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C3915 Sigma-Aldrich

Colchicine

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

Synonym: (S)-N-(5,6,7,9-Tetrahydro-1,2,3,10-tetramethoxy-9-oxobenzo[a]heptalen-7-yl)acetamide

  • CAS Number 64-86-8

  • Empirical Formula (Hill Notation) C22H25NO6

  • Molecular Weight 399.44

  •  Beilstein/REAXYS Number 2228813

  •  EC Number 200-598-5

  •  MDL number MFCD00078484

  •  PubChem Substance ID 24892656

  •  NACRES NA.72

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Properties

product line   BioReagent
assay   ≥95% (HPLC)
application(s)   cell culture | plant: suitable
mp   150-160 °C (dec.) (lit.)
Featured Industry   Agriculture
storage temp.   room temp
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 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

Preparation and Use

Safety & Documentation

Safety Information

Symbol 
Signal word 
Danger
Hazard statements 
Precautionary statements 
RIDADR 
UN 1544PSN1 6.1 / PGI
WGK Germany 
WGK 3
RTECS 
GH0700000
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable

Documents

Certificate of Analysis (COA)

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Certificate of Origin (COO)

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Protocols & Articles

Articles

Using Global Reach to Source and Deliver Critical Plant Breeding Chemicals

For many crops, colchicine is used to produce doubled haploids, enabling homozygosity in a single generation. When used, this process enables seed development companies to deliver better-performing v...
Keywords: Agriculture

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Peer-Reviewed Papers
15

References

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