Frequent Links
Mumps Infections Top Journalsonline physiology information journalsOpen Access Journals on ProteinsStem cell transplantation top journalshuman factors open accessVaccines Peer Review JournalsAnesthesia Open Access JournalsSedimentologyopen access articles on alkaloidsaromatic plants articles open accesspollution-effects-articlesIschemic stroke Peer-review Journals Sensor networksLivestock Journals Listautomobile engineering in industries
Cypenamine
| File:Trans-(±)-Cypenamine Enantiomers Structural Formulae.png | |
| Systematic (IUPAC) name | |
|---|---|
| (±)-trans-2-phenylcyclopentan-1-amine | |
| Clinical data | |
| Identifiers | |
| 15301-54-9 7px | |
| None | |
| PubChem | CID 21786 |
| ChemSpider | 20476 7px |
| UNII | VP9115827H 7px |
| ChEMBL | CHEMBL2110918 |
| Chemical data | |
| Formula | C11H15N |
| 161.2435 g/mol | |
| |
| 14px (what is this?) (verify) | |
-Cypenamine_Enantiomers_Structural_Formulae.png){kind=link}
Cypenamine, or phenylcyclopentamine, is a stimulant drug developed by a team at the William S. Merrill company in the 1940s.[1] 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 (Glucoenergan, Reactivan), it is likely that it is too distant for it to be considered an illicit analogue under the United States (U.S.) Federal Analogue Act (FAA) of the Controlled Substances Act (CSA).
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.[2] Furthermore, the kinetic resolution of (±)-trans-2-phenylcyclopentan-1-amine by lipase B from Candida antarctica may effectivily performed by an aminolysis reaction.[2]
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
- ^ US patent 2520516, van Zoeren, G. J., "Cyclic Amines and Method of Making Them", issued 1950-08-29
- ^ 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.
| ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||