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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D000079:Acetaldehyde / Q000378:metabolism; D000818:Animals; D002855:Chromatography, Thin Layer; D005557:Formaldehyde / Q000378:metabolism; D006037:Glyoxal / Q000378:metabolism; D006861:Hydrogen Peroxide; D007501:Iron; D008862:Microsomes, Liver / Q000378:metabolism*; D008956:Models, Chemical; D009602:Nitrosamines / Q000378:metabolism*; D010084:Oxidation-Reduction; D051381:Rats
C045076:Fenton's reagent; D009602:Nitrosamines; D005557:Formaldehyde; C002741:N-nitrosomorpholine; D006037:Glyoxal; C043883:N-nitroso-2-hydroxymorpholine; D006861:Hydrogen Peroxide; D007501:Iron; D000079:Acetaldehyde