2-Amino-3,4,8-trimethyl-3H-imidazo[4,5-f]quinoxaline (CHEM027225)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 23:35:08 UTC
Update Date2016-11-09 01:18:25 UTC
Accession NumberCHEM027225
Identification
Common Name2-Amino-3,4,8-trimethyl-3H-imidazo[4,5-f]quinoxaline
ClassSmall Molecule
DescriptionPyrolysis produced from creatine, threonine and glucose in cooked food.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
2-amino-3,4,8-trimethylimidazo(4,5-F)QuinoxalineHMDB, MeSH
2-amino-3,4,8-trimethylimidazo[4,5-F ]QuinoxalineHMDB
3,4,8-Trimethyl-3H-imidazo(4,5-F)quinoxalin-2-amineHMDB
3,4,8-Trimethyl-3H-imidazo[4,5-F]quinoxalin-2-amine, 9ciHMDB
3,4,8-trimethylimidazo(4,5-F)Quinoxalin-2-amineHMDB, MeSH
4,8-Di-meiqxHMDB
4,8-Dimethyl iqxHMDB
4,8-Dimethyl-iqxHMDB
Di-meiqxHMDB
Dimethyl-iqxHMDB
3,4,8-MeIQXMeSH, HMDB
4,8-DiMeIQxMeSH, HMDB
Chemical FormulaC12H13N5
Average Molecular Mass227.265 g/mol
Monoisotopic Mass227.117 g/mol
CAS Registry Number95896-78-9
IUPAC Name3,4,8-trimethyl-3H-imidazo[4,5-f]quinoxalin-2-amine
Traditional Name3,4,8-trimethylimidazo[4,5-f]quinoxalin-2-amine
SMILESCN1C(N)=NC2=C1C(C)=CC1=C2N=C(C)C=N1
InChI IdentifierInChI=1S/C12H13N5/c1-6-4-8-9(15-7(2)5-14-8)10-11(6)17(3)12(13)16-10/h4-5H,1-3H3,(H2,13,16)
InChI KeyLAZSIJHHPMHKQI-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 DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.43 g/LALOGPS
logP1.35ALOGPS
logP1.31ChemAxon
logS-2.7ALOGPS
pKa (Strongest Basic)5.14ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area69.62 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity65.06 m³·mol⁻¹ChemAxon
Polarizability25.02 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0h9a-0940000000-287862590f79af87e30cSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0090000000-7abee065db4c96324989Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-0190000000-5ddf35b2e0858da7c22cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05am-1910000000-ff5135ab675447c758c2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0090000000-21bed679607205f1e60aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0190000000-213c797e2d539b492d32Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03dl-5590000000-dea2ecb8b10fa6387dffSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0090000000-eaa75a9a8c9828a1b313Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0390000000-51dde21eb5f0e0f76453Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05fs-0900000000-155b8adfd1cb3b5950cfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0090000000-7d0a9d062589b22b4fafSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-0090000000-490293f154e2cc683e9fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a6s-4920000000-c9f7bda89466009a3457Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0032928
FooDB IDFDB010913
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID94552
ChEBI IDNot Available
PubChem Compound ID104739
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Puangsombat K, Gadgil P, Houser TA, Hunt MC, Smith JS: Occurrence of heterocyclic amines in cooked meat products. Meat Sci. 2012 Mar;90(3):739-46. doi: 10.1016/j.meatsci.2011.11.005. Epub 2011 Nov 9.
2. Van Hemelrijck M, Rohrmann S, Steinbrecher A, Kaaks R, Teucher B, Linseisen J: Heterocyclic aromatic amine [HCA] intake and prostate cancer risk: effect modification by genetic variants. Nutr Cancer. 2012;64(5):704-13. doi: 10.1080/01635581.2012.678548. Epub 2012 May 7.
3. 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.
4. 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.
5. 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.
6. Jahurul MH, Jinap S, Ang SJ, Abdul-Hamid A, Hajeb P, Lioe HN, Zaidul IS: Dietary exposure to heterocyclic amines in high-temperature cooked meat and fish in Malaysia. Food Addit Contam Part A Chem Anal Control Expo Risk Assess. 2010 Aug;27(8):1060-71. doi: 10.1080/19440041003801190.
7. Dundar A, Saricoban C, Yilmaz MT: Response surface optimization of effects of some processing variables on carcinogenic/mutagenic heterocyclic aromatic amine (HAA) content in cooked patties. Meat Sci. 2012 Jul;91(3):325-33. doi: 10.1016/j.meatsci.2012.02.011. Epub 2012 Feb 22.
8. Daniel CR, Sinha R, Park Y, Graubard BI, Hollenbeck AR, Morton LM, Cross AJ: Meat intake is not associated with risk of non-Hodgkin lymphoma in a large prospective cohort of U.S. men and women. J Nutr. 2012 Jun;142(6):1074-80. doi: 10.3945/jn.112.158113. Epub 2012 Apr 25.
9. Shao B, Peng Z, Yang H, Wu G, Yao Y, Wan K: [Simultaneous determination of 9 heterocyclic aromatic amine in poultry products by solid-phase extraction-high performance liquid chromatography]. Se Pu. 2011 Aug;29(8):755-61.
10. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.