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class="vector-toc-numb">3.1</span> <span>History</span> </div> </a> <ul id="toc-History-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Mechanisms_of_action" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Mechanisms_of_action"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.2</span> <span>Mechanisms of action</span> </div> </a> <ul id="toc-Mechanisms_of_action-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Toxicity_and_toxicology" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Toxicity_and_toxicology"> <div class="vector-toc-text"> <span class="vector-toc-numb">4</span> <span>Toxicity and toxicology</span> </div> </a> <button aria-controls="toc-Toxicity_and_toxicology-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> <span class="vector-icon mw-ui-icon-wikimedia-expand"></span> <span>Toggle 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Unsourced or poorly sourced material may be challenged and removed.</span> <span class="date-container"><i>(<span class="date">February 2017</span>)</i></span><span class="hide-when-compact"><i> (<small><a href="/wiki/Help:Maintenance_template_removal" title="Help:Maintenance template removal">Learn how and when to remove this message</a></small>)</i></span></div></td></tr></tbody></table> <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): Gelsemine">Gelsemine</span></caption><tbody><tr><td colspan="2" class="infobox-image notheme" style="background-color: #f8f9fa;"><span typeof="mw:File"><a href="/wiki/File:Gelsemine.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/5/57/Gelsemine.svg/240px-Gelsemine.svg.png" decoding="async" width="240" height="204" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/5/57/Gelsemine.svg/360px-Gelsemine.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/5/57/Gelsemine.svg/480px-Gelsemine.svg.png 2x" data-file-width="435" data-file-height="370" /></a></span><div class="infobox-caption">Gelsemine (gelsemin), an <a href="/wiki/Indole_alkaloid" title="Indole alkaloid">indole alkaloid</a></div></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/Anatomical_Therapeutic_Chemical_Classification_System" title="Anatomical Therapeutic Chemical Classification System">ATC code</a></th><td class="infobox-data"><style data-mw-deduplicate="TemplateStyles:r1126788409">.mw-parser-output .plainlist ol,.mw-parser-output .plainlist ul{line-height:inherit;list-style:none;margin:0;padding:0}.mw-parser-output .plainlist ol li,.mw-parser-output .plainlist ul li{margin-bottom:0}</style><div class="plainlist"><ul><li>none</li></ul></div></td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd">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%;">3-ethenyl-1-methyl-2,3,3a,7,8,8a-hexahydro-1h,5h-spiro[3,8,5-(ethane[1,1,2]triyl)oxepino[4,5-b]pyrrole-4,3'-indol]-2'(1'h)-one</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=509-15-9">509-15-9</a></span></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/279057">279057</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.4536577.html">4536577</a></span></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/5Y13A78Z72">5Y13A78Z72</a></span></li></ul></div></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>20</sub><span title="Hydrogen">H</span><sub>22</sub><span title="Nitrogen">N</span><sub>2</sub><span title="Oxygen">O</span><sub>2</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="7002322408000000000♠"></span>322.408</span> g·mol<sup>−1</sup></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;">3D model (<a href="/wiki/JSmol" class="mw-redirect" title="JSmol">JSmol</a>)</th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="chemapps.stolaf.edu (3D interactive model)"><a rel="nofollow" class="external text" href="https://chemapps.stolaf.edu/jmol/jmol.php?model=CN1C%28C2CO3%29%5BC%40%40H%5D4%5BC%40%5D5%28C%28C%3DCC%3DC6%29%3DC6NC5%3DO%29%5BC%40H%5D3C%5BC%40H%5D2%5BC%40%5D4%28C%3DC%29C1">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%;">CN1C(C2CO3)[C@@H]4[C@]5(C(C=CC=C6)=C6NC5=O)[C@H]3C[C@H]2[C@]4(C=C)C1</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/C20H22N2O2/c1-3-19-10-22(2)16-11-9-24-15(8-13(11)19)20(17(16)19)12-6-4-5-7-14(12)21-18(20)23/h3-7,11,13,15-17H,1,8-10H2,2H3,(H,21,23)/t11-,13+,15+,16+,17-,19-,20-/m0/s1</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:NFYYATWFXNPTRM-QJICHLCESA-N</div></li></ul> </div></td></tr></tbody></table> <p><b>Gelsemine</b> (C<sub>20</sub>H<sub>22</sub>N<sub>2</sub>O<sub>2</sub>) is an indole <a href="/wiki/Alkaloid" title="Alkaloid">alkaloid</a> isolated from flowering plants of the genus <i><a href="/wiki/Gelsemium_sempervirens" title="Gelsemium sempervirens">Gelsemium</a></i>, a plant native to the subtropical and tropical Americas, and southeast Asia, and is a highly toxic compound that acts as a paralytic, exposure to which can result in death. It has generally potent activity as an agonist of the mammalian <a href="/wiki/Glycine_receptor" title="Glycine receptor">glycine receptor</a>, the activation of which leads to an inhibitory <a href="/wiki/Postsynaptic_potential" title="Postsynaptic potential">postsynaptic potential</a> in neurons following <a href="/wiki/Chloride" title="Chloride">chloride</a> ion influx, and systemically, to muscle relaxation of varying intensity and deleterious effect. Despite its danger and toxicity, recent pharmacological research has suggested that the biological activities of this compound may offer opportunities for developing treatments related to <a href="/wiki/Xenobiotic" title="Xenobiotic">xenobiotic</a> or diet-induced <a href="/wiki/Oxidative_stress" title="Oxidative stress">oxidative stress</a>, and of anxiety and other conditions, with ongoing research including attempts to identify safer derivatives and analogs to make use of gelsemine's beneficial effects.<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><sup id="cite_ref-2" class="reference"><a href="#cite_note-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Natural_sources">Natural sources</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Gelsemine&action=edit&section=1" title="Edit section: Natural sources"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure class="mw-default-size mw-halign-right" typeof="mw:File/Thumb"><a href="/wiki/File:Gelsemium_sempervirens_001.JPG" class="mw-file-description"><img alt="Picture of plant climbing a trellis, with dar green foliage, and numerous bright yellow flowers." src="//upload.wikimedia.org/wikipedia/commons/thumb/d/d3/Gelsemium_sempervirens_001.JPG/170px-Gelsemium_sempervirens_001.JPG" decoding="async" width="170" height="227" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/d/d3/Gelsemium_sempervirens_001.JPG/255px-Gelsemium_sempervirens_001.JPG 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/d/d3/Gelsemium_sempervirens_001.JPG/340px-Gelsemium_sempervirens_001.JPG 2x" data-file-width="1553" data-file-height="2070" /></a><figcaption> Example of a <i>Gelsemium</i> species, from which gelsemine is isolated <i>Gelsemium sempervirens</i>, its principal source in the Americas.<sup id="cite_ref-ZhangWang14r_3-0" class="reference"><a href="#cite_note-ZhangWang14r-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Ornduff70_4-0" class="reference"><a href="#cite_note-Ornduff70-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup></figcaption></figure> <p>Gelsemine is found in, and can be isolated from, the subtropical to tropical flowering plant genus <i><a href="/wiki/Gelsemium_sempervirens" title="Gelsemium sempervirens">Gelsemium</a></i>, family <a href="/wiki/Loganiaceae" title="Loganiaceae">Loganiaceae</a>, which as of 2014 included five species, where <i>G. sempervirens</i> Ait., the type species, is prevalent in the Americas and <i>G. elegans</i> Benth. in China and East Asia.<sup id="cite_ref-ZhangWang14r_3-1" class="reference"><a href="#cite_note-ZhangWang14r-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Ornduff70_4-1" class="reference"><a href="#cite_note-Ornduff70-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> The species in the Americas, <i>G. sempervirens</i>, has a number of common names that include yellow or Carolina jasmine (or jessamine), gelsemium, evening trumpetflower, and woodbine.<sup id="cite_ref-GRIN_5-0" class="reference"><a href="#cite_note-GRIN-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-AFVP_6-0" class="reference"><a href="#cite_note-AFVP-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> The plant genus is native to the subtropical and tropical <a href="/wiki/Americas" title="Americas">Americas</a>, e.g., in <a href="/wiki/Mexico" title="Mexico">Mexico</a>, <a href="/wiki/Honduras" title="Honduras">Honduras</a>, <a href="/wiki/Guatemala" title="Guatemala">Guatemala</a>, and <a href="/wiki/Belize" title="Belize">Belize</a>,<sup id="cite_ref-Ornduff70_4-2" class="reference"><a href="#cite_note-Ornduff70-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> as well as to China and southeast Asia.<sup id="cite_ref-Ornduff70_4-3" class="reference"><a href="#cite_note-Ornduff70-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> The species is prized for its "heavily fragrant yellow flowers," and has been cultivated since mid-seventeenth century (in Europe).<sup id="cite_ref-Ornduff70_4-4" class="reference"><a href="#cite_note-Ornduff70-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> It is found in southeastern and south-central states of the U.S.,<sup id="cite_ref-GRIN_5-1" class="reference"><a href="#cite_note-GRIN-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> and as a garden plant in warmer areas where it can be trained to grow over arbors or to cover walls (see image).<sup id="cite_ref-7" class="reference"><a href="#cite_note-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> </p><p>All plant parts of the herbage and exudates of this genus, including its sap and nectar, appear to contain gelsemine and related compounds,<sup id="cite_ref-drugsDOTcom_8-0" class="reference"><a href="#cite_note-drugsDOTcom-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> as well as a wide variety of further alkaloids and other natural products.<sup id="cite_ref-ZhangWang14r_3-2" class="reference"><a href="#cite_note-ZhangWang14r-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> The plant's herbage, in particular, is known to contain several toxic alkaloids, and is generally known to be poisonous to livestock and humans.<sup id="cite_ref-Ornduff70_4-5" class="reference"><a href="#cite_note-Ornduff70-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Chemistry">Chemistry</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Gelsemine&action=edit&section=2" title="Edit section: Chemistry"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1236090951">.mw-parser-output .hatnote{font-style:italic}.mw-parser-output div.hatnote{padding-left:1.6em;margin-bottom:0.5em}.mw-parser-output .hatnote i{font-style:normal}.mw-parser-output .hatnote+link+.hatnote{margin-top:-0.5em}@media print{body.ns-0 .mw-parser-output .hatnote{display:none!important}}</style><div role="note" class="hatnote navigation-not-searchable">See also: <a class="mw-selflink-fragment" href="#Chemical_synthesis">Gelsemine § Chemical synthesis</a></div> <figure class="mw-default-size mw-halign-left" typeof="mw:File/Thumb"><a href="/wiki/File:GELSEMINA.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/6/67/GELSEMINA.png/170px-GELSEMINA.png" decoding="async" width="170" height="128" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/6/67/GELSEMINA.png 1.5x" data-file-width="217" data-file-height="164" /></a><figcaption>Numbering of gelsemine</figcaption></figure> <p>Gelsemine was isolated from <i>G. sempervirens</i> Ait., in 1870.<sup id="cite_ref-QiuEtal15_9-0" class="reference"><a href="#cite_note-QiuEtal15-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Lin03_10-0" class="reference"><a href="#cite_note-Lin03-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> Its chemical formula was determined to be C<sub>20</sub>H<sub>22</sub>N<sub>2</sub>O<sub>2</sub>, thus with a molecular weight of 322.44 g/mol.<sup id="cite_ref-Toxnet_11-0" class="reference"><a href="#cite_note-Toxnet-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> Its structure was finally determined, by X-ray crystallographic analysis and by nuclear magnetic resonance (NMR) spectroscopy, in 1959 by Conroy and Chakrabarti.<sup id="cite_ref-:1_12-0" class="reference"><a href="#cite_note-:1-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-QiuEtal15_9-1" class="reference"><a href="#cite_note-QiuEtal15-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Lin03_10-1" class="reference"><a href="#cite_note-Lin03-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> </p><p>It is a <a href="/wiki/Monoterpenoid" class="mw-redirect" title="Monoterpenoid">monoterpenoid</a> type of <a href="/wiki/Indole" title="Indole">indole</a> alkaloid,<sup id="cite_ref-Seigler98_13-0" class="reference"><a href="#cite_note-Seigler98-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup> and a close relative of the natural product gelseminine, which is also present from the same natural sources.<sup id="cite_ref-drugsDOTcom_8-1" class="reference"><a href="#cite_note-drugsDOTcom-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> The gelsemine class of alkaloids are some of a wide variety of the alkaloid and other natural products that have been isolated from this genus of plants.<sup id="cite_ref-ZhangWang14r_3-3" class="reference"><a href="#cite_note-ZhangWang14r-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> </p> <style data-mw-deduplicate="TemplateStyles:r1237032888/mw-parser-output/.tmulti">.mw-parser-output .tmulti .multiimageinner{display:flex;flex-direction:column}.mw-parser-output .tmulti 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.trow>.thumbcaption{text-align:center}}@media screen{html.skin-theme-clientpref-night .mw-parser-output .tmulti .multiimageinner img{background-color:white}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .tmulti .multiimageinner img{background-color:white}}</style><div class="thumb tmulti tright"><div class="thumbinner multiimageinner" style="width:492px;max-width:492px"><div class="trow"><div class="tsingle" style="width:192px;max-width:192px"><div class="thumbimage"><span typeof="mw:File"><a href="/wiki/File:Secologanin.png" class="mw-file-description"><img alt="" src="//upload.wikimedia.org/wikipedia/commons/thumb/c/c1/Secologanin.png/190px-Secologanin.png" decoding="async" width="190" height="123" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/c/c1/Secologanin.png/285px-Secologanin.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/c/c1/Secologanin.png/380px-Secologanin.png 2x" data-file-width="1800" data-file-height="1163" /></a></span></div><div class="thumbcaption"><b><a href="/wiki/Secologanin" title="Secologanin">secologanin</a></b></div></div><div class="tsingle" style="width:102px;max-width:102px"><div class="thumbimage"><span typeof="mw:File"><a href="/wiki/File:Tryptamine.svg" class="mw-file-description"><img alt="" src="//upload.wikimedia.org/wikipedia/commons/thumb/0/09/Tryptamine.svg/100px-Tryptamine.svg.png" decoding="async" width="100" height="54" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/0/09/Tryptamine.svg/150px-Tryptamine.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/0/09/Tryptamine.svg/200px-Tryptamine.svg.png 2x" data-file-width="306" data-file-height="166" /></a></span></div><div class="thumbcaption"><b><a href="/wiki/Tryptamine" title="Tryptamine">tryptamine</a></b></div></div><div class="tsingle" style="width:192px;max-width:192px"><div class="thumbimage"><span typeof="mw:File"><a href="/wiki/File:Strictosidine.svg" class="mw-file-description"><img alt="" src="//upload.wikimedia.org/wikipedia/commons/thumb/3/36/Strictosidine.svg/190px-Strictosidine.svg.png" decoding="async" width="190" height="169" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/3/36/Strictosidine.svg/285px-Strictosidine.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/3/36/Strictosidine.svg/380px-Strictosidine.svg.png 2x" data-file-width="359" data-file-height="320" /></a></span></div><div class="thumbcaption"><b>3α(<i>S</i>)-<a href="/wiki/Strictosidine" title="Strictosidine">strictosidine</a></b> (isovincoside)</div></div></div><div class="trow" style="display:flex"><div class="thumbcaption"><b><a href="/wiki/Strictosidine" title="Strictosidine">Strictosidine</a> and its precursors, line-angle representations.</b> 3α(<i>S</i>)-<a href="/wiki/Strictosidine" title="Strictosidine">strictosidine</a> (isovincoside) is a key intermediate on the biosynthetic pathway of gelsemine, and it is the common precursor for essentially all monoterpenoid indole alkaloids. Strictosidine is derived in one enzyme-catalyzed step from <a href="/wiki/Tryptamine" title="Tryptamine">tryptamine</a> and <a href="/wiki/Secologanin" title="Secologanin">secologanin</a> (the latter of which, a terpene, is ultimately derived from <a href="/wiki/Mevalonic_acid" title="Mevalonic acid">mevalonic acid</a>).</div></div></div></div> <p>Gelsemine's biosynthesis, as of 1998, is thought to proceed from 3α(<i>S</i>)-<a href="/wiki/Strictosidine" title="Strictosidine">strictosidine</a> (isovincoside), the common precursor for essentially all monoterpenoid indole alkaloids—itself deriving directly from <a href="/wiki/Mevalonic_acid" title="Mevalonic acid">mevalonic acid</a>-derived <a href="/wiki/Secologanin" title="Secologanin">secologanin</a> and <a href="/wiki/Tryptamine" title="Tryptamine">tryptamine</a>.<sup id="cite_ref-14" class="reference"><a href="#cite_note-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Seigler98_13-1" class="reference"><a href="#cite_note-Seigler98-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup><sup class="reference nowrap"><span title="Page / location: p. 629">: p. 629 </span></sup> From strictosidine, the biosynthesis proceeds through five intermediates—including <a href="/w/index.php?title=Koumicine&action=edit&redlink=1" class="new" title="Koumicine (page does not exist)">koumicine</a> (<a href="/w/index.php?title=Akkuammidine&action=edit&redlink=1" class="new" title="Akkuammidine (page does not exist)">akkuammidine</a>), <a href="/w/index.php?title=Koumidine&action=edit&redlink=1" class="new" title="Koumidine (page does not exist)">koumidine</a>, <a href="/w/index.php?title=Vobasindiol&action=edit&redlink=1" class="new" title="Vobasindiol (page does not exist)">vobasindiol</a>, <a href="/w/index.php?title=Anhydrovobasindiol&action=edit&redlink=1" class="new" title="Anhydrovobasindiol (page does not exist)">anhydrovobasindiol</a>, and <a href="/w/index.php?title=Gelsenidine&action=edit&redlink=1" class="new" title="Gelsenidine (page does not exist)">gelsenidine</a> (<a href="/w/index.php?title=Humantienine&action=edit&redlink=1" class="new" title="Humantienine (page does not exist)">humantienine</a>-type).<sup id="cite_ref-Seigler98_13-2" class="reference"><a href="#cite_note-Seigler98-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup><sup class="reference nowrap"><span title="Page / location: p. 629">: p. 629 </span></sup><sup id="cite_ref-LiuLu88_15-0" class="reference"><a href="#cite_note-LiuLu88-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup> The related alkaloids <a href="/w/index.php?title=Koumine&action=edit&redlink=1" class="new" title="Koumine (page does not exist)">koumine</a> and <a href="/w/index.php?title=Gelsemicine&action=edit&redlink=1" class="new" title="Gelsemicine (page does not exist)">gelsemicine</a> also derive from this pathway (koumine from anhydrovobasindiol via oxidation and rearrangement, and gelsemicine from gelsemine itself, via aromatic oxidation and O-methylation).<sup id="cite_ref-Seigler98_13-3" class="reference"><a href="#cite_note-Seigler98-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup><sup class="reference nowrap"><span title="Page / location: p. 629">: p. 629 </span></sup> <sup id="cite_ref-LiuLu88_15-1" class="reference"><a href="#cite_note-LiuLu88-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup><sup class="reference nowrap"><span title="Page / location: p. 132ff">: p. 132ff </span></sup> For the chemical synthesis (natural product synthesis, studies and total synthesis), see the separate section below. </p> <div class="mw-heading mw-heading2"><h2 id="Summary_of_biological_activities">Summary of biological activities</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Gelsemine&action=edit&section=3" title="Edit section: Summary of biological activities"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Full sections in following are devoted to specific activities of gelsemine. Noted are the facts that it is a highly toxic compound, where exposure can result in paralysis and death. It is reported to be a <a href="/wiki/Glycine_receptor" title="Glycine receptor">glycine receptor</a> agonist with significantly higher binding affinity for some of these receptors than its native agonist, <a href="/wiki/Glycine" title="Glycine">glycine</a>. In addition, it has been shown to have effects on pathways/systems in model animals (rat, rabbit), related to xenobiotic- or diet-induced oxidative stress, and in the treatment of anxiety and other conditions. </p> <div class="mw-heading mw-heading3"><h3 id="History">History</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Gelsemine&action=edit&section=4" title="Edit section: History"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Gelsimium extracts, and so gelsemine, indirectly, have been the subject of serious scientific study for over a hundred years. On the medical side, gelsemium <a href="/wiki/Tincture" title="Tincture">tinctures</a> were used in the treatment of <a href="/wiki/Neuralgia" title="Neuralgia">neuralgia</a> by physicians in England, in the late 19th century; <a href="/wiki/Arthur_Conan_Doyle" title="Arthur Conan Doyle">Arthur Conan Doyle</a>, the <a href="/wiki/Sherlock_Holmes" title="Sherlock Holmes">noted author</a> who first trained as a physician, after observing the success of such treatments, ingested increasing doses of a tincture daily, to “ascertain how far one might go in taking the drug, and what the primary symptoms of an overdose might be,” submitting his first career publication on this in the <i>British Medical Journal.</i><sup id="cite_ref-16" class="reference"><a href="#cite_note-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup><sup>[<i>primary source</i>]</sup> On the chemistry side, the December 1910 meeting of the Division of Pharmaceutical Chemistry, of the <a href="/wiki/American_Chemical_Society" title="American Chemical Society">American Chemical Society</a>, reports among the papers read, the "Assay of Gelsemium" by L.E. Sayre.<sup id="cite_ref-17" class="reference"><a href="#cite_note-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup><sup>[<i>primary source</i>]</sup> </p> <div class="mw-heading mw-heading3"><h3 id="Mechanisms_of_action">Mechanisms of action</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Gelsemine&action=edit&section=5" title="Edit section: Mechanisms of action"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Gelsemine is an <a href="/wiki/Agonist" title="Agonist">agonist</a> for the <a href="/wiki/Glycine_receptor" title="Glycine receptor">glycine receptor</a> (GlyR) with a much greater affinity for studied examples of this receptor than glycine.<sup id="cite_ref-18" class="reference"><a href="#cite_note-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup> These receptors are ligand-gated ion channels which affect a variety of physiological processes. When glycine receptors are activated by agonist binding to at least two of the five agonist binding sites, chloride ions enter the <a href="/wiki/Neuron" title="Neuron">neuron</a>. This causes an inhibitory <a href="/wiki/Postsynaptic_potential" title="Postsynaptic potential">postsynaptic potential</a>, which, systemically, leads to muscle relaxation.<sup id="cite_ref-:2_19-0" class="reference"><a href="#cite_note-:2-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-20" class="reference"><a href="#cite_note-20"><span class="cite-bracket">[</span>20<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Toxicity_and_toxicology">Toxicity and toxicology</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Gelsemine&action=edit&section=6" title="Edit section: Toxicity and toxicology"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>In mice, it has been shown to have an LD<sub>50</sub> of 56 mg/kg (intraperitoneal),<sup id="cite_ref-21" class="reference"><a href="#cite_note-21"><span class="cite-bracket">[</span>21<span class="cite-bracket">]</span></a></sup> and a lowest lethal dose (LD<sub>Lo</sub>) of 0.1-0.12 mg/kg (intravenous).<sup id="cite_ref-:0_22-0" class="reference"><a href="#cite_note-:0-22"><span class="cite-bracket">[</span>22<span class="cite-bracket">]</span></a></sup> In rabbits, the LD<sub>Lo</sub> was 0.05-0.06 mg/kg (intravenous).<sup id="cite_ref-:0_22-1" class="reference"><a href="#cite_note-:0-22"><span class="cite-bracket">[</span>22<span class="cite-bracket">]</span></a></sup> In frogs, the LD<sub>Lo</sub> was 20–30 mg/kg (subcutaneous).<sup id="cite_ref-:0_22-2" class="reference"><a href="#cite_note-:0-22"><span class="cite-bracket">[</span>22<span class="cite-bracket">]</span></a></sup> In dogs, the LD<sub>Lo</sub> was 0.5-1.0 mg/kg (intravenous).<sup id="cite_ref-:0_22-3" class="reference"><a href="#cite_note-:0-22"><span class="cite-bracket">[</span>22<span class="cite-bracket">]</span></a></sup> In parson, the LD<sub>50</sub> was 0.05 mg/kg </p><p>The <a href="/wiki/Sap" title="Sap">sap</a> of the plant may cause skin irritation in sensitive individuals, and there are reports that inhalation from the flowers alone may, in some cases, lead to human poisoning (see below, where insect death at such flowers is likewise reported).<sup id="cite_ref-Ornduff70_4-6" class="reference"><a href="#cite_note-Ornduff70-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> </p><p>The plant's herbage is known to contain several toxic alkaloids, and while there is report of its feeding to pigs, it is generally considered to be an abortifacient and lethal poison when livestock or other animals feed on its leaves.<sup id="cite_ref-Ornduff70_4-7" class="reference"><a href="#cite_note-Ornduff70-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> It has been reportedly used as a fish poison as well, e.g., on the island of <a href="/wiki/Borneo" title="Borneo">Borneo</a>.<sup id="cite_ref-Ornduff70_4-8" class="reference"><a href="#cite_note-Ornduff70-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> </p><p>Human poisonings are known, including pediatric and adult cases, and in the case of adults, both accidental and intentional poisonings. At lower doses in humans, the inhibitory <a href="/wiki/Postsynaptic_potential" title="Postsynaptic potential">postsynaptic potential</a> induced by gelsemine action at the glycine receptor can result in nausea, diarrhea and muscle spasms caused by loss of involuntary muscle control; at higher doses, vision impairment or blindness, paralysis, and death can occur.<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (February 2017)">citation needed</span></a></i>]</sup> Children, mistaking the flower of <i><a href="/wiki/Gelsemium_sempervirens" title="Gelsemium sempervirens">G. sempervirens</a></i> for <a href="/wiki/Honeysuckle" title="Honeysuckle">honeysuckle</a>, have been poisoned by sucking the <a href="/wiki/Nectar" title="Nectar">nectar</a> from the flower; its ingestion has been associated with honey bee (but not bumble bee) fatalities as well (e.g., in the southeast U.S.).<sup id="cite_ref-KnightWalter01_23-0" class="reference"><a href="#cite_note-KnightWalter01-23"><span class="cite-bracket">[</span>23<span class="cite-bracket">]</span></a></sup><sup class="noprint Inline-Template" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citing_sources" title="Wikipedia:Citing sources"><span title="This citation requires a reference to the specific page or range of pages in which the material appears. (February 2017)">page needed</span></a></i>]</sup><sup id="cite_ref-Ornduff70_4-9" class="reference"><a href="#cite_note-Ornduff70-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-24" class="reference"><a href="#cite_note-24"><span class="cite-bracket">[</span>24<span class="cite-bracket">]</span></a></sup> It has been reportedly used, via ingestion or smoking, as a poison in cases of <a href="/wiki/Suicide" title="Suicide">suicide</a>, in <a href="/wiki/China" title="China">China</a>, <a href="/wiki/Vietnam" title="Vietnam">Vietnam</a>, and <a href="/wiki/Borneo" title="Borneo">Borneo</a>.<sup id="cite_ref-Ornduff70_4-10" class="reference"><a href="#cite_note-Ornduff70-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Treatment">Treatment</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Gelsemine&action=edit&section=7" title="Edit section: Treatment"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Gelsemine is a highly toxic and therefore possibly fatal substance for which there is no <a href="/wiki/Antidote" title="Antidote">antidote</a>, but the symptoms can be managed in low dose intoxications. In the case of an oral exposure a <a href="/wiki/Gastric_lavage" title="Gastric lavage">gastric lavage</a> is performed, which must be done within approximately one hour of ingestion. <a href="/wiki/Activated_charcoal" class="mw-redirect" title="Activated charcoal">Activated charcoal</a> is then administered to bind the free toxin in the gastrointestinal tract to prevent absorption. <a href="/wiki/Benzodiazepine" title="Benzodiazepine">Benzodiazepine</a> or <a href="/wiki/Phenobarbital" title="Phenobarbital">phenobarbital</a> is also generally administered to help control seizing, and <a href="/wiki/Atropine" title="Atropine">atropine</a> can be used to treat <a href="/wiki/Bradycardia" title="Bradycardia">bradycardia</a>. <a href="/wiki/Electrolyte" title="Electrolyte">Electrolyte</a> and nutrient levels are monitored and controlled.<sup id="cite_ref-Toxnet_11-1" class="reference"><a href="#cite_note-Toxnet-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> </p><p>In the case of a skin exposure, the area is washed with soap and water for 15 minutes to avoid <a href="/wiki/Dermal" class="mw-redirect" title="Dermal">skin</a> damage.<sup id="cite_ref-Toxnet_11-2" class="reference"><a href="#cite_note-Toxnet-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> </p><p>While there is no current treatment to reverse the effects of gelsemine poisoning, preliminary research done in rats has suggested that <a href="/wiki/Strychnine" title="Strychnine">strychnine</a> has potential therapeutic applications due to its antagonistic effects at the glycine receptor, resulting in a counteraction of some downstream effects such as the increase in <a href="/wiki/Allopregnanolone" title="Allopregnanolone">allopregnanolone</a> production associated with gelsemine poisoning.<sup id="cite_ref-25" class="reference"><a href="#cite_note-25"><span class="cite-bracket">[</span>25<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-:2_19-1" class="reference"><a href="#cite_note-:2-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Chemical_synthesis">Chemical synthesis</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Gelsemine&action=edit&section=8" title="Edit section: Chemical synthesis"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The chemical synthesis of gelsemine has been an active target of interest since the early 1990s, given its place among the alkaloids, and its complex structure (seven contiguous <a href="/wiki/Stereocenter" title="Stereocenter">stereocenters</a> and six rings).<sup id="cite_ref-QiuEtal15_9-2" class="reference"><a href="#cite_note-QiuEtal15-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-:1_12-1" class="reference"><a href="#cite_note-:1-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup> Although the full mechanism of its biosynthesis is still being investigated, many research groups have successfully synthesized it using chemical means.<sup id="cite_ref-:1_12-2" class="reference"><a href="#cite_note-:1-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-26" class="reference"><a href="#cite_note-26"><span class="cite-bracket">[</span>26<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-27" class="reference"><a href="#cite_note-27"><span class="cite-bracket">[</span>27<span class="cite-bracket">]</span></a></sup> The first racemic total synthesis of gelsemine was in 1994, by W.N. Speckamp's group, with a remarkable first yield of 0.83% (given the subsequent range, prior to 2014, of 0.02-1.2%).<sup id="cite_ref-28" class="reference"><a href="#cite_note-28"><span class="cite-bracket">[</span>28<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-QiuEtal15_9-3" class="reference"><a href="#cite_note-QiuEtal15-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-29" class="reference"><a href="#cite_note-29"><span class="cite-bracket">[</span>29<span class="cite-bracket">]</span></a></sup> </p><p>Eight further total syntheses have been reported in the literature, including from the groups of A.P. Johnson in 1994, T. Fukuyama in 1996 and again in 2000, D.J. Hart in 1997, L.E. Overman in 1999, S.J. Danishefsky in 2002, and Y. Qin in 2012, with the latter Fukuyama group synthesis (31 steps, 0.86%) and the Qin group synthesis (25 steps, 1%) being asymmetric.<sup id="cite_ref-30" class="reference"><a href="#cite_note-30"><span class="cite-bracket">[</span>30<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-31" class="reference"><a href="#cite_note-31"><span class="cite-bracket">[</span>31<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-32" class="reference"><a href="#cite_note-32"><span class="cite-bracket">[</span>32<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-33" class="reference"><a href="#cite_note-33"><span class="cite-bracket">[</span>33<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-34" class="reference"><a href="#cite_note-34"><span class="cite-bracket">[</span>34<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-35" class="reference"><a href="#cite_note-35"><span class="cite-bracket">[</span>35<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-36" class="reference"><a href="#cite_note-36"><span class="cite-bracket">[</span>36<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-QiuEtal15_9-4" class="reference"><a href="#cite_note-QiuEtal15-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> A further asymmetric synthesis using an organocatalytic Diels–Alder approach from the F.G. Qiu and H. Zhai groups in China, reporting a remarkable 12 steps and a 5% yield, was reported in 2015.<sup id="cite_ref-QiuEtal15_9-5" class="reference"><a href="#cite_note-QiuEtal15-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> Additional synthetic approaches were discussed by notable scientists such as Fleming, Stork, Penkett, Pearson, Aubé, Vanderwal, and Simpkins.<sup id="cite_ref-37" class="reference"><a href="#cite_note-37"><span class="cite-bracket">[</span>37<span class="cite-bracket">]</span></a></sup> </p> <figure typeof="mw:File/Thumb"><a href="/wiki/File:Gelsemine_first_synthesis.jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/7/7e/Gelsemine_first_synthesis.jpg/856px-Gelsemine_first_synthesis.jpg" decoding="async" width="856" height="912" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/7/7e/Gelsemine_first_synthesis.jpg 1.5x" data-file-width="1070" data-file-height="1140" /></a><figcaption>Reaction scheme for W.N. Speckamp's first racemic total synthesis of gelsemine.</figcaption></figure> <div class="mw-heading mw-heading2"><h2 id="Potential_medical_applications">Potential medical applications</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Gelsemine&action=edit&section=9" title="Edit section: Potential medical applications"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1251242444"><table class="box-Refimprove_science plainlinks metadata ambox ambox-content ambox-Primary_sources" role="presentation"><tbody><tr><td class="mbox-image"><div class="mbox-image-div"><span typeof="mw:File"><span><img src="//upload.wikimedia.org/wikipedia/en/thumb/9/99/Question_book-new.svg/50px-Question_book-new.svg.png" decoding="async" width="50" height="39" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/9/99/Question_book-new.svg/75px-Question_book-new.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/9/99/Question_book-new.svg/100px-Question_book-new.svg.png 2x" data-file-width="512" data-file-height="399" /></span></span></div></td><td class="mbox-text"><div class="mbox-text-span">This section <b>needs additional <a href="/wiki/Wikipedia:Scientific_citation_guidelines" title="Wikipedia:Scientific citation guidelines">citations</a> to <a href="/wiki/Wikipedia:Reliable_sources#Scholarship" title="Wikipedia:Reliable sources">secondary or tertiary sources</a></b>.<span class="hide-when-compact"> Help add sources such as review articles, monographs, or textbooks. Please also establish the relevance for any <a href="/wiki/Wikipedia:No_original_research#Primary,_secondary_and_tertiary_sources" title="Wikipedia:No original research">primary research articles</a> cited. Unsourced or poorly sourced material may be challenged and removed.</span> <span class="date-container"><i>(<span class="date">February 2017</span>)</i></span><span class="hide-when-compact"><i> (<small><a href="/wiki/Help:Maintenance_template_removal" title="Help:Maintenance template removal">Learn how and when to remove this message</a></small>)</i></span></div></td></tr></tbody></table> <div class="mw-heading mw-heading3"><h3 id="Modern_medical_utility">Modern medical utility</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Gelsemine&action=edit&section=10" title="Edit section: Modern medical utility"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Pharmacological research has suggested gelsemine activities to have potential related to the treatment of anxiety, and in treatments of conditions involving oxidative stress. In addition, gelsemine has been noted to have anti-inflammatory and anti-cancer activities. Recent research on gelsemine has included investigations aimed at developing safer gelsemine analogs and derivatives that might allow safe application of the compounds beneficial effects.<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (February 2017)">citation needed</span></a></i>]</sup> </p><p>The identified <a href="/wiki/Anxiolytic" title="Anxiolytic">anxiolytic</a> effects of preparations derived from <i>Gelsemium sempervirens</i> are believed due to in largest part to the presence of gelsemine in such preparations.<sup id="cite_ref-38" class="reference"><a href="#cite_note-38"><span class="cite-bracket">[</span>38<span class="cite-bracket">]</span></a></sup><sup class="noprint Inline-Template" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Verifiability" title="Wikipedia:Verifiability"><span title="The material near this tag needs to be fact-checked with the cited source(s). (February 2017)">verification needed</span></a></i>]</sup> Based on a rat study, use of gelsemine has been reported as being potentially effective, where the comparison was to treatment with Diazepam.<sup id="cite_ref-BBR13Meyer_39-0" class="reference"><a href="#cite_note-BBR13Meyer-39"><span class="cite-bracket">[</span>39<span class="cite-bracket">]</span></a></sup><sup>[<i>primary source</i>]</sup> </p><p>Gelsemine has been suggested to have potential in offering protective effects against <a href="/wiki/Oxidative_stress" title="Oxidative stress">oxidative stress</a>. In a small rat study, the off-target effects of cisplatin—nephrotoxicity arising from its induction of pathways that generate reactive oxygen species, a factor impacting its use in cancer treatment—were examined, and gelsemine was found to significantly attenuate cisplatin-induced damage to DNA, and further general damage due to oxidative mechanisms. Inhibition of xanthine oxidase and lipid peroxidation activities were noted, along with "increased production and/or activity of anti-oxidants, both enzymatic... and non-enzymatic...".<sup id="cite_ref-LinCbb15_40-0" class="reference"><a href="#cite_note-LinCbb15-40"><span class="cite-bracket">[</span>40<span class="cite-bracket">]</span></a></sup><sup>[<i>primary source</i>]</sup><sup class="noprint Inline-Template noprint noexcerpt Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:NOTRS" class="mw-redirect" title="Wikipedia:NOTRS"><span title="This claim needs references to better sources. (February 2017)">better source needed</span></a></i>]</sup> </p><p>In a small rabbit study, the impact of gelsemine administration on parameters relating to diet-induced hyperlipidemia was examined, where gelsemine was observed to improve lipid profile parameters associated with hyperlipidemia to a significant extent, as well as to "decreas[e] hyperlipidemia-induced oxidative stress in a dose-dependent manner," as determined by altered activities of a number of relevant metabolite and enzyme activity levels. The results, taken together, led the study authors to conclude that supplements of gelsemine to animals exposed to high fat diets may be of use in reversing the effects and in protecting tissues from oxidative stress resulting from such diets.<sup id="cite_ref-41" class="reference"><a href="#cite_note-41"><span class="cite-bracket">[</span>41<span class="cite-bracket">]</span></a></sup><sup>[<i>primary source</i>]</sup><sup class="noprint Inline-Template noprint noexcerpt Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:NOTRS" class="mw-redirect" title="Wikipedia:NOTRS"><span title="This claim needs references to better sources. (February 2017)">better source needed</span></a></i>]</sup> </p><p>Gelsemine has been observed to have anti-inflammatory activity.<sup class="noprint Inline-Template" style="margin-left:0.1em; white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Please_clarify" title="Wikipedia:Please clarify"><span title="The text near this tag may need clarification or removal of jargon. (February 2017)">clarification needed</span></a></i>]</sup><sup id="cite_ref-LinCbb15_40-1" class="reference"><a href="#cite_note-LinCbb15-40"><span class="cite-bracket">[</span>40<span class="cite-bracket">]</span></a></sup><sup>[<i>primary source</i>]</sup><sup class="noprint Inline-Template noprint noexcerpt Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:NOTRS" class="mw-redirect" title="Wikipedia:NOTRS"><span title="This claim needs references to better sources. (February 2017)">better source needed</span></a></i>]</sup> </p><p>Gelsemine has been observed to have anti-cancer activity.<sup class="noprint Inline-Template" style="margin-left:0.1em; white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Please_clarify" title="Wikipedia:Please clarify"><span title="The text near this tag may need clarification or removal of jargon. (February 2017)">clarification needed</span></a></i>]</sup><sup id="cite_ref-LinCbb15_40-2" class="reference"><a href="#cite_note-LinCbb15-40"><span class="cite-bracket">[</span>40<span class="cite-bracket">]</span></a></sup><sup>[<i>primary source</i>]</sup><sup class="noprint Inline-Template noprint noexcerpt Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:NOTRS" class="mw-redirect" title="Wikipedia:NOTRS"><span title="This claim needs references to better sources. (February 2017)">better source needed</span></a></i>]</sup> </p> <div class="mw-heading mw-heading3"><h3 id="Traditional_medical_uses">Traditional medical uses</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Gelsemine&action=edit&section=11" title="Edit section: Traditional medical uses"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Preparations from the plant from which gelsemine derives, <i>Gelsemium sempervirens</i>, have been used as treatment for a variety of ailments, for instance, through use of Gelsemium tinctures.<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (February 2017)">citation needed</span></a></i>]</sup> Applications have included treatment of acne, anxiety, ear pain, migraine, and more generally with diseases associated with an inflammatory response, and in cases of abnormal nervous function (paralysis, “pins and needles” feeling, neuralgia, etc.).<sup id="cite_ref-42" class="reference"><a href="#cite_note-42"><span class="cite-bracket">[</span>42<span class="cite-bracket">]</span></a></sup><sup class="noprint Inline-Template noprint noexcerpt Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:NOTRS" class="mw-redirect" title="Wikipedia:NOTRS"><span title="This claim needs references to better sources. (February 2017)">better source needed</span></a></i>]</sup><sup>[<i>primary source</i>]</sup><sup class="noprint Inline-Template" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Reliable_sources" title="Wikipedia:Reliable sources"><span title="The material near this tag relies on an unreliable source. dated, biased (February 2017)">unreliable source</span></a></i>]</sup> </p> <div class="mw-heading mw-heading2"><h2 id="Popular_culture">Popular culture</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Gelsemine&action=edit&section=12" title="Edit section: Popular culture"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Gelsemine is used indirectly, via the use of "yellow jasmine", in the 1927 Agatha Christie novel, <i><a href="/wiki/The_Big_Four_(novel)" title="The Big Four (novel)">The Big Four</a></i>, where an injection of this natural preparation is used to kill the character Mr. Paynter.<sup id="cite_ref-43" class="reference"><a href="#cite_note-43"><span class="cite-bracket">[</span>43<span class="cite-bracket">]</span></a></sup><sup class="noprint Inline-Template" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citing_sources" title="Wikipedia:Citing sources"><span title="This citation requires a reference to the specific page or range of pages in which the material appears. (February 2017)">page needed</span></a></i>]</sup> It is then used directly, in 2013, as gelsemine, in <a href="/wiki/List_of_Agatha_Christie%27s_Poirot_episodes#Series_13_.282013.29" title="List of Agatha Christie's Poirot episodes">series 13</a> of the <a href="/wiki/ITV_(TV_network)" title="ITV (TV network)">ITV</a> series, <i><a href="/wiki/Agatha_Christie%27s_Poirot" title="Agatha Christie's Poirot">Agatha Christie's Poirot</a></i>, as the agent to immobilize the character Stephen Paynter (played by Steven Pacey) before his being burnt to death, thus implicating the character Madame Olivier, a research neuroscientist (played by Patricia Hodge); and also, directly, to paralyze and immobilize Olivier and another character after their kidnappings.<sup id="cite_ref-44" class="reference"><a href="#cite_note-44"><span class="cite-bracket">[</span>44<span class="cite-bracket">]</span></a></sup> </p><p>In <i><a href="/wiki/House_of_Cards_(U.S._TV_series)" class="mw-redirect" title="House of Cards (U.S. TV series)">House of Cards</a></i> season 5 episode 12, Jane Davis offers Claire Underwood gelsemine as a headache reliever, noting that she should only use two drops. Later on, Claire uses the gelsemine to murder Tom Yates, her lover, by putting it into his drink without his knowledge.<sup id="cite_ref-45" class="reference"><a href="#cite_note-45"><span class="cite-bracket">[</span>45<span class="cite-bracket">]</span></a></sup> </p><p>In episode 9 of season 3 of <i><a href="/wiki/IZombie_(TV_series)" title="IZombie (TV series)">iZombie</a></i>, the victim is poisoned by gelsemine.<sup id="cite_ref-46" class="reference"><a href="#cite_note-46"><span class="cite-bracket">[</span>46<span class="cite-bracket">]</span></a></sup> </p> <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=Gelsemine&action=edit&section=13" title="Edit section: See also"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1184024115">.mw-parser-output .div-col{margin-top:0.3em;column-width:30em}.mw-parser-output .div-col-small{font-size:90%}.mw-parser-output .div-col-rules{column-rule:1px solid #aaa}.mw-parser-output .div-col dl,.mw-parser-output .div-col ol,.mw-parser-output .div-col ul{margin-top:0}.mw-parser-output .div-col li,.mw-parser-output .div-col dd{page-break-inside:avoid;break-inside:avoid-column}</style><div class="div-col" style="column-width: 18em;"> <ul><li><i><a href="/wiki/Gelsemium_sempervirens" title="Gelsemium sempervirens">Gelsemium sempervirens</a></i></li> <li><a href="/wiki/Strychnine" title="Strychnine">Strychnine</a></li> <li><a href="/wiki/Alkaloids" class="mw-redirect" title="Alkaloids">Alkaloids</a></li></ul> </div> <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=Gelsemine&action=edit&section=14" 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">Lin, Lin; Zheng, Jing; Zhu, Weiping; Jia, Ning (2015-03). "Nephroprotective Effect of Gelsemine Against Cisplatin-Induced Toxicity is Mediated Via Attenuation of Oxidative Stress". <i>Cell Biochemistry and Biophysics</i>. <b>71</b> (2): 535–541. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:10.1007/s12013-014-0231-y. <a href="/wiki/ISSN_(identifier)" class="mw-redirect" title="ISSN (identifier)">ISSN</a> 1085-9195.</span> </li> <li id="cite_note-2"><span class="mw-cite-backlink"><b><a href="#cite_ref-2">^</a></b></span> <span class="reference-text">Liu, Ming; Huang, Hui-Hui; Yang, Jian; Su, Yan-Ping; Lin, Hong-Wei; Lin, Li-Qing; Liao, Wei-Jian; Yu, Chang-Xi (2013-02). "The active alkaloids of Gelsemium elegans Benth. are potent anxiolytics". <i>Psychopharmacology</i>. <b>225</b> (4): 839–851. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:10.1007/s00213-012-2867-x. <a href="/wiki/ISSN_(identifier)" class="mw-redirect" title="ISSN (identifier)">ISSN</a> 0033-3158 </span> </li> <li id="cite_note-ZhangWang14r-3"><span class="mw-cite-backlink">^ <a href="#cite_ref-ZhangWang14r_3-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-ZhangWang14r_3-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-ZhangWang14r_3-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-ZhangWang14r_3-3"><sup><i><b>d</b></i></sup></a></span> <span class="reference-text"><style data-mw-deduplicate="TemplateStyles:r1238218222">.mw-parser-output cite.citation{font-style:inherit;word-wrap:break-word}.mw-parser-output .citation q{quotes:"\"""\"""'""'"}.mw-parser-output .citation:target{background-color:rgba(0,127,255,0.133)}.mw-parser-output .id-lock-free.id-lock-free a{background:url("//upload.wikimedia.org/wikipedia/commons/6/65/Lock-green.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-limited.id-lock-limited a,.mw-parser-output .id-lock-registration.id-lock-registration a{background:url("//upload.wikimedia.org/wikipedia/commons/d/d6/Lock-gray-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-subscription.id-lock-subscription a{background:url("//upload.wikimedia.org/wikipedia/commons/a/aa/Lock-red-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .cs1-ws-icon a{background:url("//upload.wikimedia.org/wikipedia/commons/4/4c/Wikisource-logo.svg")right 0.1em center/12px no-repeat}body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-free a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-limited a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-registration a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-subscription a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .cs1-ws-icon a{background-size:contain;padding:0 1em 0 0}.mw-parser-output .cs1-code{color:inherit;background:inherit;border:none;padding:inherit}.mw-parser-output .cs1-hidden-error{display:none;color:var(--color-error,#d33)}.mw-parser-output .cs1-visible-error{color:var(--color-error,#d33)}.mw-parser-output .cs1-maint{display:none;color:#085;margin-left:0.3em}.mw-parser-output .cs1-kern-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right{padding-right:0.2em}.mw-parser-output .citation .mw-selflink{font-weight:inherit}@media screen{.mw-parser-output .cs1-format{font-size:95%}html.skin-theme-clientpref-night .mw-parser-output .cs1-maint{color:#18911f}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .cs1-maint{color:#18911f}}</style><cite id="CITEREFZhangWang2015" class="citation journal cs1">Zhang JY, Wang YX (January 2015). "Gelsemium analgesia and the spinal glycine receptor/allopregnanolone pathway". <i>Fitoterapia</i>. <b>100</b> (C, November): 35–43. <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.fitote.2014.11.002">10.1016/j.fitote.2014.11.002</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/25447163">25447163</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Fitoterapia&rft.atitle=Gelsemium+analgesia+and+the+spinal+glycine+receptor%2Fallopregnanolone+pathway&rft.volume=100&rft.issue=C%2C+November&rft.pages=35-43&rft.date=2015-01&rft_id=info%3Adoi%2F10.1016%2Fj.fitote.2014.11.002&rft_id=info%3Apmid%2F25447163&rft.aulast=Zhang&rft.aufirst=JY&rft.au=Wang%2C+YX&rfr_id=info%3Asid%2Fen.wikipedia.org%3AGelsemine" class="Z3988"></span></span> </li> <li id="cite_note-Ornduff70-4"><span class="mw-cite-backlink">^ <a href="#cite_ref-Ornduff70_4-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Ornduff70_4-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-Ornduff70_4-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-Ornduff70_4-3"><sup><i><b>d</b></i></sup></a> <a href="#cite_ref-Ornduff70_4-4"><sup><i><b>e</b></i></sup></a> <a href="#cite_ref-Ornduff70_4-5"><sup><i><b>f</b></i></sup></a> <a href="#cite_ref-Ornduff70_4-6"><sup><i><b>g</b></i></sup></a> <a href="#cite_ref-Ornduff70_4-7"><sup><i><b>h</b></i></sup></a> <a href="#cite_ref-Ornduff70_4-8"><sup><i><b>i</b></i></sup></a> <a href="#cite_ref-Ornduff70_4-9"><sup><i><b>j</b></i></sup></a> <a href="#cite_ref-Ornduff70_4-10"><sup><i><b>k</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFOrnduff1970" class="citation journal cs1">Ornduff R (1970). <a rel="nofollow" class="external text" href="https://www.biodiversitylibrary.org/item/41431#page/7/mode/1up">"The Systematics and Breeding System of <i>Gelsemium</i> (Loganiceae)"</a> <span class="cs1-format">(review)</span>. <i>Journal of the Arnold Arboretum</i>. <b>51</b> (1): 1–17. <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/10.5962%2Fbhl.part.7036">10.5962/bhl.part.7036</a></span><span class="reference-accessdate">. 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Retrieved <span class="nowrap">February 18,</span> 2017</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=A+Guide+to+Plant+Poisoning+of+Animals+in+North+America&rft.place=Jackson%2C+WY&rft.series=Manson+Series&rft.pub=Teton+NewMedia&rft.date=2001&rft.isbn=978-1893441118&rft.aulast=Knight&rft.aufirst=A&rft.au=Walter%2C+R&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fisbn%3D1893441113&rfr_id=info%3Asid%2Fen.wikipedia.org%3AGelsemine" class="Z3988"></span><sup class="noprint Inline-Template" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citing_sources" title="Wikipedia:Citing sources"><span title="This citation requires a reference to the specific page or range of pages in which the material appears. (February 2017)">page needed</span></a></i>]</sup></span> </li> <li id="cite_note-24"><span class="mw-cite-backlink"><b><a href="#cite_ref-24">^</a></b></span> <span class="reference-text">In the case of <i><a href="/wiki/Bombus_impatiens" title="Bombus impatiens">Bombus impatiens</a></i> (bumblebees), feeding on gelsemine may reduce the load of the parasite <i><a href="/wiki/Crithidia" title="Crithidia">Crithidia bombi</a></i>, which, in improving bee health, increases foraging efficiency, a possible case of selective advantage of a pollinator self-medicating through collection of an otherwise generally toxic secondary metabolite. 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(February 2017)">page needed</span></a></i>]</sup></span> </li> <li id="cite_note-44"><span class="mw-cite-backlink"><b><a href="#cite_ref-44">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFEirik2013" class="citation web cs1">Eirik (30 October 2013). <a rel="nofollow" class="external text" href="http://investigatingpoirot.blogspot.com/2013/10/episode-by-episode-big-four.html">"Investigating Agatha Christie's Poirot: Episode-by-episode: The Big Four"</a>. <i>investigatingpoirot.blogspot.com</i><span class="reference-accessdate">. Retrieved <span class="nowrap">19 February</span> 2017</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=investigatingpoirot.blogspot.com&rft.atitle=Investigating+Agatha+Christie%27s+Poirot%3A+Episode-by-episode%3A+The+Big+Four&rft.date=2013-10-30&rft.au=Eirik&rft_id=http%3A%2F%2Finvestigatingpoirot.blogspot.com%2F2013%2F10%2Fepisode-by-episode-big-four.html&rfr_id=info%3Asid%2Fen.wikipedia.org%3AGelsemine" class="Z3988"></span></span> </li> <li id="cite_note-45"><span class="mw-cite-backlink"><b><a href="#cite_ref-45">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://www.springfieldspringfield.co.uk/view_episode_scripts.php?tv-show=house-of-cards-2013&episode=s05e12">"House of Cards (2013) s05e12"</a>. 2013.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=House+of+Cards+%282013%29+s05e12&rft.date=2013&rft_id=https%3A%2F%2Fwww.springfieldspringfield.co.uk%2Fview_episode_scripts.php%3Ftv-show%3Dhouse-of-cards-2013%26episode%3Ds05e12&rfr_id=info%3Asid%2Fen.wikipedia.org%3AGelsemine" class="Z3988"></span></span> </li> <li id="cite_note-46"><span class="mw-cite-backlink"><b><a href="#cite_ref-46">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://www.springfieldspringfield.co.uk/view_episode_scripts.php?tv-show=izombie-2015&episode=s03e09">"iZombie (2015) s03e09 Episode Script"</a>. 2015.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=iZombie+%282015%29+s03e09+Episode+Script&rft.date=2015&rft_id=https%3A%2F%2Fwww.springfieldspringfield.co.uk%2Fview_episode_scripts.php%3Ftv-show%3Dizombie-2015%26episode%3Ds03e09&rfr_id=info%3Asid%2Fen.wikipedia.org%3AGelsemine" class="Z3988"></span></span> </li> </ol></div> <div class="mw-heading mw-heading2"><h2 id="Further_reading">Further reading</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Gelsemine&action=edit&section=15" title="Edit section: Further reading"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1239549316">.mw-parser-output .refbegin{margin-bottom:0.5em}.mw-parser-output .refbegin-hanging-indents>ul{margin-left:0}.mw-parser-output .refbegin-hanging-indents>ul>li{margin-left:0;padding-left:3.2em;text-indent:-3.2em}.mw-parser-output .refbegin-hanging-indents ul,.mw-parser-output .refbegin-hanging-indents ul li{list-style:none}@media(max-width:720px){.mw-parser-output .refbegin-hanging-indents>ul>li{padding-left:1.6em;text-indent:-1.6em}}.mw-parser-output .refbegin-columns{margin-top:0.3em}.mw-parser-output .refbegin-columns ul{margin-top:0}.mw-parser-output .refbegin-columns li{page-break-inside:avoid;break-inside:avoid-column}@media screen{.mw-parser-output .refbegin{font-size:90%}}</style><div class="refbegin" style=""> <ul><li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFJinSuLiuXu2014" class="citation journal cs1">Jin GL, Su YP, Liu M, Xu Y, Yang J, Liao KJ, Yu CX (February 2014). "Medicinal plants of the genus Gelsemium (Gelsemiaceae, Gentianales)--a review of their phytochemistry, pharmacology, toxicology and traditional use". <i>Journal of Ethnopharmacology</i>. <b>152</b> (1): 33–52. <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.jep.2014.01.003">10.1016/j.jep.2014.01.003</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/24434844">24434844</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Journal+of+Ethnopharmacology&rft.atitle=Medicinal+plants+of+the+genus+Gelsemium+%28Gelsemiaceae%2C+Gentianales%29--a+review+of+their+phytochemistry%2C+pharmacology%2C+toxicology+and+traditional+use&rft.volume=152&rft.issue=1&rft.pages=33-52&rft.date=2014-02&rft_id=info%3Adoi%2F10.1016%2Fj.jep.2014.01.003&rft_id=info%3Apmid%2F24434844&rft.aulast=Jin&rft.aufirst=GL&rft.au=Su%2C+YP&rft.au=Liu%2C+M&rft.au=Xu%2C+Y&rft.au=Yang%2C+J&rft.au=Liao%2C+KJ&rft.au=Yu%2C+CX&rfr_id=info%3Asid%2Fen.wikipedia.org%3AGelsemine" class="Z3988"></span></li> <li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFPatte-MensahMeyerTalebMensah-Nyagan2014" class="citation journal cs1">Patte-Mensah C, Meyer L, Taleb O, Mensah-Nyagan AG (February 2014). "Potential role of allopregnanolone for a safe and effective therapy of neuropathic pain". <i>Progress in Neurobiology</i>. <b>113</b> (February): 70–78. <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.pneurobio.2013.07.004">10.1016/j.pneurobio.2013.07.004</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/23948490">23948490</a>. <a href="/wiki/S2CID_(identifier)" class="mw-redirect" title="S2CID (identifier)">S2CID</a> <a rel="nofollow" class="external text" href="https://api.semanticscholar.org/CorpusID:207407077">207407077</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Progress+in+Neurobiology&rft.atitle=Potential+role+of+allopregnanolone+for+a+safe+and+effective+therapy+of+neuropathic+pain&rft.volume=113&rft.issue=February&rft.pages=70-78&rft.date=2014-02&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A207407077%23id-name%3DS2CID&rft_id=info%3Apmid%2F23948490&rft_id=info%3Adoi%2F10.1016%2Fj.pneurobio.2013.07.004&rft.aulast=Patte-Mensah&rft.aufirst=C&rft.au=Meyer%2C+L&rft.au=Taleb%2C+O&rft.au=Mensah-Nyagan%2C+AG&rfr_id=info%3Asid%2Fen.wikipedia.org%3AGelsemine" class="Z3988"></span></li> <li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFDuttThakurDharSharma2010" class="citation journal cs1">Dutt V, Thakur S, Dhar VJ, Sharma A (July 2010). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3249920">"The genus Gelsemium: An update"</a>. <i>Pharmacognosy Reviews</i>. <b>4</b> (8): 185–194. <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/10.4103%2F0973-7847.70916">10.4103/0973-7847.70916</a></span>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3249920">3249920</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/22228960">22228960</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Pharmacognosy+Reviews&rft.atitle=The+genus+Gelsemium%3A+An+update&rft.volume=4&rft.issue=8&rft.pages=185-194&rft.date=2010-07&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC3249920%23id-name%3DPMC&rft_id=info%3Apmid%2F22228960&rft_id=info%3Adoi%2F10.4103%2F0973-7847.70916&rft.aulast=Dutt&rft.aufirst=V&rft.au=Thakur%2C+S&rft.au=Dhar%2C+VJ&rft.au=Sharma%2C+A&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC3249920&rfr_id=info%3Asid%2Fen.wikipedia.org%3AGelsemine" class="Z3988"></span></li> <li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFZhangWang2015" class="citation journal cs1">Zhang JY, Wang YX (January 2015). "Gelsemium analgesia and the spinal glycine receptor/allopregnanolone pathway". <i>Fitoterapia</i>. <b>100</b> (C, November): 35–43. <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.fitote.2014.11.002">10.1016/j.fitote.2014.11.002</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/25447163">25447163</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Fitoterapia&rft.atitle=Gelsemium+analgesia+and+the+spinal+glycine+receptor%2Fallopregnanolone+pathway&rft.volume=100&rft.issue=C%2C+November&rft.pages=35-43&rft.date=2015-01&rft_id=info%3Adoi%2F10.1016%2Fj.fitote.2014.11.002&rft_id=info%3Apmid%2F25447163&rft.aulast=Zhang&rft.aufirst=JY&rft.au=Wang%2C+YX&rfr_id=info%3Asid%2Fen.wikipedia.org%3AGelsemine" class="Z3988"></span></li> <li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFBrower2014" class="citation cs2">Brower J (August 12, 2014), <a rel="nofollow" class="external text" href="http://naturespoisons.com/2014/08/12/gelsemium-and-arthur-conan-doyle-the-self-poisoner-gelsemine-sherlock-holmes/"><i>Gelsemium and Sir Arthur Conan Doyle, the Self-Poisoner</i></a>, Nature's Poisons</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Gelsemium+and+Sir+Arthur+Conan+Doyle%2C+the+Self-Poisoner&rft.pub=Nature%27s+Poisons&rft.date=2014-08-12&rft.aulast=Brower&rft.aufirst=J&rft_id=http%3A%2F%2Fnaturespoisons.com%2F2014%2F08%2F12%2Fgelsemium-and-arthur-conan-doyle-the-self-poisoner-gelsemine-sherlock-holmes%2F&rfr_id=info%3Asid%2Fen.wikipedia.org%3AGelsemine" class="Z3988"></span></li></ul> </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 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 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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 class="mw-selflink selflink">Gelsemine</a></li> <li><a href="/w/index.php?title=Iso-THAZ&action=edit&redlink=1" class="new" title="Iso-THAZ (page does not exist)">iso-THAZ</a></li> <li><a href="/wiki/Isobutyric_acid" title="Isobutyric acid">Isobutyric acid</a></li> <li><a href="/wiki/Isonipecotic_acid" title="Isonipecotic acid">Isonipecotic acid</a></li> <li><a href="/w/index.php?title=Isostrychnine&action=edit&redlink=1" class="new" title="Isostrychnine (page does not exist)">Isostrychnine</a></li> <li><a href="/wiki/Laudanosine" title="Laudanosine">Laudanosine</a></li> <li><a href="/w/index.php?title=N-Methylbicuculline&action=edit&redlink=1" class="new" title="N-Methylbicuculline (page does not exist)">N-Methylbicuculline</a></li> <li><a href="/w/index.php?title=N-Methylstrychnine&action=edit&redlink=1" class="new" title="N-Methylstrychnine (page does not exist)">N-Methylstrychnine</a></li> <li><a href="/w/index.php?title=N,N-Dimethylmuscimol&action=edit&redlink=1" class="new" title="N,N-Dimethylmuscimol (page does not exist)">N,N-Dimethylmuscimol</a></li> <li><a href="/wiki/Nipecotic_acid" title="Nipecotic acid">Nipecotic acid</a></li> <li><a href="/wiki/Pitrazepin" title="Pitrazepin">Pitrazepin</a></li> <li><a href="/w/index.php?title=Pseudostrychnine&action=edit&redlink=1" class="new" title="Pseudostrychnine (page does not exist)">Pseudostrychnine</a></li> <li><a href="/wiki/Quinoline" title="Quinoline">Quinolines</a> (e.g., <a href="/w/index.php?title=4-hydroxyquinoline&action=edit&redlink=1" class="new" title="4-hydroxyquinoline (page does not exist)">4-hydroxyquinoline</a>, <a href="/w/index.php?title=4-hydroxyquinoline-3-carboxylic_acid&action=edit&redlink=1" class="new" title="4-hydroxyquinoline-3-carboxylic acid (page does not exist)">4-hydroxyquinoline-3-carboxylic acid</a>, <a href="/w/index.php?title=5,7-dichloro-4-hydroxyquinoline-3-carboxylic_acid&action=edit&redlink=1" class="new" title="5,7-dichloro-4-hydroxyquinoline-3-carboxylic acid (page does not exist)">5,7-CIQA</a>, <a href="/w/index.php?title=7-chloro-4-hydroxyquinoline&action=edit&redlink=1" class="new" title="7-chloro-4-hydroxyquinoline (page does not exist)">7-CIQ</a>, <a href="/w/index.php?title=7-trifluoromethyl-4-hydroxyquinoline&action=edit&redlink=1" class="new" title="7-trifluoromethyl-4-hydroxyquinoline (page does not exist)">7-TFQ</a>, <a href="/w/index.php?title=7-trifluoromethyl-4-hydroxyquinoline-3-carboxylic_acid&action=edit&redlink=1" class="new" title="7-trifluoromethyl-4-hydroxyquinoline-3-carboxylic acid (page does not exist)">7-TFQA</a>)</li> <li><a href="/w/index.php?title=RU-5135&action=edit&redlink=1" class="new" title="RU-5135 (page does not exist)">RU-5135</a></li> <li><a href="/wiki/Sinomenine" title="Sinomenine">Sinomenine</a></li> <li><a href="/wiki/Strychnine" title="Strychnine">Strychnine</a></li> <li><a href="/wiki/Thiocolchicoside" title="Thiocolchicoside">Thiocolchicoside</a></li> <li><a href="/wiki/Tutin_(toxin)" title="Tutin (toxin)">Tutin</a></li></ul> <ul><li><b>Negative modulators:</b> <a href="/wiki/Amiloride" title="Amiloride">Amiloride</a></li> <li><a href="/wiki/Benzodiazepine" title="Benzodiazepine">Benzodiazepines</a> (e.g., <a href="/wiki/Bromazepam" title="Bromazepam">bromazepam</a>, <a href="/wiki/Clonazepam" title="Clonazepam">clonazepam</a>, <a href="/wiki/Diazepam" title="Diazepam">diazepam</a>, <a href="/wiki/Flunitrazepam" title="Flunitrazepam">flunitrazepam</a>, <a href="/wiki/Flurazepam" title="Flurazepam">flurazepam</a>)</li> <li><a href="/wiki/Corymine" title="Corymine">Corymine</a></li> <li><a href="/w/index.php?title=Cyanotriphenylborate&action=edit&redlink=1" class="new" title="Cyanotriphenylborate (page does not exist)">Cyanotriphenylborate</a></li> <li><a href="/wiki/Daidzein" title="Daidzein">Daidzein</a></li> <li><a href="/wiki/Dihydropyridine" class="mw-redirect" title="Dihydropyridine">Dihydropyridines</a> (e.g., <a href="/wiki/Nicardipine" title="Nicardipine">nicardipine</a>, <a href="/wiki/Nifedipine" title="Nifedipine">nifedipine</a>, <a href="/wiki/Nitrendipine" title="Nitrendipine">nitrendipine</a>)</li> <li><a href="/wiki/Furosemide" title="Furosemide">Furosemide</a></li> <li><a href="/wiki/Genistein" title="Genistein">Genistein</a></li> <li><a href="/wiki/Ginkgo_biloba" title="Ginkgo biloba">Ginkgo</a> constituents (e.g., <a href="/wiki/Bilobalide" title="Bilobalide">bilobalide</a>, <a href="/wiki/Ginkgolide" title="Ginkgolide">ginkgolides</a> (e.g., <a href="/w/index.php?title=Ginkgolide_A&action=edit&redlink=1" class="new" title="Ginkgolide A (page does not exist)">ginkgolide A</a>, <a href="/wiki/Ginkgolide_B" class="mw-redirect" title="Ginkgolide B">ginkgolide B</a>, <a href="/w/index.php?title=Ginkgolide_C&action=edit&redlink=1" class="new" title="Ginkgolide C (page does not exist)">ginkgolide C</a>, <a href="/w/index.php?title=Ginkgolide_J&action=edit&redlink=1" class="new" title="Ginkgolide J (page does not exist)">ginkgolide J</a>, <a href="/w/index.php?title=Ginkgolide_M&action=edit&redlink=1" class="new" title="Ginkgolide M (page does not exist)">ginkgolide M</a>))</li> <li><a href="/wiki/Imipramine" title="Imipramine">Imipramine</a></li> <li><a href="/wiki/NBQX" title="NBQX">NBQX</a></li> <li><a href="/wiki/Neuroactive_steroid" class="mw-redirect" title="Neuroactive steroid">Neuroactive steroids</a> (e.g., <a href="/wiki/3%CE%B1-androsterone_sulfate" class="mw-redirect" title="3α-androsterone sulfate">3α-androsterone sulfate</a>, <a href="/w/index.php?title=3%CE%B2-androsterone_sulfate&action=edit&redlink=1" class="new" title="3β-androsterone sulfate (page does not exist)">3β-androsterone sulfate</a>, <a href="/wiki/11-deoxycorticosterone" class="mw-redirect" title="11-deoxycorticosterone">deoxycorticosterone</a>, <a href="/wiki/DHEA_sulfate" class="mw-redirect" title="DHEA sulfate">DHEA sulfate</a>, <a href="/wiki/Pregnenolone_sulfate" title="Pregnenolone sulfate">pregnenolone sulfate</a>, <a href="/wiki/Progesterone" title="Progesterone">progesterone</a>)</li> <li><a href="/wiki/Opioid" title="Opioid">Opioids</a> (e.g., <a href="/wiki/Codeine" title="Codeine">codeine</a>, <a href="/wiki/Dextromethorphan" title="Dextromethorphan">dextromethorphan</a>, <a href="/wiki/Dextrorphan" title="Dextrorphan">dextrorphan</a>, <a href="/wiki/Levomethadone" title="Levomethadone">levomethadone</a>, <a href="/wiki/Levorphanol" title="Levorphanol">levorphanol</a>, <a href="/wiki/Morphine" title="Morphine">morphine</a>, <a href="/wiki/Oripavine" title="Oripavine">oripavine</a>, <a href="/wiki/Pethidine" title="Pethidine">pethidine</a>, <a href="/wiki/Thebaine" title="Thebaine">thebaine</a>)</li> <li><a href="/wiki/Picrotoxin" title="Picrotoxin">Picrotoxin</a> (i.e., <a href="/wiki/Picrotin" class="mw-redirect" title="Picrotin">picrotin</a> and <a href="/wiki/Picrotoxinin" class="mw-redirect" title="Picrotoxinin">picrotoxinin</a>)</li> <li><a href="/w/index.php?title=Phenylbenzene_%CF%89-phosphono-%CE%B1-amino_acid&action=edit&redlink=1" class="new" title="Phenylbenzene ω-phosphono-α-amino acid (page does not exist)">PMBA</a></li> <li><a href="/wiki/Riluzole" title="Riluzole">Riluzole</a></li> <li><a href="/w/index.php?title=Tropeine&action=edit&redlink=1" class="new" title="Tropeine (page does not exist)">Tropeines</a> (e.g., <a href="/wiki/Bemesetron" title="Bemesetron">bemesetron</a>, <a href="/w/index.php?title=LY-278584&action=edit&redlink=1" class="new" title="LY-278584 (page does not exist)">LY-278584</a>, <a href="/wiki/Tropisetron" title="Tropisetron">tropisetron</a>, <a href="/wiki/Zatosetron" title="Zatosetron">zatosetron</a>)</li> <li><a href="/wiki/Verapamil" title="Verapamil">Verapamil</a></li> <li><a href="/wiki/Zinc" title="Zinc">Zinc</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:4em;;text-align:center;"><a href="/wiki/N-Methyl-D-aspartate_receptor" class="mw-redirect" title="N-Methyl-D-aspartate receptor"><abbr title="N-Methyl-D-aspartate receptor">NMDAR</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip N-Methyl-D-aspartate receptor</span></th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li>See <a href="/wiki/Template:Ionotropic_glutamate_receptor_modulators" title="Template:Ionotropic glutamate receptor modulators">here</a> instead.</li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Neurotransmitter_transporter" title="Neurotransmitter transporter">Transporter</a><br /><small>(<a href="/wiki/Reuptake_inhibitor" title="Reuptake inhibitor">blockers</a>)</small></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:4em;;text-align:center;"><a href="/wiki/Glycine_transporter_1" class="mw-redirect" title="Glycine transporter 1"><abbr title="Glycine transporter 1">GlyT1</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Glycine transporter 1</span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/w/index.php?title=ACPPB&action=edit&redlink=1" class="new" title="ACPPB (page does not exist)">ACPPB</a></li> <li><a href="/w/index.php?title=ALX-5407&action=edit&redlink=1" class="new" title="ALX-5407 (page does not exist)">ALX-5407 (NFPS)</a></li> <li><a href="/wiki/ASP2535" title="ASP2535">ASP2535</a></li> <li><a href="/wiki/Bitopertin" title="Bitopertin">Bitopertin (RG1678/RO4917838)</a></li> <li><a href="/w/index.php?title=CP-802079&action=edit&redlink=1" class="new" title="CP-802079 (page does not exist)">CP-802079</a></li> <li><a href="/wiki/Alcohol_(drug)" title="Alcohol (drug)">Ethanol (alcohol)</a></li> <li><a href="/w/index.php?title=Glycyldodecylamide&action=edit&redlink=1" class="new" title="Glycyldodecylamide (page does not exist)">Glycyldodecylamide</a></li> <li><a href="/w/index.php?title=GSK1018921&action=edit&redlink=1" class="new" title="GSK1018921 (page does not exist)">GSK1018921</a></li> <li><a href="/wiki/Iclepertin" title="Iclepertin">Iclepertin</a></li> <li><a href="/wiki/LY-2365109" title="LY-2365109">LY-2365109</a></li> <li><a href="/wiki/Mardepodect" title="Mardepodect">Mardepodect</a></li> <li><a href="/wiki/ORG-24598" title="ORG-24598">ORG-24598</a></li> <li><a href="/wiki/ORG-25935" title="ORG-25935">ORG-25935 (SCH-900435)</a></li> <li><a href="/wiki/Pesampator" title="Pesampator">Pesampator (BIIB-104, PF-04958242)</a></li> <li><a href="/w/index.php?title=PF-03463275&action=edit&redlink=1" class="new" title="PF-03463275 (page does not exist)">PF-03463275</a></li> <li><a href="/wiki/Sarcosine" title="Sarcosine">Sarcosine</a></li> <li><a href="/wiki/SNG-12" title="SNG-12">SNG-12 (Synapsinae)</a></li> <li><a href="/w/index.php?title=SSR-103,800&action=edit&redlink=1" class="new" title="SSR-103,800 (page does not exist)">SSR-103,800</a></li> <li><a href="/w/index.php?title=SSR-504,734&action=edit&redlink=1" class="new" title="SSR-504,734 (page does not exist)">SSR-504,734</a></li> <li><a href="/wiki/Tilapertin" title="Tilapertin">Tilapertin</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:4em;;text-align:center;"><a href="/wiki/Glycine_transporter_2" class="mw-redirect" title="Glycine transporter 2"><abbr title="Glycine transporter 2">GlyT2</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Glycine transporter 2</span></th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/ALX-1393" title="ALX-1393">ALX-1393</a></li> <li><a href="/wiki/Amoxapine" title="Amoxapine">Amoxapine</a></li> <li><a href="/wiki/Alcohol_(drug)" title="Alcohol (drug)">Ethanol (alcohol)</a></li> <li><a href="/wiki/N-Arachidonylglycine" title="N-Arachidonylglycine">NAGly</a></li> <li><a href="/wiki/Opiranserin" title="Opiranserin">Opiranserin (VVZ-149)</a></li> <li><a href="/w/index.php?title=ORG-25543&action=edit&redlink=1" class="new" title="ORG-25543 (page does not exist)">ORG-25543</a></li> <li><a href="/w/index.php?title=VVZ-368&action=edit&redlink=1" class="new" title="VVZ-368 (page does not exist)">VVZ-368</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><td class="navbox-abovebelow" colspan="2"><div> <dl><dt>See also</dt> <dd><i><a href="/wiki/Template:Receptor_modulators" title="Template:Receptor modulators">Receptor/signaling modulators</a></i></dd> <dd><i><a href="/wiki/Template:GABA_receptor_modulators" title="Template:GABA receptor modulators">GABA receptor modulators</a></i></dd> <dd><i><a href="/wiki/Template:GABAA_receptor_positive_modulators" title="Template:GABAA receptor positive modulators">GABA<sub>A</sub> receptor positive modulators</a></i></dd> <dd><i><a href="/wiki/Template:Ionotropic_glutamate_receptor_modulators" title="Template:Ionotropic glutamate receptor modulators">Ionotropic glutamate receptor modulators</a></i></dd></dl> </div></td></tr></tbody></table></div>    </div><noscript><img src="https://login.wikimedia.org/wiki/Special:CentralAutoLogin/start?type=1x1" alt="" width="1" height="1" style="border: none; position: absolute;"></noscript> <div class="printfooter" data-nosnippet="">Retrieved from "<a dir="ltr" href="https://en.wikipedia.org/w/index.php?title=Gelsemine&oldid=1188198626">https://en.wikipedia.org/w/index.php?title=Gelsemine&oldid=1188198626</a>"</div></div> <div id="catlinks" class="catlinks" data-mw="interface"><div id="mw-normal-catlinks" class="mw-normal-catlinks"><a href="/wiki/Help:Category" title="Help:Category">Categories</a>: <ul><li><a href="/wiki/Category:Drugs_not_assigned_an_ATC_code" title="Category:Drugs not assigned an ATC code">Drugs not assigned an ATC code</a></li><li><a href="/wiki/Category:Indole_alkaloids" title="Category:Indole alkaloids">Indole alkaloids</a></li><li><a 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