/wiki/Betaine-aldehyde_dehydrogenase" title="Betaine-aldehyde dehydrogenase">betaine-aldehyde dehydrogenases</a> to trimethylglycine.<sup id="cite_ref-eu_6-18" class="reference"><a href="#cite_note-eu-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> Trimethylglycine is a necessary osmoregulator. It also works as a substrate for the <a href="/wiki/BHMT" class="mw-redirect" title="BHMT">BHMT</a>-enzyme, which methylates <a href="/wiki/Homocysteine" title="Homocysteine">homocysteine</a> to <a href="/wiki/Methionine" title="Methionine">methionine</a>. This is a <i>S</i>-adenosylmethionine (SAM) precursor. SAM is a common reagent in biological <a href="/wiki/Methylation" title="Methylation">methylation</a> reactions. For example, it methylates <a href="/wiki/Guanidine" title="Guanidine">guanidines</a> of <a href="/wiki/DNA" title="DNA">DNA</a> and certain <a href="/wiki/Lysine" title="Lysine">lysines</a> of <a href="/wiki/Histone" title="Histone">histones</a>. Thus it is part of <a href="/wiki/Gene_expression" title="Gene expression">gene expression</a> and <a href="/wiki/Epigenetic_regulation" class="mw-redirect" title="Epigenetic regulation">epigenetic regulation</a>. Choline deficiency thus leads to elevated homocysteine levels and decreased SAM levels in blood.<sup id="cite_ref-eu_6-19" class="reference"><a href="#cite_note-eu-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Content_in_foods">Content in foods</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Choline&action=edit&section=13" title="Edit section: Content in foods"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Choline occurs in foods as a free cation and in the form of phospholipids, especially as phosphatidylcholines. Choline is highest in <a href="/wiki/Organ_meats" class="mw-redirect" title="Organ meats">organ meats</a> and <a href="/wiki/Egg_yolks" class="mw-redirect" title="Egg yolks">egg yolks</a> though it is found to a lesser degree in non-organ meats, grains, vegetables, fruit and <a href="/wiki/Dairy_products" class="mw-redirect" title="Dairy products">dairy products</a>.<sup id="cite_ref-ods_5-10" class="reference"><a href="#cite_note-ods-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> <a href="/wiki/Cooking_oil" title="Cooking oil">Cooking oils</a> and other food fats have about 5 mg/100 g of total choline.<sup id="cite_ref-eu_6-20" class="reference"><a href="#cite_note-eu-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> In the United States, <a href="/wiki/Nutrition_facts_label" title="Nutrition facts label">food labels</a> express the amount of choline in a serving as a percentage of <a href="/wiki/Daily_Value" class="mw-redirect" title="Daily Value">Daily Value</a> (%DV) based on the <a href="/wiki/Adequate_Intake" class="mw-redirect" title="Adequate Intake">Adequate Intake</a> of 550 mg/day. 100% of the daily value means that a serving of food has 550 mg of choline.<sup id="cite_ref-ods_5-11" class="reference"><a href="#cite_note-ods-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> "Total choline" is defined as the sum of free choline and choline-containing phospholipids, without accounting for mass fraction.<sup id="cite_ref-ods_5-12" class="reference"><a href="#cite_note-ods-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Zeisel_2003_18-0" class="reference"><a href="#cite_note-Zeisel_2003-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup> </p><p><a href="/wiki/Human_breast_milk" class="mw-redirect" title="Human breast milk">Human breast milk</a> is rich in choline.<sup id="cite_ref-lpi_4-16" class="reference"><a href="#cite_note-lpi-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-ods_5-13" class="reference"><a href="#cite_note-ods-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> Exclusive <a href="/wiki/Breastfeeding" title="Breastfeeding">breastfeeding</a> corresponds to about 120 mg of choline per day for the baby. Increase in a mother's choline intake raises the choline content of breast milk and low intake decreases it.<sup id="cite_ref-eu_6-21" class="reference"><a href="#cite_note-eu-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> <a href="/wiki/Infant_formula" title="Infant formula">Infant formulas</a> may or may not contain enough choline. In the EU and the US, it is mandatory to add at least 7 mg of choline per 100 <a href="/wiki/Kilocalories" class="mw-redirect" title="Kilocalories">kilocalories</a> (kcal) to every infant formula. In the EU, levels above 50 mg/100 kcal are not allowed.<sup id="cite_ref-eu_6-22" class="reference"><a href="#cite_note-eu-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-19" class="reference"><a href="#cite_note-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup> </p><p>Trimethylglycine is a functional <a href="/wiki/Metabolite" title="Metabolite">metabolite</a> of choline. It substitutes for choline nutritionally, but only partially.<sup id="cite_ref-ze_3-8" class="reference"><a href="#cite_note-ze-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> High amounts of trimethylglycine occur in <a href="/wiki/Wheat_bran" class="mw-redirect" title="Wheat bran">wheat bran</a> (1,339 mg/100 g), toasted <a href="/wiki/Wheat_germ" class="mw-redirect" title="Wheat germ">wheat germ</a> (1,240 mg/100 g) and <a href="/wiki/Spinach" title="Spinach">spinach</a> (600–645 mg/100 g), for example.<sup id="cite_ref-Zeisel_2003_18-1" class="reference"><a href="#cite_note-Zeisel_2003-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup> </p> <table class="wikitable"> <caption>Choline content of foods (mg/100 g)<sup id="cite_ref-cholinecontent_table_20-0" class="reference"><a href="#cite_note-cholinecontent_table-20"><span class="cite-bracket">[</span>a<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Zeisel_2003_18-2" class="reference"><a href="#cite_note-Zeisel_2003-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup> </caption> <tbody><tr> <th colspan="2">Meats </th> <th colspan="2">Vegetables </th></tr> <tr> <td><a href="/wiki/Bacon" title="Bacon">Bacon</a>, cooked </td> <td>124.89 </td> <td><a href="/wiki/Green_bean" title="Green bean">Bean, snap</a> </td> <td>13.46 </td></tr> <tr> <td>Beef, trim-cut, cooked </td> <td>78.15 </td> <td><a href="/wiki/Beetroot" title="Beetroot">Beetroot</a> </td> <td>6.01 </td></tr> <tr> <td><a href="/wiki/Beef_liver" class="mw-redirect" title="Beef liver">Beef liver</a>, pan fried </td> <td>418.22 </td> <td><a href="/wiki/Broccoli" title="Broccoli">Broccoli</a> </td> <td>40.06 </td></tr> <tr> <td>Chicken, roasted, with skin </td> <td>65.83 </td> <td><a href="/wiki/Brussels_sprout" title="Brussels sprout">Brussels sprout</a> </td> <td>40.61 </td></tr> <tr> <td>Chicken, roasted, no skin </td> <td>78.74 </td> <td><a href="/wiki/Cabbage" title="Cabbage">Cabbage</a> </td> <td>15.45 </td></tr> <tr> <td><a href="/wiki/Chicken_liver" class="mw-redirect" title="Chicken liver">Chicken liver</a> </td> <td>290.03 </td> <td><a href="/wiki/Carrot" title="Carrot">Carrot</a> </td> <td>8.79 </td></tr> <tr> <td><a href="/wiki/Atlantic_cod" title="Atlantic cod">Cod, atlantic</a> </td> <td>83.63 </td> <td><a href="/wiki/Cauliflower" title="Cauliflower">Cauliflower</a> </td> <td>39.10 </td></tr> <tr> <td><a href="/wiki/Ground_beef" title="Ground beef">Ground beef</a>, 75–85% lean, broiled </td> <td>79.32–82.35 </td> <td><a href="/wiki/Maize" title="Maize">Sweetcorn</a>, yellow </td> <td>21.95 </td></tr> <tr> <td><a href="/wiki/Pork_loin" title="Pork loin">Pork loin</a> cooked </td> <td>102.76 </td> <td><a href="/wiki/Cucumber" title="Cucumber">Cucumber</a> </td> <td>5.95 </td></tr> <tr> <td><a href="/wiki/Shrimp" title="Shrimp">Shrimp</a>, canned </td> <td>70.60 </td> <td><a href="/wiki/Lettuce,_iceberg" class="mw-redirect" title="Lettuce, iceberg">Lettuce, iceberg</a> </td> <td>6.70 </td></tr> <tr> <th colspan="2">Dairy products (cow) </th> <td><a href="/wiki/Romaine_lettuce" title="Romaine lettuce">Lettuce, romaine</a> </td> <td>9.92 </td></tr> <tr> <td>Butter, salted </td> <td>18.77 </td> <td><a href="/wiki/Pea" title="Pea">Pea</a> </td> <td>27.51 </td></tr> <tr> <td>Cheese </td> <td>16.50–27.21 </td> <td><a href="/wiki/Sauerkraut" title="Sauerkraut">Sauerkraut</a> </td> <td>10.39 </td></tr> <tr> <td><a href="/wiki/Cottage_cheese" title="Cottage cheese">Cottage cheese</a> </td> <td>18.42 </td> <td><a href="/wiki/Spinach" title="Spinach">Spinach</a> </td> <td>22.08 </td></tr> <tr> <td>Milk, whole/skimmed </td> <td>14.29–16.40 </td> <td><a href="/wiki/Sweet_potato" title="Sweet potato">Sweet potato</a> </td> <td>13.11 </td></tr> <tr> <td><a href="/wiki/Sour_cream" title="Sour cream">Sour cream</a> </td> <td>20.33 </td> <td><a href="/wiki/Tomato" title="Tomato">Tomato</a> </td> <td>6.74 </td></tr> <tr> <td><a href="/wiki/Yogurt" title="Yogurt">Yogurt</a>, plain </td> <td>15.20 </td> <td><a href="/wiki/Zucchini" title="Zucchini">Zucchini</a> </td> <td>9.36 </td></tr> <tr> <th colspan="2">Grains </th> <th colspan="2">Fruits </th></tr> <tr> <td>Oat <a href="/wiki/Bran" title="Bran">bran</a>, raw </td> <td>58.57 </td> <td><a href="/wiki/Apple" title="Apple">Apple</a> </td> <td>3.44 </td></tr> <tr> <td><a href="/wiki/Oatmeal" title="Oatmeal">Oats</a>, plain </td> <td>7.42 </td> <td><a href="/wiki/Avocado" title="Avocado">Avocado</a> </td> <td>14.18 </td></tr> <tr> <td><a href="/wiki/White_rice" title="White rice">Rice, white</a> </td> <td>2.08 </td> <td><a href="/wiki/Banana" title="Banana">Banana</a> </td> <td>9.76 </td></tr> <tr> <td><a href="/wiki/Brown_rice" title="Brown rice">Rice, brown</a> </td> <td>9.22 </td> <td><a href="/wiki/Blueberry" title="Blueberry">Blueberry</a> </td> <td>6.04 </td></tr> <tr> <td>Wheat <a href="/wiki/Bran" title="Bran">bran</a> </td> <td>74.39 </td> <td><a href="/wiki/Cantaloupe" title="Cantaloupe">Cantaloupe</a> </td> <td>7.58 </td></tr> <tr> <td><a href="/wiki/Wheat_germ" class="mw-redirect" title="Wheat germ">Wheat germ</a>, toasted </td> <td>152.08 </td> <td><a href="/wiki/Grape" title="Grape">Grape</a> </td> <td>7.53 </td></tr> <tr> <th colspan="2">Others </th> <td><a href="/wiki/Grapefruit" title="Grapefruit">Grapefruit</a> </td> <td>5.63 </td></tr> <tr> <td><a href="/wiki/Navy_bean" title="Navy bean">Bean, navy</a> </td> <td>26.93 </td> <td>Orange </td> <td>8.38 </td></tr> <tr> <td><a href="/wiki/Chicken_egg" class="mw-redirect" title="Chicken egg">Egg, chicken</a> </td> <td>251.00 </td> <td><a href="/wiki/Peach" title="Peach">Peach</a> </td> <td>6.10 </td></tr> <tr> <td><a href="/wiki/Olive_oil" title="Olive oil">Olive oil</a> </td> <td>0.29 </td> <td><a href="/wiki/Pear" title="Pear">Pear</a> </td> <td>5.11 </td></tr> <tr> <td><a href="/wiki/Peanut" title="Peanut">Peanut</a> </td> <td>52.47 </td> <td><a href="/wiki/Prune" title="Prune">Prune</a> </td> <td>9.66 </td></tr> <tr> <td><a href="/wiki/Soybean" title="Soybean">Soybean</a>, raw </td> <td>115.87 </td> <td><a href="/wiki/Strawberry" title="Strawberry">Strawberry</a> </td> <td>5.65 </td></tr> <tr> <td><a href="/wiki/Tofu" title="Tofu">Tofu</a>, soft </td> <td>27.37 </td> <td><a href="/wiki/Watermelon" title="Watermelon">Watermelon</a> </td> <td>4.07 </td></tr></tbody></table> <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-lower-alpha"> <div class="mw-references-wrap"><ol class="references"> <li id="cite_note-cholinecontent_table-20"><span class="mw-cite-backlink"><b><a href="#cite_ref-cholinecontent_table_20-0">^</a></b></span> <span class="reference-text">Foods are raw unless noted otherwise. Contents are "total choline" as defined above.</span> </li> </ol></div></div> <div class="mw-heading mw-heading3"><h3 id="Daily_values">Daily values</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Choline&action=edit&section=14" title="Edit section: Daily values"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1251242444">.mw-parser-output .ambox{border:1px solid #a2a9b1;border-left:10px solid #36c;background-color:#fbfbfb;box-sizing:border-box}.mw-parser-output .ambox+link+.ambox,.mw-parser-output .ambox+link+style+.ambox,.mw-parser-output .ambox+link+link+.ambox,.mw-parser-output .ambox+.mw-empty-elt+link+.ambox,.mw-parser-output .ambox+.mw-empty-elt+link+style+.ambox,.mw-parser-output .ambox+.mw-empty-elt+link+link+.ambox{margin-top:-1px}html body.mediawiki .mw-parser-output .ambox.mbox-small-left{margin:4px 1em 4px 0;overflow:hidden;width:238px;border-collapse:collapse;font-size:88%;line-height:1.25em}.mw-parser-output .ambox-speedy{border-left:10px solid #b32424;background-color:#fee7e6}.mw-parser-output .ambox-delete{border-left:10px solid #b32424}.mw-parser-output .ambox-content{border-left:10px solid #f28500}.mw-parser-output .ambox-style{border-left:10px solid #fc3}.mw-parser-output .ambox-move{border-left:10px solid #9932cc}.mw-parser-output .ambox-protection{border-left:10px solid #a2a9b1}.mw-parser-output .ambox .mbox-text{border:none;padding:0.25em 0.5em;width:100%}.mw-parser-output .ambox .mbox-image{border:none;padding:2px 0 2px 0.5em;text-align:center}.mw-parser-output .ambox .mbox-imageright{border:none;padding:2px 0.5em 2px 0;text-align:center}.mw-parser-output .ambox .mbox-empty-cell{border:none;padding:0;width:1px}.mw-parser-output .ambox .mbox-image-div{width:52px}@media(min-width:720px){.mw-parser-output .ambox{margin:0 10%}}@media print{body.ns-0 .mw-parser-output .ambox{display:none!important}}</style><table class="box-Cleanup plainlinks metadata ambox ambox-style ambox-Cleanup" role="presentation"><tbody><tr><td class="mbox-image"><div class="mbox-image-div"><span typeof="mw:File"><span><img alt="" src="//upload.wikimedia.org/wikipedia/en/thumb/f/f2/Edit-clear.svg/40px-Edit-clear.svg.png" decoding="async" width="40" height="40" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/f2/Edit-clear.svg/60px-Edit-clear.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/f2/Edit-clear.svg/80px-Edit-clear.svg.png 2x" data-file-width="48" data-file-height="48" /></span></span></div></td><td class="mbox-text"><div class="mbox-text-span">This section may <b>require <a href="/wiki/Wikipedia:Cleanup" title="Wikipedia:Cleanup">cleanup</a></b> to meet Wikipedia's <a href="/wiki/Wikipedia:Manual_of_Style" title="Wikipedia:Manual of Style">quality standards</a>. The specific problem is: <b>Should be merged to above list. The overlaps are quite large to the extent that the values (when converted to 100g) are virtually identical. DV calculation is quite trivial, so this isn't adding anything useful for now.</b><span class="hide-when-compact"> Please help <a href="/wiki/Special:EditPage/Choline" title="Special:EditPage/Choline">improve this section</a> if you can.</span> <span class="date-container"><i>(<span class="date">September 2022</span>)</i></span><span class="hide-when-compact"><i> (<small><a href="/wiki/Help:Maintenance_template_removal" title="Help:Maintenance template removal">Learn how and when to remove this message</a></small>)</i></span></div></td></tr></tbody></table> <p>The following table contains updated sources of choline to reflect the new Daily Value and the new Nutrition Facts and Supplement Facts Labels.<sup id="cite_ref-ods_5-14" class="reference"><a href="#cite_note-ods-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> It reflects data from the U.S. Department of Agriculture, Agricultural Research Service. FoodData Central, 2019.<sup id="cite_ref-ods_5-15" class="reference"><a href="#cite_note-ods-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> </p> <table class="wikitable"> <caption>Selected Food Sources of Choline<sup id="cite_ref-ods_5-16" class="reference"><a href="#cite_note-ods-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> </caption> <tbody><tr> <td>Food </td> <td>Milligrams (mg) per serving </td> <td>Percent DV* </td></tr> <tr> <td><a href="/wiki/Beef_liver" class="mw-redirect" title="Beef liver">Beef liver</a>, pan fried, 3 oz (85 g) </td> <td>356 </td> <td>65 </td></tr> <tr> <td>Egg, hard boiled, 1 large egg </td> <td>147 </td> <td>27 </td></tr> <tr> <td>Beef <a href="/wiki/Top_round" class="mw-redirect" title="Top round">top round</a>, separable lean only, braised, 3 oz (85 g) </td> <td>117 </td> <td>21 </td></tr> <tr> <td><a href="/wiki/Soybean" title="Soybean">Soybeans</a>, roasted, <style data-mw-deduplicate="TemplateStyles:r1154941027">.mw-parser-output .frac{white-space:nowrap}.mw-parser-output .frac .num,.mw-parser-output .frac .den{font-size:80%;line-height:0;vertical-align:super}.mw-parser-output .frac .den{vertical-align:sub}.mw-parser-output .sr-only{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}</style><span class="frac"><span class="num">1</span>⁄<span class="den">2</span></span> cup </td> <td>107 </td> <td>19 </td></tr> <tr> <td>Chicken breast, roasted, 3 oz (85 g) </td> <td>72 </td> <td>13 </td></tr> <tr> <td>Beef, ground, 93% lean meat, broiled, 3 oz (85 g) </td> <td>72 </td> <td>13 </td></tr> <tr> <td><a href="/wiki/Atlantic_cod" title="Atlantic cod">Cod, Atlantic</a>, cooked, dry heat, 3 oz (85 g) </td> <td>71 </td> <td>13 </td></tr> <tr> <td><a href="/wiki/Shiitake" title="Shiitake">Mushrooms, shiitake</a>, cooked, <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1154941027"><span class="frac"><span class="num">1</span>⁄<span class="den">2</span></span> cup pieces </td> <td>58 </td> <td>11 </td></tr> <tr> <td><a href="/wiki/Red_potato" class="mw-redirect" title="Red potato">Potatoes, red</a>, baked, flesh and skin, 1 large potato </td> <td>57 </td> <td>10 </td></tr> <tr> <td><a href="/wiki/Wheat_germ" class="mw-redirect" title="Wheat germ">Wheat germ</a>, toasted, 1 oz (28 g) </td> <td>51 </td> <td>9 </td></tr> <tr> <td><a href="/wiki/Kidney_bean" title="Kidney bean">Beans, kidney</a>, canned, <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1154941027"><span class="frac"><span class="num">1</span>⁄<span class="den">2</span></span> cup </td> <td>45 </td> <td>8 </td></tr> <tr> <td><a href="/wiki/Quinoa" title="Quinoa">Quinoa</a>, cooked, 1 cup </td> <td>43 </td> <td>8 </td></tr> <tr> <td><a href="/wiki/Cow%27s_milk" class="mw-redirect" title="Cow's milk">Milk</a>, 1% fat, 1 cup </td> <td>43 </td> <td>8 </td></tr> <tr> <td><a href="/wiki/Yogurt" title="Yogurt">Yogurt</a>, vanilla, nonfat, 1 cup </td> <td>38 </td> <td>7 </td></tr> <tr> <td><a href="/wiki/Brussels_sprout" title="Brussels sprout">Brussels sprouts</a>, boiled, <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1154941027"><span class="frac"><span class="num">1</span>⁄<span class="den">2</span></span> cup </td> <td>32 </td> <td>6 </td></tr> <tr> <td><a href="/wiki/Broccoli" title="Broccoli">Broccoli</a>, chopped, boiled, drained, <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1154941027"><span class="frac"><span class="num">1</span>⁄<span class="den">2</span></span> cup </td> <td>31 </td> <td>6 </td></tr> <tr> <td><a href="/wiki/Cottage_cheese" title="Cottage cheese">Cottage cheese</a>, nonfat, 1 cup </td> <td>26 </td> <td>5 </td></tr> <tr> <td><a href="/wiki/Tuna" title="Tuna">Tuna</a>, white, canned in water, drained in solids, 3 oz (85 g) </td> <td>25 </td> <td>5 </td></tr> <tr> <td><a href="/wiki/Peanut" title="Peanut">Peanuts</a>, dry roasted, <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1154941027"><span class="frac"><span class="num">1</span>⁄<span class="den">4</span></span> cup </td> <td>24 </td> <td>4 </td></tr> <tr> <td><a href="/wiki/Cauliflower" title="Cauliflower">Cauliflower</a>, 1 in (2.5 cm) pieces, boiled, drained, <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1154941027"><span class="frac"><span class="num">1</span>⁄<span class="den">2</span></span> cup </td> <td>24 </td> <td>4 </td></tr> <tr> <td><a href="/wiki/Green_peas" class="mw-redirect" title="Green peas">Peas, green</a>, boiled, <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1154941027"><span class="frac"><span class="num">1</span>⁄<span class="den">2</span></span> cup </td> <td>24 </td> <td>4 </td></tr> <tr> <td><a href="/wiki/Sunflower_seeds" class="mw-redirect" title="Sunflower seeds">Sunflower seeds</a>, oil roasted, <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1154941027"><span class="frac"><span class="num">1</span>⁄<span class="den">4</span></span> cup </td> <td>19 </td> <td>3 </td></tr> <tr> <td><a href="/wiki/Brown_rice" title="Brown rice">Rice, brown</a>, long-grain, cooked, 1 cup </td> <td>19 </td> <td>3 </td></tr> <tr> <td><a href="/wiki/Pita" title="Pita">Bread, pita</a>, whole wheat, 1 large (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1154941027"><span class="frac">6<span class="sr-only">+</span><span class="num">1</span>⁄<span class="den">2</span></span> in or 17 cm diameter) </td> <td>17 </td> <td>3 </td></tr> <tr> <td><a href="/wiki/Cabbage" title="Cabbage">Cabbage</a>, boiled, <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1154941027"><span class="frac"><span class="num">1</span>⁄<span class="den">2</span></span> cup </td> <td>15 </td> <td>3 </td></tr> <tr> <td><a href="/wiki/Tangerine" title="Tangerine">Tangerine</a> (<a href="/wiki/Mandarin_orange" title="Mandarin orange">mandarin orange</a>), sections, <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1154941027"><span class="frac"><span class="num">1</span>⁄<span class="den">2</span></span> cup </td> <td>10 </td> <td>2 </td></tr> <tr> <td><a href="/wiki/Snap_bean" class="mw-redirect" title="Snap bean">Beans, snap</a>, raw, <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1154941027"><span class="frac"><span class="num">1</span>⁄<span class="den">2</span></span> cup </td> <td>8 </td> <td>1 </td></tr> <tr> <td><a href="/wiki/Kiwifruit" title="Kiwifruit">Kiwifruit</a>, raw, <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1154941027"><span class="frac"><span class="num">1</span>⁄<span class="den">2</span></span> cup sliced </td> <td>7 </td> <td>1 </td></tr> <tr> <td>Carrots, raw, chopped, <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1154941027"><span class="frac"><span class="num">1</span>⁄<span class="den">2</span></span> cup </td> <td>6 </td> <td>1 </td></tr> <tr> <td><a href="/wiki/Apple" title="Apple">Apples</a>, raw, with skin, quartered or chopped, <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1154941027"><span class="frac"><span class="num">1</span>⁄<span class="den">2</span></span> cup </td> <td>2 </td> <td>0 </td></tr></tbody></table> <p><small>DV = Daily Value. The U.S. Food and Drug Administration (FDA) developed DVs to help consumers compare the nutrient contents of foods and dietary supplements within the context of a total diet. The DV for choline is 550 mg for adults and children age 4 years and older.<sup id="cite_ref-21" class="reference"><a href="#cite_note-21"><span class="cite-bracket">[</span>20<span class="cite-bracket">]</span></a></sup> The FDA does not require food labels to list choline content unless choline has been added to the food. Foods providing 20% or more of the DV are considered to be high sources of a nutrient, but foods providing lower percentages of the DV also contribute to a healthful diet.<sup id="cite_ref-ods_5-17" class="reference"><a href="#cite_note-ods-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup></small> </p><p><small>The U.S. Department of Agriculture's (USDA's) FoodData Central lists the nutrient content of many foods and provides a comprehensive list of foods containing choline arranged by nutrient content.<sup id="cite_ref-ods_5-18" class="reference"><a href="#cite_note-ods-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup></small> </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=Choline&action=edit&section=15" title="Edit section: Dietary recommendations"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Insufficient data is available to establish an estimated average requirement (EAR) for choline, so the Food and Nutrition Board established adequate intakes (AIs).<sup id="cite_ref-ods_5-19" class="reference"><a href="#cite_note-ods-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-22" class="reference"><a href="#cite_note-22"><span class="cite-bracket">[</span>21<span class="cite-bracket">]</span></a></sup> For adults, the AI for choline was set at 550 mg/day for men and 425 mg/day for women.<sup id="cite_ref-ods_5-20" class="reference"><a href="#cite_note-ods-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> These values have been shown to prevent hepatic alteration in men. However, the study used to derive these values did not evaluate whether less choline would be effective, as researchers only compared a choline-free diet to a diet containing 550 mg of choline per day. From this, the AIs for children and adolescents were extrapolated.<sup id="cite_ref-23" class="reference"><a href="#cite_note-23"><span class="cite-bracket">[</span>22<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-24" class="reference"><a href="#cite_note-24"><span class="cite-bracket">[</span>23<span class="cite-bracket">]</span></a></sup> </p><p>Recommendations are in milligrams per day (mg/day). The <a href="/wiki/European_Food_Safety_Authority" title="European Food Safety Authority">European Food Safety Authority</a> (EFSA) recommendations are general recommendations for the <a href="/wiki/EU_countries" class="mw-redirect" title="EU countries">EU countries</a>. The EFSA has not set any upper limits for intake.<sup id="cite_ref-eu_6-23" class="reference"><a href="#cite_note-eu-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> Individual EU countries may have more specific recommendations. The <a href="/wiki/National_Academy_of_Medicine" title="National Academy of Medicine">National Academy of Medicine</a> (NAM) recommendations apply in the United States,<sup id="cite_ref-ods_5-21" class="reference"><a href="#cite_note-ods-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> Australia and New Zealand.<sup id="cite_ref-25" class="reference"><a href="#cite_note-25"><span class="cite-bracket">[</span>24<span class="cite-bracket">]</span></a></sup> </p> <table class="wikitable" style="text-align:center"> <caption>Choline recommendations (mg/day) </caption> <tbody><tr> <th>Age </th> <th>EFSA <a href="/wiki/Adequate_intake" class="mw-redirect" title="Adequate intake">adequate intake</a><sup id="cite_ref-eu_6-24" class="reference"><a href="#cite_note-eu-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> </th> <th>US NAM adequate intake<sup id="cite_ref-ods_5-22" class="reference"><a href="#cite_note-ods-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> </th> <th>US NAM <a href="/wiki/Tolerable_upper_intake_levels" class="mw-redirect" title="Tolerable upper intake levels">tolerable upper intake levels</a><sup id="cite_ref-ods_5-23" class="reference"><a href="#cite_note-ods-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> </th></tr> <tr> <td colspan="4"><b>Infants and children</b> </td></tr> <tr> <td>0–6 months </td> <td>Not established </td> <td>125 </td> <td>Not established </td></tr> <tr> <td>7–12 months </td> <td>160 </td> <td>150 </td> <td>Not established </td></tr> <tr> <td>1–3 years </td> <td>140 </td> <td>200 </td> <td>1,000 </td></tr> <tr> <td>4–6 years </td> <td>170 </td> <td>250 </td> <td>1,000 </td></tr> <tr> <td>7–8 years </td> <td>250 </td> <td>250 </td> <td>1,000 </td></tr> <tr> <td>9–10 years </td> <td>250 </td> <td>375 </td> <td>1,000 </td></tr> <tr> <td>11–13 years </td> <td>340 </td> <td>375 </td> <td>2,000 </td></tr> <tr> <td colspan="4"><b>Males</b> </td></tr> <tr> <td>14 years </td> <td>340 </td> <td>550 </td> <td>3,000 </td></tr> <tr> <td>15–18 years </td> <td>400 </td> <td>550 </td> <td>3,000 </td></tr> <tr> <td>19+ years </td> <td>400 </td> <td>550 </td> <td>3,500 </td></tr> <tr> <td colspan="4"><b>Females</b> </td></tr> <tr> <td>14 years </td> <td>340 </td> <td>400 </td> <td>3,000 </td></tr> <tr> <td>15–18 years </td> <td>400 </td> <td>400 </td> <td>3,000 </td></tr> <tr> <td>19+ y </td> <td>400 </td> <td>425 </td> <td>3,500 </td></tr> <tr> <td><b>If pregnant</b> </td> <td>480 </td> <td>450 </td> <td>3,500 (3,000 if ≤18 y) </td></tr> <tr> <td><b>If breastfeeding</b> </td> <td>520 </td> <td>550 </td> <td>3,500 (3,000 if ≤18 y) </td></tr></tbody></table> <div class="mw-heading mw-heading2"><h2 id="Intake_in_populations">Intake in populations</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Choline&action=edit&section=16" title="Edit section: Intake in populations"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Twelve surveys undertaken in 9 EU countries between 2000 and 2011 estimated choline intake of adults in these countries to be 269–468 milligrams per day. Intake was 269–444 mg/day in adult women and 332–468 mg/day in adult men. Intake was 75–127 mg/day in infants, 151–210 mg/day in 1- to 3-year-olds, 177–304 mg/day in 3- to 10-year-olds and 244–373 mg/day in 10- to 18-year-olds. The total choline intake mean estimate was 336 mg/day in pregnant adolescents and 356 mg/day in pregnant women.<sup id="cite_ref-eu_6-25" class="reference"><a href="#cite_note-eu-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> </p><p>A study based on the <a href="/wiki/NHANES" class="mw-redirect" title="NHANES">NHANES</a> 2009–2012 survey estimated the choline intake to be too low in some US subpopulations. Intake was 315.2–318.8 mg/d in 2+ year olds between this time period. Out of 2+ year olds, only <span class="nowrap"><span data-sort-value="7001156000000000000♠"></span>15.6<span style="margin-left:0.3em;margin-right:0.15em;">±</span>0.8</span>% of males and <span class="nowrap"><span data-sort-value="7000610000000000000♠"></span>6.1<span style="margin-left:0.3em;margin-right:0.15em;">±</span>0.6</span>% of females exceeded the adequate intake (AI). AI was exceeded by <span class="nowrap"><span data-sort-value="7001629000000000000♠"></span>62.9<span style="margin-left:0.3em;margin-right:0.15em;">±</span>3.1</span>% of 2- to 3-year-olds, <span class="nowrap"><span data-sort-value="7001454000000000000♠"></span>45.4<span style="margin-left:0.3em;margin-right:0.15em;">±</span>1.6</span>% of 4- to 8-year-olds, <span class="nowrap"><span data-sort-value="7000900000000000000♠"></span>9.0<span style="margin-left:0.3em;margin-right:0.15em;">±</span>1.0</span>% of 9- to 13-year-olds, <span class="nowrap"><span data-sort-value="7000180000000000000♠"></span>1.8<span style="margin-left:0.3em;margin-right:0.15em;">±</span>0.4</span>% of 14–18 and <span class="nowrap"><span data-sort-value="7000660000000000000♠"></span>6.6<span style="margin-left:0.3em;margin-right:0.15em;">±</span>0.5</span>% of 19+ year olds. Upper intake level was not exceeded in any subpopulations.<sup id="cite_ref-26" class="reference"><a href="#cite_note-26"><span class="cite-bracket">[</span>25<span class="cite-bracket">]</span></a></sup> </p><p>A 2013–2014 NHANES study of the US population found the choline intake of 2- to 19-year-olds to be <span class="nowrap"><span data-sort-value="7002256000000000000♠"></span>256<span style="margin-left:0.3em;margin-right:0.15em;">±</span>3.8</span> mg/day and <span class="nowrap"><span data-sort-value="7002339000000000000♠"></span>339<span style="margin-left:0.3em;margin-right:0.15em;">±</span>3.9</span> mg/day in adults 20 and over. Intake was <span class="nowrap"><span data-sort-value="7002402000000000000♠"></span>402<span style="margin-left:0.3em;margin-right:0.15em;">±</span>6.1</span> mg/d in men 20 and over and 278 mg/d in women 20 and over.<sup id="cite_ref-27" class="reference"><a href="#cite_note-27"><span class="cite-bracket">[</span>26<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=Choline&action=edit&section=17" title="Edit section: Deficiency"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Signs_and_symptoms">Signs and symptoms</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Choline&action=edit&section=18" title="Edit section: Signs and symptoms"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Symptomatic choline deficiency is rare in humans. Most obtain sufficient amounts of it from the diet and are able to biosynthesize limited amounts of it via <a href="/wiki/Phosphatidylethanolamine_N-methyltransferase" title="Phosphatidylethanolamine N-methyltransferase">PEMT</a>.<sup id="cite_ref-ze_3-9" class="reference"><a href="#cite_note-ze-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> Symptomatic deficiency is often caused by certain diseases or by other indirect causes. Severe deficiency causes muscle damage and <a href="/wiki/Non-alcoholic_fatty_liver_disease" class="mw-redirect" title="Non-alcoholic fatty liver disease">non-alcoholic fatty liver disease</a>, which may develop into <a href="/wiki/Cirrhosis" title="Cirrhosis">cirrhosis</a>.<sup id="cite_ref-Corbin_2012_28-0" class="reference"><a href="#cite_note-Corbin_2012-28"><span class="cite-bracket">[</span>27<span class="cite-bracket">]</span></a></sup> </p><p>Besides humans, fatty liver is also a typical sign of choline deficiency in other animals. Bleeding in the kidneys can also occur in some species. This is suspected to be due to deficiency of choline derived trimethylglycine, which functions as an osmoregulator.<sup id="cite_ref-ze_3-10" class="reference"><a href="#cite_note-ze-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Causes_and_mechanisms">Causes and mechanisms</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Choline&action=edit&section=19" title="Edit section: Causes and mechanisms"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><a href="/wiki/Estrogen" title="Estrogen">Estrogen</a> production is a relevant factor which predisposes individuals to deficiency along with low dietary choline intake. Estrogens activate phosphatidylcholine producing PEMT enzymes. Women before menopause have lower dietary need for choline than men due to women's higher estrogen production. Without <a href="/wiki/Estrogen_therapy" class="mw-redirect" title="Estrogen therapy">estrogen therapy</a>, the choline needs of post-menopausal women are similar to men's. Some <a href="/wiki/Single-nucleotide_polymorphism" title="Single-nucleotide polymorphism">single-nucleotide polymorphisms</a> (genetic factors) affecting choline and <a href="/wiki/Folate" title="Folate">folate</a> metabolism are also relevant. Certain gut microbes also degrade choline more efficiently than others, so they are also relevant.<sup id="cite_ref-Corbin_2012_28-1" class="reference"><a href="#cite_note-Corbin_2012-28"><span class="cite-bracket">[</span>27<span class="cite-bracket">]</span></a></sup> </p><p>In deficiency, availability of phosphatidylcholines in the liver are decreased – these are needed for formation of VLDLs. Thus VLDL-mediated <a href="/wiki/Fatty_acid" title="Fatty acid">fatty acid</a> transport out of the liver decreases leading to fat accumulation in the liver.<sup id="cite_ref-eu_6-26" class="reference"><a href="#cite_note-eu-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> Other simultaneously occurring mechanisms explaining the observed liver damage have also been suggested. For example, choline phospholipids are also needed in <a href="/wiki/Mitochondrial" class="mw-redirect" title="Mitochondrial">mitochondrial</a> membranes. Their unavailability leads to the inability of mitochondrial membranes to maintain proper <a href="/wiki/Electrochemical_gradient" title="Electrochemical gradient">electrochemical gradient</a>, which, among other things, is needed for degrading fatty acids via <a href="/wiki/%CE%92-oxidation" class="mw-redirect" title="Β-oxidation">β-oxidation</a>. Fat metabolism within liver therefore decreases.<sup id="cite_ref-Corbin_2012_28-2" class="reference"><a href="#cite_note-Corbin_2012-28"><span class="cite-bracket">[</span>27<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Excess_intake">Excess intake</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Choline&action=edit&section=20" title="Edit section: Excess intake"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Excessive doses of choline can have adverse effects. Daily 8–20 g doses of choline, for example, have been found to cause <a href="/wiki/Low_blood_pressure" class="mw-redirect" title="Low blood pressure">low blood pressure</a>, <a href="/wiki/Nausea" title="Nausea">nausea</a>, <a href="/wiki/Diarrhea" title="Diarrhea">diarrhea</a> and <a href="/wiki/Fish-odor_disease" class="mw-redirect" title="Fish-odor disease">fish-like body odor</a>. The odor is due to trimethylamine (TMA) formed by the gut microbes from the unabsorbed choline (see <a href="/wiki/Trimethylaminuria" title="Trimethylaminuria">trimethylaminuria</a>).<sup id="cite_ref-eu_6-27" class="reference"><a href="#cite_note-eu-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> </p><p>The liver oxidizes TMA to trimethylamine <i>N</i>-oxide (TMAO). Elevated levels of TMA and TMAO in the body have been linked to increased risk of <a href="/wiki/Atherosclerosis" title="Atherosclerosis">atherosclerosis</a> and mortality. Thus, excessive choline intake has been hypothetized to increase these risks in addition to <a href="/wiki/Carnitine" title="Carnitine">carnitine</a>, which also is formed into TMA and TMAO by gut bacteria. However, choline intake has not been shown to increase the risk of dying from <a href="/wiki/Cardiovascular_disease" title="Cardiovascular disease">cardiovascular diseases</a>.<sup id="cite_ref-DiNicolantonio_2019_29-0" class="reference"><a href="#cite_note-DiNicolantonio_2019-29"><span class="cite-bracket">[</span>28<span class="cite-bracket">]</span></a></sup> It is plausible that elevated TMA and TMAO levels are just a symptom of other underlying illnesses or genetic factors that predispose individuals for increased mortality. Such factors may have not been properly accounted for in certain studies observing TMA and TMAO level related mortality. Causality may be reverse or confounding and large choline intake might not increase mortality in humans. For example, <a href="/wiki/Kidney_dysfunction" class="mw-redirect" title="Kidney dysfunction">kidney dysfunction</a> predisposes for cardiovascular diseases, but can also decrease TMA and TMAO excretion.<sup id="cite_ref-30" class="reference"><a href="#cite_note-30"><span class="cite-bracket">[</span>29<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Health_effects">Health effects</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Choline&action=edit&section=21" title="Edit section: Health effects"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Neural_tube_closure">Neural tube closure</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Choline&action=edit&section=22" title="Edit section: Neural tube closure"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Low maternal intake of choline is associated with an increased risk of <a href="/wiki/Neural_tube_defect" title="Neural tube defect">neural tube defects</a>. Higher maternal intake of choline is likely associated with better neurocognition/neurodevelopment in children.<sup id="cite_ref-31" class="reference"><a href="#cite_note-31"><span class="cite-bracket">[</span>30<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-lpi_4-17" class="reference"><a href="#cite_note-lpi-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> Choline and folate, interacting with <a href="/wiki/Vitamin_B12" title="Vitamin B12">vitamin B<sub>12</sub></a>, act as methyl donors to homocysteine to form methionine, which can then go on to form SAM (<i>S</i>-adenosylmethionine).<sup id="cite_ref-lpi_4-18" class="reference"><a href="#cite_note-lpi-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> SAM is the substrate for almost all methylation reactions in mammals. It has been suggested that disturbed methylation via SAM could be responsible for the relation between folate and NTDs.<sup id="cite_ref-32" class="reference"><a href="#cite_note-32"><span class="cite-bracket">[</span>31<span class="cite-bracket">]</span></a></sup> This may also apply to choline.<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (January 2020)">citation needed</span></a></i>]</sup> Certain <a href="/wiki/Mutation" title="Mutation">mutations</a> that disturb choline metabolism increase the prevalence of NTDs in newborns, but the role of dietary choline deficiency remains unclear, as of 2015.<sup class="plainlinks noexcerpt noprint asof-tag update" style="display:none;"><a class="external text" href="https://en.wikipedia.org/w/index.php?title=Choline&action=edit">[update]</a></sup><sup id="cite_ref-lpi_4-19" class="reference"><a href="#cite_note-lpi-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Cardiovascular_diseases_and_cancer">Cardiovascular diseases and cancer</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Choline&action=edit&section=23" title="Edit section: Cardiovascular diseases and cancer"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Choline deficiency can cause <a href="/wiki/Fatty_liver" class="mw-redirect" title="Fatty liver">fatty liver</a>, which increases cancer and cardiovascular disease risk. Choline deficiency also decreases SAM production, which partakes in <a href="/wiki/DNA_methylation" title="DNA methylation">DNA methylation</a> – this decrease may also contribute to <a href="/wiki/Carcinogenesis" title="Carcinogenesis">carcinogenesis</a>. Thus, deficiency and its association with such diseases has been studied.<sup id="cite_ref-eu_6-28" class="reference"><a href="#cite_note-eu-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> However, <a href="/wiki/Observational_studies" class="mw-redirect" title="Observational studies">observational studies</a> of free populations have not convincingly shown an association between low choline intake and cardiovascular diseases or most cancers.<sup id="cite_ref-lpi_4-20" class="reference"><a href="#cite_note-lpi-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-eu_6-29" class="reference"><a href="#cite_note-eu-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> Studies on <a href="/wiki/Prostate_cancer" title="Prostate cancer">prostate cancer</a> have been contradictory.<sup id="cite_ref-33" class="reference"><a href="#cite_note-33"><span class="cite-bracket">[</span>32<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-34" class="reference"><a href="#cite_note-34"><span class="cite-bracket">[</span>33<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Cognition">Cognition</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Choline&action=edit&section=24" title="Edit section: Cognition"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Studies observing the effect between higher choline intake and <a href="/wiki/Cognition" title="Cognition">cognition</a> have been conducted in human adults, with contradictory results.<sup id="cite_ref-lpi_4-21" class="reference"><a href="#cite_note-lpi-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-35" class="reference"><a href="#cite_note-35"><span class="cite-bracket">[</span>34<span class="cite-bracket">]</span></a></sup> Similar studies on human infants and children have been contradictory and also limited.<sup id="cite_ref-lpi_4-22" class="reference"><a href="#cite_note-lpi-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Perinatal_development">Perinatal development</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Choline&action=edit&section=25" title="Edit section: Perinatal development"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1251242444"><table class="box-More_citations_needed_section plainlinks metadata ambox ambox-content ambox-Refimprove" role="presentation"><tbody><tr><td class="mbox-image"><div class="mbox-image-div"><span typeof="mw:File"><a href="/wiki/File:Question_book-new.svg" class="mw-file-description"><img alt="" src="//upload.wikimedia.org/wikipedia/en/thumb/9/99/Question_book-new.svg/50px-Question_book-new.svg.png" decoding="async" width="50" height="39" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/9/99/Question_book-new.svg/75px-Question_book-new.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/9/99/Question_book-new.svg/100px-Question_book-new.svg.png 2x" data-file-width="512" data-file-height="399" /></a></span></div></td><td class="mbox-text"><div class="mbox-text-span">This section <b>needs additional citations for <a href="/wiki/Wikipedia:Verifiability" title="Wikipedia:Verifiability">verification</a></b>.<span class="hide-when-compact"> Please help <a href="/wiki/Special:EditPage/Choline" title="Special:EditPage/Choline">improve this article</a> by <a href="/wiki/Help:Referencing_for_beginners" title="Help:Referencing for beginners">adding citations to reliable sources</a> in this section. Unsourced material may be challenged and removed.</span> <span class="date-container"><i>(<span class="date">December 2016</span>)</i></span><span class="hide-when-compact"><i> (<small><a href="/wiki/Help:Maintenance_template_removal" title="Help:Maintenance template removal">Learn how and when to remove this message</a></small>)</i></span></div></td></tr></tbody></table> <p>Both pregnancy and lactation increase demand for choline dramatically. This demand may be met by upregulation of <a href="/wiki/Phosphatidyl_ethanolamine_methyltransferase" class="mw-redirect" title="Phosphatidyl ethanolamine methyltransferase">PEMT</a> via increasing <a href="/wiki/Estrogen" title="Estrogen">estrogen</a> levels to produce more choline <i>de novo</i>, but even with increased PEMT activity, the demand for choline is still so high that bodily stores are generally depleted. This is exemplified by the observation that <i>Pemt −/−</i> mice (mice lacking functional PEMT) will abort at 9–10 days unless fed supplemental choline.<sup id="cite_ref-Zeisel,_SH._Choline_2006_36-0" class="reference"><a href="#cite_note-Zeisel,_SH._Choline_2006-36"><span class="cite-bracket">[</span>35<span class="cite-bracket">]</span></a></sup> </p><p>While maternal stores of choline are depleted during pregnancy and lactation, the placenta accumulates choline by pumping choline against the concentration gradient into the tissue, where it is then stored in various forms, mostly as acetylcholine. Choline concentrations in <a href="/wiki/Amniotic_fluid" title="Amniotic fluid">amniotic fluid</a> can be ten times higher than in maternal blood.<sup id="cite_ref-Zeisel,_SH._Choline_2006_36-1" class="reference"><a href="#cite_note-Zeisel,_SH._Choline_2006-36"><span class="cite-bracket">[</span>35<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Functions_in_the_fetus">Functions in the fetus</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Choline&action=edit&section=26" title="Edit section: Functions in the fetus"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Choline is in high demand during pregnancy as a substrate for building <a href="/wiki/Cellular_membrane" class="mw-redirect" title="Cellular membrane">cellular membranes</a> (rapid fetal and mother tissue expansion), increased need for one-carbon <a href="/wiki/Moiety_(chemistry)" title="Moiety (chemistry)">moieties</a> (a substrate for methylation of DNA and other functions), raising choline stores in fetal and placental tissues, and for increased production of lipoproteins (proteins containing "fat" portions).<sup id="cite_ref-37" class="reference"><a href="#cite_note-37"><span class="cite-bracket">[</span>36<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-38" class="reference"><a href="#cite_note-38"><span class="cite-bracket">[</span>37<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-39" class="reference"><a href="#cite_note-39"><span class="cite-bracket">[</span>38<span class="cite-bracket">]</span></a></sup> In particular, there is interest in the impact of choline consumption on the brain. This stems from choline's use as a material for making cellular membranes (particularly in making phosphatidylcholine). Human brain growth is most rapid during the <a href="/wiki/Third_trimester" class="mw-redirect" title="Third trimester">third trimester</a> of pregnancy and continues to be rapid to approximately five years of age.<sup id="cite_ref-40" class="reference"><a href="#cite_note-40"><span class="cite-bracket">[</span>39<span class="cite-bracket">]</span></a></sup> During this time, the demand is high for sphingomyelin, which is made from phosphatidylcholine (and thus from choline), because this material is used to <a href="/wiki/Myelinated_nerve_fibers" class="mw-redirect" title="Myelinated nerve fibers">myelinate</a> (insulate) <a href="/wiki/Nerve_fiber" class="mw-redirect" title="Nerve fiber">nerve fibers</a>.<sup id="cite_ref-41" class="reference"><a href="#cite_note-41"><span class="cite-bracket">[</span>40<span class="cite-bracket">]</span></a></sup> Choline is also in demand for the production of the neurotransmitter acetylcholine, which can influence the structure and organization of brain regions, <a href="/wiki/Neurogenesis" title="Neurogenesis">neurogenesis</a>, myelination, and <a href="/wiki/Synapse" title="Synapse">synapse</a> formation. Acetylcholine is even present in the placenta and may help control <a href="/wiki/Cell_proliferation" title="Cell proliferation">cell proliferation</a> and <a href="/wiki/Cell_differentiation" class="mw-redirect" title="Cell differentiation">differentiation</a> (increases in cell number and changes of multiuse cells into dedicated cellular functions) and <a href="/wiki/Parturition" class="mw-redirect" title="Parturition">parturition</a>.<sup id="cite_ref-42" class="reference"><a href="#cite_note-42"><span class="cite-bracket">[</span>41<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-43" class="reference"><a href="#cite_note-43"><span class="cite-bracket">[</span>42<span class="cite-bracket">]</span></a></sup> </p><p>Choline uptake into the brain is controlled by a low-affinity transporter located at the blood–brain barrier.<sup id="cite_ref-44" class="reference"><a href="#cite_note-44"><span class="cite-bracket">[</span>43<span class="cite-bracket">]</span></a></sup> Transport occurs when arterial blood plasma choline concentrations increase above 14 μmol/L, which can occur during a spike in choline concentration after consuming choline-rich foods. Neurons, conversely, acquire choline by both high- and low-affinity transporters. Choline is stored as membrane-bound phosphatidylcholine, which can then be used for acetylcholine neurotransmitter synthesis later. Acetylcholine is formed as needed, travels across the synapse, and transmits the signal to the following neuron. Afterwards, <a href="/wiki/Acetylcholinesterase" title="Acetylcholinesterase">acetylcholinesterase</a> degrades it, and the free choline is taken up by a high-affinity transporter into the neuron again.<sup id="cite_ref-45" class="reference"><a href="#cite_note-45"><span class="cite-bracket">[</span>44<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Uses">Uses</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Choline&action=edit&section=27" title="Edit section: Uses"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Choline <a href="/wiki/Chloride" title="Chloride">chloride</a> and choline <a href="/wiki/Bitartrate" title="Bitartrate">bitartrate</a> are used in <a href="/wiki/Dietary_supplement" title="Dietary supplement">dietary supplements</a>. Bitartrate is used more often due to its lower hygroscopicity.<sup id="cite_ref-ze_3-11" class="reference"><a href="#cite_note-ze-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> Certain choline salts are used to supplement chicken, turkey and some other <a href="/wiki/Animal_feed" title="Animal feed">animal feeds</a>. Some salts are also used as industrial chemicals: for example, in <a href="/wiki/Photolithography" title="Photolithography">photolithography</a> to remove <a href="/wiki/Photoresist" title="Photoresist">photoresist</a>.<sup id="cite_ref-Kirk_2000_2-7" class="reference"><a href="#cite_note-Kirk_2000-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> <a href="/wiki/Choline_theophyllinate" title="Choline theophyllinate">Choline theophyllinate</a> and choline <a href="/wiki/Salicylate" class="mw-redirect" title="Salicylate">salicylate</a> are used as medicines,<sup id="cite_ref-Kirk_2000_2-8" class="reference"><a href="#cite_note-Kirk_2000-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-46" class="reference"><a href="#cite_note-46"><span class="cite-bracket">[</span>45<span class="cite-bracket">]</span></a></sup> as well as <a href="/wiki/Structural_analog" title="Structural analog">structural analogs</a>, like <a href="/wiki/Methacholine" title="Methacholine">methacholine</a> and <a href="/wiki/Carbachol" title="Carbachol">carbachol</a>.<sup id="cite_ref-KOECT_47-0" class="reference"><a href="#cite_note-KOECT-47"><span class="cite-bracket">[</span>46<span class="cite-bracket">]</span></a></sup> <a href="/wiki/Radiolabeled" class="mw-redirect" title="Radiolabeled">Radiolabeled</a> cholines, like <a href="/wiki/Carbon-11-choline" title="Carbon-11-choline"><sup>11</sup>C-choline</a>, are used in <a href="/wiki/Medical_imaging" title="Medical imaging">medical imaging</a>.<sup id="cite_ref-48" class="reference"><a href="#cite_note-48"><span class="cite-bracket">[</span>47<span class="cite-bracket">]</span></a></sup> Other commercially used salts include tricholine <a href="/wiki/Citrate" class="mw-redirect" title="Citrate">citrate</a> and choline <a href="/wiki/Bicarbonate" title="Bicarbonate">bicarbonate</a>.<sup id="cite_ref-Kirk_2000_2-9" class="reference"><a href="#cite_note-Kirk_2000-2"><span class="cite-bracket">[</span>2<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=Choline&action=edit&section=28" title="Edit section: History"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Discovery">Discovery</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Choline&action=edit&section=29" title="Edit section: Discovery"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>In 1849, <a href="/wiki/Adolph_Strecker" title="Adolph Strecker">Adolph Strecker</a> was the first to isolate choline from pig bile.<sup id="cite_ref-49" class="reference"><a href="#cite_note-49"><span class="cite-bracket">[</span>48<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Sebrell_1971_50-0" class="reference"><a href="#cite_note-Sebrell_1971-50"><span class="cite-bracket">[</span>49<span class="cite-bracket">]</span></a></sup> In 1852, L. Babo and M. Hirschbrunn extracted choline from <a href="/wiki/White_mustard" title="White mustard">white mustard</a> seeds and named it <i>sinkaline</i>.<sup id="cite_ref-Sebrell_1971_50-1" class="reference"><a href="#cite_note-Sebrell_1971-50"><span class="cite-bracket">[</span>49<span class="cite-bracket">]</span></a></sup> In 1862, Strecker repeated his experiment with pig and ox bile, calling the substance <i>choline</i> for the first time after the Greek word for bile, <i>chole</i>, and identifying it with the <a href="/wiki/Chemical_formula" title="Chemical formula">chemical formula</a> C<sub>5</sub>H<sub>13</sub>NO.<sup id="cite_ref-Strecker_1862_51-0" class="reference"><a href="#cite_note-Strecker_1862-51"><span class="cite-bracket">[</span>50<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-his_12-1" class="reference"><a href="#cite_note-his-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup> In 1850, <a href="/wiki/Theodore_Nicolas_Gobley" class="mw-redirect" title="Theodore Nicolas Gobley">Theodore Nicolas Gobley</a> extracted from the brains and <a href="/wiki/Roe" title="Roe">roe</a> of <a href="/wiki/Carp" title="Carp">carps</a> a substance he named <i>lecithin</i> after the Greek word for egg <a href="/wiki/Yolk" title="Yolk">yolk</a>, <span title="Greek-language romanization"><i lang="el-Latn">lekithos</i></span>, showing in 1874 that it was a mixture of <a href="/wiki/Phosphatidylcholines" class="mw-redirect" title="Phosphatidylcholines">phosphatidylcholines</a>.<sup id="cite_ref-52" class="reference"><a href="#cite_note-52"><span class="cite-bracket">[</span>51<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-53" class="reference"><a href="#cite_note-53"><span class="cite-bracket">[</span>52<span class="cite-bracket">]</span></a></sup> </p><p>In 1865, <a href="/wiki/Oscar_Liebreich" title="Oscar Liebreich">Oscar Liebreich</a> isolated "<i>neurine</i>" from animal brains.<sup id="cite_ref-54" class="reference"><a href="#cite_note-54"><span class="cite-bracket">[</span>53<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-his_12-2" class="reference"><a href="#cite_note-his-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup> The <a href="/wiki/Structural_formula" title="Structural formula">structural formulas</a> of acetylcholine and Liebreich's "neurine" were resolved by <a href="/wiki/Adolf_von_Baeyer" title="Adolf von Baeyer">Adolf von Baeyer</a> in 1867.<sup id="cite_ref-b_55-0" class="reference"><a href="#cite_note-b-55"><span class="cite-bracket">[</span>54<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Sebrell_1971_50-2" class="reference"><a href="#cite_note-Sebrell_1971-50"><span class="cite-bracket">[</span>49<span class="cite-bracket">]</span></a></sup> Later that year "neurine" and sinkaline were shown to be the same substances as Strecker's choline. Thus, Bayer was the first to resolve the structure of choline.<sup id="cite_ref-56" class="reference"><a href="#cite_note-56"><span class="cite-bracket">[</span>55<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-57" class="reference"><a href="#cite_note-57"><span class="cite-bracket">[</span>56<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Sebrell_1971_50-3" class="reference"><a href="#cite_note-Sebrell_1971-50"><span class="cite-bracket">[</span>49<span class="cite-bracket">]</span></a></sup> The compound now known as <a href="/wiki/Neurine" title="Neurine">neurine</a> is unrelated to choline.<sup id="cite_ref-his_12-3" class="reference"><a href="#cite_note-his-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Discovery_as_a_nutrient">Discovery as a nutrient</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Choline&action=edit&section=30" title="Edit section: Discovery as a nutrient"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>In the early 1930s, <a href="/wiki/Charles_Best_(medical_scientist)" title="Charles Best (medical scientist)">Charles Best</a> and colleagues noted that fatty liver in rats on a special diet and <a href="/wiki/Diabetic" class="mw-redirect" title="Diabetic">diabetic</a> dogs could be prevented by feeding them lecithin,<sup id="cite_ref-his_12-4" class="reference"><a href="#cite_note-his-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup> proving in 1932 that choline in lecithin was solely responsible for this preventive effect.<sup id="cite_ref-58" class="reference"><a href="#cite_note-58"><span class="cite-bracket">[</span>57<span class="cite-bracket">]</span></a></sup> In 1998, the US National Academy of Medicine reported their first recommendations for choline in the human diet.<sup id="cite_ref-59" class="reference"><a href="#cite_note-59"><span class="cite-bracket">[</span>58<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=Choline&action=edit&section=31" title="Edit section: References"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239543626"><div class="reflist reflist-lower-alpha"> </div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239543626"><div class="reflist"> <div class="mw-references-wrap mw-references-columns"><ol class="references"> <li id="cite_note-pubchem-1"><span class="mw-cite-backlink">^ <a href="#cite_ref-pubchem_1-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-pubchem_1-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-pubchem_1-2"><sup><i><b>c</b></i></sup></a></span> <span class="reference-text"><style data-mw-deduplicate="TemplateStyles:r1238218222">.mw-parser-output cite.citation{font-style:inherit;word-wrap:break-word}.mw-parser-output .citation q{quotes:"\"""\"""'""'"}.mw-parser-output .citation:target{background-color:rgba(0,127,255,0.133)}.mw-parser-output .id-lock-free.id-lock-free a{background:url("//upload.wikimedia.org/wikipedia/commons/6/65/Lock-green.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-limited.id-lock-limited a,.mw-parser-output .id-lock-registration.id-lock-registration a{background:url("//upload.wikimedia.org/wikipedia/commons/d/d6/Lock-gray-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-subscription.id-lock-subscription a{background:url("//upload.wikimedia.org/wikipedia/commons/a/aa/Lock-red-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .cs1-ws-icon a{background:url("//upload.wikimedia.org/wikipedia/commons/4/4c/Wikisource-logo.svg")right 0.1em center/12px no-repeat}body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-free a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-limited a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-registration a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-subscription a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .cs1-ws-icon a{background-size:contain;padding:0 1em 0 0}.mw-parser-output .cs1-code{color:inherit;background:inherit;border:none;padding:inherit}.mw-parser-output .cs1-hidden-error{display:none;color:var(--color-error,#d33)}.mw-parser-output .cs1-visible-error{color:var(--color-error,#d33)}.mw-parser-output .cs1-maint{display:none;color:#085;margin-left:0.3em}.mw-parser-output .cs1-kern-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right{padding-right:0.2em}.mw-parser-output .citation .mw-selflink{font-weight:inherit}@media screen{.mw-parser-output .cs1-format{font-size:95%}html.skin-theme-clientpref-night .mw-parser-output .cs1-maint{color:#18911f}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .cs1-maint{color:#18911f}}</style><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/Choline">"Choline"</a>. PubChem, National Library of Medicine, US National Institutes of Health. 26 October 2024<span class="reference-accessdate">. Retrieved <span class="nowrap">31 October</span> 2024</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=Choline&rft.pub=PubChem%2C+National+Library+of+Medicine%2C+US+National+Institutes+of+Health&rft.date=2024-10-26&rft_id=https%3A%2F%2Fpubchem.ncbi.nlm.nih.gov%2Fcompound%2FCholine&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACholine" class="Z3988"></span></span> </li> <li id="cite_note-Kirk_2000-2"><span class="mw-cite-backlink">^ <a href="#cite_ref-Kirk_2000_2-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Kirk_2000_2-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-Kirk_2000_2-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-Kirk_2000_2-3"><sup><i><b>d</b></i></sup></a> <a href="#cite_ref-Kirk_2000_2-4"><sup><i><b>e</b></i></sup></a> <a href="#cite_ref-Kirk_2000_2-5"><sup><i><b>f</b></i></sup></a> <a href="#cite_ref-Kirk_2000_2-6"><sup><i><b>g</b></i></sup></a> <a href="#cite_ref-Kirk_2000_2-7"><sup><i><b>h</b></i></sup></a> <a href="#cite_ref-Kirk_2000_2-8"><sup><i><b>i</b></i></sup></a> <a href="#cite_ref-Kirk_2000_2-9"><sup><i><b>j</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFKirk2000" class="citation book cs1">Kirk RE, et al. (2000). <i>Kirk-Othmer encyclopedia of chemical technology</i>. Vol. 6 (4th ed.). John Wiley & Sons. pp. 100–102. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/9780471484943" title="Special:BookSources/9780471484943"><bdi>9780471484943</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Kirk-Othmer+encyclopedia+of+chemical+technology&rft.pages=100-102&rft.edition=4th&rft.pub=John+Wiley+%26+Sons&rft.date=2000&rft.isbn=9780471484943&rft.aulast=Kirk&rft.aufirst=RE&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACholine" class="Z3988"></span></span> </li> <li id="cite_note-ze-3"><span class="mw-cite-backlink">^ <a href="#cite_ref-ze_3-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-ze_3-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-ze_3-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-ze_3-3"><sup><i><b>d</b></i></sup></a> <a href="#cite_ref-ze_3-4"><sup><i><b>e</b></i></sup></a> <a href="#cite_ref-ze_3-5"><sup><i><b>f</b></i></sup></a> <a href="#cite_ref-ze_3-6"><sup><i><b>g</b></i></sup></a> <a href="#cite_ref-ze_3-7"><sup><i><b>h</b></i></sup></a> <a href="#cite_ref-ze_3-8"><sup><i><b>i</b></i></sup></a> <a href="#cite_ref-ze_3-9"><sup><i><b>j</b></i></sup></a> <a href="#cite_ref-ze_3-10"><sup><i><b>k</b></i></sup></a> <a href="#cite_ref-ze_3-11"><sup><i><b>l</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFRuckerZempleniSuttieMcCormick2007" class="citation book cs1">Rucker RB, Zempleni J, Suttie JW, et al. (2007). <span class="id-lock-limited" title="Free access subject to limited trial, subscription normally required"><a rel="nofollow" class="external text" href="https://archive.org/details/handbookvitamins00jzem"><i>Handbook of vitamins</i></a></span> (4th ed.). Taylor & Francis. pp. <a rel="nofollow" class="external text" href="https://archive.org/details/handbookvitamins00jzem/page/n471">459</a>–477. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/9780849340222" title="Special:BookSources/9780849340222"><bdi>9780849340222</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Handbook+of+vitamins&rft.pages=459-477&rft.edition=4th&rft.pub=Taylor+%26+Francis&rft.date=2007&rft.isbn=9780849340222&rft.aulast=Rucker&rft.aufirst=RB&rft.au=Zempleni%2C+J&rft.au=Suttie%2C+JW&rft.au=McCormick%2C+DB&rft_id=https%3A%2F%2Farchive.org%2Fdetails%2Fhandbookvitamins00jzem&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACholine" class="Z3988"></span></span> </li> <li id="cite_note-lpi-4"><span class="mw-cite-backlink">^ <a href="#cite_ref-lpi_4-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-lpi_4-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-lpi_4-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-lpi_4-3"><sup><i><b>d</b></i></sup></a> <a href="#cite_ref-lpi_4-4"><sup><i><b>e</b></i></sup></a> <a href="#cite_ref-lpi_4-5"><sup><i><b>f</b></i></sup></a> <a href="#cite_ref-lpi_4-6"><sup><i><b>g</b></i></sup></a> <a href="#cite_ref-lpi_4-7"><sup><i><b>h</b></i></sup></a> <a href="#cite_ref-lpi_4-8"><sup><i><b>i</b></i></sup></a> <a href="#cite_ref-lpi_4-9"><sup><i><b>j</b></i></sup></a> <a href="#cite_ref-lpi_4-10"><sup><i><b>k</b></i></sup></a> <a href="#cite_ref-lpi_4-11"><sup><i><b>l</b></i></sup></a> <a href="#cite_ref-lpi_4-12"><sup><i><b>m</b></i></sup></a> <a href="#cite_ref-lpi_4-13"><sup><i><b>n</b></i></sup></a> <a href="#cite_ref-lpi_4-14"><sup><i><b>o</b></i></sup></a> <a href="#cite_ref-lpi_4-15"><sup><i><b>p</b></i></sup></a> <a href="#cite_ref-lpi_4-16"><sup><i><b>q</b></i></sup></a> <a href="#cite_ref-lpi_4-17"><sup><i><b>r</b></i></sup></a> <a href="#cite_ref-lpi_4-18"><sup><i><b>s</b></i></sup></a> <a href="#cite_ref-lpi_4-19"><sup><i><b>t</b></i></sup></a> <a href="#cite_ref-lpi_4-20"><sup><i><b>u</b></i></sup></a> <a href="#cite_ref-lpi_4-21"><sup><i><b>v</b></i></sup></a> <a href="#cite_ref-lpi_4-22"><sup><i><b>w</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://lpi.oregonstate.edu/mic/other-nutrients/choline">"Choline"</a>. Micronutrient Information Center, Linus Pauling Institute, Oregon State University, Corvallis. July 2023<span class="reference-accessdate">. Retrieved <span class="nowrap">31 October</span> 2024</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=Choline&rft.pub=Micronutrient+Information+Center%2C+Linus+Pauling+Institute%2C+Oregon+State+University%2C+Corvallis&rft.date=2023-07&rft_id=https%3A%2F%2Flpi.oregonstate.edu%2Fmic%2Fother-nutrients%2Fcholine&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACholine" class="Z3988"></span></span> </li> <li id="cite_note-ods-5"><span class="mw-cite-backlink">^ <a href="#cite_ref-ods_5-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-ods_5-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-ods_5-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-ods_5-3"><sup><i><b>d</b></i></sup></a> <a href="#cite_ref-ods_5-4"><sup><i><b>e</b></i></sup></a> <a href="#cite_ref-ods_5-5"><sup><i><b>f</b></i></sup></a> <a href="#cite_ref-ods_5-6"><sup><i><b>g</b></i></sup></a> <a href="#cite_ref-ods_5-7"><sup><i><b>h</b></i></sup></a> <a href="#cite_ref-ods_5-8"><sup><i><b>i</b></i></sup></a> <a href="#cite_ref-ods_5-9"><sup><i><b>j</b></i></sup></a> <a href="#cite_ref-ods_5-10"><sup><i><b>k</b></i></sup></a> <a href="#cite_ref-ods_5-11"><sup><i><b>l</b></i></sup></a> <a href="#cite_ref-ods_5-12"><sup><i><b>m</b></i></sup></a> <a href="#cite_ref-ods_5-13"><sup><i><b>n</b></i></sup></a> <a href="#cite_ref-ods_5-14"><sup><i><b>o</b></i></sup></a> <a href="#cite_ref-ods_5-15"><sup><i><b>p</b></i></sup></a> <a href="#cite_ref-ods_5-16"><sup><i><b>q</b></i></sup></a> <a href="#cite_ref-ods_5-17"><sup><i><b>r</b></i></sup></a> <a href="#cite_ref-ods_5-18"><sup><i><b>s</b></i></sup></a> <a href="#cite_ref-ods_5-19"><sup><i><b>t</b></i></sup></a> <a href="#cite_ref-ods_5-20"><sup><i><b>u</b></i></sup></a> <a href="#cite_ref-ods_5-21"><sup><i><b>v</b></i></sup></a> <a href="#cite_ref-ods_5-22"><sup><i><b>w</b></i></sup></a> <a href="#cite_ref-ods_5-23"><sup><i><b>x</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://ods.od.nih.gov/factsheets/Choline-HealthProfessional/">"Choline"</a>. Office of Dietary Supplements, US National Institutes of Health. 2 June 2022<span class="reference-accessdate">. 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title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=J+Prakt+Chem&rft.atitle=%C3%9Ceber+neurin+und+sinkalin&rft.volume=102&rft.issue=1&rft.pages=24-27&rft.date=1867&rft_id=info%3Adoi%2F10.1002%2Fprac.18671020104&rft.aulast=Claus&rft.aufirst=A&rft.au=Kees%C3%A9%2C+C&rft_id=https%3A%2F%2Fzenodo.org%2Frecord%2F2464361&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACholine" class="Z3988"></span></span> </li> <li id="cite_note-58"><span class="mw-cite-backlink"><b><a href="#cite_ref-58">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFBestHersheyHuntsman1932" class="citation journal cs1">Best CH, Hershey JM, Huntsman ME (May 1932). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1394511">"The effect of lecithine on fat deposition in the liver of the normal rat"</a>. <i>The Journal of Physiology</i>. <b>75</b> (1): 56–66. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1113%2Fjphysiol.1932.sp002875">10.1113/jphysiol.1932.sp002875</a>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1394511">1394511</a></span>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/16994301">16994301</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=The+Journal+of+Physiology&rft.atitle=The+effect+of+lecithine+on+fat+deposition+in+the+liver+of+the+normal+rat&rft.volume=75&rft.issue=1&rft.pages=56-66&rft.date=1932-05&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC1394511%23id-name%3DPMC&rft_id=info%3Apmid%2F16994301&rft_id=info%3Adoi%2F10.1113%2Fjphysiol.1932.sp002875&rft.aulast=Best&rft.aufirst=CH&rft.au=Hershey%2C+JM&rft.au=Huntsman%2C+ME&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC1394511&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACholine" class="Z3988"></span></span> </li> <li id="cite_note-59"><span class="mw-cite-backlink"><b><a href="#cite_ref-59">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation book cs1">"Choline". <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/books/NBK114308/"><i>Institute of Medicine (US) Standing Committee on the scientific evaluation of dietary reference intakes and its panel on folate, other B. vitamins, and choline</i></a>. National Academies Press (US). 1998. pp. xi, 402–413. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/9780309064118" title="Special:BookSources/9780309064118"><bdi>9780309064118</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Choline&rft.btitle=Institute+of+Medicine+%28US%29+Standing+Committee+on+the+scientific+evaluation+of+dietary+reference+intakes+and+its+panel+on+folate%2C+other+B.+vitamins%2C+and+choline&rft.pages=xi%2C+402-413&rft.pub=National+Academies+Press+%28US%29&rft.date=1998&rft.isbn=9780309064118&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fbooks%2FNBK114308%2F&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACholine" class="Z3988"></span></span> </li> </ol></div></div> <div class="navbox-styles"><style data-mw-deduplicate="TemplateStyles:r1129693374">.mw-parser-output .hlist dl,.mw-parser-output .hlist ol,.mw-parser-output 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.navbar{display:none!important}}</style><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template: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_supplements" 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 href="/wiki/Pantothenic_acid" title="Pantothenic acid">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 class="mw-selflink selflink">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:r1236075235"></div><div role="navigation" class="navbox" aria-labelledby="Acetylcholine_receptor_modulators" style="padding:3px"><table class="nowraplinks mw-collapsible mw-collapsed navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2" style="background:#e8e8ff;"><div id="Acetylcholine_receptor_modulators" style="font-size:114%;margin:0 4em"><a href="/wiki/Acetylcholine_receptor" title="Acetylcholine receptor">Acetylcholine receptor</a> <a href="/wiki/Receptor_modulator" title="Receptor modulator">modulators</a></div></th></tr><tr><td colspan="2" class="navbox-list navbox-odd" style="width:100%;padding:0;font-size:114%"><div style="padding:0px"> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"></div><div role="navigation" class="navbox" aria-labelledby="Muscarinic_acetylcholine_receptor_modulators" style="padding:3px"><table class="nowraplinks hlist mw-collapsible mw-collapsed navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Muscarinic_acetylcholine_receptor_modulators" title="Template:Muscarinic acetylcholine receptor modulators"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Muscarinic_acetylcholine_receptor_modulators" title="Template talk:Muscarinic acetylcholine receptor modulators"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Muscarinic_acetylcholine_receptor_modulators" title="Special:EditPage/Template:Muscarinic acetylcholine receptor modulators"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Muscarinic_acetylcholine_receptor_modulators" style="font-size:114%;margin:0 4em"><a href="/wiki/Muscarinic_acetylcholine_receptor" title="Muscarinic acetylcholine receptor">Muscarinic acetylcholine receptor</a> <a href="/wiki/Receptor_modulator" title="Receptor modulator">modulators</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Muscarinic_acetylcholine_receptors" class="mw-redirect" title="Muscarinic acetylcholine receptors"><abbr title="Muscarinic acetylcholine receptors">mAChRs</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Muscarinic acetylcholine receptors</span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Muscarinic_agonist" title="Muscarinic agonist">Agonists</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/77-LH-28-1" title="77-LH-28-1">77-LH-28-1</a></li> <li><a href="/wiki/AC-42" title="AC-42">AC-42</a></li> <li><a href="/w/index.php?title=AC-260,584&action=edit&redlink=1" class="new" title="AC-260,584 (page does not exist)">AC-260,584</a></li> <li><a href="/wiki/Aceclidine" title="Aceclidine">Aceclidine</a></li> <li><a href="/wiki/Acetylcholine" title="Acetylcholine">Acetylcholine</a></li> <li><a href="/w/index.php?title=AF30&action=edit&redlink=1" class="new" title="AF30 (page does not exist)">AF30</a></li> <li><a href="/w/index.php?title=AF150(S)&action=edit&redlink=1" class="new" title="AF150(S) (page does not exist)">AF150(S)</a></li> <li><a href="/w/index.php?title=AF267B&action=edit&redlink=1" class="new" title="AF267B (page does not exist)">AF267B</a></li> <li><a href="/wiki/Alvameline" title="Alvameline">Alvameline</a></li> <li><a href="/w/index.php?title=AQRA-741&action=edit&redlink=1" class="new" title="AQRA-741 (page does not exist)">AQRA-741</a></li> <li><a href="/wiki/Arecoline" title="Arecoline">Arecoline</a></li> <li><a href="/wiki/Bethanechol" title="Bethanechol">Bethanechol</a></li> <li><a href="/wiki/Butyrylcholine" title="Butyrylcholine">Butyrylcholine</a></li> <li><a href="/wiki/Carbachol" title="Carbachol">Carbachol</a></li> <li><a href="/w/index.php?title=CDD-0034&action=edit&redlink=1" class="new" title="CDD-0034 (page does not exist)">CDD-0034</a></li> <li><a href="/w/index.php?title=CDD-0078&action=edit&redlink=1" class="new" title="CDD-0078 (page does not exist)">CDD-0078</a></li> <li><a href="/w/index.php?title=CDD-0097&action=edit&redlink=1" class="new" title="CDD-0097 (page does not exist)">CDD-0097</a></li> <li><a href="/w/index.php?title=CDD-0098&action=edit&redlink=1" class="new" title="CDD-0098 (page does not exist)">CDD-0098</a></li> <li><a href="/w/index.php?title=CDD-0102&action=edit&redlink=1" class="new" title="CDD-0102 (page does not exist)">CDD-0102</a></li> <li><a href="/wiki/Cevimeline" title="Cevimeline">Cevimeline</a></li> <li><a class="mw-selflink selflink">Choline</a></li> <li><a href="/wiki/Cis-Dioxolane" class="mw-redirect" title="Cis-Dioxolane">cis-Dioxolane</a></li> <li><a href="/wiki/Clozapine" title="Clozapine">Clozapine</a></li> <li><a href="/wiki/Desmethylclozapine" title="Desmethylclozapine">Desmethylclozapine (norclozapine)</a></li> <li><a href="/w/index.php?title=Ethoxysebacylcholine&action=edit&redlink=1" class="new" title="Ethoxysebacylcholine (page does not exist)">Ethoxysebacylcholine</a></li> <li><a href="/wiki/Itameline" title="Itameline">Itameline</a></li> <li><a href="/w/index.php?title=LY-593,039&action=edit&redlink=1" class="new" title="LY-593,039 (page does not exist)">LY-593,039</a></li> <li><a href="/w/index.php?title=L-689,660&action=edit&redlink=1" class="new" title="L-689,660 (page does not exist)">L-689,660</a></li> <li><a href="/w/index.php?title=LY-2,033,298&action=edit&redlink=1" class="new" title="LY-2,033,298 (page does not exist)">LY-2,033,298</a></li> <li><a href="/w/index.php?title=McNA343&action=edit&redlink=1" class="new" title="McNA343 (page does not exist)">McNA343</a></li> <li><a href="/wiki/Methacholine" title="Methacholine">Methacholine</a></li> <li><a href="/wiki/Milameline" title="Milameline">Milameline</a></li> <li><a href="/wiki/Muscarine" title="Muscarine">Muscarine</a></li> <li><a href="/w/index.php?title=NGX-267&action=edit&redlink=1" class="new" title="NGX-267 (page does not exist)">NGX-267</a></li> <li><a href="/w/index.php?title=Ocvimeline&action=edit&redlink=1" class="new" title="Ocvimeline (page does not exist)">Ocvimeline</a></li> <li><a href="/wiki/Oxotremorine" title="Oxotremorine">Oxotremorine</a></li> <li><a href="/w/index.php?title=PD-151,832&action=edit&redlink=1" class="new" title="PD-151,832 (page does not exist)">PD-151,832</a></li> <li><a href="/wiki/Pilocarpine" title="Pilocarpine">Pilocarpine</a></li> <li><a href="/w/index.php?title=RS86&action=edit&redlink=1" class="new" title="RS86 (page does not exist)">RS86</a></li> <li><a href="/wiki/Sabcomeline" title="Sabcomeline">Sabcomeline</a></li> <li><a href="/w/index.php?title=SDZ_210-086&action=edit&redlink=1" class="new" title="SDZ 210-086 (page does not exist)">SDZ 210-086</a></li> <li><a href="/w/index.php?title=Sebacylcholine&action=edit&redlink=1" class="new" title="Sebacylcholine (page does not exist)">Sebacylcholine</a></li> <li><a href="/w/index.php?title=Suberyldicholine&action=edit&redlink=1" class="new" title="Suberyldicholine (page does not exist)">Suberyldicholine</a></li> <li><a href="/wiki/Talsaclidine" title="Talsaclidine">Talsaclidine</a></li> <li><a href="/wiki/Tazomeline" title="Tazomeline">Tazomeline</a></li> <li><a href="/w/index.php?title=Thiopilocarpine&action=edit&redlink=1" class="new" title="Thiopilocarpine (page does not exist)">Thiopilocarpine</a></li> <li><a href="/wiki/Vedaclidine" title="Vedaclidine">Vedaclidine</a></li> <li><a href="/w/index.php?title=VU-0029767&action=edit&redlink=1" class="new" title="VU-0029767 (page does not exist)">VU-0029767</a></li> <li><a href="/w/index.php?title=VU-0090157&action=edit&redlink=1" class="new" title="VU-0090157 (page does not exist)">VU-0090157</a></li> <li><a href="/wiki/VU-0152099" title="VU-0152099">VU-0152099</a></li> <li><a href="/wiki/VU-0152100" title="VU-0152100">VU-0152100</a></li> <li><a href="/wiki/VU-0238429" title="VU-0238429">VU-0238429</a></li> <li><a href="/w/index.php?title=WAY-132,983&action=edit&redlink=1" class="new" title="WAY-132,983 (page does not exist)">WAY-132,983</a></li> <li><a href="/wiki/Xanomeline" title="Xanomeline">Xanomeline</a></li> <li><a href="/w/index.php?title=YM-796&action=edit&redlink=1" class="new" title="YM-796 (page does not exist)">YM-796</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Muscarinic_antagonist" title="Muscarinic antagonist">Antagonists</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/3-Quinuclidinyl_benzilate" title="3-Quinuclidinyl benzilate">3-Quinuclidinyl benzilate</a></li> <li><a href="/wiki/4-DAMP" title="4-DAMP">4-DAMP</a></li> <li><a href="/wiki/Aclidinium_bromide" title="Aclidinium bromide">Aclidinium bromide</a> (<a href="/wiki/Aclidinium_bromide/formoterol" title="Aclidinium bromide/formoterol">+formoterol</a>)</li> <li><a href="/wiki/Abediterol" title="Abediterol">Abediterol</a></li> <li><a href="/w/index.php?title=AF-DX_250&action=edit&redlink=1" class="new" title="AF-DX 250 (page does not exist)">AF-DX 250</a></li> <li><a href="/wiki/AFDX-384" title="AFDX-384">AF-DX 384</a></li> <li><a href="/wiki/Ambutonium_bromide" title="Ambutonium bromide">Ambutonium bromide</a></li> <li><a href="/wiki/Anisodamine" title="Anisodamine">Anisodamine</a></li> <li><a href="/wiki/Anisodine" title="Anisodine">Anisodine</a></li> <li><a href="/wiki/First-generation_antihistamine" class="mw-redirect" title="First-generation antihistamine">Antihistamines (first-generation)</a> (e.g., <a href="/wiki/Brompheniramine" title="Brompheniramine">brompheniramine</a>, <a href="/wiki/Buclizine" title="Buclizine">buclizine</a>, <a href="/wiki/Captodiame" title="Captodiame">captodiame</a>, <a href="/wiki/Chlorphenamine" title="Chlorphenamine">chlorphenamine (chlorpheniramine)</a>, <a href="/wiki/Cinnarizine" title="Cinnarizine">cinnarizine</a>, <a href="/wiki/Clemastine" title="Clemastine">clemastine</a>, <a href="/wiki/Cyproheptadine" title="Cyproheptadine">cyproheptadine</a>, <a href="/wiki/Dimenhydrinate" title="Dimenhydrinate">dimenhydrinate</a>, <a href="/wiki/Dimetindene" title="Dimetindene">dimetindene</a>, <a href="/wiki/Diphenhydramine" title="Diphenhydramine">diphenhydramine</a>, <a href="/wiki/Doxylamine" title="Doxylamine">doxylamine</a>, <a href="/wiki/Meclizine" title="Meclizine">meclizine</a>, <a href="/wiki/Mequitazine" title="Mequitazine">mequitazine</a>, <a href="/wiki/Perlapine" title="Perlapine">perlapine</a>, <a href="/wiki/Phenindamine" title="Phenindamine">phenindamine</a>, <a href="/wiki/Pheniramine" title="Pheniramine">pheniramine</a>, <a href="/wiki/Phenyltoloxamine" title="Phenyltoloxamine">phenyltoloxamine</a>, <a href="/wiki/Promethazine" title="Promethazine">promethazine</a>, <a href="/wiki/Propiomazine" title="Propiomazine">propiomazine</a>, <a href="/wiki/Triprolidine" title="Triprolidine">triprolidine</a>)</li> <li><a href="/w/index.php?title=AQ-RA_741&action=edit&redlink=1" class="new" title="AQ-RA 741 (page does not exist)">AQ-RA 741</a></li> <li><a href="/wiki/Atropine" title="Atropine">Atropine</a></li> <li><a href="/wiki/Atropine_methonitrate" class="mw-redirect" title="Atropine methonitrate">Atropine methonitrate</a></li> <li><a href="/wiki/Atypical_antipsychotic" title="Atypical antipsychotic">Atypical antipsychotics</a> (e.g., <a href="/wiki/Clozapine" title="Clozapine">clozapine</a>, <a href="/wiki/Fluperlapine" title="Fluperlapine">fluperlapine</a>, <a href="/wiki/Olanzapine" title="Olanzapine">olanzapine</a> (<a href="/wiki/Olanzapine/fluoxetine" title="Olanzapine/fluoxetine">+fluoxetine</a>), <a href="/w/index.php?title=Rilapine&action=edit&redlink=1" class="new" title="Rilapine (page does not exist)">rilapine</a>, <a href="/wiki/Quetiapine" title="Quetiapine">quetiapine</a>, <a href="/wiki/Tenilapine" title="Tenilapine">tenilapine</a>, <a href="/wiki/Zotepine" title="Zotepine">zotepine</a>)</li> <li><a href="/wiki/Benactyzine" title="Benactyzine">Benactyzine</a></li> <li><a href="/wiki/Benzatropine" title="Benzatropine">Benzatropine (benztropine)</a></li> <li><a href="/wiki/Benzilone" title="Benzilone">Benzilone</a></li> <li><a href="/wiki/Benzilylcholine_mustard" title="Benzilylcholine mustard">Benzilylcholine mustard</a></li> <li><a href="/wiki/Benzydamine" title="Benzydamine">Benzydamine</a></li> <li><a href="/wiki/Bevonium" title="Bevonium">Bevonium</a></li> <li><a href="/w/index.php?title=BIBN_99&action=edit&redlink=1" class="new" title="BIBN 99 (page does not exist)">BIBN 99</a></li> <li><a href="/wiki/Biperiden" title="Biperiden">Biperiden</a></li> <li><a href="/wiki/Bornaprine" title="Bornaprine">Bornaprine</a></li> <li><a href="/wiki/Camylofin" title="Camylofin">Camylofin</a></li> <li><a href="/wiki/CAR-226,086" title="CAR-226,086">CAR-226,086</a></li> <li><a href="/wiki/CAR-301,060" title="CAR-301,060">CAR-301,060</a></li> <li><a href="/wiki/CAR-302,196" title="CAR-302,196">CAR-302,196</a></li> <li><a href="/wiki/CAR-302,282" title="CAR-302,282">CAR-302,282</a></li> <li><a href="/w/index.php?title=CAR-302,368&action=edit&redlink=1" class="new" title="CAR-302,368 (page does not exist)">CAR-302,368</a></li> <li><a href="/w/index.php?title=CAR-302,537&action=edit&redlink=1" class="new" title="CAR-302,537 (page does not exist)">CAR-302,537</a></li> <li><a href="/wiki/CAR-302,668" title="CAR-302,668">CAR-302,668</a></li> <li><a href="/wiki/Caramiphen" title="Caramiphen">Caramiphen</a></li> <li><a href="/wiki/Cimetropium_bromide" title="Cimetropium bromide">Cimetropium bromide</a></li> <li><a href="/wiki/Clidinium_bromide" title="Clidinium bromide">Clidinium bromide</a></li> <li><a href="/wiki/Cloperastine" title="Cloperastine">Cloperastine</a></li> <li><a href="/wiki/CS-27349" title="CS-27349">CS-27349</a></li> <li><a href="/wiki/Cyclobenzaprine" title="Cyclobenzaprine">Cyclobenzaprine</a></li> <li><a href="/wiki/Cyclopentolate" title="Cyclopentolate">Cyclopentolate</a></li> <li><a href="/wiki/Darifenacin" title="Darifenacin">Darifenacin</a></li> <li><a href="/w/index.php?title=DAU-5884&action=edit&redlink=1" class="new" title="DAU-5884 (page does not exist)">DAU-5884</a></li> <li><a href="/wiki/Desfesoterodine" title="Desfesoterodine">Desfesoterodine</a></li> <li><a href="/wiki/Dexetimide" title="Dexetimide">Dexetimide</a></li> <li><a href="/w/index.php?title=DIBD&action=edit&redlink=1" class="new" title="DIBD (page does not exist)">DIBD</a></li> <li><a href="/wiki/Dicycloverine" title="Dicycloverine">Dicycloverine (dicyclomine)</a></li> <li><a href="/wiki/Dihexyverine" title="Dihexyverine">Dihexyverine</a></li> <li><a href="/wiki/Difemerine" title="Difemerine">Difemerine</a></li> <li><a href="/wiki/Diphemanil_metilsulfate" title="Diphemanil metilsulfate">Diphemanil metilsulfate</a></li> <li><a href="/wiki/Ditran" title="Ditran">Ditran</a></li> <li><a href="/wiki/Drofenine" title="Drofenine">Drofenine</a></li> <li><a href="/wiki/EA-3167" title="EA-3167">EA-3167</a></li> <li><a href="/wiki/EA-3443" title="EA-3443">EA-3443</a></li> <li><a href="/wiki/EA-3580" title="EA-3580">EA-3580</a></li> <li><a href="/wiki/EA-3834" title="EA-3834">EA-3834</a></li> <li><a href="/wiki/Emepronium_bromide" title="Emepronium bromide">Emepronium bromide</a></li> <li><a href="/wiki/Etanautine" title="Etanautine">Etanautine</a></li> <li><a href="/wiki/Etybenzatropine" title="Etybenzatropine">Etybenzatropine (ethybenztropine)</a></li> <li><a href="/wiki/Fenpiverinium" title="Fenpiverinium">Fenpiverinium</a></li> <li><a href="/wiki/Fentonium_bromide" title="Fentonium bromide">Fentonium bromide</a></li> <li><a href="/wiki/Fesoterodine" title="Fesoterodine">Fesoterodine</a></li> <li><a href="/wiki/Flavoxate" title="Flavoxate">Flavoxate</a></li> <li><a href="/wiki/Glycopyrronium_bromide" title="Glycopyrronium bromide">Glycopyrronium bromide</a> (<a href="/wiki/Beclometasone/formoterol/glycopyrronium_bromide" title="Beclometasone/formoterol/glycopyrronium bromide">+beclometasone/formoterol</a>, <a href="/wiki/Indacaterol/glycopyrronium_bromide" title="Indacaterol/glycopyrronium bromide">+indacaterol</a>, <a href="/wiki/Neostigmine/glycopyrronium_bromide" title="Neostigmine/glycopyrronium bromide">+neostigmine</a>)</li> <li><a href="/w/index.php?title=Hexahydrodifenidol&action=edit&redlink=1" class="new" title="Hexahydrodifenidol (page does not exist)">Hexahydrodifenidol</a></li> <li><a href="/w/index.php?title=Hexahydrosiladifenidol&action=edit&redlink=1" class="new" title="Hexahydrosiladifenidol (page does not exist)">Hexahydrosiladifenidol</a></li> <li><a href="/w/index.php?title=Hexbutinol&action=edit&redlink=1" class="new" title="Hexbutinol (page does not exist)">Hexbutinol</a></li> <li><a href="/wiki/Hexocyclium" title="Hexocyclium">Hexocyclium</a></li> <li><a href="/wiki/Himbacine" title="Himbacine">Himbacine</a></li> <li><a href="/w/index.php?title=HL-031,120&action=edit&redlink=1" class="new" title="HL-031,120 (page does not exist)">HL-031,120</a></li> <li><a href="/wiki/Homatropine" title="Homatropine">Homatropine</a></li> <li><a href="/wiki/Imidafenacin" title="Imidafenacin">Imidafenacin</a></li> <li><a href="/wiki/Ipratropium_bromide" title="Ipratropium bromide">Ipratropium bromide</a> (<a href="/wiki/Ipratropium_bromide/salbutamol" title="Ipratropium bromide/salbutamol">+salbutamol</a>)</li> <li><a href="/wiki/Isopropamide" title="Isopropamide">Isopropamide</a></li> <li><a href="/w/index.php?title=J-104,129&action=edit&redlink=1" class="new" title="J-104,129 (page does not exist)">J-104,129</a></li> <li><a href="/wiki/Hyoscyamine" title="Hyoscyamine">Hyoscyamine</a></li> <li><a href="/wiki/Mamba#Mamba_toxins" title="Mamba">Mamba toxin 3</a></li> <li><a href="/wiki/Mamba#Mamba_toxins" title="Mamba">Mamba toxin 7</a></li> <li><a href="/wiki/Mazaticol" title="Mazaticol">Mazaticol</a></li> <li><a href="/wiki/Mebeverine" title="Mebeverine">Mebeverine</a></li> <li><a href="/wiki/Meladrazine" title="Meladrazine">Meladrazine</a></li> <li><a href="/wiki/Mepenzolate" title="Mepenzolate">Mepenzolate</a></li> <li><a href="/wiki/Methantheline" title="Methantheline">Methantheline</a></li> <li><a href="/wiki/Methoctramine" title="Methoctramine">Methoctramine</a></li> <li><a href="/wiki/Methylatropine" title="Methylatropine">Methylatropine</a></li> <li><a href="/wiki/Methylhomatropine" class="mw-redirect" title="Methylhomatropine">Methylhomatropine</a></li> <li><a href="/wiki/Methylscopolamine_bromide" title="Methylscopolamine bromide">Methylscopolamine</a></li> <li><a href="/wiki/Metixene" title="Metixene">Metixene</a></li> <li><a href="/wiki/Muscarinic_toxin_7" title="Muscarinic toxin 7">Muscarinic toxin 7</a></li> <li><a href="/wiki/N-Ethyl-3-piperidyl_benzilate" title="N-Ethyl-3-piperidyl benzilate">N-Ethyl-3-piperidyl benzilate</a></li> <li><a href="/wiki/N-Methyl-3-piperidyl_benzilate" title="N-Methyl-3-piperidyl benzilate">N-Methyl-3-piperidyl benzilate</a></li> <li><a href="/wiki/Nefopam" title="Nefopam">Nefopam</a></li> <li><a href="/wiki/Octatropine_methylbromide" title="Octatropine methylbromide">Octatropine methylbromide (anisotropine methylbromide)</a></li> <li><a href="/wiki/Orphenadrine" title="Orphenadrine">Orphenadrine</a></li> <li><a href="/wiki/Otenzepad" title="Otenzepad">Otenzepad (AF-DX 116)</a></li> <li><a href="/wiki/Otilonium_bromide" title="Otilonium bromide">Otilonium bromide</a></li> <li><a href="/wiki/Oxapium_iodide" title="Oxapium iodide">Oxapium iodide</a></li> <li><a href="/wiki/Oxitropium_bromide" title="Oxitropium bromide">Oxitropium bromide</a></li> <li><a href="/wiki/Oxybutynin" title="Oxybutynin">Oxybutynin</a></li> <li><a href="/wiki/Oxyphencyclimine" title="Oxyphencyclimine">Oxyphencyclimine</a></li> <li><a href="/wiki/Oxyphenonium_bromide" title="Oxyphenonium bromide">Oxyphenonium bromide</a></li> <li><a href="/w/index.php?title=PBID&action=edit&redlink=1" class="new" title="PBID (page does not exist)">PBID</a></li> <li><a href="/wiki/PD-102,807" title="PD-102,807">PD-102,807</a></li> <li><a href="/wiki/PD-0298029" title="PD-0298029">PD-0298029</a></li> <li><a href="/wiki/Penthienate" title="Penthienate">Penthienate</a></li> <li><a href="/wiki/Pethidine" title="Pethidine">Pethidine</a></li> <li><a href="/w/index.php?title=PFHHSiD&action=edit&redlink=1" class="new" title="PFHHSiD (page does not exist)">pFHHSiD</a></li> <li><a href="/wiki/Phenglutarimide" title="Phenglutarimide">Phenglutarimide</a></li> <li><a href="/wiki/Phenyltoloxamine" title="Phenyltoloxamine">Phenyltoloxamine</a></li> <li><a href="/wiki/Pipenzolate_bromide" title="Pipenzolate bromide">Pipenzolate bromide</a></li> <li><a href="/wiki/Piperidolate" title="Piperidolate">Piperidolate</a></li> <li><a href="/wiki/Pirenzepine" title="Pirenzepine">Pirenzepine</a></li> <li><a href="/wiki/Piroheptine" title="Piroheptine">Piroheptine</a></li> <li><a href="/wiki/Pizotifen" title="Pizotifen">Pizotifen</a></li> <li><a href="/wiki/Poldine" title="Poldine">Poldine</a></li> <li><a href="/wiki/Pridinol" title="Pridinol">Pridinol</a></li> <li><a href="/wiki/Prifinium_bromide" title="Prifinium bromide">Prifinium bromide</a></li> <li><a href="/wiki/Procyclidine" title="Procyclidine">Procyclidine</a></li> <li><a href="/wiki/Profenamine" title="Profenamine">Profenamine (ethopropazine)</a></li> <li><a href="/wiki/Propantheline_bromide" title="Propantheline bromide">Propantheline bromide</a></li> <li><a href="/wiki/Propiverine" title="Propiverine">Propiverine</a></li> <li><a href="/wiki/Quinidine" title="Quinidine">Quinidine</a></li> <li><a href="/wiki/3-Quinuclidinyl_thiochromane-4-carboxylate" title="3-Quinuclidinyl thiochromane-4-carboxylate">3-Quinuclidinyl thiochromane-4-carboxylate</a></li> <li><a href="/wiki/Revefenacin" title="Revefenacin">Revefenacin</a></li> <li><a href="/wiki/Rociverine" title="Rociverine">Rociverine</a></li> <li><a href="/w/index.php?title=RU-47,213&action=edit&redlink=1" class="new" title="RU-47,213 (page does not exist)">RU-47,213</a></li> <li><a href="/w/index.php?title=SCH-57,790&action=edit&redlink=1" class="new" title="SCH-57,790 (page does not exist)">SCH-57,790</a></li> <li><a href="/w/index.php?title=SCH-72,788&action=edit&redlink=1" class="new" title="SCH-72,788 (page does not exist)">SCH-72,788</a></li> <li><a href="/w/index.php?title=SCH-217,443&action=edit&redlink=1" class="new" title="SCH-217,443 (page does not exist)">SCH-217,443</a></li> <li><a href="/wiki/Hyoscine" class="mw-redirect" title="Hyoscine">Scopolamine (hyoscine)</a></li> <li><a href="/wiki/Hyoscine_butylbromide" title="Hyoscine butylbromide">Scopolamine butylbromide (hyoscine butylbromide)</a></li> <li><a href="/w/index.php?title=Silahexacyclium&action=edit&redlink=1" class="new" title="Silahexacyclium (page does not exist)">Silahexacyclium</a></li> <li><a href="/wiki/Sofpironium_bromide" title="Sofpironium bromide">Sofpironium bromide</a></li> <li><a href="/wiki/Solifenacin" title="Solifenacin">Solifenacin</a></li> <li><a href="/wiki/Selective_serotonin_reuptake_inhibitors" class="mw-redirect" title="Selective serotonin reuptake inhibitors"><abbr title="Selective serotonin reuptake inhibitors">SSRIs</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Selective serotonin reuptake inhibitors</span> (e.g., <a href="/wiki/Femoxetine" title="Femoxetine">femoxetine</a>, <a href="/wiki/Paroxetine" title="Paroxetine">paroxetine</a>)</li> <li><a href="/wiki/Telenzepine" title="Telenzepine">Telenzepine</a></li> <li><a href="/wiki/Terodiline" title="Terodiline">Terodiline</a></li> <li><a href="/wiki/Tetracyclic_antidepressant" title="Tetracyclic antidepressant">Tetracyclic antidepressants</a> (e.g., <a href="/wiki/Amoxapine" title="Amoxapine">amoxapine</a>, <a href="/wiki/Maprotiline" title="Maprotiline">maprotiline</a>, <a href="/wiki/Mianserin" title="Mianserin">mianserin</a>, <a href="/wiki/Mirtazapine" title="Mirtazapine">mirtazapine</a>)</li> <li><a href="/wiki/Tiemonium_iodide" title="Tiemonium iodide">Tiemonium iodide</a></li> <li><a href="/wiki/Timepidium_bromide" title="Timepidium bromide">Timepidium bromide</a></li> <li><a href="/wiki/Tiotropium_bromide" title="Tiotropium bromide">Tiotropium bromide</a></li> <li><a href="/w/index.php?title=Tiquizium_bromide&action=edit&redlink=1" class="new" title="Tiquizium bromide (page does not exist)">Tiquizium bromide</a></li> <li><a href="/wiki/Tofenacin" title="Tofenacin">Tofenacin</a></li> <li><a href="/wiki/Tolterodine" title="Tolterodine">Tolterodine</a></li> <li><a href="/wiki/Tricyclic_antidepressant" title="Tricyclic antidepressant">Tricyclic antidepressants</a> (e.g., <a href="/wiki/Amitriptyline" title="Amitriptyline">amitriptyline</a> (<a href="/wiki/Amitriptyline/perphenazine" title="Amitriptyline/perphenazine">+perphenazine</a>), <a href="/wiki/Amitriptylinoxide" title="Amitriptylinoxide">amitriptylinoxide</a>, <a href="/wiki/Butriptyline" title="Butriptyline">butriptyline</a>, <a href="/wiki/Cidoxepin" title="Cidoxepin">cidoxepin</a>, <a href="/wiki/Clomipramine" title="Clomipramine">clomipramine</a>, <a href="/wiki/Desipramine" title="Desipramine">desipramine</a>, <a href="/w/index.php?title=Desmethyldesipramine&action=edit&redlink=1" class="new" title="Desmethyldesipramine (page does not exist)">desmethyldesipramine</a>, <a href="/wiki/Dibenzepin" title="Dibenzepin">dibenzepin</a>, <a href="/wiki/Dosulepin" title="Dosulepin">dosulepin (dothiepin)</a>, <a href="/wiki/Doxepin" title="Doxepin">doxepin</a>, <a href="/wiki/Imipramine" title="Imipramine">imipramine</a>, <a href="/wiki/Lofepramine" title="Lofepramine">lofepramine</a>, <a href="/wiki/Nitroxazepine" title="Nitroxazepine">nitroxazepine</a>, <a href="/wiki/Northiaden" title="Northiaden">northiaden (desmethyldosulepin)</a>, <a href="/wiki/Nortriptyline" title="Nortriptyline">nortriptyline</a>, <a href="/wiki/Protriptyline" title="Protriptyline">protriptyline</a>, <a href="/wiki/Quinupramine" title="Quinupramine">quinupramine</a>, <a href="/wiki/Trimipramine" title="Trimipramine">trimipramine</a>)</li> <li><a href="/wiki/Tridihexethyl" title="Tridihexethyl">Tridihexethyl</a></li> <li><a href="/wiki/Trihexyphenidyl" title="Trihexyphenidyl">Trihexyphenidyl</a></li> <li><a href="/wiki/Trimebutine" title="Trimebutine">Trimebutine</a></li> <li><a href="/wiki/Tripitamine" class="mw-redirect" title="Tripitamine">Tripitamine (tripitramine)</a></li> <li><a href="/w/index.php?title=Tropacine&action=edit&redlink=1" class="new" title="Tropacine (page does not exist)">Tropacine</a></li> <li><a href="/wiki/Tropatepine" title="Tropatepine">Tropatepine</a></li> <li><a href="/wiki/Tropicamide" title="Tropicamide">Tropicamide</a></li> <li><a href="/wiki/Trospium_chloride" title="Trospium chloride">Trospium chloride</a></li> <li><a href="/wiki/Typical_antipsychotic" title="Typical antipsychotic">Typical antipsychotics</a> (e.g., <a href="/wiki/Chlorpromazine" title="Chlorpromazine">chlorpromazine</a>, <a href="/wiki/Chlorprothixene" title="Chlorprothixene">chlorprothixene</a>, <a href="/wiki/Cyamemazine" title="Cyamemazine">cyamemazine (cyamepromazine)</a>, <a href="/wiki/Loxapine" title="Loxapine">loxapine</a>, <a href="/wiki/Mesoridazine" title="Mesoridazine">mesoridazine</a>, <a href="/wiki/Thioridazine" title="Thioridazine">thioridazine</a>)</li> <li><a href="/wiki/Umeclidinium_bromide" title="Umeclidinium bromide">Umeclidinium bromide</a> (<a href="/wiki/Umeclidinium_bromide/vilanterol" title="Umeclidinium bromide/vilanterol">+vilanterol</a>)</li> <li><a href="/wiki/WIN-2299" title="WIN-2299">WIN-2299</a></li> <li><a href="/wiki/Xanomeline" title="Xanomeline">Xanomeline</a></li> <li><a href="/w/index.php?title=Zamifenacin&action=edit&redlink=1" class="new" title="Zamifenacin (page does not exist)">Zamifenacin</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Precursor_(chemistry)" title="Precursor (chemistry)">Precursors</a><br /><small>(and <a href="/wiki/Prodrug" title="Prodrug">prodrugs</a>)</small></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Acetyl-coA" class="mw-redirect" title="Acetyl-coA">Acetyl-coA</a></li> <li><a href="/wiki/Adafenoxate" title="Adafenoxate">Adafenoxate</a></li> <li><a class="mw-selflink selflink">Choline</a> (<a href="/wiki/Lecithin" title="Lecithin">lecithin</a>)</li> <li><a href="/wiki/Citicoline" title="Citicoline">Citicoline</a></li> <li><a href="/wiki/Cyprodenate" title="Cyprodenate">Cyprodenate</a></li> <li><a href="/wiki/Dimethylethanolamine" title="Dimethylethanolamine">Dimethylethanolamine</a></li> <li><a href="/wiki/Glycerophosphocholine" class="mw-redirect" title="Glycerophosphocholine">Glycerophosphocholine</a></li> <li><a href="/wiki/Meclofenoxate" title="Meclofenoxate">Meclofenoxate (centrophenoxine)</a></li> <li><a href="/wiki/Phosphatidylcholine" title="Phosphatidylcholine">Phosphatidylcholine</a></li> <li><a href="/wiki/Phosphatidylethanolamine" title="Phosphatidylethanolamine">Phosphatidylethanolamine</a></li> <li><a href="/wiki/Phosphorylcholine" title="Phosphorylcholine">Phosphorylcholine</a></li> <li><a href="/wiki/Pirisudanol" title="Pirisudanol">Pirisudanol</a></li></ul> </div></td></tr><tr><td class="navbox-abovebelow" colspan="2"><div> <dl><dt>See also</dt> <dd><a href="/wiki/Template:Receptor_modulators" title="Template:Receptor modulators">Receptor/signaling modulators</a></dd> <dd><a href="/wiki/Template:Nicotinic_acetylcholine_receptor_modulators" title="Template:Nicotinic acetylcholine receptor modulators">Nicotinic acetylcholine receptor modulators</a></dd> <dd><a href="/wiki/Template:Acetylcholine_metabolism_and_transport_modulators" title="Template:Acetylcholine metabolism and transport modulators">Acetylcholine metabolism/transport modulators</a></dd></dl> </div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"></div><div role="navigation" class="navbox" aria-labelledby="Nicotinic_acetylcholine_receptor_modulators" style="padding:3px"><table class="nowraplinks hlist mw-collapsible mw-collapsed navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Nicotinic_acetylcholine_receptor_modulators" title="Template:Nicotinic acetylcholine receptor modulators"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Nicotinic_acetylcholine_receptor_modulators" title="Template talk:Nicotinic acetylcholine receptor modulators"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Nicotinic_acetylcholine_receptor_modulators" title="Special:EditPage/Template:Nicotinic acetylcholine receptor modulators"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Nicotinic_acetylcholine_receptor_modulators" style="font-size:114%;margin:0 4em"><a href="/wiki/Nicotinic_acetylcholine_receptor" title="Nicotinic acetylcholine receptor">Nicotinic acetylcholine receptor</a> <a href="/wiki/Receptor_modulator" title="Receptor modulator">modulators</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Nicotinic_acetylcholine_receptors" class="mw-redirect" title="Nicotinic acetylcholine receptors"><abbr title="Nicotinic acetylcholine receptors">nAChRs</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Nicotinic acetylcholine receptors</span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Receptor_agonist" class="mw-redirect" title="Receptor agonist">Agonists</a><br />(and <a href="/wiki/Positive_allosteric_modulators" class="mw-redirect" title="Positive allosteric modulators"><abbr title="positive allosteric modulators">PAMs</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip positive allosteric modulators</span>)</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/5-Hydroxyindoleacetic_acid" title="5-Hydroxyindoleacetic acid">5-HIAA</a></li> <li><a href="/wiki/6-Chloronicotine" title="6-Chloronicotine">6-Chloronicotine</a></li> <li><a href="/wiki/A-84,543" title="A-84,543">A-84,543</a></li> <li><a href="/wiki/A-366,833" title="A-366,833">A-366,833</a></li> <li><a href="/w/index.php?title=A-582,941&action=edit&redlink=1" class="new" title="A-582,941 (page does not exist)">A-582,941</a></li> <li><a href="/w/index.php?title=A-867,744&action=edit&redlink=1" class="new" title="A-867,744 (page does not exist)">A-867,744</a></li> <li><a href="/wiki/ABT-202" title="ABT-202">ABT-202</a></li> <li><a href="/wiki/ABT-418" title="ABT-418">ABT-418</a></li> <li><a href="/w/index.php?title=ABT-560&action=edit&redlink=1" class="new" title="ABT-560 (page does not exist)">ABT-560</a></li> <li><a href="/w/index.php?title=ABT-894&action=edit&redlink=1" class="new" title="ABT-894 (page does not exist)">ABT-894</a></li> <li><a href="/wiki/Acetylcholine" title="Acetylcholine">Acetylcholine</a></li> <li><a href="/wiki/Altinicline" title="Altinicline">Altinicline</a></li> <li><a href="/wiki/Anabasine" title="Anabasine">Anabasine</a></li> <li><a href="/wiki/Anatabine" title="Anatabine">Anatabine</a></li> <li><a href="/wiki/Anatoxin-a" title="Anatoxin-a">Anatoxin-a</a></li> <li><a href="/wiki/AR-R17779" title="AR-R17779">AR-R17779</a></li> <li><a href="/wiki/Bephenium_hydroxynaphthoate" title="Bephenium hydroxynaphthoate">Bephenium hydroxynaphthoate</a></li> <li><a href="/wiki/Butinoline" title="Butinoline">Butinoline</a></li> <li><a href="/wiki/Butyrylcholine" title="Butyrylcholine">Butyrylcholine</a></li> <li><a href="/wiki/Carbachol" title="Carbachol">Carbachol</a></li> <li><a class="mw-selflink selflink">Choline</a></li> <li><a href="/wiki/Cotinine" title="Cotinine">Cotinine</a></li> <li><a href="/wiki/Cytisine" title="Cytisine">Cytisine</a></li> <li><a href="/wiki/Decamethonium" title="Decamethonium">Decamethonium</a></li> <li><a href="/wiki/Desformylflustrabromine" title="Desformylflustrabromine">Desformylflustrabromine</a></li> <li><a href="/wiki/Dianicline" title="Dianicline">Dianicline</a></li> <li><a href="/wiki/Dimethylphenylpiperazinium" title="Dimethylphenylpiperazinium">Dimethylphenylpiperazinium</a></li> <li><a href="/wiki/Epibatidine" title="Epibatidine">Epibatidine</a></li> <li><a href="/wiki/Epiboxidine" title="Epiboxidine">Epiboxidine</a></li> <li><a href="/wiki/Alcohol_(drug)" title="Alcohol (drug)">Ethanol (alcohol)</a></li> <li><a href="/w/index.php?title=Ethoxysebacylcholine&action=edit&redlink=1" class="new" title="Ethoxysebacylcholine (page does not exist)">Ethoxysebacylcholine</a></li> <li><a href="/w/index.php?title=EVP-4473&action=edit&redlink=1" class="new" title="EVP-4473 (page does not exist)">EVP-4473</a></li> <li><a href="/wiki/EVP-6124" class="mw-redirect" title="EVP-6124">EVP-6124</a></li> <li><a href="/wiki/Galantamine" title="Galantamine">Galantamine</a></li> <li><a href="/wiki/GTS-21" title="GTS-21">GTS-21</a></li> <li><a href="/wiki/Ispronicline" title="Ispronicline">Ispronicline</a></li> <li><a href="/wiki/Ivermectin" title="Ivermectin">Ivermectin</a></li> <li><a href="/wiki/JNJ-39393406" title="JNJ-39393406">JNJ-39393406</a></li> <li><a href="/wiki/Levamisole" title="Levamisole">Levamisole</a></li> <li><a href="/wiki/Lobeline" title="Lobeline">Lobeline</a></li> <li><a href="/w/index.php?title=MEM-63,908&action=edit&redlink=1" class="new" title="MEM-63,908 (page does not exist)">MEM-63,908 (RG-3487)</a></li> <li><a href="/wiki/Morantel" title="Morantel">Morantel</a></li> <li><a href="/wiki/Nicotine" title="Nicotine">Nicotine</a> (<a href="/wiki/Tobacco" title="Tobacco">tobacco</a>)</li> <li><a href="/w/index.php?title=NS-1738&action=edit&redlink=1" class="new" title="NS-1738 (page does not exist)">NS-1738</a></li> <li><a href="/wiki/PHA-543,613" title="PHA-543,613">PHA-543,613</a></li> <li><a href="/w/index.php?title=PHA-709,829&action=edit&redlink=1" class="new" title="PHA-709,829 (page does not exist)">PHA-709,829</a></li> <li><a href="/wiki/PNU-120,596" title="PNU-120,596">PNU-120,596</a></li> <li><a href="/wiki/PNU-282,987" title="PNU-282,987">PNU-282,987</a></li> <li><a href="/wiki/Pozanicline" title="Pozanicline">Pozanicline</a></li> <li><a href="/wiki/Pyrantel" title="Pyrantel">Pyrantel</a></li> <li><a href="/wiki/Rivanicline" title="Rivanicline">Rivanicline</a></li> <li><a href="/wiki/RJR-2429" title="RJR-2429">RJR-2429</a></li> <li><a href="/wiki/Sazetidine_A" title="Sazetidine A">Sazetidine A</a></li> <li><a href="/wiki/SB-206553" title="SB-206553">SB-206553</a></li> <li><a href="/w/index.php?title=Sebacylcholine&action=edit&redlink=1" class="new" title="Sebacylcholine (page does not exist)">Sebacylcholine</a></li> <li><a href="/wiki/SIB-1508Y" class="mw-redirect" title="SIB-1508Y">SIB-1508Y</a></li> <li><a href="/wiki/SIB-1553A" title="SIB-1553A">SIB-1553A</a></li> <li><a href="/wiki/SSR-180,711" title="SSR-180,711">SSR-180,711</a></li> <li><a href="/w/index.php?title=Suberyldicholine&action=edit&redlink=1" class="new" title="Suberyldicholine (page does not exist)">Suberyldicholine</a></li> <li><a href="/wiki/Suxamethonium" class="mw-redirect" title="Suxamethonium">Suxamethonium (succinylcholine)</a></li> <li><a href="/wiki/Suxethonium_chloride" title="Suxethonium chloride">Suxethonium (succinyldicholine)</a></li> <li><a href="/wiki/TC-1698" title="TC-1698">TC-1698</a></li> <li><a href="/w/index.php?title=TC-1734&action=edit&redlink=1" class="new" title="TC-1734 (page does not exist)">TC-1734</a></li> <li><a href="/wiki/TC-1827" title="TC-1827">TC-1827</a></li> <li><a href="/wiki/TC-2216" title="TC-2216">TC-2216</a></li> <li><a href="/wiki/TC-5214" class="mw-redirect" title="TC-5214">TC-5214</a></li> <li><a href="/wiki/TC-5619" class="mw-redirect" title="TC-5619">TC-5619</a></li> <li><a href="/w/index.php?title=TC-6683&action=edit&redlink=1" class="new" title="TC-6683 (page does not exist)">TC-6683</a></li> <li><a href="/wiki/Tebanicline" title="Tebanicline">Tebanicline</a></li> <li><a href="/wiki/Tribendimidine" title="Tribendimidine">Tribendimidine</a></li> <li><a href="/wiki/Tropisetron" title="Tropisetron">Tropisetron</a></li> <li><a href="/wiki/UB-165" title="UB-165">UB-165</a></li> <li><a href="/wiki/Varenicline" title="Varenicline">Varenicline</a></li> <li><a href="/wiki/WAY-317,538" class="mw-redirect" title="WAY-317,538">WAY-317,538</a></li> <li><a href="/w/index.php?title=XY-4083&action=edit&redlink=1" class="new" title="XY-4083 (page does not exist)">XY-4083</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Receptor_antagonist" title="Receptor antagonist">Antagonists</a><br />(and <a href="/wiki/Negative_allosteric_modulators" class="mw-redirect" title="Negative allosteric modulators"><abbr title="negative allosteric modulators">NAMs</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip negative allosteric modulators</span>)</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/18-Methylaminocoronaridine" title="18-Methylaminocoronaridine">18-MAC</a></li> <li><a href="/wiki/18-Methoxycoronaridine" title="18-Methoxycoronaridine">18-MC</a></li> <li><a href="/wiki/%CE%91-Neurotoxin" title="Α-Neurotoxin">α-Neurotoxins</a> (e.g., <a href="/wiki/%CE%91-bungarotoxin" class="mw-redirect" title="Α-bungarotoxin">α-bungarotoxin</a>, <a href="/wiki/%CE%91-cobratoxin" class="mw-redirect" title="Α-cobratoxin">α-cobratoxin</a>, <a href="/wiki/%CE%91-conotoxin" class="mw-redirect" title="Α-conotoxin">α-conotoxin</a>, many others)</li> <li><a href="/w/index.php?title=ABT-126&action=edit&redlink=1" class="new" title="ABT-126 (page does not exist)">ABT-126</a></li> <li><a href="/wiki/Alcuronium" class="mw-redirect" title="Alcuronium">Alcuronium</a></li> <li><a href="/wiki/Allopregnanolone" title="Allopregnanolone">Allopregnanolone</a></li> <li><a href="/wiki/Amantadine" title="Amantadine">Amantadine</a></li> <li><a href="/w/index.php?title=Anatruxonium&action=edit&redlink=1" class="new" title="Anatruxonium (page does not exist)">Anatruxonium</a></li> <li><a href="/w/index.php?title=AQW051&action=edit&redlink=1" class="new" title="AQW051 (page does not exist)">AQW051</a></li> <li><a href="/wiki/Atracurium" class="mw-redirect" title="Atracurium">Atracurium</a></li> <li><a href="/wiki/Barbiturates" class="mw-redirect" title="Barbiturates">Barbiturates</a> (e.g., <a href="/wiki/Pentobarbital" title="Pentobarbital">pentobarbital</a>, <a href="/wiki/Sodium_thiopental" title="Sodium thiopental">sodium thiopental</a>)</li> <li><a href="/wiki/BNC-210" title="BNC-210">BNC-210</a></li> <li><a href="/wiki/Bungarotoxin" title="Bungarotoxin">Bungarotoxins</a> (e.g., <a href="/wiki/%CE%91-bungarotoxin" class="mw-redirect" title="Α-bungarotoxin">α-bungarotoxin</a>, <a href="/wiki/%CE%9A-bungarotoxin" class="mw-redirect" title="Κ-bungarotoxin">κ-bungarotoxin</a>)</li> <li><a href="/wiki/Bupropion" title="Bupropion">Bupropion</a></li> <li><a href="/wiki/BW284C51" title="BW284C51">BW284C51</a></li> <li><a href="/wiki/BW-A444" title="BW-A444">BW-A444</a></li> <li><a href="/wiki/Candocuronium_iodide" title="Candocuronium iodide">Candocuronium iodide (chandonium iodide)</a></li> <li><a href="/wiki/Chlorisondamine" title="Chlorisondamine">Chlorisondamine</a></li> <li><a href="/wiki/Cisatracurium" class="mw-redirect" title="Cisatracurium">Cisatracurium</a></li> <li><a href="/wiki/Coclaurine" title="Coclaurine">Coclaurine</a></li> <li><a href="/wiki/Coronaridine" title="Coronaridine">Coronaridine</a></li> <li><a href="/wiki/Curare" title="Curare">Curare</a></li> <li><a href="/wiki/Cyclopropane" title="Cyclopropane">Cyclopropane</a></li> <li><a href="/wiki/Dacuronium_bromide" title="Dacuronium bromide">Dacuronium bromide</a></li> <li><a href="/wiki/Decamethonium" title="Decamethonium">Decamethonium</a></li> <li><a href="/wiki/Dehydronorketamine" title="Dehydronorketamine">Dehydronorketamine</a></li> <li><a href="/wiki/Desflurane" title="Desflurane">Desflurane</a></li> <li><a href="/wiki/Dextromethorphan" title="Dextromethorphan">Dextromethorphan</a></li> <li><a href="/wiki/Dextropropoxyphene" title="Dextropropoxyphene">Dextropropoxyphene</a></li> <li><a href="/wiki/Dextrorphan" title="Dextrorphan">Dextrorphan</a></li> <li><a href="/w/index.php?title=Diadonium&action=edit&redlink=1" class="new" title="Diadonium (page does not exist)">Diadonium</a></li> <li><a href="/w/index.php?title=Dihydro-beta-erythroidine&action=edit&redlink=1" class="new" title="Dihydro-beta-erythroidine (page does not exist)">DHβE</a></li> <li><a href="/wiki/Dihydrochandonium" title="Dihydrochandonium">Dihydrochandonium</a></li> <li><a href="/wiki/Dimethyltubocurarine" class="mw-redirect" title="Dimethyltubocurarine">Dimethyltubocurarine (metocurine)</a></li> <li><a href="/wiki/Dioscorine" title="Dioscorine">Dioscorine</a></li> <li><a href="/wiki/Dipyrandium" title="Dipyrandium">Dipyrandium</a></li> <li><a href="/wiki/Dizocilpine" title="Dizocilpine">Dizocilpine (MK-801)</a></li> <li><a href="/wiki/Doxacurium" class="mw-redirect" title="Doxacurium">Doxacurium</a></li> <li><a href="/wiki/Encenicline" title="Encenicline">Encenicline</a></li> <li><a href="/wiki/Enflurane" title="Enflurane">Enflurane</a></li> <li><a href="/wiki/Erythravine" title="Erythravine">Erythravine</a></li> <li><a href="/wiki/Esketamine" title="Esketamine">Esketamine</a></li> <li><a href="/wiki/Fazadinium" class="mw-redirect" title="Fazadinium">Fazadinium</a></li> <li><a href="/wiki/Gallamine" class="mw-redirect" title="Gallamine">Gallamine</a></li> <li><a href="/wiki/Gantacurium_chloride" title="Gantacurium chloride">Gantacurium chloride</a></li> <li><a href="/wiki/Halothane" title="Halothane">Halothane</a></li> <li><a href="/wiki/Hexafluronium" class="mw-redirect" title="Hexafluronium">Hexafluronium</a></li> <li><a href="/wiki/Hexamethonium" title="Hexamethonium">Hexamethonium (benzohexonium)</a></li> <li><a href="/wiki/Hydroxybupropion" title="Hydroxybupropion">Hydroxybupropion</a></li> <li><a href="/wiki/Hydroxynorketamine" title="Hydroxynorketamine">Hydroxynorketamine</a></li> <li><a href="/wiki/Ibogaine" title="Ibogaine">Ibogaine</a></li> <li><a href="/wiki/Isoflurane" title="Isoflurane">Isoflurane</a></li> <li><a href="/wiki/Ketamine" title="Ketamine">Ketamine</a></li> <li><a href="/wiki/Kynurenic_acid" title="Kynurenic acid">Kynurenic acid</a></li> <li><a href="/wiki/Laudanosine" title="Laudanosine">Laudanosine</a></li> <li><a href="/wiki/Laudexium" class="mw-redirect" title="Laudexium">Laudexium (laudolissin)</a></li> <li><a href="/wiki/Levacetylmethadol" title="Levacetylmethadol">Levacetylmethadol</a></li> <li><a href="/wiki/Levomethadone" title="Levomethadone">Levomethadone</a></li> <li><a href="/wiki/Malouetine" title="Malouetine">Malouetine</a></li> <li><a href="/wiki/2-Methoxyethyl-18-methoxycoronaridinate" title="2-Methoxyethyl-18-methoxycoronaridinate">ME-18-MC</a></li> <li><a href="/wiki/Mecamylamine" title="Mecamylamine">Mecamylamine</a></li> <li><a href="/wiki/Memantine" title="Memantine">Memantine</a></li> <li><a href="/wiki/Methadone" title="Methadone">Methadone</a></li> <li><a href="/wiki/Methorphan" title="Methorphan">Methorphan (racemethorphan)</a></li> <li><a href="/wiki/Methyllycaconitine" title="Methyllycaconitine">Methyllycaconitine</a></li> <li><a href="/wiki/Metocurine" title="Metocurine">Metocurine</a></li> <li><a href="/wiki/Mivacurium" class="mw-redirect" title="Mivacurium">Mivacurium</a></li> <li><a href="/wiki/Morphanol" class="mw-redirect" title="Morphanol">Morphanol (racemorphan)</a></li> <li><a href="/wiki/Neramexane" title="Neramexane">Neramexane</a></li> <li><a href="/wiki/Nitrous_oxide" title="Nitrous oxide">Nitrous oxide</a></li> <li><a href="/wiki/Norketamine" title="Norketamine">Norketamine</a></li> <li><a href="/wiki/Pancuronium_bromide" title="Pancuronium bromide">Pancuronium bromide</a></li> <li><a href="/wiki/Pempidine" title="Pempidine">Pempidine</a></li> <li><a href="/wiki/Pentamine" title="Pentamine">Pentamine</a></li> <li><a href="/wiki/Pentolinium" title="Pentolinium">Pentolinium</a></li> <li><a href="/wiki/Phencyclidine" title="Phencyclidine">Phencyclidine</a></li> <li><a href="/wiki/Pipecuronium_bromide" title="Pipecuronium bromide">Pipecuronium bromide</a></li> <li><a href="/wiki/Progesterone" title="Progesterone">Progesterone</a></li> <li><a href="/wiki/Promegestone" title="Promegestone">Promegestone</a></li> <li><a href="/wiki/Radafaxine" title="Radafaxine">Radafaxine</a></li> <li><a href="/wiki/Rapacuronium_bromide" title="Rapacuronium bromide">Rapacuronium bromide</a></li> <li><a href="/wiki/Reboxetine" title="Reboxetine">Reboxetine</a></li> <li><a href="/wiki/Rocuronium_bromide" title="Rocuronium bromide">Rocuronium bromide</a></li> <li><a href="/wiki/Sevoflurane" title="Sevoflurane">Sevoflurane</a></li> <li><a href="/wiki/Stercuronium_iodide" title="Stercuronium iodide">Stercuronium iodide</a></li> <li><a href="/wiki/Surugatoxin" title="Surugatoxin">Surugatoxin</a></li> <li><a href="/wiki/Thiocolchicoside" title="Thiocolchicoside">Thiocolchicoside</a></li> <li><a href="/wiki/Threohydrobupropion" title="Threohydrobupropion">Threohydrobupropion</a></li> <li><a href="/wiki/Toxiferine" title="Toxiferine">Toxiferine</a></li> <li><a href="/wiki/Tramadol" title="Tramadol">Tramadol</a></li> <li><a href="/wiki/Trimetaphan_camsilate" title="Trimetaphan camsilate">Trimetaphan camsilate (trimethaphan camsylate)</a></li> <li><a href="/w/index.php?title=Tropeinium&action=edit&redlink=1" class="new" title="Tropeinium (page does not exist)">Tropeinium</a></li> <li><a href="/wiki/Tubocurarine" class="mw-redirect" title="Tubocurarine">Tubocurarine</a></li> <li><a href="/wiki/Vanoxerine" title="Vanoxerine">Vanoxerine</a></li> <li><a href="/wiki/Vecuronium_bromide" title="Vecuronium bromide">Vecuronium bromide</a></li> <li><a href="/wiki/Xenon" title="Xenon">Xenon</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Precursor_(chemistry)" title="Precursor (chemistry)">Precursors</a><br /><small>(and <a href="/wiki/Prodrug" title="Prodrug">prodrugs</a>)</small></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Acetyl-coA" class="mw-redirect" title="Acetyl-coA">Acetyl-coA</a></li> <li><a href="/wiki/Adafenoxate" title="Adafenoxate">Adafenoxate</a></li> <li><a class="mw-selflink selflink">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"></div><div role="navigation" class="navbox" aria-labelledby="Acetylcholine_metabolism_and_transport_modulators" style="padding:3px"><table class="nowraplinks hlist mw-collapsible mw-collapsed navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Acetylcholine_metabolism_and_transport_modulators" title="Template:Acetylcholine metabolism and transport modulators"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Acetylcholine_metabolism_and_transport_modulators" title="Template talk:Acetylcholine metabolism and transport modulators"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Acetylcholine_metabolism_and_transport_modulators" title="Special:EditPage/Template:Acetylcholine metabolism and transport modulators"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Acetylcholine_metabolism_and_transport_modulators" style="font-size:114%;margin:0 4em"><a href="/wiki/Acetylcholine" title="Acetylcholine">Acetylcholine</a> <a href="/wiki/Metabolism" title="Metabolism">metabolism</a> and <a href="/wiki/Neurotransmitter_transporter" title="Neurotransmitter transporter">transport</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/Enzyme" title="Enzyme">Enzyme</a><br /><small>(<a href="/wiki/Enzyme_modulator" title="Enzyme modulator">modulators</a>)</small></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:6em;;text-align:center;"><a href="/wiki/Choline_acetyltransferase" title="Choline acetyltransferase"><abbr title="Choline acetyltransferase">ChAT</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 Choline acetyltransferase</span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><b>Inhibitors:</b> <a href="/w/index.php?title=1-(-Benzoylethyl)pyridinium&action=edit&redlink=1" class="new" title="1-(-Benzoylethyl)pyridinium (page does not exist)">1-(-Benzoylethyl)pyridinium</a></li> <li><a href="/w/index.php?title=2-(%CE%B1-Naphthoyl)ethyltrimethylammonium&action=edit&redlink=1" class="new" title="2-(α-Naphthoyl)ethyltrimethylammonium (page does not exist)">2-(α-Naphthoyl)ethyltrimethylammonium</a></li> <li><a href="/w/index.php?title=3-Chloro-4-stillbazole&action=edit&redlink=1" class="new" title="3-Chloro-4-stillbazole (page does not exist)">3-Chloro-4-stillbazole</a></li> <li><a href="/w/index.php?title=4-(1-Naphthylvinyl)pyridine&action=edit&redlink=1" class="new" title="4-(1-Naphthylvinyl)pyridine (page does not exist)">4-(1-Naphthylvinyl)pyridine</a></li> <li><a href="/w/index.php?title=Acetylseco_hemicholinium-3&action=edit&redlink=1" class="new" title="Acetylseco hemicholinium-3 (page does not exist)">Acetylseco hemicholinium-3</a></li> <li><a href="/w/index.php?title=Acryloylcholine&action=edit&redlink=1" class="new" title="Acryloylcholine (page does not exist)">Acryloylcholine</a></li> <li><a href="/wiki/AF64A" class="mw-redirect" title="AF64A">AF64A</a></li> <li><a href="/w/index.php?title=(E)-1-Methyl-4-(1-naphthylvinyl)-1,2,3,6-tetrahydropyridine&action=edit&redlink=1" class="new" title="(E)-1-Methyl-4-(1-naphthylvinyl)-1,2,3,6-tetrahydropyridine (page does not exist)">B115</a></li> <li><a href="/w/index.php?title=(2-Benzoylethyl)trimethylammonium&action=edit&redlink=1" class="new" title="(2-Benzoylethyl)trimethylammonium (page does not exist)">BETA</a></li> <li><a href="/w/index.php?title=N,N-Dimethylamino-2-ethoxyimino-2-adamantane&action=edit&redlink=1" class="new" title="N,N-Dimethylamino-2-ethoxyimino-2-adamantane (page does not exist)">CM-54,903</a></li> <li><a href="/w/index.php?title=N,N-Dimethylaminoethylacrylate&action=edit&redlink=1" class="new" title="N,N-Dimethylaminoethylacrylate (page does not exist)">N,N-Dimethylaminoethylacrylate</a></li> <li><a href="/w/index.php?title=N,N-Dimethylaminoethylchloroacetate&action=edit&redlink=1" class="new" title="N,N-Dimethylaminoethylchloroacetate (page does not exist)">N,N-Dimethylaminoethylchloroacetate</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:6em;;text-align:center;"><a href="/wiki/Acetylcholinesterase" title="Acetylcholinesterase"><abbr title="Acetylcholinesterase">AChE</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 Acetylcholinesterase</span></th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><b><a href="/wiki/Acetylcholinesterase_inhibitor" title="Acetylcholinesterase inhibitor">Inhibitors</a>:</b> <i>Reversible:</i> Carbamates: <a href="/wiki/Aldicarb" title="Aldicarb">Aldicarb</a></li> <li><a href="/wiki/Aminocarb" title="Aminocarb">Aminocarb</a></li> <li><a href="/wiki/Bendiocarb" title="Bendiocarb">Bendiocarb</a></li> <li><a href="/w/index.php?title=Bufencarb&action=edit&redlink=1" class="new" title="Bufencarb (page does not exist)">Bufencarb</a></li> <li><a href="/wiki/Carbaryl" title="Carbaryl">Carbaryl</a></li> <li><a href="/wiki/Carbendazim" title="Carbendazim">Carbendazim</a></li> <li><a href="/w/index.php?title=Carbetamide&action=edit&redlink=1" class="new" title="Carbetamide (page does not exist)">Carbetamide</a></li> <li><a href="/wiki/Carbofuran" title="Carbofuran">Carbofuran</a></li> <li><a href="/wiki/Carbosulfan" title="Carbosulfan">Carbosulfan</a></li> <li><a href="/w/index.php?title=Chlorbufam&action=edit&redlink=1" class="new" title="Chlorbufam (page does not exist)">Chlorbufam</a></li> <li><a href="/w/index.php?title=Chloropropham&action=edit&redlink=1" class="new" title="Chloropropham (page does not exist)">Chloropropham</a></li> <li><a href="/wiki/Dimetilan" title="Dimetilan">Dimetilan</a></li> <li><a href="/wiki/Ethienocarb" class="mw-redirect" title="Ethienocarb">Ethienocarb</a></li> <li><a href="/wiki/Ethiofencarb" title="Ethiofencarb">Ethiofencarb</a></li> <li><a href="/wiki/Fenobucarb" title="Fenobucarb">Fenobucarb</a></li> <li><a href="/wiki/Formetanate" title="Formetanate">Formetanate</a></li> <li><a href="/wiki/Formparanate" title="Formparanate">Formparanate</a></li> <li><a href="/wiki/Methiocarb" title="Methiocarb">Methiocarb</a></li> <li><a href="/wiki/Methomyl" title="Methomyl">Methomyl</a></li> <li><a href="/wiki/Metolcarb" title="Metolcarb">Metolcarb</a></li> <li><a href="/wiki/Miotine" title="Miotine">Miotine</a></li> <li><a href="/wiki/Oxamyl" title="Oxamyl">Oxamyl</a></li> <li><a href="/w/index.php?title=Phenmedipham&action=edit&redlink=1" class="new" title="Phenmedipham (page does not exist)">Phenmedipham</a></li> <li><a href="/w/index.php?title=Pinmicarb&action=edit&redlink=1" class="new" title="Pinmicarb (page does not exist)">Pinmicarb</a></li> <li><a href="/wiki/Pirimicarb" title="Pirimicarb">Pirimicarb</a></li> <li><a href="/wiki/Promecarb" title="Promecarb">Promecarb</a></li> <li><a href="/wiki/Propamocarb" title="Propamocarb">Propamocarb</a></li> <li><a href="/w/index.php?title=Propham&action=edit&redlink=1" class="new" title="Propham (page does not exist)">Propham</a></li> <li><a href="/wiki/Propoxur" title="Propoxur">Propoxur</a></li> <li><a href="/w/index.php?title=Thiodicarb&action=edit&redlink=1" class="new" title="Thiodicarb (page does not exist)">Thiodicarb</a></li> <li><a href="/wiki/Thiofanox" title="Thiofanox">Thiofanox</a>; Stigmines: <a href="/wiki/Distigmine" title="Distigmine">Distigmine</a></li> <li><a href="/w/index.php?title=Eptastigmine&action=edit&redlink=1" class="new" title="Eptastigmine (page does not exist)">Eptastigmine</a></li> <li><a href="/w/index.php?title=Ganstigmine&action=edit&redlink=1" class="new" title="Ganstigmine (page does not exist)">Ganstigmine</a></li> <li><a href="/wiki/Neostigmine" title="Neostigmine">Neostigmine</a> <a href="/wiki/Neostigmine/glycopyrronium_bromide" title="Neostigmine/glycopyrronium bromide">+glycopyrronium bromide</a></li> <li><a href="/wiki/Phenserine" title="Phenserine">Phenserine</a></li> <li><a href="/wiki/Physostigmine" title="Physostigmine">Physostigmine</a></li> <li><a href="/wiki/Pyridostigmine" title="Pyridostigmine">Pyridostigmine</a></li> <li><a href="/w/index.php?title=Quilostigmine&action=edit&redlink=1" class="new" title="Quilostigmine (page does not exist)">Quilostigmine</a></li> <li><a href="/wiki/Rivastigmine" title="Rivastigmine">Rivastigmine</a></li> <li><a href="/w/index.php?title=Terestigmine&action=edit&redlink=1" class="new" title="Terestigmine (page does not exist)">Terestigmine</a>; Others: <a href="/wiki/Acotiamide" title="Acotiamide">Acotiamide</a></li> <li><a href="/wiki/Ambenonium" class="mw-redirect" title="Ambenonium">Ambenonium</a></li> <li><a href="/wiki/Caffeine" title="Caffeine">Caffeine</a></li> <li><a href="/wiki/Donepezil" title="Donepezil">Donepezil</a></li> <li><a href="/wiki/EA-3990" title="EA-3990">EA-3990</a></li> <li><a href="/wiki/EA-4056" title="EA-4056">EA-4056</a></li> <li><a href="/wiki/Edrophonium" title="Edrophonium">Edrophonium</a></li> <li><a href="/wiki/Galantamine" title="Galantamine">Galantamine</a></li> <li><a href="/wiki/Huperzine_A" title="Huperzine A">Huperzine A</a></li> <li><a href="/w/index.php?title=Huprine_W&action=edit&redlink=1" class="new" title="Huprine W (page does not exist)">Huprine W</a></li> <li><a href="/wiki/Huprine_X" title="Huprine X">Huprine X</a></li> <li><a href="/w/index.php?title=Huprine_Y&action=edit&redlink=1" class="new" title="Huprine Y (page does not exist)">Huprine Y</a></li> <li><a href="/wiki/Ipidacrine" title="Ipidacrine">Ipidacrine</a></li> <li><a href="/wiki/Itopride" title="Itopride">Itopride</a></li> <li><a href="/wiki/Ladostigil" title="Ladostigil">Ladostigil</a></li> <li><a href="/wiki/Minaprine" title="Minaprine">Minaprine</a></li> <li><a href="/wiki/Octamethylene-bis(5-dimethylcarbamoxyisoquinolinium_bromide)" title="Octamethylene-bis(5-dimethylcarbamoxyisoquinolinium bromide)">Octamethylene-bis(5-dimethylcarbamoxyisoquinolinium bromide)</a></li> <li><a href="/wiki/T-1123" title="T-1123">T-1123</a></li> <li><a href="/wiki/T-1152" title="T-1152">T-1152</a></li> <li><a href="/wiki/T-1194" title="T-1194">T-1194</a></li> <li><a href="/wiki/TL-599" title="TL-599">TL-599</a></li> <li><a href="/wiki/TL-1238" title="TL-1238">TL-1238</a></li> <li><a href="/wiki/Tacrine" title="Tacrine">Tacrine</a></li> <li><a href="/w/index.php?title=Zanapezil&action=edit&redlink=1" class="new" title="Zanapezil (page does not exist)">Zanapezil</a></li></ul> <ul><li><i>Irreversible:</i> Organophosphates: <a href="/wiki/2-Ethoxycarbonyl-1-methylvinyl_cyclohexyl_methylphosphonate" title="2-Ethoxycarbonyl-1-methylvinyl cyclohexyl methylphosphonate">2-Ethoxycarbonyl-1-methylvinyl cyclohexyl methylphosphonate</a></li> <li><a href="/wiki/Acephate" title="Acephate">Acephate</a></li> <li><a href="/wiki/Armine_(chemical)" title="Armine (chemical)">Armine</a></li> <li><a href="/wiki/Azinphos-ethyl" title="Azinphos-ethyl">Azinphos-ethyl</a></li> <li><a href="/wiki/Azinphos-methyl" title="Azinphos-methyl">Azinphos-methyl</a></li> <li><a href="/wiki/BAY-29952" title="BAY-29952">BAY-29952</a></li> <li><a href="/wiki/Bensulide" title="Bensulide">Bensulide</a></li> <li><a href="/wiki/Cadusafos" title="Cadusafos">Cadusafos</a></li> <li><a href="/wiki/Carbophenothion" title="Carbophenothion">Carbophenothion</a></li> <li><a href="/wiki/Chlorethoxyfos" title="Chlorethoxyfos">Chlorethoxyfos</a></li> <li><a href="/wiki/Chlorfenvinphos" title="Chlorfenvinphos">Chlorfenvinphos</a></li> <li><a href="/wiki/Chlorpyrifos" title="Chlorpyrifos">Chlorpyrifos</a></li> <li><a href="/wiki/Chlorpyrifos-methyl" class="mw-redirect" title="Chlorpyrifos-methyl">Chlorpyrifos-methyl</a></li> <li><a href="/wiki/Coumaphos" title="Coumaphos">Coumaphos</a></li> <li><a href="/wiki/Crotylsarin" title="Crotylsarin">Crotylsarin</a></li> <li><a href="/wiki/Cyanophos" title="Cyanophos">Cyanophos</a></li> <li><a href="/wiki/Cyclosarin" title="Cyclosarin">Cyclosarin (GF)</a></li> <li><a href="/wiki/Demephion" title="Demephion">Demephion</a></li> <li><a href="/wiki/Demeton" title="Demeton">Demeton</a></li> <li><a href="/wiki/Demeton-S-methyl" title="Demeton-S-methyl">Demeton-S-methyl</a></li> <li><a href="/wiki/Dialifor" title="Dialifor">Dialifor</a></li> <li><a href="/wiki/Diazinon" title="Diazinon">Diazinon</a></li> <li><a href="/wiki/Dichlorvos" title="Dichlorvos">Dichlorvos</a></li> <li><a href="/wiki/Dicrotophos" title="Dicrotophos">Dicrotophos</a></li> <li><a href="/wiki/Dicyclohexyl_phosphorofluoridate" title="Dicyclohexyl phosphorofluoridate">Dicyclohexyl phosphorofluoridate</a></li> <li><a href="/wiki/Diisopropylphosphate" title="Diisopropylphosphate">Diisopropylphosphate</a></li> <li><a href="/wiki/Diisopropyl_fluorophosphate" title="Diisopropyl fluorophosphate">Diisopropyl fluorophosphate</a></li> <li><a href="/wiki/Dimefox" title="Dimefox">Dimefox</a></li> <li><a href="/wiki/Dimethoate" title="Dimethoate">Dimethoate</a></li> <li><a href="/wiki/Dimethyl_4-(methylthio)phenyl_phosphate" title="Dimethyl 4-(methylthio)phenyl phosphate">Dimethyl 4-(methylthio)phenyl phosphate</a></li> <li><a href="/wiki/Dioxathion" title="Dioxathion">Dioxathion</a></li> <li><a href="/wiki/Disulfoton" title="Disulfoton">Disulfoton</a></li> <li><a href="/wiki/EA-2012" title="EA-2012">EA-2012</a></li> <li><a href="/wiki/EA-2054" title="EA-2054">EA-2054</a></li> <li><a href="/wiki/EA-2098" title="EA-2098">EA-2098</a></li> <li><a href="/wiki/EA-2192" title="EA-2192">EA-2192</a></li> <li><a href="/wiki/EA-2613" title="EA-2613">EA-2613</a></li> <li><a href="/wiki/EA-3148" title="EA-3148">EA-3148</a></li> <li><a href="/wiki/EA-4352" title="EA-4352">EA-4352</a></li> <li><a href="/wiki/Echothiophate" title="Echothiophate">Echothiophate</a></li> <li><a href="/wiki/Ethylsarin" title="Ethylsarin">Ethylsarin (GE)</a></li> <li><a href="/wiki/Endothion" title="Endothion">Endothion</a></li> <li><a href="/wiki/EPN_(insecticide)" title="EPN (insecticide)">EPN</a></li> <li><a href="/wiki/Ethion" title="Ethion">Ethion</a></li> <li><a href="/wiki/Ethoprop" class="mw-redirect" title="Ethoprop">Ethoprop</a></li> <li><a href="/wiki/Fenamiphos" title="Fenamiphos">Fenamiphos</a></li> <li><a href="/wiki/Fenitrothion" title="Fenitrothion">Fenitrothion</a></li> <li><a href="/wiki/Fenthion" title="Fenthion">Fenthion</a></li> <li><a href="/wiki/Fluorotabun" title="Fluorotabun">Fluorotabun</a></li> <li><a href="/wiki/Fonofos" title="Fonofos">Fonofos</a></li> <li><a href="/wiki/Formothion" title="Formothion">Formothion</a></li> <li><a href="/w/index.php?title=Fosthiazate&action=edit&redlink=1" class="new" title="Fosthiazate (page does not exist)">Fosthiazate</a></li> <li><a href="/wiki/GD-42" title="GD-42">GD-42</a></li> <li><a href="/wiki/GH_(nerve_agent)" title="GH (nerve agent)">GH</a></li> <li><a href="/w/index.php?title=GT-45&action=edit&redlink=1" class="new" title="GT-45 (page does not exist)">GT-45</a></li> <li><a href="/wiki/GV_(nerve_agent)" title="GV (nerve agent)">GV</a></li> <li><a href="/wiki/Guanitoxin" title="Guanitoxin">Guanitoxin</a></li> <li><a href="/wiki/Hexaethyl_tetraphosphate" title="Hexaethyl tetraphosphate">Hexaethyl tetraphosphate (HETP)</a></li> <li><a href="/wiki/Isofluorophate" class="mw-redirect" title="Isofluorophate">Isofluorophate</a></li> <li><a href="/wiki/Isoxathion" title="Isoxathion">Isoxathion</a></li> <li><a href="/wiki/Leptophos" title="Leptophos">Leptophos</a></li> <li><a href="/wiki/Malaoxon" title="Malaoxon">Malaoxon</a></li> <li><a href="/wiki/Malathion" title="Malathion">Malathion</a></li> <li><a href="/w/index.php?title=Mazidox&action=edit&redlink=1" class="new" title="Mazidox (page does not exist)">Mazidox</a></li> <li><a href="/wiki/Methamidophos" title="Methamidophos">Methamidophos</a></li> <li><a href="/wiki/Methidathion" title="Methidathion">Methidathion</a></li> <li><a href="/wiki/Methyl_phenkapton" title="Methyl phenkapton">Methyl phenkapton</a></li> <li><a href="/wiki/Methylfluorophosphonylcholine" title="Methylfluorophosphonylcholine">Methylfluorophosphonylcholine (MFPCh)</a></li> <li><a href="/wiki/Metrifonate" title="Metrifonate">Metrifonate</a></li> <li><a href="/wiki/Mevinphos" title="Mevinphos">Mevinphos</a></li> <li><a href="/wiki/Mipafox" title="Mipafox">Mipafox</a></li> <li><a href="/wiki/Monocrotophos" title="Monocrotophos">Monocrotophos</a></li> <li><a href="/wiki/MSPI_(nerve_agent)" title="MSPI (nerve agent)">MSPI</a></li> <li><a href="/wiki/Naled" title="Naled">Naled</a></li> <li><a href="/wiki/Novichok_agent" class="mw-redirect" title="Novichok agent">Novichok agent</a></li> <li><a href="/wiki/Omethoate" title="Omethoate">Omethoate</a></li> <li><a href="/wiki/Oxydemeton-methyl" title="Oxydemeton-methyl">Oxydemeton-methyl</a></li> <li><a href="/wiki/Paraoxon" title="Paraoxon">Paraoxon</a></li> <li><a href="/wiki/Parathion" title="Parathion">Parathion</a></li> <li><a href="/wiki/Parathion-methyl" class="mw-redirect" title="Parathion-methyl">Parathion-methyl</a></li> <li><a href="/wiki/Phorate" title="Phorate">Phorate</a></li> <li><a href="/wiki/Phosalone" title="Phosalone">Phosalone</a></li> <li><a href="/wiki/Phosfolan" title="Phosfolan">Phosfolan</a></li> <li><a href="/wiki/Phosmet" title="Phosmet">Phosmet</a></li> <li><a href="/wiki/Phosphamidon" title="Phosphamidon">Phosphamidon</a></li> <li><a href="/wiki/Phoxim" title="Phoxim">Phoxim</a></li> <li><a href="/wiki/Pirimiphos-methyl" title="Pirimiphos-methyl">Pirimiphos-methyl</a></li> <li><a href="/wiki/Profenofos" title="Profenofos">Profenofos</a></li> <li><a href="/wiki/Prothoate" title="Prothoate">Prothoate</a></li> <li><a href="/wiki/R-16661" title="R-16661">R-16661</a></li> <li><a href="/w/index.php?title=Ro_3-0340&action=edit&redlink=1" class="new" title="Ro 3-0340 (page does not exist)">Ro 3-0340</a></li> <li><a href="/w/index.php?title=Ro_3-0346&action=edit&redlink=1" class="new" title="Ro 3-0346 (page does not exist)">Ro 3-0346</a></li> <li><a href="/w/index.php?title=Ro_3-0347&action=edit&redlink=1" class="new" title="Ro 3-0347 (page does not exist)">Ro 3-0347</a></li> <li><a href="/w/index.php?title=Ro_3-0351&action=edit&redlink=1" class="new" title="Ro 3-0351 (page does not exist)">Ro 3-0351</a></li> <li><a href="/w/index.php?title=Ro_3-0352&action=edit&redlink=1" class="new" title="Ro 3-0352 (page does not exist)">Ro 3-0352</a></li> <li><a href="/w/index.php?title=Ro_3-0397&action=edit&redlink=1" class="new" title="Ro 3-0397 (page does not exist)">Ro 3-0397</a></li> <li><a href="/w/index.php?title=Ro_3-0411&action=edit&redlink=1" class="new" title="Ro 3-0411 (page does not exist)">Ro 3-0411</a></li> <li><a href="/wiki/Ro_3-0412" title="Ro 3-0412">Ro 3-0412</a></li> <li><a href="/w/index.php?title=Ro_3-0417&action=edit&redlink=1" class="new" title="Ro 3-0417 (page does not exist)">Ro 3-0417</a></li> <li><a href="/wiki/Ro_3-0419" title="Ro 3-0419">Ro 3-0419</a></li> <li><a href="/wiki/Ro_3-0422" title="Ro 3-0422">Ro 3-0422</a></li> <li><a href="/w/index.php?title=Ro_3-0433&action=edit&redlink=1" class="new" title="Ro 3-0433 (page does not exist)">Ro 3-0433</a></li> <li><a href="/w/index.php?title=Ronnel&action=edit&redlink=1" class="new" title="Ronnel (page does not exist)">Ronnel</a></li> <li><a href="/wiki/Sarin" title="Sarin">Sarin (GB)</a></li> <li><a href="/wiki/Schradan" title="Schradan">Schradan</a></li> <li><a href="/wiki/Soman" title="Soman">Soman (GD)</a></li> <li><a href="/wiki/Sulfotep" title="Sulfotep">Sulfotep (TEDP)</a></li> <li><a href="/wiki/Tabun_(nerve_agent)" title="Tabun (nerve agent)">Tabun (GA)</a></li> <li><a href="/wiki/Tebupirimfos" title="Tebupirimfos">Tebupirimfos</a></li> <li><a href="/wiki/Temefos" title="Temefos">Temefos</a></li> <li><a href="/wiki/Terbufos" title="Terbufos">Terbufos</a></li> <li><a href="/wiki/Tetrachlorvinphos" title="Tetrachlorvinphos">Tetrachlorvinphos</a></li> <li><a href="/wiki/Tetraethyl_pyrophosphate" title="Tetraethyl pyrophosphate">Tetraethyl pyrophosphate (TEPP)</a></li> <li><a href="/wiki/Triazofos" title="Triazofos">Triazofos</a></li> <li><a href="/w/index.php?title=Tribufos&action=edit&redlink=1" class="new" title="Tribufos (page does not exist)">Tribufos</a></li> <li><a href="/wiki/Trichlorfon" class="mw-redirect" title="Trichlorfon">Trichlorfon</a></li> <li><a href="/wiki/Trichloronate" title="Trichloronate">Trichloronate</a></li> <li><a href="/wiki/Tricresyl_phosphate" title="Tricresyl phosphate">Tricresyl phosphate</a></li> <li><a href="/wiki/VE_(nerve_agent)" title="VE (nerve agent)">VE</a></li> <li><a href="/wiki/VG_(nerve_agent)" title="VG (nerve agent)">VG</a></li> <li><a href="/wiki/VM_(nerve_agent)" title="VM (nerve agent)">VM</a></li> <li><a href="/wiki/VP_(nerve_agent)" class="mw-redirect" title="VP (nerve agent)">VP</a></li> <li><a href="/wiki/VS_(nerve_agent)" title="VS (nerve agent)">VS</a></li> <li><a href="/wiki/VR_(nerve_agent)" title="VR (nerve agent)">VR</a></li> <li><a href="/wiki/VX_(nerve_agent)" title="VX (nerve agent)">VX</a>; Others: <a href="/wiki/Demecarium" class="mw-redirect" title="Demecarium">Demecarium</a></li> <li><a href="/wiki/Fasciculin" title="Fasciculin">Fasciculins (green mamba toxins)</a> (<a href="/w/index.php?title=Fasciculin_1&action=edit&redlink=1" class="new" title="Fasciculin 1 (page does not exist)">1</a>, <a href="/w/index.php?title=Fasciculin_2&action=edit&redlink=1" class="new" title="Fasciculin 2 (page does not exist)">2</a>, <a href="/w/index.php?title=Fasciculin_3&action=edit&redlink=1" class="new" title="Fasciculin 3 (page does not exist)">3</a>, <a href="/w/index.php?title=Fasciculin_4&action=edit&redlink=1" class="new" title="Fasciculin 4 (page does not exist)">4</a>)</li> <li><a href="/wiki/Onchidal" title="Onchidal">Onchidal</a> (<i><a href="/wiki/Onchidella_binneyi" title="Onchidella binneyi">Onchidella binneyi</a></i>)</li> <li><a href="/wiki/Methanesulfonyl_fluoride" title="Methanesulfonyl fluoride">Methanesulfonyl fluoride</a></li></ul> <ul><li><i>Unsorted:</i> <a href="/wiki/%CE%91-Pinene" title="Α-Pinene">α-Pinene</a></li> <li><a href="/wiki/%CE%91-Viniferin" title="Α-Viniferin">α-Viniferin</a></li> <li><a href="/wiki/Affinine" title="Affinine">Affinine</a></li> <li><a href="/wiki/Affinisine" title="Affinisine">Affinisine</a></li> <li><a href="/wiki/Arisugacin_A" title="Arisugacin A">Arisugacin A</a></li> <li><a href="/wiki/Bulbocapnine" title="Bulbocapnine">Bulbocapnine</a></li> <li><a href="/wiki/Conodurine" title="Conodurine">Conodurine</a></li> <li><a href="/wiki/Coronaridine" title="Coronaridine">Coronaridine</a></li> <li><a href="/wiki/Corydaline" title="Corydaline">Corydaline</a></li> <li><a href="/wiki/Corynoline" title="Corynoline">Corynoline</a></li> <li><a href="/wiki/Crimidine" title="Crimidine">Crimidine</a></li> <li><a href="/wiki/Cyclanoline" title="Cyclanoline">Cyclanoline</a></li> <li><a href="/wiki/Cymserine" title="Cymserine">Cymserine</a></li> <li><a href="/wiki/Harmaline" title="Harmaline">Harmaline</a></li> <li><a href="/wiki/Kobophenol_A" title="Kobophenol A">Kobophenol A</a></li> <li><a href="/wiki/Lactucopicrin" title="Lactucopicrin">Lactucopicrin</a></li> <li><a href="/wiki/Lycorine" title="Lycorine">Lycorine</a></li> <li><a href="/wiki/Phosacetim" title="Phosacetim">Phosacetim</a></li> <li><a href="/wiki/Rosmarinic_acid" title="Rosmarinic acid">Rosmarinic acid</a></li> <li><a href="/wiki/Stercuronium_iodide" title="Stercuronium iodide">Stercuronium iodide</a></li> <li><a href="/wiki/Taspine" title="Taspine">Taspine</a></li> <li><a href="/wiki/Tetrahydrocannabinol" title="Tetrahydrocannabinol">Tetrahydrocannabinol</a></li> <li><a href="/wiki/Ungeremine" title="Ungeremine">Ungeremine</a></li> <li><a href="/wiki/Ungiminorine" title="Ungiminorine">Ungiminorine</a></li> <li><a href="/wiki/Dimethylcarbamoyl_fluoride" title="Dimethylcarbamoyl fluoride">Dimethylcarbamoyl fluoride</a></li> <li><a href="/wiki/BW284C51" title="BW284C51">BW284C51</a></li> <li><a href="/wiki/TMTFA" title="TMTFA">TMTFA</a></li> <li><a href="/wiki/3152_CT" title="3152 CT">3152 CT</a></li></ul> <ul><li><a href="/wiki/Cholinesterase_reactivator" title="Cholinesterase reactivator">Reactivators</a>: <a href="/wiki/Asoxime_chloride" title="Asoxime chloride">Asoxime chloride</a></li> <li><a href="/w/index.php?title=Methoxime&action=edit&redlink=1" class="new" title="Methoxime (page does not exist)">Methoxime</a></li> <li><a href="/wiki/Obidoxime" title="Obidoxime">Obidoxime</a></li> <li><a href="/wiki/Pralidoxime" title="Pralidoxime">Pralidoxime</a></li> <li><a href="/wiki/Trimedoxime_bromide" title="Trimedoxime bromide">Trimedoxime bromide</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:6em;;text-align:center;"><a href="/wiki/Butyrylcholinesterase" title="Butyrylcholinesterase"><abbr title="Butyrylcholinesterase">BChE</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 Butyrylcholinesterase</span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><b>Inhibitors:</b> <a href="/wiki/Affinine" title="Affinine">Affinine</a></li> <li><a href="/wiki/Affinisine" title="Affinisine">Affinisine</a></li> <li><a href="/wiki/Conodurine" title="Conodurine">Conodurine</a></li> <li><a href="/wiki/Cymserine" title="Cymserine">Cymserine</a></li> <li><a href="/wiki/Ladostigil" title="Ladostigil">Ladostigil</a></li> <li><a href="/wiki/Profenamine" title="Profenamine">Profenamine (ethopropazine)</a></li> <li><a href="/wiki/Rivastigmine" title="Rivastigmine">Rivastigmine</a></li> <li><a href="/wiki/Tacrine" title="Tacrine">Tacrine</a></li> <li><a href="/w/index.php?title=ZINC-12613047&action=edit&redlink=1" class="new" title="ZINC-12613047 (page does not exist)">ZINC-12613047</a></li> <li>Many of the other AChE inhibitors listed above</li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Neurotransmitter_transporter" title="Neurotransmitter transporter">Transporter</a><br /><small>(<a href="/wiki/Transporter_modulator" class="mw-redirect" title="Transporter modulator">modulators</a>)</small></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:6em;;text-align:center;"><a href="/wiki/Choline_transporter" title="Choline transporter"><abbr title="Choline transporter">CHT</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 Choline transporter</span></th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><b>Inhibitors:</b> <a href="/wiki/Hemicholinium-3" title="Hemicholinium-3">Hemicholinium-3 (hemicholine)</a></li> <li><a href="/wiki/Triethylcholine" title="Triethylcholine">Triethylcholine</a></li></ul> <ul><li><b>Enhancers:</b> <a href="/wiki/Coluracetam" title="Coluracetam">Coluracetam</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:6em;;text-align:center;"><a href="/wiki/Vesicular_acetylcholine_transporter" title="Vesicular acetylcholine transporter"><abbr title="Vesicular acetylcholine transporter">VAChT</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 Vesicular acetylcholine transporter</span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><b>Inhibitors:</b> <a href="/wiki/Vesamicol" title="Vesamicol">Vesamicol</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/Neurotransmitter_release" class="mw-redirect" title="Neurotransmitter release">Release</a><br /><small>(<a href="/wiki/Release_modulator" title="Release modulator">modulators</a>)</small></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:6em;;text-align:center;"><a href="/wiki/Release_inhibitor" class="mw-redirect" title="Release inhibitor">Inhibitors</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><b><a href="/wiki/Synaptosomal-associated_protein_25" class="mw-redirect" title="Synaptosomal-associated protein 25"><abbr title="Synaptosomal-associated protein 25">SNAP-25</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 Synaptosomal-associated protein 25</span> inactivators:</b> <a href="/wiki/Botulinum_toxin" title="Botulinum toxin">Botulinum toxin</a> (<a href="/wiki/Botulinum_toxin_A" class="mw-redirect" title="Botulinum toxin A">A</a>, <a href="/wiki/Botulinum_toxin_C" class="mw-redirect" title="Botulinum toxin C">C</a>, <a href="/wiki/Botulinum_toxin_E" class="mw-redirect" title="Botulinum toxin E">E</a>)</li></ul> <ul><li><b><a href="/wiki/Vesicle-associated_membrane_protein" title="Vesicle-associated membrane protein"><abbr title="Vesicle-associated membrane protein">VAMP</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 Vesicle-associated membrane protein</span> inactivators:</b> <a href="/wiki/Botulinum_toxin" title="Botulinum toxin">Botulinum toxin</a> (<a href="/wiki/Botulinum_toxin_B" class="mw-redirect" title="Botulinum toxin B">B</a>, <a href="/wiki/Botulinum_toxin_D" class="mw-redirect" title="Botulinum toxin D">D</a>, <a href="/wiki/Botulinum_toxin_F" class="mw-redirect" title="Botulinum toxin F">F</a>, <a href="/wiki/Botulinum_toxin_G" class="mw-redirect" title="Botulinum toxin G">G</a>)</li></ul> <ul><li><b>Others:</b> <a href="/wiki/Bungarotoxin" title="Bungarotoxin">Bungarotoxins</a> (<a href="/wiki/Beta-Bungarotoxin" class="mw-redirect" title="Beta-Bungarotoxin">β-bungarotoxin</a>, <a href="/wiki/%CE%93-bungarotoxin" class="mw-redirect" title="Γ-bungarotoxin">γ-bungarotoxin</a>)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:6em;;text-align:center;"><a href="/wiki/Release_enhancer" class="mw-redirect" title="Release enhancer">Enhancers</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><b><a href="/wiki/Latrophilin" title="Latrophilin"><abbr title="Latrophilin">LPHN</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 Latrophilin</span> agonists:</b> <a href="/wiki/Alpha-Latrotoxin" class="mw-redirect" title="Alpha-Latrotoxin">α-Latrotoxin</a></li></ul> <ul><li><b>Others:</b> Atracotoxins (e.g., <a href="/wiki/Robustoxin" class="mw-redirect" title="Robustoxin">robustoxin</a>, <a href="/wiki/Versutoxin" title="Versutoxin">versutoxin</a>)</li> <li><a href="/wiki/Crotoxin" title="Crotoxin">Crotoxin</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><td class="navbox-abovebelow" colspan="2"><div> <dl><dt>See also</dt> <dd><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:Nicotinic_acetylcholine_receptor_modulators" title="Template:Nicotinic acetylcholine receptor modulators">Nicotinic acetylcholine receptor 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 authority-control" aria-label="Navbox" style="padding:3px"><table class="nowraplinks hlist navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Help:Authority_control" title="Help:Authority control">Authority control databases</a>: National <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q193166#identifiers" 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></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"><ul><li><span class="uid"><a rel="nofollow" class="external text" href="https://d-nb.info/gnd/4147865-4">Germany</a></span></li><li><span class="uid"><a rel="nofollow" class="external text" href="https://id.loc.gov/authorities/sh85024656">United States</a></span></li><li><span class="uid"><a rel="nofollow" class="external text" href="https://catalogue.bnf.fr/ark:/12148/cb122695833">France</a></span></li><li><span class="uid"><a rel="nofollow" class="external text" href="https://data.bnf.fr/ark:/12148/cb122695833">BnF data</a></span></li><li><span class="uid"><a rel="nofollow" class="external text" href="https://id.ndl.go.jp/auth/ndlna/00566629">Japan</a></span></li><li><span class="uid"><a rel="nofollow" class="external text" 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