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Merck
CN

27650

Colchicine

≥96.0% (HPLC)

Synonym(s):

(S)-N-(5,6,7,9-Tetrahydro-1,2,3,10-tetramethoxy-9-oxobenzo[a]heptalen-7-yl)acetamide

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About This Item

Empirical Formula (Hill Notation):
C22H25NO6
CAS Number:
64-86-8
Molecular Weight:
399.44
EC Number:
200-598-5
UNSPSC Code:
12352200
PubChem Substance ID:
329753008
Beilstein/REAXYS Number:
2228813
MDL number:
MFCD00078484

Key Documents

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impurities

≤3% water, ≤10% ethyl acetate + H2O

InChI key

IAKHMKGGTNLKSZ-INIZCTEOSA-N

InChI

1S/C22H25NO6/c1-12(24)23-16-8-6-13-10-19(27-3)21(28-4)22(29-5)20(13)14-7-9-18(26-2)17(25)11-15(14)16/h7,9-11,16H,6,8H2,1-5H3,(H,23,24)/t16-/m0/s1

SMILES string

COC1=CC=C2C(=CC1=O)[C@H](CCc3cc(OC)c(OC)c(OC)c23)NC(C)=O

biological source

plant

assay

≥96.0% (HPLC)

form

fine crystals

mp

150-160 °C (dec.) (lit.)

solubility

water: soluble

Gene Information

human ... TUBA1A(7846), TUBA1B(10376), TUBA1C(84790), TUBA3C(7278), TUBA3E(112714), TUBA4A(7277), TUBB(203068), TUBB1(81027), TUBB2A(7280), TUBB2B(347733), TUBB3(10381), TUBB4A(10382), TUBB4B(10383), TUBB6(84617), TUBB8(347688)

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Other Notes

Binds specifically with tubulin thus interfering with microtubule organization.

pictograms

Skull and crossbonesHealth hazard
GHS06,GHS08

signalword

Danger

hcodes

H300,H340

Hazard Classifications

Acute Tox. 2 Oral - Muta. 1B

Storage Class

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges

Regulatory Information

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P. Dustin
Microtubles, 11-11 (1978)
Spyridon Deftereos et al.
Journal of the American College of Cardiology, 61(16), 1679-1685 (2013-03-19)
This study sought to test the hypothesis that colchicine treatment after percutaneous coronary intervention (PCI) can lead to a decrease in in-stent restenosis (ISR). ISR rates are particularly high in certain patient subsets, including diabetic patients, especially when a bare-metal
Romeo Romagnoli et al.
Journal of medicinal chemistry, 56(22), 9296-9309 (2013-10-30)
The biological importance of microtubules make them an interesting target for the synthesis of antitumor agents. The 2-(3',4',5'-trimethoxybenzoyl)-5-aminobenzo[b]thiophene moiety was identified as a novel scaffold for the preparation of potent inhibitors of microtubule polymerization acting through the colchicine site of
Liliya V Frolova et al.
Journal of medicinal chemistry, 56(17), 6886-6900 (2013-08-10)
We developed synthetic chemistry to access the marine alkaloid rigidins and over 40 synthetic analogues based on the 7-deazaxanthine, 7-deazaadenine, 7-deazapurine, and 7-deazahypoxanthine skeletons. Analogues based on the 7-deazahypoxanthine skeleton exhibited nanomolar potencies against cell lines representing cancers with dismal
Rimi Chakrabarti et al.
PloS one, 8(3), e57302-e57302 (2013-03-19)
Curcumin has been widely investigated for its myriad cellular effects resulting in reduced proliferation of various eukaryotic cells including cancer cells and the human malaria parasite Plasmodium falciparum. Studies with human cancer cell lines HT-29, Caco-2, and MCF-7 suggest that
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