Phenylpropylaminopentane

PPAP
Clinical data
Other namesPPAP; (–)-PPAP; (2R)-PPAP; MK-306; α,N-Dipropylphenethylamine; DPPEA; α-Desmethyl-α,N-dipropylamphetamine; 1-Phenyl-2-propylaminopentane; 1-Phenyl-2-propylamino-pentane; 1-Phenyl-2-propyl-aminopentane
Drug classCatecholaminergic activity enhancer; Stimulant
Legal status
Legal status
  • CA: Schedule 1 due to being an amphetamine derivative
  • UK: Class A
Identifiers
  • (2R)-1-Phenyl-N-propylpentan-2-amine
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC14H23N
Molar mass205.345 g·mol−1
3D model (JSmol)
  • CCCN[C@H](CCC)Cc1ccccc1
  • InChI=1S/C14H23N/c1-3-8-14(15-11-4-2)12-13-9-6-5-7-10-13/h5-7,9-10,14-15H,3-4,8,11-12H2,1-2H3/t14-/m1/s1
  • Key:PBENSVGEGPJNFJ-CQSZACIVSA-N

1-Phenyl-2-propylaminopentane (PPAP), also known as α,N-dipropylphenethylamine (DPPEA) and by the developmental code name MK-306, is an experimental drug related to selegiline which acts as a catecholaminergic activity enhancer (CAE).

PPAP is a CAE and enhances the nerve impulse propagation-mediated release of norepinephrine and dopamine. It produces psychostimulant-like effects in animals. The drug is a phenethylamine and amphetamine derivative and was derived from selegiline.

PPAP was first described in the literature in 1988 and in the first major paper in 1992. It led to the development of the improved monoaminergic activity enhancer (MAE) benzofuranylpropylaminopentane (BPAP) in 1999. PPAP was a reference compound for studying the MAE system for many years. However, it was superseded by BPAP, which is more potent, selective, and also enhances serotonin. There has been interest in PPAP for potential clinical use in humans, including in the treatment of depression, attention deficit hyperactivity disorder (ADHD), and Alzheimer's disease.