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

Category::rowspan    Reuptake::cocaine    Potent::similar    Potent::dopamine    Dopamine::title    HDMP-::small

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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.<ref name="titleFurther SAR Studies of Piperidine-Based Analogues of Cocaine. 2. Potent Dopamine and Serotonin Reuptake Inhibitors">{{#invoke:citation/CS1|citation |CitationClass=web }}</ref> 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.

N,O-Dimethyl-4-(2-naphthyl)piperidine-3-carboxylate sections
Intro  Effect of N-demethylation  See also  References  

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