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class="vector-toc-text"> <span class="vector-toc-numb">2</span> <span>Dietary requirements and sources</span> </div> </a> <ul id="toc-Dietary_requirements_and_sources-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Biosynthesis" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Biosynthesis"> <div class="vector-toc-text"> <span class="vector-toc-numb">3</span> <span>Biosynthesis</span> </div> </a> <ul id="toc-Biosynthesis-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Metabolism" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Metabolism"> <div class="vector-toc-text"> <span class="vector-toc-numb">4</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-Phosphorylation_and_sulfation" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Phosphorylation_and_sulfation"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.1</span> <span>Phosphorylation and sulfation</span> </div> </a> <ul id="toc-Phosphorylation_and_sulfation-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Precursor_to_neurotransmitters_and_hormones" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Precursor_to_neurotransmitters_and_hormones"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.2</span> <span>Precursor to neurotransmitters and hormones</span> </div> </a> <ul id="toc-Precursor_to_neurotransmitters_and_hormones-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Precursor_to_other_compounds" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Precursor_to_other_compounds"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.3</span> <span>Precursor to other compounds</span> </div> </a> <ul id="toc-Precursor_to_other_compounds-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Degradation" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Degradation"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.4</span> <span>Degradation</span> </div> </a> <ul id="toc-Degradation-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Ortho-_and_meta-tyrosine" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Ortho-_and_meta-tyrosine"> <div class="vector-toc-text"> <span class="vector-toc-numb">5</span> <span>Ortho- and meta-tyrosine</span> </div> </a> <ul id="toc-Ortho-_and_meta-tyrosine-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Medical_use" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Medical_use"> <div class="vector-toc-text"> <span class="vector-toc-numb">6</span> <span>Medical use</span> </div> </a> <ul id="toc-Medical_use-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Industrial_synthesis" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Industrial_synthesis"> <div class="vector-toc-text"> <span class="vector-toc-numb">7</span> <span>Industrial synthesis</span> </div> </a> <ul id="toc-Industrial_synthesis-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-See_also" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#See_also"> <div class="vector-toc-text"> <span class="vector-toc-numb">8</span> <span>See also</span> </div> </a> <ul id="toc-See_also-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-References" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#References"> <div class="vector-toc-text"> <span class="vector-toc-numb">9</span> <span>References</span> </div> </a> <ul id="toc-References-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-External_links" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#External_links"> <div class="vector-toc-text"> <span class="vector-toc-numb">10</span> <span>External links</span> </div> </a> <ul id="toc-External_links-sublist" class="vector-toc-list"> </ul> </li> </ul> </div> </div> </nav> </div> </div> <div class="mw-content-container"> <main id="content" class="mw-body"> <header class="mw-body-header vector-page-titlebar"> <nav aria-label="Contents" class="vector-toc-landmark"> <div id="vector-page-titlebar-toc" class="vector-dropdown vector-page-titlebar-toc vector-button-flush-left" > <input type="checkbox" id="vector-page-titlebar-toc-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-vector-page-titlebar-toc" class="vector-dropdown-checkbox " aria-label="Toggle the table of contents" > <label id="vector-page-titlebar-toc-label" for="vector-page-titlebar-toc-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--icon-only " aria-hidden="true" ><span class="vector-icon mw-ui-icon-listBullet mw-ui-icon-wikimedia-listBullet"></span> <span class="vector-dropdown-label-text">Toggle the table of contents</span> </label> <div class="vector-dropdown-content"> <div id="vector-page-titlebar-toc-unpinned-container" class="vector-unpinned-container"> </div> </div> </div> </nav> <h1 id="firstHeading" class="firstHeading mw-first-heading"><span class="mw-page-title-main">Tyrosine</span></h1> <div id="p-lang-btn" class="vector-dropdown mw-portlet mw-portlet-lang" > <input type="checkbox" id="p-lang-btn-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-p-lang-btn" class="vector-dropdown-checkbox mw-interlanguage-selector" aria-label="Go to an article in another language. Available in 60 languages" > <label id="p-lang-btn-label" for="p-lang-btn-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--action-progressive mw-portlet-lang-heading-60" aria-hidden="true" ><span class="vector-icon mw-ui-icon-language-progressive mw-ui-icon-wikimedia-language-progressive"></span> <span class="vector-dropdown-label-text">60 languages</span> </label> <div class="vector-dropdown-content"> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li class="interlanguage-link interwiki-ar mw-list-item"><a href="https://ar.wikipedia.org/wiki/%D8%AA%D9%8A%D8%B1%D9%88%D8%B3%D9%8A%D9%86" title="تيروسين – Arabic" lang="ar" hreflang="ar" data-title="تيروسين" data-language-autonym="العربية" data-language-local-name="Arabic" class="interlanguage-link-target"><span>العربية</span></a></li><li class="interlanguage-link interwiki-azb mw-list-item"><a href="https://azb.wikipedia.org/wiki/%D8%AA%DB%8C%D8%B1%D9%88%D8%B2%DB%8C%D9%86" title="تیروزین – South Azerbaijani" lang="azb" hreflang="azb" data-title="تیروزین" data-language-autonym="تۆرکجه" data-language-local-name="South Azerbaijani" class="interlanguage-link-target"><span>تۆرکجه</span></a></li><li class="interlanguage-link interwiki-zh-min-nan mw-list-item"><a href="https://zh-min-nan.wikipedia.org/wiki/Tyrosin" title="Tyrosin – Minnan" lang="nan" hreflang="nan" data-title="Tyrosin" data-language-autonym="閩南語 / Bân-lâm-gú" data-language-local-name="Minnan" class="interlanguage-link-target"><span>閩南語 / Bân-lâm-gú</span></a></li><li class="interlanguage-link interwiki-bg mw-list-item"><a href="https://bg.wikipedia.org/wiki/%D0%A2%D0%B8%D1%80%D0%BE%D0%B7%D0%B8%D0%BD" title="Тирозин – Bulgarian" lang="bg" hreflang="bg" data-title="Тирозин" 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/Tirozin" title="Tirozin – Bosnian" lang="bs" hreflang="bs" data-title="Tirozin" 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/Tirosina" title="Tirosina – Catalan" lang="ca" hreflang="ca" data-title="Tirosina" 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/Tyrosin" title="Tyrosin – Czech" lang="cs" hreflang="cs" data-title="Tyrosin" data-language-autonym="Čeština" data-language-local-name="Czech" class="interlanguage-link-target"><span>Čeština</span></a></li><li class="interlanguage-link interwiki-da mw-list-item"><a href="https://da.wikipedia.org/wiki/Tyrosin" title="Tyrosin – Danish" lang="da" hreflang="da" data-title="Tyrosin" 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/Tyrosin" title="Tyrosin – German" lang="de" hreflang="de" data-title="Tyrosin" 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/T%C3%BCrosiin" title="Türosiin – Estonian" lang="et" hreflang="et" data-title="Türosiin" 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%A4%CF%85%CF%81%CE%BF%CF%83%CE%AF%CE%BD%CE%B7" title="Τυροσίνη – Greek" lang="el" hreflang="el" data-title="Τυροσίνη" 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/Tirosina" title="Tirosina – Spanish" lang="es" hreflang="es" data-title="Tirosina" 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/Tirozino" title="Tirozino – Esperanto" lang="eo" hreflang="eo" data-title="Tirozino" 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/Tirosina" title="Tirosina – Basque" lang="eu" hreflang="eu" data-title="Tirosina" data-language-autonym="Euskara" data-language-local-name="Basque" class="interlanguage-link-target"><span>Euskara</span></a></li><li class="interlanguage-link interwiki-fa mw-list-item"><a href="https://fa.wikipedia.org/wiki/%D8%AA%DB%8C%D8%B1%D9%88%D8%B2%DB%8C%D9%86" title="تیروزین – Persian" lang="fa" hreflang="fa" data-title="تیروزین" 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/Tyrosine" title="Tyrosine – French" lang="fr" hreflang="fr" data-title="Tyrosine" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target"><span>Français</span></a></li><li class="interlanguage-link interwiki-fy mw-list-item"><a href="https://fy.wikipedia.org/wiki/Tyrosine" title="Tyrosine – Western Frisian" lang="fy" hreflang="fy" data-title="Tyrosine" data-language-autonym="Frysk" data-language-local-name="Western Frisian" class="interlanguage-link-target"><span>Frysk</span></a></li><li class="interlanguage-link interwiki-gl mw-list-item"><a href="https://gl.wikipedia.org/wiki/Tirosina" title="Tirosina – Galician" lang="gl" hreflang="gl" data-title="Tirosina" data-language-autonym="Galego" data-language-local-name="Galician" class="interlanguage-link-target"><span>Galego</span></a></li><li class="interlanguage-link interwiki-ko mw-list-item"><a href="https://ko.wikipedia.org/wiki/%ED%8B%B0%EB%A1%9C%EC%8B%A0_(%EC%95%84%EB%AF%B8%EB%85%B8%EC%82%B0)" title="티로신 (아미노산) – Korean" lang="ko" hreflang="ko" data-title="티로신 (아미노산)" data-language-autonym="한국어" data-language-local-name="Korean" class="interlanguage-link-target"><span>한국어</span></a></li><li class="interlanguage-link interwiki-hy mw-list-item"><a href="https://hy.wikipedia.org/wiki/%D4%B9%D5%AB%D6%80%D5%B8%D5%A6%D5%AB%D5%B6" title="Թիրոզին – Armenian" lang="hy" hreflang="hy" data-title="Թիրոզին" data-language-autonym="Հայերեն" data-language-local-name="Armenian" class="interlanguage-link-target"><span>Հայերեն</span></a></li><li class="interlanguage-link interwiki-hr mw-list-item"><a href="https://hr.wikipedia.org/wiki/Tirozin" title="Tirozin – Croatian" lang="hr" hreflang="hr" data-title="Tirozin" data-language-autonym="Hrvatski" data-language-local-name="Croatian" class="interlanguage-link-target"><span>Hrvatski</span></a></li><li class="interlanguage-link interwiki-io mw-list-item"><a href="https://io.wikipedia.org/wiki/Tirozino" title="Tirozino – Ido" lang="io" hreflang="io" data-title="Tirozino" data-language-autonym="Ido" data-language-local-name="Ido" class="interlanguage-link-target"><span>Ido</span></a></li><li class="interlanguage-link interwiki-id mw-list-item"><a href="https://id.wikipedia.org/wiki/Tirosina" title="Tirosina – Indonesian" lang="id" hreflang="id" data-title="Tirosina" 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/Tirosina" title="Tirosina – Italian" lang="it" hreflang="it" data-title="Tirosina" 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%98%D7%99%D7%A8%D7%95%D7%96%D7%99%D7%9F" title="טירוזין – Hebrew" lang="he" hreflang="he" data-title="טירוזין" data-language-autonym="עברית" data-language-local-name="Hebrew" class="interlanguage-link-target"><span>עברית</span></a></li><li class="interlanguage-link interwiki-ku mw-list-item"><a href="https://ku.wikipedia.org/wiki/T%C3%AEros%C3%AEn" title="Tîrosîn – Kurdish" lang="ku" hreflang="ku" data-title="Tîrosîn" data-language-autonym="Kurdî" data-language-local-name="Kurdish" class="interlanguage-link-target"><span>Kurdî</span></a></li><li class="interlanguage-link interwiki-lv mw-list-item"><a href="https://lv.wikipedia.org/wiki/Tiroz%C4%ABns" title="Tirozīns – Latvian" lang="lv" hreflang="lv" data-title="Tirozīns" data-language-autonym="Latviešu" data-language-local-name="Latvian" class="interlanguage-link-target"><span>Latviešu</span></a></li><li class="interlanguage-link interwiki-lb mw-list-item"><a href="https://lb.wikipedia.org/wiki/Tyrosin" title="Tyrosin – Luxembourgish" lang="lb" hreflang="lb" data-title="Tyrosin" data-language-autonym="Lëtzebuergesch" data-language-local-name="Luxembourgish" class="interlanguage-link-target"><span>Lëtzebuergesch</span></a></li><li class="interlanguage-link interwiki-lt mw-list-item"><a href="https://lt.wikipedia.org/wiki/Tirozinas" title="Tirozinas – Lithuanian" lang="lt" hreflang="lt" data-title="Tirozinas" 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/Tirozin" title="Tirozin – Hungarian" lang="hu" hreflang="hu" data-title="Tirozin" data-language-autonym="Magyar" data-language-local-name="Hungarian" class="interlanguage-link-target"><span>Magyar</span></a></li><li class="interlanguage-link interwiki-mk mw-list-item"><a href="https://mk.wikipedia.org/wiki/%D0%A2%D0%B8%D1%80%D0%BE%D0%B7%D0%B8%D0%BD" title="Тирозин – Macedonian" lang="mk" hreflang="mk" data-title="Тирозин" data-language-autonym="Македонски" data-language-local-name="Macedonian" class="interlanguage-link-target"><span>Македонски</span></a></li><li class="interlanguage-link interwiki-arz mw-list-item"><a href="https://arz.wikipedia.org/wiki/%D8%AA%D9%8A%D8%B1%D9%88%D8%B3%D9%8A%D9%86" title="تيروسين – Egyptian Arabic" lang="arz" hreflang="arz" data-title="تيروسين" data-language-autonym="مصرى" data-language-local-name="Egyptian Arabic" class="interlanguage-link-target"><span>مصرى</span></a></li><li class="interlanguage-link interwiki-ms mw-list-item"><a href="https://ms.wikipedia.org/wiki/Tirosina" title="Tirosina – Malay" lang="ms" hreflang="ms" data-title="Tirosina" data-language-autonym="Bahasa Melayu" data-language-local-name="Malay" class="interlanguage-link-target"><span>Bahasa Melayu</span></a></li><li class="interlanguage-link interwiki-mn mw-list-item"><a href="https://mn.wikipedia.org/wiki/%D0%A2%D0%B8%D1%80%D0%BE%D0%B7%D0%B8%D0%BD" title="Тирозин – Mongolian" lang="mn" hreflang="mn" data-title="Тирозин" data-language-autonym="Монгол" data-language-local-name="Mongolian" class="interlanguage-link-target"><span>Монгол</span></a></li><li class="interlanguage-link interwiki-nl badge-Q17437796 badge-featuredarticle mw-list-item" title="featured article badge"><a href="https://nl.wikipedia.org/wiki/Tyrosine" title="Tyrosine – Dutch" lang="nl" hreflang="nl" data-title="Tyrosine" data-language-autonym="Nederlands" data-language-local-name="Dutch" class="interlanguage-link-target"><span>Nederlands</span></a></li><li class="interlanguage-link interwiki-ja mw-list-item"><a href="https://ja.wikipedia.org/wiki/%E3%83%81%E3%83%AD%E3%82%B7%E3%83%B3" title="チロシン – Japanese" lang="ja" hreflang="ja" data-title="チロシン" data-language-autonym="日本語" data-language-local-name="Japanese" class="interlanguage-link-target"><span>日本語</span></a></li><li class="interlanguage-link interwiki-no mw-list-item"><a href="https://no.wikipedia.org/wiki/Tyrosin" title="Tyrosin – Norwegian Bokmål" lang="nb" hreflang="nb" data-title="Tyrosin" data-language-autonym="Norsk bokmål" data-language-local-name="Norwegian Bokmål" class="interlanguage-link-target"><span>Norsk bokmål</span></a></li><li class="interlanguage-link interwiki-nn mw-list-item"><a href="https://nn.wikipedia.org/wiki/Tyrosin" title="Tyrosin – Norwegian Nynorsk" lang="nn" hreflang="nn" data-title="Tyrosin" data-language-autonym="Norsk nynorsk" data-language-local-name="Norwegian Nynorsk" class="interlanguage-link-target"><span>Norsk nynorsk</span></a></li><li class="interlanguage-link interwiki-oc mw-list-item"><a href="https://oc.wikipedia.org/wiki/Tirosina" title="Tirosina – Occitan" lang="oc" hreflang="oc" data-title="Tirosina" data-language-autonym="Occitan" data-language-local-name="Occitan" class="interlanguage-link-target"><span>Occitan</span></a></li><li class="interlanguage-link interwiki-uz mw-list-item"><a href="https://uz.wikipedia.org/wiki/Tirozin" title="Tirozin – Uzbek" lang="uz" hreflang="uz" data-title="Tirozin" data-language-autonym="Oʻzbekcha / ўзбекча" data-language-local-name="Uzbek" class="interlanguage-link-target"><span>Oʻzbekcha / ўзбекча</span></a></li><li class="interlanguage-link interwiki-pl mw-list-item"><a href="https://pl.wikipedia.org/wiki/Tyrozyna" title="Tyrozyna – Polish" lang="pl" hreflang="pl" data-title="Tyrozyna" 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/Tirosina" title="Tirosina – Portuguese" lang="pt" hreflang="pt" data-title="Tirosina" 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/Tirozin%C4%83" title="Tirozină – Romanian" lang="ro" hreflang="ro" data-title="Tirozină" data-language-autonym="Română" data-language-local-name="Romanian" class="interlanguage-link-target"><span>Română</span></a></li><li class="interlanguage-link interwiki-ru mw-list-item"><a href="https://ru.wikipedia.org/wiki/%D0%A2%D0%B8%D1%80%D0%BE%D0%B7%D0%B8%D0%BD" title="Тирозин – Russian" lang="ru" hreflang="ru" data-title="Тирозин" data-language-autonym="Русский" data-language-local-name="Russian" class="interlanguage-link-target"><span>Русский</span></a></li><li class="interlanguage-link interwiki-simple mw-list-item"><a href="https://simple.wikipedia.org/wiki/Tyrosine" title="Tyrosine – Simple English" lang="en-simple" hreflang="en-simple" data-title="Tyrosine" 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/Tyroz%C3%ADn" title="Tyrozín – Slovak" lang="sk" hreflang="sk" data-title="Tyrozín" data-language-autonym="Slovenčina" data-language-local-name="Slovak" class="interlanguage-link-target"><span>Slovenčina</span></a></li><li class="interlanguage-link interwiki-sl 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class="vector-pinnable-header-toggle-button vector-pinnable-header-unpin-button" data-event-name="pinnable-header.vector-appearance.unpin">hide</button> </div> </div> </div> </nav> </div> </div> <div id="bodyContent" class="vector-body" aria-labelledby="firstHeading" data-mw-ve-target-container> <div class="vector-body-before-content"> <div class="mw-indicators"> </div> <div id="siteSub" class="noprint">From Wikipedia, the free encyclopedia</div> </div> <div id="contentSub"><div id="mw-content-subtitle"><span class="mw-redirectedfrom">(Redirected from <a href="/w/index.php?title=L-tyrosine&redirect=no" class="mw-redirect" title="L-tyrosine">L-tyrosine</a>)</span></div></div> <div id="mw-content-text" class="mw-body-content"><div class="mw-content-ltr mw-parser-output" lang="en" dir="ltr"><div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Amino acid</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>Tyrosine </caption> <tbody><tr> <td colspan="2" style="text-align:center; padding:2px;"><span typeof="mw:File"><a href="/wiki/File:L-Tyrosin_-_L-Tyrosine.svg" class="mw-file-description" title="Skeletal formula of the L-isomer"><img alt="Skeletal formula of the L-isomer" src="//upload.wikimedia.org/wikipedia/commons/thumb/4/40/L-Tyrosin_-_L-Tyrosine.svg/220px-L-Tyrosin_-_L-Tyrosine.svg.png" decoding="async" width="220" height="104" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/4/40/L-Tyrosin_-_L-Tyrosine.svg/330px-L-Tyrosin_-_L-Tyrosine.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/4/40/L-Tyrosin_-_L-Tyrosine.svg/440px-L-Tyrosin_-_L-Tyrosine.svg.png 2x" data-file-width="290" data-file-height="137" /></a></span><br /><div style="text-align:center;"><a href="/wiki/Skeletal_formula" title="Skeletal formula">Skeletal formula</a> of <small>L</small>-tyrosine</div> </td></tr> <tr> <td colspan="2" style="text-align:center; padding:2px;"><span typeof="mw:File"><a href="/wiki/File:L-Tyrosin_phys.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/b/b7/L-Tyrosin_phys.svg/220px-L-Tyrosin_phys.svg.png" decoding="async" width="220" height="78" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/b/b7/L-Tyrosin_phys.svg/330px-L-Tyrosin_phys.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/b/b7/L-Tyrosin_phys.svg/440px-L-Tyrosin_phys.svg.png 2x" data-file-width="282" data-file-height="100" /></a></span><br /><div style="text-align:center;"><small>L</small>-Tyrosine at physiological pH</div> </td></tr> <tr> <td colspan="2" class="borderless" style="text-align:center"> <table border="0" style="width:100%;display:inline-table;"> <tbody><tr> <td style="border-right:1px solid #aaa; width:50%;"><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Tyrosine-from-xtal-3D-bs-17.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/4/4a/Tyrosine-from-xtal-3D-bs-17.png/110px-Tyrosine-from-xtal-3D-bs-17.png" decoding="async" width="110" height="70" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/4/4a/Tyrosine-from-xtal-3D-bs-17.png/165px-Tyrosine-from-xtal-3D-bs-17.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/4/4a/Tyrosine-from-xtal-3D-bs-17.png/220px-Tyrosine-from-xtal-3D-bs-17.png 2x" data-file-width="3000" data-file-height="1922" /></a><figcaption></figcaption></figure><div style="text-align:center"><a href="/wiki/Ball-and-stick_model" title="Ball-and-stick model">ball-and-stick model</a><sup id="cite_ref-Frey_1-0" class="reference"><a href="#cite_note-Frey-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup></div> </td> <td style="width:50%;"><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Tyrosine-from-xtal-3D-sf.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/e/e3/Tyrosine-from-xtal-3D-sf.png/110px-Tyrosine-from-xtal-3D-sf.png" decoding="async" width="110" height="80" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/e3/Tyrosine-from-xtal-3D-sf.png/165px-Tyrosine-from-xtal-3D-sf.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/e/e3/Tyrosine-from-xtal-3D-sf.png/220px-Tyrosine-from-xtal-3D-sf.png 2x" data-file-width="3000" data-file-height="2194" /></a><figcaption></figcaption></figure><div style="text-align:center"><a href="/wiki/Space-filling_model" title="Space-filling model">space-filling model</a><sup id="cite_ref-Frey_1-1" class="reference"><a href="#cite_note-Frey-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup></div> </td></tr></tbody></table> </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;">(<i>S</i>)-Tyrosine</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;"><small>L</small>-2-Amino-3-(4-hydroxyphenyl)propanoic acid</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><style data-mw-deduplicate="TemplateStyles:r1126788409">.mw-parser-output .plainlist ol,.mw-parser-output .plainlist ul{line-height:inherit;list-style:none;margin:0;padding:0}.mw-parser-output .plainlist ol li,.mw-parser-output .plainlist ul li{margin-bottom:0}</style><div class="plainlist"><ul><li><span title="commonchemistry.cas.org"><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=60-18-4">60-18-4</a></span> (<small>L</small>)<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=N%5BC%40%40H%5D%28Cc1ccc%28O%29cc1%29C%28O%29%3DO">Interactive image</a></span></li><li><a href="/wiki/Zwitterion" title="Zwitterion">Zwitterion</a>: <span title="chemapps.stolaf.edu (3D interactive model)"><a rel="nofollow" class="external text" href="https://chemapps.stolaf.edu/jmol/jmol.php?model=%5BNH3%2B%5D%5BC%40%40H%5D%28Cc1ccc%28O%29cc1%29C%28%5BO-%5D%29%3DO">Interactive image</a></span></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ChEBI" title="ChEBI">ChEBI</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.ebi.ac.uk"><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chebi/searchId.do?chebiId=17895">CHEBI:17895</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ChEMBL" title="ChEMBL">ChEMBL</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.ebi.ac.uk"><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chembl/explore/compound/ChEMBL925">ChEMBL925</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.5833.html">5833</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/DB00135">DB00135</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/100.000.419">100.000.419</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q188017#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><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=4791">4791</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/C00082">C00082</a></span></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/6057">6057</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/42HK56048U">42HK56048U</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/DTXSID1023730">DTXSID1023730</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q188017#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/C9H11NO3/c10-8(9(12)13)5-6-1-3-7(11)4-2-6/h1-4,8,11H,5,10H2,(H,12,13)/t8-/m0/s1<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: OUYCCCASQSFEME-QMMMGPOBSA-N<sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></div></div></li><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.5em; text-align:left;"><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">Key: OUYCCCASQSFEME-UHFFFAOYSA-N</div></div></li><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.5em; text-align:left;"><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">Key: OUYCCCASQSFEME-MRVPVSSYSA-N</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%;">N[C@@H](Cc1ccc(O)cc1)C(O)=O</div></li><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.6em; word-wrap:break-word; text-indent:-1.5em; text-align:left; font-size:97%; line-height:120%;"><a href="/wiki/Zwitterion" title="Zwitterion">Zwitterion</a>: [NH3+][C@@H](Cc1ccc(O)cc1)C([O-])=O</div></li></ul> </div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Properties </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Chemical_formula" title="Chemical formula">Chemical formula</a></div> </td> <td><span title="Carbon">C</span><sub>9</sub><span title="Hydrogen">H</span><sub>11</sub><span title="Nitrogen">N</span><span title="Oxygen">O</span><sub>3</sub> </td></tr> <tr> <td><a href="/wiki/Molar_mass" title="Molar mass">Molar mass</a> </td> <td><span class="nowrap"><span data-sort-value="7002181191000000000♠"></span>181.191</span> g·mol<sup>−1</sup>   </td></tr> <tr> <td>Appearance </td> <td>white solid </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>.0453 g/100 mL </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Magnetic_susceptibility" title="Magnetic susceptibility">Magnetic susceptibility</a> (χ)</div> </td> <td>-105.3·10<sup>−6</sup> cm<sup>3</sup>/mol </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Hazards </th></tr> <tr> <td><a href="/wiki/NFPA_704" title="NFPA 704"><b>NFPA 704</b></a> (fire diamond) </td> <td><style data-mw-deduplicate="TemplateStyles:r1170367383">.mw-parser-output .nfpa-704-diamond-ref{float:right;padding:1px;text-align:right}.mw-parser-output .nfpa-704-diamond-container{width:82px;font-family:sans-serif;margin:0 auto}.mw-parser-output .nfpa-704-diamond-container-ref{float:left;margin-left:1em}.mw-parser-output .nfpa-704-diamond-images{float:left;font-size:20px;text-align:center;position:relative;height:80px;width:80px;padding:1px}.mw-parser-output .nfpa-704-diamond-map{position:absolute;height:80px;width:80px}.mw-parser-output .nfpa-704-diamond .noresize{margin:0 auto}.mw-parser-output .nfpa-704-diamond-code{line-height:1em;text-align:center;position:absolute}.mw-parser-output .nfpa-704-diamond-code>a{color:black}.mw-parser-output .nfpa-704-diamond-blue{width:13px;top:31px;left:15px}.mw-parser-output .nfpa-704-diamond-red{width:12px;top:12px;left:35px}.mw-parser-output .nfpa-704-diamond-yellow{width:13px;top:31px;left:54px}.mw-parser-output .nfpa-704-diamond-white-image{position:relative;top:51px;left:0}.mw-parser-output .nfpa-704-diamond-white-text{vertical-align:middle;text-align:center;line-height:80%;position:absolute;top:52px}.mw-parser-output .nfpa-704-diamond-white-text a>span{position:absolute;color:black}.mw-parser-output .nfpa-704-diamond-white-wors{font-size:15px;width:23px;left:29px}.mw-parser-output .nfpa-704-diamond-white-wox{font-size:15px;font-stretch:condensed;width:21px;line-height:80%;top:-4px;left:29px}.mw-parser-output .nfpa-704-diamond-white-abcp{font-size:13.5px;font-stretch:condensed;width:28px;left:26px}.mw-parser-output .nfpa-704-diamond-white-ac{font-size:10px;width:30px;left:25px}.mw-parser-output .nfpa-704-diamond-white-strike{text-decoration:line-through}</style><div class="nfpa-704-diamond notheme"><div class="nfpa-704-diamond-container"><div class="nfpa-704-diamond-images nounderlines"> <div class="nfpa-704-diamond-map"><figure class="noresize" typeof="mw:File"><span><img alt="NFPA 704 four-colored diamond" src="//upload.wikimedia.org/wikipedia/commons/thumb/6/6f/NFPA_704.svg/80px-NFPA_704.svg.png" decoding="async" width="80" height="80" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/6f/NFPA_704.svg/120px-NFPA_704.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/6f/NFPA_704.svg/160px-NFPA_704.svg.png 2x" data-file-width="512" data-file-height="512" usemap="#ImageMap_811dcee2cbfc5fb2" /></span><map name="ImageMap_811dcee2cbfc5fb2"><area href="/wiki/NFPA_704#Blue" shape="poly" coords="23,23,47,47,23,70,0,47" alt="Health 1: Exposure would cause irritation but only minor residual injury. E.g. turpentine" title="Health 1: Exposure would cause irritation but only minor residual injury. E.g. turpentine" /><area href="/wiki/NFPA_704#Red" shape="poly" coords="47,0,70,23,47,47,23,23" alt="Flammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oil" title="Flammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oil" /><area href="/wiki/NFPA_704#Yellow" shape="poly" coords="70,23,94,47,70,70,47,47" alt="Instability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogen" title="Instability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogen" /><area href="/wiki/NFPA_704#White" shape="poly" coords="47,47,70,70,47,94,23,70" alt="Special hazards (white): no code" title="Special hazards (white): no code" /></map><figcaption></figcaption></figure></div><div class="nfpa-704-diamond-code nfpa-704-diamond-blue"> <a href="/wiki/NFPA_704#Blue" title="NFPA 704"><span title="Health 1: Exposure would cause irritation but only minor residual injury. E.g. turpentine" class="notheme mw-no-invert">1</span></a></div><div class="nfpa-704-diamond-code nfpa-704-diamond-red"> <a href="/wiki/NFPA_704#Red" title="NFPA 704"><span title="Flammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oil" class="notheme mw-no-invert">1</span></a></div><div class="nfpa-704-diamond-code nfpa-704-diamond-yellow"> <a href="/wiki/NFPA_704#Yellow" title="NFPA 704"><span title="Instability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogen" class="notheme mw-no-invert">0</span></a></div></div></div></div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Supplementary data page </th></tr> <tr> <td colspan="2" style="text-align:center"><a href="/wiki/Tyrosine_(data_page)" title="Tyrosine (data page)">Tyrosine (data page)</a> </td></tr> <tr> <td colspan="2" style="text-align:left; background:#f8eaba; border:1px solid #a2a9b1;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">Except where otherwise noted, data are given for materials in their <a href="/wiki/Standard_state" title="Standard state">standard state</a> (at 25 °C [77 °F], 100 kPa).</div> <div style="margin-top: 0.3em;"></div> <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><span style="font-size:85%;">L</span>-Tyrosine</b> or <b>tyrosine</b> (symbol <b>Tyr</b> or <b>Y</b>)<sup id="cite_ref-2" class="reference"><a href="#cite_note-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> or <b>4-hydroxyphenylalanine</b> is one of the 20 standard <a href="/wiki/Proteinogenic_amino_acid" title="Proteinogenic amino acid">amino acids</a> that are used by <a href="/wiki/Cell_(biology)" title="Cell (biology)">cells</a> to <a href="/wiki/Protein_biosynthesis" title="Protein biosynthesis">synthesize proteins</a>. It is a <a href="/wiki/Conditionally_essential_amino_acid" class="mw-redirect" title="Conditionally essential amino acid">conditionally essential amino acid</a> with a <a href="/wiki/Proteinogenic_amino_acid#Side-chain_properties" title="Proteinogenic amino acid">polar side group</a>. The word "tyrosine" is from the <a href="/wiki/Greek_language" title="Greek language">Greek</a> <i>tyrós</i>, meaning <i><a href="/wiki/Cheese" title="Cheese">cheese</a></i>, as it was first discovered in 1846 by German chemist <a href="/wiki/Justus_von_Liebig" title="Justus von Liebig">Justus von Liebig</a> in the protein <a href="/wiki/Casein" title="Casein">casein</a> from cheese.<sup id="cite_ref-urltyrosine_—_Infoplease.com_3-0" class="reference"><a href="#cite_note-urltyrosine_—_Infoplease.com-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-urlOnline_Etymology_Dictionary_4-0" class="reference"><a href="#cite_note-urlOnline_Etymology_Dictionary-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> It is called <b>tyrosyl</b> when referred to as a <a href="/wiki/Functional_group" title="Functional group">functional group</a> or side chain. While tyrosine is generally classified as a <a href="/wiki/Hydrophobe" title="Hydrophobe">hydrophobic</a> amino acid, it is more hydrophilic than <a href="/wiki/Phenylalanine" title="Phenylalanine">phenylalanine</a>.<sup id="cite_ref-5" class="reference"><a href="#cite_note-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> It is <a href="/wiki/Genetic_code" title="Genetic code">encoded</a> by the <a href="/wiki/Genetic_code#Codons" title="Genetic code">codons</a> UAC and UAU in <a href="/wiki/Messenger_RNA" title="Messenger RNA">messenger RNA</a>. </p><p>The one-letter symbol Y was assigned to tyrosine for being alphabetically nearest of those letters available. Note that T was assigned to the structurally simpler threonine, U was avoided for its similarity with V for valine, W was assigned to tryptophan, while X was reserved for undetermined or atypical amino acids.<sup id="cite_ref-:0_6-0" class="reference"><a href="#cite_note-:0-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> The mnemonic t<i>Y</i>rosine was also proposed.<sup id="cite_ref-:1_7-0" class="reference"><a href="#cite_note-:1-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Functions">Functions</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Tyrosine&action=edit&section=1" title="Edit section: Functions"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Aside from being a <a href="/wiki/Proteinogenic_amino_acid" title="Proteinogenic amino acid">proteinogenic amino acid</a>, tyrosine has a special role by virtue of the <a href="/wiki/Phenol" title="Phenol">phenol</a> functionality. Its hydroxy group is able to form the <a href="/wiki/Ester_linkage" class="mw-redirect" title="Ester linkage">ester linkage</a>, with phosphate in particular. Phosphate groups are transferred to tyrosine residues by way of <a href="/wiki/Protein_kinase" title="Protein kinase">protein kinases</a>. This is one of the <a href="/wiki/Post-translational_modification" title="Post-translational modification">post-translational modifications</a>. Phosphorylated tyrosine occurs in proteins that are part of <a href="/wiki/Signal_transduction" title="Signal transduction">signal transduction</a> processes. </p><p>Similar functionality is also presented in <a href="/wiki/Serine" title="Serine">serine</a> and <a href="/wiki/Threonine" title="Threonine">threonine</a>, whose side chains have a hydroxy group, but are <a href="/wiki/Alcohol_(chemistry)" title="Alcohol (chemistry)">alcohols</a>. Phosphorylation of these three amino acids' moieties (including tyrosine) creates a negative charge on their ends, that is greater than the negative charge of the only negatively charged <a href="/wiki/Aspartic_acid" title="Aspartic acid">aspartic</a> and <a href="/wiki/Glutamic_acid" title="Glutamic acid">glutamic</a> acids. Phosphorylated proteins keep these same properties—which are useful for more reliable protein-protein interactions—by means of phosphotyrosine, phosphoserine and phosphothreonine.<sup id="cite_ref-8" class="reference"><a href="#cite_note-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> </p><p>Binding sites for a signalling phosphoprotein may be diverse in their chemical structure.<sup id="cite_ref-9" class="reference"><a href="#cite_note-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> </p><p>Phosphorylation of the hydroxyl group can change the activity of the target protein, or may form part of a signaling cascade via <a href="/wiki/SH2_domain" title="SH2 domain">SH2 domain</a> binding.<sup id="cite_ref-10" class="reference"><a href="#cite_note-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> </p><p>A tyrosine residue also plays an important role in <a href="/wiki/Photosynthesis" title="Photosynthesis">photosynthesis</a>. In <a href="/wiki/Chloroplast" title="Chloroplast">chloroplasts</a> (<a href="/wiki/Photosystem_II" title="Photosystem II">photosystem II</a>), it acts as an electron donor in the <a href="/wiki/Redox" title="Redox">reduction</a> of oxidized <a href="/wiki/Chlorophyll" title="Chlorophyll">chlorophyll</a>. In this process, it loses the hydrogen atom of its phenolic OH-group. This radical is subsequently reduced in the photosystem II by the four core <a href="/wiki/Oxygen-evolving_complex" title="Oxygen-evolving complex">manganese clusters</a>.<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> <div class="mw-heading mw-heading2"><h2 id="Dietary_requirements_and_sources">Dietary requirements and sources</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Tyrosine&action=edit&section=2" title="Edit section: Dietary requirements and sources"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The <a href="/wiki/Dietary_Reference_Intake" title="Dietary Reference Intake">Dietary Reference Intake</a> for tyrosine is usually estimated together with <a href="/wiki/Phenylalanine" title="Phenylalanine">phenylalanine</a>. It varies depending on an estimate method, however the ideal proportion of these two amino acids is considered to be 60:40 (phenylalanine:tyrosine) as a human body has such composition.<sup id="cite_ref-12" class="reference"><a href="#cite_note-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup> Tyrosine, which can also be synthesized in the body from phenylalanine, is found in many high-<a href="/wiki/Protein" title="Protein">protein</a> food products such as <a href="/wiki/Meat" title="Meat">meat</a>, <a href="/wiki/Fish_(food)" class="mw-redirect" title="Fish (food)">fish</a>, <a href="/wiki/Cheese" title="Cheese">cheese</a>, <a href="/wiki/Cottage_cheese" title="Cottage cheese">cottage cheese</a>, <a href="/wiki/Milk" title="Milk">milk</a>, <a href="/wiki/Yogurt" title="Yogurt">yogurt</a>, <a href="/wiki/Peanut" title="Peanut">peanuts</a>, <a href="/wiki/Almond" title="Almond">almonds</a>, <a href="/wiki/Pumpkin_seed" title="Pumpkin seed">pumpkin seeds</a>, <a href="/wiki/Sesame_seed" class="mw-redirect" title="Sesame seed">sesame seeds</a>, <a href="/wiki/Soy_products" class="mw-redirect" title="Soy products">soy protein</a> and <a href="/wiki/Lima_bean" title="Lima bean">lima beans</a>.<sup id="cite_ref-13" class="reference"><a href="#cite_note-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup><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> For example, the white of an egg has about 250 mg per egg,<sup id="cite_ref-HF_15-0" class="reference"><a href="#cite_note-HF-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup> while beef, lamb, pork, tuna, salmon, chicken, and turkey contain about 500–1000 mg per 3 ounces (85 g) portion.<sup id="cite_ref-HF_15-1" class="reference"><a href="#cite_note-HF-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-16" class="reference"><a href="#cite_note-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Biosynthesis">Biosynthesis</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Tyrosine&action=edit&section=3" title="Edit section: Biosynthesis"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure class="mw-halign-center" typeof="mw:File/Thumb"><a href="/wiki/File:Tyrosine_biosynthesis.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/0/05/Tyrosine_biosynthesis.svg/400px-Tyrosine_biosynthesis.svg.png" decoding="async" width="400" height="172" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/0/05/Tyrosine_biosynthesis.svg/600px-Tyrosine_biosynthesis.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/0/05/Tyrosine_biosynthesis.svg/800px-Tyrosine_biosynthesis.svg.png 2x" data-file-width="650" data-file-height="280" /></a><figcaption>Plant biosynthesis of tyrosine from <a href="/wiki/Prephenate" class="mw-redirect" title="Prephenate">prephenate</a>.</figcaption></figure> <p>In plants and most microorganisms, tyrosine is produced via <a href="/wiki/Prephenic_acid" title="Prephenic acid">prephenate</a>, an intermediate on the <a href="/wiki/Shikimate_pathway" title="Shikimate pathway">shikimate pathway</a>. Prephenate is <a href="/wiki/Oxidative_decarboxylation" title="Oxidative decarboxylation">oxidatively decarboxylated</a> with retention of the <a href="/wiki/Hydroxyl" class="mw-redirect" title="Hydroxyl">hydroxyl</a> group to give <i>p</i>-hydroxyphenylpyruvate, which is <a href="/wiki/Transamination" title="Transamination">transaminated</a> using <a href="/wiki/Glutamic_acid" title="Glutamic acid">glutamate</a> as the nitrogen source to give tyrosine and <a href="/wiki/Alpha-Ketoglutaric_acid" class="mw-redirect" title="Alpha-Ketoglutaric acid">α-ketoglutarate</a>. </p><p><a href="/wiki/Mammal" title="Mammal">Mammals</a> synthesize tyrosine from the essential amino acid <a href="/wiki/Phenylalanine" title="Phenylalanine">phenylalanine</a> (Phe), which is derived from food. The conversion of Phe to Tyr is catalyzed by the <a href="/wiki/Enzyme" title="Enzyme">enzyme</a> <a href="/wiki/Phenylalanine_hydroxylase" title="Phenylalanine hydroxylase">phenylalanine hydroxylase</a>, a monooxygenase. This enzyme catalyzes the reaction causing the addition of a hydroxyl group to the end of the 6-carbon aromatic ring of <a href="/wiki/Phenylalanine" title="Phenylalanine">phenylalanine</a>, such that it becomes tyrosine. </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=Tyrosine&action=edit&section=4" title="Edit section: Metabolism"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure class="mw-halign-center" typeof="mw:File/Thumb"><a href="/wiki/File:Conversion_of_phenylalanine_and_tyrosine_to_its_biologically_important_derivatives.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/d/dd/Conversion_of_phenylalanine_and_tyrosine_to_its_biologically_important_derivatives.png/800px-Conversion_of_phenylalanine_and_tyrosine_to_its_biologically_important_derivatives.png" decoding="async" width="800" height="315" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/d/dd/Conversion_of_phenylalanine_and_tyrosine_to_its_biologically_important_derivatives.png/1200px-Conversion_of_phenylalanine_and_tyrosine_to_its_biologically_important_derivatives.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/d/dd/Conversion_of_phenylalanine_and_tyrosine_to_its_biologically_important_derivatives.png/1600px-Conversion_of_phenylalanine_and_tyrosine_to_its_biologically_important_derivatives.png 2x" data-file-width="4434" data-file-height="1747" /></a><figcaption>Conversion of phenylalanine and tyrosine to its biologically important derivatives.</figcaption></figure> <div class="mw-heading mw-heading3"><h3 id="Phosphorylation_and_sulfation">Phosphorylation and sulfation</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Tyrosine&action=edit&section=5" title="Edit section: Phosphorylation and sulfation"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Some of the tyrosine residues can be <i>tagged</i> (at the hydroxyl group) with a phosphate group (<a href="/wiki/Phosphorylation" title="Phosphorylation">phosphorylated</a>) by <a href="/wiki/Protein_kinase" title="Protein kinase">protein kinases</a>. In its phosphorylated form, tyrosine is called <b>phosphotyrosine</b>. Tyrosine phosphorylation is considered to be one of the key steps in signal transduction and regulation of enzymatic activity. Phosphotyrosine can be detected through specific <a href="/wiki/Antibody" title="Antibody">antibodies</a>. Tyrosine residues may also be modified by the addition of a sulfate group, a process known as <a href="/wiki/Tyrosine_sulfation" title="Tyrosine sulfation">tyrosine sulfation</a>.<sup id="cite_ref-pmid17046811_17-0" class="reference"><a href="#cite_note-pmid17046811-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup> <a href="/wiki/Tyrosine_sulfation" title="Tyrosine sulfation">Tyrosine sulfation</a> is catalyzed by <a href="/wiki/Tyrosylprotein_sulfotransferase" title="Tyrosylprotein sulfotransferase">tyrosylprotein sulfotransferase</a> (TPST). Like the phosphotyrosine antibodies mentioned above, antibodies have recently been described that specifically detect sulfotyrosine.<sup id="cite_ref-18" class="reference"><a href="#cite_note-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Precursor_to_neurotransmitters_and_hormones">Precursor to neurotransmitters and hormones</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Tyrosine&action=edit&section=6" title="Edit section: Precursor to neurotransmitters and hormones"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>In dopaminergic cells in the <a href="/wiki/Brain" title="Brain">brain</a>, tyrosine is converted to <a href="/wiki/L-DOPA" title="L-DOPA">L-DOPA</a> by the <a href="/wiki/Enzyme" title="Enzyme">enzyme</a> <a href="/wiki/Tyrosine_hydroxylase" title="Tyrosine hydroxylase">tyrosine hydroxylase</a> (TH). TH is the <a href="/wiki/Rate-limiting_enzyme" class="mw-redirect" title="Rate-limiting enzyme">rate-limiting enzyme</a> involved in the synthesis of the <a href="/wiki/Neurotransmitter" title="Neurotransmitter">neurotransmitter</a> <a href="/wiki/Dopamine" title="Dopamine">dopamine</a>. Dopamine can then be converted into other <a href="/wiki/Catecholamine" title="Catecholamine">catecholamines</a>, such as <a href="/wiki/Norepinephrine" title="Norepinephrine">norepinephrine</a> (noradrenaline) and <a href="/wiki/Epinephrine" class="mw-redirect" title="Epinephrine">epinephrine</a> (adrenaline). </p><p>The <a href="/wiki/Thyroid" title="Thyroid">thyroid</a> hormones <a href="/wiki/Triiodothyronine" title="Triiodothyronine">triiodothyronine</a> (T<sub>3</sub>) and <a href="/wiki/Thyroxine" class="mw-redirect" title="Thyroxine">thyroxine</a> (T<sub>4</sub>) in the <a href="/wiki/Colloid" title="Colloid">colloid</a> of the <a href="/wiki/Thyroid" title="Thyroid">thyroid</a> are also derived from tyrosine. </p> <div class="skin-invert-image"> <table role="presentation" cellpadding="0" style="border-spacing:0; margin-left: auto; margin-right: auto; border: none;"> <tbody><tr> <td><div class="thumb center" style="margin: 1em auto;"> <div class="thumbinner" style="width:592px;"> <div style="clear: both; font-weight: bold; font-size: 106.4%; text-align: center; background-color: #F0F8FF;margin-bottom:3px;">Biosynthetic pathways for <a href="/wiki/Catecholamine" title="Catecholamine">catecholamines</a> and <a href="/wiki/Trace_amine" title="Trace amine">trace amines</a> in the <a href="/wiki/Human_brain" title="Human brain">human brain</a><sup id="cite_ref-Trace_amine_template_1_19-0" class="reference"><a href="#cite_note-Trace_amine_template_1-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Trace_amine_template_2_20-0" class="reference"><a href="#cite_note-Trace_amine_template_2-20"><span class="cite-bracket">[</span>20<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-CYP2D6_tyramine-dopamine_metabolism_21-0" class="reference"><a href="#cite_note-CYP2D6_tyramine-dopamine_metabolism-21"><span class="cite-bracket">[</span>21<span class="cite-bracket">]</span></a></sup></div> <div style="position:relative; width:590px; height:465px; overflow:hidden; border:solid #ccc 1px; background-color:white;"> <div style="left:5px; top:0px; width:580px; position:absolute"> <span typeof="mw:File"><a href="https://commons.wikimedia.org/wiki/File:Catecholamine_and_trace_amine_biosynthesis.svg" title="commons:File:Catecholamine and trace amine biosynthesis.svg"><img alt="Graphic of catecholamine and trace amine biosynthesis" src="//upload.wikimedia.org/wikipedia/commons/thumb/4/46/Catecholamine_and_trace_amine_biosynthesis.svg/580px-Catecholamine_and_trace_amine_biosynthesis.svg.png" decoding="async" width="580" height="458" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/4/46/Catecholamine_and_trace_amine_biosynthesis.svg/870px-Catecholamine_and_trace_amine_biosynthesis.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/4/46/Catecholamine_and_trace_amine_biosynthesis.svg/1160px-Catecholamine_and_trace_amine_biosynthesis.svg.png 2x" data-file-width="512" data-file-height="404" /></a></span> </div> <div style="text-align:center; font-size:14px; line-height:110%"> <div style="background-color:transparent; color:black"><div id="annotation_40x60" style="position:absolute; left:40px; top:60px; line-height:110%;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/Phenylalanine" title="Phenylalanine"><small>L</small>-Phenylalanine</a></span></div> <div id="annotation_50x185" style="position:absolute; left:50px; top:185px; line-height:110%;"><span style="background-color:transparent; color:inherit;"><span style="color:black;background:yellow"><b><small>L</small>-Tyrosine</b></span></span></div> <div id="annotation_60x315" style="position:absolute; left:60px; top:315px; line-height:110%;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/L-DOPA" title="L-DOPA"><small>L</small>-DOPA</a></span></div> <div id="annotation_50x445" style="position:absolute; left:50px; top:445px; line-height:110%;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/Adrenaline" title="Adrenaline">Epinephrine</a></span></div> <div id="annotation_245x60" style="position:absolute; left:245px; top:60px; line-height:110%;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/Phenethylamine" title="Phenethylamine">Phenethylamine</a></span></div> <div id="annotation_245x185" style="position:absolute; left:245px; top:185px; line-height:110%;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/Tyramine" title="Tyramine"><i>p</i>-Tyramine</a></span></div> <div id="annotation_245x315" style="position:absolute; left:245px; top:315px; line-height:110%;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/Dopamine" title="Dopamine">Dopamine</a></span></div> <div id="annotation_245x445" style="position:absolute; left:245px; top:445px; line-height:110%;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/Norepinephrine" title="Norepinephrine">Norepinephrine</a></span></div> <div id="annotation_415x60" style="position:absolute; left:415px; top:60px; line-height:110%;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/N-Methylphenethylamine" title="N-Methylphenethylamine"><i>N</i>-Methylphenethylamine</a></span></div> <div id="annotation_440x138" style="position:absolute; left:440px; top:138px; line-height:110%;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/N-Methyltyramine" title="N-Methyltyramine"><i>N</i>-Methyltyramine</a></span></div> <div id="annotation_440x228" style="position:absolute; left:440px; top:228px; line-height:110%;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/Octopamine" title="Octopamine"><i>p</i>-Octopamine</a></span></div> <div id="annotation_455x350" style="position:absolute; left:455px; top:350px; line-height:110%;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/Synephrine" title="Synephrine">Synephrine</a></span></div> <div id="annotation_445x445" style="position:absolute; left:445px; top:445px; line-height:110%;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/3-Methoxytyramine" title="3-Methoxytyramine">3-Methoxytyramine</a></span></div> <div id="annotation_167x16" style="position:absolute; left:167px; top:16px; line-height:110%;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/Aromatic_L-amino_acid_decarboxylase" title="Aromatic L-amino acid decarboxylase">AADC</a></span></div> <div id="annotation_167x145" style="position:absolute; left:167px; top:145px; line-height:110%;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/Aromatic_L-amino_acid_decarboxylase" title="Aromatic L-amino acid decarboxylase">AADC</a></span></div> <div id="annotation_167x275" style="position:absolute; left:167px; top:275px; line-height:110%;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/Aromatic_L-amino_acid_decarboxylase" title="Aromatic L-amino acid decarboxylase">AADC</a></span></div> <div id="annotation_164x295" style="position:absolute; left:164px; top:295px; font-size:12px; font-size:12; line-height:14px;"><span style="background-color:transparent; color:inherit;">primary<br />pathway</span></div> <div id="annotation_370x17" style="position:absolute; left:370px; top:17px; line-height:110%;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/Phenylethanolamine_N-methyltransferase" title="Phenylethanolamine N-methyltransferase">PNMT</a></span></div> <div id="annotation_360x120" style="position:absolute; left:360px; top:120px; line-height:110%;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/Phenylethanolamine_N-methyltransferase" title="Phenylethanolamine N-methyltransferase">PNMT</a></span></div> <div id="annotation_445x255" style="position:absolute; left:445px; top:255px; line-height:110%;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/Phenylethanolamine_N-methyltransferase" title="Phenylethanolamine N-methyltransferase">PNMT</a></span></div> <div id="annotation_176x407" style="position:absolute; left:176px; top:407px; line-height:110%;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/Phenylethanolamine_N-methyltransferase" title="Phenylethanolamine N-methyltransferase">PNMT</a></span></div> <div id="annotation_40x90" style="position:absolute; left:40px; top:90px; line-height:110%;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/Biopterin-dependent_aromatic_amino_acid_hydroxylase" title="Biopterin-dependent aromatic amino acid hydroxylase">AAAH</a></span></div> <div id="annotation_40x220" style="position:absolute; left:40px; top:220px; line-height:110%;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/Biopterin-dependent_aromatic_amino_acid_hydroxylase" title="Biopterin-dependent aromatic amino acid hydroxylase">AAAH</a></span></div> <div id="annotation_225x215" style="position:absolute; left:225px; top:215px; line-height:110%;"><span style="background-color:transparent; color:inherit;">brain<br /><a href="/wiki/CYP2D6" title="CYP2D6">CYP2D6</a></span></div> <div id="annotation_291x217" style="position:absolute; left:291px; top:217px; font-size:12px; font-size:12; line-height:14px; text-align:left;"><span style="background-color:transparent; color:inherit;">minor<br />pathway</span></div> <div id="annotation_325x350" style="position:absolute; left:325px; top:350px; line-height:110%;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/Catechol-O-methyltransferase" title="Catechol-O-methyltransferase">COMT</a></span></div> <div id="annotation_250x350" style="position:absolute; left:250px; top:350px; line-height:110%;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/Dopamine_beta-hydroxylase" title="Dopamine beta-hydroxylase">DBH</a></span></div> <div id="annotation_360x185" style="position:absolute; left:360px; top:185px; line-height:110%;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/Dopamine_beta-hydroxylase" title="Dopamine beta-hydroxylase">DBH</a></span></div></div> </div> </div> <div class="thumbcaption" style="clear:left"><div style="float:left;margin-right:0.5em"><span typeof="mw:File"><span title="The image above contains clickable links"><img alt="The image above contains clickable links" src="//upload.wikimedia.org/wikipedia/commons/thumb/e/e6/Interactive_icon.svg/18px-Interactive_icon.svg.png" decoding="async" width="18" height="27" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/e6/Interactive_icon.svg/27px-Interactive_icon.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/e/e6/Interactive_icon.svg/36px-Interactive_icon.svg.png 2x" data-file-width="133" data-file-height="200" /></span></span></div>Tyrosine is a precursor to trace amine compounds and the catecholamines.</div> </div> </div> </td></tr></tbody></table> </div> <p><br /> </p> <div class="mw-heading mw-heading3"><h3 id="Precursor_to_other_compounds">Precursor to other compounds</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Tyrosine&action=edit&section=7" title="Edit section: Precursor to other compounds"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The latex of <i><a href="/wiki/Papaver_somniferum" title="Papaver somniferum">Papaver somniferum</a></i>, the opium poppy, has been shown to convert tyrosine into the <a href="/wiki/Alkaloid" title="Alkaloid">alkaloid</a> <a href="/wiki/Morphine" title="Morphine">morphine</a> and the bio-synthetic pathway has been established from tyrosine to morphine by using Carbon-14 radio-labelled tyrosine to trace the in-vivo synthetic route.<sup id="cite_ref-22" class="reference"><a href="#cite_note-22"><span class="cite-bracket">[</span>22<span class="cite-bracket">]</span></a></sup><a href="/wiki/Tyrosine_ammonia_lyase" class="mw-redirect" title="Tyrosine ammonia lyase">Tyrosine ammonia lyase</a> (TAL) is an enzyme in the natural phenols biosynthesis pathway. It transforms L-tyrosine into <a href="/wiki/P-coumaric_acid" class="mw-redirect" title="P-coumaric acid">p-coumaric acid</a>. Tyrosine is also the precursor to the pigment <i><a href="/wiki/Melanin" title="Melanin">melanin</a></i>. Tyrosine (or its precursor phenylalanine) is needed to synthesize the benzoquinone structure which forms part of <a href="/wiki/Coenzyme_Q10" title="Coenzyme Q10">coenzyme Q10</a>.<sup id="cite_ref-23" class="reference"><a href="#cite_note-23"><span class="cite-bracket">[</span>23<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-24" class="reference"><a href="#cite_note-24"><span class="cite-bracket">[</span>24<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Degradation">Degradation</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Tyrosine&action=edit&section=8" title="Edit section: Degradation"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure class="mw-halign-center" typeof="mw:File/Thumb"><a href="/wiki/File:Tyrosinedegradation2.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/c/c9/Tyrosinedegradation2.png/750px-Tyrosinedegradation2.png" decoding="async" width="750" height="213" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/c/c9/Tyrosinedegradation2.png/1125px-Tyrosinedegradation2.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/c/c9/Tyrosinedegradation2.png/1500px-Tyrosinedegradation2.png 2x" data-file-width="4518" data-file-height="1283" /></a><figcaption>The decomposition of tyrosine to <a href="/wiki/Acetoacetic_acid" title="Acetoacetic acid">acetoacetate</a> and <a href="/wiki/Fumarate" class="mw-redirect" title="Fumarate">fumarate</a>. Two dioxygenases are necessary for the decomposition path. The end products can then enter into the <a href="/wiki/Citric_acid_cycle" title="Citric acid cycle">citric acid cycle</a>.</figcaption></figure><p><sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (November 2023)">citation needed</span></a></i>]</sup> </p><p>The decomposition of L-tyrosine (syn. <i>para</i>-hydroxyphenylalanine) begins with an α-ketoglutarate dependent <a href="/wiki/Transamination" title="Transamination">transamination</a> through the <a href="/wiki/Tyrosine_transaminase" class="mw-redirect" title="Tyrosine transaminase">tyrosine transaminase</a> to <a href="/wiki/Para-Hydroxyphenylpyruvate" class="mw-redirect" title="Para-Hydroxyphenylpyruvate"><i>para</i>-hydroxyphenylpyruvate</a>. The positional description <i>para</i>, abbreviated <i>p</i>, mean that the hydroxyl group and side chain on the phenyl ring are across from each other (see the illustration below). </p><p>The next oxidation step catalyzes by <a href="/wiki/P-Hydroxyphenylpyruvate_dioxygenase" class="mw-redirect" title="P-Hydroxyphenylpyruvate dioxygenase"><i>p</i>-hydroxyphenylpyruvate dioxygenase</a> and splitting off CO<sub>2</sub> <a href="/wiki/Homogentisic_acid" title="Homogentisic acid">homogentisate</a> (2,5-dihydroxyphenyl-1-acetate).<sup id="cite_ref-25" class="reference"><a href="#cite_note-25"><span class="cite-bracket">[</span>25<span class="cite-bracket">]</span></a></sup> In order to split the aromatic ring of homogentisate, a further dioxygenase, <a href="/wiki/Homogentisate_1,2-dioxygenase" title="Homogentisate 1,2-dioxygenase">homogentisate 1,2-dioxygenase</a> is required. Thereby, through the incorporation of a further O<sub>2</sub> molecule, <a href="/wiki/Maleylacetoacetate" class="mw-redirect" title="Maleylacetoacetate">maleylacetoacetate</a> is created. </p><p><a href="/wiki/Fumarylacetoacetate" class="mw-redirect" title="Fumarylacetoacetate">Fumarylacetoacetate</a> is created by <a href="/wiki/4-maleylacetoacetate_cis-trans-isomerase" class="mw-redirect" title="4-maleylacetoacetate cis-trans-isomerase">maleylacetoacetate <i>cis</i>-<i>trans</i>-isomerase</a> through rotation of the carboxyl group created from the hydroxyl group via oxidation. This <i>cis-trans</i>-isomerase contains <a href="/wiki/Glutathione" title="Glutathione">glutathione</a> as a <a href="/wiki/Coenzyme" class="mw-redirect" title="Coenzyme">coenzyme</a>. Fumarylacetoacetate is finally split by the enzyme <a href="/wiki/Fumarylacetoacetate_hydrolase" title="Fumarylacetoacetate hydrolase">fumarylacetoacetate hydrolase</a> through the addition of a water molecule. </p><p>Thereby <a href="/wiki/Fumarate" class="mw-redirect" title="Fumarate">fumarate</a> (also a metabolite of the citric acid cycle) and <a href="/wiki/Acetoacetic_acid" title="Acetoacetic acid">acetoacetate</a> (3-ketobutyroate) are liberated. Acetoacetate is a <a href="/wiki/Ketone_body" class="mw-redirect" title="Ketone body">ketone body</a>, which is activated with succinyl-CoA, and thereafter it can be converted into <a href="/wiki/Acetyl-CoA" title="Acetyl-CoA">acetyl-CoA</a>, which in turn can be oxidized by the <a href="/wiki/Citric_acid_cycle" title="Citric acid cycle">citric acid cycle</a> or be used for <a href="/wiki/Fatty_acid_synthesis" title="Fatty acid synthesis">fatty acid synthesis</a>. </p><p><a href="/wiki/Phloretic_acid" title="Phloretic acid">Phloretic acid</a> is also a urinary metabolite of tyrosine in rats.<sup id="cite_ref-26" class="reference"><a href="#cite_note-26"><span class="cite-bracket">[</span>26<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Ortho-_and_meta-tyrosine">Ortho- and meta-tyrosine</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Tyrosine&action=edit&section=9" title="Edit section: Ortho- and meta-tyrosine"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure class="mw-halign-right" typeof="mw:File/Thumb"><a href="/wiki/File:Phe_Tyr.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/6/6d/Phe_Tyr.png/500px-Phe_Tyr.png" decoding="async" width="500" height="212" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/6d/Phe_Tyr.png/750px-Phe_Tyr.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/6d/Phe_Tyr.png/1000px-Phe_Tyr.png 2x" data-file-width="5291" data-file-height="2246" /></a><figcaption>Enzymatic <a href="/wiki/Oxidation" class="mw-redirect" title="Oxidation">oxidation</a> of tyrosine by <a href="/wiki/Phenylalanine_hydroxylase" title="Phenylalanine hydroxylase">phenylalanine hydroxylase</a> (top) and non-enyzmatic oxidation by hydroxyl <a href="/wiki/Free_radical" class="mw-redirect" title="Free radical">free radicals</a> (middle and bottom).</figcaption></figure> <p>Three <a href="/wiki/Structural_isomers" class="mw-redirect" title="Structural isomers">structural isomers</a> of L-tyrosine are known. In addition to the common amino acid L-tyrosine, which is the <a href="/wiki/Para_isomer" class="mw-redirect" title="Para isomer">para isomer</a> (<i>para</i>-tyr, <i>p</i>-tyr or 4-hydroxyphenylalanine), there are two additional regioisomers, namely <b><i>meta</i>-tyrosine</b> (also known as <span class="nowrap"><b>3-hydroxyphenylalanine</b></span>, <b>L-<i>m</i>-tyrosine</b>, and <i>m</i>-tyr) and <i>ortho</i>-tyrosine (<i>o</i>-tyr or 2-hydroxyphenylalanine), that occur in nature. The <i>m</i>-tyr and <i>o</i>-tyr isomers, which are rare, arise through non-enzymatic <a href="/wiki/Free-radical" class="mw-redirect" title="Free-radical">free-radical</a> hydroxylation of phenylalanine under conditions of <a href="/wiki/Oxidative_stress" title="Oxidative stress">oxidative stress</a>.<sup id="cite_ref-pmid16221230_27-0" class="reference"><a href="#cite_note-pmid16221230-27"><span class="cite-bracket">[</span>27<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-pmid16298866_28-0" class="reference"><a href="#cite_note-pmid16298866-28"><span class="cite-bracket">[</span>28<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Medical_use">Medical use</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Tyrosine&action=edit&section=10" title="Edit section: Medical use"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Tyrosine is a precursor to <a href="/wiki/Neurotransmitter" title="Neurotransmitter">neurotransmitters</a> and increases plasma neurotransmitter levels (particularly dopamine and norepinephrine),<sup id="cite_ref-pmid6885965_29-0" class="reference"><a href="#cite_note-pmid6885965-29"><span class="cite-bracket">[</span>29<span class="cite-bracket">]</span></a></sup> but has little if any effect on mood in normal subjects.<sup id="cite_ref-DietMood_30-0" class="reference"><a href="#cite_note-DietMood-30"><span class="cite-bracket">[</span>30<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-CognBPStress_31-0" class="reference"><a href="#cite_note-CognBPStress-31"><span class="cite-bracket">[</span>31<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-DietNeur_32-0" class="reference"><a href="#cite_note-DietNeur-32"><span class="cite-bracket">[</span>32<span class="cite-bracket">]</span></a></sup> </p><p>A 2015 <a href="/wiki/Systematic_review" title="Systematic review">systematic review</a> found that "tyrosine loading acutely counteracts decrements in working memory and information processing that are induced by demanding situational conditions such as extreme weather or <a href="/wiki/Cognitive_load" title="Cognitive load">cognitive load</a>" and therefore "tyrosine may benefit healthy individuals exposed to demanding situational conditions".<sup id="cite_ref-33" class="reference"><a href="#cite_note-33"><span class="cite-bracket">[</span>33<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Industrial_synthesis">Industrial synthesis</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Tyrosine&action=edit&section=11" title="Edit section: Industrial synthesis"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>L-tyrosine is used in <a href="/wiki/Pharmaceuticals" class="mw-redirect" title="Pharmaceuticals">pharmaceuticals</a>, <a href="/wiki/Dietary_supplements" class="mw-redirect" title="Dietary supplements">dietary supplements</a>, and <a href="/wiki/Food_additives" class="mw-redirect" title="Food additives">food additives</a>. Two methods were formerly used to manufacture L-tyrosine. The first involves the extraction of the desired amino acid from protein hydrolysates using a chemical approach. The second utilizes enzymatic synthesis from phenolics, pyruvate, and ammonia through the use of <a href="/wiki/Tyrosine_phenol-lyase" title="Tyrosine phenol-lyase">tyrosine phenol-lyase</a>.<sup id="cite_ref-Perspectives_of_biotechnological_pr_34-0" class="reference"><a href="#cite_note-Perspectives_of_biotechnological_pr-34"><span class="cite-bracket">[</span>34<span class="cite-bracket">]</span></a></sup> Advances in <a href="/wiki/Genetic_engineering" title="Genetic engineering">genetic engineering</a> and the advent of <a href="/wiki/Industrial_fermentation" title="Industrial fermentation">industrial fermentation</a> have shifted the synthesis of L-tyrosine to the use of engineered strains of <i>E. coli</i>.<sup id="cite_ref-35" class="reference"><a href="#cite_note-35"><span class="cite-bracket">[</span>35<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Perspectives_of_biotechnological_pr_34-1" class="reference"><a href="#cite_note-Perspectives_of_biotechnological_pr-34"><span class="cite-bracket">[</span>34<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="See_also">See also</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Tyrosine&action=edit&section=12" title="Edit section: See also"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a href="/wiki/Albinism" title="Albinism">Albinism</a></li> <li><a href="/wiki/Alkaptonuria" title="Alkaptonuria">Alkaptonuria</a></li> <li><a href="/wiki/Betalain" title="Betalain">Betalain</a></li> <li><a href="/wiki/Category:Iodinated_tyrosine_derivatives" title="Category:Iodinated tyrosine derivatives">Iodinated tyrosine derivatives</a></li> <li><a href="/wiki/Pauly_reaction" title="Pauly reaction">Pauly reaction</a></li> <li><a href="/wiki/Tyramine" title="Tyramine">Tyramine</a></li> <li><a href="/wiki/Tyrosine_sulfation" title="Tyrosine sulfation">Tyrosine sulfation</a></li> <li><a href="/wiki/Tyrosinemia" title="Tyrosinemia">Tyrosinemia</a></li></ul> <div class="mw-heading mw-heading2"><h2 id="References">References</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Tyrosine&action=edit&section=13" title="Edit section: References"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1239543626">.mw-parser-output .reflist{margin-bottom:0.5em;list-style-type:decimal}@media screen{.mw-parser-output .reflist{font-size:90%}}.mw-parser-output .reflist .references{font-size:100%;margin-bottom:0;list-style-type:inherit}.mw-parser-output .reflist-columns-2{column-width:30em}.mw-parser-output .reflist-columns-3{column-width:25em}.mw-parser-output .reflist-columns{margin-top:0.3em}.mw-parser-output .reflist-columns ol{margin-top:0}.mw-parser-output .reflist-columns li{page-break-inside:avoid;break-inside:avoid-column}.mw-parser-output .reflist-upper-alpha{list-style-type:upper-alpha}.mw-parser-output .reflist-upper-roman{list-style-type:upper-roman}.mw-parser-output .reflist-lower-alpha{list-style-type:lower-alpha}.mw-parser-output .reflist-lower-greek{list-style-type:lower-greek}.mw-parser-output .reflist-lower-roman{list-style-type:lower-roman}</style><div class="reflist"> <div class="mw-references-wrap mw-references-columns"><ol class="references"> <li id="cite_note-Frey-1"><span class="mw-cite-backlink">^ <a href="#cite_ref-Frey_1-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Frey_1-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><style data-mw-deduplicate="TemplateStyles:r1238218222">.mw-parser-output cite.citation{font-style:inherit;word-wrap:break-word}.mw-parser-output .citation q{quotes:"\"""\"""'""'"}.mw-parser-output .citation:target{background-color:rgba(0,127,255,0.133)}.mw-parser-output .id-lock-free.id-lock-free a{background:url("//upload.wikimedia.org/wikipedia/commons/6/65/Lock-green.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-limited.id-lock-limited a,.mw-parser-output .id-lock-registration.id-lock-registration a{background:url("//upload.wikimedia.org/wikipedia/commons/d/d6/Lock-gray-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-subscription.id-lock-subscription a{background:url("//upload.wikimedia.org/wikipedia/commons/a/aa/Lock-red-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .cs1-ws-icon a{background:url("//upload.wikimedia.org/wikipedia/commons/4/4c/Wikisource-logo.svg")right 0.1em center/12px no-repeat}body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-free a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-limited a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-registration a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-subscription a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .cs1-ws-icon a{background-size:contain;padding:0 1em 0 0}.mw-parser-output .cs1-code{color:inherit;background:inherit;border:none;padding:inherit}.mw-parser-output .cs1-hidden-error{display:none;color:var(--color-error,#d33)}.mw-parser-output .cs1-visible-error{color:var(--color-error,#d33)}.mw-parser-output .cs1-maint{display:none;color:#085;margin-left:0.3em}.mw-parser-output .cs1-kern-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right{padding-right:0.2em}.mw-parser-output .citation .mw-selflink{font-weight:inherit}@media screen{.mw-parser-output .cs1-format{font-size:95%}html.skin-theme-clientpref-night .mw-parser-output .cs1-maint{color:#18911f}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .cs1-maint{color:#18911f}}</style><cite id="CITEREFFreyKoetzleLehmannHamilton1973" class="citation journal cs1">Frey MN, Koetzle TF, 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"Perspectives of biotechnological production of L-tyrosine and its applications". <i>Applied Microbiology and Biotechnology</i>. <b>77</b> (4): 751–62. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1007%2Fs00253-007-1243-y">10.1007/s00253-007-1243-y</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/17968539">17968539</a>. <a href="/wiki/S2CID_(identifier)" class="mw-redirect" title="S2CID (identifier)">S2CID</a> <a rel="nofollow" class="external text" href="https://api.semanticscholar.org/CorpusID:23088822">23088822</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Applied+Microbiology+and+Biotechnology&rft.atitle=Perspectives+of+biotechnological+production+of+L-tyrosine+and+its+applications&rft.volume=77&rft.issue=4&rft.pages=751-62&rft.date=2007-12&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A23088822%23id-name%3DS2CID&rft_id=info%3Apmid%2F17968539&rft_id=info%3Adoi%2F10.1007%2Fs00253-007-1243-y&rft.aulast=L%C3%BCtke-Eversloh&rft.aufirst=T&rft.au=Santos%2C+CN&rft.au=Stephanopoulos%2C+G&rfr_id=info%3Asid%2Fen.wikipedia.org%3ATyrosine" class="Z3988"></span></span> </li> <li id="cite_note-35"><span class="mw-cite-backlink"><b><a href="#cite_ref-35">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFChavez-BejarBaez-ViverosMartinezBolivar2012" class="citation journal cs1">Chavez-Bejar M, Baez-Viveros J, Martinez A, Bolivar F, Gosset G (2012). "Biotechnological production of L-tyrosine and derived compounds". <i>Process Biochemistry</i>. <b>47</b> (7): 1017–1026. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2Fj.procbio.2012.04.005">10.1016/j.procbio.2012.04.005</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Process+Biochemistry&rft.atitle=Biotechnological+production+of+L-tyrosine+and+derived+compounds&rft.volume=47&rft.issue=7&rft.pages=1017-1026&rft.date=2012&rft_id=info%3Adoi%2F10.1016%2Fj.procbio.2012.04.005&rft.aulast=Chavez-Bejar&rft.aufirst=M&rft.au=Baez-Viveros%2C+J&rft.au=Martinez%2C+A&rft.au=Bolivar%2C+F&rft.au=Gosset%2C+G&rfr_id=info%3Asid%2Fen.wikipedia.org%3ATyrosine" class="Z3988"></span></span> </li> </ol></div></div> <div class="mw-heading mw-heading2"><h2 id="External_links">External links</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Tyrosine&action=edit&section=14" title="Edit section: External links"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a rel="nofollow" class="external text" href="http://gmd.mpimp-golm.mpg.de/Spectrums/e8b4de66-fbb5-4629-9e12-0cce4503c881.aspx">Tyrosine MS Spectrum</a></li> <li><a rel="nofollow" class="external text" href="http://www.genome.jp/kegg/pathway/map/map00350.html">Tyrosine metabolism</a> <a rel="nofollow" class="external text" href="https://web.archive.org/web/20190726082244/http://www.genome.jp/kegg/pathway/map/map00350.html">Archived</a> 2019-07-26 at the <a href="/wiki/Wayback_Machine" title="Wayback Machine">Wayback Machine</a></li> <li><a rel="nofollow" class="external text" href="http://www.chem.qmul.ac.uk/iubmb/enzyme/reaction/AminoAcid/PheTyr.html">Phenylalanine and tyrosine biosynthesis</a></li> <li><a rel="nofollow" class="external text" href="http://www.genome.jp/kegg/pathway/map/map00400.html">Phenylalanine, Tyrosine, and tryptophan biosynthesis</a> <a rel="nofollow" class="external text" href="https://web.archive.org/web/20210506123540/http://www.genome.jp/kegg/pathway/map/map00400.html">Archived</a> 2021-05-06 at the <a href="/wiki/Wayback_Machine" title="Wayback Machine">Wayback Machine</a></li></ul> <div class="navbox-styles"><style data-mw-deduplicate="TemplateStyles:r1129693374">.mw-parser-output .hlist dl,.mw-parser-output .hlist ol,.mw-parser-output .hlist ul{margin:0;padding:0}.mw-parser-output .hlist dd,.mw-parser-output .hlist dt,.mw-parser-output .hlist li{margin:0;display:inline}.mw-parser-output .hlist.inline,.mw-parser-output .hlist.inline dl,.mw-parser-output .hlist.inline ol,.mw-parser-output .hlist.inline ul,.mw-parser-output .hlist dl dl,.mw-parser-output .hlist dl ol,.mw-parser-output .hlist dl ul,.mw-parser-output .hlist ol dl,.mw-parser-output .hlist ol ol,.mw-parser-output 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2px"><div><span typeof="mw:File"><a href="/wiki/File:L-amino_acid_any.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/0/0e/L-amino_acid_any.png/182px-L-amino_acid_any.png" decoding="async" width="182" height="160" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/0/0e/L-amino_acid_any.png/273px-L-amino_acid_any.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/0/0e/L-amino_acid_any.png/364px-L-amino_acid_any.png 2x" data-file-width="728" data-file-height="640" /></a></span></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">By properties</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Aliphatic_compound" title="Aliphatic compound">Aliphatic</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/Branched-chain_amino_acid" title="Branched-chain amino acid">Branched-chain amino acids</a> (<a href="/wiki/Valine" title="Valine">Valine</a></li> <li><a href="/wiki/Isoleucine" title="Isoleucine">Isoleucine</a></li> <li><a href="/wiki/Leucine" title="Leucine">Leucine</a>)</li> <li><a href="/wiki/Methionine" title="Methionine">Methionine</a></li> <li><a href="/wiki/Alanine" title="Alanine">Alanine</a></li> <li><a href="/wiki/Proline" title="Proline">Proline</a></li> <li><a href="/wiki/Glycine" title="Glycine">Glycine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Aromatic_amino_acid" title="Aromatic amino acid">Aromatic</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/Histidine" title="Histidine">Histidine</a></li> <li><a class="mw-selflink selflink">Tyrosine</a></li> <li><a href="/wiki/Tryptophan" title="Tryptophan">Tryptophan</a></li> <li><a href="/wiki/Phenylalanine" title="Phenylalanine">Phenylalanine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Chemical_polarity" title="Chemical polarity">Polar</a>, uncharged</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/Asparagine" title="Asparagine">Asparagine</a></li> <li><a href="/wiki/Glutamine" title="Glutamine">Glutamine</a></li> <li><a href="/wiki/Serine" title="Serine">Serine</a></li> <li><a href="/wiki/Threonine" title="Threonine">Threonine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Positive charge (p<i>K</i><sub>a</sub>)</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Lysine" title="Lysine">Lysine</a> (≈10.8)</li> <li><a href="/wiki/Arginine" title="Arginine">Arginine</a> (≈12.5)</li> <li><a href="/wiki/Histidine" title="Histidine">Histidine</a> (≈6.1)</li> <li><a href="/wiki/Pyrrolysine" title="Pyrrolysine">Pyrrolysine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Negative charge (p<i>K</i><sub>a</sub>)</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Aspartic_acid" title="Aspartic acid">Aspartic acid</a> (≈3.9)</li> <li><a href="/wiki/Glutamic_acid" title="Glutamic acid">Glutamic acid</a> (≈4.1)</li> <li><a href="/wiki/Selenocysteine" title="Selenocysteine">Selenocysteine</a> (≈5.4)</li> <li><a href="/wiki/Cysteine" title="Cysteine">Cysteine</a> (≈8.3)</li> <li><a class="mw-selflink selflink">Tyrosine</a> (≈10.1)</li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><td class="navbox-abovebelow" colspan="3"><div><div class="hlist" style="font-size:88%;"> <ul><li><b><a href="/wiki/Amino_acids" class="mw-redirect" title="Amino acids">Amino acids</a> types</b>: <a href="/wiki/Template:Encoded_amino_acids" class="mw-redirect" title="Template:Encoded amino acids">Encoded (proteins)</a></li> <li><a href="/wiki/Essential_amino_acids" class="mw-redirect" title="Essential amino acids">Essential</a></li> <li><a href="/wiki/Template:Non-proteinogenic_amino_acids" title="Template:Non-proteinogenic amino acids">Non-proteinogenic</a></li> <li><a href="/wiki/Ketogenic_amino_acids" class="mw-redirect" title="Ketogenic amino acids">Ketogenic</a></li> <li><a href="/wiki/Glucogenic_amino_acids" class="mw-redirect" title="Glucogenic amino acids">Glucogenic</a></li> <li><a href="/wiki/Secondary_amino_acid" title="Secondary amino acid">Secondary amino</a></li> <li><a href="/wiki/Imino_acid" title="Imino acid">Imino acids</a></li> <li><a href="/wiki/D-amino_acids" class="mw-redirect" title="D-amino acids">D-amino acids</a></li> <li><a href="/wiki/Dehydroamino_acid" title="Dehydroamino acid">Dehydroamino acids</a></li></ul> </div></div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"></div><div role="navigation" class="navbox" aria-labelledby="Amino_acid_metabolism_metabolic_intermediates" style="padding:3px"><table class="nowraplinks mw-collapsible mw-collapsed navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Amino_acid_metabolism_intermediates" title="Template:Amino acid metabolism intermediates"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Amino_acid_metabolism_intermediates" title="Template talk:Amino acid metabolism intermediates"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Amino_acid_metabolism_intermediates" title="Special:EditPage/Template:Amino acid metabolism intermediates"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Amino_acid_metabolism_metabolic_intermediates" style="font-size:114%;margin:0 4em"><a href="/wiki/Amino_acid" title="Amino acid">Amino acid</a> <a href="/wiki/Amino_acid_synthesis" title="Amino acid synthesis">metabolism</a> <a href="/wiki/Metabolic_intermediate" title="Metabolic intermediate">metabolic intermediates</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Ketogenic_amino_acid" title="Ketogenic amino acid">K</a>→<a href="/wiki/Acetyl-CoA" title="Acetyl-CoA">acetyl-CoA</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Lysine" title="Lysine">lysine</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/Saccharopine" title="Saccharopine">Saccharopine</a></li> <li><a href="/wiki/Allysine" title="Allysine">Allysine</a></li> <li><a href="/wiki/Alpha-Aminoadipic_acid" class="mw-redirect" title="Alpha-Aminoadipic acid">α-Aminoadipic acid</a></li> <li><a href="/wiki/2-Oxoadipic_acid" title="2-Oxoadipic acid">2-Oxoadipic acid</a></li> <li><a href="/wiki/Glutaryl-CoA" title="Glutaryl-CoA">Glutaryl-CoA</a></li> <li><a href="/wiki/Glutaconyl-CoA" title="Glutaconyl-CoA">Glutaconyl-CoA</a></li> <li><a href="/wiki/Crotonyl-CoA" title="Crotonyl-CoA">Crotonyl-CoA</a></li> <li><a href="/wiki/Beta-Hydroxybutyryl-CoA" class="mw-redirect" title="Beta-Hydroxybutyryl-CoA">β-Hydroxybutyryl-CoA</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Leucine" title="Leucine">leucine</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/Beta-Hydroxy_beta-methylbutyric_acid" class="mw-redirect" title="Beta-Hydroxy beta-methylbutyric acid">β-Hydroxy β-methylbutyric acid</a></li> <li><a href="/wiki/Beta-Hydroxy_beta-methylbutyryl-CoA" class="mw-redirect" title="Beta-Hydroxy beta-methylbutyryl-CoA">β-Hydroxy β-methylbutyryl-CoA</a></li> <li><a href="/wiki/Isovaleryl-CoA" title="Isovaleryl-CoA">Isovaleryl-CoA</a></li> <li><a href="/wiki/Alpha-Ketoisocaproic_acid" class="mw-redirect" title="Alpha-Ketoisocaproic acid">α-Ketoisocaproic acid</a></li> <li><a href="/wiki/Beta-Ketoisocaproic_acid" class="mw-redirect" title="Beta-Ketoisocaproic acid">β-Ketoisocaproic acid</a></li> <li><a href="/w/index.php?title=Beta-Ketoisocaproyl-CoA&action=edit&redlink=1" class="new" title="Beta-Ketoisocaproyl-CoA (page does not exist)">β-Ketoisocaproyl-CoA</a></li> <li><a href="/wiki/%CE%92-Leucine" title="Β-Leucine">β-Leucine</a></li> <li><a href="/wiki/Methylcrotonyl-CoA" title="Methylcrotonyl-CoA">β-Methylcrotonyl-CoA</a></li> <li><a href="/wiki/%CE%92-Methylglutaconyl-CoA" class="mw-redirect" title="Β-Methylglutaconyl-CoA">β-Methylglutaconyl-CoA</a></li> <li><a href="/wiki/HMG-CoA" title="HMG-CoA">β-Hydroxy β-methylglutaryl-CoA</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Tryptophan" title="Tryptophan">tryptophan</a>→<a href="/wiki/Alanine" title="Alanine">alanine</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/N%27-Formylkynurenine" title="N'-Formylkynurenine"><i>N</i>′-Formylkynurenine</a></li> <li><a href="/wiki/Kynurenine" title="Kynurenine">Kynurenine</a></li> <li><a href="/wiki/Anthranilic_acid" title="Anthranilic acid">Anthranilic acid</a></li> <li><a href="/wiki/3-Hydroxykynurenine" title="3-Hydroxykynurenine">3-Hydroxykynurenine</a></li> <li><a href="/wiki/3-Hydroxyanthranilic_acid" title="3-Hydroxyanthranilic acid">3-Hydroxyanthranilic acid</a></li> <li><a href="/wiki/2-Amino-3-carboxymuconic_semialdehyde" title="2-Amino-3-carboxymuconic semialdehyde">2-Amino-3-carboxymuconic semialdehyde</a></li> <li><a href="/wiki/2-Aminomuconic_semialdehyde" title="2-Aminomuconic semialdehyde">2-Aminomuconic semialdehyde</a></li> <li><a href="/wiki/2-Aminomuconic_acid" title="2-Aminomuconic acid">2-Aminomuconic acid</a></li> <li><a href="/wiki/Glutaryl-CoA" title="Glutaryl-CoA">Glutaryl-CoA</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Glucogenic_amino_acid" title="Glucogenic amino acid">G</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%">G→<a href="/wiki/Pyruvate" class="mw-redirect" title="Pyruvate">pyruvate</a>→ <br /><a href="/wiki/Citrate" class="mw-redirect" title="Citrate">citrate</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th id="glycine→serine→" scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Glycine" title="Glycine">glycine</a>→<br /><a href="/wiki/Serine" title="Serine">serine</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-Phosphoglyceric_acid" title="3-Phosphoglyceric acid">3-Phosphoglyceric acid</a></li></ul> <ul><li><a href="/wiki/Glycine" title="Glycine">glycine</a>→<a href="/wiki/Creatine" title="Creatine">creatine</a>: <a href="/wiki/Glycocyamine" title="Glycocyamine">Glycocyamine</a></li> <li><a href="/wiki/Phosphocreatine" title="Phosphocreatine">Phosphocreatine</a></li> <li><a href="/wiki/Creatinine" title="Creatinine">Creatinine</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">G→<a href="/wiki/Glutamate" class="mw-redirect" title="Glutamate">glutamate</a>→<br /><a href="/wiki/Alpha-Ketoglutaric_acid" class="mw-redirect" title="Alpha-Ketoglutaric acid">α-ketoglutarate</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Histidine" title="Histidine">histidine</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/Urocanic_acid" title="Urocanic acid">Urocanic acid</a></li> <li><a href="/wiki/Imidazol-4-one-5-propionic_acid" title="Imidazol-4-one-5-propionic acid">Imidazol-4-one-5-propionic acid</a></li> <li><a href="/wiki/Formiminoglutamic_acid" title="Formiminoglutamic acid">Formiminoglutamic acid</a></li> <li><a href="/wiki/Glutamate-1-semialdehyde" title="Glutamate-1-semialdehyde">Glutamate-1-semialdehyde</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Proline" title="Proline">proline</a>→</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/1-Pyrroline-5-carboxylic_acid" title="1-Pyrroline-5-carboxylic acid">1-Pyrroline-5-carboxylic acid</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Arginine" title="Arginine">arginine</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/Agmatine" title="Agmatine">Agmatine</a></li> <li><a href="/wiki/Ornithine" title="Ornithine">Ornithine</a></li> <li><a href="/wiki/Citrulline" title="Citrulline">Citrulline</a></li> <li><a href="/wiki/Cadaverine" title="Cadaverine">Cadaverine</a></li> <li><a href="/wiki/Putrescine" title="Putrescine">Putrescine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">other</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Cysteine" title="Cysteine">cysteine</a>+<a href="/wiki/Glutamate" class="mw-redirect" title="Glutamate">glutamate</a>→<a href="/wiki/Glutathione" title="Glutathione">glutathione</a>: <a href="/wiki/Gamma-Glutamylcysteine" class="mw-redirect" title="Gamma-Glutamylcysteine">γ-Glutamylcysteine</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">G→<a href="/wiki/Propionyl-CoA" title="Propionyl-CoA">propionyl-CoA</a>→<br /><a href="/wiki/Succinyl-CoA" title="Succinyl-CoA">succinyl-CoA</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Valine" title="Valine">valine</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/Alpha-Ketoisovaleric_acid" class="mw-redirect" title="Alpha-Ketoisovaleric acid">α-Ketoisovaleric acid</a></li> <li><a href="/wiki/Isobutyryl-CoA" title="Isobutyryl-CoA">Isobutyryl-CoA</a></li> <li><a href="/wiki/Methacrylyl-CoA" title="Methacrylyl-CoA">Methacrylyl-CoA</a></li> <li><a href="/wiki/3-Hydroxyisobutyryl-CoA" title="3-Hydroxyisobutyryl-CoA">3-Hydroxyisobutyryl-CoA</a></li> <li><a href="/wiki/3-Hydroxyisobutyric_acid" title="3-Hydroxyisobutyric acid">3-Hydroxyisobutyric acid</a></li> <li><a href="/wiki/2-Methyl-3-oxopropanoic_acid" class="mw-redirect" title="2-Methyl-3-oxopropanoic acid">2-Methyl-3-oxopropanoic acid</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Isoleucine" title="Isoleucine">isoleucine</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/2,3-Dihydroxy-3-methylpentanoic_acid" title="2,3-Dihydroxy-3-methylpentanoic acid">2,3-Dihydroxy-3-methylpentanoic acid</a></li> <li><a href="/wiki/2-Methylbutyryl-CoA" title="2-Methylbutyryl-CoA">2-Methylbutyryl-CoA</a></li> <li><a href="/wiki/Tiglyl-CoA" title="Tiglyl-CoA">Tiglyl-CoA</a></li> <li><a href="/wiki/2-Methylacetoacetyl-CoA" title="2-Methylacetoacetyl-CoA">2-Methylacetoacetyl-CoA</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Methionine" title="Methionine">methionine</a>→</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i><a href="/wiki/Methionine#Generation_of_homocysteine" title="Methionine">generation of homocysteine</a>:</i> <a href="/wiki/S-Adenosyl_methionine" title="S-Adenosyl methionine"><i>S</i>-Adenosyl methionine</a></li> <li><a href="/wiki/S-Adenosyl-L-homocysteine" 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></li> <li><a href="/wiki/Homocysteine" title="Homocysteine">Homocysteine</a></li></ul> <ul><li><i><a href="/wiki/Methionine#Conversion_to_cysteine" title="Methionine">conversion to cysteine</a>:</i> <a href="/wiki/Cystathionine" title="Cystathionine">Cystathionine</a></li> <li><a href="/wiki/Alpha-Ketobutyric_acid" class="mw-redirect" title="Alpha-Ketobutyric acid">α-Ketobutyric acid</a> + <a href="/wiki/Cysteine" title="Cysteine">Cysteine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Threonine" title="Threonine">threonine</a>→</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Alpha-Ketobutyric_acid" class="mw-redirect" title="Alpha-Ketobutyric acid">α-Ketobutyric acid</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Propionyl-CoA" title="Propionyl-CoA">propionyl-CoA</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/Methylmalonyl-CoA" title="Methylmalonyl-CoA">Methylmalonyl-CoA</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">G→<a href="/wiki/Fumarate" class="mw-redirect" title="Fumarate">fumarate</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Phenylalanine" title="Phenylalanine">phenylalanine</a>→<a class="mw-selflink selflink">tyrosine</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/4-Hydroxyphenylpyruvic_acid" title="4-Hydroxyphenylpyruvic acid">4-Hydroxyphenylpyruvic acid</a></li> <li><a href="/wiki/Homogentisic_acid" title="Homogentisic acid">Homogentisic acid</a></li> <li><a href="/wiki/4-Maleylacetoacetic_acid" title="4-Maleylacetoacetic acid">4-Maleylacetoacetic acid</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">G→<a href="/wiki/Oxaloacetate" class="mw-redirect" title="Oxaloacetate">oxaloacetate</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i>see <a href="/wiki/Urea_cycle" title="Urea cycle">urea cycle</a></i></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Other</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Cysteine_metabolism" title="Cysteine metabolism">Cysteine metabolism</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/Cysteine_sulfinic_acid" title="Cysteine sulfinic acid">Cysteine sulfinic acid</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"></div><div role="navigation" class="navbox" aria-labelledby="Neurotransmitter_metabolic_intermediates" style="padding:3px"><table class="nowraplinks mw-collapsible autocollapse navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Neurotransmitter_metabolism_intermediates" title="Template:Neurotransmitter metabolism intermediates"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Neurotransmitter_metabolism_intermediates" title="Template talk:Neurotransmitter metabolism intermediates"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Neurotransmitter_metabolism_intermediates" title="Special:EditPage/Template:Neurotransmitter metabolism intermediates"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Neurotransmitter_metabolic_intermediates" style="font-size:114%;margin:0 4em"><a href="/wiki/Neurotransmitter" title="Neurotransmitter">Neurotransmitter</a> <a href="/wiki/Metabolic_intermediate" title="Metabolic intermediate">metabolic intermediates</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Catecholamine" title="Catecholamine">Catecholamines</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Anabolism" title="Anabolism">Anabolism</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/Phenylalanine" title="Phenylalanine">Phenylalanine</a> → <a class="mw-selflink selflink">Tyrosine</a> → <a href="/wiki/L-DOPA" title="L-DOPA">DOPA (levodopa)</a> → <a href="/wiki/Dopamine" title="Dopamine">Dopamine</a> → <a href="/wiki/Norepinephrine" title="Norepinephrine">Norepinephrine</a> → <a href="/wiki/Epinephrine" class="mw-redirect" title="Epinephrine">Epinephrine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Catabolism" title="Catabolism">Catabolism</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Dopamine" title="Dopamine">Dopamine</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/3,4-Dihydroxyphenylacetaldehyde" title="3,4-Dihydroxyphenylacetaldehyde">3,4-Dihydroxyphenylacetaldehyde (DOPAL)</a></li> <li><a href="/wiki/3,4-Dihydroxyphenylacetic_acid" title="3,4-Dihydroxyphenylacetic acid">3,4-Dihydroxyphenylacetic acid (DOPAC)</a></li> <li><a href="/wiki/Homovanillyl_alcohol" title="Homovanillyl alcohol">Homovanillyl alcohol</a></li> <li><a href="/wiki/Hydroxytyrosol" title="Hydroxytyrosol">Hydroxytyrosol (3,4-dihydroxyphenylethanol; DOPET)</a></li> <li><a href="/wiki/3-Methoxytyramine" title="3-Methoxytyramine">3-Methoxytyramine (3-MT)</a></li> <li><a href="/wiki/Homovanillic_acid" title="Homovanillic acid">Homovanillic acid (HVA)</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Norepinephrine" title="Norepinephrine">Norepinephrine</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/3,4-Dihydroxyphenylglycolaldehyde" title="3,4-Dihydroxyphenylglycolaldehyde">3,4-Dihydroxyphenylglycolaldehyde (DOPEGAL, DHMAL)</a></li> <li><a href="/wiki/3,4-Dihydroxymandelic_acid" title="3,4-Dihydroxymandelic acid">3,4-Dihydroxymandelic acid (DHMA)</a></li> <li><a href="/wiki/Normetanephrine" title="Normetanephrine">Normetanephrine</a></li> <li><a href="/w/index.php?title=3-Methoxy-4-hydroxymandelaldehyde&action=edit&redlink=1" class="new" title="3-Methoxy-4-hydroxymandelaldehyde (page does not exist)">3-Methoxy-4-hydroxymandelaldehyde (MHMAL)</a></li> <li><a href="/wiki/Vanillylmandelic_acid" title="Vanillylmandelic acid">Vanillylmandelic acid (VMA)</a></li> <li><a href="/wiki/Dihydroxyphenylethylene_glycol" title="Dihydroxyphenylethylene glycol">3,4-Dihydroxyphenylethylene glycol (DOPEG, DHPG)</a></li> <li><a href="/wiki/3-Methoxy-4-hydroxyphenylglycol" title="3-Methoxy-4-hydroxyphenylglycol">3-Methoxy-4-hydroxyphenylglycol (MHPG, MOPEG)</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Epinephrine" class="mw-redirect" title="Epinephrine">Epinephrine</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/3,4-Dihydroxyphenylglycolaldehyde" title="3,4-Dihydroxyphenylglycolaldehyde">3,4-Dihydroxyphenylglycolaldehyde (DOPEGAL, DHMAL)</a></li> <li><a href="/wiki/Metanephrine" title="Metanephrine">Metanephrine</a></li> <li><a href="/w/index.php?title=3-Methoxy-4-hydroxymandelaldehyde&action=edit&redlink=1" class="new" title="3-Methoxy-4-hydroxymandelaldehyde (page does not exist)">3-Methoxy-4-hydroxymandelaldehyde (MHMAL)</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Tryptophan" title="Tryptophan">Tryptophan</a>→<a href="/wiki/Serotonin" title="Serotonin">Serotonin</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Anabolism" title="Anabolism">Anabolism</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/Tryptophan" title="Tryptophan">Tryptophan</a></li> <li><a href="/wiki/5-Hydroxytryptophan" title="5-Hydroxytryptophan">5-Hydroxytryptophan (5-HTP)</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Catabolism" title="Catabolism">Catabolism</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/5-Hydroxyindoleacetaldehyde" title="5-Hydroxyindoleacetaldehyde">5-Hydroxyindoleacetaldehyde (5-HIAL)</a></li> <li><a href="/wiki/5-Hydroxyindoleacetic_acid" title="5-Hydroxyindoleacetic acid">5-Hydroxyindoleacetic acid (5-HIAA)</a></li> <li><a href="/w/index.php?title=5-Hydroxytryptophol&action=edit&redlink=1" class="new" title="5-Hydroxytryptophol (page does not exist)">5-Hydroxytryptophol (5-HTOL)</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Serotonin" title="Serotonin">Serotonin</a>→<a href="/wiki/Melatonin" title="Melatonin">Melatonin</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/N-Acetylserotonin" title="N-Acetylserotonin"><i>N</i>-Acetylserotonin (NAS; normelatonin)</a></li> <li><a href="/wiki/5-Methoxytryptamine" title="5-Methoxytryptamine">5-Methoxytryptamine (5-MT)</a></li> <li><a href="/w/index.php?title=5-Methoxyindoleacetaldehyde&action=edit&redlink=1" class="new" title="5-Methoxyindoleacetaldehyde (page does not exist)">5-Methoxyindoleacetaldehyde (5-MIAL)</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Trace_amine" title="Trace amine">Trace amines</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="/w/index.php?title=3-Methoxy-4-hydroxyphenylacetaldehyde&action=edit&redlink=1" class="new" title="3-Methoxy-4-hydroxyphenylacetaldehyde (page does not exist)">3-Methoxy-4-hydroxyphenylacetaldehyde (HMPAL)</a></li> <li><a href="/wiki/4-Hydroxyphenylacetaldehyde" title="4-Hydroxyphenylacetaldehyde">4-Hydroxyphenylacetaldehyde (HPAL)</a></li> <li><a href="/wiki/Indole-3-acetaldehyde" title="Indole-3-acetaldehyde">Indoleacetaldehyde (IAL)</a></li> <li><a href="/w/index.php?title=Phenacetaldehyde&action=edit&redlink=1" class="new" title="Phenacetaldehyde (page does not exist)">Phenacetaldehyde (PAL)</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/%CE%93-Aminobutyric_acid" class="mw-redirect" title="Γ-Aminobutyric acid">GABA</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Glutamate" class="mw-redirect" title="Glutamate">Glutamate</a></li> <li><a href="/wiki/Putrescine" title="Putrescine">Putrescine</a></li> <li><a href="/wiki/%CE%93-Aminobutyraldehyde" title="Γ-Aminobutyraldehyde">γ-Aminobutyraldehyde (GABAL)</a></li> <li><a href="/wiki/N-Acetylputrescine" title="N-Acetylputrescine"><i>N</i>-Acetylputrescine</a></li> <li><a href="/wiki/N-Acetyl-%CE%B3-aminobutyraldehyde" title="N-Acetyl-γ-aminobutyraldehyde"><i>N</i>-Acetyl-γ-aminobutyraldehyde (<i>N</i>-acetyl-GABAL)</a></li> <li><a href="/wiki/N-Acetyl-%CE%B3-aminobutyric_acid" title="N-Acetyl-γ-aminobutyric acid"><i>N</i>-Acetyl-γ-aminobutyric acid (<i>N</i>-acetyl-GABA)</a></li></ul> </div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"></div><div role="navigation" class="navbox" aria-labelledby="Adrenergic_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:Adrenergic_receptor_modulators" title="Template:Adrenergic receptor modulators"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Adrenergic_receptor_modulators" title="Template talk:Adrenergic receptor modulators"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Adrenergic_receptor_modulators" title="Special:EditPage/Template:Adrenergic receptor modulators"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Adrenergic_receptor_modulators" style="font-size:114%;margin:0 4em"><a href="/wiki/Adrenergic_receptor" title="Adrenergic receptor">Adrenergic 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%"><a href="/wiki/Alpha-1_adrenergic_receptor" title="Alpha-1 adrenergic receptor">α<sub>1</sub></a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%">Agonists</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/6-Fluoronorepinephrine" title="6-Fluoronorepinephrine">6-FNE</a></li> <li><a href="/wiki/Amidephrine" title="Amidephrine">Amidephrine</a></li> <li><a href="/wiki/Buspirone" title="Buspirone">Buspirone</a></li> <li><a href="/wiki/Cirazoline" title="Cirazoline">Cirazoline</a></li> <li><a href="/wiki/Corbadrine" title="Corbadrine">Corbadrine</a></li> <li><a href="/wiki/Deoxyepinephrine" title="Deoxyepinephrine">Deoxyepinephrine (epinine, <i>N</i>-methyldopamine)</a></li> <li><a href="/wiki/Desglymidodrine" title="Desglymidodrine">Desglymidodrine</a></li> <li><a href="/w/index.php?title=Dexisometheptene&action=edit&redlink=1" class="new" title="Dexisometheptene (page does not exist)">Dexisometheptene</a></li> <li><a href="/wiki/Dipivefrine" title="Dipivefrine">Dipivefrine</a></li> <li><a href="/wiki/Dopamine" title="Dopamine">Dopamine</a></li> <li><a href="/wiki/Droxidopa" title="Droxidopa">Droxidopa (L-DOPS)</a></li> <li><a href="/wiki/Epinephrine" class="mw-redirect" title="Epinephrine">Epinephrine</a></li> <li><a href="/wiki/Etilefrine" title="Etilefrine">Etilefrine</a></li> <li><a href="/wiki/Etilevodopa" title="Etilevodopa">Etilevodopa</a></li> <li><a href="/wiki/Ethylnorepinephrine" title="Ethylnorepinephrine">Ethylnorepinephrine</a></li> <li><a href="/wiki/Ibopamine" title="Ibopamine">Ibopamine</a></li> <li><a href="/wiki/Indanidine" title="Indanidine">Indanidine</a></li> <li><a href="/wiki/Isometheptene" title="Isometheptene">Isometheptene</a></li> <li><a href="/wiki/L-DOPA" title="L-DOPA">L-DOPA (levodopa)</a></li> <li><a href="/wiki/Phenylalanine" title="Phenylalanine">L-Phenylalanine</a></li> <li><a class="mw-selflink selflink">L-Tyrosine</a></li> <li><a href="/wiki/Melevodopa" title="Melevodopa">Melevodopa</a></li> <li><a href="/wiki/Metaraminol" title="Metaraminol">Metaraminol</a></li> <li><a href="/wiki/Methoxamine" title="Methoxamine">Methoxamine</a></li> <li><a href="/wiki/Methyldopa" title="Methyldopa">Methyldopa</a></li> <li><a href="/wiki/Midodrine" title="Midodrine">Midodrine</a></li> <li><a href="/wiki/Naphazoline" title="Naphazoline">Naphazoline</a></li> <li><a href="/wiki/Norepinephrine" title="Norepinephrine">Norepinephrine</a></li> <li><a href="/wiki/Octopamine" title="Octopamine">Octopamine</a></li> <li><a href="/wiki/Oxymetazoline" title="Oxymetazoline">Oxymetazoline</a></li> <li><a href="/wiki/Phenylephrine" title="Phenylephrine">Phenylephrine</a></li> <li><a href="/wiki/Phenylpropanolamine" title="Phenylpropanolamine">Phenylpropanolamine</a></li> <li><a href="/wiki/Synephrine" title="Synephrine">Synephrine</a></li> <li><a href="/wiki/Tetryzoline" title="Tetryzoline">Tetryzoline</a></li> <li><a href="/wiki/Tiamenidine" title="Tiamenidine">Tiamenidine</a></li> <li><a href="/wiki/XP21279" class="mw-redirect" title="XP21279">XP21279</a></li> <li><a href="/wiki/Xylometazoline" title="Xylometazoline">Xylometazoline</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Antagonists</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/Abanoquil" title="Abanoquil">Abanoquil</a></li> <li><a href="/wiki/Ajmalicine" title="Ajmalicine">Ajmalicine</a></li> <li><a href="/wiki/Alfuzosin" title="Alfuzosin">Alfuzosin</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/Atiprosin" title="Atiprosin">Atiprosin</a></li> <li><a href="/wiki/Atypical_antipsychotic" title="Atypical antipsychotic">Atypical antipsychotics</a> (e.g., <a href="/wiki/Brexpiprazole" title="Brexpiprazole">brexpiprazole</a>, <a href="/wiki/Clozapine" title="Clozapine">clozapine</a>, <a href="/wiki/Olanzapine" title="Olanzapine">olanzapine</a>, <a href="/wiki/Quetiapine" title="Quetiapine">quetiapine</a>, <a href="/wiki/Risperidone" title="Risperidone">risperidone</a>)</li> <li><a href="/wiki/Benoxathian" title="Benoxathian">Benoxathian</a></li> <li><a href="/wiki/Beta_blocker" title="Beta blocker">Beta blockers</a> (e.g., <a href="/wiki/Adimolol" title="Adimolol">adimolol</a>, <a href="/wiki/Amosulalol" title="Amosulalol">amosulalol</a>, <a href="/wiki/Arotinolol" title="Arotinolol">arotinolol</a>, <a href="/wiki/Carvedilol" title="Carvedilol">carvedilol</a>, <a href="/wiki/Eugenodilol" title="Eugenodilol">eugenodilol</a>, <a href="/wiki/Labetalol" title="Labetalol">labetalol</a>)</li> <li><a href="/wiki/Buflomedil" title="Buflomedil">Buflomedil</a></li> <li><a href="/wiki/Bunazosin" title="Bunazosin">Bunazosin</a></li> <li><a href="/wiki/Corynanthine" title="Corynanthine">Corynanthine</a></li> <li><a href="/wiki/Dapiprazole" title="Dapiprazole">Dapiprazole</a></li> <li><a href="/wiki/Domesticine" title="Domesticine">Domesticine</a></li> <li><a href="/wiki/Doxazosin" title="Doxazosin">Doxazosin</a></li> <li><a href="/wiki/Ergoline" title="Ergoline">Ergolines</a> (e.g., <a href="/wiki/Acetergamine" title="Acetergamine">acetergamine</a>, <a href="/wiki/Ergotamine" title="Ergotamine">ergotamine</a>, <a href="/wiki/Dihydroergotamine" title="Dihydroergotamine">dihydroergotamine</a>, <a href="/wiki/Lisuride" title="Lisuride">lisuride</a>, <a href="/wiki/Nicergoline" title="Nicergoline">nicergoline</a>, <a href="/wiki/Terguride" title="Terguride">terguride</a>)</li> <li><a href="/wiki/Etoperidone" title="Etoperidone">Etoperidone</a></li> <li><a href="/wiki/Fenspiride" title="Fenspiride">Fenspiride</a></li> <li><a href="/wiki/Hydroxyzine" title="Hydroxyzine">Hydroxyzine</a></li> <li><a href="/wiki/Indoramin" title="Indoramin">Indoramin</a></li> <li><a href="/wiki/Ketanserin" title="Ketanserin">Ketanserin</a></li> <li><a href="/wiki/L-765,314" title="L-765,314">L-765,314</a></li> <li><a href="/wiki/Meta-Chlorophenylpiperazine" title="Meta-Chlorophenylpiperazine">mCPP</a></li> <li><a href="/wiki/Mepiprazole" title="Mepiprazole">Mepiprazole</a></li> <li><a href="/wiki/Metazosin" title="Metazosin">Metazosin</a></li> <li><a href="/wiki/Monatepil" title="Monatepil">Monatepil</a></li> <li><a href="/wiki/Moxisylyte" title="Moxisylyte">Moxisylyte</a></li> <li><a href="/wiki/Naftopidil" title="Naftopidil">Naftopidil</a></li> <li><a href="/wiki/Nantenine" title="Nantenine">Nantenine</a></li> <li><a href="/wiki/Neldazosin" title="Neldazosin">Neldazosin</a></li> <li><a href="/wiki/Niaprazine" title="Niaprazine">Niaprazine</a></li> <li><a href="/wiki/Niguldipine" title="Niguldipine">Niguldipine</a></li> <li><a href="/wiki/Pardoprunox" title="Pardoprunox">Pardoprunox</a></li> <li><a href="/wiki/Pelanserin" title="Pelanserin">Pelanserin</a></li> <li><a href="/wiki/Perlapine" title="Perlapine">Perlapine</a></li> <li><a href="/wiki/Phendioxan" title="Phendioxan">Phendioxan</a></li> <li><a href="/wiki/Phenoxybenzamine" title="Phenoxybenzamine">Phenoxybenzamine</a></li> <li><a href="/wiki/Phentolamine" title="Phentolamine">Phentolamine</a></li> <li><a href="/wiki/Phenylpiperazine" title="Phenylpiperazine">Phenylpiperazine</a> <a href="/wiki/Antidepressant" title="Antidepressant">antidepressants</a> (e.g., <a href="/wiki/Hydroxynefazodone" title="Hydroxynefazodone">hydroxynefazodone</a>, <a href="/wiki/Nefazodone" title="Nefazodone">nefazodone</a>, <a href="/wiki/Trazodone" title="Trazodone">trazodone</a>, <a href="/wiki/Triazoledione" title="Triazoledione">triazoledione</a>)</li> <li><a href="/wiki/Piperoxan" title="Piperoxan">Piperoxan</a></li> <li><a href="/wiki/Prazosin" title="Prazosin">Prazosin</a></li> <li><a href="/wiki/Quinazosin" title="Quinazosin">Quinazosin</a></li> <li><a href="/wiki/Quinidine" title="Quinidine">Quinidine</a></li> <li><a href="/wiki/Silodosin" title="Silodosin">Silodosin</a></li> <li><a href="/wiki/Spegatrine" title="Spegatrine">Spegatrine</a></li> <li><a href="/wiki/Spiperone" title="Spiperone">Spiperone</a></li> <li><a href="/wiki/Talipexole" title="Talipexole">Talipexole</a></li> <li><a href="/wiki/Tamsulosin" title="Tamsulosin">Tamsulosin</a></li> <li><a href="/wiki/Terazosin" title="Terazosin">Terazosin</a></li> <li><a href="/wiki/Tiodazosin" title="Tiodazosin">Tiodazosin</a></li> <li><a href="/wiki/Tolazoline" title="Tolazoline">Tolazoline</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>)</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/Clomipramine" title="Clomipramine">clomipramine</a>, <a href="/wiki/Doxepin" title="Doxepin">doxepin</a>, <a href="/wiki/Imipramine" title="Imipramine">imipramine</a>, <a href="/wiki/Trimipramine" title="Trimipramine">trimipramine</a>)</li> <li><a href="/wiki/Trimazosin" title="Trimazosin">Trimazosin</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/Fluphenazine" title="Fluphenazine">fluphenazine</a>, <a href="/wiki/Loxapine" title="Loxapine">loxapine</a>, <a href="/wiki/Thioridazine" title="Thioridazine">thioridazine</a>)</li> <li><a href="/wiki/Urapidil" title="Urapidil">Urapidil</a></li> <li><a href="/wiki/WB-4101" title="WB-4101">WB-4101</a></li> <li><a href="/wiki/Zolertine" title="Zolertine">Zolertine</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Alpha-2_adrenergic_receptor" title="Alpha-2 adrenergic receptor">α<sub>2</sub></a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%">Agonists</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/(R)-3-Nitrobiphenyline" title="(R)-3-Nitrobiphenyline">(R)-3-Nitrobiphenyline</a></li> <li><a href="/wiki/4-NEMD" title="4-NEMD">4-NEMD</a></li> <li><a href="/wiki/6-Fluoronorepinephrine" title="6-Fluoronorepinephrine">6-FNE</a></li> <li><a href="/wiki/Amitraz" title="Amitraz">Amitraz</a></li> <li><a href="/wiki/Apraclonidine" title="Apraclonidine">Apraclonidine</a></li> <li><a href="/wiki/Brimonidine" title="Brimonidine">Brimonidine</a></li> <li><a href="/wiki/Clonidine" title="Clonidine">Clonidine</a></li> <li><a href="/wiki/Corbadrine" title="Corbadrine">Corbadrine</a></li> <li><a href="/wiki/Deoxyepinephrine" title="Deoxyepinephrine">Deoxyepinephrine (epinine, <i>N</i>-methyldopamine)</a></li> <li><a href="/wiki/Detomidine" title="Detomidine">Detomidine</a></li> <li><a href="/wiki/Dexmedetomidine" title="Dexmedetomidine">Dexmedetomidine</a></li> <li><a href="/wiki/Dihydroergotamine" title="Dihydroergotamine">Dihydroergotamine</a></li> <li><a href="/wiki/Dipivefrine" title="Dipivefrine">Dipivefrine</a></li> <li><a href="/wiki/Dopamine" title="Dopamine">Dopamine</a></li> <li><a href="/wiki/Droxidopa" title="Droxidopa">Droxidopa (L-DOPS)</a></li> <li><a href="/wiki/Etilevodopa" title="Etilevodopa">Etilevodopa</a></li> <li><a href="/wiki/Ergotamine" title="Ergotamine">Ergotamine</a></li> <li><a href="/wiki/Epinephrine" class="mw-redirect" title="Epinephrine">Epinephrine</a></li> <li><a href="/wiki/Etilefrine" title="Etilefrine">Etilefrine</a></li> <li><a href="/wiki/Ethylnorepinephrine" title="Ethylnorepinephrine">Ethylnorepinephrine</a></li> <li><a href="/wiki/Guanabenz" title="Guanabenz">Guanabenz</a></li> <li><a href="/wiki/Guanfacine" title="Guanfacine">Guanfacine</a></li> <li><a href="/wiki/Guanoxabenz" title="Guanoxabenz">Guanoxabenz</a></li> <li><a href="/wiki/L-DOPA" title="L-DOPA">L-DOPA (levodopa)</a></li> <li><a href="/wiki/Phenylalanine" title="Phenylalanine">L-Phenylalanine</a></li> <li><a class="mw-selflink selflink">L-Tyrosine</a></li> <li><a href="/wiki/Ibopamine" title="Ibopamine">Ibopamine</a></li> <li><a href="/wiki/Lofexidine" title="Lofexidine">Lofexidine</a></li> <li><a href="/wiki/Medetomidine" title="Medetomidine">Medetomidine</a></li> <li><a href="/wiki/Melevodopa" title="Melevodopa">Melevodopa</a></li> <li><a href="/wiki/Methyldopa" title="Methyldopa">Methyldopa</a></li> <li><a href="/wiki/Mivazerol" title="Mivazerol">Mivazerol</a></li> <li><a href="/wiki/Moxonidine" title="Moxonidine">Moxonidine</a></li> <li><a href="/wiki/Naphazoline" title="Naphazoline">Naphazoline</a></li> <li><a href="/wiki/Norepinephrine" title="Norepinephrine">Norepinephrine</a></li> <li><a href="/wiki/Oxymetazoline" title="Oxymetazoline">Oxymetazoline</a></li> <li><a href="/wiki/Phenylpropanolamine" title="Phenylpropanolamine">Phenylpropanolamine</a></li> <li><a href="/wiki/Piperoxan" title="Piperoxan">Piperoxan</a></li> <li><a href="/wiki/PS75" title="PS75">PS75</a></li> <li><a href="/w/index.php?title=Rezatomidine&action=edit&redlink=1" class="new" title="Rezatomidine (page does not exist)">Rezatomidine</a></li> <li><a href="/wiki/Rilmenidine" title="Rilmenidine">Rilmenidine</a></li> <li><a href="/wiki/Romifidine" title="Romifidine">Romifidine</a></li> <li><a href="/wiki/Talipexole" title="Talipexole">Talipexole</a></li> <li><a href="/w/index.php?title=Tasipimidine&action=edit&redlink=1" class="new" title="Tasipimidine (page does not exist)">Tasipimidine</a></li> <li><a href="/wiki/Tetryzoline" title="Tetryzoline">Tetryzoline</a></li> <li><a href="/wiki/Tiamenidine" title="Tiamenidine">Tiamenidine</a></li> <li><a href="/wiki/Tizanidine" title="Tizanidine">Tizanidine</a></li> <li><a href="/wiki/Tolonidine" title="Tolonidine">Tolonidine</a></li> <li><a href="/wiki/Urapidil" title="Urapidil">Urapidil</a></li> <li><a href="/wiki/Vatinoxan" class="mw-redirect" title="Vatinoxan">Vatinoxan</a></li> <li><a href="/wiki/XP21279" class="mw-redirect" title="XP21279">XP21279</a></li> <li><a href="/wiki/Xylazine" title="Xylazine">Xylazine</a></li> <li><a href="/wiki/Xylometazoline" title="Xylometazoline">Xylometazoline</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Antagonists</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/Pyrimidinylpiperazine" title="Pyrimidinylpiperazine">1-PP</a></li> <li><a href="/wiki/Adimolol" title="Adimolol">Adimolol</a></li> <li><a href="/wiki/Amesergide" title="Amesergide">Amesergide</a></li> <li><a href="/wiki/Aptazapine" title="Aptazapine">Aptazapine</a></li> <li><a href="/wiki/Atipamezole" title="Atipamezole">Atipamezole</a></li> <li><a href="/wiki/Atypical_antipsychotic" title="Atypical antipsychotic">Atypical antipsychotics</a> (e.g., <a href="/wiki/Asenapine" title="Asenapine">asenapine</a>, <a href="/wiki/Brexpiprazole" title="Brexpiprazole">brexpiprazole</a>, <a href="/wiki/Clozapine" title="Clozapine">clozapine</a>, <a href="/wiki/Lurasidone" title="Lurasidone">lurasidone</a>, <a href="/wiki/Olanzapine" title="Olanzapine">olanzapine</a>, <a href="/wiki/Paliperidone" title="Paliperidone">paliperidone</a>, <a href="/wiki/Quetiapine" title="Quetiapine">quetiapine</a>, <a href="/wiki/Risperidone" title="Risperidone">risperidone</a>, <a href="/wiki/Zotepine" title="Zotepine">zotepine</a>)</li> <li><a href="/wiki/Azapirone" title="Azapirone">Azapirones</a> (e.g., <a href="/wiki/Buspirone" title="Buspirone">buspirone</a>, <a href="/wiki/Gepirone" title="Gepirone">gepirone</a>, <a href="/wiki/Ipsapirone" title="Ipsapirone">ipsapirone</a>, <a href="/wiki/Tandospirone" title="Tandospirone">tandospirone</a>)</li> <li><a href="/wiki/BRL-44408" title="BRL-44408">BRL-44408</a></li> <li><a href="/wiki/Buflomedil" title="Buflomedil">Buflomedil</a></li> <li><a href="/wiki/Cirazoline" title="Cirazoline">Cirazoline</a></li> <li><a href="/wiki/Efaroxan" title="Efaroxan">Efaroxan</a></li> <li><a href="/wiki/Esmirtazapine" title="Esmirtazapine">Esmirtazapine</a></li> <li><a href="/wiki/Fenmetozole" title="Fenmetozole">Fenmetozole</a></li> <li><a href="/wiki/Fluparoxan" title="Fluparoxan">Fluparoxan</a></li> <li><a href="/wiki/Idazoxan" title="Idazoxan">Idazoxan</a></li> <li><a href="/wiki/Ketanserin" title="Ketanserin">Ketanserin</a></li> <li><a href="/wiki/Lisuride" title="Lisuride">Lisuride</a></li> <li><a href="/wiki/Meta-Chlorophenylpiperazine" title="Meta-Chlorophenylpiperazine">mCPP</a></li> <li><a href="/wiki/Mianserin" title="Mianserin">Mianserin</a></li> <li><a href="/wiki/Mirtazapine" title="Mirtazapine">Mirtazapine</a></li> <li><a href="/wiki/NAN-190" title="NAN-190">NAN-190</a></li> <li><a href="/wiki/Pardoprunox" title="Pardoprunox">Pardoprunox</a></li> <li><a href="/wiki/Phentolamine" title="Phentolamine">Phentolamine</a></li> <li><a href="/wiki/Phenoxybenzamine" title="Phenoxybenzamine">Phenoxybenzamine</a></li> <li><a href="/wiki/Piperoxan" title="Piperoxan">Piperoxan</a></li> <li><a href="/wiki/Piribedil" title="Piribedil">Piribedil</a></li> <li><a href="/wiki/Rauwolscine" title="Rauwolscine">Rauwolscine</a></li> <li><a href="/wiki/Rotigotine" title="Rotigotine">Rotigotine</a></li> <li><a href="/wiki/Setiptiline" title="Setiptiline">Setiptiline</a></li> <li><a href="/wiki/Spegatrine" title="Spegatrine">Spegatrine</a></li> <li><a href="/wiki/Spiroxatrine" title="Spiroxatrine">Spiroxatrine</a></li> <li><a href="/wiki/Sunepitron" title="Sunepitron">Sunepitron</a></li> <li><a href="/wiki/Terguride" title="Terguride">Terguride</a></li> <li><a href="/wiki/Tolazoline" title="Tolazoline">Tolazoline</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/Fluphenazine" title="Fluphenazine">fluphenazine</a>, <a href="/wiki/Loxapine" title="Loxapine">loxapine</a>, <a href="/wiki/Thioridazine" title="Thioridazine">thioridazine</a>)</li> <li><a href="/wiki/Yohimbine" title="Yohimbine">Yohimbine</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/%CE%92-adrenergic_receptor" class="mw-redirect" title="Β-adrenergic receptor">β</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%">Agonists</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/Abediterol" title="Abediterol">Abediterol</a></li> <li><a href="/wiki/Alifedrine" title="Alifedrine">Alifedrine</a></li> <li><a href="/wiki/Amibegron" title="Amibegron">Amibegron</a></li> <li><a href="/wiki/Arbutamine" title="Arbutamine">Arbutamine</a></li> <li><a href="/wiki/Arformoterol" title="Arformoterol">Arformoterol</a></li> <li><a href="/wiki/Arotinolol" title="Arotinolol">Arotinolol</a></li> <li><a href="/wiki/Bromoacetylalprenololmenthane" title="Bromoacetylalprenololmenthane">BAAM</a></li> <li><a href="/wiki/Bambuterol" title="Bambuterol">Bambuterol</a></li> <li><a href="/wiki/Befunolol" title="Befunolol">Befunolol</a></li> <li><a href="/wiki/Bitolterol" title="Bitolterol">Bitolterol</a></li> <li><a href="/wiki/Broxaterol" title="Broxaterol">Broxaterol</a></li> <li><a href="/wiki/Buphenine" title="Buphenine">Buphenine</a></li> <li><a href="/wiki/Carbuterol" title="Carbuterol">Carbuterol</a></li> <li><a href="/wiki/Carmoterol" title="Carmoterol">Carmoterol</a></li> <li><a href="/wiki/Cimaterol" title="Cimaterol">Cimaterol</a></li> <li><a href="/wiki/Clenbuterol" title="Clenbuterol">Clenbuterol</a></li> <li><a href="/wiki/Colterol" title="Colterol">Colterol</a></li> <li><a href="/wiki/Corbadrine" title="Corbadrine">Corbadrine</a></li> <li><a href="/wiki/Denopamine" title="Denopamine">Denopamine</a></li> <li><a href="/wiki/Deoxyepinephrine" title="Deoxyepinephrine">Deoxyepinephrine (epinine, <i>N</i>-methyldopamine)</a></li> <li><a href="/wiki/Dipivefrine" title="Dipivefrine">Dipivefrine</a></li> <li><a href="/wiki/Dobutamine" title="Dobutamine">Dobutamine</a></li> <li><a href="/wiki/Dopamine" title="Dopamine">Dopamine</a></li> <li><a href="/wiki/Dopexamine" title="Dopexamine">Dopexamine</a></li> <li><a href="/wiki/Droxidopa" title="Droxidopa">Droxidopa (L-DOPS)</a></li> <li><a href="/wiki/Epinephrine" class="mw-redirect" title="Epinephrine">Epinephrine</a></li> <li><a href="/wiki/Etafedrine" title="Etafedrine">Etafedrine</a></li> <li><a href="/wiki/Etilefrine" title="Etilefrine">Etilefrine</a></li> <li><a href="/wiki/Etilevodopa" title="Etilevodopa">Etilevodopa</a></li> <li><a href="/wiki/Ethylnorepinephrine" title="Ethylnorepinephrine">Ethylnorepinephrine</a></li> <li><a href="/wiki/Eugenodilol" title="Eugenodilol">Eugenodilol</a></li> <li><a href="/wiki/Fenoterol" title="Fenoterol">Fenoterol</a></li> <li><a href="/wiki/Formoterol" title="Formoterol">Formoterol</a></li> <li><a href="/wiki/Hexoprenaline" title="Hexoprenaline">Hexoprenaline</a></li> <li><a href="/wiki/Higenamine" title="Higenamine">Higenamine</a></li> <li><a href="/wiki/Ibopamine" title="Ibopamine">Ibopamine</a></li> <li><a href="/wiki/Indacaterol" title="Indacaterol">Indacaterol</a></li> <li><a href="/wiki/Isoetarine" title="Isoetarine">Isoetarine</a></li> <li><a href="/wiki/Isoprenaline" title="Isoprenaline">Isoprenaline</a></li> <li><a href="/wiki/Isoxsuprine" title="Isoxsuprine">Isoxsuprine</a></li> <li><a href="/wiki/L-DOPA" title="L-DOPA">L-DOPA (levodopa)</a></li> <li><a href="/wiki/Phenylalanine" title="Phenylalanine">L-Phenylalanine</a></li> <li><a class="mw-selflink selflink">L-Tyrosine</a></li> <li><a href="/wiki/Levosalbutamol" title="Levosalbutamol">Levosalbutamol</a></li> <li><a href="/wiki/Lubabegron" title="Lubabegron">Lubabegron</a></li> <li><a href="/wiki/Mabuterol" title="Mabuterol">Mabuterol</a></li> <li><a href="/wiki/Melevodopa" title="Melevodopa">Melevodopa</a></li> <li><a href="/wiki/Methoxyphenamine" title="Methoxyphenamine">Methoxyphenamine</a></li> <li><a href="/wiki/Methyldopa" title="Methyldopa">Methyldopa</a></li> <li><a href="/wiki/Mirabegron" title="Mirabegron">Mirabegron</a></li> <li><a href="/wiki/Norepinephrine" title="Norepinephrine">Norepinephrine</a></li> <li><a href="/wiki/Orciprenaline" title="Orciprenaline">Orciprenaline</a></li> <li><a href="/wiki/Oxyfedrine" title="Oxyfedrine">Oxyfedrine</a></li> <li><a href="/wiki/PF-610355" title="PF-610355">PF-610355</a></li> <li><a href="/wiki/Phenylpropanolamine" title="Phenylpropanolamine">Phenylpropanolamine</a></li> <li><a href="/wiki/Pirbuterol" title="Pirbuterol">Pirbuterol</a></li> <li><a href="/wiki/Prenalterol" title="Prenalterol">Prenalterol</a></li> <li><a href="/wiki/Ractopamine" title="Ractopamine">Ractopamine</a></li> <li><a href="/wiki/Procaterol" title="Procaterol">Procaterol</a></li> <li><a href="/wiki/Reproterol" title="Reproterol">Reproterol</a></li> <li><a href="/wiki/Rimiterol" title="Rimiterol">Rimiterol</a></li> <li><a href="/wiki/Ritodrine" title="Ritodrine">Ritodrine</a></li> <li><a href="/wiki/Salbutamol" title="Salbutamol">Salbutamol</a></li> <li><a href="/wiki/Salmeterol" title="Salmeterol">Salmeterol</a></li> <li><a href="/wiki/Solabegron" title="Solabegron">Solabegron</a></li> <li><a href="/wiki/Terbutaline" title="Terbutaline">Terbutaline</a></li> <li><a href="/wiki/Tretoquinol" title="Tretoquinol">Tretoquinol</a></li> <li><a href="/wiki/Tulobuterol" title="Tulobuterol">Tulobuterol</a></li> <li><a href="/wiki/Vibegron" title="Vibegron">Vibegron</a></li> <li><a href="/wiki/Vilanterol" title="Vilanterol">Vilanterol</a></li> <li><a href="/wiki/Xamoterol" title="Xamoterol">Xamoterol</a></li> <li><a href="/wiki/XP21279" class="mw-redirect" title="XP21279">XP21279</a></li> <li><a href="/wiki/Zilpaterol" title="Zilpaterol">Zilpaterol</a></li> <li><a href="/wiki/Zinterol" title="Zinterol">Zinterol</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Antagonists</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/Acebutolol" title="Acebutolol">Acebutolol</a></li> <li><a href="/wiki/Adaprolol" title="Adaprolol">Adaprolol</a></li> <li><a href="/wiki/Adimolol" title="Adimolol">Adimolol</a></li> <li><a href="/wiki/Afurolol" title="Afurolol">Afurolol</a></li> <li><a href="/wiki/Alprenolol" title="Alprenolol">Alprenolol</a></li> <li><a href="/wiki/Alprenoxime" title="Alprenoxime">Alprenoxime</a></li> <li><a href="/wiki/Amosulalol" title="Amosulalol">Amosulalol</a></li> <li><a href="/wiki/Ancarolol" title="Ancarolol">Ancarolol</a></li> <li><a href="/wiki/Arnolol" title="Arnolol">Arnolol</a></li> <li><a href="/wiki/Arotinolol" title="Arotinolol">Arotinolol</a></li> <li><a href="/wiki/Atenolol" title="Atenolol">Atenolol</a></li> <li><a href="/wiki/Befunolol" title="Befunolol">Befunolol</a></li> <li><a href="/wiki/Betaxolol" title="Betaxolol">Betaxolol</a></li> <li><a href="/wiki/Bevantolol" title="Bevantolol">Bevantolol</a></li> <li><a href="/wiki/Bisoprolol" title="Bisoprolol">Bisoprolol</a></li> <li><a href="/wiki/Bopindolol" title="Bopindolol">Bopindolol</a></li> <li><a href="/wiki/Bornaprolol" title="Bornaprolol">Bornaprolol</a></li> <li><a href="/wiki/Brefonalol" title="Brefonalol">Brefonalol</a></li> <li><a href="/wiki/Bucindolol" title="Bucindolol">Bucindolol</a></li> <li><a href="/wiki/Bucumolol" title="Bucumolol">Bucumolol</a></li> <li><a href="/wiki/Bufetolol" title="Bufetolol">Bufetolol</a></li> <li><a href="/wiki/Bufuralol" title="Bufuralol">Bufuralol</a></li> <li><a href="/wiki/Bunitrolol" title="Bunitrolol">Bunitrolol</a></li> <li><a href="/wiki/Bunolol" class="mw-redirect" title="Bunolol">Bunolol</a></li> <li><a href="/wiki/Bupranolol" title="Bupranolol">Bupranolol</a></li> <li><a href="/wiki/Butaxamine" title="Butaxamine">Butaxamine</a></li> <li><a href="/wiki/Butidrine" title="Butidrine">Butidrine</a></li> <li><a href="/wiki/Butofilolol" title="Butofilolol">Butofilolol</a></li> <li><a href="/wiki/Capsinolol" title="Capsinolol">Capsinolol</a></li> <li><a href="/wiki/Carazolol" title="Carazolol">Carazolol</a></li> <li><a href="/wiki/Carpindolol" title="Carpindolol">Carpindolol</a></li> <li><a href="/wiki/Carteolol" title="Carteolol">Carteolol</a></li> <li><a href="/wiki/Carvedilol" title="Carvedilol">Carvedilol</a></li> <li><a href="/wiki/Celiprolol" title="Celiprolol">Celiprolol</a></li> <li><a href="/wiki/Cetamolol" title="Cetamolol">Cetamolol</a></li> <li><a href="/wiki/Cicloprolol" title="Cicloprolol">Cicloprolol</a></li> <li><a href="/wiki/Cinamolol" title="Cinamolol">Cinamolol</a></li> <li><a href="/wiki/Cloranolol" title="Cloranolol">Cloranolol</a></li> <li><a href="/wiki/Cyanopindolol" title="Cyanopindolol">Cyanopindolol</a></li> <li><a href="/wiki/Dalbraminol" title="Dalbraminol">Dalbraminol</a></li> <li><a href="/wiki/Dexpropranolol" class="mw-redirect" title="Dexpropranolol">Dexpropranolol</a></li> <li><a href="/wiki/Diacetolol" title="Diacetolol">Diacetolol</a></li> <li><a href="/wiki/Dichloroisoprenaline" title="Dichloroisoprenaline">Dichloroisoprenaline</a></li> <li><a href="/wiki/Dihydroalprenolol" title="Dihydroalprenolol">Dihydroalprenolol</a></li> <li><a href="/wiki/Dilevalol" class="mw-redirect" title="Dilevalol">Dilevalol</a></li> <li><a href="/wiki/Diprafenone" title="Diprafenone">Diprafenone</a></li> <li><a href="/wiki/Draquinolol" title="Draquinolol">Draquinolol</a></li> <li><a href="/wiki/Ecastolol" title="Ecastolol">Ecastolol</a></li> <li><a href="/wiki/Epanolol" title="Epanolol">Epanolol</a></li> <li><a href="/wiki/Ericolol" title="Ericolol">Ericolol</a></li> <li><a href="/wiki/Ersentilide" title="Ersentilide">Ersentilide</a></li> <li><a href="/wiki/Esatenolol" class="mw-redirect" title="Esatenolol">Esatenolol</a></li> <li><a href="/wiki/Esprolol" class="mw-redirect" title="Esprolol">Esprolol</a></li> <li><a href="/wiki/Eugenodilol" title="Eugenodilol">Eugenodilol</a></li> <li><a href="/wiki/Exaprolol" title="Exaprolol">Exaprolol</a></li> <li><a href="/wiki/Falintolol" title="Falintolol">Falintolol</a></li> <li><a href="/wiki/Flestolol" title="Flestolol">Flestolol</a></li> <li><a href="/wiki/Flusoxolol" title="Flusoxolol">Flusoxolol</a></li> <li><a href="/wiki/Hydroxycarteolol" title="Hydroxycarteolol">Hydroxycarteolol</a></li> <li><a href="/wiki/Hydroxytertatolol" title="Hydroxytertatolol">Hydroxytertatolol</a></li> <li><a href="/wiki/ICI-118,551" title="ICI-118,551">ICI-118,551</a></li> <li><a href="/wiki/Idropranolol" class="mw-redirect" title="Idropranolol">Idropranolol</a></li> <li><a href="/wiki/Indenolol" title="Indenolol">Indenolol</a></li> <li><a href="/wiki/Indopanolol" title="Indopanolol">Indopanolol</a></li> <li><a href="/wiki/Iodocyanopindolol" title="Iodocyanopindolol">Iodocyanopindolol</a></li> <li><a href="/wiki/Iprocrolol" title="Iprocrolol">Iprocrolol</a></li> <li><a href="/wiki/Isoxaprolol" title="Isoxaprolol">Isoxaprolol</a></li> <li><a href="/wiki/Isamoltane" title="Isamoltane">Isamoltane</a></li> <li><a href="/wiki/Labetalol" title="Labetalol">Labetalol</a></li> <li><a href="/wiki/Landiolol" title="Landiolol">Landiolol</a></li> <li><a href="/wiki/Levobetaxolol" title="Levobetaxolol">Levobetaxolol</a></li> <li><a href="/wiki/Levobunolol" title="Levobunolol">Levobunolol</a></li> <li><a href="/wiki/Levomoprolol" title="Levomoprolol">Levomoprolol</a></li> <li><a href="/wiki/Medroxalol" title="Medroxalol">Medroxalol</a></li> <li><a href="/wiki/Mepindolol" title="Mepindolol">Mepindolol</a></li> <li><a href="/wiki/Metipranolol" title="Metipranolol">Metipranolol</a></li> <li><a href="/wiki/Metoprolol" title="Metoprolol">Metoprolol</a></li> <li><a href="/wiki/Moprolol" title="Moprolol">Moprolol</a></li> <li><a href="/wiki/Nadolol" title="Nadolol">Nadolol</a></li> <li><a href="/wiki/Nadoxolol" title="Nadoxolol">Nadoxolol</a></li> <li><a href="/wiki/Nebivolol" title="Nebivolol">Nebivolol</a></li> <li><a href="/wiki/Nifenalol" title="Nifenalol">Nifenalol</a></li> <li><a href="/wiki/Nipradilol" title="Nipradilol">Nipradilol</a></li> <li><a href="/wiki/Oxprenolol" title="Oxprenolol">Oxprenolol</a></li> <li><a href="/wiki/Pacrinolol" title="Pacrinolol">Pacrinolol</a></li> <li><a href="/wiki/Pafenolol" title="Pafenolol">Pafenolol</a></li> <li><a href="/wiki/Pamatolol" title="Pamatolol">Pamatolol</a></li> <li><a href="/wiki/Pargolol" title="Pargolol">Pargolol</a></li> <li><a href="/wiki/Penbutolol" title="Penbutolol">Penbutolol</a></li> <li><a href="/wiki/Pindolol" title="Pindolol">Pindolol</a></li> <li><a href="/wiki/Practolol" title="Practolol">Practolol</a></li> <li><a href="/wiki/Primidolol" title="Primidolol">Primidolol</a></li> <li><a href="/wiki/Procinolol" title="Procinolol">Procinolol</a></li> <li><a href="/wiki/Pronethalol" title="Pronethalol">Pronethalol</a></li> <li><a href="/wiki/Propafenone" title="Propafenone">Propafenone</a></li> <li><a href="/wiki/Propranolol" title="Propranolol">Propranolol</a></li> <li><a href="/wiki/Ridazolol" title="Ridazolol">Ridazolol</a></li> <li><a href="/wiki/Ronactolol" title="Ronactolol">Ronactolol</a></li> <li><a href="/wiki/Soquinolol" title="Soquinolol">Soquinolol</a></li> <li><a href="/wiki/Sotalol" title="Sotalol">Sotalol</a></li> <li><a href="/wiki/Spirendolol" title="Spirendolol">Spirendolol</a></li> <li><a href="/wiki/SR_59230A" title="SR 59230A">SR 59230A</a></li> <li><a href="/wiki/Sulfinalol" title="Sulfinalol">Sulfinalol</a></li> <li><a href="/wiki/Talinolol" title="Talinolol">Talinolol</a></li> <li><a href="/wiki/Tazolol" title="Tazolol">Tazolol</a></li> <li><a href="/wiki/Tertatolol" title="Tertatolol">Tertatolol</a></li> <li><a href="/wiki/Tienoxolol" title="Tienoxolol">Tienoxolol</a></li> <li><a href="/wiki/Tilisolol" title="Tilisolol">Tilisolol</a></li> <li><a href="/wiki/Timolol" title="Timolol">Timolol</a></li> <li><a href="/wiki/Tiprenolol" title="Tiprenolol">Tiprenolol</a></li> <li><a href="/wiki/Tolamolol" title="Tolamolol">Tolamolol</a></li> <li><a href="/wiki/Toliprolol" title="Toliprolol">Toliprolol</a></li> <li><a href="/wiki/Xibenolol" title="Xibenolol">Xibenolol</a></li> <li><a href="/wiki/Xipranolol" title="Xipranolol">Xipranolol</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><td class="navbox-abovebelow" colspan="2"><div> <ul><li><i><b>See also:</b> <a href="/wiki/Template:Receptor_modulators" title="Template:Receptor modulators">Receptor/signaling modulators</a></i></li> <li><i><a href="/wiki/Template:Dopamine_receptor_modulators" title="Template:Dopamine receptor modulators">Dopaminergics</a></i></li> <li><i><a href="/wiki/Template:Serotonin_receptor_modulators" title="Template:Serotonin receptor modulators">Serotonergics</a></i></li> <li><i><a href="/wiki/Template:Monoamine_reuptake_inhibitors" title="Template:Monoamine reuptake inhibitors">Monoamine reuptake inhibitors</a></i></li> <li><i><a href="/wiki/Template:Monoamine_releasing_agents" title="Template:Monoamine releasing agents">Monoamine releasing agents</a></i></li> <li><i><a href="/wiki/Template:Monoamine_metabolism_modulators" title="Template:Monoamine metabolism modulators">Monoamine metabolism modulators</a></i></li> <li><i><a href="/wiki/Template:Monoamine_neurotoxins" title="Template:Monoamine neurotoxins">Monoamine neurotoxins</a></i></li></ul> </div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"></div><div role="navigation" class="navbox" aria-labelledby="Dopamine_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:Dopamine_receptor_modulators" title="Template:Dopamine receptor modulators"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Dopamine_receptor_modulators" title="Template talk:Dopamine receptor modulators"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Dopamine_receptor_modulators" title="Special:EditPage/Template:Dopamine receptor modulators"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Dopamine_receptor_modulators" style="font-size:114%;margin:0 4em"><a href="/wiki/Dopamine_receptor" title="Dopamine receptor">Dopamine 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/D1-like_receptor" title="D1-like receptor">D<sub>1</sub>-like</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;">Agonists</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i>Benzazepines</i>: <a href="/wiki/6-Br-APB" title="6-Br-APB">6-Br-APB</a></li> <li><a href="/wiki/Fenoldopam" title="Fenoldopam">Fenoldopam</a></li> <li><a href="/wiki/SKF-38,393" title="SKF-38,393">SKF-38,393</a></li> <li><a href="/wiki/SKF-77,434" title="SKF-77,434">SKF-77,434</a></li> <li><a href="/wiki/SKF-81,297" title="SKF-81,297">SKF-81,297</a></li> <li><a href="/wiki/SKF-82,958" title="SKF-82,958">SKF-82,958</a></li> <li><a href="/wiki/SKF-83,959" title="SKF-83,959">SKF-83,959</a></li> <li><a href="/wiki/Trepipam" title="Trepipam">Trepipam</a></li> <li><a href="/wiki/Zelandopam" title="Zelandopam">Zelandopam</a></li></ul> <ul><li><i>Ergolines</i>: <a href="/wiki/Cabergoline" title="Cabergoline">Cabergoline</a></li> <li><a href="/wiki/CY-208,243" title="CY-208,243">CY-208,243</a></li> <li><a href="/wiki/Dihydroergocryptine" title="Dihydroergocryptine">Dihydroergocryptine</a></li> <li><a href="/w/index.php?title=LEK-8829&action=edit&redlink=1" class="new" title="LEK-8829 (page does not exist)">LEK-8829</a></li> <li><a href="/wiki/Lisuride" title="Lisuride">Lisuride</a></li> <li><a href="/wiki/Pergolide" title="Pergolide">Pergolide</a></li> <li><a href="/wiki/Terguride" title="Terguride">Terguride</a></li></ul> <ul><li><i>Dihydrexidine derivatives</i>: <a href="/wiki/A-77636" title="A-77636">A-77636</a></li> <li><a href="/wiki/A-86929" title="A-86929">A-86929</a></li> <li><a href="/wiki/Adrogolide" class="mw-redirect" title="Adrogolide">Adrogolide (ABT-431, DAS-431)</a></li> <li><a href="/wiki/Dihydrexidine" title="Dihydrexidine">Dihydrexidine</a></li> <li><a href="/wiki/Dinapsoline" title="Dinapsoline">Dinapsoline</a></li> <li><a href="/wiki/Dinoxyline" title="Dinoxyline">Dinoxyline</a></li> <li><a href="/wiki/Doxanthrine" title="Doxanthrine">Doxanthrine</a></li></ul> <ul><li><i>Phenethylamines</i>: <a href="/w/index.php?title=BCO-001&action=edit&redlink=1" class="new" title="BCO-001 (page does not exist)">BCO-001</a></li> <li><a href="/wiki/Deoxyepinephrine" title="Deoxyepinephrine">Deoxyepinephrine (N-methyldopamine, epinine)</a></li> <li><a href="/wiki/Dopexamine" title="Dopexamine">Dopexamine</a></li> <li><a href="/wiki/Etilevodopa" title="Etilevodopa">Etilevodopa</a></li> <li><a href="/wiki/Ibopamine" title="Ibopamine">Ibopamine</a></li> <li><a href="/wiki/L-DOPA" title="L-DOPA"><small>L</small>-DOPA (levodopa)</a></li> <li><a href="/wiki/Melevodopa" title="Melevodopa">Melevodopa</a></li> <li><a href="/wiki/Phenylalanine" title="Phenylalanine"><small>L</small>-Phenylalanine</a></li> <li><a class="mw-selflink selflink"><small>L</small>-Tyrosine</a></li> <li><a href="/wiki/XP21279" class="mw-redirect" title="XP21279">XP21279</a></li></ul> <ul><li><i>Others</i>: <a href="/wiki/A-68930" title="A-68930">A-68930</a></li> <li><a href="/wiki/Apomorphine" title="Apomorphine">Apomorphine</a></li> <li><a href="/w/index.php?title=Isocorypalmine&action=edit&redlink=1" class="new" title="Isocorypalmine (page does not exist)">Isocorypalmine</a></li> <li><a href="/wiki/Nuciferine" title="Nuciferine">Nuciferine</a></li> <li><a href="/wiki/PF-6649751" class="mw-redirect" title="PF-6649751">PF-6649751</a></li> <li><a href="/w/index.php?title=PF_6669571&action=edit&redlink=1" class="new" title="PF 6669571 (page does not exist)">PF 6669571</a></li> <li><a href="/wiki/Propylnorapomorphine" title="Propylnorapomorphine">Propylnorapomorphine</a></li> <li><a href="/wiki/Rotigotine" title="Rotigotine">Rotigotine</a></li> <li><a href="/wiki/SKF-89,145" title="SKF-89,145">SKF-89,145</a></li> <li><a href="/w/index.php?title=SKF-89,626&action=edit&redlink=1" class="new" title="SKF-89,626 (page does not exist)">SKF-89,626</a></li> <li><a href="/wiki/Stepholidine" title="Stepholidine">Stepholidine</a></li> <li><a href="/wiki/Tavapadon" title="Tavapadon">Tavapadon</a></li> <li><a href="/wiki/Tetrahydropalmatine" title="Tetrahydropalmatine">Tetrahydropalmatine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;">PAMs<sup class="noprint Inline-Template" style="margin-left:0.1em; white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Please_clarify" title="Wikipedia:Please clarify"><span title="The text near this tag may need clarification or removal of jargon. (September 2024)">clarification needed</span></a></i>]</sup></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i>Tetrahydroisoquinolines</i>: <a href="/w/index.php?title=DETQ&action=edit&redlink=1" class="new" title="DETQ (page does not exist)">DETQ</a></li> <li><a href="/w/index.php?title=DPTQ&action=edit&redlink=1" class="new" title="DPTQ (page does not exist)">DPTQ</a></li> <li><a href="/wiki/Mevidalen" title="Mevidalen">Mevidalen</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;">Antagonists</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i>Typical antipsychotics</i>: <a href="/wiki/Butaclamol" title="Butaclamol">Butaclamol</a></li> <li><a href="/wiki/Chlorpromazine" title="Chlorpromazine">Chlorpromazine</a></li> <li><a href="/wiki/Chlorprothixene" title="Chlorprothixene">Chlorprothixene</a></li> <li><a href="/wiki/Flupentixol" title="Flupentixol">Flupentixol (flupenthixol)</a> (<a href="/wiki/Flupentixol/melitracen" title="Flupentixol/melitracen">+melitracen</a>)</li> <li><a href="/wiki/Fluphenazine" title="Fluphenazine">Fluphenazine</a></li> <li><a href="/wiki/Loxapine" title="Loxapine">Loxapine</a></li> <li><a href="/wiki/Perphenazine" title="Perphenazine">Perphenazine</a> (<a href="/wiki/Amitriptyline/perphenazine" title="Amitriptyline/perphenazine">+amitriptyline</a>)</li> <li><a href="/w/index.php?title=Pifluthixol&action=edit&redlink=1" class="new" title="Pifluthixol (page does not exist)">Pifluthixol</a></li> <li><a href="/wiki/Thioridazine" title="Thioridazine">Thioridazine</a></li> <li><a href="/wiki/Thiothixene" class="mw-redirect" title="Thiothixene">Thiothixene</a></li> <li><a href="/wiki/Trifluoperazine" title="Trifluoperazine">Trifluoperazine</a> (<a href="/wiki/Tranylcypromine/trifluoperazine" title="Tranylcypromine/trifluoperazine">+tranylcypromine</a>)</li> <li><a href="/wiki/Zuclopenthixol" title="Zuclopenthixol">Zuclopenthixol</a></li></ul> <ul><li><i>Atypical antipsychotics</i>: <a href="/wiki/Asenapine" title="Asenapine">Asenapine</a></li> <li><a href="/wiki/Clorotepine" title="Clorotepine">Clorotepine</a></li> <li><a href="/wiki/Clotiapine" title="Clotiapine">Clotiapine</a></li> <li><a href="/wiki/Clozapine" title="Clozapine">Clozapine</a></li> <li><a href="/wiki/DHA-clozapine" title="DHA-clozapine">DHA-clozapine</a></li> <li><a href="/wiki/Fluperlapine" title="Fluperlapine">Fluperlapine</a></li> <li><a href="/wiki/Iloperidone" title="Iloperidone">Iloperidone</a></li> <li><a href="/wiki/Norclozapine" class="mw-redirect" title="Norclozapine">Norclozapine</a></li> <li><a href="/w/index.php?title=Norquetiapine&action=edit&redlink=1" class="new" title="Norquetiapine (page does not exist)">Norquetiapine</a></li> <li><a href="/wiki/Olanzapine" title="Olanzapine">Olanzapine</a> (<a href="/wiki/Olanzapine/fluoxetine" title="Olanzapine/fluoxetine">+fluoxetine</a>)</li> <li><a href="/wiki/Paliperidone" title="Paliperidone">Paliperidone</a></li> <li><a href="/wiki/Quetiapine" title="Quetiapine">Quetiapine</a></li> <li><a href="/wiki/Risperidone" title="Risperidone">Risperidone</a></li> <li><a href="/w/index.php?title=Tefludazine&action=edit&redlink=1" class="new" title="Tefludazine (page does not exist)">Tefludazine</a></li> <li><a href="/wiki/Zicronapine" title="Zicronapine">Zicronapine</a></li> <li><a href="/wiki/Ziprasidone" title="Ziprasidone">Ziprasidone</a></li> <li><a href="/wiki/Zotepine" title="Zotepine">Zotepine</a></li></ul> <ul><li><i>Others</i>: <a href="/wiki/Berupipam" title="Berupipam">Berupipam</a></li> <li><a href="/wiki/Ecopipam" title="Ecopipam">Ecopipam</a></li> <li><a href="/wiki/N-Ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline" title="N-Ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline">EEDQ</a></li> <li><a href="/wiki/Metitepine" title="Metitepine">Metitepine (methiothepin)</a></li> <li><a href="/wiki/Odapipam" title="Odapipam">Odapipam</a></li> <li><a href="/wiki/Perlapine" title="Perlapine">Perlapine</a></li> <li><a href="/wiki/SCH-23390" title="SCH-23390">SCH-23390</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/D2-like_receptor" title="D2-like receptor">D<sub>2</sub>-like</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;">Agonists</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i>Adamantanes</i>: <a href="/wiki/Amantadine" title="Amantadine">Amantadine</a></li> <li><a href="/wiki/Memantine" title="Memantine">Memantine</a></li> <li><a href="/wiki/Rimantadine" title="Rimantadine">Rimantadine</a></li></ul> <ul><li><i>Aminotetralins</i>: <a href="/wiki/5-OH-DPAT" title="5-OH-DPAT">5-OH-DPAT</a></li> <li><a href="/wiki/7-OH-DPAT" title="7-OH-DPAT">7-OH-DPAT</a></li> <li><a href="/wiki/8-OH-PBZI" title="8-OH-PBZI">8-OH-PBZI</a></li> <li><a href="/wiki/Rotigotine" title="Rotigotine">Rotigotine</a></li> <li><a href="/wiki/UH-232" title="UH-232">UH-232</a></li></ul> <ul><li><i>Ergolines</i>: <a href="/wiki/Bromocriptine" title="Bromocriptine">Bromocriptine</a></li> <li><a href="/wiki/Cabergoline" title="Cabergoline">Cabergoline</a></li> <li><a href="/wiki/Chanoclavine" title="Chanoclavine">Chanoclavine</a></li> <li><a href="/wiki/Dihydroergocryptine" title="Dihydroergocryptine">Dihydroergocryptine</a></li> <li><a href="/wiki/Epicriptine" title="Epicriptine">Epicriptine</a></li> <li><a href="/wiki/Ergocornine" title="Ergocornine">Ergocornine</a></li> <li><a href="/wiki/Lergotrile" title="Lergotrile">Lergotrile</a></li> <li><a href="/wiki/Lisuride" title="Lisuride">Lisuride</a></li> <li><a href="/wiki/LSD" title="LSD">LSD</a></li> <li><a href="/wiki/Pergolide" title="Pergolide">Pergolide</a></li> <li><a href="/wiki/Terguride" title="Terguride">Terguride</a></li></ul> <ul><li><i>Dihydrexidine derivatives</i>: <a href="/wiki/2-OH-NPA" title="2-OH-NPA">2-OH-NPA</a></li> <li><a href="/wiki/Ciladopa" title="Ciladopa">Ciladopa</a></li> <li><a href="/wiki/Dihydrexidine" title="Dihydrexidine">Dihydrexidine</a></li> <li><a href="/wiki/Dinoxyline" title="Dinoxyline">Dinoxyline</a></li> <li><a href="/w/index.php?title=N,N-Propyldihydrexidine&action=edit&redlink=1" class="new" title="N,N-Propyldihydrexidine (page does not exist)">N,N-Propyldihydrexidine</a></li></ul> <ul><li><i>Phenethylamines</i>: <a href="/wiki/Deoxyepinephrine" title="Deoxyepinephrine">Deoxyepinephrine (N-methyldopamine, epinine)</a></li> <li><a href="/wiki/Dopexamine" title="Dopexamine">Dopexamine</a></li> <li><a href="/wiki/Etilevodopa" title="Etilevodopa">Etilevodopa</a></li> <li><a href="/wiki/Ibopamine" title="Ibopamine">Ibopamine</a></li> <li><a href="/wiki/L-DOPA" title="L-DOPA"><small>L</small>-DOPA (levodopa)</a></li> <li><a href="/wiki/Phenylalanine" title="Phenylalanine"><small>L</small>-Phenylalanine</a></li> <li><a class="mw-selflink selflink"><small>L</small>-Tyrosine</a></li> <li><a href="/wiki/Melevodopa" title="Melevodopa">Melevodopa</a></li> <li><a href="/wiki/XP21279" class="mw-redirect" title="XP21279">XP21279</a></li></ul> <ul><li><i>Atypical antipsychotics</i>: <a href="/wiki/Alentemol" title="Alentemol">Alentemol (U-66444B)</a></li> <li><a href="/wiki/Aripiprazole" title="Aripiprazole">Aripiprazole</a> (<a href="/wiki/Aripiprazole/sertraline" title="Aripiprazole/sertraline">+sertraline</a>)</li> <li><a href="/wiki/Aripiprazole_lauroxil" title="Aripiprazole lauroxil">Aripiprazole lauroxil</a></li> <li><a href="/wiki/Bifeprunox" title="Bifeprunox">Bifeprunox</a></li> <li><a href="/wiki/Brexpiprazole" title="Brexpiprazole">Brexpiprazole</a></li> <li><a href="/wiki/Brilaroxazine" title="Brilaroxazine">Brilaroxazine</a></li> <li><a href="/wiki/Cariprazine" title="Cariprazine">Cariprazine</a></li> <li><a href="/wiki/F-15063" title="F-15063">F-15063</a></li> <li><a href="/wiki/Lumateperone" title="Lumateperone">Lumateperone</a></li> <li><a href="/wiki/Norclozapine" class="mw-redirect" title="Norclozapine">Norclozapine</a></li></ul> <ul><li><i>Others</i>: <a href="/wiki/3-PPP" title="3-PPP">3-PPP</a></li> <li><a href="/wiki/A-412997" title="A-412997">A-412997</a></li> <li><a href="/wiki/ABT-670" title="ABT-670">ABT-670</a></li> <li><a href="/wiki/ABT-724" title="ABT-724">ABT-724</a></li> <li><a href="/wiki/Adrafinil" title="Adrafinil">Adrafinil</a></li> <li><a href="/wiki/Aplindore" title="Aplindore">Aplindore</a></li> <li><a href="/wiki/Apomorphine" title="Apomorphine">Apomorphine</a></li> <li><a href="/wiki/Arketamine" title="Arketamine">Arketamine</a></li> <li><a href="/wiki/Armodafinil" title="Armodafinil">Armodafinil</a></li> <li><a href="/wiki/BP-897" title="BP-897">BP-897</a></li> <li><a href="/wiki/Captodiame" title="Captodiame">Captodiame</a></li> <li><a href="/wiki/CP-226,269" title="CP-226,269">CP-226,269</a></li> <li><a href="/wiki/Dizocilpine" title="Dizocilpine">Dizocilpine</a></li> <li><a href="/wiki/Esketamine" title="Esketamine">Esketamine</a></li> <li><a href="/wiki/Flibanserin" title="Flibanserin">Flibanserin</a></li> <li><a href="/wiki/Ketamine" title="Ketamine">Ketamine</a></li> <li><a href="/wiki/Mesulergine" title="Mesulergine">Mesulergine</a></li> <li><a href="/wiki/Modafinil" title="Modafinil">Modafinil</a></li> <li><a href="/wiki/OSU-6162" title="OSU-6162">OSU-6162</a></li> <li><a href="/wiki/Pardoprunox" title="Pardoprunox">Pardoprunox</a></li> <li><a href="/wiki/PD-128,907" title="PD-128,907">PD-128,907</a></li> <li><a href="/wiki/PD-168,077" title="PD-168,077">PD-168,077</a></li> <li><a href="/wiki/PF-219,061" title="PF-219,061">PF-219,061</a></li> <li><a href="/wiki/PF-592,379" title="PF-592,379">PF-592,379</a></li> <li><a href="/wiki/Phencyclidine" title="Phencyclidine">Phencyclidine</a></li> <li><a href="/wiki/Piribedil" title="Piribedil">Piribedil</a></li> <li><a href="/wiki/Pramipexole" title="Pramipexole">Pramipexole</a></li> <li><a href="/wiki/Preclamol" class="mw-redirect" title="Preclamol">Preclamol</a></li> <li><a href="/wiki/Propylnorapomorphine" title="Propylnorapomorphine">Propylnorapomorphine</a></li> <li><a href="/wiki/Pukateine" title="Pukateine">Pukateine</a></li> <li><a href="/wiki/Quinagolide" title="Quinagolide">Quinagolide</a></li> <li><a href="/wiki/Quinelorane" title="Quinelorane">Quinelorane</a></li> <li><a href="/wiki/Quinpirole" title="Quinpirole">Quinpirole</a></li> <li><a href="/wiki/RDS-127" title="RDS-127">RDS-127</a></li> <li><a href="/wiki/Ro10-5824" title="Ro10-5824">Ro10-5824</a></li> <li><a href="/wiki/Ropinirole" title="Ropinirole">Ropinirole</a></li> <li><a href="/wiki/Roxindole" title="Roxindole">Roxindole</a></li> <li><a href="/wiki/Salvinorin_A" title="Salvinorin A">Salvinorin A</a></li> <li><a href="/wiki/SKF-83,959" title="SKF-83,959">SKF-83,959</a></li> <li><a href="/wiki/Sumanirole" title="Sumanirole">Sumanirole</a></li> <li><a href="/wiki/Talipexole" title="Talipexole">Talipexole</a></li> <li><a href="/wiki/Umespirone" title="Umespirone">Umespirone</a></li> <li><a href="/wiki/WAY-100,635" class="mw-redirect" title="WAY-100,635">WAY-100,635</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;">Antagonists</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i>Typical antipsychotics</i>: <a href="/wiki/Acepromazine" title="Acepromazine">Acepromazine</a></li> <li><a href="/wiki/Acetophenazine" title="Acetophenazine">Acetophenazine</a></li> <li><a href="/wiki/Azaperone" title="Azaperone">Azaperone</a></li> <li><a href="/wiki/Benperidol" title="Benperidol">Benperidol</a></li> <li><a href="/wiki/Bromperidol" title="Bromperidol">Bromperidol</a></li> <li><a href="/wiki/Butaclamol" title="Butaclamol">Butaclamol</a></li> <li><a href="/wiki/Butaperazine" title="Butaperazine">Butaperazine</a></li> <li><a href="/wiki/Chloracizine" class="mw-redirect" title="Chloracizine">Chloracizine</a></li> <li><a href="/wiki/Chlorproethazine" title="Chlorproethazine">Chlorproethazine</a></li> <li><a href="/wiki/Chlorpromazine" title="Chlorpromazine">Chlorpromazine</a></li> <li><a href="/wiki/Chlorprothixene" title="Chlorprothixene">Chlorprothixene</a></li> <li><a href="/wiki/Ciclindole" title="Ciclindole">Ciclindole</a></li> <li><a href="/wiki/Clopenthixol" title="Clopenthixol">Clopenthixol</a></li> <li><a href="/w/index.php?title=Clothixamide&action=edit&redlink=1" class="new" title="Clothixamide (page does not exist)">Clothixamide</a></li> <li><a href="/wiki/Clopimozide" title="Clopimozide">Clopimozide</a></li> <li><a href="/wiki/Droperidol" title="Droperidol">Droperidol</a></li> <li><a href="/wiki/Fluacizine" title="Fluacizine">Fluacizine</a></li> <li><a href="/wiki/Fluanisone" title="Fluanisone">Fluanisone</a></li> <li><a href="/wiki/Flucindole" title="Flucindole">Flucindole</a></li> <li><a href="/wiki/Fluotracen" title="Fluotracen">Fluotracen</a></li> <li><a href="/wiki/Flupentixol" title="Flupentixol">Flupentixol (flupenthixol)</a> (<a href="/wiki/Flupentixol/melitracen" title="Flupentixol/melitracen">+melitracen</a>)</li> <li><a href="/wiki/Fluphenazine" title="Fluphenazine">Fluphenazine</a></li> <li><a href="/w/index.php?title=Fluprothixene&action=edit&redlink=1" class="new" title="Fluprothixene (page does not exist)">Fluprothixene</a></li> <li><a href="/wiki/Fluspirilene" title="Fluspirilene">Fluspirilene</a></li> <li><a href="/wiki/Haloperidol" title="Haloperidol">Haloperidol</a></li> <li><a href="/wiki/Homopipramol" title="Homopipramol">Homopipramol</a></li> <li><a href="/wiki/Lenperone" title="Lenperone">Lenperone</a></li> <li><a href="/wiki/Levomepromazine" title="Levomepromazine">Levomepromazine (methotrimeprazine)</a></li> <li><a href="/wiki/Levosulpiride" title="Levosulpiride">Levosulpiride</a></li> <li><a href="/wiki/Loxapine" title="Loxapine">Loxapine</a></li> <li><a href="/wiki/Mesoridazine" title="Mesoridazine">Mesoridazine</a></li> <li><a href="/wiki/Moperone" title="Moperone">Moperone</a></li> <li><a href="/wiki/Naranol" title="Naranol">Naranol</a></li> <li><a href="/wiki/Nemonapride" title="Nemonapride">Nemonapride</a></li> <li><a href="/wiki/Penfluridol" title="Penfluridol">Penfluridol</a></li> <li><a href="/wiki/Perathiepin" title="Perathiepin">Perathiepin</a></li> <li><a href="/wiki/Perazine" title="Perazine">Perazine</a></li> <li><a href="/wiki/Periciazine" title="Periciazine">Pericyazine (periciazine)</a></li> <li><a href="/wiki/Perphenazine" title="Perphenazine">Perphenazine</a> (<a href="/wiki/Amitriptyline/perphenazine" title="Amitriptyline/perphenazine">+amitriptyline</a>)</li> <li><a href="/w/index.php?title=Piflutixol&action=edit&redlink=1" class="new" title="Piflutixol (page does not exist)">Piflutixol (pifluthixol)</a></li> <li><a href="/wiki/Pimozide" title="Pimozide">Pimozide</a></li> <li><a href="/wiki/Pipamperone" title="Pipamperone">Pipamperone</a></li> <li><a href="/wiki/Preclamol" class="mw-redirect" title="Preclamol">Preclamol</a></li> <li><a href="/wiki/Prochlorperazine" title="Prochlorperazine">Prochlorperazine</a></li> <li><a href="/wiki/Promazine" title="Promazine">Promazine</a></li> <li><a href="/wiki/Prothipendyl" title="Prothipendyl">Prothipendyl</a></li> <li><a href="/wiki/Spiperone" title="Spiperone">Spiperone (spiroperidol)</a></li> <li><a href="/wiki/Sulforidazine" title="Sulforidazine">Sulforidazine</a></li> <li><a href="/wiki/Sulpiride" title="Sulpiride">Sulpiride</a></li> <li><a href="/wiki/Sultopride" title="Sultopride">Sultopride</a></li> <li><a href="/w/index.php?title=Teflutixol&action=edit&redlink=1" class="new" title="Teflutixol (page does not exist)">Teflutixol</a></li> <li><a href="/wiki/Thiopropazate" title="Thiopropazate">Thiopropazate</a></li> <li><a href="/wiki/Thioproperazine" title="Thioproperazine">Thioproperazine</a></li> <li><a href="/wiki/Thioridazine" title="Thioridazine">Thioridazine</a></li> <li><a href="/wiki/Thiothixene" class="mw-redirect" title="Thiothixene">Thiothixene</a></li> <li><a href="/wiki/Timiperone" title="Timiperone">Timiperone</a></li> <li><a href="/wiki/Trifluoperazine" title="Trifluoperazine">Trifluoperazine</a> (<a href="/wiki/Tranylcypromine/trifluoperazine" title="Tranylcypromine/trifluoperazine">+tranylcypromine</a>)</li> <li><a href="/wiki/Triflupromazine" title="Triflupromazine">Triflupromazine</a></li> <li><a href="/wiki/Trifluperidol" title="Trifluperidol">Trifluperidol</a></li> <li><a href="/w/index.php?title=Zetidoline&action=edit&redlink=1" class="new" title="Zetidoline (page does not exist)">Zetidoline</a></li> <li><a href="/wiki/Zuclopenthixol" title="Zuclopenthixol">Zuclopenthixol</a></li></ul> <ul><li><i>Atypical antipsychotics</i>: <a href="/wiki/Amisulpride" title="Amisulpride">Amisulpride</a></li> <li><a href="/wiki/Asenapine" title="Asenapine">Asenapine</a></li> <li><a href="/wiki/BL-1020" title="BL-1020">BL-1020</a></li> <li><a href="/wiki/Blonanserin" title="Blonanserin">Blonanserin</a></li> <li><a href="/wiki/Carpipramine" title="Carpipramine">Carpipramine</a></li> <li><a href="/w/index.php?title=Cinuperone&action=edit&redlink=1" class="new" title="Cinuperone (page does not exist)">Cinuperone</a></li> <li><a href="/wiki/Clocapramine" title="Clocapramine">Clocapramine</a></li> <li><a href="/wiki/Clorotepine" title="Clorotepine">Clorotepine</a></li> <li><a href="/wiki/Clotiapine" title="Clotiapine">Clotiapine (clothiapine)</a></li> <li><a href="/wiki/Clozapine" title="Clozapine">Clozapine</a></li> <li><a href="/wiki/Cyamemazine" title="Cyamemazine">Cyamemazine</a></li> <li><a href="/wiki/DHA-clozapine" title="DHA-clozapine">DHA-clozapine</a></li> <li><a href="/wiki/Dixyrazine" title="Dixyrazine">Dixyrazine</a></li> <li><a href="/wiki/Elopiprazole" title="Elopiprazole">Elopiprazole</a></li> <li><a href="/wiki/Flumezapine" title="Flumezapine">Flumezapine</a></li> <li><a href="/wiki/Fluperlapine" title="Fluperlapine">Fluperlapine</a></li> <li><a href="/wiki/Gevotroline" title="Gevotroline">Gevotroline</a></li> <li><a href="/wiki/Iloperidone" title="Iloperidone">Iloperidone</a></li> <li><a href="/wiki/Lurasidone" title="Lurasidone">Lurasidone</a></li> <li><a href="/wiki/Mazapertine" title="Mazapertine">Mazapertine</a></li> <li><a href="/wiki/Melperone" title="Melperone">Melperone</a></li> <li><a href="/wiki/Molindone" title="Molindone">Molindone</a></li> <li><a href="/wiki/Mosapramine" title="Mosapramine">Mosapramine</a></li> <li><a href="/wiki/Ocaperidone" title="Ocaperidone">Ocaperidone</a></li> <li><a href="/wiki/Olanzapine" title="Olanzapine">Olanzapine</a> (<a href="/wiki/Olanzapine/fluoxetine" title="Olanzapine/fluoxetine">+fluoxetine</a>)</li> <li><a href="/wiki/Paliperidone" title="Paliperidone">Paliperidone</a></li> <li><a href="/wiki/Perospirone" title="Perospirone">Perospirone</a></li> <li><a href="/wiki/Piperacetazine" title="Piperacetazine">Piperacetazine</a></li> <li><a href="/wiki/Pipotiazine" title="Pipotiazine">Pipotiazine</a></li> <li><a href="/wiki/Piquindone" title="Piquindone">Piquindone</a></li> <li><a href="/wiki/Quetiapine" title="Quetiapine">Quetiapine</a></li> <li><a href="/wiki/Remoxipride" title="Remoxipride">Remoxipride</a></li> <li><a href="/wiki/Risperidone" title="Risperidone">Risperidone</a></li> <li><a href="/wiki/Sertindole" title="Sertindole">Sertindole</a></li> <li><a href="/w/index.php?title=Tefludazine&action=edit&redlink=1" class="new" title="Tefludazine (page does not exist)">Tefludazine</a></li> <li><a href="/wiki/Tenilapine" title="Tenilapine">Tenilapine</a></li> <li><a href="/wiki/Tiospirone" title="Tiospirone">Tiospirone</a></li> <li><a href="/wiki/Veralipride" title="Veralipride">Veralipride</a></li> <li><a href="/wiki/Zicronapine" title="Zicronapine">Zicronapine</a></li> <li><a href="/wiki/Ziprasidone" title="Ziprasidone">Ziprasidone</a></li> <li><a href="/wiki/Zotepine" title="Zotepine">Zotepine</a></li></ul> <ul><li><i>Antiemetics/gastroprokinetics/sedatives</i>: <a href="/wiki/Aceprometazine" title="Aceprometazine">Aceprometazine</a></li> <li><a href="/wiki/AS-8112" title="AS-8112">AS-8112</a></li> <li><a href="/wiki/Alimemazine" title="Alimemazine">Alimemazine</a></li> <li><a href="/wiki/Alizapride" title="Alizapride">Alizapride</a></li> <li><a href="/wiki/Benzquinamide" title="Benzquinamide">Benzquinamide</a></li> <li><a href="/wiki/Bromopride" title="Bromopride">Bromopride</a></li> <li><a href="/wiki/Clebopride" title="Clebopride">Clebopride</a></li> <li><a href="/wiki/Deudomperidone" title="Deudomperidone">Deudomperidone</a></li> <li><a href="/wiki/Domperidone" title="Domperidone">Domperidone</a></li> <li><a href="/wiki/Eticlopride" title="Eticlopride">Eticlopride</a></li> <li><a href="/wiki/Hydroxyzine" title="Hydroxyzine">Hydroxyzine</a></li> <li><a href="/wiki/Itopride" title="Itopride">Itopride</a></li> <li><a href="/wiki/Metoclopramide" title="Metoclopramide">Metoclopramide</a></li> <li><a href="/wiki/Metopimazine" title="Metopimazine">Metopimazine</a></li> <li><a href="/wiki/Promethazine" title="Promethazine">Promethazine</a></li> <li><a href="/wiki/Thiethylperazine" title="Thiethylperazine">Thiethylperazine</a></li> <li><a href="/wiki/Trazpiroben" title="Trazpiroben">Trazpiroben</a></li> <li><a href="/wiki/Trimethobenzamide" title="Trimethobenzamide">Trimethobenzamide</a></li></ul> <ul><li><i>Antidepressants</i>: <a href="/wiki/Amoxapine" title="Amoxapine">Amoxapine</a></li> <li><a href="/wiki/Nefazodone" title="Nefazodone">Nefazodone</a></li> <li><a href="/wiki/Opipramol" title="Opipramol">Opipramol</a></li> <li><a href="/wiki/Propiomazine" title="Propiomazine">Propiomazine</a></li> <li><a href="/wiki/Trimipramine" title="Trimipramine">Trimipramine</a></li></ul> <ul><li><i>Others</i>: <a href="/wiki/3-PPP" title="3-PPP">3-PPP</a></li> <li><a href="/wiki/Alpiropride" title="Alpiropride">Alpiropride</a></li> <li><a href="/wiki/Azapride" title="Azapride">Azapride</a></li> <li><a href="/wiki/Bromerguride" title="Bromerguride">Bromerguride</a></li> <li><a href="/wiki/Bromocriptine" title="Bromocriptine">Bromocriptine</a></li> <li><a href="/wiki/Buspirone" title="Buspirone">Buspirone</a></li> <li><a href="/wiki/Desmethoxyfallypride" title="Desmethoxyfallypride">Desmethoxyfallypride</a></li> <li><a href="/wiki/N-Ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline" title="N-Ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline">EEDQ</a></li> <li><a href="/wiki/F-15063" title="F-15063">F-15063</a></li> <li><a href="/wiki/Fallypride" title="Fallypride">Fallypride</a></li> <li><a href="/wiki/Fananserin" title="Fananserin">Fananserin</a></li> <li><a href="/wiki/Fenfluramine" title="Fenfluramine">Fenfluramine</a></li> <li><a href="/wiki/Iodobenzamide" title="Iodobenzamide">Iodobenzamide</a></li> <li><a href="/w/index.php?title=Isocorypalmine&action=edit&redlink=1" class="new" title="Isocorypalmine (page does not exist)">Isocorypalmine</a></li> <li><a href="/wiki/L-741,626" title="L-741,626">L-741,626</a></li> <li><a href="/wiki/L-745,870" title="L-745,870">L-745,870</a></li> <li><a href="/wiki/Levofenfluramine" title="Levofenfluramine">Levofenfluramine</a></li> <li><a href="/w/index.php?title=LEK-8829&action=edit&redlink=1" class="new" title="LEK-8829 (page does not exist)">LEK-8829</a></li> <li><a href="/wiki/Metergoline" title="Metergoline">Metergoline</a></li> <li><a href="/wiki/Metitepine" title="Metitepine">Metitepine (methiothepin)</a></li> <li><a href="/wiki/N-Methylspiperone" title="N-Methylspiperone">N-Methylspiperone</a></li> <li><a href="/wiki/Nafadotride" title="Nafadotride">Nafadotride</a></li> <li><a href="/wiki/Nuciferine" title="Nuciferine">Nuciferine</a></li> <li><a href="/wiki/PNU-99,194" title="PNU-99,194">PNU-99,194</a></li> <li><a href="/wiki/Pridopidine" title="Pridopidine">Pridopidine</a></li> <li><a href="/wiki/Raclopride" title="Raclopride">Raclopride</a></li> <li><a href="/wiki/Sarizotan" title="Sarizotan">Sarizotan</a></li> <li><a href="/wiki/SB-277,011-A" title="SB-277,011-A">SB-277,011-A</a></li> <li><a href="/w/index.php?title=Seridopidine&action=edit&redlink=1" class="new" title="Seridopidine (page does not exist)">Seridopidine</a></li> <li><a href="/wiki/Sonepiprazole" title="Sonepiprazole">Sonepiprazole</a></li> <li><a href="/wiki/Spiroxatrine" title="Spiroxatrine">Spiroxatrine</a></li> <li><a href="/wiki/Stepholidine" title="Stepholidine">Stepholidine</a></li> <li><a href="/w/index.php?title=SV-293&action=edit&redlink=1" class="new" title="SV-293 (page does not exist)">SV-293</a></li> <li><a href="/wiki/Terguride" title="Terguride">Terguride</a></li> <li><a href="/wiki/Tetrahydropalmatine" title="Tetrahydropalmatine">Tetrahydropalmatine</a></li> <li><a href="/wiki/Tiapride" title="Tiapride">Tiapride</a></li> <li><a href="/wiki/UH-232" title="UH-232">UH-232</a></li> <li><a href="/wiki/Yohimbine" title="Yohimbine">Yohimbine</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><td class="navbox-abovebelow" colspan="2"><div> <ul><li><small><i><b>See also:</b> <a href="/wiki/Template:Receptor_modulators" title="Template:Receptor modulators">Receptor/signaling modulators</a></i></small></li> <li><small><i><a href="/wiki/Template:Adrenergic_receptor_modulators" title="Template:Adrenergic receptor modulators">Adrenergics</a></i></small></li> <li><small><i><a href="/wiki/Template:Serotonin_receptor_modulators" title="Template:Serotonin receptor modulators">Serotonergics</a></i></small></li> <li><small><i><a href="/wiki/Template:Monoamine_reuptake_inhibitors" title="Template:Monoamine reuptake inhibitors">Monoamine reuptake inhibitors</a></i></small></li> <li><small><i><a href="/wiki/Template:Monoamine_releasing_agents" title="Template:Monoamine releasing agents">Monoamine releasing agents</a></i></small></li> <li><small><i><a href="/wiki/Template:Monoamine_metabolism_modulators" title="Template:Monoamine metabolism modulators">Monoamine metabolism modulators</a></i></small></li> <li><small><i><a href="/wiki/Template:Monoamine_neurotoxins" title="Template:Monoamine neurotoxins">Monoamine neurotoxins</a></i></small></li></ul> </div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"></div><div role="navigation" class="navbox" aria-labelledby="Thyroid_hormone_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:Thyroid_hormone_receptor_modulators" title="Template:Thyroid hormone receptor modulators"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Thyroid_hormone_receptor_modulators" title="Template talk:Thyroid hormone receptor modulators"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Thyroid_hormone_receptor_modulators" title="Special:EditPage/Template:Thyroid hormone receptor modulators"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Thyroid_hormone_receptor_modulators" style="font-size:114%;margin:0 4em"><a href="/wiki/Thyroid_hormone_receptor" title="Thyroid hormone receptor">Thyroid hormone receptor</a> <a href="/wiki/Receptor_modulator" title="Receptor modulator">modulators</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Receptor_(biochemistry)" title="Receptor (biochemistry)">Receptor</a><br /><small>(<a href="/wiki/Ligand_(biochemistry)" title="Ligand (biochemistry)">ligands</a>)</small></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th id="THRTooltip_Thyroid_hormone_receptor" scope="row" class="navbox-group" style="width:3em;;text-align:center;"><a href="/wiki/Thyroid_hormone_receptor" title="Thyroid hormone receptor"><abbr title="Thyroid hormone receptor">THR</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 Thyroid hormone receptor</span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th id="Agonists" scope="row" class="navbox-group" style="width:3em;;text-align:center;">Agonists</th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Dextrothyroxine" title="Dextrothyroxine">Dextrothyroxine</a></li> <li><a href="/w/index.php?title=DIMIT&action=edit&redlink=1" class="new" title="DIMIT (page does not exist)">DIMIT</a></li> <li><a href="/w/index.php?title=DITPA&action=edit&redlink=1" class="new" title="DITPA (page does not exist)">DITPA</a></li> <li><a href="/wiki/Levothyroxine" title="Levothyroxine">Levothyroxine</a></li> <li><a href="/wiki/Liothyronine" title="Liothyronine">Liothyronine</a></li> <li><a href="/wiki/Liotrix" title="Liotrix">Liotrix</a></li> <li><a href="/wiki/Thyroxine" class="mw-redirect" title="Thyroxine">Thyroxine</a></li> <li><a href="/wiki/Tiratricol" title="Tiratricol">Tiratricol (TRIAC)</a></li> <li><a href="/wiki/Triiodothyronine" title="Triiodothyronine">Triiodothyronine</a></li> <li><a href="/wiki/Desiccated_thyroid_extract" title="Desiccated thyroid extract">Thyroid extract</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:3em;;text-align:center;"><a href="/wiki/Thyromimetic" title="Thyromimetic">Thyromimetics</a><br />(selective agonists)</th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Eprotirome" title="Eprotirome">Eprotirome (KB-2115)</a></li> <li><a href="/w/index.php?title=KB-141&action=edit&redlink=1" class="new" title="KB-141 (page does not exist)">KB-141</a></li> <li><a href="/w/index.php?title=KB-2611&action=edit&redlink=1" class="new" title="KB-2611 (page does not exist)">KB-2611</a></li> <li><a href="/w/index.php?title=KB-130015&action=edit&redlink=1" class="new" title="KB-130015 (page does not exist)">KB-130015</a></li> <li><a href="/w/index.php?title=MB-07344&action=edit&redlink=1" class="new" title="MB-07344 (page does not exist)">MB-07344</a></li> <li><a href="/w/index.php?title=MB-07811&action=edit&redlink=1" class="new" title="MB-07811 (page does not exist)">MB-07811</a></li> <li><a href="/wiki/Resmetirom" title="Resmetirom">Resmetirom</a></li> <li><a href="/wiki/Sobetirome" title="Sobetirome">Sobetirome (GC-1, GRX-431)</a></li> <li><a href="/w/index.php?title=VK-0214&action=edit&redlink=1" class="new" title="VK-0214 (page does not exist)">VK-0214</a></li> <li><a href="/wiki/VK-2809" class="mw-redirect" title="VK-2809">VK-2809</a></li> <li><a href="/w/index.php?title=ZYT1&action=edit&redlink=1" class="new" title="ZYT1 (page does not exist)">ZYT1</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:3em;;text-align:center;">Antagonists</th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/w/index.php?title=1-850&action=edit&redlink=1" class="new" title="1-850 (page does not exist)">1-850</a></li> <li><a href="/w/index.php?title=NH3_(THR_antagonist)&action=edit&redlink=1" class="new" title="NH3 (THR antagonist) (page does not exist)">NH3</a></li> <li><a href="/w/index.php?title=Tetraiodothyroacetic_acid&action=edit&redlink=1" class="new" title="Tetraiodothyroacetic acid (page does not exist)">Tetraiodothyroacetic acid (Tetrac)</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Membrane_transport_protein" title="Membrane transport protein">Transporter</a><br /><small>(<a href="/wiki/Transporter_blocker" class="mw-redirect" title="Transporter blocker">blockers</a>)</small></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th id="NISTooltip_Sodium-iodide_symporter" scope="row" class="navbox-group" style="width:3em;;text-align:center;"><a href="/wiki/Sodium-iodide_symporter" class="mw-redirect" title="Sodium-iodide symporter"><abbr title="Sodium-iodide symporter">NIS</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 Sodium-iodide symporter</span><br /> </th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><i>Inhibitors:</i> <a href="/wiki/Cyanogenic_glycoside" class="mw-redirect" title="Cyanogenic glycoside">Cyanogenic glycosides</a></li> <li><a href="/wiki/Perchlorate" title="Perchlorate">Perchlorates</a> (e.g., <a href="/wiki/Potassium_perchlorate" title="Potassium perchlorate">potassium perchlorate</a>)</li> <li><a href="/wiki/Pertechnetate" title="Pertechnetate">Pertechnetates</a> (e.g., <a href="/wiki/Sodium_pertechnetate" title="Sodium pertechnetate">sodium pertechnetate</a>)</li> <li><a href="/wiki/Thiocyanate" title="Thiocyanate">Thiocyanates</a><br /></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/Enzyme" title="Enzyme">Enzyme</a><br /><small>(<a href="/wiki/Enzyme_inhibitor" title="Enzyme inhibitor">inhibitors</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:3em;;text-align:center;"><a href="/wiki/Thyroid_peroxidase" title="Thyroid peroxidase"><abbr title="Thyroid peroxidase">TPO</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 Thyroid peroxidase</span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><i>Inhibitors:</i> <a href="/wiki/Benzylthiouracil" title="Benzylthiouracil">Benzylthiouracil</a></li> <li><a href="/wiki/Carbimazole" title="Carbimazole">Carbimazole</a></li> <li><a href="/wiki/Genistein" title="Genistein">Genistein</a></li> <li><a href="/wiki/Methimazole" class="mw-redirect" title="Methimazole">Methimazole</a></li> <li><a href="/wiki/Methylthiouracil" title="Methylthiouracil">Methylthiouracil</a></li> <li><a href="/wiki/Propylthiouracil" title="Propylthiouracil">Propylthiouracil</a></li> <li><a href="/wiki/2-Thiouracil" title="2-Thiouracil">2-Thiouracil</a></li> <li><a href="/wiki/Thiourea" title="Thiourea">Thiourea</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:3em;;text-align:center;"><a href="/wiki/Iodothyronine_deiodinase" title="Iodothyronine deiodinase"><abbr title="Iodothyronine deiodinase">DIO</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 Iodothyronine deiodinase</span></th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><i>Inhibitors:</i> <a href="/wiki/Dexpropranolol" class="mw-redirect" title="Dexpropranolol">Dexpropranolol</a></li> <li><a href="/wiki/Iopanoic_acid" title="Iopanoic acid">Iopanoic acid</a></li> <li><a href="/wiki/Ipodate_sodium" title="Ipodate sodium">Ipodate sodium (sodium iopodate)</a></li> <li><a href="/wiki/Propranolol" title="Propranolol">Propranolol</a></li> <li><a href="/wiki/Propylthiouracil" title="Propylthiouracil">Propylthiouracil</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;">Others</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Iodine" title="Iodine">Iodine</a></li> <li><a href="/wiki/Iodine-131" title="Iodine-131">Iodine-131</a></li> <li><a href="/wiki/Selenium" title="Selenium">Selenium</a></li> <li><a href="/wiki/Thyroglobulin" title="Thyroglobulin">Thyroglobulin</a></li> <li><a class="mw-selflink selflink">Tyrosine</a></li></ul> </div></td></tr><tr><td class="navbox-abovebelow" colspan="2"><div> <ul><li><i><b>See also:</b> <a href="/wiki/Template:Receptor_modulators" title="Template:Receptor modulators">Receptor/signaling modulators</a></i></li></ul> </div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"></div><div role="navigation" class="navbox" aria-labelledby="Chocolate" style="padding:3px"><table class="nowraplinks mw-collapsible autocollapse navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2" style="background: #7B3F00; color: white;"><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:Chocolate" title="Template:Chocolate"><abbr title="View this template" style="color: white">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Chocolate" title="Template talk:Chocolate"><abbr title="Discuss this template" style="color: white">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Chocolate" title="Special:EditPage/Template:Chocolate"><abbr title="Edit this template" style="color: white">e</abbr></a></li></ul></div><div id="Chocolate" style="font-size:114%;margin:0 4em"><a href="/wiki/Chocolate" title="Chocolate"><span style="color:white">Chocolate</span></a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%;background: #7B3F00; color: white;"><a href="/wiki/Cocoa_bean" title="Cocoa bean"><span style="color:white">Cocoa bean</span></a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Chocolate_liquor" title="Chocolate liquor">Chocolate liquor</a></li> <li><a href="/wiki/Cocoa_butter" title="Cocoa butter">Cocoa butter</a></li> <li><a href="/wiki/Cocoa_solids" title="Cocoa solids">Cocoa solids</a></li> <li><i><a href="/wiki/Theobroma_cacao" title="Theobroma cacao">Theobroma cacao</a></i></li> <li><a href="/wiki/Types_of_cocoa_beans" title="Types of cocoa beans">Types</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;background: #7B3F00; color: white;">Components</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/Anandamide" title="Anandamide">Anandamide</a></li> <li><a href="/wiki/Caffeine" title="Caffeine">Caffeine</a></li> <li><a href="/wiki/Endorphins" title="Endorphins">Endorphins</a></li> <li><a href="/wiki/Enkephalin" title="Enkephalin">Enkephalin</a></li> <li><a href="/wiki/Flavan-3-ol" title="Flavan-3-ol">Flavan-3-ol</a></li> <li><a href="/wiki/Lecithin" title="Lecithin">Lecithin</a></li> <li><a href="/wiki/Phenethylamine" title="Phenethylamine">Phenethylamine</a></li> <li><a href="/wiki/Phenylalanine" title="Phenylalanine">Phenylalanine</a></li> <li><a href="/wiki/Salsolinol" title="Salsolinol">Salsolinol</a></li> <li><a href="/wiki/Tetramethylpyrazine" title="Tetramethylpyrazine">Tetramethylpyrazine</a></li> <li><a href="/wiki/Theobromine" title="Theobromine">Theobromine</a></li> <li><a href="/wiki/Theophylline" title="Theophylline">Theophylline</a></li> <li><a href="/wiki/Tryptamine" title="Tryptamine">Tryptamine</a></li> <li><a href="/wiki/Tryptophan" title="Tryptophan">Tryptophan</a></li> <li><a href="/wiki/Tyramine" title="Tyramine">Tyramine</a></li> <li><a class="mw-selflink selflink">Tyrosine</a></li> <li><a href="/wiki/Valeric_acid" title="Valeric acid">Valeric acid</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;background: #7B3F00; color: white;"><a href="/wiki/Types_of_chocolate" title="Types of chocolate"><span style="color:white">Types</span></a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Baking_chocolate" title="Baking chocolate">Baking</a></li> <li><a href="/wiki/Dark_chocolate" title="Dark chocolate">Dark</a></li> <li><a href="/wiki/Gianduja_(chocolate)" title="Gianduja (chocolate)">Gianduja</a></li> <li><a href="/wiki/Milk_chocolate" title="Milk chocolate">Milk</a></li> <li><a href="/wiki/Organic_chocolate" title="Organic chocolate">Organic</a></li> <li><a href="/wiki/Raw_chocolate" title="Raw chocolate">Raw</a></li> <li><a href="/wiki/Ruby_chocolate" title="Ruby chocolate">Ruby</a></li> <li><a href="/wiki/White_chocolate" title="White chocolate">White</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;background: #7B3F00; color: white;">Products</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/Caff%C3%A8_mocha" title="Caffè mocha">Caffè mocha</a></li> <li><a href="/wiki/Chocolate_bar" title="Chocolate bar">Chocolate bar</a> <ul><li><a href="/wiki/List_of_chocolate_bar_brands" title="List of chocolate bar brands">Brands</a></li></ul></li> <li><a href="/wiki/Chocolate_biscuit" title="Chocolate biscuit">Chocolate biscuit</a></li> <li><a href="/wiki/Chocolate_brownie" title="Chocolate brownie">Chocolate brownie</a></li> <li><a href="/wiki/Chocolate_cake" title="Chocolate cake">Chocolate cake</a></li> <li><a href="/wiki/Chocolate_chip_cookie" title="Chocolate chip cookie">Chocolate chip cookie</a></li> <li><a href="/wiki/Chocolate_chip" title="Chocolate chip">Chocolate chip</a></li> <li><a href="/wiki/Chocolate_coin" title="Chocolate coin">Chocolate coins</a></li> <li><a href="/wiki/Chocolate_crackles" title="Chocolate crackles">Chocolate crackles</a></li> <li><a href="/wiki/Chocolate_gravy" title="Chocolate gravy">Chocolate gravy</a></li> <li><a href="/wiki/Chocolate_ice_cream" title="Chocolate ice cream">Chocolate ice cream</a></li> <li><a href="/wiki/Chocolate_liqueur" title="Chocolate liqueur">Chocolate liqueur</a></li> <li><a href="/wiki/Chocolate_milk" title="Chocolate milk">Chocolate milk</a></li> <li><a href="/wiki/Chocolate_pudding" title="Chocolate pudding">Chocolate pudding</a></li> <li><a href="/wiki/Chocolate_spread" title="Chocolate spread">Chocolate spread</a></li> <li><a href="/wiki/Chocolate_syrup" title="Chocolate syrup">Chocolate syrup</a></li> <li><a href="/wiki/Chocolate_truffle" title="Chocolate truffle">Chocolate truffle</a></li> <li><a href="/wiki/Cioccolato_di_Modica" title="Cioccolato di Modica">Cioccolato di Modica</a></li> <li><a href="/wiki/Fudge" title="Fudge">Fudge</a></li> <li><a href="/wiki/Ganache" title="Ganache">Ganache</a></li> <li><a href="/wiki/Hot_chocolate" title="Hot chocolate">Hot chocolate</a></li> <li><a href="/wiki/List_of_chocolate_drinks" title="List of chocolate drinks">Other beverages</a></li> <li><a href="/wiki/List_of_chocolate-covered_foods" title="List of chocolate-covered foods">Chocolate-covered foods</a></li> <li><a href="/wiki/Mint_chocolate" title="Mint chocolate">Mint chocolate</a></li> <li><a href="/wiki/Mole_(sauce)" title="Mole (sauce)">Mole</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;background: #7B3F00; color: white;">Processes</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/Aerated_chocolate" title="Aerated chocolate">Aerated chocolate</a></li> <li><a href="/wiki/Broma_process" title="Broma process">Broma process</a></li> <li><a href="/wiki/Conching" title="Conching">Conching</a></li> <li><a href="/wiki/Dutch_process_cocoa" title="Dutch process cocoa">Dutch process</a></li> <li><a href="/wiki/Enrober" title="Enrober">Enrober</a></li> <li><a href="/wiki/Sugar_crust" title="Sugar crust">Sugar crust</a></li> <li><a href="/wiki/Tempered_chocolate" title="Tempered chocolate">Tempering</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;background: #7B3F00; color: white;">Industry</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/Bean-to-bar" title="Bean-to-bar">Bean-to-bar</a> <ul><li><a href="/wiki/List_of_bean-to-bar_chocolate_manufacturers" title="List of bean-to-bar chocolate manufacturers">Manufacturers</a></li></ul></li> <li><a href="/wiki/Big_Chocolate" title="Big Chocolate">Big Chocolate</a></li> <li><a href="/wiki/Chocolaterie" title="Chocolaterie">Chocolaterie</a></li> <li><a href="/wiki/Chocolatier" title="Chocolatier">Chocolatier</a></li> <li><a href="/wiki/C%C3%B4te_d%27Ivoire%E2%80%93Ghana_Cocoa_Initiative" title="Côte d'Ivoire–Ghana Cocoa Initiative">Côte d'Ivoire–Ghana Cocoa Initiative</a></li> <li><i><a href="/wiki/The_Dark_Side_of_Chocolate" title="The Dark Side of Chocolate">The Dark Side of Chocolate</a></i></li> <li><a href="/wiki/Environmental_impact_of_cocoa_production" title="Environmental impact of cocoa production">Environmental impact</a></li> <li><a href="/wiki/European_Cocoa_and_Chocolate_Directive" title="European Cocoa and Chocolate Directive">European Cocoa and Chocolate Directive</a></li> <li><a href="/wiki/Fair_trade_cocoa" title="Fair trade cocoa">Fair trade cocoa</a> <ul><li><a href="/wiki/Child_labour_in_cocoa_production" title="Child labour in cocoa production">Child labour in cocoa production</a></li></ul></li> <li><a href="/wiki/Harkin%E2%80%93Engel_Protocol" title="Harkin–Engel Protocol">Harkin–Engel Protocol</a></li> <li><a href="/wiki/International_Cocoa_Organization" title="International Cocoa Organization">International Cocoa Organization</a></li> <li><a href="/wiki/International_Cocoa_Quarantine_Centre" title="International Cocoa Quarantine Centre">International Cocoa Quarantine Centre</a></li> <li><a href="/wiki/Chocolate_industry_in_the_Philippines" title="Chocolate industry in the Philippines">Philippine chocolate industry</a></li> <li><a href="/wiki/Cocoa_production_in_Ghana" title="Cocoa production in Ghana">Production in Ghana</a> <ul><li><a href="/wiki/Ghana_Cocoa_Board" title="Ghana Cocoa Board">Ghana Cocoa Board</a></li></ul></li> <li><a href="/wiki/Cocoa_production_in_Ivory_Coast" title="Cocoa production in Ivory Coast">Production in Ivory Coast</a></li> <li><a href="/wiki/Cocoa_production_in_Nigeria" title="Cocoa production in Nigeria">Production in Nigeria</a></li> <li><a href="/wiki/Cocoa_production_in_S%C3%A3o_Tom%C3%A9_and_Pr%C3%ADncipe" title="Cocoa production in São Tomé and Príncipe">Production in São Tomé and Príncipe</a></li> <li><a href="/wiki/World_Cocoa_Foundation" title="World Cocoa Foundation">World Cocoa Foundation</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;background: #7B3F00; color: white;">By country</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/Belgian_chocolate" title="Belgian chocolate">Belgium</a></li> <li><a href="/wiki/French_chocolate" title="French chocolate">France</a></li> <li><a href="/wiki/Swiss_chocolate" title="Swiss chocolate">Switzerland</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;background: #7B3F00; color: white;">Other topics</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/Chocolate_addiction" title="Chocolate addiction">Chocolate addiction</a></li> <li><a href="/wiki/Chocolate_bloom" title="Chocolate bloom">Chocolate bloom</a></li> <li><a href="/wiki/Chocolate_fountain" title="Chocolate fountain">Chocolate fountain</a></li> <li><a href="/wiki/List_of_chocolate_museums" title="List of chocolate museums">Chocolate museums</a></li> <li><a href="/wiki/List_of_chocolatiers" title="List of chocolatiers">Chocolatiers</a></li> <li><a href="/wiki/Cocoa_smuggling" title="Cocoa smuggling">Cocoa smuggling</a></li> <li><a href="/wiki/History_of_chocolate" title="History of chocolate">History</a></li> <li><a href="/wiki/Chocolate_in_savory_cooking" title="Chocolate in savory cooking">In savory cooking</a></li> <li>Military chocolate <ul><li><a href="/wiki/Military_chocolate_(Switzerland)" title="Military chocolate (Switzerland)">Switzerland</a></li> <li><a href="/wiki/Military_chocolate_(United_States)" title="Military chocolate (United States)">United States</a></li></ul></li></ul> </div></td></tr><tr><td class="navbox-abovebelow" colspan="2" style="background: #7B3F00; color: white;"><div><div class="plainlist"> <ul><li><span class="noviewer" typeof="mw:File"><span title="Category"><img alt="" src="//upload.wikimedia.org/wikipedia/en/thumb/9/96/Symbol_category_class.svg/16px-Symbol_category_class.svg.png" decoding="async" width="16" height="16" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/9/96/Symbol_category_class.svg/23px-Symbol_category_class.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/9/96/Symbol_category_class.svg/31px-Symbol_category_class.svg.png 2x" data-file-width="180" data-file-height="185" /></span></span> <b><a href="/wiki/Category:Chocolate" title="Category:Chocolate"><span style="color:white">Category</span></a></b></li> <li><span class="noviewer" typeof="mw:File"><span title="Outline"><img alt="" src="//upload.wikimedia.org/wikipedia/commons/thumb/4/41/Global_thinking.svg/10px-Global_thinking.svg.png" decoding="async" width="10" height="16" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/4/41/Global_thinking.svg/15px-Global_thinking.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/4/41/Global_thinking.svg/21px-Global_thinking.svg.png 2x" data-file-width="130" data-file-height="200" /></span></span> <b><a href="/wiki/Outline_of_chocolate" title="Outline of chocolate"><span style="color:white">Outline</span></a></b></li></ul> </div></div></td></tr></tbody></table></div>    </div><noscript><img src="https://login.wikimedia.org/wiki/Special:CentralAutoLogin/start?type=1x1" alt="" width="1" height="1" style="border: none; position: 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