Formation of a new mutagenic DiMeIQx compound in a model system by heating creatinine, alanine and fructose.
A mixture of creatinine, D-fructose and DL-alanine was heated in diethylene glycol containing 14% water for 2 h at ca. 128 degrees C. The mutagens formed were extracted with 1-butanol, and purified by cation-exchange column chromatography, C18 reversed-phase Sep-Pak treatment and reversed-phase HPLC. According to its UV absorption, mass and 1H NMR spectra, one isolated fraction was tentatively assigned the chemical name, 3,4,8-trimethyl-3H-imidazo[4,5-f]quinoxalin-2-amine (4,8-DiMeIQx). This finding is in agreement with the suggestion that sugars, amino acids and creatinine present in meat may be the precursors of the mutagenic imidazoquinolin- and imidazoquinoxalin-2-amines (IQ compounds).
D000409:Alanine; D003404:Creatinine; D005632:Fructose; D006358:Hot Temperature; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D009153:Mutagens / Q000138:chemical synthesis; D011810:Quinoxalines / Q000138:chemical synthesis*; D013056:Spectrophotometry, Ultraviolet
D009153:Mutagens; D011810:Quinoxalines; D005632:Fructose; D003404:Creatinine; D000409:Alanine; C045421:3,4,8-trimethylimidazo(4,5-f)quinoxalin-2-amine