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855774

Sigma-Aldrich

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:
64-86-8
Molecular Weight:
399.44
Beilstein:
2228813
EC Number:
200-598-5
MDL number:
MFCD00078484
UNSPSC Code:
12352103

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

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Application

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

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Product No.
Description
Pricing

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 Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

EU REACH Annex XVII (Restriction List)

CAS No.

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Certificates of Analysis (COA)

Lot/Batch Number
09124CG
07016MO
05723CF
12331KF
07730DY

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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
Sébastien Fortin et al.
European journal of medicinal chemistry, 46(11), 5327-5342 (2011-09-17)
The importance of the bridge linking the two phenyl moieties of substituted phenyl 4-(2-oxoimidazolidin-1-yl)benzenesulfonates (PIB-SOs) was assessed using a sulfonamide group, which is a bioisostere of sulfonate and ethenyl groups. Forty one phenyl 4-(2-oxoimidazolidin-1-yl)benzenesulfonamide (PIB-SA) derivatives were prepared and biologically
Chih-Ying Nien et al.
Journal of medicinal chemistry, 53(5), 2309-2313 (2010-02-13)
A series of aroylquinoline derivatives were synthesized and evaluated for anticancer activity. 5-Amino-6-methoxy-2-aroylquinoline 15 showed more potent antiproliferative activity (IC(50) values ranging from 0.2 to 0.4 nM) as compared to 1a (combretastatin A-4) (IC(50) = 1.9-835 nM) against various human
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