C3915

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: 64-86-8
• Molecular Weight: 399.44
• UNSPSC Code: 10171502
• NACRES: NA.72
• PubChem Substance ID: 24892656
• EC Number: 200-598-5
• Beilstein/REAXYS Number: 2228813
• MDL number: MFCD00078484
• Assay: ≥95% (HPLC)
• Form: powder
• Quality level: 200

Properties

• InChI key: IAKHMKGGTNLKSZ-INIZCTEOSA-N
• 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
• SMILES string: COC1=CC=C2C(=CC1=O)[C@H](CCc3cc(OC)c(OC)c(OC)c23)NC(C)=O
• product line: BioReagent
• assay: ≥95% (HPLC)
• form: powder
• technique(s): cell culture | plant: suitable
• mp: 150-160 °C (dec.) (lit.)
• application(s): agriculture
• Quality Level: 200
• 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

Application

Colchicine has been used:

• as an inhibitor of tubulin polymerization in bone-marrow-derived macrophages[1]
• for the inhibition of in vitro neurite outgrowth in human neuronal cells[2]
• as microtubule destabilizer to induce peripheral neuropathy in induced pluripotent stem cell derived neurons (iPSC-Neurons)[3]

Biochem/physiol Actions

Colchicine interacts with albumin and binds to tubulin. Its association with tubulin impacts autophagic vacuole fusion with lysosomes.[4] It inhibits tyrosine kinases and phospholipases. Colchicine may be useful for treating acute coronary syndromes.[5] It is prescribed for treating rheumatologic conditions including familial mediterranean fever (FMF) and acute gouty arthritis.[6]

Colchicine is an inhibitor of microtubule polymerization which blocks chromosome segregation during meiosis. Consequently, Colchicine is used to induce polyploidy (tetraploid) in plant cells.

General description

Colchicine is a tricyclic alkaloid that can stay in circulation for 20 to 40 hours post intake. Leucocytes harbour maximum colchicine.[4] It contains three hexameric rings termed A, B and C.[5]

Preparation Note

Preparation and Use

Safety Information

• pictograms: GHS06,GHS08
• signalword: Danger
• hcodes: H300,H340
• pcodes: P202 - P264 - P270 - P280 - P301 + P310 - P405
• 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