|CompTox Dashboard (EPA)|
|Chemical and physical data|
|Molar mass||283.371 g·mol−1|
|3D model (JSmol)|
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.
|Ki Affinity of Piperidine Based MAT Inhibitors|
Clearly it is not just the SS enantiomer of the title compound that is an active MAT inhibitor.
For the SR enantiomer, increased DAT affinity is seen upon demethylation.
This is the same choice of isomer used in the production of Paxil.
A substantially simpler method that ablates the carbomethoxy ester substituent can be found by D. Koch in Ex2: U.S. Patent 6,303,627
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