115044-41-2

Basic information

• Product Name: 2-Hydroxyamino-3,8-dimethylimidazo[4,5-f]quinoxaline
• Synonyms: N-HYDROXY-MEIQX;2-Hydroxyamino-3,8-dimethylimidazo[4,5-f]quinoxaline Discontinued;N-(3,8-DIMETHYL-3H-IMIDAZO[4,5-F]QUINOXALIN-2-YL)HYDROXYLAMINE
• CAS NO: 115044-41-2
• Molecular Formula: C₁₁H₁₁N₅O
• Molecular Weight: 229.24
• Product Categories: Detergents;Mutagenesis Research Chemicals
• Mol File: 115044-41-2.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 427.8°Cat760mmHg
• Flash Point: 212.5°C
• Appearance: /
• Density: 1.53g/cm³
• Vapor Pressure: 1.59E-07mmHg at 25°C
• Refractive Index: 1.772
• Solubility: Methanol, THF
• PKA: 10.91±0.20(Predicted)
• Stability: Light Sensitive
• CAS DataBase Reference: 2-Hydroxyamino-3,8-dimethylimidazo[4,5-f]quinoxaline(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Hydroxyamino-3,8-dimethylimidazo[4,5-f]quinoxaline(115044-41-2)
• EPA Substance Registry System: 2-Hydroxyamino-3,8-dimethylimidazo[4,5-f]quinoxaline(115044-41-2)

Safety Data

• Hazardous Substances Data: 115044-41-2(Hazardous Substances Data)

Usage

Chemical Properties

Red-Brown Solid

Uses

Different sources of media describe the Uses of 115044-41-2 differently. You can refer to the following data:
1. Mutagenic derivative of the heterocyclic arylamine, MeIQx
2. Mutagenic derivative of the heterocyclic arylamine, MeIQx.

InChI:InChI=1/C11H11N5O/c1-6-5-12-7-3-4-8-10(9(7)13-6)14-11(15-17)16(8)2/h3-5,12-13H,1-2H3

Upstream product

• 115044-40-1 2-nitro-3,8-dimethylimidazo[4,5-f]quinoxaline 

Downstream Products

• 130146-80-4 N²-(β-1-glucosiduronyl)-2-(hydroxyamino)-3,8-dimethylimidazo[4,5-f]quinoxaline 
• 115781-42-5 N²-(β-1-Glucosiduronyl)-2-amino-3,8-dimethylimidazo[4,5-f]quinoxaline 
• 446253-36-7 N-acetyl-2-amino-5-acetoxy-3,8-dimethylimidazo[4,5-f]quinoxaline 

Relevant articles and documents

Cytochrome P450-mediated metabolism and DNA binding of 2-Amino-1,7- dimethylimidazo[4,5-g]quinoxaline and its carcinogenic isomer 2-amino-3,8-dimethylimidazo[4,5-f]quinoxaline in mice

2-Amino-1,7-dimethylimidazo[4,5-g]quinoxaline (MeIgQx) is a recently discovered heterocyclic aromatic amine (HAA) that is formed during the cooking of meats. MeIgQx is an isomer of 2-amino-3,8-dimethylmidazo[4,5-f]quinoxaline (MeIQx), a rodent carcinogen and possible human carcinogen that also occurs in cooked meats. MeIgQx is a bacterial mutagen, but knowledge about its metabolism and carcinogenic potential is lacking. Metabolism studies on MeIgQx and MeIQx were conducted with human and mouse liver microsomes, and recombinant human P450s. DNA binding studies were also investigated in mice to ascertain the genotoxic potential of MeIgQx in comparison to MeIQx. Both HAAs underwent comparable rates of N-oxidation to form genotoxic N-hydroxylated metabolites with mouse liver microsomes (0.2-0.3 nmol/min/mg protein). The rate of N-oxidation of MeIQx was 4-fold greater than the rate of N-oxidation of MeIgQx with human liver microsomes (1.7 vs 0.4 nmol/min/mg protein). The rate of N-oxidation, by recombinant human P450 1A2, was comparable for both substrates (6 pmol/min/pmol P450 1A2). MeIgQx also underwent N-oxidation by human P450s 1A1 and 1B1 at appreciable rates, whereas MeIQx was poorly metabolized by these P450s. The potential of MeIgQx and MeIQx to form DNA adducts was assessed in female C57BL/6 mice given [14C]-MeIgQx (10 μCi, 9.68 mg/kg body wt) or [14C]-MeIQx (10 μCi, 2.13 mg/kg body wt). DNA adduct formation in the liver, pancreas, and colorectum was measured by accelerator mass spectrometry at 4, 24, or 48 h post-treatment. Variable levels of adducts were detected in all organs. The adduct levels were similar for both HAAs, when adjusted for dose, and ranged from 1 to 600 adducts per 107 nucleotides per mg/kg dose. Thus, MeIgQx undergoes metabolic activation and binds to DNA at levels that are comparable to MeIQx. Given the high amounts of MeIgQx formed in cooked meats, further investigations are warranted to assess the carcinogenic potential of this HAA.