112631
2-Methoxy-4-nitroaniline
98%
Synonym(s):
4-Nitro-o-anisidine
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About This Item
Linear Formula:
CH3OC6H3(NO2)NH2
CAS Number:
Molecular Weight:
168.15
Beilstein:
879619
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22
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Quality Level
Assay
98%
mp
140-142 °C (lit.)
SMILES string
COc1cc(ccc1N)[N+]([O-])=O
InChI
1S/C7H8N2O3/c1-12-7-4-5(9(10)11)2-3-6(7)8/h2-4H,8H2,1H3
InChI key
GVBHRNIWBGTNQA-UHFFFAOYSA-N
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General description
2-Methoxy-4-nitroaniline is an important inducer of CYP1A2 owing to its small molecular size.
Application
2-Methoxy-4-nitroaniline is used as a photometric reagent for the determination of ethinylestradiol (ETE), a semi-synthetic estrogen that is widely used in oral contraceptives.
Biochem/physiol Actions
The metabolism of 2-methoxy-4-nitroaniline (MNA) occurs via the hydroxylation of the phenyl ring to form 6-hydroxy MNA in Harlan Sprague Dawley rats and B6C3F(1)/N mice.
Signal Word
Warning
Hazard Statements
Precautionary Statements
Hazard Classifications
Acute Tox. 4 Oral - Aquatic Chronic 2 - Carc. 2
Storage Class Code
11 - Combustible Solids
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
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Use of nitroanilines for spectrophotometric determination of ethinylestradiol in pharmaceutical formulations.
Leonardo SG, et al.
Analytical Methods : Advancing Methods and Applications, 3(5), 1198-1201 (2011)
James M Mathews et al.
Xenobiotica; the fate of foreign compounds in biological systems, 42(12), 1213-1224 (2012-06-26)
The disposition of 2-Methoxy-4-nitroaniline (MNA) was investigated in male and female Harlan Sprague Dawley rats and B6C3F(1)/N mice following oral, intravenous, and dermal exposure to [(14)C]MNA at 2, 15, or 150 mg/kg. Clearance of MNA was investigated in male and
M Degawa et al.
Cancer letters, 96(1), 95-98 (1995-09-04)
Male F344 rats were treated with a chemical (aniline, nitrobenzene, 2-methoxy-p-phenylenediamine, 2-methoxy-4-nitroaniline or 2-methoxy-4-nitroazobenzene) produced by the azo-reduction and/or N-oxidation of 2-methoxy-4-amino-azo-benzene, a selective inducer of cytochrome P450IA2 (CYP1A2), and their effects on the induction of CYP1A enzymes in the
Rachel P Frawley et al.
Toxicology, 441, 152474-152474 (2020-05-08)
2-Methoxy-4-nitroaniline (MNA), an intermediate in the synthesis of azo dyes used in textiles and paints, is structurally similar to carcinogenic anilines. Human exposure occurs primarily in the occupational setting through handling of dye dust, and through use and disposal of
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