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| Clinical data | |
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| Other names | 3-Phenyl-1-propylamine |
| Drug class | Norepinephrine–dopamine releasing agent |
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| CompTox Dashboard(EPA) | |
| ECHA InfoCard | 100.016.376 |
| Chemical and physical data | |
| Formula | C9H13N |
| Molar mass | 135.210 g·mol−1 |
| 3D model (JSmol) | |
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Phenylpropylamine, also known as3-phenylpropylamine, is amonoamine releasing agent (MRA) related tophenethylamine (2-phenylethylamine).[1][2] It is theanalogue of phenethylamine in which theethylamineside chain has been lengthened by onecarbonatom to instead be apropylamine chain.[1][2]
Phenylpropylamine wassynthesized and characterized during investigations of thestructure–activity relationships (SAR) of phenethylamine andamphetamine MRAs.[1][2] It acts as anorepinephrine–dopamine releasing agent (NDRA).[1][2] However, phenylpropylamine is dramatically lesspotent than phenethylamine as an NDRA in rat brainsynaptosomesin vitro and shows ~7-fold preference for induction ofnorepinephrine release overdopamine release.[1][2]
The analogue of phenethylamine with the ethylamine side chain shortened by one carbon atom to instead be amethylamine chain isbenzylamine (phenylmethylamine).[3] In contrast to phenethylamine and phenylpropylamine, benzylamine is said to be inactive as anorepinephrine releasing agent (NRA).[3] However, certainderivatives of benzylamine have nonetheless been found to show MRA-like effects in animals.[4][5] In addition,benzylpiperazine, an analogue of benzylamine with a methylamine-like side chain, is a potent MRA andpsychostimulant.[6][2][7]
| Compound | NETooltip Norepinephrine | DATooltip Dopamine | 5-HTTooltip Serotonin | Ref |
|---|---|---|---|---|
| Phenethylamine (2-phenylethylamine) | 10.9 | 39.5 | >10,000 | [8][1][2] |
| Phenylpropylamine (3-phenylpropylamine) | 222 | 1,491 | ND | [1][2] |
| β-Methylphenethylamine (2-phenylpropylamine) | 126 | 627 | ND | [9] |
| Dextroamphetamine (d-phenylisopropylamine) | 6.6–7.2 | 5.8–24.8 | 698–1,765 | [10][11] |
| Notes: The smaller the value, the more strongly the drug releases the neurotransmitter. Theassays were done in rat brainsynaptosomes and humanpotencies may be different. See alsoMonoamine releasing agent § Activity profiles for a larger table with more compounds.Refs:[12][6] | ||||
The β-phenethylamine skeleton is a critical feature of the molecule since either increasing or decreasing the number of carbons between the phenyl ring and the nitrogen reduced or abolished the activity. Both the γ-phenylpropylamines (e.g., 1-phenyl-3-aminobutane, γ-phenylpropylamine, γ-phenyl-N,N-dimethylpropylamine) and the benzylamines (e.g., α-methylbenzylamine, N,N-diethylbenzylamine, benzylamine) were found to be inactive as releasers of norepinephrine (Daly et al., 1966).
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