115781-42-5

Basic information

• Product Name: N-(3,8-dimethyl-3H-imidazo[4,5-f]quinoxalin-2-yl)-beta-D-glucopyranuronosylamine
• CAS NO: 115781-42-5
• Molecular Formula: C₁₇H₁₉N₅O₆
• Molecular Weight: 389.3627
• Mol File: 115781-42-5.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 742.1°C at 760 mmHg
• Flash Point: 402.6°C
• Density: 1.82g/cm³
• Vapor Pressure: 3.99E-23mmHg at 25°C
• Refractive Index: 1.813
• CAS DataBase Reference: N-(3,8-dimethyl-3H-imidazo[4,5-f]quinoxalin-2-yl)-beta-D-glucopyranuronosylamine(CAS DataBase Reference)
• NIST Chemistry Reference: N-(3,8-dimethyl-3H-imidazo[4,5-f]quinoxalin-2-yl)-beta-D-glucopyranuronosylamine(115781-42-5)
• EPA Substance Registry System: N-(3,8-dimethyl-3H-imidazo[4,5-f]quinoxalin-2-yl)-beta-D-glucopyranuronosylamine(115781-42-5)

Safety Data

• Hazardous Substances Data: 115781-42-5(Hazardous Substances Data)

Upstream product

• 2616-64-0 uridine diphosphoglucuronic acid 
• 115044-41-2 N-hydroxy-MeIQx 

Relevant articles and documents

Metabolism of the food-borne mutagen 2-amino-3,8-dimethylimidazo[4,5-f] quinoxaline in humans

The metabolism of 2-amino-3,8-dimethylimidazo[4,5-f]quinoxaline (MeIQx) was investigated in five human volunteers given a dietary equivalent of 14C-labeled MeIQx. The amount of the dose excreted in urine ranged from 20.2% to 58.6%, with unmetabolized MeIQx accounting for 0.7-2.8% of the dose. Five principal metabolites were detected in urine, and four of the derivatives were characterized by on-line UV spectroscopy and by HPLC-MS following immunoaffinity chromatography. Two metabolites were identified as the phase II conjugates N2,(3,8-dimethylimidazo[4,5-f]quinoxalin-2- yl)sulfamic acid (MeIQx-N2-SO3-) and N2-(β-1-glucosiduronyl)-2-amino- 3,8-dimethylimidazo[4,5-f]quinoxaline (MeIQx-N2-Gl). Two other metabolites were the cytochrome P450-mediated (P450) oxidation products 2-amino-8- (hydroxymethyl)-3-methylimidazo[4,5-f]quinoxaline (8-CH2OH-MeIQx), and N2- (β-1-glucosi duronyl)-N-hydroxy-2-amino-3,8-dimethylimidazo[4,5- f]quinoxaline (NOH-MeIQx-N2-Gl). The latter product is a conjugate of the genotoxic metabolite 2-(hydroxyamino)-3,8-dimethylimidazo- [4,5- f]quinoxaline (NHOH-MeIQx). A large interindividual variation was observed in the metabolism and disposition of MeIQx; these four metabolites and unchanged MeIQx combined accounted for 6.3-26.7% of the total dose. The remaining principal metabolite found in all subjects accounted for 7.6-28% of the dose. It has not been previously identified in rodents or nonhuman primates, and its structure remains unknown. P450-mediated ring oxidation of MeIQx at the C-5 position, a major pathway of detoxication in rodents, was not detected in humans. Both 8-CH2OH-MeIQx formation and NHOH-MeIQx formation are catalyzed by P450 1A2 and may be useful biomarkers of P450 1A2 activity in humans. The levels of NHOH- MeIQx-N2-Gl found in human urine ranged from 1.4% to 10.0% of the dose, which is significantly higher than that formed in rodents and nonhuman primates undergoing cancer bioassays. Thus, bioactivation of MeIQx by P450-mediated N-oxidation is extensive in humans.