Tetramethylpyrazine

Names

[ Name ]:
Tetramethylpyrazine

[Synonym ]:
Pyrazine, 2,3,5,6-tetramethyl-
MFCD00006146
Chuanxingzine
Ligustrazine
2,3,5,6-Tetramethylpyrazine
EINECS 214-391-2
2,3,5,6,-Tetramethyl-1,4-pyrazine
PPyrazine, tetramethyl-
Tetramethyl-1,4-diazine
Tetramethylpyrazine
2,3,5,6-TETRA METHYL PYRAZINE

Biological Activity

[Description]:

Tetramethylpyrazine (Ligustrazine), an alkylpyrazine isolated from Ligusticum wallichii (Chuan Xiong)[1], is present in french fries, bread, cooked meats, tea, cocoa, coffee, beer, spirits, peanuts, filberts, dairy products and soy products as fragrance and flavouring ingredienexhibits. Tetramethylpyrazine (Ligustrazine) also has potential nootropic and anti-inflammatory activities in rats[2][3].

[Related Catalog]:

Research Areas >> Cancer

Research Areas >> Cardiovascular Disease

Signaling Pathways >> Others >> Others

Research Areas >> Inflammation/Immunology

Research Areas >> Metabolic Disease

Research Areas >> Neurological Disease

[In Vitro]

Tetramethylpyrazine has been extensively used in China for cardiovascular and cerebrovascular diseases for about 40 years. Because of its effectiveness in multisystem, especially in cardiovascular. Tetramethylpyrazine also has been used in various diseases, such as coronary heart disease, diabetes, cancers, and liver injury[1].

[References]

[1]. Zhao Y, et al. Mechanisms and Clinical Application of Tetramethylpyrazine (an Interesting Natural Compound Isolated from Ligusticum Wallichii): Current Status and Perspective. Oxid Med Cell Longev. 2016;2016:2124638.

[2]. Wu W, et al. Tetramethylpyrazine protects against scopolamine-induced memory impairments in rats by reversing the cAMP/PKA/CREB pathway. Behav Brain Res. 2013 Sep 15;253:212-6.

[3]. Kao TK, et al. Tetramethylpyrazine reduces cellular inflammatory response following permanent focal cerebral ischemia in rats. Exp Neurol. 2013 Sep;247:188-201.

Chemical & Physical Properties

[ Density]:
1.0±0.1 g/cm3

[ Boiling Point ]:
192.7±35.0 °C at 760 mmHg

[ Melting Point ]:
77-80 °C(lit.)

[ Molecular Formula ]:
C₈H₁₂N₂

[ Molecular Weight ]:
136.19

[ Flash Point ]:
71.6±17.6 °C

[ Exact Mass ]:
136.100052

[ PSA ]:
25.78000

[ LogP ]:
1.56

[ Vapour Pressure ]:
0.7±0.4 mmHg at 25°C

[ Index of Refraction ]:
1.504

[ Stability ]:
Stable. Incompatible with strong acids, strong oxidizing agents.

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: UQ3905000

CHEMICAL NAME :: Pyrazine, tetramethyl-

CAS REGISTRY NUMBER :: 1124-11-4

LAST UPDATED :: 199701

DATA ITEMS CITED :: 4

MOLECULAR FORMULA :: C8-H12-N2

MOLECULAR WEIGHT :: 136.22

WISWESSER LINE NOTATION :: T6N DNJ B1 C1 E1 F1

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 1910 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: DCTODJ Drug and Chemical Toxicology. (Marcel Dekker, 270 Madison Ave., New York, NY 10016) V.1- 1977/78- Volume(issue)/page/year: 3,249,1980

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 800 ug/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: IJCREE International Journal of Crude Drug Research. (Swets & Zeitlinger B.V., POB 825, 2160 SZ Lisse, Netherlands) V.20- 1982- Volume(issue)/page/year: 23,119,1985

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 239 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: CMJODS Chinese Medical Journal (Beijing, English Edition). (China International Book Trading Corp., POB 2820, Beijing, Peop. Rep. China) V.1- 1975- Adopted vol. no. 92 in 1979. Volume(issue)/page/year: 4,319,1978

Safety Information

[ Symbol ]:

GHS05, GHS07

[ Signal Word ]:
Danger

[ Hazard Statements ]:
H302-H315-H318-H335

[ Precautionary Statements ]:
P261-P280-P305 + P351 + P338

[ Personal Protective Equipment ]:
dust mask type N95 (US);Eyeshields;Gloves

[ Hazard Codes ]:
Xn:Harmful

[ Risk Phrases ]:
R22

[ Safety Phrases ]:
S26-S39-S24/25

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

[ RTECS ]:
UQ3905000

[ HS Code ]:
29339990

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2933990090

[ Summary ]:
2933990090. heterocyclic compounds with nitrogen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

Articles

Characterization of Volatile Flavor Compounds in Chinese Rice Wine Fermented from Enzymatic Extruded Rice.

J. Food Sci. 80 , C1476-89, (2015)

Enzymatic extrusion, instead of traditional steam cooking, to treat rice is an efficient and alternative pretreatment for Chinese rice wine fermentation. In order to determine the formation of volatil...

Induction of human CYP3A4 by huperzine A, ligustrazine and oridonin through pregnane X receptor-mediated pathways.

Pharmazie 69(7) , 532-6, (2014)

The pregnane X receptor (PXR) is a key regulator of CYP3A4, which is involved in catalyzing the metabolic conversion of a number of endogenous substrates. In this study, we screened 22 compounds isola...

Antioxidative and thrombolytic TMP nitrone for treatment of ischemic stroke.

Bioorg. Med. Chem. 16 , 8868-74, (2008)

Ischemic stroke results from brain blood vessel blockage by thrombus, and produces neuronal cell damage and death. While thrombolytic therapy with tPA has achieved some success in clinic, the strategy...