DEMECOLCINE

DEMECOLCINE Basic information
Product Name:DEMECOLCINE
Synonyms:substancef;Colcemide;DEMECOLCINE HYBRI-MAXR;DEMECOLCINE SOLUTION 10 UG/ML;Colcemid-D3=Demecolcine-D3;N-Deacetyl-N-methyl(deutero)colchicine;COLCEMID;COLCEMIDE(R)
CAS:477-30-5
MF:C21H25NO5
MW:371.43
EINECS:207-514-6
Product Categories:All Inhibitors;Inhibitors
Mol File:477-30-5.mol
DEMECOLCINE Structure
DEMECOLCINE Chemical Properties
Melting point 73-75°C
alpha D20 -129.0° (c = 1 in chloroform)
Boiling point 501.11°C (rough estimate)
density 1.2350 (rough estimate)
refractive index 1.5614 (estimate)
storage temp. 2-8°C
solubility DMSO: 10 mg/mL
pka8.48±0.40(Predicted)
form powder
Sensitive Air & Light Sensitive
BRN 2822892
Stability:Hygroscopic
Safety Information
Hazard Codes T,T+
Risk Statements 25-26/27/28
Safety Statements 22-24/25-45-36/37/39
RIDADR UN 2811 6.1/PG 2
WGK Germany 3
RTECS GH0800000
8-10-23
HazardClass 6.1(a)
PackingGroup II
ToxicityLD50 oral in mouse: 25530ug/kg
MSDS Information
ProviderLanguage
SigmaAldrich English
DEMECOLCINE Usage And Synthesis
DescriptionColcemid 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.
Chemical PropertiesFaintly Yellow Crystalline Powder
UsesAn 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.
UsesInhibitor of spindle fiber formation
UsesCell synchronization agent; for chromosome visualization; to induce oocyte enucleation for somatic cell cloning.
DefinitionChEBI: A secondary amino compound that is (S)-colchicine in which the N-acetyl group is replaced by an N-methyl group. Isolable from the autumn crocus, Colchicum autumnale, it is less toxic than olchicine and is used as an antineoplastic.
General DescriptionColcemid is also known as demecolcine. Its generic name is N-methyl-N-deacetyl-colchicine. Colcemid depolymerizes microtubules and blocks mitosis at metaphase.
Biochem/physiol ActionsOften in karyotyping and cell cycle research it is desirable to increase the yield of mitotic cells in a particular phase of the cell cycle. This can be achieved in a variety of ways with the most popular being the use of a cell cycle synchronizing agent such as demecolcine. Demecolcine will arrest cells in metaphase with no remarkable effect on the biochemical events in mitotic cells or in synchronized G1 and S phase cells. White blood cells are often treated with demecolcine to arrest cells in metaphase.
Safety ProfilePoison by ingestion, intraperitoneal, parenteral, intravenous, and intramuscular routes. Human systemic effects by ingestion: (skin and appendages) hair effects. Human mutation data reported. An experimental teratogen. Experimental reproductive effects. When heated to decomposition it emits toxic fumes of NOx.
Purification MethodsColcemide is purified by chromatography on silica and eluting with CHCl3/MeOH (9:1), and by recrystallisation from EtOAc/Et2O to form yellow prisms. UV in EtOH has max 243nm ( 30,200) and 350nm ( 16,3000). [Synthesis, IR, NMR, MS: Capraro & Brossi Helv Chim Acta 62 965 1979, Beilstein 8 IV 3319.]
DEMECOLCINE Preparation Products And Raw materials
Preparation ProductsN-Formyldemecolcine
DEMECOLCIN-D3 DEMECOLCINE COLCHICINE-D6 DEMECOLCINE HYDROGEN BROMIDE SALT N-(2-MERCAPTOETHYL) DEMECOLCINE N-TRIFLUOROACETYL DEACETYLCOLCHICINE Colchicine GLORIOSINE DEMECOLCINE-D6 N-TRIFLUOROACETYL-N-METHYL-DEACETYLCOLCHICINE COLCHICINE-D3 (S)-7-[(2-HYDROXY-BENZYL)-METHYL-AMINO]-1,2,3,10-TETRAMETHOXY-6,7-DIHYDRO-5H-BENZO[A]HEPTALEN-9-ONE COLCHICINE SALICYLATE COLCHICINE METHANETHIOSULFONATE COLCHICINE, [RING C, METHOXY-3H] COLCHICINE, [RING C, METHOXY-14C] NBD-DEMECOLCIN COLCHICOSIDE

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