Demecolcine

Title: Demecolcine
CAS Registry Number: 477-30-5
CAS Name: 6,7-Dihydro-1,2,3,10-tetramethoxy-7-(methylamino)benzo[a]heptalen-9(5H)-one
Additional Names: N-deacetyl-N-methylcolchicine; N-methyl-N-desacetylcolchicine; colchamine; Santavy's substance F; colcemid
Molecular Formula: C21H25NO5
Molecular Weight: 371.43
Percent Composition: C 67.91%, H 6.78%, N 3.77%, O 21.54%
Literature References: Antitumor alkaloid; depolymerizes microtubules and inhibits spindle formation during metaphase. Isoln from Colchicum autumnale L., Liliaceae: Santavy, Pharm. Acta Helv. 25, 248 (1950); Santavy, Reichstein, Helv. Chim. Acta 33, 1606 (1950); Schlittler, Uffer, DE 936268 (1955 to Ciba), C.A. 53, 1396 (1959). Structure: Santavy et al., Helv. Chim. Acta 36, 1319 (1953). Synthesis: Uffer et al., ibid. 37, 18 (1954); H. G. Capraro, A. Brossi, ibid. 62, 965 (1979). Effect on the mitotic cycle: C. L. Rieder, R. E. Palazzo, J. Cell Sci. 102, 387 (1992). Use in oocyte enucleation: E. Ibáñez et al., Biol. Reprod. 68, 1249 (2003).
Properties: Pale yellow prisms from ethyl acetate + ether, mp 186°. [a]D20 -129.0° (c = 1 in chloroform). uv max (alc): 245, 355 nm (log e 4.55, 4.24). Basic reaction. Soluble in acidified water, in alcohol, ether, chloroform, benzene.
Melting point: mp 186°
Optical Rotation: [a]D20 -129.0° (c = 1 in chloroform)
Absorption maximum: uv max (alc): 245, 355 nm (log e 4.55, 4.24)
Use: Cell synchronization agent; for chromosome visualization; to induce oocyte enucleation for somatic cell cloning.
Demeton Demexiptiline Denatonium Benzoate Dendrotoxins Denileukin Diftitox

Demecolcine
Demecolcine.png
Systematic (IUPAC) name
(S)-1,2,3,10-Tetramethoxy-7-methylamino-6,7-dihydro-5H-benzo[a]heptalen-9-one
Clinical data
Legal status  ?
Identifiers
CAS number 477-30-5 YesY
ATC code L01CC01
PubChem CID 2832
ChemSpider 191135 YesY
UNII Z01IVE25KI YesY
ChEMBL CHEMBL312862 YesY
Chemical data
Formula C21H25NO5 
Mol. mass 371.43 g/mol
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Demecolcine, also known as colcemid, is a drug used in chemotherapy.It is closely related to the natural alkaloid colchicine with the replacement of the acetyl group on the amino moiety with methyl, but it is less toxic. It depolymerises microtubules and limits microtubule formation (inactivates spindle fibre formation), thus arresting cells in metaphase and allowing cell harvest and karyotyping to be performed.

During cell division Demecolcine inhibits mitosis at metaphase by inhibiting spindle formation. Medically Demecolcine has been used to improve the results of cancer radiotherapy by synchronising tumour cells at metaphase, the radiosensitive stage of the cell cycle.[1]

In animal cloning procedures Demecolcine makes an ovum eject its nucleus, creating space for insertion of a new nucleus.[2]