2-Amino-3-methylimidazo pyridine

Figure 13.8 Mutagenic and carcinogenic heterocyclic amines (a) IQ (2-amino-3-methylimidazo[4,5-/ quinoline), (b) IQx (2-amino-3-methylimidazo[4,5-/ quinoxaline), (c) PhIP, (2-amino-l-methyl-6-phenylimidazo[4,5- ] pyridine), (d) 1,5,6-TMIP (2-amino-l,5,6-trimethylimidazo[4,5-6] p5ridine).

Amino-2-methylanthraquinone 2-Amino-3-methylimidazo[4,5-/]quinoline (see IQ) 2-Amino-6-methyldipyrido[l,2-a 3, 2 -fil]imidazole (see Glu-P-1) 2-Amino-l-methyl-6-phenylimidazo[4,5-6]pyridine (see PhIP)... 

Note FAP familial adenomatous polyposis ACF aberrant crypt foci FAD focal areas of dysplasia B[a]P benzo[a]pyrene DMBA 7,I2-dimethylbenz[a]nthracene TPA 12-O-tetradecanoyl-phorbol-13-acetate NNK 4-(methyl-nitrosamino)-I-(3-pyridyl)-l-butanone NQO 4-mtroquinoline 1-oxidase DMAB 3,2 -dimethyl-4-aminobiphenol PhIP 2-amino-l-methylimidazo[4,5-b]pyridine DHPN 2,2 -dihydroxy-di-n-propylnitrosamine EHEN jV-ethyl-jV-hydroxyethylnitrosamine. 

Figure 11.4. Structures of various heterocyclic amines. IQ is 2-amino-3-methylimidazo-quinoline. MelQx is 2-amino-3,8-dimethylLtnidazo-quinoxalme. 4,8-DiMelQx is 2-amino-3,4,8-trimethylimidazo-quinoxaline. PhIP is 2-amino-l-methyl-6-phenylimidazo-pyridine. These and other related compounds can be found in fried or broil beef, fish, and chicken, but can also be created by cooking mixtures of creatinine, amino acids, and glucose. Microwave cooking, or cooking in aluminum foil, reduces the formation of heterocyclic amines. (From Sugimura, 1997.)...

IQ 2-amino-3-methylimidazo[4,5-/]quinoline MelQx 2-amino-3,8-dimethylimizado[4,5-/]quinoline PhIP 2-amino-l-methyl-6-phenylimizado[4,5-h]pyridine... 

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)... 

In reaction [46] with equimolar amount or twice the amount of N-bromosuccinimide (NBS) 2-(l-adamantyl)-7- methylimidazo[l,2-a]pyridine (52), obtained from 2-amino-4-methylpyridine and bromomethyl 1-adamantyl ketone, is converted into 2-(l-adamantyl)-3-bromo-7-methylimidazo[l,2-a]pyridine (55). In reaction with three times the amount of N-bromosuccinimide in the presence of trace quantities of water 2-(l-adamantyl)-3-bromo-7-formylimidazo-[l,2-fl]pyridine (54 ) is formed. They suppose that compound 54 is the product from hydrolysis of 2-(l-adamantyl)-3-bromo-7-dibromomethylimidazo[l,2-a]pyridine (b) formed dming the reaction [46]. 

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