Cyclopentamine

Cyclopentamine (trade names Clopane, Cyclonarol, Cyclosal, Cyklosan, Nazett, Sinos, among others) is a sympathomimetic alkylamine, classified as a vasoconstrictor. Cyclopentamine was indicated in the past as an over-the-counter (OTC) medication for use as a nasal decongestant, notably in Europe and Australia, but has now been largely discontinued.

Cyclopentamine
Clinical data
Other namesN,α-dimethyl-cyclopenaneethylamine
Routes of
administration		Topical (nasal spray)
ATC code
Legal status
Legal status
  • In general: uncontrolled
Identifiers
IUPAC name
  • (RS)-1-Cyclopentyl-N-methylpropan-2-amine
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
Chemical and physical data
FormulaC9H19N
Molar mass141.258 g·mol−1
3D model (JSmol)
ChiralityRacemic mixture
Boiling point171 °C (340 °F)
SMILES
  • N(C)C(CC1CCCC1)C
InChI
  • InChI=1S/C9H19N/c1-8(10-2)7-9-5-3-4-6-9/h8-10H,3-7H2,1-2H3 Y
  • Key:HFXKQSZZZPGLKQ-UHFFFAOYSA-N Y
 NY (what is this?)  (verify)

Pharmacology

Cyclopentamine acts as a releasing agent of the catecholamine neurotransmitters norepinephrine (noradrenaline), epinephrine (adrenaline), and dopamine.[1] Its effects on norepinephrine and epinephrine mediate its decongestant effects, while its effects on all three neurotransmitters are responsible for its stimulant properties. When ingested orally in sufficient quantities, cyclopentamine produces similar effects to amphetamine, methamphetamine, and propylhexedrine.[2][3]

Chemistry

Cyclopentamine is the cyclopentane homolog of propylhexedrine, differing only in terms of the contracted ring size of a cyclopentane, containing one —CH2— unit less than the cyclohexyl group.

In terms of the acyclic part of the molecule, both cyclopentamine and propylhexedrine are the same as methamphetamine, all three molecules containing the 2-methylaminopropyl side-chain. The difference between them is that whereas methamphetamine is an aromatic molecule containing a phenyl group, cyclopentamine and propylhexedrine are entirely aliphatic and contain no delocalized electrons at all. The effect that this has on potency is that the reduced alicyclic-alkylamines are weaker than unsaturated (meth)amphetamine.

See also

References
  1. Schmidt JL, Fleming WW (July 1964). "A Nonsympathomimetic Effect of Cyclopentamine and Beta-Mercaptoethylamine in the Rabbit Ileum". The Journal of Pharmacology and Experimental Therapeutics. 145: 83–6. PMID 14209515.
  2. Ghouri MS, Haley TJ (July 1969). "In vitro evaluation of a series of sympathomimetic amines and the beta-adrenergic blocking properties of cyclopentamine". Journal of Pharmaceutical Sciences. 58 (7): 882–4. doi:10.1002/jps.2600580722. PMID 4390216.
  3. Marley E, Stephenson JD (August 1971). "Actions of dexamphetamine and amphetamine-like amines in chickens with brain transections". British Journal of Pharmacology. 42 (4): 522–42. doi:10.1111/j.1476-5381.1971.tb07138.x. PMC 1665761. PMID 5116035.
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