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Carcinogenesis. 1986 Apr;7(4):559-65.

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


The metabolism of N-nitrosomorpholine by rat liver microsomes gave acetaldehyde, formaldehyde, glyoxal and N-nitroso-2-hydroxymorpholine. Oxidation of N-nitrosomorpholine by Fenton's reagent gave acetaldehyde, glycolaldehyde, glyoxal, (2-hydroxyethoxy)acetaldehyde and N-nitroso-2-hydroxymorpholine. N-Nitroso-3-hydroxymorpholine was synthesised. In water the new compound gave mainly acetaldehyde, with glycolaldehyde, (2-hydroxyethoxy)acetaldehyde and glyoxal. These observations indicated the probability of 3-hydroxylation in the biological and chemical oxidations. N-Nitroso-3-morpholone behaved similarly in water to the 3-hydroxy compound, and gave mainly acetaldehyde, with glycollic acid, (2-hydroxyethoxy)acetic acid and glyoxal. N-Nitroso-3-morpholone and N-nitroso-3-hydroxymorpholine reacted with 3,4-dichlorobenzenethiol. The action of light or alkali on N-nitrosomorpholine gave glyoxal and labile glyoxal-yielding compounds.

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