Structure via PubChem · Public domain (PubChem)
ligustrazine
Sign in to saveAlso known as 2,3,5,6-tetramethylpyrazine, tetramethylpyrazine
Tetramethylpyrazine, also known as ligustrazine, is a chemical compound found in nattō and in fermented cocoa beans. In an observational study, tetramethylpyrazine was the dominant volatile organic compound in one sourdough starter. When purified, tetramethylpyrazine is a colorless solid. It is classified as an alkylpyrazine. Its biosynthesis involves amination of acetoin, the latter derived from pyruvate. It exhibits potential nootropic and antiinflammatory activities in rats.
In the Vinony graph
Vinony's link graph records 339 inbound references to ligustrazine, and connects out to adenosine receptor, diquafosol and copper.
Vinony files it under Anti-inflammatory agents, Chembox image size set and Components of chocolate.
Vinony links it to 10 Wikipedia language editions.
Chemical data
- Formula
- C8H12N2
- Molecular weight
- 136.19 g/mol
- IUPAC name
- 2,3,5,6-tetramethylpyrazine
via PubChem
Drug data · ChEMBL
- Molecule type
- Small molecule
via ChEMBL · EBI
Research
1,751 papers- Ligustrazine as a multitarget scaffold in drug design and discovery.Bioorganic & medicinal chemistry · 2025
- Astragaloside IV combined with ligustrazine ameliorates abnormal mitochondrial dynamics via Drp1 SUMO/deSUMOylation in cerebral ischemia-reperfusion injury.CNS neuroscience & therapeutics · 2024
- Ligustrazine monomer against cerebral ischemia/reperfusion injury.Neural regeneration research · 2015
- Ligustrazine nano-drug delivery system ameliorates doxorubicin-mediated myocardial injury via piezo-type mechanosensitive ion channel component 1-prohibitin 2-mediated mitochondrial quality surveillance.Journal of nanobiotechnology · 2025
- N-butylphthalide (NBP) and ligustrazine (TMP) triazole hybrids target the KEAP1-NRF2 pathway to inhibit ferroptosis and exert brain neuroprotectivity.Redox biology · 2025
via PubMed
Wikidata facts
- Mass
- 136.1
Show 4 more facts
- canonical SMILES
- CC1=C(N=C(C(=N1)C)C)C
- chemical formula
- C₈H₁₂N₂
- melting point
- 85
- Commons category
- Tetramethylpyrazine
via Wikidata · CC0
~1 min read
Encyclopedic overview
1 sectionsContents
- References
Tetramethylpyrazine, also known as ligustrazine, is a chemical compound found in nattō and in fermented cocoa beans. In an observational study, tetramethylpyrazine was the dominant volatile organic compound in one sourdough starter. When purified, tetramethylpyrazine is a colorless solid. It is classified as an alkylpyrazine. Its biosynthesis involves amination of acetoin, the latter derived from pyruvate. It exhibits potential nootropic and antiinflammatory activities in rats.
== References ==
Excerpted from Wikipedia’s “ligustrazine” article, available under the CC BY-SA 4.0 licence.