Coptisine chloride

Base Information

• Chemical Name: Coptisine chloride
• CAS No.: 6020-18-4
• Molecular Formula: C19H14ClNO4
• Molecular Weight: 355.777
• European Community (EC) Number: 611-948-5
• NSC Number: 119754
• UNII: 4RSB8UY88E
• DSSTox Substance ID: DTXSID00975628
• Metabolomics Workbench ID: 139322
• ChEMBL ID: CHEMBL498722
• Mol file: 6020-18-4.mol

Synonyms:7,8,13,13a-tetradehydro-2,3-9,10-bis(methylenedioxy)berbinium;coptisine;coptisine chloride

Chemical Property of Coptisine chloride

Chemical Property:

• Vapor Pressure: 2E-14mmHg at 25°C
• Melting Point: >258oC (dec.)
• Refractive Index: 1.749
• Boiling Point: 601.5oC at 760 mmHg
• Flash Point: 190.4oC
• Density: 1.51g/cm3
• Storage Temp.: Hygroscopic, Refrigerator, Under Inert Atmosphere
• Solubility.: DMSO (Slightly), Methanol (Slightly, Sonicated)
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 0
• Exact Mass: 355.0611356
• Heavy Atom Count: 25
• Complexity: 502

Purity/Quality:

98% ^*data from raw suppliers

Coptisine Chloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C[N+]2=C(C=C3C=CC4=C(C3=C2)OCO4)C5=CC6=C(C=C51)OCO6.[Cl-]
• Uses: Coptisine is an alkaloid found in Chinese goldthread (Coptis chinensis). A bacterial collagenase inhibitor. Coptisine has been found to reversibly inhibit Monoamine oxidase A in mice, pointing to a potential role as a natural antidepressant. Coptisine is an alkaloid found in Chinese goldthread (Coptis chinensis). A bacterial collagenase inhibitor. Coptisine has been found to reversibly inhibit Monoamine oxidase A in mice, pointing to a potential role as a natural antidepressant.

Technology Process of Coptisine chloride

There total 16 articles about Coptisine chloride 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: 100.0%

Stylopine (84-39-9,2884-83-5,4312-32-7,7461-02-1) → coptisine chloride (6020-18-4)

Guidance literature:

With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In acetonitrile; for 2h; Solvent; Time; Reflux; Inert atmosphere;

Reference yield: 81.0%

N-methyl-13,14-dehydrostylopinium chloride (53777-79-0) → coptisine chloride (6020-18-4)

Guidance literature:

In dimethyl sulfoxide; at 115 ℃; for 1.5h;

DOI:10.1016/S0040-4020(02)00467-2

Reference yield:

Glyoxal (131543-46-9,107-22-2) + N-(2,3-methyleneoxy-N-benzyl)-β-(3,4-methyleneoxyphenyl)ethylamine → coptisine chloride (6020-18-4)

Guidance literature:

Glyoxal; With formic acid; copper(II) sulfate; sodium chloride; at 50 ℃; for 0.5h;

N-(2,3-methyleneoxy-N-benzyl)-β-(3,4-methyleneoxyphenyl)ethylamine; at 90 ℃; for 3h; Reagent/catalyst; Further stages;

upstream raw materials:

N-methyl-13,14-dehydrostylopinium chloride

protopine

dichloromethane

berberine chloride

Downstream raw materials:

Stylopine

Refernces

• 1、 Mori-Quiroz, Luis M.,Hedrick, Sidnee L.,De Los Santos, Andrew R.,Clift, Michael D.. "A Unified Strategy for the Syntheses of the Isoquinolinium Alkaloids Berberine, Coptisine, and Jatrorrhizine". . p. 4281 - 4284. Retrieved 2018/07/29.
• 2、 Cui, Xiang Juan,Lu, Ying Ying,Zhao, Min,Qian, Shan,Wu, Yong. "The new shortcut synthesis of 8-oxocoptisine". body text. p. 1281 - 1282. Retrieved 2011/10/08.