2-Amino-3-methyl-3H-imidazo[4,5-F]quinoline - ≥95% , CAS No.76180-96-6

CAS: 76180-96-6 Cat. No.: A330795 Molecular Weight: 198.22 EC Number: 689-809-3

GRADE & PURITY ≥95%

Synonyms

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

Storage

Store at 2-8°C

Shipped In

Wet ice

Overview

2-Amino-3-methyl-3H-imidazo[4,5-F]quinoline is a highly mutagenic compound in the Ames test that is present in protein pyrolysates along with other sources.

Specifications

Synonyms

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

Specifications & Purity

≥95%

Storage

Store at 2-8°C

Shipped In

Wet ice

This product requires cold chain shipping. Ground and other economy services are not available.

Purity

≥95%

Names and Identifiers

• Canonical Smiles: CN1C2=C(C3=C(C=C2)N=CC=C3)N=C1N
• IUPAC Name: 3-methylimidazo[4,5-f]quinolin-2-amine
• InChIKey: ARZWATDYIYAUTA-UHFFFAOYSA-N
• 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)
• Isomeric SMILES: CN1C2=C(C3=C(C=C2)N=CC=C3)N=C1N
• Molecular Weight: 198.22
• Reaxy-Rn: 5014055
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=5014055&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organoheterocyclic compounds
    • Class Quinolines and derivatives

• Kingdom: Organic compounds
• Superclass: Organoheterocyclic compounds
• Class: Quinolines and derivatives
• Subclass: Not available
• Intermediate Tree Nodes: Not available
• Direct Parent: Quinolines and derivatives
• Alternative Parents: Benzimidazoles Pyridines and derivatives N-substituted imidazoles Benzenoids Heteroaromatic compounds Azacyclic compounds Organopnictogen compounds Organonitrogen compounds Hydrocarbon derivatives
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Quinoline - Benzimidazole - Benzenoid - Pyridine - N-substituted imidazole - Heteroaromatic compound - Imidazole - Azole - Azacycle - Organic nitrogen compound - Organopnictogen compound - Hydrocarbon derivative - Organonitrogen compound - Aromatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as quinolines and derivatives. These are compounds containing a quinoline moiety, which consists of a benzene ring fused to a pyrimidine ring to form benzo[b]azabenzene.
• External Descriptors: imidazoquinoline

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Chemical and Physical Properties

• Solubility: Soluble in DMSO, Hydrochloric Acid (aq) and Methanol Slightly
• Melt Point(°C): >292° C (dec.)
• Molecular Weight: 198.220 g/mol
• XLogP3: 1.500
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 198.091 Da
• Monoisotopic Mass: 198.091 Da
• Topological Polar Surface Area: 56.700 Ų
• Heavy Atom Count: 15
• Formal Charge: 0
• Complexity: 245.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

References

1. Shaoxuan Wang, Fei Pan, Xinyan Xu, Qian Fan, Yangyang Wang, Lei Zhao, Liang Zhao.  (2025)  Cyanidin-3-O-Glucoside Mitigates Hepatotoxicity Induced by 2-Amino-3-Methylimidazo[4,5-f]Quinoline via Endogenous and Exogenous Apoptotic Signaling Pathways: Evidence From In Vivo and In Silico Studies.  MOLECULAR NUTRITION & FOOD RESEARCH,  70  (1): (e70363).  [PMID:41452282] [10.1002/mnfr.70363]