Tetramethylpyrazine

Tetramethylpyrazine, also known as ligustrazine, is a chemical compound found in nattō and in fermented cocoa beans.^[1] In an observational study, tetramethylpyrazine was the dominant volatile organic compound in one sourdough starter.^[2] When purified, tetramethylpyrazine is a colorless solid. It is classified as an alkylpyrazine. Its biosynthesis involves amination of acetoin, the latter derived from pyruvate.^[3] It exhibits potential nootropic and antiinflammatory activities in rats.^[4][5]

Tetramethylpyrazine

Names
Preferred IUPAC name Tetramethylpyrazine
Other names Ligustrazine; Tetrapyrazine
Identifiers
CAS Number	1124-11-4
3D model (JSmol)	Interactive image
ChEBI	CHEBI:133246
ChemSpider	13658
ECHA InfoCard	100.013.084
EC Number	214-391-2
PubChem CID	14296
UNII	V80F4IA5XG Y
CompTox Dashboard (EPA)	DTXSID6047070
InChI InChI=1S/C8H12N2/c1-5-6(2)10-8(4)7(3)9-5/h1-4H3 Key: FINHMKGKINIASC-UHFFFAOYSA-N InChI=1S/C8H12N2/c1-5-6(2)10-8(4)7(3)9-5/h1-4H3 Key: FINHMKGKINIASC-UHFFFAOYSA-N
SMILES CC1=C(N=C(C(=N1)C)C)C
Properties
Chemical formula	C8H12N2
Molar mass	136.198 g·mol−1
Melting point	84–86 °C (183–187 °F; 357–359 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references