209810-38-8

Basic information

• Product Name: (R/S)-Colchicine
• Synonyms: (R/S)-Colchicine
• CAS NO: 209810-38-8
• Molecular Formula: C22H25NO6
• Molecular Weight: 399.437
• Product Categories: Amines;Heterocycles;Inhibitors;Intermediates & Fine Chemicals;Pharmaceuticals;Amines, Heterocycles, Inhibitors, Pharmaceuticals, Intermediates & Fine Chemicals
• Mol File: 209810-38-8.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (R/S)-Colchicine(CAS DataBase Reference)
• NIST Chemistry Reference: (R/S)-Colchicine(209810-38-8)
• EPA Substance Registry System: (R/S)-Colchicine(209810-38-8)

Safety Data

• Hazardous Substances Data: 209810-38-8(Hazardous Substances Data)

Usage

Chemical Properties

Grayish Yellow Solid

Uses

Racemic Colchicine.

Upstream product

• 102491-73-6 (+/-)-N-deacetylcolchicine 
• 108-24-7 acetic anhydride 
• 64-86-8 colchicine 
• 7469-68-3 (S)-7-((Ξ)-benzylidenamino)-10-hydroxy-1,2,3-trimethoxy-6,7-dihydro-5H-benzo[a]heptalen-9-one 
• 73307-44-5 7-amino-10-hydroxy-1,2,3-trimethoxy-6,7-dihydro-5H-benzo[a]heptalen-9-one 
• 143702-47-0 C₂₁H₂₆O₇ 
• 143702-49-2 (7RS)-7-azido-1,2,3,10-tetramethoxy-6,7-dihydrobenzo[a]heptalen-9(5H)-one 
• 143702-48-1 (7RS)-methanesulfonic acid 1,2,3,10-tetramethoxy-9-oxo-5,6,7-trihydrobenzo[a]heptalen-7-yl ester 
• 143731-66-2 (7RS)-7-hydroxy-1,2,3,10-tetramethoxy-6,7-dihydrobenzo[a]heptalen-9(5H)-one 
• 186581-53-3 diazomethane 
• 102491-69-0 (+/-)-colchiceine 

Downstream Products

• 55340-40-4 10-hydroxyethylamino-10-demethoxycolchicine 
• 102419-91-0 (+)-N-deacetylcolchicine 
• 75520-89-7 (+)-colchicine 
• 477-27-0 (+)-colchiceine 
• 102491-70-3 (+/-)-N-(trifluoroacetyl)deacetylcolchiceine 
• 26195-65-3 N-(5,6,7,9-tetrahydro-1,2,3,10-tetramethoxy-9-oxobenzoheptalen-7-yl)-(S)-2,2,2-trifluoroacetamide 
• 102491-73-6 (+/-)-N-deacetylcolchicine 
• 47477-04-3 (-)-N-deacetylisocolchicine 

Relevant articles and documents

Total synthesis of (-)-colchicine via a Rh-triggered cycloaddition cascade

(Chemical Equation Presented) A synthesis of the antimitotic alkaloids (-)-colchicine and (-)-isocolchicine is reported. Important steps are (a) enantioselective transfer-hydrogenation of an alkynone, (b) iodine/magnesium exchange with subsequent aromatic

Biological Effects of Modified Colchicines. Improved Preparation of 2-Demethylcolchicine, 3-Demethylcolchicine, and (+)-Colchicine and Reassignment of the Position of the Double Bond in Dehydro-7-deacetamidocolchicines

A variety of colchicine, demecolcine, and isocolchicine derivatives were examined for their potency in the lymphocytic leukemia P388 screen in mice, for their toxicity in mice, and for their binding to microtubule protein.A qualitatively direct correlation was found between in vivo potency and toxicity; potency appeared to be less well correlated with tubulin binding.The most potent compounds were N-acylated analogues of colchicine and demecolcine.Among the monophenols, only 3-demethylcolchicine showed an appreciable effect in vitro and in vivo and was less toxic than colchicine.Improved methods were found for the preparation of 3- and 2-demethylcolchicine, which involved the use of 85percent phosphoric acid and concentrated sulfuric acid, respectively.Decoupling experiments with 1H NMR proved that the double bond of dehydro-7-deacetamidocolchiceine and its derived tropolonic methyl ethers 24 and 25 was in the 5,6 position, rather than the 6,7 position formerly tentatively assigned.