Colchicine

Colchicine
Compound Structure:
Synonyms: colchicine , Colchisol, Colchineos, Colchicinum
Compound ID: NMPC-1673
PubChem ID:

6167

Molecular Formula: C22H25NO6
Canonical SMILES: CC(=O)N[C@H]1CCC2=CC(=C(C(=C2C3=CC=C(C(=O)C=C13)OC)OC)OC)OC
InChIKey: IAKHMKGGTNLKSZ-INIZCTEOSA-N
About the compound:

Colchicine (PubChem CID 6167) is a naturally occurring tricyclic alkaloid obtained from the plant Colchicum autumnale (autumn crocus) with the molecular formula C₂₂H₂₅NO₆ and a molecular weight of about 399.4 g/mol. It appears as a pale yellow crystalline solid, is sparingly soluble in water, and is sensitive to light. Biologically, colchicine binds to tubulin and inhibits microtubule polymerization, thereby blocking mitosis and suppressing neutrophil activity, which explains its strong anti-inflammatory effect. Clinically, it is widely used in the treatment and prevention of gout and in familial Mediterranean fever. However, colchicine has a narrow therapeutic index, meaning that small dosing errors or drug interactions (especially involving CYP3A4 or P-glycoprotein inhibitors) can lead to serious toxicity.

Properties:
CategoryProperty
Compound nameColchicine
PubChem CID6167
CAS number64-86-8
Molecular formulaC₂₂H₂₅NO₆
Molecular weight~399.4 g/mol
Chemical classAlkaloid (tricyclic)
SourceColchicum autumnale (autumn crocus)
AppearancePale yellow to yellowish-white crystalline solid
SolubilitySparingly soluble in water; soluble in organic solvents
Melting point~142–150 °C
StabilityLight-sensitive (photoisomerization possible)
Mechanism of actionBinds tubulin → inhibits microtubule polymerization
Biological effectAntimitotic, anti-inflammatory
Therapeutic usesGout, Familial Mediterranean fever
ToxicityNarrow therapeutic index; toxic at high doses
MetabolismCYP3A4 and P-glycoprotein pathways
Special noteErrors in dosing or drug interactions can cause severe toxicity
Source Species: Physostigma venenosum
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