Synthesis and biological activity of two metabolites of 1-methyl-5-(1-methylethyl)-2-nitro-1 H-imidazole, an antiprotozoal agent.

5-(-Hydroxyl-1-methylethyl-)-1-methyl-2-nitro-1 H-imidazole (6) and 5-(1,2-dihydroxyl-1-methylethyl)-1-methyl-2-nitro-1 H-imidazole (9) are the principal metabolites found in urines of animals (mice, rats, and dogs) treated with 1-methyl-5-(1-methylethyl)-2-nitro-1 H-imidazole (1), an effective antitrichomonas agent. These two metabolites have been synthesized. Compound 6 was found to be less toxic than the parent compound 1 and to possess essentially the same activity against Trichomonas vaginalis in experimental infections. Compound 9 showed a low degree of in vivo activity.