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class="vector-toc-list"> <li id="toc-Apomorphine" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Apomorphine"> <div class="vector-toc-text"> <span class="vector-toc-numb">1.1</span> <span>Apomorphine</span> </div> </a> <ul id="toc-Apomorphine-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Effects" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Effects"> <div class="vector-toc-text"> <span class="vector-toc-numb">2</span> <span>Effects</span> </div> </a> <ul id="toc-Effects-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Synthesis" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Synthesis"> <div class="vector-toc-text"> <span class="vector-toc-numb">3</span> <span>Synthesis</span> </div> </a> <ul id="toc-Synthesis-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Toxicity" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Toxicity"> <div class="vector-toc-text"> <span class="vector-toc-numb">4</span> <span>Toxicity</span> </div> </a> <ul id="toc-Toxicity-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Pharmacology" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Pharmacology"> <div class="vector-toc-text"> <span class="vector-toc-numb">5</span> <span>Pharmacology</span> </div> </a> <ul id="toc-Pharmacology-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Pharmacokinetics" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Pharmacokinetics"> <div class="vector-toc-text"> <span class="vector-toc-numb">6</span> <span>Pharmacokinetics</span> </div> </a> <ul id="toc-Pharmacokinetics-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Psychoactive_effects" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Psychoactive_effects"> <div class="vector-toc-text"> <span class="vector-toc-numb">7</span> <span>Psychoactive effects</span> </div> </a> <ul id="toc-Psychoactive_effects-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Effects_on_animals" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Effects_on_animals"> <div class="vector-toc-text"> <span class="vector-toc-numb">8</span> <span>Effects on animals</span> </div> </a> <ul id="toc-Effects_on_animals-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-See_also" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#See_also"> <div class="vector-toc-text"> <span class="vector-toc-numb">9</span> <span>See also</span> </div> </a> <ul id="toc-See_also-sublist" 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href="https://es.wikipedia.org/wiki/Aporfina" title="Aporfina – Spanish" lang="es" hreflang="es" data-title="Aporfina" 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/%D8%A2%D9%BE%D9%88%D8%B1%D9%81%DB%8C%D9%86" title="آپورفین – Persian" lang="fa" hreflang="fa" data-title="آپورفین" data-language-autonym="فارسی" data-language-local-name="Persian" class="interlanguage-link-target"><span>فارسی</span></a></li><li class="interlanguage-link interwiki-ja mw-list-item"><a href="https://ja.wikipedia.org/wiki/%E3%82%A2%E3%83%9D%E3%83%AB%E3%83%95%E3%82%A3%E3%83%B3" title="アポルフィン – Japanese" lang="ja" hreflang="ja" data-title="アポルフィン" 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-pt mw-list-item"><a href="https://pt.wikipedia.org/wiki/Aporfina" title="Aporfina – Portuguese" lang="pt" hreflang="pt" data-title="Aporfina" data-language-autonym="Português" data-language-local-name="Portuguese" class="interlanguage-link-target"><span>Português</span></a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/Aporfin" title="Aporfin – Serbian" lang="sr" hreflang="sr" data-title="Aporfin" 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/Aporfin" title="Aporfin – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Aporfin" data-language-autonym="Srpskohrvatski / српскохрватски" data-language-local-name="Serbo-Croatian" class="interlanguage-link-target"><span>Srpskohrvatski / српскохрватски</span></a></li> </ul> <div class="after-portlet 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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): Aporphine">Aporphine</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:Aporphine.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/6/66/Aporphine.svg/220px-Aporphine.svg.png" decoding="async" width="220" height="253" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/66/Aporphine.svg/330px-Aporphine.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/66/Aporphine.svg/440px-Aporphine.svg.png 2x" data-file-width="330" data-file-height="380" /></a></span></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%;">6-methyl-5,6,6a,7-tetrahydro-4<i>H</i>-dibenzo[<i>de</i>,<i>g</i>]quinoline</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"><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><span title="commonchemistry.cas.org"><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=478-57-9">478-57-9</a></span></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/PubChem#CID" title="PubChem">PubChem</a> <span style="font-weight:normal"><abbr title="Compound ID">CID</abbr></span></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="pubchem.ncbi.nlm.nih.gov"><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/114911">114911</a></span></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/ChemSpider" title="ChemSpider">ChemSpider</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.chemspider.com"><a rel="nofollow" class="external text" href="https://www.chemspider.com/Chemical-Structure.102860.html">102860</a></span></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Unique_Ingredient_Identifier" title="Unique Ingredient Identifier">UNII</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="precision.fda.gov"><a rel="nofollow" class="external text" href="https://precision.fda.gov/uniisearch/srs/unii/13NS2KTD6H">13NS2KTD6H</a></span></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:35643">CHEBI:35643</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/DTXSID80895017">DTXSID80895017</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q4780565#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 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>17</sub><span title="Nitrogen">N</span></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="7002235330000000000♠"></span>235.330</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=c12c%28cccc1%29CC4c3c%28cccc23%29CCN4C">Interactive image</a></span></li></ul></div></td></tr><tr><td colspan="2" class="infobox-full-data"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold;"><div><a href="/wiki/Simplified_molecular-input_line-entry_system" class="mw-redirect" title="Simplified molecular-input line-entry system">SMILES</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="word-wrap:break-word; text-indent:-1.5em; text-align:left; padding-left:1.5em; font-size:97%; line-height:120%;">c12c(cccc1)CC4c3c(cccc23)CCN4C</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/C17H17N/c1-18-10-9-12-6-4-8-15-14-7-3-2-5-13(14)11-16(18)17(12)15/h2-8,16H,9-11H2,1H3</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:BZKUYNBAFQJRDM-UHFFFAOYSA-N</div></li></ul> </div></td></tr></tbody></table> <p><b>Aporphine</b> is an <a href="/wiki/Alkaloid" title="Alkaloid">alkaloid</a> with the chemical formula <style data-mw-deduplicate="TemplateStyles:r1123817410">.mw-parser-output .template-chem2-su{display:inline-block;font-size:80%;line-height:1;vertical-align:-0.35em}.mw-parser-output .template-chem2-su>span{display:block;text-align:left}.mw-parser-output sub.template-chem2-sub{font-size:80%;vertical-align:-0.35em}.mw-parser-output sup.template-chem2-sup{font-size:80%;vertical-align:0.65em}</style><span class="chemf nowrap">C<sub class="template-chem2-sub">17</sub>H<sub class="template-chem2-sub">17</sub>N</span>. It is the core chemical substructure of the <a href="/wiki/Aporphine_alkaloids" title="Aporphine alkaloids">aporphine alkaloids</a>, a subclass of <a href="/wiki/Quinoline_alkaloids" title="Quinoline alkaloids">quinoline alkaloids</a>. It can exist in either of two <a href="/wiki/Enantiomer" title="Enantiomer">enantiomeric</a> forms, (<i>R</i>)-aporphine and (<i>S</i>)-aporphine. </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Derivatives">Derivatives</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Aporphine&action=edit&section=1" title="Edit section: Derivatives"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Many different <a href="/wiki/Derivative_(chemistry)" title="Derivative (chemistry)">derivatives</a> of aporphine have been isolated from plants.<sup id="cite_ref-1" class="reference"><a href="#cite_note-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> For example, many <a href="/wiki/Nymphaeaceae" title="Nymphaeaceae">water lilies</a> (<i><a href="/wiki/Nymphaea" title="Nymphaea">Nymphaea</a></i> species) produce aporphine alkaloids such as nymphaeine, nymphaline, nupharine, α- and β-nupharidine.<sup id="cite_ref-2" class="reference"><a href="#cite_note-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> </p><p><i><a href="/wiki/In_vitro" title="In vitro">In vitro</a>,</i> tests of some aporphine derivatives isolated from <i><a href="/wiki/Cassytha_filiformis" title="Cassytha filiformis">Cassytha filiformis</a></i>, namely, actinodaphnine, cassythine, and <a href="/wiki/Dicentrine" title="Dicentrine">dicentrine</a>, showed <a href="/wiki/Antiparasitic" title="Antiparasitic">antiparasitic</a> activity against <i><a href="/wiki/Trypanosoma_brucei" title="Trypanosoma brucei">Trypanosoma brucei</a></i>. Investigation of possible mechanisms revealed that the compounds bind to DNA and act as <a href="/wiki/Intercalation_(biochemistry)" title="Intercalation (biochemistry)">intercalating</a> agents, in addition to inhibiting <a href="/wiki/Topoisomerase" title="Topoisomerase">topoisomerase</a> activity.<sup id="cite_ref-3" class="reference"><a href="#cite_note-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> </p><p>Aporphine natural products occur with either the (R)- or (S)- <a href="/wiki/Isomer" title="Isomer">isomeric forms</a>, or they can be <a href="/wiki/Chirality" title="Chirality">achiral</a>. Furthermore, <a href="/wiki/Morphine" title="Morphine">morphine</a>-based natural products can be heated in acid to give aporphine degradation products; one example is the FDA-approved Parkinson's drug apomorphine, which was first discovered by the Finnish chemist Adolf Edvard Arppe in 1845.<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> </p> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:Aporphines.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/f/fa/Aporphines.png/220px-Aporphines.png" decoding="async" width="220" height="74" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/f/fa/Aporphines.png/330px-Aporphines.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/f/fa/Aporphines.png/440px-Aporphines.png 2x" data-file-width="960" data-file-height="324" /></a><figcaption>Aporphines can occur as either (R)- or (S)-isomers, or as achiral compounds, and while many of these are toxic, some have been used for their medicinal value and have been approved by the FDA and world markets.</figcaption></figure> <div class="mw-heading mw-heading3"><h3 id="Apomorphine">Apomorphine</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Aporphine&action=edit&section=2" title="Edit section: Apomorphine"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><a href="/wiki/Apomorphine" title="Apomorphine">Apomorphine</a> is a derivative of aporphine. The compound is historically obtained by heating morphine with <a href="/wiki/Hydrochloric_acid" title="Hydrochloric acid">hydrochloric acid</a>. Contrary to its name, apomorphine does not contain morphine or its skeleton, nor does it bind to <a href="/wiki/Opioid_receptor" title="Opioid receptor">opioid receptors</a>. The apo- prefix indicates that it is a morphine derivative. </p><p>Historically, apomorphine has seen a variety of clinical uses including as a treatment for <a href="/wiki/Anxiety" title="Anxiety">anxiety</a> and cravings in alcoholics, as an <a href="/wiki/Vomiting" title="Vomiting">emetic</a>, and more recently in treating <a href="/wiki/Erectile_dysfunction" title="Erectile dysfunction">erectile dysfunction</a>. It was also used as a private treatment for heroin addiction. Still, there is no clinical evidence that apomorphine is an effective and safe treatment for <a href="/wiki/Opioid_use_disorder" title="Opioid use disorder">opiate addiction</a>. </p><p>Currently, apomorphine is used in the treatment of <a href="/wiki/Parkinson%27s_disease" title="Parkinson's disease">Parkinson's disease</a>. It is a potent <a href="/wiki/Emetic" class="mw-redirect" title="Emetic">emetic</a>, typically administered with an antiemetic such as <a href="/wiki/Domperidone" title="Domperidone">domperidone</a>. Apomorphine is also utilized in <a href="/wiki/Veterinary_medicine" title="Veterinary medicine">veterinary medicine</a> to induce therapeutic <a href="/wiki/Emesis" class="mw-redirect" title="Emesis">emesis</a> in canines that have recently ingested toxic or foreign substances.<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> </p> <div class="mw-heading mw-heading2"><h2 id="Effects">Effects</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Aporphine&action=edit&section=3" title="Edit section: Effects"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Aporphine is a <a href="/wiki/Dopamine_receptor_agonist" class="mw-redirect" title="Dopamine receptor agonist">dopamine receptor agonist</a> targeting the <a href="/wiki/Dopamine_receptor_D1" title="Dopamine receptor D1">D1</a> and <a href="/wiki/Dopamine_receptor_D2" title="Dopamine receptor D2">D2</a> receptors.<sup id="cite_ref-Goldman_Kebabian_1984_pp._18–23_6-0" class="reference"><a href="#cite_note-Goldman_Kebabian_1984_pp._18–23-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> In rodents, aporphine administration has been demonstrated to activate <a href="/wiki/Gene" title="Gene">gene</a> expression, specifically in the nuclei of the <a href="/wiki/Hypothalamus" title="Hypothalamus">hypothalamus</a>, resulting in stereotypical behavior of erection and yawning. In humans, aporphine produces nonsexual erections that are enhanced by erotic stimulation without changes in libido, but significant side effects can occur. A sublingual formulation of aporphine 2-4 mg with a rapid onset of action has been developed, proven to be efficacious in erectile dysfunction patients with controlled <a href="/wiki/Diabetes" title="Diabetes">diabetes</a>, <a href="/wiki/Hypertension" title="Hypertension">hypertension</a>, <a href="/wiki/Benign_prostatic_hyperplasia" title="Benign prostatic hyperplasia">benign prostatic hyperplasia</a> or <a href="/wiki/Coronary_artery_disease" title="Coronary artery disease">coronary artery disease</a>.<sup id="cite_ref-7" class="reference"><a href="#cite_note-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Synthesis">Synthesis</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Aporphine&action=edit&section=4" title="Edit section: Synthesis"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Aporphine and its derivatives can be obtained through various synthetic methods. </p><p>Several natural products including semisynthetic analogs belonging to the aporphine class have been synthesized. These include apomorphine by Neumeyer<sup id="cite_ref-8" class="reference"><a href="#cite_note-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> and Raminelli,<sup id="cite_ref-9" class="reference"><a href="#cite_note-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> Pukateine by Happel,<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> Isocorydine by Di,<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> Nuciferine and Oliveroline by Cuny,<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><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> Glaucine by Meyers,<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> Dicentrine by Cava,<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> and Lysicamine by Raminelli.<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> </p> <div class="mw-heading mw-heading2"><h2 id="Toxicity">Toxicity</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Aporphine&action=edit&section=5" title="Edit section: Toxicity"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Most aporphine <a href="/wiki/Alkaloid" title="Alkaloid">alkaloids</a> are toxic and typically exhibit antagonistic effects to dopamine. Many of them have anticonvulsant activity or induce convulsions in animals due to <a href="/wiki/Cytotoxicity" title="Cytotoxicity">cytotoxic</a> activity.<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><p>Some aporphine alkaloids (such as crebanine) have been found to present <a href="/wiki/Arrhythmia" title="Arrhythmia">arrhythmic</a> activity and higher toxicity. In one study, a couple of target derivatives were evaluated for their anti-arrhythmic potential in the mouse model of <a href="/wiki/Ventricular_fibrillation" title="Ventricular fibrillation">ventricular fibrillation</a>. Here, preliminary structure-activity/toxicity relationship analyses were carried out. Of these target derivatives, a certain bromo-substituted product of crebanine displayed significant anti-arrhythmic activity and a lower toxicity. In a significant number of rats, this product caused reduction in the incidence of VF, increase in the resumption of <a href="/wiki/Sinus_rhythm" title="Sinus rhythm">sinus rhythm</a> from arrhythmia, and increase in maintaining sinus rhythm. The results from this limited study indicate that this specific aporphine alkaloid could be considered as a promising candidate in the treatment of arrhythmia.<sup id="cite_ref-18" class="reference"><a href="#cite_note-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup> </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=Aporphine&action=edit&section=6" title="Edit section: Pharmacology"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>According to the U.S. Patent & Trademark Office, aporphine derivatives can treat oxidative stress-induced diseases. Specifically, it inhibits lipid <a href="/wiki/Peroxidase" title="Peroxidase">peroxidase</a> and performs free radical-scavenging activities, thereby exhibiting a protective effect on <a href="/wiki/Endothelium" title="Endothelium">endothelial cells</a>. This reduces oxidative stress which may induce diseases such as cardiovascular disease, Alzheimer's disease, kidney disease, diabetes, cancer etc.<sup id="cite_ref-19" class="reference"><a href="#cite_note-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup> </p><p>Aporphine alkaloids present in <a href="/wiki/Litsea_glutinosa" title="Litsea glutinosa">Litsea glutinosa</a>, a tropical plant with antioxidant and anti-parasitic properties, are claimed to contribute to anti-cancer activity. Research has illustrated the <a href="/wiki/Antiproliferative" class="mw-redirect" title="Antiproliferative">antiproliferative</a> and cytotoxic effects of aporphine-containing extracts of Litsea glutinosa.<sup id="cite_ref-20" class="reference"><a href="#cite_note-20"><span class="cite-bracket">[</span>20<span class="cite-bracket">]</span></a></sup> </p><p>(<i>R</i>)-Aporphine is a <a href="/wiki/Dopamine_receptor_D1" title="Dopamine receptor D1">dopamine receptor D<sub>1</sub></a> antagonist with a <i>K</i><sub>i</sub> of 717nM<sup id="cite_ref-pmid8784448_21-0" class="reference"><a href="#cite_note-pmid8784448-21"><span class="cite-bracket">[</span>21<span class="cite-bracket">]</span></a></sup> and a <a href="/wiki/Dopamine_receptor_D2" title="Dopamine receptor D2">dopamine receptor D<sub>2</sub></a> antagonist with a <i>K</i><sub>i</sub> of 527nM.<sup id="cite_ref-pmid11311055_22-0" class="reference"><a href="#cite_note-pmid11311055-22"><span class="cite-bracket">[</span>22<span class="cite-bracket">]</span></a></sup> Aporphine and its related alkaloids <a href="/wiki/Bulbocapnine" title="Bulbocapnine">bulbocapnine</a>, <a href="/wiki/Boldine" title="Boldine">boldine</a>, <a href="/wiki/Glaucine" title="Glaucine">glaucine</a>, and corytuberine are antipsychotic, exert <a href="/wiki/Naloxone" title="Naloxone">naloxone</a>-reversible <a href="/wiki/Nociception" title="Nociception">antinociceptive</a> activity and, except for corytuberine, are anticonvulsant.<sup id="cite_ref-pmid2907279_23-0" class="reference"><a href="#cite_note-pmid2907279-23"><span class="cite-bracket">[</span>23<span class="cite-bracket">]</span></a></sup> Some derivatives of aporphine such as (<i>S</i>)-(+)-<i>N</i>-propylnorapomorphine have potential as low side effect profile antipsychotics. (<i>S</i>)-(+)-<i>N</i>-<a href="/wiki/Propylnorapomorphine" title="Propylnorapomorphine">Propylnorapomorphine</a> is highly selective for <i>meso</i>-limbic dopaminergic tracts and function as efficacious partial agonists, with no elevation in prolactin.<sup id="cite_ref-pmid7830962_24-0" class="reference"><a href="#cite_note-pmid7830962-24"><span class="cite-bracket">[</span>24<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=Aporphine&action=edit&section=7" title="Edit section: Pharmacokinetics"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Aporphine is <a href="/wiki/Hydroxylated" class="mw-redirect" title="Hydroxylated">hydroxylated</a> in the body to form <a href="/wiki/Apomorphine" title="Apomorphine">apomorphine</a>.<sup id="cite_ref-25" class="reference"><a href="#cite_note-25"><span class="cite-bracket">[</span>25<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Psychoactive_effects">Psychoactive effects</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Aporphine&action=edit&section=8" title="Edit section: Psychoactive effects"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The <i><a href="/wiki/Nymphaea" title="Nymphaea">Nymphaea</a></i> species, particularly <i><a href="/wiki/Nymphaea_caerulea" class="mw-redirect" title="Nymphaea caerulea">Nymphaea Caerulea</a>,</i> contains aporphine alkaloids and is utilized in various contexts.<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> Extracts of this plant when ingested or smoken in high doses are reported to produce <a href="/wiki/Euphoria" title="Euphoria">euphoria</a> and <a href="/wiki/Hallucination" title="Hallucination">hallucinations</a>. Commonly known as the blue lotus, <i>Nymphaea Caerulea</i> is available in several forms, including dried plant material, <a href="/wiki/Tea" title="Tea">teas</a>, and extracts for <a href="/wiki/Electronic_cigarette" title="Electronic cigarette">electronic cigarettes.</a> The psychoactive effects of the flower are attributed to two aporphine alkaloids: apomorphine and <a href="/wiki/Nuciferine" title="Nuciferine">nuciferine</a>. These compounds have mixed effects on <a href="/wiki/Serotonin" title="Serotonin">serotonin</a> and <a href="/wiki/Dopamine" title="Dopamine">dopamine</a> receptors, functioning as a dopaminergic agonist.<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> </p> <div class="mw-heading mw-heading2"><h2 id="Effects_on_animals">Effects on animals</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Aporphine&action=edit&section=9" title="Edit section: Effects on animals"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>There are no studies on aporphine in animals. However, studies on subcutaneous apomorphine injection, the bioactive form of aporphine, have been carried out. In a 5-day study, mice were administered up to 10 mg/kg apomorphine subcutaneously daily. No adverse effects were observed other than a slight increase in dopamine levels.<sup id="cite_ref-28" class="reference"><a href="#cite_note-28"><span class="cite-bracket">[</span>28<span class="cite-bracket">]</span></a></sup> Notably, apomorphine is used in veterinary clinics as an emetic due to severe off-target effects that lead to vomiting.<sup id="cite_ref-29" class="reference"><a href="#cite_note-29"><span class="cite-bracket">[</span>29<span class="cite-bracket">]</span></a></sup> </p><p>In another study, mice were administered a single 40 mg/kg dose of apomorphine. Slight DNA damage was observed in brain tissue three hours after treatment.<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="See_also">See also</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Aporphine&action=edit&section=10" title="Edit section: See also"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a href="/wiki/Anonaine" title="Anonaine">Anonaine</a></li> <li><a href="/wiki/Liriodenine" title="Liriodenine">Liriodenine</a></li> <li><a href="/wiki/Magnoflorine" title="Magnoflorine">Magnoflorine</a></li> <li><a href="/wiki/Nantenine" title="Nantenine">Nantenine</a></li> <li><a href="/wiki/Nuciferine" title="Nuciferine">Nuciferine</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=Aporphine&action=edit&section=11" 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-1"><span class="mw-cite-backlink"><b><a href="#cite_ref-1">^</a></b></span> <span class="reference-text"><style data-mw-deduplicate="TemplateStyles:r1238218222">.mw-parser-output cite.citation{font-style:inherit;word-wrap:break-word}.mw-parser-output .citation q{quotes:"\"""\"""'""'"}.mw-parser-output .citation:target{background-color:rgba(0,127,255,0.133)}.mw-parser-output .id-lock-free.id-lock-free a{background:url("//upload.wikimedia.org/wikipedia/commons/6/65/Lock-green.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-limited.id-lock-limited a,.mw-parser-output .id-lock-registration.id-lock-registration a{background:url("//upload.wikimedia.org/wikipedia/commons/d/d6/Lock-gray-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-subscription.id-lock-subscription a{background:url("//upload.wikimedia.org/wikipedia/commons/a/aa/Lock-red-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .cs1-ws-icon a{background:url("//upload.wikimedia.org/wikipedia/commons/4/4c/Wikisource-logo.svg")right 0.1em center/12px no-repeat}body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-free a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-limited a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-registration a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-subscription a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .cs1-ws-icon a{background-size:contain;padding:0 1em 0 0}.mw-parser-output .cs1-code{color:inherit;background:inherit;border:none;padding:inherit}.mw-parser-output .cs1-hidden-error{display:none;color:var(--color-error,#d33)}.mw-parser-output .cs1-visible-error{color:var(--color-error,#d33)}.mw-parser-output .cs1-maint{display:none;color:#085;margin-left:0.3em}.mw-parser-output .cs1-kern-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right{padding-right:0.2em}.mw-parser-output .citation .mw-selflink{font-weight:inherit}@media screen{.mw-parser-output .cs1-format{font-size:95%}html.skin-theme-clientpref-night .mw-parser-output .cs1-maint{color:#18911f}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .cs1-maint{color:#18911f}}</style><cite id="CITEREFStévignyBaillyQuetin-Leclercq2005" class="citation journal cs1">Stévigny C, Bailly C, Quetin-Leclercq J (March 2005). 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Molecular Brain Research</i>. <b>114</b> (1): 80–85. <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%2Fs0169-328x%2803%2900127-x">10.1016/s0169-328x(03)00127-x</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/12782396">12782396</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Brain+Research.+Molecular+Brain+Research&rft.atitle=DNA+damage+in+brain+cells+of+mice+treated+with+an+oxidized+form+of+apomorphine&rft.volume=114&rft.issue=1&rft.pages=80-85&rft.date=2003-05&rft_id=info%3Adoi%2F10.1016%2Fs0169-328x%2803%2900127-x&rft_id=info%3Apmid%2F12782396&rft.aulast=Picada&rft.aufirst=JN&rft.au=Flores%2C+DG&rft.au=Zettler%2C+CG&rft.au=Marroni%2C+NP&rft.au=Roesler%2C+R&rft.au=Henriques%2C+JA&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAporphine" class="Z3988"></span></span> </li> </ol></div></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=Aporphine&oldid=1257279095">https://en.wikipedia.org/w/index.php?title=Aporphine&oldid=1257279095</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">Category</a>: <ul><li><a href="/wiki/Category:Aporphine_alkaloids" title="Category:Aporphine alkaloids">Aporphine alkaloids</a></li></ul></div><div id="mw-hidden-catlinks" class="mw-hidden-catlinks mw-hidden-cats-hidden">Hidden categories: <ul><li><a href="/wiki/Category:Articles_with_short_description" title="Category:Articles with short description">Articles with short description</a></li><li><a href="/wiki/Category:Short_description_matches_Wikidata" title="Category:Short description matches Wikidata">Short description matches Wikidata</a></li><li><a href="/wiki/Category:Infobox_drug_articles_with_non-default_infobox_title" title="Category:Infobox drug articles with non-default infobox title">Infobox drug articles with non-default infobox title</a></li><li><a href="/wiki/Category:Chemical_pages_without_DrugBank_identifier" title="Category:Chemical pages without DrugBank identifier">Chemical pages without DrugBank identifier</a></li><li><a href="/wiki/Category:Articles_without_KEGG_source" title="Category:Articles without KEGG source">Articles without KEGG source</a></li><li><a href="/wiki/Category:Drugs_missing_an_ATC_code" title="Category:Drugs missing an ATC code">Drugs missing an ATC code</a></li><li><a href="/wiki/Category:Drugs_with_no_legal_status" title="Category:Drugs with no legal status">Drugs with no legal status</a></li><li><a href="/wiki/Category:Articles_containing_unverified_chemical_infoboxes" title="Category:Articles containing unverified chemical infoboxes">Articles containing unverified chemical infoboxes</a></li></ul></div></div> </div> </main> </div> <div class="mw-footer-container"> <footer id="footer" class="mw-footer" > <ul id="footer-info"> <li id="footer-info-lastmod"> This page was last edited on 14 November 2024, at 03:12<span class="anonymous-show"> (UTC)</span>.</li> <li id="footer-info-copyright">Text is available under the <a href="/wiki/Wikipedia:Text_of_the_Creative_Commons_Attribution-ShareAlike_4.0_International_License" title="Wikipedia:Text of the Creative Commons Attribution-ShareAlike 4.0 International License">Creative Commons Attribution-ShareAlike 4.0 License</a>; additional terms may apply. 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