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class="vector-toc-text"> <span class="vector-toc-numb">2</span> <span>Production</span> </div> </a> <ul id="toc-Production-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Chemical_reactions" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Chemical_reactions"> <div class="vector-toc-text"> <span class="vector-toc-numb">3</span> <span>Chemical reactions</span> </div> </a> <ul id="toc-Chemical_reactions-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Metabolism" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Metabolism"> <div class="vector-toc-text"> <span class="vector-toc-numb">4</span> <span>Metabolism</span> </div> </a> <button aria-controls="toc-Metabolism-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> <span class="vector-icon mw-ui-icon-wikimedia-expand"></span> <span>Toggle Metabolism subsection</span> </button> <ul id="toc-Metabolism-sublist" class="vector-toc-list"> <li id="toc-Biosynthesis" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Biosynthesis"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.1</span> <span>Biosynthesis</span> </div> </a> <ul id="toc-Biosynthesis-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Degradation" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Degradation"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.2</span> <span>Degradation</span> </div> </a> <ul id="toc-Degradation-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Physiological_function" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Physiological_function"> <div class="vector-toc-text"> <span class="vector-toc-numb">5</span> <span>Physiological function</span> </div> </a> <button aria-controls="toc-Physiological_function-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> <span class="vector-icon mw-ui-icon-wikimedia-expand"></span> <span>Toggle Physiological function subsection</span> </button> <ul id="toc-Physiological_function-sublist" class="vector-toc-list"> <li id="toc-As_a_biosynthetic_intermediate" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#As_a_biosynthetic_intermediate"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.1</span> <span>As a biosynthetic intermediate</span> </div> </a> <ul id="toc-As_a_biosynthetic_intermediate-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-As_a_neurotransmitter" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#As_a_neurotransmitter"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.2</span> <span>As a neurotransmitter</span> </div> </a> <ul id="toc-As_a_neurotransmitter-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-As_a_toxin_conjugation_agent" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#As_a_toxin_conjugation_agent"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.3</span> <span>As a toxin conjugation agent</span> </div> </a> <ul id="toc-As_a_toxin_conjugation_agent-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Uses" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Uses"> <div class="vector-toc-text"> <span class="vector-toc-numb">6</span> <span>Uses</span> </div> </a> <button aria-controls="toc-Uses-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 Uses subsection</span> </button> <ul id="toc-Uses-sublist" class="vector-toc-list"> <li id="toc-Animal_and_human_foods" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Animal_and_human_foods"> <div class="vector-toc-text"> <span class="vector-toc-numb">6.1</span> <span>Animal and human foods</span> </div> </a> <ul id="toc-Animal_and_human_foods-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Chemical_feedstock" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Chemical_feedstock"> <div class="vector-toc-text"> <span class="vector-toc-numb">6.2</span> <span>Chemical feedstock</span> </div> </a> <ul id="toc-Chemical_feedstock-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Laboratory_research" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Laboratory_research"> <div class="vector-toc-text"> <span class="vector-toc-numb">6.3</span> <span>Laboratory research</span> </div> </a> <ul id="toc-Laboratory_research-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Presence_in_space" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Presence_in_space"> <div class="vector-toc-text"> <span class="vector-toc-numb">7</span> <span>Presence in space</span> </div> </a> <ul id="toc-Presence_in_space-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Evolution" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Evolution"> <div class="vector-toc-text"> <span class="vector-toc-numb">8</span> <span>Evolution</span> </div> </a> <ul id="toc-Evolution-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Presence_in_foods" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Presence_in_foods"> <div class="vector-toc-text"> <span class="vector-toc-numb">9</span> <span>Presence in foods</span> </div> </a> <ul id="toc-Presence_in_foods-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-Further_reading" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Further_reading"> <div class="vector-toc-text"> <span class="vector-toc-numb">12</span> <span>Further reading</span> </div> </a> <ul id="toc-Further_reading-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">13</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" title="Table of Contents" > <input type="checkbox" id="vector-page-titlebar-toc-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-vector-page-titlebar-toc" class="vector-dropdown-checkbox " aria-label="Toggle the table of contents" > <label id="vector-page-titlebar-toc-label" for="vector-page-titlebar-toc-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--icon-only " aria-hidden="true" ><span class="vector-icon mw-ui-icon-listBullet mw-ui-icon-wikimedia-listBullet"></span> <span class="vector-dropdown-label-text">Toggle the table of contents</span> </label> <div class="vector-dropdown-content"> <div id="vector-page-titlebar-toc-unpinned-container" class="vector-unpinned-container"> </div> </div> </div> </nav> <h1 id="firstHeading" class="firstHeading mw-first-heading"><span class="mw-page-title-main">Glycine</span></h1> <div id="p-lang-btn" class="vector-dropdown mw-portlet mw-portlet-lang" > <input type="checkbox" id="p-lang-btn-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-p-lang-btn" class="vector-dropdown-checkbox mw-interlanguage-selector" aria-label="Go to an article in another language. Available in 73 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-73" 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">73 languages</span> </label> <div class="vector-dropdown-content"> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li class="interlanguage-link interwiki-af mw-list-item"><a href="https://af.wikipedia.org/wiki/Glisien" title="Glisien – Afrikaans" lang="af" hreflang="af" data-title="Glisien" data-language-autonym="Afrikaans" data-language-local-name="Afrikaans" class="interlanguage-link-target"><span>Afrikaans</span></a></li><li class="interlanguage-link interwiki-ar mw-list-item"><a href="https://ar.wikipedia.org/wiki/%D8%AC%D9%84%D8%A7%D9%8A%D8%B3%D9%8A%D9%86" title="جلايسين – Arabic" lang="ar" hreflang="ar" data-title="جلايسين" data-language-autonym="العربية" data-language-local-name="Arabic" class="interlanguage-link-target"><span>العربية</span></a></li><li class="interlanguage-link interwiki-az mw-list-item"><a href="https://az.wikipedia.org/wiki/Qlisin" title="Qlisin – Azerbaijani" lang="az" hreflang="az" data-title="Qlisin" data-language-autonym="Azərbaycanca" data-language-local-name="Azerbaijani" class="interlanguage-link-target"><span>Azərbaycanca</span></a></li><li class="interlanguage-link interwiki-azb mw-list-item"><a href="https://azb.wikipedia.org/wiki/%D9%82%D9%84%DB%8C%D8%B3%DB%8C%D9%86" title="قلیسین – South Azerbaijani" lang="azb" hreflang="azb" data-title="قلیسین" 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%97%E0%A7%8D%E0%A6%B2%E0%A6%BE%E0%A6%87%E0%A6%B8%E0%A6%BF%E0%A6%A8" title="গ্লাইসিন – Bangla" lang="bn" hreflang="bn" data-title="গ্লাইসিন" data-language-autonym="বাংলা" data-language-local-name="Bangla" class="interlanguage-link-target"><span>বাংলা</span></a></li><li class="interlanguage-link interwiki-zh-min-nan mw-list-item"><a href="https://zh-min-nan.wikipedia.org/wiki/Glycin" title="Glycin – Minnan" lang="nan" hreflang="nan" data-title="Glycin" data-language-autonym="閩南語 / Bân-lâm-gú" data-language-local-name="Minnan" class="interlanguage-link-target"><span>閩南語 / Bân-lâm-gú</span></a></li><li class="interlanguage-link interwiki-be mw-list-item"><a href="https://be.wikipedia.org/wiki/%D0%93%D0%BB%D1%96%D1%86%D1%8B%D0%BD" title="Гліцын – Belarusian" lang="be" hreflang="be" data-title="Гліцын" 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%93%D0%BB%D0%B8%D1%86%D0%B8%D0%BD" title="Глицин – Bulgarian" lang="bg" hreflang="bg" data-title="Глицин" 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/Glicin" title="Glicin – Bosnian" lang="bs" hreflang="bs" data-title="Glicin" 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/Glicina" title="Glicina – Catalan" lang="ca" hreflang="ca" data-title="Glicina" 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/Glycin" title="Glycin – Czech" lang="cs" hreflang="cs" data-title="Glycin" data-language-autonym="Čeština" data-language-local-name="Czech" class="interlanguage-link-target"><span>Čeština</span></a></li><li class="interlanguage-link interwiki-cy mw-list-item"><a href="https://cy.wikipedia.org/wiki/Glycin" title="Glycin – Welsh" lang="cy" hreflang="cy" data-title="Glycin" data-language-autonym="Cymraeg" data-language-local-name="Welsh" class="interlanguage-link-target"><span>Cymraeg</span></a></li><li class="interlanguage-link interwiki-da mw-list-item"><a href="https://da.wikipedia.org/wiki/Glycin" title="Glycin – Danish" lang="da" hreflang="da" data-title="Glycin" 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/Glycin" title="Glycin – German" lang="de" hreflang="de" data-title="Glycin" 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/Gl%C3%BCtsiin" title="Glütsiin – Estonian" lang="et" hreflang="et" data-title="Glütsiin" 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%93%CE%BB%CF%85%CE%BA%CE%AF%CE%BD%CE%B7" title="Γλυκίνη – Greek" lang="el" hreflang="el" data-title="Γλυκίνη" 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/Glicina" title="Glicina – Spanish" lang="es" hreflang="es" data-title="Glicina" 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/Glicino" title="Glicino – Esperanto" lang="eo" hreflang="eo" data-title="Glicino" 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/Glizina_(aminoazidoa)" title="Glizina (aminoazidoa) – Basque" lang="eu" hreflang="eu" data-title="Glizina (aminoazidoa)" data-language-autonym="Euskara" data-language-local-name="Basque" class="interlanguage-link-target"><span>Euskara</span></a></li><li class="interlanguage-link interwiki-fa mw-list-item"><a href="https://fa.wikipedia.org/wiki/%DA%AF%D9%84%D8%A7%DB%8C%D8%B3%DB%8C%D9%86" title="گلایسین – Persian" lang="fa" hreflang="fa" data-title="گلایسین" 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/Glycine_(acide_amin%C3%A9)" title="Glycine (acide aminé) – French" lang="fr" hreflang="fr" data-title="Glycine (acide aminé)" 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/Glic%C3%ADn" title="Glicín – Irish" lang="ga" hreflang="ga" data-title="Glicín" 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/Glicina" title="Glicina – Galician" lang="gl" hreflang="gl" data-title="Glicina" 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/%EA%B8%80%EB%9D%BC%EC%9D%B4%EC%8B%A0" title="글라이신 – Korean" lang="ko" hreflang="ko" data-title="글라이신" data-language-autonym="한국어" data-language-local-name="Korean" class="interlanguage-link-target"><span>한국어</span></a></li><li class="interlanguage-link interwiki-hy mw-list-item"><a href="https://hy.wikipedia.org/wiki/%D4%B3%D5%AC%D5%AB%D6%81%D5%AB%D5%B6" title="Գլիցին – Armenian" lang="hy" hreflang="hy" data-title="Գլիցին" data-language-autonym="Հայերեն" data-language-local-name="Armenian" class="interlanguage-link-target"><span>Հայերեն</span></a></li><li class="interlanguage-link interwiki-hr mw-list-item"><a href="https://hr.wikipedia.org/wiki/Glicin" title="Glicin – Croatian" lang="hr" hreflang="hr" data-title="Glicin" 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/Glisina" title="Glisina – Indonesian" lang="id" hreflang="id" data-title="Glisina" 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/Glicina" title="Glicina – Italian" lang="it" hreflang="it" data-title="Glicina" 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%92%D7%9C%D7%99%D7%A6%D7%99%D7%9F" title="גליצין – Hebrew" lang="he" hreflang="he" data-title="גליצין" data-language-autonym="עברית" data-language-local-name="Hebrew" class="interlanguage-link-target"><span>עברית</span></a></li><li class="interlanguage-link interwiki-ka mw-list-item"><a href="https://ka.wikipedia.org/wiki/%E1%83%92%E1%83%9A%E1%83%98%E1%83%AA%E1%83%98%E1%83%9C%E1%83%98" title="გლიცინი – Georgian" lang="ka" hreflang="ka" data-title="გლიცინი" data-language-autonym="ქართული" data-language-local-name="Georgian" class="interlanguage-link-target"><span>ქართული</span></a></li><li class="interlanguage-link interwiki-kk mw-list-item"><a href="https://kk.wikipedia.org/wiki/%D0%93%D0%BB%D0%B8%D1%86%D0%B8%D0%BD" title="Глицин – Kazakh" lang="kk" hreflang="kk" data-title="Глицин" data-language-autonym="Қазақша" data-language-local-name="Kazakh" class="interlanguage-link-target"><span>Қазақша</span></a></li><li class="interlanguage-link interwiki-ku mw-list-item"><a href="https://ku.wikipedia.org/wiki/Gl%C3%AEs%C3%AEn" title="Glîsîn – Kurdish" lang="ku" hreflang="ku" data-title="Glîsîn" data-language-autonym="Kurdî" data-language-local-name="Kurdish" class="interlanguage-link-target"><span>Kurdî</span></a></li><li class="interlanguage-link interwiki-ky mw-list-item"><a href="https://ky.wikipedia.org/wiki/%D0%93%D0%BB%D0%B8%D1%86%D0%B8%D0%BD" title="Глицин – Kyrgyz" lang="ky" hreflang="ky" data-title="Глицин" 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/Glycinum" title="Glycinum – Latin" lang="la" hreflang="la" data-title="Glycinum" data-language-autonym="Latina" data-language-local-name="Latin" class="interlanguage-link-target"><span>Latina</span></a></li><li class="interlanguage-link interwiki-lv mw-list-item"><a href="https://lv.wikipedia.org/wiki/Glic%C4%ABns" title="Glicīns – Latvian" lang="lv" hreflang="lv" data-title="Glicīns" data-language-autonym="Latviešu" data-language-local-name="Latvian" class="interlanguage-link-target"><span>Latviešu</span></a></li><li class="interlanguage-link interwiki-lb mw-list-item"><a href="https://lb.wikipedia.org/wiki/Glycin" title="Glycin – Luxembourgish" lang="lb" hreflang="lb" data-title="Glycin" data-language-autonym="Lëtzebuergesch" data-language-local-name="Luxembourgish" class="interlanguage-link-target"><span>Lëtzebuergesch</span></a></li><li class="interlanguage-link interwiki-lt mw-list-item"><a href="https://lt.wikipedia.org/wiki/Glicinas" title="Glicinas – Lithuanian" lang="lt" hreflang="lt" data-title="Glicinas" 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/Glicin" title="Glicin – Hungarian" lang="hu" hreflang="hu" data-title="Glicin" 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%93%D0%BB%D0%B8%D1%86%D0%B8%D0%BD" title="Глицин – Macedonian" lang="mk" hreflang="mk" data-title="Глицин" 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%97%E0%B5%8D%E0%B4%B2%E0%B5%88%E0%B4%B8%E0%B5%80%E0%B5%BB" title="ഗ്ലൈസീൻ – Malayalam" lang="ml" hreflang="ml" data-title="ഗ്ലൈസീൻ" 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/Glisina" title="Glisina – Malay" lang="ms" hreflang="ms" data-title="Glisina" data-language-autonym="Bahasa Melayu" data-language-local-name="Malay" class="interlanguage-link-target"><span>Bahasa Melayu</span></a></li><li class="interlanguage-link interwiki-mn mw-list-item"><a href="https://mn.wikipedia.org/wiki/%D0%93%D0%BB%D0%B8%D1%86%D0%B8%D0%BD" title="Глицин – Mongolian" lang="mn" hreflang="mn" data-title="Глицин" data-language-autonym="Монгол" data-language-local-name="Mongolian" class="interlanguage-link-target"><span>Монгол</span></a></li><li class="interlanguage-link interwiki-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/Glycine_(aminozuur)" title="Glycine (aminozuur) – Dutch" lang="nl" hreflang="nl" data-title="Glycine (aminozuur)" data-language-autonym="Nederlands" data-language-local-name="Dutch" class="interlanguage-link-target"><span>Nederlands</span></a></li><li class="interlanguage-link interwiki-ja mw-list-item"><a href="https://ja.wikipedia.org/wiki/%E3%82%B0%E3%83%AA%E3%82%B7%E3%83%B3" title="グリシン – Japanese" lang="ja" hreflang="ja" data-title="グリシン" data-language-autonym="日本語" data-language-local-name="Japanese" class="interlanguage-link-target"><span>日本語</span></a></li><li class="interlanguage-link interwiki-no mw-list-item"><a href="https://no.wikipedia.org/wiki/Glycin" title="Glycin – Norwegian Bokmål" lang="nb" hreflang="nb" data-title="Glycin" data-language-autonym="Norsk bokmål" data-language-local-name="Norwegian Bokmål" class="interlanguage-link-target"><span>Norsk bokmål</span></a></li><li class="interlanguage-link interwiki-nn mw-list-item"><a href="https://nn.wikipedia.org/wiki/Glysin" title="Glysin – Norwegian Nynorsk" lang="nn" hreflang="nn" data-title="Glysin" data-language-autonym="Norsk nynorsk" data-language-local-name="Norwegian Nynorsk" class="interlanguage-link-target"><span>Norsk nynorsk</span></a></li><li class="interlanguage-link interwiki-oc mw-list-item"><a href="https://oc.wikipedia.org/wiki/Glicina" title="Glicina – Occitan" lang="oc" hreflang="oc" data-title="Glicina" 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/Glitsin" title="Glitsin – Uzbek" lang="uz" hreflang="uz" data-title="Glitsin" 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/Glicyna" title="Glicyna – Polish" lang="pl" hreflang="pl" data-title="Glicyna" 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/Glicina" title="Glicina – Portuguese" lang="pt" hreflang="pt" data-title="Glicina" 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/Glicin%C4%83" title="Glicină – Romanian" lang="ro" hreflang="ro" data-title="Glicină" 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%BB%D0%B8%D1%86%D0%B8%D0%BD" title="Глицин – Russian" lang="ru" hreflang="ru" data-title="Глицин" 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/Glycine" title="Glycine – Scots" lang="sco" hreflang="sco" data-title="Glycine" data-language-autonym="Scots" data-language-local-name="Scots" class="interlanguage-link-target"><span>Scots</span></a></li><li class="interlanguage-link interwiki-scn mw-list-item"><a href="https://scn.wikipedia.org/wiki/Glicina" title="Glicina – Sicilian" lang="scn" hreflang="scn" data-title="Glicina" data-language-autonym="Sicilianu" data-language-local-name="Sicilian" class="interlanguage-link-target"><span>Sicilianu</span></a></li><li class="interlanguage-link interwiki-sk mw-list-item"><a href="https://sk.wikipedia.org/wiki/Glyc%C3%ADn" title="Glycín – Slovak" lang="sk" hreflang="sk" data-title="Glycín" 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/Glicin" title="Glicin – Slovenian" lang="sl" hreflang="sl" data-title="Glicin" data-language-autonym="Slovenščina" data-language-local-name="Slovenian" class="interlanguage-link-target"><span>Slovenščina</span></a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/%D0%93%D0%BB%D0%B8%D1%86%D0%B8%D0%BD" title="Глицин – Serbian" lang="sr" hreflang="sr" data-title="Глицин" 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/Glicin" title="Glicin – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Glicin" data-language-autonym="Srpskohrvatski / српскохрватски" data-language-local-name="Serbo-Croatian" class="interlanguage-link-target"><span>Srpskohrvatski / српскохрватски</span></a></li><li class="interlanguage-link interwiki-su mw-list-item"><a href="https://su.wikipedia.org/wiki/Glisin" title="Glisin – Sundanese" lang="su" hreflang="su" data-title="Glisin" data-language-autonym="Sunda" data-language-local-name="Sundanese" class="interlanguage-link-target"><span>Sunda</span></a></li><li class="interlanguage-link interwiki-fi mw-list-item"><a href="https://fi.wikipedia.org/wiki/Glysiini" title="Glysiini – Finnish" lang="fi" hreflang="fi" data-title="Glysiini" 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/Glycin" title="Glycin – Swedish" lang="sv" hreflang="sv" data-title="Glycin" data-language-autonym="Svenska" data-language-local-name="Swedish" class="interlanguage-link-target"><span>Svenska</span></a></li><li class="interlanguage-link interwiki-ta mw-list-item"><a href="https://ta.wikipedia.org/wiki/%E0%AE%95%E0%AE%BF%E0%AE%B3%E0%AF%88%E0%AE%9A%E0%AE%BF%E0%AE%A9%E0%AF%8D" title="கிளைசின் – Tamil" lang="ta" hreflang="ta" data-title="கிளைசின்" 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%97%E0%B1%8D%E0%B0%B2%E0%B1%88%E0%B0%B8%E0%B1%80%E0%B0%A8%E0%B1%8D" title="గ్లైసీన్ – Telugu" lang="te" hreflang="te" data-title="గ్లైసీన్" 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%B9%84%E0%B8%81%E0%B8%A5%E0%B8%8B%E0%B8%B5%E0%B8%99" title="ไกลซีน – Thai" lang="th" hreflang="th" data-title="ไกลซีน" data-language-autonym="ไทย" data-language-local-name="Thai" class="interlanguage-link-target"><span>ไทย</span></a></li><li class="interlanguage-link interwiki-tg mw-list-item"><a href="https://tg.wikipedia.org/wiki/%D0%93%D0%BB%D0%B8%D1%82%D1%81%D0%B8%D0%BD" title="Глитсин – Tajik" lang="tg" hreflang="tg" data-title="Глитсин" data-language-autonym="Тоҷикӣ" data-language-local-name="Tajik" class="interlanguage-link-target"><span>Тоҷикӣ</span></a></li><li class="interlanguage-link interwiki-tr mw-list-item"><a href="https://tr.wikipedia.org/wiki/Glisin" title="Glisin – Turkish" lang="tr" hreflang="tr" data-title="Glisin" 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%D0%BB%D1%96%D1%86%D0%B8%D0%BD" title="Гліцин – Ukrainian" lang="uk" hreflang="uk" data-title="Гліцин" 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/Glycin" title="Glycin – Vietnamese" lang="vi" hreflang="vi" data-title="Glycin" 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-vls mw-list-item"><a href="https://vls.wikipedia.org/wiki/Glycine" title="Glycine – West Flemish" lang="vls" hreflang="vls" data-title="Glycine" data-language-autonym="West-Vlams" data-language-local-name="West Flemish" class="interlanguage-link-target"><span>West-Vlams</span></a></li><li class="interlanguage-link interwiki-war mw-list-item"><a href="https://war.wikipedia.org/wiki/Glycin" title="Glycin – Waray" lang="war" hreflang="war" data-title="Glycin" 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%94%98%E6%B0%A8%E9%85%B8" title="甘氨酸 – Wu" lang="wuu" hreflang="wuu" data-title="甘氨酸" 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%94%98%E6%B0%A8%E9%85%B8" title="甘氨酸 – Cantonese" lang="yue" hreflang="yue" data-title="甘氨酸" data-language-autonym="粵語" data-language-local-name="Cantonese" class="interlanguage-link-target"><span>粵語</span></a></li><li class="interlanguage-link interwiki-zh mw-list-item"><a href="https://zh.wikipedia.org/wiki/%E7%94%98%E6%B0%A8%E9%85%B8" title="甘氨酸 – Chinese" lang="zh" hreflang="zh" data-title="甘氨酸" data-language-autonym="中文" data-language-local-name="Chinese" class="interlanguage-link-target"><span>中文</span></a></li> </ul> <div class="after-portlet after-portlet-lang"><span class="wb-langlinks-edit wb-langlinks-link"><a href="https://www.wikidata.org/wiki/Special:EntityPage/Q620730#sitelinks-wikipedia" title="Edit interlanguage links" class="wbc-editpage">Edit links</a></span></div> </div> 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.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-Technical plainlinks metadata ambox ambox-style ambox-technical" role="presentation"><tbody><tr><td class="mbox-image"><div class="mbox-image-div"><span typeof="mw:File"><span><img alt="" src="//upload.wikimedia.org/wikipedia/en/thumb/f/f2/Edit-clear.svg/40px-Edit-clear.svg.png" decoding="async" width="40" height="40" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/f2/Edit-clear.svg/60px-Edit-clear.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/f2/Edit-clear.svg/80px-Edit-clear.svg.png 2x" data-file-width="48" data-file-height="48" /></span></span></div></td><td class="mbox-text"><div class="mbox-text-span">This article's lead section <b>may be too technical for most readers to understand</b>.<span class="hide-when-compact"> Please <a class="external text" href="https://en.wikipedia.org/w/index.php?title=Glycine&action=edit">help improve it</a> to <a href="/wiki/Wikipedia:Make_technical_articles_understandable" title="Wikipedia:Make technical articles understandable">make it understandable to non-experts</a>, without removing the technical details.</span> <span class="date-container"><i>(<span class="date">February 2025</span>)</i></span><span class="hide-when-compact"><i> (<small><a href="/wiki/Help:Maintenance_template_removal" title="Help:Maintenance template removal">Learn how and when to remove this message</a></small>)</i></span></div></td></tr></tbody></table> <div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Amino acid</div> <p class="mw-empty-elt"> </p> <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 other uses, see <a href="/wiki/Glycine_(disambiguation)" class="mw-disambig" title="Glycine (disambiguation)">Glycine (disambiguation)</a>.</div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951" /><div role="note" class="hatnote navigation-not-searchable">Not to be confused with <a href="/wiki/Glycerin" class="mw-redirect" title="Glycerin">Glycerin</a>.</div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951" /><div role="note" class="hatnote navigation-not-searchable">"Gly" redirects here. For other uses, see <a href="/wiki/Gly_(disambiguation)" class="mw-disambig" title="Gly (disambiguation)">Gly (disambiguation)</a>.</div> <p> <style data-mw-deduplicate="TemplateStyles:r1268415487">.mw-parser-output .ib-chembox{border-collapse:collapse;text-align:left}.mw-parser-output .ib-chembox td,.mw-parser-output .ib-chembox th{border:1px solid #a2a9b1;width:40%}.mw-parser-output .ib-chembox td+td{width:60%}@media screen{html.skin-theme-clientpref-night .mw-parser-output .ib-chembox figure:not(.skin-invert-image):not(.skin-invert):not(.bg-transparent){background:var(--background-color-inverted,#f8f9fa)}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .ib-chembox figure:not(.skin-invert-image):not(.skin-invert):not(.bg-transparent){background:var(--background-color-inverted,#f8f9fa)}}</style> </p> <table class="infobox ib-chembox"> <caption>Glycine<sup id="cite_ref-1" class="reference"><a href="#cite_note-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> </caption> <tbody><tr> <td colspan="2" class="borderless" style="text-align:center"> <table border="0" style="width:100%;display:inline-table;"> <tbody><tr> <td style="border-right:1px solid #aaa; width:50%;"><figure class="mw-halign-center skin-invert-image" typeof="mw:File"><a href="/wiki/File:Glycine-2D-skeletal.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/1/18/Glycine-2D-skeletal.svg/120px-Glycine-2D-skeletal.svg.png" decoding="async" width="120" height="69" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/1/18/Glycine-2D-skeletal.svg/250px-Glycine-2D-skeletal.svg.png 1.5x" data-file-width="1100" data-file-height="631" /></a><figcaption></figcaption></figure><div style="text-align:center"><a href="/wiki/Skeletal_formula" title="Skeletal formula">Skeletal formula</a> of neutral glycine</div> </td> <td style="width:50%;"><figure class="mw-halign-center skin-invert-image" typeof="mw:File"><a href="/wiki/File:Glycine-zwitterion-2D-skeletal.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/b/b8/Glycine-zwitterion-2D-skeletal.svg/120px-Glycine-zwitterion-2D-skeletal.svg.png" decoding="async" width="120" height="68" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/b/b8/Glycine-zwitterion-2D-skeletal.svg/250px-Glycine-zwitterion-2D-skeletal.svg.png 1.5x" data-file-width="380" data-file-height="214" /></a><figcaption></figcaption></figure><div style="text-align:center">Skeletal formula of <a href="/wiki/Zwitterion" title="Zwitterion">zwitterionic</a> glycine</div> </td></tr></tbody></table> </td></tr> <tr> <td colspan="2" class="borderless" style="text-align:center"> <table border="0" style="width:100%;display:inline-table;"> <tbody><tr> <td style="border-right:1px solid #aaa; width:50%;"><figure class="mw-halign-center bg-transparent" typeof="mw:File"><a href="/wiki/File:Glycine-neutral-Ipttt-conformer-3D-bs-17.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/0/01/Glycine-neutral-Ipttt-conformer-3D-bs-17.png/120px-Glycine-neutral-Ipttt-conformer-3D-bs-17.png" decoding="async" width="120" height="80" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/0/01/Glycine-neutral-Ipttt-conformer-3D-bs-17.png/250px-Glycine-neutral-Ipttt-conformer-3D-bs-17.png 1.5x" data-file-width="2983" data-file-height="2000" /></a><figcaption></figcaption></figure><div style="text-align:center"><a href="/wiki/Ball-and-stick_model" title="Ball-and-stick model">Ball-and-stick model</a> of the gas-phase structure</div> </td> <td style="width:50%;"><figure class="mw-halign-center bg-transparent" typeof="mw:File"><a href="/wiki/File:Glycine-zwitterion-from-xtal-3D-bs-17.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/9/9e/Glycine-zwitterion-from-xtal-3D-bs-17.png/120px-Glycine-zwitterion-from-xtal-3D-bs-17.png" decoding="async" width="120" height="86" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/9/9e/Glycine-zwitterion-from-xtal-3D-bs-17.png/250px-Glycine-zwitterion-from-xtal-3D-bs-17.png 1.5x" data-file-width="3000" data-file-height="2150" /></a><figcaption></figcaption></figure><div style="text-align:center">Ball-and-stick model of the zwitterionic solid-state structure</div> </td></tr></tbody></table> </td></tr> <tr> <td colspan="2" class="borderless" style="text-align:center"> <table border="0" style="width:100%;display:inline-table;"> <tbody><tr> <td style="border-right:1px solid #aaa; width:50%;"><figure class="mw-halign-center bg-transparent" typeof="mw:File"><a href="/wiki/File:Glycine-neutral-Ipttt-conformer-3D-sf.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/9/9d/Glycine-neutral-Ipttt-conformer-3D-sf.png/120px-Glycine-neutral-Ipttt-conformer-3D-sf.png" decoding="async" width="120" height="96" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/9/9d/Glycine-neutral-Ipttt-conformer-3D-sf.png/180px-Glycine-neutral-Ipttt-conformer-3D-sf.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/9/9d/Glycine-neutral-Ipttt-conformer-3D-sf.png/240px-Glycine-neutral-Ipttt-conformer-3D-sf.png 2x" data-file-width="2950" data-file-height="2351" /></a><figcaption></figcaption></figure><div style="text-align:center"><a href="/wiki/Space-filling_model" title="Space-filling model">Space-filling model</a> of the gas-phase structure</div> </td> <td style="width:50%;"><figure class="mw-halign-center bg-transparent" typeof="mw:File"><a href="/wiki/File:Glycine-zwitterion-from-xtal-3D-sf.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/f/fa/Glycine-zwitterion-from-xtal-3D-sf.png/120px-Glycine-zwitterion-from-xtal-3D-sf.png" decoding="async" width="120" height="97" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/f/fa/Glycine-zwitterion-from-xtal-3D-sf.png/250px-Glycine-zwitterion-from-xtal-3D-sf.png 1.5x" data-file-width="2973" data-file-height="2408" /></a><figcaption></figcaption></figure><div style="text-align:center">Space-filling model of the zwitterionic solid-state structure</div> </td></tr></tbody></table> </td></tr> <tr> <th colspan="2" style="background: #f8eaba;color:inherit; text-align: center;">Names </th></tr> <tr> <td colspan="2" style="text-align:left;"><a href="/wiki/Chemical_nomenclature" title="Chemical nomenclature">IUPAC name</a> <div style="max-width:22em; word-wrap:break-word; padding-left:1.7em;">Glycine</div> </td></tr> <tr> <td colspan="2" style="text-align:left;"><a href="/wiki/Chemical_nomenclature#Systematic_name" title="Chemical nomenclature">Systematic IUPAC name</a> <div style="max-width:22em; word-wrap:break-word; padding-left:1.7em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0; max-width:22em;">Aminoacetic acid<sup id="cite_ref-2" class="reference"><a href="#cite_note-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup></div></div> </td></tr> <tr> <td colspan="2" style="text-align:left;">Other names <div style="max-width:22em; word-wrap:break-word; padding-left:1.7em;"><style data-mw-deduplicate="TemplateStyles:r1126788409">.mw-parser-output .plainlist ol,.mw-parser-output .plainlist ul{line-height:inherit;list-style:none;margin:0;padding:0}.mw-parser-output .plainlist ol li,.mw-parser-output .plainlist ul li{margin-bottom:0}</style><div class="plainlist"><ul><li>2-Aminoethanoic acid</li><li>Glycocol</li><li>Glycic acid</li><li>Dicarbamic acid</li></ul></div></div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba;color:inherit; text-align: center;">Identifiers </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/CAS_Registry_Number" title="CAS Registry Number">CAS Number</a></div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><span title="commonchemistry.cas.org"><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=56-40-6">56-40-6</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><li><span title="commonchemistry.cas.org"><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=6000-43-7">6000-43-7</a></span> (<a href="/wiki/Hydrochloride" title="Hydrochloride">HCl salt</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></sup></li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">3D model (<a href="/wiki/JSmol" class="mw-redirect" title="JSmol">JSmol</a>)</div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><span title="chemapps.stolaf.edu (3D interactive model)"><a rel="nofollow" class="external text" href="https://chemapps.stolaf.edu/jmol/jmol.php?model=C%28C%28%3DO%29O%29N">Interactive image</a></span></li><li><a href="/wiki/Zwitterion" title="Zwitterion">Zwitterion</a>: <span title="chemapps.stolaf.edu (3D interactive model)"><a rel="nofollow" class="external text" href="https://chemapps.stolaf.edu/jmol/jmol.php?model=C%28C%28%3DO%29%5BO-%5D%29%5BNH3%2B%5D">Interactive image</a></span></li><li><span title="chemapps.stolaf.edu (3D interactive model)"><a rel="nofollow" class="external text" href="https://chemapps.stolaf.edu/jmol/jmol.php?model=C%28C%28%3DO%29O%29N.Cl">Interactive image</a></span></li></ul></div> </td></tr> <tr> <td>Abbreviations </td> <td><b>Gly</b>, <b>G</b> </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=15428">CHEBI:15428</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/ChEMBL773">ChEMBL773</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.730.html">730</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li><li><span title="www.chemspider.com"><a rel="nofollow" class="external text" href="https://www.chemspider.com/Chemical-Structure.20944.html">20944</a></span></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/DB00145">DB00145</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ECHA_InfoCard" class="mw-redirect" title="ECHA InfoCard"><span title="echa.europa.eu">ECHA InfoCard</span></a> </td> <td><a rel="nofollow" class="external text" href="https://echa.europa.eu/substance-information/-/substanceinfo/100.000.248">100.000.248</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q620730#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/20px-OOjs_UI_icon_edit-ltr-progressive.svg.png" decoding="async" width="10" height="10" class="mw-file-element" data-file-width="20" data-file-height="20" /></a></span> </td></tr> <tr> <td><a href="/wiki/European_Community_number" title="European Community number"><span title="European Community number (chemical identifier)">EC Number</span></a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li>200-272-2</li><li>227-841-8</li></ul></div> </td></tr> <tr> <td><a href="/wiki/E_number" title="E number"><span title="E number (food additive code)">E number</span></a> </td> <td>E640 <a href="/wiki/E_number#E600–E699" title="E number">(flavour enhancer)</a> </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=727">727</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/D00011">D00011</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/PubChem" title="PubChem">PubChem</a> <abbr title="Compound ID">CID</abbr></div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><span title="pubchem.ncbi.nlm.nih.gov"><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/750">750</a></span></li><li><span title="pubchem.ncbi.nlm.nih.gov"><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/22316">22316</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/TE7660XO1C">TE7660XO1C</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li><li><span title="precision.fda.gov"><a rel="nofollow" class="external text" href="https://precision.fda.gov/uniisearch/srs/unii/225ZLC74HX">225ZLC74HX</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/DTXSID9020667">DTXSID9020667</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q620730#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/20px-OOjs_UI_icon_edit-ltr-progressive.svg.png" decoding="async" width="10" height="10" class="mw-file-element" data-file-width="20" data-file-height="20" /></a></span></span></li></ul></div> </td></tr> <tr> <td colspan="2"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold; text-align:left; font-weight:normal;"><div><a href="/wiki/International_Chemical_Identifier" title="International Chemical Identifier">InChI</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.5em; text-align:left;"><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">InChI=1S/C2H5NH2/c3-1-2(4)5/h1,3H2,(H,4,5)<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: DHMQDGOQFOQNFH-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=1S/C2H5NO2/c3-1-2(4)5/h1,3H2,(H,4,5)</div><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">Key: DHMQDGOQFOQNFH-UHFFFAOYAW</div></div></li></ul> </div> </td></tr> <tr> <td colspan="2"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold; text-align:left; font-weight:normal;"><div><a href="/wiki/Simplified_molecular-input_line-entry_system" class="mw-redirect" title="Simplified molecular-input line-entry system">SMILES</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.6em; word-wrap:break-word; text-indent:-1.5em; text-align:left; font-size:97%; line-height:120%;">C(C(=O)O)N</div></li><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.6em; word-wrap:break-word; text-indent:-1.5em; text-align:left; font-size:97%; line-height:120%;"><a href="/wiki/Zwitterion" title="Zwitterion">Zwitterion</a>: C(C(=O)[O-])[NH3+]</div></li><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.6em; word-wrap:break-word; text-indent:-1.5em; text-align:left; font-size:97%; line-height:120%;">C(C(=O)O)N.Cl</div></li></ul> </div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba;color:inherit; text-align: center;">Properties </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Chemical_formula" title="Chemical formula">Chemical formula</a></div> </td> <td><span title="Carbon">C</span><sub>2</sub><span title="Hydrogen">H</span><sub>5</sub><span title="Nitrogen">N</span><span title="Oxygen">O</span><sub>2</sub> </td></tr> <tr> <td><a href="/wiki/Molar_mass" title="Molar mass">Molar mass</a> </td> <td><span class="nowrap"><span data-sort-value="7001750669999999999♠"></span>75.067</span> g·mol<sup>−1</sup>   </td></tr> <tr> <td>Appearance </td> <td>White solid </td></tr> <tr> <td><a href="/wiki/Density" title="Density">Density</a> </td> <td>1.1607 g/cm<sup>3</sup><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> </td></tr> <tr> <td><a href="/wiki/Melting_point" title="Melting point">Melting point</a> </td> <td>233 °C (451 °F; 506 K) (decomposition) </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>249.9 g/L (25 °C)<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> </td></tr> <tr> <td><a href="/wiki/Solubility" title="Solubility">Solubility</a> </td> <td>soluble in <a href="/wiki/Pyridine" title="Pyridine">pyridine</a> <br /> sparingly soluble in <a href="/wiki/Ethanol" title="Ethanol">ethanol</a> <br /> insoluble in <a href="/wiki/Diethyl_ether" title="Diethyl ether">ether</a> </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>2.34 (carboxyl), 9.6 (amino)<sup id="cite_ref-5" class="reference"><a href="#cite_note-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Magnetic_susceptibility" title="Magnetic susceptibility">Magnetic susceptibility</a> (χ)</div> </td> <td>−40.3·10<sup>−6</sup> cm<sup>3</sup>/mol </td></tr> <tr> <th colspan="2" style="background: #f8eaba;color:inherit; 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_B05" title="ATC code B05">B05CX03</a> (<span title="www.whocc.no"><a rel="nofollow" class="external text" href="https://www.whocc.no/atc_ddd_index/?code=B05CX03">WHO</a></span>)  </td></tr> <tr> <th colspan="2" style="background: #f8eaba;color:inherit; text-align: center;">Hazards </th></tr> <tr> <td colspan="2" style="text-align:left; background-color:#eaeaea;color:inherit;"><b>Lethal dose</b> or concentration (LD, LC): </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">LD<sub>50</sub> (<a href="/wiki/Lethal_dose#LD50" title="Lethal dose">median dose</a>)</div> </td> <td>2600 mg/kg (mouse, oral) </td></tr> <tr> <th colspan="2" style="background: #f8eaba;color:inherit; text-align: center;">Supplementary data page </th></tr> <tr> <td colspan="2" style="text-align:center"><a href="/wiki/Glycine_(data_page)" title="Glycine (data page)">Glycine (data page)</a> </td></tr> <tr> <td colspan="2" style="text-align:left; background:#f8eaba; color:inherit; border:1px solid #a2a9b1;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">Except where otherwise noted, data are given for materials in their <a href="/wiki/Standard_state" title="Standard state">standard state</a> (at 25 °C [77 °F], 100 kPa).</div> <div style="margin-top: 0.3em;"><div style="text-align:center;"><span typeof="mw:File"><span><img alt="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=464190930&page2=Glycine">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> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:Glycine-spin.gif" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/9/9e/Glycine-spin.gif/250px-Glycine-spin.gif" decoding="async" width="220" height="220" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/9/9e/Glycine-spin.gif/330px-Glycine-spin.gif 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/9/9e/Glycine-spin.gif/440px-Glycine-spin.gif 2x" data-file-width="480" data-file-height="480" /></a><figcaption>L-Glycine ball and stick model spinning</figcaption></figure> <p><b>Glycine</b> (symbol <b>Gly</b> or <b>G</b>;<sup id="cite_ref-6" class="reference"><a href="#cite_note-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> <span class="rt-commentedText nowrap"><span class="IPA nopopups noexcerpt" lang="en-fonipa"><a href="/wiki/Help:IPA/English" title="Help:IPA/English">/<span style="border-bottom:1px dotted"><span title="/ˈ/: primary stress follows">ˈ</span><span title="/ɡ/: 'g' in 'guy'">ɡ</span><span title="'l' in 'lie'">l</span><span title="/aɪ/: 'i' in 'tide'">aɪ</span><span title="'s' in 'sigh'">s</span><span title="/iː/: 'ee' in 'fleece'">iː</span><span title="'n' in 'nigh'">n</span></span>/</a></span> <span class="ext-phonos"><span data-nosnippet="" id="ooui-php-1" class="noexcerpt ext-phonos-PhonosButton ext-phonos-PhonosButton-emptylabel oo-ui-widget oo-ui-widget-enabled oo-ui-buttonElement oo-ui-buttonElement-frameless oo-ui-iconElement oo-ui-buttonWidget" data-ooui="{"_":"mw.Phonos.PhonosButton","href":"\/\/upload.wikimedia.org\/wikipedia\/commons\/transcoded\/8\/84\/En-us-Glycine.ogg\/En-us-Glycine.ogg.mp3","rel":["nofollow"],"framed":false,"icon":"volumeUp","data":{"ipa":"","text":"","lang":"en","wikibase":"","file":"En-us-Glycine.ogg"},"classes":["noexcerpt","ext-phonos-PhonosButton","ext-phonos-PhonosButton-emptylabel"]}"><a role="button" tabindex="0" href="//upload.wikimedia.org/wikipedia/commons/transcoded/8/84/En-us-Glycine.ogg/En-us-Glycine.ogg.mp3" rel="nofollow" aria-label="Play audio" title="Play audio" class="oo-ui-buttonElement-button"><span class="oo-ui-iconElement-icon oo-ui-icon-volumeUp"></span><span class="oo-ui-labelElement-label"></span><span class="oo-ui-indicatorElement-indicator oo-ui-indicatorElement-noIndicator"></span></a></span><sup class="ext-phonos-attribution noexcerpt navigation-not-searchable"><a href="/wiki/File:En-us-Glycine.ogg" title="File:En-us-Glycine.ogg">ⓘ</a></sup></span></span>)<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> is an <a href="/wiki/Amino_acid" title="Amino acid">amino acid</a> that has a single <a href="/wiki/Hydrogen" title="Hydrogen">hydrogen</a> atom as its <a href="/wiki/Side_chain" title="Side chain">side chain</a>. It is the simplest stable amino acid. Glycine is one of the <a href="/wiki/Proteinogenic_amino_acid" title="Proteinogenic amino acid">proteinogenic amino acids</a>. It is <a href="/wiki/Genetic_code" title="Genetic code">encoded</a> by all the <a href="/wiki/Codon" class="mw-redirect" title="Codon">codons</a> starting with GG (GGU, GGC, GGA, GGG).<sup id="cite_ref-:3_8-0" class="reference"><a href="#cite_note-:3-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> Glycine is integral to the formation of <a href="/wiki/Alpha_helix" title="Alpha helix">alpha-helices</a> in <a href="/wiki/Secondary_protein_structure" class="mw-redirect" title="Secondary protein structure">secondary protein structure</a> due to the <a href="/wiki/Molecular_geometry" title="Molecular geometry">"flexibility"</a> caused by such a small R group. Glycine is also an inhibitory <a href="/wiki/Neurotransmitter" title="Neurotransmitter">neurotransmitter</a><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> – interference with its release within the spinal cord (such as during a <i><a href="/wiki/Clostridium_tetani" title="Clostridium tetani">Clostridium tetani</a></i> infection) can cause <a href="/wiki/Spasticity" title="Spasticity">spastic</a> paralysis due to uninhibited muscle contraction.<sup id="cite_ref-10" class="reference"><a href="#cite_note-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> </p><p>It is the only <a href="/wiki/Chirality_(chemistry)" title="Chirality (chemistry)">achiral</a> <a href="/wiki/Proteinogenic_amino_acid" title="Proteinogenic amino acid">proteinogenic amino acid</a>.<sup id="cite_ref-11" class="reference"><a href="#cite_note-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> It can fit into both <a href="/wiki/Hydrophile" title="Hydrophile">hydrophilic</a> and <a href="/wiki/Hydrophobe" title="Hydrophobe">hydrophobic</a> environments, due to its minimal side chain of only one hydrogen atom.<sup id="cite_ref-12" class="reference"><a href="#cite_note-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup> </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="History_and_etymology">History and etymology</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Glycine&action=edit&section=1" title="Edit section: History and etymology"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Glycine was discovered in 1820 by French chemist <a href="/wiki/Henri_Braconnot" title="Henri Braconnot">Henri Braconnot</a> when he hydrolyzed <a href="/wiki/Gelatin" title="Gelatin">gelatin</a> by boiling it with <a href="/wiki/Sulfuric_acid" title="Sulfuric acid">sulfuric acid</a>.<sup id="cite_ref-13" class="reference"><a href="#cite_note-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup> He originally called it "sugar of gelatin",<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><sup id="cite_ref-15" class="reference"><a href="#cite_note-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup> but French chemist <a href="/wiki/Jean-Baptiste_Boussingault" title="Jean-Baptiste Boussingault">Jean-Baptiste Boussingault</a> showed in 1838 that it contained nitrogen.<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> In 1847 American scientist <a href="/wiki/Eben_Norton_Horsford" title="Eben Norton Horsford">Eben Norton Horsford</a>, then a student of the German chemist <a href="/wiki/Justus_von_Liebig" title="Justus von Liebig">Justus von Liebig</a>, proposed the name "glycocoll";<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><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> however, the <a href="/wiki/Sweden" title="Sweden">Swedish</a> chemist <a href="/wiki/J%C3%B6ns_Jacob_Berzelius" title="Jöns Jacob Berzelius">Berzelius</a> suggested the simpler current name a year later.<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><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> The name comes from the <a href="/wiki/Ancient_Greek" title="Ancient Greek">Greek</a> word γλυκύς "sweet tasting"<sup id="cite_ref-21" class="reference"><a href="#cite_note-21"><span class="cite-bracket">[</span>21<span class="cite-bracket">]</span></a></sup> (which is also related to the prefixes <i><a href="https://en.wiktionary.org/wiki/glyco-#Prefix" class="extiw" title="wikt:glyco-">glyco-</a></i> and <i><a href="https://en.wiktionary.org/wiki/gluco-#Prefix" class="extiw" title="wikt:gluco-">gluco-</a></i>, as in <i><a href="/wiki/Glycoprotein" title="Glycoprotein">glycoprotein</a></i> and <i><a href="/wiki/Glucose" title="Glucose">glucose</a></i>). In 1858, the French chemist <a href="/wiki/Auguste_Andr%C3%A9_Thomas_Cahours" title="Auguste André Thomas Cahours">Auguste Cahours</a> determined that glycine was an <a href="/wiki/Amine" title="Amine">amine</a> of <a href="/wiki/Acetic_acid" title="Acetic acid">acetic acid</a>.<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="Production">Production</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Glycine&action=edit&section=2" title="Edit section: Production"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Although glycine can be isolated from <a href="/wiki/Hydrolyzed_protein" title="Hydrolyzed protein">hydrolyzed proteins</a>, this route is not used for industrial production, as it can be manufactured more conveniently by chemical synthesis.<sup id="cite_ref-23" class="reference"><a href="#cite_note-23"><span class="cite-bracket">[</span>23<span class="cite-bracket">]</span></a></sup> The two main processes are <a href="/wiki/Amination" title="Amination">amination</a> of <a href="/wiki/Chloroacetic_acid" title="Chloroacetic acid">chloroacetic acid</a> with <a href="/wiki/Ammonia" title="Ammonia">ammonia</a>, giving glycine and <a href="/wiki/Hydrochloric_acid" title="Hydrochloric acid">hydrochloric acid</a>,<sup id="cite_ref-24" class="reference"><a href="#cite_note-24"><span class="cite-bracket">[</span>24<span class="cite-bracket">]</span></a></sup> and the <a href="/wiki/Strecker_amino_acid_synthesis" title="Strecker amino acid synthesis">Strecker amino acid synthesis</a>,<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> which is the main synthetic method in the United States and Japan.<sup id="cite_ref-usitc.gov_26-0" class="reference"><a href="#cite_note-usitc.gov-26"><span class="cite-bracket">[</span>26<span class="cite-bracket">]</span></a></sup> About 15 thousand <a href="/wiki/Tonne" title="Tonne">tonnes</a> are produced annually in this way.<sup id="cite_ref-Ull_27-0" class="reference"><a href="#cite_note-Ull-27"><span class="cite-bracket">[</span>27<span class="cite-bracket">]</span></a></sup> </p><p>Glycine is also co-generated as an impurity in the synthesis of <a href="/wiki/EDTA" class="mw-redirect" title="EDTA">EDTA</a>, arising from reactions of the ammonia co-product.<sup id="cite_ref-Ullmann/Roger_28-0" class="reference"><a href="#cite_note-Ullmann/Roger-28"><span class="cite-bracket">[</span>28<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Chemical_reactions">Chemical reactions</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Glycine&action=edit&section=3" title="Edit section: Chemical reactions"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Its acid–base properties are most important. In aqueous solution, glycine is <a href="/wiki/Amphoteric" class="mw-redirect" title="Amphoteric">amphoteric</a>: below pH = 2.4, it converts to the ammonium cation called glycinium. Above about pH 9.6, it converts to glycinate. </p> <dl><dd><span class="skin-invert-image" typeof="mw:File"><a href="/wiki/File:Glycine-protonation-states-2D-skeletal.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/1/14/Glycine-protonation-states-2D-skeletal.png/540px-Glycine-protonation-states-2D-skeletal.png" decoding="async" width="540" height="154" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/1/14/Glycine-protonation-states-2D-skeletal.png/810px-Glycine-protonation-states-2D-skeletal.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/1/14/Glycine-protonation-states-2D-skeletal.png/1080px-Glycine-protonation-states-2D-skeletal.png 2x" data-file-width="2100" data-file-height="600" /></a></span></dd></dl> <p>Glycine functions as a <a href="/wiki/Bidentate_ligand" class="mw-redirect" title="Bidentate ligand">bidentate ligand</a> for many metal ions, forming <a href="/wiki/Amino_acid_complex" class="mw-redirect" title="Amino acid complex">amino acid complexes</a>.<sup id="cite_ref-29" class="reference"><a href="#cite_note-29"><span class="cite-bracket">[</span>29<span class="cite-bracket">]</span></a></sup> A typical complex is Cu(glycinate)<sub>2</sub>, i.e. Cu(H<sub>2</sub>NCH<sub>2</sub>CO<sub>2</sub>)<sub>2</sub>, which exists both in cis and trans isomers.<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><sup id="cite_ref-31" class="reference"><a href="#cite_note-31"><span class="cite-bracket">[</span>31<span class="cite-bracket">]</span></a></sup> </p><p>With acid chlorides, glycine converts to the amidocarboxylic acid, such as <a href="/wiki/Hippuric_acid" title="Hippuric acid">hippuric acid</a><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> and <a href="/wiki/Acetylglycine" class="mw-redirect" title="Acetylglycine">acetylglycine</a>.<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> With <a href="/wiki/Nitrous_acid" title="Nitrous acid">nitrous acid</a>, one obtains <a href="/wiki/Glycolic_acid" title="Glycolic acid">glycolic acid</a> (<a href="/wiki/Van_Slyke_determination" title="Van Slyke determination">van Slyke determination</a>). With <a href="/wiki/Methyl_iodide" class="mw-redirect" title="Methyl iodide">methyl iodide</a>, the amine becomes <a href="/wiki/Quaternary_compound" title="Quaternary compound">quaternized</a> to give <a href="/wiki/Trimethylglycine" title="Trimethylglycine">trimethylglycine</a>, a natural product: </p> <dl><dd><span class="chemf nowrap">H<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline"></sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">3</sub></span></span>N<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:0.8em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline">+</sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline"></sub></span></span>CH<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline"></sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">2</sub></span></span>COO<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:0.8em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline">−</sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline"></sub></span></span></span> + 3 CH<sub>3</sub>I → <span class="chemf nowrap">(CH<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline"></sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">3</sub></span></span>)<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline"></sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">3</sub></span></span>N<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:0.8em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline">+</sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline"></sub></span></span>CH<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline"></sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">2</sub></span></span>COO<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:0.8em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline">−</sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline"></sub></span></span></span> + 3 HI</dd></dl> <p>Glycine condenses with itself to give peptides, beginning with the formation of <a href="/wiki/Glycylglycine" title="Glycylglycine">glycylglycine</a>:<sup id="cite_ref-34" class="reference"><a href="#cite_note-34"><span class="cite-bracket">[</span>34<span class="cite-bracket">]</span></a></sup> </p> <dl><dd>2 <span class="chemf nowrap">H<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline"></sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">3</sub></span></span>N<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:0.8em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline">+</sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline"></sub></span></span>CH<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline"></sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">2</sub></span></span>COO<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:0.8em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline">−</sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline"></sub></span></span></span> → <span class="chemf nowrap">H<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline"></sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">3</sub></span></span>N<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:0.8em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline">+</sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline"></sub></span></span>CH<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline"></sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">2</sub></span></span>CONHCH<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline"></sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">2</sub></span></span>COO<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:0.8em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline">−</sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline"></sub></span></span></span> + H<sub>2</sub>O</dd></dl> <p>Pyrolysis of glycine or glycylglycine gives <a href="/wiki/2,5-diketopiperazine" class="mw-redirect" title="2,5-diketopiperazine">2,5-diketopiperazine</a>, the cyclic diamide.<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>Glycine forms <a href="/wiki/Ester" title="Ester">esters</a> with <a href="/wiki/Alcohol_(chemistry)" title="Alcohol (chemistry)">alcohols</a>. They are often isolated as their <a href="/wiki/Hydrochloride" title="Hydrochloride">hydrochloride</a>, such as <a href="/wiki/Glycine_methyl_ester_hydrochloride" title="Glycine methyl ester hydrochloride">glycine methyl ester hydrochloride</a>. Otherwise, the free ester tends to convert to <a href="/wiki/Diketopiperazine" title="Diketopiperazine">diketopiperazine</a>. </p><p>As a bifunctional molecule, glycine reacts with many reagents. These can be classified into N-centered and carboxylate-center reactions. </p> <div class="mw-heading mw-heading2"><h2 id="Metabolism">Metabolism</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Glycine&action=edit&section=4" title="Edit section: Metabolism"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Biosynthesis">Biosynthesis</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Glycine&action=edit&section=5" title="Edit section: Biosynthesis"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Glycine is not <a href="/wiki/Essential_amino_acid#Essentiality_in_humans" title="Essential amino acid">essential to the human diet</a>, as it is biosynthesized in the body from the amino acid <a href="/wiki/Serine" title="Serine">serine</a>, which is in turn derived from <a href="/wiki/3-phosphoglycerate" class="mw-redirect" title="3-phosphoglycerate">3-phosphoglycerate</a>. In most organisms, the enzyme <a href="/wiki/Serine_hydroxymethyltransferase" title="Serine hydroxymethyltransferase">serine hydroxymethyltransferase</a> catalyses this transformation via the cofactor <a href="/wiki/Pyridoxal_phosphate" title="Pyridoxal phosphate">pyridoxal phosphate</a>:<sup id="cite_ref-Lehninger_36-0" class="reference"><a href="#cite_note-Lehninger-36"><span class="cite-bracket">[</span>36<span class="cite-bracket">]</span></a></sup> </p> <dl><dd>serine + <a href="/wiki/Tetrahydrofolate" class="mw-redirect" title="Tetrahydrofolate">tetrahydrofolate</a> → glycine + <a href="/wiki/5,10-Methylenetetrahydrofolate" title="5,10-Methylenetetrahydrofolate"><i>N<sup>5</sup></i>,<i>N<sup>10</sup></i>-methylene tetrahydrofolate</a> + H<sub>2</sub>O</dd></dl> <p>In <i>E. coli</i>, antibiotics that target folate depletes the supply of active tetrahydrofolates, halting glycine biosynthesis as a consequence.<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><p>In the liver of <a href="/wiki/Vertebrate" title="Vertebrate">vertebrates</a>, glycine synthesis is catalyzed by <a href="/wiki/Glycine_synthase" class="mw-redirect" title="Glycine synthase">glycine synthase</a> (also called glycine cleavage enzyme). This conversion is readily <a href="/wiki/Reversible_reaction" title="Reversible reaction">reversible</a>:<sup id="cite_ref-Lehninger_36-1" class="reference"><a href="#cite_note-Lehninger-36"><span class="cite-bracket">[</span>36<span class="cite-bracket">]</span></a></sup> </p> <dl><dd>CO<sub>2</sub> + NH<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1.2em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline">+</sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">4</sub></span></span> + <i>N<sup>5</sup></i>,<i>N<sup>10</sup></i>-methylene tetrahydrofolate + <a href="/wiki/Nicotinamide_adenine_dinucleotide" title="Nicotinamide adenine dinucleotide">NADH</a> + H<sup>+</sup> ⇌ Glycine + tetrahydrofolate + <a href="/wiki/Nicotinamide_adenine_dinucleotide" title="Nicotinamide adenine dinucleotide">NAD</a><sup>+</sup></dd></dl> <p>In addition to being synthesized from serine, glycine can also be derived from <a href="/wiki/Threonine" title="Threonine">threonine</a>, <a href="/wiki/Choline" title="Choline">choline</a> or hydroxyproline via inter-organ metabolism of the liver and kidneys.<sup id="cite_ref-38" class="reference"><a href="#cite_note-38"><span class="cite-bracket">[</span>38<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Degradation">Degradation</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Glycine&action=edit&section=6" title="Edit section: Degradation"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Glycine is degraded via three pathways. The predominant pathway in animals and plants is the reverse of the glycine synthase pathway mentioned above. In this context, the enzyme system involved is usually called the <a href="/wiki/Glycine_cleavage_system" title="Glycine cleavage system">glycine cleavage system</a>:<sup id="cite_ref-Lehninger_36-2" class="reference"><a href="#cite_note-Lehninger-36"><span class="cite-bracket">[</span>36<span class="cite-bracket">]</span></a></sup> </p> <dl><dd>Glycine + tetrahydrofolate + NAD<sup>+</sup> ⇌ CO<sub>2</sub> + NH<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1.2em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline">+</sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">4</sub></span></span> + <i>N<sup>5</sup></i>,<i>N<sup>10</sup></i>-methylene tetrahydrofolate + <a href="/wiki/NADH" class="mw-redirect" title="NADH">NADH</a> + H<sup>+</sup></dd></dl> <p>In the second pathway, glycine is degraded in two steps. The first step is the reverse of glycine biosynthesis from serine with serine hydroxymethyl transferase. Serine is then converted to <a href="/wiki/Pyruvate" class="mw-redirect" title="Pyruvate">pyruvate</a> by <a href="/wiki/Serine_dehydratase" title="Serine dehydratase">serine dehydratase</a>.<sup id="cite_ref-Lehninger_36-3" class="reference"><a href="#cite_note-Lehninger-36"><span class="cite-bracket">[</span>36<span class="cite-bracket">]</span></a></sup> </p><p>In the third pathway of its degradation, glycine is converted to <a href="/wiki/Glyoxylate" class="mw-redirect" title="Glyoxylate">glyoxylate</a> by <a href="/wiki/D-amino_acid_oxidase" title="D-amino acid oxidase">D-amino acid oxidase</a>. Glyoxylate is then oxidized by hepatic <a href="/wiki/Lactate_dehydrogenase" title="Lactate dehydrogenase">lactate dehydrogenase</a> to <a href="/wiki/Oxalate" title="Oxalate">oxalate</a> in an NAD<sup>+</sup>-dependent reaction.<sup id="cite_ref-Lehninger_36-4" class="reference"><a href="#cite_note-Lehninger-36"><span class="cite-bracket">[</span>36<span class="cite-bracket">]</span></a></sup> </p><p>The half-life of glycine and its elimination from the body varies significantly based on dose.<sup id="cite_ref-:0_39-0" class="reference"><a href="#cite_note-:0-39"><span class="cite-bracket">[</span>39<span class="cite-bracket">]</span></a></sup> In one study, the half-life varied between 0.5 and 4.0 hours.<sup id="cite_ref-:0_39-1" class="reference"><a href="#cite_note-:0-39"><span class="cite-bracket">[</span>39<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Physiological_function">Physiological function</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Glycine&action=edit&section=7" title="Edit section: Physiological function"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The principal function of glycine is it acts as a <a href="/wiki/Protein_precursor" title="Protein precursor">precursor to proteins</a>. Most proteins incorporate only small quantities of glycine, a notable exception being <a href="/wiki/Collagen" title="Collagen">collagen</a>, which contains about 35% glycine due to its periodically repeated role in the formation of collagen's helix structure in conjunction with <a href="/wiki/Hydroxyproline" title="Hydroxyproline">hydroxyproline</a>.<sup id="cite_ref-Lehninger_36-5" class="reference"><a href="#cite_note-Lehninger-36"><span class="cite-bracket">[</span>36<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-SzpakJAS_40-0" class="reference"><a href="#cite_note-SzpakJAS-40"><span class="cite-bracket">[</span>40<span class="cite-bracket">]</span></a></sup> In the <a href="/wiki/Genetic_code" title="Genetic code">genetic code</a>, glycine is coded by all <a href="/wiki/Codons" class="mw-redirect" title="Codons">codons</a> starting with GG, namely GGU, GGC, GGA and GGG.<sup id="cite_ref-:3_8-1" class="reference"><a href="#cite_note-:3-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="As_a_biosynthetic_intermediate">As a biosynthetic intermediate</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Glycine&action=edit&section=8" title="Edit section: As a biosynthetic intermediate"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>In higher <a href="/wiki/Eukaryotes" class="mw-redirect" title="Eukaryotes">eukaryotes</a>, <a href="/wiki/%CE%94-aminolevulinic_acid" class="mw-redirect" title="Δ-aminolevulinic acid">δ-aminolevulinic acid</a>, the key precursor to <a href="/wiki/Porphyrins" class="mw-redirect" title="Porphyrins">porphyrins</a>, is biosynthesized from glycine and <a href="/wiki/Succinyl-CoA" title="Succinyl-CoA">succinyl-CoA</a> by the enzyme <a href="/wiki/ALA_synthase" class="mw-redirect" title="ALA synthase">ALA synthase</a>. Glycine provides the central C<sub>2</sub>N subunit of all <a href="/wiki/Purine" title="Purine">purines</a>.<sup id="cite_ref-Lehninger_36-6" class="reference"><a href="#cite_note-Lehninger-36"><span class="cite-bracket">[</span>36<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="As_a_neurotransmitter">As a neurotransmitter</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Glycine&action=edit&section=9" title="Edit section: As a neurotransmitter"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Glycine is an inhibitory <a href="/wiki/Neurotransmitter" title="Neurotransmitter">neurotransmitter</a> in the <a href="/wiki/Central_nervous_system" title="Central nervous system">central nervous system</a>, especially in the <a href="/wiki/Spinal_cord" title="Spinal cord">spinal cord</a>, <a href="/wiki/Brainstem" title="Brainstem">brainstem</a>, and <a href="/wiki/Retina" title="Retina">retina</a>. When <a href="/wiki/Glycine_receptors" class="mw-redirect" title="Glycine receptors">glycine receptors</a> are activated, <a href="/wiki/Chloride" title="Chloride">chloride</a> enters the neuron via ionotropic receptors, causing an <a href="/wiki/Inhibitory_postsynaptic_potential" title="Inhibitory postsynaptic potential">inhibitory postsynaptic potential</a> (IPSP). <a href="/wiki/Strychnine" title="Strychnine">Strychnine</a> is a strong antagonist at ionotropic glycine receptors, whereas <a href="/wiki/Bicuculline" title="Bicuculline">bicuculline</a> is a weak one. Glycine is a required <a href="/wiki/Co-agonist" class="mw-redirect" title="Co-agonist">co-agonist</a> along with <a href="/wiki/Glutamate" class="mw-redirect" title="Glutamate">glutamate</a> for <a href="/wiki/NMDA_receptor" title="NMDA receptor">NMDA receptors</a>. In contrast to the inhibitory role of glycine in the spinal cord, this behaviour is facilitated at the (<a href="/wiki/NMDA" class="mw-redirect" title="NMDA">NMDA</a>) <a href="/wiki/Glutamatergic" title="Glutamatergic">glutamatergic</a> receptors which are excitatory.<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> The <a href="/wiki/Median_lethal_dose" title="Median lethal dose">LD<sub style="font-size:-1">50</sub></a> of glycine is 7930 mg/kg in rats (oral),<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 it usually causes death by hyperexcitability.<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (December 2024)">citation needed</span></a></i>]</sup> </p> <div class="mw-heading mw-heading3"><h3 id="As_a_toxin_conjugation_agent">As a toxin conjugation agent</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Glycine&action=edit&section=10" title="Edit section: As a toxin conjugation agent"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Glycine <a href="/wiki/Drug_metabolism#Phase_II_–_conjugation" title="Drug metabolism">conjugation</a> pathway has not been fully investigated.<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> Glycine is thought to be a hepatic detoxifier of a number endogenous and xenobiotic organic acids.<sup id="cite_ref-44" class="reference"><a href="#cite_note-44"><span class="cite-bracket">[</span>44<span class="cite-bracket">]</span></a></sup> <a href="/wiki/Bile_acid" title="Bile acid">Bile acids</a> are normally conjugated to glycine in order to increase their solubility in water.<sup id="cite_ref-45" class="reference"><a href="#cite_note-45"><span class="cite-bracket">[</span>45<span class="cite-bracket">]</span></a></sup> </p><p>The human body rapidly clears <a href="/wiki/Sodium_benzoate" title="Sodium benzoate">sodium benzoate</a> by combining it with glycine to form <a href="/wiki/Hippuric_acid" title="Hippuric acid">hippuric acid</a> which is then excreted.<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> The metabolic pathway for this begins with the conversion of benzoate by <a href="/wiki/Butyrate-CoA_ligase" class="mw-redirect" title="Butyrate-CoA ligase">butyrate-CoA ligase</a> into an intermediate product, <a href="/wiki/Benzoyl-CoA" title="Benzoyl-CoA">benzoyl-CoA</a>,<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> which is then metabolized by <a href="/wiki/Glycine_N-acyltransferase" title="Glycine N-acyltransferase">glycine <i>N</i>-acyltransferase</a> into hippuric acid.<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> </p> <div class="mw-heading mw-heading2"><h2 id="Uses">Uses</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Glycine&action=edit&section=11" title="Edit section: Uses"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>In the US, glycine is typically sold in two grades: <a href="/wiki/United_States_Pharmacopeia" title="United States Pharmacopeia">United States Pharmacopeia</a> ("USP"), and technical grade. USP grade sales account for approximately 80 to 85 percent of the U.S. market for glycine. If purity greater than the USP standard is needed, for example for <a href="/wiki/Intravenous" class="mw-redirect" title="Intravenous">intravenous</a> injections, a more expensive pharmaceutical grade glycine can be used. Technical grade glycine, which may or may not meet USP grade standards, is sold at a lower price for use in industrial applications, e.g., as an agent in metal complexing and finishing.<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> </p> <div class="mw-heading mw-heading3"><h3 id="Animal_and_human_foods">Animal and human foods</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Glycine&action=edit&section=12" title="Edit section: Animal and human foods"><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:Cu(gly)2(OH2).png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/7/75/Cu%28gly%292%28OH2%29.png/250px-Cu%28gly%292%28OH2%29.png" decoding="async" width="220" height="133" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/7/75/Cu%28gly%292%28OH2%29.png/330px-Cu%28gly%292%28OH2%29.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/7/75/Cu%28gly%292%28OH2%29.png/500px-Cu%28gly%292%28OH2%29.png 2x" data-file-width="1200" data-file-height="725" /></a><figcaption>Structure of <i>cis</i>-Cu(glycinate)<sub>2</sub>(H<sub>2</sub>O)<sup id="cite_ref-50" class="reference"><a href="#cite_note-50"><span class="cite-bracket">[</span>50<span class="cite-bracket">]</span></a></sup></figcaption></figure> <p>Glycine is not widely used in foods for its nutritional value, except in infusions. Instead, glycine's role in food chemistry is as a flavorant. It is mildly sweet, and it counters the aftertaste of <a href="/wiki/Saccharine" class="mw-redirect" title="Saccharine">saccharine</a>. It also has preservative properties, perhaps owing to its complexation to metal ions. Metal glycinate complexes, e.g. <a href="/wiki/Copper(II)_glycinate" title="Copper(II) glycinate">copper(II) glycinate</a> are used as supplements for animal feeds.<sup id="cite_ref-Ull_27-1" class="reference"><a href="#cite_note-Ull-27"><span class="cite-bracket">[</span>27<span class="cite-bracket">]</span></a></sup> </p><p>As of 1971<sup class="plainlinks noexcerpt noprint asof-tag update" style="display:none;"><a class="external text" href="https://en.wikipedia.org/w/index.php?title=Glycine&action=edit">[update]</a></sup>, the U.S. <a href="/wiki/Food_and_Drug_Administration" title="Food and Drug Administration">Food and Drug Administration</a> "no longer regards glycine and its salts as <a href="/wiki/Generally_recognized_as_safe" title="Generally recognized as safe">generally recognized as safe</a> for use in human food",<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> and only permits food uses of glycine under certain conditions.<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> </p><p>Glycine has been researched for its potential to <a href="/wiki/Life_extension" title="Life extension">extend life</a>.<sup id="cite_ref-:2_53-0" class="reference"><a href="#cite_note-:2-53"><span class="cite-bracket">[</span>53<span class="cite-bracket">]</span></a></sup><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> The proposed mechanisms of this effect are its ability to clear <a href="/wiki/Methionine" title="Methionine">methionine</a> from the body, and activating <a href="/wiki/Autophagy" title="Autophagy">autophagy</a>.<sup id="cite_ref-:2_53-1" class="reference"><a href="#cite_note-:2-53"><span class="cite-bracket">[</span>53<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Chemical_feedstock">Chemical feedstock</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Glycine&action=edit&section=13" title="Edit section: Chemical feedstock"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Glycine is an intermediate in the synthesis of a variety of chemical products. It is used in the manufacture of the <a href="/wiki/Herbicide" title="Herbicide">herbicides</a> <a href="/wiki/Glyphosate" title="Glyphosate">glyphosate</a>,<sup id="cite_ref-55" class="reference"><a href="#cite_note-55"><span class="cite-bracket">[</span>55<span class="cite-bracket">]</span></a></sup> <a href="/wiki/Iprodione" title="Iprodione">iprodione</a>, glyphosine, <a href="/wiki/Imiprothrin" title="Imiprothrin">imiprothrin</a>, and eglinazine.<sup id="cite_ref-Ull_27-2" class="reference"><a href="#cite_note-Ull-27"><span class="cite-bracket">[</span>27<span class="cite-bracket">]</span></a></sup> It is used as an intermediate of <a href="/wiki/Antibiotic" title="Antibiotic">antibiotics</a> such as <a href="/wiki/Thiamphenicol" title="Thiamphenicol">thiamphenicol</a>.<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (July 2019)">citation needed</span></a></i>]</sup> </p> <div class="mw-heading mw-heading3"><h3 id="Laboratory_research">Laboratory research</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Glycine&action=edit&section=14" title="Edit section: Laboratory research"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Glycine is a significant component of some solutions used in the <a href="/wiki/Polyacrylamide_gel_electrophoresis" title="Polyacrylamide gel electrophoresis">SDS-PAGE</a> method of protein analysis. It serves as a buffering agent, maintaining pH and preventing sample damage during electrophoresis.<sup id="cite_ref-56" class="reference"><a href="#cite_note-56"><span class="cite-bracket">[</span>56<span class="cite-bracket">]</span></a></sup> Glycine is also used to remove protein-labeling antibodies from <a href="/wiki/Western_blot" title="Western blot">Western blot</a> membranes to enable the probing of numerous proteins of interest from SDS-PAGE gel. This allows more data to be drawn from the same specimen, increasing the reliability of the data, reducing the amount of sample processing, and number of samples required.<sup id="cite_ref-57" class="reference"><a href="#cite_note-57"><span class="cite-bracket">[</span>57<span class="cite-bracket">]</span></a></sup> This process is known as stripping. </p> <div class="mw-heading mw-heading2"><h2 id="Presence_in_space">Presence in space</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Glycine&action=edit&section=15" title="Edit section: Presence in space"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The presence of glycine outside the Earth was confirmed in 2009, based on the analysis of samples that had been taken in 2004 by the <a href="/wiki/NASA" title="NASA">NASA</a> spacecraft <i><a href="/wiki/Stardust_(spacecraft)" title="Stardust (spacecraft)">Stardust</a></i> from comet <a href="/wiki/Wild_2" class="mw-redirect" title="Wild 2">Wild 2</a> and subsequently returned to Earth. Glycine had previously been identified in the <a href="/wiki/Murchison_meteorite" title="Murchison meteorite">Murchison meteorite</a> in 1970.<sup id="cite_ref-58" class="reference"><a href="#cite_note-58"><span class="cite-bracket">[</span>58<span class="cite-bracket">]</span></a></sup> The discovery of glycine in outer space bolstered the hypothesis of so-called <a href="/wiki/Pseudo-panspermia" title="Pseudo-panspermia">soft-panspermia</a>, which claims that the "building blocks" of life are widespread throughout the universe.<sup id="cite_ref-59" class="reference"><a href="#cite_note-59"><span class="cite-bracket">[</span>59<span class="cite-bracket">]</span></a></sup> In 2016, detection of glycine within Comet <a href="/wiki/67P/Churyumov%E2%80%93Gerasimenko" title="67P/Churyumov–Gerasimenko">67P/Churyumov–Gerasimenko</a> by the <a href="/wiki/Rosetta_(spacecraft)" title="Rosetta (spacecraft)"><i>Rosetta</i> spacecraft</a> was announced.<sup id="cite_ref-60" class="reference"><a href="#cite_note-60"><span class="cite-bracket">[</span>60<span class="cite-bracket">]</span></a></sup> </p><p>The detection of glycine outside the <a href="/wiki/Solar_System" title="Solar System">Solar System</a> in the <a href="/wiki/Interstellar_medium" title="Interstellar medium">interstellar medium</a> has been debated.<sup id="cite_ref-Snyder_61-0" class="reference"><a href="#cite_note-Snyder-61"><span class="cite-bracket">[</span>61<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Evolution">Evolution</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Glycine&action=edit&section=16" title="Edit section: Evolution"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Glycine is proposed to be defined by early genetic codes.<sup id="cite_ref-62" class="reference"><a href="#cite_note-62"><span class="cite-bracket">[</span>62<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-63" class="reference"><a href="#cite_note-63"><span class="cite-bracket">[</span>63<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-64" class="reference"><a href="#cite_note-64"><span class="cite-bracket">[</span>64<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-:1_65-0" class="reference"><a href="#cite_note-:1-65"><span class="cite-bracket">[</span>65<span class="cite-bracket">]</span></a></sup> For example, <a href="/wiki/Low_complexity_regions_in_proteins" title="Low complexity regions in proteins">low complexity regions</a> (in proteins), that may resemble the proto-peptides of the early <a href="/wiki/Genetic_code" title="Genetic code">genetic code</a> are highly enriched in glycine.<sup id="cite_ref-:1_65-1" class="reference"><a href="#cite_note-:1-65"><span class="cite-bracket">[</span>65<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Presence_in_foods">Presence in foods</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Glycine&action=edit&section=17" title="Edit section: Presence in foods"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <table class="wikitable"> <caption>Food sources of glycine<sup id="cite_ref-66" class="reference"><a href="#cite_note-66"><span class="cite-bracket">[</span>66<span class="cite-bracket">]</span></a></sup> </caption> <tbody><tr> <th>Food </th> <th>Percentage<br />content<br />by weight<br />(g/100g) </th></tr> <tr> <td>Snacks, <a href="/wiki/Pork_skins" class="mw-redirect" title="Pork skins">pork skins</a></td> <td>11.04 </td></tr> <tr> <td><a href="/wiki/Sesame_seed" class="mw-redirect" title="Sesame seed">Sesame seeds</a> flour (low fat)</td> <td>3.43 </td></tr> <tr> <td>Beverages, <a href="/wiki/Protein_powder" class="mw-redirect" title="Protein powder">protein powder</a> (<a href="/wiki/Soy" class="mw-redirect" title="Soy">soy</a>-based)</td> <td>2.37 </td></tr> <tr> <td>Seeds, safflower seed meal, partially defatted</td> <td>2.22 </td></tr> <tr> <td>Meat, bison, beef and others (various parts)</td> <td>1.5–2.0 </td></tr> <tr> <td>Gelatin desserts</td> <td>1.96 </td></tr> <tr> <td>Seeds, <a href="/wiki/Pumpkin" title="Pumpkin">pumpkin</a> and <a href="/wiki/Squash_(plant)" class="mw-redirect" title="Squash (plant)">squash</a> seed kernels</td> <td>1.82 </td></tr> <tr> <td>Turkey, all classes, back, meat and skin</td> <td>1.79 </td></tr> <tr> <td>Chicken, broilers or fryers, meat and skin</td> <td>1.74 </td></tr> <tr> <td>Pork, ground, 96% lean / 4% fat, cooked, crumbles</td> <td>1.71 </td></tr> <tr> <td>Bacon and beef sticks</td> <td>1.64 </td></tr> <tr> <td><a href="/wiki/Peanut" title="Peanut">Peanuts</a></td> <td>1.63 </td></tr> <tr> <td><a href="/wiki/Crustacean" title="Crustacean">Crustaceans</a>, spiny lobster</td> <td>1.59 </td></tr> <tr> <td>Spices, <a href="/wiki/Mustard_seed" title="Mustard seed">mustard seed</a>, ground</td> <td>1.59 </td></tr> <tr> <td><a href="/wiki/Salami" title="Salami">Salami</a></td> <td>1.55 </td></tr> <tr> <td>Nuts, <a href="/wiki/Juglans_cinerea" title="Juglans cinerea">butternuts</a>, dried</td> <td>1.51 </td></tr> <tr> <td>Fish, salmon, pink, canned, drained solids</td> <td>1.42 </td></tr> <tr> <td><a href="/wiki/Almond" title="Almond">Almonds</a></td> <td>1.42 </td></tr> <tr> <td>Fish, <a href="/wiki/Mackerel" title="Mackerel">mackerel</a></td> <td>0.93 </td></tr> <tr> <td>Cereals ready-to-eat, granola, homemade</td> <td>0.81 </td></tr> <tr> <td><a href="/wiki/Leeks" class="mw-redirect" title="Leeks">Leeks</a>, (bulb and lower-leaf portion), freeze-dried</td> <td>0.7 </td></tr> <tr> <td>Cheese, <a href="/wiki/Parmesan" title="Parmesan">parmesan</a> (and others), grated</td> <td>0.56 </td></tr> <tr> <td><a href="/wiki/Soybeans" class="mw-redirect" title="Soybeans">Soybeans</a>, green, cooked, boiled, drained, without salt</td> <td>0.51 </td></tr> <tr> <td>Bread, protein (includes gluten)</td> <td>0.47 </td></tr> <tr> <td>Egg, whole, cooked, fried</td> <td>0.47 </td></tr> <tr> <td>Beans, white, mature seeds, cooked, boiled, with salt</td> <td>0.38 </td></tr> <tr> <td>Lentils, mature seeds, cooked, boiled, with salt</td> <td>0.37 </td></tr></tbody></table> <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=Glycine&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/Trimethylglycine" title="Trimethylglycine">Trimethylglycine</a></li> <li><a href="/wiki/Amino_acid_neurotransmitter" title="Amino acid neurotransmitter">Amino acid neurotransmitter</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=Glycine&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"> <div class="mw-references-wrap mw-references-columns"><ol class="references"> <li id="cite_note-1"><span class="mw-cite-backlink"><b><a href="#cite_ref-1">^</a></b></span> <span class="reference-text"><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 book cs1"><i><a href="/wiki/Merck_Index" title="Merck Index">The Merck Index: An Encyclopedia of Chemicals, Drugs, and Biologicals</a></i> (11th ed.). 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"Achiral amino acid glycine acts as an origin of homochirality in asymmetric autocatalysis". <i>Organic & Biomolecular Chemistry</i>. <b>17</b> (17): <span class="nowrap">4200–</span>4203. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1039%2FC9OB00345B">10.1039/C9OB00345B</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/30932119">30932119</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Organic+%26+Biomolecular+Chemistry&rft.atitle=Achiral+amino+acid+glycine+acts+as+an+origin+of+homochirality+in+asymmetric+autocatalysis&rft.volume=17&rft.issue=17&rft.pages=%3Cspan+class%3D%22nowrap%22%3E4200-%3C%2Fspan%3E4203&rft.date=2019-04&rft_id=info%3Adoi%2F10.1039%2FC9OB00345B&rft_id=info%3Apmid%2F30932119&rft.aulast=Matsumoto&rft.aufirst=A&rft.au=Ozaki%2C+H&rft.au=Tsuchiya%2C+S&rft.au=Asahi%2C+T&rft.au=Lahav%2C+M&rft.au=Kawasaki%2C+T&rft.au=Soai%2C+K&rfr_id=info%3Asid%2Fen.wikipedia.org%3AGlycine" class="Z3988"></span></span> </li> <li id="cite_note-12"><span class="mw-cite-backlink"><b><a href="#cite_ref-12">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFAlvesBassotBulteauPirola2019" class="citation journal cs1">Alves A, Bassot A, Bulteau AL, Pirola L, Morio B (June 2019). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6627940">"Glycine Metabolism and Its Alterations in Obesity and Metabolic Diseases"</a>. <i>Nutrients</i>. <b>11</b> (6): 1356. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://doi.org/10.3390%2Fnu11061356">10.3390/nu11061356</a></span>. <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/PMC6627940">6627940</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/31208147">31208147</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Nutrients&rft.atitle=Glycine+Metabolism+and+Its+Alterations+in+Obesity+and+Metabolic+Diseases&rft.volume=11&rft.issue=6&rft.pages=1356&rft.date=2019-06&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC6627940%23id-name%3DPMC&rft_id=info%3Apmid%2F31208147&rft_id=info%3Adoi%2F10.3390%2Fnu11061356&rft.aulast=Alves&rft.aufirst=A&rft.au=Bassot%2C+A&rft.au=Bulteau%2C+AL&rft.au=Pirola%2C+L&rft.au=Morio%2C+B&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC6627940&rfr_id=info%3Asid%2Fen.wikipedia.org%3AGlycine" class="Z3988"></span></span> </li> <li id="cite_note-13"><span class="mw-cite-backlink"><b><a href="#cite_ref-13">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFPlimmer1912" class="citation book cs1 cs1-prop-long-vol"><a href="/wiki/R._H._A._Plimmer" title="R. H. A. Plimmer">Plimmer RH</a> (1912) [1908]. Plimmer RH, Hopkins F (eds.). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=7JM8AAAAIAAJ&pg=PA112"><i>The chemical composition of the proteins</i></a>. Monographs on biochemistry. Vol. Part I. Analysis (2nd ed.). London: Longmans, Green and Co. p. 82<span class="reference-accessdate">. Retrieved <span class="nowrap">January 18,</span> 2010</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=The+chemical+composition+of+the+proteins&rft.place=London&rft.series=Monographs+on+biochemistry&rft.pages=82&rft.edition=2nd&rft.pub=Longmans%2C+Green+and+Co.&rft.date=1912&rft.aulast=Plimmer&rft.aufirst=RH&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3D7JM8AAAAIAAJ%26pg%3DPA112&rfr_id=info%3Asid%2Fen.wikipedia.org%3AGlycine" class="Z3988"></span></span> </li> <li id="cite_note-14"><span class="mw-cite-backlink"><b><a href="#cite_ref-14">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFBraconnot1820" class="citation journal cs1 cs1-prop-foreign-lang-source">Braconnot H (1820). <a rel="nofollow" class="external text" href="https://babel.hathitrust.org/cgi/pt?id=hvd.hx3dvk;view=1up;seq=119">"Sur la conversion des matières animales en nouvelles substances par le moyen de l'acide sulfurique"</a> [On the conversion of animal materials into new substances by means of sulfuric acid]. <i>Annales de Chimie et de Physique</i>. 2nd series (in French). <b>13</b>: <span class="nowrap">113–</span>125.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Annales+de+Chimie+et+de+Physique&rft.atitle=Sur+la+conversion+des+mati%C3%A8res+animales+en+nouvelles+substances+par+le+moyen+de+l%27acide+sulfurique&rft.volume=13&rft.pages=%3Cspan+class%3D%22nowrap%22%3E113-%3C%2Fspan%3E125&rft.date=1820&rft.aulast=Braconnot&rft.aufirst=H&rft_id=https%3A%2F%2Fbabel.hathitrust.org%2Fcgi%2Fpt%3Fid%3Dhvd.hx3dvk%3Bview%3D1up%3Bseq%3D119&rfr_id=info%3Asid%2Fen.wikipedia.org%3AGlycine" class="Z3988"></span> ; see p. 114.</span> </li> <li id="cite_note-15"><span class="mw-cite-backlink"><b><a href="#cite_ref-15">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFMacKenzie1822" class="citation book cs1">MacKenzie C (1822). <a rel="nofollow" class="external text" href="https://archive.org/details/onethousandexpe01mackgoog"><i>One Thousand Experiments in Chemistry: With Illustrations of Natural Phenomena; and Practical Observations on the Manufacturing and Chemical Processes at Present Pursued in the Successful Cultivation of the Useful Arts ...</i></a> Sir R. Phillips and Company. p. <a rel="nofollow" class="external text" href="https://archive.org/details/onethousandexpe01mackgoog/page/n650">557</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=One+Thousand+Experiments+in+Chemistry%3A+With+Illustrations+of+Natural+Phenomena%3B+and+Practical+Observations+on+the+Manufacturing+and+Chemical+Processes+at+Present+Pursued+in+the+Successful+Cultivation+of+the+Useful+Arts+...&rft.pages=557&rft.pub=Sir+R.+Phillips+and+Company&rft.date=1822&rft.aulast=MacKenzie&rft.aufirst=C&rft_id=https%3A%2F%2Farchive.org%2Fdetails%2Fonethousandexpe01mackgoog&rfr_id=info%3Asid%2Fen.wikipedia.org%3AGlycine" class="Z3988"></span></span> </li> <li id="cite_note-16"><span class="mw-cite-backlink"><b><a href="#cite_ref-16">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFBoussingault1838" class="citation journal cs1 cs1-prop-foreign-lang-source">Boussingault (1838). <a rel="nofollow" class="external text" href="https://babel.hathitrust.org/cgi/pt?id=mdp.39015035450702;view=1up;seq=515">"Sur la composition du sucre de gélatine et de l'acide nitro-saccharique de Braconnot"</a> [On the composition of sugar of gelatine and of nitro-glucaric acid of Braconnot]. <i>Comptes Rendus</i> (in French). <b>7</b>: <span class="nowrap">493–</span>495.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Comptes+Rendus&rft.atitle=Sur+la+composition+du+sucre+de+g%C3%A9latine+et+de+l%27acide+nitro-saccharique+de+Braconnot&rft.volume=7&rft.pages=%3Cspan+class%3D%22nowrap%22%3E493-%3C%2Fspan%3E495&rft.date=1838&rft.au=Boussingault&rft_id=https%3A%2F%2Fbabel.hathitrust.org%2Fcgi%2Fpt%3Fid%3Dmdp.39015035450702%3Bview%3D1up%3Bseq%3D515&rfr_id=info%3Asid%2Fen.wikipedia.org%3AGlycine" class="Z3988"></span></span> </li> <li id="cite_note-17"><span class="mw-cite-backlink"><b><a href="#cite_ref-17">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFHorsford1847" class="citation journal cs1">Horsford EN (1847). <a rel="nofollow" class="external text" href="https://babel.hathitrust.org/cgi/pt?id=hvd.32044102902764;view=1up;seq=381">"Glycocoll (gelatine sugar) and some of its products of decomposition"</a>. <i>The American Journal of Science and Arts</i>. 2nd series. <b>3</b>: <span class="nowrap">369–</span>381.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=The+American+Journal+of+Science+and+Arts&rft.atitle=Glycocoll+%28gelatine+sugar%29+and+some+of+its+products+of+decomposition&rft.volume=3&rft.pages=%3Cspan+class%3D%22nowrap%22%3E369-%3C%2Fspan%3E381&rft.date=1847&rft.aulast=Horsford&rft.aufirst=EN&rft_id=https%3A%2F%2Fbabel.hathitrust.org%2Fcgi%2Fpt%3Fid%3Dhvd.32044102902764%3Bview%3D1up%3Bseq%3D381&rfr_id=info%3Asid%2Fen.wikipedia.org%3AGlycine" class="Z3988"></span></span> </li> <li id="cite_note-18"><span class="mw-cite-backlink"><b><a href="#cite_ref-18">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFIhde1984" class="citation book cs1">Ihde AJ (1984). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=89BIAwAAQBAJ&pg=PA167"><i>The Development of Modern Chemistry</i></a>. Courier Corporation. p. 167. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-486-64235-2" title="Special:BookSources/978-0-486-64235-2"><bdi>978-0-486-64235-2</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=The+Development+of+Modern+Chemistry&rft.pages=167&rft.pub=Courier+Corporation&rft.date=1984&rft.isbn=978-0-486-64235-2&rft.aulast=Ihde&rft.aufirst=Aaron+J.&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3D89BIAwAAQBAJ%26pg%3DPA167&rfr_id=info%3Asid%2Fen.wikipedia.org%3AGlycine" class="Z3988"></span></span> </li> <li id="cite_note-19"><span class="mw-cite-backlink"><b><a href="#cite_ref-19">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFBerzelius1848" class="citation book cs1">Berzelius J (1848). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=mDc4AQAAIAAJ&q=%22glycin%22&pg=PA654"><i>Jahres-Bericht über die Fortschritte der Chemie und Mineralogie (Annual Report on the Progress of Chemistry and Mineralogy)</i></a>. Vol. 47. Tübigen, (Germany): Laupp. p. 654.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Jahres-Bericht+%C3%BCber+die+Fortschritte+der+Chemie+und+Mineralogie+%28Annual+Report+on+the+Progress+of+Chemistry+and+Mineralogy%29&rft.place=T%C3%BCbigen%2C+%28Germany%29&rft.pages=654&rft.pub=Laupp&rft.date=1848&rft.aulast=Berzelius&rft.aufirst=J&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DmDc4AQAAIAAJ%26q%3D%2522glycin%2522%26pg%3DPA654&rfr_id=info%3Asid%2Fen.wikipedia.org%3AGlycine" class="Z3988"></span> From p. 654: <i>"Er hat dem Leimzucker als Basis den Namen </i>Glycocoll<i> gegeben. ... </i>Glycin<i> genannt werden, und diesen Namen werde ich anwenden."</i> (He [i.e., the American scientist <a href="/wiki/Eben_Norton_Horsford" title="Eben Norton Horsford">Eben Norton Horsford</a>, then a student of the German chemist <a href="/wiki/Justus_von_Liebig" title="Justus von Liebig">Justus von Liebig</a>] gave the name "glycocoll" to <i>Leimzucker</i> [sugar of gelatine], a base. This name is not euphonious and has besides the flaw that it clashes with the names of the rest of the bases. It is compounded from γλυχυς (sweet) and χολλα (animal glue). Since this organic base is the only [one] which tastes sweet, then it can much more briefly be named "glycine", and I will use this name.)</span> </li> <li id="cite_note-20"><span class="mw-cite-backlink"><b><a href="#cite_ref-20">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFNye1999" class="citation book cs1">Nye MJ (1999). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=qKjxtZvnBKQC&pg=PA141"><i>Before Big Science: The Pursuit of Modern Chemistry and Physics, 1800-1940</i></a>. Harvard University Press. p. 141. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-674-06382-2" title="Special:BookSources/978-0-674-06382-2"><bdi>978-0-674-06382-2</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Before+Big+Science%3A+The+Pursuit+of+Modern+Chemistry+and+Physics%2C+1800-1940&rft.pages=141&rft.pub=Harvard+University+Press&rft.date=1999&rft.isbn=978-0-674-06382-2&rft.aulast=Nye&rft.aufirst=Mary+Jo&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DqKjxtZvnBKQC%26pg%3DPA141&rfr_id=info%3Asid%2Fen.wikipedia.org%3AGlycine" class="Z3988"></span></span> </li> <li id="cite_note-21"><span class="mw-cite-backlink"><b><a href="#cite_ref-21">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://web.archive.org/web/20141113010813/http://www.oxforddictionaries.com/definition/american_english/glycine">"glycine"</a>. <i>Oxford Dictionaries</i>. 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Retrieved <span class="nowrap">May 26,</span> 2024</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=fdc.nal.usda.gov&rft.atitle=FoodData+Central+Search+Results+for+%22Glycine+%28g%29%22&rft_id=https%3A%2F%2Ffdc.nal.usda.gov%2Ffood-search%3Fcomponent%3D1225&rfr_id=info%3Asid%2Fen.wikipedia.org%3AGlycine" class="Z3988"></span></span> </li> </ol></div></div> <div class="mw-heading mw-heading2"><h2 id="Further_reading">Further reading</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Glycine&action=edit&section=20" title="Edit section: Further reading"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1239549316">.mw-parser-output .refbegin{margin-bottom:0.5em}.mw-parser-output .refbegin-hanging-indents>ul{margin-left:0}.mw-parser-output .refbegin-hanging-indents>ul>li{margin-left:0;padding-left:3.2em;text-indent:-3.2em}.mw-parser-output .refbegin-hanging-indents ul,.mw-parser-output .refbegin-hanging-indents ul li{list-style:none}@media(max-width:720px){.mw-parser-output .refbegin-hanging-indents>ul>li{padding-left:1.6em;text-indent:-1.6em}}.mw-parser-output .refbegin-columns{margin-top:0.3em}.mw-parser-output .refbegin-columns ul{margin-top:0}.mw-parser-output .refbegin-columns li{page-break-inside:avoid;break-inside:avoid-column}@media screen{.mw-parser-output .refbegin{font-size:90%}}</style><div class="refbegin" style=""> <ul><li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFNestlerHelm2017" class="citation journal cs1">Nestler P, Helm CA (October 2017). <a rel="nofollow" class="external text" href="https://doi.org/10.1086%2F375637">"Determination of refractive index and layer thickness of nm-thin films via ellipsometry"</a>. <i>Optics Express</i>. <b>25</b> (22): <span class="nowrap">27077–</span>27085. <a href="/wiki/Bibcode_(identifier)" class="mw-redirect" title="Bibcode (identifier)">Bibcode</a>:<a rel="nofollow" class="external text" href="https://ui.adsabs.harvard.edu/abs/2003ApJ...593..848K">2003ApJ...593..848K</a>. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://doi.org/10.1086%2F375637">10.1086/375637</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/29092189">29092189</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Optics+Express&rft.atitle=Determination+of+refractive+index+and+layer+thickness+of+nm-thin+films+via+ellipsometry&rft.volume=25&rft.issue=22&rft.pages=%3Cspan+class%3D%22nowrap%22%3E27077-%3C%2Fspan%3E27085&rft.date=2017-10&rft_id=info%3Apmid%2F29092189&rft_id=info%3Adoi%2F10.1086%2F375637&rft_id=info%3Abibcode%2F2003ApJ...593..848K&rft.aulast=Nestler&rft.aufirst=P&rft.au=Helm%2C+CA&rft_id=https%3A%2F%2Fdoi.org%2F10.1086%252F375637&rfr_id=info%3Asid%2Fen.wikipedia.org%3AGlycine" class="Z3988"></span></li> <li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFNowak2002" class="citation news cs1">Nowak R (July 18, 2002). <a rel="nofollow" class="external text" href="https://www.newscientist.com/article/dn2558-amino-acid-found-in-deep-space/">"Amino acid found in deep space"</a>. <i>New Scientist</i>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=New+Scientist&rft.atitle=Amino+acid+found+in+deep+space&rft.date=2002-07-18&rft.aulast=Nowak&rft.aufirst=Rachel&rft_id=https%3A%2F%2Fwww.newscientist.com%2Farticle%2Fdn2558-amino-acid-found-in-deep-space%2F&rfr_id=info%3Asid%2Fen.wikipedia.org%3AGlycine" class="Z3988"></span></li> <li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFTsai2008" class="citation journal cs1">Tsai GE (December 1, 2008). <a rel="nofollow" class="external text" href="https://web.archive.org/web/20121003063816/http://www.psychiatrictimes.com/display/article/10168/1357569">"A New Class of Antipsychotic Drugs: Enhancing Neurotransmission Mediated by NMDA Receptors"</a>. <i>Psychiatric Times</i>. <b>25</b> (14). Archived from <a rel="nofollow" class="external text" href="http://www.psychiatrictimes.com/display/article/10168/1357569">the original</a> on October 3, 2012<span class="reference-accessdate">. Retrieved <span class="nowrap">January 23,</span> 2009</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Psychiatric+Times&rft.atitle=A+New+Class+of+Antipsychotic+Drugs%3A+Enhancing+Neurotransmission+Mediated+by+NMDA+Receptors&rft.volume=25&rft.issue=14&rft.date=2008-12-01&rft.aulast=Tsai&rft.aufirst=GE&rft_id=http%3A%2F%2Fwww.psychiatrictimes.com%2Fdisplay%2Farticle%2F10168%2F1357569&rfr_id=info%3Asid%2Fen.wikipedia.org%3AGlycine" class="Z3988"></span></li> <li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite class="citation pressrelease cs1"><a rel="nofollow" class="external text" href="https://www.sciencedaily.com/releases/2008/03/080326161658.htm">"Organic Molecule, Amino Acid-Like, Found In Constellation Sagittarius"</a>. <i>ScienceDaily</i> (Press release). Max-Planck-Gesellschaft. March 27, 2008.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=Organic+Molecule%2C+Amino+Acid-Like%2C+Found+In+Constellation+Sagittarius&rft.pub=Max-Planck-Gesellschaft&rft.date=2008-03-27&rft_id=https%3A%2F%2Fwww.sciencedaily.com%2Freleases%2F2008%2F03%2F080326161658.htm&rfr_id=info%3Asid%2Fen.wikipedia.org%3AGlycine" class="Z3988"></span></li></ul> </div> <div class="mw-heading mw-heading2"><h2 id="External_links">External links</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Glycine&action=edit&section=21" title="Edit section: External links"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1235681985">.mw-parser-output .side-box{margin:4px 0;box-sizing:border-box;border:1px solid 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href="https://commons.wikimedia.org/wiki/Category:Glycine" class="extiw" title="commons:Category:Glycine">Glycine</a></span>.</div></div> </div> <ul><li><a rel="nofollow" class="external text" href="http://gmd.mpimp-golm.mpg.de/Spectrums/8a79d6c1-4849-4634-afe1-112d6e346bfb.aspx">Glycine MS Spectrum</a></li> <li><a rel="nofollow" class="external text" href="https://en.longevitywiki.org/wiki/Glycine">Glycine</a></li> <li><a rel="nofollow" class="external text" href="https://web.archive.org/web/20110511151841/http://www.chem.qmul.ac.uk/iubmb/enzyme/reaction/AminoAcid/GlyCleave.html">Glycine cleavage system</a></li> <li><a rel="nofollow" class="external text" href="https://web.archive.org/web/20141221164448/http://www.schizophrenia.com/glycinetreat.htm">Glycine Therapy - A New Direction for Schizophrenia Treatment?</a></li> <li><a rel="nofollow" class="external text" href="http://chemsub.online.fr/name/glycine.html">ChemSub Online (Glycine)</a>.</li> <li><a rel="nofollow" class="external text" href="https://www.nasa.gov/mission_pages/stardust/news/stardust_amino_acid.html">NASA scientists have discovered glycine, a fundamental building block of life, in samples of comet Wild 2 returned by NASA's Stardust spacecraft.</a></li></ul> <div class="navbox-styles"><style data-mw-deduplicate="TemplateStyles:r1129693374">.mw-parser-output .hlist dl,.mw-parser-output .hlist ol,.mw-parser-output .hlist ul{margin:0;padding:0}.mw-parser-output .hlist dd,.mw-parser-output .hlist dt,.mw-parser-output .hlist li{margin:0;display:inline}.mw-parser-output .hlist.inline,.mw-parser-output .hlist.inline dl,.mw-parser-output .hlist.inline ol,.mw-parser-output .hlist.inline ul,.mw-parser-output .hlist dl dl,.mw-parser-output .hlist dl ol,.mw-parser-output .hlist dl ul,.mw-parser-output .hlist ol dl,.mw-parser-output .hlist ol ol,.mw-parser-output .hlist ol ul,.mw-parser-output .hlist ul dl,.mw-parser-output .hlist ul ol,.mw-parser-output .hlist ul ul{display:inline}.mw-parser-output .hlist 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aria-labelledby="Encoded_(proteinogenic)_amino_acids563" 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="3"><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:Proteinogenic_amino_acids" title="Template:Proteinogenic amino acids"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Proteinogenic_amino_acids" title="Template talk:Proteinogenic amino acids"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Proteinogenic_amino_acids" title="Special:EditPage/Template:Proteinogenic amino acids"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Encoded_(proteinogenic)_amino_acids563" style="font-size:114%;margin:0 4em"><a href="/wiki/Proteinogenic_amino_acid" title="Proteinogenic amino acid">Encoded (proteinogenic) amino acids</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%">General topics</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Protein" title="Protein">Protein</a></li> <li><a href="/wiki/Peptide" title="Peptide">Peptide</a></li> <li><a href="/wiki/Genetic_code" title="Genetic code">Genetic code</a></li></ul> </div></td><td class="noviewer navbox-image" rowspan="2" style="width:1px;padding:0 0 0 2px"><div><figure typeof="mw:File/Thumb"><a href="/wiki/File:L-amino_acid_any.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/0/0e/L-amino_acid_any.png/120px-L-amino_acid_any.png" decoding="async" width="100" height="88" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/0/0e/L-amino_acid_any.png/250px-L-amino_acid_any.png 1.5x" data-file-width="728" data-file-height="640" /></a><figcaption>Unspecified L-amino acid</figcaption></figure></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">By properties</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Aliphatic_compound" title="Aliphatic compound">Aliphatic</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Branched-chain_amino_acid" title="Branched-chain amino acid">Branched-chain amino acids</a> (<a href="/wiki/Valine" title="Valine">Valine</a></li> <li><a href="/wiki/Isoleucine" title="Isoleucine">Isoleucine</a></li> <li><a href="/wiki/Leucine" title="Leucine">Leucine</a>)</li> <li><a href="/wiki/Methionine" title="Methionine">Methionine</a></li> <li><a href="/wiki/Alanine" title="Alanine">Alanine</a></li> <li><a href="/wiki/Proline" title="Proline">Proline</a></li> <li><a class="mw-selflink selflink">Glycine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Aromatic_amino_acid" title="Aromatic amino acid">Aromatic</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Histidine" title="Histidine">Histidine</a></li> <li><a href="/wiki/Tyrosine" title="Tyrosine">Tyrosine</a></li> <li><a href="/wiki/Tryptophan" title="Tryptophan">Tryptophan</a></li> <li><a href="/wiki/Phenylalanine" title="Phenylalanine">Phenylalanine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Chemical_polarity" title="Chemical polarity">Polar</a>, uncharged</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Asparagine" title="Asparagine">Asparagine</a></li> <li><a href="/wiki/Glutamine" title="Glutamine">Glutamine</a></li> <li><a href="/wiki/Serine" title="Serine">Serine</a></li> <li><a href="/wiki/Threonine" title="Threonine">Threonine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Positive charge (p<i>K</i><sub>a</sub>)</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Lysine" title="Lysine">Lysine</a> (≈10.8)</li> <li><a href="/wiki/Arginine" title="Arginine">Arginine</a> (≈12.5)</li> <li><a href="/wiki/Histidine" title="Histidine">Histidine</a> (≈6.1)</li> <li><a href="/wiki/Pyrrolysine" title="Pyrrolysine">Pyrrolysine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Negative charge (p<i>K</i><sub>a</sub>)</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Aspartic_acid" title="Aspartic acid">Aspartic acid</a> (≈3.9)</li> <li><a href="/wiki/Glutamic_acid" title="Glutamic acid">Glutamic acid</a> (≈4.1)</li> <li><a href="/wiki/Selenocysteine" title="Selenocysteine">Selenocysteine</a> (≈5.4)</li> <li><a href="/wiki/Cysteine" title="Cysteine">Cysteine</a> (≈8.3)</li> <li><a href="/wiki/Tyrosine" title="Tyrosine">Tyrosine</a> (≈10.1)</li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><td class="navbox-abovebelow" colspan="3"><div><div class="hlist" style="font-size:88%;"> <ul><li><b><a href="/wiki/Amino_acids" class="mw-redirect" title="Amino acids">Amino acids</a> types</b>: <a href="/wiki/Template:Encoded_amino_acids" class="mw-redirect" title="Template:Encoded amino acids">Encoded (proteins)</a></li> <li><a href="/wiki/Essential_amino_acids" class="mw-redirect" title="Essential amino acids">Essential</a></li> <li><a href="/wiki/Template:Non-proteinogenic_amino_acids" title="Template:Non-proteinogenic amino acids">Non-proteinogenic</a></li> <li><a href="/wiki/Ketogenic_amino_acids" class="mw-redirect" title="Ketogenic amino acids">Ketogenic</a></li> <li><a href="/wiki/Glucogenic_amino_acids" class="mw-redirect" title="Glucogenic amino acids">Glucogenic</a></li> <li><a href="/wiki/Secondary_amino_acid" title="Secondary amino acid">Secondary amino</a></li> <li><a href="/wiki/Imino_acid" title="Imino acid">Imino acids</a></li> <li><a href="/wiki/D-amino_acids" class="mw-redirect" title="D-amino acids">D-amino acids</a></li> <li><a href="/wiki/Dehydroamino_acid" title="Dehydroamino acid">Dehydroamino acids</a></li></ul> </div></div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374" /><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235" /></div><div role="navigation" class="navbox" aria-labelledby="Amino_acid_metabolism_metabolic_intermediates153" style="padding:3px"><table class="nowraplinks mw-collapsible mw-collapsed navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374" /><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231" /><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Amino_acid_metabolism_intermediates" title="Template:Amino acid metabolism intermediates"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Amino_acid_metabolism_intermediates" title="Template talk:Amino acid metabolism intermediates"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Amino_acid_metabolism_intermediates" title="Special:EditPage/Template:Amino acid metabolism intermediates"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Amino_acid_metabolism_metabolic_intermediates153" style="font-size:114%;margin:0 4em"><a href="/wiki/Amino_acid" title="Amino acid">Amino acid</a> <a href="/wiki/Amino_acid_synthesis" title="Amino acid synthesis">metabolism</a> <a href="/wiki/Metabolic_intermediate" title="Metabolic intermediate">metabolic intermediates</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Ketogenic_amino_acid" title="Ketogenic amino acid">K</a>→<a href="/wiki/Acetyl-CoA" title="Acetyl-CoA">acetyl-CoA</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Lysine" title="Lysine">lysine</a>→</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Saccharopine" title="Saccharopine">Saccharopine</a></li> <li><a href="/wiki/Allysine" title="Allysine">Allysine</a></li> <li><a href="/wiki/Alpha-Aminoadipic_acid" class="mw-redirect" title="Alpha-Aminoadipic acid">α-Aminoadipic acid</a></li> <li><a href="/wiki/2-Oxoadipic_acid" title="2-Oxoadipic acid">2-Oxoadipic acid</a></li> <li><a href="/wiki/Glutaryl-CoA" title="Glutaryl-CoA">Glutaryl-CoA</a></li> <li><a href="/wiki/Glutaconyl-CoA" title="Glutaconyl-CoA">Glutaconyl-CoA</a></li> <li><a href="/wiki/Crotonyl-CoA" title="Crotonyl-CoA">Crotonyl-CoA</a></li> <li><a href="/wiki/Beta-Hydroxybutyryl-CoA" class="mw-redirect" title="Beta-Hydroxybutyryl-CoA">β-Hydroxybutyryl-CoA</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Leucine" title="Leucine">leucine</a>→</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Beta-Hydroxy_beta-methylbutyric_acid" class="mw-redirect" title="Beta-Hydroxy beta-methylbutyric acid">β-Hydroxy β-methylbutyric acid</a></li> <li><a href="/wiki/Beta-Hydroxy_beta-methylbutyryl-CoA" class="mw-redirect" title="Beta-Hydroxy beta-methylbutyryl-CoA">β-Hydroxy β-methylbutyryl-CoA</a></li> <li><a href="/wiki/Isovaleryl-CoA" title="Isovaleryl-CoA">Isovaleryl-CoA</a></li> <li><a href="/wiki/Alpha-Ketoisocaproic_acid" class="mw-redirect" title="Alpha-Ketoisocaproic acid">α-Ketoisocaproic acid</a></li> <li><a href="/wiki/Beta-Ketoisocaproic_acid" class="mw-redirect" title="Beta-Ketoisocaproic acid">β-Ketoisocaproic acid</a></li> <li><a href="/w/index.php?title=Beta-Ketoisocaproyl-CoA&action=edit&redlink=1" class="new" title="Beta-Ketoisocaproyl-CoA (page does not exist)">β-Ketoisocaproyl-CoA</a></li> <li><a href="/wiki/%CE%92-Leucine" title="Β-Leucine">β-Leucine</a></li> <li><a href="/wiki/Methylcrotonyl-CoA" title="Methylcrotonyl-CoA">β-Methylcrotonyl-CoA</a></li> <li><a href="/wiki/%CE%92-Methylglutaconyl-CoA" class="mw-redirect" title="Β-Methylglutaconyl-CoA">β-Methylglutaconyl-CoA</a></li> <li><a href="/wiki/HMG-CoA" title="HMG-CoA">β-Hydroxy β-methylglutaryl-CoA</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Tryptophan" title="Tryptophan">tryptophan</a>→<a href="/wiki/Alanine" title="Alanine">alanine</a>→</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/N%27-Formylkynurenine" title="N'-Formylkynurenine"><i>N</i>′-Formylkynurenine</a></li> <li><a href="/wiki/Kynurenine" title="Kynurenine">Kynurenine</a></li> <li><a href="/wiki/Anthranilic_acid" title="Anthranilic acid">Anthranilic acid</a></li> <li><a href="/wiki/3-Hydroxykynurenine" title="3-Hydroxykynurenine">3-Hydroxykynurenine</a></li> <li><a href="/wiki/3-Hydroxyanthranilic_acid" title="3-Hydroxyanthranilic acid">3-Hydroxyanthranilic acid</a></li> <li><a href="/wiki/2-Amino-3-carboxymuconic_semialdehyde" title="2-Amino-3-carboxymuconic semialdehyde">2-Amino-3-carboxymuconic semialdehyde</a></li> <li><a href="/wiki/2-Aminomuconic_semialdehyde" title="2-Aminomuconic semialdehyde">2-Aminomuconic semialdehyde</a></li> <li><a href="/wiki/2-Aminomuconic_acid" title="2-Aminomuconic acid">2-Aminomuconic acid</a></li> <li><a href="/wiki/Glutaryl-CoA" title="Glutaryl-CoA">Glutaryl-CoA</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Glucogenic_amino_acid" title="Glucogenic amino acid">G</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%">G→<a href="/wiki/Pyruvate" class="mw-redirect" title="Pyruvate">pyruvate</a>→ <br /><a href="/wiki/Citrate" class="mw-redirect" title="Citrate">citrate</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th id="glycine→serine→31" scope="row" class="navbox-group" style="width:1%"><a class="mw-selflink selflink">glycine</a>→<br /><a href="/wiki/Serine" title="Serine">serine</a>→</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/3-Phosphoglyceric_acid" title="3-Phosphoglyceric acid">3-Phosphoglyceric acid</a></li></ul> <ul><li><a class="mw-selflink selflink">glycine</a>→<a href="/wiki/Creatine" title="Creatine">creatine</a>: <a href="/wiki/Glycocyamine" title="Glycocyamine">Glycocyamine</a></li> <li><a href="/wiki/Phosphocreatine" title="Phosphocreatine">Phosphocreatine</a></li> <li><a href="/wiki/Creatinine" title="Creatinine">Creatinine</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">G→<a href="/wiki/Glutamate" class="mw-redirect" title="Glutamate">glutamate</a>→<br /><a href="/wiki/Alpha-Ketoglutaric_acid" class="mw-redirect" title="Alpha-Ketoglutaric acid">α-ketoglutarate</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Histidine" title="Histidine">histidine</a>→</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Urocanic_acid" title="Urocanic acid">Urocanic acid</a></li> <li><a href="/wiki/Imidazol-4-one-5-propionic_acid" title="Imidazol-4-one-5-propionic acid">Imidazol-4-one-5-propionic acid</a></li> <li><a href="/wiki/Formiminoglutamic_acid" title="Formiminoglutamic acid">Formiminoglutamic acid</a></li> <li><a href="/wiki/Glutamate-1-semialdehyde" title="Glutamate-1-semialdehyde">Glutamate-1-semialdehyde</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Proline" title="Proline">proline</a>→</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/1-Pyrroline-5-carboxylic_acid" title="1-Pyrroline-5-carboxylic acid">1-Pyrroline-5-carboxylic acid</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Arginine" title="Arginine">arginine</a>→</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Agmatine" title="Agmatine">Agmatine</a></li> <li><a href="/wiki/Ornithine" title="Ornithine">Ornithine</a></li> <li><a href="/wiki/Citrulline" title="Citrulline">Citrulline</a></li> <li><a href="/wiki/Cadaverine" title="Cadaverine">Cadaverine</a></li> <li><a href="/wiki/Putrescine" title="Putrescine">Putrescine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">other</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Cysteine" title="Cysteine">cysteine</a>+<a href="/wiki/Glutamate" class="mw-redirect" title="Glutamate">glutamate</a>→<a href="/wiki/Glutathione" title="Glutathione">glutathione</a>: <a href="/wiki/Gamma-Glutamylcysteine" class="mw-redirect" title="Gamma-Glutamylcysteine">γ-Glutamylcysteine</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">G→<a href="/wiki/Propionyl-CoA" title="Propionyl-CoA">propionyl-CoA</a>→<br /><a href="/wiki/Succinyl-CoA" title="Succinyl-CoA">succinyl-CoA</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Valine" title="Valine">valine</a>→</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Alpha-Ketoisovaleric_acid" class="mw-redirect" title="Alpha-Ketoisovaleric acid">α-Ketoisovaleric acid</a></li> <li><a href="/wiki/Isobutyryl-CoA" title="Isobutyryl-CoA">Isobutyryl-CoA</a></li> <li><a href="/wiki/Methacrylyl-CoA" title="Methacrylyl-CoA">Methacrylyl-CoA</a></li> <li><a href="/wiki/3-Hydroxyisobutyryl-CoA" title="3-Hydroxyisobutyryl-CoA">3-Hydroxyisobutyryl-CoA</a></li> <li><a href="/wiki/3-Hydroxyisobutyric_acid" title="3-Hydroxyisobutyric acid">3-Hydroxyisobutyric acid</a></li> <li><a href="/wiki/2-Methyl-3-oxopropanoic_acid" class="mw-redirect" title="2-Methyl-3-oxopropanoic acid">2-Methyl-3-oxopropanoic acid</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Isoleucine" title="Isoleucine">isoleucine</a>→</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/2,3-Dihydroxy-3-methylpentanoic_acid" title="2,3-Dihydroxy-3-methylpentanoic acid">2,3-Dihydroxy-3-methylpentanoic acid</a></li> <li><a href="/wiki/2-Methylbutyryl-CoA" title="2-Methylbutyryl-CoA">2-Methylbutyryl-CoA</a></li> <li><a href="/wiki/Tiglyl-CoA" title="Tiglyl-CoA">Tiglyl-CoA</a></li> <li><a href="/wiki/2-Methylacetoacetyl-CoA" title="2-Methylacetoacetyl-CoA">2-Methylacetoacetyl-CoA</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Methionine" title="Methionine">methionine</a>→</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i><a href="/wiki/Methionine#Generation_of_homocysteine" title="Methionine">generation of homocysteine</a>:</i> <a href="/wiki/S-Adenosyl_methionine" title="S-Adenosyl methionine"><i>S</i>-Adenosyl methionine</a></li> <li><a href="/wiki/S-Adenosyl-L-homocysteine" title="S-Adenosyl-L-homocysteine"><i>S</i>-Adenosyl-<span class="smallcaps"><span style="font-variant: small-caps; text-transform: lowercase;">L</span></span>-homocysteine</a></li> <li><a href="/wiki/Homocysteine" title="Homocysteine">Homocysteine</a></li></ul> <ul><li><i><a href="/wiki/Methionine#Conversion_to_cysteine" title="Methionine">conversion to cysteine</a>:</i> <a href="/wiki/Cystathionine" title="Cystathionine">Cystathionine</a></li> <li><a href="/wiki/Alpha-Ketobutyric_acid" class="mw-redirect" title="Alpha-Ketobutyric acid">α-Ketobutyric acid</a> + <a href="/wiki/Cysteine" title="Cysteine">Cysteine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Threonine" title="Threonine">threonine</a>→</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Alpha-Ketobutyric_acid" class="mw-redirect" title="Alpha-Ketobutyric acid">α-Ketobutyric acid</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Propionyl-CoA" title="Propionyl-CoA">propionyl-CoA</a>→</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Methylmalonyl-CoA" title="Methylmalonyl-CoA">Methylmalonyl-CoA</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">G→<a href="/wiki/Fumarate" class="mw-redirect" title="Fumarate">fumarate</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Phenylalanine" title="Phenylalanine">phenylalanine</a>→<a href="/wiki/Tyrosine" title="Tyrosine">tyrosine</a>→</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/4-Hydroxyphenylpyruvic_acid" title="4-Hydroxyphenylpyruvic acid">4-Hydroxyphenylpyruvic acid</a></li> <li><a href="/wiki/Homogentisic_acid" title="Homogentisic acid">Homogentisic acid</a></li> <li><a href="/wiki/4-Maleylacetoacetic_acid" title="4-Maleylacetoacetic acid">4-Maleylacetoacetic acid</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">G→<a href="/wiki/Oxaloacetate" class="mw-redirect" title="Oxaloacetate">oxaloacetate</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i>see <a href="/wiki/Urea_cycle" title="Urea cycle">urea cycle</a></i></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Other</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Cysteine_metabolism" title="Cysteine metabolism">Cysteine metabolism</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Cysteine_sulfinic_acid" title="Cysteine sulfinic acid">Cysteine sulfinic acid</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374" /><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235" /></div><div role="navigation" class="navbox" aria-labelledby="Neurotransmitters114" 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="Neurotransmitters114" 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 class="mw-selflink selflink">Glycine</a></li> <li><a href="/wiki/S-Nitrosoglutathione" title="S-Nitrosoglutathione">GSNO</a></li> <li><a href="/wiki/Glutathione_disulfide" title="Glutathione disulfide">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/GABA" title="GABA">GABA</a></li> <li><a href="/wiki/%CE%93-Amino-%CE%B2-hydroxybutyric_acid" title="Γ-Amino-β-hydroxybutyric acid">GABOB</a></li> <li><a href="/wiki/%CE%93-Hydroxybutyric_acid" title="Γ-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 class="mw-selflink selflink">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/%CE%93-Hydroxybutyric_acid" title="Γ-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 href="/wiki/Histamine" title="Histamine">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="Endocannabinoids33" 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="Nucleosides11" 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_system20" 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_system18" 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="Gasotransmitters16" 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="Candidates10" 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="Glycine_receptor_modulators592" style="padding:3px"><table class="nowraplinks hlist mw-collapsible mw-collapsed navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374" /><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231" /><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Glycine_receptor_modulators" title="Template:Glycine receptor modulators"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Glycine_receptor_modulators" title="Template talk:Glycine receptor modulators"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Glycine_receptor_modulators" title="Special:EditPage/Template:Glycine receptor modulators"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Glycine_receptor_modulators592" style="font-size:114%;margin:0 4em"><a href="/wiki/Glycine_receptor" title="Glycine receptor">Glycine receptor</a> <a href="/wiki/Receptor_modulator" title="Receptor modulator">modulators</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Receptor_(biochemistry)" title="Receptor (biochemistry)">Receptor</a><br /><small>(<a href="/wiki/Ligand_(biochemistry)" title="Ligand (biochemistry)">ligands</a>)</small></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:4em;;text-align:center;"><a href="/wiki/Glycine_receptor" title="Glycine receptor"><abbr title="Glycine receptor">GlyR</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Glycine receptor</span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><b>Agonists:</b> <a href="/wiki/%CE%92-Alanine" title="Β-Alanine">β-Alanine</a></li> <li><a href="/wiki/Beta-Aminobutyric_acid" class="mw-redirect" title="Beta-Aminobutyric acid">β-ABA (BABA)</a></li> <li><a href="/wiki/%CE%92-Aminoisobutyric_acid" class="mw-redirect" title="Β-Aminoisobutyric acid">β-AIBA</a></li> <li><a href="/wiki/Caesium" title="Caesium">Caesium</a></li> <li><a href="/wiki/Alanine" title="Alanine"><small>D</small>-Alanine</a></li> <li><a href="/wiki/Serine" title="Serine"><small>D</small>-Serine</a></li> <li><a href="/wiki/Gamma-Aminobutyric_acid" class="mw-redirect" title="Gamma-Aminobutyric acid">GABA</a></li> <li><a class="mw-selflink selflink">Glycine</a></li> <li><a href="/wiki/Hypotaurine" title="Hypotaurine">Hypotaurine</a></li> <li><a href="/wiki/Ivermectin" title="Ivermectin">Ivermectin</a></li> <li><a href="/wiki/Alanine" title="Alanine"><small>L</small>-Alanine</a></li> <li><a href="/wiki/Proline" title="Proline"><small>L</small>-Proline</a></li> <li><a href="/wiki/Serine" title="Serine"><small>L</small>-Serine</a></li> <li><a href="/wiki/Threonine" title="Threonine"><small>L</small>-Threonine</a></li> <li><a href="/w/index.php?title=MDL-27531&action=edit&redlink=1" class="new" title="MDL-27531 (page does not exist)">MDL-27531</a></li> <li><a href="/wiki/Milacemide" title="Milacemide">Milacemide</a></li> <li><a href="/wiki/Picolinic_acid" title="Picolinic acid">Picolinic acid</a></li> <li><a href="/wiki/Propofol" title="Propofol">Propofol</a></li> <li><a href="/wiki/Quisqualamine" title="Quisqualamine">Quisqualamine</a></li> <li><a href="/wiki/Sarcosine" title="Sarcosine">Sarcosine</a></li> <li><a href="/wiki/Taurine" title="Taurine">Taurine</a></li></ul> <ul><li><b>Positive modulators:</b> <a href="/wiki/Alcohol_(chemistry)" title="Alcohol (chemistry)">Alcohols</a> (e.g., <a href="/w/index.php?title=Brometone&action=edit&redlink=1" class="new" title="Brometone (page does not exist)">brometone</a>, <a href="/wiki/Chlorobutanol" title="Chlorobutanol">chlorobutanol (chloretone)</a>, <a href="/wiki/Alcohol_(drug)" title="Alcohol (drug)">ethanol (alcohol)</a>, <a href="/wiki/Tert-Butyl_alcohol" title="Tert-Butyl alcohol"><i>tert</i>-butanol (2M2P)</a>, <a href="/wiki/Tribromoethanol" title="Tribromoethanol">tribromoethanol</a>, <a href="/wiki/Trichloroethanol" class="mw-redirect" title="Trichloroethanol">trichloroethanol</a>, <a href="/wiki/Trifluoroethanol" class="mw-redirect" title="Trifluoroethanol">trifluoroethanol</a>)</li> <li><a href="/wiki/Alkylbenzene_sulfonate" title="Alkylbenzene sulfonate">Alkylbenzene sulfonate</a></li> <li><a href="/wiki/Anandamide" title="Anandamide">Anandamide</a></li> <li><a href="/wiki/Barbiturate" title="Barbiturate">Barbiturates</a> (e.g., <a href="/wiki/Pentobarbital" title="Pentobarbital">pentobarbital</a>, <a href="/wiki/Sodium_thiopental" title="Sodium thiopental">sodium thiopental</a>)</li> <li><a href="/wiki/Chlormethiazole" class="mw-redirect" title="Chlormethiazole">Chlormethiazole</a></li> <li><a href="/w/index.php?title=D12-116&action=edit&redlink=1" class="new" title="D12-116 (page does not exist)">D12-116</a></li> <li><a href="/wiki/Dihydropyridine" class="mw-redirect" title="Dihydropyridine">Dihydropyridines</a> (e.g., <a href="/wiki/Nicardipine" title="Nicardipine">nicardipine</a>)</li> <li><a href="/wiki/Etomidate" title="Etomidate">Etomidate</a></li> <li><a href="/wiki/Ginseng" title="Ginseng">Ginseng</a> constituents (e.g., <a href="/wiki/Ginsenoside" title="Ginsenoside">ginsenosides</a> (e.g., <a href="/w/index.php?title=Ginsenoside-Rf&action=edit&redlink=1" class="new" title="Ginsenoside-Rf (page does not exist)">ginsenoside-Rf</a>))</li> <li><a href="/wiki/Glutamic_acid" title="Glutamic acid">Glutamic acid (glutamate)</a></li> <li><a href="/wiki/Ivermectin" title="Ivermectin">Ivermectin</a></li> <li><a href="/wiki/Ketamine" title="Ketamine">Ketamine</a></li> <li><a href="/wiki/Neuroactive_steroid" class="mw-redirect" title="Neuroactive steroid">Neuroactive steroids</a> (e.g., <a href="/wiki/Alfaxolone" class="mw-redirect" title="Alfaxolone">alfaxolone</a>, <a href="/wiki/Pregnenolone" title="Pregnenolone">pregnenolone (eltanolone)</a>, <a href="/wiki/Pregnenolone_acetate" title="Pregnenolone acetate">pregnenolone acetate</a>, <a href="/wiki/Minaxolone" title="Minaxolone">minaxolone</a>, <a href="/wiki/ORG-20599" title="ORG-20599">ORG-20599</a>)</li> <li><a href="/wiki/Nitrous_oxide" title="Nitrous oxide">Nitrous oxide</a></li> <li><a href="/wiki/Penicillin_G" class="mw-redirect" title="Penicillin G">Penicillin G</a></li> <li><a href="/wiki/Propofol" title="Propofol">Propofol</a></li> <li><a href="/wiki/Tamoxifen" title="Tamoxifen">Tamoxifen</a></li> <li><a href="/wiki/Tetrahydrocannabinol" title="Tetrahydrocannabinol">Tetrahydrocannabinol</a></li> <li><a href="/wiki/Triclofos" title="Triclofos">Triclofos</a></li> <li><a href="/w/index.php?title=Tropeine&action=edit&redlink=1" class="new" title="Tropeine (page does not exist)">Tropeines</a> (e.g., <a href="/wiki/Atropine" title="Atropine">atropine</a>, <a href="/wiki/Bemesetron" title="Bemesetron">bemesetron</a>, <a href="/wiki/Cocaine" title="Cocaine">cocaine</a>, <a href="/w/index.php?title=LY-278584&action=edit&redlink=1" class="new" title="LY-278584 (page does not exist)">LY-278584</a>, <a href="/wiki/Tropisetron" title="Tropisetron">tropisetron</a>, <a href="/wiki/Zatosetron" title="Zatosetron">zatosetron</a>)</li> <li><a href="/wiki/Volatility_(chemistry)" title="Volatility (chemistry)">Volatiles</a>/<a href="/wiki/Gas" title="Gas">gases</a> (e.g., <a href="/wiki/Chloral_hydrate" title="Chloral hydrate">chloral hydrate</a>, <a href="/wiki/Chloroform" title="Chloroform">chloroform</a>, <a href="/wiki/Desflurane" title="Desflurane">desflurane</a>, <a href="/wiki/Diethyl_ether" title="Diethyl ether">diethyl ether (ether)</a>, <a href="/wiki/Enflurane" title="Enflurane">enflurane</a>, <a href="/wiki/Halothane" title="Halothane">halothane</a>, <a href="/wiki/Isoflurane" title="Isoflurane">isoflurane</a>, <a href="/wiki/Methoxyflurane" title="Methoxyflurane">methoxyflurane</a>, <a href="/wiki/Sevoflurane" title="Sevoflurane">sevoflurane</a>, <a href="/wiki/Toluene" title="Toluene">toluene</a>, <a href="/wiki/1,1,1-trichloroethane" class="mw-redirect" title="1,1,1-trichloroethane">trichloroethane (methyl chloroform)</a>, <a href="/wiki/Trichloroethylene" title="Trichloroethylene">trichloroethylene</a>)</li> <li><a href="/wiki/Xenon" title="Xenon">Xenon</a></li> <li><a href="/wiki/Zinc" title="Zinc">Zinc</a></li></ul> <ul><li><b>Antagonists:</b> <a href="/w/index.php?title=2-Aminostrychnine&action=edit&redlink=1" class="new" title="2-Aminostrychnine (page does not exist)">2-Aminostrychnine</a></li> <li><a href="/w/index.php?title=2-Nitrostrychnine&action=edit&redlink=1" class="new" title="2-Nitrostrychnine (page does not exist)">2-Nitrostrychnine</a></li> <li><a href="/w/index.php?title=4-Phenyl-4-formyl-N-methylpiperidine&action=edit&redlink=1" class="new" title="4-Phenyl-4-formyl-N-methylpiperidine (page does not exist)">4-Phenyl-4-formyl-N-methylpiperidine</a></li> <li><a href="/w/index.php?title=%CE%91-Ethyl-%CE%B1-methyl-%CE%B3-thiobutyrolactone&action=edit&redlink=1" class="new" title="Α-Ethyl-α-methyl-γ-thiobutyrolactone (page does not exist)">αEMBTL</a></li> <li><a href="/wiki/Bicuculline" title="Bicuculline">Bicuculline</a></li> <li><a href="/wiki/Brucine" title="Brucine">Brucine</a></li> <li><a href="/wiki/Cacotheline" title="Cacotheline">Cacotheline</a></li> <li><a href="/wiki/Caffeine" title="Caffeine">Caffeine</a></li> <li><a href="/wiki/Colchicine" title="Colchicine">Colchicine</a></li> <li><a href="/wiki/Colubrine" class="mw-redirect" title="Colubrine">Colubrine</a></li> <li><a href="/w/index.php?title=Cyanotriphenylborate&action=edit&redlink=1" class="new" title="Cyanotriphenylborate (page does not exist)">Cyanotriphenylborate</a></li> <li><a href="/wiki/Dendrobine" title="Dendrobine">Dendrobine</a></li> <li><a href="/w/index.php?title=Diaboline&action=edit&redlink=1" class="new" title="Diaboline (page does not exist)">Diaboline</a></li> <li><a href="/wiki/Endocannabinoid" class="mw-redirect" title="Endocannabinoid">Endocannabinoids</a> (e.g., <a href="/wiki/2-arachidonylglycerol" class="mw-redirect" title="2-arachidonylglycerol">2-AG</a>, <a href="/wiki/Anandamide" title="Anandamide">anandamide (AEA)</a>)</li> <li><a href="/wiki/Gaboxadol" title="Gaboxadol">Gaboxadol (THIP)</a></li> <li><a href="/wiki/Gelsemine" title="Gelsemine">Gelsemine</a></li> <li><a href="/w/index.php?title=Iso-THAZ&action=edit&redlink=1" class="new" title="Iso-THAZ (page does not exist)">iso-THAZ</a></li> <li><a href="/wiki/Isobutyric_acid" title="Isobutyric acid">Isobutyric acid</a></li> <li><a href="/wiki/Isonipecotic_acid" title="Isonipecotic acid">Isonipecotic acid</a></li> <li><a href="/w/index.php?title=Isostrychnine&action=edit&redlink=1" class="new" title="Isostrychnine (page does not exist)">Isostrychnine</a></li> <li><a href="/wiki/Laudanosine" title="Laudanosine">Laudanosine</a></li> <li><a href="/w/index.php?title=N-Methylbicuculline&action=edit&redlink=1" class="new" title="N-Methylbicuculline (page does not exist)">N-Methylbicuculline</a></li> <li><a href="/w/index.php?title=N-Methylstrychnine&action=edit&redlink=1" class="new" title="N-Methylstrychnine (page does not exist)">N-Methylstrychnine</a></li> <li><a href="/w/index.php?title=N,N-Dimethylmuscimol&action=edit&redlink=1" class="new" title="N,N-Dimethylmuscimol (page does not exist)">N,N-Dimethylmuscimol</a></li> <li><a href="/wiki/Nipecotic_acid" title="Nipecotic acid">Nipecotic acid</a></li> <li><a href="/wiki/Pitrazepin" title="Pitrazepin">Pitrazepin</a></li> <li><a href="/w/index.php?title=Pseudostrychnine&action=edit&redlink=1" class="new" title="Pseudostrychnine (page does not exist)">Pseudostrychnine</a></li> <li><a href="/wiki/Quinoline" title="Quinoline">Quinolines</a> (e.g., <a href="/w/index.php?title=4-hydroxyquinoline&action=edit&redlink=1" class="new" title="4-hydroxyquinoline (page does not exist)">4-hydroxyquinoline</a>, <a href="/w/index.php?title=4-hydroxyquinoline-3-carboxylic_acid&action=edit&redlink=1" class="new" title="4-hydroxyquinoline-3-carboxylic acid (page does not exist)">4-hydroxyquinoline-3-carboxylic acid</a>, <a href="/w/index.php?title=5,7-dichloro-4-hydroxyquinoline-3-carboxylic_acid&action=edit&redlink=1" class="new" title="5,7-dichloro-4-hydroxyquinoline-3-carboxylic acid (page does not exist)">5,7-CIQA</a>, <a href="/w/index.php?title=7-chloro-4-hydroxyquinoline&action=edit&redlink=1" class="new" title="7-chloro-4-hydroxyquinoline (page does not exist)">7-CIQ</a>, <a href="/w/index.php?title=7-trifluoromethyl-4-hydroxyquinoline&action=edit&redlink=1" class="new" title="7-trifluoromethyl-4-hydroxyquinoline (page does not exist)">7-TFQ</a>, <a href="/w/index.php?title=7-trifluoromethyl-4-hydroxyquinoline-3-carboxylic_acid&action=edit&redlink=1" class="new" title="7-trifluoromethyl-4-hydroxyquinoline-3-carboxylic acid (page does not exist)">7-TFQA</a>)</li> <li><a href="/w/index.php?title=RU-5135&action=edit&redlink=1" class="new" title="RU-5135 (page does not exist)">RU-5135</a></li> <li><a href="/wiki/Sinomenine" title="Sinomenine">Sinomenine</a></li> <li><a href="/wiki/Strychnine" title="Strychnine">Strychnine</a></li> <li><a href="/wiki/Thiocolchicoside" title="Thiocolchicoside">Thiocolchicoside</a></li> <li><a href="/wiki/Tutin_(toxin)" title="Tutin (toxin)">Tutin</a></li></ul> <ul><li><b>Negative modulators:</b> <a href="/wiki/Amiloride" title="Amiloride">Amiloride</a></li> <li><a href="/wiki/Benzodiazepine" title="Benzodiazepine">Benzodiazepines</a> (e.g., <a href="/wiki/Bromazepam" title="Bromazepam">bromazepam</a>, <a href="/wiki/Clonazepam" title="Clonazepam">clonazepam</a>, <a href="/wiki/Diazepam" title="Diazepam">diazepam</a>, <a href="/wiki/Flunitrazepam" title="Flunitrazepam">flunitrazepam</a>, <a href="/wiki/Flurazepam" title="Flurazepam">flurazepam</a>)</li> <li><a href="/wiki/Corymine" title="Corymine">Corymine</a></li> <li><a href="/w/index.php?title=Cyanotriphenylborate&action=edit&redlink=1" class="new" title="Cyanotriphenylborate (page does not exist)">Cyanotriphenylborate</a></li> <li><a href="/wiki/Daidzein" title="Daidzein">Daidzein</a></li> <li><a href="/wiki/Dihydropyridine" class="mw-redirect" title="Dihydropyridine">Dihydropyridines</a> (e.g., <a href="/wiki/Nicardipine" title="Nicardipine">nicardipine</a>, <a href="/wiki/Nifedipine" title="Nifedipine">nifedipine</a>, <a href="/wiki/Nitrendipine" title="Nitrendipine">nitrendipine</a>)</li> <li><a href="/wiki/Furosemide" title="Furosemide">Furosemide</a></li> <li><a href="/wiki/Genistein" title="Genistein">Genistein</a></li> <li><a href="/wiki/Ginkgo_biloba" title="Ginkgo biloba">Ginkgo</a> constituents (e.g., <a href="/wiki/Bilobalide" title="Bilobalide">bilobalide</a>, <a href="/wiki/Ginkgolide" title="Ginkgolide">ginkgolides</a> (e.g., <a href="/w/index.php?title=Ginkgolide_A&action=edit&redlink=1" class="new" title="Ginkgolide A (page does not exist)">ginkgolide A</a>, <a href="/wiki/Ginkgolide_B" class="mw-redirect" title="Ginkgolide B">ginkgolide B</a>, <a href="/w/index.php?title=Ginkgolide_C&action=edit&redlink=1" class="new" title="Ginkgolide C (page does not exist)">ginkgolide C</a>, <a href="/w/index.php?title=Ginkgolide_J&action=edit&redlink=1" class="new" title="Ginkgolide J (page does not exist)">ginkgolide J</a>, <a href="/w/index.php?title=Ginkgolide_M&action=edit&redlink=1" class="new" title="Ginkgolide M (page does not exist)">ginkgolide M</a>))</li> <li><a href="/wiki/Imipramine" title="Imipramine">Imipramine</a></li> <li><a href="/wiki/NBQX" title="NBQX">NBQX</a></li> <li><a href="/wiki/Neuroactive_steroid" class="mw-redirect" title="Neuroactive steroid">Neuroactive steroids</a> (e.g., <a href="/wiki/3%CE%B1-androsterone_sulfate" class="mw-redirect" title="3α-androsterone sulfate">3α-androsterone sulfate</a>, <a href="/w/index.php?title=3%CE%B2-androsterone_sulfate&action=edit&redlink=1" class="new" title="3β-androsterone sulfate (page does not exist)">3β-androsterone sulfate</a>, <a href="/wiki/11-deoxycorticosterone" class="mw-redirect" title="11-deoxycorticosterone">deoxycorticosterone</a>, <a href="/wiki/DHEA_sulfate" class="mw-redirect" title="DHEA sulfate">DHEA sulfate</a>, <a href="/wiki/Pregnenolone_sulfate" title="Pregnenolone sulfate">pregnenolone sulfate</a>, <a href="/wiki/Progesterone" title="Progesterone">progesterone</a>)</li> <li><a href="/wiki/Opioid" title="Opioid">Opioids</a> (e.g., <a href="/wiki/Codeine" title="Codeine">codeine</a>, <a href="/wiki/Dextromethorphan" title="Dextromethorphan">dextromethorphan</a>, <a href="/wiki/Dextrorphan" title="Dextrorphan">dextrorphan</a>, <a href="/wiki/Levomethadone" title="Levomethadone">levomethadone</a>, <a href="/wiki/Levorphanol" title="Levorphanol">levorphanol</a>, <a href="/wiki/Morphine" title="Morphine">morphine</a>, <a href="/wiki/Oripavine" title="Oripavine">oripavine</a>, <a href="/wiki/Pethidine" title="Pethidine">pethidine</a>, <a href="/wiki/Thebaine" title="Thebaine">thebaine</a>)</li> <li><a href="/wiki/Picrotoxin" title="Picrotoxin">Picrotoxin</a> (i.e., <a href="/wiki/Picrotin" class="mw-redirect" title="Picrotin">picrotin</a> and <a href="/wiki/Picrotoxinin" class="mw-redirect" title="Picrotoxinin">picrotoxinin</a>)</li> <li><a href="/w/index.php?title=Phenylbenzene_%CF%89-phosphono-%CE%B1-amino_acid&action=edit&redlink=1" class="new" title="Phenylbenzene ω-phosphono-α-amino acid (page does not exist)">PMBA</a></li> <li><a href="/wiki/Riluzole" title="Riluzole">Riluzole</a></li> <li><a href="/w/index.php?title=Tropeine&action=edit&redlink=1" class="new" title="Tropeine (page does not exist)">Tropeines</a> (e.g., <a href="/wiki/Bemesetron" title="Bemesetron">bemesetron</a>, <a href="/w/index.php?title=LY-278584&action=edit&redlink=1" class="new" title="LY-278584 (page does not exist)">LY-278584</a>, <a href="/wiki/Tropisetron" title="Tropisetron">tropisetron</a>, <a href="/wiki/Zatosetron" title="Zatosetron">zatosetron</a>)</li> <li><a href="/wiki/Verapamil" title="Verapamil">Verapamil</a></li> <li><a href="/wiki/Zinc" title="Zinc">Zinc</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:4em;;text-align:center;"><a href="/wiki/N-Methyl-D-aspartate_receptor" class="mw-redirect" title="N-Methyl-D-aspartate receptor"><abbr title="N-Methyl-D-aspartate receptor">NMDAR</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip N-Methyl-D-aspartate receptor</span></th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li>See <a href="/wiki/Template:Ionotropic_glutamate_receptor_modulators" title="Template:Ionotropic glutamate receptor modulators">here</a> instead.</li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Neurotransmitter_transporter" title="Neurotransmitter transporter">Transporter</a><br /><small>(<a href="/wiki/Reuptake_inhibitor" title="Reuptake inhibitor">blockers</a>)</small></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:4em;;text-align:center;"><a href="/wiki/Glycine_transporter_1" class="mw-redirect" title="Glycine transporter 1"><abbr title="Glycine transporter 1">GlyT1</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Glycine transporter 1</span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/w/index.php?title=ACPPB&action=edit&redlink=1" class="new" title="ACPPB (page does not exist)">ACPPB</a></li> <li><a href="/w/index.php?title=ALX-5407&action=edit&redlink=1" class="new" title="ALX-5407 (page does not exist)">ALX-5407 (NFPS)</a></li> <li><a href="/wiki/ASP2535" title="ASP2535">ASP2535</a></li> <li><a href="/wiki/Bitopertin" title="Bitopertin">Bitopertin (RG1678/RO4917838)</a></li> <li><a href="/w/index.php?title=CP-802079&action=edit&redlink=1" class="new" title="CP-802079 (page does not exist)">CP-802079</a></li> <li><a href="/wiki/Alcohol_(drug)" title="Alcohol (drug)">Ethanol (alcohol)</a></li> <li><a href="/w/index.php?title=Glycyldodecylamide&action=edit&redlink=1" class="new" title="Glycyldodecylamide (page does not exist)">Glycyldodecylamide</a></li> <li><a href="/w/index.php?title=GSK1018921&action=edit&redlink=1" class="new" title="GSK1018921 (page does not exist)">GSK1018921</a></li> <li><a href="/wiki/Iclepertin" title="Iclepertin">Iclepertin</a></li> <li><a href="/wiki/LY-2365109" title="LY-2365109">LY-2365109</a></li> <li><a href="/wiki/Mardepodect" title="Mardepodect">Mardepodect</a></li> <li><a href="/wiki/ORG-24598" title="ORG-24598">ORG-24598</a></li> <li><a href="/wiki/ORG-25935" title="ORG-25935">ORG-25935 (SCH-900435)</a></li> <li><a href="/wiki/Pesampator" title="Pesampator">Pesampator (BIIB-104, PF-04958242)</a></li> <li><a href="/w/index.php?title=PF-03463275&action=edit&redlink=1" class="new" title="PF-03463275 (page does not exist)">PF-03463275</a></li> <li><a href="/wiki/Sarcosine" title="Sarcosine">Sarcosine</a></li> <li><a href="/wiki/SNG-12" title="SNG-12">SNG-12 (Synapsinae)</a></li> <li><a href="/w/index.php?title=SSR-103,800&action=edit&redlink=1" class="new" title="SSR-103,800 (page does not exist)">SSR-103,800</a></li> <li><a href="/w/index.php?title=SSR-504,734&action=edit&redlink=1" class="new" title="SSR-504,734 (page does not exist)">SSR-504,734</a></li> <li><a href="/wiki/Tilapertin" title="Tilapertin">Tilapertin</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:4em;;text-align:center;"><a href="/wiki/Glycine_transporter_2" class="mw-redirect" title="Glycine transporter 2"><abbr title="Glycine transporter 2">GlyT2</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Glycine transporter 2</span></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/ALX-1393" title="ALX-1393">ALX-1393</a></li> <li><a href="/wiki/Amoxapine" title="Amoxapine">Amoxapine</a></li> <li><a href="/wiki/Alcohol_(drug)" title="Alcohol (drug)">Ethanol (alcohol)</a></li> <li><a href="/wiki/N-Arachidonylglycine" title="N-Arachidonylglycine">NAGly</a></li> <li><a href="/wiki/Opiranserin" title="Opiranserin">Opiranserin (VVZ-149)</a></li> <li><a href="/w/index.php?title=ORG-25543&action=edit&redlink=1" class="new" title="ORG-25543 (page does not exist)">ORG-25543</a></li> <li><a href="/w/index.php?title=VVZ-368&action=edit&redlink=1" class="new" title="VVZ-368 (page does not exist)">VVZ-368</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><i><a href="/wiki/Template:Receptor_modulators" title="Template:Receptor modulators">Receptor/signaling modulators</a></i></dd> <dd><i><a href="/wiki/Template:GABA_receptor_modulators" title="Template:GABA receptor modulators">GABA receptor modulators</a></i></dd> <dd><i><a href="/wiki/Template:GABAA_receptor_positive_modulators" title="Template:GABAA receptor positive modulators">GABA<sub>A</sub> receptor positive modulators</a></i></dd> <dd><i><a href="/wiki/Template:Ionotropic_glutamate_receptor_modulators" title="Template:Ionotropic glutamate receptor modulators">Ionotropic glutamate receptor modulators</a></i></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="Ionotropic_glutamate_receptor_modulators1643" style="padding:3px"><table class="nowraplinks hlist mw-collapsible mw-collapsed navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374" /><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231" /><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Ionotropic_glutamate_receptor_modulators" title="Template:Ionotropic glutamate receptor modulators"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Ionotropic_glutamate_receptor_modulators" title="Template talk:Ionotropic glutamate receptor modulators"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Ionotropic_glutamate_receptor_modulators" title="Special:EditPage/Template:Ionotropic glutamate receptor modulators"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Ionotropic_glutamate_receptor_modulators1643" style="font-size:114%;margin:0 4em"><a href="/wiki/Ionotropic_glutamate_receptor" title="Ionotropic glutamate receptor">Ionotropic glutamate 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/%CE%91-Amino-3-hydroxy-5-methyl-4-isoxazolepropionic_acid_receptor" class="mw-redirect" title="Α-Amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid receptor"><abbr title="α-Amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid receptor">AMPAR</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip α-Amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid receptor</span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><b>Agonists:</b> <i>Main site agonists:</i> <a href="/wiki/5-Fluorowillardiine" title="5-Fluorowillardiine">5-Fluorowillardiine</a></li> <li><a href="/wiki/Acromelic_acid_A" title="Acromelic acid A">Acromelic acid (acromelate)</a></li> <li><a href="/wiki/AMPA" title="AMPA">AMPA</a></li> <li><a href="/w/index.php?title=%CE%92-N-Oxalylamino-L-Alanine&action=edit&redlink=1" class="new" title="Β-N-Oxalylamino-L-Alanine (page does not exist)">BOAA</a></li> <li><a href="/wiki/Domoic_acid" title="Domoic acid">Domoic acid</a></li> <li><a href="/wiki/Glutamate" class="mw-redirect" title="Glutamate">Glutamate</a></li> <li><a href="/wiki/Ibotenic_acid" title="Ibotenic acid">Ibotenic acid</a></li> <li><a href="/wiki/Proline" title="Proline">Proline</a></li> <li><a href="/wiki/Quisqualic_acid" title="Quisqualic acid">Quisqualic acid</a></li> <li><a href="/wiki/Willardiine" title="Willardiine">Willardiine</a>; <i>Positive allosteric modulators:</i> <a href="/wiki/Aniracetam" title="Aniracetam">Aniracetam</a></li> <li><a href="/wiki/Cyclothiazide" title="Cyclothiazide">Cyclothiazide</a></li> <li><a href="/wiki/CX-516" title="CX-516">CX-516</a></li> <li><a href="/wiki/CX-546" title="CX-546">CX-546</a></li> <li><a href="/wiki/CX614" title="CX614">CX-614</a></li> <li><a href="/wiki/Farampator" title="Farampator">Farampator (CX-691, ORG-24448)</a></li> <li><a href="/wiki/CX717" title="CX717">CX-717</a></li> <li><a href="/wiki/CX-1739" class="mw-redirect" title="CX-1739">CX-1739</a></li> <li><a href="/w/index.php?title=CX-1942&action=edit&redlink=1" class="new" title="CX-1942 (page does not exist)">CX-1942</a></li> <li><a href="/wiki/Diazoxide" title="Diazoxide">Diazoxide</a></li> <li><a href="/wiki/Hydrochlorothiazide" title="Hydrochlorothiazide">Hydrochlorothiazide (HCTZ)</a></li> <li><a href="/wiki/IDRA-21" title="IDRA-21">IDRA-21</a></li> <li><a href="/w/index.php?title=LY-392098&action=edit&redlink=1" class="new" title="LY-392098 (page does not exist)">LY-392098</a></li> <li><a href="/w/index.php?title=LY-395153&action=edit&redlink=1" class="new" title="LY-395153 (page does not exist)">LY-395153</a></li> <li><a href="/wiki/LY-404187" title="LY-404187">LY-404187</a></li> <li><a href="/w/index.php?title=LY-451646&action=edit&redlink=1" class="new" title="LY-451646 (page does not exist)">LY-451646</a></li> <li><a href="/wiki/LY-503430" title="LY-503430">LY-503430</a></li> <li><a href="/wiki/Mibampator" title="Mibampator">Mibampator (LY-451395)</a></li> <li><a href="/wiki/Nooglutyl" title="Nooglutyl">Nooglutyl</a></li> <li><a href="/wiki/ORG-26576" title="ORG-26576">ORG-26576</a></li> <li><a href="/wiki/Oxiracetam" title="Oxiracetam">Oxiracetam</a></li> <li><a href="/wiki/PEPA_(drug)" title="PEPA (drug)">PEPA</a></li> <li><a href="/wiki/Pesampator" title="Pesampator">Pesampator (BIIB-104, PF-04958242)</a></li> <li><a href="/wiki/Piracetam" title="Piracetam">Piracetam</a></li> <li><a href="/wiki/Pramiracetam" title="Pramiracetam">Pramiracetam</a></li> <li><a href="/wiki/S-18986" title="S-18986">S-18986</a></li> <li><a href="/wiki/Tulrampator" title="Tulrampator">Tulrampator (S-47445, CX-1632)</a></li></ul> <ul><li><b>Antagonists:</b> <a href="/w/index.php?title=ACEA-1011&action=edit&redlink=1" class="new" title="ACEA-1011 (page does not exist)">ACEA-1011</a></li> <li><a href="/w/index.php?title=ATPO&action=edit&redlink=1" class="new" title="ATPO (page does not exist)">ATPO</a></li> <li><a href="/wiki/Becampanel" title="Becampanel">Becampanel</a></li> <li><a href="/wiki/Caroverine" title="Caroverine">Caroverine</a></li> <li><a href="/wiki/CNQX" title="CNQX">CNQX</a></li> <li><a href="/wiki/Dasolampanel" title="Dasolampanel">Dasolampanel</a></li> <li><a href="/wiki/DNQX" title="DNQX">DNQX</a></li> <li><a href="/wiki/Fanapanel" title="Fanapanel">Fanapanel (MPQX)</a></li> <li><a href="/w/index.php?title=Gamma-D-Glutamylaminomethylsulfonic_acid&action=edit&redlink=1" class="new" title="Gamma-D-Glutamylaminomethylsulfonic acid (page does not exist)">GAMS</a></li> <li><a href="/wiki/Kaitocephalin" title="Kaitocephalin">Kaitocephalin</a></li> <li><a href="/wiki/Kynurenic_acid" title="Kynurenic acid">Kynurenic acid</a></li> <li><a href="/wiki/Kynurenine" title="Kynurenine">Kynurenine</a></li> <li><a href="/wiki/Licostinel" title="Licostinel">Licostinel (ACEA-1021)</a></li> <li><a href="/wiki/NBQX" title="NBQX">NBQX</a></li> <li><a href="/w/index.php?title=PNQX&action=edit&redlink=1" class="new" title="PNQX (page does not exist)">PNQX</a></li> <li><a href="/wiki/Selurampanel" title="Selurampanel">Selurampanel</a></li> <li><a href="/wiki/Tezampanel" title="Tezampanel">Tezampanel</a></li> <li><a href="/wiki/Theanine" title="Theanine">Theanine</a></li> <li><a href="/wiki/Topiramate" title="Topiramate">Topiramate</a></li> <li><a href="/w/index.php?title=YM90K&action=edit&redlink=1" class="new" title="YM90K (page does not exist)">YM90K</a></li> <li><a href="/wiki/Zonampanel" title="Zonampanel">Zonampanel</a>; <i>Negative allosteric modulators:</i> <a href="/wiki/Barbiturates" class="mw-redirect" title="Barbiturates">Barbiturates</a> (e.g., <a href="/wiki/Pentobarbital" title="Pentobarbital">pentobarbital</a>, <a href="/wiki/Sodium_thiopental" title="Sodium thiopental">sodium thiopental</a>)</li> <li><a href="/wiki/Cyclopropane" title="Cyclopropane">Cyclopropane</a></li> <li><a href="/wiki/Enflurane" title="Enflurane">Enflurane</a></li> <li><a href="/wiki/Alcohol_(drug)" title="Alcohol (drug)">Ethanol (alcohol)</a></li> <li><a href="/wiki/Evans_blue_(dye)" title="Evans blue (dye)">Evans blue</a></li> <li><a href="/wiki/GYKI_52466" title="GYKI 52466">GYKI-52466</a></li> <li><a href="/w/index.php?title=GYKI-53655&action=edit&redlink=1" class="new" title="GYKI-53655 (page does not exist)">GYKI-53655</a></li> <li><a href="/wiki/Halothane" title="Halothane">Halothane</a></li> <li><a href="/wiki/Irampanel" title="Irampanel">Irampanel</a></li> <li><a href="/wiki/Isoflurane" title="Isoflurane">Isoflurane</a></li> <li><a href="/wiki/Perampanel" title="Perampanel">Perampanel</a></li> <li><a href="/wiki/Pregnenolone_sulfate" title="Pregnenolone sulfate">Pregnenolone sulfate</a></li> <li><a href="/wiki/Sevoflurane" title="Sevoflurane">Sevoflurane</a></li> <li><a href="/wiki/Talampanel" title="Talampanel">Talampanel</a>; <i>Unknown/unsorted antagonists:</i> <a href="/wiki/Minocycline" title="Minocycline">Minocycline</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Kainate_receptor" title="Kainate receptor"><abbr title="Kainate receptor">KAR</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Kainate receptor</span></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><b>Agonists:</b> <i>Main site agonists:</i> <a href="/w/index.php?title=5-Bromowillardiine&action=edit&redlink=1" class="new" title="5-Bromowillardiine (page does not exist)">5-Bromowillardiine</a></li> <li><a href="/wiki/5-Iodowillardiine" title="5-Iodowillardiine">5-Iodowillardiine</a></li> <li><a href="/w/index.php?title=Acromelic_acid&action=edit&redlink=1" class="new" title="Acromelic acid (page does not exist)">Acromelic acid (acromelate)</a></li> <li><a href="/wiki/AMPA" title="AMPA">AMPA</a></li> <li><a href="/w/index.php?title=ATPA&action=edit&redlink=1" class="new" title="ATPA (page does not exist)">ATPA</a></li> <li><a href="/wiki/Domoic_acid" title="Domoic acid">Domoic acid</a></li> <li><a href="/wiki/Glutamate" class="mw-redirect" title="Glutamate">Glutamate</a></li> <li><a href="/wiki/Ibotenic_acid" title="Ibotenic acid">Ibotenic acid</a></li> <li><a href="/wiki/Kainic_acid" title="Kainic acid">Kainic acid</a></li> <li><a href="/w/index.php?title=LY-339434&action=edit&redlink=1" class="new" title="LY-339434 (page does not exist)">LY-339434</a></li> <li><a href="/wiki/Proline" title="Proline">Proline</a></li> <li><a href="/wiki/Quisqualic_acid" title="Quisqualic acid">Quisqualic acid</a></li> <li><a href="/wiki/SYM-2081" title="SYM-2081">SYM-2081</a>; <i>Positive allosteric modulators:</i> <a href="/wiki/Cyclothiazide" title="Cyclothiazide">Cyclothiazide</a></li> <li><a href="/wiki/Diazoxide" title="Diazoxide">Diazoxide</a></li> <li><a href="/wiki/Enflurane" title="Enflurane">Enflurane</a></li> <li><a href="/wiki/Halothane" title="Halothane">Halothane</a></li> <li><a href="/wiki/Isoflurane" title="Isoflurane">Isoflurane</a></li></ul> <ul><li><b>Antagonists:</b> <a href="/w/index.php?title=ACEA-1011&action=edit&redlink=1" class="new" title="ACEA-1011 (page does not exist)">ACEA-1011</a></li> <li><a href="/wiki/CNQX" title="CNQX">CNQX</a></li> <li><a href="/wiki/Dasolampanel" title="Dasolampanel">Dasolampanel</a></li> <li><a href="/wiki/DNQX" title="DNQX">DNQX</a></li> <li><a href="/w/index.php?title=Gamma-D-Glutamylaminomethylsulfonic_acid&action=edit&redlink=1" class="new" title="Gamma-D-Glutamylaminomethylsulfonic acid (page does not exist)">GAMS</a></li> <li><a href="/wiki/Kaitocephalin" title="Kaitocephalin">Kaitocephalin</a></li> <li><a href="/wiki/Kynurenic_acid" title="Kynurenic acid">Kynurenic acid</a></li> <li><a href="/wiki/Licostinel" title="Licostinel">Licostinel (ACEA-1021)</a></li> <li><a href="/w/index.php?title=LY-382884&action=edit&redlink=1" class="new" title="LY-382884 (page does not exist)">LY-382884</a></li> <li><a href="/wiki/NBQX" title="NBQX">NBQX</a></li> <li><a href="/wiki/NS102" title="NS102">NS102</a></li> <li><a href="/wiki/Selurampanel" title="Selurampanel">Selurampanel</a></li> <li><a href="/wiki/Tezampanel" title="Tezampanel">Tezampanel</a></li> <li><a href="/wiki/Theanine" title="Theanine">Theanine</a></li> <li><a href="/wiki/Topiramate" title="Topiramate">Topiramate</a></li> <li><a href="/wiki/UBP-302" title="UBP-302">UBP-302</a>; <i>Negative allosteric modulators:</i> <a href="/wiki/Barbiturates" class="mw-redirect" title="Barbiturates">Barbiturates</a> (e.g., <a href="/wiki/Pentobarbital" title="Pentobarbital">pentobarbital</a>, <a href="/wiki/Sodium_thiopental" title="Sodium thiopental">sodium thiopental</a>)</li> <li><a href="/wiki/Enflurane" title="Enflurane">Enflurane</a></li> <li><a href="/wiki/Alcohol_(drug)" title="Alcohol (drug)">Ethanol (alcohol)</a></li> <li><a href="/wiki/Evans_blue_(dye)" title="Evans blue (dye)">Evans blue</a></li> <li><a href="/w/index.php?title=NS-3763&action=edit&redlink=1" class="new" title="NS-3763 (page does not exist)">NS-3763</a></li> <li><a href="/wiki/Pregnenolone_sulfate" title="Pregnenolone sulfate">Pregnenolone sulfate</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/N-Methyl-D-aspartate_receptor" class="mw-redirect" title="N-Methyl-D-aspartate receptor"><abbr title="N-Methyl-D-aspartate receptor">NMDAR</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip N-Methyl-D-aspartate receptor</span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><b>Agonists:</b> <i>Main site agonists:</i> <a href="/w/index.php?title=2-Amino-2-(3-hydroxy-5-methylisoxazol-4-yl)acetic_acid&action=edit&redlink=1" class="new" title="2-Amino-2-(3-hydroxy-5-methylisoxazol-4-yl)acetic acid (page does not exist)">AMAA</a></li> <li><a href="/wiki/Aspartate" class="mw-redirect" title="Aspartate">Aspartate</a></li> <li><a href="/wiki/Glutamate" class="mw-redirect" title="Glutamate">Glutamate</a></li> <li><a href="/wiki/Homocysteic_acid" title="Homocysteic acid">Homocysteic acid (<small>L</small>-HCA)</a></li> <li><a href="/wiki/Homoquinolinic_acid" title="Homoquinolinic acid">Homoquinolinic acid</a></li> <li><a href="/wiki/Ibotenic_acid" title="Ibotenic acid">Ibotenic acid</a></li> <li><a href="/wiki/N-Methyl-D-aspartic_acid" title="N-Methyl-D-aspartic acid">NMDA</a></li> <li><a href="/wiki/Proline" title="Proline">Proline</a></li> <li><a href="/wiki/Quinolinic_acid" title="Quinolinic acid">Quinolinic acid</a></li> <li><a href="/wiki/Tetrazolylglycine" title="Tetrazolylglycine">Tetrazolylglycine</a></li> <li><a href="/wiki/Theanine" title="Theanine">Theanine</a>; <i>Glycine site agonists:</i> <a href="/w/index.php?title=%CE%92-Fluoro-D-alanine&action=edit&redlink=1" class="new" title="Β-Fluoro-D-alanine (page does not exist)">β-Fluoro-<small>D</small>-alanine</a></li> <li><a href="/w/index.php?title=ACBD_(drug)&action=edit&redlink=1" class="new" title="ACBD (drug) (page does not exist)">ACBD</a></li> <li><a href="/wiki/1-Aminocyclopropanecarboxylic_acid" class="mw-redirect" title="1-Aminocyclopropanecarboxylic acid">ACC (ACPC)</a></li> <li><a href="/wiki/ACPD" title="ACPD">ACPD</a></li> <li><a href="/w/index.php?title=AK-51_(drug)&action=edit&redlink=1" class="new" title="AK-51 (drug) (page does not exist)">AK-51</a></li> <li><a href="/wiki/Apimostinel" title="Apimostinel">Apimostinel (NRX-1074)</a></li> <li><a href="/wiki/B6B21" class="mw-redirect" title="B6B21">B6B21</a></li> <li><a href="/w/index.php?title=Carboxycyclopropylglycine&action=edit&redlink=1" class="new" title="Carboxycyclopropylglycine (page does not exist)">CCG</a></li> <li><a href="/wiki/Alanine" title="Alanine"><small>D</small>-Alanine</a></li> <li><a href="/wiki/Cycloserine" title="Cycloserine"><small>D</small>-Cycloserine</a></li> <li><a href="/wiki/Serine" title="Serine"><small>D</small>-Serine</a></li> <li><a href="/w/index.php?title=N-(3,3-Diphenylpropyl)glycinamide&action=edit&redlink=1" class="new" title="N-(3,3-Diphenylpropyl)glycinamide (page does not exist)">DHPG</a></li> <li><a href="/wiki/Dimethylglycine" title="Dimethylglycine">Dimethylglycine</a></li> <li><a class="mw-selflink selflink">Glycine</a></li> <li><a href="/wiki/HA-966" title="HA-966">HA-966</a></li> <li><a href="/wiki/L-687,414" title="L-687,414">L-687,414</a></li> <li><a href="/wiki/Alanine" title="Alanine"><small>L</small>-Alanine</a></li> <li><a href="/wiki/Serine" title="Serine"><small>L</small>-Serine</a></li> <li><a href="/wiki/Milacemide" title="Milacemide">Milacemide</a></li> <li><a href="/wiki/Neboglamine" title="Neboglamine">Neboglamine (nebostinel)</a></li> <li><a href="/wiki/Rapastinel" title="Rapastinel">Rapastinel (GLYX-13)</a></li> <li><a href="/wiki/Sarcosine" title="Sarcosine">Sarcosine</a>; <i>Polyamine site agonists:</i> <a href="/wiki/Neomycin" title="Neomycin">Neomycin</a></li> <li><a href="/wiki/Spermidine" title="Spermidine">Spermidine</a></li> <li><a href="/wiki/Spermine" title="Spermine">Spermine</a>; <i>Other positive allosteric modulators:</i> <a href="/wiki/24S-Hydroxycholesterol" title="24S-Hydroxycholesterol">24<i>S</i>-Hydroxycholesterol</a></li> <li><a href="/wiki/Dehydroepiandrosterone" title="Dehydroepiandrosterone"><abbr title="Dehydroepiandrosterone">DHEA</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Dehydroepiandrosterone</span> (<a href="/wiki/Prasterone" title="Prasterone">prasterone</a>)</li> <li><a href="/wiki/Dehydroepiandrosterone_sulfate" title="Dehydroepiandrosterone sulfate"><abbr title="Dehydroepiandrosterone">DHEA</abbr> sulfate</a> (<a href="/wiki/Prasterone_sulfate" title="Prasterone sulfate">prasterone sulfate</a>)</li> <li><a href="/w/index.php?title=Epipregnanolone_sulfate&action=edit&redlink=1" class="new" title="Epipregnanolone sulfate (page does not exist)">Epipregnanolone sulfate</a></li> <li><a href="/w/index.php?title=Plazinemdor&action=edit&redlink=1" class="new" title="Plazinemdor (page does not exist)">Plazinemdor</a></li> <li><a href="/wiki/Pregnenolone_sulfate" title="Pregnenolone sulfate">Pregnenolone sulfate</a></li> <li><a href="/w/index.php?title=SAGE-201&action=edit&redlink=1" class="new" title="SAGE-201 (page does not exist)">SAGE-201</a></li> <li><a href="/w/index.php?title=SAGE-301&action=edit&redlink=1" class="new" title="SAGE-301 (page does not exist)">SAGE-301</a></li> <li><a href="/wiki/SAGE-718" class="mw-redirect" title="SAGE-718">SAGE-718</a></li></ul> <ul><li><b>Antagonists:</b> <i>Competitive antagonists:</i> <a href="/wiki/AP5" title="AP5">AP5 (APV)</a></li> <li><a href="/wiki/AP-7_(drug)" title="AP-7 (drug)">AP7</a></li> <li><a href="/wiki/CGP-37849" title="CGP-37849">CGP-37849</a></li> <li><a href="/wiki/CGP-39551" title="CGP-39551">CGP-39551</a></li> <li><a href="/w/index.php?title=CGP-39653&action=edit&redlink=1" class="new" title="CGP-39653 (page does not exist)">CGP-39653</a></li> <li><a href="/w/index.php?title=CGP-40116&action=edit&redlink=1" class="new" title="CGP-40116 (page does not exist)">CGP-40116</a></li> <li><a href="/wiki/CGS-19755" class="mw-redirect" title="CGS-19755">CGS-19755</a></li> <li><a href="/w/index.php?title=3-(2-carboxypiperazin-4-yl)propyl-1-phosphonic_acid&action=edit&redlink=1" class="new" title="3-(2-carboxypiperazin-4-yl)propyl-1-phosphonic acid (page does not exist)">CPP</a></li> <li><a href="/wiki/Kaitocephalin" title="Kaitocephalin">Kaitocephalin</a></li> <li><a href="/w/index.php?title=LY-233053&action=edit&redlink=1" class="new" title="LY-233053 (page does not exist)">LY-233053</a></li> <li><a href="/wiki/LY-235959" title="LY-235959">LY-235959</a></li> <li><a href="/w/index.php?title=LY-274614&action=edit&redlink=1" class="new" title="LY-274614 (page does not exist)">LY-274614</a></li> <li><a href="/w/index.php?title=MDL-100453&action=edit&redlink=1" class="new" title="MDL-100453 (page does not exist)">MDL-100453</a></li> <li><a href="/wiki/Midafotel" title="Midafotel">Midafotel (d-CPPene)</a></li> <li><a href="/w/index.php?title=NPC-12626&action=edit&redlink=1" class="new" title="NPC-12626 (page does not exist)">NPC-12626</a></li> <li><a href="/w/index.php?title=NPC-17742&action=edit&redlink=1" class="new" title="NPC-17742 (page does not exist)">NPC-17742</a></li> <li><a href="/w/index.php?title=PBPD&action=edit&redlink=1" class="new" title="PBPD (page does not exist)">PBPD</a></li> <li><a href="/wiki/PEAQX" title="PEAQX">PEAQX</a></li> <li><a href="/wiki/Perzinfotel" title="Perzinfotel">Perzinfotel</a></li> <li><a href="/w/index.php?title=Cis-1-(phenanthrene-2-carbonyl)piperazine-2,3-dicarboxylic_acid&action=edit&redlink=1" class="new" title="Cis-1-(phenanthrene-2-carbonyl)piperazine-2,3-dicarboxylic acid (page does not exist)">PPDA</a></li> <li><a href="/w/index.php?title=SDZ-220581&action=edit&redlink=1" class="new" title="SDZ-220581 (page does not exist)">SDZ-220581</a></li> <li><a href="/wiki/Selfotel" title="Selfotel">Selfotel</a>; <i>Glycine site antagonists:</i> <a href="/wiki/4-Chlorokynurenine" title="4-Chlorokynurenine">4-Cl-KYN (AV-101)</a></li> <li><a href="/wiki/5,7-Dichlorokynurenic_acid" title="5,7-Dichlorokynurenic acid">5,7-DCKA</a></li> <li><a href="/wiki/7-Chlorokynurenic_acid" title="7-Chlorokynurenic acid">7-CKA</a></li> <li><a href="/wiki/1-Aminocyclopropane-1-carboxylic_acid" title="1-Aminocyclopropane-1-carboxylic acid">ACC</a></li> <li><a href="/w/index.php?title=ACEA-1011&action=edit&redlink=1" class="new" title="ACEA-1011 (page does not exist)">ACEA-1011</a></li> <li><a href="/w/index.php?title=ACEA-1328&action=edit&redlink=1" class="new" title="ACEA-1328 (page does not exist)">ACEA-1328</a></li> <li><a href="/wiki/Apimostinel" title="Apimostinel">Apimostinel (NRX-1074)</a></li> <li><a href="/wiki/AV-101" class="mw-redirect" title="AV-101">AV-101</a></li> <li><a href="/wiki/Carisoprodol" title="Carisoprodol">Carisoprodol</a></li> <li><a href="/w/index.php?title=CGP-39653&action=edit&redlink=1" class="new" title="CGP-39653 (page does not exist)">CGP-39653</a></li> <li><a href="/wiki/CNQX" title="CNQX">CNQX</a></li> <li><a href="/wiki/Cycloserine" title="Cycloserine"><small>D</small>-Cycloserine</a></li> <li><a href="/wiki/DNQX" title="DNQX">DNQX</a></li> <li><a href="/wiki/Felbamate" title="Felbamate">Felbamate</a></li> <li><a href="/wiki/Gavestinel" title="Gavestinel">Gavestinel</a></li> <li><a href="/w/index.php?title=GV-196771&action=edit&redlink=1" class="new" title="GV-196771 (page does not exist)">GV-196771</a></li> <li><a href="/w/index.php?title=Harkoseride&action=edit&redlink=1" class="new" title="Harkoseride (page does not exist)">Harkoseride</a></li> <li><a href="/wiki/Kynurenic_acid" title="Kynurenic acid">Kynurenic acid</a></li> <li><a href="/wiki/Kynurenine" title="Kynurenine">Kynurenine</a></li> <li><a href="/w/index.php?title=L-689560&action=edit&redlink=1" class="new" title="L-689560 (page does not exist)">L-689560</a></li> <li><a href="/wiki/L-701324" title="L-701324">L-701324</a></li> <li><a href="/wiki/Licostinel" title="Licostinel">Licostinel (ACEA-1021)</a></li> <li><a href="/w/index.php?title=LU-73068&action=edit&redlink=1" class="new" title="LU-73068 (page does not exist)">LU-73068</a></li> <li><a href="/w/index.php?title=MDL-105519&action=edit&redlink=1" class="new" title="MDL-105519 (page does not exist)">MDL-105519</a></li> <li><a href="/wiki/Meprobamate" title="Meprobamate">Meprobamate</a></li> <li><a href="/w/index.php?title=MRZ_2/576&action=edit&redlink=1" class="new" title="MRZ 2/576 (page does not exist)">MRZ 2/576</a></li> <li><a href="/w/index.php?title=PNQX&action=edit&redlink=1" class="new" title="PNQX (page does not exist)">PNQX</a></li> <li><a href="/wiki/Rapastinel" title="Rapastinel">Rapastinel (GLYX-13)</a></li> <li><a href="/wiki/ZD-9379" title="ZD-9379">ZD-9379</a>; <i>Polyamine site antagonists:</i> <a href="/w/index.php?title=Arcaine&action=edit&redlink=1" class="new" title="Arcaine (page does not exist)">Arcaine</a></li> <li><a href="/w/index.php?title=Co_101676&action=edit&redlink=1" class="new" title="Co 101676 (page does not exist)">Co 101676</a></li> <li><a href="/wiki/1,3-Diaminopropane" title="1,3-Diaminopropane">Diaminopropane</a></li> <li><a href="/wiki/Diethylenetriamine" title="Diethylenetriamine">Diethylenetriamine</a></li> <li><a href="/wiki/Huperzine_A" title="Huperzine A">Huperzine A</a></li> <li><a href="/wiki/Putrescine" title="Putrescine">Putrescine</a>; <i>Uncompetitive pore blockers (mostly dizocilpine site):</i> <a href="/wiki/2-MDP" title="2-MDP">2-MDP</a></li> <li><a href="/wiki/3-HO-PCP" title="3-HO-PCP">3-HO-PCP</a></li> <li><a href="/wiki/3-MeO-PCE" title="3-MeO-PCE">3-MeO-PCE</a></li> <li><a href="/wiki/3-MeO-PCMo" title="3-MeO-PCMo">3-MeO-PCMo</a></li> <li><a href="/wiki/3-MeO-PCP" title="3-MeO-PCP">3-MeO-PCP</a></li> <li><a href="/wiki/4-MeO-PCP" title="4-MeO-PCP">4-MeO-PCP</a></li> <li><a href="/wiki/8a-Phenyldecahydroquinoline" class="mw-redirect" title="8a-Phenyldecahydroquinoline">8A-PDHQ</a></li> <li><a href="/wiki/18-Methoxycoronaridine" title="18-Methoxycoronaridine">18-MC</a></li> <li><a href="/wiki/Alpha-Endopsychosin" class="mw-redirect" title="Alpha-Endopsychosin">α-Endopsychosin</a></li> <li><a href="/wiki/Alaproclate" title="Alaproclate">Alaproclate</a></li> <li><a href="/wiki/Alazocine" title="Alazocine">Alazocine (SKF-10047)</a></li> <li><a href="/wiki/Amantadine" title="Amantadine">Amantadine</a></li> <li><a href="/wiki/Aptiganel" title="Aptiganel">Aptiganel</a></li> <li><a href="/w/index.php?title=Argiotoxin-636&action=edit&redlink=1" class="new" title="Argiotoxin-636 (page does not exist)">Argiotoxin-636</a></li> <li><a href="/wiki/Arketamine" title="Arketamine">Arketamine</a></li> <li><a href="/w/index.php?title=ARL-12495&action=edit&redlink=1" class="new" title="ARL-12495 (page does not exist)">ARL-12495</a></li> <li><a href="/wiki/ARL-15896-AR" class="mw-redirect" title="ARL-15896-AR">ARL-15896-AR</a></li> <li><a href="/wiki/ARL-16247" class="mw-redirect" title="ARL-16247">ARL-16247</a></li> <li><a href="/wiki/Budipine" title="Budipine">Budipine</a></li> <li><a href="/wiki/Coronaridine" title="Coronaridine">Coronaridine</a></li> <li><a href="/wiki/Delucemine" title="Delucemine">Delucemine (NPS-1506)</a></li> <li><a href="/wiki/Dexoxadrol" title="Dexoxadrol">Dexoxadrol</a></li> <li><a href="/wiki/Dextrallorphan" title="Dextrallorphan">Dextrallorphan</a></li> <li><a href="/wiki/Dextromethadone" class="mw-redirect" title="Dextromethadone">Dextromethadone</a></li> <li><a href="/wiki/Dextromethorphan" title="Dextromethorphan">Dextromethorphan</a></li> <li><a href="/wiki/Dextrorphan" title="Dextrorphan">Dextrorphan</a></li> <li><a href="/wiki/Dieticyclidine" title="Dieticyclidine">Dieticyclidine</a></li> <li><a href="/wiki/Diphenidine" title="Diphenidine">Diphenidine</a></li> <li><a href="/wiki/Dizocilpine" title="Dizocilpine">Dizocilpine</a></li> <li><a href="/wiki/Ephenidine" title="Ephenidine">Ephenidine</a></li> <li><a href="/wiki/Esketamine" title="Esketamine">Esketamine</a></li> <li><a href="/wiki/Etoxadrol" title="Etoxadrol">Etoxadrol</a></li> <li><a href="/wiki/Eticyclidine" title="Eticyclidine">Eticyclidine</a></li> <li><a href="/wiki/Fluorolintane" title="Fluorolintane">Fluorolintane</a></li> <li><a href="/wiki/Gacyclidine" title="Gacyclidine">Gacyclidine</a></li> <li><a href="/wiki/Ibogaine" title="Ibogaine">Ibogaine</a></li> <li><a href="/wiki/Ibogamine" title="Ibogamine">Ibogamine</a></li> <li><a href="/wiki/Indantadol" title="Indantadol">Indantadol</a></li> <li><a href="/wiki/Ketamine" title="Ketamine">Ketamine</a></li> <li><a href="/wiki/Ketobemidone" title="Ketobemidone">Ketobemidone</a></li> <li><a href="/wiki/Lanicemine" title="Lanicemine">Lanicemine</a></li> <li><a href="/wiki/Levomethadone" title="Levomethadone">Levomethadone</a></li> <li><a href="/wiki/Levomethorphan" title="Levomethorphan">Levomethorphan</a></li> <li><a href="/wiki/Levomilnacipran" title="Levomilnacipran">Levomilnacipran</a></li> <li><a href="/wiki/Levorphanol" title="Levorphanol">Levorphanol</a></li> <li><a href="/wiki/Loperamide" title="Loperamide">Loperamide</a></li> <li><a href="/wiki/Memantine" title="Memantine">Memantine</a></li> <li><a href="/wiki/Methadone" title="Methadone">Methadone</a></li> <li><a href="/wiki/Methorphan" title="Methorphan">Methorphan</a></li> <li><a href="/wiki/Methoxetamine" title="Methoxetamine">Methoxetamine</a></li> <li><a href="/wiki/Methoxphenidine" title="Methoxphenidine">Methoxphenidine</a></li> <li><a href="/wiki/Milnacipran" title="Milnacipran">Milnacipran</a></li> <li><a href="/wiki/Morphanol" class="mw-redirect" title="Morphanol">Morphanol</a></li> <li><a href="/wiki/NEFA_(drug)" title="NEFA (drug)">NEFA</a></li> <li><a href="/wiki/Neramexane" title="Neramexane">Neramexane</a></li> <li><a href="/wiki/Nitromemantine" title="Nitromemantine">Nitromemantine</a></li> <li><a href="/wiki/Noribogaine" title="Noribogaine">Noribogaine</a></li> <li><a href="/wiki/Norketamine" title="Norketamine">Norketamine</a></li> <li><a href="/wiki/Orphenadrine" title="Orphenadrine">Orphenadrine</a></li> <li><a href="/wiki/PCPr" title="PCPr">PCPr</a></li> <li><a href="/wiki/PD-137889" title="PD-137889">PD-137889</a></li> <li><a href="/wiki/Pethidine" title="Pethidine">Pethidine (meperidine)</a></li> <li><a href="/wiki/Phencyclamine" class="mw-redirect" title="Phencyclamine">Phencyclamine</a></li> <li><a href="/wiki/Phencyclidine" title="Phencyclidine">Phencyclidine</a></li> <li><a href="/wiki/Propoxyphene" class="mw-redirect" title="Propoxyphene">Propoxyphene</a></li> <li><a href="/wiki/Remacemide" title="Remacemide">Remacemide</a></li> <li><a href="/wiki/Rhynchophylline" title="Rhynchophylline">Rhynchophylline</a></li> <li><a href="/wiki/Rimantadine" title="Rimantadine">Rimantadine</a></li> <li><a href="/wiki/Rolicyclidine" title="Rolicyclidine">Rolicyclidine</a></li> <li><a href="/wiki/Sabeluzole" title="Sabeluzole">Sabeluzole</a></li> <li><a href="/wiki/Tabernanthine" title="Tabernanthine">Tabernanthine</a></li> <li><a href="/wiki/Tenocyclidine" title="Tenocyclidine">Tenocyclidine</a></li> <li><a href="/wiki/Tiletamine" title="Tiletamine">Tiletamine</a></li> <li><a href="/wiki/Tramadol" title="Tramadol">Tramadol</a>; <i>Ifenprodil (NR2B) site antagonists:</i></li> <li><a href="/wiki/Besonprodil" title="Besonprodil">Besonprodil</a></li> <li><a href="/wiki/Buphenine" title="Buphenine">Buphenine (nylidrin)</a></li> <li><a href="/w/index.php?title=CO-101244&action=edit&redlink=1" class="new" title="CO-101244 (page does not exist)">CO-101244 (PD-174494)</a></li> <li><a href="/wiki/Eliprodil" title="Eliprodil">Eliprodil</a></li> <li><a href="/wiki/Haloperidol" title="Haloperidol">Haloperidol</a></li> <li><a href="/wiki/Isoxsuprine" title="Isoxsuprine">Isoxsuprine</a></li> <li><a href="/w/index.php?title=Radiprodil&action=edit&redlink=1" class="new" title="Radiprodil (page does not exist)">Radiprodil (RGH-896)</a></li> <li><a href="/wiki/Rislenemdaz" title="Rislenemdaz">Rislenemdaz (CERC-301, MK-0657)</a></li> <li><a href="/w/index.php?title=Ro_8-4304&action=edit&redlink=1" class="new" title="Ro 8-4304 (page does not exist)">Ro 8-4304</a></li> <li><a href="/w/index.php?title=Ro_25-6981&action=edit&redlink=1" class="new" title="Ro 25-6981 (page does not exist)">Ro 25-6981</a></li> <li><a href="/wiki/Safaprodil" class="mw-redirect" title="Safaprodil">Safaprodil</a></li> <li><a href="/wiki/Traxoprodil" title="Traxoprodil">Traxoprodil (CP-101606)</a>; <i>NR2A-selective antagonists:</i> <a href="/w/index.php?title=MPX-004&action=edit&redlink=1" class="new" title="MPX-004 (page does not exist)">MPX-004</a></li> <li><a href="/w/index.php?title=MPX-007&action=edit&redlink=1" class="new" title="MPX-007 (page does not exist)">MPX-007</a></li> <li><a href="/w/index.php?title=TCN-201&action=edit&redlink=1" class="new" title="TCN-201 (page does not exist)">TCN-201</a></li> <li><a href="/w/index.php?title=TCN-213&action=edit&redlink=1" class="new" title="TCN-213 (page does not exist)">TCN-213</a>; <i>Cations:</i> <a href="/wiki/Hydrogen" title="Hydrogen">Hydrogen</a></li> <li><a href="/wiki/Magnesium" title="Magnesium">Magnesium</a></li> <li><a href="/wiki/Zinc" title="Zinc">Zinc</a>; <i>Alcohols/volatile anesthetics/related:</i> <a href="/wiki/Benzene" title="Benzene">Benzene</a></li> <li><a href="/wiki/Butane" title="Butane">Butane</a></li> <li><a href="/wiki/Chloroform" title="Chloroform">Chloroform</a></li> <li><a href="/wiki/Cyclopropane" title="Cyclopropane">Cyclopropane</a></li> <li><a href="/wiki/Desflurane" title="Desflurane">Desflurane</a></li> <li><a href="/wiki/Diethyl_ether" title="Diethyl ether">Diethyl ether</a></li> <li><a href="/wiki/Enflurane" title="Enflurane">Enflurane</a></li> <li><a href="/wiki/Alcohol_(drug)" title="Alcohol (drug)">Ethanol (alcohol)</a></li> <li><a href="/wiki/Halothane" title="Halothane">Halothane</a></li> <li><a href="/wiki/Hexanol" title="Hexanol">Hexanol</a></li> <li><a href="/wiki/Isoflurane" title="Isoflurane">Isoflurane</a></li> <li><a href="/wiki/Methoxyflurane" title="Methoxyflurane">Methoxyflurane</a></li> <li><a href="/wiki/Nitrous_oxide" title="Nitrous oxide">Nitrous oxide</a></li> <li><a href="/wiki/Octanol" title="Octanol">Octanol</a></li> <li><a href="/wiki/Sevoflurane" title="Sevoflurane">Sevoflurane</a></li> <li><a href="/wiki/Toluene" title="Toluene">Toluene</a></li> <li><a href="/wiki/1,1,1-Trichloroethane" title="1,1,1-Trichloroethane">Trichloroethane</a></li> <li><a href="/wiki/2,2,2-Trichloroethanol" title="2,2,2-Trichloroethanol">Trichloroethanol</a></li> <li><a href="/wiki/Trichloroethylene" title="Trichloroethylene">Trichloroethylene</a></li> <li><a href="/wiki/Ethyl_carbamate" title="Ethyl carbamate">Urethane</a></li> <li><a href="/wiki/Xenon" title="Xenon">Xenon</a></li> <li><a href="/wiki/Xylene" title="Xylene">Xylene</a>; <i>Unknown/unsorted antagonists:</i> <a href="/w/index.php?title=ARR-15896&action=edit&redlink=1" class="new" title="ARR-15896 (page does not exist)">ARR-15896</a></li> <li><a href="/wiki/Bumetanide" title="Bumetanide">Bumetanide</a></li> <li><a href="/wiki/Caroverine" title="Caroverine">Caroverine</a></li> <li><a href="/wiki/Conantokin" title="Conantokin">Conantokin</a></li> <li><a href="/wiki/D-%CE%B1-Aminoadipate" class="mw-redirect" title="D-α-Aminoadipate"><small>D</small>-αAA</a></li> <li><a href="/wiki/Dexanabinol" title="Dexanabinol">Dexanabinol</a></li> <li><a href="/wiki/Flufenamic_acid" title="Flufenamic acid">Flufenamic acid</a></li> <li><a href="/wiki/Flupirtine" title="Flupirtine">Flupirtine</a></li> <li><a href="/w/index.php?title=FPL-12495&action=edit&redlink=1" class="new" title="FPL-12495 (page does not exist)">FPL-12495</a></li> <li><a href="/w/index.php?title=FR-115427&action=edit&redlink=1" class="new" title="FR-115427 (page does not exist)">FR-115427</a></li> <li><a href="/wiki/Furosemide" title="Furosemide">Furosemide</a></li> <li><a href="/wiki/Hodgkinsine" title="Hodgkinsine">Hodgkinsine</a></li> <li><a href="/w/index.php?title=Ipenoxazone&action=edit&redlink=1" class="new" title="Ipenoxazone (page does not exist)">Ipenoxazone (MLV-6976)</a></li> <li><a href="/w/index.php?title=MDL-27266&action=edit&redlink=1" class="new" title="MDL-27266 (page does not exist)">MDL-27266</a></li> <li><a href="/wiki/Metaphit" title="Metaphit">Metaphit</a></li> <li><a href="/wiki/Minocycline" title="Minocycline">Minocycline</a></li> <li><a href="/wiki/2-Methyl-6-(phenylethynyl)pyridine" title="2-Methyl-6-(phenylethynyl)pyridine">MPEP</a></li> <li><a href="/wiki/Niflumic_acid" title="Niflumic acid">Niflumic acid</a></li> <li><a href="/wiki/Pentamidine" title="Pentamidine">Pentamidine</a></li> <li><a href="/wiki/Pentamidine_isethionate" class="mw-redirect" title="Pentamidine isethionate">Pentamidine isethionate</a></li> <li><a href="/wiki/Piretanide" title="Piretanide">Piretanide</a></li> <li><a href="/wiki/Psychotridine" title="Psychotridine">Psychotridine</a></li> <li><a href="/wiki/Transcrocetin" class="mw-redirect" title="Transcrocetin">Transcrocetin</a> (<a href="/wiki/Saffron" title="Saffron">saffron</a>)</li></ul> <ul><li><b>Unsorted:</b> <i>Allosteric modulators:</i> <a href="/wiki/AGN-241751" class="mw-redirect" title="AGN-241751">AGN-241751</a></li></ul> </div></td></tr><tr><td class="navbox-abovebelow" colspan="2"><div> <ul><li><i><b>See also:</b> <a href="/wiki/Template:Receptor_modulators" title="Template:Receptor modulators">Receptor/signaling modulators</a></i></li> <li><i><a href="/wiki/Template:Metabotropic_glutamate_receptor_modulators" title="Template:Metabotropic glutamate receptor modulators">Metabotropic glutamate receptor modulators</a></i></li> <li><i><a href="/wiki/Template:Glutamate_metabolism_and_transport_modulators" title="Template:Glutamate metabolism and transport modulators">Glutamate metabolism/transport modulators</a></i></li></ul> </div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374" /><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235" /></div><div role="navigation" class="navbox" aria-labelledby="Molecules_detected_in_outer_space800" style="padding:3px"><table class="nowraplinks hlist mw-collapsible mw-collapsed navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374" /><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231" /><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Molecules_detected_in_outer_space" title="Template:Molecules detected in outer space"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Molecules_detected_in_outer_space" title="Template talk:Molecules detected in outer space"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Molecules_detected_in_outer_space" title="Special:EditPage/Template:Molecules detected in outer space"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Molecules_detected_in_outer_space800" style="font-size:114%;margin:0 4em"><a href="/wiki/List_of_interstellar_and_circumstellar_molecules" title="List of interstellar and circumstellar molecules">Molecules detected in outer space</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Molecule" title="Molecule">Molecules</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Diatomic_molecule" title="Diatomic molecule">Diatomic</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Aluminium_monochloride" title="Aluminium monochloride">Aluminium monochloride</a></li> <li><a href="/wiki/Aluminium_monofluoride" title="Aluminium monofluoride">Aluminium monofluoride</a></li> <li><a href="/wiki/Aluminium(II)_oxide" title="Aluminium(II) oxide">Aluminium(II) oxide</a></li> <li><a href="/wiki/Argonium" title="Argonium">Argonium</a></li> <li><a href="/wiki/Carbon_cation" class="mw-redirect" title="Carbon cation">Carbon cation</a></li> <li><a href="/wiki/Carbon_monophosphide" title="Carbon monophosphide">Carbon monophosphide</a></li> <li><a href="/wiki/Carbon_monosulfide" title="Carbon monosulfide">Carbon monosulfide</a></li> <li><a href="/wiki/Carbon_monoxide" title="Carbon monoxide">Carbon monoxide</a></li> <li><a href="/wiki/Cyano_radical" title="Cyano radical">Cyano radical</a></li> <li><a href="/wiki/Diatomic_carbon" title="Diatomic carbon">Diatomic carbon</a></li> <li><a href="/w/index.php?title=Fluoromethylidynium&action=edit&redlink=1" class="new" title="Fluoromethylidynium (page does not exist)">Fluoromethylidynium</a></li> <li><a href="/wiki/Helium_hydride_ion" title="Helium hydride ion">Helium hydride ion</a></li> <li><a href="/wiki/Hydrogen_chloride" title="Hydrogen chloride">Hydrogen chloride</a></li> <li><a href="/wiki/Hydrogen_fluoride" title="Hydrogen fluoride">Hydrogen fluoride</a></li> <li><a href="/wiki/Hydrogen" title="Hydrogen">Hydrogen</a> (molecular)</li> <li><a href="/wiki/Hydroxyl_radical" title="Hydroxyl radical">Hydroxyl radical</a></li> <li><a href="/wiki/Imidogen" title="Imidogen">Imidogen</a></li> <li><a href="/wiki/Iron(II)_oxide" title="Iron(II) oxide">Iron(II) oxide</a></li> <li><a href="/wiki/Magnesium_monohydride" title="Magnesium monohydride">Magnesium monohydride</a></li> <li><a href="/wiki/Methylidyne_radical" title="Methylidyne radical">Methylidyne radical</a></li> <li><a href="/wiki/Nitric_oxide" title="Nitric oxide">Nitric oxide</a></li> <li><a href="/wiki/Nitrogen" title="Nitrogen">Nitrogen</a> (molecular)</li> <li><a href="/wiki/Oxygen" title="Oxygen">Oxygen</a> (molecular)</li> <li><a href="/wiki/Phosphorus_monoxide" title="Phosphorus monoxide">Phosphorus monoxide</a></li> <li><a href="/wiki/Phosphorus_mononitride" title="Phosphorus mononitride">Phosphorus mononitride</a></li> <li><a href="/wiki/Potassium_chloride" title="Potassium chloride">Potassium chloride</a></li> <li><a href="/wiki/Silicon_carbide" title="Silicon carbide">Silicon carbide</a></li> <li><a href="/wiki/Silicon_monoxide" title="Silicon monoxide">Silicon monoxide</a></li> <li><a href="/wiki/Silicon_monosulfide" title="Silicon monosulfide">Silicon monosulfide</a></li> <li><a href="/wiki/Sodium_chloride" title="Sodium chloride">Sodium chloride</a></li> <li><a href="/wiki/Sodium_iodide" title="Sodium iodide">Sodium iodide</a></li> <li><a href="/wiki/Sulfanyl" title="Sulfanyl">Sulfanyl</a></li> <li><a href="/wiki/Sulfur_mononitride" title="Sulfur mononitride">Sulfur mononitride</a></li> <li><a href="/wiki/Sulfur_monoxide" title="Sulfur monoxide">Sulfur monoxide</a></li> <li><a href="/wiki/Titanium(II)_oxide" title="Titanium(II) oxide">Titanium(II) oxide</a></li></ul> </div></td><td class="noviewer navbox-image" rowspan="9" style="width:1px;padding:0 0 0 2px"><div><span typeof="mw:File"><a href="/wiki/Nitrous_oxide" title="Nitrous oxide"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/9/93/Nitrous-oxide-3D-balls.png/60px-Nitrous-oxide-3D-balls.png" decoding="async" width="60" height="24" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/9/93/Nitrous-oxide-3D-balls.png/90px-Nitrous-oxide-3D-balls.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/9/93/Nitrous-oxide-3D-balls.png/120px-Nitrous-oxide-3D-balls.png 2x" data-file-width="1100" data-file-height="441" /></a></span> <br /><br /><br /><br /> <span typeof="mw:File"><a href="/wiki/Ethanol" title="Ethanol"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/b/b0/Ethanol-3D-balls.png/60px-Ethanol-3D-balls.png" decoding="async" width="60" height="41" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/b/b0/Ethanol-3D-balls.png/120px-Ethanol-3D-balls.png 1.5x" data-file-width="1100" data-file-height="754" /></a></span> <br /><br /><br /><br /> <span typeof="mw:File"><a href="/wiki/Buckminsterfullerene" title="Buckminsterfullerene"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/0/0f/Buckminsterfullerene-perspective-3D-balls.png/60px-Buckminsterfullerene-perspective-3D-balls.png" decoding="async" width="60" height="63" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/0/0f/Buckminsterfullerene-perspective-3D-balls.png/120px-Buckminsterfullerene-perspective-3D-balls.png 1.5x" data-file-width="1056" data-file-height="1100" /></a></span></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Triatomic_molecule" title="Triatomic molecule">Triatomic</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/Aluminium(I)_hydroxide" class="mw-redirect" title="Aluminium(I) hydroxide">Aluminium(I) hydroxide</a></li> <li><a href="/w/index.php?title=Aluminium_isocyanide&action=edit&redlink=1" class="new" title="Aluminium isocyanide (page does not exist)">Aluminium isocyanide</a></li> <li><a href="/wiki/Amino_radical" title="Amino radical">Amino radical</a></li> <li><a href="/wiki/Carbon_dioxide" title="Carbon dioxide">Carbon dioxide</a></li> <li><a href="/wiki/Carbonyl_sulfide" title="Carbonyl sulfide">Carbonyl sulfide</a></li> <li><a href="/w/index.php?title=CCP_radical&action=edit&redlink=1" class="new" title="CCP radical (page does not exist)">CCP radical</a></li> <li><a href="/wiki/Halonium_ion" title="Halonium ion">Chloronium</a></li> <li><a href="/wiki/Diazenylium" title="Diazenylium">Diazenylium</a></li> <li><a href="/wiki/Dicarbon_monoxide" title="Dicarbon monoxide">Dicarbon monoxide</a></li> <li><a href="/w/index.php?title=Disilicon_carbide&action=edit&redlink=1" class="new" title="Disilicon carbide (page does not exist)">Disilicon carbide</a></li> <li><a href="/wiki/Ethynyl_radical" title="Ethynyl radical">Ethynyl radical</a></li> <li><a href="/w/index.php?title=Formyl_radical&action=edit&redlink=1" class="new" title="Formyl radical (page does not exist)">Formyl radical</a></li> <li><a href="/wiki/Hydrogen_cyanide" title="Hydrogen cyanide">Hydrogen cyanide</a> (HCN)</li> <li><a href="/wiki/Hydrogen_isocyanide" title="Hydrogen isocyanide">Hydrogen isocyanide</a> (HNC)</li> <li><a href="/wiki/Hydrogen_sulfide" title="Hydrogen sulfide">Hydrogen sulfide</a></li> <li><a href="/wiki/Hydroperoxyl" title="Hydroperoxyl">Hydroperoxyl</a></li> <li><a href="/wiki/Iron(II)_cyanide" title="Iron(II) cyanide">Iron cyanide</a></li> <li><a href="/w/index.php?title=Isoformyl&action=edit&redlink=1" class="new" title="Isoformyl (page does not exist)">Isoformyl</a></li> <li><a href="/wiki/Magnesium_cyanide" title="Magnesium cyanide">Magnesium cyanide</a></li> <li><a href="/w/index.php?title=Magnesium_isocyanide&action=edit&redlink=1" class="new" title="Magnesium isocyanide (page does not exist)">Magnesium isocyanide</a></li> <li><a href="/wiki/Methylene_(compound)" title="Methylene (compound)">Methylene</a></li> <li><a href="/wiki/Methylidynephosphane" title="Methylidynephosphane">Methylidynephosphane</a></li> <li><a href="/wiki/Diazenylium" title="Diazenylium">N<sub>2</sub>H<sup>+</sup></a></li> <li><a href="/wiki/Nitrous_oxide" title="Nitrous oxide">Nitrous oxide</a></li> <li><a href="/wiki/Nitroxyl" title="Nitroxyl">Nitroxyl</a></li> <li><a href="/wiki/Ozone" title="Ozone">Ozone</a></li> <li><a href="/wiki/Potassium_cyanide" title="Potassium cyanide">Potassium cyanide</a></li> <li><a href="/wiki/Sodium_cyanide" title="Sodium cyanide">Sodium cyanide</a></li> <li><a href="/wiki/Sodium_hydroxide" title="Sodium hydroxide">Sodium hydroxide</a></li> <li><a href="/w/index.php?title=Silicon_carbonitride&action=edit&redlink=1" class="new" title="Silicon carbonitride (page does not exist)">Silicon carbonitride</a></li> <li><a href="/w/index.php?title=C-Silicon_dicarbide&action=edit&redlink=1" class="new" title="C-Silicon dicarbide (page does not exist)">c-Silicon dicarbide</a></li> <li><a href="/w/index.php?title=SiNC&action=edit&redlink=1" class="new" title="SiNC (page does not exist)">SiNC</a></li> <li><a href="/wiki/Sulfur_dioxide" title="Sulfur dioxide">Sulfur dioxide</a></li> <li><a href="/w/index.php?title=Thioformyl&action=edit&redlink=1" class="new" title="Thioformyl (page does not exist)">Thioformyl</a></li> <li><a href="/wiki/Thioxoethenylidene" title="Thioxoethenylidene">Thioxoethenylidene</a></li> <li><a href="/wiki/Titanium_dioxide" title="Titanium dioxide">Titanium dioxide</a></li> <li><a href="/wiki/Tricarbon" title="Tricarbon">Tricarbon</a></li> <li><a href="/wiki/Trihydrogen_cation" title="Trihydrogen cation">Trihydrogen cation</a></li> <li><a href="/wiki/Water" title="Water">Water</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/List_of_interstellar_and_circumstellar_molecules#Molecules" title="List of interstellar and circumstellar molecules">Four<br />atoms</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Acetylene" title="Acetylene">Acetylene</a></li> <li><a href="/wiki/Ammonia" title="Ammonia">Ammonia</a></li> <li><a href="/wiki/Polyyne" title="Polyyne">Cyanoethynyl</a></li> <li><a href="/wiki/Interstellar_formaldehyde" title="Interstellar formaldehyde">Formaldehyde</a></li> <li><a href="/wiki/Fulminic_acid" title="Fulminic acid">Fulminic acid</a></li> <li><a href="/w/index.php?title=HCCN&action=edit&redlink=1" class="new" title="HCCN (page does not exist)">HCCN</a></li> <li><a href="/wiki/Hydrogen_peroxide" title="Hydrogen peroxide">Hydrogen peroxide</a></li> <li><a href="/w/index.php?title=Hydromagnesium_isocyanide&action=edit&redlink=1" class="new" title="Hydromagnesium isocyanide (page does not exist)">Hydromagnesium isocyanide</a></li> <li><a href="/wiki/Isocyanic_acid" title="Isocyanic acid">Isocyanic acid</a></li> <li><a href="/wiki/Thiocyanic_acid" title="Thiocyanic acid">Isothiocyanic acid</a></li> <li><a href="/w/index.php?title=Ketenyl&action=edit&redlink=1" class="new" title="Ketenyl (page does not exist)">Ketenyl</a></li> <li><a href="/wiki/Methyl_cation" class="mw-redirect" title="Methyl cation">Methyl cation</a></li> <li><a href="/wiki/Methyl_radical" title="Methyl radical">Methyl radical</a></li> <li><a href="/w/index.php?title=Methylene_amidogen&action=edit&redlink=1" class="new" title="Methylene amidogen (page does not exist)">Methylene amidogen</a></li> <li><a href="/wiki/Propynylidyne" title="Propynylidyne">Propynylidyne</a></li> <li><a href="/w/index.php?title=Protonated_carbon_dioxide&action=edit&redlink=1" class="new" title="Protonated carbon dioxide (page does not exist)">Protonated carbon dioxide</a></li> <li><a href="/wiki/Protonated_hydrogen_cyanide" title="Protonated hydrogen cyanide">Protonated hydrogen cyanide</a></li> <li><a href="/w/index.php?title=Silicon_tricarbide&action=edit&redlink=1" class="new" title="Silicon tricarbide (page does not exist)">Silicon tricarbide</a></li> <li><a href="/wiki/Thiocyanic_acid" title="Thiocyanic acid">Thiocyanic acid</a></li> <li><a href="/wiki/Thioformaldehyde" title="Thioformaldehyde">Thioformaldehyde</a></li> <li><a href="/wiki/Tricarbon_monosulfide" title="Tricarbon monosulfide">Tricarbon monosulfide</a></li> <li><a href="/wiki/Tricarbon_monoxide" title="Tricarbon monoxide">Tricarbon monoxide</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/List_of_interstellar_and_circumstellar_molecules#Molecules" title="List of interstellar and circumstellar molecules">Five<br />atoms</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/Ammonium" title="Ammonium">Ammonium</a> ion</li> <li><a href="/wiki/Polyyne" title="Polyyne">Butadiynyl</a></li> <li><a href="/wiki/Carbodiimide" title="Carbodiimide">Carbodiimide</a></li> <li><a href="/wiki/Cyanamide" title="Cyanamide">Cyanamide</a></li> <li><a href="/wiki/Cyanoacetylene" title="Cyanoacetylene">Cyanoacetylene</a></li> <li><a href="/w/index.php?title=Cyanoformaldehyde&action=edit&redlink=1" class="new" title="Cyanoformaldehyde (page does not exist)">Cyanoformaldehyde</a></li> <li><a href="/wiki/Cyanomethyl" title="Cyanomethyl">Cyanomethyl</a></li> <li><a href="/wiki/Cyclopropenylidene" title="Cyclopropenylidene">Cyclopropenylidene</a></li> <li><a href="/wiki/Formic_acid" title="Formic acid">Formic acid</a></li> <li><a href="/w/index.php?title=Isocyanoacetylene&action=edit&redlink=1" class="new" title="Isocyanoacetylene (page does not exist)">Isocyanoacetylene</a></li> <li><a href="/wiki/Ketene" title="Ketene">Ketene</a></li> <li><a href="/wiki/Methane" title="Methane">Methane</a></li> <li><a href="/wiki/Methoxy" class="mw-redirect" title="Methoxy">Methoxy radical</a></li> <li><a href="/w/index.php?title=Methylenimine&action=edit&redlink=1" class="new" title="Methylenimine (page does not exist)">Methylenimine</a></li> <li><a href="/w/index.php?title=Propadienylidene&action=edit&redlink=1" class="new" title="Propadienylidene (page does not exist)">Propadienylidene</a></li> <li><a href="/w/index.php?title=Protonated_formaldehyde&action=edit&redlink=1" class="new" title="Protonated formaldehyde (page does not exist)">Protonated formaldehyde</a></li> <li><a href="/wiki/Silane" title="Silane">Silane</a></li> <li><a href="/w/index.php?title=Silicon-carbide_cluster&action=edit&redlink=1" class="new" title="Silicon-carbide cluster (page does not exist)">Silicon-carbide cluster</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/List_of_interstellar_and_circumstellar_molecules#Molecules" title="List of interstellar and circumstellar molecules">Six<br />atoms</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Acetonitrile" title="Acetonitrile">Acetonitrile</a></li> <li><a href="/w/index.php?title=Cyanobutadiynyl_radical&action=edit&redlink=1" class="new" title="Cyanobutadiynyl radical (page does not exist)">Cyanobutadiynyl radical</a></li> <li><a href="/wiki/Cyclopropenone" title="Cyclopropenone">Cyclopropenone</a></li> <li><a href="/wiki/Diacetylene" title="Diacetylene">Diacetylene</a></li> <li><a href="/w/index.php?title=E-Cyanomethanimine&action=edit&redlink=1" class="new" title="E-Cyanomethanimine (page does not exist)">E-Cyanomethanimine</a></li> <li><a href="/wiki/Ethylene" title="Ethylene">Ethylene</a></li> <li><a href="/wiki/Formamide" title="Formamide">Formamide</a></li> <li><a href="/w/index.php?title=HC4N&action=edit&redlink=1" class="new" title="HC4N (page does not exist)">HC<sub>4</sub>N</a></li> <li><a href="/wiki/Ketenimine" class="mw-redirect" title="Ketenimine">Ketenimine</a></li> <li><a href="/wiki/Methanethiol" title="Methanethiol">Methanethiol</a></li> <li><a href="/wiki/Methanol" title="Methanol">Methanol</a></li> <li><a href="/wiki/Methyl_isocyanide" title="Methyl isocyanide">Methyl isocyanide</a></li> <li><a href="/wiki/Polyyne" title="Polyyne">Pentynylidyne</a></li> <li><a href="/wiki/Propynal" class="mw-redirect" title="Propynal">Propynal</a></li> <li><a href="/w/index.php?title=Protonated_cyanoacetylene&action=edit&redlink=1" class="new" title="Protonated cyanoacetylene (page does not exist)">Protonated cyanoacetylene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/List_of_interstellar_and_circumstellar_molecules#Molecules" title="List of interstellar and circumstellar molecules">Seven<br />atoms</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/Acetaldehyde" title="Acetaldehyde">Acetaldehyde</a></li> <li><a href="/wiki/Acrylonitrile" title="Acrylonitrile">Acrylonitrile</a> <ul><li><a href="/wiki/Vinyl_cyanide" class="mw-redirect" title="Vinyl cyanide">Vinyl cyanide</a></li></ul></li> <li><a href="/wiki/Cyanopolyyne" title="Cyanopolyyne">Cyanodiacetylene</a></li> <li><a href="/wiki/Ethylene_oxide" title="Ethylene oxide">Ethylene oxide</a></li> <li><a href="/wiki/Glycolonitrile" title="Glycolonitrile">Glycolonitrile</a></li> <li><a href="/wiki/Hexatriynyl_radical" title="Hexatriynyl radical">Hexatriynyl radical</a></li> <li><a href="/wiki/Methyl_isocyanate" title="Methyl isocyanate">Methyl isocyanate</a></li> <li><a href="/wiki/Methylamine" title="Methylamine">Methylamine</a></li> <li><a href="/wiki/Propyne" title="Propyne">Propyne</a></li> <li><a href="/wiki/Vinyl_alcohol" title="Vinyl alcohol">Vinyl alcohol</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/List_of_interstellar_and_circumstellar_molecules#Molecules" title="List of interstellar and circumstellar molecules">Eight<br />atoms</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Acetic_acid" title="Acetic acid">Acetic acid</a></li> <li><a href="/wiki/Acrolein" title="Acrolein">Acrolein</a></li> <li><a href="/wiki/Aminoacetonitrile" title="Aminoacetonitrile">Aminoacetonitrile</a></li> <li><a href="/w/index.php?title=Cyanoallene&action=edit&redlink=1" class="new" title="Cyanoallene (page does not exist)">Cyanoallene</a></li> <li><a href="/wiki/Ethanimine" title="Ethanimine">Ethanimine</a></li> <li><a href="/wiki/Glycolaldehyde" title="Glycolaldehyde">Glycolaldehyde</a></li> <li><a href="/wiki/Polyyne" title="Polyyne">Hexapentaenylidene</a></li> <li><a href="/wiki/Methyl_formate" title="Methyl formate">Methyl formate</a></li> <li><a href="/wiki/Polyyne" title="Polyyne">Methylcyanoacetylene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/List_of_interstellar_and_circumstellar_molecules#Molecules" title="List of interstellar and circumstellar molecules">Nine<br />atoms</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/Acetamide" title="Acetamide">Acetamide</a></li> <li><a href="/wiki/Cyanopolyyne" title="Cyanopolyyne">Cyanohexatriyne</a></li> <li><a href="/wiki/Dimethyl_ether" title="Dimethyl ether">Dimethyl ether</a></li> <li><a href="/wiki/Ethanethiol" title="Ethanethiol">Ethanethiol</a></li> <li><a href="/wiki/Ethanol" title="Ethanol">Ethanol</a></li> <li><a href="/wiki/Polyyne" title="Polyyne">Methyldiacetylene</a></li> <li><a href="/wiki/N-Methylformamide" title="N-Methylformamide">N-Methylformamide</a></li> <li><a href="/wiki/Octatetraynyl_radical" title="Octatetraynyl radical">Octatetraynyl radical</a></li> <li><a href="/wiki/Propene" class="mw-redirect" title="Propene">Propene</a></li> <li><a href="/wiki/Propionitrile" title="Propionitrile">Propionitrile</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/List_of_interstellar_and_circumstellar_molecules#Molecules" title="List of interstellar and circumstellar molecules">Ten<br />atoms<br />or more</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Acetone" title="Acetone">Acetone</a></li> <li><a href="/wiki/Benzene" title="Benzene">Benzene</a></li> <li><a href="/wiki/Benzonitrile" title="Benzonitrile">Benzonitrile</a></li> <li><a href="/wiki/Buckminsterfullerene" title="Buckminsterfullerene">Buckminsterfullerene</a> (C<sub>60</sub>, C<sub>60</sub><sup>+</sup>, fullerene, buckyball)</li> <li><a href="/wiki/Butyronitrile" title="Butyronitrile">Butyronitrile</a></li> <li><a href="/wiki/C70_fullerene" title="C70 fullerene">C<sub>70</sub> fullerene</a></li> <li><a href="/wiki/Cyanopolyyne" title="Cyanopolyyne">Cyanodecapentayne</a></li> <li><a href="/wiki/Ethyl_formate" title="Ethyl formate">Ethyl formate</a></li> <li><a href="/wiki/Ethylene_glycol" title="Ethylene glycol">Ethylene glycol</a></li> <li><a href="/w/index.php?title=Heptatrienyl_radical&action=edit&redlink=1" class="new" title="Heptatrienyl radical (page does not exist)">Heptatrienyl radical</a></li> <li><a href="/wiki/Methyl_acetate" title="Methyl acetate">Methyl acetate</a></li> <li><a href="/wiki/Cyanopolyyne" title="Cyanopolyyne">Methyl-cyano-diacetylene</a></li> <li><a href="/wiki/Polyyne" title="Polyyne">Methyltriacetylene</a></li> <li><a href="/wiki/Propionaldehyde" title="Propionaldehyde">Propionaldehyde</a></li> <li><a href="/wiki/Pyrimidine" title="Pyrimidine">Pyrimidine</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Deuterium" title="Deuterium">Deuterated</a><br />molecules</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/Ammonia" title="Ammonia">Ammonia</a></li> <li><a href="/wiki/Ammonium" title="Ammonium">Ammonium</a> ion</li> <li><a href="/wiki/Formaldehyde" title="Formaldehyde">Formaldehyde</a></li> <li><a href="/wiki/Interstellar_formaldehyde#Interstellar_reactions" title="Interstellar formaldehyde">Formyl radical</a></li> <li><a href="/wiki/Heavy_water" title="Heavy water">Heavy water</a></li> <li><a href="/wiki/Hydrogen_cyanide" title="Hydrogen cyanide">Hydrogen cyanide</a></li> <li><a href="/wiki/Hydrogen_deuteride" title="Hydrogen deuteride">Hydrogen deuteride</a></li> <li><a href="/wiki/Hydrogen_isocyanide" title="Hydrogen isocyanide">Hydrogen isocyanide</a></li> <li><a href="/wiki/Diazenylium" title="Diazenylium">N<sub>2</sub>D<sup>+</sup></a></li> <li><a href="/wiki/Propyne" title="Propyne">Propyne</a></li> <li><a href="/wiki/Trihydrogen_cation" title="Trihydrogen cation">Trihydrogen cation</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/List_of_interstellar_and_circumstellar_molecules#Molecules" title="List of interstellar and circumstellar molecules">Unconfirmed</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Anthracene" title="Anthracene">Anthracene</a></li> <li><a href="/wiki/Dihydroxyacetone" title="Dihydroxyacetone">Dihydroxyacetone</a></li> <li><a class="mw-selflink selflink">Glycine</a></li> <li><a href="/wiki/Graphene" title="Graphene">Graphene</a></li> <li><a href="/w/index.php?title=H2NCO%2B&action=edit&redlink=1" class="new" title="H2NCO+ (page does not exist)">H<sub>2</sub>NCO<sup>+</sup></a></li> <li><a href="/wiki/Hemolithin" title="Hemolithin">Hemolithin</a></li> <li><a href="/wiki/Carbon" title="Carbon">Linear C<sub>5</sub></a></li> <li><a href="/wiki/Methoxyethane" title="Methoxyethane">Methoxyethane</a></li> <li><a href="/wiki/Naphthalene" title="Naphthalene">Naphthalene cation</a></li> <li><a href="/wiki/Phosphine" title="Phosphine">Phosphine</a></li> <li><a href="/wiki/Pyrene" title="Pyrene">Pyrene</a></li> <li><a href="/wiki/Silylidyne" title="Silylidyne">Silylidyne</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/List_of_interstellar_and_circumstellar_molecules#See_also" title="List of interstellar and circumstellar molecules">Related</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/Abiogenesis" title="Abiogenesis">Abiogenesis</a></li> <li><a href="/wiki/Astrobiology" title="Astrobiology">Astrobiology</a></li> <li><a href="/wiki/Astrochemistry" title="Astrochemistry">Astrochemistry</a></li> <li><a href="/wiki/Atomic_and_molecular_astrophysics" title="Atomic and molecular astrophysics">Atomic and molecular astrophysics</a></li> <li><a href="/wiki/Chemical_formula" title="Chemical formula">Chemical formula</a></li> <li><a href="/wiki/Circumstellar_dust" title="Circumstellar dust">Circumstellar dust</a></li> <li><a href="/wiki/Circumstellar_envelope" title="Circumstellar envelope">Circumstellar envelope</a></li> <li><a href="/wiki/Cosmic_dust" title="Cosmic dust">Cosmic dust</a></li> <li><a href="/wiki/Cosmic_ray" title="Cosmic ray">Cosmic ray</a></li> <li><a href="/wiki/Cosmochemistry" title="Cosmochemistry">Cosmochemistry</a></li> <li><a href="/wiki/Diffuse_interstellar_band" class="mw-redirect" title="Diffuse interstellar band">Diffuse interstellar band</a></li> <li><a href="/wiki/Earliest_known_life_forms" title="Earliest known life forms">Earliest known life forms</a></li> <li><a href="/wiki/Extraterrestrial_life" title="Extraterrestrial life">Extraterrestrial life</a></li> <li><a href="/wiki/Extraterrestrial_liquid_water" title="Extraterrestrial liquid water">Extraterrestrial liquid water</a></li> <li><a href="/wiki/Forbidden_mechanism" title="Forbidden mechanism">Forbidden mechanism</a></li> <li><a href="/wiki/Homochirality" title="Homochirality">Homochirality</a></li> <li><a href="/wiki/Intergalactic_dust" title="Intergalactic dust">Intergalactic dust</a></li> <li><a href="/wiki/Interplanetary_medium" title="Interplanetary medium">Interplanetary medium</a></li> <li><a href="/wiki/Interstellar_medium" title="Interstellar medium">Interstellar medium</a></li> <li><a href="/wiki/Iron%E2%80%93sulfur_world_theory" class="mw-redirect" title="Iron–sulfur world theory">Iron–sulfur world theory</a></li> <li><a href="/wiki/Kerogen" title="Kerogen">Kerogen</a></li> <li><a href="/wiki/Molecules_in_stars" title="Molecules in stars">Molecules in stars</a></li> <li><a href="/wiki/Nexus_for_Exoplanet_System_Science" title="Nexus for Exoplanet System Science">Nexus for Exoplanet System Science</a></li> <li><a href="/wiki/Organic_compound" title="Organic compound">Organic compound</a></li> <li><a href="/wiki/Outer_space" title="Outer space">Outer space</a></li> <li><a href="/wiki/PAH_world_hypothesis" title="PAH world hypothesis">PAH world hypothesis</a></li> <li><a href="/wiki/Photodissociation_region" title="Photodissociation region">Photodissociation region</a></li> <li><a href="/wiki/Polycyclic_aromatic_hydrocarbon" title="Polycyclic aromatic hydrocarbon">Polycyclic aromatic hydrocarbon</a> (PAH)</li> <li><a href="/wiki/Pseudo-panspermia" title="Pseudo-panspermia">Pseudo-panspermia</a></li> <li><a href="/wiki/RNA_world_hypothesis" class="mw-redirect" title="RNA world hypothesis">RNA world hypothesis</a></li> <li><a href="/wiki/Spectroscopy" title="Spectroscopy">Spectroscopy</a></li> <li><a href="/wiki/Tholin" title="Tholin">Tholin</a></li></ul> </div></td></tr><tr><td class="navbox-abovebelow" colspan="2" style="font-weight: bold;"><div> <ul><li><b><span class="noviewer" typeof="mw:File"><span title="Category"><img alt="" src="//upload.wikimedia.org/wikipedia/en/thumb/9/96/Symbol_category_class.svg/20px-Symbol_category_class.svg.png" decoding="async" width="16" height="16" class="mw-file-element" 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