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id="toc-Metabolism-sublist" class="vector-toc-list"> <li id="toc-Biosynthesis" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Biosynthesis"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.1</span> <span>Biosynthesis</span> </div> </a> <ul id="toc-Biosynthesis-sublist" class="vector-toc-list"> <li id="toc-Regulation_of_biosynthesis" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Regulation_of_biosynthesis"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.1.1</span> <span>Regulation of biosynthesis</span> </div> </a> <ul id="toc-Regulation_of_biosynthesis-sublist" class="vector-toc-list"> </ul> </li> </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">2.2</span> <span>Degradation</span> </div> </a> <ul id="toc-Degradation-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Conversion_to_other_biologically_active_amines" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Conversion_to_other_biologically_active_amines"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.3</span> <span>Conversion to other biologically active amines</span> </div> </a> <ul id="toc-Conversion_to_other_biologically_active_amines-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Requirements" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Requirements"> <div class="vector-toc-text"> <span class="vector-toc-numb">3</span> <span>Requirements</span> </div> </a> <ul id="toc-Requirements-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">4</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">5</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">6</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">Histidine</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/%D9%87%D8%B3%D8%AA%D9%8A%D8%AF%D9%8A%D9%86" title="هستيدين – Arabic" lang="ar" hreflang="ar" data-title="هستيدين" data-language-autonym="العربية" data-language-local-name="Arabic" class="interlanguage-link-target"><span>العربية</span></a></li><li class="interlanguage-link interwiki-azb mw-list-item"><a href="https://azb.wikipedia.org/wiki/%D9%87%DB%8C%D8%B3%D8%AA%DB%8C%D8%AF%DB%8C%D9%86" title="هیستیدین – South Azerbaijani" lang="azb" hreflang="azb" data-title="هیستیدین" 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/Histidin" title="Histidin – Minnan" lang="nan" hreflang="nan" data-title="Histidin" 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-be mw-list-item"><a href="https://be.wikipedia.org/wiki/%D0%93%D1%96%D1%81%D1%82%D1%8B%D0%B4%D1%8B%D0%BD" title="Гістыдын – Belarusian" lang="be" hreflang="be" data-title="Гістыдын" data-language-autonym="Беларуская" data-language-local-name="Belarusian" class="interlanguage-link-target"><span>Беларуская</span></a></li><li class="interlanguage-link interwiki-bg mw-list-item"><a href="https://bg.wikipedia.org/wiki/%D0%A5%D0%B8%D1%81%D1%82%D0%B8%D0%B4%D0%B8%D0%BD" title="Хистидин – Bulgarian" lang="bg" hreflang="bg" data-title="Хистидин" 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/Histidin" title="Histidin – Bosnian" lang="bs" hreflang="bs" data-title="Histidin" 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/Histidina" title="Histidina – Catalan" lang="ca" hreflang="ca" data-title="Histidina" 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/Histidin" title="Histidin – Czech" lang="cs" hreflang="cs" data-title="Histidin" 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/Histidin" title="Histidin – Danish" lang="da" hreflang="da" data-title="Histidin" 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/Histidin" title="Histidin – German" lang="de" hreflang="de" data-title="Histidin" 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/Histidiin" title="Histidiin – Estonian" lang="et" hreflang="et" data-title="Histidiin" 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%99%CF%83%CF%84%CE%B9%CE%B4%CE%AF%CE%BD%CE%B7" title="Ιστιδίνη – Greek" lang="el" hreflang="el" data-title="Ιστιδίνη" 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/Histidina" title="Histidina – Spanish" lang="es" hreflang="es" data-title="Histidina" 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/Histidino" title="Histidino – Esperanto" lang="eo" hreflang="eo" data-title="Histidino" 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/Histidina" title="Histidina – Basque" lang="eu" hreflang="eu" data-title="Histidina" 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/%D9%87%DB%8C%D8%B3%D8%AA%DB%8C%D8%AF%DB%8C%D9%86" title="هیستیدین – Persian" lang="fa" hreflang="fa" data-title="هیستیدین" 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/Histidine" title="Histidine – French" lang="fr" hreflang="fr" data-title="Histidine" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target"><span>Français</span></a></li><li class="interlanguage-link interwiki-gl mw-list-item"><a href="https://gl.wikipedia.org/wiki/Histidina" title="Histidina – Galician" lang="gl" hreflang="gl" data-title="Histidina" 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%9E%88%EC%8A%A4%ED%8B%B0%EB%94%98" title="히스티딘 – Korean" lang="ko" hreflang="ko" data-title="히스티딘" data-language-autonym="한국어" data-language-local-name="Korean" class="interlanguage-link-target"><span>한국어</span></a></li><li class="interlanguage-link interwiki-hy mw-list-item"><a href="https://hy.wikipedia.org/wiki/%D5%80%D5%AB%D5%BD%D5%BF%D5%AB%D5%A4%D5%AB%D5%B6" title="Հիստիդին – Armenian" lang="hy" hreflang="hy" data-title="Հիստիդին" data-language-autonym="Հայերեն" data-language-local-name="Armenian" class="interlanguage-link-target"><span>Հայերեն</span></a></li><li class="interlanguage-link interwiki-hi mw-list-item"><a href="https://hi.wikipedia.org/wiki/%E0%A4%B9%E0%A4%BF%E0%A4%B8%E0%A5%8D%E0%A4%9F%E0%A4%BF%E0%A4%A1%E0%A4%BF%E0%A4%A8" title="हिस्टिडिन – Hindi" lang="hi" hreflang="hi" data-title="हिस्टिडिन" data-language-autonym="हिन्दी" data-language-local-name="Hindi" class="interlanguage-link-target"><span>हिन्दी</span></a></li><li class="interlanguage-link interwiki-hr mw-list-item"><a href="https://hr.wikipedia.org/wiki/Histidin" title="Histidin – Croatian" lang="hr" hreflang="hr" data-title="Histidin" data-language-autonym="Hrvatski" data-language-local-name="Croatian" class="interlanguage-link-target"><span>Hrvatski</span></a></li><li class="interlanguage-link interwiki-id mw-list-item"><a href="https://id.wikipedia.org/wiki/Histidina" title="Histidina – Indonesian" lang="id" hreflang="id" data-title="Histidina" 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/Istidina" title="Istidina – Italian" lang="it" hreflang="it" data-title="Istidina" 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%94%D7%99%D7%A1%D7%98%D7%99%D7%93%D7%99%D7%9F" title="היסטידין – Hebrew" lang="he" hreflang="he" data-title="היסטידין" data-language-autonym="עברית" data-language-local-name="Hebrew" class="interlanguage-link-target"><span>עברית</span></a></li><li class="interlanguage-link interwiki-ka mw-list-item"><a href="https://ka.wikipedia.org/wiki/%E1%83%B0%E1%83%98%E1%83%A1%E1%83%A2%E1%83%98%E1%83%93%E1%83%98%E1%83%9C%E1%83%98" title="ჰისტიდინი – Georgian" lang="ka" hreflang="ka" data-title="ჰისტიდინი" data-language-autonym="ქართული" data-language-local-name="Georgian" class="interlanguage-link-target"><span>ქართული</span></a></li><li class="interlanguage-link interwiki-kk mw-list-item"><a href="https://kk.wikipedia.org/wiki/%D0%93%D0%B8%D1%81%D1%82%D0%B8%D0%B4%D0%B8%D0%BD" title="Гистидин – Kazakh" lang="kk" hreflang="kk" data-title="Гистидин" data-language-autonym="Қазақша" data-language-local-name="Kazakh" class="interlanguage-link-target"><span>Қазақша</span></a></li><li class="interlanguage-link interwiki-lv mw-list-item"><a href="https://lv.wikipedia.org/wiki/Histid%C4%ABns" title="Histidīns – Latvian" lang="lv" hreflang="lv" data-title="Histidīns" 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/Histidin" title="Histidin – Luxembourgish" lang="lb" hreflang="lb" data-title="Histidin" 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/Histidinas" title="Histidinas – Lithuanian" lang="lt" hreflang="lt" data-title="Histidinas" 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/Hisztidin" title="Hisztidin – Hungarian" lang="hu" hreflang="hu" data-title="Hisztidin" data-language-autonym="Magyar" data-language-local-name="Hungarian" class="interlanguage-link-target"><span>Magyar</span></a></li><li class="interlanguage-link interwiki-mk mw-list-item"><a href="https://mk.wikipedia.org/wiki/%D0%A5%D0%B8%D1%81%D1%82%D0%B8%D0%B4%D0%B8%D0%BD" title="Хистидин – Macedonian" lang="mk" hreflang="mk" data-title="Хистидин" data-language-autonym="Македонски" data-language-local-name="Macedonian" class="interlanguage-link-target"><span>Македонски</span></a></li><li class="interlanguage-link interwiki-ms mw-list-item"><a href="https://ms.wikipedia.org/wiki/Histidina" title="Histidina – Malay" lang="ms" hreflang="ms" data-title="Histidina" data-language-autonym="Bahasa Melayu" data-language-local-name="Malay" class="interlanguage-link-target"><span>Bahasa Melayu</span></a></li><li class="interlanguage-link interwiki-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/Histidine" title="Histidine – Dutch" lang="nl" hreflang="nl" data-title="Histidine" 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%92%E3%82%B9%E3%83%81%E3%82%B8%E3%83%B3" title="ヒスチジン – Japanese" lang="ja" hreflang="ja" data-title="ヒスチジン" 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/Histidin" title="Histidin – Norwegian Bokmål" lang="nb" hreflang="nb" data-title="Histidin" 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/Histidin" title="Histidin – Norwegian Nynorsk" lang="nn" hreflang="nn" data-title="Histidin" 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/Istidina" title="Istidina – Occitan" lang="oc" hreflang="oc" data-title="Istidina" 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/Gistidin" title="Gistidin – Uzbek" lang="uz" hreflang="uz" data-title="Gistidin" 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-ps mw-list-item"><a href="https://ps.wikipedia.org/wiki/%D9%87%D8%B3%D9%BC%D8%A7%D9%8A%DA%89%D9%8A%D9%86" title="هسټايډين – Pashto" lang="ps" hreflang="ps" data-title="هسټايډين" data-language-autonym="پښتو" data-language-local-name="Pashto" class="interlanguage-link-target"><span>پښتو</span></a></li><li class="interlanguage-link interwiki-pl mw-list-item"><a href="https://pl.wikipedia.org/wiki/Histydyna" title="Histydyna – Polish" lang="pl" hreflang="pl" data-title="Histydyna" 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/Histidina" title="Histidina – Portuguese" lang="pt" hreflang="pt" data-title="Histidina" 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/Histidin%C4%83" title="Histidină – Romanian" lang="ro" hreflang="ro" data-title="Histidină" 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%93%D0%B8%D1%81%D1%82%D0%B8%D0%B4%D0%B8%D0%BD" title="Гистидин – Russian" lang="ru" hreflang="ru" data-title="Гистидин" data-language-autonym="Русский" data-language-local-name="Russian" class="interlanguage-link-target"><span>Русский</span></a></li><li class="interlanguage-link interwiki-scn mw-list-item"><a href="https://scn.wikipedia.org/wiki/Istidina" title="Istidina – Sicilian" lang="scn" hreflang="scn" data-title="Istidina" data-language-autonym="Sicilianu" data-language-local-name="Sicilian" class="interlanguage-link-target"><span>Sicilianu</span></a></li><li class="interlanguage-link interwiki-simple mw-list-item"><a href="https://simple.wikipedia.org/wiki/Histidine" title="Histidine – Simple English" lang="en-simple" hreflang="en-simple" data-title="Histidine" 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/Histid%C3%ADn" title="Histidín – Slovak" lang="sk" hreflang="sk" data-title="Histidín" data-language-autonym="Slovenčina" data-language-local-name="Slovak" class="interlanguage-link-target"><span>Slovenčina</span></a></li><li class="interlanguage-link interwiki-sl mw-list-item"><a href="https://sl.wikipedia.org/wiki/Histidin" title="Histidin – Slovenian" lang="sl" hreflang="sl" data-title="Histidin" data-language-autonym="Slovenščina" data-language-local-name="Slovenian" class="interlanguage-link-target"><span>Slovenščina</span></a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/%D0%A5%D0%B8%D1%81%D1%82%D0%B8%D0%B4%D0%B8%D0%BD" title="Хистидин – Serbian" lang="sr" hreflang="sr" data-title="Хистидин" data-language-autonym="Српски / srpski" data-language-local-name="Serbian" class="interlanguage-link-target"><span>Српски / srpski</span></a></li><li class="interlanguage-link interwiki-sh mw-list-item"><a href="https://sh.wikipedia.org/wiki/Histidin" title="Histidin – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Histidin" data-language-autonym="Srpskohrvatski / српскохрватски" data-language-local-name="Serbo-Croatian" class="interlanguage-link-target"><span>Srpskohrvatski / српскохрватски</span></a></li><li class="interlanguage-link interwiki-su mw-list-item"><a href="https://su.wikipedia.org/wiki/Histidin" title="Histidin – Sundanese" lang="su" hreflang="su" data-title="Histidin" data-language-autonym="Sunda" data-language-local-name="Sundanese" class="interlanguage-link-target"><span>Sunda</span></a></li><li class="interlanguage-link interwiki-fi mw-list-item"><a href="https://fi.wikipedia.org/wiki/Histidiini" title="Histidiini – Finnish" lang="fi" hreflang="fi" data-title="Histidiini" data-language-autonym="Suomi" data-language-local-name="Finnish" class="interlanguage-link-target"><span>Suomi</span></a></li><li class="interlanguage-link interwiki-sv mw-list-item"><a href="https://sv.wikipedia.org/wiki/Histidin" title="Histidin – Swedish" lang="sv" hreflang="sv" data-title="Histidin" data-language-autonym="Svenska" data-language-local-name="Swedish" class="interlanguage-link-target"><span>Svenska</span></a></li><li class="interlanguage-link interwiki-ta mw-list-item"><a href="https://ta.wikipedia.org/wiki/%E0%AE%B9%E0%AE%BF%E0%AE%B8%E0%AF%8D%E0%AE%9F%E0%AE%BF%E0%AE%9F%E0%AE%BF%E0%AE%A9%E0%AF%8D" title="ஹிஸ்டிடின் – Tamil" lang="ta" hreflang="ta" data-title="ஹிஸ்டிடின்" data-language-autonym="தமிழ்" data-language-local-name="Tamil" class="interlanguage-link-target"><span>தமிழ்</span></a></li><li class="interlanguage-link interwiki-tr mw-list-item"><a href="https://tr.wikipedia.org/wiki/Histidin" title="Histidin – Turkish" lang="tr" hreflang="tr" data-title="Histidin" data-language-autonym="Türkçe" data-language-local-name="Turkish" class="interlanguage-link-target"><span>Türkçe</span></a></li><li class="interlanguage-link interwiki-uk mw-list-item"><a href="https://uk.wikipedia.org/wiki/%D0%93%D1%96%D1%81%D1%82%D0%B8%D0%B4%D0%B8%D0%BD" title="Гістидин – Ukrainian" lang="uk" hreflang="uk" data-title="Гістидин" data-language-autonym="Українська" data-language-local-name="Ukrainian" class="interlanguage-link-target"><span>Українська</span></a></li><li class="interlanguage-link interwiki-vi mw-list-item"><a href="https://vi.wikipedia.org/wiki/Histidin" title="Histidin – Vietnamese" lang="vi" hreflang="vi" data-title="Histidin" data-language-autonym="Tiếng Việt" data-language-local-name="Vietnamese" class="interlanguage-link-target"><span>Tiếng Việt</span></a></li><li class="interlanguage-link interwiki-wuu mw-list-item"><a href="https://wuu.wikipedia.org/wiki/%E7%BB%84%E6%B0%A8%E9%85%B8" title="组氨酸 – Wu" lang="wuu" hreflang="wuu" data-title="组氨酸" 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title="Structured data on this page hosted by Wikidata [g]" accesskey="g"><span>Wikidata item</span></a></li> </ul> </div> </div> </div> </div> </div> </div> </nav> </div> </div> </div> <div class="vector-column-end"> <div class="vector-sticky-pinned-container"> <nav class="vector-page-tools-landmark" aria-label="Page tools"> <div id="vector-page-tools-pinned-container" class="vector-pinned-container"> </div> </nav> <nav class="vector-appearance-landmark" aria-label="Appearance"> <div id="vector-appearance-pinned-container" class="vector-pinned-container"> <div id="vector-appearance" class="vector-appearance vector-pinnable-element"> <div class="vector-pinnable-header vector-appearance-pinnable-header vector-pinnable-header-pinned" data-feature-name="appearance-pinned" data-pinnable-element-id="vector-appearance" data-pinned-container-id="vector-appearance-pinned-container" data-unpinned-container-id="vector-appearance-unpinned-container" > <div class="vector-pinnable-header-label">Appearance</div> <button class="vector-pinnable-header-toggle-button vector-pinnable-header-pin-button" data-event-name="pinnable-header.vector-appearance.pin">move to sidebar</button> <button 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-Histidine&redirect=no" class="mw-redirect" title="L-Histidine">L-Histidine</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">Chemical compound</div> <style data-mw-deduplicate="TemplateStyles:r1084375498">.mw-parser-output .ib-chembox{border-collapse:collapse;text-align:left}.mw-parser-output .ib-chembox td,.mw-parser-output .ib-chembox th{border:1px solid #a2a9b1;width:40%}.mw-parser-output .ib-chembox td+td{width:60%}</style> <table class="infobox ib-chembox"> <caption>Histidine </caption> <tbody><tr> <td colspan="2" style="text-align:center; padding:2px;"><span typeof="mw:File"><a href="/wiki/File:Amino_Acid_Histidine.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/a/ac/Amino_Acid_Histidine.png/175px-Amino_Acid_Histidine.png" decoding="async" width="175" height="104" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/ac/Amino_Acid_Histidine.png/263px-Amino_Acid_Histidine.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/ac/Amino_Acid_Histidine.png/350px-Amino_Acid_Histidine.png 2x" data-file-width="516" data-file-height="306" /></a></span><br /><div style="text-align:center;">Structure of Histidine</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:Histidine-from-xtal-3D-bs-17.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/e/e7/Histidine-from-xtal-3D-bs-17.png/125px-Histidine-from-xtal-3D-bs-17.png" decoding="async" width="125" height="131" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/e7/Histidine-from-xtal-3D-bs-17.png/188px-Histidine-from-xtal-3D-bs-17.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/e/e7/Histidine-from-xtal-3D-bs-17.png/250px-Histidine-from-xtal-3D-bs-17.png 2x" data-file-width="2180" data-file-height="2287" /></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></div> </td> <td style="width:50%;"><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Histidine-from-xtal-3D-sf.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/c/c4/Histidine-from-xtal-3D-sf.png/125px-Histidine-from-xtal-3D-sf.png" decoding="async" width="125" height="129" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/c/c4/Histidine-from-xtal-3D-sf.png/188px-Histidine-from-xtal-3D-sf.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/c/c4/Histidine-from-xtal-3D-sf.png/250px-Histidine-from-xtal-3D-sf.png 2x" data-file-width="2229" data-file-height="2308" /></a><figcaption></figcaption></figure><div style="text-align:center"><a href="/wiki/Space-filling_model" title="Space-filling model">Space-filling model</a></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;">Histidine</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;">2-Amino-3-(1<i>H</i>-imidazol-4-yl)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=71-00-1">71-00-1</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">3D model (<a href="/wiki/JSmol" class="mw-redirect" title="JSmol">JSmol</a>)</div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="chemapps.stolaf.edu (3D interactive model)"><a rel="nofollow" class="external text" href="https://chemapps.stolaf.edu/jmol/jmol.php?model=O%3DC%28%5BC%40H%5D%28CC1%3DCNC%3DN1%29N%29O">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=O%3DC%28%5BC%40H%5D%28CC1%3DCNC%3DN1%29%5BNH3%2B%5D%29%5BO-%5D">Interactive image</a></span></li><li>Protonated zwitterion: <span title="chemapps.stolaf.edu (3D interactive model)"><a rel="nofollow" class="external text" href="https://chemapps.stolaf.edu/jmol/jmol.php?model=O%3DC%28%5BC%40H%5D%28CC1%3DCNC%3D%5BNH1%2B%5D1%29%5BNH3%2B%5D%29%5BO-%5D">Interactive image</a></span></li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Beilstein_database" title="Beilstein database">Beilstein Reference</a></div> </td> <td>84088 </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=15971">CHEBI:15971</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ChEMBL" title="ChEMBL">ChEMBL</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.ebi.ac.uk"><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chembldb/index.php/compound/inspect/ChEMBL17962">ChEMBL17962</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.6038.html">6038</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/DB00117">DB00117</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/100.000.678">100.000.678</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q485277#P2566" title="Edit this at Wikidata"><img alt="Edit this at Wikidata" src="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/10px-OOjs_UI_icon_edit-ltr-progressive.svg.png" decoding="async" width="10" height="10" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/15px-OOjs_UI_icon_edit-ltr-progressive.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/20px-OOjs_UI_icon_edit-ltr-progressive.svg.png 2x" data-file-width="20" data-file-height="20" /></a></span> </td></tr> <tr> <td><a href="/wiki/European_Community_number" title="European Community number"><span title="European Community number (chemical identifier)">EC Number</span></a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li>200-745-3</li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Gmelin_database" title="Gmelin database">Gmelin Reference</a></div> </td> <td>83042 </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=3310">3310</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/D00032">D00032</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/PubChem" title="PubChem">PubChem</a> <abbr title="Compound ID">CID</abbr></div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="pubchem.ncbi.nlm.nih.gov"><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/6274">6274</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/4QD397987E">4QD397987E</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/DTXSID9023126">DTXSID9023126</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q485277#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/C6H9N3O2/c7-5(6(10)11)1-4-2-8-3-9-4/h2-3,5H,1,7H2,(H,8,9)(H,10,11)/t5-/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: HNDVDQJCIGZPNO-YFKPBYRVSA-N<sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></div></div></li></ul> </div> </td></tr> <tr> <td colspan="2"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold; text-align:left; font-weight:normal; background:transparent;"><div><a href="/wiki/Simplified_molecular-input_line-entry_system" class="mw-redirect" title="Simplified molecular-input line-entry system">SMILES</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.6em; word-wrap:break-word; text-indent:-1.5em; text-align:left; font-size:97%; line-height:120%;">O=C([C@H](CC1=CNC=N1)N)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>: O=C([C@H](CC1=CNC=N1)[NH3+])[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%;">Protonated zwitterion: O=C([C@H](CC1=CNC=[NH1+]1)[NH3+])[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>6</sub><span title="Hydrogen">H</span><sub>9</sub><span title="Nitrogen">N</span><sub>3</sub><span title="Oxygen">O</span><sub>2</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="7002155157000000000♠"></span>155.157</span> g·mol<sup>−1</sup>   </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Aqueous_solution" title="Aqueous solution">Solubility in water</a></div> </td> <td>4.19g/100g @ 25 °C <sup id="cite_ref-1" class="reference"><a href="#cite_note-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> </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/Histidine_(data_page)" title="Histidine (data page)">Histidine (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>Histidine</b> (symbol <b>His</b> or <b>H</b>)<sup id="cite_ref-:7_2-0" class="reference"><a href="#cite_note-:7-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> is an <a href="/wiki/Essential_amino_acid" title="Essential amino acid">essential amino acid</a> that is used in the biosynthesis of <a href="/wiki/Protein" title="Protein">proteins</a>. It contains an <a href="/wiki/Amine" title="Amine">α-amino group</a> (which is in the <a href="/wiki/Protonated" class="mw-redirect" title="Protonated">protonated</a> –NH<sub>3</sub><sup>+</sup> form under <a href="/wiki/Physiological_condition" title="Physiological condition">biological conditions</a>), a <a href="/wiki/Carboxylic_acid" title="Carboxylic acid">carboxylic acid</a> group (which is in the deprotonated –COO<sup>−</sup> form under biological conditions), and an <a href="/wiki/Imidazole" title="Imidazole">imidazole</a> side chain (which is partially protonated), classifying it as a positively charged amino acid at physiological <a href="/wiki/PH" title="PH">pH</a>. Initially thought <a href="/wiki/Essential_amino_acid" title="Essential amino acid">essential</a> only for infants, it has now been shown in longer-term studies to be essential for adults also.<sup id="cite_ref-3" class="reference"><a href="#cite_note-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> It is <a href="/wiki/Genetic_code" title="Genetic code">encoded</a> by the <a href="/wiki/Genetic_code" title="Genetic code">codons</a> CAU and CAC. </p><p>Histidine was first isolated by <a href="/wiki/Albrecht_Kossel" title="Albrecht Kossel">Albrecht Kossel</a> and <a href="/wiki/Sven_Gustaf_Hedin" title="Sven Gustaf Hedin">Sven Gustaf Hedin</a> in 1896.<sup id="cite_ref-4" class="reference"><a href="#cite_note-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> The name stems from its discovery in tissue, from <span lang="grc"><a href="https://en.wiktionary.org/wiki/%E1%BC%B1%CF%83%CF%84%CF%8C%CF%82#Ancient_Greek" class="extiw" title="wikt:ἱστός">ἱστός</a></span> <i>histós</i> "tissue".<sup id="cite_ref-:7_2-1" class="reference"><a href="#cite_note-:7-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> It is also a <a href="/wiki/Precursor_(chemistry)" title="Precursor (chemistry)">precursor</a> to <a href="/wiki/Histamine" title="Histamine">histamine</a>, a vital inflammatory agent in immune responses. The acyl <a href="/wiki/Radical_(chemistry)" title="Radical (chemistry)">radical</a> is <b>histidyl</b>. </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Properties_of_the_imidazole_side_chain">Properties of the imidazole side chain</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Histidine&action=edit&section=1" title="Edit section: Properties of the imidazole side chain"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The conjugate acid (protonated form) of the <a href="/wiki/Imidazole" title="Imidazole">imidazole</a> <a href="/wiki/Side_chain" title="Side chain">side chain</a> in histidine has a <a href="/wiki/Acid_dissociation_constant" title="Acid dissociation constant">p<i>K</i><sub>a</sub></a> of approximately 6.0. Thus, below a pH of 6, the imidazole ring is mostly <a href="/wiki/Protonation" title="Protonation">protonated</a> (as described by the <a href="/wiki/Henderson%E2%80%93Hasselbalch_equation" title="Henderson–Hasselbalch equation">Henderson–Hasselbalch equation</a>). The resulting imidazolium ring bears two NH bonds and has a positive charge. The positive charge is equally distributed between both <a href="/wiki/Nitrogen" title="Nitrogen">nitrogens</a> and can be represented with two equally important <a href="/wiki/Resonance_structure" class="mw-redirect" title="Resonance structure">resonance structures</a>. Sometimes, the symbol <b>Hip</b> is used for this protonated form instead of the usual His.<sup id="cite_ref-:4_5-0" class="reference"><a href="#cite_note-:4-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-:5_6-0" class="reference"><a href="#cite_note-:5-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-:6_7-0" class="reference"><a href="#cite_note-:6-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> Above pH 6, one of the two protons is lost. The remaining proton of the imidazole ring can reside on either nitrogen, giving rise to what are known as the N3-H or N1-H <a href="/wiki/Tautomer" title="Tautomer">tautomers</a>. The N3-H tautomer is shown in the figure above. In the N1-H tautomer, the NH is nearer the backbone. These neutral tautomers, also referred to as Nε and Nδ, are sometimes referred to with symbols <b>Hie</b> and <b>Hid</b>, respectively.<sup id="cite_ref-:4_5-1" class="reference"><a href="#cite_note-:4-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-:5_6-1" class="reference"><a href="#cite_note-:5-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-:6_7-1" class="reference"><a href="#cite_note-:6-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> The imidazole/imidazolium ring of histidine is <a href="/wiki/Aromatic" class="mw-redirect" title="Aromatic">aromatic</a> at all pH values.<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> Under certain conditions, all three ion-forming groups of histidine can be charged forming the histidinium cation.<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>The acid-base properties of the imidazole side chain are relevant to the <a href="/wiki/Catalyst" class="mw-redirect" title="Catalyst">catalytic mechanism</a> of many <a href="/wiki/Enzyme" title="Enzyme">enzymes</a>.<sup id="cite_ref-:0_10-0" class="reference"><a href="#cite_note-:0-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> In <a href="/wiki/Catalytic_triad" title="Catalytic triad">catalytic triads</a>, the basic nitrogen of histidine abstracts a proton from <a href="/wiki/Serine" title="Serine">serine</a>, <a href="/wiki/Threonine" title="Threonine">threonine</a>, or <a href="/wiki/Cysteine" title="Cysteine">cysteine</a> to activate it as a <a href="/wiki/Nucleophile" title="Nucleophile">nucleophile</a>. In a histidine <a href="/w/index.php?title=Proton_shuttle&action=edit&redlink=1" class="new" title="Proton shuttle (page does not exist)">proton shuttle</a>, histidine is used to quickly shuttle protons. It can do this by abstracting a proton with its basic nitrogen to make a positively charged intermediate and then use another molecule, a buffer, to extract the proton from its acidic nitrogen. In <a href="/wiki/Carbonic_anhydrase" title="Carbonic anhydrase">carbonic anhydrases</a>, a histidine proton shuttle is utilized to rapidly shuttle protons away from a <a href="/wiki/Zinc" title="Zinc">zinc</a>-bound water molecule to quickly regenerate the active form of the enzyme. In helices E and F of <a href="/wiki/Hemoglobin" title="Hemoglobin">hemoglobin</a>, histidine influences binding of dioxygen as well as <a href="/wiki/Carbon_monoxide" title="Carbon monoxide">carbon monoxide</a>. This interaction enhances the affinity of Fe(II) for O2 but destabilizes the binding of CO, which binds only 200 times stronger in hemoglobin, compared to 20,000 times stronger in free <a href="/wiki/Heme" title="Heme">heme</a>. </p><p>The tautomerism and acid-base properties of the imidazole side chain has been characterized by <sup>15</sup>N NMR spectroscopy. The two <sup>15</sup>N chemical shifts are similar (about 200 ppm, relative to <a href="/wiki/Nitric_acid" title="Nitric acid">nitric acid</a> on the sigma scale, on which increased shielding corresponds to increased <a href="/wiki/Chemical_shift" title="Chemical shift">chemical shift</a>). <a href="/wiki/NMR" class="mw-redirect" title="NMR">NMR</a> spectral measurements shows that the chemical shift of N1-H drops slightly, whereas the chemical shift of N3-H drops considerably (about 190 vs. 145 ppm). This change indicates that the N1-H tautomer is preferred, possibly due to hydrogen bonding to the neighboring <a href="/wiki/Ammonium" title="Ammonium">ammonium</a>. The shielding at N3 is substantially reduced due to the second-order <a href="/wiki/Paramagnetism" title="Paramagnetism">paramagnetic</a> effect, which involves a symmetry-allowed interaction between the nitrogen lone pair and the excited π* states of the <a href="/wiki/Aromatic_ring" class="mw-redirect" title="Aromatic ring">aromatic ring</a>. At pH > 9, the chemical shifts of N1 and N3 are approximately 185 and 170 ppm.<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-heading3"><h3 id="Ligand">Ligand</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Histidine&action=edit&section=2" title="Edit section: Ligand"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure class="mw-halign-left" typeof="mw:File/Thumb"><a href="/wiki/File:Succinate_Dehygrogenase_1YQ3_Haem_group.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/b/bd/Succinate_Dehygrogenase_1YQ3_Haem_group.png/205px-Succinate_Dehygrogenase_1YQ3_Haem_group.png" decoding="async" width="205" height="205" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/b/bd/Succinate_Dehygrogenase_1YQ3_Haem_group.png/308px-Succinate_Dehygrogenase_1YQ3_Haem_group.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/b/bd/Succinate_Dehygrogenase_1YQ3_Haem_group.png/410px-Succinate_Dehygrogenase_1YQ3_Haem_group.png 2x" data-file-width="1620" data-file-height="1620" /></a><figcaption>The histidine-bound <a href="/wiki/Heme" title="Heme">heme</a> group of <a href="/wiki/Succinate_dehydrogenase" title="Succinate dehydrogenase">succinate dehydrogenase</a>, an <a href="/wiki/Electron_carrier" class="mw-redirect" title="Electron carrier">electron carrier</a> in the <a href="/wiki/Mitochondria" class="mw-redirect" title="Mitochondria">mitochondrial</a> <a href="/wiki/Electron_transfer_chain" class="mw-redirect" title="Electron transfer chain">electron transfer chain</a>. The large semi-transparent sphere indicates the location of the <a href="/wiki/Iron" title="Iron">iron</a> <a href="/wiki/Ion" title="Ion">ion</a>. From <span class="plainlinks"><a href="/wiki/Protein_Data_Bank" title="Protein Data Bank">PDB</a>: <a rel="nofollow" class="external text" href="https://www.rcsb.org/structure/1YQ3">1YQ3</a></span>.</figcaption></figure> <figure class="mw-default-size mw-halign-left" typeof="mw:File/Thumb"><a href="/wiki/File:Cu3Im8laccase.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/b/b3/Cu3Im8laccase.png/220px-Cu3Im8laccase.png" decoding="async" width="220" height="236" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/b/b3/Cu3Im8laccase.png/330px-Cu3Im8laccase.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/b/b3/Cu3Im8laccase.png/440px-Cu3Im8laccase.png 2x" data-file-width="717" data-file-height="768" /></a><figcaption>The tricopper site found in many <a href="/wiki/Laccase" title="Laccase">laccases</a>, notice that each <a href="/wiki/Copper" title="Copper">copper</a> center is bound to the <a href="/wiki/Imidazole" title="Imidazole">imidazole</a> sidechains of histidine (color code: copper is brown, <a href="/wiki/Nitrogen" title="Nitrogen">nitrogen</a> is blue).</figcaption></figure> <p>Histidine forms <a href="/wiki/Amino_acid_complex" class="mw-redirect" title="Amino acid complex">complexes</a> with many metal ions. The imidazole sidechain of the histidine residue commonly serves as a <a href="/wiki/Ligand" title="Ligand">ligand</a> in <a href="/wiki/Metalloprotein" title="Metalloprotein">metalloproteins</a>. One example is the axial base attached to Fe in myoglobin and hemoglobin. Poly-histidine tags (of six or more consecutive H residues) are utilized for protein purification by binding to columns with nickel or cobalt, with micromolar affinity.<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> Natural poly-histidine peptides, found in the venom of the viper <i><a href="/wiki/Atheris_squamigera" title="Atheris squamigera">Atheris squamigera</a></i> have been shown to bind Zn(2+), Ni(2+) and Cu(2+) and affect the function of venom metalloproteases.<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> </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=Histidine&action=edit&section=3" title="Edit section: Metabolism"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Biosynthesis">Biosynthesis</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Histidine&action=edit&section=4" title="Edit section: Biosynthesis"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure typeof="mw:File/Thumb"><a href="/wiki/File:WP514_85639.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/4/4c/WP514_85639.svg/308px-WP514_85639.svg.png" decoding="async" width="308" height="775" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/4/4c/WP514_85639.svg/463px-WP514_85639.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/4/4c/WP514_85639.svg/617px-WP514_85639.svg.png 2x" data-file-width="535" data-file-height="1344" /></a><figcaption><b>Histidine Biosynthesis Pathway</b> Eight different enzymes can catalyze ten reactions. In this image, His4 catalyzes four different reactions in the pathway. </figcaption></figure> <p><style data-mw-deduplicate="TemplateStyles:r920966791">.mw-parser-output span.smallcaps{font-variant:small-caps}.mw-parser-output span.smallcaps-smaller{font-size:85%}</style><span class="smallcaps">l</span>-Histidine is an essential amino acid that is not synthesized <i><a href="/wiki/De_novo_synthesis" title="De novo synthesis">de novo</a></i> in humans.<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> Humans and other animals must ingest histidine or histidine-containing proteins. The biosynthesis of histidine has been widely studied in prokaryotes such as <i>E. coli</i>. Histidine synthesis in <i>E. coli</i> involves eight gene products (His1, 2, 3, 4, 5, 6, 7, and 8) and it occurs in ten steps. This is possible because a single gene product has the ability to catalyze more than one reaction. For example, as shown in the pathway, <a href="/wiki/Histidinol_dehydrogenase" title="Histidinol dehydrogenase">His4</a> catalyzes 4 different steps in the pathway.<sup id="cite_ref-:1_15-0" class="reference"><a href="#cite_note-:1-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup> </p><p>Histidine is synthesized from <a href="/wiki/Phosphoribosyl_pyrophosphate" title="Phosphoribosyl pyrophosphate">phosphoribosyl pyrophosphate</a> (PRPP), which is made from <a href="/wiki/Ribose-5-phosphate" class="mw-redirect" title="Ribose-5-phosphate">ribose-5-phosphate</a> by <a href="/wiki/Ribose-phosphate_diphosphokinase" title="Ribose-phosphate diphosphokinase">ribose-phosphate diphosphokinase</a> in the <a href="/wiki/Pentose_phosphate_pathway" title="Pentose phosphate pathway">pentose phosphate pathway</a>. The first reaction of histidine biosynthesis is the condensation of PRPP and <a href="/wiki/Adenosine_triphosphate" title="Adenosine triphosphate">adenosine triphosphate</a> (ATP) by the enzyme <a href="/wiki/ATP_phosphoribosyltransferase" title="ATP phosphoribosyltransferase">ATP-phosphoribosyl transferase</a>. ATP-phosphoribosyl transferase is indicated by His1 in the image.<sup id="cite_ref-:1_15-1" class="reference"><a href="#cite_note-:1-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup> His4 gene product then hydrolyzes the product of the condensation, phosphoribosyl-ATP, producing phosphoribosyl-AMP (PRAMP), which is an irreversible step. His4 then catalyzes the formation of phosphoribosylformiminoAICAR-phosphate, which is then converted to phosphoribulosylformimino-AICAR-P by the His6 gene product.<sup id="cite_ref-:2_16-0" class="reference"><a href="#cite_note-:2-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup> His7 splits phosphoribulosylformimino-AICAR-P to form <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r920966791"><span class="smallcaps">d</span>-erythro-imidazole-glycerol-phosphate. After, His3 forms imidazole acetol-phosphate releasing water. His5 then makes <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r920966791"><span class="smallcaps">l</span>-histidinol-phosphate, which is then hydrolyzed by His2 making <a href="/w/index.php?title=Histidinol&action=edit&redlink=1" class="new" title="Histidinol (page does not exist)">histidinol</a>. <a href="/wiki/Histidinol_dehydrogenase" title="Histidinol dehydrogenase">His4</a> catalyzes the oxidation of <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r920966791"><span class="smallcaps">l</span>-histidinol to form <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r920966791"><span class="smallcaps">l</span>-histidinal, an amino aldehyde. In the last step, <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r920966791"><span class="smallcaps">l</span>-histidinal is converted to <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r920966791"><span class="smallcaps">l</span>-histidine.<sup id="cite_ref-:2_16-1" class="reference"><a href="#cite_note-:2-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-17" class="reference"><a href="#cite_note-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup> </p><p>The histidine biosynthesis pathway has been studied in the fungus <i><a href="/wiki/Neurospora_crassa" title="Neurospora crassa">Neurospora crassa</a></i>, and a gene (<i>His-3</i>) encoding a <a href="/wiki/Multienzyme_complex" title="Multienzyme complex">multienzyme complex</a> was found that was similar to the <i>His4</i> gene of the bacterium <i><a href="/wiki/Escherichia_coli" title="Escherichia coli">E. coli</a></i>.<sup id="cite_ref-Ahmed1968_18-0" class="reference"><a href="#cite_note-Ahmed1968-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup> A genetic study of <i>N. crassa</i> histidine <a href="/wiki/Mutant" title="Mutant">mutants</a> indicated that the individual activities of the multienzyme complex occur in discrete, contiguous sections of the <i>His-3</i> <a href="/wiki/Gene_mapping" title="Gene mapping">genetic map</a>, suggesting that the different activities of the multienzyme complex are encoded separately from each other.<sup id="cite_ref-Ahmed1968_18-1" class="reference"><a href="#cite_note-Ahmed1968-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup> However, mutants were also found that lacked all three activities simultaneously, suggesting that some mutations cause loss of function of the complex as a whole. </p><p>Just like animals and microorganisms, plants need histidine for their growth and development.<sup id="cite_ref-:0_10-1" class="reference"><a href="#cite_note-:0-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> Microorganisms and plants are similar in that they can synthesize histidine.<sup id="cite_ref-19" class="reference"><a href="#cite_note-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup> Both synthesize histidine from the biochemical intermediate phosphoribosyl pyrophosphate. In general, the histidine biosynthesis is very similar in plants and microorganisms.<sup id="cite_ref-20" class="reference"><a href="#cite_note-20"><span class="cite-bracket">[</span>20<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading4"><h4 id="Regulation_of_biosynthesis">Regulation of biosynthesis</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Histidine&action=edit&section=5" title="Edit section: Regulation of biosynthesis"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>This pathway requires energy in order to occur therefore, the presence of ATP activates the first enzyme of the pathway, ATP-phosphoribosyl transferase (shown as His1 in the image on the right). ATP-phosphoribosyl transferase is the rate determining enzyme, which is regulated through feedback inhibition meaning that it is inhibited in the presence of the product, histidine.<sup id="cite_ref-21" class="reference"><a href="#cite_note-21"><span class="cite-bracket">[</span>21<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Degradation">Degradation</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Histidine&action=edit&section=6" title="Edit section: Degradation"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Histidine is one of the amino acids that can be converted to intermediates of the tricarboxylic acid (TCA) cycle (also known as the citric acid cycle).<sup id="cite_ref-:3_22-0" class="reference"><a href="#cite_note-:3-22"><span class="cite-bracket">[</span>22<span class="cite-bracket">]</span></a></sup> Histidine, along with other amino acids such as proline and arginine, takes part in deamination, a process in which its amino group is removed. In <a href="/wiki/Prokaryote" title="Prokaryote">prokaryotes</a>, histidine is first converted to urocanate by histidase. Then, urocanase converts urocanate to 4-imidazolone-5-propionate. Imidazolonepropionase catalyzes the reaction to form <a href="/wiki/Formiminoglutamate" class="mw-redirect" title="Formiminoglutamate">formiminoglutamate</a> (FIGLU) from 4-imidazolone-5-propionate.<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> The formimino group is transferred to <a href="/wiki/Tetrahydrofolate" class="mw-redirect" title="Tetrahydrofolate">tetrahydrofolate</a>, and the remaining five carbons form glutamate.<sup id="cite_ref-:3_22-1" class="reference"><a href="#cite_note-:3-22"><span class="cite-bracket">[</span>22<span class="cite-bracket">]</span></a></sup> Overall, these reactions result in the formation of glutamate and ammonia.<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> Glutamate can then be deaminated by <a href="/wiki/Glutamate_dehydrogenase" title="Glutamate dehydrogenase">glutamate dehydrogenase</a> or transaminated to form α-ketoglutarate.<sup id="cite_ref-:3_22-2" class="reference"><a href="#cite_note-:3-22"><span class="cite-bracket">[</span>22<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Conversion_to_other_biologically_active_amines">Conversion to other biologically active amines</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Histidine&action=edit&section=7" title="Edit section: Conversion to other biologically active amines"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li>The histidine amino acid is a precursor for <a href="/wiki/Histamine" title="Histamine">histamine</a>, an amine produced in the body necessary for inflammation.<sup id="cite_ref-25" class="reference"><a href="#cite_note-25"><span class="cite-bracket">[</span>25<span class="cite-bracket">]</span></a></sup></li> <li>The enzyme <a href="/wiki/Histidine_ammonia-lyase" title="Histidine ammonia-lyase">histidine ammonia-lyase</a> converts histidine into <a href="/wiki/Ammonia" title="Ammonia">ammonia</a> and <a href="/wiki/Urocanic_acid" title="Urocanic acid">urocanic acid</a>. A deficiency in this enzyme is present in the rare metabolic disorder <a href="/wiki/Histidinemia" title="Histidinemia">histidinemia</a>, producing <a href="/wiki/Urocanic_aciduria" title="Urocanic aciduria">urocanic aciduria</a> as a key diagnostic finding.</li> <li>Histidine can be converted to <a href="/wiki/3-methylhistidine" class="mw-redirect" title="3-methylhistidine">3-methylhistidine</a>, which serves as a <a href="/wiki/Biomarker_(medicine)" title="Biomarker (medicine)">biomarker</a> for skeletal muscle damage, by certain <a href="/wiki/Methyltransferase" title="Methyltransferase">methyltransferase</a> enzymes.<sup id="cite_ref-HMDB_3-Methylhistidine_26-0" class="reference"><a href="#cite_note-HMDB_3-Methylhistidine-26"><span class="cite-bracket">[</span>26<span class="cite-bracket">]</span></a></sup></li> <li>Histidine is also a precursor for <a href="/wiki/Carnosine" title="Carnosine">carnosine</a> <a href="/wiki/Biosynthesis" title="Biosynthesis">biosynthesis</a>, which is a dipeptide found in skeletal muscle.<sup id="cite_ref-27" class="reference"><a href="#cite_note-27"><span class="cite-bracket">[</span>27<span class="cite-bracket">]</span></a></sup></li> <li>In <a href="/wiki/Actinomycetota" title="Actinomycetota">Actinomycetota</a> and filamentous fungi, such as <i><a href="/wiki/Neurospora_crassa" title="Neurospora crassa">Neurospora crassa</a></i>, histidine can be converted into the <a href="/wiki/Antioxidant" title="Antioxidant">antioxidant</a> <a href="/wiki/Ergothioneine" title="Ergothioneine">ergothioneine</a>.<sup id="cite_ref-Fahey_28-0" class="reference"><a href="#cite_note-Fahey-28"><span class="cite-bracket">[</span>28<span class="cite-bracket">]</span></a></sup></li></ul> <figure class="mw-halign-center" typeof="mw:File/Thumb"><a href="/wiki/File:Histidine_decarboxylase.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/b/b7/Histidine_decarboxylase.svg/400px-Histidine_decarboxylase.svg.png" decoding="async" width="400" height="113" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/b/b7/Histidine_decarboxylase.svg/600px-Histidine_decarboxylase.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/b/b7/Histidine_decarboxylase.svg/800px-Histidine_decarboxylase.svg.png 2x" data-file-width="512" data-file-height="145" /></a><figcaption>Conversion of histidine to <a href="/wiki/Histamine" title="Histamine">histamine</a> by <a href="/wiki/Histidine_decarboxylase" title="Histidine decarboxylase">histidine decarboxylase</a></figcaption></figure> <div class="mw-heading mw-heading2"><h2 id="Requirements">Requirements</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Histidine&action=edit&section=8" title="Edit section: Requirements"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The <a href="/wiki/Food_and_Nutrition_Board" class="mw-redirect" title="Food and Nutrition Board">Food and Nutrition Board</a> (FNB) of the <a href="/wiki/U.S._Institute_of_Medicine" class="mw-redirect" title="U.S. Institute of Medicine">U.S. Institute of Medicine</a> set <a href="/wiki/Recommended_Dietary_Allowances" class="mw-redirect" title="Recommended Dietary Allowances">Recommended Dietary Allowances</a> (RDAs) for <a href="/wiki/Essential_amino_acid" title="Essential amino acid">essential amino acids</a> in 2002. For histidine, for adults 19 years and older, 14 mg/kg body weight/day.<sup id="cite_ref-DRItext_29-0" class="reference"><a href="#cite_note-DRItext-29"><span class="cite-bracket">[</span>29<span class="cite-bracket">]</span></a></sup> Supplemental histidine is being investigated for use in a variety of different conditions, including neurological disorders, atopic dermatitis, metabolic syndrome, diabetes, uraemic anaemia, ulcers, inflammatory bowel diseases, malignancies, and muscle performance during strenuous exercise.<sup id="cite_ref-30" class="reference"><a href="#cite_note-30"><span class="cite-bracket">[</span>30<span class="cite-bracket">]</span></a></sup> </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=Histidine&action=edit&section=9" title="Edit section: See also"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a href="/wiki/Carnosinemia" title="Carnosinemia">Carnosinemia</a></li> <li><a href="/wiki/Beta-Alanine" class="mw-redirect" title="Beta-Alanine">Beta-Alanine</a></li> <li><a href="/wiki/Diphthamide" title="Diphthamide">Diphthamide</a></li> <li><a href="/wiki/Pauly_reaction" title="Pauly reaction">Pauly reaction</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=Histidine&action=edit&section=10" title="Edit section: References"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1239543626">.mw-parser-output .reflist{margin-bottom:0.5em;list-style-type:decimal}@media screen{.mw-parser-output .reflist{font-size:90%}}.mw-parser-output .reflist .references{font-size:100%;margin-bottom:0;list-style-type:inherit}.mw-parser-output .reflist-columns-2{column-width:30em}.mw-parser-output .reflist-columns-3{column-width:25em}.mw-parser-output .reflist-columns{margin-top:0.3em}.mw-parser-output .reflist-columns ol{margin-top:0}.mw-parser-output .reflist-columns li{page-break-inside:avoid;break-inside:avoid-column}.mw-parser-output .reflist-upper-alpha{list-style-type:upper-alpha}.mw-parser-output .reflist-upper-roman{list-style-type:upper-roman}.mw-parser-output .reflist-lower-alpha{list-style-type:lower-alpha}.mw-parser-output .reflist-lower-greek{list-style-type:lower-greek}.mw-parser-output .reflist-lower-roman{list-style-type:lower-roman}</style><div class="reflist"> <div class="mw-references-wrap mw-references-columns"><ol class="references"> <li id="cite_note-1"><span class="mw-cite-backlink"><b><a href="#cite_ref-1">^</a></b></span> <span class="reference-text"><a rel="nofollow" class="external free" href="http://prowl.rockefeller.edu/aainfo/solub.htm">http://prowl.rockefeller.edu/aainfo/solub.htm</a><sup class="noprint Inline-Template" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citing_sources#What_information_to_include" title="Wikipedia:Citing sources"><span title="A complete citation is needed. (March 2015)">full citation needed</span></a></i>]</sup></span> </li> <li id="cite_note-:7-2"><span class="mw-cite-backlink">^ <a href="#cite_ref-:7_2-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-:7_2-1"><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 class="citation web cs1"><a rel="nofollow" class="external text" href="https://web.archive.org/web/20081009023202/http://www.chem.qmul.ac.uk/iupac/AminoAcid/AA1n2.html">"Nomenclature and Symbolism for Amino Acids and Peptides"</a>. 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Washington, DC: The National Academies Press. pp. 589–768. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.17226%2F10490">10.17226/10490</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-309-08525-0" title="Special:BookSources/978-0-309-08525-0"><bdi>978-0-309-08525-0</bdi></a>.</cite><span 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href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7146355">"Histidine in Health and Disease: Metabolism, Physiological Importance, and Use as a Supplement"</a>. <i>Nutrients</i>. <b>12</b> (3): 848. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://doi.org/10.3390%2Fnu12030848">10.3390/nu12030848</a></span>. <a href="/wiki/ISSN_(identifier)" class="mw-redirect" title="ISSN (identifier)">ISSN</a> <a rel="nofollow" class="external text" href="https://search.worldcat.org/issn/2072-6643">2072-6643</a>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7146355">7146355</a></span>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/32235743">32235743</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Nutrients&rft.atitle=Histidine+in+Health+and+Disease%3A+Metabolism%2C+Physiological+Importance%2C+and+Use+as+a+Supplement&rft.volume=12&rft.issue=3&rft.pages=848&rft.date=2020-03-22&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC7146355%23id-name%3DPMC&rft.issn=2072-6643&rft_id=info%3Apmid%2F32235743&rft_id=info%3Adoi%2F10.3390%2Fnu12030848&rft.aulast=Hole%C4%8Dek&rft.aufirst=Milan&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC7146355&rfr_id=info%3Asid%2Fen.wikipedia.org%3AHistidine" 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 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a>span,.mw-parser-output .navbar a>abbr{text-decoration:inherit}.mw-parser-output .navbar-mini abbr{font-variant:small-caps;border-bottom:none;text-decoration:none;cursor:inherit}.mw-parser-output .navbar-ct-full{font-size:114%;margin:0 7em}.mw-parser-output .navbar-ct-mini{font-size:114%;margin:0 4em}html.skin-theme-clientpref-night .mw-parser-output .navbar li a abbr{color:var(--color-base)!important}@media(prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .navbar li a abbr{color:var(--color-base)!important}}@media print{.mw-parser-output .navbar{display:none!important}}</style><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Proteinogenic_amino_acids" title="Template:Proteinogenic amino acids"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Proteinogenic_amino_acids" title="Template talk:Proteinogenic amino acids"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Proteinogenic_amino_acids" title="Special:EditPage/Template:Proteinogenic amino acids"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Encoded_(proteinogenic)_amino_acids" style="font-size:114%;margin:0 4em"><a href="/wiki/Proteinogenic_amino_acid" title="Proteinogenic amino acid">Encoded (proteinogenic) amino acids</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%">General topics</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/Protein" title="Protein">Protein</a></li> <li><a href="/wiki/Peptide" title="Peptide">Peptide</a></li> <li><a href="/wiki/Genetic_code" title="Genetic code">Genetic code</a></li></ul> </div></td><td class="noviewer navbox-image" rowspan="2" style="width:1px;padding:0 0 0 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 class="mw-selflink selflink">Histidine</a></li> <li><a href="/wiki/Tyrosine" title="Tyrosine">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 class="mw-selflink selflink">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 href="/wiki/Tyrosine" title="Tyrosine">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 class="mw-selflink selflink">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 href="/wiki/Tyrosine" title="Tyrosine">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="Histamine_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:Histamine_receptor_modulators" title="Template:Histamine receptor modulators"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Histamine_receptor_modulators" title="Template talk:Histamine receptor modulators"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Histamine_receptor_modulators" title="Special:EditPage/Template:Histamine receptor modulators"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Histamine_receptor_modulators" style="font-size:114%;margin:0 4em"><a href="/wiki/Histamine_receptor" title="Histamine receptor">Histamine 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/Histamine_H1_receptor" title="Histamine H1 receptor">H<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/2-Pyridylethylamine" title="2-Pyridylethylamine">2-Pyridylethylamine</a></li> <li><a href="/wiki/Betahistine" title="Betahistine">Betahistine</a></li> <li><a href="/wiki/Histamine" title="Histamine">Histamine</a></li> <li><a href="/wiki/Histamine_trifluoromethyl_toluidide" title="Histamine trifluoromethyl toluidide">HTMT</a></li> <li><a href="/wiki/L-Histidine" class="mw-redirect" title="L-Histidine"><span style="font-size:85%;">L</span>-Histidine</a></li> <li><a href="/wiki/UR-AK49" title="UR-AK49">UR-AK49</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><i>First-generation:</i> <a href="/wiki/4-Methyldiphenhydramine" title="4-Methyldiphenhydramine">4-Methyldiphenhydramine</a></li> <li><a href="/wiki/Alimemazine" title="Alimemazine">Alimemazine</a></li> <li><a href="/wiki/Antazoline" title="Antazoline">Antazoline</a></li> <li><a href="/wiki/Azatadine" title="Azatadine">Azatadine</a></li> <li><a href="/wiki/Bamipine" title="Bamipine">Bamipine</a></li> <li><a href="/wiki/Benzatropine" title="Benzatropine">Benzatropine (benztropine)</a></li> <li><a href="/wiki/Bepotastine" title="Bepotastine">Bepotastine</a></li> <li><a href="/wiki/Bromazine" title="Bromazine">Bromazine</a></li> <li><a href="/wiki/Brompheniramine" title="Brompheniramine">Brompheniramine</a></li> <li><a href="/wiki/Buclizine" title="Buclizine">Buclizine</a></li> <li><a href="/wiki/Captodiame" title="Captodiame">Captodiame</a></li> <li><a href="/wiki/Carbinoxamine" title="Carbinoxamine">Carbinoxamine</a></li> <li><a href="/wiki/Chlorcyclizine" title="Chlorcyclizine">Chlorcyclizine</a></li> <li><a href="/wiki/Chloropyramine" title="Chloropyramine">Chloropyramine</a></li> <li><a href="/wiki/Chlorothen" title="Chlorothen">Chlorothen</a></li> <li><a href="/wiki/Chlorphenamine" title="Chlorphenamine">Chlorphenamine</a></li> <li><a href="/wiki/Chlorphenoxamine" title="Chlorphenoxamine">Chlorphenoxamine</a></li> <li><a href="/wiki/Cinnarizine" title="Cinnarizine">Cinnarizine</a></li> <li><a href="/wiki/Clemastine" title="Clemastine">Clemastine</a></li> <li><a href="/wiki/Clobenzepam" title="Clobenzepam">Clobenzepam</a></li> <li><a href="/wiki/Clocinizine" title="Clocinizine">Clocinizine</a></li> <li><a href="/wiki/Cloperastine" title="Cloperastine">Cloperastine</a></li> <li><a href="/wiki/Cyclizine" title="Cyclizine">Cyclizine</a></li> <li><a href="/wiki/Cyproheptadine" title="Cyproheptadine">Cyproheptadine</a></li> <li><a href="/wiki/Dacemazine" title="Dacemazine">Dacemazine</a></li> <li><a href="/w/index.php?title=Decloxizine&action=edit&redlink=1" class="new" title="Decloxizine (page does not exist)">Decloxizine</a></li> <li><a href="/wiki/Deptropine" title="Deptropine">Deptropine</a></li> <li><a href="/wiki/Dexbrompheniramine" title="Dexbrompheniramine">Dexbrompheniramine</a></li> <li><a href="/wiki/Dexchlorpheniramine" title="Dexchlorpheniramine">Dexchlorpheniramine</a></li> <li><a href="/wiki/Dimenhydrinate" title="Dimenhydrinate">Dimenhydrinate</a></li> <li><a href="/wiki/Dimetindene" title="Dimetindene">Dimetindene</a></li> <li><a href="/wiki/Diphenhydramine" title="Diphenhydramine">Diphenhydramine</a></li> <li><a href="/wiki/Diphenylpyraline" title="Diphenylpyraline">Diphenylpyraline</a></li> <li><a href="/wiki/Doxylamine" title="Doxylamine">Doxylamine</a></li> <li><a href="/wiki/Embramine" title="Embramine">Embramine</a></li> <li><a href="/wiki/Etodroxizine" title="Etodroxizine">Etodroxizine</a></li> <li><a href="/wiki/Etybenzatropine" title="Etybenzatropine">Etybenzatropine (ethylbenztropine)</a></li> <li><a href="/wiki/Etymemazine" title="Etymemazine">Etymemazine</a></li> <li><a href="/wiki/Fenethazine" title="Fenethazine">Fenethazine</a></li> <li><a href="/wiki/Flunarizine" title="Flunarizine">Flunarizine</a></li> <li><a href="/wiki/Histapyrrodine" title="Histapyrrodine">Histapyrrodine</a></li> <li><a href="/wiki/Homochlorcyclizine" title="Homochlorcyclizine">Homochlorcyclizine</a></li> <li><a href="/wiki/Hydroxyethylpromethazine" title="Hydroxyethylpromethazine">Hydroxyethylpromethazine</a></li> <li><a href="/wiki/Hydroxyzine" title="Hydroxyzine">Hydroxyzine</a></li> <li><a href="/wiki/Isopromethazine" title="Isopromethazine">Isopromethazine</a></li> <li><a href="/wiki/Isothipendyl" title="Isothipendyl">Isothipendyl</a></li> <li><a href="/wiki/Meclozine" class="mw-redirect" title="Meclozine">Meclozine</a></li> <li><a href="/wiki/Medrylamine" title="Medrylamine">Medrylamine</a></li> <li><a href="/wiki/Mepyramine" title="Mepyramine">Mepyramine (pyrilamine)</a></li> <li><a href="/wiki/Mequitazine" title="Mequitazine">Mequitazine</a></li> <li><a href="/wiki/Methafurylene" title="Methafurylene">Methafurylene</a></li> <li><a href="/wiki/Methapyrilene" title="Methapyrilene">Methapyrilene</a></li> <li><a href="/wiki/Methdilazine" title="Methdilazine">Methdilazine</a></li> <li><a href="/wiki/Moxastine" title="Moxastine">Moxastine</a></li> <li><a href="/wiki/Orphenadrine" title="Orphenadrine">Orphenadrine</a></li> <li><a href="/wiki/Oxatomide" title="Oxatomide">Oxatomide</a></li> <li><a href="/wiki/Oxomemazine" title="Oxomemazine">Oxomemazine</a></li> <li><a href="/wiki/Perlapine" title="Perlapine">Perlapine</a></li> <li><a href="/wiki/Phenindamine" title="Phenindamine">Phenindamine</a></li> <li><a href="/wiki/Pheniramine" title="Pheniramine">Pheniramine</a></li> <li><a href="/wiki/Phenyltoloxamine" title="Phenyltoloxamine">Phenyltoloxamine</a></li> <li><a href="/wiki/Pimethixene" title="Pimethixene">Pimethixene</a></li> <li><a href="/wiki/Piperoxan" title="Piperoxan">Piperoxan</a></li> <li><a href="/wiki/Pipoxizine" title="Pipoxizine">Pipoxizine</a></li> <li><a href="/wiki/Promethazine" title="Promethazine">Promethazine</a></li> <li><a href="/wiki/Propiomazine" title="Propiomazine">Propiomazine</a></li> <li><a href="/wiki/Pyrrobutamine" title="Pyrrobutamine">Pyrrobutamine</a></li> <li><a href="/wiki/Talastine" title="Talastine">Talastine</a></li> <li><a href="/wiki/Thenalidine" title="Thenalidine">Thenalidine</a></li> <li><a href="/wiki/Thenyldiamine" title="Thenyldiamine">Thenyldiamine</a></li> <li><a href="/wiki/Thiazinamium" class="mw-redirect" title="Thiazinamium">Thiazinamium</a></li> <li><a href="/wiki/Thonzylamine" title="Thonzylamine">Thonzylamine</a></li> <li><a href="/wiki/Tolpropamine" title="Tolpropamine">Tolpropamine</a></li> <li><a href="/wiki/Tripelennamine" title="Tripelennamine">Tripelennamine</a></li> <li><a href="/wiki/Triprolidine" title="Triprolidine">Triprolidine</a></li></ul> <ul><li><i>Second/third-generation:</i> <a href="/wiki/Acrivastine" title="Acrivastine">Acrivastine</a></li> <li><a href="/w/index.php?title=Alinastine&action=edit&redlink=1" class="new" title="Alinastine (page does not exist)">Alinastine</a></li> <li><a href="/wiki/Astemizole" title="Astemizole">Astemizole</a></li> <li><a href="/wiki/Azelastine" title="Azelastine">Azelastine</a></li> <li><a href="/w/index.php?title=Bamirastine&action=edit&redlink=1" class="new" title="Bamirastine (page does not exist)">Bamirastine</a></li> <li><a href="/w/index.php?title=Barmastine&action=edit&redlink=1" class="new" title="Barmastine (page does not exist)">Barmastine</a></li> <li><a href="/w/index.php?title=Bepiastine&action=edit&redlink=1" class="new" title="Bepiastine (page does not exist)">Bepiastine</a></li> <li><a href="/wiki/Bepotastine" title="Bepotastine">Bepotastine</a></li> <li><a href="/wiki/Bilastine" title="Bilastine">Bilastine</a></li> <li><a href="/w/index.php?title=Cabastinen&action=edit&redlink=1" class="new" title="Cabastinen (page does not exist)">Cabastinen</a></li> <li><a href="/w/index.php?title=Carebastine&action=edit&redlink=1" class="new" title="Carebastine (page does not exist)">Carebastine</a></li> <li><a href="/wiki/Cetirizine" title="Cetirizine">Cetirizine</a></li> <li><a href="/wiki/Clemastine" title="Clemastine">Clemastine</a></li> <li><a href="/wiki/Clemizole" title="Clemizole">Clemizole</a></li> <li><a href="/wiki/Clobenztropine" title="Clobenztropine">Clobenztropine</a></li> <li><a href="/wiki/Desloratadine" title="Desloratadine">Desloratadine</a></li> <li><a href="/w/index.php?title=Dorastine&action=edit&redlink=1" class="new" title="Dorastine (page does not exist)">Dorastine</a></li> <li><a href="/wiki/Ebastine" title="Ebastine">Ebastine</a></li> <li><a href="/w/index.php?title=Efletirizine&action=edit&redlink=1" class="new" title="Efletirizine (page does not exist)">Efletirizine</a></li> <li><a href="/wiki/Emedastine" title="Emedastine">Emedastine</a></li> <li><a href="/wiki/Epinastine" title="Epinastine">Epinastine</a></li> <li><a href="/wiki/Fexofenadine" title="Fexofenadine">Fexofenadine</a></li> <li><a href="/w/index.php?title=Flezelastine&action=edit&redlink=1" class="new" title="Flezelastine (page does not exist)">Flezelastine</a></li> <li><a href="/wiki/Ketotifen" title="Ketotifen">Ketotifen</a></li> <li><a href="/wiki/Latrepirdine" title="Latrepirdine">Latrepirdine</a></li> <li><a href="/wiki/Levocabastine" title="Levocabastine">Levocabastine</a></li> <li><a href="/wiki/Levocetirizine" title="Levocetirizine">Levocetirizine</a></li> <li><a href="/w/index.php?title=Linetastine&action=edit&redlink=1" class="new" title="Linetastine (page does not exist)">Linetastine</a></li> <li><a href="/wiki/Loratadine" title="Loratadine">Loratadine</a></li> <li><a href="/w/index.php?title=Mapinastine&action=edit&redlink=1" class="new" title="Mapinastine (page does not exist)">Mapinastine</a></li> <li><a href="/wiki/Mebhydrolin" title="Mebhydrolin">Mebhydrolin</a></li> <li><a href="/wiki/Mizolastine" title="Mizolastine">Mizolastine</a></li> <li><a href="/wiki/Moxastine" title="Moxastine">Moxastine</a></li> <li><a href="/w/index.php?title=Noberastine&action=edit&redlink=1" class="new" title="Noberastine (page does not exist)">Noberastine</a></li> <li><a href="/w/index.php?title=Octastine&action=edit&redlink=1" class="new" title="Octastine (page does not exist)">Octastine</a></li> <li><a href="/wiki/Olopatadine" title="Olopatadine">Olopatadine</a></li> <li><a href="/w/index.php?title=Perastine&action=edit&redlink=1" class="new" title="Perastine (page does not exist)">Perastine</a></li> <li><a href="/w/index.php?title=Pibaxizine&action=edit&redlink=1" class="new" title="Pibaxizine (page does not exist)">Pibaxizine</a></li> <li><a href="/w/index.php?title=Piclopastine&action=edit&redlink=1" class="new" title="Piclopastine (page does not exist)">Piclopastine</a></li> <li><a href="/wiki/Quifenadine" title="Quifenadine">Quifenadine (phencarol)</a></li> <li><a href="/w/index.php?title=Rocastine&action=edit&redlink=1" class="new" title="Rocastine (page does not exist)">Rocastine</a></li> <li><a href="/wiki/Rupatadine" title="Rupatadine">Rupatadine</a></li> <li><a href="/wiki/Setastine" title="Setastine">Setastine</a></li> <li><a href="/w/index.php?title=Sequifenadine&action=edit&redlink=1" class="new" title="Sequifenadine (page does not exist)">Sequifenadine (bicarphen)</a></li> <li><a href="/wiki/Talastine" title="Talastine">Talastine</a></li> <li><a href="/w/index.php?title=Temelastine&action=edit&redlink=1" class="new" title="Temelastine (page does not exist)">Temelastine</a></li> <li><a href="/wiki/Terfenadine" title="Terfenadine">Terfenadine</a></li> <li><a href="/w/index.php?title=Vapitadine&action=edit&redlink=1" class="new" title="Vapitadine (page does not exist)">Vapitadine</a></li> <li><a href="/w/index.php?title=Zepastine&action=edit&redlink=1" class="new" title="Zepastine (page does not exist)">Zepastine</a></li></ul> <ul><li><i>Others:</i> <a href="/wiki/Atypical_antipsychotic" title="Atypical antipsychotic">Atypical antipsychotics</a> (e.g., <a href="/wiki/Aripiprazole" title="Aripiprazole">aripiprazole</a>, <a href="/wiki/Asenapine" title="Asenapine">asenapine</a>, <a href="/wiki/Brexpiprazole" title="Brexpiprazole">brexpiprazole</a>, <a href="/wiki/Brilaroxazine" title="Brilaroxazine">brilaroxazine</a>, <a href="/wiki/Clozapine" title="Clozapine">clozapine</a>, <a href="/wiki/Iloperidone" title="Iloperidone">iloperidone</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/Ziprasidone" title="Ziprasidone">ziprasidone</a>, <a href="/wiki/Zotepine" title="Zotepine">zotepine</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/Tetracyclic_antidepressant" title="Tetracyclic antidepressant">Tetracyclic antidepressants</a> (e.g., <a href="/wiki/Amoxapine" title="Amoxapine">amoxapine</a>, <a href="/wiki/Loxapine" title="Loxapine">loxapine</a>, <a href="/wiki/Maprotiline" title="Maprotiline">maprotiline</a>, <a href="/wiki/Mianserin" title="Mianserin">mianserin</a>, <a href="/wiki/Mirtazapine" title="Mirtazapine">mirtazapine</a>, <a href="/wiki/Oxaprotiline" title="Oxaprotiline">oxaprotiline</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/Butriptyline" title="Butriptyline">butriptyline</a>, <a href="/wiki/Clomipramine" title="Clomipramine">clomipramine</a>, <a href="/wiki/Desipramine" title="Desipramine">desipramine</a>, <a href="/wiki/Dosulepin" title="Dosulepin">dosulepin (dothiepin)</a>, <a href="/wiki/Doxepin" title="Doxepin">doxepin</a>, <a href="/wiki/Imipramine" title="Imipramine">imipramine</a>, <a href="/wiki/Iprindole" title="Iprindole">iprindole</a>, <a href="/wiki/Lofepramine" title="Lofepramine">lofepramine</a>, <a href="/wiki/Nortriptyline" title="Nortriptyline">nortriptyline</a>, <a href="/wiki/Protriptyline" title="Protriptyline">protriptyline</a>, <a href="/wiki/Trimipramine" title="Trimipramine">trimipramine</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/Flupenthixol" class="mw-redirect" title="Flupenthixol">flupenthixol</a>, <a href="/wiki/Fluphenazine" title="Fluphenazine">fluphenazine</a>, <a href="/wiki/Loxapine" title="Loxapine">loxapine</a>, <a href="/wiki/Perphenazine" title="Perphenazine">perphenazine</a>, <a href="/wiki/Prochlorperazine" title="Prochlorperazine">prochlorperazine</a>, <a href="/wiki/Thioridazine" title="Thioridazine">thioridazine</a>, <a href="/wiki/Thiothixene" class="mw-redirect" title="Thiothixene">thiothixene</a>)</li></ul> <ul><li><i>Unknown/unsorted:</i> <a href="/w/index.php?title=Azanator&action=edit&redlink=1" class="new" title="Azanator (page does not exist)">Azanator</a></li> <li><a href="/w/index.php?title=Belarizine&action=edit&redlink=1" class="new" title="Belarizine (page does not exist)">Belarizine</a></li> <li><a href="/w/index.php?title=Elbanizine&action=edit&redlink=1" class="new" title="Elbanizine (page does not exist)">Elbanizine</a></li> <li><a href="/w/index.php?title=Flotrenizine&action=edit&redlink=1" class="new" title="Flotrenizine (page does not exist)">Flotrenizine</a></li> <li><a href="/w/index.php?title=GSK1004723&action=edit&redlink=1" class="new" title="GSK1004723 (page does not exist)">GSK1004723</a></li> <li><a href="/w/index.php?title=Napactadine&action=edit&redlink=1" class="new" title="Napactadine (page does not exist)">Napactadine</a></li> <li><a href="/w/index.php?title=Tagorizine&action=edit&redlink=1" class="new" title="Tagorizine (page does not exist)">Tagorizine</a></li> <li><a href="/w/index.php?title=Trelnarizine&action=edit&redlink=1" class="new" title="Trelnarizine (page does not exist)">Trelnarizine</a></li> <li><a href="/w/index.php?title=Trenizine&action=edit&redlink=1" class="new" title="Trenizine (page does not exist)">Trenizine</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/Histamine_H2_receptor" title="Histamine H2 receptor">H<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/Amthamine" title="Amthamine">Amthamine</a></li> <li><a href="/wiki/Betazole" title="Betazole">Betazole</a></li> <li><a href="/wiki/Dimaprit" title="Dimaprit">Dimaprit</a></li> <li><a href="/wiki/Histamine" title="Histamine">Histamine</a></li> <li><a href="/wiki/Histamine_trifluoromethyl_toluidide" title="Histamine trifluoromethyl toluidide">HTMT</a></li> <li><a href="/wiki/Impromidine" title="Impromidine">Impromidine</a></li> <li><a href="/wiki/L-Histidine" class="mw-redirect" title="L-Histidine"><span style="font-size:85%;">L</span>-Histidine</a></li> <li><a href="/wiki/UR-AK49" title="UR-AK49">UR-AK49</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="/w/index.php?title=Bisfentidine&action=edit&redlink=1" class="new" title="Bisfentidine (page does not exist)">Bisfentidine</a></li> <li><a href="/wiki/Burimamide" title="Burimamide">Burimamide</a></li> <li><a href="/wiki/Cimetidine" title="Cimetidine">Cimetidine</a></li> <li><a href="/w/index.php?title=Dalcotidine&action=edit&redlink=1" class="new" title="Dalcotidine (page does not exist)">Dalcotidine</a></li> <li><a href="/w/index.php?title=Donetidine&action=edit&redlink=1" class="new" title="Donetidine (page does not exist)">Donetidine</a></li> <li><a href="/wiki/Ebrotidine" title="Ebrotidine">Ebrotidine</a></li> <li><a href="/w/index.php?title=Etintidine&action=edit&redlink=1" class="new" title="Etintidine (page does not exist)">Etintidine</a></li> <li><a href="/wiki/Famotidine" title="Famotidine">Famotidine</a></li> <li><a href="/w/index.php?title=Isolamtidine&action=edit&redlink=1" class="new" title="Isolamtidine (page does not exist)">Isolamtidine</a></li> <li><a href="/wiki/Lafutidine" title="Lafutidine">Lafutidine</a></li> <li><a href="/w/index.php?title=Lamtidine&action=edit&redlink=1" class="new" title="Lamtidine (page does not exist)">Lamtidine</a></li> <li><a href="/wiki/Lavoltidine" title="Lavoltidine">Lavoltidine (loxtidine)</a></li> <li><a href="/wiki/Lupitidine" title="Lupitidine">Lupitidine</a></li> <li><a href="/wiki/Metiamide" title="Metiamide">Metiamide</a></li> <li><a href="/w/index.php?title=Mifentidine&action=edit&redlink=1" class="new" title="Mifentidine (page does not exist)">Mifentidine</a></li> <li><a href="/wiki/Niperotidine" title="Niperotidine">Niperotidine</a></li> <li><a href="/wiki/Nizatidine" title="Nizatidine">Nizatidine</a></li> <li><a href="/w/index.php?title=Osutidine&action=edit&redlink=1" class="new" title="Osutidine (page does not exist)">Osutidine</a></li> <li><a href="/wiki/Oxmetidine" title="Oxmetidine">Oxmetidine</a></li> <li><a href="/w/index.php?title=Pibutidine&action=edit&redlink=1" class="new" title="Pibutidine (page does not exist)">Pibutidine</a></li> <li><a href="/w/index.php?title=Quisultazine&action=edit&redlink=1" class="new" title="Quisultazine (page does not exist)">Quisultazine (quisultidine)</a></li> <li><a href="/w/index.php?title=Ramixotidine&action=edit&redlink=1" class="new" title="Ramixotidine (page does not exist)">Ramixotidine</a></li> <li><a href="/wiki/Ranitidine" title="Ranitidine">Ranitidine</a></li> <li><a href="/wiki/Roxatidine" class="mw-redirect" title="Roxatidine">Roxatidine</a></li> <li><a href="/wiki/Sufotidine" title="Sufotidine">Sufotidine</a></li> <li><a href="/w/index.php?title=Tiotidine&action=edit&redlink=1" class="new" title="Tiotidine (page does not exist)">Tiotidine</a></li> <li><a href="/w/index.php?title=Tuvatidine&action=edit&redlink=1" class="new" title="Tuvatidine (page does not exist)">Tuvatidine</a></li> <li><a href="/w/index.php?title=Venritidine&action=edit&redlink=1" class="new" title="Venritidine (page does not exist)">Venritidine</a></li> <li><a href="/w/index.php?title=Xaltidine&action=edit&redlink=1" class="new" title="Xaltidine (page does not exist)">Xaltidine</a></li> <li><a href="/wiki/Zolantidine" title="Zolantidine">Zolantidine</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/Histamine_H3_receptor" title="Histamine H3 receptor">H<sub>3</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/Alpha-Methylhistamine" class="mw-redirect" title="Alpha-Methylhistamine">α-Methylhistamine</a></li> <li><a href="/wiki/Cipralisant" title="Cipralisant">Cipralisant</a></li> <li><a href="/wiki/Histamine" title="Histamine">Histamine</a></li> <li><a href="/wiki/Imetit" title="Imetit">Imetit</a></li> <li><a href="/wiki/Immepip" title="Immepip">Immepip</a></li> <li><a href="/wiki/Immethridine" title="Immethridine">Immethridine</a></li> <li><a href="/wiki/L-Histidine" class="mw-redirect" title="L-Histidine"><span style="font-size:85%;">L</span>-Histidine</a></li> <li><a href="/wiki/Methimepip" title="Methimepip">Methimepip</a></li> <li><a href="/wiki/Proxyfan" title="Proxyfan">Proxyfan</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/A-349821" title="A-349821">A-349821</a></li> <li><a href="/wiki/A-423579" title="A-423579">A-423579</a></li> <li><a href="/wiki/ABT-239" title="ABT-239">ABT-239</a></li> <li><a href="/w/index.php?title=ABT-652&action=edit&redlink=1" class="new" title="ABT-652 (page does not exist)">ABT-652</a></li> <li><a href="/w/index.php?title=AZD5213&action=edit&redlink=1" class="new" title="AZD5213 (page does not exist)">AZD5213</a></li> <li><a href="/w/index.php?title=Bavisant&action=edit&redlink=1" class="new" title="Bavisant (page does not exist)">Bavisant</a></li> <li><a href="/wiki/Betahistine" title="Betahistine">Betahistine</a></li> <li><a href="/wiki/Burimamide" title="Burimamide">Burimamide</a></li> <li><a href="/wiki/Ciproxifan" title="Ciproxifan">Ciproxifan</a></li> <li><a href="/wiki/Clobenpropit" title="Clobenpropit">Clobenpropit</a></li> <li><a href="/wiki/Conessine" title="Conessine">Conessine</a></li> <li><a href="/w/index.php?title=Enerisant&action=edit&redlink=1" class="new" title="Enerisant (page does not exist)">Enerisant</a></li> <li><a href="/wiki/GSK-189254" title="GSK-189254">GSK-189254</a></li> <li><a href="/wiki/Impentamine" title="Impentamine">Impentamine</a></li> <li><a href="/wiki/Iodophenpropit" title="Iodophenpropit">Iodophenpropit</a></li> <li><a href="/w/index.php?title=Irdabisant&action=edit&redlink=1" class="new" title="Irdabisant (page does not exist)">Irdabisant</a></li> <li><a href="/wiki/JNJ-5207852" title="JNJ-5207852">JNJ-5207852</a></li> <li><a href="/wiki/NNC_38-1049" title="NNC 38-1049">NNC 38-1049</a></li> <li><a href="/wiki/PF-03654746" title="PF-03654746">PF-03654746</a></li> <li><a href="/wiki/Pitolisant" title="Pitolisant">Pitolisant</a></li> <li><a href="/wiki/SCH-79687" title="SCH-79687">SCH-79687</a></li> <li><a href="/wiki/Thioperamide" title="Thioperamide">Thioperamide</a></li> <li><a href="/wiki/VUF-5681" title="VUF-5681">VUF-5681</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/Histamine_H4_receptor" title="Histamine H4 receptor">H<sub>4</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/4-Methylhistamine" title="4-Methylhistamine">4-Methylhistamine</a></li> <li><a href="/wiki/Alpha-Methylhistamine" class="mw-redirect" title="Alpha-Methylhistamine">α-Methylhistamine</a></li> <li><a href="/wiki/Histamine" title="Histamine">Histamine</a></li> <li><a href="/wiki/L-Histidine" class="mw-redirect" title="L-Histidine"><span style="font-size:85%;">L</span>-Histidine</a></li> <li><a href="/wiki/OUP-16" title="OUP-16">OUP-16</a></li> <li><a href="/wiki/VUF-8430" title="VUF-8430">VUF-8430</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/JNJ-7777120" title="JNJ-7777120">JNJ-7777120</a></li> <li><a href="/wiki/Mianserin" title="Mianserin">Mianserin</a></li> <li><a href="/w/index.php?title=Seliforant&action=edit&redlink=1" class="new" title="Seliforant (page does not exist)">Seliforant</a></li> <li><a href="/wiki/Thioperamide" title="Thioperamide">Thioperamide</a></li> <li><a href="/wiki/Toreforant" title="Toreforant">Toreforant</a></li> <li><a href="/wiki/VUF-6002" title="VUF-6002">VUF-6002</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><td class="navbox-abovebelow" colspan="2"><div> <dl><dt>See also</dt> <dd><a href="/wiki/Template:Receptor_modulators" title="Template:Receptor modulators">Receptor/signaling modulators</a></dd> <dd><a href="/wiki/Template:Monoamine_metabolism_modulators" title="Template:Monoamine metabolism modulators">Monoamine metabolism modulators</a></dd> <dd><a href="/wiki/Template:Monoamine_reuptake_inhibitors" title="Template:Monoamine reuptake inhibitors">Monoamine reuptake inhibitors</a></dd></dl> </div></td></tr></tbody></table></div> <style data-mw-deduplicate="TemplateStyles:r1235681985">.mw-parser-output .side-box{margin:4px 0;box-sizing:border-box;border:1px solid #aaa;font-size:88%;line-height:1.25em;background-color:var(--background-color-interactive-subtle,#f8f9fa);display:flow-root}.mw-parser-output .side-box-abovebelow,.mw-parser-output .side-box-text{padding:0.25em 0.9em}.mw-parser-output .side-box-image{padding:2px 0 2px 0.9em;text-align:center}.mw-parser-output .side-box-imageright{padding:2px 0.9em 2px 0;text-align:center}@media(min-width:500px){.mw-parser-output .side-box-flex{display:flex;align-items:center}.mw-parser-output .side-box-text{flex:1;min-width:0}}@media(min-width:720px){.mw-parser-output .side-box{width:238px}.mw-parser-output .side-box-right{clear:right;float:right;margin-left:1em}.mw-parser-output .side-box-left{margin-right:1em}}</style><style data-mw-deduplicate="TemplateStyles:r1237033735">@media print{body.ns-0 .mw-parser-output .sistersitebox{display:none!important}}@media screen{html.skin-theme-clientpref-night .mw-parser-output .sistersitebox img[src*="Wiktionary-logo-en-v2.svg"]{background-color:white}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .sistersitebox img[src*="Wiktionary-logo-en-v2.svg"]{background-color:white}}</style><div class="side-box side-box-right plainlinks sistersitebox"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"> <div class="side-box-flex"> <div class="side-box-image"><span class="noviewer" typeof="mw:File"><span><img alt="" src="//upload.wikimedia.org/wikipedia/en/thumb/4/4a/Commons-logo.svg/30px-Commons-logo.svg.png" decoding="async" width="30" height="40" class="mw-file-element" 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