Cyclopentamine

Cyclopentamine

Clinical data
Routes of administration	Topical (nasal spray)
ATC code	R01AA02 (WHO)
Legal status
Legal status	Uncontrolled
Identifiers
IUPAC name (RS)-1-Cyclopentyl-N-methylpropan-2-amine
Synonyms	N,α-dimethyl-cyclopenaneethylamine
CAS Number	102-45-4 Y
PubChem CID	7608
DrugBank	DB08999 N
ChemSpider	7326 Y
UNII	WB9Q6M8O60
KEGG	D07370 Y
ChEMBL	CHEMBL329203 Y
Chemical and physical data
Formula	C9H19N
Molar mass	141.254
3D model (Jmol)	Interactive image
Chirality	Racemic mixture
Boiling point	171 °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?)

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 possibly due to the availability, effectiveness, and safety of a structurally similar drug, propylhexedrine.

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.

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.