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N,O-Dimethyl-4-(2-naphthyl)piperidine-3-carboxylate

Chemical compound

Chemical compound

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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. DMNPC racemate has been sold online as a designer drug since late 2024.

DMNPC has four stereoisomers, each of which has different binding affinities, with the 3S,4S enantiomer having the highest overall activity. The 3R,4S enantiomer demonstrates the highest selectivity for 5-HTT.

3S,4R1227138

In animal studies, DMNPC exhibits similar potency as fluoxetine, but with greater activity for DAT and NET. N-Demethylation of DMNPC has shown to produce a 3-fold increase in potency for 5-HTT.

Synthesis

A racemic mixture of DMNPC can be synthesized from freebase arecoline in a grignard reaction with 2-naphthylmagnesium bromide. Further reactions and separation methods can be used to produce enantiomerically pure products.

A substantially simpler method that ablates the carbomethoxy ester substituent has been demonstrated by D. Koch.

References

References

  1. (March 2000). "Further SAR Studies of Piperidine-Based Analogues of Cocaine. 2. Potent Dopamine and Serotonin Reuptake Inhibitors". Journal of Medicinal Chemistry.
  2. {{US Patent. 6303627
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4-phenylpiperidines serotonin–dopamine-reuptake-inhibitors stimulants 2-naphthyl-compounds
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