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| Other names | 2-Phenylcyclopentanamine |
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| Formula | C11H15N |
| Molar mass | 161.248 g·mol−1 |
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| Chirality | Racemic mixture |
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Cypenamine (INN,BAN), orcypenamine hydrochloride (USAN), also known as2-phenylcyclopentylamine, is apsychostimulantdrug which was developed by a group at theWilliam S. Merrell Chemical Company in the 1940s.[1][2] It is currently known only inscientific research and has never beendeveloped formarketuse. Cypenamine is currentlylegal throughout the entireworld, and though itschemical structure has a vague similarity to certaincontrolled stimulants likefencamfamine, it is likely that it is too distant for it to be considered anillicitanalogue under theUnited StatesFederal Analogue Act of theControlled Substances Act.
2-Phenylcyclopentan-1-amine is a compound with twostereocenters. Thus, the following twoenantiomeric pairs may exist:
Theracemate (±)-trans-2-phenylcyclopentan-1-amine [1:1 mixture of (1R,2S)-trans-2-phenylcyclopentan-1-amine (box, left) and (1S,2R)-trans-2-phenylcyclopentan-1-amine (box, right)] is the active ingredient of cypenamine.[3] Furthermore, thekinetic resolution of (±)-trans-2-phenylcyclopentan-1-amine by lipase B fromCandida antarctica may be effectively performed by an aminolysis reaction.[3]
Racemiccis-2-phenylcyclopentan-1-amine [1:1 mixture of (1R,2R)-cis-2-phenylcyclopentan-1-amine and (1S,2S)-cis-2-phenylcyclopentan-1-amine] has found no pharmacological application.[citation needed]
Cypenamine is ahomolog oftranylcypromine, containing an expanded alicyclic ring that is twomethylene 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.[citation needed]
