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

  1. Effect of N-demethylation

  2. Simplification

  3. See also

  4. References

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| verifiedrevid = 424701119
| drug_name = N,O-Dimethyl-4-(2-naphthyl)piperidine-3-carboxylate
| IUPAC_name = methyl (3S,4S)- 1-methyl- 4-(2-naphthyl)piperidine- 3-carboxylate
| image=MMNPC.png
| width= 220
| CAS_number=
| ATC_prefix=
| ATC_suffix=
| PubChem= 10684403
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank=
| C=18 | H=21 | N=1 | O=2
| molecular_weight = 283.364 g/mol
| smiles = COC(=O)C1CN(C)CCC1c3ccc2ccccc2c3
| bioavailability=
| metabolism =
| elimination_half-life=
| excretion =
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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.[1] It is a structural isomer of another potent dopamine reuptake inhibitor, HDMP-28.

Ki Affinity of Piperidine Based MAT Inhibitors
∗∗XN5HTDANE
SSp-VinylMe138131175
p-Ethyl255>1.7K>1.1K
p-Allyl309964>1K
p-Ethynyl175187364
p-Phenyl62173203
β-Naphthyl7.62134
3R,4S42947241
RR1928727
3S,4R1227138
H2Cl3.59030
SS/RRα-NaphthylMe101304281

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: {{US Patent|6303627}}

See also

  • Naphthylamphetamine
  • Naphyrone
  • List of cocaine analogues

References

1. ^{{cite web |url=http://pubs.acs.org/cgi-bin/abstract.cgi/jmcmar/2000/43/i06/abs/jm9905561.html |title=Further SAR Studies of Piperidine-Based Analogues of Cocaine. 2. Potent Dopamine and Serotonin Reuptake Inhibitors |accessdate=2008-01-11 |website=}}
{{Stimulants}}{{Dopaminergics}}{{DEFAULTSORT:Dimethyl-4-(2-naphthyl)piperidine-3-carboxylate, N,O-}}{{nervous-system-drug-stub}}

4 : Piperidines|Serotonin-dopamine reuptake inhibitors|Stimulants|Naphthalenes

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