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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2015/07/31 14:45:43」(JST)
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| Systematic (IUPAC) name | |
|---|---|
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(RS)-1-cyclopentyl-N-methyl-propan-2-amine
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| Clinical data | |
| Legal status |
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| Routes of administration |
Inhalation |
| Identifiers | |
| CAS Registry Number | 102-45-4 Y |
| ATC code | R01AA02 |
| PubChem | CID: 7608 |
| DrugBank | DB08999 N |
| ChemSpider | 7326 Y |
| UNII | WB9Q6M8O60 Y |
| KEGG | D07370 Y |
| ChEMBL | CHEMBL329203 Y |
| Synonyms | N,α-dimethyl-cyclopenaneethylamine |
| Chemical data | |
| Formula | C9H19N |
| Molecular mass | 141.254 |
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SMILES
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InChI
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| Physical data | |
| Boiling point | 171 °C (340 °F) |
| N (what is this?) (verify) | |
Cyclopentamine (Clopane, Cyclonarol, Cyclosal, Cyklosan, Nazett, Sinos) is a sympathomimetic alkylamine, classified as a vasoconstrictor. Cyclopentamine was indicated in the past as an over-the-counter (OTC) 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.[citation needed]
Contents
- 1 Pharmacology
- 2 Chemistry
- 3 See also
- 4 References
Pharmacology
Cyclopentamine acts as a releasing agent of the catecholamine neurotransmitters norepinephrine (noradrenaline), epinephrine (adrenaline), and dopamine.[1] Its effects on norepinephrine and epinephrine mediate its decongestant effects, while its effects on all three neurotransmitters are responsible for its stimulant properties. When ingested orally in sufficient quantities, cyclopentamine produces similar effects to amphetamine, methamphetamine, and propylhexedrine.[2][3]
Chemistry
Cyclopentamine is the cyclopentane homolog of propylhexedrine, differing only in terms of the contracted ring size of a cyclopentane, containing one -CH2- unit less than the cyclohexyl group.
In terms of the acyclic part of the molecule, both cyclopentamine and propylhexedrine are the same as methamphetamine, all three molecules containing the 2-methylaminopropyl side-chain. The difference between them is that whereas methamphetamine is an aromatic molecule containing a phenyl group, cyclopentamine and propylhexedrine are entirely aliphatic and contain no delocalized electrons at all. The effect that this has on potency is that the reduced alicyclic-alkylamines are weaker than unsaturated (meth)amphetamine.[citation needed]
See also
- Amphetamine
- Cypenamine (which is trans-2-phenylcyclopentylamine)
- Methamphetamine
- Propylhexedrine (also known as cyclohexamine)
- Tranylcypromine (which is trans-2-phenylcyclopropylamine)
- Methiopropamine
References
- ^ Schmidt JL, Fleming WW (July 1964). "A Nonsympathomimetic Effect of Cyclopentamine and Beta-Mercaptoethylamine in the Rabbit Ileum.". The Journal of Pharmacology and Experimental Therapeutics 145: 83–6. PMID 14209515.
- ^ Ghouri MS, Haley TJ (July 1969). "In vitro evaluation of a series of sympathomimetic amines and the beta-adrenergic blocking properties of cyclopentamine". Journal of Pharmaceutical Sciences 58 (7): 882–4. doi:10.1002/jps.2600580722. PMID 4390216.
- ^ Marley E, Stephenson JD (August 1971). "Actions of dexamphetamine and amphetamine-like amines in chickens with brain transections.". British Journal of Pharmacology 42 (4): 522–42. doi:10.1111/j.1476-5381.1971.tb07138.x. PMC 1665761. PMID 5116035.
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English Journal
- Simultaneous semiautomated assay of pyrrobutamine phosphate, cyclopentamine hydrochloride, and methapyrilene hydrochloride in pharmaceutical mixtures.
- Hale JL.
- Journal of pharmaceutical sciences.J Pharm Sci.1976 Nov;65(11):1590-2.
- Antihistamine preparations containing methapyrilene hydrochloride, pyrrobutamine phosphate, and cyclopentamine hydrochloride were assayed by introducing an aqueous sample solution into the appropriate automated system. Methapyrilene hydrochloride was determined by UV spectrophotometry. Pyrrobutamine
- PMID 11331
- Actions of dexamphetamine and amphetamine-like amines in chickens with brain transections.
- Marley E, Stephenson JD.
- British journal of pharmacology.Br J Pharmacol.1971 Aug;42(4):522-42.
- 1. A method for preparing the encéphale isolé preparation in young fowls is described. Certain important differences were found between electrocortical activity of chicken and mammalian encéphale isolé preparations. Electrocortical effects of excitant sympathomimetic amines and their antagonism
- PMID 5116035
- In vitro evaluation of a series of sympathomimetic amines and the beta-adrenergic blocking properties of cyclopentamine.
- Ghouri MS, Haley TJ.
- Journal of pharmaceutical sciences.J Pharm Sci.1969 Jul;58(7):882-4.
- PMID 4390216
Related Links
- Cyclopentamine (Clopane, Cyclonarol, Cyclosal, Cyklosan, Nazett, Sinos) is a sympathomimetic alkylamine, classified as a vasoconstrictor. Cyclopentamine was indicated in the past as an over-the-counter (OTC) medication for use as a nasal ...
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