Human Metabolome Database Version 3.5

Showing metabocard for Pyrazine (HMDB34176)

Record Information
Version 3.5
Creation Date 2012-09-11 12:58:10 -0600
Update Date 2013-06-29 19:23:58 -0600
Secondary Accession Numbers None
Metabolite Identification
Common Name Pyrazine
Description Pyrazine is found in fenugreek. Pyrazine is a maillard product In the Staedel-Rugheimer pyrazine synthesis (1876) 2-chloroacetophenone is reacted with ammonia to the amino ketone, then condensed and then oxidized to a pyrazine A variation is the Gutknecht Pyrazine Synthesis (1879) also based on this selfcondensation but differing in the way the alpha-ketoamine is synthesised (the chlorine compound in the above method is a lachrymatory agent); Pyrazine is a heterocyclic aromatic organic compound. Pyrazine is a symmetrical molecule with point group D2h. It is found in folic acid in the form of pterin. Derivatives like Phenazine are well known for their antitumor, antibiotic and diuretic activity. Pyrazine is less basic in nature than pyridine, pyridazine and pyrimidine. Tetramethylpyrazine (also known as ligustrazine) is reported to scavenge superoxide anion and decrease nitric oxide production in human polymorphonuclear leukocytes. Tetramethylpyrazine is also a component of some herbs in Traditional Chinese Medicine.
Structure Thumb
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
  1. 1, 4-Diazabenzene
  2. 1,4-Diazabenzene
  3. 1,4-Diazin
  4. 1,4-Diazine
  5. 2-Cyanopyrazine
  6. Cyanopyrazine
  7. P-Diazine
  8. Paradiazine
  9. Piazine
  10. Piazine (obsol.)
  11. Pyrazin
  12. PYZ
Chemical Formula C4H4N2
Average Molecular Weight 80.088
Monoisotopic Molecular Weight 80.037448138
IUPAC Name pyrazine
Traditional IUPAC Name pyrazine
CAS Registry Number 290-37-9
InChI Identifier InChI=1S/C4H4N2/c1-2-6-4-3-5-1/h1-4H
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Aromatic Heteromonocyclic Compounds
Class Diazines
Sub Class Pyrazines
Other Descriptors
  • Aromatic Heteromonocyclic Compounds
  • diazine(ChEBI)
  • pyrazines(ChEBI)
Substituents None
Direct Parent Pyrazines
Status Expected and Not Quantified
  • Food
  • Nutrient
  • Nutrient
Cellular locations
  • Cytoplasm
  • Extracellular
Physical Properties
State Not Available
Experimental Properties
Property Value Reference
Melting Point 54 - 56 °C Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP -0.26 Not Available
Predicted Properties
Property Value Source
LogP -0.29 ALOGPS
LogP -0.46 ChemAxon
LogS 0.82 ALOGPS
pKa (strongest basic) 0.88 ChemAxon
Hydrogen Acceptor Count 2 ChemAxon
Hydrogen Donor Count 0 ChemAxon
Polar Surface Area 25.78 A2 ChemAxon
Rotatable Bond Count 0 ChemAxon
Refractivity 21.74 ChemAxon
Polarizability 7.62 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 0 ChemAxon
Not Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biofluid Locations Not Available
Tissue Location Not Available
Pathways Not Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
DrugBank Metabolite ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB012468
KNApSAcK ID Not Available
Chemspider ID 8904 Link_out
KEGG Compound ID C02018 Link_out
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Pyrazine Link_out
NuGOwiki Link HMDB34176 Link_out
Metagene Link HMDB34176 Link_out
METLIN ID Not Available
PubChem Compound 9261 Link_out
PDB ID Not Available
ChEBI ID 30953 Link_out
Synthesis Reference Not Available
Material Safety Data Sheet (MSDS) Download (PDF)
General References
  1. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.