Phenylpropylaminopentane
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| Other names | (-)-PPAP; N,α-Dipropylphenethylamine |
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| Formula | C14H23N |
| Molar mass | 205.345 g·mol−1 |
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(-)-1-Phenyl-2-propylaminopentane (also known as (-)-PPAP and N,α-dipropylphenethylamine)[1][2][3] is a monoaminergic drug of the substituted phenethylamine and amphetamine families that has been derived from selegiline.[4] It is described as a psychostimulant in terms of its effects.[4] When compared with selegiline and other substituted phenethylamines however, (-)-PPAP has a notably different mechanism of action and pharmacological effects.[4]
(-)-PPAP is classified as a monoaminergic activity enhancer that stimulates the impulse propagation-mediated release of the monoamine 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 neighboring neuron. Both amphetamine and (-)-PPAP promote the release of monoamines and deuteramines, however while amphetamine causes neurons to release 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] Unlike the related compound selegiline, (-)-PPAP has no monoamine oxidase inhibitory activity.[6]
The therapeutic index for PPAP in animal models is greater than that of amphetamine while producing comparable improvements in learning, retention, and antidepressant effects. It has been proposed as a potential therapeutic agent for attention deficit hyperactivity disorder (ADHD), Alzheimer's disease, and depression based on preclinical findings.[7]
Unlike the related compound selegiline, (-)-PPAP has no monoamine oxidase inhibitory activity.[8]
The developers of PPAP attempted to have it clinically studied, but were unsuccessful and it was never assessed in humans.[9]
See also
[edit]- (-)-BPAP
- Propylamphetamine
- 3,4-Methylenedioxy-N-propylamphetamine
- Methylenedioxyallylamphetamine
- MBDP
- Prolintane
- Pentedrone
- Propylphenidine
References
[edit]- ^ US 5220068, Knoll J, Simay A, Szinnyei E, Somfai E, Torok Z, Mozsolits K, Bergmann J, "Psychostimulant agent", issued 15 June 1993, assigned to Chinoin Private Co Ltd.
- ^ US 6214859, Yoneda F, Knoll J, Ode H, Sakae M, Katurada M, Moto T, Ando T, Shimazu S, Takahata K, Fujimoto M, "Ethylamine derivatives", issued 10 April 2001, assigned to Fujimoto Brothers Co Ltd.
- ^ US 5075338, Knoll J, Simay A, Szinnyei E, Somfai E, Torok Z, Mozsolits K, Bergmann J, "Method of treatment of learning deficiency", issued 24 December 2001, assigned to Chinoin Private Co Ltd.
- ^ a b c 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.
- ^ 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.
- ^ 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.
- ^ 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. PMID 1356324.
- ^ 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.
- ^ Knoll J (2001). "Antiaging compounds: (-)deprenyl (selegeline) and (-)1-(benzofuran-2-yl)-2-propylaminopentane, [(-)BPAP], a selective highly potent enhancer of the impulse propagation mediated release of catecholamine and serotonin in the brain". CNS Drug Rev. 7 (3): 317–45. doi:10.1111/j.1527-3458.2001.tb00202.x. PMC 6494119. PMID 11607046.
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