A food-derived carcinogen
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2-Amino-3,8-dimethylimidazo-[4,5-f]-quinoxaline

Item No. 34812

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
3,8-dimethyl-3H-imidazo[4,5-f]quinoxalin-2-amine
CAS Number
77500-04-0
Synonyms
  • MeIQx
Molecular Formula
C11H11N5
Formula Weight
213.2
Purity
≥95%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMSO: Slightly solubleMethanol: Slightly soluble
SMILES
NC(N1C)=NC2=C1C=CC3=NC=C(C)N=C32
InChi Code
InChI=1S/C11H11N5/c1-6-5-13-7-3-4-8-10(9(7)14-6)15-11(12)16(8)2/h3-5H,1-2H3,(H2,12,15)
InChi Key
DVCCCQNKIYNAKB-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Cayman Chemical
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    Product Description

    2-Amino-3,8-dimethylimidazo-[4,5-f]-quinoxaline (MeIQx) is a food-derived carcinogen that has been found in high temperature-cooked fish and meats.1 It is activated by hydroxylation and subsequent O-acetylation via the cytochrome P450 (CYP) isoform CYP1A2 and N-acetyltransferase 2, respectively, in UV5 cells expressing the human enzymes to a metabolite that reacts with DNA to form adducts.2 MeIQx (200 and 400 ppm in the diet) induces tumor formation in rats.3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Johansson, M.A., and Jägerstad, M. Occurrence of mutagenic/carcinogenic heterocyclic amines in meat and fish products, including pan residues, prepared under domestic conditions. Carcinogenesis 15(8), 1511-1518 (1994).

    2. Metry, K.J., Neale, J.R., Doll, M.A., et al. Effect of rapid human N-acetyltransferase 2 haplotype on DNA damage and mutagenesis induced by 2-amino-3-methylimidazo-[4,5-f]quinoline (IQ) and 2-amino-3,8-dimethylimidazo-[4,5-f]quinoxaline (MeIQx). Mutat. Res. 684(1-2), 66-73 (2010).

    3. Kushida, H., Wakabayashi, K., Sato, H., et al. Dose-response study of MeIQx carcinogenicity in F344 male rats. Cancer Lett. 83(1-2), 31-35 (1994).