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.
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
- Subclass of
- alkylpyrazine
- Mass
- 136.1
Show 5 more facts
- canonical SMILES
- CC1=C(N=C(C(=N1)C)C)C
- chemical formula
- C₈H₁₂N₂
- subject has role
- vasodilator agent
- 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.