Coptisine

Base Information

• Chemical Name: Coptisine
• CAS No.: 3486-66-6
• Molecular Formula: C19H14 N O4
• Molecular Weight: 320.324
• UNII: 0GCL71VN14
• DSSTox Substance ID: DTXSID10188404
• Nikkaji Number: J8.657F
• Wikipedia: Coptisine
• Wikidata: Q5169053
• Metabolomics Workbench ID: 132840
• ChEMBL ID: CHEMBL362071
• Mol file: 3486-66-6.mol

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

Chemical Property of Coptisine

Chemical Property:

• Melting Point: 212-217 °C
• Boiling Point: °Cat760mmHg
• Flash Point: °C
• PSA: 40.80000
• Density: g/cm³
• LogP: 2.80780
• XLogP3: 3.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 0
• Exact Mass: 320.09228293
• Heavy Atom Count: 24
• Complexity: 502

Purity/Quality:

HPLC≥98% ^*data from raw suppliers

Coptisine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): A poison.
• Hazard Codes: A poison.:
• Safety Statements: A poison by ingestion. When heated to decomposition it emits toxic vapors of NO:

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

Technology Process of Coptisine

There total 17 articles about Coptisine 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: 74.0%

C19H15NO5 → coptisine (3486-66-6)

Guidance literature:

With methanesulfonyl chloride; triethylamine; In dichloromethane; at 20 ℃; for 6h;

Reference yield:

N-Methyl-dihydrocoptisinium-Kation (20105-28-6) → coptisine (3486-66-6)

Guidance literature:

In dimethyl sulfoxide; at 115 - 120 ℃; for 25.5h;

DOI:10.1080/14786419.2013.867344

Reference yield:

Dihydrocoptisine (53777-78-9) → coptisine (3486-66-6)

Guidance literature:

With iodine; potassium acetate; In ethanol; at 20 ℃; Inert atmosphere;

DOI:10.1002/chem.201601245

upstream raw materials:

berberine

dichloromethane

protopine

N-Methyl-dihydrocoptisinium-Kation

Downstream raw materials:

coptisinone

Stylopine

C₂₀H₁₉NO₆

(+/-)-Ochrobirin

Refernces

• 1、 Zhou, Shiqiang,Tong, Rongbiao. "A General, Concise Strategy that Enables Collective Total Syntheses of over 50 Protoberberine and Five Aporhoeadane Alkaloids within Four to Eight Steps". supporting information. p. 7084 - 7089. Retrieved 2016/05/19.
• 2、 Wu, Jian Bo,Lei, Fan,Cui, Xiang Juan,He, Yun,Hai, Li,Zhang, Juan,Wu, Yong. "Design, synthesis and multidrug resistance reversal activity evaluation of 8-oxocoptisine derivatives". experimental part. p. 742 - 748. Retrieved 2012/09/08.