76180-96-6 Usage
Chemical Properties
Beige Powder
Uses
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
Definition
ChEBI: An imidazoquinoline that is 3H-imidazo[4,5-f]quinoline substituted by a methyl group at position 3 and an amino group at position 2.
Synthesis Reference(s)
Chemical and Pharmaceutical Bulletin, 30, p. 1857, 1982 DOI: 10.1248/cpb.30.1857Synthetic Communications, 18, p. 973, 1988 DOI: 10.1080/00397918808060881
General Description
Light tan crystalline solid or tan powder.
Air & Water Reactions
2-AMINO-3-METHYL-3H-IMIDAZO[4,5-F]QUINOLINE is sensitive to light and air. Insoluble in water.
Reactivity Profile
2-AMINO-3-METHYL-3H-IMIDAZO[4,5-F]QUINOLINE may be sensitive to prolonged exposure to heat. 2-AMINO-3-METHYL-3H-IMIDAZO[4,5-F]QUINOLINE is stable under moderately acidic and alkaline conditions and in cold dilute aqueous solutions when protected from light. 2-AMINO-3-METHYL-3H-IMIDAZO[4,5-F]QUINOLINE is rapidly degraded by dilute hypochlorite.
Health Hazard
ACUTE/CHRONIC HAZARDS: It may emit potentially toxic fumes when involved in a fire.
Fire Hazard
Flash point data for 2-AMINO-3-METHYL-3H-IMIDAZO[4,5-F]QUINOLINE are not available; however, 2-AMINO-3-METHYL-3H-IMIDAZO[4,5-F]QUINOLINE is probably combustible.
Safety Profile
Confirmed carcinogen with experimental carcinogenic and tumorigenic data. Mutation data reported. When heated to decomposition it emits toxic fumes of NOx,
Carcinogenicity
IQ is reasonably anticipated to be a human carcinogen based on sufficient evidence of carcinogenicity from studies in experimental animals.
Check Digit Verification of cas no
The CAS Registry Mumber 76180-96-6 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 7,6,1,8 and 0 respectively; the second part has 2 digits, 9 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 76180-96:
(7*7)+(6*6)+(5*1)+(4*8)+(3*0)+(2*9)+(1*6)=146
146 % 10 = 6
So 76180-96-6 is a valid CAS Registry Number.
InChI:InChI=1/C11H10N4.BrH/c1-15-9-5-4-8-7(3-2-6-13-8)10(9)14-11(15)12;/h2-6H,1H3,(H2,12,14);1H
76180-96-6Relevant articles and documents
Characterization of the mutagen 2-amino-3-methylimidazoquinoline prepared from a 2-methylpyridine/creatinine/acetylformaldehyde model system
Lee, Huei,Lin, Ming-Yang,Lin, Shaw Tao
, p. 157 - 162 (1994)
A mixture of 2-methylpyridine, creatinine and aldehydes was heated in diethylene glycol containing 5 percent water for 1 h at 140 deg C. The mutagenic compounds were purified by XAD-2 column chromatography, acid/base partition, blue cotton treatment, thin layer chromatography and HPLC. The active substances purified from each step were monitored by their mutagenicity with Salmonella typhimurium TA98 in the presence of S9 mix. Among the mutagens collected, 2-amino-3-methylimidazoquinoline (IQ) was isolated from HPLC, and was identified by its UV and mass spectrum using a photodiode array detector and mass spectrometry. Our findings appear to be the first experimental evidence to substantiate of hypothetical pathway for the formation of IQ mutagens from a heated model system consisting of a pyridine or pyrazine derivatives, an aldehyde and creatinine or creatine.
2-amino-X-nitrobenzimidazoles as precursors of food-borne carcinogens: A new approach to IQ synthesis
Bella, Maros,Milata, Viktor,Larina, Lyudmila I.
, p. 293 - 296 (2012/06/04)
Cyclization of (non)-methylated nitro-o-phenylenediamines with cyanogen bromide provided nitro-substituted 2-aminobenzimidazoles in good up to excellent yields. Catalytic hydrogenation of 2-amino-1-methyl-5-nitrobenzimidazole yielded 2,5-diamino-1-methylbenzimidazole, which on treatment with 1,1,3,3-tetramethoxypropane in methanol and subsequently after removal of methanol in polyphosphoric acid afforded food-borne carcinogen 2-amino-3-methylimidazo[4,5-f]quinoline (IQ) in 20% yield. Copyright
THE SYNTHESIS OF THREE ISOMERS OF THE FOOD CARCINOGEN IQ
Ronne, Erik,Grivas, Spiros
, p. 101 - 105 (2007/10/02)
2-Amino-3-methyl-3H-imidazoquinoline, 2-amino-3-methyl-3H-imidazoisoquinoline and 2-amino-3-methyl-3H-imidazoisoquinoline were synthesized from 7-methoxyquinoline, 6- and 7-methoxyisoquinolines in 21-28percent overall yields.
