All Photos(5)

C9754

Sigma-Aldrich

Colchicine

≥95% (HPLC), powder

Synonym(s):
(S)-N-(5,6,7,9-Tetrahydro-1,2,3,10-tetramethoxy-9-oxobenzo[a]heptalen-7-yl)acetamide
Empirical Formula (Hill Notation):
C22H25NO6
CAS Number:
Molecular Weight:
399.44
Beilstein:
2228813
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.77

Quality Level

assay

≥95% (HPLC)

form

powder

color

white to yellow

mp

150-160 °C (dec.) (lit.)

solubility

ethanol: 50 mg/mL

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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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.

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

Packaging

100, 500 mg in poly bottle
1, 5 g in poly bottle

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.

Pictograms

Skull and crossbonesHealth hazard

Signal Word

Danger

Hazard Statements

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 Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

Certificate of Analysis

Certificate of Origin

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)
Colchicine-an overview for plant biotechnologists
Ramawat KG and Merillon JM
Bioactive Molecules and Medicinal Plants, 215-232 (2008)
Lynette J Oost et al.
Journal of cachexia, sarcopenia and muscle, 10(3), 630-642 (2019-03-22)
Skeletal muscle is a plastic tissue that adapts to changes in exercise, nutrition, and stress by secreting myokines and myometabolites. These muscle-secreted factors have autocrine, paracrine, and endocrine effects, contributing to whole body homeostasis. Muscle dysfunction in aging sarcopenia, cancer...
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)

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