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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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Chem. Abstr., 118, 32389e-32389e (1993)
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
Samir Messaoudi et al.
Journal of medicinal chemistry, 52(14), 4538-4542 (2009-06-18)
Herein is reported a convergent synthesis of isocombretastatins A, a novel class of potent antitubulin agents. These compounds having a 1,1-diarylethylene scaffold constitute the simplest isomers of natural Z-combretastatins A that are easy to synthesize without need to control the
Ravi Kumar Anchoori et al.
Journal of medicinal chemistry, 51(19), 5953-5957 (2008-09-10)
Current microtubule inhibitory agents used in the clinic to treat cancer have severe side effects, and development of resistance is frequent. We have evaluated the antitumor effect of a novel 30-compound library of phenoxy pyridine and phenyl sulfanyl pyridine derivatives.
Sébastien Fortin et al.
Journal of medicinal chemistry, 54(13), 4559-4580 (2011-05-25)
Sixty-one phenyl 4-(2-oxoimidazolidin-1-yl)benzenesulfonates (PIB-SOs) and 13 of their tetrahydro-2-oxopyrimidin-1(2H)-yl analogues (PPB-SOs) were prepared and biologically evaluated. The antiproliferative activities of PIB-SOs on 16 cancer cell lines are in the nanomolar range and unaffected in cancer cells resistant to colchicine, paclitaxel
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