78411-56-0

Basic information

• Product Name: 2-Amino-3,7-dimethylimidazo[4,5-f]quinoxaline
• Synonyms: 7-MEIQX;3,7-DiMethyl-3H-iMidazo[4,5-f]quinoxalin-2-aMine
• CAS NO: 78411-56-0
• Molecular Formula: C11H11N5
• Molecular Weight: 213.24
• Product Categories: Detergents;Mutagenesis Research Chemicals
• Mol File: 78411-56-0.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 458.4°C at 760 mmHg
• Flash Point: 231°C
• Appearance: /
• Density: 1.47g/cm³
• Vapor Pressure: 1.38E-08mmHg at 25°C
• Refractive Index: 1.776
• CAS DataBase Reference: 2-Amino-3,7-dimethylimidazo[4,5-f]quinoxaline(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Amino-3,7-dimethylimidazo[4,5-f]quinoxaline(78411-56-0)
• EPA Substance Registry System: 2-Amino-3,7-dimethylimidazo[4,5-f]quinoxaline(78411-56-0)

Safety Data

• Hazardous Substances Data: 78411-56-0(Hazardous Substances Data)

Usage

General Description

2-Amino-3,7-dimethylimidazo[4,5-f]quinoxaline is a chemical compound that belongs to the class of heterocyclic aromatic amines (HAAs), which are formed during the cooking and processing of meat and fish. It is a potent mutagen and carcinogen, known to induce DNA damage and gene mutations. Exposure to 2-Amino-3,7-dimethylimidazo[4,5-f]quinoxaline has been linked to an increased risk of developing certain types of cancer, particularly in the colon and pancreas. It is often formed during high-temperature cooking methods such as grilling, frying, and broiling, making it a potential health concern for individuals with a diet high in charred and well-done meats. Measures to reduce exposure to this chemical, such as avoiding overcooked meats and using cooking methods that produce fewer HAAs, are recommended to reduce the risk of associated health effects.

InChI:InChI=1/C11H11N5/c1-6-5-13-9-7(14-6)3-4-8-10(9)15-11(12)16(8)2/h3-5H,1-2H3,(H2,12,15)

Upstream product

• 506-68-3 bromocyane 
• 96600-58-7 2-methyl-6-methylamino-5-nitroquinoxaline 
• 138336-28-4 2-(N-benzylamino)-3,7-dimethylimidazo<4,5-f>quinoxaline 
• 367-31-7 4-fluoro-1,2-phenylenediamine 
• 364-78-3 2-nitro-4-fluoroaniline 
• 138336-12-6 2-Bromo-3,7-dimethyl-3H-imidazo[4,5-f]quinoxaline 
• 138336-13-7 3,7-dimethyl-2-(methylthio)imidazo<4,5-f>quinoxaline 
• 138336-22-8 3,7-dimethyl-2-(methylsulfonyl)imidazo<4,5-f>quinoxaline 
• 115726-32-4 2-Methyl-5-nitro-quinoxalin-6-ylamine 
• 99-56-9 4-Nitrophenylene-1,2-diamine 
• 615-71-4 benzene-1,2,4-triamine 
• 4188-17-4 2-methyl-6-amino-quinoxaline 
• 2942-02-1 2-methyl-6-nitroquinoxaline 

Relevant articles and documents

Regiospecific Synthesis of the Aminoimidazoquinoxaline (IQx) Mutagens from Cooked Foods

A versatile regiospecific synthesis has been developed to prepare the six dimethyl- and trimethyl-substituted 2-aminoimidazoquinoxaline (IQx) regioisomers 35, 36, 37, 38, 39, and 40 for complete and unambiguous characterization.The key reaction step in the synthetic sequence for these angular tricycles is a photodehydrohalogenative cyclization of suitably substituted pyrazinylimidazolylethylene intermediates derived from common pyrazine and fully functionalized imidazole precursors.The reaction sequence developed allows for versatility in the substitution pattern as well as total regioisomeric control for the synthesis of all possible methyl and polymethyl analogues of IQx.Comparison of the physical properties among the isomeric di- and trimethyl-IQx's has established the value of unambiguous regiospecific synthesis for structural assignments in this food mutagen series.

SYNTHESIS OF 2-AMINO-3,8-DIMETHYLIMIDAZOQUINOXALINE (Me-IQx), A POTENT MUTAGEN ISOLATED FROM FRIED BEEF

A potent mutagen, 2-amino-3,8-dimethylimidazoquinoxaline (Me-IQx), isolated from fried beef and its 3,7-dimethyl derivative were synthesized from 6-amino-3-methylquinoxaline and 6-amino-2-methylquinoxaline, respectively.These compounds showed strong mutagenic activity towards Salmonella typhimurium TA98 in the presence of S9 Mix.