76180-96-6

Basic information

• Product Name: 2-AMINO-3-METHYL-3H-IMIDAZO[4,5-F]QUINOLINE
• Synonyms: 3-methyl-3h-imidazo(4,5-f)quinolin-2-amine;5-f)quinoline,2-amino-3-methyl-3h-imidazo(;2-AMINO-3-METHYLIMIDAZO(4,5-F)QUINOLINE;2-AMINO-3-METHYL-3H-IMIDAZO[4,5-F]QUINOLINE;IQ;3H-Imidazo(4,5-f)quinoline, 2-amino-3-methyl.;3H-Imidazo[4,5-f]quinolin-2-amine,3-methyl-(9CI);2-AMINO-3-METHYLIMIDAZO[4,5F]CHINOLIN
• CAS NO: 76180-96-6
• Molecular Formula: C₁₁H₁₀N₄
• Molecular Weight: 198.22
• Product Categories: BENZIMIDAZOLE;Detergents;Mutagenesis Research Chemicals;Amines;Heterocycles
• Mol File: 76180-96-6.mol
• Article Data: 9

Chemical Properties

• Melting Point: >300
• Boiling Point: 325.54°C (rough estimate)
• Flash Point: 231.2 °C
• Appearance: light tan crystalline solid or tan powder
• Density: 1.2366 (rough estimate)
• Vapor Pressure: 1.34E-08mmHg at 25°C
• Refractive Index: 1.4260 (estimate)
• Storage Temp.: Refrigerator
• Solubility: DMSO (Slightly, Heated), Methanol (Slightly)
• CAS DataBase Reference: 2-AMINO-3-METHYL-3H-IMIDAZO[4,5-F]QUINOLINE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-AMINO-3-METHYL-3H-IMIDAZO[4,5-F]QUINOLINE(76180-96-6)
• EPA Substance Registry System: 2-AMINO-3-METHYL-3H-IMIDAZO[4,5-F]QUINOLINE(76180-96-6)

Safety Data

• Hazard Codes: T
• Hazardous Substances Data: 76180-96-6(Hazardous Substances Data)

Usage

Uses

Used in Food Industry:
2-AMINO-3-METHYL-3H-IMIDAZO[4,5-F]QUINOLINE is used as a compound that may be present in various cooked or processed food products for [application reason]. It has been found in broiled fish, fried beef, commercial beef extracts, and protein pyrolysates, which are commonly consumed in the food industry.
Used in Research and Development:
2-AMINO-3-METHYL-3H-IMIDAZO[4,5-F]QUINOLINE is used as a mutagenic compound in the Ames test for [application reason]. The Ames test is a widely used method to determine the mutagenic potential of various compounds, including IQ, which can help researchers understand the effects of these substances on genetic material and their potential implications for human health.

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

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.

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

Upstream product

• 75-59-2 tetramethyl ammoniumhydroxide 
• 76180-97-7 2-amino-3H-imidazo<4,5-f>quinoline 
• 506-68-3 bromocyane 
• 14204-98-9 5-amino-6-methylaminoquinoline 
• 4637-24-5 N,N-dimethyl-formamide dimethyl acetal 
• 107002-97-1 imidazo<4,5-f>quinoline-2(3H)-thione 
• 147-85-3 L-proline 
• 57-00-1 Creatinine 
• 73-22-3 L-Tryptophan 
• 72-18-4 L-valine 
• 56-45-1 L-serin 
• 72-19-5 L-threonine 
• 63-68-3 L-methionine 
• 112-80-1 cis-Octadecenoic acid 

Downstream Products

• 769141-89-1 O⁶-benzyl-8-[(3-methyl-3H-imidazo[4,5-f]quinolin-2-yl)amino]-N9-[3',5'-O-(1,1,3,3-tetrakis(isopropyl)-1,3-disiloxanediyl)-β-D-2'-deoxyribofuranosyl]guanine 
• 896719-51-0 6-benzyloxy-N²-[bis-(4-methoxy-phenyl)-phenyl-methyl]-9-[4-(tert-butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-N⁸-(3-methyl-3H-imidazo[4,5-f]quinolin-2-yl)-9H-purine-2,8-diamine 
• 896719-56-5 6-benzyloxy-9-[4-(tert-butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-N⁸-(3-methyl-3H-imidazo[4,5-f]quinolin-2-yl)-9H-purine-2,8-diamine 
• 115747-35-8 N²-(2'-deoxyguanosin-8-yl)-2-amino-3-methylimidazo[4,5-f]quinoline 
• 832748-19-3 [6-benzyloxy-9-(5,5,7,7-tetraisopropyl-tetrahydro-1,4,6,8-tetraoxa-5,7-disila-cyclopentacycloocten-2-yl)-9H-purin-2-yl]-(3-methyl-2-nitro-3H-imidazo[4,5-f]quinolin-5-yl)-amine 
• 832748-21-7 N²-[2-(2-(4-tert-butylphenoxyacetylamino)-3-methyl-3H-imidazo[4,5-f]quinolin-5-yl)]-[3',5'-O-(1,1,3,3-tetrakis(isopropyl)-1,3-disiloxanediyl)]-2'-deoxyguanosine 
• 113638-86-1 4-Amino-N-[3-(3-methyl-3H-imidazo[4,5-f]quinolin-2-ylamino)-propyl]-benzamide 
• 113638-82-7 N-[3-(3-Methyl-3H-imidazo[4,5-f]quinolin-2-ylamino)-propyl]-4-nitro-benzamide 

Relevant articles and documents

Characterization of the mutagen 2-amino-3-methylimidazoquinoline prepared from a 2-methylpyridine/creatinine/acetylformaldehyde model system

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

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

Synthetic Routes to the Carcinogen IQ and Related 3H-Imidazoquinolines

2-Amino-3-methyl-3H-imidazoquinoline (IQ, 1a) and four new IQ homologues, viz. its 7-methyl, 8-methyl, 9-methyl and 7,9-dimethyl derivatives 1c-1f, have been conveniently synthesized from the appropriate 6-methoxyquinolines 3 rather than from the p

THE SYNTHESIS OF THREE ISOMERS OF THE FOOD CARCINOGEN IQ

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.

CONVENIENT SYNTHESIS OF THE FOOD MUTAGEN 2-AMINO-3-METHYLIMIDAZOQUINOLINE (iq), AND IQ-D3

The title compounds (5 and 10) were each prepared in four steps from commercially available 5-amino-6-nitroquinoline (1) in 41percent overall yield.The key step was the displacement of the methylsulfonyl group of 4 by sodamine.

A Potent Mutagen in Broiled Fish. Part 1. 2-Amino-3-methyl-3H-imidazoloquinoline

A potent mutagen isolated from a methanol extract of sardines broiled under normal domestic conditions was strongly mutagenic to Salmonella typhimurium TA98.Its identity has been established as 2-amino-3-methyl-3H-imidazoquinoline on the basis of spectral evidence and by chemical synthesis.