Demecolcine

Base Information

• Chemical Name: Demecolcine
• CAS No.: 477-30-5
• Molecular Formula: C21H25 N O5
• Molecular Weight: 371.433
• European Community (EC) Number: 207-514-6
• NSC Number: 403147,3096
• UNII: Z01IVE25KI
• DSSTox Substance ID: DTXSID7020342
• Nikkaji Number: J9.231B
• Wikipedia: Demecolcine
• Wikidata: Q903666
• NCI Thesaurus Code: C419
• Metabolomics Workbench ID: 53125
• ChEMBL ID: CHEMBL312862
• Mol file: 477-30-5.mol

Synonyms:Colcemid;Colcemide;Colchamine;Demecolcine;Demecolcine, (+-)-Isomer

Chemical Property of Demecolcine

Chemical Property:

• Vapor Pressure: 1.46E-15mmHg at 25°C
• Melting Point: 73-75°C
• Refractive Index: 1.5614 (estimate)
• Boiling Point: 625.5°Cat760mmHg
• PKA: 8.48±0.40(Predicted)
• Flash Point: 332.1°C
• PSA: 66.02000
• Density: 1.21g/cm³
• LogP: 3.34580
• Storage Temp.: 2-8°C
• Sensitive.: Air & Light Sensitive
• Solubility.: DMSO: 10 mg/mL
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 5
• Exact Mass: 371.17327290
• Heavy Atom Count: 27
• Complexity: 653

Purity/Quality:

99% ^*data from raw suppliers

Demecolcine ^*data from reagent suppliers

Safty Information:

• Hazard Codes: T,T+
• Statements: 25-26/27/28
• Safety Statements: 22-24/25-45-36/37/39

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Uses -> Biochemical Research
• Canonical SMILES: CNC1CCC2=CC(=C(C(=C2C3=CC=C(C(=O)C=C13)OC)OC)OC)OC
• Isomeric SMILES: CN[C@H]1CCC2=CC(=C(C(=C2C3=CC=C(C(=O)C=C13)OC)OC)OC)OC
• Description: Colcemid is a colchicine derivative that inhibits tubulin polymerization as potently as colchicine (IC50 = 2.1 and 2.4 μM, respectively) but is less toxic. At very low (nanomolar) concentrations, colcemid suppresses microtubule dynamicity and inhibits cell migration, while at micromolar levels it blocks microtubule assembly, arresting cells in metaphase. Mitotic block by colcemid is used to synchronize cells and for karyotyping in cytogenetic studies. Prolonged exposure to colcemid can activate p53, leading to apoptosis.
• Uses: An antimitotic agent that disrupts microtubles by binding to tubulin and preventing its polymerization. Stimulates the intrinsic GTPase activity of tubulin. Induces apoptosis in several normal and tumor cell lines and activates the JNK/SAPK signaling pathway. Inhibitor of spindle fiber formation Cell synchronization agent; for chromosome visualization; to induce oocyte enucleation for somatic cell cloning.

Technology Process of Demecolcine

There total 8 articles about Demecolcine 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: 40.0%

(-)-N-formyldemecolcine (14686-61-4) → (-)-demecolcine (477-30-5)

Guidance literature:

With sulfuric acid; water; at 100 ℃; for 20h;

DOI:10.1039/a803851a

Reference yield:

colchicine (64-86-8,54192-66-4) → (-)-demecolcine (477-30-5)

Guidance literature:

Multi-step reaction with 3 steps

1: aqueous HCl

2: CH₂Cl₂; diethyl ether

3: benzene

With hydrogenchloride; diethyl ether; dichloromethane; benzene;

DOI:10.1002/hlca.19540370104

Reference yield:

colchiceine (477-27-0,1990-46-1) → (-)-demecolcine (477-30-5)

Guidance literature:

Multi-step reaction with 3 steps

1: aqueous HCl

2: CH₂Cl₂; diethyl ether

3: benzene

With hydrogenchloride; diethyl ether; dichloromethane; benzene;

DOI:10.1002/hlca.19540370104

upstream raw materials:

diazomethane

(-)-2-demethyldemecolcine

demecolceine

(-)-N-formyldemecolcine

Downstream raw materials:

thiodemecolcine

demecolceine

N-(hydroxyacetyl)demecolcine

(-)-N-formyldemecolcine

Refernces