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
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
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/5116035
Curator's Comment: Known to be CNS penetrant in chicken. Human data not available. Cyclopentamine evoked electrocortical desynchronization in chick encéphale isolé preparations, confirming the central origin of these effects. Behavioural changes were also observed.
Originator
Sources: https://www.google.com/patents/US2520015 | http://www.trademarkia.com/clopane-71582088.html
Curator's Comment: Cyclopentamine was registered by Eli Lilly under the trade name Clopane in 12/5/1950 # Rohrmann Ewald, Eli Lilly
Approval Year
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Sources: https://www.drugbank.ca/drugs/DB08999 |
Palliative | Unknown Approved UseUnknown |
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Sources: https://www.drugbank.ca/drugs/DB08999 |
Palliative | Clopane Approved UseAdrenergic (vasoconstrictor); nasal decongestant. Launch Date1950 |
PubMed
Title | Date | PubMed |
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Clinical observations with clopane in asthma, hay fever and allergic rhinitis. | 1951 Mar-Apr |
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COUNCIL on Pharmacy and Chemistry: cyclopentamine hydrochloride. | 1951 Sep 8 |
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Clinical experiences with clopane hydrochloride; a preliminary report. | 1953 Jan-Feb |
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[The vasoconstrictor action of the nasal mucosa of cyclopentamine, phenylephrine, Otrivin and Rineptyl. Rhinomanometric observations]. | 1960 Nov-Dec |
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A NONSYMPATHOMIMETIC EFFECT OF CYCLOPENTAMINE AND BETA-MERCAPTOETHYLAMINE IN THE RABBIT ILEUM. | 1964 Jul |
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In vitro evaluation of a series of sympathomimetic amines and the beta-adrenergic blocking properties of cyclopentamine. | 1969 Jul |
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Actions of dexamphetamine and amphetamine-like amines in chickens with brain transections. | 1971 Aug |
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Simultaneous semiautomated assay of pyrrobutamine phosphate, cyclopentamine hydrochloride, and methapyrilene hydrochloride in pharmaceutical mixtures. | 1976 Nov |
Patents
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Classification Tree | Code System | Code | ||
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WHO-VATC |
QR01AA02
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NCI_THESAURUS |
C29747
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WHO-ATC |
R01AA02
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135
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100000083773
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C81341
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DB08999
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WB9Q6M8O60
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SUB06856MIG
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102-45-4
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CYCLOPENTAMINE
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DTXSID60861710
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755
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CHEMBL329203
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m4005
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59094
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7608
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ACTIVE MOIETY
SALT/SOLVATE (PARENT)