''N'',''O''-Dimethyl-4β-(2-naphthyl)piperidine-3β-carboxylate (DMNPC) is a

piperidine Piperidine is an organic compound with the molecular formula (CH2)5NH. This heterocyclic amine consists of a six-membered ring containing five methylene bridges (–CH2–) and one amine bridge (–NH–). It is a colorless liquid with an odor de ...

based

stimulant Stimulants (also known as central nervous system stimulants, or psychostimulants, or colloquially as uppers) are a class of drugs that increase alertness. They are used for various purposes, such as enhancing attention, motivation, cognition, ...

drug which is synthesised from

arecoline Arecoline is a cholinergic agent, stimulant, and natural product, naturally occurring alkaloid found in areca nut, areca (betel) nuts of the areca palm (''Areca catechu'') found in South Asia, South and Southeast Asia. Its effects, depending on ...

. It is similar to

nocaine (+)-CPCA (nocaine, 3α-carbomethoxy-4β-(4-chlorophenyl)-''N''-methylpiperidine aka CTDP 31,446) is a stimulant drug similar in structure to pethidine (an opioid that possesses NDRI actions) and to RTI-31, but nocaine lacks the two-carbon brid ...

in chemical structure, and has two and a half times more activity than

cocaine Cocaine is a tropane alkaloid and central nervous system stimulant, derived primarily from the leaves of two South American coca plants, ''Erythroxylum coca'' and ''Erythroxylum novogranatense, E. novogranatense'', which are cultivated a ...

as a

dopamine reuptake inhibitor A dopamine reuptake inhibitor (DRI) is a class of drug which acts as a reuptake inhibitor of the monoamine neurotransmitter dopamine by blocking the action of the dopamine transporter (DAT). Reuptake inhibition is achieved when extracellular dop ...

. However it is also a potent

serotonin reuptake inhibitor A serotonin reuptake inhibitor (SRI) is a type of drug which acts as a reuptake inhibitor of the neurotransmitter serotonin (5-hydroxytryptamine, or 5-HT) by blocking the drug action, action of the serotonin transporter (SERT). This in turn lea ...

, with similar affinity to

fluoxetine Fluoxetine, sold under the brand name Prozac, among others, is an Antidepressant, antidepressant medication of the selective serotonin reuptake inhibitor (SSRI) class used for the treatment of major depressive disorder, Anxiety disorder, anx ...

. DMNPC has four

stereoisomers In stereochemistry, stereoisomerism, or spatial isomerism, is a form of isomerism in which molecules have the same molecular formula and sequence of bonded atoms (constitution), but differ in the three-dimensional orientations of their atoms i ...

, 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. In animal studies, DMNPC exhibits similar potency as

, 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.

Synthesis

A racemic mixture of DMNPC can be synthesized from freebase arecoline in a grignard reaction with 2-naphthylmagnesium bromide. Further reactions and separation methods can be used to produce enantiomerically pure products. A substantially simpler method that ablates the carbomethoxy ester substituent has been demonstrated by D. Koch.

References

{{DEFAULTSORT:Dimethyl-4-(2-naphthyl)piperidine-3-carboxylate, N,O- 4-Phenylpiperidines Serotonin–dopamine reuptake inhibitors Stimulants 2-Naphthyl compounds

Synthesis

See also

References