N,O-Dimethyl-4-(2-naphthyl)piperidine-3-carboxylate
N,O-Dimethyl-4β-piperidine-3β-carboxylate is a piperidine based stimulant drug which is synthesised from arecoline. It is similar to nocaine in chemical structure, and has two and a half times more activity than cocaine as a dopamine reuptake inhibitor. However it is also a potent serotonin reuptake inhibitor, with similar affinity to fluoxetine. It is a structural isomer of another potent dopamine reuptake inhibitor, HDMP-28.
Clearly it is not just the SS enantiomer of the title compound that is an active MAT inhibitor.Effect of ''N''-demethylation
For the SR enantiomer, increased DAT affinity is seen upon demethylation.
This is the same choice of isomer used in the production of Paxil.Simplification
A substantially simpler method that ablates the carbomethoxy ester substituent can be found by D. Koch in Ex2:
