CAS 76180-96-6

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

Description:

2-Amino-3-methylimidazo[4,5-f]quinoline (CAS 76180-96-6) is a heterocyclic aromatic amine known for its potential mutagenic and carcinogenic properties. It is a derivative of imidazoquinoline, characterized by the presence of an amino group and a methyl group at specific positions on the imidazo ring system. This compound is typically formed during the cooking of certain meats at high temperatures, particularly through the Maillard reaction, which occurs between amino acids and reducing sugars. 2-Amino-3-methylimidazo[4,5-f]quinoline is soluble in organic solvents but has limited solubility in water. Its structure allows it to intercalate into DNA, potentially leading to mutations. Due to its biological activity, it has been the subject of extensive research in the fields of toxicology and cancer studies, particularly concerning its role in the development of various cancers. Safety precautions are necessary when handling this compound, as it poses health risks associated with exposure.

Formula: C₁₁H₁₀N₄

InChI: 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: InChIKey=ARZWATDYIYAUTA-UHFFFAOYSA-N

SMILES: CN1C2=C(C=3C(C=C2)=NC=CC3)N=C1N

Synonyms:

• 2-Amino-3-methylimidazo(4,5-f)quinoline
• 3-Methyl-3H-imidazo(4,5-f)quinolin-2-amine
• 3-methyl-3H-imidazo[4,5-f]quinolin-2-amine hydrobromide (1:1)
• 3H-Imidazo(4,5-f)quinolin-2-amine, 3-methyl-
• 3H-Imidazo(4,5-f)quinoline, 2-amino-3-methyl-
• Brn 5014055
• Ccris 1767
• Hsdb 7085
• IQ
• N3-Iq
• 2-Amino-3-methyl-3H-imidazo[4,5-f]quinoline

2-Amino-3-methyl-3H-imidazo[4,5-f]quinoline

CAS: 76180-96-6

2-Amino-3-methyl-3H-imidazo[4,5-f]quinoline

Formula: C₁₁H₁₀N₄

Purity: ≥95%

Color and Shape: brown to gray solid

Molecular weight: 198.22g/mol

Ref: 54-OR1650T

2-Amino-3-methyl-3H-imidazo[4,5-f]quinoline

Controlled Product

CAS: 76180-96-6

Applications 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.
References Ohgaki, H., et al.: Carcinogenesis, 5, 921 (1984), Stavric, B., et al.: Fd. Chem. Toxic., 31, 12, 981 (1993), Sugimura, T., et al.: Mutation Research, 290, 43 (1993), Eisenbrand & Tang: Toxicology, 84, 1 (1993), Josephy, P.D., et al.: Carcinogenesis, 16, 9, 2037 (1995)

Formula: C₁₁H₁₀N₄

Color and Shape: Off-White To Grey

Molecular weight: 198.22

Ref: TR-A616500

3-Methyl-3H-imidazo[4,5-f]quinolin-2-amine

CAS: 76180-96-6

Purity: 97%

Molecular weight: 198.22900390625

Ref: 10-F726346