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C9754

Sigma-Aldrich

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

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About This Item

Empirical Formula (Hill Notation):
C22H25NO6
CAS Number:
64-86-8
Molecular Weight:
399.44
Beilstein/REAXYS Number:
2228813
EC Number:
200-598-5
MDL number:
MFCD00078484
UNSPSC Code:
12352200
PubChem Substance ID:
24278348
NACRES:
NA.77

Key Documents

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Product Name

Colchicine, ≥95% (HPLC), powder

Quality Level

200

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)

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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

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.

pictograms

Skull and crossbonesHealth hazard
GHS06,GHS08

signalword

Danger

hcodes

H300,H340

Hazard Classifications

Acute Tox. 2 Oral - Muta. 1B

Storage Class

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

ppe

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges

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Certificates of Analysis (COA)

Lot/Batch Number
SLCL7913
SLCK9701
SLCF3790
WXBD1252V
WXBC9938V

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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)
Colchicine today
Niel E and Scherrmann JM
Joint, Bone, Spine : Revue du Rhumatisme, 73(6), 672-678 (2006)
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)
A leukemia fusion protein attenuates the spindle checkpoint and promotes aneuploidy
Boyapati A, et al.
Blood, 109(9), 3963-3971 (2007)
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
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