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183938

Sigma-Aldrich

2,3,5,6-Tetramethylpyrazine

98%

Synonym(s):

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

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$50.53
100 G
$156.00

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25 G
$50.53
100 G
$156.00

About This Item

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

$50.53

List Price$63.40Save 20%
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Available to ship onApril 22, 2025Details

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Quality Level

100

assay

98%

form

solid

bp

190 °C (lit.)

mp

77-80 °C (lit.)

SMILES string

Cc1nc(C)c(C)nc1C

InChI

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

InChI key

FINHMKGKINIASC-UHFFFAOYSA-N

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General description

2,3,5,6-Tetramethylpyrazine has been isolated from Ephedra sinica[1]. It is useful in the treatment of several disorders such as asthma, heart failure, rhinitis and urinary incontinence[1]. It is a flavor ingredient of tobacco[2]. It forms cocrystal with 4-hydroxybenzoic acid which exhibits supramolecular synthon polymorphism[3].

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_germany

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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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
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
Xian-Chao Cheng et al.
Bioorganic & medicinal chemistry, 15(10), 3315-3320 (2007-03-27)
A series of novel Ligustrazine derivatives was designed, synthesized, and assayed for their protective effects on damaged ECV-304 cells and antiplatelet aggregation activities. The results showed that most Ligustrazine derivatives exhibited lower EC(50) values for protective effects on the ECV-304
Hongfei Chen et al.
European journal of medicinal chemistry, 46(11), 5609-5615 (2011-10-14)
A series of novel ligustrazinyloxy-cinnamic acid derivatives were designed, synthesized and evaluated for their inhibitory effect on adenosine diphosphate (ADP)-induced platelet aggregation in vitro, and also assayed for their protective effect against hydrogen peroxide (H(2)O(2))-induced oxidative damage on ECV-304 cells.
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