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About This Item
Empirical Formula (Hill Notation):
C22H25NO6
CAS Number:
Molecular Weight:
399.44
NACRES:
NA.77
PubChem Substance ID:
UNSPSC Code:
12352200
EC Number:
200-598-5
MDL number:
Beilstein/REAXYS Number:
2228813
Product Name
Colchicine, ≥95% (HPLC), powder
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
Gene Information
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
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.
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.
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signalword
Danger
hcodes
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
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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)

