Phenylpropylaminopentane

Phenylpropylaminopentane

Systematic (IUPAC) name
(R)-1-Phenyl-N-propylpentan-2-amine
Identifiers
CAS Number	784118-64-5
PubChem	CID 10262369
ChemSpider	21106218
Chemical data
Formula	C14H23N
Molar mass	205.35

(-)-1-Phenyl-2-propylaminopentane ((-)-PPAP)^[1] 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.^[2]

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, norepinephrine and serotonin in the brain (although unlike the newer and more potent compound BPAP, it has less impact on serotonin release and affects mainly the catecholamines). Unlike stimulant drugs like amphetamine, which release a flood of monoamine neurotransmitters in an uncontrolled manner, PPAP instead only increases the amount of neurotransmitters that gets released when a neuron is stimulated by receiving an impulse from a neighbouring neuron. So while both amphetamine and PPAP increase the amount of neurotransmitters that get released, amphetamine causes 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 neurotransmitters, a larger amount than normal is released.^[3]

However, while selegiline is a potent monoamine oxidase inhibitor, PPAP has no monoamine oxidase inhibitory activity, and produces only the activity enhancer effect.^[4]

References

1. US Patent 5075338
2. 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 Thérapie. 1992 Mar-Apr;316:5-29.
3. 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.
4. 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.