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| Other names | 1-Phenyl-2-aminopentane; 1-Benzylbutylamine; α-Propylphenethylamine; α-Pr-PEA; APPEA; α-Phenyl-β-aminopentane; PAL-550; PAL550 |
| Drug class | Monoamine reuptake inhibitor;Stimulant |
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| CAS Number | |
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| Chemical and physical data | |
| Formula | C11H17N |
| Molar mass | 163.264 g·mol−1 |
| 3D model (JSmol) | |
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α-Propylphenethylamine (APPEA orα-Pr-PEA), also known as1-phenyl-2-aminopentane, is astimulantdrug of thephenethylamine andamphetamine families.[1][2] It is theanalogue of theβ-phenethylamine (PEA)derivativesamphetamine (α-methylphenethylamine; "AMPEA") andphenylisobutylamine (α-ethylphenethylamine; AEPEA) in which theα-alkylchain has been further lengthened to be apropyl group.[1][2]
APPEA is known to act as a low-potencydopamine reuptake inhibitor.[1][2] Conversely, the drug was inactive as aserotonin reuptake inhibitor and was not assessed in terms ofnorepinephrine reuptake inhibition.[1][2] It was similarly inactive as areleasing agent of eitherdopamine orserotonin, being predominantly areuptake inhibitor.[1][2] APPEA'sIC50Tooltip half-maximal inhibitory concentration values forinhibition of monoamine reuptake were 2,596 nM for dopamine and >10,000 nM for serotonin.[1][2] Analogues of APPEA like phenylisobutylamine (AEPEA) arenorepinephrine–dopamine releasing agents (NDRAs) andnorepinephrine–dopamine reuptake inhibitors (NDRIs) and have been found to producestimulant-like andreinforcing effects in rodents.[3]
Numerous derivatives of APPEA exist.[4][5][6] These include1,3-benzodioxolylpentanamine (BDP; K) and its derivatives likeMBDP (methyl-K) andEBDP (ethyl-K);pentedrone (α-propyl-β-keto-N-methylphenethylamine) and its derivatives likeephylone (N-ethylpentedrone),4-methylpentedrone,pentylone, anddipentylone; andprolintane and its derivatives likeα-pyrrolidinopentiophenone (α-PVP),pyrovalerone,methylenedioxypyrovalerone (MDPV), andnaphyrone, among others.[4][5][6] Another notable analogue, instead with athiophenering, isα-pyrrolidinopentiothiophenone (α-PVT).[5]1-Phenyl-2-propylaminopentane (PPAP; α,N-dipropylphenethylamine) is the combined derivative of APPEA andpropylamphetamine (N-propylamphetamine).[7][8][9][10]Methylenedioxyphenylpropylaminopentane (MPAP) is the 3,4-methylenedioxy derivative of PPAP.[11]
