Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C12H12N4 |
| Molecular Weight | 212.2505 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CN1C(N)=NC2=C1C(C)=CC3=NC=CC=C23
InChI
InChIKey=GMGWMIJIGUYNAY-UHFFFAOYSA-N
InChI=1S/C12H12N4/c1-7-6-9-8(4-3-5-14-9)10-11(7)16(2)12(13)15-10/h3-6H,1-2H3,(H2,13,15)
| Molecular Formula | C12H12N4 |
| Molecular Weight | 212.2505 |
| 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 |
|---|---|---|
| Naturally occurring food toxins. | 2010-09 |
|
| Determination of heterocyclic amines in urine samples by capillary liquid chromatography with evaporated light-scattering detection. | 2010-05 |
|
| Validation of an in vitro screening test for predicting the tumor promoting potential of chemicals based on gene expression. | 2010-04 |
|
| Implication of replicative stress-related stem cell ageing in radiation-induced murine leukaemia. | 2009-07-21 |
|
| Effect of beer/red wine marinades on the formation of heterocyclic aromatic amines in pan-fried beef. | 2008-11-26 |
|
| In vitro inhibitory activity of probiotic spore-forming bacilli against genotoxins. | 2008-03 |
|
| Biochemical basis of genotoxicity of heterocyclic arylamine food mutagens: Human DNA polymerase eta selectively produces a two-base deletion in copying the N2-guanyl adduct of 2-amino-3-methylimidazo[4,5-f]quinoline but not the C8 adduct at the NarI G3 site. | 2006-09-01 |
|
| Differential effects of heterocyclic amines on poly(ADP-ribose) polymerase-1 and mono-ADP-ribosyltransferase A. | 2006-09 |
|
| Lack of formation of heterocyclic amines in fumes from frying French fries. | 2006-09 |
|
| Effect of pH on binding of mutagenic heterocyclic amines by the natural biopolymer poly(gamma-glutamic acid). | 2006-08-23 |
|
| Suppression of MeIQ-induced SOS response by allylbenzenes from Asiasarum heterotropoides in the Salmonella typhimurium OY1001/1A2 umu test. | 2006-06 |
|
| 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. | 2005-10-25 |
|
| Induction of colon tumors in C57BL/6J mice fed MeIQx, IQ, or PhIP followed by dextran sulfate sodium treatment. | 2005-04 |
|
| Suppression of chemical mutagen-induced SOS response by allylbenzen from Asiasarum heterotropoides in the Salmonella typhimurium TA1535/PSK1002 umu test. | 2005-01 |
|
| Determination of heterocyclic aromatic amines (HAs) content in samples of household-prepared meat dishes. | 2004-03-25 |
|
| Uptake of heterocyclic aromatic amine by insoluble dietary fiber in artificial gastric and intestinal juice. | 2004-03 |
|
| Selection of human cytochrome P450 1A2 mutants with enhanced catalytic activity for heterocyclic amine N-hydroxylation. | 2004-02-03 |
|
| Functional characterization of four allelic variants of human cytochrome P450 1A2. | 2004-02-01 |
|
| Biphasic effects of the flavonoids quercetin and naringenin on the metabolic activation of 2-amino-3,5-dimethylimidazo[4,5-f]quinoline by Salmonella typhimurium TA1538 co-expressing human cytochrome P450 1A2, NADPH-cytochrome P450 reductase, and cytochrome b5. | 2004-01-12 |
|
| Selected heterocyclic amines. | 2004 |
|
| Regional mutagenicity of heterocyclic amines in the intestine: mutation analysis of the cII gene in lambda/lacZ transgenic mice. | 2003-08-05 |
|
| Beta-catenin mutations in liver tumors induced by 2-amino-3,4-dimethylimidazo[4,5-f]quinoline in CDF1 mice. | 2003-07-30 |
|
| Enhancing risk of ethanol on MeIQx-induced rat hepatocarcinogenesis is accompanied with increased levels of cellular proliferation and oxidative stress. | 2003-03-20 |
|
| Inhibition of mutagenicity of food-derived heterocyclic amines by sulforaphane--a constituent of broccoli. | 2003-03 |
|
| Inhibitory effect of dibenzoylmethane on mutagenicity of food-derived heterocyclic amine mutagens. | 2003 |
|
| Inhibitory effect of curcumin and its natural analogues on genotoxicity of heterocyclic amines from cooked food. | 2002-12 |
|
| Estimation of dietary HCA intakes in a large-scale population-based prospective study in Japan. | 2002-09-30 |
|
| Mutagenicity of food-derived carcinogens and the effect of antioxidant vitamins. | 2002 |
|
| Chromosome aberrations induced in mice by chronic feeding of 2-amino-3,4-dimethylimidazo[4,5-f]quinoline (MeIQ). | 1998-06 |
|
| No direct correlation between mutant frequencies and cancer incidence induced by MeIQ in various organs of Big Blue mice. | 1998-05-25 |
|
| Establishment of a Salmonella tester strain highly sensitive to mutagenic heterocyclic amines. | 1998-05-01 |
|
| Three-dimensional modelling of human cytochrome P450 1A2 and its interaction with caffeine and MeIQ. | 1997-07 |
|
| p53 mutations in MeIQ-induced mouse forestomach tumors. | 1997-02 |
|
| Simultaneous expression of human CYP3A7 and N-acetyltransferase in Chinese hamster CHL cells results in high cytotoxicity for carcinogenic heterocyclic amines. | 1995-07-10 |
|
| Mutation, loss of heterozygosity, and recombination of the p53 gene in mouse forestomach tumors induced by 2-amino-3,4-dimethylimidazo[4,5-f]quinoline. | 1995-01 |
|
| Genetic alterations in HCA-induced tumors. | 1995 |
|
| Function and localization of cytochromes P450 involved in the metabolic activation of food-derived heterocyclic amines. | 1995 |
|
| Dietary carcinogens and mammary carcinogenesis. Induction of rat mammary carcinomas by administration of heterocyclic amines in cooked foods. | 1994-08-01 |
|
| 2-Amino-3,4-dimethylimidazo[4,5-f]quinoline induces and inhibits cytochrome P450 from the IA subfamily in chick and rat hepatocytes. | 1992-07-01 |
|
| Uroporphyrinogen oxidation catalyzed by reconstituted cytochrome P450IA2. | 1992-05-01 |
|
| Metabolism of food-derived heterocyclic amines in human and rabbit tissues by P4503A proteins in the presence of flavonoids. | 1992-04-01 |
|
| Detection of a Ha-ras point mutation by polymerase chain reaction-single strand conformation polymorphism analysis in 2-amino-3,4-dimethylimidazo[4,5-f]quinoline-induced mouse forestomach tumors. | 1992-02-29 |
|
| Enhancement of GST-P positive liver cell foci development by combined treatment of rats with five heterocyclic amines at low doses. | 1991-05 |
|
| Metabolism of 2-acetylaminofluorene and benzo(a)pyrene and activation of food-derived heterocyclic amine mutagens by human cytochromes P-450. | 1990-06-01 |
|
| Carcinogenic potential of cooked food mutagens (IQ and MeIQ) in Wistar rats after short-term exposure. | 1989-11 |
|
| Human liver microsomal cytochrome P-450 enzymes involved in the bioactivation of procarcinogens detected by umu gene response in Salmonella typhimurium TA 1535/pSK1002. | 1989-06-15 |
|
| Induction of tumors in the Zymbal gland, oral cavity, colon, skin and mammary gland of F344 rats by a mutagenic compound, 2-amino-3,4-dimethylimidazo[4,5-f]quinoline. | 1989-03 |
|
| Induction of hepatocellular carcinoma and highly metastatic squamous cell carcinomas in the forestomach of mice by feeding 2-amino-3,4-dimethylimidazo[4,5-f]quinoline. | 1986-11 |
|
| Carcinogenicity in mice and rats of heterocyclic amines in cooked foods. | 1986-08 |
|
| Carcinogenicities in mice and rats of IQ, MeIQ, and MeIQx. | 1985 |
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 19:12:21 GMT 2025
by
admin
on
Mon Mar 31 19:12:21 GMT 2025
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| Record UNII |
G2Q7M1P33X
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| Record Status |
Validated (UNII)
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| Record Version |
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Systematic Name | English | ||
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77094-11-2
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7766
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62274
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G2Q7M1P33X
Created by
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PRIMARY |
| Related Record | Type | Details | ||
|---|---|---|---|---|
|
PARENT -> CONSTITUENT ALWAYS PRESENT |
Heterocyclic amine skin content in cooked food sample. 375?52 pg/g sample.
Heterocyclic amine flesh content in cooked food sample. 67 pg/g sample.
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|
PARENT -> CONSTITUENT ALWAYS PRESENT |
Heterocyclic amine content in cooked food sample. 424?87 pg/g sample.
|
||
|
PARENT -> CONSTITUENT ALWAYS PRESENT |
Heterocyclic amine flesh content in cooked food sample. 180 pg/g sample.
|
||
|
PARENT -> CONSTITUENT ALWAYS PRESENT |
Heterocyclic amine skin content in cooked food sample. 317?14 pg/g sample.
|
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|
PARENT -> CONSTITUENT ALWAYS PRESENT |
Heterocyclic amine in cooked meat sample. 86?12 pg/g sample.
|
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PARENT -> CONSTITUENT ALWAYS PRESENT |
Heterocyclic amine in cooked meat sample. 142?22 pg/g sample.
|
||
|
PARENT -> CONSTITUENT ALWAYS PRESENT |
Semi-Dried(Aji-Hiraki) JAPANESE HORSE MACKEREL SKIN, COOKED
Heterocyclic amine skin content in cooked food sample. 262?41 pg/g sample.
Heterocyclic amine flesh content in cooked food sample. 70 pg/g sample.
|
||
|
PARENT -> CONSTITUENT ALWAYS PRESENT |
Heterocyclic amine skin content in cooked food sample. 435?57 pg/g sample.
Heterocyclic amine flesh content in cooked food sample. 98 pg/g sample.
|
||
|
PARENT -> CONSTITUENT ALWAYS PRESENT |
Heterocyclic amine flesh content in cooked food sample. 319 pg/g sample.
|
||
|
PARENT -> CONSTITUENT ALWAYS PRESENT |
Heterocyclic amine in well cooked meat sample. 94?12 pg/g sample.
Heterocyclic amine in medium cooked meat sample. 125?31 pg/g sample.
|
