Cyclopentamine (trade names Clopane, Cyclonarol, Cyclosal, Cyklosan, Nazett, Sinos, among others) is a

sympathomimetic Sympathomimetic drugs (also known as adrenergic drugs and adrenergic amines) are stimulant compounds which mimic the effects of endogenous agonists of the sympathetic nervous system. Examples of sympathomimetic effects include increases in hea ...

alkylamine, classified as a vasoconstrictor. Cyclopentamine was

indicated In medicine, an indication is a valid reason to use a certain test, medication, procedure, or surgery. There can be multiple indications to use a procedure or medication. An indication can commonly be confused with the term diagnosis. A diagnosis ...

in the past as an over-the-counter (OTC) medication for use as a

nasal Nasal is an adjective referring to the nose, part of human or animal anatomy. It may also be shorthand for the following uses in combination: * With reference to the human nose: ** Nasal administration, a method of pharmaceutical drug delivery ** ...

decongestant, notably in Europe and

Australia Australia, officially the Commonwealth of Australia, is a Sovereign state, sovereign country comprising the mainland of the Australia (continent), Australian continent, the island of Tasmania, and numerous List of islands of Australia, sma ...

, but has now been largely discontinued.

Pharmacology

Cyclopentamine acts as a releasing agent of the catecholamine

neurotransmitter A neurotransmitter is a signaling molecule secreted by a neuron to affect another cell across a synapse. The cell receiving the signal, any main body part or target cell, may be another neuron, but could also be a gland or muscle cell. Neuro ...

s norepinephrine (noradrenaline),

epinephrine Adrenaline, also known as epinephrine, is a hormone and medication which is involved in regulating visceral functions (e.g., respiration). It appears as a white microcrystalline granule. Adrenaline is normally produced by the adrenal glands and ...

(adrenaline), and

dopamine Dopamine (DA, a contraction of 3,4-dihydroxyphenethylamine) is a neuromodulatory molecule that plays several important roles in cells. It is an organic compound, organic chemical of the catecholamine and phenethylamine families. Dopamine const ...

. 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 Amphetamine (contracted from alpha- methylphenethylamine) is a strong central nervous system (CNS) stimulant that is used in the treatment of attention deficit hyperactivity disorder (ADHD), narcolepsy, and obesity. It is also commonly used ...

, methamphetamine, and propylhexedrine.

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 Methamphetamine (contracted from ) is a potent central nervous system (CNS) stimulant that is mainly used as a recreational drug and less commonly as a second-line treatment for attention deficit hyperactivity disorder and obesity. Methamph ...

, 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 In organic chemistry, the phenyl group, or phenyl ring, is a cyclic group of atoms with the formula C6 H5, and is often represented by the symbol Ph. Phenyl group is closely related to benzene and can be viewed as a benzene ring, minus a hydrogen ...

, 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 In organic chemistry, an alicyclic compound contains one or more all-carbon rings which may be either saturated or unsaturated, but do not have aromatic character. Alicyclic compounds may have one or more aliphatic side chains attached. The ...

-alkylamines are weaker than unsaturated (meth)amphetamine.

References

{{Monoamine releasing agents Alkylamines Decongestants Norepinephrine-dopamine releasing agents Stimulants Sympathomimetics Cyclopentyl compounds

Pharmacology

Chemistry

See also

References