3-PPP


3-PPP is a mixed sigma σ1 and σ2 receptor agonist and D2 receptor partial agonist which is used in scientific research. It shows stereoselectivity in its pharmacodynamics. -3-PPP is the enantiomer that acts as an agonist of the sigma receptors; it is also an agonist of both D2 presynaptic and postsynaptic receptors. Conversely, -3-PPP, also known as preclamol, acts as an agonist of presynaptic D2 receptors but as an antagonist of postsynaptic D2 receptors, and has antipsychotic effects. 3-PPP has also been reported to be a monoamine reuptake inhibitor and possibly to act at adrenergic receptors or some other non-sigma receptor.

Synthesis

The Grignard reagent was prepared for 3-Bromoanisole and this was reacted with 3-Bromopyridine to give 3-pyridine . Reaction with 1-bromopropane occurred to give the quaternary salt PC13695099. Catalytic hydrogenation of the quat cation gave 3--1-propylpiperidine . Demethylation with hydrogen bromide then completed the synthesis of preclamol.