[7S-(7alpha,7bbeta,10abeta)]-N-(5,6,7,7b,8,10a-hexahydro-1,2,3,9-tetramethoxy-8-oxobenzo[a]cyclopenta[3,4]cyclobuta[1,2-c]cyclohepten-7-yl)acetamide

[7S-(7alpha,7bbeta,10abeta)]-N-(5,6,7,7b,8,10a-hexahydro-1,2,3,9-tetramethoxy-8-oxobenzo[a]cyclopenta[3,4]cyclobuta[1,2-c]cyclohepten-7-yl)acetamide Basic information
Product Name:[7S-(7alpha,7bbeta,10abeta)]-N-(5,6,7,7b,8,10a-hexahydro-1,2,3,9-tetramethoxy-8-oxobenzo[a]cyclopenta[3,4]cyclobuta[1,2-c]cyclohepten-7-yl)acetamide
Synonyms:[7S-(7alpha,7bbeta,10abeta)]-N-(5,6,7,7b,8,10a-hexahydro-1,2,3,9-tetramethoxy-8-oxobenzo[a]cyclopenta[3,4]cyclobuta[1,2-c]cyclohepten-7-yl)acetamide;N-[(7S)-5,6,7,7bβ,8,10aβ-Hexahydro-1,2,3,9-tetramethoxy-8-oxobenzo[a]cyclopenta[3,4]cyclobuta[1,2-c]cyclohepten-7-yl]acetamide;N-[(7S,7bR,10aS)-5,6,7,7b,8,10a-Hexahydro-1,2,3,9-tetraMethoxy-8-oxobenzo[a]cyclopenta[3,4]cyclobuta[1,2-c]cyclohepten-7-yl]acetaMide;Colchicine Impurity 3(Colchicine EP Impurity C);Colchicine EP Impurity C;N-[(7S,7bR,10aS)-1,2,3,9-Tetrametho;Acetamide, N-[(7S,7bR,10aS)-5,6,7,7b,8,10a-hexahydro-1,2,3,9-tetramethoxy-8-oxobenzo[a]cyclopenta[3,4]cyclobuta[1,2-c]cyclohepten-7-yl]-;N-((7S,7bR,10aS)-1,2,3,9-tetramethoxy-8-oxo-5,6,7,7b,8,10a-hexahydrobenzo[a]cyclopenta[3,4]cyclobuta[1,2-c][7]annulen-7-yl)acetamide
CAS:6901-13-9
MF:C22H25NO6
MW:399.437
EINECS:2300081
Product Categories:Amines;Chiral Reagents;Heterocycles;Inhibitors;Intermediates & Fine Chemicals;Pharmaceuticals;Alkaloids
Mol File:6901-13-9.mol
[7S-(7alpha,7bbeta,10abeta)]-N-(5,6,7,7b,8,10a-hexahydro-1,2,3,9-tetramethoxy-8-oxobenzo[a]cyclopenta[3,4]cyclobuta[1,2-c]cyclohepten-7-yl)acetamide Structure
[7S-(7alpha,7bbeta,10abeta)]-N-(5,6,7,7b,8,10a-hexahydro-1,2,3,9-tetramethoxy-8-oxobenzo[a]cyclopenta[3,4]cyclobuta[1,2-c]cyclohepten-7-yl)acetamide Chemical Properties
Melting point 177-180°C
density 1.30±0.1 g/cm3 (20 ºC 760 Torr)
storage temp. Amber Vial, -20°C Freezer, Under Inert Atmosphere
solubility Chloroform (Slightly), Methanol (Sparingly)
form Solid
color Off-White to Pale Orange
Stability:Light Sensitive
Safety Information
MSDS Information
[7S-(7alpha,7bbeta,10abeta)]-N-(5,6,7,7b,8,10a-hexahydro-1,2,3,9-tetramethoxy-8-oxobenzo[a]cyclopenta[3,4]cyclobuta[1,2-c]cyclohepten-7-yl)acetamide Usage And Synthesis
DescriptionThis alkaloid has been isolated from a number of plants including Colchicum kesselringii, C. luteum Baker, Merendera jolanta E. Czerniak, M. raddeana Rgl.and M. robusta Bge. It forms colourless crystals from CHC13-Et20. It is possible that this base may be an artifact formed during the isolation process.
Chemical PropertiesPale Yellow Solid
UsesAn analog of Colchicine (C640000), β-lumicolchicine, does not bind tubulin or disrupt microtubules. A GABAA receptor chloride channel.
DefinitionChEBI: LSM-4236 is a carbotricyclic compound, a member of acetamides and an alkaloid.
ReferencesSantavy, Collect. Czech. Chem. Commun., 16,665 (1951)
Santavy, Pharm. Zent., 96, 307 (1957)
Yusupov, Sadykov, Tr. Nauch. Tashkent. Gos. Univ., 203, 3, 15 (1962)
YUSUpOY, SadykoY, J. Gen. Chem. USSR, 34, 1672 (1964)
Yusupov, Sadykov, Tr. Nauch. Tashkent. Gos. Univ., 286,11,56 (1966)
Chommedov, Yusupov, Sadykov, Khim. Prir. Soedin., 6, 82, 275 (1970)
Trozyan, Yusupov, Sadykov, ibid, 7,541 (1971)
Santavy, Tr. Nauchi. Tashkent, 11 (1972)






[7S-(7alpha,7bbeta,10abeta)]-N-(5,6,7,7b,8,10a-hexahydro-1,2,3,9-tetramethoxy-8-oxobenzo[a]cyclopenta[3,4]cyclobuta[1,2-c]cyclohepten-7-yl)acetamide Preparation Products And Raw materials
Preparation ProductsAcetamide, N,N'-[(7S,7bR,8aS,8bS,9aR,10S,16cS,16dR,16eR,16fS)-5,6,7,7b,8,8a,8b,9,9a,10,11,12,16c,16d,16e,16f-hexadecahydro-1,2,3,8a,8b,14,15,16-octamethoxy-8,9-dioxobisbenzo[3',4']cyclohepta[1',2':3,4]cyclobuta[1,2-c:1',2'-c']cyclobuta[1,2-a:4,3-a']dicyclopentene-7,10-diyl]bis--->GAMMA-LUMICOLCHICINE
Colchicine

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