Summary
1. After intravenous injections into cats of 0.2 mmoles/kg N,N-dimethylaniline, the N,N-dimethylaniline-N-oxide blood levels of 30–45 mμmoles/ml were estimated. These concentrations are too low to be the main cause of haemoglobin oxidation.
2. In suspensions of cow erythrocytes and in solutions of haemoglobin N,N-dimethylaminoazobenzene-N-oxide (DAB-N-oxide) was more active in producing methaemoglobin as compared with N,N-dimethylaniline-N-oxide. Dealkylation and rearrangement of the N-oxides to form dimethylamino compounds proceeded at a corresponding rate. The nature of the oxidizing molecule is not clear. 1 molecule of DAB-N-oxide produced 10 molecules of methaemoglobin in haemolysates at low concentrations of the N-oxide.
3. Kinetics of dealkylation and rearrangement of both the N-oxides and dialkylamines by ferrous iron and by the model hydroxylase system of Udenfriend have been compared.
4. DAB-N-oxide was dealkylated more rapidly than dimethylaniline-N-oxide by isolated rat liver microsomes, even in the absence of NADPH. Rapid binding to proteins occurs during dealkylation.
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Uehleke, H., Stahn, V. Zur biologischen Bildung von N,N-Dimethylanilin-N-Oxyd und N,N-Dimethylaminoazobenzol-N4-Oxyd aus den Aminen sowie ihre Reaktionen mit Hämoglobin und mit Lebermikrosomen. Naunyn-Schmiedebergs Arch. Pharmak. u. Exp. Path. 255, 287–300 (1966). https://doi.org/10.1007/BF00541022
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DOI: https://doi.org/10.1007/BF00541022