Phenylpropylaminopentane
Legal status
Legal status
Identifiers
  • (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)
  • 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 (also known as (-)-PPAP and N,α-dipropylphenethylamine)[1][2][3] is a stimulant of the substituted phenethylamine class that has been derived from selegiline.[4] When compared with selegiline and other substituted phenethylamines (-)-PPAP has a notably different mechanism of action and pharmacological effect.[4]

(-)-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]

Pre-clinical research

The therapeutic index for PPAP in animal models is greater than that of amphetamine while producing comparable improvements in learning, retention, and antidepressant effects in animal models. It has been proposed as a potential therapeutic for ADHD, Alzheimer's disease , and depression based on preclinical findings.[7]

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. ^ a b 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.
  7. ^ Knoll J, Knoll B, Török Z, Timár J, Yasar S (1992). "The pharmacology of 1-phenyl-2-propylamino-pentane (PPAP), a deprenyl-derived new spectrum psychostimulant". Archives Internationales de Pharmacodynamie et de Therapie. 316: 5–29. ISSN 0003-9780. PMID 1356324.
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