510-77-0

Basic information

• Product Name: GALANTHAMINONE
• Synonyms: GALANTHAMINONE;Narwedine;(4aS;8aS)-;(4aS,8aS)-4a,5,9,10,11,12-Hexahydro-3-Methoxy-11-Methyl-6H-benzofuro[3a,3,2-ef][2]benzazepin-6-one;GalantaMine interMediate ((-)-Narwedine);GalantaMinone (GalantaMine IMpurity A);6H-Benzofuro[3a,3,2-ef][2]benzazepin-6-one,4a,5,9,10,11,12-hexahydro-3-Methoxy-11-Methyl-, (4aS,8aS)-
• CAS NO: 510-77-0
• Molecular Formula: C₁₇H₁₉NO₃
• Molecular Weight: 285.34
• Product Categories: Various Metabolites and Impurities;Heterocycles;Intermediates & Fine Chemicals;Metabolites;Pharmaceuticals;raw materials
• Mol File: 510-77-0.mol
• Article Data: 24

Chemical Properties

• Melting Point: 175-180°C (dec.)
• Boiling Point: 397.388 °C at 760 mmHg
• Flash Point: 194.134 °C
• Appearance: /
• Density: 1.28 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.626
• Storage Temp.: -20°C Freezer
• PKA: 7.84±0.20(Predicted)
• CAS DataBase Reference: GALANTHAMINONE(CAS DataBase Reference)
• NIST Chemistry Reference: GALANTHAMINONE(510-77-0)
• EPA Substance Registry System: GALANTHAMINONE(510-77-0)

Safety Data

• Hazardous Substances Data: 510-77-0(Hazardous Substances Data)

Usage

Description

This alkaloid occurs in several families of the Amaryllidaceae and is obtained as colourless prisms when crystallized from Me2CO. It is dextrorotatory with [α]25D + 100° (c 0.2, CHC13). It forms a crystalline picrate, m.p. 123°C; a methiodide, m.p. 195-6°C and a semicarbazone, indicative of a keto group, m.p. 240-1 °c (dec.).

Chemical Properties

White to Off-White

References

Boit, Dapke, Beitner., Chem. Ber., 90,2197 (1957)

InChI:InChI=1/C17H19NO3/c1-18-8-7-17-6-5-12(19)9-14(17)21-16-13(20-2)4-3-11(10-18)15(16)17/h3-6,14H,7-10H2,1-2H3/t14-,17-/m0/s1

Upstream product

• 1668-85-5 (-)-epigalanthamine 
• 357-70-0 Galantamine 
• 357-70-0 4a,5,9,10,11,12-hexahydro-3-methoxy-11-methyl-6H-benzofuro[3a,3,2-ef ][2]benzazepin-6-ol 
• 603-35-0 triphenylphosphine 
• 74-89-5 methylamine 
• 179107-93-8 N-(p-hydroxyphenylethyl)-N-(6-bromo-3-hydroxy-4-methoxybenzyl)amine 
• 2973-59-3 2-bromoisovanillin 
• 120-14-9 3,4-dimethoxy-benzaldehyde 
• 5392-10-9 2-bromo-4,5-dimethoxybenzaldehyde 
• 122584-18-3 N-(4-hydroxyphenethyl)-N-(2-bromo-5-hydroxy-4-methoxybenzyl)formamide 
• 934415-11-9 galantamine 
• 94753-90-9 4'-O-methyl-N-methylnorbelladine 
• 4579-60-6 N-(p-hydroxyphenylethyl)-N-(3-hydroxy-4-methoxybenzyl)amine 
• 510-77-0 (4aS,8aS)-rel-3-methoxy-11-methyl-4a,5,9,10,11,12-hexahydro-6H-benzo[2,3]benzofuro[4,3-cd]azepin-6-one 

Downstream Products

• 357-70-0 galanthamine 
• 193146-85-9 galantamine hydrobromide 
• 510-77-0 (-)-narwedine 
• 357-70-0 Galantamine 
• 1953-04-4 Galantamine hydrobromide 
• 7318-55-0 (4aR,8aR)-4a,5,9,10,11,12-hexahydro-3-methoxy-11-methyl-6H-benzofuro[3a,3,2-ef][2]benzazepin-6-one 
• 1668-85-5 (-)-epigalanthamine 
• 261961-58-4 (4aR,6R,8aR)-4a,5,9,10,11,12-hexahydro-3-methoxy-11-methyl-6H-benzofuro[3a,3,2-ef][2] benzezapine-6-ol 
• 1556014-63-1 (4aR,6S,8aR)-4a,5,9,10,11,12-hexahydro-3-methoxy-11-methyl-6H-benzofuro[3a,3,2-ef][2] benzazepine-6-ol hydrobromide 
• 357-70-0 (±)-4a,5,9,10,11,12-hexahydro-3-methoxy-11-methyl-6H-benzofuro[3a,3,2-ef][2]benzezapine-6-ol 
• 510-77-0 (4aS,8aS)-rel-3-methoxy-11-methyl-4a,5,9,10,11,12-hexahydro-6H-benzo[2,3]benzofuro[4,3-cd]azepin-6-one 

Relevant articles and documents

A Nivalin industrial preparation method (by machine translation)

The invention relates to a technical field of drug synthesis, in particular relates to a preparation method of the galanthamine hydrobromide. Preparation method of this invention comprises the following steps: (1) the racemate narwedine as raw materials, adding resolution solvent to get levorotation narwedine; (2) L narwedine [...] butyl boron lithium hydride reduction shall be galantamine free alkali, further and hydrobromic acid shall be galanthamine hydrobromide. (by machine translation)

An Eleven-Step Synthesis of Galanthamine from Commercially Available Materials

Narwedine, an immediate precursor to the therapeutically valuable alkaloid (–)-galanthamine, has been synthesised by engaging an iodinated isovanillin derivative in an intermolecular Mitsunobu reaction with a 2-cyclohexen-1-ol derivative. The resulting aryl ether participated in an exceptionally efficient intramolecular Heck reaction to give a tetracyclic lactol after the hydrolysis of the primary cyclisation product. This last compound is an advanced intermediate associated with the Magnus synthesis of narwedine and could be elaborated to narwedine itself under reductive amination conditions. As a result, an eleven-step synthesis of galanthamine has been established.

A total synthesis of galanthamine involving de novo construction of the aromatic C-ring

The tetracyclic alkaloid galanthamine is used clinically in a number of countries for the symptomatic treatment of mild to moderate forms of Alzheimer's disease, and this feature coupled with its novel molecular architecture has prompted an extensive focus on its synthesis. The present study reports a new and distinct synthesis of galanthamine wherein the AB-ring substructure and associated quaternary carbon centre are constructed by using a palladium-catalyzed intramolecular Alder-ene reaction. The product of this process is engaged in a Tsuji-Trost-type reaction to generate a semicyclic diene that participates in a normal-electron-demand Diels-Alder reaction to generate, after oxidation of the initially formed adduct, the aromatic C-ring of the target alkaloid. Modified Bischler-Napieralski chemistry is then deployed to construct the seven-membered D-ring and thereby furnishing narwedine, an established precursor to both (+)- and (-)-galanthamine. The first synthesis of the alkaloid galanthamine is reported in which the aromatic C-ring is assembled from non-aromatic precursors. This was accomplished by a Diels-Alder cycloaddition reaction. The diene used embodies the AB-ring system (and associated quaternary carbon centre) and was constructed by intramolecular Alder-ene and Tsuji-Trost-type chemistries. The D-ring was closed by a modified Bischler-Napieralski reaction.