CAS 92180-79-5

2-Amino-3,7,8-trimethylimidazo[4,5-f]quinoxaline

Description:

2-Amino-3,7,8-trimethylimidazo[4,5-f]quinoxaline, commonly referred to as TMQ, is a heterocyclic aromatic amine that is primarily recognized for its presence as a mutagenic compound formed during the cooking of certain foods, particularly those subjected to high-temperature processes like grilling or frying. This compound features a fused imidazoquinoxaline structure, which contributes to its biological activity. TMQ is characterized by its amino group and multiple methyl substituents, which influence its chemical reactivity and potential interactions with biological systems. It is known to exhibit mutagenic properties, raising concerns regarding its role in carcinogenesis, particularly in relation to dietary exposure. The compound is typically analyzed in food safety assessments and toxicological studies to evaluate its impact on human health. Due to its complex structure, TMQ can be challenging to synthesize and isolate, making it a subject of interest in both environmental chemistry and food science research.

Formula: C₁₂H₁₃N₅

InChI: InChI=1/C12H13N5/c1-6-7(2)15-10-8(14-6)4-5-9-11(10)16-12(13)17(9)3/h4-5H,1-3H3,(H2,13,16)

InChI key: InChIKey=JFQHIQJNQCWLNR-UHFFFAOYSA-N

SMILES: CN1C2=C(C=3C(C=C2)=NC(C)=C(C)N3)N=C1N

Synonyms:

• 2-Amino-3,7,8-trimethylimidazo(4,5-f)quinoxaline
• 3,7,8-Trimethyl-3H-imidazo(4,5-f)quinoxalin-2-amine
• 3,7,8-Trimethylimidazo[4,5-f]quinoxalin-2-amine
• 3H-Imidazo(4,5-f)quinoxalin-2-amine, 3,7,8-trimethyl-
• 7,8-DimeIQX
• 7,8-Dimethyl-IQX
• Brn 6062569
• Ccris 6401
• (3,7,8-trimethylimidazo[4,5-f]quinoxalin-2-yl)amine
• 7,8-DiMeIQ
• 2-AMINO-3,7,8-TRIMETHYL-3H-IMIDAZO[4,5-F]QUINOXALINE

2-Amino-3,7,8-trimethyl-3H-imidazo[4,5-f]quinoxaline

CAS: 92180-79-5

Formula: C₁₂H₁₃N₅

Purity: 97%

Color and Shape: Solid

Molecular weight: 227.2651

Ref: IN-DA00631O

2-Amino-3,7,8-trimethyl-3H-imidazo[4,5-f]quinoxaline

CAS: 92180-79-5

2-Amino-3,7,8-trimethyl-3H-imidazo[4,5-f]quinoxaline

Purity: 97%

Ref: 54-OR3160T

2-Amino-3,7,8-trimethyl-3H-imidazo[4,5-f]quinoxaline

Controlled Product

CAS: 92180-79-5

Applications A mutagenic/carcinogenic heterocyclic amine under moderate conditions such as 37°C and 50°C.
References Sugimura, T., et al.: Mutation Research, 290, 43 (1993), Eisenbrand & Tang: Toxicology, 84, 1 (1993), Vikse, R., et al.: Mutation Research, 298, 207 (1993)

Formula: C₁₂H₁₃N₅

Color and Shape: Yellow

Molecular weight: 227.27

Ref: TR-A631600

2-Amino-3,7,8-trimethyl-3H-imidazo[4,5-f]quinoxaline

CAS: 92180-79-5

2-Amino-3,7,8-trimethyl-3H-imidazo[4,5-f]quinoxaline is a synthetic compound that is used as an analytical reagent. It has been shown to inhibit the growth of cancer cells by reacting with amines in the cell nucleus and forming the corresponding quinone. This reaction products then react with alkoxy radical to form reactive oxygen species that induce apoptosis. The use of 2-amino-3,7,8-trimethyl-3H-imidazo[4,5-f]quinoxaline as an analytical reagent has been shown to be effective in the determination of creatine and creatinine levels.

Formula: C₁₂H₁₃N₅

Purity: Min. 95%

Molecular weight: 227.27 g/mol

Ref: 3D-FA17506