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Merck
CN

27650

Sigma-Aldrich

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
Beilstein:
2228813
EC Number:
200-598-5
MDL number:
MFCD00078484
UNSPSC Code:
12352200
PubChem Substance ID:
329753008

Key Documents

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biological source

plant

Assay

≥96.0% (HPLC)

form

fine crystals

impurities

≤10% ethyl acetate + H2O
≤3% water

mp

150-160 °C (dec.) (lit.)

solubility

water: soluble

SMILES string

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

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

InChI key

IAKHMKGGTNLKSZ-INIZCTEOSA-N

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

Signal Word

Danger

Hazard Statements

H300,H340

Hazard Classifications

Acute Tox. 2 Oral - Muta. 1B

Storage Class Code

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

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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P. Dustin
Microtubles, 11-11 (1978)
Romeo Romagnoli et al.
Journal of medicinal chemistry, 56(6), 2606-2618 (2013-03-01)
Two new series of inhibitors of tubulin polymerization based on the 2-(alkoxycarbonyl)-3-(3',4',5'-trimethoxyanilino)benzo[b]thiophene and thieno[2,3-b]pyridine molecular skeletons were synthesized and evaluated for antiproliferative activity on a panel of cancer cell lines, inhibition of tubulin polymerization, cell cycle effects, and in vivo
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
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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