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Available in 16 languages" > <label id="p-lang-btn-label" for="p-lang-btn-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--action-progressive mw-portlet-lang-heading-16" aria-hidden="true" ><span class="vector-icon mw-ui-icon-language-progressive mw-ui-icon-wikimedia-language-progressive"></span> <span class="vector-dropdown-label-text">16 languages</span> </label> <div class="vector-dropdown-content"> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li class="interlanguage-link interwiki-de mw-list-item"><a href="https://de.wikipedia.org/wiki/Spartein" title="Spartein – German" lang="de" hreflang="de" data-title="Spartein" data-language-autonym="Deutsch" data-language-local-name="German" class="interlanguage-link-target"><span>Deutsch</span></a></li><li class="interlanguage-link interwiki-el mw-list-item"><a href="https://el.wikipedia.org/wiki/%CE%A3%CF%80%CE%B1%CF%81%CF%84%CE%B5%CE%90%CE%BD%CE%B7" title="Σπαρτεΐνη – Greek" lang="el" hreflang="el" data-title="Σπαρτεΐνη" data-language-autonym="Ελληνικά" data-language-local-name="Greek" class="interlanguage-link-target"><span>Ελληνικά</span></a></li><li class="interlanguage-link interwiki-es mw-list-item"><a href="https://es.wikipedia.org/wiki/Esparte%C3%ADna" title="Esparteína – Spanish" lang="es" hreflang="es" data-title="Esparteína" data-language-autonym="Español" data-language-local-name="Spanish" class="interlanguage-link-target"><span>Español</span></a></li><li class="interlanguage-link interwiki-fr mw-list-item"><a href="https://fr.wikipedia.org/wiki/Spart%C3%A9ine" title="Spartéine – French" lang="fr" hreflang="fr" data-title="Spartéine" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target"><span>Français</span></a></li><li class="interlanguage-link interwiki-id mw-list-item"><a href="https://id.wikipedia.org/wiki/Sparteina" title="Sparteina – Indonesian" lang="id" hreflang="id" data-title="Sparteina" data-language-autonym="Bahasa Indonesia" data-language-local-name="Indonesian" class="interlanguage-link-target"><span>Bahasa Indonesia</span></a></li><li class="interlanguage-link interwiki-it mw-list-item"><a href="https://it.wikipedia.org/wiki/Sparteina" title="Sparteina – Italian" lang="it" hreflang="it" data-title="Sparteina" 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/Sparte%C3%AFne" title="Sparteïne – Dutch" lang="nl" hreflang="nl" data-title="Sparteïne" 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%B9%E3%83%91%E3%83%AB%E3%83%86%E3%82%A4%E3%83%B3" title="スパルテイン – Japanese" lang="ja" hreflang="ja" data-title="スパルテイン" 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-pl mw-list-item"><a href="https://pl.wikipedia.org/wiki/Sparteina" title="Sparteina – Polish" lang="pl" hreflang="pl" data-title="Sparteina" 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/Esparte%C3%ADna" title="Esparteína – Portuguese" lang="pt" hreflang="pt" data-title="Esparteína" 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 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mw-list-item"><a href="https://sh.wikipedia.org/wiki/Spartein" title="Spartein – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Spartein" 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/Sparteiini" title="Sparteiini – Finnish" lang="fi" hreflang="fi" data-title="Sparteiini" data-language-autonym="Suomi" data-language-local-name="Finnish" class="interlanguage-link-target"><span>Suomi</span></a></li><li class="interlanguage-link interwiki-zh mw-list-item"><a href="https://zh.wikipedia.org/wiki/%E5%8F%B8%E5%B7%B4%E4%B8%81" title="司巴丁 – Chinese" lang="zh" hreflang="zh" data-title="司巴丁" data-language-autonym="中文" data-language-local-name="Chinese" class="interlanguage-link-target"><span>中文</span></a></li> </ul> <div class="after-portlet 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dir="ltr"><div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Chemical compound</div> <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): Sparteine">Sparteine</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:(%E2%88%92)-Sparteine.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/d/dc/%28%E2%88%92%29-Sparteine.svg/220px-%28%E2%88%92%29-Sparteine.svg.png" decoding="async" width="220" height="119" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/d/dc/%28%E2%88%92%29-Sparteine.svg/330px-%28%E2%88%92%29-Sparteine.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/d/dc/%28%E2%88%92%29-Sparteine.svg/440px-%28%E2%88%92%29-Sparteine.svg.png 2x" data-file-width="984" data-file-height="532" /></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;">Other names</th><td class="infobox-data">(6<i>R</i>,8<i>S</i>,10<i>R</i>,12<i>S</i>)-7,15-diazatetracyclo[7.7.1.0<sup>2,7</sup>.0<sup>10,15</sup>]heptadecane</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/international/sparteine.html">International Drug Names</a></span></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Anatomical_Therapeutic_Chemical_Classification_System" title="Anatomical Therapeutic Chemical Classification System">ATC code</a></th><td class="infobox-data"><style data-mw-deduplicate="TemplateStyles:r1126788409">.mw-parser-output .plainlist ol,.mw-parser-output .plainlist ul{line-height:inherit;list-style:none;margin:0;padding:0}.mw-parser-output .plainlist ol li,.mw-parser-output .plainlist ul li{margin-bottom:0}</style><div class="plainlist"><ul><li><a href="/wiki/ATC_code_C01" title="ATC code C01">C01BA04</a> (<span title="www.whocc.no"><a rel="nofollow" class="external text" href="https://www.whocc.no/atc_ddd_index/?code=C01BA04">WHO</a></span>) </li></ul></div></td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd">Identifiers</th></tr><tr><td colspan="2" class="infobox-full-data"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold;"><div><a href="/wiki/IUPAC_nomenclature_of_chemistry" title="IUPAC nomenclature of chemistry">IUPAC name</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all; text-align:left; padding-left:1.5em; text-indent:-1.5em;"><li style="line-height: inherit; margin: 0"><div style="font-size: 97%;">(7α,9α)-sparteine</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=90-39-1">90-39-1</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/644020">644020</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/DB06727">DB06727</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.559096.html">559096</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/298897D62S">298897D62S</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/D01041">D01041</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:28827">CHEBI:28827</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/ChEMBL44625">ChEMBL44625</a></span><sup> <span typeof="mw:File"><span><img alt="☒" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/7px-X_mark.svg.png" decoding="async" width="7" height="8" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/11px-X_mark.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/14px-X_mark.svg.png 2x" data-file-width="525" data-file-height="600" /></span></span><span style="display:none">N</span></sup></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/DTXSID4023591">DTXSID4023591</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q419552#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/100.001.808">100.001.808</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q419552#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>15</sub><span title="Hydrogen">H</span><sub>26</sub><span title="Nitrogen">N</span><sub>2</sub></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Molar_mass" title="Molar mass">Molar mass</a></th><td class="infobox-data"><span class="nowrap"><span data-sort-value="7002234387000000000♠"></span>234.387</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=C1CCN2C%5BC%40%40H%5D3C%5BC%40H%5D%28%5BC%40H%5D2C1%29CN4%5BC%40H%5D3CCCC4">Interactive image</a></span></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Density" title="Density">Density</a></th><td class="infobox-data">1.02 g/cm<sup>3</sup></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">30 °C (86 °F)</td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Boiling_point" title="Boiling point">Boiling point</a></th><td class="infobox-data">325 °C (617 °F)</td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Aqueous_solution" title="Aqueous solution">Solubility in water</a></th><td class="infobox-data">3.04 mg/mL (20 °C)</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%;">C1CCN2C[C@@H]3C[C@H]([C@H]2C1)CN4[C@H]3CCCC4</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/C15H26N2/c1-3-7-16-11-13-9-12(14(16)5-1)10-17-8-4-2-6-15(13)17/h12-15H,1-11H2/t12-,13-,14-,15+/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:SLRCCWJSBJZJBV-ZQDZILKHSA-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"> <sup><span typeof="mw:File"><span><img alt="☒" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/7px-X_mark.svg.png" decoding="async" width="7" height="8" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/11px-X_mark.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/14px-X_mark.svg.png 2x" data-file-width="525" data-file-height="600" /></span></span><span style="display:none">N</span><span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup> <a href="/wiki/Wikipedia:WikiProject_Chemicals/Chembox_validation" title="Wikipedia:WikiProject Chemicals/Chembox validation">(what is this?)</a></span><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r886047488"><span class="nobold">  <span class="reflink plainlinks nourlexpansion"><a class="external text" href="https://en.wikipedia.org/w/index.php?title=Special:ComparePages&rev1=464405926&page2=Sparteine">(verify)</a></span></span></td></tr></tbody></table> <p><b>Sparteine</b> is a class 1a <a href="/wiki/Antiarrhythmic_agent" title="Antiarrhythmic agent">antiarrhythmic agent</a> and sodium channel blocker. It is an <a href="/wiki/Alkaloid" title="Alkaloid">alkaloid</a> and can be extracted from <a href="/wiki/Scotch_broom" class="mw-redirect" title="Scotch broom">scotch broom</a>. It is the predominant alkaloid in <i><a href="/wiki/Lupinus_mutabilis" title="Lupinus mutabilis">Lupinus mutabilis</a></i>, and is thought to <a href="/wiki/Chelate" class="mw-redirect" title="Chelate">chelate</a> the bivalent metals <a href="/wiki/Calcium" title="Calcium">calcium</a> and <a href="/wiki/Magnesium" title="Magnesium">magnesium</a>. It is not FDA approved for human use as an antiarrhythmic agent, and it is not included in the <a href="/wiki/Antiarrhythmic_agent#Vaughan_Williams_antiarrhythmic_classification" title="Antiarrhythmic agent">Vaughan Williams classification of antiarrhythmic drugs</a>. </p><p>It is also used as a <a href="/wiki/Chirality_(chemistry)" title="Chirality (chemistry)">chiral</a> <a href="/wiki/Ligand" title="Ligand">ligand</a> in <a href="/wiki/Organic_chemistry" title="Organic chemistry">organic chemistry</a>, especially in syntheses involving <a href="/wiki/Organolithium_reagent" title="Organolithium reagent">organolithium reagents</a>. </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Biosynthesis">Biosynthesis</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Sparteine&action=edit&section=1" title="Edit section: Biosynthesis"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure class="mw-halign-left" typeof="mw:File/Frame"><a href="/wiki/File:BiosynthesisofSparteine.png" class="mw-file-description"><img alt="" src="//upload.wikimedia.org/wikipedia/commons/a/a4/BiosynthesisofSparteine.png" decoding="async" width="418" height="427" class="mw-file-element" data-file-width="418" data-file-height="427" /></a><figcaption>Originally proposed biosynthesis pathway of sparteine</figcaption></figure> <p>Sparteine is a lupin <a href="/wiki/Alkaloid" title="Alkaloid">alkaloid</a> containing a tetracyclic bis-quinolizidine ring system derived from three C<sub>5</sub> chains of <a href="/wiki/Lysine" title="Lysine">lysine</a>, or more specifically, <span style="font-size:85%;">L</span>-lysine.<sup id="cite_ref-NatProdBook_1-0" class="reference"><a href="#cite_note-NatProdBook-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> The first intermediate in the biosynthesis is <a href="/wiki/Cadaverine" title="Cadaverine">cadaverine</a>, the decarboxylation product of lysine catalyzed by the enzyme lysine decarboxylase (LDC).<sup id="cite_ref-Spenser_2-0" class="reference"><a href="#cite_note-Spenser-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> Three units of cadaverine are used to form the quinolizidine skeleton. The mechanism of formation has been studied enzymatically, as well as with tracer experiments, but the exact route of synthesis still remains unclear. </p><p>Tracer studies using <sup>13</sup>C-<sup>15</sup>N-doubly labeled cadaverine have shown three units of cadaverine are incorporated into sparteine and two of the C-N bonds from two of the cadaverine units remain intact.<sup id="cite_ref-Rana_3-0" class="reference"><a href="#cite_note-Rana-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> The observations have also been confirmed using <sup>2</sup>H NMR labeling experiments.<sup id="cite_ref-Fraser_4-0" class="reference"><a href="#cite_note-Fraser-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> </p><p>Enzymatic evidence then showed that the three molecules of cadaverine are transformed to the quinolizidine ring via enzyme bound intermediates, without the generation of any free intermediates. Originally, it was thought that conversion of cadaverine to the corresponding aldehyde, 5-aminopentanal, was catalyzed by the enzyme diamine oxidase.<sup id="cite_ref-SecretLife_5-0" class="reference"><a href="#cite_note-SecretLife-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> The aldehyde then spontaneously converts to the corresponding Schiff base, Δ<sup>1</sup>-piperideine. Coupling of two molecules occurs between the two tautomers of Δ<sup>1</sup>-piperideine in an aldol-type reaction. The imine is then hydrolyzed to the corresponding aldehyde/amine. The primary amine is then oxidized to an aldehyde followed by formation of the imine to yield the quinolizidine ring.<sup id="cite_ref-SecretLife_5-1" class="reference"><a href="#cite_note-SecretLife-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Via_17-oxosparteine_synthase">Via 17-oxosparteine synthase</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Sparteine&action=edit&section=2" title="Edit section: Via 17-oxosparteine synthase"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>More recent enzymatic evidence has indicated the presence of <a href="/w/index.php?title=17-oxosparteine_synthase&action=edit&redlink=1" class="new" title="17-oxosparteine synthase (page does not exist)">17-oxosparteine synthase</a> (OS), a transaminase enzyme.<sup id="cite_ref-Wink85_6-0" class="reference"><a href="#cite_note-Wink85-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-7" class="reference"><a href="#cite_note-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Wink79_8-0" class="reference"><a href="#cite_note-Wink79-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Perrey_9-0" class="reference"><a href="#cite_note-Perrey-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Saito_10-0" class="reference"><a href="#cite_note-Saito-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Roberts_11-0" class="reference"><a href="#cite_note-Roberts-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> The deaminated cadaverine is not released from the enzyme, thus is can be assumed that the enzyme catalyzes the formation of the quinolizidine skeleton in a channeled fashion .<sup id="cite_ref-Perrey_9-1" class="reference"><a href="#cite_note-Perrey-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Saito_10-1" class="reference"><a href="#cite_note-Saito-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Roberts_11-1" class="reference"><a href="#cite_note-Roberts-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> 7-oxosparteine requires four units of pyruvate as the NH<sub>2</sub> acceptors and produces four molecules of alanine. Both lysine decarboxylase and the quinolizidine skeleton-forming enzyme are localized in chloroplasts.<sup id="cite_ref-Wink80_12-0" class="reference"><a href="#cite_note-Wink80-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup> </p> <style data-mw-deduplicate="TemplateStyles:r1237032888/mw-parser-output/.tmulti">.mw-parser-output .tmulti .multiimageinner{display:flex;flex-direction:column}.mw-parser-output .tmulti .trow{display:flex;flex-direction:row;clear:left;flex-wrap:wrap;width:100%;box-sizing:border-box}.mw-parser-output .tmulti .tsingle{margin:1px;float:left}.mw-parser-output .tmulti .theader{clear:both;font-weight:bold;text-align:center;align-self:center;background-color:transparent;width:100%}.mw-parser-output .tmulti .thumbcaption{background-color:transparent}.mw-parser-output .tmulti .text-align-left{text-align:left}.mw-parser-output .tmulti .text-align-right{text-align:right}.mw-parser-output .tmulti .text-align-center{text-align:center}@media all and (max-width:720px){.mw-parser-output .tmulti .thumbinner{width:100%!important;box-sizing:border-box;max-width:none!important;align-items:center}.mw-parser-output .tmulti .trow{justify-content:center}.mw-parser-output .tmulti .tsingle{float:none!important;max-width:100%!important;box-sizing:border-box;text-align:center}.mw-parser-output .tmulti .tsingle .thumbcaption{text-align:left}.mw-parser-output .tmulti .trow>.thumbcaption{text-align:center}}@media screen{html.skin-theme-clientpref-night .mw-parser-output .tmulti .multiimageinner img{background-color:white}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .tmulti .multiimageinner img{background-color:white}}</style><div class="thumb tmulti tright"><div class="thumbinner multiimageinner" style="width:392px;max-width:392px"><div class="trow"><div class="theader">Biosynthesis of sparteine by 17-oxosparteine synthase</div></div><div class="trow"><div class="tsingle" style="width:390px;max-width:390px"><div class="thumbimage" style="height:237px;overflow:hidden"><span typeof="mw:File"><a href="/wiki/File:BiosynthesisSparteine2.png" class="mw-file-description"><img alt="" src="//upload.wikimedia.org/wikipedia/commons/thumb/b/b0/BiosynthesisSparteine2.png/388px-BiosynthesisSparteine2.png" decoding="async" width="388" height="238" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/b/b0/BiosynthesisSparteine2.png 1.5x" data-file-width="534" data-file-height="327" /></a></span></div><div class="thumbcaption">Proposed ring cyclization steps</div></div></div><div class="trow"><div class="tsingle" style="width:390px;max-width:390px"><div class="thumbimage" style="height:56px;overflow:hidden"><span typeof="mw:File"><a href="/wiki/File:GeneralbiosynthesisSparteine.gif" class="mw-file-description"><img alt="" src="//upload.wikimedia.org/wikipedia/commons/thumb/0/06/GeneralbiosynthesisSparteine.gif/388px-GeneralbiosynthesisSparteine.gif" decoding="async" width="388" height="57" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/0/06/GeneralbiosynthesisSparteine.gif 1.5x" data-file-width="438" data-file-height="64" /></a></span></div><div class="thumbcaption">Overall schematic</div></div></div></div></div> <div class="mw-heading mw-heading2"><h2 id="See_also">See also</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Sparteine&action=edit&section=3" title="Edit section: See also"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a href="/wiki/Lupinus" title="Lupinus">Lupinus</a></li> <li><a href="/wiki/Lupin_poisoning" class="mw-redirect" title="Lupin poisoning">Lupin poisoning</a></li></ul> <div class="mw-heading mw-heading2"><h2 id="References">References</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Sparteine&action=edit&section=4" title="Edit section: References"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-references-wrap mw-references-columns"><ol class="references"> <li id="cite_note-NatProdBook-1"><span class="mw-cite-backlink"><b><a href="#cite_ref-NatProdBook_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 id="CITEREFDewick2009" class="citation book cs1">Dewick PM (2009). <i>Medicinal Natural Products: A Biosynthetic Approach</i> (3rd ed.). Wiley. pp. 328–329. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2F9780470742761">10.1002/9780470742761</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-470-74276-1" title="Special:BookSources/978-0-470-74276-1"><bdi>978-0-470-74276-1</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Medicinal+Natural+Products%3A+A+Biosynthetic+Approach&rft.pages=328-329&rft.edition=3rd&rft.pub=Wiley&rft.date=2009&rft_id=info%3Adoi%2F10.1002%2F9780470742761&rft.isbn=978-0-470-74276-1&rft.aulast=Dewick&rft.aufirst=PM&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASparteine" class="Z3988"></span></span> </li> <li id="cite_note-Spenser-2"><span class="mw-cite-backlink"><b><a href="#cite_ref-Spenser_2-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFGolebiewskiSpenser1988" class="citation journal cs1">Golebiewski WM, Spenser ID (1988). <a rel="nofollow" class="external text" href="https://doi.org/10.1139%2Fv88-280">"Biosynthesis of the lupine alkaloids. II. Sparteine and lupanine"</a>. <i>Canadian Journal of Chemistry</i>. <b>66</b> (7): 1734–1748. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://doi.org/10.1139%2Fv88-280">10.1139/v88-280</a></span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Canadian+Journal+of+Chemistry&rft.atitle=Biosynthesis+of+the+lupine+alkaloids.+II.+Sparteine+and+lupanine&rft.volume=66&rft.issue=7&rft.pages=1734-1748&rft.date=1988&rft_id=info%3Adoi%2F10.1139%2Fv88-280&rft.aulast=Golebiewski&rft.aufirst=WM&rft.au=Spenser%2C+ID&rft_id=https%3A%2F%2Fdoi.org%2F10.1139%252Fv88-280&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASparteine" class="Z3988"></span></span> </li> <li id="cite_note-Rana-3"><span class="mw-cite-backlink"><b><a href="#cite_ref-Rana_3-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFRanaRobins1983" class="citation journal cs1">Rana J, Robins DJ (1983). "Quinolizidine alkaloid biosynthesis: Incorporation of [1-<i>amino</i>-<sup>15</sup>N,1-<sup>13</sup>C]cadaverine into sparteine". <i>Journal of the Chemical Society, Chemical Communications</i>. <b>1983</b> (22): 1335–1336. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1039%2FC39830001335">10.1039/C39830001335</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Journal+of+the+Chemical+Society%2C+Chemical+Communications&rft.atitle=Quinolizidine+alkaloid+biosynthesis%3A+Incorporation+of+%5B1-amino-%3Csup%3E15%3C%2Fsup%3EN%2C1-%3Csup%3E13%3C%2Fsup%3EC%5Dcadaverine+into+sparteine&rft.volume=1983&rft.issue=22&rft.pages=1335-1336&rft.date=1983&rft_id=info%3Adoi%2F10.1039%2FC39830001335&rft.aulast=Rana&rft.aufirst=J&rft.au=Robins%2C+DJ&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASparteine" class="Z3988"></span></span> </li> <li id="cite_note-Fraser-4"><span class="mw-cite-backlink"><b><a href="#cite_ref-Fraser_4-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFFraserRobins1984" class="citation journal cs1">Fraser AM, Robins DJ (1984). "Incorporation of chiral [1-<sup>2</sup>H]cadaverines into the quinolizidine alkaloids sparteine, lupanine, and angustifoline". <i>Journal of the Chemical Society, Chemical Communications</i>. <b>1984</b> (22): 1477–1479. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1039%2FC39840001477">10.1039/C39840001477</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Journal+of+the+Chemical+Society%2C+Chemical+Communications&rft.atitle=Incorporation+of+chiral+%5B1-%3Csup%3E2%3C%2Fsup%3EH%5Dcadaverines+into+the+quinolizidine+alkaloids+sparteine%2C+lupanine%2C+and+angustifoline&rft.volume=1984&rft.issue=22&rft.pages=1477-1479&rft.date=1984&rft_id=info%3Adoi%2F10.1039%2FC39840001477&rft.aulast=Fraser&rft.aufirst=AM&rft.au=Robins%2C+DJ&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASparteine" class="Z3988"></span></span> </li> <li id="cite_note-SecretLife-5"><span class="mw-cite-backlink">^ <a href="#cite_ref-SecretLife_5-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-SecretLife_5-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFAniszewski2007" class="citation book cs1">Aniszewski T (2007). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=a1Z6oJL-dgMC&pg=PA98"><i>Alkaloids – Secrets of Life: Alkaloid Chemistry, Biological Significance, Applications and Ecological Role</i></a>. Elsevier. pp. 98–101. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2FB978-0-444-52736-3.X5000-4">10.1016/B978-0-444-52736-3.X5000-4</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-444-52736-3" title="Special:BookSources/978-0-444-52736-3"><bdi>978-0-444-52736-3</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Alkaloids+%E2%80%93+Secrets+of+Life%3A+Alkaloid+Chemistry%2C+Biological+Significance%2C+Applications+and+Ecological+Role&rft.pages=98-101&rft.pub=Elsevier&rft.date=2007&rft_id=info%3Adoi%2F10.1016%2FB978-0-444-52736-3.X5000-4&rft.isbn=978-0-444-52736-3&rft.aulast=Aniszewski&rft.aufirst=T&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3Da1Z6oJL-dgMC%26pg%3DPA98&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASparteine" class="Z3988"></span></span> </li> <li id="cite_note-Wink85-6"><span class="mw-cite-backlink"><b><a href="#cite_ref-Wink85_6-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFWinkHartmann1985" class="citation book cs1">Wink M, Hartmann T (1985). <span class="id-lock-registration" title="Free registration required"><a rel="nofollow" class="external text" href="https://archive.org/details/naturalproductsc0000inte/page/511/mode/1up">"Enzymology of quinolizidine alkaloid biosynthesis"</a></span>. In Zalewski RI, Skolik JJ (eds.). <span class="id-lock-registration" title="Free registration required"><a rel="nofollow" class="external text" href="https://archive.org/details/naturalproductsc0000inte"><i>Natural Products Chemistry 1984: A Collection of Invited Section and Colloquium Lectures Presented at the 14th IUPAC International Symposium on the Chemistry of Natural Products, Poznań, Poland, 9–14 July 1984</i></a></span>. Studies in Organic Chemistry. Vol. 20. 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</li> <li id="cite_note-7"><span class="mw-cite-backlink"><b><a href="#cite_ref-7">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFWink1987" class="citation journal cs1">Wink M (1987). <a rel="nofollow" class="external text" href="https://doi.org/10.1055%2Fs-2006-962797">"Quinolizidine alkaloids: Biochemistry, metabolism, and function in plants and cell suspension cultures"</a>. <i>Planta Medica</i>. <b>53</b> (6): 509–514. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://doi.org/10.1055%2Fs-2006-962797">10.1055/s-2006-962797</a></span>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/17269092">17269092</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Planta+Medica&rft.atitle=Quinolizidine+alkaloids%3A+Biochemistry%2C+metabolism%2C+and+function+in+plants+and+cell+suspension+cultures&rft.volume=53&rft.issue=6&rft.pages=509-514&rft.date=1987&rft_id=info%3Adoi%2F10.1055%2Fs-2006-962797&rft_id=info%3Apmid%2F17269092&rft.aulast=Wink&rft.aufirst=M&rft_id=https%3A%2F%2Fdoi.org%2F10.1055%252Fs-2006-962797&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASparteine" class="Z3988"></span></span> </li> <li id="cite_note-Wink79-8"><span class="mw-cite-backlink"><b><a href="#cite_ref-Wink79_8-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFWinkHartmann1979" class="citation journal cs1">Wink M, Hartmann T (1979). <a rel="nofollow" class="external text" href="https://doi.org/10.1016%2F0014-5793%2879%2981040-6">"Cadaverine–pyruvate transamination: The principal step of enzymatic quinolizidine alkaloid biosynthesis in <i>Lupinus polyphyllus</i> cell suspension cultures"</a>. <i>FEBS Letters</i>. <b>101</b> (2): 343–346. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://doi.org/10.1016%2F0014-5793%2879%2981040-6">10.1016/0014-5793(79)81040-6</a></span>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/446758">446758</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=FEBS+Letters&rft.atitle=Cadaverine%E2%80%93pyruvate+transamination%3A+The+principal+step+of+enzymatic+quinolizidine+alkaloid+biosynthesis+in+Lupinus+polyphyllus+cell+suspension+cultures&rft.volume=101&rft.issue=2&rft.pages=343-346&rft.date=1979&rft_id=info%3Adoi%2F10.1016%2F0014-5793%2879%2981040-6&rft_id=info%3Apmid%2F446758&rft.aulast=Wink&rft.aufirst=M&rft.au=Hartmann%2C+T&rft_id=https%3A%2F%2Fdoi.org%2F10.1016%252F0014-5793%252879%252981040-6&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASparteine" class="Z3988"></span></span> </li> <li id="cite_note-Perrey-9"><span class="mw-cite-backlink">^ <a href="#cite_ref-Perrey_9-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Perrey_9-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFPerreyWink1988" class="citation journal cs1">Perrey R, Wink M (1988). <a rel="nofollow" class="external text" href="https://doi.org/10.1515%2Fznc-1988-5-607">"On the role of Δ1-piperideine and tripiperideine in the biosynthesis of quinolizidine alkaloids"</a>. <i>Zeitschrift für Naturforschung</i>. <b>43c</b> (5–6): 363–369. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://doi.org/10.1515%2Fznc-1988-5-607">10.1515/znc-1988-5-607</a></span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Zeitschrift+f%C3%BCr+Naturforschung&rft.atitle=On+the+role+of+%CE%941-piperideine+and+tripiperideine+in+the+biosynthesis+of+quinolizidine+alkaloids&rft.volume=43c&rft.issue=5%E2%80%936&rft.pages=363-369&rft.date=1988&rft_id=info%3Adoi%2F10.1515%2Fznc-1988-5-607&rft.aulast=Perrey&rft.aufirst=R&rft.au=Wink%2C+M&rft_id=https%3A%2F%2Fdoi.org%2F10.1515%252Fznc-1988-5-607&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASparteine" class="Z3988"></span></span> </li> <li id="cite_note-Saito-10"><span class="mw-cite-backlink">^ <a href="#cite_ref-Saito_10-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Saito_10-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFSaitoMurakoshi1995" class="citation book cs1">Saito K, Murakoshi I (1995). "Chemistry, biochemistry and chemotaxonomy of lupine alkaloids in the Leguminosae". In Atta-ur-Rahman (ed.). <i>Structure and Chemistry (Part C)</i>. Studies in Natural Products Chemistry. Vol. 15. Elsevier. p. 537. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2FS1572-5995%2806%2980142-0">10.1016/S1572-5995(06)80142-0</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-444-82083-9" title="Special:BookSources/978-0-444-82083-9"><bdi>978-0-444-82083-9</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Chemistry%2C+biochemistry+and+chemotaxonomy+of+lupine+alkaloids+in+the+Leguminosae&rft.btitle=Structure+and+Chemistry+%28Part+C%29&rft.series=Studies+in+Natural+Products+Chemistry&rft.pages=537&rft.pub=Elsevier&rft.date=1995&rft_id=info%3Adoi%2F10.1016%2FS1572-5995%2806%2980142-0&rft.isbn=978-0-444-82083-9&rft.aulast=Saito&rft.aufirst=K&rft.au=Murakoshi%2C+I&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASparteine" class="Z3988"></span></span> </li> <li id="cite_note-Roberts-11"><span class="mw-cite-backlink">^ <a href="#cite_ref-Roberts_11-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Roberts_11-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFRoberts1998" class="citation book cs1">Roberts MF (1998). <span class="id-lock-registration" title="Free registration required"><a rel="nofollow" class="external text" href="https://archive.org/details/alkaloidsbiochem0000unse">"Enzymology of alkaloid biosynthesis"</a></span>. In Roberts MF, Wink M (eds.). <span class="id-lock-registration" title="Free registration required"><a rel="nofollow" class="external text" href="https://archive.org/details/alkaloidsbiochem0000unse/page/112/mode/1up"><i>Alkaloids: Biochemistry, Ecology, and Medicinal Applications</i></a></span>. Plenum Press. pp. 112–114. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1007%2F978-1-4757-2905-4_5">10.1007/978-1-4757-2905-4_5</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1-4757-2905-4" title="Special:BookSources/978-1-4757-2905-4"><bdi>978-1-4757-2905-4</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Enzymology+of+alkaloid+biosynthesis&rft.btitle=Alkaloids%3A+Biochemistry%2C+Ecology%2C+and+Medicinal+Applications&rft.pages=112-114&rft.pub=Plenum+Press&rft.date=1998&rft_id=info%3Adoi%2F10.1007%2F978-1-4757-2905-4_5&rft.isbn=978-1-4757-2905-4&rft.aulast=Roberts&rft.aufirst=MF&rft_id=https%3A%2F%2Farchive.org%2Fdetails%2Falkaloidsbiochem0000unse&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASparteine" class="Z3988"></span></span> </li> <li id="cite_note-Wink80-12"><span class="mw-cite-backlink"><b><a href="#cite_ref-Wink80_12-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFWinkHartmann1980" class="citation journal cs1">Wink M, Hartmann T (1980). <a rel="nofollow" class="external text" href="https://doi.org/10.1515%2Fznc-1980-1-218">"Enzymatic synthesis of quinolizidine alkaloids in lupin chloroplasts"</a>. <i>Zeitschrift für Naturforschung</i>. <b>35c</b> (1–2): 93–97. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://doi.org/10.1515%2Fznc-1980-1-218">10.1515/znc-1980-1-218</a></span>.</cite><span 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blockers</a>)</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%">class Ia (<a href="/wiki/Cardiac_action_potential#Phase_0" title="Cardiac action potential">Phase 0</a>→ and <a href="/wiki/Cardiac_action_potential#Phase_3" title="Cardiac action potential">Phase 3</a>→)</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/Ajmaline" title="Ajmaline">Ajmaline</a></li> <li><a href="/wiki/Disopyramide" title="Disopyramide">Disopyramide</a></li> <li><a href="/wiki/Dihydroquinidine" title="Dihydroquinidine">Hydroquinidine</a></li> <li><a href="/wiki/Lorajmine" title="Lorajmine">Lorajmine</a></li> <li><a href="/wiki/Prajmaline" title="Prajmaline">Prajmaline</a></li> <li><a href="/wiki/Procainamide" title="Procainamide">Procainamide</a><sup>#</sup></li> <li><a href="/wiki/Quinidine" title="Quinidine">Quinidine</a><sup>#</sup></li> <li><a class="mw-selflink selflink">Sparteine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">class Ib (<a href="/wiki/Cardiac_action_potential#Phase_3" title="Cardiac action potential">Phase 3</a>←)</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i><a href="/wiki/Intravenous_therapy" title="Intravenous therapy">IV</a></i> <ul><li><a href="/wiki/Lidocaine" title="Lidocaine">Lidocaine</a><sup>#</sup></li></ul></li> <li><i><a href="/wiki/Enteral" class="mw-redirect" title="Enteral">enteral</a></i> <ul><li><a href="/wiki/Aprindine" title="Aprindine">Aprindine</a></li> <li><a href="/wiki/Mexiletine" title="Mexiletine">Mexiletine</a></li> <li><a href="/wiki/Tocainide" title="Tocainide">Tocainide</a></li></ul></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">class Ic (<a href="/wiki/Cardiac_action_potential#Phase_0" title="Cardiac action potential">Phase 0</a>→)</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/Encainide" title="Encainide">Encainide</a><sup>‡</sup></li> <li><a href="/wiki/Ethacizine" title="Ethacizine">Ethacizine</a></li> <li><a href="/wiki/Flecainide" title="Flecainide">Flecainide</a></li> <li><a href="/wiki/Indecainide" title="Indecainide">Indecainide</a><sup>‡</sup></li> <li><a href="/wiki/Lorcainide" title="Lorcainide">Lorcainide</a></li> <li><a href="/wiki/Moracizine" title="Moracizine">Moracizine</a><sup>‡</sup></li> <li><a href="/wiki/Propafenone" title="Propafenone">Propafenone</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Antiarrhythmic_agent#Class_III_agents" title="Antiarrhythmic agent">class III</a><br />(<a href="/wiki/Cardiac_action_potential#Phase_3" title="Cardiac action potential">Phase 3</a>→, <a href="/wiki/Potassium_channel_blocker" title="Potassium channel blocker">K<sup>+</sup> channel blockers</a>)</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/Amiodarone" title="Amiodarone">Amiodarone</a></li> <li><a href="/wiki/Bretylium" title="Bretylium">Bretylium</a></li> <li><a href="/wiki/Bunaftine" title="Bunaftine">Bunaftine</a></li> <li><a href="/wiki/Celivarone" title="Celivarone">Celivarone</a><sup>†</sup></li> <li><a href="/wiki/Dofetilide" title="Dofetilide">Dofetilide</a></li> <li><a href="/wiki/Dronedarone" title="Dronedarone">Dronedarone</a></li> <li><a href="/wiki/E-4031" title="E-4031">E-4031</a><sup>†</sup></li> <li><a href="/wiki/Ibutilide" title="Ibutilide">Ibutilide</a></li> <li><a href="/wiki/Nifekalant" title="Nifekalant">Nifekalant</a></li> <li><a href="/wiki/Sotalol" title="Sotalol">Sotalol</a></li> <li><a href="/wiki/Tedisamil" title="Tedisamil">Tedisamil</a></li> <li><a href="/wiki/Vernakalant" title="Vernakalant">Vernakalant</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Antiarrhythmic_agent#Class_IV_agents" title="Antiarrhythmic agent">class IV</a><br />(<a href="/wiki/Cardiac_action_potential#Phase_4" title="Cardiac action potential">Phase 4</a>→, <a href="/wiki/Calcium_channel_blocker" title="Calcium channel blocker">Ca<sup>2+</sup> channel blockers</a>)</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/Diltiazem" title="Diltiazem">Diltiazem</a></li> <li><a href="/wiki/Verapamil" title="Verapamil">Verapamil</a><sup>#</sup></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Receptor_(biochemistry)" title="Receptor (biochemistry)">Receptor</a> <a href="/wiki/Agonist" title="Agonist">agonists</a><br />and <a href="/wiki/Receptor_antagonist" title="Receptor antagonist">antagonists</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Antiarrhythmic_agent#Class_II_agents" title="Antiarrhythmic agent">class II</a><br />(<a href="/wiki/Cardiac_action_potential#Phase_4" title="Cardiac action potential">Phase 4</a>→, <a href="/wiki/Beta_blocker" title="Beta blocker">β blockers</a>)</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/Nadolol" title="Nadolol">Nadolol</a></li> <li><a href="/wiki/Pindolol" title="Pindolol">Pindolol</a></li> <li><a href="/wiki/Propranolol" title="Propranolol">Propranolol</a></li> <li><i>cardioselective</i> <ul><li><a href="/wiki/Acebutolol" title="Acebutolol">Acebutolol</a></li> <li><a href="/wiki/Atenolol" title="Atenolol">Atenolol</a></li> <li><a href="/wiki/Esmolol" title="Esmolol">Esmolol</a></li> <li><a href="/wiki/Landiolol" title="Landiolol">Landiolol</a></li> <li><a href="/wiki/Metoprolol" title="Metoprolol">Metoprolol</a></li></ul></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Adenosine_A1_receptor" title="Adenosine A1 receptor">A<sub>1</sub> agonist</a></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/Adenosine" title="Adenosine">Adenosine</a></li> <li><a href="/wiki/Benzodiazepine" title="Benzodiazepine">Benzodiazepines</a></li> <li><a href="/wiki/Barbiturate" title="Barbiturate">Barbiturates</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Muscarinic_acetylcholine_receptor_M2" title="Muscarinic acetylcholine receptor M2">M<sub>2</sub></a></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/Muscarinic_antagonist" title="Muscarinic antagonist">muscarinic antagonist</a>: <a href="/wiki/Atropine" title="Atropine">Atropine</a></li> <li><a href="/wiki/Disopyramide" title="Disopyramide">Disopyramide</a></li> <li><a href="/wiki/Quinidine" title="Quinidine">Quinidine</a><br /><a href="/wiki/Muscarinic_agonist" title="Muscarinic agonist">muscarinic agonist</a>: <a href="/wiki/Digoxin" title="Digoxin">Digoxin</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Adrenergic_receptor#.CE.B1_receptors" title="Adrenergic receptor">α receptors</a></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/Amiodarone" title="Amiodarone">Amiodarone</a></li> <li><a href="/wiki/Bretylium" title="Bretylium">Bretylium</a></li> <li><a href="/wiki/Quinidine" title="Quinidine">Quinidine</a></li> <li><a href="/wiki/Verapamil" title="Verapamil">Verapamil</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Ion_transporter" title="Ion transporter">Ion transporters</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th id="Na+/_K+-ATPase" scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Na%2B/K%2B-ATPase" class="mw-redirect" title="Na+/K+-ATPase">Na<sup>+</sup>/ K<sup>+</sup>-ATPase</a></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/Digitoxin" title="Digitoxin">Digitoxin</a></li> <li><a href="/wiki/Digoxin" title="Digoxin">Digoxin</a></li> <li><a href="/wiki/Ouabain" title="Ouabain">Ouabain</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><td colspan="2" class="navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"><div class="hlist"> <ul><li><sup>#</sup><a href="/wiki/WHO_Model_List_of_Essential_Medicines" title="WHO Model List of Essential Medicines">WHO-EM</a></li> <li><sup>‡</sup><a href="/wiki/List_of_withdrawn_drugs" title="List of withdrawn drugs">Withdrawn</a> from market</li> <li><a href="/wiki/Clinical_trial" title="Clinical trial">Clinical trials</a>: <ul><li><sup>†</sup><a href="/wiki/Phases_of_clinical_research#Phase_III" title="Phases of clinical research">Phase III</a></li> <li><sup>§</sup>Never to phase III</li></ul></li></ul> </div></div></td></tr></tbody></table></div>    </div><noscript><img src="https://login.wikimedia.org/wiki/Special:CentralAutoLogin/start?type=1x1" alt="" width="1" height="1" style="border: none; position: absolute;"></noscript> <div class="printfooter" data-nosnippet="">Retrieved from "<a dir="ltr" href="https://en.wikipedia.org/w/index.php?title=Sparteine&oldid=1212895601">https://en.wikipedia.org/w/index.php?title=Sparteine&oldid=1212895601</a>"</div></div> <div id="catlinks" class="catlinks" data-mw="interface"><div id="mw-normal-catlinks" class="mw-normal-catlinks"><a href="/wiki/Help:Category" title="Help:Category">Categories</a>: <ul><li><a href="/wiki/Category:Antiarrhythmic_agents" title="Category:Antiarrhythmic agents">Antiarrhythmic agents</a></li><li><a href="/wiki/Category:Quinolizidine_alkaloids" title="Category:Quinolizidine alkaloids">Quinolizidine alkaloids</a></li><li><a href="/wiki/Category:Sodium_channel_blockers" title="Category:Sodium 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