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Vanoxerin – Wikipedia

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margin-top:0; width:350px;" summary="Infobox Chemikalie"> <tbody><tr> <th colspan="2" style="background:#FFDEAD; color:#202122;">Strukturformel </th></tr> <tr> <td colspan="2" class="hintergrundfarbe-basis skin-invert-image" style="text-align:center;"><span typeof="mw:File"><a href="/wiki/Datei:Vanoxerine.svg" class="mw-file-description" title="Struktur von Vanoxerin"><img alt="Struktur von Vanoxerin" src="//upload.wikimedia.org/wikipedia/commons/thumb/f/f7/Vanoxerine.svg/300px-Vanoxerine.svg.png" decoding="async" width="300" height="140" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/f/f7/Vanoxerine.svg/450px-Vanoxerine.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/f/f7/Vanoxerine.svg/600px-Vanoxerine.svg.png 2x" data-file-width="1012" data-file-height="472" /></a></span> </td></tr> <tr> <th colspan="2" style="background:#FFDEAD; color:#202122;">Allgemeines </th></tr> <tr> <td style="width:33%;"><a href="/wiki/Internationaler_Freiname" title="Internationaler Freiname">Freiname</a> </td> <td>Vanoxerin </td></tr> <tr> <td>Andere Namen </td> <td> <ul><li>1-[2-(4,4-Difluorbenzhydryloxy)ethyl]-4-(3-phenylpropyl)piperazin</li> <li>GBR-12909</li></ul> </td></tr> <tr> <td><a href="/wiki/Summenformel" title="Summenformel">Summenformel</a> </td> <td>C<sub>28</sub>H<sub>32</sub>F<sub>2</sub>N<sub>2</sub>O </td></tr> <tr> <th colspan="2" style="background:#FFDEAD; color:#202122;">Externe Identifikatoren/Datenbanken </th></tr> <tr> <td colspan="2" style="padding:0;"> <table class="mw-collapsible mw-collapsed wikitable" data-expandtext="+" data-collapsetext="−" style="border-top:none; margin:-1px; width:calc(100% + 2px);"> <tbody><tr> <td style="width:33%;"><a href="/wiki/CAS-Nummer" title="CAS-Nummer">CAS-Nummer</a> </td> <td> <ul><li><span title="Untervorlage eingebunden: CASRN"></span><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?ref=67469-69-6">67469-69-6</a><span class="editoronly" style="display:none;"></span></li> <li><span title="Untervorlage eingebunden: CASRN"></span><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?ref=67469-78-7">67469-78-7</a><span class="editoronly" style="display:none;"></span> (Di<a href="/wiki/Hydrochlorid" class="mw-redirect" title="Hydrochlorid">hydrochlorid</a>)</li></ul> </td> <td style="background:#FFDEAD; color:#202122; border-top:1px solid #FFDEAD; padding:0.2em 0; vertical-align:bottom; width:5%;"> </td></tr> <tr> <td><a href="/wiki/PubChem" title="PubChem">PubChem</a> </td> <td colspan="2"><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/3455">3455</a> </td></tr> <tr> <td><a href="/wiki/ChemSpider" title="ChemSpider">ChemSpider</a> </td> <td colspan="2"><a rel="nofollow" class="external text" href="https://www.chemspider.com/Chemical-Structure.3337.html">3337</a> </td></tr> <tr> <td><a href="/wiki/DrugBank" title="DrugBank">DrugBank</a> </td> <td colspan="2"><a rel="nofollow" class="external text" href="https://www.drugbank.ca/drugs/DB03701">DB03701</a> </td></tr> <tr> <td style="border-right:1px solid #a2a9b1;"><a href="/wiki/Wikidata" title="Wikidata">Wikidata</a> </td> <td colspan="2"><a href="https://www.wikidata.org/wiki/Q2510480" class="extiw" title="d:Q2510480">Q2510480</a> </td></tr></tbody></table> </td></tr> <tr> <th colspan="2" style="background:#FFDEAD; color:#202122;">Arzneistoffangaben </th></tr> <tr> <td><a href="/wiki/Wirkstoffklasse" title="Wirkstoffklasse">Wirkstoffklasse</a> </td> <td> <p><a href="/wiki/Dopamin" title="Dopamin">Dopamin</a>-Wiederaufnahme-Hemmer </p> </td></tr> <tr> <th colspan="2" style="background:#FFDEAD; color:#202122;">Eigenschaften </th></tr> <tr> <td><a href="/wiki/Molare_Masse" title="Molare Masse">Molare Masse</a> </td> <td>450,56 <a href="/wiki/Gramm" title="Gramm">g</a>·<a href="/wiki/Mol" title="Mol">mol</a><sup>−1</sup> </td></tr> <tr> <th colspan="2" style="background:#FFDEAD; color:#202122;">Sicherheitshinweise </th></tr> <tr> <td colspan="2"> <table cellspacing="0" cellpadding="2" style="width:100%;"> <tbody><tr> <td colspan="2" style="text-align:center"><b><a href="/wiki/Global_harmonisiertes_System_zur_Einstufung_und_Kennzeichnung_von_Chemikalien" title="Global harmonisiertes System zur Einstufung und Kennzeichnung von Chemikalien">GHS-Gefahrstoffkennzeichnung</a></b><sup id="cite_ref-Sigma_1-0" class="reference"><a href="#cite_note-Sigma-1"><span class="cite-bracket">&#91;</span>1<span class="cite-bracket">&#93;</span></a></sup> <table id="Piktogramme-" class="hintergrundfarbe-neutral" style="text-align:center; margin-left:auto; margin-right:auto; display:flex; justify-content:center;"> <tbody><tr> <td><i>keine GHS-Piktogramme</i> </td></tr></tbody></table> <p>&#32; </p> </td></tr> <tr> <td rowspan="2" width="33%" style="border-top:1px #A7A7A7 dashed; border-right:1px #A7A7A7 dashed;"><a href="/wiki/H-_und_P-S%C3%A4tze" title="H- und P-Sätze">H- und P-Sätze</a> </td> <td style="border-top:1px #A7A7A7 dashed;">H: <span title="Untervorlage eingebunden: H-Sätze"></span><i>keine H-Sätze</i> </td></tr> <tr> <td style="border-top:1px #A7A7A7 dashed;">P: <span title="Untervorlage eingebunden: P-Sätze"></span><i>keine P-Sätze</i> </td></tr> </tbody></table> </td></tr> <tr> <td colspan="2" style="background:#FFDEAD; color:#202122; font-size:80%; text-align:center; line-height:150%; padding:.25em;">Soweit möglich und gebräuchlich, werden <a href="/wiki/Internationales_Einheitensystem" title="Internationales Einheitensystem">SI-Einheiten</a> verwendet.<br />Wenn nicht anders vermerkt, gelten die angegebenen Daten bei <a href="/wiki/Standardbedingungen" title="Standardbedingungen">Standardbedingungen</a> (0&#8239;°C, 1000&#160;hPa). </td></tr></tbody></table><p><span class="editoronly" style="display:none;"></span> </p><p><b>Vanoxerin</b>, auch unter dem Namen <b>GBR-12909</b> bekannt, ist ein <a href="/wiki/Piperazin" title="Piperazin">Piperazin</a>-<a href="/wiki/Derivat_(Chemie)" title="Derivat (Chemie)">Derivat</a>, das beim Menschen als selektiver <a href="/wiki/Dopamin-Wiederaufnahmehemmer" title="Dopamin-Wiederaufnahmehemmer">Dopamin-Wiederaufnahmehemmer</a> (SDRI) wirkt.<sup id="cite_ref-:0_2-0" class="reference"><a href="#cite_note-:0-2"><span class="cite-bracket">&#91;</span>2<span class="cite-bracket">&#93;</span></a></sup> Es wurde als Ersatzstoff zur Behandlung von Kokainabhängigen entwickelt, um die psychischen <a href="/wiki/Entzugserscheinung" class="mw-redirect" title="Entzugserscheinung">Entzugserscheinungen</a> abzumildern. GBR-12909 bindet hierbei wie <a href="/wiki/Kokain" title="Kokain">Kokain</a> den Dopaminwiederaufnahmetransporter, jedoch 100 Mal stärker ohne dabei einen nennenswerten <a href="/wiki/Stimulans" title="Stimulans">stimulierenden</a> Effekt zu haben, da es im Gegensatz zu Kokain die gleichzeitige Ausschüttung von Dopamin unterbindet. Auch die Halbwertszeit von Vanoxerin ist wesentlich länger als bei Kokain.<sup id="cite_ref-3" class="reference"><a href="#cite_note-3"><span class="cite-bracket">&#91;</span>3<span class="cite-bracket">&#93;</span></a></sup> </p><p>Vanoxerin wurde in Versuchen an Menschen zur Behandlung der Kokainabhängigkeit untersucht.<sup id="cite_ref-4" class="reference"><a href="#cite_note-4"><span class="cite-bracket">&#91;</span>4<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-5" class="reference"><a href="#cite_note-5"><span class="cite-bracket">&#91;</span>5<span class="cite-bracket">&#93;</span></a></sup> Die Entwicklung und Untersuchung an Menschen wurden jedoch aufgrund der beobachteten QTc-Effekte (unerwünschte Arzneimittelwirkungen) im Zusammenhang mit Kokainkonsum eingestellt.<sup id="cite_ref-6" class="reference"><a href="#cite_note-6"><span class="cite-bracket">&#91;</span>6<span class="cite-bracket">&#93;</span></a></sup> In jüngerer Zeit wurde Vanoxerin aufgrund seiner Fähigkeit, den hKV11.1 (hERG)-Kaliumkanal des Herzens zu blockieren, als potenzielles Mittel gegen Herzrhythmusstörungen und Vorhofflimmern getestet.<sup id="cite_ref-7" class="reference"><a href="#cite_note-7"><span class="cite-bracket">&#91;</span>7<span class="cite-bracket">&#93;</span></a></sup> Vanoxerin ist ein Prüfpräparat und wurde nicht für die therapeutische Verwendung zugelassen.<sup id="cite_ref-:0_2-1" class="reference"><a href="#cite_note-:0-2"><span class="cite-bracket">&#91;</span>2<span class="cite-bracket">&#93;</span></a></sup> </p><p>An Tieren wird weiterhin die Wirkung des Stoffes untersucht.<sup id="cite_ref-8" class="reference"><a href="#cite_note-8"><span class="cite-bracket">&#91;</span>8<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-9" class="reference"><a href="#cite_note-9"><span class="cite-bracket">&#91;</span>9<span class="cite-bracket">&#93;</span></a></sup> </p><p>Es wurde auch ein <a href="/wiki/Caprins%C3%A4ure" title="Caprinsäure">Caprinsäure</a>-<a href="/wiki/Ester" title="Ester">Ester</a> eines Hydroxy-Vanoxerins entwickelt (DBL-583), der als <a href="/wiki/Depotspritze" class="mw-redirect" title="Depotspritze">Depotspritze</a> gegeben werden kann und etwa für einen Monat wirkt. </p> <div class="mw-heading mw-heading2"><h2 id="Einzelnachweise">Einzelnachweise</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Vanoxerin&amp;veaction=edit&amp;section=1" title="Abschnitt bearbeiten: Einzelnachweise" class="mw-editsection-visualeditor"><span>Bearbeiten</span></a><span class="mw-editsection-divider"> | </span><a href="/w/index.php?title=Vanoxerin&amp;action=edit&amp;section=1" title="Quellcode des Abschnitts bearbeiten: Einzelnachweise"><span>Quelltext bearbeiten</span></a><span class="mw-editsection-bracket">]</span></span></div> <ol class="references"> <li id="cite_note-Sigma-1"><span class="mw-cite-backlink"><a href="#cite_ref-Sigma_1-0">↑</a></span> <span class="reference-text">Datenblatt <span style="font-style:italic;"><a rel="nofollow" class="external text" href="https://www.sigmaaldrich.com/catalog/product/SIGMA/D052">GBR 12909 dihydrochloride</a></span> bei <a href="/wiki/Sigma-Aldrich" title="Sigma-Aldrich">Sigma-Aldrich</a>,&#32;abgerufen am 14.&#160;Dezember 2012 (<a rel="nofollow" class="external text" href="https://www.sigmaaldrich.com/DE/de/sds/SIGMA/D052?userType=anonymous">PDF</a>).<span class="editoronly" style="display:none;"></span></span> </li> <li id="cite_note-:0-2"><span class="mw-cite-backlink">↑ <sup><a href="#cite_ref-:0_2-0">a</a></sup> <sup><a href="#cite_ref-:0_2-1">b</a></sup></span> <span class="reference-text"><span class="cite"><a rel="nofollow" class="external text" href="https://go.drugbank.com/drugs/DB03701"><i>Vanoxerine.</i></a>&#32;DrugBank online,&#32;2022&#44;<span class="Abrufdatum">&#32;abgerufen am 15.&#160;Mai 2024</span>&#32;(englisch).</span><span style="display: none;" class="Z3988" title="ctx_ver=Z39.88-2004&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Adc&amp;rfr_id=info%3Asid%2Fde.wikipedia.org%3AVanoxerin&amp;rft.title=Vanoxerine&amp;rft.description=Vanoxerine&amp;rft.identifier=https%3A%2F%2Fgo.drugbank.com%2Fdrugs%2FDB03701&amp;rft.publisher=DrugBank+online&amp;rft.date=2022&amp;rft.language=en">&#160;</span></span> </li> <li id="cite_note-3"><span class="mw-cite-backlink"><a href="#cite_ref-3">↑</a></span> <span class="reference-text">Srihari R. Tella, Bruce Ladenheim, Anne M. Andrews, Steven R. Goldberg, and Jean Lud Cadet&#58; <cite style="font-style:italic">Differential Reinforcing Effects of Cocaine and GBR-12909: Biochemical Evidence for Divergent Neuroadaptive Changes in the Mesolimbic Dopaminergic System</cite>. In: <cite style="font-style:italic">The Journal of Neuroscience</cite>. <span style="white-space:nowrap">Band<span style="display:inline-block;width:.2em">&#160;</span>16</span>, <span style="white-space:nowrap">Nr.<span style="display:inline-block;width:.2em">&#160;</span>23</span>, 1996, <span style="white-space:nowrap">S.<span style="display:inline-block;width:.2em">&#160;</span>7416–7427</span> (<a rel="nofollow" class="external text" href="https://www.jneurosci.org/content/jneuro/16/23/7416.full.pdf">jneurosci.org</a> &#91;PDF; abgerufen am 15.&#160;Mai 2024&#93;).<span class="Z3988" title="ctx_ver=Z39.88-2004&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&amp;rfr_id=info:sid/de.wikipedia.org:Vanoxerin&amp;rft.atitle=Differential+Reinforcing+Effects+of+Cocaine+and+GBR-12909%3A%0ABiochemical+Evidence+for+Divergent+Neuroadaptive+Changes+in+the%0AMesolimbic+Dopaminergic+System&amp;rft.au=Srihari+R.+Tella%2C+Bruce+Ladenheim%2C+Anne+M.+Andrews%2C+...&amp;rft.date=1996&amp;rft.genre=journal&amp;rft.issue=23&amp;rft.jtitle=The+Journal+of+Neuroscience&amp;rft.pages=7416-7427&amp;rft.volume=16" style="display:none">&#160;</span></span> </li> <li id="cite_note-4"><span class="mw-cite-backlink"><a href="#cite_ref-4">↑</a></span> <span class="reference-text">U. Søgaard, J. Michalow, B. Butler, A. Lund Laursen, S. H. Ingersen, B. K. Skrumsager, O. J. Rafaelsen&#58; <cite style="font-style:italic">A Tolerance Study of Single and Multiple Dosing of the Selective Dopamine Uptake Inhibitor GBR 12909 in Healthy Subjects</cite>. In: <cite style="font-style:italic">International Clinical Psychopharmacology</cite>. <span style="white-space:nowrap">Band<span style="display:inline-block;width:.2em">&#160;</span>5</span>, <span style="white-space:nowrap">Nr.<span style="display:inline-block;width:.2em">&#160;</span>4</span>, Oktober 1990, <span style="white-space:nowrap">S.<span style="display:inline-block;width:.2em">&#160;</span>237</span>, <a href="/wiki/Digital_Object_Identifier" title="Digital Object Identifier">doi</a>:<span class="uri-handle" style="white-space:nowrap"><a rel="nofollow" class="external text" href="https://doi.org/10.1097/00004850-199010000-00001">10.1097/00004850-199010000-00001</a></span>.<span class="Z3988" title="ctx_ver=Z39.88-2004&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&amp;rfr_id=info:sid/de.wikipedia.org:Vanoxerin&amp;rft.atitle=A+Tolerance+Study+of+Single+and+Multiple+Dosing+of+the+Selective+Dopamine+Uptake+Inhibitor+GBR+12909+in+Healthy+Subjects&amp;rft.au=U.+S%C3%B8gaard%2C+J.+Michalow%2C+B.+Butler%2C+...&amp;rft.date=1990-10&amp;rft.doi=10.1097%2F00004850-199010000-00001&amp;rft.genre=journal&amp;rft.issue=4&amp;rft.jtitle=International+Clinical+Psychopharmacology&amp;rft.pages=237&amp;rft.volume=5" style="display:none">&#160;</span></span> </li> <li id="cite_note-5"><span class="mw-cite-backlink"><a href="#cite_ref-5">↑</a></span> <span class="reference-text">David A. Gorelick, Eliot L. Gardner, Zheng-Xiong Xi&#58; <cite style="font-style:italic">Agents in Development for the Management of Cocaine Abuse</cite>. In: <cite style="font-style:italic">Drugs</cite>. <span style="white-space:nowrap">Band<span style="display:inline-block;width:.2em">&#160;</span>64</span>, <span style="white-space:nowrap">Nr.<span style="display:inline-block;width:.2em">&#160;</span>14</span>, 1.&#160;Juli 2004, <span style="white-space:nowrap">S.<span style="display:inline-block;width:.2em">&#160;</span>1547–1573</span>, <a href="/wiki/Digital_Object_Identifier" title="Digital Object Identifier">doi</a>:<span class="uri-handle" style="white-space:nowrap"><a rel="nofollow" class="external text" href="https://doi.org/10.2165/00003495-200464140-00004">10.2165/00003495-200464140-00004</a></span>.<span class="Z3988" title="ctx_ver=Z39.88-2004&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&amp;rfr_id=info:sid/de.wikipedia.org:Vanoxerin&amp;rft.atitle=Agents+in+Development+for+the+Management+of+Cocaine+Abuse&amp;rft.au=David+A.+Gorelick%2C+Eliot+L.+Gardner%2C+Zheng-Xiong+Xi&amp;rft.date=2004-07-01&amp;rft.doi=10.2165%2F00003495-200464140-00004&amp;rft.genre=journal&amp;rft.issue=14&amp;rft.jtitle=Drugs&amp;rft.pages=1547-1573&amp;rft.volume=64" style="display:none">&#160;</span></span> </li> <li id="cite_note-6"><span class="mw-cite-backlink"><a href="#cite_ref-6">↑</a></span> <span class="reference-text">Barbara H. Herman, Ahmed Elkashef, Frank Vocci&#58; <cite style="font-style:italic">Medications for the treatment of cocaine addiction: Emerging candidates</cite>. In: <cite style="font-style:italic">Drug Discovery Today: Therapeutic Strategies</cite>. <span style="white-space:nowrap">Band<span style="display:inline-block;width:.2em">&#160;</span>2</span>, <span style="white-space:nowrap">Nr.<span style="display:inline-block;width:.2em">&#160;</span>1</span>, März 2005, <span style="white-space:nowrap">S.<span style="display:inline-block;width:.2em">&#160;</span>87–92</span>, <a href="/wiki/Digital_Object_Identifier" title="Digital Object Identifier">doi</a>:<span class="uri-handle" style="white-space:nowrap"><a rel="nofollow" class="external text" href="https://doi.org/10.1016/j.ddstr.2005.05.014">10.1016/j.ddstr.2005.05.014</a></span>.<span class="Z3988" title="ctx_ver=Z39.88-2004&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&amp;rfr_id=info:sid/de.wikipedia.org:Vanoxerin&amp;rft.atitle=Medications+for+the+treatment+of+cocaine+addiction%3A+Emerging+candidates&amp;rft.au=Barbara+H.+Herman%2C+Ahmed+Elkashef%2C+Frank+Vocci&amp;rft.date=2005-03&amp;rft.doi=10.1016%2Fj.ddstr.2005.05.014&amp;rft.genre=journal&amp;rft.issue=1&amp;rft.jtitle=Drug+Discovery+Today%3A+Therapeutic+Strategies&amp;rft.pages=87-92&amp;rft.volume=2" style="display:none">&#160;</span></span> </li> <li id="cite_note-7"><span class="mw-cite-backlink"><a href="#cite_ref-7">↑</a></span> <span class="reference-text">Antonio E. Lacerda, Yuri A. Kuryshev, Gan‐Xin Yan, Albert L. Waldo, Arthur M. Brown&#58; <cite style="font-style:italic">Vanoxerine: Cellular Mechanism of a New Antiarrhythmic</cite>. In: <cite style="font-style:italic">Journal of Cardiovascular Electrophysiology</cite>. <span style="white-space:nowrap">Band<span style="display:inline-block;width:.2em">&#160;</span>21</span>, <span style="white-space:nowrap">Nr.<span style="display:inline-block;width:.2em">&#160;</span>3</span>, März 2010, <span style="white-space:nowrap">S.<span style="display:inline-block;width:.2em">&#160;</span>301–310</span>, <a href="/wiki/Digital_Object_Identifier" title="Digital Object Identifier">doi</a>:<span class="uri-handle" style="white-space:nowrap"><a rel="nofollow" class="external text" href="https://doi.org/10.1111/j.1540-8167.2009.01623.x">10.1111/j.1540-8167.2009.01623.x</a></span>, <a class="external mw-magiclink-pmid" rel="nofollow" href="//www.ncbi.nlm.nih.gov/pubmed/19817928?dopt=Abstract">PMID 19817928</a>.<span class="Z3988" title="ctx_ver=Z39.88-2004&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&amp;rfr_id=info:sid/de.wikipedia.org:Vanoxerin&amp;rft.atitle=Vanoxerine%3A+Cellular+Mechanism+of+a+New+Antiarrhythmic&amp;rft.au=Antonio+E.+Lacerda%2C+Yuri+A.+Kuryshev%2C+Gan%E2%80%90Xin+Yan%2C+...&amp;rft.date=2010-03&amp;rft.doi=10.1111%2Fj.1540-8167.2009.01623.x&amp;rft.genre=journal&amp;rft.issue=3&amp;rft.jtitle=Journal+of+Cardiovascular+Electrophysiology&amp;rft.pages=301-310&amp;rft.pmid=19817928&amp;rft.volume=21" style="display:none">&#160;</span></span> </li> <li id="cite_note-8"><span class="mw-cite-backlink"><a href="#cite_ref-8">↑</a></span> <span class="reference-text">Ana Isabelle G. Queiroz, Maíra Moraes de Araújo, Tatiane da Silva Araújo, Greicy Coelho de Souza, Lígia Menezes Cavalcante, Michel de Jesus Souza Machado, David Freitas de Lucena, João Quevedo, Danielle Macêdo&#58; <cite style="font-style:italic">GBR 12909 administration as an animal model of bipolar mania: time course of behavioral, brain oxidative alterations and effect of mood stabilizing drugs</cite>. In: <cite style="font-style:italic">Metabolic Brain Disease</cite>. <span style="white-space:nowrap">Band<span style="display:inline-block;width:.2em">&#160;</span>30</span>, <span style="white-space:nowrap">Nr.<span style="display:inline-block;width:.2em">&#160;</span>5</span>, 1.&#160;Oktober 2015, <span style="white-space:nowrap">S.<span style="display:inline-block;width:.2em">&#160;</span>1207–1215</span>, <a href="/wiki/Digital_Object_Identifier" title="Digital Object Identifier">doi</a>:<span class="uri-handle" style="white-space:nowrap"><a rel="nofollow" class="external text" href="https://doi.org/10.1007/s11011-015-9697-6">10.1007/s11011-015-9697-6</a></span>.<span class="Z3988" title="ctx_ver=Z39.88-2004&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&amp;rfr_id=info:sid/de.wikipedia.org:Vanoxerin&amp;rft.atitle=GBR+12909+administration+as+an+animal+model+of+bipolar+mania%3A+time+course+of+behavioral%2C+brain+oxidative+alterations+and+effect+of+mood+stabilizing+drugs&amp;rft.au=Ana+Isabelle+G.+Queiroz%2C+Ma%C3%ADra+Moraes+de+Ara%C3%BAjo%2C+Tatiane+da+Silva+Ara%C3%BAjo%2C+...&amp;rft.date=2015-10-01&amp;rft.doi=10.1007%2Fs11011-015-9697-6&amp;rft.genre=journal&amp;rft.issue=5&amp;rft.jtitle=Metabolic+Brain+Disease&amp;rft.pages=1207-1215&amp;rft.volume=30" style="display:none">&#160;</span></span> </li> <li id="cite_note-9"><span class="mw-cite-backlink"><a href="#cite_ref-9">↑</a></span> <span class="reference-text">Jared W. Young, Andrew K. L. Goey, Arpi Minassian, William Perry, Martin P. Paulus, Mark A. Geyer&#58; <cite style="font-style:italic">GBR 12909 administration as a mouse model of bipolar disorder mania: mimicking quantitative assessment of manic behavior</cite>. In: <cite style="font-style:italic">Psychopharmacology</cite>. <span style="white-space:nowrap">Band<span style="display:inline-block;width:.2em">&#160;</span>208</span>, <span style="white-space:nowrap">Nr.<span style="display:inline-block;width:.2em">&#160;</span>3</span>, 1.&#160;Februar 2010, <span style="white-space:nowrap">S.<span style="display:inline-block;width:.2em">&#160;</span>443–454</span>, <a href="/wiki/Digital_Object_Identifier" title="Digital Object Identifier">doi</a>:<span class="uri-handle" style="white-space:nowrap"><a rel="nofollow" class="external text" href="https://doi.org/10.1007/s00213-009-1744-8">10.1007/s00213-009-1744-8</a></span>, <a class="external mw-magiclink-pmid" rel="nofollow" href="//www.ncbi.nlm.nih.gov/pubmed/20020109?dopt=Abstract">PMID 20020109</a>.<span class="Z3988" title="ctx_ver=Z39.88-2004&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&amp;rfr_id=info:sid/de.wikipedia.org:Vanoxerin&amp;rft.atitle=GBR+12909+administration+as+a+mouse+model+of+bipolar+disorder+mania%3A+mimicking+quantitative+assessment+of+manic+behavior&amp;rft.au=Jared+W.+Young%2C+Andrew+K.+L.+Goey%2C+Arpi+Minassian%2C+...&amp;rft.date=2010-02-01&amp;rft.doi=10.1007%2Fs00213-009-1744-8&amp;rft.genre=journal&amp;rft.issue=3&amp;rft.jtitle=Psychopharmacology&amp;rft.pages=443-454&amp;rft.pmid=20020109&amp;rft.volume=208" style="display:none">&#160;</span></span> </li> </ol> <div class="hintergrundfarbe1 rahmenfarbe1 navigation-not-searchable" style="border-top-style: solid; border-top-width: 1px; clear: both; font-size:95%; margin-top:1em; padding: 0.25em; overflow: hidden; word-break: break-word; word-wrap: break-word;" id="Vorlage_Gesundheitshinweis"><div class="noviewer noresize nomobile" style="display: table-cell; padding-bottom: 0.2em; padding-left: 0.25em; padding-right: 1em; padding-top: 0.2em; vertical-align: middle;" aria-hidden="true" role="presentation"><span typeof="mw:File"><a href="/wiki/Wikipedia:Hinweis_Gesundheitsthemen" title="Gesundheitshinweis"><img alt="" src="//upload.wikimedia.org/wikipedia/commons/thumb/0/03/P_medicine_caution.svg/25px-P_medicine_caution.svg.png" decoding="async" width="25" height="29" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/0/03/P_medicine_caution.svg/38px-P_medicine_caution.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/0/03/P_medicine_caution.svg/50px-P_medicine_caution.svg.png 2x" data-file-width="261" data-file-height="305" /></a></span></div> <div style="display: table-cell; vertical-align: middle; width: 100%;"> <div> Dieser Artikel behandelt ein Gesundheitsthema. 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