Phenylpropylaminopentane

(-)-1-Phenyl-2-propylaminopentane (also known as (-)-PPAP and N,α-dipropylphenethylamine)[1][2][3] is a stimulant of the substituted phenethylamine class and a derivative of Selegiline.[4] When compared with Selegiline and other substituted phenethylamines (-)-PPAP has a notably different mechanism of action and pharmacological effect.[4]

Phenylpropylaminopentane
Legal status
Legal status
Identifiers
IUPAC name
  • (R)-1-Phenyl-N-propylpentan-2-amine
CAS Number
PubChem CID
ChemSpider
UNII
Chemical and physical data
FormulaC14H23N
Molar mass205.345 g·mol−1
3D model (JSmol)
SMILES
  • CCCN[C@H](CCC)Cc1ccccc1
InChI
  • 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

(-)-PPAP is classified as a monoaminergic activity enhancer that stimulates the impulse propagation mediated transmitter release of the neurotransmitters dopamine, norepinephrine and serotonin in the brain. Unlike stimulants such as amphetamine, which release a flood of monoamine neurotransmitters in an uncontrolled manner, (-)-PPAP instead only increases the amount of neurotransmitters that get released when a neuron is stimulated by receiving an impulse from a neighbouring neuron. Both amphetamine and (-)-PPAP promote the release of monoamines and deuteramines, however while amphetamine causes neurons to dump neurotransmitter stores into the synapse regardless of external input, (-)-PPAP does not influence the pattern of neurotransmitter release and instead releases a larger amount of neurotransmitters than normal.[5]

(-)-PPAP has no monoamine oxidase inhibitory activity.[6]

See also

References
  1. Jozsef Knoll (15 June 1993). "Patent US 5220068 - Psychostimulant agent".
  2. Fumio Yoneda (10 April 2001). "Patent US 6214859 - Ethylamine derivatives".
  3. Jozsef Knoll (24 December 2001). "Patent US 5075338 - Method of treatment of learning deficiency".
  4. Knoll J, Knoll B, Török Z, Timár J, Yasar S (March–April 1992). "The pharmacology of 1-phenyl-2-propylamino-pentane (PPAP), a deprenyl-derived new spectrum psychostimulant". Archives Internationales de Pharmacodynamie et de Therapie. 316 (316): 5–29. PMID 1356324.
  5. Knoll J, Miklya I, Knoll B, Markó R, Kelemen K (February 1996). "(-)Deprenyl and (-)1-phenyl-2-propylaminopentane, [(-)PPAP], act primarily as potent stimulants of action potential-transmitter release coupling in the catecholaminergic neurons". Life Sciences. 58 (10): 817–27. doi:10.1016/0024-3205(96)00014-8. PMID 8602114.
  6. Csaba G, Kovács P, Pállinger E (January–February 2006). "Acute and delayed effect of (-) deprenyl and (-) 1-phenyl-2-propylaminopentane (PPAP) on the serotonin content of peritoneal cells (white blood cells and mast cells)". Cell Biochemistry and Function. 24 (1): 49–53. doi:10.1002/cbf.1183. PMID 15584092. S2CID 11027835.
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