China Largest Manufacturer factory Supply Sinomenine CAS 115-53-7

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Sinomenine Basic information Product Name: Sinomenine Synonyms: 7,8-didehydro-4-hydroxy-3,7-dimethoxy-17-methyl-9-alpha,13-alpha,14-alpha-mo;9-alpha,13-alpha,14-alpha-morphinan-6-one,7,8-didehydro-4-hydroxy-3,7-dimethox;rphinan-6-one;y-17-methyl-;SABIANINE A;SINOMENIN;SINOMENINE;(9alpha,13alpha,14alpha)-7,8-didehydro-4-hydroxy-3,7-dimethoxy-17-methylmorphinan-6-one CAS: 115-53-7 MF: C19H23NO4 MW: 329.39 EINECS: 204-094-6 Product Categories: chemical reagent;pharmaceutical intermediate;API;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract;Alkaloids;Natural Plant Extract;Asymmetric Synthesis;Chiral Building Blocks;Complex Molecules;Inhibitors Mol File: 115-53-7.mol   Sinomenine Chemical Properties Melting point  180 °C (dec.)(lit.) alpha  D26 -71° (c = 2.1 in alc) Boiling point  466.98°C (rough estimate) density  1.2012 (rough estimate) refractive index  1.5000 (estimate) storage temp.  Store at +4°C pka 9.72±0.40(Predicted) form  neat Merck  13,8620 InChIKey YMEVIMJAUHZFMW-VUIDNZEBSA-N   Safety Information Hazard Codes  T,Xn Risk Statements  45-46-23/24/25-36/37/38-20/21/22-48/20/22-40-22-63 Safety Statements  53-22-26-36/37/39-45-36/37-24/25 RIDADR  1544 WGK Germany  3 RTECS  QD2170000 F  9 HazardClass  6.1(b) PackingGroup  III HS Code  29399990 Toxicity LD50 orally in mice: 580 mg/kg (Fu) MSDS Information Provider Language (9alpha,13alpha,14alpha)-7,8-Didehydro-4-hydroxy-3,7-dimethoxy-17-methylmorphinan-6-one English SigmaAldrich English   Sinomenine Usage And Synthesis Description Isolated by Ohta from Cocculus diversifolius DC., this alkaloid forms colourless crystals from MeOH. It is stated to possess a powerful reflex action and to be aspasm stimulant, finally causing paralysis and death in toxic doses. It is also said to suppress the hypotensive action of dihydroxyphenylethanolethylamine. Physical properties Appearance: acicular crystals (crystallized from benzene). Solubility: soluble in ethanol, acetone, chloroform, and dilute alkali; slightly soluble in water, ether, and benzene. Melting point: 219–221 °C. Specific optical rotation: – 71° (c = 2.1, ethanol). Its hydrochloride, crystallization (water or ethanol), decomposed at 278 °C. Its hydroiodide, needle crystal (crystallized from water), decomposed at 272 °C. Its picrate, which is yellow needle crystal, decomposed at 176 °C. Sinomenine is sensitive to light and heat to decompose. History The chemical structure of sinomenine is composed of four rings, A, B, C, and D, similar to the structure of morphine. Ring A is a benzene ring, and ring B is a half-chair-shaped, six-member ring. The C ring is a twisted-chair-type, sixmember ring that has an a, β-unsaturated ketone structure attached to the B ring. The D ring is a nitrogen-containing, sixmember ring under the B ring. Its structure is shown below; the current structural modification of sinomenine is mainly focused on the A/C active group. Based on the transformation of the A ring, it was found that the 1-substituted formyl derivative of sinomenine showed the strongest inhibitory effect on the inflammatory response of the mouse ear. The 4-substituted p-chlorobenzoyl-sinomenine has the strongest anti-inflammatory and analgesic activity. The biotransformation and chemical synthesis were also used to prepare the di-sinomenine derivatives linked by carbon and carbon, which was stronger than that of sinomenine and had a strong inhibitory effect on cell inflammatory factors. Sinomenine derivatives of the C ring with a pyrazine ring have a strong inhibitory effect on T, B lymphocyte proliferation reaction, which can be used for the preparation of immunomodulatory drugs. The transformation of C ring carbonyl yielded a series of shift alkali derivatives, with strong anti-inflammatory and analgesic effects. These attempts are important for the development of new drugs. Uses weak abortifacient, immunosuppressant, analgesic, antiinflammatory; LD50 (po) 580 mg/kg; (ip) 285 mg/kg(mouse) Indications It is mainly used for the treatment of rheumatoid arthritis and other types of rheumatism and arrhythmia in clinical. Biological Activity Natural anti-inflammatory morphinan analog. Causes degranulation of mast cells in mammalian tissues to release histamine and suppresses production of proinflammatory cytokines. Also displays antinociceptive activity, possibly through activation of the μ -opioid receptor. Stimulates short-term renewal of human embryonic stem cells (ESCs) in vitro . Pharmacology Sinomenine has anti-inflammatory, immunosuppressive, analgesic sedation, antiarrhythmic, detoxification, and other pharmacological effects, while the half-life of sinomenine is short. In addition, sinomenine also causes a strong histamine release, which leads to rash, gastrointestinal reactions, and other side effects, limiting its wide range of clinical applications. 1. Effects on central nervous system (a) Analgesic effect: The chemical structure of sinomenine and morphine are similar (Fig. 3). They both act on the central nervous system with a significant analgesic effect, but the mechanisms are different. It has been shown that the analgesic effect of sinomenine has nothing to do with the release of histamine. (b) Sedative effect: Sinomenine has an inhibitory effect on the central nervous system. The sedative effect works by inhibiting the excitement of advanced neurological activity. Sinomenine can also eliminate the “anger” response of mice caused by electrical stimulation, showing a stabilizing effect. In addition, although, like morphine, it had mainly a sedative effect on the central nervous system, sinomenine also has some excitatory effects on some parts of the central nervous system, especially the spinal cord. Other effects on the central nervous system: Sinomenine may, to a slight degree, induce vomiting. Sinomenine also has local anesthetic effects on frog nerve endings and rabbit cornea that could be applied for local infiltration anesthesia. 2. Effects on peripheral nervous system Sinomenine can reversibly block the neuromuscular transmission, which showed a concentration-dependent inhibitory effect. Sinomenine had no significant effect on nerve stem excitability and conductivity. 3. Impact on cardiovascular system Sinomenine has a significant antihypertensive effect. Sinomenine also has a significant antagonistic effect on ischemic arrhythmia. 4. Anti-inflammatory and antiallergic effects The anti-inflammatory effect of sinomenine is significant. Clinical Use The treatment of rheumatism and rheumatoid arthritis is one of the most important clinical applications of sinomenine. Sinomenine is particularly suitable for the treatment of arrhythmia caused by organic heart disease. Sinomenine is used for the treatment of glomerular disease, which can reduce urinary protein and relieve hematuria symptoms, and the side effects were significantly lower than that of tripterygium glycoside tablets, which are commonly used in clinical practice. In addition, sinomenine can significantly inhibit renal interstitial fibrosis and the production of tissue growth and growth factor TGF-β1. Sinomenine can significantly delay the development of chronic renal failure and effectively treat ankylosing spondylitis. Purification Methods Crystallise the salt from water (1g/1.5mL) or EtOH. The free base [115-53-7] M 329.4, has m 161o (from EtOH) (and again at 182o) after crystallisation from *C6H6, and [] D -78.9o (c 1, EtOH). The picrate has m 159-162o(dec) (from H2O). [Beilstein 21 II 470, 21 III/IV 6670.] References Ohta., Ber. ges. Physiol., 33, 352 (1925) Ohta, Kitasato., Arch. expo Med., 6, 259, 283 (1925) Raymond-Hamet., Compt. rend. Soc. Biol., 125, 509 (1937)

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Leader Biochemical Group is a large leader incorporated industry manufacturers and suppliers of advanced refined raw materials From the year of 1996 when our factory was put into production to year of 2020, our group has successively invested in more than 52 factories with shares and subordinates.We focus on manufacture Pharm & chemicals, functional active ingredients, nutritional Ingredients, health care products, cosmetics, pharmaceutical and refined feed, oil, natural plant ingredients industries to provide top quality of GMP standards products.All the invested factories' product lines cover API and intermediates, vitamins, amino acids, plant extracts, daily chemical products, cosmetics raw materials, nutrition and health care products, food additives, feed additives, essential oil products, fine chemical products and agricultural chemical raw materials And flavors and fragrances. Especially in the field of vitamins, amino acids, pharmaceutical raw materials and cosmetic raw materials, we have more than 20 years of production and sales experience. All products meet the requirements of high international export standards and have been recognized by customers all over the world. Our manufacture basement & R&D center located in National Aerospace Economic & Technical Development Zone Xi`an Shaanxi China. Now not only relying on self-cultivation and development as well as maintains good cooperative relations with many famous research institutes and universities in China. Now, we have closely cooperation with Shanghai Institute of Organic Chemistry of Chinese Academy of Science, Beijing Institute of Material Medical of Chinese Academy of Medical Science, China Pharmaceutical University, Zhejiang University. Closely cooperation with them not only integrating Science and technology resources, but also increasing the R&D speed and improving our R&D power. Offering Powerful Tech supporting Platform for group development. Keep serve the manufacture and the market as the R&D central task, focus on the technical research.  Now there are 3 technology R & D platforms including biological extract, microorganism fermentation and chemical synthesis, and can independently research and develop kinds of difficult APIs and pharmaceutical intermediates. With the strong support of China State Institute of Pharmaceutical Industry (hereinafter short for CSIPI), earlier known as Shanghai Institute of Pharmaceutical Industry (SIPI), we have unique advantages in the R & D and industrialization of high-grade, precision and advanced products.  Now our Group technical force is abundant, existing staff more that 1000 people, senior professional and technical staff accounted for more than 50% of the total number of employees, including 15 PhD research and development personnel, 5 master′ S degree in technical and management personnel 9 people. We have advanced equipment like fermentation equipment and technology also extraction, isolation, purification, synthesis with rich production experience and strict quality control system, According to the GMP required, quickly transforming the R&D results to industrial production in time, it is our advantages and our products are exported to North and South America, Europe, Middle East, Africa, and other five continents and scale the forefront in the nation, won good international reputation.  We believe only good quality can bring good cooperation, quality is our key spirit during our production, we are warmly welcome clients and partner from all over the world contact us for everlasting cooperation, Leader will be your strong, sincere and reliable partner in China.

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