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2-Amino-3,4,8-trimethyl-3H-imidazo[4,5-f]quinoxaline (CAS 95896-78-9)

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Alternate Names:
3,4,8-Trimethyl-3H-imidazo[4,5-f]quinoxalin-2-amine; 4,8-DiMeIQx
CAS Number:
95896-78-9
Molecular Weight:
227.27
Molecular Formula:
C12H13N5
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
* Refer to Certificate of Analysis for lot specific data.

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2-Amino-3,4,8-trimethyl-3H-imidazo[4,5-f]quinoxaline (ATQ) is a heterocyclic aromatic compound found to be associated with the formation of carcinogenic/mutagenic heterocyclic amines in fried beef steak. Within the realm of scientific research, 2-Amino-3,4,8-trimethyl-3H-imidazo[4,5-f]quinoxaline has demonstrated a broad range of applications. As a derivative of the quinoxaline family, known for their electron-donating properties, 2-Amino-3,4,8-trimethyl-3H-imidazo[4,5-f]quinoxaline has been employed in various capacities, including as a fluorescent dye, a fluorescent probe, and a reporter molecule. In scientific research, 2-Amino-3,4,8-trimethyl-3H-imidazo[4,5-f]quinoxaline has been utilized extensively as a fluorescent dye, leveraging its strong fluorescence and its capacity to interact with specific proteins and enzymes. This characteristic makes it an invaluable tool for studying the structure, dynamics, and function of these molecules. Additionally, 2-Amino-3,4,8-trimethyl-3H-imidazo[4,5-f]quinoxaline has found use as a fluorescent probe, facilitating investigations into the intricate workings of proteins. Moreover, in studies pertaining to gene expression and protein-protein interactions, 2-Amino-3,4,8-trimethyl-3H-imidazo[4,5-f]quinoxaline has served as a reporter molecule. The precise mechanism of action of 2-Amino-3,4,8-trimethyl-3H-imidazo[4,5-f]quinoxaline is not yet fully understood, but it is believed to interact with the amino acid tryptophan and the enzyme cytochrome P450. Furthermore, 2-Amino-3,4,8-trimethyl-3H-imidazo[4,5-f]quinoxaline exhibits interactions with other proteins and enzymes, including thioredoxin reductase and glutathione reductase. As a consequence, it has been discovered to inhibit the activity of certain enzymes, such as thioredoxin reductase and glutathione reductase. Notably, 2-Amino-3,4,8-trimethyl-3H-imidazo[4,5-f]quinoxaline has also demonstrated the ability to modulate the expression of specific genes, particularly those involved in apoptosis and cell cycle regulation. In addition to its diverse molecular interactions, 2-Amino-3,4,8-trimethyl-3H-imidazo[4,5-f]quinoxaline has exhibited anti-inflammatory and antioxidant effects.


2-Amino-3,4,8-trimethyl-3H-imidazo[4,5-f]quinoxaline (CAS 95896-78-9) References

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  2. Effects of (+)-catechin and (-)-epicatechin on heterocyclic amines-induced oxidative DNA damage.  |  Haza, AI. and Morales, P. 2011. J Appl Toxicol. 31: 53-62. PMID: 20583320
  3. Genotoxicity and induction of DNA damage responsive genes by food-borne heterocyclic aromatic amines in human hepatoma HepG2 cells.  |  Pezdirc, M., et al. 2013. Food Chem Toxicol. 59: 386-94. PMID: 23810796
  4. Strong luminescence of carbon dots induced by acetone passivation: efficient sensor for a rapid analysis of two different pollutants.  |  Cayuela, A., et al. 2013. Anal Chim Acta. 804: 246-51. PMID: 24267089
  5. Inhibitory profiles of chilli pepper and capsaicin on heterocyclic amine formation in roast beef patties.  |  Zeng, M., et al. 2017. Food Chem. 221: 404-411. PMID: 27979221
  6. Inhibitory effects of Sichuan pepper (Zanthoxylum bungeanum) and sanshoamide extract on heterocyclic amine formation in grilled ground beef patties.  |  Zeng, M., et al. 2018. Food Chem. 239: 111-118. PMID: 28873528
  7. Genotoxicity of heterocyclic amines (HCAs) on freshly isolated human peripheral blood mononuclear cells (PBMC) and prevention by phenolic extracts derived from olive, olive oil and olive leaves.  |  Fuccelli, R., et al. 2018. Food Chem Toxicol. 122: 234-241. PMID: 30321573
  8. Formation of DNA adducts by the food mutagen 2-amino-3,4,8-trimethyl-3H-imidazo[4,5-f]quinoxaline (4,8-DiMeIQx) in vitro and in vivo. Identification of a N2-(2'-deoxyguanosin-8-yl)-4,8-DiMeIQx adduct.  |  Frandsen, H., et al. 1994. Carcinogenesis. 15: 2553-8. PMID: 7955105

Ordering Information

Product NameCatalog #UNITPriceQtyFAVORITES

2-Amino-3,4,8-trimethyl-3H-imidazo[4,5-f]quinoxaline, 10 mg

sc-209027
10 mg
$372.00