2-AMINO-3-METHYLIMIDAZO(4,5-F)QUINOLINE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C11H10N4
Molecular Weight	198.2239
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure of 2-AMINO-3-METHYLIMIDAZO(4,5-F)QUINOLINE

Structure Search

SMILES

CN1C(N)=NC2=C1C=CC3=NC=CC=C23

InChI

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)

HIDE SMILES / InChI

Molecular Formula	C11H10N4
Molecular Weight	198.2239
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Approval Year

PubMed

Title	Date	PubMed
Establishment of a Salmonella tester strain highly sensitive to mutagenic heterocylic amines.	1999 Sep 1	10503888
Colonic cell proliferation, apoptosis and aberrant crypt foci development in rats given 2-amino-3-methylimidaz.	2001 Apr	11330454
Potent antimutagenic activity of white tea in comparison with green tea in the Salmonella assay.	2001 Aug 22	11448643
Contrasting effects of acute and chronic dietary exposure to 2-amino-3-methyl-imidazo[4,5-f]quinoline (IQ) on xenobiotic metabolising enzymes in the male Fischer 344 rat: implications for chemoprevention studies.	2001 Feb	11315504
DNA adduct formation by 2-amino-3-methylimidazo [4,5-f] quinoline (IQ) in rat colon.	2001 Feb	11286010
beta-Catenin mutation in rat colon tumors initiated by 1,2-dimethylhydrazine and 2-amino-3-methylimidazo[4,5-f]quinoline, and the effect of post-initiation treatment with chlorophyllin and indole-3-carbinol.	2001 Feb	11181454
Post-initiation effects of chlorophyllin and indole-3-carbinol in rats given 1,2-dimethylhydrazine or 2-amino-3-methyl- imidazo.	2001 Feb	11181453
Synthesis of the C8-deoxyguanosine adduct of the food mutagen IQ.	2001 Feb 22	11178826
Assessing carcinogen exposure with MS.	2001 Jul 1	11467580
Contributions of major components to the antimutagenic effect of Hsian-tsao (Mesona procumbens Hemsl.).	2001 Oct	11600058
Intestinal microflora plays a crucial role in the genotoxicity of the cooked food mutagen 2-amino-3-methylimidazo [4,5-f]quinoline.	2001 Oct	11577015
Nitrosation and nitration of 2-amino-3-methylimidazo[4,5-f]quinoline by reactive nitrogen oxygen species.	2002 Aug	12184790
Mutagenicity of 2-amino-3-methylimidazo[4,5-f]quinoline in colon and liver of Big Blue rats: role of DNA adducts, strand breaks, DNA repair and oxidative stress.	2002 Aug	12151358
Flavonoids inhibit genetic toxicity produced by carcinogens in cells expressing CYP1A2 and CYP1A1.	2002 Jan	11752233
Effects of soy sauce and sugar on the formation of heterocyclic amines in marinated foods.	2002 Jul	12065221
Reactivity and selectivity of the N-acetyl-Glu-P-1, N-acetyl-Glu-P-2, N-acetyl-MeIQx, and N-acetyl-IQx nitrenium ions: comparison to carbocyclic N-arylnitrenium ions.	2002 Jul 10	12095341
Antimutagenic activities of various lactic acid bacteria against food mutagens: heterocyclic amines.	2002 May	12222811
One dose of 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) or 2-amino-3-methylimidazo[4,5-f]quinoline (IQ) induces tumours in Min/+ mice by truncation mutations or LOH in the Apc gene.	2002 May 27	12034317
Effect of CYP1A2 deficiency on heterocyclic amine DNA adduct levels in mice.	2002 Oct	12387319
Induction of tumors in the colon and liver of the immunodeficient (SCID) mouse by 2-amino-3-methylimidazo[4,5-f ]quinoline (IQ)-modulation by long-chain fatty acids.	2002 Sep	12189196
Mammary gland carcinogenesis by food-derived heterocyclic amines and studies on the mechanisms of carcinogenesis of 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP).	2002 Sep 30	12351154
Modulation by flavonoids of the effects of a food mutagen in different thalassaemia genotypes in the Comet assay.	2003	14691983
Prevention of heterocyclic amine-induced DNA damage in colon and liver of rats by different lactobacillus strains.	2003 Dec	12970070
Chemoprevention of 2-amino-3-methylimidazo[4,5-f]quinoline (IQ)-induced colonic and hepatic preneoplastic lesions in the F344 rat by cruciferous vegetables administered simultaneously with the carcinogen.	2003 Feb	12584175
Promotion versus suppression of rat colon carcinogenesis by chlorophyllin and chlorophyll: modulation of apoptosis, cell proliferation, and beta-catenin/Tcf signaling.	2003 Feb-Mar	12628520
Contrasting effects of non-starch polysaccharide and resistant starch-based diets on the disposition and excretion of the food carcinogen, 2-amino-3-methylimidazo[4,5-f]quinoline (IQ), in a rat model.	2003 Jun	12738184
Dietary low-dose sucrose modulation of IQ-induced genotoxicity in the colon and liver of Big Blue rats.	2003 Jun 19	12787917
Effects of dietary antioxidants and 2-amino-3-methylimidazo[4,5-f]- quinoline (IQ) on preneoplastic lesions and on oxidative damage, hormonal status, and detoxification capacity in the rat.	2003 Oct	12909264
Formation and reduction of aryl and heterocyclic nitroso compounds and significance in the flux of hydroxylamines.	2004 Apr	15089095
Inhibitory effects of beer on heterocyclic amine-induced mutagenesis and PhIP-induced aberrant crypt foci in rat colon.	2004 Apr 11	15066585
An improved method for the extraction of mutagens from human urine and cooked meat using blue rayon.	2004 Apr 11	15066580
Anti-genotoxic activity of the mushroom Lactarius vellereus extract in bacteria and in mammalian cells in vitro.	2004 Mar	15074597
Protective effects of Brussels sprouts, oligosaccharides and fermented milk towards 2-amino-3-methylimidazo[4,5-f]quinoline (IQ)-induced genotoxicity in the human flora associated F344 rat: role of xenobiotic metabolising enzymes and intestinal microflora.	2004 Mar 25	15036016
Effect of common Brassica vegetables (Brussels sprouts and red cabbage) on the development of preneoplastic lesions induced by 2-amino-3-methylimidazo[4,5-f]quinoline (IQ) in liver and colon of Fischer 344 rats.	2004 Mar 25	15036015
Effect of intestinal microfloras from vegetarians and meat eaters on the genotoxicity of 2-amino-3-methylimidazo[4,5-f]quinoline, a carcinogenic heterocyclic amine.	2004 Mar 25	15036013
Sucrose and IQ induced mutations in rat colon by independent mechanism.	2004 Oct 4	15450425
Induction of colon tumors in C57BL/6J mice fed MeIQx, IQ, or PhIP followed by dextran sulfate sodium treatment.	2005 Apr	15635146
The effects of thyme volatiles on the induction of DNA damage by the heterocyclic amine IQ and mitomycin C.	2005 Mar 7	15725604
Investigation of the separation of heterocyclic aromatic amines by reversed phase ion-pair liquid chromatography coupled with tandem mass spectrometry: the role of ion pair reagents on LC-MS/MS sensitivity.	2005 Oct 25	15878313

Substance Class	Chemical Created by `admin` on `Fri Dec 15 17:26:44 GMT 2023` Edited by `admin` on `Fri Dec 15 17:26:44 GMT 2023`
Record UNII	30GL3D3T0G
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

2-AMINO-3-METHYLIMIDAZO(4,5-F)QUINOLINE

Systematic Name

English

IQ [IARC]

Common Name

English

2-AMINO-3-METHYL-3H-IMIDAZO(4,5-F)QUINOLINE

Systematic Name

English

N3-IQ

Common Name

English

2-AMINO-3-METHYLIMIDAZO(4,5-F)QUINOLINE [HSDB]

Common Name

English

3H-IMIDAZO(4,5-F)QUINOLIN-2-AMINE, 3-METHYL-

Systematic Name

English

3-METHYL-3H-IMIDAZO(4,5-F)QUINOLIN-2-AMINE

Systematic Name

English

IQ

Common Name

English

Code System Code Type Description

PUBCHEM

53462