IUPAC name
Other names
Ligustrazine; Tetrapyrazine
3D model (Jmol) Interactive image
ChEBI CHEBI:133246
ECHA InfoCard 100.013.084
PubChem 14296
Molar mass 136.20 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

Tetramethylpyrazine, also known as ligustrazine, is an antiinflammatory compound isolated from the fermented food natto. When purified, it is a colorless solid. Its biosynthesis involves amination of acetoin, the latter derived from pyruvate.[1]

The compound has attracted much attention for its medicinal properties.[2][2] and in fermented cocoa beans.[3]

It exhibited in vivo nootropic activity in rats.[4]


  1. Takuo Kosuge, Tahei Adachi & Hiroko Kamiya "Isolation Of Tetramethylpyrazine From Culture Of Bacillus Natto, And Biosynthetic Pathways Of Tetramethylpyrazine" Nature 1962, volume 195, 1103 .doi:10.1038/1951103a0
  2. 1 2 Kao, TK; Chang, CY; Ou, YC; Chen, WY; Kuan, YH; Pan, HC; Liao, SL; Li, GZ; Chen, CJ (2013). "Tetramethylpyrazine reduces cellular inflammatory response following permanent focal cerebral ischemia in rats". Experimental neurology. 247: 188–201. doi:10.1016/j.expneurol.2013.04.010. PMID 23644042.
  3. Effect of mass and turning time on free amino acid, peptide-N, sugar and pyrazine concentration during cocoa fermentation. P Hashim, J Selamat, S Muhammad, S Kharidah and A Ali, Journal of the Science of Food and Agriculture, 1998, Volume 78, pages 543–550. doi:10.1002/(SICI)1097-0010(199812)78:4<543::AID-JSFA152>3.0.CO;2-2
  4. Wu, W; Yu, X; Luo, XP; Yang, SH; Zheng, D (2013). "Tetramethylpyrazine protects against scopolamine-induced memory impairments in rats by reversing the cAMP/PKA/CREB pathway". Behavioural Brain Research. 253: 212–6. doi:10.1016/j.bbr.2013.07.052. PMID 23916742.
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