(-)-1-Phenyl-2-propylaminopentane

Drugbox
IUPAC_name = ("R")-1-Phenyl-"N"-propylpentan-2-amine

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CAS_number= 784118-64-5
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PubChem=10262369
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C=14 | H=23 | N=1
molecular_weight = 205.35
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(-)-1-Phenyl-2-propylaminopentane ((-)-PPAP) is a drug with an unusual effects profile. It can loosely be grouped with the stimulant or antidepressant drug families, but its mechanism of action is quite different. [Knoll J, Knoll B, Torok Z, Timar J, Yasar S. The pharmacology of 1-phenyl-2-propylamino-pentane (PPAP), a deprenyl-derived new spectrum psychostimulant. "Archives Internationales de Pharmacodynamie et de Therapie". 1992 Mar-Apr;316:5-29.]

PPAP is classified as a catecholaminergic and serotonergic activity enhancer. This means that it stimulates the impulse propagation mediated transmitter release of the neurotransmitters dopamine, noradrenaline and serotonin in the brain (although unlike the newer and more potent compound BPAP it has less impact on serotonin release and affects mainly dopamine and noradrenaline). Unlike stimulant drugs like amphetamines, which release a flood of monoamine neurotransmitters in an uncontrolled manner, PPAP instead only increases the amount of neurotransmitter that gets released when a neuron is stimulated by receiving an impulse from a neighbouring neuron. So while both amphetamines and PPAP increase the amount of neurotransmitters that get released, amphetamines cause neurons to dump neurotransmitter stores into the synapse regardless of external input, while with PPAP the pattern of neurotransmitter release is not changed, but when the neuron would normally release neurotransmitter, a larger amount than normal is released. [Knoll J, Miklya I, Knoll B, Marko R, Kelemen K. (-)Deprenyl and (-)1-phenyl-2-propylaminopentane, [(-)PPAP] , act primarily as potent stimulants of action potential-transmitter release coupling in the catecholaminergic neurons. "Life Sciences". 1996;58(10):817-27. ]

Other drugs which produce this effect are the endogenous trace amines phenethylamine and tyramine, [Knoll J, Miklya I, Knoll B, Marko R, Racz D. Phenylethylamine and tyramine are mixed-acting sympathomimetic amines in the brain. "Life Sciences". 1996;58(23):2101-14.] and the neuroprotective MAO-B inhibitor selegiline. However while selegiline is a potent monoamine oxidase inhibitor, PPAP has no monoamine oxidase inhibitory activity, and produces only the activity enhancer effect. [Csaba G, Kovacs P, Pallinger E. 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". 2006 Jan-Feb;24(1):49-53.]

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