6020-18-4

Basic information

• Product Name: Coptisine chloride
• Synonyms: 2,3,9,10-BISMETHYLENEDIOXYPROTOBERBERINE;COPTISINE CHLORIDE;COPTISINE CHLORIDE(P);7,8,13,13a-Tetradehydro-2,3:9,10-bis(methylenedioxy)berbinium chloride;Coptisine Hcl;Coptisine Hydrochloride;COPTISINECHLORIDE(P)(PLEASECALL);6,7-Dihydrobis[1,3]benzodioxolo[5,6-a:4',5'-g]quinoliziniuM Chloride
• CAS NO: 6020-18-4
• Molecular Formula: C₁₉H₁₄NO₄*Cl
• Molecular Weight: 355.77
• EINECS: 1592732-453-0
• Product Categories: Amines;Heterocycles;Inhibitor;Intermediates & Fine Chemicals;Pharmaceuticals;chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract
• Mol File: 6020-18-4.mol
• Article Data: 5

Chemical Properties

• Melting Point: >258°C (dec.)
• Boiling Point: 601.5oC at 760 mmHg
• Flash Point: 190.4oC
• Appearance: /
• Density: 1.51g/cm3
• Vapor Pressure: 2E-14mmHg at 25°C
• Refractive Index: 1.749
• Storage Temp.: Hygroscopic, Refrigerator, Under Inert Atmosphere
• Solubility: DMSO (Slightly), Methanol (Slightly, Sonicated)
• Stability: Hygroscopic
• CAS DataBase Reference: Coptisine chloride(CAS DataBase Reference)
• NIST Chemistry Reference: Coptisine chloride(6020-18-4)
• EPA Substance Registry System: Coptisine chloride(6020-18-4)

Safety Data

• Hazardous Substances Data: 6020-18-4(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 6020-18-4 differently. You can refer to the following data:
1. 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.
2. 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.

InChI:InChI=1/C19H15NO4/c1-2-16-19(24-10-21-16)14-8-20-4-3-12-6-17-18(23-9-22-17)7-13(12)15(20)5-11(1)14/h1-2,5-8,15H,3-4,9-10H2

Upstream product

• 53777-79-0 N-methyl-13,14-dehydrostylopinium chloride 
• 1484-85-1 3,4-methylenedioxyphenylethylamine 
• 191847-31-1 (2-benzo[1,3]dioxol-5-yl-ethyl) carbaminic acid tert-butyl ester 
• 65842-89-9 5-(6-bromo-benzo[1,3]dioxol-5-ylmethyl)-5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]isoquinoline 
• 89045-84-1 5-(6-bromo-benzo[1,3]dioxol-5-ylmethyl)-6-formyl-5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]isoquinoline 
• 65826-53-1 14-bromo-6,7,12b,13-tetrahydro-4H-[1,3]dioxolo[4,5-g][1,3]dioxolo[4',5':7,8]isoquino[3,2-a]isoquinoline 
• 84-39-9 Stylopine 
• 889115-21-3 2-{5-bromobenzo[d][1,3]dioxol-6-yl}acetaldehyde 
• 837361-47-4 5-bromo-6-(2-methoxyvinyl)benzo[d][1,3]dioxole 
• 131543-46-9 Glyoxal 
• 633-65-8 berberine chloride 
• 75-09-2 dichloromethane 
• 130-86-9 protopine 
• 53777-78-9 Dihydrocoptisine 

Downstream Products

• 53777-78-9 Dihydrocoptisine 
• 19716-61-1 coptisinone 

Relevant articles and documents

A Unified Strategy for the Syntheses of the Isoquinolinium Alkaloids Berberine, Coptisine, and Jatrorrhizine

Total syntheses of the antibacterial alkaloids berberine, coptisine, and jatrorrhizine have been achieved in four steps through a unified route. The key step of this strategy is an efficient intramolecular Friedel-Crafts alkoxyalkylation which, following oxidation, establishes the isoquinolinium core of these natural products. Herein, the design and development of this synthetic strategy, which has enabled the shortest and most efficient syntheses of these alkaloids reported to date, is described.

Rhizoma Coptidis alkali salt of the synthetic method and its use

The invention discloses a synthetic method and application of coptisine halate; the synthetic method of the coptisine halate comprises the following steps: 1) using formic acid and phosphoric acid accounting for 0-10% of by volume of the formic acid as solvents, adding anhydrous copper sulfate, sodium chloride and oxalaldehyde for reflux and stirring for reaction; 2) adding N-(2, 3-methylenedioxy-N-benzyl)-beta-(3, 4-methylenedioxy phenyl) ethylamine into the reaction system, continuing reflux for reaction; 3) after the reaction is completed, washing the filter cake with water to remove reaction residues; and 4) putting the filter cake into a NaHCO3 solution, heating, stirring, filtering while the solution is hot, adding haloid acid into the filtrate, and cooling for crystallization. The method sharply improve the coptisine halate yield from 23.4% to more than 70.2%, the coptisine halate yield is far beyond the range of expected yield, and an unexpected technical effect is achieved. The coptisine halate prepared by the method can be used for preparing weight reducing medicines and cardiovascular disease preventing drugs.

From protopines to berbines: Synthesis of 1-methoxystylopine and its N-metho salts from coulteropine

The transformation of protopines into berbines under improved conditions has been used to synthesize 1-methoxystylopine. Coulteropine, the main alkaloid from Romneya coulteri, was used as the starting protopine to accomplish the stereocontrolled synthesis of both cis and trans N-methyl-1-methoxystylopinium salts. The results of ab initio calculations (B3LYP/6-31G**) which are consistent with experimental data, sustain the influence of the C-1 substituent on both the conformational equilibrium of berbines and the rate of N-methylation.