Metabolism of dibucaine: isolation and identification of urinary basic metabolites in the rat, rabbit and man.
The metabolism of dibucaine was studied in the rat, rabbit and man. A total of ten basic metabolites other than dibucaine were detected in the urine samples of three species by thin-layer chromatography (TLC) and gas chromatography (GC), and structures of these metabolites were identified by comparison of the properties given by TLC, GC and gas chromatography-mass spectrometry (GC-MS) with those of authentic compounds. Four of these metabolites were new metabolites which were found in the rabbit or human urine; two were identified as the 2', 3'-dihydroxybutoxy product (M-6, diol) and its N-deethyl product (M-2), and others were identified as the 2'-hydroxyethoxy product (M-8, alcohol) and its N-deethyl product (M-3). One of the two hydroxyl groups on M-5 was at 6-position on the quinoline ring, while another was assumed to be at 3'-position on the O-alkyl side chain. There were apparent species differences with regard to the major metabolites found in each species; i.e. M-10 and M-5 in rat, M-6 and M-4 in rabbit, and M-8 and M-4 in man. Small amounts of the conjugated basic metabolites were observed in the urine of all three species. The new metabolic pathways to the diols (M-2 and M-6) or the alcohols (M-3 and M-8) were also discussed.
D000328:Adult; D000818:Animals; D002849:Chromatography, Gas; D002855:Chromatography, Thin Layer; D003992:Dibucaine / Q000378:metabolism* / Q000652:urine; D008401:Gas Chromatography-Mass Spectrometry; D006801:Humans; D008297:Male; D011817:Rabbits; D051381:Rats; D011919:Rats, Inbred Strains
D003992:Dibucaine