75520-89-7

Basic information

• Product Name: (+)-Colchicine
• Synonyms: Acetamide, N-(5,6,7,9-tetrahydro-1,2,3,10-tetramethoxy-9-oxobenzo[a]heptalen-7-yl)-, (R)-;Benzo[a]heptalene, acetamide deriv.;(-)-N-[(R)-5,6,7,9-Tetrahydro-1,2,3,10-tetramethoxy-9-oxobenzo[a]heptalene-7-yl]acetamide;(R)-7-Acetylamino-5,6,7,9-tetrahydro-1,2,3,10-tetramethoxybenzo[a]heptalene-9-one;(R)-Colchicine;(R)-N-(5,6,7,9-Tetrahydro-1,2,3,10-tetraMethoxy-9-oxobenzo[a]heptalen-7-yl)acetaMide
• CAS NO: 75520-89-7
• Molecular Formula: C22H25NO6
• Molecular Weight: 399.44
• Product Categories: Amines;Chiral Reagents;Heterocycles;Inhibitors;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 75520-89-7.mol
• Article Data: 3

Chemical Properties

• Melting Point: 106-132°C
• Boiling Point: 726°C at 760 mmHg
• Flash Point: 392.9°C
• Appearance: /
• Density: 1.25g/cm³
• Vapor Pressure: 6.21E-21mmHg at 25°C
• Refractive Index: 1.584
• Storage Temp.: -20?C Freezer
• CAS DataBase Reference: (+)-Colchicine(CAS DataBase Reference)
• NIST Chemistry Reference: (+)-Colchicine(75520-89-7)
• EPA Substance Registry System: (+)-Colchicine(75520-89-7)

Safety Data

• Hazardous Substances Data: 75520-89-7(Hazardous Substances Data)

Usage

Description

(+)-Colchicine, also known as the R-enantiomer of Colchicine (C640000), is a pale yellow solid with potent antimitotic properties. It is derived from the Colchicum autumnale plant and has been widely studied for its effects on microtubules and its potential applications in various fields.

Uses

Used in Pharmaceutical Industry:
(+)-Colchicine is used as an antimitotic agent for its ability to disrupt microtubules by binding to tubulin and preventing its polymerization. This action stimulates the intrinsic GTPase activity of tubulin, leading to the induction of apoptosis in several normal and tumor cell lines. Additionally, it activates the JNK/SAPK signaling pathway, which has implications for the treatment of various diseases.
Used in Cancer Treatment:
(+)-Colchicine is used as a therapeutic agent in the treatment of certain types of cancer, particularly those involving rapid cell division and the formation of microtubules. Its ability to inhibit microtubule polymerization and induce apoptosis makes it a valuable tool in the fight against cancer.
Used in Research Applications:
(+)-Colchicine is also used as a research tool in the study of microtubule dynamics, cell division, and apoptosis. Its unique properties allow scientists to investigate the mechanisms underlying these processes and develop new strategies for targeting cancer cells and other diseases related to abnormal cell division.

InChI:InChI=1/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-/m1/s1

Upstream product

• 186581-53-3 diazomethane 
• 477-27-0 (+)-colchiceine 
• 108-24-7 acetic anhydride 
• 102419-91-0 (+)-N-deacetylcolchicine 
• 73307-44-5 7-amino-10-hydroxy-1,2,3-trimethoxy-6,7-dihydro-5H-benzo[a]heptalen-9-one 
• 209810-38-8 N-(5,6,7,9-tetrahydro-1,2,3,10-tetramethoxy-9-oxobenzo[a]heptalen-7-yl) acetamide 
• 102491-73-6 (+/-)-N-deacetylcolchicine 
• 102491-70-3 (+/-)-N-(trifluoroacetyl)deacetylcolchiceine 
• 102491-71-4 (+/-)-N-(trifluoroacetyl)deacetylcolchicine 
• 3482-37-9 (+)-N-deacetylcolchiceine 
• 7469-68-3 (S)-7-((Ξ)-benzylidenamino)-10-hydroxy-1,2,3-trimethoxy-6,7-dihydro-5H-benzo[a]heptalen-9-one 
• 2103-57-3 2,3,4-trimethoxybenzaldehyde 

Relevant articles and documents

Enantioselective total synthesis of (-)-colchicine, (+)-demecolcinone and metacolchicine: Determination of the absolute configurations of the latter two alkaloids

Here, we describe a concise, enantioselective, and scalable synthesis of (-)-colchicine (9.2% overall yield, >99% ee). Moreover, we have also achieved the first syntheses of (+)-demecolcinone and metacolchicine, and determined their absolute configurations. The challenging tricyclic 6-7-7 core of colchicinoids was efficiently introduced using an intramolecular oxidopyrylium-mediated [5 + 2] cycloaddition reaction. Notably, the synthesized colchicinoid 23 exhibited potent inhibitory activity toward the cell growth of human cancer cell lines (IC50 = ～3.0 nM), and greater inhibitory activity towards microtubule assembly than colchicine, making it a promising lead in the search for novel anticancer agents.

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.