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C3915

Sigma-Aldrich

Colchicine

suitable for plant cell culture, BioReagent, ≥95% (HPLC)

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.72

Quality Level

product line

BioReagent

assay

≥95% (HPLC)

application(s)

cell culture | plant: suitable

mp

150-160 °C (dec.) (lit.)

Featured Industry

Agriculture

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 tricyclic alkaloid that can stay in circulation for 20 to 40 hours post intake. Leucocytes harbour maximum colchicine. It contains three hexameric rings termed A, B and C.

Application

Colchicine has been used:
  • as an inhibitor of tubulin polymerization in bone-marrow-derived macrophages
  • for the inhibition of in vitro neurite outgrowth in human neuronal cells
  • as microtubule destabilizer to induce peripheral neuropathy in induced pluripotent stem cell derived neurons (iPSC-Neurons)

Packaging

1, 5 g in glass bottle
500 mg in glass bottle

Biochem/physiol Actions

Colchicine interacts with albumin and binds to tubulin. Its association with tubulin impacts autophagic vacuole fusion with lysosomes. It inhibits tyrosine kinases and phospholipases. Colchicine may be useful for treating acute coronary syndromes. It is prescribed for treating rheumatologic conditions including familial mediterranean fever (FMF) and acute gouty arthritis.
Colchicine is an inhibitor of microtubule polymerization which blocks chromosome segregation during meiosis. Consequently, Colchicine is used to induce polyploidy (tetraploid) in plant cells.

Preparation Note

pictograms

Skull and crossbonesHealth hazard

signalword

Danger

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

Colchicine: old and new
Slobodnick A, et al.
The American Journal of Medicine, 128(5), 461-470 (2015)
NEK7 is an essential mediator of NLRP3 activation downstream of potassium efflux
He Y, et al.
Nature, 530(7590), 354-354 (2016)
The effects of colchicine and hydroxychloroquine on the cyclo-oxygenases COX-1 and COX-2
Ben-Chetrit E, et al.
Rheumatology International, 25(5), 332-335 (2005)
Mechanism of the anti-inflammatory effect of colchicine in rheumatic diseases: a possible new outlook through microarray analysis
Ben-Chetrit E, et al.
Rheumatology (Basel), 45(3), 274-282 (2005)
Comparative Sensitivity of Human-Induced Pluripotent Stem Cell-Derived Neuronal Subtypes to Chemically Induced Neurodegeneration
Cohen JD and Tanaka Y
Applied In Vitro Toxicology, 4(4), 347-364 (2018)

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