U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry RACEMIC
Molecular Formula C9H19N.ClH
Molecular Weight 177.715
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CYCLOPENTAMINE HYDROCHLORIDE

SMILES

Cl.CNC(C)CC1CCCC1

InChI

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

HIDE SMILES / InChI

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

Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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
Substance Class Chemical
Created
by admin
on Fri Dec 15 16:36:28 GMT 2023
Edited
by admin
on Fri Dec 15 16:36:28 GMT 2023
Record UNII
F551446KF3
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CYCLOPENTAMINE HYDROCHLORIDE
MART.   MI   WHO-DD  
Common Name English
CYCLOPENTANEETHANAMINE, N,.ALPHA.-DIMETHYL-, HYDROCHLORIDE (1:1)
Systematic Name English
Cyclopentamine hydrochloride [WHO-DD]
Common Name English
CYCLOPENTAMINE HYDROCHLORIDE [MI]
Common Name English
N,α-Dimethylcyclopentaneethylamine hydrochloride
Systematic Name English
CYCLOPENTANEETHANAMINE, N-.ALPHA.-DIMETHYL-, HYDROCHLORIDE
Common Name English
CYCLOPENTAMINE HYDROCHLORIDE [MART.]
Common Name English
CYCLOPENTAMINE HCL
Common Name English
(±)-CYCLOPENTAMINE HYDROCHLORIDE
Common Name English
CLOPANE HYDROCHLORIDE
Brand Name English
Classification Tree Code System Code
NCI_THESAURUS C29747
Created by admin on Fri Dec 15 16:36:28 GMT 2023 , Edited by admin on Fri Dec 15 16:36:28 GMT 2023
Code System Code Type Description
FDA UNII
F551446KF3
Created by admin on Fri Dec 15 16:36:28 GMT 2023 , Edited by admin on Fri Dec 15 16:36:28 GMT 2023
PRIMARY
CAS
538-02-3
Created by admin on Fri Dec 15 16:36:28 GMT 2023 , Edited by admin on Fri Dec 15 16:36:28 GMT 2023
PRIMARY
RXCUI
1300303
Created by admin on Fri Dec 15 16:36:28 GMT 2023 , Edited by admin on Fri Dec 15 16:36:28 GMT 2023
PRIMARY
EVMPD
SUB01528MIG
Created by admin on Fri Dec 15 16:36:28 GMT 2023 , Edited by admin on Fri Dec 15 16:36:28 GMT 2023
PRIMARY
EPA CompTox
DTXSID00923189
Created by admin on Fri Dec 15 16:36:28 GMT 2023 , Edited by admin on Fri Dec 15 16:36:28 GMT 2023
PRIMARY
SMS_ID
100000084694
Created by admin on Fri Dec 15 16:36:28 GMT 2023 , Edited by admin on Fri Dec 15 16:36:28 GMT 2023
PRIMARY
DRUG BANK
DBSALT002451
Created by admin on Fri Dec 15 16:36:28 GMT 2023 , Edited by admin on Fri Dec 15 16:36:28 GMT 2023
PRIMARY
NCI_THESAURUS
C75030
Created by admin on Fri Dec 15 16:36:28 GMT 2023 , Edited by admin on Fri Dec 15 16:36:28 GMT 2023
PRIMARY
PUBCHEM
92798
Created by admin on Fri Dec 15 16:36:28 GMT 2023 , Edited by admin on Fri Dec 15 16:36:28 GMT 2023
PRIMARY
CAS
3459-06-1
Created by admin on Fri Dec 15 16:36:28 GMT 2023 , Edited by admin on Fri Dec 15 16:36:28 GMT 2023
SUPERSEDED
ECHA (EC/EINECS)
208-681-8
Created by admin on Fri Dec 15 16:36:28 GMT 2023 , Edited by admin on Fri Dec 15 16:36:28 GMT 2023
PRIMARY
MERCK INDEX
m4005
Created by admin on Fri Dec 15 16:36:28 GMT 2023 , Edited by admin on Fri Dec 15 16:36:28 GMT 2023
PRIMARY Merck Index
ChEMBL
CHEMBL329203
Created by admin on Fri Dec 15 16:36:28 GMT 2023 , Edited by admin on Fri Dec 15 16:36:28 GMT 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY