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Available in 22 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-22" 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">22 languages</span> </label> <div class="vector-dropdown-content"> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li class="interlanguage-link interwiki-ca mw-list-item"><a href="https://ca.wikipedia.org/wiki/Teanina" title="Teanina – Catalan" lang="ca" hreflang="ca" data-title="Teanina" data-language-autonym="Català" data-language-local-name="Catalan" class="interlanguage-link-target"><span>Català</span></a></li><li class="interlanguage-link interwiki-de mw-list-item"><a href="https://de.wikipedia.org/wiki/Theanin" title="Theanin – German" lang="de" hreflang="de" data-title="Theanin" 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/Teaniin" title="Teaniin – Estonian" lang="et" hreflang="et" data-title="Teaniin" data-language-autonym="Eesti" data-language-local-name="Estonian" class="interlanguage-link-target"><span>Eesti</span></a></li><li class="interlanguage-link interwiki-es mw-list-item"><a href="https://es.wikipedia.org/wiki/Teanina" title="Teanina – Spanish" lang="es" hreflang="es" data-title="Teanina" data-language-autonym="Español" data-language-local-name="Spanish" class="interlanguage-link-target"><span>Español</span></a></li><li class="interlanguage-link interwiki-fa mw-list-item"><a href="https://fa.wikipedia.org/wiki/%D8%AA%DB%8C%D8%A7%D9%86%DB%8C%D9%86" title="تیانین – Persian" lang="fa" hreflang="fa" data-title="تیانین" 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/Th%C3%A9anine" title="Théanine – French" lang="fr" hreflang="fr" data-title="Théanine" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target"><span>Français</span></a></li><li class="interlanguage-link interwiki-ko mw-list-item"><a href="https://ko.wikipedia.org/wiki/%ED%85%8C%EC%95%84%EB%8B%8C" title="테아닌 – Korean" lang="ko" hreflang="ko" data-title="테아닌" data-language-autonym="한국어" data-language-local-name="Korean" class="interlanguage-link-target"><span>한국어</span></a></li><li class="interlanguage-link interwiki-it mw-list-item"><a href="https://it.wikipedia.org/wiki/Teanina" title="Teanina – Italian" lang="it" hreflang="it" data-title="Teanina" data-language-autonym="Italiano" data-language-local-name="Italian" class="interlanguage-link-target"><span>Italiano</span></a></li><li class="interlanguage-link interwiki-lv mw-list-item"><a href="https://lv.wikipedia.org/wiki/Tean%C4%ABns" title="Teanīns – Latvian" lang="lv" hreflang="lv" data-title="Teanīns" data-language-autonym="Latviešu" data-language-local-name="Latvian" class="interlanguage-link-target"><span>Latviešu</span></a></li><li class="interlanguage-link interwiki-mk mw-list-item"><a href="https://mk.wikipedia.org/wiki/%D0%A2%D0%B5%D0%B0%D0%BD%D0%B8%D0%BD" title="Теанин – Macedonian" lang="mk" hreflang="mk" data-title="Теанин" data-language-autonym="Македонски" data-language-local-name="Macedonian" class="interlanguage-link-target"><span>Македонски</span></a></li><li class="interlanguage-link interwiki-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/Theanine" title="Theanine – Dutch" lang="nl" hreflang="nl" data-title="Theanine" data-language-autonym="Nederlands" data-language-local-name="Dutch" class="interlanguage-link-target"><span>Nederlands</span></a></li><li class="interlanguage-link interwiki-ja mw-list-item"><a href="https://ja.wikipedia.org/wiki/%E3%83%86%E3%82%A2%E3%83%8B%E3%83%B3" title="テアニン – Japanese" lang="ja" hreflang="ja" data-title="テアニン" 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-uz mw-list-item"><a href="https://uz.wikipedia.org/wiki/Teanin" title="Teanin – Uzbek" lang="uz" hreflang="uz" data-title="Teanin" 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/Teanina" title="Teanina – Polish" lang="pl" hreflang="pl" data-title="Teanina" data-language-autonym="Polski" data-language-local-name="Polish" class="interlanguage-link-target"><span>Polski</span></a></li><li class="interlanguage-link interwiki-ru mw-list-item"><a href="https://ru.wikipedia.org/wiki/%D0%A2%D0%B5%D0%B0%D0%BD%D0%B8%D0%BD" title="Теанин – Russian" lang="ru" hreflang="ru" data-title="Теанин" data-language-autonym="Русский" data-language-local-name="Russian" class="interlanguage-link-target"><span>Русский</span></a></li><li class="interlanguage-link interwiki-simple mw-list-item"><a href="https://simple.wikipedia.org/wiki/Theanine" title="Theanine – Simple English" lang="en-simple" hreflang="en-simple" data-title="Theanine" data-language-autonym="Simple English" data-language-local-name="Simple English" class="interlanguage-link-target"><span>Simple English</span></a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/Teanin" title="Teanin – Serbian" lang="sr" hreflang="sr" data-title="Teanin" 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/Teanin" title="Teanin – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Teanin" data-language-autonym="Srpskohrvatski / српскохрватски" data-language-local-name="Serbo-Croatian" class="interlanguage-link-target"><span>Srpskohrvatski / српскохрватски</span></a></li><li class="interlanguage-link interwiki-fi mw-list-item"><a href="https://fi.wikipedia.org/wiki/Teaniini" title="Teaniini – Finnish" lang="fi" hreflang="fi" data-title="Teaniini" 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/Teanin" title="Teanin – Swedish" lang="sv" hreflang="sv" data-title="Teanin" data-language-autonym="Svenska" 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.hatnote+link+.hatnote{margin-top:-0.5em}@media print{body.ns-0 .mw-parser-output .hatnote{display:none!important}}</style><div role="note" class="hatnote navigation-not-searchable">Not to be confused with <i><a href="/wiki/Threonine" title="Threonine">threonine</a></i>, a distinct <a href="/wiki/Amino_acid" title="Amino acid">amino acid</a>, or <i>theine</i>, an archaic synonym of <a href="/wiki/Caffeine" title="Caffeine">caffeine</a>.</div> <p class="mw-empty-elt"> </p> <div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Pharmaceutical compound</div> <style data-mw-deduplicate="TemplateStyles:r1269284339">@media screen{html.skin-theme-clientpref-night .mw-parser-output .dark_mode_safe img{background-color:var(--background-color-inverted,#f8f9fa)}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .dark_mode_safe img{background-color:var(--background-color-inverted,#f8f9fa)}}</style> <style data-mw-deduplicate="TemplateStyles:r1257001546">.mw-parser-output .infobox-subbox{padding:0;border:none;margin:-3px;width:auto;min-width:100%;font-size:100%;clear:none;float:none;background-color:transparent}.mw-parser-output .infobox-3cols-child{margin:auto}.mw-parser-output .infobox .navbar{font-size:100%}@media screen{html.skin-theme-clientpref-night .mw-parser-output .infobox-full-data:not(.notheme)>div:not(.notheme)[style]{background:#1f1f23!important;color:#f8f9fa}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .infobox-full-data:not(.notheme) div:not(.notheme){background:#1f1f23!important;color:#f8f9fa}}@media(min-width:640px){body.skin--responsive .mw-parser-output .infobox-table{display:table!important}body.skin--responsive .mw-parser-output .infobox-table>caption{display:table-caption!important}body.skin--responsive .mw-parser-output .infobox-table>tbody{display:table-row-group}body.skin--responsive .mw-parser-output .infobox-table tr{display:table-row!important}body.skin--responsive .mw-parser-output .infobox-table th,body.skin--responsive .mw-parser-output .infobox-table td{padding-left:inherit;padding-right:inherit}}</style><table class="infobox" style="border-spacing:2px;"><caption class="infobox-title"><span title="International nonproprietary name (INN): Theanine">Theanine</span></caption><tbody><tr><td colspan="2" class="infobox-image"><span class="mw-default-size dark_mode_safe" typeof="mw:File/Frameless"><a href="/wiki/File:Theanine-3D-balls.png" class="mw-file-description"><img alt="skeletal formula of L-theanine" src="//upload.wikimedia.org/wikipedia/commons/thumb/c/c7/Theanine-3D-balls.png/250px-Theanine-3D-balls.png" decoding="async" width="220" height="106" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/c/c7/Theanine-3D-balls.png/330px-Theanine-3D-balls.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/c/c7/Theanine-3D-balls.png/500px-Theanine-3D-balls.png 2x" data-file-width="1100" data-file-height="530" /></a></span></td></tr><tr><td colspan="2" class="infobox-image"><span class="mw-default-size dark_mode_safe" typeof="mw:File/Frameless"><a href="/wiki/File:L-Theanine.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/9/92/L-Theanine.svg/220px-L-Theanine.svg.png" decoding="async" width="220" height="99" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/9/92/L-Theanine.svg/330px-L-Theanine.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/9/92/L-Theanine.svg/440px-L-Theanine.svg.png 2x" data-file-width="565" data-file-height="255" /></a></span><div class="infobox-caption"><small>L</small>-Theanine</div></td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd;color:inherit;">Clinical data</th></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;">Other names</th><td class="infobox-data">γ-<small>L</small>-Glutamylethylamide</td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Substance_dependence" title="Substance dependence">Dependence<br />liability</a></th><td class="infobox-data">None</td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Route_of_administration" title="Route of administration">Routes of<br />administration</a></th><td class="infobox-data"><a href="/wiki/Oral_route" class="mw-redirect" title="Oral route">Oral</a></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Drug_class" title="Drug class">Drug class</a></th><td class="infobox-data"><a href="/wiki/Dietary_supplement" title="Dietary supplement">dietary supplement</a></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Anatomical_Therapeutic_Chemical_Classification_System" title="Anatomical Therapeutic Chemical Classification System">ATC code</a></th><td class="infobox-data"><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>none</li></ul></div></td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd;color:inherit;">Legal status</th></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Regulation_of_therapeutic_goods" title="Regulation of therapeutic goods">Legal status</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"> <ul><li><small><abbr class="country-name" title="United States">US</abbr>:</small> <a href="/wiki/Over-the-counter_drug" title="Over-the-counter drug">OTC</a></li> <li><small><abbr class="country-name" title="United Nations">UN</abbr>:</small> Unscheduled</li></ul></div> </td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd;color:inherit;"><a href="/wiki/Pharmacokinetics" title="Pharmacokinetics">Pharmacokinetic</a> data</th></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Onset_of_action" title="Onset of action">Onset of action</a></th><td class="infobox-data">about 1 hour<sup id="cite_ref-PK_1-0" class="reference"><a href="#cite_note-PK-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Biological_half-life" title="Biological half-life">Elimination <span class="nowrap">half-life</span></a></th><td class="infobox-data">Capsule ~1.2 hours <br /> Green Tea ~0.8 hours<sup id="cite_ref-PK_1-1" class="reference"><a href="#cite_note-PK-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup></td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd;color:inherit;">Identifiers</th></tr><tr><td colspan="2" class="infobox-full-data"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold;"><div><a href="/wiki/IUPAC_nomenclature_of_chemistry" title="IUPAC nomenclature of chemistry">IUPAC name</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; text-align:left; padding-left:1.5em; text-indent:-1.5em;"><li style="line-height: inherit; margin: 0"><div style="font-size: 97%;">(2<i>S</i>)-2-Ammonio-5-(ethylamino)-5-oxopentanoate<sup id="cite_ref-RSC_Chemspider_2-0" class="reference"><a href="#cite_note-RSC_Chemspider-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> or <i>N</i>-Ethyl-<small>L</small>-glutamine</div></li></ul> </div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/CAS_Registry_Number" title="CAS Registry Number">CAS Number</a></th><td class="infobox-data"><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=3081-61-6">3081-61-6</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/PubChem#CID" title="PubChem">PubChem</a> <span style="font-weight:normal"><abbr title="Compound ID">CID</abbr></span></th><td class="infobox-data"><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/439378">439378</a></span></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/DrugBank" title="DrugBank">DrugBank</a></th><td class="infobox-data"><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/DB12444">DB12444</a></span></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/ChemSpider" title="ChemSpider">ChemSpider</a></th><td class="infobox-data"><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.388498.html">388498</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><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Unique_Ingredient_Identifier" title="Unique Ingredient Identifier">UNII</a></th><td class="infobox-data"><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/8021PR16QO">8021PR16QO</a></span></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/KEGG" title="KEGG">KEGG</a></th><td class="infobox-data"><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/C01047">C01047</a></span></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/ChEBI" title="ChEBI">ChEBI</a></th><td class="infobox-data"><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=CHEBI:17394">CHEBI:17394</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><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/ChEMBL" title="ChEMBL">ChEMBL</a></th><td class="infobox-data"><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/ChEMBL3039113">ChEMBL3039113</a></span></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><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></th><td class="infobox-data"><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/DTXSID80184817">DTXSID80184817</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q909931#P3117" title="Edit this at Wikidata"><img alt="Edit this at Wikidata" src="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/10px-OOjs_UI_icon_edit-ltr-progressive.svg.png" decoding="async" width="10" height="10" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/15px-OOjs_UI_icon_edit-ltr-progressive.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/20px-OOjs_UI_icon_edit-ltr-progressive.svg.png 2x" data-file-width="20" data-file-height="20" /></a></span></span></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/ECHA_InfoCard" class="mw-redirect" title="ECHA InfoCard"><span title="echa.europa.eu">ECHA InfoCard</span></a></th><td class="infobox-data"><a rel="nofollow" class="external text" href="https://echa.europa.eu/substance-information/-/substanceinfo/100.019.436">100.019.436</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q909931#P2566" title="Edit this at Wikidata"><img alt="Edit this at Wikidata" src="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/10px-OOjs_UI_icon_edit-ltr-progressive.svg.png" decoding="async" width="10" height="10" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/15px-OOjs_UI_icon_edit-ltr-progressive.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/20px-OOjs_UI_icon_edit-ltr-progressive.svg.png 2x" data-file-width="20" data-file-height="20" /></a></span></td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd;color:inherit;">Chemical and physical data</th></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Chemical_formula" title="Chemical formula">Formula</a></th><td class="infobox-data"><span title="Carbon">C</span><sub>7</sub><span title="Hydrogen">H</span><sub>14</sub><span title="Nitrogen">N</span><sub>2</sub><span title="Oxygen">O</span><sub>3</sub></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Molar_mass" title="Molar mass">Molar mass</a></th><td class="infobox-data"><span class="nowrap"><span data-sort-value="7002174200000000000♠"></span>174.200</span> g·mol<sup>−1</sup></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;">3D model (<a href="/wiki/JSmol" class="mw-redirect" title="JSmol">JSmol</a>)</th><td class="infobox-data"><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=CCNC%28%3DO%29CC%5BC%40H%5D%28N%29C%28%3DO%29O">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=CCNC%28%3DO%29CCC%28N%29C%28O%29%3DO">Interactive image</a></span></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Melting_point" title="Melting point">Melting point</a></th><td class="infobox-data">174.20 °C (345.56 °F) <sup id="cite_ref-pubchem_3-0" class="reference"><a href="#cite_note-pubchem-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Boiling_point" title="Boiling point">Boiling point</a></th><td class="infobox-data">215 °C (419 °F) <sup id="cite_ref-pubchem_3-1" class="reference"><a href="#cite_note-pubchem-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup></td></tr><tr><td colspan="2" class="infobox-full-data"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold;"><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="word-wrap:break-word; text-indent:-1.5em; text-align:left; padding-left:1.5em; font-size:97%; line-height:120%;">CCNC(=O)CC[C@H](N)C(=O)O</div></li><li style="line-height: inherit; margin: 0"><br /><div style="word-wrap:break-word; text-indent:-1.5em; text-align:left; padding-left:1.5em; font-size:97%; line-height:120%;">CCNC(=O)CCC(N)C(O)=O</div></li></ul> </div></td></tr><tr><td colspan="2" class="infobox-full-data"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold;"><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="word-wrap:break-word; text-indent:-1.5em; text-align:left; padding-left:1.5em; font-size:97%; line-height:120%;">InChI=1S/C7H14N2O3/c1-2-9-6(10)4-3-5(8)7(11)12/h5H,2-4,8H2,1H3,(H,9,10)(H,11,12)<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></li><li style="line-height: inherit; margin: 0"><div style="word-wrap:break-word; text-indent:-1.5em; text-align:left; padding-left:1.5em; font-size:97%; line-height:120%;">Key:DATAGRPVKZEWHA-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></li></ul> </div></td></tr></tbody></table> <p><b>Theanine</b> <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="/θ/: 'th' in 'thigh'">θ</span><span title="/iː/: 'ee' in 'fleece'">iː</span><span title="/ən/: 'on' in 'button'">ən</span><span title="/iː/: 'ee' in 'fleece'">iː</span><span title="'n' in 'nigh'">n</span></span>/</a></span></span>, also known as <b>L-theanine</b>, <b>L-gamma-glutamylethylamide</b>, or <b><i>N</i><sup>5</sup>-ethyl-<small>L</small>-glutamine</b>, is a <a href="/wiki/Non-proteinogenic_amino_acid" class="mw-redirect" title="Non-proteinogenic amino acid">non-proteinogenic amino acid</a> similar to <a href="/wiki/Glutamic_acid" title="Glutamic acid"><small>L</small>-glutamate</a> and <a href="/wiki/Glutamine" title="Glutamine"><small>L</small>-glutamine</a>. It is produced by certain plants such as <i><a href="/wiki/Camellia_sinensis" title="Camellia sinensis">Camellia sinensis</a></i> (the <a href="/wiki/Tea" title="Tea">tea</a> plant), and by some <a href="/wiki/Fungi" class="mw-redirect" title="Fungi">fungi</a>.<sup id="cite_ref-pubchem_3-2" class="reference"><a href="#cite_note-pubchem-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-drugs_4-0" class="reference"><a href="#cite_note-drugs-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> It was discovered in 1949 as a constituent of <a href="/wiki/Green_tea" title="Green tea">green tea</a> and isolated from <a href="/wiki/Gyokuro" title="Gyokuro">gyokuro</a> leaves in 1950.<sup id="cite_ref-5" class="reference"><a href="#cite_note-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> It constitutes about 1–2% of the dry weight of green tea leaves.<sup id="cite_ref-drugs_4-1" class="reference"><a href="#cite_note-drugs-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> </p><p>The name <i>theanine</i> usually refers to the <a href="/wiki/Enantiomer" title="Enantiomer">enantiomer</a> <i><small>L</small>-theanine</i>, which is the form found in <a href="/wiki/Tea_leaves" class="mw-redirect" title="Tea leaves">tea leaves</a> from which it is <a href="/wiki/Extract" title="Extract">extracted</a> as a powder.<sup id="cite_ref-drugs_4-2" class="reference"><a href="#cite_note-drugs-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup><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> The right-handed enantiomer, <i><small>D</small>-theanine</i>, is less-studied. </p><p>Theanine is sold as a <a href="/wiki/Dietary_supplement" title="Dietary supplement">dietary supplement</a>.<sup id="cite_ref-drugs_4-3" class="reference"><a href="#cite_note-drugs-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> It is packaged in <a href="/wiki/Gelatin_capsule" class="mw-redirect" title="Gelatin capsule">gelatin capsules</a>, <a href="/wiki/Tablet_(pharmacy)" title="Tablet (pharmacy)">tablets</a>, and as a <a href="/wiki/Powder" title="Powder">powder</a>, and may be an ingredient in branded supplements with <a href="/wiki/Caffeine" title="Caffeine">caffeine</a>. </p><p>It is also used as an <a href="/wiki/Ingredient" title="Ingredient">ingredient</a> in food and beverages. In 1964 Japan approved its unlimited use in all foods (including chocolates, soft drinks, and herb teas) except infant food,<sup id="cite_ref-drugs_4-4" class="reference"><a href="#cite_note-drugs-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup><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> while since 2007 it is considered to be <a href="/wiki/Generally_recognized_as_safe" title="Generally recognized as safe">safe</a> at doses up to 250 <a href="/wiki/Milligram" class="mw-redirect" title="Milligram">milligrams</a> (mg) per serving by the US <a href="/wiki/Food_and_Drug_Administration" title="Food and Drug Administration">Food and Drug Administration</a>.<sup id="cite_ref-gras_8-0" class="reference"><a href="#cite_note-gras-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> </p><p>In 2011 the <a href="/wiki/European_Food_Safety_Authority" title="European Food Safety Authority">European Food Safety Authority</a> found there was insufficient evidence for a <a href="/wiki/Causality" title="Causality">causal relationship</a> between theanine consumption and improved cognitive function, alleviation of psychological stress, maintenance of normal sleep, or reduction of menstrual discomfort.<sup id="cite_ref-efsa_9-0" class="reference"><a href="#cite_note-efsa-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Structure_and_properties">Structure and properties</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Theanine&action=edit&section=1" title="Edit section: Structure and properties"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The chemical name <i>N</i><sup>5</sup>-ethyl-<small>L</small>-glutamine<sup id="cite_ref-RSC_Chemspider_2-1" class="reference"><a href="#cite_note-RSC_Chemspider-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> and other synonyms (see box) for theanine reflect its chemical structure. The name theanine, without prefix, is generally understood to imply the <small>L</small>- (<i>S-</i>) <a href="/wiki/Enantiomer" title="Enantiomer">enantiomer</a>, derived from the related <a href="/wiki/Proteinogenic_amino_acid" title="Proteinogenic amino acid">proteinogenic L-amino acid</a> <a href="/wiki/Glutamic_acid" title="Glutamic acid">glutamic acid</a>. Theanine is an analog of this amino acid, and its primary <a href="/wiki/Amide" title="Amide">amide</a>, <small>L</small>-<a href="/wiki/Glutamine" title="Glutamine">glutamine</a> (also a proteinogenic amino acid). Theanine is a derivative of glutamine that is ethylated on the <a href="/wiki/Amide" title="Amide">amide</a> nitrogen (as the name <i>N</i><sup>5</sup>-ethyl-<small>L</small>-glutamine describes), or alternatively, to the amide formed from <a href="/wiki/Ethylamine" title="Ethylamine">ethylamine</a> and <small>L</small>-glutamic acid at its γ- (5-) side chain <a href="/wiki/Carboxylic_acid" title="Carboxylic acid">carboxylic acid</a> group (as the name γ-L-glutamylethylamide describes).<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. (April 2023)">citation needed</span></a></i>]</sup> </p><p>Relative to theanine, the opposite (<small>D</small>-, <i>R-</i>) enantiomer is largely absent from the literature,<sup id="cite_ref-RSC_Chemspider_2-2" class="reference"><a href="#cite_note-RSC_Chemspider-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> except implicitly. While natural extracts that are not harshly treated are presumed to contain only the <a href="/wiki/Biosynthesis" title="Biosynthesis">biosynthetic</a> <small>L</small>- enantiomeric form, mishandled isolates and racemic chemical preparations of theanines necessarily contain both theanine and its <small>D</small>-enantiomer (and from <a href="/wiki/Racemic" class="mw-redirect" title="Racemic">racemic</a> syntheses, in equal proportion), and studies have suggested that the <small>D</small>-isomer may actually <i>predominate</i> in some commercial supplement preparations.<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><sup id="cite_ref-DisomerDesai_11-0" class="reference"><a href="#cite_note-DisomerDesai-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> Amino acid <a href="/wiki/Racemization" title="Racemization">racemization</a> in aqueous media is a well-established chemical process promoted by elevated temperature and non-neutral pH values; prolonged heating of <i>Camellia</i> extracts—possible for oversteeped teas and in undisclosed commercial preparative processes—has been reported to result in increasing racemization of theanine to give increasing proportions of the nonnatural D-theanine, up to equal proportions of each enantiomer.<sup id="cite_ref-DisomerDesai_11-1" class="reference"><a href="#cite_note-DisomerDesai-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Discovery_and_distribution">Discovery and distribution</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Theanine&action=edit&section=2" title="Edit section: Discovery and distribution"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Theanine is found primarily in plant and fungal species. It was discovered as a constituent of tea (<i><a href="/wiki/Camellia_sinensis" title="Camellia sinensis">Camellia sinensis</a>)</i> in 1949, and in 1950 a laboratory in Kyoto<sup id="cite_ref-SAKATO_Y._J_1949_12-0" class="reference"><a href="#cite_note-SAKATO_Y._J_1949-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup> successfully isolated it from <a href="/wiki/Gyokuro" title="Gyokuro">gyokuro</a> leaf, which has high theanine content.<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> Theanine is substantially present in black, green, and white <a href="/wiki/Tea" title="Tea">teas</a> from <i>Camellia sinensis</i> in quantities of about 1% of the dry weight.<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-casimir_15-0" class="reference"><a href="#cite_note-casimir-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup> Deliberately shading tea plants from direct sunlight, as is done for <a href="/wiki/Matcha" title="Matcha">matcha</a> and <a href="/wiki/Gyokuro" title="Gyokuro">gyokuro</a> green tea, increases L-theanine content.<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> The <small>L</small>-<a href="/wiki/Enantiomer" title="Enantiomer">enantiomer</a><sup id="cite_ref-RSC_Chemspider_2-3" class="reference"><a href="#cite_note-RSC_Chemspider-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> is the form found in freshly prepared teas and some human dietary supplements.<sup id="cite_ref-DisomerDesai_11-2" class="reference"><a href="#cite_note-DisomerDesai-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Digestion_and_metabolism">Digestion and metabolism</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Theanine&action=edit&section=3" title="Edit section: Digestion and metabolism"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>As a <a href="/wiki/Structural_analog" title="Structural analog">structural analog</a> of <a href="/wiki/Glutamate" class="mw-redirect" title="Glutamate">glutamate</a> and <a href="/wiki/Glutamine" title="Glutamine">glutamine</a>, the theanine in teas or supplements is absorbed in the <a href="/wiki/Small_intestine" title="Small intestine">small intestine</a> after oral ingestion; its <a href="/wiki/Hydrolysis" title="Hydrolysis">hydrolysis</a> to <small>L</small>-glutamate and <a href="/wiki/Ethylamine" title="Ethylamine">ethylamine</a> occur both in the intestine and liver, possibly functioning as a donor for glutamate synthesis.<sup id="cite_ref-17" class="reference"><a href="#cite_note-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Pharmacology">Pharmacology</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Theanine&action=edit&section=4" title="Edit section: Pharmacology"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="In_vitro">In vitro</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Theanine&action=edit&section=5" title="Edit section: In vitro"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Theanine is structurally similar to the excitatory neurotransmitter <a href="/wiki/Glutamate_(neurotransmitter)" title="Glutamate (neurotransmitter)">glutamate</a>, and binds to <a href="/wiki/Glutamate_receptor" title="Glutamate receptor">glutamate receptors</a> <a href="/wiki/In_vitro" title="In vitro">in vitro</a>, though with much lower affinity in comparison. Specifically, it binds to <a href="/wiki/Ionotropic_glutamate_receptor" title="Ionotropic glutamate receptor">ionotropic glutamate receptors</a> in the <a href="/wiki/Micromolar" class="mw-redirect" title="Micromolar">micromolar</a> range, including the <a href="/wiki/AMPA_receptor" title="AMPA receptor">AMPA</a> and <a href="/wiki/Kainate_receptor" title="Kainate receptor">kainate receptors</a> and, to a lesser extent, the <a href="/wiki/NMDA_receptor" title="NMDA receptor">NMDA receptor</a>.<sup id="cite_ref-nathan_18-0" class="reference"><a href="#cite_note-nathan-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-pmid21477654_19-0" class="reference"><a href="#cite_note-pmid21477654-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup> It acts as an <a href="/wiki/Receptor_antagonist" title="Receptor antagonist">antagonist</a> of the former two sites, and a <a href="/wiki/Partial_agonist" title="Partial agonist">partial co-agonist</a> of the <a href="/wiki/NMDA_receptor" title="NMDA receptor">NMDA receptors</a>.<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> In vitro, theanine also binds to <a href="/wiki/Metabotropic_glutamate_receptor#Group_I" title="Metabotropic glutamate receptor">group I</a> <a href="/wiki/Metabotropic_glutamate_receptor" title="Metabotropic glutamate receptor">mGluRs</a>.<sup id="cite_ref-nathan_18-1" class="reference"><a href="#cite_note-nathan-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-pmid15207710_21-0" class="reference"><a href="#cite_note-pmid15207710-21"><span class="cite-bracket">[</span>21<span class="cite-bracket">]</span></a></sup> In addition, it inhibits <a href="/wiki/Glutamine_transporter" class="mw-redirect" title="Glutamine transporter">glutamine transporters</a> and <a href="/wiki/Glutamate_transporter" title="Glutamate transporter">glutamate transporters</a>, and thus blocks the <a href="/wiki/Reuptake" title="Reuptake">reuptake</a> of glutamine and glutamate.<sup id="cite_ref-pmid21477654_19-1" class="reference"><a href="#cite_note-pmid21477654-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-pmid11325559_22-0" class="reference"><a href="#cite_note-pmid11325559-22"><span class="cite-bracket">[</span>22<span class="cite-bracket">]</span></a></sup> </p><p>Theanine may elicit <a href="/wiki/Umami" title="Umami">umami</a> taste, a consequence potentially associated with binding to and activation of the <a href="/wiki/TAS1R1" title="TAS1R1">T1R1</a> + <a href="/wiki/TAS1R3" title="TAS1R3">T1R3</a> <a href="/wiki/Heterodimer" class="mw-redirect" title="Heterodimer">heterodimer</a> or <a href="/wiki/Umami#Taste_receptors" title="Umami">umami (savory) taste receptor</a>.<sup id="cite_ref-pmid24633359_23-0" class="reference"><a href="#cite_note-pmid24633359-23"><span class="cite-bracket">[</span>23<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Regulatory_status">Regulatory status</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Theanine&action=edit&section=6" title="Edit section: Regulatory status"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The regulatory status of theanine varies by country. It is sold as a dietary supplement across the United States and European Union. <sup id="cite_ref-drugs_4-5" class="reference"><a href="#cite_note-drugs-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-24" class="reference"><a href="#cite_note-24"><span class="cite-bracket">[</span>24<span class="cite-bracket">]</span></a></sup> In Japan, <small>L</small>-theanine has been approved for use in all foods, with some restrictions in the case of infant foods.<sup id="cite_ref-SAKATO_Y._J_1949_12-1" class="reference"><a href="#cite_note-SAKATO_Y._J_1949-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-25" class="reference"><a href="#cite_note-25"><span class="cite-bracket">[</span>25<span class="cite-bracket">]</span></a></sup> In the United States, the FDA considers it to be <a href="/wiki/Generally_recognized_as_safe" title="Generally recognized as safe">GRAS</a> and allows its use as an ingredient in foods and beverages up to a maximum of 250 mg per serving.<sup id="cite_ref-gras_8-1" class="reference"><a href="#cite_note-gras-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> </p><p>In 2003, the German Federal Institute for Risk Assessment (<i>Bundesinstitut für Risikobewertung</i>, BfR), an agency of their <a href="/wiki/Federal_Ministry_of_Food_and_Agriculture" class="mw-redirect" title="Federal Ministry of Food and Agriculture">Federal Ministry of Food and Agriculture</a>, objected to the addition of isolated theanine to beverages.<sup id="cite_ref-26" class="reference"><a href="#cite_note-26"><span class="cite-bracket">[</span>26<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-KanarekLieberman2011_27-0" class="reference"><a href="#cite_note-KanarekLieberman2011-27"><span class="cite-bracket">[</span>27<span class="cite-bracket">]</span></a></sup> While it was estimated the quantity of green tea consumed by the average Japanese tea drinker per day contains about 20 mg of the substance, there were no studies measuring the amount of theanine being extracted by typical preparation methods, or the percentage lost by discarding the first infusion. Therefore, with the Japanese being exposed to possibly much less than 20 mg per day, it was the opinion of the BfR that <a href="/wiki/Pharmacological" class="mw-redirect" title="Pharmacological">pharmacological</a> reactions to drinks typically containing 50 mg of theanine per 500 milliliters could not be excluded—reactions such as impairment of <a href="/wiki/Psychomotor_learning" title="Psychomotor learning">psychomotor</a> skills and amplification of the <a href="/wiki/Sedating" class="mw-redirect" title="Sedating">sedating</a> effects of <a href="/wiki/Alcohol_(drug)" title="Alcohol (drug)">alcohol</a> and <a href="/wiki/Hypnotics" class="mw-redirect" title="Hypnotics">hypnotics</a>.<sup id="cite_ref-BfR2_28-0" class="reference"><a href="#cite_note-BfR2-28"><span class="cite-bracket">[</span>28<span class="cite-bracket">]</span></a></sup> </p><p>On 13 November 2023, the Inspection by the Administration of Food Safety, Veterinary Medicine and Plant Protection of the Republic of Slovenia banned the sale of <a href="/wiki/Prime_(drink)" title="Prime (drink)">Prime</a> energy drinks in Slovenia as they contain L-theanine, which is not allowed in non-alcoholic beverages. Prime Hydration may be freely sold.<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> </p> <div class="mw-heading mw-heading2"><h2 id="Research_on_supplement_use">Research on supplement use</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Theanine&action=edit&section=7" title="Edit section: Research on supplement use"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>A 2020 review suggested that L-theanine supplementation of 200–400 <a href="/wiki/Milligram" class="mw-redirect" title="Milligram">milligrams</a> per day may reduce stress and anxiety in people with acute stress, but there was insufficient evidence for the use of L-theanine as a <a href="/wiki/Medication" title="Medication">medication</a> to treat stress and anxiety.<sup id="cite_ref-pmid31758301_30-0" class="reference"><a href="#cite_note-pmid31758301-30"><span class="cite-bracket">[</span>30<span class="cite-bracket">]</span></a></sup> Evidence from a systematic review of randomised controlled trials suggests that L-theanine supplementation may be more effective than placebo in alleviating psychopathological symptoms associated with <a href="/wiki/Anxiety_disorder" title="Anxiety disorder">anxiety disorders</a>, <a href="/wiki/ADHD" class="mw-redirect" title="ADHD">ADHD</a>, and <a href="/wiki/Schizophrenia" title="Schizophrenia">schizophrenia</a>.<sup id="cite_ref-u648_31-0" class="reference"><a href="#cite_note-u648-31"><span class="cite-bracket">[</span>31<span class="cite-bracket">]</span></a></sup> </p><p>Theanine supplements have been marketed with a variety of claims that they improve cognitive performance, reduce stress, improve sleep quality, and alleviate <a href="/wiki/Menstrual_cramps" class="mw-redirect" title="Menstrual cramps">menstrual cramps</a>. Evaluating these claims in 2011, the <a href="/wiki/European_Food_Safety_Authority" title="European Food Safety Authority">European Food Safety Authority</a> assessed they were not supported by evidence.<sup id="cite_ref-efsa_9-1" class="reference"><a href="#cite_note-efsa-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="See_also">See also</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Theanine&action=edit&section=8" title="Edit section: See also"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a href="/wiki/Caffeine" title="Caffeine">Caffeine</a></li> <li><a href="/wiki/Gamma-Glutamylmethylamide" class="mw-redirect" title="Gamma-Glutamylmethylamide"><i>gamma</i>-Glutamylmethylamide</a></li> <li><a href="/wiki/Green_tea" title="Green tea">Green tea</a></li> <li><a href="/wiki/Nootropic" title="Nootropic">Nootropic</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=Theanine&action=edit&section=9" 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-PK-1"><span class="mw-cite-backlink">^ <a href="#cite_ref-PK_1-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-PK_1-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><style data-mw-deduplicate="TemplateStyles:r1238218222">.mw-parser-output cite.citation{font-style:inherit;word-wrap:break-word}.mw-parser-output .citation q{quotes:"\"""\"""'""'"}.mw-parser-output .citation:target{background-color:rgba(0,127,255,0.133)}.mw-parser-output .id-lock-free.id-lock-free a{background:url("//upload.wikimedia.org/wikipedia/commons/6/65/Lock-green.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-limited.id-lock-limited a,.mw-parser-output .id-lock-registration.id-lock-registration a{background:url("//upload.wikimedia.org/wikipedia/commons/d/d6/Lock-gray-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-subscription.id-lock-subscription a{background:url("//upload.wikimedia.org/wikipedia/commons/a/aa/Lock-red-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .cs1-ws-icon a{background:url("//upload.wikimedia.org/wikipedia/commons/4/4c/Wikisource-logo.svg")right 0.1em center/12px no-repeat}body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-free a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-limited a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-registration a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-subscription a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .cs1-ws-icon a{background-size:contain;padding:0 1em 0 0}.mw-parser-output .cs1-code{color:inherit;background:inherit;border:none;padding:inherit}.mw-parser-output .cs1-hidden-error{display:none;color:var(--color-error,#d33)}.mw-parser-output .cs1-visible-error{color:var(--color-error,#d33)}.mw-parser-output .cs1-maint{display:none;color:#085;margin-left:0.3em}.mw-parser-output .cs1-kern-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right{padding-right:0.2em}.mw-parser-output .citation .mw-selflink{font-weight:inherit}@media screen{.mw-parser-output .cs1-format{font-size:95%}html.skin-theme-clientpref-night .mw-parser-output .cs1-maint{color:#18911f}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .cs1-maint{color:#18911f}}</style><cite id="CITEREFScheidEllingerAlteheldHerholz2012" class="citation journal cs1">Scheid L, Ellinger S, Alteheld B, Herholz H, Ellinger J, Henn T, et al. 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(March 2020). "The Effects of Green Tea Amino Acid L-Theanine Consumption on the Ability to Manage Stress and Anxiety Levels: a Systematic Review". <i>Plant Foods for Human Nutrition</i>. <b>75</b> (1): <span class="nowrap">12–</span>23. <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/2020PFHN...75...12W">2020PFHN...75...12W</a>. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1007%2Fs11130-019-00771-5">10.1007/s11130-019-00771-5</a>. <a href="/wiki/Hdl_(identifier)" class="mw-redirect" title="Hdl (identifier)">hdl</a>:<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://hdl.handle.net/11392%2F2459663">11392/2459663</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/31758301">31758301</a>. <a href="/wiki/S2CID_(identifier)" class="mw-redirect" title="S2CID (identifier)">S2CID</a> <a rel="nofollow" class="external text" href="https://api.semanticscholar.org/CorpusID:208213702">208213702</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Plant+Foods+for+Human+Nutrition&rft.atitle=The+Effects+of+Green+Tea+Amino+Acid+L-Theanine+Consumption+on+the+Ability+to+Manage+Stress+and+Anxiety+Levels%3A+a+Systematic+Review&rft.volume=75&rft.issue=1&rft.pages=%3Cspan+class%3D%22nowrap%22%3E12-%3C%2Fspan%3E23&rft.date=2020-03&rft_id=info%3Ahdl%2F11392%2F2459663&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A208213702%23id-name%3DS2CID&rft_id=info%3Abibcode%2F2020PFHN...75...12W&rft_id=info%3Apmid%2F31758301&rft_id=info%3Adoi%2F10.1007%2Fs11130-019-00771-5&rft.aulast=Williams&rft.aufirst=JL&rft.au=Everett%2C+JM&rft.au=D%27Cunha%2C+NM&rft.au=Sergi%2C+D&rft.au=Georgousopoulou%2C+EN&rft.au=Keegan%2C+RJ&rft.au=McKune%2C+AJ&rft.au=Mellor%2C+DD&rft.au=Anstice%2C+N&rft.au=Naumovski%2C+N&rfr_id=info%3Asid%2Fen.wikipedia.org%3ATheanine" class="Z3988"></span></span> </li> <li id="cite_note-u648-31"><span class="mw-cite-backlink"><b><a href="#cite_ref-u648_31-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFMoshfeghiniaSanaeiMostafaviAssadian2024" class="citation journal cs1">Moshfeghinia R, Sanaei E, Mostafavi S, Assadian K, Sanaei A, Ayano G (December 2024). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11616108">"The effects of L-theanine supplementation on the outcomes of patients with mental disorders: a systematic review"</a>. <i>BMC Psychiatry</i>. <b>24</b> (1): 886. <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/10.1186%2Fs12888-024-06285-y">10.1186/s12888-024-06285-y</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/PMC11616108">11616108</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/39633316">39633316</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=BMC+Psychiatry&rft.atitle=The+effects+of+L-theanine+supplementation+on+the+outcomes+of+patients+with+mental+disorders%3A+a+systematic+review&rft.volume=24&rft.issue=1&rft.pages=886&rft.date=2024-12&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC11616108%23id-name%3DPMC&rft_id=info%3Apmid%2F39633316&rft_id=info%3Adoi%2F10.1186%2Fs12888-024-06285-y&rft.aulast=Moshfeghinia&rft.aufirst=R&rft.au=Sanaei%2C+E&rft.au=Mostafavi%2C+S&rft.au=Assadian%2C+K&rft.au=Sanaei%2C+A&rft.au=Ayano%2C+G&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC11616108&rfr_id=info%3Asid%2Fen.wikipedia.org%3ATheanine" 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=Theanine&action=edit&section=10" 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="CITEREFKeenanFinnieJonesRogers2011" class="citation journal cs1">Keenan EK, Finnie MD, Jones PS, Rogers PJ, Priestley CM (2011). "How much theanine in a cup of tea? Effects of tea type and method of preparation". <i>Food Chemistry</i>. <b>125</b> (2): <span class="nowrap">588–</span>594. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2Fj.foodchem.2010.08.071">10.1016/j.foodchem.2010.08.071</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Food+Chemistry&rft.atitle=How+much+theanine+in+a+cup+of+tea%3F+Effects+of+tea+type+and+method+of+preparation&rft.volume=125&rft.issue=2&rft.pages=%3Cspan+class%3D%22nowrap%22%3E588-%3C%2Fspan%3E594&rft.date=2011&rft_id=info%3Adoi%2F10.1016%2Fj.foodchem.2010.08.071&rft.aulast=Keenan&rft.aufirst=EK&rft.au=Finnie%2C+MD&rft.au=Jones%2C+PS&rft.au=Rogers%2C+PJ&rft.au=Priestley%2C+CM&rfr_id=info%3Asid%2Fen.wikipedia.org%3ATheanine" class="Z3988"></span></li></ul> </div><div class="navbox-styles"><style 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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:Glutamate_metabolism_and_transport_modulators" title="Template:Glutamate metabolism and transport modulators"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Glutamate_metabolism_and_transport_modulators" title="Template talk:Glutamate metabolism and transport modulators"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Glutamate_metabolism_and_transport_modulators" title="Special:EditPage/Template:Glutamate metabolism and transport modulators"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Glutamate_metabolism_and_transport_modulators542" style="font-size:114%;margin:0 4em"><a href="/wiki/Glutamate" class="mw-redirect" title="Glutamate">Glutamate</a> <a href="/wiki/Metabolism" title="Metabolism">metabolism</a> and <a href="/wiki/Glutamate_transporter" title="Glutamate transporter">transport</a> <a href="/wiki/Ligand_(biochemistry)" title="Ligand (biochemistry)">modulators</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Neurotransmitter_transporter" title="Neurotransmitter transporter">Transporter</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:4em;;text-align:center;"><a href="/wiki/Excitatory_amino_acid_transporters" class="mw-redirect" title="Excitatory amino acid transporters"><abbr title="Excitatory amino acid transporters">EAATs</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 Excitatory amino acid transporters</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="/wiki/Amphetamine" title="Amphetamine">Amphetamine</a></li> <li><a href="/wiki/Aspartic_acid" title="Aspartic acid">Aspartic acid (aspartate)</a></li> <li><a href="/w/index.php?title=Cis-1-Aminocyclobutane-1,3-dicarboxylic_acid&action=edit&redlink=1" class="new" title="Cis-1-Aminocyclobutane-1,3-dicarboxylic acid (page does not exist)"><i>cis</i>-ACBD</a></li> <li><a href="/wiki/Dihydrokainic_acid" title="Dihydrokainic acid">DHKA</a></li> <li><a href="/wiki/Glutamic_acid" title="Glutamic acid">Glutamic acid (glutamate)</a></li> <li><a href="/w/index.php?title=3-Hydroxy-4,5,6,6a-tetrahydro-3aH-pyrrolo(3,4-d)isoxazole-4-carboxylic_acid&action=edit&redlink=1" class="new" title="3-Hydroxy-4,5,6,6a-tetrahydro-3aH-pyrrolo(3,4-d)isoxazole-4-carboxylic acid (page does not exist)">HIP-A</a></li> <li><a href="/w/index.php?title=3-Hydroxy-4,5,6,6a-tetrahydro-3aH-pyrrolo(3,4-d)isoxazole-6-carboxylic_acid&action=edit&redlink=1" class="new" title="3-Hydroxy-4,5,6,6a-tetrahydro-3aH-pyrrolo(3,4-d)isoxazole-6-carboxylic acid (page does not exist)">HIP-B</a></li> <li><a href="/wiki/Kainic_acid" title="Kainic acid">Kainic acid</a></li> <li><a href="/wiki/3-Hydroxyaspartic_acid" title="3-Hydroxyaspartic acid"><small>L</small>-(-)-<i>threo</i>-3-Hydroxyaspartic acid</a></li> <li><a href="/wiki/L-%CE%B1-Aminoadipate" class="mw-redirect" title="L-α-Aminoadipate"><small>L</small>-αAA</a></li> <li><a href="/w/index.php?title=(2S,1%27S,2%27R)-2-(Carboxycyclopropyl)glycine&action=edit&redlink=1" class="new" title="(2S,1'S,2'R)-2-(Carboxycyclopropyl)glycine (page does not exist)"><small>L</small>-CCG-III ((2S,3S,4R)-CCG)</a></li> <li><a href="/w/index.php?title=L-Serine-O-sulphate&action=edit&redlink=1" class="new" title="L-Serine-O-sulphate (page does not exist)"><small>L</small>-Serine-O-sulphate (SOS)</a></li> <li><a href="/w/index.php?title=L-trans-Pyrrolidine-2,4-dicarboxylic_acid&action=edit&redlink=1" class="new" title="L-trans-Pyrrolidine-2,4-dicarboxylic acid (page does not exist)"><small>L</small>-<i>trans</i>-2,4-PDC</a></li> <li><a href="/w/index.php?title=L-anti-endo-3,4-Methanopyrrolidinedicarboxylic_acid&action=edit&redlink=1" class="new" title="L-anti-endo-3,4-Methanopyrrolidinedicarboxylic acid (page does not exist)">MPDC</a></li> <li><a href="/wiki/Maslinic_acid" title="Maslinic acid">Maslinic acid</a></li> <li><a href="/wiki/SYM-2081" title="SYM-2081">SYM-2081</a></li> <li><a href="/w/index.php?title=Threo-%CE%B2-Benzyloxyaspartic_acid&action=edit&redlink=1" class="new" title="Threo-β-Benzyloxyaspartic acid (page does not exist)">TBOA</a></li> <li><a href="/w/index.php?title=TFB-TBOA&action=edit&redlink=1" class="new" title="TFB-TBOA (page does not exist)">TFB-TBOA</a></li> <li><a class="mw-selflink selflink">Theanine</a></li> <li><a href="/w/index.php?title=Threo-3-Methylglutamic_acid&action=edit&redlink=1" class="new" title="Threo-3-Methylglutamic acid (page does not exist)"><i>threo</i>-3-Methylglutamic acid</a></li> <li><a href="/w/index.php?title=UCPH-101&action=edit&redlink=1" class="new" title="UCPH-101 (page does not exist)">UCPH-101</a></li> <li><a href="/wiki/WAY-213,613" title="WAY-213,613">WAY-213,613</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:4em;;text-align:center;"><a href="/wiki/Vesicular_glutamate_transporters" class="mw-redirect" title="Vesicular glutamate transporters"><abbr title="Vesicular glutamate transporters">vGluTs</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Vesicular glutamate transporters</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="/w/index.php?title=4-Methylene-L-glutamate&action=edit&redlink=1" class="new" title="4-Methylene-L-glutamate (page does not exist)">4-Methylene-<small>L</small>-glutamate</a></li> <li><a href="/w/index.php?title=6-(4%27-Phenylstyryl)-quinoline-2,4-dicarboxylic_acid&action=edit&redlink=1" class="new" title="6-(4'-Phenylstyryl)-quinoline-2,4-dicarboxylic acid (page does not exist)">6-(4'-Phenylstyryl)-QDC</a></li> <li><a href="/w/index.php?title=6-Biphenyl-4-yl-quinoline-2,4-dicarboxylic_acid&action=edit&redlink=1" class="new" title="6-Biphenyl-4-yl-quinoline-2,4-dicarboxylic acid (page does not exist)">6-Biphenyl-4-yl-QDC</a></li> <li><a href="/wiki/7-Chlorokynurenic_acid" title="7-Chlorokynurenic acid">7-CKA</a></li> <li><a href="/w/index.php?title=Acid_red_114&action=edit&redlink=1" class="new" title="Acid red 114 (page does not exist)">Acid red 114</a></li> <li><a href="/wiki/Amido_black_10B" title="Amido black 10B">Amido black 10B (naphthol blue black)</a></li> <li><a href="/wiki/Bafilomycin_A1" class="mw-redirect" title="Bafilomycin A1">Bafilomycin A1</a></li> <li><a href="/w/index.php?title=Benzopurpurin_4B&action=edit&redlink=1" class="new" title="Benzopurpurin 4B (page does not exist)">Benzopurpurin 4B</a></li> <li><a href="/w/index.php?title=Bumetamide&action=edit&redlink=1" class="new" title="Bumetamide (page does not exist)">Bumetamide</a></li> <li><a href="/w/index.php?title=Chicago_sky_blue_6B&action=edit&redlink=1" class="new" title="Chicago sky blue 6B (page does not exist)">Chicago sky blue 6B</a></li> <li><a href="/wiki/Aspartic_acid" title="Aspartic acid">Aspartic acid (aspartate)</a></li> <li><a href="/wiki/DIDS" title="DIDS">DIDS</a></li> <li><a href="/w/index.php?title=Direct_blue_71&action=edit&redlink=1" class="new" title="Direct blue 71 (page does not exist)">Direct blue 71</a></li> <li><a href="/w/index.php?title=Erythro-4-methyl-L-glutamic_acid&action=edit&redlink=1" class="new" title="Erythro-4-methyl-L-glutamic acid (page does not exist)">Erythro-4-methyl-<small>L</small>-glutamic acid</a></li> <li><a href="/wiki/Evans_blue_(dye)" title="Evans blue (dye)">Evans blue</a></li> <li><a href="/wiki/Furosemide" title="Furosemide">Furosemide</a></li> <li><a href="/wiki/Glutamic_acid" title="Glutamic acid">Glutamic acid (glutamate)</a></li> <li><a href="/wiki/Kynurenic_acid" title="Kynurenic acid">Kynurenic acid</a></li> <li><a href="/wiki/Nigericin" title="Nigericin">Nigericin</a></li> <li><a href="/w/index.php?title=5-Nitro-2-(3-phenylpropylamino)benzoic_acid&action=edit&redlink=1" class="new" title="5-Nitro-2-(3-phenylpropylamino)benzoic acid (page does not exist)">NPPB (N144)</a></li> <li><a href="/w/index.php?title=Ponceau_SS&action=edit&redlink=1" class="new" title="Ponceau SS (page does not exist)">Ponceau SS</a></li> <li><a href="/w/index.php?title=Reactive_blue_2&action=edit&redlink=1" class="new" title="Reactive blue 2 (page does not exist)">Reactive blue 2</a></li> <li><a href="/wiki/Rose_bengal" title="Rose bengal">Rose bengal</a></li> <li><a href="/w/index.php?title=4,4%27-Diisothiocyanostilbene-2,2%27-disulfonic_acid&action=edit&redlink=1" class="new" title="4,4'-Diisothiocyanostilbene-2,2'-disulfonic acid (page does not exist)">SITS</a></li> <li><a href="/w/index.php?title=Trans-1-aminocyclopentane-1,3-dicarboxylic_acid&action=edit&redlink=1" class="new" title="Trans-1-aminocyclopentane-1,3-dicarboxylic acid (page does not exist)"><i>trans</i>-ACDP</a></li> <li><a href="/wiki/Trypan_blue" title="Trypan blue">Trypan blue</a></li> <li><a href="/wiki/Valinomycin" title="Valinomycin">Valinomycin</a></li> <li><a href="/wiki/Xanthurenic_acid" title="Xanthurenic acid">Xanthurenic acid</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Enzyme" title="Enzyme">Enzyme</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:4em;;text-align:center;"><a href="/wiki/Glutamine_aminohydrolase_(glutaminase)" class="mw-redirect" title="Glutamine aminohydrolase (glutaminase)"><abbr title="Glutamine aminohydrolase (glutaminase)">GAH</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 Glutamine aminohydrolase (glutaminase)</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=BPTES&action=edit&redlink=1" class="new" title="BPTES (page does not exist)">BPTES</a></li> <li><a href="/w/index.php?title=CB-839&action=edit&redlink=1" class="new" title="CB-839 (page does not exist)">CB-839</a></li> <li><a href="/wiki/6-Diazo-5-oxo-L-norleucine" title="6-Diazo-5-oxo-L-norleucine">DON</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:4em;;text-align:center;"><a href="/wiki/Aspartate_aminotransferase" class="mw-redirect" title="Aspartate aminotransferase"><abbr title="Aspartate aminotransferase">AST</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 Aspartate aminotransferase</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="/w/index.php?title=2-Amino-3-butenoic_acid&action=edit&redlink=1" class="new" title="2-Amino-3-butenoic acid (page does not exist)">2-Amino-3-butenoic acid</a></li> <li><a href="/wiki/Aminooxyacetic_acid" title="Aminooxyacetic acid">AAOA</a></li> <li><a href="/w/index.php?title=L-2-Amino-4-methoxy-trans-3-butenoic_acid&action=edit&redlink=1" class="new" title="L-2-Amino-4-methoxy-trans-3-butenoic acid (page does not exist)">AMB</a></li> <li><a href="/w/index.php?title=%CE%92-DL-Methylene-aspartate&action=edit&redlink=1" class="new" title="Β-DL-Methylene-aspartate (page does not exist)">β-<span style="font-size: 85%;">DL</span>-Methylene-aspartate</a></li> <li><a href="/w/index.php?title=Hydrazinosuccinate&action=edit&redlink=1" class="new" title="Hydrazinosuccinate (page does not exist)">Hydrazinosuccinate</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:4em;;text-align:center;"><a href="/wiki/Alanine_aminotransferase" class="mw-redirect" title="Alanine aminotransferase"><abbr title="Alanine aminotransferase">ALT</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 Alanine aminotransferase</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=%CE%92-Chloro-L-alanine&action=edit&redlink=1" class="new" title="Β-Chloro-L-alanine (page does not exist)">β-Chloro-<span style="font-size: 85%;">L</span>-alanine</a></li> <li><a href="/wiki/L-Cycloserine" class="mw-redirect" title="L-Cycloserine"><span style="font-size: 85%;">L</span>-Cycloserine</a></li> <li><a href="/w/index.php?title=Propargylglycine&action=edit&redlink=1" class="new" title="Propargylglycine (page does not exist)">Propargylglycine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:4em;;text-align:center;"><a href="/wiki/Glutamate_dehydrogenase" title="Glutamate dehydrogenase"><abbr title="Glutamate dehydrogenase">GDH</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 Glutamate dehydrogenase</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/Aminooxyacetic_acid" title="Aminooxyacetic acid">AAOA</a></li> <li><a href="/wiki/Bithionol" title="Bithionol">Bithionol</a></li> <li><a href="/wiki/Chloroquine" title="Chloroquine">Chloroquine</a></li> <li><a href="/wiki/Epigallocatechin-3-gallate" class="mw-redirect" title="Epigallocatechin-3-gallate">EGCG</a></li> <li><a href="/wiki/Guanosine-5%27-triphosphate" class="mw-redirect" title="Guanosine-5'-triphosphate">GTP</a></li> <li><a href="/w/index.php?title=GW5074&action=edit&redlink=1" class="new" title="GW5074 (page does not exist)">GW5074</a></li> <li><a href="/wiki/Hexachlorophene" title="Hexachlorophene">Hexachlorophene</a></li> <li><a href="/wiki/Hydroxylamine" title="Hydroxylamine">Hydroxylamine</a></li> <li><a href="/w/index.php?title=Palmitoyl-coenzyme_A&action=edit&redlink=1" class="new" title="Palmitoyl-coenzyme A (page does not exist)">Palmitoyl-CoA</a></li> <li><a href="/wiki/Pyridoxal_phosphate" title="Pyridoxal phosphate">Pyridoxal phosphate</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:4em;;text-align:center;"><a href="/wiki/Glutamine_synthetase" title="Glutamine synthetase"><abbr title="Glutamine synthetase">GS</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 Glutamine synthetase</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="/wiki/2-Aminoadipic_acid" class="mw-redirect" title="2-Aminoadipic acid">2-Aminoadipic acid</a></li> <li><a href="/w/index.php?title=JFD01307SC&action=edit&redlink=1" class="new" title="JFD01307SC (page does not exist)">JFD01307SC</a></li> <li><a href="/wiki/Methionine_sulfoximine" title="Methionine sulfoximine">Methionine sulfoximine</a></li> <li><a href="/wiki/Phosphinothricin" class="mw-redirect" title="Phosphinothricin">Phosphinothricin (glufosinate)</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:4em;;text-align:center;"><a href="/wiki/Glutamate_decarboxylase" title="Glutamate decarboxylase"><abbr title="Glutamate decarboxylase">GAD</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 Glutamate decarboxylase</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/3-Mercaptopropionic_acid" title="3-Mercaptopropionic acid">3-Mercaptopropionic acid</a></li> <li><a href="/wiki/Aminooxyacetic_acid" title="Aminooxyacetic acid">AAOA</a></li> <li><a href="/wiki/L-Allylglycine" class="mw-redirect" title="L-Allylglycine"><small>L</small>-Allylglycine</a></li> <li><a href="/wiki/Semicarbazide" title="Semicarbazide">Semicarbazide</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><td class="navbox-abovebelow" colspan="2"><div><i><b>See also:</b> <a href="/wiki/Template:Receptor_modulators" title="Template:Receptor modulators">Receptor/signaling modulators</a> • <a href="/wiki/Template:Ionotropic_glutamate_receptor_modulators" title="Template:Ionotropic glutamate receptor modulators">Ionotropic glutamate receptor modulators</a> • <a href="/wiki/Template:Metabotropic_glutamate_receptor_modulators" title="Template:Metabotropic glutamate receptor modulators">Metabotropic glutamate receptor modulators</a> • <a href="/wiki/Template:GABA_metabolism_and_transport_modulators" title="Template:GABA metabolism and transport modulators">GABA metabolism and transport modulators</a></i></div></td></tr></tbody></table></div>    </div><noscript><img src="https://login.wikimedia.org/wiki/Special:CentralAutoLogin/start?useformat=desktop&type=1x1&usesul3=0" alt="" width="1" height="1" style="border: none; position: absolute;"></noscript> <div class="printfooter" data-nosnippet="">Retrieved from "<a dir="ltr" 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