|Systematic (IUPAC) name|
|methyl (3S,4S)- 1-methyl- 4-(2-naphthyl)piperidine- 3-carboxylate|
|(what is this?)|
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.
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.
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