α-Propylphenethylamine (APPEA or α-Pr-PEA), 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 (PEA) derivatives amphetamine (α-methylphenethylamine; "AMPEA") and phenylisobutylamine (α-ethylphenethylamine; AEPEA) 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 (AEPEA) are norepinephrine–dopamine releasing agents (NDRAs) and norepinephrine–dopamine reuptake inhibitors (NDRIs) 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 (BDP; K) and its derivatives like MBDP (methyl-K) and EBDP (ethyl-K); pentedrone (α-propyl-β-keto-N-methylphenethylamine) and its derivatives like ephylone (N-ethylpentedrone), 4-methylpentedrone, pentylone, and dipentylone; and prolintane and its derivatives like α-pyrrolidinopentiophenone (α-PVP), pyrovalerone, methylenedioxypyrovalerone (MDPV), and naphyrone, among others. Another notable analogue, instead with a thiophene ring, is α-pyrrolidinopentiothiophenone (α-PVT). 1-Phenyl-2-propylaminopentane (PPAP; α,N-dipropylphenethylamine) is the combined derivative of APPEA and propylamphetamine (N-propylamphetamine). Methylenedioxyphenylpropylaminopentane (MPAP) is the 3,4-methylenedioxy derivative of PPAP.

See also Substituted phenethylamine N,α-Diethylphenethylamine (DEPEA) β-Methylphenethylamine (BMPEA) Phenacylamine (β-ketophenethylamine)

References

External links α-Propylphenethylamine (α-Pr-PEA) - isomer design