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Picamilon - Wikipedia

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Available in 6 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-6" 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">6 languages</span> </label> <div class="vector-dropdown-content"> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li class="interlanguage-link interwiki-es mw-list-item"><a href="https://es.wikipedia.org/wiki/Picamilon" title="Picamilon – Spanish" lang="es" hreflang="es" data-title="Picamilon" 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/%D9%BE%DB%8C%DA%A9%D8%A7%D9%85%DB%8C%D9%84%D9%88%D9%86" title="پیکامیلون – Persian" lang="fa" hreflang="fa" data-title="پیکامیلون" data-language-autonym="فارسی" data-language-local-name="Persian" class="interlanguage-link-target"><span>فارسی</span></a></li><li class="interlanguage-link interwiki-pt mw-list-item"><a href="https://pt.wikipedia.org/wiki/Picamilon" title="Picamilon – Portuguese" lang="pt" hreflang="pt" data-title="Picamilon" data-language-autonym="Português" data-language-local-name="Portuguese" class="interlanguage-link-target"><span>Português</span></a></li><li class="interlanguage-link interwiki-ru mw-list-item"><a href="https://ru.wikipedia.org/wiki/%D0%9D%D0%B8%D0%BA%D0%BE%D1%82%D0%B8%D0%BD%D0%BE%D0%B8%D0%BB_%D0%B3%D0%B0%D0%BC%D0%BC%D0%B0-%D0%B0%D0%BC%D0%B8%D0%BD%D0%BE%D0%BC%D0%B0%D1%81%D0%BB%D1%8F%D0%BD%D0%B0%D1%8F_%D0%BA%D0%B8%D1%81%D0%BB%D0%BE%D1%82%D0%B0" title="Никотиноил гамма-аминомасляная кислота – Russian" lang="ru" hreflang="ru" data-title="Никотиноил гамма-аминомасляная кислота" data-language-autonym="Русский" data-language-local-name="Russian" class="interlanguage-link-target"><span>Русский</span></a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/Pikamilon" title="Pikamilon – Serbian" lang="sr" hreflang="sr" data-title="Pikamilon" 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/Pikamilon" title="Pikamilon – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Pikamilon" data-language-autonym="Srpskohrvatski / српскохрватски" data-language-local-name="Serbo-Croatian" class="interlanguage-link-target"><span>Srpskohrvatski / српскохрватски</span></a></li> </ul> <div class="after-portlet after-portlet-lang"><span class="wb-langlinks-edit 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data-pinned-container-id="vector-appearance-pinned-container" data-unpinned-container-id="vector-appearance-unpinned-container" > <div class="vector-pinnable-header-label">Appearance</div> <button class="vector-pinnable-header-toggle-button vector-pinnable-header-pin-button" data-event-name="pinnable-header.vector-appearance.pin">move to sidebar</button> <button class="vector-pinnable-header-toggle-button vector-pinnable-header-unpin-button" data-event-name="pinnable-header.vector-appearance.unpin">hide</button> </div> </div> </div> </nav> </div> </div> <div id="bodyContent" class="vector-body" aria-labelledby="firstHeading" data-mw-ve-target-container> <div class="vector-body-before-content"> <div class="mw-indicators"> </div> <div id="siteSub" class="noprint">From Wikipedia, the free encyclopedia</div> </div> <div id="contentSub"><div id="mw-content-subtitle"></div></div> <div id="mw-content-text" class="mw-body-content"><div class="mw-content-ltr mw-parser-output" lang="en" dir="ltr"><div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Chemical compound</div> <p class="mw-empty-elt"> </p> <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): Picamilon">Picamilon</span></caption><tbody><tr><td colspan="2" class="infobox-image notheme" style="background-color: #f8f9fa;"><span class="mw-default-size" typeof="mw:File/Frameless"><a href="/wiki/File:Picamilon2d.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/1/11/Picamilon2d.png/220px-Picamilon2d.png" decoding="async" width="220" height="94" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/1/11/Picamilon2d.png/330px-Picamilon2d.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/1/11/Picamilon2d.png/440px-Picamilon2d.png 2x" data-file-width="531" data-file-height="228" /></a></span></td></tr><tr><td colspan="2" class="infobox-image notheme" style="background-color: #f8f9fa;"><span class="mw-default-size" typeof="mw:File/Frameless"><a href="/wiki/File:Picamilon3d.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/f/f2/Picamilon3d.png/220px-Picamilon3d.png" decoding="async" width="220" height="119" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/f/f2/Picamilon3d.png/330px-Picamilon3d.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/f/f2/Picamilon3d.png/440px-Picamilon3d.png 2x" data-file-width="748" data-file-height="405" /></a></span></td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd">Clinical data</th></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Drug_nomenclature#Trade_names" title="Drug nomenclature">Trade names</a></th><td class="infobox-data">НПК ЭХО</td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;">Other names</th><td class="infobox-data">nicotinoyl-GABA</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">Oral</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><a href="/wiki/ATC_code_N" title="ATC code N">N02CX</a>&#x20;(<span title="www.whocc.no"><a rel="nofollow" class="external text" href="https://www.whocc.no/atc_ddd_index/?code=N02CX">WHO</a></span>)&#x20;</li></ul></div></td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd">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>&#x20;Unapproved "New Drug" (as defined by 21 U.S. Code § 321(p)(1)). Use in <a href="/wiki/Dietary_supplement" title="Dietary supplement">dietary supplements</a>, <a href="/wiki/Food" title="Food">food</a>, or <a href="/wiki/Medicine" title="Medicine">medicine</a> is unlawful; otherwise uncontrolled.<sup id="cite_ref-1" class="reference"><a href="#cite_note-1"><span class="cite-bracket">&#91;</span>1<span class="cite-bracket">&#93;</span></a></sup></li> <li><a href="/wiki/Russia" title="Russia">RU</a>: OTC</li></ul></div> </td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd"><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/Bioavailability" title="Bioavailability">Bioavailability</a></th><td class="infobox-data">50%&#8211;88%<sup id="cite_ref-cui_2-0" class="reference"><a href="#cite_note-cui-2"><span class="cite-bracket">&#91;</span>2<span class="cite-bracket">&#93;</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">1.5 hours<sup id="cite_ref-cui_2-1" class="reference"><a href="#cite_note-cui-2"><span class="cite-bracket">&#91;</span>2<span class="cite-bracket">&#93;</span></a></sup></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Excretion" title="Excretion">Excretion</a></th><td class="infobox-data">Renal</td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd">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%;">4-(Pyridine-3-carbonylamino)butanoic acid</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=34562-97-5">34562-97-5</a></span><sup>&#160;<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/60608">60608</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.54634.html">54634</a></span><sup>&#160;<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/0S5N9SEK4N">0S5N9SEK4N</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/DTXSID40188098">DTXSID40188098</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q4362563#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/100.118.799">100.118.799</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q4362563#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">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>10</sub><span title="Hydrogen">H</span><sub>12</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="7002208217000000000♠"></span>208.217</span>&#160;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=O%3DC%28NCCCC%28%3DO%29O%29c1cccnc1">Interactive image</a></span></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/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%;">O=C(NCCCC(=O)O)c1cccnc1</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/C10H12N2O3/c13-9(14)4-2-6-12-10(15)8-3-1-5-11-7-8/h1,3,5,7H,2,4,6H2,(H,12,15)(H,13,14)<sup>&#160;<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:NAJVRARAUNYNDX-UHFFFAOYSA-N<sup>&#160;<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><tr><td colspan="2" class="infobox-below"><style data-mw-deduplicate="TemplateStyles:r886047488">.mw-parser-output .nobold{font-weight:normal}</style><span class="nobold">&#160;<sup><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><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>&#160;<a href="/wiki/Wikipedia:WikiProject_Chemicals/Chembox_validation" title="Wikipedia:WikiProject Chemicals/Chembox validation">(what is this?)</a></span><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r886047488"><span class="nobold">&#160;&#160;<span class="reflink plainlinks nourlexpansion"><a class="external text" href="https://en.wikipedia.org/w/index.php?title=Special:ComparePages&amp;rev1=464206196&amp;page2=Picamilon">(verify)</a></span></span></td></tr></tbody></table> <p><b>Picamilon</b> (also known as <b><i>N</i>-nicotinoyl-GABA</b>, <b>pycamilon</b>, and <b>pikamilon</b>) is a drug formed by a synthetic combination of <a href="/wiki/Niacin_(substance)" class="mw-redirect" title="Niacin (substance)">niacin</a> and <a href="/wiki/Gamma-aminobutyric_acid" class="mw-redirect" title="Gamma-aminobutyric acid">γ-aminobutyric acid</a> (GABA). It was developed in the <a href="/wiki/Soviet_Union" title="Soviet Union">Soviet Union</a> in 1969<sup id="cite_ref-Some_approaches_to_the_directed_search_for_new_drugs_based_on_nicotinic_acid_3-0" class="reference"><a href="#cite_note-Some_approaches_to_the_directed_search_for_new_drugs_based_on_nicotinic_acid-3"><span class="cite-bracket">&#91;</span>3<span class="cite-bracket">&#93;</span></a></sup> and further studied in both <a href="/wiki/Russia" title="Russia">Russia</a><sup id="cite_ref-pmid2707413_4-0" class="reference"><a href="#cite_note-pmid2707413-4"><span class="cite-bracket">&#91;</span>4<span class="cite-bracket">&#93;</span></a></sup> and <a href="/wiki/Japan" title="Japan">Japan</a> as a <a href="/wiki/Prodrug" title="Prodrug">prodrug</a> of GABA.<sup id="cite_ref-pmid6529802_5-0" class="reference"><a href="#cite_note-pmid6529802-5"><span class="cite-bracket">&#91;</span>5<span class="cite-bracket">&#93;</span></a></sup> </p><p>In Russia, picamilon is sold as a prescription drug. The rights to the drug belong to the Russian pharmaceutical company NPK ECHO ("НПК ЭХО"). It is not approved for sale in the United States and has been deemed an adulterating agent in <a href="/wiki/Dietary_supplements" class="mw-redirect" title="Dietary supplements">dietary supplements</a>,<sup id="cite_ref-DTA2015_6-0" class="reference"><a href="#cite_note-DTA2015-6"><span class="cite-bracket">&#91;</span>6<span class="cite-bracket">&#93;</span></a></sup> with five American companies required to remove their picamilon products from the market in November 2015.<sup id="cite_ref-nutra_7-0" class="reference"><a href="#cite_note-nutra-7"><span class="cite-bracket">&#91;</span>7<span class="cite-bracket">&#93;</span></a></sup> However, as recently as 2020, picamilon has been found in pharmaceutical dosages in over-the-counter supplements in the US.<sup id="cite_ref-neuro_8-0" class="reference"><a href="#cite_note-neuro-8"><span class="cite-bracket">&#91;</span>8<span class="cite-bracket">&#93;</span></a></sup> </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Regulation">Regulation</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Picamilon&amp;action=edit&amp;section=1" title="Edit section: Regulation"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>In the United States, the <a href="/wiki/Food_and_Drug_Administration" title="Food and Drug Administration">Food and Drug Administration</a> ruled in 2015 that picamilon does not fit any of the dietary ingredient categories in the <a href="/wiki/Dietary_Supplement_Health_and_Education_Act_of_1994" title="Dietary Supplement Health and Education Act of 1994">Dietary Supplement Health and Education Act of 1994</a>,<sup id="cite_ref-nutra_7-1" class="reference"><a href="#cite_note-nutra-7"><span class="cite-bracket">&#91;</span>7<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-9" class="reference"><a href="#cite_note-9"><span class="cite-bracket">&#91;</span>9<span class="cite-bracket">&#93;</span></a></sup> namely that it is not a <a href="/wiki/Vitamin" title="Vitamin">vitamin</a>; a <a href="/wiki/Dietary_mineral" class="mw-redirect" title="Dietary mineral">dietary mineral</a>; an <a href="/wiki/Herb" title="Herb">herb</a> or other <a href="/wiki/Botanical" class="mw-redirect" title="Botanical">botanical</a>; an <a href="/wiki/Amino_acid" title="Amino acid">amino acid</a>; a dietary substance for use by humans to supplement the diet by increasing the total dietary intake; or a concentrate, metabolite, constituent, extract, or combination of any ingredient described above that had been marketed in the United States before 1994. Despite the FDA ruling, picamilon remains an ingredient in supplements marketed as nootropics in the US.<sup id="cite_ref-neuro_8-1" class="reference"><a href="#cite_note-neuro-8"><span class="cite-bracket">&#91;</span>8<span class="cite-bracket">&#93;</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=Picamilon&amp;action=edit&amp;section=2" title="Edit section: Pharmacology"><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:Picamilon.jpg" class="mw-file-description"><img alt="Picamilon" src="//upload.wikimedia.org/wikipedia/commons/thumb/f/ff/Picamilon.jpg/220px-Picamilon.jpg" decoding="async" width="220" height="217" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/f/ff/Picamilon.jpg/330px-Picamilon.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/f/ff/Picamilon.jpg/440px-Picamilon.jpg 2x" data-file-width="700" data-file-height="692" /></a><figcaption>Picamilon 20 mg from Russia</figcaption></figure> <p>A Russian study from 1991 showed that picamilon permeated the <a href="/wiki/Blood%E2%80%93brain_barrier" title="Blood–brain barrier">blood–brain barrier</a> in cats and increased cerebral blood flow.<sup id="cite_ref-pmid1884802_10-0" class="reference"><a href="#cite_note-pmid1884802-10"><span class="cite-bracket">&#91;</span>10<span class="cite-bracket">&#93;</span></a></sup> Further work showed it crosses the blood-brain barrier in mice and rats.<sup id="cite_ref-11" class="reference"><a href="#cite_note-11"><span class="cite-bracket">&#91;</span>11<span class="cite-bracket">&#93;</span></a></sup> It is believed that picamilon is <a href="/wiki/Hydrolyzed" class="mw-redirect" title="Hydrolyzed">hydrolyzed</a> into GABA and niacin, similar to the way tocopheryl nicotinate (vitamin E nicotinate) is hydrolyzed.<sup id="cite_ref-12" class="reference"><a href="#cite_note-12"><span class="cite-bracket">&#91;</span>12<span class="cite-bracket">&#93;</span></a></sup> GABA in the brain would activate <a href="/wiki/GABA_receptor" title="GABA receptor">GABA receptors</a>, which in theory should have an <a href="/wiki/Anxiolytic" title="Anxiolytic">anxiolytic</a> effect.<sup id="cite_ref-pmid2884549_13-0" class="reference"><a href="#cite_note-pmid2884549-13"><span class="cite-bracket">&#91;</span>13<span class="cite-bracket">&#93;</span></a></sup> The second released component, <a href="/wiki/Niacin_(substance)" class="mw-redirect" title="Niacin (substance)">niacin</a>, is a <a href="/wiki/Vasodilator" class="mw-redirect" title="Vasodilator">vasodilator</a>.<sup id="cite_ref-pmid17705685_14-0" class="reference"><a href="#cite_note-pmid17705685-14"><span class="cite-bracket">&#91;</span>14<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-pmid15673472_15-0" class="reference"><a href="#cite_note-pmid15673472-15"><span class="cite-bracket">&#91;</span>15<span class="cite-bracket">&#93;</span></a></sup> A 2023 assay study showed that picamilon itself is inactive against 50 biological targets, including GABA receptors, despite being a <a href="/wiki/GABA_analogue" title="GABA analogue">GABA analogue</a>.<sup id="cite_ref-16" class="reference"><a href="#cite_note-16"><span class="cite-bracket">&#91;</span>16<span class="cite-bracket">&#93;</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Pharmacokinetics">Pharmacokinetics</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Picamilon&amp;action=edit&amp;section=3" title="Edit section: Pharmacokinetics"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Plasma picamilon concentrations are generally in the 500–3000 <i>μ</i>g/L range during the first few hours after single oral doses of 50–200&#160;mg.<sup id="cite_ref-cui_2-2" class="reference"><a href="#cite_note-cui-2"><span class="cite-bracket">&#91;</span>2<span class="cite-bracket">&#93;</span></a></sup> It exhibits linear pharmacokinetics with a <a href="/wiki/Half-life" title="Half-life">half-life</a> of 1–2 hours.<sup id="cite_ref-cui_2-3" class="reference"><a href="#cite_note-cui-2"><span class="cite-bracket">&#91;</span>2<span class="cite-bracket">&#93;</span></a></sup> As discussed previously, the drug undergoes hydrolysis to GABA and nicotinic acid. Urinary excretion of parent drug and the two metabolites accounts for up to 79% of a single dose.<sup id="cite_ref-cui_2-4" class="reference"><a href="#cite_note-cui-2"><span class="cite-bracket">&#91;</span>2<span class="cite-bracket">&#93;</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=Picamilon&amp;action=edit&amp;section=4" title="Edit section: See also"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a href="/wiki/List_of_Russian_drugs" title="List of Russian drugs">List of Russian drugs</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=Picamilon&amp;action=edit&amp;section=5" title="Edit section: References"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1239543626">.mw-parser-output .reflist{margin-bottom:0.5em;list-style-type:decimal}@media screen{.mw-parser-output .reflist{font-size:90%}}.mw-parser-output .reflist .references{font-size:100%;margin-bottom:0;list-style-type:inherit}.mw-parser-output .reflist-columns-2{column-width:30em}.mw-parser-output .reflist-columns-3{column-width:25em}.mw-parser-output .reflist-columns{margin-top:0.3em}.mw-parser-output .reflist-columns ol{margin-top:0}.mw-parser-output .reflist-columns li{page-break-inside:avoid;break-inside:avoid-column}.mw-parser-output .reflist-upper-alpha{list-style-type:upper-alpha}.mw-parser-output .reflist-upper-roman{list-style-type:upper-roman}.mw-parser-output .reflist-lower-alpha{list-style-type:lower-alpha}.mw-parser-output .reflist-lower-greek{list-style-type:lower-greek}.mw-parser-output .reflist-lower-roman{list-style-type:lower-roman}</style><div class="reflist reflist-columns references-column-width reflist-columns-2"> <ol class="references"> <li id="cite_note-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 web cs1"><a rel="nofollow" class="external text" href="https://www.fda.gov/food/dietary-supplement-ingredient-directory/picamilon-dietary-supplements">"Picamilon in Dietary Supplements"</a>. <i><a href="/wiki/FDA" class="mw-redirect" title="FDA">FDA</a></i>. November 29, 2017<span class="reference-accessdate">. Retrieved <span class="nowrap">June 9,</span> 2023</span>.</cite><span title="ctx_ver=Z39.88-2004&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&amp;rft.genre=unknown&amp;rft.jtitle=FDA&amp;rft.atitle=Picamilon+in+Dietary+Supplements&amp;rft.date=2017-11-29&amp;rft_id=https%3A%2F%2Fwww.fda.gov%2Ffood%2Fdietary-supplement-ingredient-directory%2Fpicamilon-dietary-supplements&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3APicamilon" class="Z3988"></span></span> </li> <li id="cite_note-cui-2"><span class="mw-cite-backlink">^ <a href="#cite_ref-cui_2-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-cui_2-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-cui_2-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-cui_2-3"><sup><i><b>d</b></i></sup></a> <a href="#cite_ref-cui_2-4"><sup><i><b>e</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFCuiChenZhanZhang2010" class="citation journal cs1">Cui W, Chen X, Zhan Y, Zhang Z, Zhang Y, Zhong D (May 2010). "Determination of picamilon concentration in human plasma by liquid chromatography-tandem mass spectrometry". <i>Journal of Chromatography B</i>. <b>878</b> (15–16): 1181–4. <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.jchromb.2010.03.013">10.1016/j.jchromb.2010.03.013</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a>&#160;<a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/20359966">20359966</a>.</cite><span title="ctx_ver=Z39.88-2004&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&amp;rft.genre=article&amp;rft.jtitle=Journal+of+Chromatography+B&amp;rft.atitle=Determination+of+picamilon+concentration+in+human+plasma+by+liquid+chromatography-tandem+mass+spectrometry&amp;rft.volume=878&amp;rft.issue=15%E2%80%9316&amp;rft.pages=1181-4&amp;rft.date=2010-05&amp;rft_id=info%3Adoi%2F10.1016%2Fj.jchromb.2010.03.013&amp;rft_id=info%3Apmid%2F20359966&amp;rft.aulast=Cui&amp;rft.aufirst=W&amp;rft.au=Chen%2C+X&amp;rft.au=Zhan%2C+Y&amp;rft.au=Zhang%2C+Z&amp;rft.au=Zhang%2C+Y&amp;rft.au=Zhong%2C+D&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3APicamilon" class="Z3988"></span></span> </li> <li id="cite_note-Some_approaches_to_the_directed_search_for_new_drugs_based_on_nicotinic_acid-3"><span class="mw-cite-backlink"><b><a href="#cite_ref-Some_approaches_to_the_directed_search_for_new_drugs_based_on_nicotinic_acid_3-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFKopelevichGunar1999" class="citation journal cs1">Kopelevich VM, Gunar VI (April 1999). "Some approaches to the directed search for new drugs based on nicotinic acid". <i>Pharmaceutical Chemistry Journal</i>. <b>33</b> (4): 177–187. <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%2FBF02509934">10.1007/BF02509934</a>. <a href="/wiki/S2CID_(identifier)" class="mw-redirect" title="S2CID (identifier)">S2CID</a>&#160;<a rel="nofollow" class="external text" href="https://api.semanticscholar.org/CorpusID:36930437">36930437</a>.</cite><span title="ctx_ver=Z39.88-2004&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&amp;rft.genre=article&amp;rft.jtitle=Pharmaceutical+Chemistry+Journal&amp;rft.atitle=Some+approaches+to+the+directed+search+for+new+drugs+based+on+nicotinic+acid&amp;rft.volume=33&amp;rft.issue=4&amp;rft.pages=177-187&amp;rft.date=1999-04&amp;rft_id=info%3Adoi%2F10.1007%2FBF02509934&amp;rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A36930437%23id-name%3DS2CID&amp;rft.aulast=Kopelevich&amp;rft.aufirst=VM&amp;rft.au=Gunar%2C+VI&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3APicamilon" class="Z3988"></span></span> </li> <li id="cite_note-pmid2707413-4"><span class="mw-cite-backlink"><b><a href="#cite_ref-pmid2707413_4-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFMirzoianGan&#39;shina1989" class="citation journal cs1 cs1-prop-foreign-lang-source">Mirzoian RS, Gan'shina TS (1989). "[The new cerebrovascular preparation pikamilon]". <i>Farmakologiia i Toksikologiia</i> (in Russian). <b>52</b> (1): 23–6. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a>&#160;<a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/2707413">2707413</a>.</cite><span title="ctx_ver=Z39.88-2004&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&amp;rft.genre=article&amp;rft.jtitle=Farmakologiia+i+Toksikologiia&amp;rft.atitle=%5BThe+new+cerebrovascular+preparation+pikamilon%5D&amp;rft.volume=52&amp;rft.issue=1&amp;rft.pages=23-6&amp;rft.date=1989&amp;rft_id=info%3Apmid%2F2707413&amp;rft.aulast=Mirzoian&amp;rft.aufirst=RS&amp;rft.au=Gan%27shina%2C+TS&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3APicamilon" class="Z3988"></span></span> </li> <li id="cite_note-pmid6529802-5"><span class="mw-cite-backlink"><b><a href="#cite_ref-pmid6529802_5-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFMatsuyamaYamashitaNodaGoto1984" class="citation journal cs1">Matsuyama K, Yamashita C, Noda A, Goto S, Noda H, Ichimaru Y, et&#160;al. (October 1984). <a rel="nofollow" class="external text" href="https://doi.org/10.1248%2Fcpb.32.4089">"Evaluation of isonicotinoyl-gamma-aminobutyric acid (GABA) and nicotinoyl-GABA as pro-drugs of GABA"</a>. <i>Chemical &amp; Pharmaceutical Bulletin</i>. <b>32</b> (10): 4089–95. <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/10.1248%2Fcpb.32.4089">10.1248/cpb.32.4089</a></span>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a>&#160;<a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/6529802">6529802</a>.</cite><span title="ctx_ver=Z39.88-2004&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&amp;rft.genre=article&amp;rft.jtitle=Chemical+%26+Pharmaceutical+Bulletin&amp;rft.atitle=Evaluation+of+isonicotinoyl-gamma-aminobutyric+acid+%28GABA%29+and+nicotinoyl-GABA+as+pro-drugs+of+GABA&amp;rft.volume=32&amp;rft.issue=10&amp;rft.pages=4089-95&amp;rft.date=1984-10&amp;rft_id=info%3Adoi%2F10.1248%2Fcpb.32.4089&amp;rft_id=info%3Apmid%2F6529802&amp;rft.aulast=Matsuyama&amp;rft.aufirst=K&amp;rft.au=Yamashita%2C+C&amp;rft.au=Noda%2C+A&amp;rft.au=Goto%2C+S&amp;rft.au=Noda%2C+H&amp;rft.au=Ichimaru%2C+Y&amp;rft.au=Gomita%2C+Y&amp;rft_id=https%3A%2F%2Fdoi.org%2F10.1248%252Fcpb.32.4089&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3APicamilon" class="Z3988"></span></span> </li> <li id="cite_note-DTA2015-6"><span class="mw-cite-backlink"><b><a href="#cite_ref-DTA2015_6-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFAvulaChittiboyinaSagiWang2016" class="citation journal cs1">Avula B, Chittiboyina AG, Sagi S, Wang YH, Wang M, Khan IA, et&#160;al. (March 2016). <a rel="nofollow" class="external text" href="https://doi.org/10.1002%2Fdta.1853">"Identification and quantification of vinpocetine and picamilon in dietary supplements sold in the United States"</a>. <i>Drug Testing and Analysis</i>. <b>8</b> (3–4): 334–43. <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/10.1002%2Fdta.1853">10.1002/dta.1853</a></span>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a>&#160;<a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/26426301">26426301</a>.</cite><span title="ctx_ver=Z39.88-2004&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&amp;rft.genre=article&amp;rft.jtitle=Drug+Testing+and+Analysis&amp;rft.atitle=Identification+and+quantification+of+vinpocetine+and+picamilon+in+dietary+supplements+sold+in+the+United+States&amp;rft.volume=8&amp;rft.issue=3%E2%80%934&amp;rft.pages=334-43&amp;rft.date=2016-03&amp;rft_id=info%3Adoi%2F10.1002%2Fdta.1853&amp;rft_id=info%3Apmid%2F26426301&amp;rft.aulast=Avula&amp;rft.aufirst=B&amp;rft.au=Chittiboyina%2C+AG&amp;rft.au=Sagi%2C+S&amp;rft.au=Wang%2C+YH&amp;rft.au=Wang%2C+M&amp;rft.au=Khan%2C+IA&amp;rft.au=Cohen%2C+PA&amp;rft_id=https%3A%2F%2Fdoi.org%2F10.1002%252Fdta.1853&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3APicamilon" class="Z3988"></span></span> </li> <li id="cite_note-nutra-7"><span class="mw-cite-backlink">^ <a href="#cite_ref-nutra_7-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-nutra_7-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="http://www.nutraingredients-usa.com/Regulation/FDA-sends-five-warning-letters-over-supplements-containing-picamilon/?c=7InNqGv0AjdjxWpyk%2BfGQw%3D%3D&amp;p2=">"FDA sends five warning letters over supplements containing picamilon"</a>. NutraIngredients-USA.com, William Reed Business Media. 2 December 2015<span class="reference-accessdate">. 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title="ctx_ver=Z39.88-2004&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&amp;rft.genre=article&amp;rft.jtitle=Basic+%26+Clinical+Pharmacology+%26+Toxicology&amp;rft.atitle=Picamilon%2C+a+%CE%B3-aminobutyric+acid+%28GABA%29+analogue+and+marketed+nootropic%2C+is+inactive+against+50+biological+targets&amp;rft.volume=132&amp;rft.issue=4&amp;rft.pages=355-358&amp;rft.date=2023-04&amp;rft_id=info%3Adoi%2F10.1111%2Fbcpt.13836&amp;rft_id=info%3Apmid%2F36668678&amp;rft.aulast=Santillo&amp;rft.aufirst=MF&amp;rft.au=Sprando%2C+RL&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3APicamilon" class="Z3988"></span></span> </li> </ol></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=Picamilon&amp;action=edit&amp;section=6" title="Edit section: External links"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a rel="nofollow" class="external text" href="https://meshb.nlm.nih.gov/record/ui?name=nicotinoyl-GABA">nicotinoyl-GABA</a> at the U.S. National Library of Medicine <a href="/wiki/Medical_Subject_Headings" title="Medical Subject Headings">Medical Subject Headings</a> (MeSH)</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 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.navbox-group,.mw-parser-output .navbox-subgroup .navbox-title{background-color:#ddf}.mw-parser-output .navbox-subgroup .navbox-group,.mw-parser-output .navbox-subgroup .navbox-abovebelow{background-color:#e6e6ff}.mw-parser-output .navbox-even{background-color:#f7f7f7}.mw-parser-output .navbox-odd{background-color:transparent}.mw-parser-output .navbox .hlist td dl,.mw-parser-output .navbox .hlist td ol,.mw-parser-output .navbox .hlist td ul,.mw-parser-output .navbox td.hlist dl,.mw-parser-output .navbox td.hlist ol,.mw-parser-output .navbox td.hlist ul{padding:0.125em 0}.mw-parser-output .navbox .navbar{display:block;font-size:100%}.mw-parser-output .navbox-title .navbar{float:left;text-align:left;margin-right:0.5em}body.skin--responsive .mw-parser-output .navbox-image img{max-width:none!important}@media print{body.ns-0 .mw-parser-output .navbox{display:none!important}}</style></div><div role="navigation" class="navbox" aria-labelledby="GABA_receptor_modulators" style="padding:3px"><table class="nowraplinks hlist mw-collapsible mw-collapsed navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><style data-mw-deduplicate="TemplateStyles:r1239400231">.mw-parser-output .navbar{display:inline;font-size:88%;font-weight:normal}.mw-parser-output .navbar-collapse{float:left;text-align:left}.mw-parser-output .navbar-boxtext{word-spacing:0}.mw-parser-output .navbar ul{display:inline-block;white-space:nowrap;line-height:inherit}.mw-parser-output .navbar-brackets::before{margin-right:-0.125em;content:"[ "}.mw-parser-output .navbar-brackets::after{margin-left:-0.125em;content:" ]"}.mw-parser-output .navbar li{word-spacing:-0.125em}.mw-parser-output .navbar a>span,.mw-parser-output .navbar a>abbr{text-decoration:inherit}.mw-parser-output .navbar-mini abbr{font-variant:small-caps;border-bottom:none;text-decoration:none;cursor:inherit}.mw-parser-output .navbar-ct-full{font-size:114%;margin:0 7em}.mw-parser-output .navbar-ct-mini{font-size:114%;margin:0 4em}html.skin-theme-clientpref-night .mw-parser-output .navbar li a abbr{color:var(--color-base)!important}@media(prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .navbar li a abbr{color:var(--color-base)!important}}@media print{.mw-parser-output .navbar{display:none!important}}</style><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:GABA_receptor_modulators" title="Template:GABA receptor modulators"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:GABA_receptor_modulators" title="Template talk:GABA receptor modulators"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:GABA_receptor_modulators" title="Special:EditPage/Template:GABA receptor modulators"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="GABA_receptor_modulators" style="font-size:114%;margin:0 4em"><a href="/wiki/GABA_receptor" title="GABA receptor"><abbr title="γ-Aminobutyric acid">GABA</abbr> 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/Ionotropic_GABA_receptors" class="mw-redirect" title="Ionotropic GABA receptors">Ionotropic</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:5em;text-align:center"><a href="/wiki/%CE%93-Aminobutyric_acid_A_receptor" class="mw-redirect" title="Γ-Aminobutyric acid A receptor"><abbr title="γ-Aminobutyric acid A receptor">GABA<sub>A</sub></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 γ-Aminobutyric acid A receptor</span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><i>Agonists:</i> <a href="/wiki/Catechin" title="Catechin">(+)-Catechin</a></li> <li><a href="/wiki/Bamaluzole" title="Bamaluzole">Bamaluzole</a></li> <li><a href="/wiki/Barbiturate" title="Barbiturate">Barbiturates</a> (e.g., <a href="/wiki/Phenobarbital" title="Phenobarbital">phenobarbital</a>)</li> <li><a href="/wiki/Beta-Alanine" class="mw-redirect" title="Beta-Alanine">Beta-Alanine</a></li> <li><a href="/wiki/BL-1020" title="BL-1020">BL-1020</a></li> <li><a href="/w/index.php?title=5-Aminovaleric_acid&amp;action=edit&amp;redlink=1" class="new" title="5-Aminovaleric acid (page does not exist)">DAVA</a></li> <li><a href="/w/index.php?title=Dihydromuscimol&amp;action=edit&amp;redlink=1" class="new" title="Dihydromuscimol (page does not exist)">Dihydromuscimol</a></li> <li><a href="/wiki/Gamma-Aminobutyric_acid" class="mw-redirect" title="Gamma-Aminobutyric acid">GABA</a></li> <li><a href="/w/index.php?title=Gabamide&amp;action=edit&amp;redlink=1" class="new" title="Gabamide (page does not exist)">Gabamide</a></li> <li><a href="/wiki/GABOB" class="mw-redirect" title="GABOB">GABOB</a></li> <li><a href="/wiki/Gaboxadol" title="Gaboxadol">Gaboxadol (THIP)</a></li> <li><a href="/wiki/Homotaurine" title="Homotaurine">Homotaurine (tramiprosate, 3-APS)</a></li> <li><a href="/wiki/Ibotenic_acid" title="Ibotenic acid">Ibotenic acid</a></li> <li><a href="/w/index.php?title=Iso-THAZ&amp;action=edit&amp;redlink=1" class="new" title="Iso-THAZ (page does not exist)">iso-THAZ</a></li> <li><a href="/w/index.php?title=Iso-THIP&amp;action=edit&amp;redlink=1" class="new" title="Iso-THIP (page does not exist)">iso-THIP</a></li> <li><a href="/wiki/Isoguvacine" title="Isoguvacine">Isoguvacine</a></li> <li><a href="/w/index.php?title=Isomuscimol&amp;action=edit&amp;redlink=1" class="new" title="Isomuscimol (page does not exist)">Isomuscimol</a></li> <li><a href="/wiki/Isonipecotic_acid" title="Isonipecotic acid">Isonipecotic acid</a></li> <li><a href="/w/index.php?title=Kojic_amine&amp;action=edit&amp;redlink=1" class="new" title="Kojic amine (page does not exist)">Kojic amine</a></li> <li><a href="/wiki/L-838,417" title="L-838,417">L-838,417</a></li> <li><a href="/wiki/Lignan" title="Lignan">Lignans</a> (e.g., <a href="/wiki/Honokiol" title="Honokiol">honokiol</a>)</li> <li><a href="/wiki/Methylglyoxal" title="Methylglyoxal">Methylglyoxal</a></li> <li><a href="/wiki/Monastrol" title="Monastrol">Monastrol</a></li> <li><a href="/wiki/Muscimol" title="Muscimol">Muscimol</a></li> <li><a href="/wiki/Nefiracetam" title="Nefiracetam">Nefiracetam</a></li> <li><a href="/wiki/Neuroactive_steroid" class="mw-redirect" title="Neuroactive steroid">Neuroactive steroids</a> (e.g., <a href="/wiki/Allopregnanolone" title="Allopregnanolone">allopregnanolone</a>)</li> <li><a href="/wiki/Org_20599" class="mw-redirect" title="Org 20599">Org 20599</a></li> <li><a href="/wiki/PF-6372865" class="mw-redirect" title="PF-6372865">PF-6372865</a></li> <li><a href="/wiki/Phenibut" title="Phenibut">Phenibut</a></li> <li><a class="mw-selflink selflink">Picamilon</a></li> <li><a href="/w/index.php?title=Piperidine-4-sulfonic_acid&amp;action=edit&amp;redlink=1" class="new" title="Piperidine-4-sulfonic acid (page does not exist)">P4S</a></li> <li><a href="/wiki/Progabide" title="Progabide">Progabide</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/SL-75102" title="SL-75102">SL-75102</a></li> <li><a href="/wiki/Taurine" title="Taurine">Taurine</a></li> <li><a href="/w/index.php?title=Trans-4-Aminocrotonic_acid&amp;action=edit&amp;redlink=1" class="new" title="Trans-4-Aminocrotonic acid (page does not exist)">TACA</a></li> <li><a href="/w/index.php?title=Trans-2-(Aminomethyl)cyclopropanecarboxylic_acid&amp;action=edit&amp;redlink=1" class="new" title="Trans-2-(Aminomethyl)cyclopropanecarboxylic acid (page does not exist)">TAMP</a></li> <li><a href="/wiki/Terpenoid" title="Terpenoid">Terpenoids</a> (e.g., <a href="/wiki/Borneol" title="Borneol">borneol</a>)</li> <li><a href="/wiki/Thiomuscimol" title="Thiomuscimol">Thiomuscimol</a></li> <li><a href="/wiki/Tolgabide" title="Tolgabide">Tolgabide</a></li> <li><a href="/w/index.php?title=(Z)-3-((Aminoiminomethyl)thio)prop-2-enoic_acid&amp;action=edit&amp;redlink=1" class="new" title="(Z)-3-((Aminoiminomethyl)thio)prop-2-enoic acid (page does not exist)">ZAPA</a></li></ul> <ul><li><i>Positive modulators (abridged; see <a href="/wiki/Template:GABAAR_PAMs" class="mw-redirect" title="Template:GABAAR PAMs">here</a> for a full list):</i> <a href="/w/index.php?title=%CE%91-Ethyl-%CE%B1-methylthiobutyrolactone&amp;action=edit&amp;redlink=1" class="new" title="Α-Ethyl-α-methylthiobutyrolactone (page does not exist)">α-EMTBL</a></li> <li><a href="/wiki/Alcohol_(chemistry)" title="Alcohol (chemistry)">Alcohols</a> (e.g., <a href="/wiki/Alcohol_(drug)" title="Alcohol (drug)">drinking alcohol</a>, <a href="/wiki/Tert-Amyl_alcohol" title="Tert-Amyl alcohol">2M2B</a>)</li> <li><a href="/wiki/Anabolic_steroid" title="Anabolic steroid">Anabolic steroids</a></li> <li><a href="/wiki/Avermectin" title="Avermectin">Avermectins</a> (e.g., <a href="/wiki/Ivermectin" title="Ivermectin">ivermectin</a>)</li> <li><a href="/wiki/Barbiturate" title="Barbiturate">Barbiturates</a> (e.g., <a href="/wiki/Phenobarbital" title="Phenobarbital">phenobarbital</a>)</li> <li><a href="/wiki/Benzodiazepine" title="Benzodiazepine">Benzodiazepines</a> (e.g., <a href="/wiki/Diazepam" title="Diazepam">diazepam</a>)</li> <li><a href="/wiki/Bromide" title="Bromide">Bromide</a> compounds (e.g., <a href="/wiki/Potassium_bromide" title="Potassium bromide">potassium bromide</a>)</li> <li><a href="/wiki/Carbamate" title="Carbamate">Carbamates</a> (e.g., <a href="/wiki/Meprobamate" title="Meprobamate">meprobamate</a>)</li> <li><a href="/wiki/Carbamazepine" title="Carbamazepine">Carbamazepine</a></li> <li><a href="/wiki/Chloralose" title="Chloralose">Chloralose</a></li> <li><a href="/wiki/Chlormezanone" title="Chlormezanone">Chlormezanone</a></li> <li><a href="/wiki/Clomethiazole" title="Clomethiazole">Clomethiazole</a></li> <li><a href="/wiki/Dihydroergoline" class="mw-redirect" title="Dihydroergoline">Dihydroergolines</a> (e.g., <a href="/wiki/Ergoloid" title="Ergoloid">ergoloid (dihydroergotoxine)</a>)</li> <li><a href="/wiki/Etazepine" title="Etazepine">Etazepine</a></li> <li><a href="/wiki/Etifoxine" title="Etifoxine">Etifoxine</a></li> <li><a href="/wiki/Fenamate" class="mw-redirect" title="Fenamate">Fenamates</a> (e.g., <a href="/wiki/Mefenamic_acid" title="Mefenamic acid">mefenamic acid</a>)</li> <li><a href="/wiki/Flavonoid" title="Flavonoid">Flavonoids</a> (e.g., <a href="/wiki/Apigenin" title="Apigenin">apigenin</a>, <a href="/wiki/Hispidulin" title="Hispidulin">hispidulin</a>)</li> <li><a href="/wiki/Fluoxetine" title="Fluoxetine">Fluoxetine</a></li> <li><a href="/wiki/Flupirtine" title="Flupirtine">Flupirtine</a></li> <li><a href="/wiki/Imidazole" title="Imidazole">Imidazoles</a> (e.g., <a href="/wiki/Etomidate" title="Etomidate">etomidate</a>)</li> <li><a href="/wiki/Kava" title="Kava">Kava</a> constituents (e.g., <a href="/wiki/Kavain" title="Kavain">kavain</a>)</li> <li><a href="/wiki/Lanthanum" title="Lanthanum">Lanthanum</a></li> <li><a href="/wiki/Loreclezole" title="Loreclezole">Loreclezole</a></li> <li><a href="/wiki/Monastrol" title="Monastrol">Monastrol</a></li> <li><a href="/wiki/Neuroactive_steroid" class="mw-redirect" title="Neuroactive steroid">Neuroactive steroids</a> (e.g., <a href="/wiki/Allopregnanolone" title="Allopregnanolone">allopregnanolone</a>, <a href="/wiki/Cholesterol" title="Cholesterol">cholesterol</a>, <a href="/wiki/THDOC" class="mw-redirect" title="THDOC">THDOC</a>)</li> <li><a href="/wiki/Niacin_(substance)" class="mw-redirect" title="Niacin (substance)">Niacin</a></li> <li><a href="/wiki/Niacinamide" class="mw-redirect" title="Niacinamide">Niacinamide</a></li> <li><a href="/wiki/Nonbenzodiazepine" title="Nonbenzodiazepine">Nonbenzodiazepines</a> (e.g., <a href="/wiki/%CE%92-carboline" class="mw-redirect" title="Β-carboline">β-carbolines</a> (e.g., <a href="/wiki/Abecarnil" title="Abecarnil">abecarnil</a>), <a href="/wiki/Cyclopyrrolone" class="mw-redirect" title="Cyclopyrrolone">cyclopyrrolones</a> (e.g., <a href="/wiki/Zopiclone" title="Zopiclone">zopiclone</a>), <a href="/wiki/Imidazopyridine" title="Imidazopyridine">imidazopyridines</a> (e.g., <a href="/wiki/Zolpidem" title="Zolpidem">zolpidem</a>), <a href="/wiki/Pyrazolopyrimidine" title="Pyrazolopyrimidine">pyrazolopyrimidines</a> (e.g., <a href="/wiki/Zaleplon" title="Zaleplon">zaleplon</a>))</li> <li><a href="/wiki/Norfluoxetine" class="mw-redirect" title="Norfluoxetine">Norfluoxetine</a></li> <li><a href="/wiki/Petrichloral" title="Petrichloral">Petrichloral</a></li> <li><a href="/wiki/Phenol" title="Phenol">Phenols</a> (e.g., <a href="/wiki/Propofol" title="Propofol">propofol</a>)</li> <li><a href="/wiki/Phenytoin" title="Phenytoin">Phenytoin</a></li> <li><a href="/wiki/Piperidinedione" class="mw-redirect" title="Piperidinedione">Piperidinediones</a> (e.g., <a href="/wiki/Glutethimide" title="Glutethimide">glutethimide</a>)</li> <li><a href="/wiki/Propanidid" title="Propanidid">Propanidid</a></li> <li><a href="/wiki/Pyrazolopyridine" class="mw-redirect" title="Pyrazolopyridine">Pyrazolopyridines</a> (e.g., <a href="/wiki/Etazolate" title="Etazolate">etazolate</a>)</li> <li><a href="/wiki/Quinazolinone" title="Quinazolinone">Quinazolinones</a> (e.g., <a href="/wiki/Methaqualone" title="Methaqualone">methaqualone</a>)</li> <li><a href="/wiki/Retigabine" title="Retigabine">Retigabine (ezogabine)</a></li> <li><a href="/wiki/ROD-188" title="ROD-188">ROD-188</a></li> <li><a href="/wiki/Scutellaria" title="Scutellaria">Skullcap</a> constituents (e.g., <a href="/wiki/Baicalin" title="Baicalin">baicalin</a>)</li> <li><a href="/wiki/Stiripentol" title="Stiripentol">Stiripentol</a></li> <li><a href="/w/index.php?title=Sulfonylalkane&amp;action=edit&amp;redlink=1" class="new" title="Sulfonylalkane (page does not exist)">Sulfonylalkanes</a> (e.g., <a href="/wiki/Sulfonmethane" title="Sulfonmethane">sulfonmethane (sulfonal)</a>)</li> <li><a href="/wiki/Topiramate" title="Topiramate">Topiramate</a></li> <li><a href="/wiki/Valerian_(herb)" title="Valerian (herb)">Valerian</a> constituents (e.g., <a href="/wiki/Valerenic_acid" title="Valerenic acid">valerenic acid</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/Diethyl_ether" title="Diethyl ether">diethyl ether</a>, <a href="/wiki/Paraldehyde" title="Paraldehyde">paraldehyde</a>, <a href="/wiki/Sevoflurane" title="Sevoflurane">sevoflurane</a>)</li></ul> <ul><li><i>Antagonists:</i> <a href="/wiki/Bicuculline" title="Bicuculline">Bicuculline</a></li> <li><a href="/wiki/Coriamyrtin" title="Coriamyrtin">Coriamyrtin</a></li> <li><a href="/w/index.php?title=Dihydrosecurinine&amp;action=edit&amp;redlink=1" class="new" title="Dihydrosecurinine (page does not exist)">Dihydrosecurinine</a></li> <li><a href="/wiki/Famiraprinium" title="Famiraprinium">Famiraprinium</a></li> <li><a href="/wiki/Gabazine" title="Gabazine">Gabazine (SR-95531)</a></li> <li><a href="/wiki/Hydrastine" title="Hydrastine">Hydrastine</a></li> <li><a href="/w/index.php?title=Hyenanchin&amp;action=edit&amp;redlink=1" class="new" title="Hyenanchin (page does not exist)">Hyenachin (mellitoxin)</a></li> <li><a href="/w/index.php?title=PHP-501&amp;action=edit&amp;redlink=1" class="new" title="PHP-501 (page does not exist)">PHP-501</a></li> <li><a href="/wiki/Pitrazepin" title="Pitrazepin">Pitrazepin</a></li> <li><a href="/wiki/Securinine" title="Securinine">Securinine</a></li> <li><a href="/wiki/Sinomenine" title="Sinomenine">Sinomenine</a></li> <li><a href="/w/index.php?title=SR-42641&amp;action=edit&amp;redlink=1" class="new" title="SR-42641 (page does not exist)">SR-42641</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><i>Negative modulators:</i> <a href="/w/index.php?title=5-Ethyl-5-(1,3-dimethylbut-1%27-enyl)barbituric_acid&amp;action=edit&amp;redlink=1" class="new" title="5-Ethyl-5-(1,3-dimethylbut-1&#39;-enyl)barbituric acid (page does not exist)">1,3M1B</a></li> <li><a href="/w/index.php?title=5-Ethyl-5-(3-methylbut-2%27-enyl)barbituric_acid&amp;action=edit&amp;redlink=1" class="new" title="5-Ethyl-5-(3-methylbut-2&#39;-enyl)barbituric acid (page does not exist)">3M2B</a></li> <li><a href="/wiki/11-Ketoprogesterone" title="11-Ketoprogesterone">11-Ketoprogesterone</a></li> <li><a href="/wiki/17-Phenylandrostenol" title="17-Phenylandrostenol">17-Phenylandrostenol</a></li> <li><a href="/wiki/%CE%913IA" title="Α3IA">α3IA</a></li> <li><a href="/wiki/%CE%915IA" title="Α5IA">α5IA (LS-193,268)</a></li> <li><a href="/w/index.php?title=Butyl_%CE%B2-carboline-3-carboxylate&amp;action=edit&amp;redlink=1" class="new" title="Butyl β-carboline-3-carboxylate (page does not exist)">β-CCB</a></li> <li><a href="/w/index.php?title=Ethyl_%CE%B2-carboline-3-carboxylate&amp;action=edit&amp;redlink=1" class="new" title="Ethyl β-carboline-3-carboxylate (page does not exist)">β-CCE</a></li> <li><a href="/w/index.php?title=Methyl_%CE%B2-carboline-3-carboxylate&amp;action=edit&amp;redlink=1" class="new" title="Methyl β-carboline-3-carboxylate (page does not exist)">β-CCM</a></li> <li><a href="/w/index.php?title=Propyl_%CE%B2-carboline-3-carboxylate&amp;action=edit&amp;redlink=1" class="new" title="Propyl β-carboline-3-carboxylate (page does not exist)">β-CCP</a></li> <li><a href="/w/index.php?title=%CE%92-Ethyl-%CE%B2-methyl-%CE%B3-butyrolactone&amp;action=edit&amp;redlink=1" class="new" title="Β-Ethyl-β-methyl-γ-butyrolactone (page does not exist)">β-EMGBL</a></li> <li><a href="/wiki/Anabolic_steroid" title="Anabolic steroid">Anabolic steroids</a></li> <li><a href="/wiki/Amiloride" title="Amiloride">Amiloride</a></li> <li><a href="/wiki/Anisatin" title="Anisatin">Anisatin</a></li> <li><a href="/wiki/%CE%92-Lactam" title="Β-Lactam">β-Lactams</a> (e.g., <a href="/wiki/Penicillin" title="Penicillin">penicillins</a>, <a href="/wiki/Cephalosporin" title="Cephalosporin">cephalosporins</a>, <a href="/wiki/Carbapenem" title="Carbapenem">carbapenems</a>)</li> <li><a href="/wiki/Basmisanil" title="Basmisanil">Basmisanil</a></li> <li><a href="/wiki/Bemegride" title="Bemegride">Bemegride</a></li> <li><a href="/wiki/Bicyclic_phosphate" title="Bicyclic phosphate">Bicyclic phosphates</a> (<a href="/wiki/TBPS" title="TBPS">TBPS</a>, <a href="/wiki/TBPO" title="TBPO">TBPO</a>, <a href="/wiki/IPTBO" title="IPTBO">IPTBO</a>)</li> <li><a href="/wiki/BIDN" title="BIDN">BIDN</a></li> <li><a href="/wiki/Bilobalide" title="Bilobalide">Bilobalide</a></li> <li><a href="/wiki/Bupropion" title="Bupropion">Bupropion</a></li> <li><a href="/wiki/5-(2-Cyclohexylideneethyl)-5-ethylbarbituric_acid" class="mw-redirect" title="5-(2-Cyclohexylideneethyl)-5-ethylbarbituric acid">CHEB</a></li> <li><a href="/wiki/Chlorophenylsilatrane" title="Chlorophenylsilatrane">Chlorophenylsilatrane</a></li> <li><a href="/wiki/Cicutoxin" title="Cicutoxin">Cicutoxin</a></li> <li><a href="/wiki/Cloflubicyne" title="Cloflubicyne">Cloflubicyne</a></li> <li><a href="/wiki/Cyclothiazide" title="Cyclothiazide">Cyclothiazide</a></li> <li><a href="/wiki/Dehydroepiandrosterone" title="Dehydroepiandrosterone">DHEA</a></li> <li><a href="/wiki/Dehydroepiandrosterone_sulfate" title="Dehydroepiandrosterone sulfate">DHEA-S</a></li> <li><a href="/wiki/Dieldrin" title="Dieldrin">Dieldrin</a></li> <li><a href="/wiki/(%2B)-5-(1,3-Dimethylbutyl)-5-ethylbarbituric_acid" class="mw-redirect" title="(+)-5-(1,3-Dimethylbutyl)-5-ethylbarbituric acid">(+)-DMBB</a></li> <li><a href="/wiki/DMCM" title="DMCM">DMCM</a></li> <li><a href="/w/index.php?title=5,7-Dihydroxy-6-methoxy-2(4-phenoxyphenyl)-4H-chromene-4-one&amp;action=edit&amp;redlink=1" class="new" title="5,7-Dihydroxy-6-methoxy-2(4-phenoxyphenyl)-4H-chromene-4-one (page does not exist)">DMPC</a></li> <li><a href="/wiki/EBOB" title="EBOB">EBOB</a></li> <li><a href="/w/index.php?title=Etbicyphat&amp;action=edit&amp;redlink=1" class="new" title="Etbicyphat (page does not exist)">Etbicyphat</a></li> <li><a href="/wiki/FG-7142" title="FG-7142">FG-7142 (ZK-31906)</a></li> <li><a href="/w/index.php?title=Fiprole&amp;action=edit&amp;redlink=1" class="new" title="Fiprole (page does not exist)">Fiproles</a> (e.g., <a href="/wiki/Fipronil" title="Fipronil">fipronil</a>)</li> <li><a href="/wiki/Flavonoid" title="Flavonoid">Flavonoids</a> (e.g., <a href="/wiki/Amentoflavone" title="Amentoflavone">amentoflavone</a>, <a href="/wiki/Oroxylin_A" title="Oroxylin A">oroxylin A</a>)</li> <li><a href="/wiki/Flumazenil" title="Flumazenil">Flumazenil</a></li> <li><a href="/wiki/Fluoroquinolone" class="mw-redirect" title="Fluoroquinolone">Fluoroquinolones</a> (e.g., <a href="/wiki/Ciprofloxacin" title="Ciprofloxacin">ciprofloxacin</a>)</li> <li><a href="/wiki/Flurothyl" title="Flurothyl">Flurothyl</a></li> <li><a href="/wiki/Furosemide" title="Furosemide">Furosemide</a></li> <li><a href="/wiki/Golexanolone" title="Golexanolone">Golexanolone</a></li> <li><a href="/wiki/Iomazenil_(123I)" class="mw-redirect" title="Iomazenil (123I)">Iomazenil (<sup>123</sup>I)</a></li> <li><a href="/wiki/IPTBO" title="IPTBO">IPTBO</a></li> <li><a href="/wiki/Isopregnanolone" title="Isopregnanolone">Isopregnanolone (sepranolone)</a></li> <li><a href="/wiki/L-655,708" title="L-655,708">L-655,708</a></li> <li><a href="/wiki/Laudanosine" title="Laudanosine">Laudanosine</a></li> <li><a href="/wiki/Lindane" title="Lindane">Lindane</a></li> <li><a href="/w/index.php?title=MaxiPost&amp;action=edit&amp;redlink=1" class="new" title="MaxiPost (page does not exist)">MaxiPost</a></li> <li><a href="/wiki/Morphine" title="Morphine">Morphine</a></li> <li><a href="/wiki/Morphine-3-glucuronide" title="Morphine-3-glucuronide">Morphine-3-glucuronide</a></li> <li><a href="/wiki/MRK-016" title="MRK-016">MRK-016</a></li> <li><a href="/wiki/Naloxone" title="Naloxone">Naloxone</a></li> <li><a href="/wiki/Naltrexone" title="Naltrexone">Naltrexone</a></li> <li><a href="/wiki/Nicardipine" title="Nicardipine">Nicardipine</a></li> <li><a href="/wiki/Nonsteroidal_antiandrogen" title="Nonsteroidal antiandrogen">Nonsteroidal antiandrogens</a> (e.g., <a href="/wiki/Apalutamide" title="Apalutamide">apalutamide</a>, <a href="/wiki/Bicalutamide" title="Bicalutamide">bicalutamide</a>, <a href="/wiki/Enzalutamide" title="Enzalutamide">enzalutamide</a>, <a href="/wiki/Flutamide" title="Flutamide">flutamide</a>, <a href="/wiki/Nilutamide" title="Nilutamide">nilutamide</a>)</li> <li><a href="/wiki/Oenanthotoxin" title="Oenanthotoxin">Oenanthotoxin</a></li> <li><a href="/wiki/Pentylenetetrazol" title="Pentylenetetrazol">Pentylenetetrazol (pentetrazol)</a></li> <li><a href="/wiki/Phenylsilatrane" title="Phenylsilatrane">Phenylsilatrane</a></li> <li><a href="/wiki/Picrotoxin" title="Picrotoxin">Picrotoxin</a> (i.e., <a href="/wiki/Picrotin" class="mw-redirect" title="Picrotin">picrotin</a>, <a href="/wiki/Picrotoxinin" class="mw-redirect" title="Picrotoxinin">picrotoxinin</a> and <a href="/wiki/Dihydropicrotoxinin" title="Dihydropicrotoxinin">dihydropicrotoxinin</a>)</li> <li><a href="/wiki/Pregnenolone_sulfate" title="Pregnenolone sulfate">Pregnenolone sulfate</a></li> <li><a href="/w/index.php?title=Propybicyphat&amp;action=edit&amp;redlink=1" class="new" title="Propybicyphat (page does not exist)">Propybicyphat</a></li> <li><a href="/wiki/PWZ-029" title="PWZ-029">PWZ-029</a></li> <li><a href="/wiki/Radequinil" title="Radequinil">Radequinil</a></li> <li><a href="/wiki/Ro_15-4513" class="mw-redirect" title="Ro 15-4513">Ro 15-4513</a></li> <li><a href="/wiki/Ro_19-4603" title="Ro 19-4603">Ro 19-4603</a></li> <li><a href="/w/index.php?title=RO4882224&amp;action=edit&amp;redlink=1" class="new" title="RO4882224 (page does not exist)">RO4882224</a></li> <li><a href="/wiki/RO4938581" class="mw-redirect" title="RO4938581">RO4938581</a></li> <li><a href="/wiki/Sarmazenil" title="Sarmazenil">Sarmazenil</a></li> <li><a href="/w/index.php?title=Salicylidene_salicylhydrazide&amp;action=edit&amp;redlink=1" class="new" title="Salicylidene salicylhydrazide (page does not exist)">SCS</a></li> <li><a href="/wiki/Suritozole" title="Suritozole">Suritozole</a></li> <li><a href="/wiki/TB-21007" title="TB-21007">TB-21007</a></li> <li><a href="/w/index.php?title=T-Butylbicycloorthobenzoate&amp;action=edit&amp;redlink=1" class="new" title="T-Butylbicycloorthobenzoate (page does not exist)">TBOB</a></li> <li><a href="/wiki/TBPS" title="TBPS">TBPS</a></li> <li><a href="/w/index.php?title=TCS-1105&amp;action=edit&amp;redlink=1" class="new" title="TCS-1105 (page does not exist)">TCS-1105</a></li> <li><a href="/wiki/Terbequinil" title="Terbequinil">Terbequinil</a></li> <li><a href="/wiki/Tetramethylenedisulfotetramine" title="Tetramethylenedisulfotetramine">TETS</a></li> <li><a href="/wiki/Thujone" title="Thujone">Thujone</a></li> <li><a href="/wiki/U-93631" title="U-93631">U-93631</a></li> <li><a href="/wiki/Zinc" title="Zinc">Zinc</a></li> <li><a href="/wiki/ZK-93426" title="ZK-93426">ZK-93426</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:5em;text-align:center"><a href="/wiki/%CE%93-Aminobutyric_acid_A-rho_receptor" class="mw-redirect" title="Γ-Aminobutyric acid A-rho receptor"><abbr title="γ-Aminobutyric acid A-rho receptor">GABA<sub>A</sub>-ρ</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 γ-Aminobutyric acid A-rho receptor</span></th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><i>Agonists:</i> <a href="/wiki/BL-1020" title="BL-1020">BL-1020</a></li> <li><a href="/wiki/(Z)-4-Amino-2-butenoic_acid" title="(Z)-4-Amino-2-butenoic acid">CACA</a></li> <li><a href="/wiki/(%2B)-cis-2-Aminomethylcyclopropane_carboxylic_acid" title="(+)-cis-2-Aminomethylcyclopropane carboxylic acid">CAMP</a></li> <li><a href="/w/index.php?title=Homohypotaurine&amp;action=edit&amp;redlink=1" class="new" title="Homohypotaurine (page does not exist)">Homohypotaurine</a></li> <li><a href="/wiki/Gamma-Aminobutyric_acid" class="mw-redirect" title="Gamma-Aminobutyric acid">GABA</a></li> <li><a href="/wiki/GABOB" class="mw-redirect" title="GABOB">GABOB</a></li> <li><a href="/wiki/Ibotenic_acid" title="Ibotenic acid">Ibotenic acid</a></li> <li><a href="/wiki/Isoguvacine" title="Isoguvacine">Isoguvacine</a></li> <li><a href="/wiki/Muscimol" title="Muscimol">Muscimol</a></li> <li><a href="/wiki/N4-Chloroacetylcytosine_arabinoside" title="N4-Chloroacetylcytosine arabinoside"><i>N</i><sup>4</sup>-Chloroacetylcytosine arabinoside</a></li> <li><a class="mw-selflink selflink">Picamilon</a></li> <li><a href="/wiki/Progabide" title="Progabide">Progabide</a></li> <li><a href="/w/index.php?title=Trans-4-Aminocrotonic_acid&amp;action=edit&amp;redlink=1" class="new" title="Trans-4-Aminocrotonic acid (page does not exist)">TACA</a></li> <li><a href="/w/index.php?title=Trans-2-(Aminomethyl)cyclopropanecarboxylic_acid&amp;action=edit&amp;redlink=1" class="new" title="Trans-2-(Aminomethyl)cyclopropanecarboxylic acid (page does not exist)">TAMP</a></li> <li><a href="/wiki/Thiomuscimol" title="Thiomuscimol">Thiomuscimol</a></li> <li><a href="/wiki/Tolgabide" title="Tolgabide">Tolgabide</a></li></ul> <ul><li><i>Positive modulators:</i> <a href="/wiki/Allopregnanolone" title="Allopregnanolone">Allopregnanolone</a></li> <li><a href="/wiki/Alphaxolone" class="mw-redirect" title="Alphaxolone">Alphaxolone</a></li> <li><a href="/wiki/Allotetrahydrodeoxycorticosterone" class="mw-redirect" title="Allotetrahydrodeoxycorticosterone">ATHDOC</a></li> <li><a href="/wiki/Lanthanide" title="Lanthanide">Lanthanides</a></li></ul> <ul><li><i>Antagonists:</i> <a href="/w/index.php?title=(S)-4-Amino-2-methylbutanoic_acid&amp;action=edit&amp;redlink=1" class="new" title="(S)-4-Amino-2-methylbutanoic acid (page does not exist)">(S)-2-MeGABA</a></li> <li><a href="/w/index.php?title=(S)-(4-Aminocyclopent-1-enyl)butylphosphinic_acid&amp;action=edit&amp;redlink=1" class="new" title="(S)-(4-Aminocyclopent-1-enyl)butylphosphinic acid (page does not exist)">(S)-4-ACPBPA</a></li> <li><a href="/w/index.php?title=(S)-4-Aminocyclopent-1-ene-1-carboxylic_acid&amp;action=edit&amp;redlink=1" class="new" title="(S)-4-Aminocyclopent-1-ene-1-carboxylic acid (page does not exist)">(S)-4-ACPCA</a></li> <li><a href="/w/index.php?title=Trans-4-Amino-2-methylbut-2-enoic_acid&amp;action=edit&amp;redlink=1" class="new" title="Trans-4-Amino-2-methylbut-2-enoic acid (page does not exist)">2-MeTACA</a></li> <li><a href="/w/index.php?title=3-Aminopropyl(methyl)phosphinic_acid&amp;action=edit&amp;redlink=1" class="new" title="3-Aminopropyl(methyl)phosphinic acid (page does not exist)">3-APMPA</a></li> <li><a href="/w/index.php?title=4-Aminocyclopent-1-enecarboxamide&amp;action=edit&amp;redlink=1" class="new" title="4-Aminocyclopent-1-enecarboxamide (page does not exist)">4-ACPAM</a></li> <li><a href="/w/index.php?title=4-Guanidinobutanoic_acid&amp;action=edit&amp;redlink=1" class="new" title="4-Guanidinobutanoic acid (page does not exist)">4-GBA</a></li> <li><a href="/w/index.php?title=Cis-(3-Aminocyclopentyl)butylphosphinic_acid&amp;action=edit&amp;redlink=1" class="new" title="Cis-(3-Aminocyclopentyl)butylphosphinic acid (page does not exist)"><i>cis</i>-3-ACPBPA</a></li> <li><a href="/w/index.php?title=CGP-36742&amp;action=edit&amp;redlink=1" class="new" title="CGP-36742 (page does not exist)">CGP-36742 (SGS-742)</a></li> <li><a href="/w/index.php?title=5-Aminovaleric_acid&amp;action=edit&amp;redlink=1" class="new" title="5-Aminovaleric acid (page does not exist)">DAVA</a></li> <li><a href="/wiki/Gabazine" title="Gabazine">Gabazine (SR-95531)</a></li> <li><a href="/wiki/Gaboxadol" title="Gaboxadol">Gaboxadol (THIP)</a></li> <li><a href="/w/index.php?title=Imidazole-4-acetic_acid&amp;action=edit&amp;redlink=1" class="new" title="Imidazole-4-acetic acid (page does not exist)">I4AA</a></li> <li><a href="/wiki/Isonipecotic_acid" title="Isonipecotic acid">Isonipecotic acid</a></li> <li><a href="/wiki/Loreclezole" title="Loreclezole">Loreclezole</a></li> <li><a href="/w/index.php?title=4-(Piperidin-4-yl)methylphosphinic_acid&amp;action=edit&amp;redlink=1" class="new" title="4-(Piperidin-4-yl)methylphosphinic acid (page does not exist)">P4MPA</a></li> <li><a href="/w/index.php?title=Piperidine-4-sulfonic_acid&amp;action=edit&amp;redlink=1" class="new" title="Piperidine-4-sulfonic acid (page does not exist)">P4S</a></li> <li><a href="/wiki/SKF-97541" class="mw-redirect" title="SKF-97541">SKF-97541</a></li> <li><a href="/w/index.php?title=SR-95318&amp;action=edit&amp;redlink=1" class="new" title="SR-95318 (page does not exist)">SR-95318</a></li> <li><a href="/w/index.php?title=SR-95813&amp;action=edit&amp;redlink=1" class="new" title="SR-95813 (page does not exist)">SR-95813</a></li> <li><a href="/wiki/(1,2,5,6-Tetrahydropyridin-4-yl)methylphosphinic_acid" title="(1,2,5,6-Tetrahydropyridin-4-yl)methylphosphinic acid">TPMPA</a></li> <li><a href="/w/index.php?title=Trans-(3-Aminocyclopentyl)butylphosphinic_acid&amp;action=edit&amp;redlink=1" class="new" title="Trans-(3-Aminocyclopentyl)butylphosphinic acid (page does not exist)"><i>trans</i>-3-ACPBPA</a></li> <li><a href="/w/index.php?title=(Z)-3-((Aminoiminomethyl)thio)prop-2-enoic_acid&amp;action=edit&amp;redlink=1" class="new" title="(Z)-3-((Aminoiminomethyl)thio)prop-2-enoic acid (page does not exist)">ZAPA</a></li></ul> <ul><li><i>Negative modulators:</i> <a href="/wiki/5%CE%B1-Dihydroprogesterone" title="5α-Dihydroprogesterone">5α-Dihydroprogesterone</a></li> <li><a href="/wiki/Bilobalide" title="Bilobalide">Bilobalide</a></li> <li><a href="/wiki/Loreclezole" title="Loreclezole">Loreclezole</a></li> <li><a href="/wiki/Picrotoxin" title="Picrotoxin">Picrotoxin</a> (<a href="/wiki/Picrotin" class="mw-redirect" title="Picrotin">picrotin</a>, <a href="/wiki/Picrotoxinin" class="mw-redirect" title="Picrotoxinin">picrotoxinin</a>)</li> <li><a href="/wiki/Pregnanolone" title="Pregnanolone">Pregnanolone</a></li> <li><a href="/wiki/ROD-188" title="ROD-188">ROD-188</a></li> <li><a href="/wiki/Tetrahydrodeoxycorticosterone" title="Tetrahydrodeoxycorticosterone">THDOC</a></li> <li><a href="/wiki/Zinc" title="Zinc">Zinc</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/Metabotropic" class="mw-redirect" title="Metabotropic">Metabotropic</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="GABABTooltip_γ-Aminobutyric_acid_B_receptor" scope="row" class="navbox-group" style="width:5em;text-align:center;"><a href="/wiki/%CE%93-Aminobutyric_acid_B_receptor" class="mw-redirect" title="Γ-Aminobutyric acid B receptor"><abbr title="γ-Aminobutyric acid B receptor">GABA<sub>B</sub></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 γ-Aminobutyric acid B receptor</span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><i>Agonists:</i> <a href="/wiki/1,4-Butanediol" title="1,4-Butanediol">1,4-Butanediol</a></li> <li><a href="/wiki/3-APPA" title="3-APPA">3-APPA</a></li> <li><a href="/wiki/4-Fluorophenibut" title="4-Fluorophenibut">4-Fluorophenibut</a></li> <li><a href="/wiki/Aceburic_acid" title="Aceburic acid">Aceburic acid</a></li> <li><a href="/wiki/Arbaclofen" class="mw-redirect" title="Arbaclofen">Arbaclofen</a></li> <li><a href="/wiki/Arbaclofen_placarbil" title="Arbaclofen placarbil">Arbaclofen placarbil</a></li> <li><a href="/wiki/Baclofen" title="Baclofen">Baclofen</a></li> <li><a href="/wiki/BL-1020" title="BL-1020">BL-1020</a></li> <li><a href="/wiki/Gamma-Aminobutyric_acid" class="mw-redirect" title="Gamma-Aminobutyric acid">GABA</a></li> <li><a href="/w/index.php?title=Gabamide&amp;action=edit&amp;redlink=1" class="new" title="Gabamide (page does not exist)">Gabamide</a></li> <li><a href="/wiki/GABOB" class="mw-redirect" title="GABOB">GABOB</a></li> <li><a href="/wiki/Gamma-Butyrolactone" class="mw-redirect" title="Gamma-Butyrolactone">GBL</a></li> <li><a href="/wiki/Gamma-Hydroxybutyric_acid" class="mw-redirect" title="Gamma-Hydroxybutyric acid">GHB</a></li> <li><a href="/wiki/%CE%93-Hydroxybutaldehyde" class="mw-redirect" title="Γ-Hydroxybutaldehyde">GHBAL</a></li> <li><a href="/wiki/Gamma-Hydroxyvaleric_acid" class="mw-redirect" title="Gamma-Hydroxyvaleric acid">GHV</a></li> <li><a href="/wiki/Gamma-Valerolactone" class="mw-redirect" title="Gamma-Valerolactone">GVL</a></li> <li><a href="/wiki/Isovaline" title="Isovaline">Isovaline</a></li> <li><a href="/wiki/Lesogaberan" title="Lesogaberan">Lesogaberan</a></li> <li><a href="/wiki/Phenibut" title="Phenibut">Phenibut</a></li> <li><a class="mw-selflink selflink">Picamilon</a></li> <li><a href="/wiki/Progabide" title="Progabide">Progabide</a></li> <li><a href="/wiki/Sodium_oxybate" title="Sodium oxybate">Sodium oxybate</a></li> <li><a href="/wiki/SKF-97,541" title="SKF-97,541">SKF-97,541</a></li> <li><a href="/wiki/SL_75102" class="mw-redirect" title="SL 75102">SL 75102</a></li> <li><a href="/wiki/Tolgabide" title="Tolgabide">Tolgabide</a></li> <li><a href="/wiki/Tolibut" title="Tolibut">Tolibut</a></li></ul> <ul><li><i>Positive modulators:</i> <a href="/wiki/ADX-71441" title="ADX-71441">ADX-71441</a></li> <li><a href="/wiki/BHF-177" title="BHF-177">BHF-177</a></li> <li><a href="/wiki/BHFF" title="BHFF">BHFF</a></li> <li><a href="/wiki/BSPP_(drug)" title="BSPP (drug)">BSPP</a></li> <li><a href="/wiki/CGP-7930" title="CGP-7930">CGP-7930</a></li> <li><a href="/w/index.php?title=CGP-13501&amp;action=edit&amp;redlink=1" class="new" title="CGP-13501 (page does not exist)">CGP-13501</a></li> <li><a href="/wiki/GS-39783" title="GS-39783">GS-39783</a></li> <li><a href="/w/index.php?title=Rac-BHFF&amp;action=edit&amp;redlink=1" class="new" title="Rac-BHFF (page does not exist)">rac-BHFF</a></li> <li><a href="/w/index.php?title=KK-92A&amp;action=edit&amp;redlink=1" class="new" title="KK-92A (page does not exist)">KK-92A</a></li></ul> <ul><li><i>Antagonists:</i> <a href="/wiki/2-Hydroxysaclofen" title="2-Hydroxysaclofen">2-Hydroxysaclofen</a></li> <li><a href="/wiki/CGP-35348" title="CGP-35348">CGP-35348</a></li> <li><a href="/w/index.php?title=CGP-46381&amp;action=edit&amp;redlink=1" class="new" title="CGP-46381 (page does not exist)">CGP-46381</a></li> <li><a href="/w/index.php?title=CGP-52432&amp;action=edit&amp;redlink=1" class="new" title="CGP-52432 (page does not exist)">CGP-52432</a></li> <li><a href="/w/index.php?title=CGP-54626&amp;action=edit&amp;redlink=1" class="new" title="CGP-54626 (page does not exist)">CGP-54626</a></li> <li><a href="/w/index.php?title=CGP-55845&amp;action=edit&amp;redlink=1" class="new" title="CGP-55845 (page does not exist)">CGP-55845</a></li> <li><a href="/w/index.php?title=CGP-64213&amp;action=edit&amp;redlink=1" class="new" title="CGP-64213 (page does not exist)">CGP-64213</a></li> <li><a href="/w/index.php?title=5-Aminovaleric_acid&amp;action=edit&amp;redlink=1" class="new" title="5-Aminovaleric acid (page does not exist)">DAVA</a></li> <li><a href="/wiki/Homotaurine" title="Homotaurine">Homotaurine (tramiprosate, 3-APS)</a></li> <li><a href="/wiki/Phaclofen" title="Phaclofen">Phaclofen</a></li> <li><a href="/wiki/Saclofen" title="Saclofen">Saclofen</a></li> <li><a href="/wiki/SCH-50911" title="SCH-50911">SCH-50911</a></li> <li><a href="/wiki/SKF-97541" class="mw-redirect" title="SKF-97541">SKF-97541</a></li></ul> <ul><li><i>Negative modulators:</i> <a href="/w/index.php?title=Compound_14&amp;action=edit&amp;redlink=1" class="new" title="Compound 14 (page does not exist)">Compound 14</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: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:GABA_metabolism_and_transport_modulators" title="Template:GABA metabolism and transport modulators">GABA metabolism/transport modulators</a> </i></dd></dl> </div></td></tr></tbody></table></div> <!-- NewPP limit report Parsed by mw‐web.eqiad.main‐5dc468848‐2gnwm Cached time: 20241122141836 Cache expiry: 2592000 Reduced expiry: false Complications: [vary‐revision‐sha1, show‐toc] CPU time usage: 0.658 seconds Real time usage: 0.945 seconds Preprocessor visited node count: 5632/1000000 Post‐expand include size: 153053/2097152 bytes Template argument size: 5772/2097152 bytes Highest expansion depth: 19/100 Expensive parser function count: 2/500 Unstrip 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