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Cypenamine
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<h2 id="chemistry">Chemistry</h2> <h3>Stereochemistry</h3> <p>2-Phenylcyclopentan-1-amine is a compound with two <a href="/facts/Stereocenter/t3XGwk1Q">stereocenters</a>. Thus, the following two <a href="/facts/Enantiomer/wjPv5J3y">enantiomeric</a> pairs may exist: </p> <ul><li>(1<i>RS</i>,2<i>SR</i>)-<i>trans</i>-2-phenylcyclopentan-1-amine</li> <li>(1<i>RS</i>,2<i>RS</i>)-<i>cis</i>-2-phenylcyclopentan-1-amine</li></ul> <p>The <a href="/facts/Racemate/STEagtrD">racemate</a> (±)-<i>trans</i>-2-phenylcyclopentan-1-amine [1:1 mixture of (1<i>R</i>,2<i>S</i>)-<i>trans</i>-2-phenylcyclopentan-1-amine (box, left) and (1<i>S</i>,2<i>R</i>)-<i>trans</i>-2-phenylcyclopentan-1-amine (box, right)] is the active ingredient of cypenamine.<a class="footnote-ref" id="fnref:3" href="#fn:3"><sup>3</sup></a> Furthermore, the <a href="/facts/Kinetic_resolution/ac0BKEq0">kinetic resolution</a> of (±)-<i>trans</i>-2-phenylcyclopentan-1-amine by lipase B from <i>Candida antarctica</i> may be effectively performed by an aminolysis reaction.<a class="footnote-ref" id="fnref:4" href="#fn:4"><sup>4</sup></a> </p><p>Racemic <i>cis</i>-2-phenylcyclopentan-1-amine [1:1 mixture of (1<i>R</i>,2<i>R</i>)-<i>cis</i>-2-phenylcyclopentan-1-amine and (1<i>S</i>,2<i>S</i>)-<i>cis</i>-2-phenylcyclopentan-1-amine] has found no pharmacological application. </p> <h3>Homology</h3> <p>Cypenamine is a <a href="/facts/Homologous_series/7PKCuvzm">homolog</a> of <a href="/facts/Tranylcypromine/YVIArwgA">tranylcypromine</a>, containing an expanded alicyclic ring that is two <a href="/facts/Methylene_bridge/t3lvUJuT">methylene</a> units larger than the highly strained/reactive cyclopropane. The cyclohexane homologue has been reported, although the LD50s were all less than for plain amphetamine, it was still a functional stimulant. </p> <h2 id="see-also">See also</h2> <ul><li><a href="/facts/Amphetamine/yKIpLJ9E">Amphetamine</a></li> <li><a href="/facts/Cyclopentamine/4Pp1ol3C">Cyclopentamine</a></li> <li><a href="/facts/Methamphetamine/vS1jloMe">Methamphetamine</a></li> <li><a href="/facts/Propylhexedrine/uvYwz9bx">Propylhexedrine</a></li></ul> <h2 id="references">References</h2> <ol> <li id="fn:1"><p>US patent 2520516, van Zoeren GJ, "Cyclic Amines and Method of Making Them", issued 1950-08-29 <a href="https://worldwide.espacenet.com/textdoc?DB=EPODOC&IDX=US2520516" target="_blank">https://worldwide.espacenet.com/textdoc?DB=EPODOC&IDX=US2520516</a> <a href="#fnref:1" class="footnote-back-ref">↩</a></p></li> <li id="fn:2"><p>Elks J (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 966–. ISBN 978-1-4757-2085-3. <a href="978-1-4757-2085-3" target="_blank">978-1-4757-2085-3</a> <a href="#fnref:2" class="footnote-back-ref">↩</a></p></li> <li id="fn:3"><p>González-Sabín J, Gotor V, Rebolledo F (2004). "Kinetic resolution of (±)-trans- und (±)-cis-phenylcyclopentanamine by CALB-catalyzed aminolysis of esters: The key role of the leaving group". Tetrahedron:Asymmetry. 15 (3): 481–488. doi:10.1016/j.tetasy.2003.11.013. <a href="/wiki/Doi_(identifier)" target="_blank">/wiki/Doi_(identifier)</a> <a href="#fnref:3" class="footnote-back-ref">↩</a></p></li> <li id="fn:4"><p>González-Sabín J, Gotor V, Rebolledo F (2004). "Kinetic resolution of (±)-trans- und (±)-cis-phenylcyclopentanamine by CALB-catalyzed aminolysis of esters: The key role of the leaving group". Tetrahedron:Asymmetry. 15 (3): 481–488. doi:10.1016/j.tetasy.2003.11.013. <a href="/wiki/Doi_(identifier)" target="_blank">/wiki/Doi_(identifier)</a> <a href="#fnref:4" class="footnote-back-ref">↩</a></p></li> </ol>