2,3,5,6-TETRAMETHYLPYRAZINE (CHEM007651)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-19 02:28:36 UTC
Update Date2016-11-09 01:13:38 UTC
Accession NumberCHEM007651
Identification
Common Name2,3,5,6-TETRAMETHYLPYRAZINE
ClassSmall Molecule
DescriptionA member of the class of pyrazines that is pyrazine in which all four hydrogens have been replaced by methyl groups. An alkaloid extracted from Chuanxiong (Ligusticum wallichii).
Contaminant Sources
  • EAFUS Chemicals
  • FooDB Chemicals
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical 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 Mass136.194 g/mol
Monoisotopic Mass136.100 g/mol
CAS Registry Number1124-11-4
IUPAC Nametetramethylpyrazine
Traditional Namepyrazine, tetramethyl-
SMILESCC1=NC(C)=C(C)N=C1C
InChI IdentifierInChI=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
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 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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
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
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
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
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0900000000-ac299646e14f1770c4b5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-3900000000-997da2b6ee4b7359f4d6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00kf-9000000000-38545d1df73cc3f6ffdcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-1900000000-22a6232d9fbf0c94bc77Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000l-9800000000-d3294b56735618c40d87Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00kf-9100000000-63057d96e8a5e3139795Spectrum
MSMass Spectrum (Electron Ionization)splash10-0udr-9300000000-33fe7599448be6d9a1f0Spectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
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 IDHMDB0036584
FooDB IDFDB015495
Phenol Explorer IDNot Available
KNApSAcK IDC00056171
BiGG IDNot Available
BioCyc IDCPD-15901
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkTetramethylpyrazine
Chemspider ID13658
ChEBI ID133246
PubChem Compound ID14296
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=11583735
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=18790005
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=21456940
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=23253813
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=23563941
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=2413290
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=24333010
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=25841319
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=26275042
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=26404762
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=27179035
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=27389185
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=27391608
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=27431939
15. https://www.ncbi.nlm.nih.gov/pubmed/?term=27607420
16. https://www.ncbi.nlm.nih.gov/pubmed/?term=27610159
17. https://www.ncbi.nlm.nih.gov/pubmed/?term=27717875
18. 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.
19. Dai XZ, Bache RJ: Coronary and systemic hemodynamic effects of tetramethylpyrazine in the dog. J Cardiovasc Pharmacol. 1985 Sep-Oct;7(5):841-9.
20. 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.
21. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.