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

N,O-Dimethyl-4-(2-naphthyl)piperidine-3-carboxylate
Systematic (IUPAC) name
methyl (3S,4S)- 1-methyl- 4-(2-naphthyl)piperidine- 3-carboxylate
Clinical data
Identifiers
PubChem CID 10684403
Chemical data
Formula C18H21NO2
283.364 g/mol
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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.[1] It is a structural isomer of another potent dopamine reuptake inhibitor, HDMP-28.

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

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.

See also: RTI-274

See also

References

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