Sinomenine

Base Information

• Chemical Name: Sinomenine
• CAS No.: 115-53-7
• Molecular Formula: C19H23NO4
• Molecular Weight: 329.396
• Hs Code.: 29399990
• European Community (EC) Number: 204-094-6
• UNII: 63LT81K70N
• DSSTox Substance ID: DTXSID00871595
• Wikipedia: Sinomenine
• Wikidata: Q7524904
• NCI Thesaurus Code: C64766
• Metabolomics Workbench ID: 70639
• ChEMBL ID: CHEMBL248095
• Mol file: 115-53-7.mol

Synonyms:4-hydroxy-3,7-dimethoxy-17-methylmorphin-7-en- 6-one;cocculine;cucoline;cucoline hydrochloride;cucoline, hydrochloride;cuculine;kukoline;morphinan-6-one, 7,8-didehydro-4-hydroxy-3,7-dimethoxy-17-methyl-, (9alpha,13alpha,14alpha)-;morphinan-6-one, 7,8-didehydro-4-hydroxy-3,7-dimethoxy-17-methyl-, hydrochloride (1:1), (9alpha,13alpha,14alpha)-;NSC-76021;sinomenin hydrochloride;sinomenine;sinomenine A bismethyliodide;sinomenine hydrochloride

Chemical Property of Sinomenine

Chemical Property:

• Appearance/Colour: white powder
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 180 °C (dec.)(lit.)
• Refractive Index: 1.625
• Boiling Point: 513.6 °C at 760 mmHg
• PKA: 9.72±0.40(Predicted)
• Flash Point: 264.4 °C
• PSA: 59.00000
• Density: 1.3 g/cm³
• LogP: 1.95600
• Storage Temp.: Store at +4°C
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 329.16270821
• Heavy Atom Count: 24
• Complexity: 562

Purity/Quality:

more than 98% ^*data from raw suppliers

Sinomenine 0.3mol chloroform of crystallization ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T,Xn
• 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

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CN1CCC23CC(=O)C(=CC2C1CC4=C3C(=C(C=C4)OC)O)OC
• Isomeric SMILES: CN1CC[C@@]23CC(=O)C(=C[C@@H]2[C@@H]1CC4=C3C(=C(C=C4)OC)O)OC
• Recent ClinicalTrials: Sinomenine Versus Glucocorticoid for Knee OA
• 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.
• 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.
• 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.

Technology Process of Sinomenine

There total 5 articles about Sinomenine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.0%

C22H27NO5 (1246560-79-1) → sinomenine (115-53-7)

Guidance literature:

With Aliquat 336; potassium hydroxide; In water; at 60 ℃; for 2h;

DOI:10.1039/c2gc16328d

Reference yield: 99.0%

4-acetyl-sinomenine (22610-64-6) → sinomenine (115-53-7)

Guidance literature:

With Aliquat 336; potassium hydroxide; In water; at 60 ℃; for 1h;

DOI:10.1039/c2gc16328d

Reference yield: 94.0%

Sinomenine Hydrochloride (6080-33-7,61487-22-7,70617-35-5) → sinomenine (115-53-7)

Guidance literature:

With ammonium hydroxide;

DOI:10.1080/14786419.2019.1677649

upstream raw materials:

C₂₂H₂₇NO₅

4-acetyl-sinomenine

Sinomenine Hydrochloride

sinomenine N-oxide

Downstream raw materials:

ent-4-benzoyloxy-3,7-dimethoxy-17-methyl-morphin-7-en-6-one

4-benzoyloxy-3,7-dimethoxy-17-methyl-morphin-7-en-6-one

ent-3-methoxy-17-methyl-morphinane-4,6β-diol

O-Benzylsinomenine

Refernces

• 1、 Pan, Hongmei,Lu, Tong,Wu, Xuedan,Gu, Chengwen,Tao, Naili,Zhang, Biao,Wang, Ao,Chen, Guangmei,Zhang, Kehua,Cheng, Jie,Jin, Jie. "Design and synthesis of sinomenine isoxazole derivatives via 1,3-dipolar cycloaddition reaction". supporting information. p. 2360 - 2364. Retrieved 2019/11/11.
• 2、 Cui, Xiaoxue,Li, Bo,Liu, Tianzhen,Li, Chunbao. "A practical solution for aqueous reactions of water-insoluble high-melting-point organic substrates". supporting information; experimental part. p. 668 - 672. Retrieved 2012/06/01.