Α-Propylphenethylamine
α-Propylphenethylamine, also known as 1-phenyl-2-aminopentane, is a stimulant drug of the phenethylamine and amphetamine families. It is the analogue of the β-phenethylamine derivatives amphetamine and phenylisobutylamine in which the α-alkyl chain has been further lengthened to be a propyl group.
Pharmacology
Pharmacodynamics
APPEA is known to act as a low-potency dopamine reuptake inhibitor. Conversely, the drug was inactive as a serotonin reuptake inhibitor and was not assessed in terms of norepinephrine reuptake inhibition. It was similarly inactive as a releasing agent of either dopamine or serotonin, being predominantly a reuptake inhibitor. APPEA's values for inhibition of monoamine reuptake were 2,596nM for dopamine and >10,000nM for serotonin. Analogues of APPEA like phenylisobutylamine are norepinephrine–dopamine releasing agents and norepinephrine–dopamine reuptake inhibitors and have been found to produce stimulant-like and reinforcing effects in rodents.
Chemistry
Derivatives
Numerous derivatives of APPEA exist. These include 1,3-benzodioxolylpentanamine and its derivatives like MBDP and EBDP ; pentedrone and its derivatives like ephylone, 4-methylpentedrone, pentylone, and dipentylone; and prolintane and its derivatives like α-pyrrolidinopentiophenone, pyrovalerone, methylenedioxypyrovalerone, and naphyrone, among others. Another notable analogue, instead with a thiophene ring, is α-pyrrolidinopentiothiophenone. 1-Phenyl-2-propylaminopentane is the combined derivative of APPEA and propylamphetamine. Methylenedioxyphenylpropylaminopentane is the 3,4-methylenedioxy derivative of PPAP.