词条 | N,O-Dimethyl-4-(2-naphthyl)piperidine-3-carboxylate | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
释义 |
| 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 = | pregnancy_category = | legal_status = | routes_of_administration= }} 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.
Clearly it is not just the SS enantiomer of the title compound that is an active MAT inhibitor. Effect of N-demethylationFor 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}}SimplificationA substantially simpler method that ablates the carbomethoxy ester substituent can be found by D. Koch in Ex2: {{US Patent|6303627}} See also
References1. ^{{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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