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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 21:44:31 UTC
Update Date2019-07-23 06:21:32 UTC
HMDB IDHMDB0036584
Secondary Accession Numbers
  • HMDB36584
Metabolite Identification
Common NameTetramethylpyrazine
DescriptionTetramethylpyrazine, also known as fema 3237 or TMP, 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 (based on its pKa). Its biosynthesis involves amination of acetoin, the latter derived from pyruvate. Tetramethylpyrazine is a burnt, chocolate, and cocoa tasting compound. Outside of the human body, Tetramethylpyrazine has been detected, but not quantified in, several different foods, such as pepper (c. annuum), milk and milk products, red bell peppers, potato, and yellow bell peppers. This could make tetramethylpyrazine a potential biomarker for the consumption of these foods. When purified, tetramethylpyrazine is a colorless solid. It is classified as an alkylpyrazine. It exhibits potential nootropic and antiinflammatory activities in rats.
Structure
Data?1563862892
Synonyms
ValueSource
2,3,5,6,-Tetramethyl-1,4-pyrazineChEBI
2,3,5,6-TetramethylpyrazineChEBI
FEMA 3237ChEBI
FEMA no. 3237ChEBI
LiqustrazineChEBI
TMPChEBI
2356-Tetramethyl-pyrazineHMDB
2356-TetramethylpyrazineHMDB
ChuanxiongzineHMDB
LigustizineHMDB
LigustrazineHMDB
TetramethylpyrazinHMDB
TetrapyrazineHMDB
TMP?HMDB
Tetramethyl pyrazineMeSH
Tetramethylpyrazine hydrochlorideMeSH
TMPZMeSH
Chemical FormulaC8H12N2
Average Molecular Weight136.1943
Monoisotopic Molecular Weight136.100048394
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
Water Solubility15 g/LALOGPS
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
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0udu-9300000000-5d317f2dc804e043f2b9Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0udu-9300000000-5d317f2dc804e043f2b9Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000i-3900000000-68c7df3c47d48f17b27bSpectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 5V, positivesplash10-000i-2900000000-825affe0aeefbf7abe2aSpectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 6V, positivesplash10-052r-9800000000-0e691fbfc32545d1b1aaSpectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 8V, positivesplash10-0a4r-9300000000-bd32b31ff50928daf261Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 9V, positivesplash10-0pb9-9100000000-80bdd2f5e9e721213dbaSpectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 11V, positivesplash10-0ue9-9000000000-a8ff866cfac430f29e97Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 9V, positivesplash10-0002-9000000000-acc42c048c36b7492dedSpectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 9V, positivesplash10-0a4i-9000000000-e10afcdf21ddde828d7cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0900000000-4ea5d7454e8109b365d1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0900000000-f797c5b258bf45ed5801Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udl-9100000000-465d4f375262ee01acb3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0900000000-ca8b41e13886eb5f390fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0900000000-9c6dd6eec8dafc56f825Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00kr-4900000000-a04f3b4c94a247e99232Spectrum
MSMass Spectrum (Electron Ionization)splash10-0udr-9300000000-33fe7599448be6d9a1f0Spectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB015495
KNApSAcK IDNot Available
Chemspider ID13658
KEGG Compound IDNot Available
BioCyc IDCPD-15901
BiGG IDNot Available
Wikipedia LinkTetramethylpyrazine
METLIN IDNot Available
PubChem Compound14296
PDB IDNot Available
ChEBI ID133246
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Zhu XL, Xiong LZ, Wang Q, Liu ZG, Ma X, Zhu ZH, Hu S, Gong G, Chen SY: Therapeutic time window and mechanism of tetramethylpyrazine on transient focal cerebral ischemia/reperfusion injury in rats. Neurosci Lett. 2009 Jan 2;449(1):24-7. doi: 10.1016/j.neulet.2008.09.007. Epub 2008 Sep 6. [PubMed:18790005 ]
  2. Dai XZ, Bache RJ: Coronary and systemic hemodynamic effects of tetramethylpyrazine in the dog. J Cardiovasc Pharmacol. 1985 Sep-Oct;7(5):841-9. [PubMed:2413290 ]
  3. Li M, Handa S, Ikeda Y, Goto S: Specific inhibiting characteristics of tetramethylpyrazine, one of the active ingredients of the Chinese herbal medicine 'Chuanxiong,' on platelet thrombus formation under high shear rates. Thromb Res. 2001 Oct 1;104(1):15-28. [PubMed:11583735 ]
  4. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .