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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
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

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

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

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
Unknown

Approved Use

Unknown
Palliative
Clopane

Approved Use

Adrenergic (vasoconstrictor); nasal decongestant.

Launch Date

1950
PubMed

PubMed

TitleDatePubMed
Clinical observations with clopane in asthma, hay fever and allergic rhinitis.
1951 Mar-Apr
COUNCIL on Pharmacy and Chemistry: cyclopentamine hydrochloride.
1951 Sep 8
Clinical experiences with clopane hydrochloride; a preliminary report.
1953 Jan-Feb
[The vasoconstrictor action of the nasal mucosa of cyclopentamine, phenylephrine, Otrivin and Rineptyl. Rhinomanometric observations].
1960 Nov-Dec
A NONSYMPATHOMIMETIC EFFECT OF CYCLOPENTAMINE AND BETA-MERCAPTOETHYLAMINE IN THE RABBIT ILEUM.
1964 Jul
In vitro evaluation of a series of sympathomimetic amines and the beta-adrenergic blocking properties of cyclopentamine.
1969 Jul
Actions of dexamphetamine and amphetamine-like amines in chickens with brain transections.
1971 Aug
Simultaneous semiautomated assay of pyrrobutamine phosphate, cyclopentamine hydrochloride, and methapyrilene hydrochloride in pharmaceutical mixtures.
1976 Nov
Patents

Patents

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
In Vitro Use Guide
Unknown
Name Type Language
CYCLOPENTAMINE
INN   MI   WHO-DD  
INN  
Official Name English
cyclopentamine [INN]
Common Name English
CYKLOSAL
Brand Name English
N,.ALPHA.-DIMETHYLCYCLOPENTANEETHYLAMINE
Systematic Name English
CLOPANE
Brand Name English
CYCLONAROL
Brand Name English
SINOS
Brand Name English
CYCLOPENTANEETHANAMINE, N-.ALPHA.-DIMETHYL-
Common Name English
(±)-CYCLOPENTAMINE
Common Name English
Cyclopentamine [WHO-DD]
Common Name English
CYCLOPENTAMINE [MI]
Common Name English
Classification Tree Code System Code
WHO-VATC QR01AA02
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NCI_THESAURUS C29747
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WHO-ATC R01AA02
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Code System Code Type Description
INN
135
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SMS_ID
100000083773
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NCI_THESAURUS
C81341
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DRUG BANK
DB08999
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FDA UNII
WB9Q6M8O60
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EVMPD
SUB06856MIG
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CAS
102-45-4
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WIKIPEDIA
CYCLOPENTAMINE
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EPA CompTox
DTXSID60861710
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DRUG CENTRAL
755
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ChEMBL
CHEMBL329203
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MERCK INDEX
m4005
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PRIMARY Merck Index
RXCUI
59094
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PRIMARY RxNorm
PUBCHEM
7608
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