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A1378-83 2-Amino-3-methyl-3H-imidazo[4,5-F]quinoline (IQ) CAS: 76180-96-6

Specifications
References
CAS Number
76180-96-6
Grade
Highly Purified
MDL Number
MFCD00210316
Molecular Formula
C₁₁H₁₀N₄
Molecular Weight
198.22
EU Commodity Code
38220090
Shipping Temp
RT
Storage Temp
4°C
3-Methyl-3H-imidazo[4,5-f]quinolin-2-amine; IQ

IQ is highly mutagenic in the Ames test. Investigations have shown that this compound may be present in broiled fish, fried beef, commercial beef extracts and protein pyrolysates. 2-Amino-3-methyl-3H-imidazo[4,5-f]quinoline (IQ) is a genotoxic agent that can cause DNA damage and cell death in mammalian cells. IQ is metabolized by cytochrome P450 enzymes to reactive metabolites that bind to DNA and inhibit topoisomerase II. This leads to the formation of bulky adducts in the DNA and ultimately causes cell death. IQ has been shown to be carcinogenic in mice, as it induced liver lesions and t-cell lymphomas. The drug has also been used as a model system for the study of carcinogenesis caused by 2-amino-1-methyl-6-phenylimidazo[4,5b]pyridine (PhIP).

Synonyms
3-Methyl-3H-imidazo[4,5-f]quinolin-2-amine; IQ
CAS No
76180-96-6
Molecular Formula
C₁₁H₁₀N₄
Molecular Weight
198.22
Purity (HPLC)
≥98%
Appearance
Off-white to beige solid
Melting Point
>200°C (lit)
Solubility
DMSO (Slightly), Methanol (Slightly)
Elemental Analysis
As Reported
Method of Determining identity
Proton NMR Spectroscopic and Mass Spectrometric Analysis
Storage and Stability
May be stored at RT for short-term only. Long-term storage is recommended at 4°C. For maximum recovery of product, centrifuge the original vial prior to removing the cap.
Important Note
This product as supplied is intended for research use only, not for use in human, therapeutic or diagnostic applications without the expressed written authorization of United States Biological.
Toxicity and Hazards
 All products should be handled by qualified personnel only, trained in laboratory procedures.
References
1. Ohgaki, H., et al.: Carcinogenesis, 5, 921 (1984). 2. Stavric, B., et al.: Fd. Chem. Toxic., 31, 12, 981 (1993). 3. Sugimura, T., et al.: Mutation Research, 290, 43 (1993). 4. Eisenbrand & Tang: Toxicology, 84, 1 (1993). 5. Josephy, P.D., et al.: Carcinogenesis, 16, 9, 2037 (1995)
USBio References
No references available
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