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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2012-09-11 20:14:46 UTC
Update Date2022-03-07 02:54:27 UTC
HMDB IDHMDB0035289
Secondary Accession Numbers
  • HMDB35289
Metabolite Identification
Common Name2,5-Dimethylpyrazine
Description2,5-Dimethylpyrazine, also known as fema 3272 or pyrazine,2,5-dimethyl, belongs to the class of organic compounds known as pyrazines. Pyrazines are compounds containing a pyrazine ring, which is a six-member aromatic heterocycle, that consists of two nitrogen atoms (at positions 1 and 4) and four carbon atoms. 2,5-Dimethylpyrazine is a cocoa, grass, and medicinal tasting compound. 2,5-Dimethylpyrazine is found, on average, in the highest concentration within kohlrabis. 2,5-Dimethylpyrazine has also been detected, but not quantified, in several different foods, such as green vegetables, soy beans, asparagus, tortilla chips, and fenugreeks. This could make 2,5-dimethylpyrazine a potential biomarker for the consumption of these foods. It occurs naturally in baked potato, black or green tea, crispbread, French fries, malt, peated malt, raw asparagus, roasted barley, roasted filberts or pecans, squid, wheat bread, wild rice (Zizania aquatica), and wort. Alkylpyrazines are chemical compounds based on pyrazine with different substitution patterns. Some alkylpyrazines are naturally occurring highly aromatic substances which often have a very low odor threshold and contribute to the taste and aroma of various foods including coffee and wines. Alkylpyrazines are also formed during the cooking of some foods via Maillard reactions.
Structure
Data?1563862695
Synonyms
ValueSource
25-Dimethyl-pyrazineChEMBL, HMDB
2, 5-DimethylpyrazineHMDB
2,5-Dimethyl pyrazineHMDB
2,5-Dimethyl-1,4-diazineHMDB
2,5-Dimethyl-pyrazineHMDB
2,5-DimethylparadiazineHMDB
2,5-DimethylpiazineHMDB
FEMA 3272HMDB
PYRAZINE,2,5-dimethylHMDB
2,6-DimethylpyrazineMeSH
2,5-DMPMeSH
Chemical FormulaC6H8N2
Average Molecular Weight108.1411
Monoisotopic Molecular Weight108.068748266
IUPAC Name2,5-dimethylpyrazine
Traditional Name2,5-dimethylpyrazine
CAS Registry Number123-32-0
SMILES
CC1=CN=C(C)C=N1
InChI Identifier
InChI=1S/C6H8N2/c1-5-3-8-6(2)4-7-5/h3-4H,1-2H3
InChI KeyLCZUOKDVTBMCMX-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as pyrazines. Pyrazines are compounds containing a pyrazine ring, which is a six-member aromatic heterocycle, that consists of two nitrogen atoms (at positions 1 and 4) and four carbon atoms.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassDiazines
Sub ClassPyrazines
Direct ParentPyrazines
Alternative Parents
Substituents
  • Pyrazine
  • Heteroaromatic compound
  • Azacycle
  • Organic nitrogen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological location

Source

Physical Properties
StateLiquid
Experimental Molecular Properties
PropertyValueReference
Melting Point15 °CNot Available
Boiling Point154.00 to 156.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility31970 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP0.63Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility184 g/LALOGPS
logP0.62ALOGPS
logP-0.2ChemAxon
logS0.23ALOGPS
pKa (Strongest Basic)1.59ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area25.78 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity30.93 m³·mol⁻¹ChemAxon
Polarizability11.91 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+121.64631661259
DarkChem[M-H]-118.97531661259
DeepCCS[M+H]+124.93930932474
DeepCCS[M-H]-121.83830932474
DeepCCS[M-2H]-158.60430932474
DeepCCS[M+Na]+133.54830932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
2,5-DimethylpyrazineCC1=CN=C(C)C=N11305.1Standard polar33892256
2,5-DimethylpyrazineCC1=CN=C(C)C=N1873.1Standard non polar33892256
2,5-DimethylpyrazineCC1=CN=C(C)C=N1920.3Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - 2,5-Dimethylpyrazine EI-B (Non-derivatized)splash10-052f-9300000000-081f35e3a3380ed2698b2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 2,5-Dimethylpyrazine EI-B (Non-derivatized)splash10-052f-9300000000-081f35e3a3380ed2698b2018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2,5-Dimethylpyrazine GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-8900000000-2ada7e902f3d0e2b31e92016-09-22Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2,5-Dimethylpyrazine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - 2,5-Dimethylpyrazine , positive-QTOFsplash10-0a4i-4900000000-7e680d62ffa714f804032017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,5-Dimethylpyrazine 10V, Positive-QTOFsplash10-0a4i-0900000000-9b8f23be4c9d8c94f24d2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,5-Dimethylpyrazine 20V, Positive-QTOFsplash10-0a4i-1900000000-b0964dc373b182b8f4c42015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,5-Dimethylpyrazine 40V, Positive-QTOFsplash10-0k9x-9000000000-dc3ffe8529561fb7b1cb2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,5-Dimethylpyrazine 10V, Negative-QTOFsplash10-0a4i-0900000000-032c8099a4abe667a4b92015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,5-Dimethylpyrazine 20V, Negative-QTOFsplash10-0a4i-0900000000-58fa248974f5ade4ee462015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,5-Dimethylpyrazine 40V, Negative-QTOFsplash10-0a4i-7900000000-890f0c8c1e9a4f4bf6ff2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,5-Dimethylpyrazine 10V, Negative-QTOFsplash10-0a4i-0900000000-1d4d8b4513a0185581992021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,5-Dimethylpyrazine 20V, Negative-QTOFsplash10-0a4i-5900000000-53b7bc7c89378de544822021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,5-Dimethylpyrazine 40V, Negative-QTOFsplash10-0006-9000000000-d47061f2d3232fef83182021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,5-Dimethylpyrazine 10V, Positive-QTOFsplash10-0a4i-3900000000-a2cd546c692d476da7562021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,5-Dimethylpyrazine 20V, Positive-QTOFsplash10-0a59-9400000000-696590183181b11c1a142021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,5-Dimethylpyrazine 40V, Positive-QTOFsplash10-0udl-9000000000-c5a37365c74d0ec835372021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen Locations
  • Feces
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Campylobacter jejuni infection
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Clostridium difficile infection
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Ulcerative Colitis
details
Associated Disorders and Diseases
Disease References
Ulcerative colitis
  1. Garner CE, Smith S, de Lacy Costello B, White P, Spencer R, Probert CS, Ratcliffe NM: Volatile organic compounds from feces and their potential for diagnosis of gastrointestinal disease. FASEB J. 2007 Jun;21(8):1675-88. Epub 2007 Feb 21. [PubMed:17314143 ]
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB013954
KNApSAcK IDC00052608
Chemspider ID28992
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkAlkylpyrazine
METLIN IDNot Available
PubChem Compound31252
PDB ID25R
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1008141
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .