title: Metabolism and mutagenicity of N-nitrosohexamethyleneimine and its hydroxylated derivatives.
abstract: There is a direct relationship between the metabolism and mutagenicity of N-nitrosohexamethyleneimine (NO-HEX) in the presence of uninduced and AC- and PB-induced S8 and S9 fractions from rats and hamsters. Although alpha-hydroxylation is the most important process in the formation of mutagens, NO-HEX may be hydroxylated on the beta- and gamma-carbon atoms as well. beta- and gamma-hydroxyNO-HEX do not appear to play a significant role in the total mutagenicity of NO-HEX. Using rat liver subcellular fractions, beta- and gamma-hydroxyNO-HEX are only marginally mutagenic compared with NO-HEX. With hamster S9 fractions, beta-hydroxyNO-HEX is equally as mutagenic as NO-HEX itself, but gamma-hydroxyNO-HEX is a much less potent mutagen. However, beta-hydroxyNO-HEX is produced in small amounts and therefore does not contribute greatly to the total mutagenicity of NO-HEX.
mesh_terms: D000818:Animals; D001711:Biotransformation; D006224:Cricetinae; D006900:Hydroxylation; D007700:Kinetics; D008297:Male; D008647:Mesocricetus; D008862:Microsomes, Liver / Q000378:metabolism*; D009152:Mutagenicity Tests; D009153:Mutagens / Q000378:metabolism* / Q000494:pharmacology; D009154:Mutation; D009602:Nitrosamines / Q000378:metabolism* / Q000494:pharmacology; D051381:Rats; D011916:Rats, Inbred F344; D011919:Rats, Inbred Strains; D012486:Salmonella typhimurium / Q000187:drug effects; D013329:Structure-Activity Relationship
chemical_list: D009153:Mutagens; D009602:Nitrosamines; C002742:N-nitrosoperhydroazepine