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Hoffmann, R. A wiki for the life sciences where authorship matters. Nature Genetics (2008)

Further structural analysis of rat liver microsomal metabolites of 2-methylnaphthalene.

The oxidative metabolites of 2-methylnaphthalene (2-MN) were extracted from rat liver microsome suspensions. One monohydroxylated and three isomeric dihydrodiol metabolites of 2-MN were isolated and purified by HPLC. The metabolites were characterized by GC-MS together with 1H Fourier transform (1HFT) NMR. The identification of a 2-MN-monohydroxylated product as 2-hydroxymethylnaphthalene was confirmed by comparison of its HPLC retention time and NMR spectrum with that of a synthetic standard. The three isomeric dihydrodiol metabolites had different HPLC retention times, fragmentation patterns, ultraviolet, and 1H NMR spectra. GC-MS of the silylated dihydrodiols revealed the consistent presence of an ion peak at m/z 320, indicative of a disilylated dihydrodiol. Analysis of the 1H FT NMR spectra revealed the metabolites to be the 3,4-dihydrodiol, 5,6-dihydrodiol, and 7,8-dihydrodiol of 2-methylnaphthalene.[1]


  1. Further structural analysis of rat liver microsomal metabolites of 2-methylnaphthalene. Breger, R.K., Novak, R.F., Franklin, R.B., Rickert, D., Lech, J.J. Drug Metab. Dispos. (1983) [Pubmed]
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