Showing Compound Card for 2,5-Dimethylpyrazine (CDB000725)

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Record Information
Version1.0
Created at2020-03-19 00:53:16 UTC
Updated at2021-01-04 20:37:38 UTC
CannabisDB IDCDB000725
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common Name2,5-Dimethylpyrazine
Description2,5-Dimethylpyrazine, C6H8N2, also known as 2,5-DMP, 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. Alkylpyrazines are chemical compounds based on pyrazine with different substitution patterns. 2,5-Dimethylpyrazine is a moderately basic, colorless to pale yellow clear liquid that is almost insoluble in water and is soluble in alcohol. It has a nutty, peanut, musty, earthy, powdery and slightly roasted with a cocoa powder odor and has a musty, potato, cocoa, nutty, fatty, oily taste ( Ref:DOI ).  2,5-Dimethylpyrazine is found in highest concentration in kohlrabis and has been detected in green vegetables, soy beans, asparagus, tortilla chips, 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), wort and fenugreeks. This could make 2,5-dimethylpyrazine a potential biomarker for the consumption of these foods. 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, which is a chemical reaction between amino acids and reducing sugars that gives browned food its distinctive flavor ( Ref:DOI ). It is used as a flavor additive and odorant in foods such as cereals and products such as cigarettes. It is used to impart fried notes to potato (PMID: 5842022 ), beer and chicken flavors. 2,5-Dimethylpyrazine is also a constituent of cannabis smoke. It is volatilized during the combustion of cannabis ( Ref:DOI ). 
Structure
Thumb
MOLSDFPDBSMILESInChI
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 Weight108.14
Monoisotopic Molecular Weight108.0687
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

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point15 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logP0.63Not Available
Predicted Properties
PropertyValueSource
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
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MS2,5-Dimethylpyrazine, non-derivatized, GC-MS Spectrumsplash10-052f-9300000000-081f35e3a3380ed2698bSpectrum
GC-MS2,5-Dimethylpyrazine, non-derivatized, GC-MS Spectrumsplash10-052f-9300000000-081f35e3a3380ed2698bSpectrum
Predicted GC-MS2,5-Dimethylpyrazine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0a4i-8900000000-2ada7e902f3d0e2b31e9Spectrum
Predicted GC-MS2,5-Dimethylpyrazine, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - , positivesplash10-0a4i-4900000000-7e680d62ffa714f804032017-09-14View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0900000000-9b8f23be4c9d8c94f24d2015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-1900000000-b0964dc373b182b8f4c42015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0k9x-9000000000-dc3ffe8529561fb7b1cb2015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0900000000-032c8099a4abe667a4b92015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0900000000-58fa248974f5ade4ee462015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-7900000000-890f0c8c1e9a4f4bf6ff2015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0900000000-1d4d8b4513a0185581992021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-5900000000-53b7bc7c89378de544822021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-d47061f2d3232fef83182021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-3900000000-a2cd546c692d476da7562021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a59-9400000000-696590183181b11c1a142021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udl-9000000000-c5a37365c74d0ec835372021-09-24View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0035289
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB 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
References
General References
  1. Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. [PubMed:6991645 ]
  2. Deck RE, Chang SS: Identification of 2,5-dimethyl-pyrazine in the volatile flavour compounds of potato chips. Chem Ind. 1965 Jul 24;30:1343-4. [PubMed:5842022 ]