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
Identifiers
PubChem	CID 10684403
Chemical data
Formula	C18H21NO2
Molar mass	283.364 g/mol
SMILES COC(=O)C1CN(C)CCC1c3ccc2ccccc2c3
(verify)

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

• Naphthylamphetamine
• Naphyrone
• List of cocaine analogues

References

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