Α-Propylphenethylamine

Pharmaceutical compound From Wikipedia, the free encyclopedia

α-Propylphenethylamine (APPEA or α-Pr-PEA), also known as 1-phenyl-2-aminopentane, is a stimulant drug of the phenethylamine and amphetamine families.[1][2] 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.[1][2]

Other names1-Phenyl-2-aminopentane; 1-Benzylbutylamine; α-Propylphenethylamine; α-Pr-PEA; APPEA; α-Phenyl-β-aminopentane; PAL-550; PAL550
Drug classMonoamine reuptake inhibitor; Stimulant
ATC code
  • None
CAS Number
Quick facts Clinical data, Other names ...
α-Propylphenethylamine
Clinical data
Other names1-Phenyl-2-aminopentane; 1-Benzylbutylamine; α-Propylphenethylamine; α-Pr-PEA; APPEA; α-Phenyl-β-aminopentane; PAL-550; PAL550
Drug classMonoamine reuptake inhibitor; Stimulant
ATC code
  • None
Identifiers
  • 1-phenylpentan-2-amine
CAS Number
PubChem CID
ChemSpider
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC11H17N
Molar mass163.264 g·mol−1
3D model (JSmol)
  • CCCC(CC1=CC=CC=C1)N
  • InChI=1S/C11H17N/c1-2-6-11(12)9-10-7-4-3-5-8-10/h3-5,7-8,11H,2,6,9,12H2,1H3
  • Key:VXGQDFOHLMAZIV-UHFFFAOYSA-N
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Pharmacology

Pharmacodynamics

APPEA is known to act as a low-potency dopamine reuptake inhibitor.[1][2] Conversely, the drug was inactive as a serotonin reuptake inhibitor and was not assessed in terms of norepinephrine reuptake inhibition.[1][2] It was similarly inactive as a releasing agent of either dopamine or serotonin, being predominantly a reuptake inhibitor.[1][2] APPEA's IC50Tooltip half-maximal inhibitory concentration values for inhibition of monoamine reuptake were 2,596 nM for dopamine and >10,000 nM for serotonin.[1][2] 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.[3]

Chemistry

Derivatives

Numerous derivatives of APPEA exist.[4][5][6] 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.[4][5][6] Another notable analogue, instead with a thiophene ring, is α-pyrrolidinopentiothiophenone (α-PVT).[5] 1-Phenyl-2-propylaminopentane (PPAP; α,N-dipropylphenethylamine) is the combined derivative of APPEA and propylamphetamine (N-propylamphetamine).[7][8][9][10] Methylenedioxyphenylpropylaminopentane (MPAP) is the 3,4-methylenedioxy derivative of PPAP.[11]

See also

References

External links

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