Sulfamate formation is a major route for detoxification of 2-amino-3-methylimidazo[4,5-f]quinoline in the rat.
The major biliary metabolite of 2-amino-3-methylimidazo[4,5-f]quinoline (IQ) in the rat was identified as the sulfamate derivative, N-[3-methylimidazo[4,5-f]quinolin-2-yl] sulfamic acid. Identification was accomplished primarily by u.v., 1H-n.m.r. and mass spectrometry of the material isolated from bile and confirmed by comparison with material synthesized by reaction of chlorosulfonic acid with IQ. The sulfamate was shown to be non-mutagenic in bacterial forward mutation assays. Greater than 20% of an administered dose of IQ could be recovered from feces (17%) and urine (5%) as the sulfamate. Very little unmetabolized IQ was recovered in bile, urine, or feces. Thus, the unusual process of N-sulfation is a major contributor to the detoxification and elimination of IQ in the rat.
D000818:Animals; D001646:Bile / Q000378:metabolism; D008658:Inactivation, Metabolic; D008297:Male; D009153:Mutagens / Q000378:metabolism*; D011804:Quinolines / Q000378:metabolism*; D051381:Rats; D011919:Rats, Inbred Strains; D013451:Sulfonic Acids / Q000378:metabolism*
D009153:Mutagens; D011804:Quinolines; D013451:Sulfonic Acids; C029216:2-amino-3-methylimidazo(4,5-f)quinoline; C005741:sulfamic acid