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<h1 id="firstHeading" class="firstHeading mw-first-heading"><span class="mw-page-title-main">Pregnenolon</span></h1>
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<div id="mw-content-text" class="mw-body-content mw-content-ltr" lang="de" dir="ltr"><div class="mw-content-ltr mw-parser-output" lang="de" dir="ltr"><table class="wikitable infobox float-right" id="Vorlage_Infobox_Chemikalie" style="font-size:90%; margin-top:0; width:350px;" summary="Infobox Chemikalie">
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<th colspan="2" style="background:#FFDEAD; color:#202122;">Strukturformel
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<tr>
<td colspan="2" class="hintergrundfarbe-basis skin-invert-image" style="text-align:center;"><span typeof="mw:File"></span>
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<th colspan="2" style="background:#FFDEAD; color:#202122;">Allgemeines
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<tr>
<td style="width:33%;">Name
</td>
<td>Pregnenolon
</td></tr>
<tr>
<td>Andere Namen
</td>
<td>
<p>3<i>β</i>-Hydroxypregn-5-en-20-on
</p>
</td></tr>
<tr>
<td><a href="Summenformel" title="Summenformel">Summenformel</a>
</td>
<td>C<sub>21</sub>H<sub>32</sub>O<sub>2</sub>
</td></tr>
<tr>
<td>Kurzbeschreibung
</td>
<td>
<p>farblose Nadeln<sup id="cite_ref-Römpp_1-0" class="reference"><a href="#cite_note-Römpp-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup>
</p>
</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="CAS-Nummer" title="CAS-Nummer">CAS-Nummer</a>
</td>
<td><span title="Untervorlage eingebunden: CASRN"></span><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=145-13-1">145-13-1</a><span class="editoronly" style="display:none;"></span>
</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="EG-Nummer" title="EG-Nummer">EG-Nummer</a>
</td>
<td colspan="2">205-647-4
</td></tr>
<tr>
<td><a href="Europ%C3%A4ische_Chemikalienagentur" title="Europäische Chemikalienagentur">ECHA</a>-InfoCard
</td>
<td colspan="2"><a rel="nofollow" class="external text" href="https://www.echa.europa.eu/de/substance-information/-/substanceinfo/100.005.135">100.005.135</a>
</td></tr>
<tr>
<td><a href="PubChem" title="PubChem">PubChem</a>
</td>
<td colspan="2"><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/8955">8955</a>
</td></tr>
<tr>
<td><a href="ChemSpider" title="ChemSpider">ChemSpider</a>
</td>
<td colspan="2"><a rel="nofollow" class="external text" href="https://www.chemspider.com/Chemical-Structure.8611.html">8611</a>
</td></tr>
<tr>
<td><a href="DrugBank" title="DrugBank">DrugBank</a>
</td>
<td colspan="2"><a rel="nofollow" class="external text" href="https://www.drugbank.ca/drugs/DB02789">DB02789</a>
</td></tr>
<tr>
<td style="border-right:1px solid #a2a9b1;"><a href="Wikidata" title="Wikidata">Wikidata</a>
</td>
<td colspan="2"><a href="https://www.wikidata.org/wiki/Q412158" class="extiw external" title="d:Q412158">Q412158</a>
</td></tr></tbody></table>
</td></tr>
<tr>
<th colspan="2" style="background:#FFDEAD; color:#202122;">Eigenschaften
</th></tr>
<tr>
<td><a href="Molare_Masse" title="Molare Masse">Molare Masse</a>
</td>
<td>316,48 g·mol<sup>−1</sup>
</td></tr>
<tr>
<td><a href="Aggregatzustand" title="Aggregatzustand">Aggregatzustand</a>
</td>
<td>
<p>fest
</p>
</td></tr>
<tr>
<td><a href="Schmelzpunkt" title="Schmelzpunkt">Schmelzpunkt</a>
</td>
<td>
<ul><li>185,2 °C <small>(<a href="Polymorphie_(Stoffeigenschaft)" title="Polymorphie (Stoffeigenschaft)">Polymorph</a> I)</small><sup id="cite_ref-Zhang_2-0" class="reference"><a href="#cite_note-Zhang-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup></li>
<li>192,9 °C <small>(Polymorph II)</small><sup id="cite_ref-Zhang_2-1" class="reference"><a href="#cite_note-Zhang-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup></li></ul>
</td></tr>
<tr>
<td><a href="L%C3%B6slichkeit" title="Löslichkeit">Löslichkeit</a>
</td>
<td>
<p>nahezu unlöslich in Wasser (7,06 mg·l<sup>−1</sup> bei 37 °C)<sup id="cite_ref-ChemIDplus_3-0" class="reference"><a href="#cite_note-ChemIDplus-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup>, löslich in <a href="Methanol" title="Methanol">Methanol</a>, <a href="Ethanol" title="Ethanol">Ethanol</a>, <a href="N-Propanol" class="mw-redirect" title="N-Propanol">n-Propanol</a>, <a href="I-Propanol" class="mw-redirect" title="I-Propanol">i-Propanol</a>, <a href="N-Butanol" class="mw-redirect" title="N-Butanol">n-Butanol</a>, <a href="DMF" class="mw-disambig" title="DMF">DMF</a>, <a href="NMP" class="mw-disambig" title="NMP">NMP</a>, <a href="Ethylacetat" class="mw-redirect" title="Ethylacetat">Ethylacetat</a>, <a href="Ethylformiat" class="mw-redirect" title="Ethylformiat">Ethylformiat</a>, <a href="2-Methoxyethanol" class="mw-redirect" title="2-Methoxyethanol">2-Methoxyethanol</a><sup id="cite_ref-Zhang_2-2" class="reference"><a href="#cite_note-Zhang-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup>
</p>
</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="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_4-0" class="reference"><a href="#cite_note-Sigma-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup>
<table 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>
</p>
</td></tr>
<tr>
<td rowspan="2" width="33%" style="border-top:1px #A7A7A7 dashed; border-right:1px #A7A7A7 dashed;"><a href="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;">Wenn nicht anders vermerkt, gelten die angegebenen Daten bei <a href="Standardbedingungen" title="Standardbedingungen">Standardbedingungen</a> (0 °C, 1000 hPa).
</td></tr></tbody></table><p><span class="editoronly" style="display:none;"></span>
</p><p><b>Pregnenolon</b> ist ein <a href="Derivat_(Chemie)" title="Derivat (Chemie)">Derivat</a> des <a href="Pregnan" title="Pregnan">Pregnans</a> (C<sub>21</sub>-<a href="Steroid" class="mw-redirect" title="Steroid">Steroid</a>) und wird aus <a href="Cholesterol" class="mw-redirect" title="Cholesterol">Cholesterol</a> gebildet.
</p>
<div class="mw-heading mw-heading2"><h2 id="Biosynthese">Biosynthese</h2></div>
<p>Pregnenolon wird aus Cholesterol durch <a href="Hydroxylierung" title="Hydroxylierung">Hydroxylierung</a> an C<sub>20</sub> und C<sub>22</sub> mit anschließender Abspaltung der <a href="Seitenkette" title="Seitenkette">Seitenkette</a> gebildet. Die Konversion wird durch das <a href="Enzym" title="Enzym">Enzym</a> <a href="Cholesterin-Monooxygenase" title="Cholesterin-Monooxygenase">Cholesterin-Monooxygenase</a> in den <a href="Mitochondrien" class="mw-redirect" title="Mitochondrien">Mitochondrien</a> katalysiert und durch die Hypophysenhormone <a href="Adrenocorticotropin" title="Adrenocorticotropin">ACTH</a>, <a href="Follikelstimulierendes_Hormon" title="Follikelstimulierendes Hormon">FSH</a>, <a href="Luteinisierendes_Hormon" title="Luteinisierendes Hormon">LH</a> kontrolliert.<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>
<p>Der notwendige Transport von Cholesterin vom <a href="Zytosol" class="mw-redirect" title="Zytosol">Zytosol</a> in die Mitochondrien erfolgt durch Bindung an das <a href="StAR-Protein" title="StAR-Protein">StAR-Protein</a>, ein <a href="Transportprotein" title="Transportprotein">Transportprotein</a> in der mitochondriellen Membran. Über den genauen Transport von Pregnenolon aus den Mitochondrien ist noch nichts bekannt.
</p>
<div class="mw-heading mw-heading2"><h2 id="Prohormon">Prohormon</h2></div>
<p>Pregnenolon ist ein <a href="Prohormon" title="Prohormon">Prohormon</a> der <a href="Steroidhormon" title="Steroidhormon">Steroidhormone</a> und kann enzymatisch weiter zu <a href="Progesteron" title="Progesteron">Progesteron</a> oder <a href="17%CE%B1-Hydroxypregnenolon" title="17α-Hydroxypregnenolon">17α-Hydroxypregnenolon</a> konvertiert werden.<sup id="cite_ref-6" class="reference"><a href="#cite_note-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup>
</p>
<div class="mw-heading mw-heading2"><h2 id="Verwendung_und_therapeutische_Wirksamkeit">Verwendung und therapeutische Wirksamkeit</h2></div>
<p>Pregnenolon blockiert in Tierversuchen an Mäusen und Ratten die Aktivierung des <a href="Cannabinoid-Rezeptor_1" title="Cannabinoid-Rezeptor 1">Cannabinoid-Rezeptors Typ 1</a> (CB1), der u. a. durch ∆<sup>9</sup>-<a href="Tetrahydrocannabinol" title="Tetrahydrocannabinol">Tetrahydrocannabinol</a> (THC), den <a href="Psychotrope_Substanz" title="Psychotrope Substanz">psychoaktiven</a> Hauptbestandteil von <a href="Hanf_(Art)" title="Hanf (Art)">Hanf</a> (<i>Cannabis sativa</i>), aktiviert wird. Es könnte somit als <a href="Antagonist_(Pharmakologie)" title="Antagonist (Pharmakologie)">Antagonist</a> wirken.<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-8" class="reference"><a href="#cite_note-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup>
</p>
<div class="mw-heading mw-heading2"><h2 id="Weblinks">Weblinks</h2></div>
<div class="sisterproject" style="margin:0.1em 0 0 0;"><div class="noviewer" style="display:inline-block; line-height:10px; min-width:1.6em; text-align:center;" aria-hidden="true" role="presentation"><span class="mw-default-size" typeof="mw:File"><span title="Wikibooks"></span></span></div><b><a href="https://de.wikibooks.org/wiki/Biochemie_und_Pathobiochemie:_Steroidhormon-Stoffwechsel" class="extiw external" title="b:Biochemie und Pathobiochemie: Steroidhormon-Stoffwechsel">Wikibooks: Biochemie und Pathobiochemie: Steroidhormon-Stoffwechsel</a></b> – Lern- und Lehrmaterialien</div>
<div class="mw-heading mw-heading2"><h2 id="Einzelnachweise">Einzelnachweise</h2></div>
<ol class="references">
<li id="cite_note-Römpp-1"><span class="mw-cite-backlink"><a href="#cite_ref-Römpp_1-0">↑</a></span> <span class="reference-text">Eintrag zu <a rel="nofollow" class="external text" href="https://roempp.thieme.de/lexicon/RD-16-03997"><i>Pregnenolon</i></a>. In: <i><a href="R%C3%B6mpp_Online" class="mw-redirect" title="Römpp Online">Römpp Online</a>.</i> Georg Thieme Verlag, abgerufen am 12. November 2014.<span class="editoronly" style="display:none;"></span></span>
</li>
<li id="cite_note-Zhang-2"><span class="mw-cite-backlink">↑ <sup><a href="#cite_ref-Zhang_2-0">a</a></sup> <sup><a href="#cite_ref-Zhang_2-1">b</a></sup> <sup><a href="#cite_ref-Zhang_2-2">c</a></sup></span> <span class="reference-text">Jixiu Deng; Pengshuai Zhang; Han Sun; Rongrong Wang; Binbin Wu; Yuemei Li; Beibei Feng; Haowei Sun; Shuoye Yang: <i>Insight into the solid-liquid equilibrium behavior and apparent thermodynamic analysis of polymorphic pregnenolone (Form I) in thirteen neat solvents</i> in <a href="Thermochim._Acta" class="mw-redirect" title="Thermochim. Acta">Thermochim. Acta</a> 748 (2025) 179979, <a href="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.tca.2025.179979">10.1016/j.tca.2025.179979</a></span>.</span>
</li>
<li id="cite_note-ChemIDplus-3"><span class="mw-cite-backlink"><a href="#cite_ref-ChemIDplus_3-0">↑</a></span> <span class="reference-text">Eintrag zu <span style="font-style:italic;"><a rel="nofollow" class="external text" href="https://chem.nlm.nih.gov/chemidplus/rn/145-13-1">Pregnenolone</a></span> in der <a href="ChemIDplus" title="ChemIDplus">ChemIDplus</a>-Datenbank der <a href="United_States_National_Library_of_Medicine" title="United States National Library of Medicine">United States National Library of Medicine</a> (NLM) <small>(Seite nicht mehr abrufbar<span style="display:none;" class="editoronly">, Inhalt nun verfügbar via PubChem ID <span class="wikidata-content"><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/8955">8955</a></span></span>)</small><span class="editoronly" style="display:none;"></span></span>
</li>
<li id="cite_note-Sigma-4"><span class="mw-cite-backlink"><a href="#cite_ref-Sigma_4-0">↑</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/P9129">5-Pregnen-3β-ol-20-one</a></span> bei <a href="Sigma-Aldrich" title="Sigma-Aldrich">Sigma-Aldrich</a>, abgerufen am 29. Mai 2011 (<a rel="nofollow" class="external text" href="https://www.sigmaaldrich.com/DE/de/sds/SIGMA/P9129?userType=anonymous">PDF</a>).<span class="editoronly" style="display:none;"></span></span>
</li>
<li id="cite_note-5"><span class="mw-cite-backlink"><a href="#cite_ref-5">↑</a></span> <span class="reference-text"><a rel="nofollow" class="external text" href="https://reactome.org/content/detail/R-HSA-196108">Pregnenolone biosynthesis</a> auf Reactome.Org (R-HSA-196108), abgerufen am 28. Juli 2020.</span>
</li>
<li id="cite_note-6"><span class="mw-cite-backlink"><a href="#cite_ref-6">↑</a></span> <span class="reference-text">Rassow, Hauser, Netzker, Deutzmann: <i>Biochemie</i>, 3. Auflage, Thieme-Verlagsgruppe, ISBN 978-3-13-125353-8, S. 590f</span>
</li>
<li id="cite_note-7"><span class="mw-cite-backlink"><a href="#cite_ref-7">↑</a></span> <span class="reference-text"><span class="cite"><a rel="nofollow" class="external text" href="https://www.derstandard.at/consent/tcf/1388649917020/gegenmittel-gegen-cannabis-high-entdeckt"><i>Gegenmittel gegen Cannabis-High entdeckt.</i></a> Der Standard, 3. Januar 2014,<span class="Abrufdatum"> abgerufen am 5. Januar 2014</span>.</span><span style="display: none;" class="Z3988" title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Adc&rfr_id=info%3Asid%2Fde.wikipedia.org%3APregnenolon&rft.title=Gegenmittel+gegen+Cannabis-High+entdeckt&rft.description=Gegenmittel+gegen+Cannabis-High+entdeckt&rft.identifier=https%3A%2F%2Fwww.derstandard.at%2Fconsent%2Ftcf%2F1388649917020%2Fgegenmittel-gegen-cannabis-high-entdeckt&rft.publisher=Der+Standard&rft.date=2014-01-03"> </span></span>
</li>
<li id="cite_note-8"><span class="mw-cite-backlink"><a href="#cite_ref-8">↑</a></span> <span class="reference-text">M. Vallee, S. Vitiello u. a.: <i>Pregnenolone Can Protect the Brain from Cannabis Intoxication.</i> In: <i>Science.</i> 343, 2014, S. 94–98, <a href="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/10.1126/science.1243985">10.1126/science.1243985</a></span>.</span>
</li>
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