Люмикольхицин

Description

Lumicolchicine is a product of the photochemical transformation of colchicine. Under the influence of ultraviolet radiation and sunlight, colchicine transforms into a mixture of α-, β- and γ-lumicolchicines: the β- and γ-forms are stereoisomers, the α-form is a cyclobutane dimer of the β-isomer. This position corresponds to β-lumicolchicine, also known as β-lumi-(−)-colchicine. When the methyltropolone ring C is rearranged into a conjugated system of four- and five-membered rings, the molecule loses the ability to bind to tubulin, and with it the antimitotic effect of the original alkaloid. That is why the substance is used in cell biology as an inactive control to colchicine. In pharmaceutical analysis it passes as an impurity C of colchicine: appreciable amounts of lumicolchicine were found in ampoules of colchicine for intravenous administration made of colorless glass.

Basic Attributes

• CAS No.: 6901-13-9
• Chemical Formula: C22H25NO6
• Molecular weight: 399.437
• Exact weight: 399.44
• EC number: 230-008-1
• PSA Specifications: 83.09000
• XLogP3: 2.66680

Physico-chemical characteristics

• Density: 1.3 g/cm³
• Melting point: 183 °C (solvents: ethanol, diethyl ether)
• Boiling point: 623.2 °C at 760 mm Hg. Art.
• Flash point: 330.7 °C
• Refractive index: 1.596

Scope of application

• inactive control in experiments with colchicine: the compound does not bind tubulin and does not destroy microtubules, which makes it possible to separate the specific effect of colchicine from nonspecific effects
• standard sample of an impurity for quality control of the substance and dosage forms of colchicine (impurity C), including when assessing the photostability of solutions
• reagent in studies of the photochemistry of tropolone alkaloids and skeletal rearrangements of colchicine derivatives

Safety Information

• Hazard Statements: H302 - Harmful if swallowed
• GHS classification: signal word "Warning", H302 (100%)
• Precautions: P264, P270, P301 + P312, P330, P501
• Basis of classification: aggregated GHS data from two companies for 1 notification to the ECHA C and L register

Storage and transportation conditions

Storage conditions according to the card: amber glass bottle, freezer at −20 °C, inert atmosphere. The requirements are dictated by the origin of the substance: it itself is a product of photolysis and is capable of further transformations in light, including dimerization to the α-form. Transport codes are not given on the card. Do not eat, drink or smoke while working (P270), wash your hands after work (P264). If swallowed, rinse mouth (P330) and seek medical advice (P301 + P312). Hand over waste and containers to a licensed operator (P501).