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

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.[1] It is a structural isomer of another potent dopamine reuptake inhibitor, HDMP-28.

N,O-Dimethyl-4-(2-naphthyl)piperidine-3-carboxylate
Identifiers
PubChem CID
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC18H21NO2
Molar mass283.371 g·mol−1
3D model (JSmol)
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Ki Affinity of Piperidine Based MAT Inhibitors
∗∗XN5HTDANE
SSp-VinylMe138131175
p-Ethyl255>1.7K>1.1K
p-Allyl309964>1K
p-Ethynyl175187364
p-Phenyl62173203
β-Naphthyl7.62134
3R,4S42947241
RR1928727
3S,4R1227138
H2Cl3.59030
SS/RRα-NaphthylMe101304281

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.

See also: RTI-274

Simplification

A substantially simpler method that ablates the carbomethoxy ester substituent can be found by D. Koch in Ex2: U.S. Patent 6,303,627

See also

References
  1. "Further SAR Studies of Piperidine-Based Analogues of Cocaine. 2. Potent Dopamine and Serotonin Reuptake Inhibitors". Retrieved 2008-01-11.


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