21019-23-8

Basic information

• Product Name: methyl (3alpha,14alpha,16alpha)-14,15-dihydroeburnamenine-14-carboxylate
• Synonyms: Eburnamenine-14-carboxylic acid, 14,15-dihydro-, methyl ester, (3.alpha.,14.alpha.,16.alpha.)-
• CAS NO: 21019-23-8
• Molecular Formula: C₂₁H₂₆N₂O₂
• Molecular Weight: 338.4433
• Mol File: 21019-23-8.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 486.5°C at 760 mmHg
• Flash Point: 248°C
• Density: 1.31g/cm³
• Vapor Pressure: 1.29E-09mmHg at 25°C
• Refractive Index: 1.678
• CAS DataBase Reference: methyl (3alpha,14alpha,16alpha)-14,15-dihydroeburnamenine-14-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl (3alpha,14alpha,16alpha)-14,15-dihydroeburnamenine-14-carboxylate(21019-23-8)
• EPA Substance Registry System: methyl (3alpha,14alpha,16alpha)-14,15-dihydroeburnamenine-14-carboxylate(21019-23-8)

Safety Data

• Hazardous Substances Data: 21019-23-8(Hazardous Substances Data)

Upstream product

• 4880-92-6 (+/-)-apovincamine 
• 59639-59-7 (+/-)-eburnane-16β-carbonitrile 
• 51152-47-7 (1R*,5S*,12bS*)-1-ethyl-1,2,3,4,6,7,12,12b-octahydroindolo<2,3-a>quinolizine-1-carbaldehyde 
• 66685-08-3 1-ethyl-2,3,4,6,7,12-hexahydroindolo<2,3-a>quinolizin-4(1H)-one 
• 66685-13-0 4-(4,9-dihydro-3H-β-carbolin-1-yl)-hexanoic acid methyl ester 
• 169530-52-3 (1R*,5R*,12bR*)-1-ethyl-1,2,3,4,6,7,12,12b-octahydroindolo<2,3-a>quinolizine-1-carbaldehyde 
• 74571-79-2 1-ethyl-2,3,4,6,7,12-hexahydroindolo<2,3-a>quinolizin-4-thione 
• 106498-98-0 (1R*,5R*,12bR*)-1-ethyl-1,2,3,4,6,7,12,12b-octahydroindolo<2,3-a>quinolizine-1-methanol 
• 186581-53-3 diazomethane 
• 59656-84-7 (10R,11aR,11bR)-11a-Ethyl-2,3,4,5,10,11,11a,11b-octahydro-1H-3a,9b-diaza-benzo[cd]fluoranthene-10-carboxylic acid amide 
• 59639-59-7 (10R,11aS,11bR)-11a-Ethyl-2,3,4,5,10,11,11a,11b-octahydro-1H-3a,9b-diaza-benzo[cd]fluoranthene-10-carbonitrile 
• 59639-59-7 (10S,11aS,11bR)-11a-Ethyl-2,3,4,5,10,11,11a,11b-octahydro-1H-3a,9b-diaza-benzo[cd]fluoranthene-10-carbonitrile 
• 4880-92-6 apovincamine 
• 23944-42-5 (-)-1β-methoxycarbonylethyl-1α-ethyl-1,2,3,4,6,7,12,12bα-octahydroindolo<2,3-a>quinolizine 

Downstream Products

• 23173-24-2 (13a-ethyl-2,3,5,6,12,13,13a,13b-octahydro-1H-indolo[3,2,1-de]pyrido[3,2,1-ij][1,5]naphthyridin-12-yl)-methanol 

Relevant articles and documents

Syntheses and Cardiovascular Activity of Stereoisomers and Derivatives of Eburnane Alkaloids

The synthesis of all the possible isomers of the eburnamenine-vincamine type alkaloids 1b, 2a*, 3a and derivatives 4, 8, 9, 10 is described.Structures were determined by 1H- and 13C-NMR spectroscopy including special techniques such as DR, DEPT, DNOE, and 2D-HSC.In contrast to the known cerebrovascular effects of cis-(3S,16S) compounds, trans-(3S,16R) derivatives show a significant peripheral vasodilator effect. Key Word: Eburnanes / Alkaloids / Cardiovascular effects / Indoloquinolizines

A NEW APPROACH TO (+/-)-APOVINCAMINE

A new approach to (+/-)-apovincamine, 2, is reported which bypasses the formation of (+/-)-vincamine, 1, and includes the dehydration of the β-hydroxy ester 7, obtained by regio-controlled alkylation of the stereochemically suitable aldehyde 6 with methyl chloroacetate.Using ethyl chloroacetate, the clinically useful apovincamine analogue, (+/-)-Cavinton, 3, is obtained. (+/-)-Apovincamine is then converted to (+/-)-vincamine, 1, by base-catalyzed oxygenation of the mixture of (+/-)-dihydroapovincamines 8 and 9.