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Details

Stereochemistry RACEMIC
Molecular Formula C9H19N
Molecular Weight 141.2539
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CYCLOPENTAMINE

SMILES

CNC(C)CC1CCCC1

InChI

InChIKey=HFXKQSZZZPGLKQ-UHFFFAOYSA-N
InChI=1S/C9H19N/c1-8(10-2)7-9-5-3-4-6-9/h8-10H,3-7H2,1-2H3

HIDE SMILES / InChI

Molecular Formula C9H19N
Molecular Weight 141.2539
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Description

Cyclopentamine is a sympathomimetic alkylamine, classified as a vasoconstrictor. Cyclopentamine was indicated in the past as an over-the-counter 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 used for relief of congestion due to colds, common cold, hay fever, or other allergies. Cyclopentamine acts as a releasing agent of the catecholamine neurotransmitters norepinephrine (noradrenaline), epinephrine (adrenaline), and dopamine. Cyclopentamine effects on norepinephrine and epinephrine mediate its decongestant effects, while its effects on all three neurotransmitters are responsible for its stimulant properties. Cyclopentamine was acting as nonspecific spasmolytic, similar to papaverine, in the rabbit ileum. It was demonstrated that cyclopentamine was a very weak alpha-adrenergic receptor stimulant and a weak beta-adrenergic receptor blocker. Cyclopentamine also potentiated the auto-inhibition produced by high doses of isoproterenol and the effect lasted as long as the autoinhibition persisted. It was suggested that the blockade by both drugs was the result of a direct action on the beta receptors. When ingested orally in sufficient quantities, cyclopentamine produces similar effects to amphetamine, methamphetamine, and propylhexedrine.

CNS Activity

Originator

Approval Year

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
Unknown
Palliative
Clopane

PubMed

Patents

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
In Vitro Use Guide
Unknown
Substance Class Chemical
Record UNII
WB9Q6M8O60
Record Status Validated (UNII)
Record Version