7324. PhIP

Nomenclature

CAS number: 105650-23-5
1-Methyl-6-phenyl-1H-imidazo[4,5-b]pyridin-2-amine; 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine.
C13H12N4; mol wt 224.26.
C 69.62%, H 5.39%, N 24.98%.

Description and references

Most abundant of the mutagenic heterocyclic amines found in well-cooked meat and fish. Isoln from fried ground beef: J. S. Felton et al., Carcinogenesis 7, 1081 (1986). Synthesis: M. G. Knize, J. S. Felton, Heterocycles 24, 1815 (1986); T. Choshi et al., J. Org. Chem. 58, 7952 (1993); F. S. Bavetta et al., Tetrahedron Lett. 44, 7793 (1997). Mutagenicity in Chinese hamster ovary cells: L. H. Thompson et al., Mutagenesis 2, 483 (1987). Evaluation of carcinogenic risk: IARC Monographs 56, 229-242 (1993). Review of bioavailability, content in foods, metabolism: N. J. Gooderham et al., Br. J. Clin. Pharmacol. 42, 91-98 (1996). Correlation of dietary intake with breast cancer risk: R. Sinha et al., J. Natl. Cancer Inst. 92, 1352 (2000).

Chemical structure

Properties

Gray-white crystals, mp 327-328°. uv max (methanol): 225, 273, 316 nm (log ε 4.46, 4.00, 4.46). Sol in methanol, DMSO.

Caution

This substance is reasonably anticipated to be a human carcinogen: Report on Carcinogens, Eleventh Edition (PB2005-104914, 2004) p III-135.