N,O-Dimethyl-4-(2-naphthyl)piperidine-3-carboxylate
Identifiers | |
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PubChem (CID) | 10684403 |
Chemical and physical data | |
Formula | C18H21NO2 |
Molar mass | 283.364 g/mol |
3D model (Jmol) | Interactive image |
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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 | ||||||
∗∗ | X | N | 5HT | DA | NE | |
SS | p-Vinyl | Me | 138 | 131 | 175 | |
p-Ethyl | 255 | >1.7K | >1.1K | |||
p-Allyl | 309 | 964 | >1K | |||
p-Ethynyl | 175 | 187 | 364 | |||
p-Phenyl | 62 | 173 | 203 | |||
β-Naphthyl | 7.6 | 21 | 34 | |||
3R,4S | 42 | 947 | 241 | |||
RR | 192 | 87 | 27 | |||
3S,4R | 12 | 271 | 38 | |||
H2Cl | 3.5 | 90 | 30 | |||
SS/RR | α-Naphthyl | Me | 101 | 304 | 281 | |
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
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