C9754

Colchicine

≥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
• 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: 12352200
• PubChem Substance ID: 24278348
• NACRES: NA.77

Properties

• product name: Colchicine, ≥95% (HPLC), powder
• 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: 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)

Description

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.

Storage and Stability

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.

Safety Information

• Pictograms: GHS06,GHS08
• Signal Word: Danger
• Hazard Statements: H300,H340
• Precautionary Statements: P202 - P264 - P270 - P280 - P301 + P310 - P405
• 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