Proposed structures for an amino-dimethylimidazofuropyridine mutagen in cooked meats

New analytical data allow the structure of a potent mutagen previously reported present in cooked meats to be proposed. The mutagen was isolated from a fried mixture of beef, creatine and milk, simulating a meat recipe previously shown to produce this compound. High-resolution mass spectra indicate a mol. wt of 202 and the formula C10H10N4O. Mutagenic activity was 10,000 TA1538 revertants per microgram in the Ames Salmonella test. From the NMR data, peaks showing an amino group at 6.812 p.p.m. and an N-methyl group at 3.520 p.p.m. were found, typical for the amino-imidazo structure commonly found in cooked meats. Additional signals at 2.440 p.p.m. (three protons), 7.653 (one proton) and 6.531 (one proton) were observed. A structure of 2-amino-(1 or 3),6-dimethylfuro[2,3(or 3,2)-e]imidazo- [4,5-b]pyridine was proposed based on the mass and NMR spectral data and comparison to literature compounds. The methylimidazofuropyridine reported here is probably related to another mutagen in cooked meats with a mol. wt of 216 with an additional methyl group on either the furan or pyridine rings.