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

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N,O-Dimethyl-4-(2-naphthyl)piperidine-3-carboxylate
MMNPC.png
Identifiers
IUPAC name
  • methyl (3S,4S)- 1-methyl- 4-(2-naphthyl)piperidine- 3-carboxylate
CAS Number
PubChem CID
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC18H21NO2
Molar mass283.371 g·mol−1
3D model (JSmol)
SMILES
  • COC(=O)C1CN(C)CCC1c3ccc2ccccc2c3
  

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]

MMNPC&HDMP-28.png

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[]

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. ^ Tamiz AP, Zhang J, Flippen-Anderson JL, Zhang M, Johnson KM, Deschaux O, et al. (March 2000). "Further SAR Studies of Piperidine-Based Analogues of Cocaine. 2. Potent Dopamine and Serotonin Reuptake Inhibitors". Journal of Medicinal Chemistry. 43 (6): 1215–22. doi:10.1021/jm9905561. PMID 10737754.
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