Synthesis and local anesthetic activity of some derivatives of N,N-dimethyl-2-(2-alkoxyphenylcarbamoyloxy)-1,1-dimethylethyl-ammonium chlorides.
A series of 8 new derivatives of 2-alkoxyphenylcarbamoic acid were synthesized and assayed for local anesthetic activity. The above compounds were isolated as hydrochlorides and their structure was proved by 1H NMR, 13C NMR and IR spectroscopy. The index of anesthetic activity of the compounds in infiltration and surface anesthesia increases with the length of the alkyl chain and, except for the C1-C3 congeners, all higher homologues proved to be significantly more active than the standard reference compounds, procaine and cocaine, respectively. Toxicity of the drugs decreases with increasing the chain length and is within acceptable limits.
Gregán
F
F
Departament of Organic Chemistry, Faculty of Pharmacy, Bratislava, Czechoslovakia.
Novomeský
P
P
Racanská
E
E
Kettmann
V
V
D000643:Ammonium Chloride / Q000138:chemical synthesis* / Q000494:pharmacology / Q000633:toxicity; D000779:Anesthetics, Local / Q000138:chemical synthesis* / Q000494:pharmacology / Q000633:toxicity; D000818:Animals; D002219:Carbamates / Q000138:chemical synthesis* / Q000494:pharmacology / Q000633:toxicity; D006168:Guinea Pigs; D009682:Magnetic Resonance Spectroscopy; D051379:Mice; D011817:Rabbits; D012015:Reference Standards; D012995:Solubility; D013055:Spectrophotometry, Infrared
D000779:Anesthetics, Local; D002219:Carbamates; D000643:Ammonium Chloride