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Ginkgolide - Wikipedia
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class="vector-toc-list"> <li id="toc-Ginkgolide_B" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Ginkgolide_B"> <div class="vector-toc-text"> <span class="vector-toc-numb">1.1</span> <span>Ginkgolide B</span> </div> </a> <ul id="toc-Ginkgolide_B-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Background" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Background"> <div class="vector-toc-text"> <span class="vector-toc-numb">2</span> <span>Background</span> </div> </a> <ul id="toc-Background-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Potential_applications" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Potential_applications"> <div class="vector-toc-text"> <span class="vector-toc-numb">3</span> <span>Potential applications</span> </div> </a> <ul id="toc-Potential_applications-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Spectroscopic_studies_for_the_elucidation_of_the_individual_structures_for_the_ginkgolides" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Spectroscopic_studies_for_the_elucidation_of_the_individual_structures_for_the_ginkgolides"> <div class="vector-toc-text"> <span class="vector-toc-numb">4</span> <span>Spectroscopic studies for the elucidation of the individual structures for the ginkgolides</span> </div> </a> <ul id="toc-Spectroscopic_studies_for_the_elucidation_of_the_individual_structures_for_the_ginkgolides-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Biosynthesis_of_ginkgolide_B" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Biosynthesis_of_ginkgolide_B"> <div class="vector-toc-text"> <span class="vector-toc-numb">5</span> <span>Biosynthesis of ginkgolide B</span> </div> </a> <ul id="toc-Biosynthesis_of_ginkgolide_B-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-See_also" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#See_also"> <div class="vector-toc-text"> <span class="vector-toc-numb">6</span> <span>See also</span> </div> </a> <ul id="toc-See_also-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-References" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#References"> <div class="vector-toc-text"> <span class="vector-toc-numb">7</span> <span>References</span> </div> </a> <ul id="toc-References-sublist" class="vector-toc-list"> </ul> </li> </ul> </div> </div> </nav> </div> </div> <div class="mw-content-container"> <main id="content" class="mw-body"> <header class="mw-body-header vector-page-titlebar"> <nav aria-label="Contents" class="vector-toc-landmark"> <div id="vector-page-titlebar-toc" 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href="https://fa.wikipedia.org/wiki/%D8%AC%DB%8C%D9%86%DA%A9%E2%80%8C%DA%AF%D9%88%D9%84%DB%8C%D8%AF" title="جینکگولید – Persian" lang="fa" hreflang="fa" data-title="جینکگولید" 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/Ginkgolide" title="Ginkgolide – French" lang="fr" hreflang="fr" data-title="Ginkgolide" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target"><span>Français</span></a></li><li class="interlanguage-link interwiki-ja mw-list-item"><a href="https://ja.wikipedia.org/wiki/%E3%82%AE%E3%83%B3%E3%82%B3%E3%83%A9%E3%82%A4%E3%83%89" title="ギンコライド – Japanese" lang="ja" hreflang="ja" data-title="ギンコライド" 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-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/Ginkgolid" title="Ginkgolid – Serbian" lang="sr" hreflang="sr" data-title="Ginkgolid" 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/Ginkgolid" title="Ginkgolid – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Ginkgolid" 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-tr mw-list-item"><a href="https://tr.wikipedia.org/wiki/Ginkgolid" title="Ginkgolid – Turkish" lang="tr" hreflang="tr" data-title="Ginkgolid" data-language-autonym="Türkçe" data-language-local-name="Turkish" class="interlanguage-link-target"><span>Türkçe</span></a></li><li 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src="//upload.wikimedia.org/wikipedia/commons/thumb/2/25/ACSformatstructureofginkolideb.svg/220px-ACSformatstructureofginkolideb.svg.png" decoding="async" width="220" height="231" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/2/25/ACSformatstructureofginkolideb.svg/330px-ACSformatstructureofginkolideb.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/2/25/ACSformatstructureofginkolideb.svg/440px-ACSformatstructureofginkolideb.svg.png 2x" data-file-width="512" data-file-height="538" /></a><figcaption>Chemical structure of gingkolide B</figcaption></figure> <p><b>Ginkgolides</b> are biologically active <a href="/wiki/Terpenoid" title="Terpenoid">terpenic</a> <a href="/wiki/Lactone" title="Lactone">lactones</a> present in <i><a href="/wiki/Ginkgo_biloba" title="Ginkgo biloba">Ginkgo biloba</a></i>. They are <a href="/wiki/Diterpenoid" class="mw-redirect" title="Diterpenoid">diterpenoids</a> with 20-carbon skeletons, which are biosynthesized from <a href="/wiki/Geranylgeranyl_pyrophosphate" title="Geranylgeranyl pyrophosphate">geranylgeranyl pyrophosphate</a>.<sup id="cite_ref-1" class="reference"><a href="#cite_note-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Examples">Examples</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Ginkgolide&action=edit&section=1" title="Edit section: Examples"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure class="mw-default-size mw-halign-left" typeof="mw:File/Thumb"><a href="/wiki/File:Ginkgolides_structure.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/1/1b/Ginkgolides_structure.png" decoding="async" width="162" height="125" class="mw-file-element" data-file-width="162" data-file-height="125" /></a><figcaption>Chemical structure of ginkgolides</figcaption></figure> <table class="wikitable"> <caption>Ginkgolides </caption> <tbody><tr> <td><b>Name</b></td> <td><b>R<sup>1</sup></b></td> <td><b>R<sup>2</sup></b></td> <td><b>R<sup>3</sup></b> </td></tr> <tr> <td>Ginkgolide A</td> <td>OH</td> <td>H</td> <td>H </td></tr> <tr> <td>Ginkgolide B</td> <td>OH</td> <td>OH</td> <td>H </td></tr> <tr> <td>Ginkgolide C</td> <td>OH</td> <td>OH</td> <td>OH </td></tr> <tr> <td>Ginkgolide J</td> <td>OH</td> <td>H</td> <td>OH </td></tr> <tr> <td>Ginkgolide M</td> <td>H</td> <td>OH</td> <td>OH </td></tr></tbody></table> <div style="clear:left;" class=""></div> <div class="mw-heading mw-heading3"><h3 id="Ginkgolide_B">Ginkgolide B</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Ginkgolide&action=edit&section=2" title="Edit section: Ginkgolide B"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Ginkgolide B, specifically, is a diterpenoid trilactone with six five-membered rings. It contains a spiro[4,4]-nonane carbocyclic ring, a tetrahydrofuran ring, and a very specific <a href="/wiki/Tert-butyl" class="mw-redirect" title="Tert-butyl">tert-butyl</a> group at one of the rings (Figure 1). The class of ginkgolides was first isolated from the tree <i><a href="/wiki/Ginkgo_biloba" title="Ginkgo biloba">Ginkgo biloba</a></i> in 1932.<sup id="cite_ref-PMID_15038209_2-0" class="reference"><a href="#cite_note-PMID_15038209-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> Structural elucidation was accomplished in 1967 by Maruyama <i>et al</i>.<sup id="cite_ref-autogenerated1_3-0" class="reference"><a href="#cite_note-autogenerated1-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Background">Background</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Ginkgolide&action=edit&section=3" title="Edit section: Background"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>It is extracted from the root bark and leaves of the <i><a href="/wiki/Ginkgo_biloba" title="Ginkgo biloba">Ginkgo biloba</a></i> (<i><span title="Mandarin Chinese-language text"><i lang="cmn">ginkyo</i></span></i> meaning "silver apricot") tree found native in China. It is marketed to other countries that include Korea, France, the United States, etc. for the drug and clinical properties of the extracts. Present in the tree is less than 0.1 to 0.25% of ginkgolide B, the most abundant being ginkgolide A.<sup id="cite_ref-Dewick_4-0" class="reference"><a href="#cite_note-Dewick-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Potential_applications">Potential applications</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Ginkgolide&action=edit&section=4" title="Edit section: Potential applications"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>This class of molecules has been studied for its potential to act as a <a href="/wiki/Platelet-activating_factor_receptor" title="Platelet-activating factor receptor">platelet-activating factor receptor</a> <a href="/wiki/Receptor_antagonist" title="Receptor antagonist">antagonist</a>.<sup id="cite_ref-PMID_15038209_2-1" class="reference"><a href="#cite_note-PMID_15038209-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Zen_47–52_5-0" class="reference"><a href="#cite_note-Zen_47–52-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> </p><p>Ginkgolide B has been investigated for its potential to reducing migraine frequency.<sup id="cite_ref-Usai_6-0" class="reference"><a href="#cite_note-Usai-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> </p><p>Ginkgolide B is also used in treatment for <a href="/wiki/Cerebrovascular_disease" title="Cerebrovascular disease">cerebrovascular disease</a>. Research has also proven that ginkgolide B can also treat migraines in young ages.<sup id="cite_ref-PMID_15038209_2-2" class="reference"><a href="#cite_note-PMID_15038209-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Dewick_4-1" class="reference"><a href="#cite_note-Dewick-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Usai_6-1" class="reference"><a href="#cite_note-Usai-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> The literature indicates that ginkgolide B functions as a selective antagonist of <a href="/wiki/Glycine_receptors" class="mw-redirect" title="Glycine receptors">glycine receptors</a> based on noncompetitive inhibition for the neurological system that this compound performs.<sup id="cite_ref-Zen_47–52_5-1" class="reference"><a href="#cite_note-Zen_47–52-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Spectroscopic_studies_for_the_elucidation_of_the_individual_structures_for_the_ginkgolides">Spectroscopic studies for the elucidation of the individual structures for the ginkgolides</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Ginkgolide&action=edit&section=5" title="Edit section: Spectroscopic studies for the elucidation of the individual structures for the ginkgolides"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Ginkolides A - C were isolated from a large scale <a href="/wiki/Methanol" title="Methanol">methanolic</a> extraction followed by liquid-liquid partitions, column chromatography and repeated crystallizations. The molecular formulas were determined by high resolution mass spectrometry, and the overall structures by IR and NMR spectroscopic analysis and extensive derivitization techniques. </p> <div class="mw-heading mw-heading2"><h2 id="Biosynthesis_of_ginkgolide_B">Biosynthesis of ginkgolide B</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Ginkgolide&action=edit&section=6" title="Edit section: Biosynthesis of ginkgolide B"><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:ACSformantbiosynthesisofginkgolideb.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/1/1b/ACSformantbiosynthesisofginkgolideb.svg/220px-ACSformantbiosynthesisofginkgolideb.svg.png" decoding="async" width="220" height="219" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/1/1b/ACSformantbiosynthesisofginkgolideb.svg/330px-ACSformantbiosynthesisofginkgolideb.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/1/1b/ACSformantbiosynthesisofginkgolideb.svg/440px-ACSformantbiosynthesisofginkgolideb.svg.png 2x" data-file-width="535" data-file-height="533" /></a><figcaption>The biosynthesis of ginkgolide B</figcaption></figure> <p>While researchers have published chemical pathways to make this molecule, most of the designed syntheses were too complex and produced little of the actual material to run full analyses.<sup id="cite_ref-PMID_15038209_2-3" class="reference"><a href="#cite_note-PMID_15038209-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> Therefore, studying the biosynthesis of the molecule is preferable. </p><p>Most of the natural product terpenoids start with <a href="/wiki/Isopentenyl_diphosphate" class="mw-redirect" title="Isopentenyl diphosphate">isopentenyl diphosphate</a> synthesized by the <a href="/wiki/MEP_pathway" class="mw-redirect" title="MEP pathway">MEP pathway</a>. This pathway also generates <a href="/wiki/Dimethylallyl_diphosphate" class="mw-redirect" title="Dimethylallyl diphosphate">dimethylallyl diphosphate</a>, from <a href="/wiki/Pyruvate" class="mw-redirect" title="Pyruvate">pyruvate</a> and D-glyercaldehyde 3-phosphate (GAP). When coupled together, they form one molecule of <a href="/wiki/Geranylgeranyl_diphosphate" class="mw-redirect" title="Geranylgeranyl diphosphate">geranylgeranyl diphosphate</a> with geranylgeranyl diphosphate synthase. </p><p>A molecule of <a href="/wiki/GGPP" class="mw-redirect" title="GGPP">GGPP</a> generates (<b>1</b>) (+)-copalyl in the presence of <a href="/wiki/Levopimaradiene_synthase" title="Levopimaradiene synthase">levopimaradiene synthase</a>. (<b>a</b>) Then (<b>1</b>) loses its OPP group catalyzed by this same synthase, performing an intramolecular allylic cyclization with the two <a href="/wiki/Alkene" title="Alkene">alkenes</a>, to form (<b>2</b>) the sandaracopimarenyl cation. (<b>b</b>) This cation then undergoes an internal cyclization to stabilize the <a href="/wiki/Carbocation" title="Carbocation">carbocation</a> in the ring by proton transfer to form (<b>3</b>) intermediate. (<b>c</b>) By doing this, the molecule sets itself up for a methyl migration to stabilize that secondary cation and generate that tertiary <a href="/wiki/Carbocation" title="Carbocation">carbocation</a> at (<b>4</b>). (<b>d</b>) This induces a loss of proton to get (<b>5</b>) levopimaradiene. (<b>e</b>) With oxidation, a loss of a proton to form an aromatic ring generates (<b>6</b>) <a href="/wiki/Abietatriene" title="Abietatriene">abietatriene</a>. (<b>g</b>) This newly formed <a href="/wiki/Abietatriene" title="Abietatriene">abietatriene</a> undergoes a 1,2-alkyl shift to break the 6-membered ring into (<b>7</b>) with a five-membered ring (more favorable). (<b>h</b>) Another 1,2-alkyl shift takes place at the same time a ring cleavage takes place to generate (<b>8</b>). (<b>i</b>) Oxidation at all the positions with <a href="/wiki/Alkene" title="Alkene">alkenes</a> generates (<b>9</b>) intermediate which then undergoes <a href="/wiki/Cyclic_compound" title="Cyclic compound">ring closures</a> featuring one <a href="/wiki/Hemiacetal" title="Hemiacetal">hemiacetal</a> and all three <a href="/wiki/Lactones" class="mw-redirect" title="Lactones">lactones</a> to get ginkgolide B at (<b>10</b>).<sup id="cite_ref-Dewick_4-2" class="reference"><a href="#cite_note-Dewick-4"><span class="cite-bracket">[</span>4<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=Ginkgolide&action=edit&section=7" title="Edit section: See also"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a href="/wiki/Bilobalide" title="Bilobalide">Bilobalide</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=Ginkgolide&action=edit&section=8" 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"><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 id="CITEREFNiels_H._AndersenNiels_Johan_ChristensenPeter_R._LassenTeresa_B.N._Freedman2010" class="citation journal cs1">Niels H. Andersen; Niels Johan Christensen; Peter R. Lassen; Teresa B.N. Freedman; Laurence A. Nafie; Kristian Strømgaard; Lars Hemmingsen (February 2010). <a rel="nofollow" class="external text" href="http://orbit.dtu.dk/en/publications/structure-and-absolute-configuration-of-ginkgolide-b-characterized-by-ir-and-vcd-spectroscopy(c6c07bd0-24b7-4b5c-9f1f-71f59a26a479).html">"Structure and absolute configuration of ginkgolide B characterized by IR- and VCD spectroscopy"</a>. <i>Chirality</i>. <b>22</b> (2): 217–223. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2Fchir.20730">10.1002/chir.20730</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/19455619">19455619</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Chirality&rft.atitle=Structure+and+absolute+configuration+of+ginkgolide+B+characterized+by+IR-+and+VCD+spectroscopy&rft.volume=22&rft.issue=2&rft.pages=217-223&rft.date=2010-02&rft_id=info%3Adoi%2F10.1002%2Fchir.20730&rft_id=info%3Apmid%2F19455619&rft.au=Niels+H.+Andersen&rft.au=Niels+Johan+Christensen&rft.au=Peter+R.+Lassen&rft.au=Teresa+B.N.+Freedman&rft.au=Laurence+A.+Nafie&rft.au=Kristian+Str%C3%B8mgaard&rft.au=Lars+Hemmingsen&rft_id=http%3A%2F%2Forbit.dtu.dk%2Fen%2Fpublications%2Fstructure-and-absolute-configuration-of-ginkgolide-b-characterized-by-ir-and-vcd-spectroscopy%28c6c07bd0-24b7-4b5c-9f1f-71f59a26a479%29.html&rfr_id=info%3Asid%2Fen.wikipedia.org%3AGinkgolide" class="Z3988"></span></span> </li> <li id="cite_note-PMID_15038209-2"><span class="mw-cite-backlink">^ <a href="#cite_ref-PMID_15038209_2-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-PMID_15038209_2-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-PMID_15038209_2-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-PMID_15038209_2-3"><sup><i><b>d</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFStromgaardNakanishi,_K.2004" class="citation journal cs1">Stromgaard, K.; Nakanishi, K. 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Isolation and characterization of the various groups". <i>Tetrahedron Letters</i>. <b>8</b> (4): 299–302. <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%2FS0040-4039%2800%2971538-3">10.1016/S0040-4039(00)71538-3</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Tetrahedron+Letters&rft.atitle=The+ginkgolides.+I.+Isolation+and+characterization+of+the+various+groups&rft.volume=8&rft.issue=4&rft.pages=299-302&rft.date=1967&rft_id=info%3Adoi%2F10.1016%2FS0040-4039%2800%2971538-3&rft.aulast=Maruyama&rft.aufirst=M.&rft.au=Terahara%2C+A.&rft.au=Itagaki%2C+Y.&rft.au=Nakanishi%2C+K.&rfr_id=info%3Asid%2Fen.wikipedia.org%3AGinkgolide" class="Z3988"></span></span> </li> <li id="cite_note-Dewick-4"><span class="mw-cite-backlink">^ <a href="#cite_ref-Dewick_4-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Dewick_4-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-Dewick_4-2"><sup><i><b>c</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFDewick2012" class="citation book cs1">Dewick, P.M. 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(2011). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3084934">"Gingkolide B as migraine preventive treatment in young age: results at 1-year follow-up"</a>. <i>Neurol. Sci</i>. <b>32</b> (Suppl 1): SI97–SI99. <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%2Fs10072-011-0522-7">10.1007/s10072-011-0522-7</a>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3084934">3084934</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/21533745">21533745</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Neurol.+Sci.&rft.atitle=Gingkolide+B+as+migraine+preventive+treatment+in+young+age%3A+results+at+1-year+follow-up&rft.volume=32&rft.issue=Suppl+1&rft.pages=SI97-SI99&rft.date=2011&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC3084934%23id-name%3DPMC&rft_id=info%3Apmid%2F21533745&rft_id=info%3Adoi%2F10.1007%2Fs10072-011-0522-7&rft.aulast=Usai&rft.aufirst=S.&rft.au=Grazzi%2C+L.&rft.au=Bussone%2C+G.&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC3084934&rfr_id=info%3Asid%2Fen.wikipedia.org%3AGinkgolide" class="Z3988"></span></span> </li> </ol></div></div> <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 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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="Glycine_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 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href="/wiki/Template:Glycine_receptor_modulators" title="Template:Glycine receptor modulators"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Glycine_receptor_modulators" title="Template talk:Glycine receptor modulators"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Glycine_receptor_modulators" title="Special:EditPage/Template:Glycine receptor modulators"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Glycine_receptor_modulators" style="font-size:114%;margin:0 4em"><a href="/wiki/Glycine_receptor" title="Glycine receptor">Glycine receptor</a> <a href="/wiki/Receptor_modulator" title="Receptor modulator">modulators</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Receptor_(biochemistry)" title="Receptor (biochemistry)">Receptor</a><br /><small>(<a href="/wiki/Ligand_(biochemistry)" title="Ligand (biochemistry)">ligands</a>)</small></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:4em;;text-align:center;"><a href="/wiki/Glycine_receptor" title="Glycine receptor"><abbr title="Glycine receptor">GlyR</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Glycine receptor</span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><b>Agonists:</b> <a href="/wiki/%CE%92-Alanine" title="Β-Alanine">β-Alanine</a></li> <li><a href="/wiki/Beta-Aminobutyric_acid" class="mw-redirect" title="Beta-Aminobutyric acid">β-ABA (BABA)</a></li> <li><a href="/w/index.php?title=%CE%92-Aminoisobutyric_acid&action=edit&redlink=1" class="new" title="Β-Aminoisobutyric acid (page does not exist)">β-AIBA</a></li> <li><a href="/wiki/Caesium" title="Caesium">Caesium</a></li> <li><a href="/wiki/Alanine" title="Alanine"><small>D</small>-Alanine</a></li> <li><a href="/wiki/Serine" title="Serine"><small>D</small>-Serine</a></li> <li><a href="/wiki/Gamma-Aminobutyric_acid" class="mw-redirect" title="Gamma-Aminobutyric acid">GABA</a></li> <li><a href="/wiki/Glycine" title="Glycine">Glycine</a></li> <li><a href="/wiki/Hypotaurine" title="Hypotaurine">Hypotaurine</a></li> <li><a href="/wiki/Ivermectin" title="Ivermectin">Ivermectin</a></li> <li><a href="/wiki/Alanine" title="Alanine"><small>L</small>-Alanine</a></li> <li><a href="/wiki/Proline" title="Proline"><small>L</small>-Proline</a></li> <li><a href="/wiki/Serine" title="Serine"><small>L</small>-Serine</a></li> <li><a href="/wiki/Threonine" title="Threonine"><small>L</small>-Threonine</a></li> <li><a href="/w/index.php?title=MDL-27531&action=edit&redlink=1" class="new" title="MDL-27531 (page does not exist)">MDL-27531</a></li> <li><a href="/wiki/Milacemide" title="Milacemide">Milacemide</a></li> <li><a href="/wiki/Picolinic_acid" title="Picolinic acid">Picolinic acid</a></li> <li><a href="/wiki/Propofol" title="Propofol">Propofol</a></li> <li><a href="/wiki/Quisqualamine" title="Quisqualamine">Quisqualamine</a></li> <li><a href="/wiki/Sarcosine" title="Sarcosine">Sarcosine</a></li> <li><a href="/wiki/Taurine" title="Taurine">Taurine</a></li></ul> <ul><li><b>Positive modulators:</b> <a href="/wiki/Alcohol_(chemistry)" title="Alcohol (chemistry)">Alcohols</a> (e.g., <a href="/w/index.php?title=Brometone&action=edit&redlink=1" class="new" title="Brometone (page does not exist)">brometone</a>, <a href="/wiki/Chlorobutanol" title="Chlorobutanol">chlorobutanol (chloretone)</a>, <a href="/wiki/Alcohol_(drug)" title="Alcohol (drug)">ethanol (alcohol)</a>, <a href="/wiki/Tert-Butyl_alcohol" title="Tert-Butyl alcohol"><i>tert</i>-butanol (2M2P)</a>, <a href="/wiki/Tribromoethanol" title="Tribromoethanol">tribromoethanol</a>, <a href="/wiki/Trichloroethanol" class="mw-redirect" title="Trichloroethanol">trichloroethanol</a>, <a href="/wiki/Trifluoroethanol" class="mw-redirect" title="Trifluoroethanol">trifluoroethanol</a>)</li> <li><a href="/wiki/Alkylbenzene_sulfonate" title="Alkylbenzene sulfonate">Alkylbenzene sulfonate</a></li> <li><a href="/wiki/Anandamide" title="Anandamide">Anandamide</a></li> <li><a href="/wiki/Barbiturate" title="Barbiturate">Barbiturates</a> (e.g., <a href="/wiki/Pentobarbital" title="Pentobarbital">pentobarbital</a>, <a href="/wiki/Sodium_thiopental" title="Sodium thiopental">sodium thiopental</a>)</li> <li><a href="/wiki/Chlormethiazole" class="mw-redirect" title="Chlormethiazole">Chlormethiazole</a></li> <li><a href="/w/index.php?title=D12-116&action=edit&redlink=1" class="new" title="D12-116 (page does not exist)">D12-116</a></li> <li><a href="/wiki/Dihydropyridine" class="mw-redirect" title="Dihydropyridine">Dihydropyridines</a> (e.g., <a href="/wiki/Nicardipine" title="Nicardipine">nicardipine</a>)</li> <li><a href="/wiki/Etomidate" title="Etomidate">Etomidate</a></li> <li><a href="/wiki/Ginseng" title="Ginseng">Ginseng</a> constituents (e.g., <a href="/wiki/Ginsenoside" title="Ginsenoside">ginsenosides</a> (e.g., <a href="/w/index.php?title=Ginsenoside-Rf&action=edit&redlink=1" class="new" title="Ginsenoside-Rf (page does not exist)">ginsenoside-Rf</a>))</li> <li><a href="/wiki/Glutamic_acid" title="Glutamic acid">Glutamic acid (glutamate)</a></li> <li><a href="/wiki/Ivermectin" title="Ivermectin">Ivermectin</a></li> <li><a href="/wiki/Ketamine" title="Ketamine">Ketamine</a></li> <li><a href="/wiki/Neuroactive_steroid" class="mw-redirect" title="Neuroactive steroid">Neuroactive steroids</a> (e.g., <a href="/wiki/Alfaxolone" class="mw-redirect" title="Alfaxolone">alfaxolone</a>, <a href="/wiki/Pregnenolone" title="Pregnenolone">pregnenolone (eltanolone)</a>, <a href="/wiki/Pregnenolone_acetate" title="Pregnenolone acetate">pregnenolone acetate</a>, <a href="/wiki/Minaxolone" title="Minaxolone">minaxolone</a>, <a href="/wiki/ORG-20599" title="ORG-20599">ORG-20599</a>)</li> <li><a href="/wiki/Nitrous_oxide" title="Nitrous oxide">Nitrous oxide</a></li> <li><a href="/wiki/Penicillin_G" class="mw-redirect" title="Penicillin G">Penicillin G</a></li> <li><a href="/wiki/Propofol" title="Propofol">Propofol</a></li> <li><a href="/wiki/Tamoxifen" title="Tamoxifen">Tamoxifen</a></li> <li><a href="/wiki/Tetrahydrocannabinol" title="Tetrahydrocannabinol">Tetrahydrocannabinol</a></li> <li><a href="/wiki/Triclofos" title="Triclofos">Triclofos</a></li> <li><a href="/w/index.php?title=Tropeine&action=edit&redlink=1" class="new" title="Tropeine (page does not exist)">Tropeines</a> (e.g., <a href="/wiki/Atropine" title="Atropine">atropine</a>, <a href="/wiki/Bemesetron" title="Bemesetron">bemesetron</a>, <a href="/wiki/Cocaine" title="Cocaine">cocaine</a>, <a href="/w/index.php?title=LY-278584&action=edit&redlink=1" class="new" title="LY-278584 (page does not exist)">LY-278584</a>, <a href="/wiki/Tropisetron" title="Tropisetron">tropisetron</a>, <a href="/wiki/Zatosetron" title="Zatosetron">zatosetron</a>)</li> <li><a href="/wiki/Volatility_(chemistry)" title="Volatility (chemistry)">Volatiles</a>/<a href="/wiki/Gas" title="Gas">gases</a> (e.g., <a href="/wiki/Chloral_hydrate" title="Chloral hydrate">chloral hydrate</a>, <a href="/wiki/Chloroform" title="Chloroform">chloroform</a>, <a href="/wiki/Desflurane" title="Desflurane">desflurane</a>, <a href="/wiki/Diethyl_ether" title="Diethyl ether">diethyl ether (ether)</a>, <a href="/wiki/Enflurane" title="Enflurane">enflurane</a>, <a href="/wiki/Halothane" title="Halothane">halothane</a>, <a href="/wiki/Isoflurane" title="Isoflurane">isoflurane</a>, <a href="/wiki/Methoxyflurane" title="Methoxyflurane">methoxyflurane</a>, <a href="/wiki/Sevoflurane" title="Sevoflurane">sevoflurane</a>, <a href="/wiki/Toluene" title="Toluene">toluene</a>, <a href="/wiki/1,1,1-trichloroethane" class="mw-redirect" title="1,1,1-trichloroethane">trichloroethane (methyl chloroform)</a>, <a href="/wiki/Trichloroethylene" title="Trichloroethylene">trichloroethylene</a>)</li> <li><a href="/wiki/Xenon" title="Xenon">Xenon</a></li> <li><a href="/wiki/Zinc" title="Zinc">Zinc</a></li></ul> <ul><li><b>Antagonists:</b> <a href="/w/index.php?title=2-Aminostrychnine&action=edit&redlink=1" class="new" title="2-Aminostrychnine (page does not exist)">2-Aminostrychnine</a></li> <li><a href="/w/index.php?title=2-Nitrostrychnine&action=edit&redlink=1" class="new" title="2-Nitrostrychnine (page does not exist)">2-Nitrostrychnine</a></li> <li><a href="/w/index.php?title=4-Phenyl-4-formyl-N-methylpiperidine&action=edit&redlink=1" class="new" title="4-Phenyl-4-formyl-N-methylpiperidine (page does not exist)">4-Phenyl-4-formyl-N-methylpiperidine</a></li> <li><a href="/w/index.php?title=%CE%91-Ethyl-%CE%B1-methyl-%CE%B3-thiobutyrolactone&action=edit&redlink=1" class="new" title="Α-Ethyl-α-methyl-γ-thiobutyrolactone (page does not exist)">αEMBTL</a></li> <li><a href="/wiki/Bicuculline" title="Bicuculline">Bicuculline</a></li> <li><a href="/wiki/Brucine" title="Brucine">Brucine</a></li> <li><a href="/wiki/Cacotheline" title="Cacotheline">Cacotheline</a></li> <li><a href="/wiki/Caffeine" title="Caffeine">Caffeine</a></li> <li><a href="/wiki/Colchicine" title="Colchicine">Colchicine</a></li> <li><a href="/wiki/Colubrine" class="mw-redirect" title="Colubrine">Colubrine</a></li> <li><a href="/w/index.php?title=Cyanotriphenylborate&action=edit&redlink=1" class="new" title="Cyanotriphenylborate (page does not exist)">Cyanotriphenylborate</a></li> <li><a href="/wiki/Dendrobine" title="Dendrobine">Dendrobine</a></li> <li><a href="/w/index.php?title=Diaboline&action=edit&redlink=1" class="new" title="Diaboline (page does not exist)">Diaboline</a></li> <li><a href="/wiki/Endocannabinoid" class="mw-redirect" title="Endocannabinoid">Endocannabinoids</a> (e.g., <a href="/wiki/2-arachidonylglycerol" class="mw-redirect" title="2-arachidonylglycerol">2-AG</a>, <a href="/wiki/Anandamide" title="Anandamide">anandamide (AEA)</a>)</li> <li><a href="/wiki/Gaboxadol" title="Gaboxadol">Gaboxadol (THIP)</a></li> <li><a href="/wiki/Gelsemine" title="Gelsemine">Gelsemine</a></li> <li><a href="/w/index.php?title=Iso-THAZ&action=edit&redlink=1" class="new" title="Iso-THAZ (page does not exist)">iso-THAZ</a></li> <li><a href="/wiki/Isobutyric_acid" title="Isobutyric acid">Isobutyric acid</a></li> <li><a href="/wiki/Isonipecotic_acid" title="Isonipecotic acid">Isonipecotic acid</a></li> <li><a href="/w/index.php?title=Isostrychnine&action=edit&redlink=1" class="new" title="Isostrychnine (page does not exist)">Isostrychnine</a></li> <li><a href="/wiki/Laudanosine" title="Laudanosine">Laudanosine</a></li> <li><a href="/w/index.php?title=N-Methylbicuculline&action=edit&redlink=1" class="new" title="N-Methylbicuculline (page does not exist)">N-Methylbicuculline</a></li> <li><a href="/w/index.php?title=N-Methylstrychnine&action=edit&redlink=1" class="new" title="N-Methylstrychnine (page does not exist)">N-Methylstrychnine</a></li> <li><a href="/w/index.php?title=N,N-Dimethylmuscimol&action=edit&redlink=1" class="new" title="N,N-Dimethylmuscimol (page does not exist)">N,N-Dimethylmuscimol</a></li> <li><a href="/wiki/Nipecotic_acid" title="Nipecotic acid">Nipecotic acid</a></li> <li><a href="/wiki/Pitrazepin" title="Pitrazepin">Pitrazepin</a></li> <li><a href="/w/index.php?title=Pseudostrychnine&action=edit&redlink=1" class="new" title="Pseudostrychnine (page does not exist)">Pseudostrychnine</a></li> <li><a href="/wiki/Quinoline" title="Quinoline">Quinolines</a> (e.g., <a href="/w/index.php?title=4-hydroxyquinoline&action=edit&redlink=1" class="new" title="4-hydroxyquinoline (page does not exist)">4-hydroxyquinoline</a>, <a href="/w/index.php?title=4-hydroxyquinoline-3-carboxylic_acid&action=edit&redlink=1" class="new" title="4-hydroxyquinoline-3-carboxylic acid (page does not exist)">4-hydroxyquinoline-3-carboxylic acid</a>, <a href="/w/index.php?title=5,7-dichloro-4-hydroxyquinoline-3-carboxylic_acid&action=edit&redlink=1" class="new" title="5,7-dichloro-4-hydroxyquinoline-3-carboxylic acid (page does not exist)">5,7-CIQA</a>, <a href="/w/index.php?title=7-chloro-4-hydroxyquinoline&action=edit&redlink=1" class="new" title="7-chloro-4-hydroxyquinoline (page does not exist)">7-CIQ</a>, <a href="/w/index.php?title=7-trifluoromethyl-4-hydroxyquinoline&action=edit&redlink=1" class="new" title="7-trifluoromethyl-4-hydroxyquinoline (page does not exist)">7-TFQ</a>, <a href="/w/index.php?title=7-trifluoromethyl-4-hydroxyquinoline-3-carboxylic_acid&action=edit&redlink=1" class="new" title="7-trifluoromethyl-4-hydroxyquinoline-3-carboxylic acid (page does not exist)">7-TFQA</a>)</li> <li><a href="/w/index.php?title=RU-5135&action=edit&redlink=1" class="new" title="RU-5135 (page does not exist)">RU-5135</a></li> <li><a href="/wiki/Sinomenine" title="Sinomenine">Sinomenine</a></li> <li><a href="/wiki/Strychnine" title="Strychnine">Strychnine</a></li> <li><a href="/wiki/Thiocolchicoside" title="Thiocolchicoside">Thiocolchicoside</a></li> <li><a href="/wiki/Tutin_(toxin)" title="Tutin (toxin)">Tutin</a></li></ul> <ul><li><b>Negative modulators:</b> <a href="/wiki/Amiloride" title="Amiloride">Amiloride</a></li> <li><a href="/wiki/Benzodiazepine" title="Benzodiazepine">Benzodiazepines</a> (e.g., <a href="/wiki/Bromazepam" title="Bromazepam">bromazepam</a>, <a href="/wiki/Clonazepam" title="Clonazepam">clonazepam</a>, <a href="/wiki/Diazepam" title="Diazepam">diazepam</a>, <a href="/wiki/Flunitrazepam" title="Flunitrazepam">flunitrazepam</a>, <a href="/wiki/Flurazepam" title="Flurazepam">flurazepam</a>)</li> <li><a href="/wiki/Corymine" title="Corymine">Corymine</a></li> <li><a href="/w/index.php?title=Cyanotriphenylborate&action=edit&redlink=1" class="new" title="Cyanotriphenylborate (page does not exist)">Cyanotriphenylborate</a></li> <li><a href="/wiki/Daidzein" title="Daidzein">Daidzein</a></li> <li><a href="/wiki/Dihydropyridine" class="mw-redirect" title="Dihydropyridine">Dihydropyridines</a> (e.g., <a href="/wiki/Nicardipine" title="Nicardipine">nicardipine</a>, <a href="/wiki/Nifedipine" title="Nifedipine">nifedipine</a>, <a href="/wiki/Nitrendipine" title="Nitrendipine">nitrendipine</a>)</li> <li><a href="/wiki/Furosemide" title="Furosemide">Furosemide</a></li> <li><a href="/wiki/Genistein" title="Genistein">Genistein</a></li> <li><a href="/wiki/Ginkgo_biloba" title="Ginkgo biloba">Ginkgo</a> constituents (e.g., <a href="/wiki/Bilobalide" title="Bilobalide">bilobalide</a>, <a class="mw-selflink selflink">ginkgolides</a> (e.g., <a href="/w/index.php?title=Ginkgolide_A&action=edit&redlink=1" class="new" title="Ginkgolide A (page does not exist)">ginkgolide A</a>, <a href="/wiki/Ginkgolide_B" class="mw-redirect" title="Ginkgolide B">ginkgolide B</a>, <a href="/w/index.php?title=Ginkgolide_C&action=edit&redlink=1" class="new" title="Ginkgolide C (page does not exist)">ginkgolide C</a>, <a href="/w/index.php?title=Ginkgolide_J&action=edit&redlink=1" class="new" title="Ginkgolide J (page does not exist)">ginkgolide J</a>, <a href="/w/index.php?title=Ginkgolide_M&action=edit&redlink=1" class="new" title="Ginkgolide M (page does not exist)">ginkgolide M</a>))</li> <li><a href="/wiki/Imipramine" title="Imipramine">Imipramine</a></li> <li><a href="/wiki/NBQX" title="NBQX">NBQX</a></li> <li><a href="/wiki/Neuroactive_steroid" class="mw-redirect" title="Neuroactive steroid">Neuroactive steroids</a> (e.g., <a href="/wiki/3%CE%B1-androsterone_sulfate" class="mw-redirect" title="3α-androsterone sulfate">3α-androsterone sulfate</a>, <a href="/w/index.php?title=3%CE%B2-androsterone_sulfate&action=edit&redlink=1" class="new" title="3β-androsterone sulfate (page does not exist)">3β-androsterone sulfate</a>, <a href="/wiki/11-deoxycorticosterone" class="mw-redirect" title="11-deoxycorticosterone">deoxycorticosterone</a>, <a href="/wiki/DHEA_sulfate" class="mw-redirect" title="DHEA sulfate">DHEA sulfate</a>, <a href="/wiki/Pregnenolone_sulfate" title="Pregnenolone sulfate">pregnenolone sulfate</a>, <a href="/wiki/Progesterone" title="Progesterone">progesterone</a>)</li> <li><a href="/wiki/Opioid" title="Opioid">Opioids</a> (e.g., <a href="/wiki/Codeine" title="Codeine">codeine</a>, <a href="/wiki/Dextromethorphan" title="Dextromethorphan">dextromethorphan</a>, <a href="/wiki/Dextrorphan" title="Dextrorphan">dextrorphan</a>, <a href="/wiki/Levomethadone" title="Levomethadone">levomethadone</a>, <a href="/wiki/Levorphanol" title="Levorphanol">levorphanol</a>, <a href="/wiki/Morphine" title="Morphine">morphine</a>, <a href="/wiki/Oripavine" title="Oripavine">oripavine</a>, <a href="/wiki/Pethidine" title="Pethidine">pethidine</a>, <a href="/wiki/Thebaine" title="Thebaine">thebaine</a>)</li> <li><a href="/wiki/Picrotoxin" title="Picrotoxin">Picrotoxin</a> (i.e., <a href="/wiki/Picrotin" class="mw-redirect" title="Picrotin">picrotin</a> and <a href="/wiki/Picrotoxinin" class="mw-redirect" title="Picrotoxinin">picrotoxinin</a>)</li> <li><a href="/w/index.php?title=Phenylbenzene_%CF%89-phosphono-%CE%B1-amino_acid&action=edit&redlink=1" class="new" title="Phenylbenzene ω-phosphono-α-amino acid (page does not exist)">PMBA</a></li> <li><a href="/wiki/Riluzole" title="Riluzole">Riluzole</a></li> <li><a href="/w/index.php?title=Tropeine&action=edit&redlink=1" class="new" title="Tropeine (page does not exist)">Tropeines</a> (e.g., <a href="/wiki/Bemesetron" title="Bemesetron">bemesetron</a>, <a href="/w/index.php?title=LY-278584&action=edit&redlink=1" class="new" title="LY-278584 (page does not exist)">LY-278584</a>, <a href="/wiki/Tropisetron" title="Tropisetron">tropisetron</a>, <a href="/wiki/Zatosetron" title="Zatosetron">zatosetron</a>)</li> <li><a href="/wiki/Verapamil" title="Verapamil">Verapamil</a></li> <li><a href="/wiki/Zinc" title="Zinc">Zinc</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:4em;;text-align:center;"><a href="/wiki/N-Methyl-D-aspartate_receptor" class="mw-redirect" title="N-Methyl-D-aspartate receptor"><abbr title="N-Methyl-D-aspartate receptor">NMDAR</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip N-Methyl-D-aspartate receptor</span></th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li>See <a href="/wiki/Template:Ionotropic_glutamate_receptor_modulators" title="Template:Ionotropic glutamate receptor modulators">here</a> instead.</li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Neurotransmitter_transporter" title="Neurotransmitter transporter">Transporter</a><br /><small>(<a href="/wiki/Reuptake_inhibitor" title="Reuptake inhibitor">blockers</a>)</small></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:4em;;text-align:center;"><a href="/wiki/Glycine_transporter_1" class="mw-redirect" title="Glycine transporter 1"><abbr title="Glycine transporter 1">GlyT1</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Glycine transporter 1</span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/w/index.php?title=ACPPB&action=edit&redlink=1" class="new" title="ACPPB (page does not exist)">ACPPB</a></li> <li><a href="/w/index.php?title=ALX-5407&action=edit&redlink=1" class="new" title="ALX-5407 (page does not exist)">ALX-5407 (NFPS)</a></li> <li><a href="/wiki/ASP2535" title="ASP2535">ASP2535</a></li> <li><a href="/wiki/Bitopertin" title="Bitopertin">Bitopertin (RG1678/RO4917838)</a></li> <li><a href="/w/index.php?title=CP-802079&action=edit&redlink=1" class="new" title="CP-802079 (page does not exist)">CP-802079</a></li> <li><a href="/wiki/Alcohol_(drug)" title="Alcohol (drug)">Ethanol (alcohol)</a></li> <li><a href="/w/index.php?title=Glycyldodecylamide&action=edit&redlink=1" class="new" title="Glycyldodecylamide (page does not exist)">Glycyldodecylamide</a></li> <li><a href="/w/index.php?title=GSK1018921&action=edit&redlink=1" class="new" title="GSK1018921 (page does not exist)">GSK1018921</a></li> <li><a href="/wiki/Iclepertin" title="Iclepertin">Iclepertin</a></li> <li><a href="/wiki/LY-2365109" title="LY-2365109">LY-2365109</a></li> <li><a href="/wiki/Mardepodect" title="Mardepodect">Mardepodect</a></li> <li><a href="/wiki/ORG-24598" title="ORG-24598">ORG-24598</a></li> <li><a href="/wiki/ORG-25935" title="ORG-25935">ORG-25935 (SCH-900435)</a></li> <li><a href="/wiki/Pesampator" title="Pesampator">Pesampator (BIIB-104, PF-04958242)</a></li> <li><a href="/w/index.php?title=PF-03463275&action=edit&redlink=1" class="new" title="PF-03463275 (page does not exist)">PF-03463275</a></li> <li><a href="/wiki/Sarcosine" title="Sarcosine">Sarcosine</a></li> <li><a href="/wiki/SNG-12" title="SNG-12">SNG-12 (Synapsinae)</a></li> <li><a href="/w/index.php?title=SSR-103,800&action=edit&redlink=1" class="new" title="SSR-103,800 (page does not exist)">SSR-103,800</a></li> <li><a href="/w/index.php?title=SSR-504,734&action=edit&redlink=1" class="new" title="SSR-504,734 (page does not exist)">SSR-504,734</a></li> <li><a href="/wiki/Tilapertin" title="Tilapertin">Tilapertin</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:4em;;text-align:center;"><a href="/wiki/Glycine_transporter_2" class="mw-redirect" title="Glycine transporter 2"><abbr title="Glycine transporter 2">GlyT2</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Glycine transporter 2</span></th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/ALX-1393" title="ALX-1393">ALX-1393</a></li> <li><a href="/wiki/Amoxapine" title="Amoxapine">Amoxapine</a></li> <li><a href="/wiki/Alcohol_(drug)" title="Alcohol (drug)">Ethanol (alcohol)</a></li> <li><a href="/wiki/N-Arachidonylglycine" title="N-Arachidonylglycine">NAGly</a></li> <li><a href="/wiki/Opiranserin" title="Opiranserin">Opiranserin (VVZ-149)</a></li> <li><a href="/w/index.php?title=ORG-25543&action=edit&redlink=1" class="new" title="ORG-25543 (page does not exist)">ORG-25543</a></li> <li><a href="/w/index.php?title=VVZ-368&action=edit&redlink=1" class="new" title="VVZ-368 (page does not exist)">VVZ-368</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><td class="navbox-abovebelow" colspan="2"><div> <dl><dt>See also</dt> <dd><i><a href="/wiki/Template:Receptor_modulators" title="Template:Receptor modulators">Receptor/signaling modulators</a></i></dd> <dd><i><a href="/wiki/Template:GABA_receptor_modulators" title="Template:GABA receptor modulators">GABA receptor modulators</a></i></dd> <dd><i><a href="/wiki/Template:GABAA_receptor_positive_modulators" title="Template:GABAA receptor positive modulators">GABA<sub>A</sub> receptor positive modulators</a></i></dd> <dd><i><a href="/wiki/Template:Ionotropic_glutamate_receptor_modulators" title="Template:Ionotropic glutamate receptor modulators">Ionotropic glutamate receptor modulators</a></i></dd></dl> </div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"></div><div role="navigation" class="navbox" aria-labelledby="PAF_receptor_modulators" style="padding:3px"><table class="nowraplinks hlist mw-collapsible mw-collapsed navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:PAF_receptor_modulators" title="Template:PAF receptor modulators"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:PAF_receptor_modulators" title="Template talk:PAF receptor modulators"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:PAF_receptor_modulators" title="Special:EditPage/Template:PAF receptor modulators"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="PAF_receptor_modulators" style="font-size:114%;margin:0 4em"><a href="/wiki/Platelet-activating_factor" title="Platelet-activating factor"><abbr title="Platelet-activating factor">PAF</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/Platelet-activating_factor_receptor" title="Platelet-activating factor receptor"><abbr title="Platelet-activating factor receptor">PAFR</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 Platelet-activating factor receptor</span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:6em;;text-align:center;">Agonists</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=Carbamyl-PAF&action=edit&redlink=1" class="new" title="Carbamyl-PAF (page does not exist)">C-PAF</a></li> <li><a href="/wiki/Edelfosine" title="Edelfosine">Edelfosine</a></li> <li><a href="/wiki/Platelet-activating_factor" title="Platelet-activating factor">PAF</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:6em;;text-align:center;">Antagonists</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=A-85783&action=edit&redlink=1" class="new" title="A-85783 (page does not exist)">A-85783</a></li> <li><a href="/w/index.php?title=ABT-491&action=edit&redlink=1" class="new" title="ABT-491 (page does not exist)">ABT-491</a></li> <li><a href="/wiki/Apafant" title="Apafant">Apafant</a></li> <li><a href="/w/index.php?title=BN-50739&action=edit&redlink=1" class="new" title="BN-50739 (page does not exist)">BN-50739</a></li> <li><a href="/w/index.php?title=BN-52063&action=edit&redlink=1" class="new" title="BN-52063 (page does not exist)">BN-52063</a></li> <li><a href="/wiki/Cetirizine" title="Cetirizine">Cetirizine</a></li> <li><a href="/w/index.php?title=CV-3988&action=edit&redlink=1" class="new" title="CV-3988 (page does not exist)">CV-3988</a></li> <li><a href="/w/index.php?title=CV-6209&action=edit&redlink=1" class="new" title="CV-6209 (page does not exist)">CV-6209</a></li> <li><a href="/wiki/Etizolam" title="Etizolam">Etizolam</a></li> <li><a href="/wiki/Ginkgolide_B" class="mw-redirect" title="Ginkgolide B">Ginkgolide B (BN-52021)</a></li> <li><a href="/wiki/Israpafant" title="Israpafant">Israpafant</a></li> <li><a href="/w/index.php?title=Kadsurenone&action=edit&redlink=1" class="new" title="Kadsurenone (page does not exist)">Kadsurenone</a></li> <li><a href="/w/index.php?title=L-652&action=edit&redlink=1" class="new" title="L-652 (page does not exist)">L-652</a></li> <li><a href="/wiki/Lexipafant" title="Lexipafant">Lexipafant</a></li> <li><a href="/wiki/Loratadine" title="Loratadine">Loratadine</a></li> <li><a href="/w/index.php?title=PCA-4248&action=edit&redlink=1" class="new" title="PCA-4248 (page does not exist)">PCA-4248</a></li> <li><a href="/wiki/Rupatadine" title="Rupatadine">Rupatadine</a></li> <li><a href="/wiki/SM-12502" class="mw-redirect" title="SM-12502">SM-12502</a></li> <li><a href="/w/index.php?title=SR-27417&action=edit&redlink=1" class="new" title="SR-27417 (page does not exist)">SR-27417</a></li> <li><a href="/w/index.php?title=SRI_63-441&action=edit&redlink=1" class="new" title="SRI 63-441 (page does not exist)">SRI 63-441</a></li> <li><a href="/wiki/Terfenadine" title="Terfenadine">Terfenadine</a></li> <li><a href="/w/index.php?title=WEB-2086&action=edit&redlink=1" class="new" title="WEB-2086 (page does not exist)">WEB-2086</a></li> <li><a href="/w/index.php?title=Yangambin&action=edit&redlink=1" class="new" title="Yangambin (page does not exist)">Yangambin</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;">Others</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="Precursors" scope="row" class="navbox-group" style="width:6em;;text-align:center;">Precursors</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/Choline" title="Choline">Choline</a></li> <li><a href="/wiki/Adenosine_triphosphate" title="Adenosine triphosphate">ATP</a></li> <li><a href="/wiki/Phosphocholine" title="Phosphocholine">Phosphocholine</a></li> <li><a href="/wiki/Phosphatidylcholine" title="Phosphatidylcholine">PC</a></li> <li><a href="/wiki/Lysophosphatidylcholine" title="Lysophosphatidylcholine">LPC</a></li> <li><a href="/w/index.php?title=1-O-Alkyl-2-acetyl-sn-glycerol&action=edit&redlink=1" class="new" title="1-O-Alkyl-2-acetyl-sn-glycerol (page does not exist)">AAG</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></dl> </div></td></tr></tbody></table></div> <!-- NewPP limit report Parsed by mw‐web.eqiad.main‐5dc468848‐ccfm8 Cached time: 20241122145015 Cache expiry: 2592000 Reduced expiry: false Complications: [vary‐revision‐sha1, show‐toc] CPU time usage: 0.450 seconds Real time usage: 0.569 seconds Preprocessor visited node count: 1052/1000000 Post‐expand include size: 59442/2097152 bytes Template argument size: 1071/2097152 bytes Highest expansion depth: 10/100 Expensive parser function count: 1/500 Unstrip recursion depth: 1/20 Unstrip post‐expand size: 42683/5000000 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