All Photos(2)

183938

Sigma-Aldrich

2,3,5,6-Tetramethylpyrazine

98%

Empirical Formula (Hill Notation):
C8H12N2
CAS Number:
Molecular Weight:
136.19
Beilstein:
113100
EC Number:
MDL number:
eCl@ss:
39161809
PubChem Substance ID:
NACRES:
NA.22

Quality Level

assay

98%

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. 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.

Packaging

25, 100 g in poly bottle

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

Certificate of Analysis

Certificate of Origin

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
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
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.
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
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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