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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
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

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
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 15:18:25 GMT 2023
Edited
by admin
on Fri Dec 15 15:18:25 GMT 2023
Record UNII
WB9Q6M8O60
Record Status Validated (UNII)
Record Version
  • Download
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
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
INN
135
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SMS_ID
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
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NCI_THESAURUS
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
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DRUG BANK
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
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FDA UNII
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
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EVMPD
SUB06856MIG
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CAS
102-45-4
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WIKIPEDIA
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
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EPA CompTox
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
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DRUG CENTRAL
755
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ChEMBL
CHEMBL329203
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MERCK INDEX
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
RXCUI
59094
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PRIMARY RxNorm
PUBCHEM
7608
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