N,O-Dimethyl-4-(2-naphthyl)piperidine-3-carboxylate
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| Formula | C18H21NO2 |
| Molar mass | 283.371 g·mol−1 |
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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.
| Binding affinities (Ki) | ||||||
| Stereochemistry | 5HT | DA | NE | |||
| 3S,4S | 7.6 | 21 | 34 | |||
| 3R,4S | 42 | 947 | 241 | |||
| 3R,4R | 192 | 87 | 27 | |||
| 3S,4R | 12 | 271 | 38 | |||
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.