C3915

Colchicine

BioReagent, suitable for plant cell culture, ≥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
• Beilstein: 2228813
• EC Number: 200-598-5
• MDL number: MFCD00078484
• UNSPSC Code: 10171502
• PubChem Substance ID: 24892656
• NACRES: NA.72

Properties

• product line: BioReagent
• Assay: ≥95% (HPLC)
• form: powder
• technique(s): cell culture | plant: suitable
• mp: 150-160 °C (dec.) (lit.)
• application(s): 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
• 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)

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 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