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2-Amino-3,8-dimethylimidazo[4,5-f]quinoxaline (CAS 77500-04-0)

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Alternate Names:
3,8-Dimethyl-3H-Imidazo[4,5-f]quinoxalin-2-amine; MeIQx
Application:
2-Amino-3,8-dimethylimidazo[4,5-f]quinoxaline is a white meat mutagen, heterocyclic amine colorectal adenoma recurrence.
CAS Number:
77500-04-0
Molecular Weight:
213.24
Molecular Formula:
C11H11N5
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-3,8-dimethylimidazo[4,5-f]quinoxaline functions as a potent mutagen in experimental applications. It exerts its mechanism of action by forming DNA adducts, leading to the induction of genetic mutations. 2-Amino-3,8-Dimethylimidazo[4,5-F]Quinoxaline interacts with DNA, causing structural alterations and impairing the fidelity of DNA replication and repair processes. Through its ability to induce DNA damage, 2-Amino-3,8-dimethylimidazo[4,5-f]quinoxaline plays a role in the study of mutagenesis, providing insights into the molecular mechanisms underlying these processes. Its impact on DNA integrity and stability may be relevant for investigating the effects of genotoxic agents.


2-Amino-3,8-dimethylimidazo[4,5-f]quinoxaline (CAS 77500-04-0) References

  1. In vivo genotoxicity of 2-amino-3,8-dimethylimidazo[4, 5-f]quinoxaline in lacI transgenic (Big Blue) mice.  |  Itoh, T., et al. 2000. Mutat Res. 468: 19-25. PMID: 10863154
  2. Lack of initiation activity in rat liver of low doses of 2-amino-3,8-dimethylimidazo[4,5-f]quinoxaline.  |  Fukushima, S., et al. 2003. Cancer Lett. 191: 35-40. PMID: 12609707
  3. Low dose genotoxicity of 2-amino-3,8-dimethylimidazo[4,5-f]quinoxaline (MeIQx) in gpt delta transgenic mice.  |  Masumura, K., et al. 2003. Mutat Res. 541: 91-102. PMID: 14568298
  4. Evidence of a threshold-effect for 2-amino-3,8-dimethylimidazo-[4,5-f]quinoxaline liver carcinogenicity in F344/DuCrj rats.  |  Murai, T., et al. 2008. Toxicol Pathol. 36: 472-7. PMID: 18413788
  5. A comprehensive approach to the profiling of the cooked meat carcinogens 2-amino-3,8-dimethylimidazo[4,5-f]quinoxaline, 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine, and their metabolites in human urine.  |  Gu, D., et al. 2010. Chem Res Toxicol. 23: 788-801. PMID: 20192249
  6. The presence of 2-amino-3,8-dimethylimidazo[4,5-f]quinoxaline in smoked dry bonito (katsuobushi).  |  Kikugawa, K., et al. 1986. Jpn J Cancer Res. 77: 99-102. PMID: 3082835
  7. Identification of acrolein as the reactive carbonyl responsible for the formation of 2-amino-3,8-dimethylimidazo[4,5-f]quinoxaline (MeIQx).  |  Hidalgo, FJ., et al. 2021. Food Chem. 343: 128478. PMID: 33158682
  8. Effects of Chlorophyll a and b in Reducing Genotoxicity of 2-Amino-3,8-dimethylimidazo[4,5-F]quinoxaline (MeIQx).  |  Kocaoğlu Cenkci, S. and Kaya, B. 2022. Biology (Basel). 11: PMID: 35453801
  9. Presence of 2-amino-3,8-dimethylimidazo [4,5-f]quinoxaline (MeIQx) in dialysate from patients with uremia.  |  Yanagisawa, H., et al. 1986. Biochem Biophys Res Commun. 138: 1084-9. PMID: 3753488
  10. Formation of 2-amino-3,8-dimethylimidazo[4,5-f]quinoxaline in a model system by heating creatinine, glycine and glucose.  |  Jägerstad, M., et al. 1984. Mutat Res. 126: 239-44. PMID: 6717461
  11. Urinary excretion of 2-amino-3,8-dimethylimidazo-[4,5-f]quinoxaline in white, black, and Asian men in Los Angeles County.  |  Ji, H., et al. 1994. Cancer Epidemiol Biomarkers Prev. 3: 407-11. PMID: 7920208
  12. Screening of heat-processed Finnish foods for the mutagens 2-amino-3,8-dimethylimidazo[4,5-f]quinoxaline, 2-amino-3,4,8-trimethylimidazo[4,5-f]quinoxaline and 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine.  |  Tikkanen, LM., et al. 1993. Food Chem Toxicol. 31: 717-21. PMID: 8225129
  13. Characterization of the carcinogen 2-amino-3,8-dimethylimidazo[4,5-f]quinoxaline in cooking aerosols under domestic conditions.  |  Yang, CC., et al. 1998. Carcinogenesis. 19: 359-63. PMID: 9498289

Ordering Information

Product NameCatalog #UNITPriceQtyFAVORITES

2-Amino-3,8-dimethylimidazo[4,5-f]quinoxaline, 5 mg

sc-209031
5 mg
$235.00

2-Amino-3,8-dimethylimidazo[4,5-f]quinoxaline, 250 mg

sc-209031A
250 mg
$2452.00