Urinary metabolites of some alicyclic nitrosamines.
We have studied the urinary metabolites of N-nitrosopiperidine, 3- and 4-hydroxy-N-nitrosopiperidine, N-nitroso-4-piperidone, N-nitrosohexamethyleneimine and N-nitroso-heptamethyleneimine. The N-nitrosopiperidines induce primarily oesophageal tumours in rats; N-nitrosohexamethyleneimine induces oesophageal and liver tumours and N-nitrosoheptamethyleneimine induces oesophageal and lung tumours. The products were identified by gas chromatographic comparison with standards, where possible, and by gas chromatography-mass spectrometry. The percentage of the dose excreted as metabolites in the urine increased with ring size. Hydroxy and ketone derivatives of all three of the N-nitrosoalicyclic amines were found. Pimelic acid was the major metabolite (congruent to 25%) of N-nitrosoheptamethyleneimine; adipic acid was identified as a metabolite of N-nitrosohexamethyleneimine, but not glutaric acid was found from N-nitrosopiperidine.
D000818:Animals; D002273:Carcinogens / Q000378:metabolism*; D009602:Nitrosamines / Q000008:administration & dosage / Q000378:metabolism* / Q000652:urine; D009603:Nitroso Compounds / Q000652:urine; D051381:Rats; D011916:Rats, Inbred F344
D002273:Carcinogens; D009602:Nitrosamines; D009603:Nitroso Compounds; C002148:N-nitrosoheptamethyleneimine; C045279:N-nitroso-3-hydroxypiperidine; C043305:1-nitroso-4-piperidone; C039010:N-nitroso-4-hydroxypiperidine; C002743:N-nitrosopiperidine; C002742:N-nitrosoperhydroazepine