Galanthaminone

Base Information

• Chemical Name: Galanthaminone
• CAS No.: 510-77-0
• Molecular Formula: C17H19NO3
• Molecular Weight: 285.343
• Hs Code.: 2942000000
• European Community (EC) Number: 428-690-2,605-454-9,610-608-3
• UNII: ATP706417H,38CR9WB857
• DSSTox Substance ID: DTXSID60168190
• Nikkaji Number: J34.308K
• Wikidata: Q27107506
• Metabolomics Workbench ID: 70792
• ChEMBL ID: CHEMBL2146604
• Mol file: 510-77-0.mol

Synonyms:galanthaminone

Chemical Property of Galanthaminone

Chemical Property:

• Appearance/Colour: white to off-white chemical
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 175-180 °C (dec.)
• Refractive Index: 1.626
• Boiling Point: 397.388 °C at 760 mmHg
• PKA: 7.84±0.20(Predicted)
• Flash Point: 194.134 °C
• PSA: 38.77000
• Density: 1.28 g/cm³
• LogP: 2.84850
• Storage Temp.: -20°C Freezer
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 285.13649347
• Heavy Atom Count: 21
• Complexity: 477

Purity/Quality:

99% ^*data from raw suppliers

Galanthaminone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN1CCC23C=CC(=O)CC2OC4=C(C=CC(=C34)C1)OC
• Isomeric SMILES: CN1CC[C@@]23C=CC(=O)C[C@@H]2OC4=C(C=CC(=C34)C1)OC
• 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.).

Technology Process of Galanthaminone

There total 90 articles about Galanthaminone which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 90.0%

(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 (510-77-0,1668-86-6,7318-55-0,26601-10-5) → (-)-narwedine (510-77-0,26601-10-5)

Guidance literature:

With triethylamine; In ethanol; at 40 - 80 ℃; for 72h; Product distribution / selectivity;

Reference yield: 88.0%

Galantamine (357-70-0) → (-)-narwedine (510-77-0,26601-10-5)

Guidance literature:

With oxalyl dichloride; dimethyl sulfoxide; In dichloromethane; at -55 - -40 ℃; for 0.5h;

DOI:10.1021/jo980271g

Reference yield: 85.7%

4a,5,9,10,11,12-hexahydro-3-methoxy-11-methyl-6H-benzofuro[3a,3,2-ef][2]benzazepin-6-one (296237-49-5,26601-10-5) → (-)-narwedine (510-77-0,26601-10-5)

Guidance literature:

4a,5,9,10,11,12-hexahydro-3-methoxy-11-methyl-6H-benzofuro[3a,3,2-ef][2]benzazepin-6-one; With acetic acid; In ethanol; water; Heating / reflux;

With triethylamine; In ethanol; water; at 0 - 80 ℃; for 22h;

upstream raw materials:

(-)-epigalanthamine

Galantamine

4a,5,9,10,11,12-hexahydro-3-methoxy-11-methyl-6H-benzofuro[3a,3,2-ef][2]benzazepin-6-one

N-formyl-1-bromo-narwedine

Downstream raw materials:

galanthamine

(-)-narwedine

Galantamine

Galantamine hydrobromide

Refernces

• 1、 Venkatesh, Telugu,Mainkar, Prathama S.,Chandrasekhar, Srivari. "Total synthesis of (±)-galanthamine from GABA through regioselective aryne insertion". . p. 2192 - 2198. Retrieved 2019/02/27.
• 2、 Gallagher, Ryan,Chebib, Mary,Balle, Thomas,McLeod, Malcolm D.. "Thiol-Reactive Analogues of Galanthamine, Codeine, and Morphine as Potential Probes to Interrogate Allosteric Binding within Nicotinic Acetylcholine Receptors". . p. 1834 - 1841. Retrieved 2015/12/26.