PubChem CID 10684403 Molar mass 283.364 g/mol | Formula C18H21NO2 3D model (Jmol) Interactive image | |
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N,O-Dimethyl-4β-(2-naphthyl)piperidine-3β-carboxylate (DMNPC) 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
Interestingly, for the SR enantiomer, increased DAT affinity is seen upon demethylation.
This is the same choice of isomer used in the production of Paxil.
References
N,O-Dimethyl-4-(2-naphthyl)piperidine-3-carboxylate Wikipedia(Text) CC BY-SA