Cypenamine

Chemical compound
  • none
Identifiers
  • (±)-trans-2-phenylcyclopentan-1-amine
CAS Number
  • 15301-54-9 checkY
PubChem CID
  • 21786
ChemSpider
  • 20476 checkY
UNII
  • VP9115827H
ChEMBL
  • ChEMBL2110918
CompTox Dashboard (EPA)
  • DTXSID40546452 Edit this at Wikidata
Chemical and physical dataFormulaC11H15NMolar mass161.248 g·mol−13D model (JSmol)
  • Interactive image
ChiralityRacemic mixture
  • N[C@H]1CCC[C@@H]1C2=CC=CC=C2
InChI
  • InChI=1S/C11H15N/c12-11-8-4-7-10(11)9-5-2-1-3-6-9/h1-3,5-6,10-11H,4,7-8,12H2 checkY
  • Key:VNGYTYNUZHDMPP-UHFFFAOYSA-N checkY
  (verify)

Cypenamine (INN, BAN), or cypenamine hydrochloride (USAN), also known as 2-phenylcyclopentylamine, is a psychostimulant drug which was developed by a group at the William S. Merrell Chemical Company in the 1940s.[1][2] It is currently known only in scientific research and has never been developed for market use. Cypenamine is currently legal throughout the entire world, and though its chemical structure has a vague similarity to certain controlled stimulants like fencamfamine, it is likely that it is too distant for it to be considered an illicit analogue under the United States Federal Analogue Act of the Controlled Substances Act.

Chemistry

Stereochemistry

2-Phenylcyclopentan-1-amine is a compound with two stereocenters. Thus, the following two enantiomeric pairs may exist:

  • (1RS,2SR)-trans-2-phenylcyclopentan-1-amine
  • (1RS,2RS)-cis-2-phenylcyclopentan-1-amine

The racemate (±)-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, the kinetic resolution of (±)-trans-2-phenylcyclopentan-1-amine by lipase B from Candida antarctica may be effectively performed by an aminolysis reaction.[3]

Racemic cis-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]

Homology

Cypenamine is a homolog of tranylcypromine, containing an expanded alicyclic ring that is two methylene 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]

See also

References

  1. ^ US patent 2520516, van Zoeren GJ, "Cyclic Amines and Method of Making Them", issued 1950-08-29 
  2. ^ 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.
  3. ^ a b 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.
  • v
  • t
  • e
AdamantanesAdenosine antagonistsAlkylaminesAmpakinesArylcyclohexylaminesBenzazepinesCathinonesCholinergicsConvulsantsEugeroicsOxazolinesPhenethylamines
PhenylmorpholinesPiperazinesPiperidinesPyrrolidinesRacetamsTropanesTryptaminesOthers
  • v
  • t
  • e
DRAsTooltip Dopamine releasing agents
NRAsTooltip Norepinephrine releasing agents
SRAsTooltip Serotonin releasing agents
Others
See also: Receptor/signaling modulators • Monoamine reuptake inhibitors • Adrenergics • Dopaminergics • Serotonergics • Monoamine metabolism modulators • Monoamine neurotoxins