Oxidoreductases;
Acting on paired donors, with incorporation or reduction of molecular oxygen;
With NADH or NADPH as one donor, and incorporation of one atom of oxygen into the other donor

N,N-dimethylaniline,NADPH:oxygen oxidoreductase (N-oxide-forming)

N,N-dimethylaniline + NADPH + H+ + O2 = N,N-dimethylaniline N-oxide + NADP+ + H2O [RN:R03344]

R03344;
(other) R04523 R08266

N,N-dimethylaniline [CPD:C02846];
NADPH [CPD:C00005];
H+ [CPD:C00080];
O2 [CPD:C00007]

A flavoprotein. A broad spectrum monooxygenase that accepts substrates as diverse as hydrazines, phosphines, boron-containing compounds, sulfides, selenides, iodide, as well as primary, secondary and tertiary amines [3,4]. This enzyme is distinct from other monooxygenases in that the enzyme forms a relatively stable hydroperoxy flavin intermediate [4,5]. This microsomal enzyme generally converts nucleophilic heteroatom-containing chemicals and drugs into harmless, readily excreted metabolites. For example, N-oxygenation is largely responsible for the detoxification of the dopaminergic neurotoxin 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP) [2,6]

EC 1.14.13.8 created 1972 (EC 1.13.12.11 created 1992, part-incorporated 2006), modified 2006

1  [PMID:4381353]

Ziegler DM, Pettit FH.

Microsomal oxidases. I. The isolation and dialkylarylamine oxygenase activity of pork liver microsomes.

Biochemistry 5:2932-8 (1966)

2  [PMID:3262153]

Chiba K, Kubota E, Miyakawa T, Kato Y, Ishizaki T.

Characterization of hepatic microsomal metabolism as an in vivo detoxication pathway of 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine in mice.

J Pharmacol Exp Ther 246:1108-15 (1988)

3

Cashman, J.R.

Structural and catalytic properties of the mammalian flavin-containing monooxygenase.

Chem Res Toxicol 8:165-181 (1995)

4  [PMID:16402899]

Cashman JR, Zhang J.

Human flavin-containing monooxygenases.

Annu Rev Pharmacol Toxicol 46:65-100 (2006)
DOI:10.1146/annurev.pharmtox.46.120604.141043

5  [PMID:3949735]

Jones KC, Ballou DP.

Reactions of the 4a-hydroperoxide of liver microsomal flavin-containing monooxygenase with nucleophilic and electrophilic substrates.

J Biol Chem 261:2553-9 (1986)

6  [PMID:7672012]

Chiba K, Kobayashi K, Itoh K, Itoh S, Chiba T, Ishizaki T, Kamataki T.

N-oxygenation of 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine by the rat liver flavin-containing monooxygenase expressed in yeast cells.

Eur J Pharmacol 293:97-100 (1995)