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
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 | ( + / - ) |
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 |
---|---|---|---|---|
Sources: https://www.drugbank.ca/drugs/DB08999 |
Palliative | Unknown Approved UseUnknown |
||
Sources: https://www.drugbank.ca/drugs/DB08999 |
Palliative | Clopane Approved UseAdrenergic (vasoconstrictor); nasal decongestant. Launch Date1950 |
PubMed
Title | Date | PubMed |
---|---|---|
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 |
Patents
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 15:18:25 GMT 2023
by
admin
on
Fri Dec 15 15:18:25 GMT 2023
|
Record UNII |
WB9Q6M8O60
|
Record Status |
Validated (UNII)
|
Record Version |
|
-
Download
Name | Type | Language | ||
---|---|---|---|---|
|
Official Name | English | ||
|
Common Name | English | ||
|
Brand Name | English | ||
|
Systematic Name | English | ||
|
Brand Name | English | ||
|
Brand Name | English | ||
|
Brand Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English |
Classification Tree | Code System | Code | ||
---|---|---|---|---|
|
WHO-VATC |
QR01AA02
Created by
admin on Fri Dec 15 15:18:25 GMT 2023 , Edited by admin on Fri Dec 15 15:18:25 GMT 2023
|
||
|
NCI_THESAURUS |
C29747
Created by
admin on Fri Dec 15 15:18:25 GMT 2023 , Edited by admin on Fri Dec 15 15:18:25 GMT 2023
|
||
|
WHO-ATC |
R01AA02
Created by
admin on Fri Dec 15 15:18:25 GMT 2023 , Edited by admin on Fri Dec 15 15:18:25 GMT 2023
|
Code System | Code | Type | Description | ||
---|---|---|---|---|---|
|
135
Created by
admin on Fri Dec 15 15:18:25 GMT 2023 , Edited by admin on Fri Dec 15 15:18:25 GMT 2023
|
PRIMARY | |||
|
100000083773
Created by
admin on Fri Dec 15 15:18:25 GMT 2023 , Edited by admin on Fri Dec 15 15:18:25 GMT 2023
|
PRIMARY | |||
|
C81341
Created by
admin on Fri Dec 15 15:18:25 GMT 2023 , Edited by admin on Fri Dec 15 15:18:25 GMT 2023
|
PRIMARY | |||
|
DB08999
Created by
admin on Fri Dec 15 15:18:25 GMT 2023 , Edited by admin on Fri Dec 15 15:18:25 GMT 2023
|
PRIMARY | |||
|
WB9Q6M8O60
Created by
admin on Fri Dec 15 15:18:25 GMT 2023 , Edited by admin on Fri Dec 15 15:18:25 GMT 2023
|
PRIMARY | |||
|
SUB06856MIG
Created by
admin on Fri Dec 15 15:18:25 GMT 2023 , Edited by admin on Fri Dec 15 15:18:25 GMT 2023
|
PRIMARY | |||
|
102-45-4
Created by
admin on Fri Dec 15 15:18:25 GMT 2023 , Edited by admin on Fri Dec 15 15:18:25 GMT 2023
|
PRIMARY | |||
|
CYCLOPENTAMINE
Created by
admin on Fri Dec 15 15:18:25 GMT 2023 , Edited by admin on Fri Dec 15 15:18:25 GMT 2023
|
PRIMARY | |||
|
DTXSID60861710
Created by
admin on Fri Dec 15 15:18:25 GMT 2023 , Edited by admin on Fri Dec 15 15:18:25 GMT 2023
|
PRIMARY | |||
|
755
Created by
admin on Fri Dec 15 15:18:25 GMT 2023 , Edited by admin on Fri Dec 15 15:18:25 GMT 2023
|
PRIMARY | |||
|
CHEMBL329203
Created by
admin on Fri Dec 15 15:18:25 GMT 2023 , Edited by admin on Fri Dec 15 15:18:25 GMT 2023
|
PRIMARY | |||
|
m4005
Created by
admin on Fri Dec 15 15:18:25 GMT 2023 , Edited by admin on Fri Dec 15 15:18:25 GMT 2023
|
PRIMARY | Merck Index | ||
|
59094
Created by
admin on Fri Dec 15 15:18:25 GMT 2023 , Edited by admin on Fri Dec 15 15:18:25 GMT 2023
|
PRIMARY | RxNorm | ||
|
7608
Created by
admin on Fri Dec 15 15:18:25 GMT 2023 , Edited by admin on Fri Dec 15 15:18:25 GMT 2023
|
PRIMARY |
Related Record | Type | Details | ||
---|---|---|---|---|
|
SALT/SOLVATE -> PARENT |
Related Record | Type | Details | ||
---|---|---|---|---|
|
ACTIVE MOIETY |