The metabolism of N-nitrosomorpholine by rat liver microsomes and its oxidation by the Fenton system

The metabolism of N-nitrosomorpholine by rat liver microsomesgave acetaldehyde, formaldehyde, glyoxal and N-nitroso-2-hydroxymorpholine.Oxidation of N-nitroso-morpholine by Fenton's reagent gave acetaldehyde,glycol-aldehyde, glyoxal, (2-hydroxyethoxy)acetaldehyde andN-nitroso-2-hydroxymorpholine. N-Nitroso-3-hydroxymor-pholinewas synthesised. In water the new compound gave mainly acetaldehyde,with glycolaldehyde, (2-hydroxy-ethoxy)acetaldehyde and glyoxal.These observations indicated the probability of 3-hydroxylationin the biological and chemical oxidations. N-Nitroso-3-morpholonebehaved similarly in water to the 3-hydroxy compound, and gavemainly acetaldehyde, with glycollk acid, (2-hydroxyethoxy)aceticacid and glyoxal. N-Nitroso-3-morpholone and N-nitroso-3-hydroxymorpholinereacted with 3, 4-dichlorobenzenethiol. The action of lightor alkali on N-nitrosomorpholine gave glyoxal and labile glyoxal-yieldingcompounds.