2-Amino-3,8-dimethyl-3H-imidazo[4,5-f]quinoxaline (CHEM003628)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2014-09-11 02:04:08 UTC
Update Date2026-04-02 23:27:13 UTC
Accession NumberCHEM003628
Identification
Common Name2-Amino-3,8-dimethyl-3H-imidazo[4,5-f]quinoxaline
ClassSmall Molecule
Description2-Amino-3,8-dimethyl-3H-imidazo[4,5-f]quinoxaline is found in animal foods. 2-Amino-3,8-dimethyl-3H-imidazo[4,5-f]quinoxaline is a food-related mutagen isolated from cooked meats (especially grilled/barbecued) 2-amino-3,8-dimethyl-3h-imidazo[4,5-f]quinoxaline belongs to the family of Quinoxalines. These are compounds containing a quinoxaline moiety, a bicyclic heterocycle made up of a benzene ring fused to a pyrazine ring.
Contaminant Sources
  • FooDB Chemicals
  • IARC Carcinogens Group 2B
  • Suspected Compounds
  • T3DB toxins
Contaminant Type
  • Food Additive
  • Food Toxin
  • Metabolite
  • Natural Compound
  • Organic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
2-Amino-3,8-dimethyl-3H-imidazo(4,5-F)quinoxalineChEBI
2-Amino-3,8-dimethylimidazo[4,5-F]quinoxalineChEBI
8-MeIQXChEBI
8-Methyl-iqxChEBI
2-amino-3,8-dimethylimidazo(4,5-F)QuinoxalineHMDB, MeSH
2-amino-3,8-dimethylimidazo[4,5-F ]QuinoxalineHMDB
3,8-DiMeIQXHMDB, MeSH
3,8-Dimethyl-3H-imidazo(4,5-F)quinoxalin-2-amineHMDB
3,8-Dimethyl-3H-imidazo[4,5-F]quinoxalin-2-amineHMDB
3,8-Dimethyl-3H-imidazo[4,5-F]quinoxalin-2-amine, 9ciHMDB
3,8-dimethylimidazo(4,5-F)Quinoxaline-2-amineHMDB, MeSH
Me-iqxHMDB, MeSH
MeIQxHMDB
Meiqx CPDHMDB, MeSH
Chemical FormulaC11H11N5
Average Molecular Mass213.239 g/mol
Monoisotopic Mass213.101 g/mol
CAS Registry Number77500-04-0
IUPAC Name3,8-dimethyl-3H-imidazo[4,5-f]quinoxalin-2-amine
Traditional Name3,8-dimethylimidazo[4,5-f]quinoxalin-2-amine
SMILESCN1C(N)=NC2=C1C=CC1=C2N=C(C)C=N1
InChI IdentifierInChI=1S/C11H11N5/c1-6-5-13-7-3-4-8-10(9(7)14-6)15-11(12)16(8)2/h3-5H,1-2H3,(H2,12,15)
InChI KeyDVCCCQNKIYNAKB-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as quinoxalines. Quinoxalines are compounds containing a quinoxaline moiety, a bicyclic heterocycle made up of a benzene ring fused to a pyrazine ring.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassDiazanaphthalenes
Sub ClassBenzodiazines
Direct ParentQuinoxalines
Alternative Parents
Substituents
  • Quinoxaline
  • Benzimidazole
  • Aminoimidazole
  • Benzenoid
  • Pyrazine
  • N-substituted imidazole
  • Azole
  • Heteroaromatic compound
  • Imidazole
  • Azacycle
  • Primary amine
  • Amine
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organic nitrogen compound
  • Organonitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point295 - 300 °C
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.77 g/LALOGPS
logP1.34ALOGPS
logP0.8ChemAxon
logS-2.4ALOGPS
pKa (Strongest Basic)4.76ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area69.62 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity60.02 m³·mol⁻¹ChemAxon
Polarizability22.96 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-03di-9630000000-e8a4917bbc669d325e41Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-03di-9630000000-e8a4917bbc669d325e41Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-053i-0900000000-0d6af152818e5f530c3dSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - APCI-ITFT , negativesplash10-0002-0900000000-03d709fe2574ca7fec31Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-03di-0390000000-8ed87f2afa42aabd3d50Spectrum
LC-MS/MSLC-MS/MS Spectrum - APCI-ITFT , positivesplash10-006t-0910000000-90504cc9714205cd22e3Spectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-03dj-0980000000-50411c62b97c8360d105Spectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-0002-0900000000-11e6669d06720d9153bdSpectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-03di-0090000000-f43e697cafe001331dbeSpectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-03di-0090000000-159c1d3a85e946b03ecaSpectrum
LC-MS/MSLC-MS/MS Spectrum - 50V, Positivesplash10-008a-0900000000-36b0714ea24bc0b0f53cSpectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-03dj-0980000000-52e3471483370bb41dd4Spectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-03di-0390000000-07cadffeea6f6a02ab84Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0090000000-3d4e5561b68230947db9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-0590000000-9909fec9d9bf2ce2c608Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-053r-1900000000-fa1c95b62ff0a0d20450Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0090000000-75942ba4bbc76a904bf8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0390000000-123f616c3a9c164347fcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-002b-3900000000-2678374bc011990ab3acSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0090000000-30d0b34fa4acc6bca290Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0390000000-4fe19f6505755b2da029Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-0920000000-a36acb9976b8ad2b2f1aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0090000000-36fa26cf92b7f44a3ce6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-0090000000-e822b8dab153205d5822Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-0900000000-86a61ce4e597d5f3de49Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)2B, possibly carcinogenic to humans. (9)
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0029864
FooDB IDFDB001093
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID56076
ChEBI ID76604
PubChem Compound ID62275
Kegg Compound IDC19255
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=22138251
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=23600962
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=23624435
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=23681119
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=23810796
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=23862679
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=23898916
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=24168237
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=24200580
10. Zaidi R, Kumar S, Rawat PR: Rapid detection and quantification of dietary mutagens in food using mass spectrometry and ultra performance liquid chromatography. Food Chem. 2012 Dec 15;135(4):2897-903. doi: 10.1016/j.foodchem.2012.07.065. Epub 2012 Jul 20.
11. Aschebrook-Kilfoy B, Ollberding NJ, Kolar C, Lawson TA, Smith SM, Weisenburger DD, Chiu BC: Meat intake and risk of non-Hodgkin lymphoma. Cancer Causes Control. 2012 Oct;23(10):1681-92. doi: 10.1007/s10552-012-0047-2. Epub 2012 Aug 14.
12. Gibis M, Weiss J: Antioxidant capacity and inhibitory effect of grape seed and rosemary extract in marinades on the formation of heterocyclic amines in fried beef patties. Food Chem. 2012 Sep 15;134(2):766-74. doi: 10.1016/j.foodchem.2012.02.179. Epub 2012 Mar 10.
13. Guo H, Pan H, Wang Z, Chen L, Zhang D: [Simultaneous determination of nine heterocyclic aromatic amines in mutton products by solid phase extraction-high performance liquid chromatography]. Se Pu. 2012 Oct;30(10):1074-80.
14. Liao GZ, Wang GY, Zhang YJ, Xu XL, Zhou GH: Formation of heterocyclic amines during cooking of duck meat. Food Addit Contam Part A Chem Anal Control Expo Risk Assess. 2012;29(11):1668-78. doi: 10.1080/19440049.2012.702928. Epub 2012 Jul 30.
15. Hayashi H, Taniai E, Morita R, Hayashi M, Nakamura D, Wakita A, Suzuki K, Shibutani M, Mitsumori K: Enhanced liver tumor promotion but not liver initiation activity in rats subjected to combined administration of omeprazole and beta-naphthoflavone. J Toxicol Sci. 2012;37(5):969-85.
16. Wei M, Kakehashi A, Yamano S, Tamano S, Shirai T, Wanibuchi H, Fukushima S: Lack of Hepatocarcinogenicity of Combinations of Low Doses of 2-amino-3, 8-dimethylimidazo[4,5- f ]quinoxaline and Diethylnitrosamine in Rats: Indication for the Existence of a Threshold for Genotoxic Carcinogens. J Toxicol Pathol. 2012 Sep;25(3):209-14. doi: 10.1293/tox.25.209. Epub 2012 Oct 1.
17. Miller PE, Lazarus P, Lesko SM, Cross AJ, Sinha R, Laio J, Zhu J, Harper G, Muscat JE, Hartman TJ: Meat-related compounds and colorectal cancer risk by anatomical subsite. Nutr Cancer. 2013;65(2):202-26. doi: 10.1080/01635581.2013.756534.
18. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.