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Merck
CN

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

Key Documents

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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

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Application

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

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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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)
Emma M V Johansson et al.
Bioorganic & medicinal chemistry, 18(17), 6589-6597 (2010-08-03)
Screening of a 65,536-member one-bead-one-compound (OBOC) combinatorial library of glycopeptide dendrimers of structure ((betaGal)(n)(+1)X(8)X(7)X(6)X(5))(2)DapX(4)X(3)X(2)X(1)(beta-Gal)(m) (betaGal=beta-galactosyl-thiopropionic acid, X(8-1)=variable amino acids, Dap=l-2,3-diaminopropionic acid, n, m=0, or 1 if X(8)=Lys resp. X(1)=Lys) for binding of Jurkat cells to the library beads in cell
Giuseppe La Regina et al.
Journal of medicinal chemistry, 50(12), 2865-2874 (2007-05-15)
The new arylthioindole (ATI) derivatives 10, 14-18, and 21-24, which bear a halogen atom or a small size ether group at position 5 of the indole moiety, were compared with the reference compounds colchicine and combretastatin A-4 for biological activity.
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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