A food-derived carcinogen
Technical Support & Resources

Information provided in the product description is from published literature. Due to the nature of scientific experimentation, your results (e.g., selectivity and effective concentrations) or specific application for this product may differ. If you have questions about how this product fits your application, please contact our technical support staff.

Visit our FAQ

Contact Us

Toll Free Phone (USA and Canada Only): (888) 526-5351
Direct Phone: (734) 975-3888

Request Technical Support

Technical Support Request

To streamline the process attach the appropriate questionnaire to your inquiry.

Download IHC QuestionnaireDownload WB Questionnaire

View Our Privacy Statement for details on how we use and protect your data. In addition, this site is protected by hCaptcha and its Privacy Policy and Terms of Service apply.

2-Amino-3-methylimidazo[4,5-f]quinoline

Item No. 21853

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
3-methyl-3H-imidazo[4,5-f]quinolin-2-amine
CAS Number
76180-96-6
Synonyms
  • IQ
Molecular Formula
C11H10N4
Formula Weight
198.2
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 10 mg/mlDMSO: 10 mg/mlEthanol: 15 mg/mlEthanol:PBS (pH 7.2) (1:3): 0.25 mg/ml
λmax
210, 262, 363 nm
SMILES
NC(N1C)=NC2=C1C=CC3=C2C=CC=N3
InChi Code
InChI=1S/C11H10N4/c1-15-9-5-4-8-7(3-2-6-13-8)10(9)14-11(15)12/h2-6H,1H3,(H2,12,14)
InChi Key
ARZWATDYIYAUTA-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
Recommended Products

Certificates of Analysis & Batch Specific Data

Provide batch numbers separated by commas to download or request available product inserts, QC sheets, certificates of analysis, data packs, and GC-MS data.

Download most recent Certificate of Analysis for this product

    10 mg

    $41

    Add

    50 mg

    $178

    Add

    100 mg

    $312

    Add
    Cayman Chemical
    Visit Our Environmental Toxicology Resource Center

    Explore additional resources to study natural toxins, pollutants including PFAS and 6-PPD-Q, and their biological effects.

    ENVIRONMENTAL TOXICOLOGY TOOLS & SERVICES
    Product Description

    2-Amino-3-methylimidazo[4,5-f]quinoline (IQ) is a food-derived carcinogen that is found in high temperature-cooked meats and tobacco smoke.1 In humans, IQ is metabolized by the cytochrome (CYP) P450 isoform CYP1A2 and conjugated by N-acetyltransferase or sulfotransferase to a metabolite that reacts with DNA to form adducts. It induces formation of single-base substitutions and exon deletions and increases cell death in vitro in a concentration-dependent manner. In vivo, IQ increases the incidence of squamous cell hyperplasias in the stomach of p53 knockout mice and increases hepatocellular lesions in female mice regardless of p53 status.2

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. 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).

    2. Hirata, A., Tsukamoto, T., Yamamoto, M., et al. Organ-dependent susceptibility of p53 knockout mice to 2-amino-3-methylimidazo[4,5-f]quinoline (IQ). Cancer Sci. 98(8), 1164-1173 (2007).