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id="toc-Oneirogen" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Oneirogen"> <div class="vector-toc-text"> <span class="vector-toc-numb">8.4</span> <span>Oneirogen</span> </div> </a> <ul id="toc-Oneirogen-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-References" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#References"> <div class="vector-toc-text"> <span class="vector-toc-numb">9</span> <span>References</span> </div> </a> <ul id="toc-References-sublist" class="vector-toc-list"> </ul> </li> </ul> </div> </div> </nav> </div> </div> <div class="mw-content-container"> <main id="content" class="mw-body"> <header class="mw-body-header vector-page-titlebar"> <nav aria-label="Contents" class="vector-toc-landmark"> <div id="vector-page-titlebar-toc" class="vector-dropdown vector-page-titlebar-toc vector-button-flush-left" > <input type="checkbox" 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href="https://azb.wikipedia.org/wiki/%D9%82%D8%A7%D9%84%D8%A7%D9%86%D8%AA%D8%A7%D9%85%DB%8C%D9%86" title="قالانتامین – South Azerbaijani" lang="azb" hreflang="azb" data-title="قالانتامین" data-language-autonym="تۆرکجه" data-language-local-name="South Azerbaijani" class="interlanguage-link-target"><span>تۆرکجه</span></a></li><li class="interlanguage-link interwiki-bg mw-list-item"><a href="https://bg.wikipedia.org/wiki/%D0%93%D0%B0%D0%BB%D0%B0%D0%BD%D1%82%D0%B0%D0%BC%D0%B8%D0%BD" title="Галантамин – Bulgarian" lang="bg" hreflang="bg" data-title="Галантамин" data-language-autonym="Български" data-language-local-name="Bulgarian" class="interlanguage-link-target"><span>Български</span></a></li><li class="interlanguage-link interwiki-cy mw-list-item"><a href="https://cy.wikipedia.org/wiki/Galantamin" title="Galantamin – Welsh" lang="cy" hreflang="cy" data-title="Galantamin" data-language-autonym="Cymraeg" data-language-local-name="Welsh" class="interlanguage-link-target"><span>Cymraeg</span></a></li><li class="interlanguage-link interwiki-de mw-list-item"><a href="https://de.wikipedia.org/wiki/Galantamin" title="Galantamin – German" lang="de" hreflang="de" data-title="Galantamin" data-language-autonym="Deutsch" data-language-local-name="German" class="interlanguage-link-target"><span>Deutsch</span></a></li><li class="interlanguage-link interwiki-es mw-list-item"><a href="https://es.wikipedia.org/wiki/Galantamina" title="Galantamina – Spanish" lang="es" hreflang="es" data-title="Galantamina" data-language-autonym="Español" data-language-local-name="Spanish" class="interlanguage-link-target"><span>Español</span></a></li><li class="interlanguage-link interwiki-fa mw-list-item"><a href="https://fa.wikipedia.org/wiki/%DA%AF%D8%A7%D9%84%D8%A7%D9%86%D8%AA%D8%A7%D9%85%DB%8C%D9%86" title="گالانتامین – Persian" lang="fa" hreflang="fa" data-title="گالانتامین" data-language-autonym="فارسی" data-language-local-name="Persian" class="interlanguage-link-target"><span>فارسی</span></a></li><li class="interlanguage-link interwiki-fr mw-list-item"><a href="https://fr.wikipedia.org/wiki/Galantamine" title="Galantamine – French" lang="fr" hreflang="fr" data-title="Galantamine" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target"><span>Français</span></a></li><li class="interlanguage-link interwiki-it mw-list-item"><a href="https://it.wikipedia.org/wiki/Galantamina" title="Galantamina – Italian" lang="it" hreflang="it" data-title="Galantamina" data-language-autonym="Italiano" data-language-local-name="Italian" class="interlanguage-link-target"><span>Italiano</span></a></li><li class="interlanguage-link interwiki-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/Galantamine" title="Galantamine – Dutch" lang="nl" hreflang="nl" data-title="Galantamine" data-language-autonym="Nederlands" data-language-local-name="Dutch" class="interlanguage-link-target"><span>Nederlands</span></a></li><li class="interlanguage-link interwiki-ja mw-list-item"><a href="https://ja.wikipedia.org/wiki/%E3%82%AC%E3%83%A9%E3%83%B3%E3%82%BF%E3%83%9F%E3%83%B3" title="ガランタミン – Japanese" lang="ja" hreflang="ja" data-title="ガランタミン" data-language-autonym="日本語" data-language-local-name="Japanese" class="interlanguage-link-target"><span>日本語</span></a></li><li class="interlanguage-link interwiki-or mw-list-item"><a href="https://or.wikipedia.org/wiki/%E0%AC%97%E0%AC%BE%E0%AC%B2%E0%AC%BE%E0%AC%A3%E0%AD%8D%E0%AC%9F%E0%AC%BE%E0%AC%AE%E0%AC%BE%E0%AC%87%E0%AC%A8" title="ଗାଲାଣ୍ଟାମାଇନ – Odia" lang="or" hreflang="or" data-title="ଗାଲାଣ୍ଟାମାଇନ" data-language-autonym="ଓଡ଼ିଆ" data-language-local-name="Odia" class="interlanguage-link-target"><span>ଓଡ଼ିଆ</span></a></li><li class="interlanguage-link interwiki-uz mw-list-item"><a href="https://uz.wikipedia.org/wiki/Galantamin" title="Galantamin – Uzbek" lang="uz" hreflang="uz" data-title="Galantamin" data-language-autonym="Oʻzbekcha / ўзбекча" data-language-local-name="Uzbek" class="interlanguage-link-target"><span>Oʻzbekcha / ўзбекча</span></a></li><li class="interlanguage-link interwiki-pl mw-list-item"><a href="https://pl.wikipedia.org/wiki/Galantamina" title="Galantamina – Polish" lang="pl" hreflang="pl" data-title="Galantamina" data-language-autonym="Polski" data-language-local-name="Polish" class="interlanguage-link-target"><span>Polski</span></a></li><li class="interlanguage-link interwiki-pt mw-list-item"><a href="https://pt.wikipedia.org/wiki/Galantamina" title="Galantamina – Portuguese" lang="pt" hreflang="pt" data-title="Galantamina" data-language-autonym="Português" data-language-local-name="Portuguese" class="interlanguage-link-target"><span>Português</span></a></li><li class="interlanguage-link interwiki-ro mw-list-item"><a href="https://ro.wikipedia.org/wiki/Galantamin%C4%83" title="Galantamină – Romanian" lang="ro" hreflang="ro" data-title="Galantamină" data-language-autonym="Română" data-language-local-name="Romanian" class="interlanguage-link-target"><span>Română</span></a></li><li class="interlanguage-link interwiki-ru mw-list-item"><a href="https://ru.wikipedia.org/wiki/%D0%93%D0%B0%D0%BB%D0%B0%D0%BD%D1%82%D0%B0%D0%BC%D0%B8%D0%BD" title="Галантамин – Russian" lang="ru" hreflang="ru" data-title="Галантамин" data-language-autonym="Русский" data-language-local-name="Russian" class="interlanguage-link-target"><span>Русский</span></a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/Galantamin" title="Galantamin – Serbian" lang="sr" hreflang="sr" data-title="Galantamin" data-language-autonym="Српски / srpski" data-language-local-name="Serbian" class="interlanguage-link-target"><span>Српски / srpski</span></a></li><li class="interlanguage-link interwiki-sh mw-list-item"><a href="https://sh.wikipedia.org/wiki/Galantamin" title="Galantamin – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Galantamin" data-language-autonym="Srpskohrvatski / српскохрватски" data-language-local-name="Serbo-Croatian" class="interlanguage-link-target"><span>Srpskohrvatski / српскохрватски</span></a></li><li class="interlanguage-link interwiki-fi mw-list-item"><a href="https://fi.wikipedia.org/wiki/Galantamiini" title="Galantamiini – Finnish" lang="fi" hreflang="fi" data-title="Galantamiini" data-language-autonym="Suomi" data-language-local-name="Finnish" class="interlanguage-link-target"><span>Suomi</span></a></li><li class="interlanguage-link interwiki-sv mw-list-item"><a href="https://sv.wikipedia.org/wiki/Galantamin" title="Galantamin – Swedish" lang="sv" hreflang="sv" data-title="Galantamin" data-language-autonym="Svenska" data-language-local-name="Swedish" class="interlanguage-link-target"><span>Svenska</span></a></li><li class="interlanguage-link interwiki-tg mw-list-item"><a href="https://tg.wikipedia.org/wiki/%D0%93%D0%B0%D0%BB%D0%B0%D0%BD%D1%82%D0%B0%D0%BC%D0%B8%D0%BD" 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</div> </nav> <nav class="vector-appearance-landmark" aria-label="Appearance"> <div id="vector-appearance-pinned-container" class="vector-pinned-container"> <div id="vector-appearance" class="vector-appearance vector-pinnable-element"> <div class="vector-pinnable-header vector-appearance-pinnable-header vector-pinnable-header-pinned" data-feature-name="appearance-pinned" data-pinnable-element-id="vector-appearance" data-pinned-container-id="vector-appearance-pinned-container" data-unpinned-container-id="vector-appearance-unpinned-container" > <div class="vector-pinnable-header-label">Appearance</div> <button class="vector-pinnable-header-toggle-button vector-pinnable-header-pin-button" data-event-name="pinnable-header.vector-appearance.pin">move to sidebar</button> <button class="vector-pinnable-header-toggle-button vector-pinnable-header-unpin-button" data-event-name="pinnable-header.vector-appearance.unpin">hide</button> </div> </div> </div> </nav> </div> </div> <div id="bodyContent" class="vector-body" aria-labelledby="firstHeading" data-mw-ve-target-container> <div class="vector-body-before-content"> <div class="mw-indicators"> </div> <div id="siteSub" class="noprint">From Wikipedia, the free encyclopedia</div> </div> <div id="contentSub"><div id="mw-content-subtitle"></div></div> <div id="mw-content-text" class="mw-body-content"><div class="mw-content-ltr mw-parser-output" lang="en" dir="ltr"><div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Neurological medication</div> <p class="mw-empty-elt"> </p> <style data-mw-deduplicate="TemplateStyles:r1257001546">.mw-parser-output .infobox-subbox{padding:0;border:none;margin:-3px;width:auto;min-width:100%;font-size:100%;clear:none;float:none;background-color:transparent}.mw-parser-output .infobox-3cols-child{margin:auto}.mw-parser-output .infobox .navbar{font-size:100%}@media screen{html.skin-theme-clientpref-night .mw-parser-output .infobox-full-data:not(.notheme)>div:not(.notheme)[style]{background:#1f1f23!important;color:#f8f9fa}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .infobox-full-data:not(.notheme) div:not(.notheme){background:#1f1f23!important;color:#f8f9fa}}@media(min-width:640px){body.skin--responsive .mw-parser-output .infobox-table{display:table!important}body.skin--responsive .mw-parser-output .infobox-table>caption{display:table-caption!important}body.skin--responsive .mw-parser-output .infobox-table>tbody{display:table-row-group}body.skin--responsive .mw-parser-output .infobox-table tr{display:table-row!important}body.skin--responsive .mw-parser-output .infobox-table th,body.skin--responsive .mw-parser-output .infobox-table td{padding-left:inherit;padding-right:inherit}}</style><table class="infobox" style="border-spacing:2px;"><caption class="infobox-title"><span title="International nonproprietary name (INN): Galantamine">Galantamine</span></caption><tbody><tr><td colspan="2" class="infobox-image notheme" style="background-color: #f8f9fa;"><span class="mw-default-size" typeof="mw:File/Frameless"><a href="/wiki/File:Galantamine.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/7/71/Galantamine.svg/220px-Galantamine.svg.png" decoding="async" width="220" height="225" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/7/71/Galantamine.svg/330px-Galantamine.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/7/71/Galantamine.svg/440px-Galantamine.svg.png 2x" data-file-width="512" data-file-height="523" /></a></span></td></tr><tr><td colspan="2" class="infobox-image notheme" style="background-color: #f8f9fa;"><span class="mw-default-size" typeof="mw:File/Frameless"><a href="/wiki/File:Galantamine_3D.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/8/8a/Galantamine_3D.png/220px-Galantamine_3D.png" decoding="async" width="220" height="220" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/8/8a/Galantamine_3D.png/330px-Galantamine_3D.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/8/8a/Galantamine_3D.png/440px-Galantamine_3D.png 2x" data-file-width="2999" data-file-height="2999" /></a></span></td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd">Clinical data</th></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Drug_nomenclature#Trade_names" title="Drug nomenclature">Trade names</a></th><td class="infobox-data">Razadyne, others</td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/American_Society_of_Health-System_Pharmacists" title="American Society of Health-System Pharmacists">AHFS</a>/<a href="/wiki/Drugs.com" title="Drugs.com">Drugs.com</a></th><td class="infobox-data"><span title="www.drugs.com"><a rel="nofollow" class="external text" href="https://www.drugs.com/monograph/galantamine-hydrobromide.html">Monograph</a></span></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/MedlinePlus" title="MedlinePlus">MedlinePlus</a></th><td class="infobox-data"><span title="medlineplus.gov"><a rel="nofollow" class="external text" href="https://medlineplus.gov/druginfo/meds/a699058.html">a699058</a></span></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Regulation_of_therapeutic_goods" title="Regulation of therapeutic goods">License data</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><small><abbr class="country-name" title="United States">US</abbr></small> <a href="/wiki/DailyMed" title="DailyMed">DailyMed</a>: <span title="dailymed.nlm.nih.gov"><a rel="nofollow" class="external text" href="https://dailymed.nlm.nih.gov/dailymed/search.cfm?labeltype=all&query=Razadyne">Razadyne</a></span></li></ul></div> </td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Pregnancy_category" title="Pregnancy category">Pregnancy<br />category</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"> <ul><li><small><abbr class="country-name" title="Australia">AU</abbr>:</small> B1<sup id="cite_ref-Drugs.com_pregnancy_1-0" class="reference"><a href="#cite_note-Drugs.com_pregnancy-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup></li> <li class="mw-empty-elt"></li></ul> </div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Route_of_administration" title="Route of administration">Routes of<br />administration</a></th><td class="infobox-data"><a href="/wiki/Oral_administration" title="Oral administration">By mouth</a></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Anatomical_Therapeutic_Chemical_Classification_System" title="Anatomical Therapeutic Chemical Classification System">ATC code</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><a href="/wiki/ATC_code_N06" title="ATC code N06">N06DA04</a> (<span title="www.whocc.no"><a rel="nofollow" class="external text" href="https://www.whocc.no/atc_ddd_index/?code=N06DA04">WHO</a></span>) </li></ul></div></td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd">Legal status</th></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Regulation_of_therapeutic_goods" title="Regulation of therapeutic goods">Legal status</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"> <ul><li><small><abbr class="country-name" title="Brazil">BR</abbr>:</small> <a href="/wiki/Brazilian_Controlled_Drugs_and_Substances_Act#Class_C1" title="Brazilian Controlled Drugs and Substances Act">Class C1</a> (Other controlled substances)<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></li> <li><small><abbr class="country-name" title="United States">US</abbr>:</small> <a href="/wiki/Prescription_drug" title="Prescription drug">℞-only</a><sup id="cite_ref-Razadyne_FDA_label_3-0" class="reference"><a href="#cite_note-Razadyne_FDA_label-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup></li> <li><small><abbr class="country-name" title="European Union">EU</abbr>:</small> Rx-only<sup id="cite_ref-4" class="reference"><a href="#cite_note-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup></li> <li>In general: ℞ (Prescription only)</li></ul></div> </td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd"><a href="/wiki/Pharmacokinetics" title="Pharmacokinetics">Pharmacokinetic</a> data</th></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Bioavailability" title="Bioavailability">Bioavailability</a></th><td class="infobox-data">80–100%</td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Plasma_protein_binding" title="Plasma protein binding">Protein binding</a></th><td class="infobox-data">18%</td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Drug_metabolism" title="Drug metabolism">Metabolism</a></th><td class="infobox-data"><a href="/wiki/Liver" title="Liver">Liver</a> partially <a href="/wiki/Cytochrome_P450_oxidase" class="mw-redirect" title="Cytochrome P450 oxidase">CYP450</a>:<a href="/wiki/CYP2D6" title="CYP2D6">CYP2D6</a>/<a href="/wiki/CYP3A4" title="CYP3A4">3A4</a> substrate</td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Biological_half-life" title="Biological half-life">Elimination <span class="nowrap">half-life</span></a></th><td class="infobox-data">7 hours</td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Excretion" title="Excretion">Excretion</a></th><td class="infobox-data"><a href="/wiki/Kidney" title="Kidney">Kidney</a> (95%, of which 32% unchanged), fecal (5%)</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%;">(4a<i>S</i>,6<i>R</i>,8a<i>S</i>)-5,6,9,10,11,12-Hexahydro-3-methoxy-11-methyl-4a<i>H</i>-[1]benzofuro[3a,3,2-<i>ef</i>] [2]benzazepin-6-ol</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=357-70-0">357-70-0</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/PubChem#CID" title="PubChem">PubChem</a> <span style="font-weight:normal"><abbr title="Compound ID">CID</abbr></span></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="pubchem.ncbi.nlm.nih.gov"><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/9651">9651</a></span></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Guide_to_Pharmacology" title="Guide to Pharmacology">IUPHAR/BPS</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.guidetopharmacology.org"><a rel="nofollow" class="external text" href="https://www.guidetopharmacology.org/GRAC/LigandDisplayForward?ligandId=6693">6693</a></span></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/DrugBank" title="DrugBank">DrugBank</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.drugbank.ca"><a rel="nofollow" class="external text" href="https://www.drugbank.ca/drugs/DB00674">DB00674</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/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.9272.html">9272</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Unique_Ingredient_Identifier" title="Unique Ingredient Identifier">UNII</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="precision.fda.gov"><a rel="nofollow" class="external text" href="https://precision.fda.gov/uniisearch/srs/unii/0D3Q044KCA">0D3Q044KCA</a></span></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/KEGG" title="KEGG">KEGG</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.kegg.jp"><a rel="nofollow" class="external text" href="https://www.kegg.jp/entry/D04292">D04292</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/ChEBI" title="ChEBI">ChEBI</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.ebi.ac.uk"><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:42944">CHEBI:42944</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/ChEMBL" title="ChEMBL">ChEMBL</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.ebi.ac.uk"><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chembldb/index.php/compound/inspect/ChEMBL659">ChEMBL659</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Protein_Data_Bank" title="Protein Data Bank">PDB ligand</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li>GNT (<span title="www.ebi.ac.uk"><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/pdbe-srv/PDBeXplore/ligand/?ligand=GNT">PDBe</a></span>, <span title="www.rcsb.org"><a rel="nofollow" class="external text" href="https://www.rcsb.org/ligand/GNT">RCSB PDB</a></span>)</li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/CompTox_Chemicals_Dashboard" title="CompTox Chemicals Dashboard">CompTox Dashboard</a> <span style="font-weight:normal">(<abbr title="U.S. Environmental Protection Agency">EPA</abbr>)</span></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="comptox.epa.gov"><a rel="nofollow" class="external text" href="https://comptox.epa.gov/dashboard/chemical/details/DTXSID2045606">DTXSID2045606</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q412690#P3117" title="Edit this at Wikidata"><img alt="Edit this at Wikidata" src="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/10px-OOjs_UI_icon_edit-ltr-progressive.svg.png" decoding="async" width="10" height="10" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/15px-OOjs_UI_icon_edit-ltr-progressive.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/20px-OOjs_UI_icon_edit-ltr-progressive.svg.png 2x" data-file-width="20" data-file-height="20" /></a></span></span></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/ECHA_InfoCard" class="mw-redirect" title="ECHA InfoCard"><span title="echa.europa.eu">ECHA InfoCard</span></a></th><td class="infobox-data"><a rel="nofollow" class="external text" href="https://echa.europa.eu/substance-information/-/substanceinfo/100.118.289">100.118.289</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q412690#P2566" title="Edit this at Wikidata"><img alt="Edit this at Wikidata" src="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/10px-OOjs_UI_icon_edit-ltr-progressive.svg.png" decoding="async" width="10" height="10" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/15px-OOjs_UI_icon_edit-ltr-progressive.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/20px-OOjs_UI_icon_edit-ltr-progressive.svg.png 2x" data-file-width="20" data-file-height="20" /></a></span></td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd">Chemical and physical data</th></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Chemical_formula" title="Chemical formula">Formula</a></th><td class="infobox-data"><span title="Carbon">C</span><sub>17</sub><span title="Hydrogen">H</span><sub>21</sub><span title="Nitrogen">N</span><span title="Oxygen">O</span><sub>3</sub></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Molar_mass" title="Molar mass">Molar mass</a></th><td class="infobox-data"><span class="nowrap"><span data-sort-value="7002287359000000000♠"></span>287.359</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=O%28c2c1O%5BC%40H%5D4C%5BC%40%40H%5D%28O%29%2FC%3DC%5C%5BC%40%40%5D43c1c%28cc2%29CN%28C%29CC3%29C">Interactive image</a></span></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Melting_point" title="Melting point">Melting point</a></th><td class="infobox-data">126.5 °C (259.7 °F)</td></tr><tr><td colspan="2" class="infobox-full-data"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold;"><div><a href="/wiki/Simplified_molecular-input_line-entry_system" class="mw-redirect" title="Simplified molecular-input line-entry system">SMILES</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="word-wrap:break-word; text-indent:-1.5em; text-align:left; padding-left:1.5em; font-size:97%; line-height:120%;">O(c2c1O[C@H]4C[C@@H](O)/C=C\[C@@]43c1c(cc2)CN(C)CC3)C</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/C17H21NO3/c1-18-8-7-17-6-5-12(19)9-14(17)21-16-13(20-2)4-3-11(10-18)15(16)17/h3-6,12,14,19H,7-10H2,1-2H3/t12-,14-,17-/m0/s1<sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></div></li><li style="line-height: inherit; margin: 0"><div style="word-wrap:break-word; text-indent:-1.5em; text-align:left; padding-left:1.5em; font-size:97%; line-height:120%;">Key:ASUTZQLVASHGKV-JDFRZJQESA-N<sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></div></li></ul> </div></td></tr><tr><td colspan="2" class="infobox-below"><style data-mw-deduplicate="TemplateStyles:r886047488">.mw-parser-output .nobold{font-weight:normal}</style><span class="nobold">  <span class="reflink plainlinks nourlexpansion"><a class="external text" href="https://en.wikipedia.org/w/index.php?title=Special:ComparePages&rev1=461118063&page2=Galantamine">(verify)</a></span></span></td></tr></tbody></table> <p><b>Galantamine</b> is a type of <a href="/wiki/Acetylcholinesterase_inhibitor" title="Acetylcholinesterase inhibitor">acetylcholinesterase inhibitor</a>. It is an <a href="/wiki/Alkaloid" title="Alkaloid">alkaloid</a> <a href="/wiki/Extract" title="Extract">extracted</a> from the bulbs and flowers of <i><a href="/wiki/Common_snowdrop" class="mw-redirect" title="Common snowdrop">Galanthus nivalis</a></i> (common snowdrop), <i>Galanthus caucasicus</i> (Caucasian <a href="/wiki/Snowdrop" class="mw-redirect" title="Snowdrop">snowdrop</a>), <i><a href="/wiki/Galanthus_woronowii" title="Galanthus woronowii">Galanthus woronowii</a></i> (Voronov's snowdrop), and other members of the family <i><a href="/wiki/Amaryllidaceae" title="Amaryllidaceae">Amaryllidaceae</a></i>, such as <i>Narcissus</i> (<a href="/wiki/Daffodil" class="mw-redirect" title="Daffodil">daffodil</a>), <i><a href="/wiki/Leucojum_aestivum" title="Leucojum aestivum">Leucojum aestivum</a></i> (snowflake), and <i>Lycoris</i> including <i><a href="/wiki/Lycoris_radiata" title="Lycoris radiata">Lycoris radiata</a></i> (red spider lily).<sup id="cite_ref-5" class="reference"><a href="#cite_note-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> It can also be <a href="/wiki/Galantamine_total_synthesis" title="Galantamine total synthesis">produced synthetically</a>. </p><p>Galantamine is primarily known for its potential to slow <a href="/wiki/Mild_cognitive_impairment" title="Mild cognitive impairment">cognitive decline</a>. It is used clinically for treating early-stage <a href="/wiki/Alzheimer%27s_disease" title="Alzheimer's disease">Alzheimer's disease</a> and <a href="/wiki/Memory" title="Memory">memory</a> impairments, although it has had limited success with the more advanced condition of <a href="/wiki/Dementia" title="Dementia">dementia</a>.<sup id="cite_ref-drugs_6-0" class="reference"><a href="#cite_note-drugs-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-birks_7-0" class="reference"><a href="#cite_note-birks-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-kalola_8-0" class="reference"><a href="#cite_note-kalola-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-battle_9-0" class="reference"><a href="#cite_note-battle-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> </p><p>It works by increasing the amount of a type of <a href="/wiki/Neurotransmitter" title="Neurotransmitter">neurotransmitter</a> named <a href="/wiki/Acetylcholine" title="Acetylcholine">acetylcholine</a> by the inhibiting activity of an enzyme called <a href="/wiki/Acetylcholinesterase" title="Acetylcholinesterase">acetylcholinesterase</a> known for <a href="/wiki/Hydrolysis" title="Hydrolysis">breaking down</a> acetylcholine. This elevates and prolongs acetylcholine levels boosting acetylcholine's <a href="/wiki/Neuromodulatory" class="mw-redirect" title="Neuromodulatory">neuromodulatory</a> functionality, subsequently enhancing functionality of the various <a href="/wiki/Cognitions" class="mw-redirect" title="Cognitions">cognitions</a> that acetylcholine is involved in, such as memory processing, <a href="/wiki/Reasoning" class="mw-redirect" title="Reasoning">reasoning</a>, and <a href="/wiki/Thinking" class="mw-redirect" title="Thinking">thinking</a>.<sup id="cite_ref-drugs_6-1" class="reference"><a href="#cite_note-drugs-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> Galantamine may cause serious <a href="/wiki/Adverse_effect" title="Adverse effect">adverse effects</a>, such as stomach bleeding, liver injury or chest pain.<sup id="cite_ref-drugs_6-2" class="reference"><a href="#cite_note-drugs-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-kalola_8-1" class="reference"><a href="#cite_note-kalola-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> </p><p>Galantamine was isolated for the first time from bulbs of <i><a href="/wiki/Galanthus_nivalis" title="Galanthus nivalis">Galanthus nivalis</a></i> (common snowdrop) in the Soviet Union in the 1940s.<sup id="cite_ref-10" class="reference"><a href="#cite_note-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> The active ingredient was extracted, identified, and studied, in particular in relation to <a href="/wiki/Acetylcholinesterase" title="Acetylcholinesterase">acetylcholinesterase</a> (AChE)-inhibiting properties.<sup id="cite_ref-11" class="reference"><a href="#cite_note-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-12" class="reference"><a href="#cite_note-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup> The first industrial process was developed in 1959.<sup id="cite_ref-13" class="reference"><a href="#cite_note-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup><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> However, it was not until the 1990s when full-scale synthesis was upscaled and optimized.<sup id="cite_ref-15" class="reference"><a href="#cite_note-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup> </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Medical_uses">Medical uses</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Galantamine&action=edit&section=1" title="Edit section: Medical uses"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Galantamine, sold under the brand name <b>Razadyne</b> among others, is <a href="/wiki/Indicated" class="mw-redirect" title="Indicated">indicated</a> for the treatment of mild to moderate <a href="/wiki/Multi-infarct_dementia" class="mw-redirect" title="Multi-infarct dementia">vascular dementia</a> and Alzheimer's disease.<sup id="cite_ref-drugs_6-3" class="reference"><a href="#cite_note-drugs-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-birks_7-1" class="reference"><a href="#cite_note-birks-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> The first person to extract galantamine and theorize its usefulness in medicine, was the Bulgarian chemist <a href="/wiki/Dimitar_Paskov" title="Dimitar Paskov">Dimitar Paskov</a> in 1959. In the United States, it is approved by the <a href="/wiki/Food_and_Drug_Administration" title="Food and Drug Administration">Food and Drug Administration</a> (FDA) for the treatment of mild to moderate dementia.<sup id="cite_ref-kalola_8-2" class="reference"><a href="#cite_note-kalola-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup><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> Galantamine may not be effective for treating mild cognitive impairment.<sup id="cite_ref-17" class="reference"><a href="#cite_note-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Alzheimer's_disease"><span id="Alzheimer.27s_disease"></span>Alzheimer's disease</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Galantamine&action=edit&section=2" title="Edit section: Alzheimer's disease"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Alzheimer's disease is characterized by the impairment of <a href="/wiki/Cholinergic" title="Cholinergic">cholinergic</a> function.<sup id="cite_ref-drugs_6-4" class="reference"><a href="#cite_note-drugs-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-kalola_8-3" class="reference"><a href="#cite_note-kalola-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> One hypothesis is that this impairment contributes to the cognitive deficits caused by the disease. This hypothesis forms the basis for use of galantamine as a cholinergic enhancer in the treatment of Alzheimer's.<sup id="cite_ref-drugs_6-5" class="reference"><a href="#cite_note-drugs-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-kalola_8-4" class="reference"><a href="#cite_note-kalola-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> Galantamine inhibits acetylcholinesterase, an enzyme which <a href="/wiki/Hydrolysis" title="Hydrolysis">hydrolyzes</a> acetylcholine.<sup id="cite_ref-drugs_6-6" class="reference"><a href="#cite_note-drugs-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-kalola_8-5" class="reference"><a href="#cite_note-kalola-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> As a result of acetylcholinesterase inhibition, galantamine increases the availability of acetylcholine for synaptic transmission.<sup id="cite_ref-kalola_8-6" class="reference"><a href="#cite_note-kalola-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> Additionally, galantamine binds to the <a href="/wiki/Allosteric_regulation" title="Allosteric regulation">allosteric</a> sites of <a href="/wiki/Nicotinic" class="mw-redirect" title="Nicotinic">nicotinic</a> receptors, which causes a conformational change.<sup id="cite_ref-springer_18-0" class="reference"><a href="#cite_note-springer-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup> This allosteric modulation increases the nicotinic receptor's response to acetylcholine.<sup id="cite_ref-kalola_8-7" class="reference"><a href="#cite_note-kalola-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> The activation of presynaptic nicotinic receptors increases the release of acetylcholine, further increasing the availability of acetylcholine.<sup id="cite_ref-kalola_8-8" class="reference"><a href="#cite_note-kalola-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> Galantamine's competitive inhibition of acetylcholinesterase and allosteric nicotinic modulation serves as a dual mechanism of action.<sup id="cite_ref-springer_18-1" class="reference"><a href="#cite_note-springer-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup> </p><p>To reduce the prevalence of negative side effects associated with galantamine, such as <a href="/wiki/Nausea" title="Nausea">nausea</a> and <a href="/wiki/Vomiting" title="Vomiting">vomiting</a>, a dose-escalation scheme may be used.<sup id="cite_ref-direct_19-0" class="reference"><a href="#cite_note-direct-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup> The use of a dose-escalation scheme has been well accepted in countries where galantamine is used.<sup id="cite_ref-direct_19-1" class="reference"><a href="#cite_note-direct-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup> A dose-escalation scheme for Alzheimer's treatment involves a recommended starting dosage of 4 mg galantamine tablets given twice a day (8 mg/day).<sup id="cite_ref-drugs_6-7" class="reference"><a href="#cite_note-drugs-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> After a minimum of 4 weeks, the dosage may then be increased to 8 mg given twice a day (16 mg/day).<sup id="cite_ref-drugs_6-8" class="reference"><a href="#cite_note-drugs-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> After a minimum of 4 weeks at 16 mg/day, the treatment may be increased to 12 mg given twice a day (24 mg/day).<sup id="cite_ref-drugs_6-9" class="reference"><a href="#cite_note-drugs-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> Dosage increases are based upon the assessment of clinical benefit as well as tolerability of the previous dosage.<sup id="cite_ref-drugs_6-10" class="reference"><a href="#cite_note-drugs-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> If treatment is interrupted for more than three days, the process is usually restarted, beginning at the starting dosage, and re-escalating to the current dose.<sup id="cite_ref-drugs_6-11" class="reference"><a href="#cite_note-drugs-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> It has been found that a dosage between 16–24 mg/day is the optimal dosage.<sup id="cite_ref-pmid24591834_20-0" class="reference"><a href="#cite_note-pmid24591834-20"><span class="cite-bracket">[</span>20<span class="cite-bracket">]</span></a></sup> </p><p>In December 2023, the FDA approved a <a href="/wiki/New_Drug_Application" title="New Drug Application">New Drug Application</a> (NDA) for a pro-drug of galantamine called ALPHA-1062.<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> In July 2024, The FDA approved <a href="/wiki/Benzgalantamine" title="Benzgalantamine">benzgalantamine</a> (Zunveyl), previously known as ALPHA-1062, to treat mild-to-moderate Alzheimer's disease.<sup id="cite_ref-22" class="reference"><a href="#cite_note-22"><span class="cite-bracket">[</span>22<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Side_effects">Side effects</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Galantamine&action=edit&section=3" title="Edit section: Side effects"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The <a href="/wiki/Adverse_drug_reaction" title="Adverse drug reaction">adverse effect</a> profile of galantamine includes potential for <a href="/wiki/Allergic_reaction" class="mw-redirect" title="Allergic reaction">allergic reaction</a>, including <a href="/wiki/Hives" title="Hives">hives</a>, swelling of the face or throat, and skin rash.<sup id="cite_ref-drugs_6-12" class="reference"><a href="#cite_note-drugs-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-mayo_23-0" class="reference"><a href="#cite_note-mayo-23"><span class="cite-bracket">[</span>23<span class="cite-bracket">]</span></a></sup> Using galantamine may cause chest pain, bloody urine, stomach bleeding, and liver injury, among other side effects.<sup id="cite_ref-drugs_6-13" class="reference"><a href="#cite_note-drugs-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-mayo_23-1" class="reference"><a href="#cite_note-mayo-23"><span class="cite-bracket">[</span>23<span class="cite-bracket">]</span></a></sup> Nausea, vomiting, diarrhea, dizziness, and headache are considered common side effects.<sup id="cite_ref-drugs_6-14" class="reference"><a href="#cite_note-drugs-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> </p><p>A gradual titration over more than three months may enable long-term tolerability in some people.<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> </p><p>Galantamine has a wide spectrum of <a href="/wiki/Drug_interaction" title="Drug interaction">interactions with other medications</a> and medical disorders, requiring close assessment between the physician and patient.<sup id="cite_ref-mayo_23-2" class="reference"><a href="#cite_note-mayo-23"><span class="cite-bracket">[</span>23<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Pharmacology">Pharmacology</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Galantamine&action=edit&section=4" title="Edit section: Pharmacology"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Galantamine's chemical structure contains a tertiary <a href="/wiki/Amine" title="Amine">amine</a>. At a neutral <a href="/wiki/PH" title="PH">pH</a>, this tertiary amine will often bond to a hydrogen, and appear mostly as an ammonium ion.<sup id="cite_ref-drugs_6-15" class="reference"><a href="#cite_note-drugs-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> </p><p>Galantamine is a potent <a href="/wiki/Allosteric_modulator" title="Allosteric modulator">allosteric</a> potentiating <a href="/wiki/Ligand_(biochemistry)" title="Ligand (biochemistry)">ligand</a> of human <a href="/wiki/Nicotinic_acetylcholine_receptors" class="mw-redirect" title="Nicotinic acetylcholine receptors">nicotinic acetylcholine receptors</a> (nAChRs) <a href="/wiki/%CE%914%CE%B22_nicotinic_receptor" class="mw-redirect" title="Α4β2 nicotinic receptor">α<sub>4</sub>β<sub>2</sub></a>, <a href="/wiki/%CE%913%CE%B24_nicotinic_receptor" class="mw-redirect" title="Α3β4 nicotinic receptor">α<sub>3</sub>β<sub>4</sub></a>, and <a href="/w/index.php?title=%CE%916%CE%B24&action=edit&redlink=1" class="new" title="Α6β4 (page does not exist)">α<sub>6</sub>β<sub>4</sub></a>, and chicken/mouse nAChRs <a href="/wiki/%CE%917_nicotinic_acetylcholine_receptor" class="mw-redirect" title="Α7 nicotinic acetylcholine receptor">α<sub>7</sub></a>/<a href="/wiki/5-HT3_receptor" title="5-HT3 receptor">5-HT<sub>3</sub></a> in certain areas of the brain.<sup id="cite_ref-drugs_6-16" class="reference"><a href="#cite_note-drugs-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-metabolism_25-0" class="reference"><a href="#cite_note-metabolism-25"><span class="cite-bracket">[</span>25<span class="cite-bracket">]</span></a></sup> By binding to the allosteric site of the nAChRs, a conformational change occurs which increases the receptors response to acetylcholine.<sup id="cite_ref-kalola_8-9" class="reference"><a href="#cite_note-kalola-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> This modulation of the <a href="/wiki/Nicotinic_acetylcholine_receptor" title="Nicotinic acetylcholine receptor">nicotinic cholinergic receptors</a> on cholinergic neurons in turn causes an increase in the amount of acetylcholine released.<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> However, recent studies suggest that Galantamine does not functionally act at human nAChRs <a href="/wiki/%CE%914%CE%B22_nicotinic_receptor" class="mw-redirect" title="Α4β2 nicotinic receptor">α<sub>4</sub>β<sub>2</sub></a> or <a href="/wiki/%CE%917_nicotinic_receptor" class="mw-redirect" title="Α7 nicotinic receptor">α<sub>7</sub></a> as a positive allosteric modulator.<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><sup id="cite_ref-pmid29669164_28-0" class="reference"><a href="#cite_note-pmid29669164-28"><span class="cite-bracket">[</span>28<span class="cite-bracket">]</span></a></sup> </p><p>Galantamine also works as a weak <a href="/wiki/Competitive_inhibition" title="Competitive inhibition">competitive</a> and <a href="/wiki/Enzyme_inhibitor#Reversible_inhibitors" title="Enzyme inhibitor">reversible</a> <a href="/wiki/Cholinesterase_inhibitor" title="Cholinesterase inhibitor">cholinesterase inhibitor</a> in all areas of the body.<sup id="cite_ref-drugs_6-17" class="reference"><a href="#cite_note-drugs-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> By inhibiting acetylcholinesterase, it increases the concentration and thereby action of <a href="/wiki/Acetylcholine" title="Acetylcholine">acetylcholine</a> in certain parts of the brain. Galantamine's effects on nAChRs and complementary acetylcholinesterase inhibition make up a dual mechanism of action. It is hypothesized that this action might relieve some of the symptoms of Alzheimer's. </p> <figure class="mw-default-size mw-halign-center" typeof="mw:File/Thumb"><a href="/wiki/File:Synapse_FINISHED.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/2/27/Synapse_FINISHED.png/220px-Synapse_FINISHED.png" decoding="async" width="220" height="261" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/2/27/Synapse_FINISHED.png/330px-Synapse_FINISHED.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/2/27/Synapse_FINISHED.png/440px-Synapse_FINISHED.png 2x" data-file-width="780" data-file-height="926" /></a><figcaption>Galantamine's dual mechanism of action</figcaption></figure> <p>Galantamine in its pure form is a white powder. The atomic resolution 3D structure of the complex of galantamine and its target, acetylcholinesterase, was determined by <a href="/wiki/X-ray_crystallography" title="X-ray crystallography">X-ray crystallography</a> in 1999 (PDB code: <a rel="nofollow" class="external text" href="http://oca.weizmann.ac.il/oca-bin/ocashort?id=1DX6">1DX6</a>; <a rel="nofollow" class="external text" href="http://www.proteopedia.org/wiki/index.php/1dx6">see complex</a>).<sup id="cite_ref-29" class="reference"><a href="#cite_note-29"><span class="cite-bracket">[</span>29<span class="cite-bracket">]</span></a></sup> There is no evidence that galantamine alters the course of the underlying dementing process.<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> </p> <div class="mw-heading mw-heading2"><h2 id="Pharmacokinetics">Pharmacokinetics</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Galantamine&action=edit&section=5" title="Edit section: Pharmacokinetics"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Absorption of galantamine is rapid and complete and shows linear pharmacokinetics. It is well absorbed with absolute oral <a href="/wiki/Bioavailability" title="Bioavailability">bioavailability</a> between 80 and 100%. It has a terminal elimination half-life of seven hours. Peak effect of inhibiting <a href="/wiki/Acetylcholinesterase" title="Acetylcholinesterase">acetylcholinesterase</a> was achieved about one hour after a single oral dose of 8 mg in some healthy volunteers. </p><p>The coadministration of food delays the rate of galantamine absorption, but does not affect the extent of absorption.<sup id="cite_ref-springer_18-2" class="reference"><a href="#cite_note-springer-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup> </p><p><a href="/wiki/Plasma_protein_binding" title="Plasma protein binding">Plasma protein binding</a> of galantamine is about 18%, which is relatively low. </p> <div class="mw-heading mw-heading2"><h2 id="Metabolism">Metabolism</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Galantamine&action=edit&section=6" title="Edit section: Metabolism"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Approximately 75% of a dose of galantamine is metabolised in the liver. In vitro studies have shown that hepatic <a href="/wiki/CYP2D6" title="CYP2D6">CYP2D6</a> and <a href="/wiki/CYP3A4" title="CYP3A4">CYP3A4</a> are involved in galantamine metabolism. Within 24 hours of intravenous or oral administration approximately 20% of a dose of galantamine will be excreted unreacted in the urine.<sup id="cite_ref-springer_18-3" class="reference"><a href="#cite_note-springer-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup> </p><p>In humans, several metabolic pathways for galantamine exist.<sup id="cite_ref-metabolism_25-1" class="reference"><a href="#cite_note-metabolism-25"><span class="cite-bracket">[</span>25<span class="cite-bracket">]</span></a></sup> These pathways lead to the formation of a number of different metabolites.<sup id="cite_ref-metabolism_25-2" class="reference"><a href="#cite_note-metabolism-25"><span class="cite-bracket">[</span>25<span class="cite-bracket">]</span></a></sup> One of the metabolites that may result can be formed through the <a href="/wiki/Glucuronidation" title="Glucuronidation">glucuronidation</a> of galantamine.<sup id="cite_ref-metabolism_25-3" class="reference"><a href="#cite_note-metabolism-25"><span class="cite-bracket">[</span>25<span class="cite-bracket">]</span></a></sup> Additionally, galantamine may undergo <a href="/wiki/Oxidation" class="mw-redirect" title="Oxidation">oxidation</a> or <a href="/wiki/Demethylation" title="Demethylation">demethylation</a> at its nitrogen atom, forming two other possible metabolites.<sup id="cite_ref-metabolism_25-4" class="reference"><a href="#cite_note-metabolism-25"><span class="cite-bracket">[</span>25<span class="cite-bracket">]</span></a></sup> Galantamine can undergo demethylation at its oxygen atom, forming an intermediate which can then undergo glucuronidation or sulfate conjugation.<sup id="cite_ref-metabolism_25-5" class="reference"><a href="#cite_note-metabolism-25"><span class="cite-bracket">[</span>25<span class="cite-bracket">]</span></a></sup> Lastly, galantamine may be oxidized and then reduced before finally undergoing demethylation or oxidation at its nitrogen atom, or demethylation and subsequent glucuronidation at its oxygen atom.<sup id="cite_ref-metabolism_25-6" class="reference"><a href="#cite_note-metabolism-25"><span class="cite-bracket">[</span>25<span class="cite-bracket">]</span></a></sup> </p> <figure class="mw-default-size mw-halign-center" typeof="mw:File/Thumb"><a href="/wiki/File:Galantamine_Metabolism.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/f/fd/Galantamine_Metabolism.png/220px-Galantamine_Metabolism.png" decoding="async" width="220" height="210" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/f/fd/Galantamine_Metabolism.png/330px-Galantamine_Metabolism.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/f/fd/Galantamine_Metabolism.png/440px-Galantamine_Metabolism.png 2x" data-file-width="2169" data-file-height="2071" /></a><figcaption>Metabolic pathways of galantamine</figcaption></figure> <div class="mw-heading mw-heading2"><h2 id="Drug_interactions">Drug interactions</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Galantamine&action=edit&section=7" title="Edit section: Drug interactions"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Since galantamine is metabolized by CYP2D6 and CYP3A4, inhibiting either of these <a href="/wiki/Isoenzymes" class="mw-redirect" title="Isoenzymes">isoenzymes</a> will increase the cholinergic effects of galantamine.<sup id="cite_ref-springer_18-4" class="reference"><a href="#cite_note-springer-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup> Inhibiting these enzymes may lead to adverse effects.<sup id="cite_ref-springer_18-5" class="reference"><a href="#cite_note-springer-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup> It was found that <a href="/wiki/Paroxetine" title="Paroxetine">paroxetine</a>, an inhibitor of CYP2D6, increased the <a href="/wiki/Bioavailability" title="Bioavailability">bioavailability</a> of galantamine by 40%.<sup id="cite_ref-springer_18-6" class="reference"><a href="#cite_note-springer-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup> The CYP3A4 inhibitors <a href="/wiki/Ketoconazole" title="Ketoconazole">ketoconazole</a> and <a href="/wiki/Erythromycin" title="Erythromycin">erythromycin</a> increased the <a href="/wiki/Bioavailability" title="Bioavailability">bioavailability</a> of galantamine by 30% and 12%, respectively.<sup id="cite_ref-springer_18-7" class="reference"><a href="#cite_note-springer-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Extraction_and_synthesis">Extraction and synthesis</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Galantamine&action=edit&section=8" title="Edit section: Extraction and synthesis"><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">Main article: <a href="/wiki/Galantamine_total_synthesis" title="Galantamine total synthesis">Galantamine total synthesis</a></div> <p>Since the alkaloid is isolated from botanical sources containing low amounts (0.1%) by weight, extraction yields are low.<sup id="cite_ref-pmid28337117_31-0" class="reference"><a href="#cite_note-pmid28337117-31"><span class="cite-bracket">[</span>31<span class="cite-bracket">]</span></a></sup> Although galantamine can be produced from natural resources, it also has many industrial syntheses, such as by <a href="/wiki/Janssen_Pharmaceuticals" title="Janssen Pharmaceuticals">Janssen</a>, <a href="/wiki/Ortho-McNeil_Pharmaceutical" title="Ortho-McNeil Pharmaceutical">Ortho-McNeil Pharmaceutical</a>, <a href="/wiki/Shire_(pharmaceutical_company)" title="Shire (pharmaceutical company)">Shire</a>, and <a href="/wiki/Takeda_Pharmaceutical_Company" title="Takeda Pharmaceutical Company">Takeda Pharmaceutical Company</a>.<sup id="cite_ref-32" class="reference"><a href="#cite_note-32"><span class="cite-bracket">[</span>32<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Research">Research</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Galantamine&action=edit&section=9" title="Edit section: Research"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Organophosphate_poisoning">Organophosphate poisoning</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Galantamine&action=edit&section=10" title="Edit section: Organophosphate poisoning"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The toxicity of <a href="/wiki/Organophosphate" title="Organophosphate">organophosphates</a> results primarily from their action as irreversible inhibitors of acetylcholinesterase.<sup id="cite_ref-organo_33-0" class="reference"><a href="#cite_note-organo-33"><span class="cite-bracket">[</span>33<span class="cite-bracket">]</span></a></sup> Inhibiting acetylcholinesterase causes an increase in acetylcholine, as the enzyme is no longer available to catalyze its breakdown.<sup id="cite_ref-organo_33-1" class="reference"><a href="#cite_note-organo-33"><span class="cite-bracket">[</span>33<span class="cite-bracket">]</span></a></sup> In the peripheral nervous system, acetylcholine accumulation can cause an overstimulation of muscarinic receptors followed by a desensitization of nicotinic receptors.<sup id="cite_ref-organo_33-2" class="reference"><a href="#cite_note-organo-33"><span class="cite-bracket">[</span>33<span class="cite-bracket">]</span></a></sup> This leads to severe skeletal muscle fasciculations (involuntary contractions).<sup id="cite_ref-organo_33-3" class="reference"><a href="#cite_note-organo-33"><span class="cite-bracket">[</span>33<span class="cite-bracket">]</span></a></sup> The effects on the central nervous system include <a href="/wiki/Anxiety" title="Anxiety">anxiety</a>, restlessness, <a href="/wiki/Confusion" title="Confusion">confusion</a>, <a href="/wiki/Ataxia" title="Ataxia">ataxia</a>, <a href="/wiki/Tremor" title="Tremor">tremors</a>, <a href="/wiki/Seizures" class="mw-redirect" title="Seizures">seizures</a>, cardiorespiratory paralysis, and <a href="/wiki/Coma" title="Coma">coma</a>.<sup id="cite_ref-organo_33-4" class="reference"><a href="#cite_note-organo-33"><span class="cite-bracket">[</span>33<span class="cite-bracket">]</span></a></sup> As a reversible acetylcholinesterase inhibitor, galantamine has the potential to serve as an effective organophosphate poisoning treatment by preventing irreversible acetylcholinesterase inhibition.<sup id="cite_ref-organo_33-5" class="reference"><a href="#cite_note-organo-33"><span class="cite-bracket">[</span>33<span class="cite-bracket">]</span></a></sup> Additionally, galantamine has <a href="/wiki/Anticonvulsant" title="Anticonvulsant">anticonvulsant</a> properties which may make it even more desirable as an antidote.<sup id="cite_ref-organo_33-6" class="reference"><a href="#cite_note-organo-33"><span class="cite-bracket">[</span>33<span class="cite-bracket">]</span></a></sup> </p><p>Research supported in part by the <a href="/wiki/US_Army" class="mw-redirect" title="US Army">US Army</a> has led to a <a href="/wiki/US_patent" class="mw-redirect" title="US patent">US patent</a> application for the use of galantamine and/or its derivatives for treatment of <a href="/wiki/Organophosphate_poisoning" title="Organophosphate poisoning">organophosphate poisoning</a>.<sup id="cite_ref-organo_33-7" class="reference"><a href="#cite_note-organo-33"><span class="cite-bracket">[</span>33<span class="cite-bracket">]</span></a></sup> The indications for use of galantamine in the patent application include poisoning by <a href="/wiki/Nerve_agent" title="Nerve agent">nerve agents</a> "including but not limited to <a href="/wiki/Soman" title="Soman">soman</a>, <a href="/wiki/Sarin" title="Sarin">sarin</a>, and <a href="/wiki/VX_(nerve_agent)" title="VX (nerve agent)">VX</a>, <a href="/wiki/Tabun_(nerve_agent)" title="Tabun (nerve agent)">tabun</a>, and <a href="/wiki/Novichok_agent" class="mw-redirect" title="Novichok agent">Novichok agents</a>". Galantamine was studied in the research cited in the patent application for use along with the well-recognized nerve agent antidote <a href="/wiki/Atropine" title="Atropine">atropine</a>. According to the investigators, an unexpected synergistic interaction occurred between galantamine and atropine in an amount of 6 mg/kg or higher. Increasing the dose of galantamine from 5 to 8 mg/kg decreased the dose of atropine needed to protect experimental animals from the toxicity of soman in dosages 1.5 times the dose generally required to kill half the experimental animals.<sup id="cite_ref-Albuquerque_patent_34-0" class="reference"><a href="#cite_note-Albuquerque_patent-34"><span class="cite-bracket">[</span>34<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Autism">Autism</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Galantamine&action=edit&section=11" title="Edit section: Autism"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Galantamine given in addition to <a href="/wiki/Risperidone" title="Risperidone">risperidone</a> to autistic children has been shown to improve some of the symptoms of autism such as irritability, lethargy, and social withdrawal.<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> Additionally, the cholinergic and nicotinic receptors are believed to play a role in attentional processes.<sup id="cite_ref-aut_36-0" class="reference"><a href="#cite_note-aut-36"><span class="cite-bracket">[</span>36<span class="cite-bracket">]</span></a></sup> Some studies have noted that cholinergic and nicotinic treatments have improved attention in autistic children.<sup id="cite_ref-aut_36-1" class="reference"><a href="#cite_note-aut-36"><span class="cite-bracket">[</span>36<span class="cite-bracket">]</span></a></sup> As such, it is hypothesized that galantamine's dual action mechanism might have a similar effect in treating autistic children and adolescents.<sup id="cite_ref-aut_36-2" class="reference"><a href="#cite_note-aut-36"><span class="cite-bracket">[</span>36<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Anesthesia">Anesthesia</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Galantamine&action=edit&section=12" title="Edit section: Anesthesia"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Galantamine may have some limited use in reducing the side-effects of anesthetics <a href="/wiki/Ketamine" title="Ketamine">ketamine</a> and <a href="/wiki/Diazepam" title="Diazepam">diazepam</a>. In one study, a control group of patients were given <a href="/wiki/Ketamine" title="Ketamine">ketamine</a> and <a href="/wiki/Diazepam" title="Diazepam">diazepam</a> and underwent <a href="/wiki/Anesthesia" title="Anesthesia">anesthesia</a> and surgery.<sup id="cite_ref-anesth_37-0" class="reference"><a href="#cite_note-anesth-37"><span class="cite-bracket">[</span>37<span class="cite-bracket">]</span></a></sup> The experimental group was given <a href="/wiki/Ketamine" title="Ketamine">ketamine</a>, <a href="/wiki/Diazepam" title="Diazepam">diazepam</a>, and nivalin (of which the active ingredient is galantamine).<sup id="cite_ref-anesth_37-1" class="reference"><a href="#cite_note-anesth-37"><span class="cite-bracket">[</span>37<span class="cite-bracket">]</span></a></sup> The degree of drowsiness and disorientation of the two groups was then assessed 5, 10, 15, 30 and 60 minutes after surgery.<sup id="cite_ref-anesth_37-2" class="reference"><a href="#cite_note-anesth-37"><span class="cite-bracket">[</span>37<span class="cite-bracket">]</span></a></sup> The group that had taken nivalin were found to be more alert 5, 10, and 15 minutes after the surgery.<sup id="cite_ref-anesth_37-3" class="reference"><a href="#cite_note-anesth-37"><span class="cite-bracket">[</span>37<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Oneirogen">Oneirogen</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Galantamine&action=edit&section=13" title="Edit section: Oneirogen"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Galantamine is known to have <a href="/wiki/Oneirogenic" class="mw-redirect" title="Oneirogenic">oneirogenic</a> properties. Research has demonstrated its potential to increase <a href="/wiki/Dream#Recollection" title="Dream">dream recall</a>, dream self-awareness and dream vividness. The enhancement of such <a href="/wiki/Dream" title="Dream">dream</a> properties can facilitate the induction of <a href="/wiki/Lucid_dreams" class="mw-redirect" title="Lucid dreams">lucid dreams</a>.<sup id="cite_ref-Tan_Fan_2023_p._38-0" class="reference"><a href="#cite_note-Tan_Fan_2023_p.-38"><span class="cite-bracket">[</span>38<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Sparrow_Hurd_Carlson_Molina_2018_pp._74–88_39-0" class="reference"><a href="#cite_note-Sparrow_Hurd_Carlson_Molina_2018_pp._74–88-39"><span class="cite-bracket">[</span>39<span class="cite-bracket">]</span></a></sup> </p> <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=Galantamine&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"> <div class="mw-references-wrap mw-references-columns"><ol class="references"> <li id="cite_note-Drugs.com_pregnancy-1"><span class="mw-cite-backlink"><b><a href="#cite_ref-Drugs.com_pregnancy_1-0">^</a></b></span> <span class="reference-text"><style data-mw-deduplicate="TemplateStyles:r1238218222">.mw-parser-output cite.citation{font-style:inherit;word-wrap:break-word}.mw-parser-output .citation q{quotes:"\"""\"""'""'"}.mw-parser-output .citation:target{background-color:rgba(0,127,255,0.133)}.mw-parser-output .id-lock-free.id-lock-free a{background:url("//upload.wikimedia.org/wikipedia/commons/6/65/Lock-green.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-limited.id-lock-limited a,.mw-parser-output .id-lock-registration.id-lock-registration a{background:url("//upload.wikimedia.org/wikipedia/commons/d/d6/Lock-gray-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-subscription.id-lock-subscription a{background:url("//upload.wikimedia.org/wikipedia/commons/a/aa/Lock-red-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .cs1-ws-icon a{background:url("//upload.wikimedia.org/wikipedia/commons/4/4c/Wikisource-logo.svg")right 0.1em center/12px no-repeat}body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-free a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-limited a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-registration a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-subscription a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .cs1-ws-icon a{background-size:contain;padding:0 1em 0 0}.mw-parser-output .cs1-code{color:inherit;background:inherit;border:none;padding:inherit}.mw-parser-output .cs1-hidden-error{display:none;color:var(--color-error,#d33)}.mw-parser-output .cs1-visible-error{color:var(--color-error,#d33)}.mw-parser-output .cs1-maint{display:none;color:#085;margin-left:0.3em}.mw-parser-output .cs1-kern-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right{padding-right:0.2em}.mw-parser-output .citation .mw-selflink{font-weight:inherit}@media screen{.mw-parser-output .cs1-format{font-size:95%}html.skin-theme-clientpref-night .mw-parser-output .cs1-maint{color:#18911f}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .cs1-maint{color:#18911f}}</style><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://www.drugs.com/pregnancy/galantamine.html">"Galantamine Use During Pregnancy"</a>. <i>Drugs.com</i>. 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The National Non-Food Crops Centre (NNFCC). 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transport modulators"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Acetylcholine_metabolism_and_transport_modulators" title="Template talk:Acetylcholine metabolism and transport modulators"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Acetylcholine_metabolism_and_transport_modulators" title="Special:EditPage/Template:Acetylcholine metabolism and transport modulators"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Acetylcholine_metabolism_and_transport_modulators" style="font-size:114%;margin:0 4em"><a href="/wiki/Acetylcholine" title="Acetylcholine">Acetylcholine</a> <a href="/wiki/Metabolism" title="Metabolism">metabolism</a> and <a href="/wiki/Neurotransmitter_transporter" title="Neurotransmitter transporter">transport</a> <a href="/wiki/Receptor_modulator" title="Receptor modulator">modulators</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Enzyme" title="Enzyme">Enzyme</a><br /><small>(<a href="/wiki/Enzyme_modulator" title="Enzyme modulator">modulators</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:6em;;text-align:center;"><a href="/wiki/Choline_acetyltransferase" title="Choline acetyltransferase"><abbr title="Choline acetyltransferase">ChAT</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 Choline acetyltransferase</span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><b>Inhibitors:</b> <a href="/w/index.php?title=1-(-Benzoylethyl)pyridinium&action=edit&redlink=1" class="new" title="1-(-Benzoylethyl)pyridinium (page does not exist)">1-(-Benzoylethyl)pyridinium</a></li> <li><a href="/w/index.php?title=2-(%CE%B1-Naphthoyl)ethyltrimethylammonium&action=edit&redlink=1" class="new" title="2-(α-Naphthoyl)ethyltrimethylammonium (page does not exist)">2-(α-Naphthoyl)ethyltrimethylammonium</a></li> <li><a href="/w/index.php?title=3-Chloro-4-stillbazole&action=edit&redlink=1" class="new" title="3-Chloro-4-stillbazole (page does not exist)">3-Chloro-4-stillbazole</a></li> <li><a href="/w/index.php?title=4-(1-Naphthylvinyl)pyridine&action=edit&redlink=1" class="new" title="4-(1-Naphthylvinyl)pyridine (page does not exist)">4-(1-Naphthylvinyl)pyridine</a></li> <li><a href="/w/index.php?title=Acetylseco_hemicholinium-3&action=edit&redlink=1" class="new" title="Acetylseco hemicholinium-3 (page does not exist)">Acetylseco hemicholinium-3</a></li> <li><a href="/w/index.php?title=Acryloylcholine&action=edit&redlink=1" class="new" title="Acryloylcholine (page does not exist)">Acryloylcholine</a></li> <li><a href="/wiki/AF64A" class="mw-redirect" title="AF64A">AF64A</a></li> <li><a href="/w/index.php?title=(E)-1-Methyl-4-(1-naphthylvinyl)-1,2,3,6-tetrahydropyridine&action=edit&redlink=1" class="new" title="(E)-1-Methyl-4-(1-naphthylvinyl)-1,2,3,6-tetrahydropyridine (page does not exist)">B115</a></li> <li><a href="/w/index.php?title=(2-Benzoylethyl)trimethylammonium&action=edit&redlink=1" class="new" title="(2-Benzoylethyl)trimethylammonium (page does not exist)">BETA</a></li> <li><a href="/w/index.php?title=N,N-Dimethylamino-2-ethoxyimino-2-adamantane&action=edit&redlink=1" class="new" title="N,N-Dimethylamino-2-ethoxyimino-2-adamantane (page does not exist)">CM-54,903</a></li> <li><a href="/w/index.php?title=N,N-Dimethylaminoethylacrylate&action=edit&redlink=1" class="new" title="N,N-Dimethylaminoethylacrylate (page does not exist)">N,N-Dimethylaminoethylacrylate</a></li> <li><a href="/w/index.php?title=N,N-Dimethylaminoethylchloroacetate&action=edit&redlink=1" class="new" title="N,N-Dimethylaminoethylchloroacetate (page does not exist)">N,N-Dimethylaminoethylchloroacetate</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:6em;;text-align:center;"><a href="/wiki/Acetylcholinesterase" title="Acetylcholinesterase"><abbr title="Acetylcholinesterase">AChE</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 Acetylcholinesterase</span></th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><b><a href="/wiki/Acetylcholinesterase_inhibitor" title="Acetylcholinesterase inhibitor">Inhibitors</a>:</b> <i>Reversible:</i> Carbamates: <a href="/wiki/Aldicarb" title="Aldicarb">Aldicarb</a></li> <li><a href="/wiki/Aminocarb" title="Aminocarb">Aminocarb</a></li> <li><a href="/wiki/Bendiocarb" title="Bendiocarb">Bendiocarb</a></li> <li><a href="/w/index.php?title=Bufencarb&action=edit&redlink=1" class="new" title="Bufencarb (page does not exist)">Bufencarb</a></li> <li><a href="/wiki/Carbaryl" title="Carbaryl">Carbaryl</a></li> <li><a href="/wiki/Carbendazim" title="Carbendazim">Carbendazim</a></li> <li><a href="/w/index.php?title=Carbetamide&action=edit&redlink=1" class="new" title="Carbetamide (page does not exist)">Carbetamide</a></li> <li><a href="/wiki/Carbofuran" title="Carbofuran">Carbofuran</a></li> <li><a href="/wiki/Carbosulfan" title="Carbosulfan">Carbosulfan</a></li> <li><a href="/w/index.php?title=Chlorbufam&action=edit&redlink=1" class="new" title="Chlorbufam (page does not exist)">Chlorbufam</a></li> <li><a href="/w/index.php?title=Chloropropham&action=edit&redlink=1" class="new" title="Chloropropham (page does not exist)">Chloropropham</a></li> <li><a href="/wiki/Dimetilan" title="Dimetilan">Dimetilan</a></li> <li><a href="/wiki/Ethienocarb" class="mw-redirect" title="Ethienocarb">Ethienocarb</a></li> <li><a href="/wiki/Ethiofencarb" title="Ethiofencarb">Ethiofencarb</a></li> <li><a href="/wiki/Fenobucarb" title="Fenobucarb">Fenobucarb</a></li> <li><a href="/wiki/Formetanate" title="Formetanate">Formetanate</a></li> <li><a href="/wiki/Formparanate" title="Formparanate">Formparanate</a></li> <li><a href="/wiki/Methiocarb" title="Methiocarb">Methiocarb</a></li> <li><a href="/wiki/Methomyl" title="Methomyl">Methomyl</a></li> <li><a href="/wiki/Metolcarb" title="Metolcarb">Metolcarb</a></li> <li><a href="/wiki/Miotine" title="Miotine">Miotine</a></li> <li><a href="/wiki/Oxamyl" title="Oxamyl">Oxamyl</a></li> <li><a href="/w/index.php?title=Phenmedipham&action=edit&redlink=1" class="new" title="Phenmedipham (page does not exist)">Phenmedipham</a></li> <li><a href="/w/index.php?title=Pinmicarb&action=edit&redlink=1" class="new" title="Pinmicarb (page does not exist)">Pinmicarb</a></li> <li><a href="/wiki/Pirimicarb" title="Pirimicarb">Pirimicarb</a></li> <li><a href="/wiki/Promecarb" title="Promecarb">Promecarb</a></li> <li><a href="/wiki/Propamocarb" title="Propamocarb">Propamocarb</a></li> <li><a href="/w/index.php?title=Propham&action=edit&redlink=1" class="new" title="Propham (page does not exist)">Propham</a></li> <li><a href="/wiki/Propoxur" title="Propoxur">Propoxur</a></li> <li><a href="/w/index.php?title=Thiodicarb&action=edit&redlink=1" class="new" title="Thiodicarb (page does not exist)">Thiodicarb</a></li> <li><a href="/wiki/Thiofanox" title="Thiofanox">Thiofanox</a>; Stigmines: <a href="/wiki/Distigmine" title="Distigmine">Distigmine</a></li> <li><a href="/w/index.php?title=Eptastigmine&action=edit&redlink=1" class="new" title="Eptastigmine (page does not exist)">Eptastigmine</a></li> <li><a href="/w/index.php?title=Ganstigmine&action=edit&redlink=1" class="new" title="Ganstigmine (page does not exist)">Ganstigmine</a></li> <li><a href="/wiki/Neostigmine" title="Neostigmine">Neostigmine</a> <a href="/wiki/Neostigmine/glycopyrronium_bromide" title="Neostigmine/glycopyrronium bromide">+glycopyrronium bromide</a></li> <li><a href="/wiki/Phenserine" title="Phenserine">Phenserine</a></li> <li><a href="/wiki/Physostigmine" title="Physostigmine">Physostigmine</a></li> <li><a href="/wiki/Pyridostigmine" title="Pyridostigmine">Pyridostigmine</a></li> <li><a href="/w/index.php?title=Quilostigmine&action=edit&redlink=1" class="new" title="Quilostigmine (page does not exist)">Quilostigmine</a></li> <li><a href="/wiki/Rivastigmine" title="Rivastigmine">Rivastigmine</a></li> <li><a href="/w/index.php?title=Terestigmine&action=edit&redlink=1" class="new" title="Terestigmine (page does not exist)">Terestigmine</a>; Others: <a href="/wiki/Acotiamide" title="Acotiamide">Acotiamide</a></li> <li><a href="/wiki/Ambenonium" class="mw-redirect" title="Ambenonium">Ambenonium</a></li> <li><a href="/wiki/Caffeine" title="Caffeine">Caffeine</a></li> <li><a href="/wiki/Donepezil" title="Donepezil">Donepezil</a></li> <li><a href="/wiki/EA-3990" title="EA-3990">EA-3990</a></li> <li><a href="/wiki/EA-4056" title="EA-4056">EA-4056</a></li> <li><a href="/wiki/Edrophonium" title="Edrophonium">Edrophonium</a></li> <li><a class="mw-selflink selflink">Galantamine</a></li> <li><a href="/wiki/Huperzine_A" title="Huperzine A">Huperzine A</a></li> <li><a href="/w/index.php?title=Huprine_W&action=edit&redlink=1" class="new" title="Huprine W (page does not exist)">Huprine W</a></li> <li><a href="/wiki/Huprine_X" title="Huprine X">Huprine X</a></li> <li><a href="/w/index.php?title=Huprine_Y&action=edit&redlink=1" class="new" title="Huprine Y (page does not exist)">Huprine Y</a></li> <li><a href="/wiki/Ipidacrine" title="Ipidacrine">Ipidacrine</a></li> <li><a href="/wiki/Itopride" title="Itopride">Itopride</a></li> <li><a href="/wiki/Ladostigil" title="Ladostigil">Ladostigil</a></li> <li><a href="/wiki/Minaprine" title="Minaprine">Minaprine</a></li> <li><a href="/wiki/Octamethylene-bis(5-dimethylcarbamoxyisoquinolinium_bromide)" title="Octamethylene-bis(5-dimethylcarbamoxyisoquinolinium bromide)">Octamethylene-bis(5-dimethylcarbamoxyisoquinolinium bromide)</a></li> <li><a href="/wiki/T-1123" title="T-1123">T-1123</a></li> <li><a href="/wiki/T-1152" title="T-1152">T-1152</a></li> <li><a href="/wiki/T-1194" title="T-1194">T-1194</a></li> <li><a href="/wiki/TL-599" title="TL-599">TL-599</a></li> <li><a href="/wiki/TL-1238" title="TL-1238">TL-1238</a></li> <li><a href="/wiki/Tacrine" title="Tacrine">Tacrine</a></li> <li><a href="/w/index.php?title=Zanapezil&action=edit&redlink=1" class="new" title="Zanapezil (page does not exist)">Zanapezil</a></li></ul> <ul><li><i>Irreversible:</i> Organophosphates: <a href="/wiki/2-Ethoxycarbonyl-1-methylvinyl_cyclohexyl_methylphosphonate" title="2-Ethoxycarbonyl-1-methylvinyl cyclohexyl methylphosphonate">2-Ethoxycarbonyl-1-methylvinyl cyclohexyl methylphosphonate</a></li> <li><a href="/wiki/Acephate" title="Acephate">Acephate</a></li> <li><a href="/wiki/Armine_(chemical)" title="Armine (chemical)">Armine</a></li> <li><a href="/wiki/Azinphos-ethyl" title="Azinphos-ethyl">Azinphos-ethyl</a></li> <li><a href="/wiki/Azinphos-methyl" title="Azinphos-methyl">Azinphos-methyl</a></li> <li><a href="/wiki/BAY-29952" title="BAY-29952">BAY-29952</a></li> <li><a href="/wiki/Bensulide" title="Bensulide">Bensulide</a></li> <li><a href="/wiki/Cadusafos" title="Cadusafos">Cadusafos</a></li> <li><a href="/wiki/Carbophenothion" title="Carbophenothion">Carbophenothion</a></li> <li><a href="/wiki/Chlorethoxyfos" title="Chlorethoxyfos">Chlorethoxyfos</a></li> <li><a href="/wiki/Chlorfenvinphos" title="Chlorfenvinphos">Chlorfenvinphos</a></li> <li><a href="/wiki/Chlorpyrifos" title="Chlorpyrifos">Chlorpyrifos</a></li> <li><a href="/wiki/Chlorpyrifos-methyl" class="mw-redirect" title="Chlorpyrifos-methyl">Chlorpyrifos-methyl</a></li> <li><a href="/wiki/Coumaphos" title="Coumaphos">Coumaphos</a></li> <li><a href="/wiki/Crotylsarin" title="Crotylsarin">Crotylsarin</a></li> <li><a href="/wiki/Cyanophos" title="Cyanophos">Cyanophos</a></li> <li><a href="/wiki/Cyclosarin" title="Cyclosarin">Cyclosarin (GF)</a></li> <li><a href="/wiki/Demephion" title="Demephion">Demephion</a></li> <li><a href="/wiki/Demeton" title="Demeton">Demeton</a></li> <li><a href="/wiki/Demeton-S-methyl" title="Demeton-S-methyl">Demeton-S-methyl</a></li> <li><a href="/wiki/Dialifor" title="Dialifor">Dialifor</a></li> <li><a href="/wiki/Diazinon" title="Diazinon">Diazinon</a></li> <li><a href="/wiki/Dichlorvos" title="Dichlorvos">Dichlorvos</a></li> <li><a href="/wiki/Dicrotophos" title="Dicrotophos">Dicrotophos</a></li> <li><a href="/wiki/Dicyclohexyl_phosphorofluoridate" title="Dicyclohexyl phosphorofluoridate">Dicyclohexyl phosphorofluoridate</a></li> <li><a href="/wiki/Diisopropylphosphate" title="Diisopropylphosphate">Diisopropylphosphate</a></li> <li><a href="/wiki/Diisopropyl_fluorophosphate" title="Diisopropyl fluorophosphate">Diisopropyl fluorophosphate</a></li> <li><a href="/wiki/Dimefox" title="Dimefox">Dimefox</a></li> <li><a href="/wiki/Dimethoate" title="Dimethoate">Dimethoate</a></li> <li><a href="/wiki/Dimethyl_4-(methylthio)phenyl_phosphate" title="Dimethyl 4-(methylthio)phenyl phosphate">Dimethyl 4-(methylthio)phenyl phosphate</a></li> <li><a href="/wiki/Dioxathion" title="Dioxathion">Dioxathion</a></li> <li><a href="/wiki/Disulfoton" title="Disulfoton">Disulfoton</a></li> <li><a href="/wiki/EA-2012" title="EA-2012">EA-2012</a></li> <li><a href="/wiki/EA-2054" title="EA-2054">EA-2054</a></li> <li><a href="/wiki/EA-2098" title="EA-2098">EA-2098</a></li> <li><a href="/wiki/EA-2192" title="EA-2192">EA-2192</a></li> <li><a href="/wiki/EA-2613" title="EA-2613">EA-2613</a></li> <li><a href="/wiki/EA-3148" title="EA-3148">EA-3148</a></li> <li><a href="/wiki/EA-4352" title="EA-4352">EA-4352</a></li> <li><a href="/wiki/Echothiophate" title="Echothiophate">Echothiophate</a></li> <li><a href="/wiki/Ethylsarin" title="Ethylsarin">Ethylsarin (GE)</a></li> <li><a href="/wiki/Endothion" title="Endothion">Endothion</a></li> <li><a href="/wiki/EPN_(insecticide)" title="EPN (insecticide)">EPN</a></li> <li><a href="/wiki/Ethion" title="Ethion">Ethion</a></li> <li><a href="/wiki/Ethoprop" class="mw-redirect" title="Ethoprop">Ethoprop</a></li> <li><a href="/wiki/Fenamiphos" title="Fenamiphos">Fenamiphos</a></li> <li><a href="/wiki/Fenitrothion" title="Fenitrothion">Fenitrothion</a></li> <li><a href="/wiki/Fenthion" title="Fenthion">Fenthion</a></li> <li><a href="/wiki/Fluorotabun" title="Fluorotabun">Fluorotabun</a></li> <li><a href="/wiki/Fonofos" title="Fonofos">Fonofos</a></li> <li><a href="/wiki/Formothion" title="Formothion">Formothion</a></li> <li><a href="/w/index.php?title=Fosthiazate&action=edit&redlink=1" class="new" title="Fosthiazate (page does not exist)">Fosthiazate</a></li> <li><a href="/wiki/GD-42" title="GD-42">GD-42</a></li> <li><a href="/wiki/GH_(nerve_agent)" title="GH (nerve agent)">GH</a></li> <li><a href="/w/index.php?title=GT-45&action=edit&redlink=1" class="new" title="GT-45 (page does not exist)">GT-45</a></li> <li><a href="/wiki/GV_(nerve_agent)" title="GV (nerve agent)">GV</a></li> <li><a href="/wiki/Guanitoxin" title="Guanitoxin">Guanitoxin</a></li> <li><a href="/wiki/Hexaethyl_tetraphosphate" title="Hexaethyl tetraphosphate">Hexaethyl tetraphosphate (HETP)</a></li> <li><a href="/wiki/Isofluorophate" class="mw-redirect" title="Isofluorophate">Isofluorophate</a></li> <li><a href="/wiki/Isoxathion" title="Isoxathion">Isoxathion</a></li> <li><a href="/wiki/Leptophos" title="Leptophos">Leptophos</a></li> <li><a href="/wiki/Malaoxon" title="Malaoxon">Malaoxon</a></li> <li><a href="/wiki/Malathion" title="Malathion">Malathion</a></li> <li><a href="/w/index.php?title=Mazidox&action=edit&redlink=1" class="new" title="Mazidox (page does not exist)">Mazidox</a></li> <li><a href="/wiki/Methamidophos" title="Methamidophos">Methamidophos</a></li> <li><a href="/wiki/Methidathion" title="Methidathion">Methidathion</a></li> <li><a href="/wiki/Methyl_phenkapton" title="Methyl phenkapton">Methyl phenkapton</a></li> <li><a href="/wiki/Methylfluorophosphonylcholine" title="Methylfluorophosphonylcholine">Methylfluorophosphonylcholine (MFPCh)</a></li> <li><a href="/wiki/Metrifonate" title="Metrifonate">Metrifonate</a></li> <li><a href="/wiki/Mevinphos" title="Mevinphos">Mevinphos</a></li> <li><a href="/wiki/Mipafox" title="Mipafox">Mipafox</a></li> <li><a href="/wiki/Monocrotophos" title="Monocrotophos">Monocrotophos</a></li> <li><a href="/wiki/MSPI_(nerve_agent)" title="MSPI (nerve agent)">MSPI</a></li> <li><a href="/wiki/Naled" title="Naled">Naled</a></li> <li><a href="/wiki/Novichok_agent" class="mw-redirect" title="Novichok agent">Novichok agent</a></li> <li><a href="/wiki/Omethoate" title="Omethoate">Omethoate</a></li> <li><a href="/wiki/Oxydemeton-methyl" title="Oxydemeton-methyl">Oxydemeton-methyl</a></li> <li><a href="/wiki/Paraoxon" title="Paraoxon">Paraoxon</a></li> <li><a href="/wiki/Parathion" title="Parathion">Parathion</a></li> <li><a href="/wiki/Parathion-methyl" class="mw-redirect" title="Parathion-methyl">Parathion-methyl</a></li> <li><a href="/wiki/Phorate" title="Phorate">Phorate</a></li> <li><a href="/wiki/Phosalone" title="Phosalone">Phosalone</a></li> <li><a href="/wiki/Phosfolan" title="Phosfolan">Phosfolan</a></li> <li><a href="/wiki/Phosmet" title="Phosmet">Phosmet</a></li> <li><a href="/wiki/Phosphamidon" title="Phosphamidon">Phosphamidon</a></li> <li><a href="/wiki/Phoxim" title="Phoxim">Phoxim</a></li> <li><a href="/wiki/Pirimiphos-methyl" title="Pirimiphos-methyl">Pirimiphos-methyl</a></li> <li><a href="/wiki/Profenofos" title="Profenofos">Profenofos</a></li> <li><a href="/wiki/Prothoate" title="Prothoate">Prothoate</a></li> <li><a href="/wiki/R-16661" title="R-16661">R-16661</a></li> <li><a href="/w/index.php?title=Ro_3-0340&action=edit&redlink=1" class="new" title="Ro 3-0340 (page does not exist)">Ro 3-0340</a></li> <li><a href="/w/index.php?title=Ro_3-0346&action=edit&redlink=1" class="new" title="Ro 3-0346 (page does not exist)">Ro 3-0346</a></li> <li><a href="/w/index.php?title=Ro_3-0347&action=edit&redlink=1" class="new" title="Ro 3-0347 (page does not exist)">Ro 3-0347</a></li> <li><a href="/w/index.php?title=Ro_3-0351&action=edit&redlink=1" class="new" title="Ro 3-0351 (page does not exist)">Ro 3-0351</a></li> <li><a href="/w/index.php?title=Ro_3-0352&action=edit&redlink=1" class="new" title="Ro 3-0352 (page does not exist)">Ro 3-0352</a></li> <li><a href="/w/index.php?title=Ro_3-0397&action=edit&redlink=1" class="new" title="Ro 3-0397 (page does not exist)">Ro 3-0397</a></li> <li><a href="/w/index.php?title=Ro_3-0411&action=edit&redlink=1" class="new" title="Ro 3-0411 (page does not exist)">Ro 3-0411</a></li> <li><a href="/wiki/Ro_3-0412" title="Ro 3-0412">Ro 3-0412</a></li> <li><a href="/w/index.php?title=Ro_3-0417&action=edit&redlink=1" class="new" title="Ro 3-0417 (page does not exist)">Ro 3-0417</a></li> <li><a href="/wiki/Ro_3-0419" title="Ro 3-0419">Ro 3-0419</a></li> <li><a href="/wiki/Ro_3-0422" title="Ro 3-0422">Ro 3-0422</a></li> <li><a href="/w/index.php?title=Ro_3-0433&action=edit&redlink=1" class="new" title="Ro 3-0433 (page does not exist)">Ro 3-0433</a></li> <li><a href="/w/index.php?title=Ronnel&action=edit&redlink=1" class="new" title="Ronnel (page does not exist)">Ronnel</a></li> <li><a href="/wiki/Sarin" title="Sarin">Sarin (GB)</a></li> <li><a href="/wiki/Schradan" title="Schradan">Schradan</a></li> <li><a href="/wiki/Soman" title="Soman">Soman (GD)</a></li> <li><a href="/wiki/Sulfotep" title="Sulfotep">Sulfotep (TEDP)</a></li> <li><a href="/wiki/Tabun_(nerve_agent)" title="Tabun (nerve agent)">Tabun (GA)</a></li> <li><a href="/wiki/Tebupirimfos" title="Tebupirimfos">Tebupirimfos</a></li> <li><a href="/wiki/Temefos" title="Temefos">Temefos</a></li> <li><a href="/wiki/Terbufos" title="Terbufos">Terbufos</a></li> <li><a href="/wiki/Tetrachlorvinphos" title="Tetrachlorvinphos">Tetrachlorvinphos</a></li> <li><a href="/wiki/Tetraethyl_pyrophosphate" title="Tetraethyl pyrophosphate">Tetraethyl pyrophosphate (TEPP)</a></li> <li><a href="/wiki/Triazofos" title="Triazofos">Triazofos</a></li> <li><a href="/w/index.php?title=Tribufos&action=edit&redlink=1" class="new" title="Tribufos (page does not exist)">Tribufos</a></li> <li><a href="/wiki/Trichlorfon" class="mw-redirect" title="Trichlorfon">Trichlorfon</a></li> <li><a href="/wiki/Trichloronate" title="Trichloronate">Trichloronate</a></li> <li><a href="/wiki/Tricresyl_phosphate" title="Tricresyl phosphate">Tricresyl phosphate</a></li> <li><a href="/wiki/VE_(nerve_agent)" title="VE (nerve agent)">VE</a></li> <li><a href="/wiki/VG_(nerve_agent)" title="VG (nerve agent)">VG</a></li> <li><a href="/wiki/VM_(nerve_agent)" title="VM (nerve agent)">VM</a></li> <li><a href="/wiki/VP_(nerve_agent)" class="mw-redirect" title="VP (nerve agent)">VP</a></li> <li><a href="/wiki/VS_(nerve_agent)" title="VS (nerve agent)">VS</a></li> <li><a href="/wiki/VR_(nerve_agent)" title="VR (nerve agent)">VR</a></li> <li><a href="/wiki/VX_(nerve_agent)" title="VX (nerve agent)">VX</a>; Others: <a href="/wiki/Demecarium" class="mw-redirect" title="Demecarium">Demecarium</a></li> <li><a href="/wiki/Fasciculin" title="Fasciculin">Fasciculins (green mamba toxins)</a> (<a href="/w/index.php?title=Fasciculin_1&action=edit&redlink=1" class="new" title="Fasciculin 1 (page does not exist)">1</a>, <a href="/w/index.php?title=Fasciculin_2&action=edit&redlink=1" class="new" title="Fasciculin 2 (page does not exist)">2</a>, <a href="/w/index.php?title=Fasciculin_3&action=edit&redlink=1" class="new" title="Fasciculin 3 (page does not exist)">3</a>, <a href="/w/index.php?title=Fasciculin_4&action=edit&redlink=1" class="new" title="Fasciculin 4 (page does not exist)">4</a>)</li> <li><a href="/wiki/Onchidal" title="Onchidal">Onchidal</a> (<i><a href="/wiki/Onchidella_binneyi" title="Onchidella binneyi">Onchidella binneyi</a></i>)</li> <li><a href="/wiki/Methanesulfonyl_fluoride" title="Methanesulfonyl fluoride">Methanesulfonyl fluoride</a></li></ul> <ul><li><i>Unsorted:</i> <a href="/wiki/%CE%91-Pinene" title="Α-Pinene">α-Pinene</a></li> <li><a href="/wiki/%CE%91-Viniferin" title="Α-Viniferin">α-Viniferin</a></li> <li><a href="/wiki/Affinine" title="Affinine">Affinine</a></li> <li><a href="/wiki/Affinisine" title="Affinisine">Affinisine</a></li> <li><a href="/wiki/Arisugacin_A" title="Arisugacin A">Arisugacin A</a></li> <li><a href="/wiki/Bulbocapnine" title="Bulbocapnine">Bulbocapnine</a></li> <li><a href="/wiki/Conodurine" title="Conodurine">Conodurine</a></li> <li><a href="/wiki/Coronaridine" title="Coronaridine">Coronaridine</a></li> <li><a href="/wiki/Corydaline" title="Corydaline">Corydaline</a></li> <li><a href="/wiki/Corynoline" title="Corynoline">Corynoline</a></li> <li><a href="/wiki/Crimidine" title="Crimidine">Crimidine</a></li> <li><a href="/wiki/Cyclanoline" title="Cyclanoline">Cyclanoline</a></li> <li><a href="/wiki/Cymserine" title="Cymserine">Cymserine</a></li> <li><a href="/wiki/Harmaline" title="Harmaline">Harmaline</a></li> <li><a href="/wiki/Kobophenol_A" title="Kobophenol A">Kobophenol A</a></li> <li><a href="/wiki/Lactucopicrin" title="Lactucopicrin">Lactucopicrin</a></li> <li><a href="/wiki/Lycorine" title="Lycorine">Lycorine</a></li> <li><a href="/wiki/Phosacetim" title="Phosacetim">Phosacetim</a></li> <li><a href="/wiki/Rosmarinic_acid" title="Rosmarinic acid">Rosmarinic acid</a></li> <li><a href="/wiki/Stercuronium_iodide" title="Stercuronium iodide">Stercuronium iodide</a></li> <li><a href="/wiki/Taspine" title="Taspine">Taspine</a></li> <li><a href="/wiki/Tetrahydrocannabinol" title="Tetrahydrocannabinol">Tetrahydrocannabinol</a></li> <li><a href="/wiki/Ungeremine" title="Ungeremine">Ungeremine</a></li> <li><a href="/wiki/Ungiminorine" title="Ungiminorine">Ungiminorine</a></li> <li><a href="/wiki/Dimethylcarbamoyl_fluoride" title="Dimethylcarbamoyl fluoride">Dimethylcarbamoyl fluoride</a></li> <li><a href="/wiki/BW284C51" title="BW284C51">BW284C51</a></li> <li><a href="/wiki/TMTFA" title="TMTFA">TMTFA</a></li> <li><a href="/wiki/3152_CT" title="3152 CT">3152 CT</a></li></ul> <ul><li><a href="/wiki/Cholinesterase_reactivator" title="Cholinesterase reactivator">Reactivators</a>: <a href="/wiki/Asoxime_chloride" title="Asoxime chloride">Asoxime chloride</a></li> <li><a href="/w/index.php?title=Methoxime&action=edit&redlink=1" class="new" title="Methoxime (page does not exist)">Methoxime</a></li> <li><a href="/wiki/Obidoxime" title="Obidoxime">Obidoxime</a></li> <li><a href="/wiki/Pralidoxime" title="Pralidoxime">Pralidoxime</a></li> <li><a href="/wiki/Trimedoxime_bromide" title="Trimedoxime bromide">Trimedoxime bromide</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:6em;;text-align:center;"><a href="/wiki/Butyrylcholinesterase" title="Butyrylcholinesterase"><abbr title="Butyrylcholinesterase">BChE</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 Butyrylcholinesterase</span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><b>Inhibitors:</b> <a href="/wiki/Affinine" title="Affinine">Affinine</a></li> <li><a href="/wiki/Affinisine" title="Affinisine">Affinisine</a></li> <li><a href="/wiki/Conodurine" title="Conodurine">Conodurine</a></li> <li><a href="/wiki/Cymserine" title="Cymserine">Cymserine</a></li> <li><a href="/wiki/Ladostigil" title="Ladostigil">Ladostigil</a></li> <li><a href="/wiki/Profenamine" title="Profenamine">Profenamine (ethopropazine)</a></li> <li><a href="/wiki/Rivastigmine" title="Rivastigmine">Rivastigmine</a></li> <li><a href="/wiki/Tacrine" title="Tacrine">Tacrine</a></li> <li><a href="/w/index.php?title=ZINC-12613047&action=edit&redlink=1" class="new" title="ZINC-12613047 (page does not exist)">ZINC-12613047</a></li> <li>Many of the other AChE inhibitors listed above</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/Transporter_modulator" class="mw-redirect" title="Transporter modulator">modulators</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:6em;;text-align:center;"><a href="/wiki/Choline_transporter" title="Choline transporter"><abbr title="Choline transporter">CHT</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 Choline transporter</span></th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><b>Inhibitors:</b> <a href="/wiki/Hemicholinium-3" title="Hemicholinium-3">Hemicholinium-3 (hemicholine)</a></li> <li><a href="/wiki/Triethylcholine" title="Triethylcholine">Triethylcholine</a></li></ul> <ul><li><b>Enhancers:</b> <a href="/wiki/Coluracetam" title="Coluracetam">Coluracetam</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:6em;;text-align:center;"><a href="/wiki/Vesicular_acetylcholine_transporter" title="Vesicular acetylcholine transporter"><abbr title="Vesicular acetylcholine transporter">VAChT</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Vesicular acetylcholine transporter</span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><b>Inhibitors:</b> <a href="/wiki/Vesamicol" title="Vesamicol">Vesamicol</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Neurotransmitter_release" class="mw-redirect" title="Neurotransmitter release">Release</a><br /><small>(<a href="/wiki/Release_modulator" title="Release modulator">modulators</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:6em;;text-align:center;"><a href="/wiki/Release_inhibitor" class="mw-redirect" title="Release inhibitor">Inhibitors</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><b><a href="/wiki/Synaptosomal-associated_protein_25" class="mw-redirect" title="Synaptosomal-associated protein 25"><abbr title="Synaptosomal-associated protein 25">SNAP-25</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 Synaptosomal-associated protein 25</span> inactivators:</b> <a href="/wiki/Botulinum_toxin" title="Botulinum toxin">Botulinum toxin</a> (<a href="/wiki/Botulinum_toxin_A" class="mw-redirect" title="Botulinum toxin A">A</a>, <a href="/wiki/Botulinum_toxin_C" class="mw-redirect" title="Botulinum toxin C">C</a>, <a href="/wiki/Botulinum_toxin_E" class="mw-redirect" title="Botulinum toxin E">E</a>)</li></ul> <ul><li><b><a href="/wiki/Vesicle-associated_membrane_protein" title="Vesicle-associated membrane protein"><abbr title="Vesicle-associated membrane protein">VAMP</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 Vesicle-associated membrane protein</span> inactivators:</b> <a href="/wiki/Botulinum_toxin" title="Botulinum toxin">Botulinum toxin</a> (<a href="/wiki/Botulinum_toxin_B" class="mw-redirect" title="Botulinum toxin B">B</a>, <a href="/wiki/Botulinum_toxin_D" class="mw-redirect" title="Botulinum toxin D">D</a>, <a href="/wiki/Botulinum_toxin_F" class="mw-redirect" title="Botulinum toxin F">F</a>, <a href="/wiki/Botulinum_toxin_G" class="mw-redirect" title="Botulinum toxin G">G</a>)</li></ul> <ul><li><b>Others:</b> <a href="/wiki/Bungarotoxin" title="Bungarotoxin">Bungarotoxins</a> (<a href="/wiki/Beta-Bungarotoxin" class="mw-redirect" title="Beta-Bungarotoxin">β-bungarotoxin</a>, <a href="/wiki/%CE%93-bungarotoxin" class="mw-redirect" title="Γ-bungarotoxin">γ-bungarotoxin</a>)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:6em;;text-align:center;"><a href="/wiki/Release_enhancer" class="mw-redirect" title="Release enhancer">Enhancers</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><b><a href="/wiki/Latrophilin" title="Latrophilin"><abbr title="Latrophilin">LPHN</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 Latrophilin</span> agonists:</b> <a href="/wiki/Alpha-Latrotoxin" class="mw-redirect" title="Alpha-Latrotoxin">α-Latrotoxin</a></li></ul> <ul><li><b>Others:</b> Atracotoxins (e.g., <a href="/wiki/Robustoxin" class="mw-redirect" title="Robustoxin">robustoxin</a>, <a href="/wiki/Versutoxin" title="Versutoxin">versutoxin</a>)</li> <li><a href="/wiki/Crotoxin" title="Crotoxin">Crotoxin</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><a href="/wiki/Template:Receptor_modulators" title="Template:Receptor modulators">Receptor/signaling modulators</a></dd> <dd><a href="/wiki/Template:Muscarinic_acetylcholine_receptor_modulators" title="Template:Muscarinic acetylcholine receptor modulators">Muscarinic acetylcholine receptor modulators</a></dd> <dd><a href="/wiki/Template:Nicotinic_acetylcholine_receptor_modulators" title="Template:Nicotinic acetylcholine receptor modulators">Nicotinic acetylcholine receptor modulators</a></dd></dl> </div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"></div><div role="navigation" class="navbox" aria-labelledby="Nicotinic_acetylcholine_receptor_modulators" style="padding:3px"><table class="nowraplinks hlist mw-collapsible mw-collapsed navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Nicotinic_acetylcholine_receptor_modulators" title="Template:Nicotinic acetylcholine receptor modulators"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Nicotinic_acetylcholine_receptor_modulators" title="Template talk:Nicotinic acetylcholine receptor modulators"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Nicotinic_acetylcholine_receptor_modulators" title="Special:EditPage/Template:Nicotinic acetylcholine receptor modulators"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Nicotinic_acetylcholine_receptor_modulators" style="font-size:114%;margin:0 4em"><a href="/wiki/Nicotinic_acetylcholine_receptor" title="Nicotinic acetylcholine receptor">Nicotinic acetylcholine receptor</a> <a href="/wiki/Receptor_modulator" title="Receptor modulator">modulators</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Nicotinic_acetylcholine_receptors" class="mw-redirect" title="Nicotinic acetylcholine receptors"><abbr title="Nicotinic acetylcholine receptors">nAChRs</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 Nicotinic acetylcholine receptors</span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Receptor_agonist" class="mw-redirect" title="Receptor agonist">Agonists</a><br />(and <a href="/wiki/Positive_allosteric_modulators" class="mw-redirect" title="Positive allosteric modulators"><abbr title="positive allosteric modulators">PAMs</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 positive allosteric modulators</span>)</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/5-Hydroxyindoleacetic_acid" title="5-Hydroxyindoleacetic acid">5-HIAA</a></li> <li><a href="/wiki/6-Chloronicotine" title="6-Chloronicotine">6-Chloronicotine</a></li> <li><a href="/wiki/A-84,543" title="A-84,543">A-84,543</a></li> <li><a href="/wiki/A-366,833" title="A-366,833">A-366,833</a></li> <li><a href="/w/index.php?title=A-582,941&action=edit&redlink=1" class="new" title="A-582,941 (page does not exist)">A-582,941</a></li> <li><a href="/w/index.php?title=A-867,744&action=edit&redlink=1" class="new" title="A-867,744 (page does not exist)">A-867,744</a></li> <li><a href="/wiki/ABT-202" title="ABT-202">ABT-202</a></li> <li><a href="/wiki/ABT-418" title="ABT-418">ABT-418</a></li> <li><a href="/w/index.php?title=ABT-560&action=edit&redlink=1" class="new" title="ABT-560 (page does not exist)">ABT-560</a></li> <li><a href="/w/index.php?title=ABT-894&action=edit&redlink=1" class="new" title="ABT-894 (page does not exist)">ABT-894</a></li> <li><a href="/wiki/Acetylcholine" title="Acetylcholine">Acetylcholine</a></li> <li><a href="/wiki/Altinicline" title="Altinicline">Altinicline</a></li> <li><a href="/wiki/Anabasine" title="Anabasine">Anabasine</a></li> <li><a href="/wiki/Anatabine" title="Anatabine">Anatabine</a></li> <li><a href="/wiki/Anatoxin-a" title="Anatoxin-a">Anatoxin-a</a></li> <li><a href="/wiki/AR-R17779" title="AR-R17779">AR-R17779</a></li> <li><a href="/wiki/Bephenium_hydroxynaphthoate" title="Bephenium hydroxynaphthoate">Bephenium hydroxynaphthoate</a></li> <li><a href="/wiki/Butinoline" title="Butinoline">Butinoline</a></li> <li><a href="/wiki/Butyrylcholine" title="Butyrylcholine">Butyrylcholine</a></li> <li><a href="/wiki/Carbachol" title="Carbachol">Carbachol</a></li> <li><a href="/wiki/Choline" title="Choline">Choline</a></li> <li><a href="/wiki/Cotinine" title="Cotinine">Cotinine</a></li> <li><a href="/wiki/Cytisine" title="Cytisine">Cytisine</a></li> <li><a href="/wiki/Decamethonium" title="Decamethonium">Decamethonium</a></li> <li><a href="/wiki/Desformylflustrabromine" title="Desformylflustrabromine">Desformylflustrabromine</a></li> <li><a href="/wiki/Dianicline" title="Dianicline">Dianicline</a></li> <li><a href="/wiki/Dimethylphenylpiperazinium" title="Dimethylphenylpiperazinium">Dimethylphenylpiperazinium</a></li> <li><a href="/wiki/Epibatidine" title="Epibatidine">Epibatidine</a></li> <li><a href="/wiki/Epiboxidine" title="Epiboxidine">Epiboxidine</a></li> <li><a href="/wiki/Alcohol_(drug)" title="Alcohol (drug)">Ethanol (alcohol)</a></li> <li><a href="/w/index.php?title=Ethoxysebacylcholine&action=edit&redlink=1" class="new" title="Ethoxysebacylcholine (page does not exist)">Ethoxysebacylcholine</a></li> <li><a href="/w/index.php?title=EVP-4473&action=edit&redlink=1" class="new" title="EVP-4473 (page does not exist)">EVP-4473</a></li> <li><a href="/wiki/EVP-6124" class="mw-redirect" title="EVP-6124">EVP-6124</a></li> <li><a class="mw-selflink selflink">Galantamine</a></li> <li><a href="/wiki/GTS-21" title="GTS-21">GTS-21</a></li> <li><a href="/wiki/Ispronicline" title="Ispronicline">Ispronicline</a></li> <li><a href="/wiki/Ivermectin" title="Ivermectin">Ivermectin</a></li> <li><a href="/wiki/JNJ-39393406" title="JNJ-39393406">JNJ-39393406</a></li> <li><a href="/wiki/Levamisole" title="Levamisole">Levamisole</a></li> <li><a href="/wiki/Lobeline" title="Lobeline">Lobeline</a></li> <li><a href="/w/index.php?title=MEM-63,908&action=edit&redlink=1" class="new" title="MEM-63,908 (page does not exist)">MEM-63,908 (RG-3487)</a></li> <li><a href="/wiki/Morantel" title="Morantel">Morantel</a></li> <li><a href="/wiki/Nicotine" title="Nicotine">Nicotine</a> (<a href="/wiki/Tobacco" title="Tobacco">tobacco</a>)</li> <li><a href="/w/index.php?title=NS-1738&action=edit&redlink=1" class="new" title="NS-1738 (page does not exist)">NS-1738</a></li> <li><a href="/wiki/PHA-543,613" title="PHA-543,613">PHA-543,613</a></li> <li><a href="/w/index.php?title=PHA-709,829&action=edit&redlink=1" class="new" title="PHA-709,829 (page does not exist)">PHA-709,829</a></li> <li><a href="/wiki/PNU-120,596" title="PNU-120,596">PNU-120,596</a></li> <li><a href="/wiki/PNU-282,987" title="PNU-282,987">PNU-282,987</a></li> <li><a href="/wiki/Pozanicline" title="Pozanicline">Pozanicline</a></li> <li><a href="/wiki/Pyrantel" title="Pyrantel">Pyrantel</a></li> <li><a href="/wiki/Rivanicline" title="Rivanicline">Rivanicline</a></li> <li><a href="/wiki/RJR-2429" title="RJR-2429">RJR-2429</a></li> <li><a href="/wiki/Sazetidine_A" title="Sazetidine A">Sazetidine A</a></li> <li><a href="/wiki/SB-206553" title="SB-206553">SB-206553</a></li> <li><a href="/w/index.php?title=Sebacylcholine&action=edit&redlink=1" class="new" title="Sebacylcholine (page does not exist)">Sebacylcholine</a></li> <li><a href="/wiki/SIB-1508Y" class="mw-redirect" title="SIB-1508Y">SIB-1508Y</a></li> <li><a href="/wiki/SIB-1553A" title="SIB-1553A">SIB-1553A</a></li> <li><a href="/wiki/SSR-180,711" title="SSR-180,711">SSR-180,711</a></li> <li><a href="/w/index.php?title=Suberyldicholine&action=edit&redlink=1" class="new" title="Suberyldicholine (page does not exist)">Suberyldicholine</a></li> <li><a href="/wiki/Suxamethonium" class="mw-redirect" title="Suxamethonium">Suxamethonium (succinylcholine)</a></li> <li><a href="/wiki/Suxethonium_chloride" title="Suxethonium chloride">Suxethonium (succinyldicholine)</a></li> <li><a href="/wiki/TC-1698" title="TC-1698">TC-1698</a></li> <li><a href="/w/index.php?title=TC-1734&action=edit&redlink=1" class="new" title="TC-1734 (page does not exist)">TC-1734</a></li> <li><a href="/wiki/TC-1827" title="TC-1827">TC-1827</a></li> <li><a href="/wiki/TC-2216" title="TC-2216">TC-2216</a></li> <li><a href="/wiki/TC-5214" class="mw-redirect" title="TC-5214">TC-5214</a></li> <li><a href="/wiki/TC-5619" class="mw-redirect" title="TC-5619">TC-5619</a></li> <li><a href="/w/index.php?title=TC-6683&action=edit&redlink=1" class="new" title="TC-6683 (page does not exist)">TC-6683</a></li> <li><a href="/wiki/Tebanicline" title="Tebanicline">Tebanicline</a></li> <li><a href="/wiki/Tribendimidine" title="Tribendimidine">Tribendimidine</a></li> <li><a href="/wiki/Tropisetron" title="Tropisetron">Tropisetron</a></li> <li><a href="/wiki/UB-165" title="UB-165">UB-165</a></li> <li><a href="/wiki/Varenicline" title="Varenicline">Varenicline</a></li> <li><a href="/wiki/WAY-317,538" class="mw-redirect" title="WAY-317,538">WAY-317,538</a></li> <li><a href="/w/index.php?title=XY-4083&action=edit&redlink=1" class="new" title="XY-4083 (page does not exist)">XY-4083</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Receptor_antagonist" title="Receptor antagonist">Antagonists</a><br />(and <a href="/wiki/Negative_allosteric_modulators" class="mw-redirect" title="Negative allosteric modulators"><abbr title="negative allosteric modulators">NAMs</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 negative allosteric modulators</span>)</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/18-Methylaminocoronaridine" title="18-Methylaminocoronaridine">18-MAC</a></li> <li><a href="/wiki/18-Methoxycoronaridine" title="18-Methoxycoronaridine">18-MC</a></li> <li><a href="/wiki/%CE%91-Neurotoxin" title="Α-Neurotoxin">α-Neurotoxins</a> (e.g., <a href="/wiki/%CE%91-bungarotoxin" class="mw-redirect" title="Α-bungarotoxin">α-bungarotoxin</a>, <a href="/wiki/%CE%91-cobratoxin" class="mw-redirect" title="Α-cobratoxin">α-cobratoxin</a>, <a href="/wiki/%CE%91-conotoxin" class="mw-redirect" title="Α-conotoxin">α-conotoxin</a>, many others)</li> <li><a href="/w/index.php?title=ABT-126&action=edit&redlink=1" class="new" title="ABT-126 (page does not exist)">ABT-126</a></li> <li><a href="/wiki/Alcuronium" class="mw-redirect" title="Alcuronium">Alcuronium</a></li> <li><a href="/wiki/Allopregnanolone" title="Allopregnanolone">Allopregnanolone</a></li> <li><a href="/wiki/Amantadine" title="Amantadine">Amantadine</a></li> <li><a href="/w/index.php?title=Anatruxonium&action=edit&redlink=1" class="new" title="Anatruxonium (page does not exist)">Anatruxonium</a></li> <li><a href="/w/index.php?title=AQW051&action=edit&redlink=1" class="new" title="AQW051 (page does not exist)">AQW051</a></li> <li><a href="/wiki/Atracurium" class="mw-redirect" title="Atracurium">Atracurium</a></li> <li><a href="/wiki/Barbiturates" class="mw-redirect" title="Barbiturates">Barbiturates</a> (e.g., <a href="/wiki/Pentobarbital" title="Pentobarbital">pentobarbital</a>, <a href="/wiki/Sodium_thiopental" title="Sodium thiopental">sodium thiopental</a>)</li> <li><a href="/wiki/BNC-210" title="BNC-210">BNC-210</a></li> <li><a href="/wiki/Bungarotoxin" title="Bungarotoxin">Bungarotoxins</a> (e.g., <a href="/wiki/%CE%91-bungarotoxin" class="mw-redirect" title="Α-bungarotoxin">α-bungarotoxin</a>, <a href="/wiki/%CE%9A-bungarotoxin" class="mw-redirect" title="Κ-bungarotoxin">κ-bungarotoxin</a>)</li> <li><a href="/wiki/Bupropion" title="Bupropion">Bupropion</a></li> <li><a href="/wiki/BW284C51" title="BW284C51">BW284C51</a></li> <li><a href="/wiki/BW-A444" title="BW-A444">BW-A444</a></li> <li><a href="/wiki/Candocuronium_iodide" title="Candocuronium iodide">Candocuronium iodide (chandonium iodide)</a></li> <li><a href="/wiki/Chlorisondamine" title="Chlorisondamine">Chlorisondamine</a></li> <li><a href="/wiki/Cisatracurium" class="mw-redirect" title="Cisatracurium">Cisatracurium</a></li> <li><a href="/wiki/Coclaurine" title="Coclaurine">Coclaurine</a></li> <li><a href="/wiki/Coronaridine" title="Coronaridine">Coronaridine</a></li> <li><a href="/wiki/Curare" title="Curare">Curare</a></li> <li><a href="/wiki/Cyclopropane" title="Cyclopropane">Cyclopropane</a></li> <li><a href="/wiki/Dacuronium_bromide" title="Dacuronium bromide">Dacuronium bromide</a></li> <li><a href="/wiki/Decamethonium" title="Decamethonium">Decamethonium</a></li> <li><a href="/wiki/Dehydronorketamine" title="Dehydronorketamine">Dehydronorketamine</a></li> <li><a href="/wiki/Desflurane" title="Desflurane">Desflurane</a></li> <li><a href="/wiki/Dextromethorphan" title="Dextromethorphan">Dextromethorphan</a></li> <li><a href="/wiki/Dextropropoxyphene" title="Dextropropoxyphene">Dextropropoxyphene</a></li> <li><a href="/wiki/Dextrorphan" title="Dextrorphan">Dextrorphan</a></li> <li><a href="/w/index.php?title=Diadonium&action=edit&redlink=1" class="new" title="Diadonium (page does not exist)">Diadonium</a></li> <li><a href="/w/index.php?title=Dihydro-beta-erythroidine&action=edit&redlink=1" class="new" title="Dihydro-beta-erythroidine (page does not exist)">DHβE</a></li> <li><a href="/wiki/Dihydrochandonium" title="Dihydrochandonium">Dihydrochandonium</a></li> <li><a href="/wiki/Dimethyltubocurarine" class="mw-redirect" title="Dimethyltubocurarine">Dimethyltubocurarine (metocurine)</a></li> <li><a href="/wiki/Dioscorine" title="Dioscorine">Dioscorine</a></li> <li><a href="/wiki/Dipyrandium" title="Dipyrandium">Dipyrandium</a></li> <li><a href="/wiki/Dizocilpine" title="Dizocilpine">Dizocilpine (MK-801)</a></li> <li><a href="/wiki/Doxacurium" class="mw-redirect" title="Doxacurium">Doxacurium</a></li> <li><a href="/wiki/Encenicline" title="Encenicline">Encenicline</a></li> <li><a href="/wiki/Enflurane" title="Enflurane">Enflurane</a></li> <li><a href="/wiki/Erythravine" title="Erythravine">Erythravine</a></li> <li><a href="/wiki/Esketamine" title="Esketamine">Esketamine</a></li> <li><a href="/wiki/Fazadinium" class="mw-redirect" title="Fazadinium">Fazadinium</a></li> <li><a href="/wiki/Gallamine" class="mw-redirect" title="Gallamine">Gallamine</a></li> <li><a href="/wiki/Gantacurium_chloride" title="Gantacurium chloride">Gantacurium chloride</a></li> <li><a href="/wiki/Halothane" title="Halothane">Halothane</a></li> <li><a href="/wiki/Hexafluronium" class="mw-redirect" title="Hexafluronium">Hexafluronium</a></li> <li><a href="/wiki/Hexamethonium" title="Hexamethonium">Hexamethonium (benzohexonium)</a></li> <li><a href="/wiki/Hydroxybupropion" title="Hydroxybupropion">Hydroxybupropion</a></li> <li><a href="/wiki/Hydroxynorketamine" title="Hydroxynorketamine">Hydroxynorketamine</a></li> <li><a href="/wiki/Ibogaine" title="Ibogaine">Ibogaine</a></li> <li><a href="/wiki/Isoflurane" title="Isoflurane">Isoflurane</a></li> <li><a href="/wiki/Ketamine" title="Ketamine">Ketamine</a></li> <li><a href="/wiki/Kynurenic_acid" title="Kynurenic acid">Kynurenic acid</a></li> <li><a href="/wiki/Laudanosine" title="Laudanosine">Laudanosine</a></li> <li><a href="/wiki/Laudexium" class="mw-redirect" title="Laudexium">Laudexium (laudolissin)</a></li> <li><a href="/wiki/Levacetylmethadol" title="Levacetylmethadol">Levacetylmethadol</a></li> <li><a href="/wiki/Levomethadone" title="Levomethadone">Levomethadone</a></li> <li><a href="/wiki/Malouetine" title="Malouetine">Malouetine</a></li> <li><a href="/wiki/2-Methoxyethyl-18-methoxycoronaridinate" title="2-Methoxyethyl-18-methoxycoronaridinate">ME-18-MC</a></li> <li><a href="/wiki/Mecamylamine" title="Mecamylamine">Mecamylamine</a></li> <li><a href="/wiki/Memantine" title="Memantine">Memantine</a></li> <li><a href="/wiki/Methadone" title="Methadone">Methadone</a></li> <li><a href="/wiki/Methorphan" title="Methorphan">Methorphan (racemethorphan)</a></li> <li><a href="/wiki/Methyllycaconitine" title="Methyllycaconitine">Methyllycaconitine</a></li> <li><a href="/wiki/Metocurine" title="Metocurine">Metocurine</a></li> <li><a href="/wiki/Mivacurium" class="mw-redirect" title="Mivacurium">Mivacurium</a></li> <li><a href="/wiki/Morphanol" class="mw-redirect" title="Morphanol">Morphanol (racemorphan)</a></li> <li><a href="/wiki/Neramexane" title="Neramexane">Neramexane</a></li> <li><a href="/wiki/Nitrous_oxide" title="Nitrous oxide">Nitrous oxide</a></li> <li><a href="/wiki/Norketamine" title="Norketamine">Norketamine</a></li> <li><a href="/wiki/Pancuronium_bromide" title="Pancuronium bromide">Pancuronium bromide</a></li> <li><a href="/wiki/Pempidine" title="Pempidine">Pempidine</a></li> <li><a href="/wiki/Pentamine" title="Pentamine">Pentamine</a></li> <li><a href="/wiki/Pentolinium" title="Pentolinium">Pentolinium</a></li> <li><a href="/wiki/Phencyclidine" title="Phencyclidine">Phencyclidine</a></li> <li><a href="/wiki/Pipecuronium_bromide" title="Pipecuronium bromide">Pipecuronium bromide</a></li> <li><a href="/wiki/Progesterone" title="Progesterone">Progesterone</a></li> <li><a href="/wiki/Promegestone" title="Promegestone">Promegestone</a></li> <li><a href="/wiki/Radafaxine" title="Radafaxine">Radafaxine</a></li> <li><a href="/wiki/Rapacuronium_bromide" title="Rapacuronium bromide">Rapacuronium bromide</a></li> <li><a href="/wiki/Reboxetine" title="Reboxetine">Reboxetine</a></li> <li><a href="/wiki/Rocuronium_bromide" title="Rocuronium bromide">Rocuronium bromide</a></li> <li><a href="/wiki/Sevoflurane" title="Sevoflurane">Sevoflurane</a></li> <li><a href="/wiki/Stercuronium_iodide" title="Stercuronium iodide">Stercuronium iodide</a></li> <li><a href="/wiki/Surugatoxin" title="Surugatoxin">Surugatoxin</a></li> <li><a href="/wiki/Thiocolchicoside" title="Thiocolchicoside">Thiocolchicoside</a></li> <li><a href="/wiki/Threohydrobupropion" title="Threohydrobupropion">Threohydrobupropion</a></li> <li><a href="/wiki/Toxiferine" title="Toxiferine">Toxiferine</a></li> <li><a href="/wiki/Tramadol" title="Tramadol">Tramadol</a></li> <li><a href="/wiki/Trimetaphan_camsilate" title="Trimetaphan camsilate">Trimetaphan camsilate (trimethaphan camsylate)</a></li> <li><a href="/w/index.php?title=Tropeinium&action=edit&redlink=1" class="new" title="Tropeinium (page does not exist)">Tropeinium</a></li> <li><a href="/wiki/Tubocurarine" class="mw-redirect" title="Tubocurarine">Tubocurarine</a></li> <li><a href="/wiki/Vanoxerine" title="Vanoxerine">Vanoxerine</a></li> <li><a href="/wiki/Vecuronium_bromide" title="Vecuronium bromide">Vecuronium bromide</a></li> <li><a href="/wiki/Xenon" title="Xenon">Xenon</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Precursor_(chemistry)" title="Precursor (chemistry)">Precursors</a><br /><small>(and <a href="/wiki/Prodrug" title="Prodrug">prodrugs</a>)</small></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Acetyl-coA" class="mw-redirect" title="Acetyl-coA">Acetyl-coA</a></li> <li><a href="/wiki/Adafenoxate" title="Adafenoxate">Adafenoxate</a></li> <li><a href="/wiki/Choline" title="Choline">Choline</a> (<a href="/wiki/Lecithin" title="Lecithin">lecithin</a>)</li> <li><a href="/wiki/Citicoline" title="Citicoline">Citicoline</a></li> <li><a href="/wiki/Cyprodenate" title="Cyprodenate">Cyprodenate</a></li> <li><a href="/wiki/Dimethylethanolamine" title="Dimethylethanolamine">Dimethylethanolamine</a></li> <li><a href="/wiki/Glycerophosphocholine" class="mw-redirect" title="Glycerophosphocholine">Glycerophosphocholine</a></li> <li><a href="/wiki/Meclofenoxate" title="Meclofenoxate">Meclofenoxate (centrophenoxine)</a></li> <li><a href="/wiki/Phosphatidylcholine" title="Phosphatidylcholine">Phosphatidylcholine</a></li> <li><a href="/wiki/Phosphatidylethanolamine" title="Phosphatidylethanolamine">Phosphatidylethanolamine</a></li> <li><a href="/wiki/Phosphorylcholine" title="Phosphorylcholine">Phosphorylcholine</a></li> <li><a href="/wiki/Pirisudanol" title="Pirisudanol">Pirisudanol</a></li></ul> </div></td></tr><tr><td class="navbox-abovebelow" colspan="2"><div> <dl><dt>See also</dt> <dd><a href="/wiki/Template:Receptor_modulators" title="Template:Receptor modulators">Receptor/signaling modulators</a></dd> <dd><a href="/wiki/Template:Muscarinic_acetylcholine_receptor_modulators" title="Template:Muscarinic acetylcholine receptor modulators">Muscarinic acetylcholine receptor modulators</a></dd> <dd><a href="/wiki/Template:Acetylcholine_metabolism_and_transport_modulators" title="Template:Acetylcholine metabolism and transport modulators">Acetylcholine metabolism/transport modulators</a></dd></dl> </div></td></tr></tbody></table></div> <style data-mw-deduplicate="TemplateStyles:r1130092004">.mw-parser-output .portal-bar{font-size:88%;font-weight:bold;display:flex;justify-content:center;align-items:baseline}.mw-parser-output .portal-bar-bordered{padding:0 2em;background-color:#fdfdfd;border:1px solid #a2a9b1;clear:both;margin:1em auto 0}.mw-parser-output .portal-bar-related{font-size:100%;justify-content:flex-start}.mw-parser-output .portal-bar-unbordered{padding:0 1.7em;margin-left:0}.mw-parser-output .portal-bar-header{margin:0 1em 0 0.5em;flex:0 0 auto;min-height:24px}.mw-parser-output .portal-bar-content{display:flex;flex-flow:row wrap;flex:0 1 auto;padding:0.15em 0;column-gap:1em;align-items:baseline;margin:0;list-style:none}.mw-parser-output .portal-bar-content-related{margin:0;list-style:none}.mw-parser-output .portal-bar-item{display:inline-block;margin:0.15em 0.2em;min-height:24px;line-height:24px}@media screen and (max-width:768px){.mw-parser-output .portal-bar{font-size:88%;font-weight:bold;display:flex;flex-flow:column wrap;align-items:baseline}.mw-parser-output .portal-bar-header{text-align:center;flex:0;padding-left:0.5em;margin:0 auto}.mw-parser-output .portal-bar-related{font-size:100%;align-items:flex-start}.mw-parser-output .portal-bar-content{display:flex;flex-flow:row wrap;align-items:center;flex:0;column-gap:1em;border-top:1px solid #a2a9b1;margin:0 auto;list-style:none}.mw-parser-output .portal-bar-content-related{border-top:none;margin:0;list-style:none}}.mw-parser-output .navbox+link+.portal-bar,.mw-parser-output .navbox+style+.portal-bar,.mw-parser-output .navbox+link+.portal-bar-bordered,.mw-parser-output .navbox+style+.portal-bar-bordered,.mw-parser-output .sister-bar+link+.portal-bar,.mw-parser-output .sister-bar+style+.portal-bar,.mw-parser-output .portal-bar+.navbox-styles+.navbox,.mw-parser-output .portal-bar+.navbox-styles+.sister-bar{margin-top:-1px}</style><div class="portal-bar noprint metadata noviewer portal-bar-bordered" role="navigation" aria-label="Portals"><span class="portal-bar-header"><a href="/wiki/Wikipedia:Contents/Portals" title="Wikipedia:Contents/Portals">Portal</a>:</span><ul class="portal-bar-content"><li class="portal-bar-item"><span class="nowrap"><span typeof="mw:File"><span><img alt="icon" src="//upload.wikimedia.org/wikipedia/commons/thumb/d/d6/WHO_Rod.svg/8px-WHO_Rod.svg.png" decoding="async" width="8" height="19" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/d/d6/WHO_Rod.svg/12px-WHO_Rod.svg.png 1.5x, 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