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CAS 122719-38-4

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5-hydroxy-2-amino-3-methylimidazo(4,5-f)quinoline

Description:
5-Hydroxy-2-amino-3-methylimidazo(4,5-f)quinoline, commonly referred to as 5-HO-MIQ, is a heterocyclic aromatic amine that is of interest due to its potential role as a mutagen and carcinogen. This compound is characterized by its complex structure, which includes an imidazoquinoline core with hydroxyl and amino functional groups. It 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. The presence of the hydroxyl group enhances its reactivity, potentially leading to DNA adduct formation, which is a critical step in the carcinogenic process. 5-HO-MIQ is soluble in organic solvents and exhibits a relatively high melting point. Its biological activity has been studied in various models, highlighting its potential implications in cancer research. As with many heterocyclic amines, understanding its properties and behavior in biological systems is essential for assessing its risk factors related to human health.
Formula:C11H10N4O
InChI:InChI=1/C11H10N4O/c1-15-7-5-8(16)10-6(3-2-4-13-10)9(7)14-11(15)12/h2-5,16H,1H3,(H2,12,14)
SMILES:Cn1c2cc(c3c(cccn3)c2[nH]c1=N)O
Synonyms:
  • 5-Oh-Iq
  • 3H-Imidazo(4,5-f)quinolin-5-ol, 2-amino-3-methyl-
  • 2-amino-3-methyl-3H-imidazo[4,5-f]quinolin-5-ol
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