''N'',''O''-Dimethyl-4β-(2-naphthyl)piperidine-3β-carboxylate (DMNPC) is a
piperidine based
stimulant
Stimulants (also often referred to as psychostimulants or colloquially as uppers) is an overarching term that covers many drugs including those that increase activity of the central nervous system and the body, drugs that are pleasurable and inv ...
drug which is synthesised from
arecoline. 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 is lacking the two-carbo ...
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
Fluoxetine, sold under the brand names Prozac and Sarafem, among others, is an antidepressant of the selective serotonin reuptake inhibitor (SSRI) class. It is used for the treatment of major depressive disorder, obsessive–compulsive disorde ...
.
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.
Simplification
A substantially simpler method that ablates the carbomethoxy ester substituent can be found by D. Koch in Ex2:
See also
*
1-Methyl-3-propyl-4-(p-chlorophenyl)piperidine
1-Methyl-3-propyl-4-(''p''-chlorophenyl)piperidine is a drug developed by a team led by Alan Kozikowski, which acts as a potent dopamine reuptake inhibitor, and was developed as a potential therapeutic agent for the treatment of cocaine addic ...
*
Naphthylamphetamine
*
Naphyrone
*
List of cocaine analogues
References
4-Phenylpiperidines
Serotonin–dopamine reuptake inhibitors
Stimulants
2-Naphthyl compounds
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