C9754

Colchicine

Name: Colchicine
Brand: SIGMA

≥95% (HPLC), powder, antimitotic agent

Synonym(s):

(S)-N-(5,6,7,9-Tetrahydro-1,2,3,10-tetramethoxy-9-oxobenzo[a]heptalen-7-yl)acetamide

Select a Size

All Photos(5)

About This Item

Empirical Formula (Hill Notation):

C₂₂H₂₅NO₆

CAS Number:

64-86-8

Molecular Weight:

399.44

NACRES:

NA.77

PubChem Substance ID:

24278348

UNSPSC Code:

12352200

EC Number:

200-598-5

MDL number:

MFCD00078484

Beilstein/REAXYS Number:

2228813

Product Name

Colchicine, ≥95% (HPLC), powder

InChI key

IAKHMKGGTNLKSZ-INIZCTEOSA-N

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

SMILES string

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

assay

≥95% (HPLC)

form

powder

color

white to yellow

mp

150-160 °C (dec.) (lit.)

solubility

ethanol: 50 mg/mL

Quality Level

200

Gene Information

human ... ABCB1(5243), CYP3A4(1576), 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)
mouse ... Abcb1a(18671), Abcb1b(18669)

Looking for similar products? Visit Product Comparison Guide

Related Categories

Bioactive Small Molecule Inhibitors

Bioactive Small Molecules

Application

Colchicine has been used:

in the in vitro sister-chromatid exchange (SCE) assay
to study its in vitro antiviral, antibacterial, antifungal and cytotoxic activities
in microtubule disruption
to analyse its effects on Ca²⁺ transients from taxol-treated cells

Biochem/physiol Actions

Antimitotic agent that disrupts microtubules by binding to tubulin and preventing its polymerization. Stimulates the intrinsic GTPase activity of tubulin. Induces apoptosis in several normal and tumor cell lines and activates the JNK/SAPK signaling pathway.

Features and Benefits

This compound is a featured product for ADME Tox research. Click here to discover more featured ADME Tox products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.

General description

Colchicine is a secondary metabolite, which has anti-inflammatory properties. It is used to treat gout, crystal-induced joint inflammation, familial Mediterranean fever, Behçet disease, vasculitides and pericarditis. Colchicine inhibits cell division, intracellular vesicle motility, secretion of cytokines and chemokines. It is implicated in leukocyte diapedesis and lysosomal degranulation. Colchicine also blocks fibroblast proliferation and collagen transport to extracellular space.

Preparation Note

This product in powdered format can be stored in room temperature. Colchicine powder will darken upon exposure to light. Colchicine solutions can be sterilized by autoclaving or filtration. Sterilized solutions are stable for at least six months if protected from light. No appreciable colchicine hydrolysis occurred in neutral and slightly alkaline (pH = 8.1) solutions after storage frozen for 2 months.

pictograms

GHS06,GHS08

signalword

Danger

hcodes

H300,H340

pcodes

P202 - P264 - P270 - P280 - P301 + P310 - P405

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

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Search for a COA

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Colchicine-an overview for plant biotechnologists

Ramawat KG and Merillon JM

Bioactive Molecules and Medicinal Plants, 215-232 (2008)

Genotoxic, cytostatic, antineoplastic and apoptotic effects of newly synthesized antitumour steroidal esters

Karapidaki I, et al.

Mutation Research. Genetic Toxicology and Environmental Mutagenesis, 675(1), 51-59 (2009)

Colchicine today

Niel E and Scherrmann JM

Joint, Bone, Spine : Revue du Rhumatisme, 73(6), 672-678 (2006)

Effect of the microtubule polymerizing agent taxol on contraction, Ca2+ transient and L-type Ca2+ current in rat ventricular myocytes

Howarth FC, et al.

The Journal of Physiology, 516(2), 409-419 (1999)

A leukemia fusion protein attenuates the spindle checkpoint and promotes aneuploidy

Boyapati A, et al.

Blood, 109(9), 3963-3971 (2007)

View All Related Papers

Articles

Discover Bioactive Small Molecules for ADME/Tox

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service