Conjugates of N-nitroso-tert-butylmethylamine in urine.

The glucuronide (alpha-anomer) and the mercapturic acid of N-nitroso-tert-butylhydroxymethylamine were synthesized. An analytical procedure was developed using high-performance liquid chromatography, which allowed the detection of both conjugates in a single run. A new and efficient synthesis of N-nitroso-tert-butyl-14C-methylamine was developed, based on 14C-formaldehyde. After subcutaneous administration of 23 mg/kg to a rat, the nitrosamine was metabolized to a high degree, and two conjugates were excreted in the urine.