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class="vector-toc-numb">2</span> <span>Synthesis and metabolism</span> </div> </a> <ul id="toc-Synthesis_and_metabolism-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Storage_and_release" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Storage_and_release"> <div class="vector-toc-text"> <span class="vector-toc-numb">3</span> <span>Storage and release</span> </div> </a> <ul id="toc-Storage_and_release-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Degradation" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Degradation"> <div class="vector-toc-text"> <span class="vector-toc-numb">4</span> <span>Degradation</span> </div> </a> <ul id="toc-Degradation-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Mechanism_of_action" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Mechanism_of_action"> <div class="vector-toc-text"> <span class="vector-toc-numb">5</span> <span>Mechanism of action</span> </div> </a> <ul id="toc-Mechanism_of_action-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Roles_in_the_body" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Roles_in_the_body"> <div class="vector-toc-text"> <span class="vector-toc-numb">6</span> <span>Roles in the body</span> </div> </a> <button aria-controls="toc-Roles_in_the_body-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> <span class="vector-icon mw-ui-icon-wikimedia-expand"></span> <span>Toggle Roles in the body subsection</span> </button> <ul id="toc-Roles_in_the_body-sublist" class="vector-toc-list"> <li id="toc-Vasodilation_and_fall_in_blood_pressure" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Vasodilation_and_fall_in_blood_pressure"> <div class="vector-toc-text"> <span class="vector-toc-numb">6.1</span> <span>Vasodilation and fall in blood pressure</span> </div> </a> <ul id="toc-Vasodilation_and_fall_in_blood_pressure-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Effects_on_nasal_mucous_membrane" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Effects_on_nasal_mucous_membrane"> <div class="vector-toc-text"> <span class="vector-toc-numb">6.2</span> <span>Effects on nasal mucous membrane</span> </div> </a> <ul id="toc-Effects_on_nasal_mucous_membrane-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Sleep-wake_regulation" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Sleep-wake_regulation"> <div class="vector-toc-text"> <span class="vector-toc-numb">6.3</span> <span>Sleep-wake regulation</span> </div> </a> <ul id="toc-Sleep-wake_regulation-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Gastric_acid_release" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Gastric_acid_release"> <div class="vector-toc-text"> <span class="vector-toc-numb">6.4</span> <span>Gastric acid release</span> </div> </a> <ul id="toc-Gastric_acid_release-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Protective_effects" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Protective_effects"> <div class="vector-toc-text"> <span class="vector-toc-numb">6.5</span> <span>Protective effects</span> </div> </a> <ul id="toc-Protective_effects-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Erection_and_sexual_function" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Erection_and_sexual_function"> <div class="vector-toc-text"> <span class="vector-toc-numb">6.6</span> <span>Erection and sexual function</span> </div> </a> <ul id="toc-Erection_and_sexual_function-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Schizophrenia" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Schizophrenia"> <div class="vector-toc-text"> <span class="vector-toc-numb">6.7</span> <span>Schizophrenia</span> </div> </a> <ul id="toc-Schizophrenia-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Multiple_sclerosis" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Multiple_sclerosis"> <div class="vector-toc-text"> <span class="vector-toc-numb">6.8</span> <span>Multiple sclerosis</span> </div> </a> <ul id="toc-Multiple_sclerosis-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Disorders" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Disorders"> <div class="vector-toc-text"> <span class="vector-toc-numb">7</span> <span>Disorders</span> </div> </a> <ul id="toc-Disorders-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Measurement" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Measurement"> <div class="vector-toc-text"> <span class="vector-toc-numb">8</span> <span>Measurement</span> </div> </a> <ul id="toc-Measurement-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-History" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#History"> <div class="vector-toc-text"> <span class="vector-toc-numb">9</span> <span>History</span> </div> </a> <ul id="toc-History-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-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">10</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">11</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">12</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" 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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 64 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-64" 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">64 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%D8%A7%D9%85%D9%8A%D9%86" title="هستامين – Arabic" lang="ar" hreflang="ar" data-title="هستامين" 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%D8%A7%D9%85%DB%8C%D9%86" title="هیستامین – South Azerbaijani" lang="azb" hreflang="azb" data-title="هیستامین" data-language-autonym="تۆرکجه" data-language-local-name="South Azerbaijani" class="interlanguage-link-target"><span>تۆرکجه</span></a></li><li class="interlanguage-link interwiki-bn mw-list-item"><a href="https://bn.wikipedia.org/wiki/%E0%A6%B9%E0%A6%BF%E0%A6%B8%E0%A7%8D%E0%A6%9F%E0%A6%BE%E0%A6%AE%E0%A6%BF%E0%A6%A8" title="হিস্টামিন – Bangla" lang="bn" hreflang="bn" data-title="হিস্টামিন" data-language-autonym="বাংলা" data-language-local-name="Bangla" class="interlanguage-link-target"><span>বাংলা</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%D0%B0%D0%BC%D1%96%D0%BD" title="Гістамін – Belarusian" lang="be" hreflang="be" data-title="Гістамін" 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%B0%D0%BC%D0%B8%D0%BD" title="Хистамин – Bulgarian" lang="bg" hreflang="bg" data-title="Хистамин" 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/Histamin" title="Histamin – Bosnian" lang="bs" hreflang="bs" data-title="Histamin" 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/Histamina" title="Histamina – Catalan" lang="ca" hreflang="ca" data-title="Histamina" 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/Histamin" title="Histamin – Czech" lang="cs" hreflang="cs" data-title="Histamin" 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/Histamin" title="Histamin – Danish" lang="da" hreflang="da" data-title="Histamin" 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/Histamin" title="Histamin – German" lang="de" hreflang="de" data-title="Histamin" 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/Histamiin" title="Histamiin – Estonian" lang="et" hreflang="et" data-title="Histamiin" 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%B1%CE%BC%CE%AF%CE%BD%CE%B7" title="Ισταμίνη – Greek" lang="el" hreflang="el" data-title="Ισταμίνη" 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/Histamina" title="Histamina – Spanish" lang="es" hreflang="es" data-title="Histamina" 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/Histamino" title="Histamino – Esperanto" lang="eo" hreflang="eo" data-title="Histamino" 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/Histamina" title="Histamina – Basque" lang="eu" hreflang="eu" data-title="Histamina" 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%D8%A7%D9%85%DB%8C%D9%86" title="هیستامین – Persian" lang="fa" hreflang="fa" data-title="هیستامین" 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/Histamine" title="Histamine – French" lang="fr" hreflang="fr" data-title="Histamine" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target"><span>Français</span></a></li><li class="interlanguage-link interwiki-ga mw-list-item"><a href="https://ga.wikipedia.org/wiki/Hiostaim%C3%ADn" title="Hiostaimín – Irish" lang="ga" hreflang="ga" data-title="Hiostaimín" data-language-autonym="Gaeilge" data-language-local-name="Irish" class="interlanguage-link-target"><span>Gaeilge</span></a></li><li class="interlanguage-link interwiki-gl mw-list-item"><a href="https://gl.wikipedia.org/wiki/Histamina" title="Histamina – Galician" lang="gl" hreflang="gl" data-title="Histamina" 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%83%80%EB%AF%BC" title="히스타민 – Korean" lang="ko" hreflang="ko" data-title="히스타민" 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%A1%D5%B4%D5%AB%D5%B6" title="Հիստամին – Armenian" lang="hy" hreflang="hy" data-title="Հիստամին" 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%BE%E0%A4%AE%E0%A4%BF%E0%A4%A8" title="हिस्टामिन – Hindi" lang="hi" hreflang="hi" data-title="हिस्टामिन" 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/Histamin" title="Histamin – Croatian" lang="hr" hreflang="hr" data-title="Histamin" 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/Histamin" title="Histamin – Indonesian" lang="id" hreflang="id" data-title="Histamin" 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/Istamina" title="Istamina – Italian" lang="it" hreflang="it" data-title="Istamina" 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%9E%D7%99%D7%9F" title="היסטמין – Hebrew" lang="he" hreflang="he" data-title="היסטמין" data-language-autonym="עברית" data-language-local-name="Hebrew" class="interlanguage-link-target"><span>עברית</span></a></li><li class="interlanguage-link interwiki-kk mw-list-item"><a href="https://kk.wikipedia.org/wiki/%D0%93%D0%B8%D1%81%D1%82%D0%B0%D0%BC%D0%B8%D0%BD" title="Гистамин – Kazakh" lang="kk" hreflang="kk" data-title="Гистамин" data-language-autonym="Қазақша" data-language-local-name="Kazakh" class="interlanguage-link-target"><span>Қазақша</span></a></li><li class="interlanguage-link interwiki-ky mw-list-item"><a href="https://ky.wikipedia.org/wiki/%D0%93%D0%B8%D1%81%D1%82%D0%B0%D0%BC%D0%B8%D0%BD" title="Гистамин – Kyrgyz" lang="ky" hreflang="ky" data-title="Гистамин" data-language-autonym="Кыргызча" data-language-local-name="Kyrgyz" class="interlanguage-link-target"><span>Кыргызча</span></a></li><li class="interlanguage-link interwiki-la mw-list-item"><a href="https://la.wikipedia.org/wiki/Histaminum" title="Histaminum – Latin" lang="la" hreflang="la" data-title="Histaminum" data-language-autonym="Latina" data-language-local-name="Latin" class="interlanguage-link-target"><span>Latina</span></a></li><li class="interlanguage-link interwiki-lt mw-list-item"><a href="https://lt.wikipedia.org/wiki/Histaminas" title="Histaminas – Lithuanian" lang="lt" hreflang="lt" data-title="Histaminas" 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/Hisztamin" title="Hisztamin – Hungarian" lang="hu" hreflang="hu" data-title="Hisztamin" 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%B0%D0%BC%D0%B8%D0%BD" title="Хистамин – Macedonian" lang="mk" hreflang="mk" data-title="Хистамин" data-language-autonym="Македонски" data-language-local-name="Macedonian" class="interlanguage-link-target"><span>Македонски</span></a></li><li class="interlanguage-link interwiki-ml mw-list-item"><a href="https://ml.wikipedia.org/wiki/%E0%B4%B9%E0%B4%BF%E0%B4%B8%E0%B5%8D%E0%B4%B1%E0%B5%8D%E0%B4%B1%E0%B4%AE%E0%B4%BF%E0%B5%BB" title="ഹിസ്റ്റമിൻ – Malayalam" lang="ml" hreflang="ml" data-title="ഹിസ്റ്റമിൻ" data-language-autonym="മലയാളം" data-language-local-name="Malayalam" class="interlanguage-link-target"><span>മലയാളം</span></a></li><li class="interlanguage-link interwiki-ms mw-list-item"><a href="https://ms.wikipedia.org/wiki/Histamin" title="Histamin – Malay" lang="ms" hreflang="ms" data-title="Histamin" 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/Histamine" title="Histamine – Dutch" lang="nl" hreflang="nl" data-title="Histamine" 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%82%BF%E3%83%9F%E3%83%B3" title="ヒスタミン – Japanese" lang="ja" hreflang="ja" data-title="ヒスタミン" 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/Histamin" title="Histamin – Norwegian Bokmål" lang="nb" hreflang="nb" data-title="Histamin" data-language-autonym="Norsk bokmål" data-language-local-name="Norwegian Bokmål" class="interlanguage-link-target"><span>Norsk bokmål</span></a></li><li class="interlanguage-link interwiki-oc mw-list-item"><a href="https://oc.wikipedia.org/wiki/Istamina" title="Istamina – Occitan" lang="oc" hreflang="oc" data-title="Istamina" 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/Gistamin" title="Gistamin – Uzbek" lang="uz" hreflang="uz" data-title="Gistamin" data-language-autonym="Oʻzbekcha / ўзбекча" data-language-local-name="Uzbek" class="interlanguage-link-target"><span>Oʻzbekcha / ўзбекча</span></a></li><li class="interlanguage-link interwiki-pl mw-list-item"><a href="https://pl.wikipedia.org/wiki/Histamina" title="Histamina – Polish" lang="pl" hreflang="pl" data-title="Histamina" 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/Histamina" title="Histamina – Portuguese" lang="pt" hreflang="pt" data-title="Histamina" 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/Histamin%C4%83" title="Histamină – Romanian" lang="ro" hreflang="ro" data-title="Histamină" 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%B0%D0%BC%D0%B8%D0%BD" title="Гистамин – Russian" lang="ru" hreflang="ru" data-title="Гистамин" data-language-autonym="Русский" data-language-local-name="Russian" class="interlanguage-link-target"><span>Русский</span></a></li><li class="interlanguage-link interwiki-sco mw-list-item"><a href="https://sco.wikipedia.org/wiki/Histamine" title="Histamine – Scots" lang="sco" hreflang="sco" data-title="Histamine" data-language-autonym="Scots" data-language-local-name="Scots" class="interlanguage-link-target"><span>Scots</span></a></li><li class="interlanguage-link interwiki-si mw-list-item"><a href="https://si.wikipedia.org/wiki/%E0%B7%84%E0%B7%92%E0%B7%83%E0%B7%8A%E0%B6%A7%E0%B6%B8%E0%B7%92%E0%B6%B1%E0%B7%8A" title="හිස්ටමින් – Sinhala" lang="si" hreflang="si" data-title="හිස්ටමින්" data-language-autonym="සිංහල" data-language-local-name="Sinhala" class="interlanguage-link-target"><span>සිංහල</span></a></li><li class="interlanguage-link interwiki-simple mw-list-item"><a href="https://simple.wikipedia.org/wiki/Histamine" title="Histamine – Simple English" lang="en-simple" hreflang="en-simple" data-title="Histamine" 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/Histam%C3%ADn" title="Histamín – Slovak" lang="sk" hreflang="sk" data-title="Histamín" 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/Histamin" title="Histamin – Slovenian" lang="sl" hreflang="sl" data-title="Histamin" data-language-autonym="Slovenščina" data-language-local-name="Slovenian" class="interlanguage-link-target"><span>Slovenščina</span></a></li><li class="interlanguage-link interwiki-ckb mw-list-item"><a href="https://ckb.wikipedia.org/wiki/%DA%BE%DB%8C%D8%B3%D8%AA%D8%A7%D9%85%DB%8C%D9%86" title="ھیستامین – Central Kurdish" lang="ckb" hreflang="ckb" data-title="ھیستامین" data-language-autonym="کوردی" data-language-local-name="Central Kurdish" class="interlanguage-link-target"><span>کوردی</span></a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/Histamin" title="Histamin – Serbian" lang="sr" hreflang="sr" data-title="Histamin" 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/Histamin" title="Histamin – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Histamin" data-language-autonym="Srpskohrvatski / српскохрватски" data-language-local-name="Serbo-Croatian" class="interlanguage-link-target"><span>Srpskohrvatski / српскохрватски</span></a></li><li class="interlanguage-link interwiki-fi mw-list-item"><a href="https://fi.wikipedia.org/wiki/Histamiini" title="Histamiini – Finnish" lang="fi" hreflang="fi" data-title="Histamiini" 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/Histamin" title="Histamin – Swedish" lang="sv" hreflang="sv" data-title="Histamin" data-language-autonym="Svenska" data-language-local-name="Swedish" class="interlanguage-link-target"><span>Svenska</span></a></li><li class="interlanguage-link interwiki-tl mw-list-item"><a href="https://tl.wikipedia.org/wiki/Histamina" title="Histamina – Tagalog" lang="tl" hreflang="tl" data-title="Histamina" data-language-autonym="Tagalog" data-language-local-name="Tagalog" class="interlanguage-link-target"><span>Tagalog</span></a></li><li class="interlanguage-link interwiki-ta mw-list-item"><a href="https://ta.wikipedia.org/wiki/%E0%AE%A4%E0%AE%BF%E0%AE%9A%E0%AF%81%E0%AE%A8%E0%AF%80%E0%AE%B0%E0%AF%8D%E0%AE%A4%E0%AF%8D%E0%AE%A4%E0%AF%87%E0%AE%95%E0%AF%8D%E0%AE%95%E0%AE%BF" title="திசுநீர்த்தேக்கி – Tamil" lang="ta" hreflang="ta" data-title="திசுநீர்த்தேக்கி" data-language-autonym="தமிழ்" data-language-local-name="Tamil" class="interlanguage-link-target"><span>தமிழ்</span></a></li><li class="interlanguage-link interwiki-te mw-list-item"><a href="https://te.wikipedia.org/wiki/%E0%B0%B9%E0%B0%BF%E0%B0%B8%E0%B1%8D%E0%B0%9F%E0%B0%AE%E0%B0%BF%E0%B0%A8%E0%B1%8D" title="హిస్టమిన్ – Telugu" lang="te" hreflang="te" data-title="హిస్టమిన్" data-language-autonym="తెలుగు" data-language-local-name="Telugu" class="interlanguage-link-target"><span>తెలుగు</span></a></li><li class="interlanguage-link interwiki-th mw-list-item"><a href="https://th.wikipedia.org/wiki/%E0%B8%AE%E0%B8%B4%E0%B8%AA%E0%B8%95%E0%B8%B2%E0%B8%A1%E0%B8%B5%E0%B8%99" title="ฮิสตามีน – Thai" lang="th" hreflang="th" data-title="ฮิสตามีน" data-language-autonym="ไทย" data-language-local-name="Thai" class="interlanguage-link-target"><span>ไทย</span></a></li><li class="interlanguage-link interwiki-tr mw-list-item"><a href="https://tr.wikipedia.org/wiki/Histamin" title="Histamin – Turkish" lang="tr" hreflang="tr" data-title="Histamin" 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%B0%D0%BC%D1%96%D0%BD" title="Гістамін – Ukrainian" lang="uk" hreflang="uk" data-title="Гістамін" 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/Histamin" title="Histamin – Vietnamese" lang="vi" hreflang="vi" data-title="Histamin" 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-war mw-list-item"><a href="https://war.wikipedia.org/wiki/Histamin" title="Histamin – Waray" lang="war" hreflang="war" data-title="Histamin" data-language-autonym="Winaray" data-language-local-name="Waray" class="interlanguage-link-target"><span>Winaray</span></a></li><li class="interlanguage-link interwiki-wuu mw-list-item"><a href="https://wuu.wikipedia.org/wiki/%E7%BB%84%E8%83%BA" title="组胺 – Wu" lang="wuu" hreflang="wuu" data-title="组胺" data-language-autonym="吴语" data-language-local-name="Wu" class="interlanguage-link-target"><span>吴语</span></a></li><li class="interlanguage-link interwiki-zh-yue mw-list-item"><a href="https://zh-yue.wikipedia.org/wiki/%E7%B5%84%E7%B9%94%E8%83%BA" title="組織胺 – Cantonese" lang="yue" hreflang="yue" data-title="組織胺" data-language-autonym="粵語" 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</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"></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">Organic compound involved in immune responses</div> <style data-mw-deduplicate="TemplateStyles:r1236090951">.mw-parser-output .hatnote{font-style:italic}.mw-parser-output div.hatnote{padding-left:1.6em;margin-bottom:0.5em}.mw-parser-output .hatnote i{font-style:normal}.mw-parser-output .hatnote+link+.hatnote{margin-top:-0.5em}@media print{body.ns-0 .mw-parser-output .hatnote{display:none!important}}</style><div role="note" class="hatnote navigation-not-searchable">For the use as an immunostimulant drug, see <a href="/wiki/Histamine_dihydrochloride" title="Histamine dihydrochloride">Histamine dihydrochloride</a>.</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>Histamine </caption> <tbody><tr> <td colspan="2" style="text-align:center; padding:2px;"><span typeof="mw:File"><a href="/wiki/File:Histamine.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/0/0e/Histamine.svg/220px-Histamine.svg.png" decoding="async" width="220" height="119" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/0/0e/Histamine.svg/330px-Histamine.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/0/0e/Histamine.svg/440px-Histamine.svg.png 2x" data-file-width="512" data-file-height="277" /></a></span> </td></tr> <tr> <td colspan="2" style="text-align:center; padding:2px;"><span typeof="mw:File"><a href="/wiki/File:Histamine_3D_ball.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/7/7d/Histamine_3D_ball.png/220px-Histamine_3D_ball.png" decoding="async" width="220" height="158" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/7/7d/Histamine_3D_ball.png/330px-Histamine_3D_ball.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/7/7d/Histamine_3D_ball.png/440px-Histamine_3D_ball.png 2x" data-file-width="2000" data-file-height="1438" /></a></span> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Names </th></tr> <tr> <td colspan="2" style="text-align:left;"><a href="/wiki/Chemical_nomenclature" title="Chemical nomenclature">IUPAC name</a> <div style="max-width:22em; word-wrap:break-word; padding-left:1.7em;">2-(1<i>H</i>-Imidazol-4-yl)ethanamine</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=51-45-6">51-45-6</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=NCCc1c%5BnH%5Dcn1">Interactive image</a></span></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ChEBI" title="ChEBI">ChEBI</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.ebi.ac.uk"><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chebi/searchId.do?chebiId=18295">CHEBI:18295</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ChEMBL" title="ChEMBL">ChEMBL</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.ebi.ac.uk"><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chembl/explore/compound/ChEMBL90">ChEMBL90</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.753.html">753</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/DB05381">DB05381</a></span></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/100.000.092">100.000.092</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q61233#P2566" title="Edit this at Wikidata"><img alt="Edit this at Wikidata" src="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/10px-OOjs_UI_icon_edit-ltr-progressive.svg.png" decoding="async" width="10" height="10" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/15px-OOjs_UI_icon_edit-ltr-progressive.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/20px-OOjs_UI_icon_edit-ltr-progressive.svg.png 2x" data-file-width="20" data-file-height="20" /></a></span> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/IUPHAR/BPS" class="mw-redirect" title="IUPHAR/BPS">IUPHAR/BPS</a></div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.guidetopharmacology.org"><a rel="nofollow" class="external text" href="http://www.guidetopharmacology.org/GRAC/LigandDisplayForward?tab=summary&ligandId=1204">1204</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/D08040">D08040</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><a href="/wiki/Medical_Subject_Headings" title="Medical Subject Headings">MeSH</a> </td> <td><span title="www.nlm.nih.gov"><a rel="nofollow" class="external text" href="https://www.nlm.nih.gov/cgi/mesh/2014/MB_cgi?mode=&term=Histamine">Histamine</a></span> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/PubChem" title="PubChem">PubChem</a> <abbr title="Compound ID">CID</abbr></div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="pubchem.ncbi.nlm.nih.gov"><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/774">774</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/820484N8I3">820484N8I3</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/DTXSID4023125">DTXSID4023125</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q61233#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/C5H9N3/c6-2-1-5-3-7-4-8-5/h3-4H,1-2,6H2,(H,7,8)<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: NTYJJOPFIAHURM-UHFFFAOYSA-N<sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></div></div></li><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=1/C5H9N3/c6-2-1-5-3-7-4-8-5/h3-4H,1-2,6H2,(H,7,8)</div><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">Key: NTYJJOPFIAHURM-UHFFFAOYAP</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%;">NCCc1c[nH]cn1</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>5</sub><span title="Hydrogen">H</span><sub>9</sub><span title="Nitrogen">N</span><sub>3</sub> </td></tr> <tr> <td><a href="/wiki/Molar_mass" title="Molar mass">Molar mass</a> </td> <td><span class="nowrap"><span data-sort-value="7002111148000000000♠"></span>111.148</span> g·mol<sup>−1</sup>   </td></tr> <tr> <td><a href="/wiki/Melting_point" title="Melting point">Melting point</a> </td> <td>83.5 °C (182.3 °F; 356.6 K) </td></tr> <tr> <td><a href="/wiki/Boiling_point" title="Boiling point">Boiling point</a> </td> <td>209.5 °C (409.1 °F; 482.6 K) </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>Easily soluble in cold water, hot water<sup id="cite_ref-sciencelab.com_1-0" class="reference"><a href="#cite_note-sciencelab.com-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><a href="/wiki/Solubility" title="Solubility">Solubility</a> in other solvents </td> <td>Easily soluble in methanol. Very slightly soluble in diethyl ether.<sup id="cite_ref-sciencelab.com_1-1" class="reference"><a href="#cite_note-sciencelab.com-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> Easily soluble in ethanol. </td></tr> <tr> <td><a href="/wiki/Partition_coefficient" title="Partition coefficient">log <i>P</i></a> </td> <td>−0.7<sup id="cite_ref-Vuckovic_2-0" class="reference"><a href="#cite_note-Vuckovic-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><a href="/wiki/Acid_dissociation_constant" title="Acid dissociation constant">Acidity</a> (p<i>K</i><sub>a</sub>) </td> <td><a href="/wiki/Imidazole" title="Imidazole">Imidazole</a>: 6.04 <br /> Terminal NH<sub>2</sub>: 9.75<sup id="cite_ref-Vuckovic_2-1" class="reference"><a href="#cite_note-Vuckovic-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Pharmacology </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Anatomical_Therapeutic_Chemical_Classification_System" title="Anatomical Therapeutic Chemical Classification System">ATC code</a></div> </td> <td><a href="/wiki/ATC_code_L03" title="ATC code L03">L03AX14</a> (<span title="www.whocc.no"><a rel="nofollow" class="external text" href="https://www.whocc.no/atc_ddd_index/?code=L03AX14">WHO</a></span>) <a href="/wiki/ATC_code_V04" title="ATC code V04">V04CG03</a> (<span title="www.whocc.no"><a rel="nofollow" class="external text" href="https://www.whocc.no/atc_ddd_index/?code=V04CG03">WHO</a></span>) (phosphate) </td></tr> <tr> <td colspan="2" style="text-align:left; background:#f8eaba; border:1px solid #a2a9b1;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">Except where otherwise noted, data are given for materials in their <a href="/wiki/Standard_state" title="Standard state">standard state</a> (at 25 °C [77 °F], 100 kPa).</div> <div style="margin-top: 0.3em;"><div style="text-align:center;"><span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/12px-Yes_check.svg.png" decoding="async" width="12" height="12" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/18px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/24px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span> <span class="reflink plainlinks nourlexpansion"><a class="external text" href="https://en.wikipedia.org/w/index.php?title=Special:ComparePages&rev1=443858090&page2=Histamine">verify</a></span> (<a href="/wiki/Wikipedia:WikiProject_Chemicals/Chembox_validation" title="Wikipedia:WikiProject Chemicals/Chembox validation">what is</a> <sup><span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span><span typeof="mw:File"><span><img alt="☒" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/7px-X_mark.svg.png" decoding="async" width="7" height="8" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/11px-X_mark.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/14px-X_mark.svg.png 2x" data-file-width="525" data-file-height="600" /></span></span><span style="display:none">N</span></sup> ?) </div></div> <div style="margin-top: 0.3em; text-align: center;"><a href="/wiki/Wikipedia:Chemical_infobox#References" title="Wikipedia:Chemical infobox">Infobox references</a></div> </td></tr> </tbody></table><div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Chemical compound</div> <p><b>Histamine</b> is an organic <a href="/wiki/Nitrogen" title="Nitrogen">nitrogenous</a> compound involved in local <a href="/wiki/Immune_system" title="Immune system">immune responses communication</a>, as well as regulating <a href="/wiki/Physiology" title="Physiology">physiological functions</a> in the <a href="/wiki/Gastrointestinal_tract" title="Gastrointestinal tract">gut</a> and acting as a <a href="/wiki/Neurotransmitter" title="Neurotransmitter">neurotransmitter</a> for the <a href="/wiki/Brain" title="Brain">brain</a>, <a href="/wiki/Spinal_cord" title="Spinal cord">spinal cord</a>, and <a href="/wiki/Uterus" title="Uterus">uterus</a>.<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><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> Discovered in 1910, histamine has been considered a local <a href="/wiki/Hormone" title="Hormone">hormone</a> (<a href="/wiki/Autacoid" title="Autacoid">autocoid</a>) because it's produced without involvement of the classic <a href="/wiki/Endocrine" class="mw-redirect" title="Endocrine">endocrine</a> <a href="/wiki/Gland" title="Gland">glands</a>; however, in recent years, histamine has been recognized as a central <a href="/wiki/Neurotransmitter" title="Neurotransmitter">neurotransmitter</a>.<sup id="cite_ref-pmid27028114_5-0" class="reference"><a href="#cite_note-pmid27028114-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> Histamine is involved in the <a href="/wiki/Inflammatory_response" class="mw-redirect" title="Inflammatory response">inflammatory response</a> and has a central role as a mediator of <a href="/wiki/Itching" class="mw-redirect" title="Itching">itching</a>.<sup id="cite_ref-andersen_6-0" class="reference"><a href="#cite_note-andersen-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> As part of an immune response to foreign <a href="/wiki/Pathogens" class="mw-redirect" title="Pathogens">pathogens</a>, histamine is produced by <a href="/wiki/Basophil" title="Basophil">basophils</a> and by <a href="/wiki/Mast_cell" title="Mast cell">mast cells</a> found in nearby <a href="/wiki/Connective_tissue" title="Connective tissue">connective tissues</a>. Histamine increases the <a href="/wiki/Semipermeable_membrane" title="Semipermeable membrane">permeability</a> of the <a href="/wiki/Capillaries" class="mw-redirect" title="Capillaries">capillaries</a> to <a href="/wiki/White_blood_cells" class="mw-redirect" title="White blood cells">white blood cells</a> and some <a href="/wiki/Protein" title="Protein">proteins</a>, to allow them to engage <a href="/wiki/Pathogen" title="Pathogen">pathogens</a> in the <a href="/wiki/Infection" title="Infection">infected</a> tissues.<sup id="cite_ref-7" class="reference"><a href="#cite_note-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> It consists of an <a href="/wiki/Imidazole" title="Imidazole">imidazole</a> ring attached to an <a href="/wiki/Ethylamine" title="Ethylamine">ethylamine</a> chain; under <a href="/wiki/Physiological_condition" title="Physiological condition">physiological conditions</a>, the <a href="/wiki/Amino_group" class="mw-redirect" title="Amino group">amino group</a> of the side-chain is <a href="/wiki/Protonated" class="mw-redirect" title="Protonated">protonated</a>. </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Properties">Properties</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Histamine&action=edit&section=1" title="Edit section: Properties"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Histamine base, obtained as a mineral oil <a href="/wiki/Mulling_(spectroscopy)" title="Mulling (spectroscopy)">mull</a>, melts at 83–84 °C.<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> Hydrochloride<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> and phosphorus<sup id="cite_ref-10" class="reference"><a href="#cite_note-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> salts form white <a href="/wiki/Hygroscopic" class="mw-redirect" title="Hygroscopic">hygroscopic</a> <a href="/wiki/Crystal" title="Crystal">crystals</a> and are easily dissolved in <a href="/wiki/Properties_of_water" title="Properties of water">water</a> or <a href="/wiki/Ethanol" title="Ethanol">ethanol</a>, but not in <a href="/wiki/Diethyl_ether" title="Diethyl ether">ether</a>. In <a href="/wiki/Aqueous_solution" title="Aqueous solution">aqueous solution</a>, the imidazole ring of histamine exists in two <a href="/wiki/Tautomer" title="Tautomer">tautomeric</a> forms, identified by which of the two nitrogen atoms is protonated. The nitrogen farther away from the side chain is the 'tele' nitrogen and is denoted by a lowercase tau sign and the nitrogen closer to the side chain is the 'pros' nitrogen and is denoted by the pi sign. The tele tautomer, <i>N<sup>τ</sup>-H</i>-histamine, is preferred in solution as compared to the pros tautomer, <i>N<sup>π</sup>-H</i>-histamine. </p> <figure class="mw-halign-center" typeof="mw:File/Thumb"><a href="/wiki/File:Histamine_tautomers.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/e/ea/Histamine_tautomers.svg/400px-Histamine_tautomers.svg.png" decoding="async" width="400" height="95" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/ea/Histamine_tautomers.svg/600px-Histamine_tautomers.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/e/ea/Histamine_tautomers.svg/800px-Histamine_tautomers.svg.png 2x" data-file-width="400" data-file-height="95" /></a><figcaption>The tele tautomer (<i>N<sup>τ</sup>-H</i>-histamine), on the left is more stable than the pros tautomer (<i>N<sup>π</sup>-H</i>-histamine) on the right.</figcaption></figure> <p>Histamine has two <a href="/wiki/Base_(chemistry)" title="Base (chemistry)">basic</a> centres, namely the <a href="/wiki/Aliphatic" class="mw-redirect" title="Aliphatic">aliphatic</a> amino group and whichever <a href="/wiki/Nitrogen" title="Nitrogen">nitrogen</a> atom of the imidazole ring does not already have a <a href="/wiki/Hydrogen" title="Hydrogen">proton</a>. Under physiological conditions, the aliphatic amino group (having a <a href="/wiki/Dissociation_constant" title="Dissociation constant">p<i>K</i></a><sub>a</sub> around 9.4) will be <a href="/wiki/Protonated" class="mw-redirect" title="Protonated">protonated</a>, whereas the second nitrogen of the imidazole ring (p<i>K</i><sub>a</sub> ≈ 5.8) will not be protonated.<sup id="cite_ref-Paiva_1970_11-0" class="reference"><a href="#cite_note-Paiva_1970-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> Thus, histamine is normally protonated to a singly charged <a href="/wiki/Cation" class="mw-redirect" title="Cation">cation</a>. Since human <a href="/wiki/Blood" title="Blood">blood</a> is slightly basic (with a normal pH range of 7.35 to 7.45) therefore the predominant form of histamine present in human blood is monoprotic at the aliphatic nitrogen. Histamine is a <a href="/wiki/Monoamine_neurotransmitter" title="Monoamine neurotransmitter">monoamine neurotransmitter</a>. </p> <div class="mw-heading mw-heading2"><h2 id="Synthesis_and_metabolism">Synthesis and metabolism</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Histamine&action=edit&section=2" title="Edit section: Synthesis and metabolism"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Histamine is derived from the <a href="/wiki/Decarboxylation" title="Decarboxylation">decarboxylation</a> of the <a href="/wiki/Amino_acid" title="Amino acid">amino acid</a> <a href="/wiki/Histidine" title="Histidine">histidine</a>, a reaction <a href="/wiki/Catalyst" class="mw-redirect" title="Catalyst">catalyzed</a> by the <a href="/wiki/Enzyme" title="Enzyme">enzyme</a> <a href="/wiki/L-histidine_decarboxylase" class="mw-redirect" title="L-histidine decarboxylase"><span class="smallcaps"><span style="font-variant: small-caps; text-transform: lowercase;">L</span></span>-histidine decarboxylase</a>. It is a <a href="/wiki/Hydrophilic" class="mw-redirect" title="Hydrophilic">hydrophilic</a> <a href="/wiki/Vasoactive" class="mw-redirect" title="Vasoactive">vasoactive</a> <a href="/wiki/Amine" title="Amine">amine</a>. </p> <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/433px-Histidine_decarboxylase.svg.png" decoding="async" width="433" height="123" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/b/b7/Histidine_decarboxylase.svg/650px-Histidine_decarboxylase.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/b/b7/Histidine_decarboxylase.svg/866px-Histidine_decarboxylase.svg.png 2x" data-file-width="512" data-file-height="145" /></a><figcaption>Conversion of <a href="/wiki/Histidine" title="Histidine">histidine</a> to histamine by <a href="/wiki/Histidine_decarboxylase" title="Histidine decarboxylase">histidine decarboxylase</a></figcaption></figure> <p>Once formed, histamine is either stored or rapidly inactivated by its primary <a href="/wiki/Degradative_enzyme" title="Degradative enzyme">degradative enzymes</a>, <a href="/wiki/Histamine-N-methyltransferase" class="mw-redirect" title="Histamine-N-methyltransferase">histamine-<i>N</i>-methyltransferase</a> or <a href="/wiki/Diamine_oxidase" title="Diamine oxidase">diamine oxidase</a>. In the central nervous system, histamine released into the <a href="/wiki/Synapse" title="Synapse">synapses</a> is primarily broken down by histamine-<i>N</i>-methyltransferase, while in other tissues both enzymes may play a role. Several other enzymes, including <a href="/wiki/MAO-B" class="mw-redirect" title="MAO-B">MAO-B</a> and <a href="/wiki/ALDH2" title="ALDH2">ALDH2</a>, further process the immediate metabolites of histamine for excretion or recycling. </p><p>Bacteria also are capable of producing histamine using <a href="/wiki/Histidine_decarboxylase" title="Histidine decarboxylase">histidine decarboxylase</a> enzymes unrelated to those found in animals. A non-infectious form of foodborne disease, <a href="/wiki/Scombroid_poisoning" class="mw-redirect" title="Scombroid poisoning">scombroid poisoning</a>, is due to histamine production by bacteria in spoiled food, particularly fish. Fermented foods and beverages naturally contain small quantities of histamine due to a similar conversion performed by fermenting bacteria or yeasts. <a href="/wiki/Sake" title="Sake">Sake</a> contains histamine in the 20–40 mg/L range; <a href="/wiki/Wine" title="Wine">wines</a> contain it in the 2–10 mg/L range.<sup id="cite_ref-pmid17892274_12-0" class="reference"><a href="#cite_note-pmid17892274-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Storage_and_release">Storage and release</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Histamine&action=edit&section=3" title="Edit section: Storage and release"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:SMCpolyhydroxysmall.jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a0/SMCpolyhydroxysmall.jpg/220px-SMCpolyhydroxysmall.jpg" decoding="async" width="220" height="170" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a0/SMCpolyhydroxysmall.jpg/330px-SMCpolyhydroxysmall.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a0/SMCpolyhydroxysmall.jpg/440px-SMCpolyhydroxysmall.jpg 2x" data-file-width="885" data-file-height="682" /></a><figcaption>Mast cells.</figcaption></figure> <p>Most histamine in the body is generated in granules in <a href="/wiki/Mast_cells" class="mw-redirect" title="Mast cells">mast cells</a> and in white blood cells (leukocytes) called <a href="/wiki/Basophils" class="mw-redirect" title="Basophils">basophils</a>. Mast cells are especially numerous at sites of potential injury – the nose, mouth, and feet, internal body surfaces, and blood vessels. Non-mast cell histamine is found in several tissues, including the <a href="/wiki/Hypothalamus" title="Hypothalamus">hypothalamus</a> region of the <a href="/wiki/Brain" title="Brain">brain</a>, where it functions as a neurotransmitter. Another important site of histamine storage and release is the <a href="/wiki/Enterochromaffin-like_cell" title="Enterochromaffin-like cell">enterochromaffin-like (ECL) cell</a> of the <a href="/wiki/Stomach" title="Stomach">stomach</a>. </p><p>The most important pathophysiologic mechanism of mast cell and basophil histamine release is <a href="/wiki/Immune_system" title="Immune system">immunologic</a>. These cells, if sensitized by <a href="/wiki/IgE" class="mw-redirect" title="IgE">IgE</a> <a href="/wiki/Antibody" title="Antibody">antibodies</a> attached to their <a href="/wiki/Cell_membrane" title="Cell membrane">membranes</a>, <a href="/wiki/Degranulation" title="Degranulation">degranulate</a> when exposed to the appropriate <a href="/wiki/Antigen" title="Antigen">antigen</a>. Certain <a href="/wiki/Amine" title="Amine">amines</a> and <a href="/wiki/Alkaloid" title="Alkaloid">alkaloids</a>, including such drugs as <a href="/wiki/Morphine" title="Morphine">morphine</a>, and <a href="/wiki/Curare" title="Curare">curare</a> alkaloids, can displace histamine in granules and cause its release. <a href="/wiki/Antibiotic" title="Antibiotic">Antibiotics</a> like <a href="/wiki/Polymyxin" title="Polymyxin">polymyxin</a> are also found to stimulate histamine release. </p><p>Histamine release occurs when allergens bind to mast-cell-bound IgE antibodies. Reduction of IgE overproduction may lower the likelihood of allergens finding sufficient free IgE to trigger a mast-cell-release of histamine. </p> <div class="mw-heading mw-heading2"><h2 id="Degradation">Degradation</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Histamine&action=edit&section=4" title="Edit section: Degradation"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Histamine is released by mast cells as an immune response and is later degraded primarily by two enzymes: <a href="/wiki/Diamine_oxidase" title="Diamine oxidase">diamine oxidase</a> (DAO), coded by AOC1 genes, and <a href="/wiki/Histamine-N-methyltransferase" class="mw-redirect" title="Histamine-N-methyltransferase">histamine-N-methyltransferase</a> (HNMT), coded by the HNMT gene. The presence of <a href="/wiki/Single-nucleotide_polymorphism" title="Single-nucleotide polymorphism">single nucleotide polymorphisms</a> (SNPs) at these genes are associated with a wide variety of disorders, from <a href="/wiki/Ulcerative_colitis" title="Ulcerative colitis">ulcerative colitis</a> to <a href="/wiki/Autism_spectrum" class="mw-redirect" title="Autism spectrum">autism spectrum disorder</a> (ASD).<sup id="cite_ref-Altered_expression_of_histamine_sig_13-0" class="reference"><a href="#cite_note-Altered_expression_of_histamine_sig-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup> Histamine degradation is crucial to the prevention of allergic reactions to otherwise harmless substances. </p><p>DAO is typically expressed in <a href="/wiki/Epithelium" title="Epithelium">epithelial cells</a> at the tip of the <a href="/wiki/Intestinal_villus" title="Intestinal villus">villus</a> of the small intestine mucosa.<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> Reduced DAO activity is associated with gastrointestinal disorders and widespread food intolerances. This is due to an increase in histamine absorption through <a href="/wiki/Enterocyte" title="Enterocyte">enterocytes</a>, which increases histamine concentration in the bloodstream.<sup id="cite_ref-Histamine_N-Methyltransferase_i_15-0" class="reference"><a href="#cite_note-Histamine_N-Methyltransferase_i-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup> One study found that <a href="/wiki/Migraine" title="Migraine">migraine</a> patients with <a href="/wiki/Non-celiac_gluten_sensitivity" title="Non-celiac gluten sensitivity">gluten sensitivity</a> were positively correlated with having lower DAO serum levels.<sup id="cite_ref-16" class="reference"><a href="#cite_note-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup> Low DAO activity can have more severe consequences as mutations in the ABP1 alleles of the AOC1 gene have been associated with ulcerative colitis.<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> <a href="/wiki/Zygosity" title="Zygosity">Heterozygous or homozygous</a> recessive genotypes at the rs2052129, rs2268999, rs10156191 and rs1049742 <a href="/wiki/Allele" title="Allele">alleles</a> increased the risk for reduced DAO activity.<sup id="cite_ref-18" class="reference"><a href="#cite_note-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup> People with genotypes for reduced DAO activity can avoid foods high in histamine, such as alcohol, fermented foods, and aged foods, to attenuate any allergic reactions. Additionally, they should be aware whether any <a href="/wiki/Probiotic" title="Probiotic">probiotics</a> they are taking contain any histamine-producing strains and consult with their doctor to receive proper support <sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This implicitly assumes that digested histamine can enter the bloodstream, which hasn't been established in this section. (September 2023)">citation needed</span></a></i>]</sup>. </p><p>HNMT is expressed in the <a href="/wiki/Central_nervous_system" title="Central nervous system">central nervous system</a>, where deficiencies have been shown to lead to aggressive behavior and abnormal sleep-wake cycles in mice.<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> Since brain histamine as a neurotransmitter regulates a number of neurophysiological functions, emphasis has been placed on the development of drugs to target histamine regulation. Yoshikawa et al. explores how the C314T, A939G, G179A, and T632C polymorphisms all impact HNMT enzymatic activity and the pathogenesis of various neurological disorders.<sup id="cite_ref-Histamine_N-Methyltransferase_i_15-1" class="reference"><a href="#cite_note-Histamine_N-Methyltransferase_i-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup> These mutations can have either a positive or negative impact. Some patients with <a href="/wiki/Attention_deficit_hyperactivity_disorder" title="Attention deficit hyperactivity disorder">ADHD</a> have been shown to exhibit exacerbated symptoms in response to food additives and preservatives, due in part to histamine release. In a <a href="/wiki/Blinded_experiment" title="Blinded experiment">double-blind</a> placebo-controlled crossover trial, children with ADHD who responded with aggravated symptoms after consuming a challenge beverage were more likely to have HNMT polymorphisms at T939C and Thr105Ile.<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> Histamine's role in neuroinflammation and cognition has made it a target of study for many neurological disorders, including autism spectrum disorder (ASD). De novo deletions in the HNMT gene have also been associated with ASD.<sup id="cite_ref-Altered_expression_of_histamine_sig_13-1" class="reference"><a href="#cite_note-Altered_expression_of_histamine_sig-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup> </p><p>Mast cells serve an important immunological role by defending the body from <a href="/wiki/Antigen" title="Antigen">antigens</a> and maintaining <a href="/wiki/Homeostasis" title="Homeostasis">homeostasis</a> in the <a href="/wiki/Gut_microbiota" title="Gut microbiota">gut microbiome</a>. They act as an alarm to trigger inflammatory responses by the immune system. Their presence in the digestive system enables them to serve as an early barrier to <a href="/wiki/Pathogen" title="Pathogen">pathogens</a> entering the body. People who suffer from widespread sensitivities and allergic reactions may have <a href="/wiki/Mast_cell_activation_syndrome" title="Mast cell activation syndrome">mast cell activation syndrome</a> (MCAS), in which excessive amounts of histamine are released from <a href="/wiki/Mast_cell" title="Mast cell">mast cells</a>, and cannot be properly degraded. The abnormal release of histamine can be caused by either dysfunctional internal signals from defective mast cells or by the development of clonal mast cell populations through mutations occurring in the <a href="/wiki/Tyrosine_kinase" title="Tyrosine kinase">tyrosine kinase</a> <a href="/wiki/KIT_(gene)" title="KIT (gene)">Kit</a>.<sup id="cite_ref-:0_21-0" class="reference"><a href="#cite_note-:0-21"><span class="cite-bracket">[</span>21<span class="cite-bracket">]</span></a></sup> In such cases, the body may not be able to produce sufficient degradative enzymes to properly eliminate the excess histamine. Since MCAS is symptomatically characterized as such a broad disorder, it is difficult to diagnose and can be mislabeled as a variety of diseases, including <a href="/wiki/Irritable_bowel_syndrome" title="Irritable bowel syndrome">irritable bowel syndrome</a> and <a href="/wiki/Fibromyalgia" title="Fibromyalgia">fibromyalgia</a>.<sup id="cite_ref-:0_21-1" class="reference"><a href="#cite_note-:0-21"><span class="cite-bracket">[</span>21<span class="cite-bracket">]</span></a></sup> </p><p>Histamine is often explored as a potential cause for diseases related to hyper-responsiveness of the immune system. In patients with <a href="/wiki/Asthma" title="Asthma">asthma</a>, abnormal histamine receptor activation in the lungs is associated with <a href="/wiki/Bronchospasm" title="Bronchospasm">bronchospasm</a>, airway obstruction, and production of excess mucus. Mutations in histamine degradation are more common in patients with a combination of asthma and allergen hypersensitivity than in those with just asthma. The HNMT-464 TT and HNMT-1639 TT <a href="/wiki/Polymorphism_(biology)" title="Polymorphism (biology)">polymorphisms</a> are significantly more common among children with allergic asthma, the latter of which is overrepresented in African-American children.<sup id="cite_ref-22" class="reference"><a href="#cite_note-22"><span class="cite-bracket">[</span>22<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Mechanism_of_action">Mechanism of action</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Histamine&action=edit&section=5" title="Edit section: Mechanism of action"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>In humans, histamine exerts its effects primarily by binding to <a href="/wiki/G_protein-coupled_receptor" title="G protein-coupled receptor">G protein-coupled</a> <a href="/wiki/Histamine_receptors" class="mw-redirect" title="Histamine receptors">histamine receptors</a>, designated H<sub>1</sub> through H<sub>4</sub>.<sup id="cite_ref-Histamine_receptors_23-0" class="reference"><a href="#cite_note-Histamine_receptors-23"><span class="cite-bracket">[</span>23<span class="cite-bracket">]</span></a></sup> As of 2015<sup class="plainlinks noexcerpt noprint asof-tag update" style="display:none;"><a class="external text" href="https://en.wikipedia.org/w/index.php?title=Histamine&action=edit">[update]</a></sup>, histamine is believed to activate ligand-gated chloride channels in the brain and intestinal epithelium.<sup id="cite_ref-Histamine_receptors_23-1" class="reference"><a href="#cite_note-Histamine_receptors-23"><span class="cite-bracket">[</span>23<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-FGID_mast_cell_24-0" class="reference"><a href="#cite_note-FGID_mast_cell-24"><span class="cite-bracket">[</span>24<span class="cite-bracket">]</span></a></sup> </p> <table class="wikitable"> <caption>Biological targets of histamine in the human body </caption> <tbody><tr> <th><span class="nowrap"><a href="/wiki/G-protein_coupled_receptor" class="mw-redirect" title="G-protein coupled receptor">G-protein coupled receptor</a></span></th> <th>Location</th> <th>Function</th> <th><small>Sources</small> </th></tr> <tr> <td style="text-align:center"><a href="/wiki/Histamine_H1_receptor" title="Histamine H1 receptor"><span class="nowrap">Histamine H<sub>1</sub></span> receptor</a> </td> <td style="vertical-align:top"> <p> • <b>CNS</b>: Expressed on the <a href="/wiki/Dendrite" title="Dendrite">dendrites</a> of the output neurons of the histaminergic <a href="/wiki/Tuberomammillary_nucleus" title="Tuberomammillary nucleus">tuberomammillary nucleus</a>, which projects to the <a href="/wiki/Dorsal_raphe_nucleus" title="Dorsal raphe nucleus">dorsal raphe</a>, <a href="/wiki/Locus_coeruleus" title="Locus coeruleus">locus coeruleus</a>, and additional structures.<br />  • <b>Periphery</b>: <a href="/wiki/Smooth_muscle" title="Smooth muscle">Smooth muscle</a>, <a href="/wiki/Endothelium" title="Endothelium">endothelium</a>, <a href="/wiki/Mast_cells" class="mw-redirect" title="Mast cells">mast cells</a>, sensory nerves </p> </td> <td style="vertical-align:top"> <p> •  <b>CNS</b>: <a href="/wiki/Sleep-wake_cycle" class="mw-redirect" title="Sleep-wake cycle">Sleep-wake cycle</a> (promotes wakefulness), <a href="/wiki/Body_temperature" class="mw-redirect" title="Body temperature">body temperature</a>, <a href="/wiki/Nociception" title="Nociception">nociception</a>, <a href="/wiki/Endocrine_system" title="Endocrine system">endocrine homeostasis</a>, regulates <a href="/wiki/Appetite" title="Appetite">appetite</a>, involved in cognition<br />  • <b>Periphery</b>: Causes <a href="/wiki/Bronchoconstriction" title="Bronchoconstriction">bronchoconstriction</a>, bronchial <a href="/wiki/Smooth_muscle" title="Smooth muscle">smooth muscle</a> contraction, urinary bladder contractions, <a href="/wiki/Vasodilation" title="Vasodilation">vasodilation</a>, promotes hypernociception (<a href="/wiki/Visceral_hypersensitivity" class="mw-redirect" title="Visceral hypersensitivity">visceral hypersensitivity</a>), involved in <a href="/wiki/Itch" title="Itch">itch perception</a> and <a href="/wiki/Urticaria" class="mw-redirect" title="Urticaria">urticaria</a>. </p> </td> <td><sup id="cite_ref-Histamine_receptors_23-2" class="reference"><a href="#cite_note-Histamine_receptors-23"><span class="cite-bracket">[</span>23<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-FGID_mast_cell_24-1" class="reference"><a href="#cite_note-FGID_mast_cell-24"><span class="cite-bracket">[</span>24<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-25" class="reference"><a href="#cite_note-25"><span class="cite-bracket">[</span>25<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Urinary_Bladder_26-0" class="reference"><a href="#cite_note-Urinary_Bladder-26"><span class="cite-bracket">[</span>26<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Histamine_mediated_autocrine_signal_27-0" class="reference"><a href="#cite_note-Histamine_mediated_autocrine_signal-27"><span class="cite-bracket">[</span>27<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td style="text-align:center"><a href="/wiki/Histamine_H2_receptor" title="Histamine H2 receptor"><span class="nowrap">Histamine H<sub>2</sub></span> receptor</a> </td> <td style="vertical-align:top"> <p> • <b>CNS</b>: <a href="/wiki/Dorsal_striatum" class="mw-redirect" title="Dorsal striatum">Dorsal striatum</a> (<a href="/wiki/Caudate_nucleus" title="Caudate nucleus">caudate nucleus</a> and <a href="/wiki/Putamen" title="Putamen">putamen</a>), <a href="/wiki/Cerebral_cortex" title="Cerebral cortex">cerebral cortex</a> (external layers), <a href="/wiki/Hippocampal_formation" title="Hippocampal formation">hippocampal formation</a>, <a href="/wiki/Dentate_nucleus" title="Dentate nucleus">dentate nucleus</a> of the <a href="/wiki/Cerebellum" title="Cerebellum">cerebellum</a><br />  • <b>Periphery</b>: Located on <a href="/wiki/Parietal_cells" class="mw-redirect" title="Parietal cells">parietal cells</a>, <a href="/wiki/Vascular_smooth_muscle_cells" class="mw-redirect" title="Vascular smooth muscle cells">vascular smooth muscle cells</a>, <a href="/wiki/Neutrophils" class="mw-redirect" title="Neutrophils">neutrophils</a>, <a href="/wiki/Mast_cells" class="mw-redirect" title="Mast cells">mast cells</a>, as well as on cells in the <a href="/wiki/Heart" title="Heart">heart</a> and <a href="/wiki/Uterus" title="Uterus">uterus</a> </p> </td> <td style="vertical-align:top"> <p> • <b>CNS</b>: Not established (note: most known H<sub>2</sub> receptor ligands are unable to cross the <a href="/wiki/Blood%E2%80%93brain_barrier" title="Blood–brain barrier">blood–brain barrier</a> in sufficient concentrations to allow for neuropsychological and behavioral testing)<br />  • <b>Periphery</b>: Primarily involved in vasodilation and stimulation of <a href="/wiki/Gastric_acid" title="Gastric acid">gastric acid</a> secretion. Urinary bladder relaxation. Modulates gastrointestinal function. </p> </td> <td><sup id="cite_ref-Histamine_receptors_23-3" class="reference"><a href="#cite_note-Histamine_receptors-23"><span class="cite-bracket">[</span>23<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-FGID_mast_cell_24-2" class="reference"><a href="#cite_note-FGID_mast_cell-24"><span class="cite-bracket">[</span>24<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-IUPHAR_HRH2_28-0" class="reference"><a href="#cite_note-IUPHAR_HRH2-28"><span class="cite-bracket">[</span>28<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Histamine_mediated_autocrine_signal_27-1" class="reference"><a href="#cite_note-Histamine_mediated_autocrine_signal-27"><span class="cite-bracket">[</span>27<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td style="text-align:center"><a href="/wiki/Histamine_H3_receptor" title="Histamine H3 receptor"><span class="nowrap">Histamine H<sub>3</sub></span> receptor</a> </td> <td>Located in the <a href="/wiki/Central_nervous_system" title="Central nervous system">central nervous system</a> and to a lesser extent <a href="/wiki/Peripheral_nervous_system" title="Peripheral nervous system">peripheral nervous system</a> tissue </td> <td><a href="/wiki/Autoreceptor" title="Autoreceptor">Autoreceptor</a> and <a href="/wiki/Heteroreceptor" title="Heteroreceptor">heteroreceptor</a> functions: decreased <a href="/wiki/Neurotransmitter" title="Neurotransmitter">neurotransmitter</a> release of histamine, <a href="/wiki/Acetylcholine" title="Acetylcholine">acetylcholine</a>, <a href="/wiki/Norepinephrine" title="Norepinephrine">norepinephrine</a>, <a href="/wiki/Serotonin" title="Serotonin">serotonin</a>. Modulates nociception, gastric acid secretion, and food intake. </td> <td><sup id="cite_ref-Histamine_receptors_23-4" class="reference"><a href="#cite_note-Histamine_receptors-23"><span class="cite-bracket">[</span>23<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td style="text-align:center"><a href="/wiki/Histamine_H4_receptor" title="Histamine H4 receptor"><span class="nowrap">Histamine H<sub>4</sub></span> receptor</a> </td> <td>Located primarily on <a href="/wiki/Basophil" title="Basophil">basophils</a> and in the <a href="/wiki/Bone_marrow" title="Bone marrow">bone marrow</a>. It is also expressed in the <a href="/wiki/Thymus" title="Thymus">thymus</a>, <a href="/wiki/Small_intestine" title="Small intestine">small intestine</a>, <a href="/wiki/Spleen" title="Spleen">spleen</a>, and <a href="/wiki/Colon_(anatomy)" class="mw-redirect" title="Colon (anatomy)">colon</a>. </td> <td>Plays a role in mast cell <a href="/wiki/Chemotaxis" title="Chemotaxis">chemotaxis</a>, itch perception, cytokine production and secretion, and visceral hypersensitivity. Other putative functions (e.g., inflammation, allergy, cognition, etc.) have not been fully characterized.</td> <td><sup id="cite_ref-Histamine_receptors_23-5" class="reference"><a href="#cite_note-Histamine_receptors-23"><span class="cite-bracket">[</span>23<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <th scope="col"><a href="/wiki/Ligand-gated_ion_channel" title="Ligand-gated ion channel">Ligand-gated ion channel</a></th> <th>Location</th> <th>Function</th> <th><small>Sources</small> </th></tr> <tr> <td style="text-align:center"><span class="nowrap">Histamine-gated</span> <span class="nowrap"><a href="/wiki/Chloride_channel" title="Chloride channel">chloride channel</a></span> </td> <td>Putatively: CNS (hypothalamus, thalamus) and intestinal epithelium </td> <td>Brain: Produces fast <a href="/wiki/Inhibitory_postsynaptic_potential" title="Inhibitory postsynaptic potential">inhibitory postsynaptic potentials</a><br /> Intestinal epithelium: chloride secretion (associated with <a href="/wiki/Secretory_diarrhea" class="mw-redirect" title="Secretory diarrhea">secretory diarrhea</a>) </td> <td><sup id="cite_ref-Histamine_receptors_23-6" class="reference"><a href="#cite_note-Histamine_receptors-23"><span class="cite-bracket">[</span>23<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-FGID_mast_cell_24-3" class="reference"><a href="#cite_note-FGID_mast_cell-24"><span class="cite-bracket">[</span>24<span class="cite-bracket">]</span></a></sup> </td></tr></tbody></table> <div class="mw-heading mw-heading2"><h2 id="Roles_in_the_body">Roles in the body</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Histamine&action=edit&section=6" title="Edit section: Roles in the body"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Although histamine is small compared to other biological molecules (containing only 17 atoms), it plays an important role in the body. It is known to be involved in 23 different physiological functions. Histamine is known to be involved in many physiological functions because of its chemical properties that allow it to be versatile in binding. It is Coulombic (able to carry a charge), conformational, and flexible. This allows it to interact and bind more easily.<sup id="cite_ref-Noszal,_B._pp_15-28_29-0" class="reference"><a href="#cite_note-Noszal,_B._pp_15-28-29"><span class="cite-bracket">[</span>29<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Vasodilation_and_fall_in_blood_pressure">Vasodilation and fall in blood pressure</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Histamine&action=edit&section=7" title="Edit section: Vasodilation and fall in blood pressure"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>It has been known for more than one hundred years that an intravenous injection of histamine causes a fall in the blood pressure.<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> The underlying mechanism concerns both vascular hyperpermeability and vasodilation. Histamine binding to endothelial cells causes them to contract, thus increasing vascular leak. It also stimulates synthesis and release of various vascular smooth muscle cell relaxants, such as <a href="/wiki/Nitric_oxide" title="Nitric oxide">nitric oxide</a>, <a href="/wiki/Endothelium-derived_hyperpolarizing_factor" title="Endothelium-derived hyperpolarizing factor">endothelium-derived hyperpolarizing factors</a> and other compounds, resulting in blood vessel dilation.<sup id="cite_ref-Abbas_et_al_(2018)._Cellular_and_molecular_immunology_p.447_31-0" class="reference"><a href="#cite_note-Abbas_et_al_(2018)._Cellular_and_molecular_immunology_p.447-31"><span class="cite-bracket">[</span>31<span class="cite-bracket">]</span></a></sup> These two mechanisms play a key role in the pathophysiology of <a href="/wiki/Anaphylaxis#Immunologic" title="Anaphylaxis">anaphylaxis</a>. </p> <div class="mw-heading mw-heading3"><h3 id="Effects_on_nasal_mucous_membrane">Effects on nasal mucous membrane <span class="anchor" id="Effects_on_Nasal_Mucosa"></span></h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Histamine&action=edit&section=8" title="Edit section: Effects on nasal mucous membrane"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Increased vascular permeability causes fluid to escape from capillaries into the tissues, which leads to the classic symptoms of an allergic reaction: a runny nose and watery eyes. Allergens can bind to <a href="/wiki/IgE" class="mw-redirect" title="IgE">IgE</a>-loaded <a href="/wiki/Mast_cell" title="Mast cell">mast cells</a> in the <a href="/wiki/Nasal_cavity" title="Nasal cavity">nasal cavity</a>'s <a href="/wiki/Mucous_membrane" title="Mucous membrane">mucous membranes</a>. This can lead to three clinical responses:<sup id="cite_ref-32" class="reference"><a href="#cite_note-32"><span class="cite-bracket">[</span>32<span class="cite-bracket">]</span></a></sup> </p> <ol><li>sneezing due to histamine-associated sensory neural stimulation</li> <li>hyper-<a href="/wiki/Secretion" title="Secretion">secretion</a> from glandular tissue</li> <li>nasal congestion due to vascular engorgement associated with <a href="/wiki/Vasodilation" title="Vasodilation">vasodilation</a> and increased <a href="/wiki/Capillary" title="Capillary">capillary</a> <a href="/wiki/Permeation" title="Permeation">permeability</a></li></ol> <div class="mw-heading mw-heading3"><h3 id="Sleep-wake_regulation">Sleep-wake regulation</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Histamine&action=edit&section=9" title="Edit section: Sleep-wake regulation"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">Further information: <a href="/wiki/Ascending_reticular_activating_system" class="mw-redirect" title="Ascending reticular activating system">Ascending reticular activating system</a></div> <p>Histamine is a <a href="/wiki/Neurotransmitter" title="Neurotransmitter">neurotransmitter</a> that is released from histaminergic <a href="/wiki/Neuron" title="Neuron">neurons</a> which project out of the <a href="/wiki/Mammal" title="Mammal">mammalian</a> <a href="/wiki/Hypothalamus" title="Hypothalamus">hypothalamus</a>. The cell bodies of these neurons are located in a portion of the posterior <a href="/wiki/Hypothalamus" title="Hypothalamus">hypothalamus</a> known as the <a href="/wiki/Tuberomammillary_nucleus" title="Tuberomammillary nucleus">tuberomammillary nucleus</a> (TMN). The histamine neurons in this region comprise the <a href="/wiki/Neurotransmitter#Histamine" title="Neurotransmitter">brain's histamine system</a>, which projects widely throughout the brain and includes <a href="/wiki/Axonal_projection" class="mw-redirect" title="Axonal projection">axonal projections</a> to the <a href="/wiki/Brain" title="Brain">cortex</a>, <a href="/wiki/Medial_forebrain_bundle" title="Medial forebrain bundle">medial forebrain bundle</a>, other hypothalamic nuclei, medial septum, the nucleus of the diagonal band, ventral tegmental area, amygdala, striatum, substantia nigra, hippocampus, thalamus and elsewhere.<sup id="cite_ref-33" class="reference"><a href="#cite_note-33"><span class="cite-bracket">[</span>33<span class="cite-bracket">]</span></a></sup> The histamine neurons in the TMN are involved in regulating the <a href="/wiki/Sleep-wake_cycle" class="mw-redirect" title="Sleep-wake cycle">sleep-wake cycle</a> and promote arousal when activated.<sup id="cite_ref-34" class="reference"><a href="#cite_note-34"><span class="cite-bracket">[</span>34<span class="cite-bracket">]</span></a></sup> The <a href="/wiki/Neural_firing_rate" class="mw-redirect" title="Neural firing rate">neural firing rate</a> of histamine neurons in the TMN is strongly <a href="/wiki/Positively_correlated" class="mw-redirect" title="Positively correlated">positively correlated</a> with an individual's state of arousal. These neurons fire rapidly during periods of wakefulness, fire more slowly during periods of relaxation/tiredness, and stop firing altogether during <a href="/wiki/Rapid_eye_movement_sleep" title="Rapid eye movement sleep">REM</a> and <a href="/wiki/NREM" class="mw-redirect" title="NREM">NREM</a> (non-REM) sleep.<sup id="cite_ref-35" class="reference"><a href="#cite_note-35"><span class="cite-bracket">[</span>35<span class="cite-bracket">]</span></a></sup> </p><p>First-generation <a href="/wiki/H1_antagonist" title="H1 antagonist">H<sub>1</sub> antihistamines</a> (i.e., <a href="/wiki/Receptor_antagonist" title="Receptor antagonist">antagonists</a> of <a href="/wiki/HRH1" class="mw-redirect" title="HRH1">histamine receptor H<sub>1</sub></a>) are capable of crossing the <a href="/wiki/Blood%E2%80%93brain_barrier" title="Blood–brain barrier">blood–brain barrier</a> and produce <a href="/wiki/Drowsiness" class="mw-redirect" title="Drowsiness">drowsiness</a> by antagonizing histamine H<sub>1</sub> receptors in the tuberomammillary nucleus. The newer class of <a href="/wiki/H1_antagonist#Second-generation" title="H1 antagonist">second-generation H<sub>1</sub> antihistamines</a> do not readily permeate the blood–brain barrier and thus are less likely to cause sedation, although individual reactions, concomitant medications and dosage may increase the likelihood of a sedating effect. In contrast, <a href="/wiki/H3_receptor_antagonist" title="H3 receptor antagonist">histamine H<sub>3</sub> receptor antagonists</a> increase wakefulness. Similar to the sedative effect of first-generation H<sub>1</sub> antihistamines, an inability to maintain <a href="/wiki/Alertness" title="Alertness">vigilance</a> can occur from the inhibition of histamine biosynthesis or the loss (i.e., degeneration or destruction) of histamine-releasing neurons in the TMN. </p> <div class="mw-heading mw-heading3"><h3 id="Gastric_acid_release">Gastric acid release</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Histamine&action=edit&section=10" title="Edit section: Gastric acid release"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><a href="/wiki/Enterochromaffin-like_cell" title="Enterochromaffin-like cell">Enterochromaffin-like cells</a> in the stomach release histamine, stimulating parietal cells via H<sub>2</sub> receptors. This triggers carbon dioxide and water uptake from the blood, converted to carbonic acid by carbonic anhydrase. The acid dissociates into hydrogen and bicarbonate ions within the parietal cell. Bicarbonate returns to the bloodstream, while hydrogen is pumped into the stomach lumen. Histamine release ceases as stomach pH decreases.<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Identifying_reliable_sources_(medicine)" title="Wikipedia:Identifying reliable sources (medicine)"><span title="Material near this tag needs references to reliable medical sources. (March 2024)">medical citation needed</span></a></i>]</sup> <a href="/wiki/Receptor_antagonist" title="Receptor antagonist">Antagonist</a> molecules, such as <a href="/wiki/Ranitidine" title="Ranitidine">ranitidine</a> or <a href="/wiki/Famotidine" title="Famotidine">famotidine</a>, block the H<sub>2</sub> receptor and prevent histamine from binding, causing decreased hydrogen ion secretion.<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Identifying_reliable_sources_(medicine)" title="Wikipedia:Identifying reliable sources (medicine)"><span title="Material near this tag needs references to reliable medical sources. (March 2024)">medical citation needed</span></a></i>]</sup> </p> <div class="mw-heading mw-heading3"><h3 id="Protective_effects">Protective effects</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Histamine&action=edit&section=11" title="Edit section: Protective effects"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>While histamine has stimulatory effects upon neurons, it also has suppressive ones that protect against the susceptibility to <a href="/wiki/Convulsion" title="Convulsion">convulsion</a>, drug sensitization, <a href="/wiki/Denervation_supersensitivity" title="Denervation supersensitivity">denervation supersensitivity</a>, ischemic lesions and stress.<sup id="cite_ref-36" class="reference"><a href="#cite_note-36"><span class="cite-bracket">[</span>36<span class="cite-bracket">]</span></a></sup> It has also been suggested that histamine controls the mechanisms by which memories and learning are forgotten.<sup id="cite_ref-37" class="reference"><a href="#cite_note-37"><span class="cite-bracket">[</span>37<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Erection_and_sexual_function">Erection and sexual function</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Histamine&action=edit&section=12" title="Edit section: Erection and sexual function"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1251242444">.mw-parser-output .ambox{border:1px solid #a2a9b1;border-left:10px solid #36c;background-color:#fbfbfb;box-sizing:border-box}.mw-parser-output .ambox+link+.ambox,.mw-parser-output .ambox+link+style+.ambox,.mw-parser-output .ambox+link+link+.ambox,.mw-parser-output .ambox+.mw-empty-elt+link+.ambox,.mw-parser-output .ambox+.mw-empty-elt+link+style+.ambox,.mw-parser-output .ambox+.mw-empty-elt+link+link+.ambox{margin-top:-1px}html body.mediawiki .mw-parser-output .ambox.mbox-small-left{margin:4px 1em 4px 0;overflow:hidden;width:238px;border-collapse:collapse;font-size:88%;line-height:1.25em}.mw-parser-output .ambox-speedy{border-left:10px solid #b32424;background-color:#fee7e6}.mw-parser-output .ambox-delete{border-left:10px solid #b32424}.mw-parser-output .ambox-content{border-left:10px solid #f28500}.mw-parser-output .ambox-style{border-left:10px solid #fc3}.mw-parser-output .ambox-move{border-left:10px solid #9932cc}.mw-parser-output .ambox-protection{border-left:10px solid #a2a9b1}.mw-parser-output .ambox .mbox-text{border:none;padding:0.25em 0.5em;width:100%}.mw-parser-output .ambox .mbox-image{border:none;padding:2px 0 2px 0.5em;text-align:center}.mw-parser-output .ambox .mbox-imageright{border:none;padding:2px 0.5em 2px 0;text-align:center}.mw-parser-output .ambox .mbox-empty-cell{border:none;padding:0;width:1px}.mw-parser-output .ambox .mbox-image-div{width:52px}@media(min-width:720px){.mw-parser-output .ambox{margin:0 10%}}@media print{body.ns-0 .mw-parser-output .ambox{display:none!important}}</style><table class="box-Missing_information plainlinks metadata ambox ambox-content" role="presentation"><tbody><tr><td class="mbox-image"><div class="mbox-image-div"><span typeof="mw:File"><a href="/wiki/File:Wiki_letter_w.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/en/thumb/6/6c/Wiki_letter_w.svg/44px-Wiki_letter_w.svg.png" decoding="async" width="44" height="44" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/6/6c/Wiki_letter_w.svg/66px-Wiki_letter_w.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/6/6c/Wiki_letter_w.svg/88px-Wiki_letter_w.svg.png 2x" data-file-width="44" data-file-height="44" /></a></span></div></td><td class="mbox-text"><div class="mbox-text-span">This section <b>is missing information</b> about <a href="/wiki/Female_sexual_dysfunction" class="mw-redirect" title="Female sexual dysfunction">sexual dysfunction in females</a>.<span class="hide-when-compact"> Please expand the section to include this information. Further details may exist on the <a href="/wiki/Talk:Histamine" title="Talk:Histamine">talk page</a>.</span> <span class="date-container"><i>(<span class="date">October 2023</span>)</i></span></div></td></tr></tbody></table> <p><a href="/wiki/Loss_of_libido" class="mw-redirect" title="Loss of libido">Loss of libido</a> and <a href="/wiki/Erectile_dysfunction" title="Erectile dysfunction">erectile dysfunction</a> can occur during treatment with histamine H<sub>2</sub> receptor antagonists such as <a href="/wiki/Cimetidine" title="Cimetidine">cimetidine</a>, <a href="/wiki/Ranitidine" title="Ranitidine">ranitidine</a>, and <a href="/wiki/Risperidone" title="Risperidone">risperidone</a>.<sup id="cite_ref-White_38-0" class="reference"><a href="#cite_note-White-38"><span class="cite-bracket">[</span>38<span class="cite-bracket">]</span></a></sup> The injection of histamine into the <a href="/wiki/Corpus_cavernosum_penis" title="Corpus cavernosum penis">corpus cavernosum</a> in males with psychogenic impotence produces full or partial erections in 74% of them.<sup id="cite_ref-39" class="reference"><a href="#cite_note-39"><span class="cite-bracket">[</span>39<span class="cite-bracket">]</span></a></sup> It has been suggested that H<sub>2</sub> antagonists may cause sexual dysfunction by reducing the functional binding of testosterone to its androgen receptors.<sup id="cite_ref-White_38-1" class="reference"><a href="#cite_note-White-38"><span class="cite-bracket">[</span>38<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Schizophrenia">Schizophrenia</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Histamine&action=edit&section=13" title="Edit section: Schizophrenia"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Metabolites of histamine are increased in the cerebrospinal fluid of people with <a href="/wiki/Schizophrenia" title="Schizophrenia">schizophrenia</a>, while the efficiency of H<sub>1</sub> receptor binding sites is decreased. Many atypical <a href="/wiki/Antipsychotic" title="Antipsychotic">antipsychotic</a> medications have the effect of increasing histamine production, because histamine levels seem to be imbalanced in people with that disorder.<sup id="cite_ref-40" class="reference"><a href="#cite_note-40"><span class="cite-bracket">[</span>40<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Multiple_sclerosis">Multiple sclerosis</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Histamine&action=edit&section=14" title="Edit section: Multiple sclerosis"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Histamine therapy for treatment of <a href="/wiki/Multiple_sclerosis" title="Multiple sclerosis">multiple sclerosis</a> is currently being studied. The different H receptors have been known to have different effects on the treatment of this disease. The H<sub>1</sub> and H<sub>4</sub> receptors, in one study, have been shown to be counterproductive in the treatment of MS. The H<sub>1</sub> and H<sub>4</sub> receptors are thought to increase permeability in the blood-brain barrier, thus increasing infiltration of unwanted cells in the central nervous system. This can cause inflammation, and MS symptom worsening. The H<sub>2</sub> and H<sub>3</sub> receptors are thought to be helpful when treating MS patients. Histamine has been shown to help with T-cell differentiation. This is important because in MS, the body's immune system attacks its own myelin sheaths on nerve cells (which causes loss of signaling function and eventual nerve degeneration). By helping T cells to differentiate, the T cells will be less likely to attack the body's own cells, and instead, attack invaders.<sup id="cite_ref-41" class="reference"><a href="#cite_note-41"><span class="cite-bracket">[</span>41<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Disorders">Disorders</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Histamine&action=edit&section=15" title="Edit section: Disorders"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>As an integral part of the immune system, histamine may be involved in <a href="/wiki/Immune_system_disorder" class="mw-redirect" title="Immune system disorder">immune system disorders</a><sup id="cite_ref-42" class="reference"><a href="#cite_note-42"><span class="cite-bracket">[</span>42<span class="cite-bracket">]</span></a></sup> and <a href="/wiki/Allergies" class="mw-redirect" title="Allergies">allergies</a>. <i><a href="/wiki/Mastocytosis" title="Mastocytosis">Mastocytosis</a></i> is a rare disease in which there is a proliferation of mast cells that produce excess histamine.<sup id="cite_ref-43" class="reference"><a href="#cite_note-43"><span class="cite-bracket">[</span>43<span class="cite-bracket">]</span></a></sup> </p><p><a href="/wiki/Histamine_intolerance" title="Histamine intolerance">Histamine intolerance</a> is a presumed set of adverse reactions (such as flush, itching, rhinitis, etc.) to ingested histamine in food. The mainstream theory accepts that there may exist adverse reactions to ingested histamine, but does not recognize histamine intolerance as a separate condition that can be diagnosed.<sup id="cite_ref-pmid34651098_44-0" class="reference"><a href="#cite_note-pmid34651098-44"><span class="cite-bracket">[</span>44<span class="cite-bracket">]</span></a></sup> </p><p>The role of histamine in health and disease is an area of ongoing research. For example, histamine is researched in its potential link with migraine episodes, when there is a noted elevation in the plasma concentrations of both histamine and calcitonin gene-related peptide (CGRP). These two substances are potent vasodilators, and have been demonstrated to mutually stimulate each other's release within the trigeminovascular system, a mechanism that could potentially instigate the onset of migraines. In patients with a deficiency in histamine degradation due to variants in the AOC1 gene that encodes <a href="/wiki/Diamine_oxidase" title="Diamine oxidase">diamine oxidase</a> enzyme, a diet high in histamine has been observed to trigger migraines, that suggests a potential functional relationship between exogenous histamine and CGRP, which could be instrumental in understanding the genesis of diet-induced migraines, so that the role of histamine, particularly in relation to CGRP, is a promising area of research for elucidating the mechanisms underlying migraine development and aggravation, especially relevant in the context of dietary triggers and genetic predispositions related to histamine metabolism.<sup id="cite_ref-pmid38447930_45-0" class="reference"><a href="#cite_note-pmid38447930-45"><span class="cite-bracket">[</span>45<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Measurement">Measurement</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Histamine&action=edit&section=16" title="Edit section: Measurement"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Histamine, a biogenic amine, involves many physiological functions, including the immune response, gastric acid secretion, and <a href="/wiki/Neuromodulation" title="Neuromodulation">neuromodulation</a>. However, its rapid metabolism makes it challenging to measure histamine levels directly in plasma.<sup id="cite_ref-46" class="reference"><a href="#cite_note-46"><span class="cite-bracket">[</span>46<span class="cite-bracket">]</span></a></sup> </p><p>As a solution for the rapid metabolism of histamine, the measurement of histamine and its metabolites, particularly the 1,4-methyl-imidazolacetic acid, in a 24-hour urine sample, provides an efficient alternative to histamine measurement because the values of these metabolites remain elevated for a much longer period than the histamine itself.<sup id="cite_ref-47" class="reference"><a href="#cite_note-47"><span class="cite-bracket">[</span>47<span class="cite-bracket">]</span></a></sup> </p><p>Commercial laboratories provide a <a href="/wiki/24-hour_urine" class="mw-redirect" title="24-hour urine">24-hour urine</a> sample test for 1,4-methyl-imidazolacetic acid, the metabolite of histamine. This test is a valuable tool in assessing the metabolism of histamine in the body, as direct measurement of histamine in the serum has low diagnostic value due to the specificities of histamine metabolism.<sup id="cite_ref-48" class="reference"><a href="#cite_note-48"><span class="cite-bracket">[</span>48<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-49" class="reference"><a href="#cite_note-49"><span class="cite-bracket">[</span>49<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-pmid28321587_50-0" class="reference"><a href="#cite_note-pmid28321587-50"><span class="cite-bracket">[</span>50<span class="cite-bracket">]</span></a></sup> </p><p>The urine test involves collecting all urine produced in a 24-hour period, which is then analyzed for the presence of 1,4-methyl-imidazolacetic acid. This comprehensive approach ensures a more accurate reflection of histamine metabolism over an extended period; as such, the 1,4-methyl-imidazolacetic acid urine test offered by commercial labs is currently the most reliable method to determine the rate of histamine metabolism, which may be helpful for the health care practitioners to assess individual’s health status,<sup id="cite_ref-51" class="reference"><a href="#cite_note-51"><span class="cite-bracket">[</span>51<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-52" class="reference"><a href="#cite_note-52"><span class="cite-bracket">[</span>52<span class="cite-bracket">]</span></a></sup> such as to diagnose <a href="/wiki/Interstitial_cystitis" title="Interstitial cystitis">interstitial cystitis</a>.<sup id="cite_ref-53" class="reference"><a href="#cite_note-53"><span class="cite-bracket">[</span>53<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="History">History</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Histamine&action=edit&section=17" title="Edit section: History"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The properties of histamine, then called β-imidazolylethylamine, were first described in 1910 by the British scientists <a href="/wiki/Henry_Hallett_Dale" title="Henry Hallett Dale">Henry H. Dale</a> and <a href="/wiki/Patrick_Laidlaw" title="Patrick Laidlaw">P.P. Laidlaw</a>.<sup id="cite_ref-54" class="reference"><a href="#cite_note-54"><span class="cite-bracket">[</span>54<span class="cite-bracket">]</span></a></sup> By 1913 the name <i>histamine</i> was in use, using <a href="/wiki/Classical_compound" class="mw-redirect" title="Classical compound">combining forms</a> of <i><a href="https://en.wiktionary.org/wiki/histo-#Prefix" class="extiw" title="wikt:histo-">histo-</a></i> + <i><a href="/wiki/Amine" title="Amine">amine</a></i>, yielding "tissue amine". </p><p>"H substance" or "substance H" are occasionally used in medical literature for histamine or a hypothetical histamine-like diffusible substance released in allergic reactions of skin and in the responses of tissue to inflammation. </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=Histamine&action=edit&section=18" title="Edit section: See also"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a href="/wiki/Anaphylaxis" title="Anaphylaxis">Anaphylaxis</a></li> <li><a href="/wiki/Diamine_oxidase" title="Diamine oxidase">Diamine oxidase</a></li> <li><a href="/wiki/Histamine_N-methyltransferase" title="Histamine N-methyltransferase">Histamine N-methyltransferase</a></li> <li><a href="/wiki/Allergic_rhinitis" title="Allergic rhinitis">Hay fever (allergic rhinitis)</a></li> <li><a href="/wiki/Histamine_intolerance" title="Histamine intolerance">Histamine intolerance</a></li> <li><a href="/wiki/Antihistamine" title="Antihistamine">Histamine receptor antagonist</a></li> <li><a href="/wiki/Scombroid_food_poisoning" title="Scombroid food poisoning">Scombroid food poisoning</a></li> <li><a href="/wiki/Photic_sneeze_reflex" title="Photic sneeze reflex">Photic sneeze reflex</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=Histamine&action=edit&section=19" title="Edit section: References"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1239543626">.mw-parser-output .reflist{margin-bottom:0.5em;list-style-type:decimal}@media screen{.mw-parser-output .reflist{font-size:90%}}.mw-parser-output .reflist .references{font-size:100%;margin-bottom:0;list-style-type:inherit}.mw-parser-output .reflist-columns-2{column-width:30em}.mw-parser-output .reflist-columns-3{column-width:25em}.mw-parser-output .reflist-columns{margin-top:0.3em}.mw-parser-output .reflist-columns ol{margin-top:0}.mw-parser-output .reflist-columns li{page-break-inside:avoid;break-inside:avoid-column}.mw-parser-output .reflist-upper-alpha{list-style-type:upper-alpha}.mw-parser-output .reflist-upper-roman{list-style-type:upper-roman}.mw-parser-output .reflist-lower-alpha{list-style-type:lower-alpha}.mw-parser-output .reflist-lower-greek{list-style-type:lower-greek}.mw-parser-output .reflist-lower-roman{list-style-type:lower-roman}</style><div class="reflist reflist-columns references-column-width reflist-columns-2"> <ol class="references"> <li id="cite_note-sciencelab.com-1"><span class="mw-cite-backlink">^ <a href="#cite_ref-sciencelab.com_1-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-sciencelab.com_1-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><style data-mw-deduplicate="TemplateStyles:r1238218222">.mw-parser-output cite.citation{font-style:inherit;word-wrap:break-word}.mw-parser-output .citation q{quotes:"\"""\"""'""'"}.mw-parser-output .citation:target{background-color:rgba(0,127,255,0.133)}.mw-parser-output .id-lock-free.id-lock-free a{background:url("//upload.wikimedia.org/wikipedia/commons/6/65/Lock-green.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-limited.id-lock-limited a,.mw-parser-output .id-lock-registration.id-lock-registration a{background:url("//upload.wikimedia.org/wikipedia/commons/d/d6/Lock-gray-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-subscription.id-lock-subscription a{background:url("//upload.wikimedia.org/wikipedia/commons/a/aa/Lock-red-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .cs1-ws-icon a{background:url("//upload.wikimedia.org/wikipedia/commons/4/4c/Wikisource-logo.svg")right 0.1em center/12px no-repeat}body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-free a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-limited a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-registration a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-subscription a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .cs1-ws-icon a{background-size:contain;padding:0 1em 0 0}.mw-parser-output .cs1-code{color:inherit;background:inherit;border:none;padding:inherit}.mw-parser-output .cs1-hidden-error{display:none;color:var(--color-error,#d33)}.mw-parser-output .cs1-visible-error{color:var(--color-error,#d33)}.mw-parser-output .cs1-maint{display:none;color:#085;margin-left:0.3em}.mw-parser-output .cs1-kern-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right{padding-right:0.2em}.mw-parser-output .citation .mw-selflink{font-weight:inherit}@media screen{.mw-parser-output .cs1-format{font-size:95%}html.skin-theme-clientpref-night .mw-parser-output .cs1-maint{color:#18911f}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .cs1-maint{color:#18911f}}</style><cite class="citation techreport cs1"><a rel="nofollow" class="external text" href="http://www.sciencelab.com/msds.php?msdsId=9924264"><i>Histamine Material Safety Data Sheet</i></a> (Technical report). sciencelab.com. 2013-05-21. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20120324194707/http://www.sciencelab.com/msds.php?msdsId=9924264">Archived</a> from the original on 2012-03-24.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=report&rft.btitle=Histamine+Material+Safety+Data+Sheet&rft.pub=sciencelab.com&rft.date=2013-05-21&rft_id=http%3A%2F%2Fwww.sciencelab.com%2Fmsds.php%3FmsdsId%3D9924264&rfr_id=info%3Asid%2Fen.wikipedia.org%3AHistamine" class="Z3988"></span></span> </li> <li id="cite_note-Vuckovic-2"><span class="mw-cite-backlink">^ <a href="#cite_ref-Vuckovic_2-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Vuckovic_2-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFVuckovicPawliszyn2011" class="citation journal cs1">Vuckovic D, Pawliszyn J (March 2011). 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title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Journal+of+Urology&rft.atitle=Increased+Urine+Histamine+and+Methylhistamine+in+Interstitial+Cystitis&rft.volume=152&rft.issue=2+Part+1&rft.pages=350-353&rft.date=1994&rft_id=info%3Adoi%2F10.1016%2FS0022-5347%2817%2932737-4&rft_id=info%3Apmid%2F8015069&rft.aulast=El-Mansoury&rft.aufirst=M&rft.au=Boucher%2C+W&rft.au=Sant%2C+G&rft.au=Theoharides%2C+T&rft_id=https%3A%2F%2Fdoi.org%2F10.1016%2FS0022-5347%2817%2932737-4&rfr_id=info%3Asid%2Fen.wikipedia.org%3AHistamine" class="Z3988"></span></span> </li> <li id="cite_note-54"><span class="mw-cite-backlink"><b><a href="#cite_ref-54">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFDaleLaidlaw1910" class="citation journal cs1">Dale HH, Laidlaw PP (December 1910). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1512903">"The physiological action of beta-iminazolylethylamine"</a>. <i>The Journal of Physiology</i>. <b>41</b> (5): 318–44. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1113%2Fjphysiol.1910.sp001406">10.1113/jphysiol.1910.sp001406</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/PMC1512903">1512903</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/16993030">16993030</a>.</cite><span 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id="External_links">External links</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Histamine&action=edit&section=20" title="Edit section: External links"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a rel="nofollow" class="external text" href="http://gmd.mpimp-golm.mpg.de/Spectrums/a2a57255-e29a-4df3-98ea-af64d4a95056.aspx">Histamine MS Spectrum</a></li> <li><a rel="nofollow" class="external text" href="http://www.ebi.ac.uk/pdbe-srv/PDBeXplore/ligand/?ligand=HSM">Histamine bound to proteins</a> in the <a href="/wiki/Protein_Data_Bank" title="Protein Data Bank">PDB</a></li></ul> <div class="navbox-styles"><style data-mw-deduplicate="TemplateStyles:r1129693374">.mw-parser-output .hlist dl,.mw-parser-output .hlist ol,.mw-parser-output .hlist ul{margin:0;padding:0}.mw-parser-output .hlist dd,.mw-parser-output .hlist dt,.mw-parser-output .hlist li{margin:0;display:inline}.mw-parser-output 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.navbar{display:block;font-size:100%}.mw-parser-output .navbox-title .navbar{float:left;text-align:left;margin-right:0.5em}body.skin--responsive .mw-parser-output .navbox-image img{max-width:none!important}@media print{body.ns-0 .mw-parser-output .navbox{display:none!important}}</style></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"><style data-mw-deduplicate="TemplateStyles:r1239400231">.mw-parser-output .navbar{display:inline;font-size:88%;font-weight:normal}.mw-parser-output .navbar-collapse{float:left;text-align:left}.mw-parser-output .navbar-boxtext{word-spacing:0}.mw-parser-output .navbar ul{display:inline-block;white-space:nowrap;line-height:inherit}.mw-parser-output .navbar-brackets::before{margin-right:-0.125em;content:"[ "}.mw-parser-output .navbar-brackets::after{margin-left:-0.125em;content:" ]"}.mw-parser-output .navbar li{word-spacing:-0.125em}.mw-parser-output .navbar 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: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 class="mw-selflink selflink">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="/wiki/Napactadine" title="Napactadine">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 class="mw-selflink selflink">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 class="mw-selflink selflink">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 class="mw-selflink selflink">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> <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="Neurotransmitters" style="padding:3px"><table class="nowraplinks mw-collapsible autocollapse navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2" style="text-align: center;"><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:Neurotransmitters" title="Template:Neurotransmitters"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Neurotransmitters" title="Template talk:Neurotransmitters"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Neurotransmitters" title="Special:EditPage/Template:Neurotransmitters"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Neurotransmitters" style="font-size:114%;margin:0 4em"><a href="/wiki/Neurotransmitter" title="Neurotransmitter">Neurotransmitters</a></div></th></tr><tr><th scope="row" class="navbox-group" style="text-align: center;;width:1%"><a href="/wiki/Amino_acid" title="Amino acid">Amino acid</a>-derived</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%;font-weight:normal; text-align: center;">Major excitatory /<br />inhibitory systems</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%;font-weight:normal;">Glutamate system</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/Aspartic_acid" title="Aspartic acid">Aspartic acid (aspartate)</a></li> <li><a href="/wiki/Glutamate_(neurotransmitter)" title="Glutamate (neurotransmitter)">Glutamic acid (glutamate)</a></li> <li><a href="/wiki/Glutathione" title="Glutathione">Glutathione</a></li> <li><a href="/wiki/Glycine" title="Glycine">Glycine</a></li> <li><a href="/wiki/S-Nitrosoglutathione" title="S-Nitrosoglutathione">GSNO</a></li> <li><a href="/wiki/Oxidized_glutathione" class="mw-redirect" title="Oxidized glutathione">GSSG</a></li> <li><a href="/wiki/Kynurenic_acid" title="Kynurenic acid">Kynurenic acid</a></li> <li><a href="/wiki/N-Acetylaspartic_acid" title="N-Acetylaspartic acid">NAA</a></li> <li><a href="/wiki/N-Acetylaspartylglutamic_acid" title="N-Acetylaspartylglutamic acid">NAAG</a></li> <li><a href="/wiki/Proline" title="Proline">Proline</a></li> <li><a href="/wiki/Serine" title="Serine">Serine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;font-weight:normal;">GABA system</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/Gamma-Aminobutyric_acid" class="mw-redirect" title="Gamma-Aminobutyric acid">GABA</a></li> <li><a href="/wiki/Gamma-Amino-beta-hydroxybutyric_acid" class="mw-redirect" title="Gamma-Amino-beta-hydroxybutyric acid">GABOB</a></li> <li><a href="/wiki/Gamma-Hydroxybutyric_acid" class="mw-redirect" title="Gamma-Hydroxybutyric acid">GHB</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;font-weight:normal;">Glycine system</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/Alanine" title="Alanine">α-Alanine</a></li> <li><a href="/wiki/%CE%92-Alanine" title="Β-Alanine">β-Alanine</a></li> <li><a href="/wiki/Glycine" title="Glycine">Glycine</a></li> <li><a href="/wiki/Hypotaurine" title="Hypotaurine">Hypotaurine</a></li> <li><a href="/wiki/Proline" title="Proline">Proline</a></li> <li><a href="/wiki/Sarcosine" title="Sarcosine">Sarcosine</a></li> <li><a href="/wiki/Serine" title="Serine">Serine</a></li> <li><a href="/wiki/Taurine" title="Taurine">Taurine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;font-weight:normal;"><a href="/wiki/GHB_receptor" title="GHB receptor">GHB system</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/Gamma-Hydroxybutyric_acid" class="mw-redirect" title="Gamma-Hydroxybutyric acid">GHB</a></li> <li><a href="/wiki/T-HCA" title="T-HCA">T-HCA (GHC)</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;font-weight:normal; text-align: center;"><a href="/wiki/Biogenic_amine" title="Biogenic amine">Biogenic amines</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:4em;font-weight:normal; text-align: center;">Monoamines</th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/6-Hydroxymelatonin" title="6-Hydroxymelatonin">6-OHM</a></li> <li><a href="/wiki/Dopamine" title="Dopamine">Dopamine</a></li> <li><a href="/wiki/Adrenaline" title="Adrenaline">Epinephrine (adrenaline)</a></li> <li><a href="/wiki/N-Acetylserotonin" title="N-Acetylserotonin">NAS (normelatonin)</a></li> <li><a href="/wiki/Norepinephrine" title="Norepinephrine">Norepinephrine (noradrenaline)</a></li> <li><a href="/wiki/Serotonin" title="Serotonin">Serotonin (5-HT)</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:4em;font-weight:normal; text-align: center;">Trace amines</th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/3-Iodothyronamine" title="3-Iodothyronamine">3-Iodothyronamine</a></li> <li><a href="/wiki/N-Methylphenethylamine" title="N-Methylphenethylamine">N-Methylphenethylamine</a></li> <li><a href="/wiki/N-Methyltryptamine" title="N-Methyltryptamine">N-Methyltryptamine</a></li> <li><a href="/wiki/Norfenefrine" title="Norfenefrine"><i>m</i>-Octopamine</a></li> <li><a href="/wiki/Octopamine" title="Octopamine"><i>p</i>-Octopamine</a></li> <li><a href="/wiki/Phenylethanolamine" title="Phenylethanolamine">Phenylethanolamine</a></li> <li><a href="/wiki/Phenethylamine" title="Phenethylamine">Phenethylamine</a></li> <li><a href="/wiki/Synephrine" title="Synephrine">Synephrine</a></li> <li><a href="/wiki/Tryptamine" title="Tryptamine">Tryptamine</a></li> <li><a href="/wiki/Meta-Tyramine" title="Meta-Tyramine"><i>m</i>-Tyramine</a></li> <li><a href="/wiki/Tyramine" title="Tyramine"><i>p</i>-Tyramine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:4em;font-weight:normal; text-align: center;">Others</th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a class="mw-selflink selflink">Histamine</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;font-weight:normal; text-align: center;"><a href="/wiki/Neuropeptide" title="Neuropeptide">Neuropeptides</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><td colspan="2" class="navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li>See <a href="/wiki/Template:Neuropeptides" title="Template:Neuropeptides">here</a> instead.</li></ul> </div></td></tr></tbody></table><div></div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="text-align: center;;width:1%"><a href="/wiki/Lipid" title="Lipid">Lipid</a>-derived</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th id="Endocannabinoids" scope="row" class="navbox-group" style="width:1%;font-weight:normal; text-align: center;">Endocannabinoids</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-Arachidonoylglycerol" title="2-Arachidonoylglycerol">2-AG</a></li> <li><a href="/wiki/2-Arachidonyl_glyceryl_ether" title="2-Arachidonyl glyceryl ether">2-AGE (noladin ether)</a></li> <li><a href="/w/index.php?title=2-Arachidonoyl_lysophosphatidylinositol&action=edit&redlink=1" class="new" title="2-Arachidonoyl lysophosphatidylinositol (page does not exist)">2-ALPI</a></li> <li><a href="/wiki/2-Oleoylglycerol" title="2-Oleoylglycerol">2-OG</a></li> <li><a href="/wiki/Arachidonoyl_serotonin" title="Arachidonoyl serotonin">AA-5-HT</a></li> <li><a href="/wiki/Anandamide" title="Anandamide">Anandamide (AEA)</a></li> <li><a href="/wiki/Docosatetraenoylethanolamide" title="Docosatetraenoylethanolamide">DEA</a></li> <li><a href="/wiki/Lysophosphatidylinositol" title="Lysophosphatidylinositol">LPI</a></li> <li><a href="/wiki/N-Arachidonoyl_dopamine" title="N-Arachidonoyl dopamine">NADA</a></li> <li><a href="/wiki/N-Arachidonylglycine" title="N-Arachidonylglycine">NAGly</a></li> <li><a href="/wiki/Oleoylethanolamide" title="Oleoylethanolamide">OEA</a></li> <li><a href="/wiki/Oleamide" title="Oleamide">Oleamide</a></li> <li><a href="/wiki/Palmitoylethanolamide" title="Palmitoylethanolamide">PEA</a></li> <li><a href="/wiki/RVD-Hp%CE%B1" title="RVD-Hpα">RVD-Hpα</a></li> <li><a href="/wiki/Stearoylethanolamide" title="Stearoylethanolamide">SEA</a></li> <li><a href="/wiki/Virodhamine" title="Virodhamine">Virodhamine (O-AEA)</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;font-weight:normal; text-align: center;"><a href="/wiki/Neurosteroid" title="Neurosteroid">Neurosteroids</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><td colspan="2" class="navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li>See <a href="/wiki/Template:Steroid_hormones" title="Template:Steroid hormones">here</a> instead.</li></ul> </div></td></tr></tbody></table><div></div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="text-align: center;;width:1%"><a href="/wiki/Nucleobase" class="mw-redirect" title="Nucleobase">Nucleobase</a>-derived</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th id="Nucleosides" scope="row" class="navbox-group" style="width:1%;font-weight:normal; text-align: center;">Nucleosides</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="Adenosine_system" scope="row" class="navbox-group" style="width:1%;font-weight:normal; text-align: center;"><a href="/wiki/Adenosine" title="Adenosine">Adenosine</a> system</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/Adenosine_diphosphate" title="Adenosine diphosphate">ADP</a></li> <li><a href="/wiki/Adenosine_monophosphate" title="Adenosine monophosphate">AMP</a></li> <li><a href="/wiki/Adenosine_triphosphate" title="Adenosine triphosphate">ATP</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="text-align: center;;width:1%"><a href="/wiki/Vitamin" title="Vitamin">Vitamin</a>-derived</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"></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="text-align: center;;width:1%">Miscellaneous</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th id="Cholinergic_system" scope="row" class="navbox-group" style="width:1%;font-weight:normal; text-align: center;">Cholinergic system</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/Acetylcholine" title="Acetylcholine">Acetylcholine</a></li></ul> </div></td></tr></tbody></table><div> </div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th id="Gasotransmitters" scope="row" class="navbox-group" style="width:1%;font-weight:normal; text-align: center;">Gasotransmitters</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/Carbon_monoxide" title="Carbon monoxide">Carbon monoxide (CO)</a></li> <li><a href="/wiki/Hydrogen_sulfide" title="Hydrogen sulfide">Hydrogen sulfide (H<sub>2</sub>S)</a></li> <li><a href="/wiki/Nitric_oxide" title="Nitric oxide">Nitric oxide (NO)</a></li></ul> </div></td></tr></tbody></table><div> </div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th id="Candidates" scope="row" class="navbox-group" style="width:1%;font-weight:normal; text-align: center;">Candidates</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/Acetaldehyde" title="Acetaldehyde">Acetaldehyde</a></li> <li><a href="/wiki/Ammonia" title="Ammonia">Ammonia (NH<sub>3</sub>)</a></li> <li><a href="/wiki/Carbonyl_sulfide" title="Carbonyl sulfide">Carbonyl sulfide (COS)</a></li> <li><a href="/wiki/Nitrous_oxide" title="Nitrous oxide">Nitrous oxide (N<sub>2</sub>O)</a></li> <li><a href="/wiki/Sulfur_dioxide" title="Sulfur dioxide">Sulfur dioxide (SO<sub>2</sub>)</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="Human_trace_amine-associated_receptor_ligands" style="padding:3px"><table class="nowraplinks hlist mw-collapsible autocollapse navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:TAAR_ligands" title="Template:TAAR ligands"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:TAAR_ligands" title="Template talk:TAAR ligands"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:TAAR_ligands" title="Special:EditPage/Template:TAAR ligands"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Human_trace_amine-associated_receptor_ligands" style="font-size:114%;margin:0 4em"><a href="/wiki/Human_trace_amine-associated_receptor" class="mw-redirect" title="Human trace amine-associated receptor">Human trace amine-associated receptor</a> <a href="/wiki/Ligand_(biochemistry)" title="Ligand (biochemistry)">ligands</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align: center"><a href="/wiki/TAAR1" title="TAAR1">TAAR1</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:6em;text-align: center"><a href="/wiki/Agonist" title="Agonist">Agonists</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:5em;text-align: center"><a href="/wiki/Trace_amine" title="Trace amine">Endogenous</a><sup>†</sup></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0;background:white"><div style="padding:0 0.25em"> <ul><li>Classical <a href="/wiki/Monoamine_neurotransmitter" title="Monoamine neurotransmitter">monoamine neurotransmitters</a> <ul><li><a href="/wiki/Dopamine" title="Dopamine">Dopamine</a></li> <li><a class="mw-selflink selflink">Histamine</a></li> <li><a href="/wiki/Epinephrine" class="mw-redirect" title="Epinephrine">Epinephrine (adrenaline)</a></li> <li><a href="/wiki/Norepinephrine" title="Norepinephrine">Norepinephrine (noradrenaline)</a></li> <li><a href="/wiki/Serotonin" title="Serotonin">Serotonin</a></li></ul></li> <li><a href="/wiki/Trace_amine" title="Trace amine">Trace amines</a> <ul><li><a href="/wiki/3-Iodothyronamine" title="3-Iodothyronamine">3-Iodothyronamine</a></li> <li><a href="/wiki/3-Methoxytyramine" title="3-Methoxytyramine">3-Methoxytyramine</a></li> <li><a href="/wiki/N-Methylphenethylamine" title="N-Methylphenethylamine"><i>N</i>-Methylphenethylamine</a></li> <li><a href="/wiki/N-Methyltyramine" title="N-Methyltyramine"><i>N</i>-Methyltyramine</a></li> <li><a href="/wiki/Meta-Octopamine" class="mw-redirect" title="Meta-Octopamine"><i>m</i>-Octopamine</a></li> <li><a href="/wiki/Para-Octopamine" class="mw-redirect" title="Para-Octopamine"><i>p</i>-Octopamine</a></li> <li><a href="/wiki/Phenethylamine" title="Phenethylamine">Phenethylamine</a></li> <li><a href="/wiki/Phenylethanolamine" title="Phenylethanolamine">Phenylethanolamine</a></li> <li><a href="/wiki/Synephrine" title="Synephrine">Synephrine</a></li> <li><a href="/wiki/Tryptamine" title="Tryptamine">Tryptamine</a></li> <li><a href="/wiki/Meta-Tyramine" title="Meta-Tyramine"><i>m</i>-Tyramine</a></li> <li><a href="/wiki/Para-Tyramine" class="mw-redirect" title="Para-Tyramine"><i>p</i>-Tyramine</a></li></ul></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:5em;text-align: center">Synthetic and natural<sup>‡</sup></th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0;background:white"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Amphetamine" title="Amphetamine">Amphetamine</a></li> <li><a href="/wiki/2,5-Dimethoxy-4-bromoamphetamine" title="2,5-Dimethoxy-4-bromoamphetamine">DOB</a></li> <li><a href="/wiki/2,5-Dimethoxy-4-ethylamphetamine" title="2,5-Dimethoxy-4-ethylamphetamine">DOET</a></li> <li><a href="/wiki/N,N-Dimethylphenethylamine" title="N,N-Dimethylphenethylamine"><i>N</i>,<i>N</i>-Dimethylphenethylamine</a></li> <li><a href="/wiki/Guanfacine" title="Guanfacine">Guanfacine</a></li> <li><a href="/wiki/Halostachine" title="Halostachine">Halostachine</a></li> <li><a href="/wiki/Higenamine" title="Higenamine">Higenamine</a></li> <li><a href="/wiki/Hordenine" title="Hordenine">Hordenine</a></li> <li><a href="/wiki/4-Hydroxyamphetamine" title="4-Hydroxyamphetamine">4-Hydroxyamphetamine</a></li> <li><a href="/wiki/Isopropyloctopamine" class="mw-redirect" title="Isopropyloctopamine">Isopropyloctopamine</a></li> <li><a href="/wiki/Isoprenaline" title="Isoprenaline">Isoprenaline</a></li> <li><a href="/wiki/3,4-Methylenedioxyamphetamine" title="3,4-Methylenedioxyamphetamine">MDA (tenamfetamine)</a></li> <li><a href="/wiki/MDMA" title="MDMA">MDMA (midomafetamine)</a></li> <li><a href="/wiki/2-Methylphenethylamine" title="2-Methylphenethylamine">2-Methylphenethylamine</a></li> <li><a href="/wiki/3-Methylphenethylamine" title="3-Methylphenethylamine">3-Methylphenethylamine</a></li> <li><a href="/wiki/4-Methylphenethylamine" title="4-Methylphenethylamine">4-Methylphenethylamine</a></li> <li><a href="/wiki/%CE%92-Methylphenethylamine" title="Β-Methylphenethylamine">β-Methylphenethylamine</a></li> <li><a href="/wiki/Methamphetamine" title="Methamphetamine">Methamphetamine</a></li> <li><a href="/wiki/3-Methoxymethamphetamine" title="3-Methoxymethamphetamine">3-MMA</a></li> <li><a href="/wiki/Norfenfluramine" title="Norfenfluramine">Norfenfluramine</a></li> <li><a href="/wiki/Phentermine" title="Phentermine">Phentermine</a></li> <li><a href="/wiki/O-Phenyl-3-iodotyramine" title="O-Phenyl-3-iodotyramine"><i>o</i>-PIT</a></li> <li><a href="/wiki/Propylhexedrine" title="Propylhexedrine">Propylhexedrine</a></li> <li><a href="/wiki/Ralmitaront" title="Ralmitaront">Ralmitaront (RG-7906, RO-6889450)</a></li> <li><a href="/wiki/RG-7351" title="RG-7351">RG-7351</a></li> <li><a href="/wiki/RG-7410" title="RG-7410">RG-7410</a></li> <li><a href="/wiki/RO5166017" title="RO5166017">RO-5166017</a></li> <li><a href="/wiki/RO5256390" title="RO5256390">RO-5256390</a></li> <li><a href="/wiki/RO5263397" title="RO5263397">RO-5263397</a></li> <li><a href="/wiki/Selegiline" title="Selegiline">Selegiline</a></li> <li><a href="/wiki/Solriamfetol" title="Solriamfetol">Solriamfetol</a></li> <li><a href="/wiki/Ulotaront" title="Ulotaront">Ulotaront (SEP-363856)</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:6em;text-align: center"><a href="/wiki/Neutral_antagonist" class="mw-redirect" title="Neutral antagonist">Neutral antagonists</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/RTI-7470-44" title="RTI-7470-44">RTI-7470-44</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:6em;text-align: center"><a href="/wiki/Inverse_agonist" title="Inverse agonist">Inverse agonists</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/EPPTB" title="EPPTB">EPPTB (RO-5212773)</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/TAAR2" title="TAAR2">TAAR2</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:6em;text-align: center">Agonists<sup>‡</sup></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:6em;text-align: center">Neutral antagonists</th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li> </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/TAAR5" title="TAAR5">TAAR5</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:6em;text-align: center">Agonists<sup>‡</sup></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/N,N-Dimethylethylamine" title="N,N-Dimethylethylamine"><i>N</i>,<i>N</i>-Dimethylethylamine</a></li> <li><a href="/wiki/Trimethylamine" title="Trimethylamine">Trimethylamine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:6em;text-align: center">Neutral antagonists</th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li> </li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:6em;text-align: center">Inverse agonists<sup>‡</sup></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/3-Iodothyronamine" title="3-Iodothyronamine">3-Iodothyronamine</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><td class="navbox-abovebelow" colspan="2"><div><div style="float: left;"><small><sup>†</sup> References for all endogenous human TAAR1 ligands are provided at <a href="/wiki/Trace_amine#list" title="Trace amine">List of trace amines</a></small></div> <p><br /> </p> <div style="float: left;"><small><sup>‡</sup> References for synthetic TAAR1 agonists can be found at <a href="/wiki/TAAR1" title="TAAR1">TAAR1</a> or in the associated compound articles. For TAAR2 and TAAR5 agonists and inverse agonists, see <a href="/wiki/Trace_amine-associated_receptor#Receptor_function_and_ligands" title="Trace amine-associated receptor">TAAR</a> for references.</small></div> <p><br /> </p> <small><i><b>See also:</b> <a href="/wiki/Template:Receptor_modulators" title="Template:Receptor modulators">Receptor/signaling modulators</a></i></small></div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"><style data-mw-deduplicate="TemplateStyles:r1038841319">.mw-parser-output .tooltip-dotted{border-bottom:1px dotted;cursor:help}</style><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1038841319"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1038841319"><link rel="mw-deduplicated-inline-style" 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