Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C8H12N2 |
| Molecular Weight | 136.1943 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CC1=NC(C)=C(C)N=C1C
InChI
InChIKey=FINHMKGKINIASC-UHFFFAOYSA-N
InChI=1S/C8H12N2/c1-5-6(2)10-8(4)7(3)9-5/h1-4H3
Ligustrazine (tetramethylpyrazine) is a bioactive ingredient extracted from the widely-used Chinese herb, Chuanxiong. It inhibits of platelet aggregation, enhances of vessel dilation, increases cerebral blood flow and possesses neuroprotective properties. The injection solution of ligustrazine has been used especially in China to treat ischemic stroke, coronary heart disease, diabetic nephropathy, and knee osteoarthritis. Ligustrazine was also evaluated in clinical as a remedy for pressure sores, as a salvage agent for patients with non-Hodgkin's lymphoma, as a treatment for bronchial asthma and vertebrobasilar insufficiency.
CNS Activity
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: map04611 |
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Target ID: CHEMBL2095229 |
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Target ID: GO:0002537 |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | Unknown Approved UseUnknown |
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| Primary | Unknown Approved UseUnknown |
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| Primary | Unknown Approved UseUnknown |
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| Primary | Unknown Approved UseUnknown |
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| Primary | Unknown Approved UseUnknown |
PubMed
| Title | Date | PubMed |
|---|---|---|
| [Effects of ligustrazine on blood vessels and blood components]. | 2002 Feb |
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| [Advances in the study on transdermal permeation of active elements of natural drugs in vitro]. | 2002 Jan |
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| The effects of Ligustrazine on the expression of bFGF and bFGFR in bone marrow in radiation injured mice. | 2003 |
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| [Study on the effects of tetramethylpyrazine on tumor cells: survey and prospects]. | 2003 Apr |
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| [Effect of ligustrazine on proliferative glomerulonephritis]. | 2003 Aug |
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| [Effects of tetramethylpyrazine on cytosolic free calcium concentration in penis corpus cavernsum smooth muscle cells in rabbits]. | 2003 Aug |
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| [Protective effect of ligustrazine on insulin resistance after local cerebral ischemia of rat]. | 2003 Dec |
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| Basolateral membrane mechanisms involved in ligustrazine-stimulated anion secretion in rat distal colon. | 2003 Dec 25 |
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| [Effect of ligustrazine on the expression of Bcl-2 protein and apoptosis in rabbit articular chondrocytes in monolayer culture]. | 2003 Jun |
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| Tetramethylpyrazine elicits disparate responses in cardiac contraction and intracellular Ca(2+) transients in isolated adult rat ventricular myocytes. | 2003 Nov |
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| Effect of tetramethylpyrazine on exocrine pancreatic and bile secretion. | 2003 Nov |
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| [Effect of ligustrazine on cell cycle and prostacyclin of injured vascular endothelial cells induced by hypoxia and lack of glucose]. | 2003 Oct |
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| [Effect of tetramethylpyrazine on learning, memory and cholinergic system in D-galactose-lesioned mice]. | 2003 Oct |
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| Effect of tetramethylpyrazine on potassium channels to lower calcium concentration in cultured aortic smooth muscle cells. | 2003 Oct |
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| [Ligustrazine and Salvia miltiorrhiza injection solution in complementary therapy of pregnancy-induced hypertension: clinical analysis of 60 cases]. | 2003 Sep |
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| The oxygen radical generator pyrogallol impairs cardiomyocyte contractile function via a superoxide and p38 MAP kinase-dependent pathway: protection by anisodamine and tetramethylpyrazine. | 2004 |
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| Inhibitory effects of ligustrazine, a modulator of thromboxane-prostacycline-nitric oxide balance, on renal injury in rats with passive Heyman nephritis. | 2004 |
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| Pickles, pectin, and penicillin. | 2004 |
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| Effect of ligustrazine on the expression of LFA-1, ICAM-1 following bone marrow transplantation in mice. | 2004 |
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| Inhibition of shear-induced platelet aggregation in rat by tetramethylpyrazine and salvianolic acid B. | 2004 |
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| [Effect of ligustrazine on the expression of LFA-1 and ICAM-1 in bone marrow transplantation recipient mice]. | 2004 Apr |
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| [Experimental study on prevention and treatment of bronchial asthma by compound Chinese herbal monomer recipe]. | 2004 Aug |
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| [Effects of ligustrazine on expression of PECAM-1/CD31 and hematopoietic reconstitution in syngenic bone marrow transplantation of mice]. | 2004 Aug |
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| [Effect of chuanxiongzine on the relaxation of isolated rabbit corpus cavernosum tissues]. | 2004 Aug |
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| Preparative isolation and purification of chuanxiongzine from the medicinal plant Ligusticum chuanxiong by high-speed counter-current chromatography. | 2004 Aug 27 |
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| Liquid chromatography-mass spectrometry method for determination of tetramethylpyrazine and its metabolite in dog plasma. | 2004 Dec 25 |
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| [Progress of the study on effective integredients from Chinese herbal medicine in anti-tumor metastasis]. | 2004 Feb |
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| [Effect of Ligustrazine on the expression of vascular endothelial growth factor in bone marrow stromal cells of radiation injured mice]. | 2004 Feb |
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| [Effect of tetromethylpyrazine and aminoguanidine on expression of vascular endothelial growth factor in kidney of diabetic rats]. | 2004 Jan |
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| Nitric oxide-mediated vasorelaxation by Rhizoma Ligustici wallichii in isolated rat thoracic aorta. | 2004 Jan |
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| [Chemical profiles of methylpyrazines contained in commercially available natto]. | 2004 Jan |
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| Studies on the aroma of cupuassu liquor by headspace solid-phase microextraction and gas chromatography. | 2004 Jan 30 |
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| Effect of tetramethylpyrazine on acute nociception mediated by signaling of P2X receptor activation in rat. | 2004 Jan 9 |
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| [Study on the interactions between four components in Ligusticum chuanxiong rhizome and acceptors on cardiac muscle membrane]. | 2004 Jul |
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| Preparation of cardiovascular disease-related genes microarray and its application in exploring ligustrazine-induced changes in endothelial gene expression. | 2004 Jul-Aug |
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| [The effect of ligustrazine on the expression of CD44 in bone marrow of bone marrow transplantation mice]. | 2004 Jun |
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| Differential Cl- and HCO3- mediated anion secretion by different colonic cell types in response to tetromethylpyrazine. | 2004 Jun 15 |
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| Effects of electroacupuncture plus intra-carotid drug injection on rheoencephalogram in patients with cerebral infarction. | 2004 Mar |
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| [Effect of ligustrazine on expressions of basic fibroblast growth factor and its receptor in bone marrow of mice with acute radiation injury]. | 2004 May |
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| [Cardiac hemodynamics after suprarenal ligation of the inferior vena cava and the resection of the right kidney or injection of ligustrazine in rats]. | 2004 May |
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| [Effects of combination therapy of rehin and tetramethylpyrazine on experimental hepatic fibrosis induced by tetrachloride]. | 2004 Nov |
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| Tetramethylpyrazine reduces ischemic brain injury in rats. | 2004 Nov 30 |
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| [Study on ligustrazine in reversing multidrug resistance of HepG2/ADM cell in vitro]. | 2004 Oct |
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| [Protective effect of tetramethylpyrazine and L-arginine on rats with acute myocardial infarction]. | 2004 Oct |
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| [Effect of tetramethylpyrazine on lipopolysaccharides induced macrophage cyclo-oxidase-2 expression and apoptosis of cardiac myocytes]. | 2004 Oct |
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| The electrochemistry and determination of Ligustrazine hydrochloride. | 2004 Oct |
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| Effect of ligustrazine on ischemia-reperfusion injury in murine kidney. | 2004 Sep |
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| Protective effect of tetramethylpyrazine on learning and memory function in D-galactose-lesioned mice. | 2004 Sep |
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| The protective effects of ligustrazine on ischemia-reperfusion and DPPH free radical-induced myocardial injury in isolated rat hearts. | 2004 Sep |
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| Improvement of barrier function and stimulation of colonic epithelial anion secretion by Menoease Pills. | 2004 Sep 1 |
Patents
Sample Use Guides
In a clinical trial for the treatment of pressure sores, ligustrazine was applied with a transdermal patch. For treatment of bronchial asthma, ligustrazine was administered by inhalation. For treatment of vertebrobasilar insufficiency, ligustrazine was administered intravenously (80 mg of ligustrazine in 250 ml of 5% glucose or 0.9% normal saline for 15 days).
Route of Administration:
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JECFA EVALUATION |
2,3,5,6-TETRAMETHYLPYRAZINE
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214-391-2
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Tetramethylpyrazine
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1124-11-4
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100000127845
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SUB34026
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DTXSID6047070
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V80F4IA5XG
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837
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ACTIVE MOIETY
SALT/SOLVATE (PARENT)
