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Merck
CN

855774

Colchicine

95%

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:
Molecular Weight:
399.44
EC Number:
200-598-5
UNSPSC Code:
12352103
MDL number:
Beilstein/REAXYS Number:
2228813
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assay

95%

optical activity

[α]24/D −443°, c = 1.7 in H2O

impurities

10% ethyl acetate and chloroform

mp

150-160 °C (dec.) (lit.)

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

Application

For a review summarizing the metabolism and pharmacokinetics of this alkaloid, see Z. Gastroenterol. .


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pictograms

Skull and crossbonesHealth hazard

signalword

Danger

hcodes

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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A Sabouraud et al.
Zeitschrift fur Gastroenterologie, 30 Suppl 1, 35-39 (1992-03-01)
Thanks to the development of a sensitive and specific radioimmunoassay for colchicine, the pharmacokinetics of colchicine is now well-established after single oral doses. Absorption is characterized by a zero-order rate constant while disposition appears biexponential with a rapid distribution phase
Chem. Abstr., 118, 32389e-32389e (1993)
Bernard L Flynn et al.
Journal of medicinal chemistry, 54(17), 6014-6027 (2011-07-22)
A structure-activity relationship (SAR) guided design of novel tubulin polymerization inhibitors has resulted in a series of benzo[b]furans with exceptional potency toward cancer cells and activated endothelial cells. The potency of early lead compounds has been substantially improved through the