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

form 

powder

pka

8.48±0.40(Predicted)

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

F 

8-10-23

HazardClass 

6.1(a)

PackingGroup 

II

Toxicity

LD50 oral in mouse: 25530ug/kg

MSDS

• Language:English Provider:SigmaAldrich

DEMECOLCINE Usage And Synthesis

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.

Chemical Properties

Faintly Yellow Crystalline Powder

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.

Uses

Inhibitor of spindle fiber formation

Uses

Cell synchronization agent; for chromosome visualization; to induce oocyte enucleation for somatic cell cloning.

Definition

ChEBI: 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 Description

Colcemid is also known as demecolcine. Its generic name is N-methyl-N-deacetyl-colchicine. Colcemid depolymerizes microtubules and blocks mitosis at metaphase.

Biochem/physiol Actions

Often 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 Profile

Poison 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 Methods

Colcemide 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(477-30-5)Related Product Information

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• Colchicine
• COLCHICOSIDE
• DEMECOLCINE
• COLCHICINE, [RING C, METHOXY-14C]
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• N-(2-MERCAPTOETHYL) DEMECOLCINE
• N-TRIFLUOROACETYL DEACETYLCOLCHICINE
• N-TRIFLUOROACETYL-N-METHYL-DEACETYLCOLCHICINE
• COLCHICINE METHANETHIOSULFONATE
• COLCHICINE-D3
• DEMECOLCINE HYDROGEN BROMIDE SALT
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• (S)-7-[(2-HYDROXY-BENZYL)-METHYL-AMINO]-1,2,3,10-TETRAMETHOXY-6,7-DIHYDRO-5H-BENZO[A]HEPTALEN-9-ONE
• COLCHICINE SALICYLATE
• DEMECOLCIN-D3