Тетраметилпиразин

Описание

2,3,5,6-Tetramethylpyrazine is an alkaloid that has been found in L. wallichii and has diverse biological activities. It reduces kainate-induced increases in production of reactive oxygen species (ROS) and cytotoxicity in primary rat hippocampal neurons when used at a concentration of 5 μM. 2,3,5,6-Tetramethylpyrazine (0.1 mM) induces vasodilation in precontracted isolated and endothelium-denuded rat tail artery strips and reduces blood pressure in anesthetized rats. It decreases infarct volume, caspase-3 activation, and hypoxia-inducible factor-1α (HIF-1α) levels in a rat model of focal cerebral ischemia induced by middle cerebral artery occlusion (MCAO) when administered at a dose of 20 mg/kg.

Химические свойства

2,3,5,6-Tetramethylpyrazine has musty, fermented, coffee odor

Физические свойства

Appearance: colorless needle crystal. Solubility: soluble in hot water, petroleum ether, chloroform, dilute hydrochloric acid, slightly soluble in ether, insoluble in cold water. Melting point: 77–80°C. Boiling point: 190°C. Flash point: 128– 130°C/200mm. Ligustrazine has a particular odor, moisture absorption, and sublimation.

Вхождение

Reported found in French fried potato, bell pepper, wheat bread, emmental cheese, Swiss cheese, Camembert cheese, Gruyere cheese, boiled and cooked beef, grilled and roasted beef, fried beef, cooked lamb and mutton, lamb and mutton liver, grilled and roasted uncured pork, beer, black tea, green tea. Also reported present in cocoa products, coffee, dairy products, oatmeal, galbanum oil, roasted peanuts, soybean, beans, mushroom, trassi, coriander seed, rice bran, trassi, sukiyaki, soy sauce, malt, licorice, dried bonito, wild rice, shrimp, crab, clam, scallop, filberts, rum, sake, wine, whiskey, burley tobacco and soy products.

История

Ligusticum walliichi has a long medicinal history in China and is used in the treatment of headache, promoting blood and Qi circulation, curing chills and alleviating pain”. Clinically, it is mainly used for the treatment of cardiovascular and cerebrovascular diseases. Ligustrazine (2,3,5,6-tetramethylpyrazine) is the main active ingredient of Ligusticum walliich. It was first isolated in 1962 .
In recent years, studies have found that ligustrazine can inhibit the activity of the cerebral cortex and medullary respiratory center, excite vasomotors, induce the expansion of peripheral blood vessels, promote the blood flow of the coronary artery and lower limbs, and reduce blood pressure. Ligustrazine can also paralyze the nerve center and has sedative and analgesic effects.
Studies have suggested that ligustrazine has a variety of new effects, including improving leptomeningeal and peripheral microcirculation and increasing cerebral blood flow, and its effect is better than that of papaverine. Ligustrazine can also protect against experimental cerebral ischemia and alleviate brain edema and the deposition of fibrin in microvessels. Ligustrazine is also used in the treatment of pulmonary heart disease, heart failure, dilated heart disease, portal hypertension, type II diabetes mellitus, tumor and coronary heart disease, and restenosis after stent implantation .

Использование

etramethylpyrazine is an anti-inflammatory compound isolated from the fermented food natto. Tetramethylpyrazine demonstrated in vivo nootropic activity in rats.

Подготовка

From2,5-dimethylpyrazine by ring alkylationwithMeLi; also by condensation of 2,3-butanedionewith 2,3-butanediamine.

Показания

Ligustrazine is used for occlusive vascular diseases, cerebral thrombosis, vasculitis, coronary heart disease, angina pectoris, and others

Определение

ChEBI: A member of the class of pyrazines that is pyrazine in which all four hydrogens have been replaced by methyl groups. An alkaloid extracted from Chuanxiong (Ligusticum wallichii).

Общее описание

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.

Клиническое использование

The main clinical formulation of ligustrazine is ligustrazine hydrochloride injection. Ligustrazine hydrochloride injection was used to prevent restenosis following coronary stent implantation and to treat acute coronary syndrome and ischemic stroke. Ligustrazine hydrochloride injection is helpful in alleviating pulmonary hypertension in patients with pulmonary heart disease. The therapeutic effect of ligustrazine hydrochloride injection on severe cholestatic liver cirrhosis caused by chronic heart failure of rheumatic heart disease is remarkable. In addition, ligustrazine is widely used in the treatment of vertigo syndrome, vertebrobasilar insufficiency, tension headache, and so on. It has a good symptomatic-treatment effect .
Ligustrazine is also reported for the treatment of children with viral myocarditis, chronic renal failure, hepatic fibrosis, portal hypertension, tumors, and diabetic nephropathy. Ligustrazine can relieve symptoms rapidly, and its effect is stable and lasting. It has good clinical promotion value .

Профиль безопасности

Poison by intravenous and intraperitoneal routes. Moderately toxic by ingestion. When heated to decomposition it emits toxic fumes of NOx.