Cyclopentamine

Cyclopentamine

260px
Systematic (IUPAC) name
(RS)-1-cyclopentyl-N-methyl-propan-2-amine
Clinical data
Legal status	Uncontrolled
Routes of administration	Inhalation
Identifiers
CAS Number	102-45-4 Y
ATC code	R01AA02 (WHO)
PubChem	CID: 7608
DrugBank	DB08999 N
ChemSpider	7326 Y
UNII	WB9Q6M8O60 Y
KEGG	D07370 Y
ChEMBL	CHEMBL329203 Y
Synonyms	N,α-dimethyl-cyclopenaneethylamine
Chemical data
Formula	C9H19N
Molecular mass	141.254
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
Physical data
Boiling point	171 °C (340 °F)
NY (what is this?)  (verify)

Cyclopentamine (Clopane, Cyclonarol, Cyclosal, Cyklosan, Nazett, Sinos) 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 possibly due to the availability, effectiveness, and safety of a structurally similar drug, propylhexedrine.

Pharmacology

Cyclopentamine acts as a releasing agent of the catecholamine neurotransmitters norepinephrine (noradrenaline), epinephrine (adrenaline), and dopamine. 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.

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

• Amphetamine
• Cypenamine (which is trans-2-phenylcyclopentylamine)
• Methamphetamine
• Propylhexedrine (also known as cyclohexamine)
• Tranylcypromine (which is trans-2-phenylcyclopropylamine)
• Methiopropamine