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Merck
CN

183938

2,3,5,6-Tetramethylpyrazine

98%

Synonym(s):

2,3,5,6-Tetramethylpyrazine, Ligustrazin, Ligustrazine, Tetrapyrazine

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About This Item

Empirical Formula (Hill Notation):
C8H12N2
CAS Number:
1124-11-4
Molecular Weight:
136.19
NACRES:
NA.22
PubChem Substance ID:
24851081
eCl@ss:
39161809
UNSPSC Code:
12352100
EC Number:
214-391-2
MDL number:
MFCD00006146
Beilstein/REAXYS Number:
113100

Key Documents

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Product Name

2,3,5,6-Tetramethylpyrazine, 98%

InChI key

FINHMKGKINIASC-UHFFFAOYSA-N

InChI

1S/C8H12N2/c1-5-6(2)10-8(4)7(3)9-5/h1-4H3

SMILES string

Cc1nc(C)c(C)nc1C

assay

98%

form

solid

bp

190 °C (lit.)

mp

77-80 °C (lit.)

Quality Level

100

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General description

2,3,5,6-Tetramethylpyrazine has been isolated from Ephedra sinica. It is useful in the treatment of several disorders such as asthma, heart failure, rhinitis and urinary incontinence. It is a flavor ingredient of tobacco. It forms cocrystal with 4-hydroxybenzoic acid which exhibits supramolecular synthon polymorphism.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
02618KV
04024EE
14003DE
14425DD
18530KI

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B R Sreekanth et al.
Chemical communications (Cambridge, England), (23)(23), 2375-2377 (2007-09-12)
Co-crystals of 4-hydroxybenzoic acid and 2,3,5,6-tetramethylpyrazine (2 : 1) exhibit the first supramolecular synthon polymorphism in a co-crystal; metastable anti-hierarchic polymorph I converts to stable hierarchic form II.
Christopher R E Coggins et al.
Inhalation toxicology, 23 Suppl 1, 84-89 (2011-04-05)
Three heterocyclic nitrogen compounds, 2,3-diethylpyrazine (DEP), 2,3,5,6-tetramethylpyrazine (TMP), and 2-acetyl pyridine (AP), are naturally present in tobacco and are also added to tobacco as flavor ingredients. A battery of tests was used to compare the toxicity of mainstream smoke from
Gyoseon Goya M Yeom et al.
International immunopharmacology, 18(2), 262-269 (2013-12-18)
2,3,5,6-Tetramethylpyrazine (TMP) is known as a composition of Ephedra sinica and it has been used in the treatment of several disorders such as asthma, heart failure, rhinitis, and urinary incontinence. It has been reported that TMP inhibits melanoma metastasis and
Xian-Chao Cheng et al.
Bioorganic & medicinal chemistry, 17(8), 3018-3024 (2009-03-31)
A series of novel acylpiperazinyl Ligustrazine derivatives was designed, synthesized, and their protective effects on damaged ECV-304 cells and antiplatelet aggregation activities were evaluated. The results showed that compound E33 displayed most potential protective effects on the ECV-304 cells damaged
Huda M AlKreathy et al.
Saudi pharmaceutical journal : SPJ : the official publication of the Saudi Pharmaceutical Society, 28(8), 916-926 (2020-08-15)
Available antiulcer medications reveal partial efficacy and numerous adverse reactions. Tetramethylpyrazine (TMP) was known for its potential antioxidant, anti-inflammatory and angiogenic properties. The aim of current study was to investigate the potential gastroprotective effect of TMP against indomethacin-induced gastric ulcer
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