2-amino-1 -methyl-6-phenyl-imidazo pyridine

Trp-P-2 (3-amino-l-methyl-5//-pyrido[4,3-h]indole), AaC (2-amino-9//-pyrido[2,3-bJindole), MeAaC (2-amino-3-methyl-9//-pyrido[2,3- ]indole), and PhIP (2-amino-1-methyl-6-phenyl-imidazo[4,5-h]pyridine) and two /3-carbolines comutagens harman (l-methyl-9//-pyrido[4,3-h]indole) and norharman (9//-pyrido[4,3-h]indole). The optimized SPE procedure for isolation and preconcentration comprises the use of diatomaceous earth, propylsulfonyl silica gel, and C18 cartridges to separate selectively the imidazopyridine and indolpyridine derivatives from those of... 

Eriesen, M. D., Garren, L., Bereziat, J.-C., Kadlubar, F., and Lin, D., Gas chromatography-mass spectrometry analysis of 2-amino-l-methyl-6-phenyl imidazo [4,5-6] pyridine in urine and feces. Environ. Health Perspect, 99, 179-181, 1993. 

Tikkanen, L. M., Sauri, T. M., and Latva-kala, K. J., Screening of heat-processed Fitmish foods for the mutagens 2-amino-3,8-dimethyl imidazole [4,5f] quinoxahne, 2-amino-3,4,8-trimethyl imidazole [4,5f] quinoxahne and 2-amino-l-methyl-6-phenyl imidazo [4,5b] pyridine. Food Chem. Toxicol, 31, 717-721, 1993. 

AaC = 2-amino-9Tf-pyrido[2,3-fe]indole MeAaC = 2-amino-3-methyl-9Tf-pyrido[2,3-fe]indole Glu-P-1 = 2-amino-6-methyldipyrido[l,2-a 3 ,2 -ai] imidazole Glu-P-2 = 2-aminodipyrido[l,2-a 3 ,2 -ii]imidazole PhIP = 2-amino-l-methyl-6-phenyl-lH-imidazo[4,5-i)]pyridine IQ = 2-amino-3-methyl-3//-imidazo[4,5-/ quinoline MelQ = 2-amino-3,4-dimethyl-3Tf-imidazo[4,5-/ quinoline Trp-P-1 = 3-amino-l,4-dimethyl-5Tf-pyrido[4,3-i)]indole Trp-P-2 = 3-amino-l-methyl-5//-pyrido[4,3-I>]indole. 

Glu-P-1 = 2-amino-6-methyldipyTido[l,2-a 3 ,2 -al]imidazole Glu-P-2 = 2-aminodipyrido[l,2-a 3 ,2 -rf]imidazole PhIP = 2-amino-l-methyl-6-phenyl-177-imidazo[4,5-fe]pyridine IQ = 2-amino-3-methyl-377-imidazo[4,5-/ quinoline... 

Vanderlaan, M. Watkins, B.E. Hwang, M. Knize, M. Felton, J. S. Development of an immunoassay for 2-amino-l-methyl-6-phenyl-imidazo[4,5-f]-pyridine (PhIP) in cooked meats. Carcinogenesis, 10 2215-21. 1989. 

Imidazo[4,5-b]pyridin-5(4H)-one, 3-amino-7-methyI-2-phenyl-methylation, 5, 616-617... 

SYNS IMIDAZO(4,5-B)PYRIDINE, 2-AMINO-1-METHYL-6-PHENYL- lH-IMIDAZO(4,5-B)PYRIDIN-2-... 

In the laboratory of J.S. Felton, the synthesis of 2-amino-1-methyl-6-phenyl-1/-/-imidazo[4,5- i]pyridine (PHIP), a mutagenic compound isolated from cooked beef, and its 3-methyl isomer have been accomplished. The synthesis of PHIP began with the commercially available 3-phenylpyridine, which was aminated at the 6-position with sodium amide in toluene by the Chichibabin reaction in 58% yield. 

Kinae et al. (2095a) reported that A-heterocyclic amines [2-amino-3-methylimidazo[4,5-/ quinoline (IQ), 2-amino-3,4-dimethylimidazo[4,5-/ quinoline (MelQ), l-methyl-6-phenyl-l//-imidazo[4,5-/7]pyridin-2-amine (PhIP)] were produced in an incubated solution of D-glucose and several amino acids at much lower temperatures and longer time periods than those encountered in the cooking of various foodstuffs (beef, poultry, fish). Several A-heterocyclic amines not found in CSC were also generated. The generation of the A-heterocyclic amines, as measured by the Ames test (Salmonella typhimurium TA 98), increased in proportion to the conditions imposed 37°C (90 d), 50°C (30 d), 128°C (2 h)... 

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