Showing Compound Card for Tetramethylpyrazine (CDB005429)

Jump To Section:
IdentificationTaxonomyOntologyPhysical propertiesSpectraProtein targetPathwaysConcentrationsLinksReferencesXML
Record Information
Version1.0
Created at2020-04-27 16:19:41 UTC
Updated at2021-01-04 20:37:43 UTC
CannabisDB IDCDB005429
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameTetramethylpyrazine
DescriptionTetramethylpyrazine, or 2,3,5,6-tetramethylpyrazine, or TMP  and also known as FEMA 3237, is an alkylpyrazine and 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. Tetramethylpyrazine is a moderately basic compound with white crystals that are soluble in alcohol, fixed oils, propylene glycol and water. Its odor is described as nutty, musty and vanilla with dry, brown cocoa nuances and it taste is described as nutty, musty, cocoa, drying, peanut-like with raw coffee notes. Tetramethylpyrazine has been detected in roasted beef, cheddar cheese, dairy products, red and yellow bell peppers (c. annuum), potato, filberts, boiled egg, coconut endosperm, cocoa products, green tea, tea leaf, soybean products, soybean seed, macadamia nut, peanut, meat, guava fruit, shrimp, rum and whiskey ( Ref:DOI ). This could make tetramethylpyrazine a potential biomarker for the consumption of these foods. It has been used as a perfuming agent in soaps, detergents, toiletries, fabric softeners, bleach, alcoholic beverages, and fine fragrances. Its biosynthesis in Bacillus involves the amination of acetoin, the latter being derived from pyruvate (doi:10.1038/1951103a0). It exhibits potential nootropic (improved executive function; ¬†PMID:¬†23916742) and anti-inflammatory activities against induced cerebral ischemic in rats (PMID:¬†23644042). Tetramethylpyrazine is also found in cannabis smoke and is formed during the combustion of cannabis ( Ref:DOI ). 
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
2,3,5,6,-Tetramethyl-1,4-pyrazineChEBI
2,3,5,6-TetramethylpyrazineChEBI
FEMA 3237ChEBI
FEMA no. 3237ChEBI
LiqustrazineChEBI
TMPChEBI
TMPZMeSH
ChuanxiongzineMeSH
LigustrazineMeSH
Tetramethyl pyrazineMeSH
Tetramethylpyrazine hydrochlorideMeSH
2356-Tetramethyl-pyrazineChEMBL, HMDB
2356-TetramethylpyrazineChEMBL, HMDB
LigustizineHMDB
TetramethylpyrazinHMDB
TetrapyrazineHMDB
TMP?HMDB
Chemical FormulaC8H12N2
Average Molecular Weight136.19
Monoisotopic Molecular Weight136.1
IUPAC Nametetramethylpyrazine
Traditional Namepyrazine, tetramethyl-
CAS Registry Number1124-11-4
SMILES
CC1=NC(C)=C(C)N=C1C
InChI Identifier
InChI=1S/C8H12N2/c1-5-6(2)10-8(4)7(3)9-5/h1-4H3
InChI KeyFINHMKGKINIASC-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 Point86 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logP1.28Not Available
Predicted Properties
PropertyValueSource
logP1.46ALOGPS
logP0.063ChemAxon
logS-0.96ALOGPS
pKa (Strongest Basic)2.19ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area25.78 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity40.11 m³·mol⁻¹ChemAxon
Polarizability16.02 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-0udr-9300000000-33fe7599448be6d9a1f02015-03-01View Spectrum
GC-MSTetramethylpyrazine, non-derivatized, GC-MS Spectrumsplash10-0udu-9300000000-5d317f2dc804e043f2b9Spectrum
GC-MSTetramethylpyrazine, non-derivatized, GC-MS Spectrumsplash10-0udu-9300000000-5d317f2dc804e043f2b9Spectrum
Predicted GC-MSTetramethylpyrazine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-000i-3900000000-68c7df3c47d48f17b27bSpectrum
Predicted GC-MSTetramethylpyrazine, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Orbitrap 5V, positivesplash10-000i-2900000000-825affe0aeefbf7abe2a2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 6V, positivesplash10-052r-9800000000-0e691fbfc32545d1b1aa2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 8V, positivesplash10-0a4r-9300000000-bd32b31ff50928daf2612020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 9V, positivesplash10-0pb9-9100000000-80bdd2f5e9e721213dba2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 11V, positivesplash10-0ue9-9000000000-a8ff866cfac430f29e972020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 9V, positivesplash10-0002-9000000000-acc42c048c36b7492ded2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 9V, positivesplash10-0a4i-9000000000-e10afcdf21ddde828d7c2020-07-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0900000000-4ea5d7454e8109b365d12016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0900000000-f797c5b258bf45ed58012016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udl-9100000000-465d4f375262ee01acb32016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0900000000-ca8b41e13886eb5f390f2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0900000000-9c6dd6eec8dafc56f8252016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00kr-4900000000-a04f3b4c94a247e992322016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0900000000-ac299646e14f1770c4b52021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-3900000000-997da2b6ee4b7359f4d62021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00kf-9000000000-38545d1df73cc3f6ffdc2021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-1900000000-22a6232d9fbf0c94bc772021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000l-9800000000-d3294b56735618c40d872021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00kf-9100000000-63057d96e8a5e31397952021-09-25View Spectrum
NMR
TypeDescriptionView
1D NMR13C NMR Spectrum (1D, 25.16 MHz, CDCl3, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0036584
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB015495
KNApSAcK IDC00056171
Chemspider ID13658
KEGG Compound IDNot Available
BioCyc IDCPD-15901
BiGG IDNot Available
Wikipedia LinkTetramethylpyrazine
METLIN IDNot Available
PubChem Compound14296
PDB IDNot Available
ChEBI ID133246
References
General ReferencesNot Available