Local anesthetics. 2-Diethylamino-2',6'-acylxylidides.
A series of C-alkylated derivatives of lidocaine has been synthesized, and the local anesthetic potencies were determined. Activity reached a miximum with the butyroxylidide (alpha-ethyl group), but toxicity increased regularly with the number of carboons in the side chain. Spectral data showed the compounds to exist as associated H-bonded structures, the free base most likely as intramolecularly bonded trans amides and the hydrochlorides most likely as associated cis amindes.
D000779:Anesthetics, Local / Q000138:chemical synthesis* / Q000633:toxicity; D000818:Animals; D005260:Female; D007928:Lethal Dose 50; D008012:Lidocaine / Q000031:analogs & derivatives*; D009682:Magnetic Resonance Spectroscopy; D051379:Mice; D009407:Nerve Block; D051381:Rats; D013055:Spectrophotometry, Infrared; D014992:Xylenes / Q000138:chemical synthesis* / Q000494:pharmacology / Q000633:toxicity
D000779:Anesthetics, Local; D014992:Xylenes; D008012:Lidocaine