Epigalanthamin

Base Information

• Chemical Name: Epigalanthamin
• CAS No.: 357-70-0
• Molecular Formula: C17H21NO3
• Molecular Weight: 287.359
• Hs Code.: 2942000000
• NSC Number: 100058
• DSSTox Substance ID: DTXSID70859345
• Nikkaji Number: J1.441.242E
• Wikidata: Q27163546
• Metabolomics Workbench ID: 123725
• ChEMBL ID: CHEMBL1623394
• Mol file: 357-70-0.mol

Synonyms:Epigalanthamin;ENT- GALANTHAMINE;MLS000766281;NSC100058;9-methoxy-4-methyl-11-oxa-4-azatetracyclo[8.6.1.01,12.06,17]heptadeca-6(17),7,9,15-tetraen-14-ol;epigalanthamine;Galanthamine #;Dihydrogalantamine;Galanthamine,(3.alpha.-;Galantamine;HSDB 7361;Oprea1_097473;Oprea1_098077;SCHEMBL220427;CERAPP_13557;CHEMBL1623394;CHEBI:91735;DTXSID70859345;HMS2269H23;HMS3561F13;BCP28966;LSM-1597;BBL028838;STL146336;AKOS000635322;NCI60_000004;SMR000528869;FT-0667895;FT-0668941;FT-0668942;FT-0668943;Q-201144;BRD-A49148672-001-07-9;BRD-A49148672-004-01-6;Q27163546;(1S,12S,14R)-9-methoxy-4-methyl-11-oxa-4-azatetracyclo[8.6.1.0^{1,12.0^{6,17]heptadeca-6(17),7,9,15-tetraen-14-ol;6H-Benzofuro(3a,3,2-ef)(2)benzazepin-6-ol, 4a,5,9,10,11,12-hexahydro-3-methoxy-11-methyl-, (4aS-(4a.alpha.,6.beta.,8aR*))-;6H-Benzofuro[3a,2-ef][2]benzazepin-6-ol, 4a,5,9,10,11,12-hexahydro-3-methoxy-11-methyl-, [4aS-(4a.alpha.,6.beta.,8aR*)]-

Chemical Property of Epigalanthamin

Chemical Property:

• Appearance/Colour: Off-white sSolid
• Vapor Pressure: 1.71E-08mmHg at 25°C
• Melting Point: 119-121 °C
• Refractive Index: 1.5022 (estimate)
• Boiling Point: 439.3 °C at 760 mmHg
• PKA: pKa 8.32 (Uncertain)
• Flash Point: 219.5 °C
• PSA: 41.93000
• Density: 1.28 g/cm³
• LogP: 1.78820
• Storage Temp.: -20°C Freezer
• Solubility.: ≥14.37 mg/mL in DMSO; ≥14.43 mg/mL in H2O with gentle warming; ≥45 mg/mL in EtOH with gentle warming
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 287.15214353
• Heavy Atom Count: 21
• Complexity: 440

Purity/Quality:

≥98% ^*data from raw suppliers

Galanthamine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN1CCC23C=CC(CC2OC4=C(C=CC(=C34)C1)OC)O
• General Description: Galanthamine is an Amaryllidaceae alkaloid with cholinesterase inhibitory properties, clinically used to treat neuromuscular disorders and Alzheimer's dementia. Its analogs, such as 6H-benzofuro[3a,3,2-e,f][1]benzazepine and 6H-benzofuro[3a,3,2-e,f][3]benzazepine, are synthesized by modifying the nitrogen position in the azepine ring to explore potential enhancements in therapeutic efficacy. These structural variations aim to optimize reactivity and pharmacological activity while retaining or improving upon galanthamine's established benefits.

Technology Process of Epigalanthamin

There total 261 articles about Epigalanthamin 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: 99.7%

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

Guidance literature:

With L-Selectride; In tetrahydrofuran; at -78 ℃; for 2h;

DOI:10.1021/jo00097a060

Reference yield: 94.0%

N-formyl-N-norgalanthamine (109606-37-3) → Galantamine (357-70-0)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; at 20 ℃; for 7h;

DOI:10.1002/anie.200353636

Reference yield: 91.0%

[(-)-narwedine]2[di-p-toluoyl-D-tartrate] → Galantamine (357-70-0)

Guidance literature:

With L-Selectride; In tetrahydrofuran; at 20 ℃; for 0.5h;

upstream raw materials:

diazomethane

O-Demethylgalantamine

leucotamine

Galantamine hydrobromide

Downstream raw materials:

10-benzyl-3β-hydroxy-6-methoxy-10-methyl-galantham-1-enium; iodide

(-)-narwedine

(-)-epigalanthamine

O-trisiopropylsilylgalanthamine

Refernces

Galanthamine analogs: 6H-benzofuro[3a,3,2,-e,f][1]benzazepine and 6H-benzofuro[3a,3,2-e,f][3]benzazepine

10.1016/j.tet.2005.05.055

The study focuses on the synthesis and evaluation of galanthamine analogs, specifically 6H-benzofuro[3a,3,2-e,f][1]benzazepine and 6H-benzofuro[3a,3,2-e,f][3]benzazepine, which are derivatives of the Amarylidaceae alkaloid galanthamine. Galanthamine is known for its cholinesterase inhibitory properties and is used in the treatment of neuromuscular diseases and Alzheimer's dementia. The purpose of the study was to alter the position of the nitrogen within the azepine ring of galanthamine to create analogs that might have similar or improved therapeutic effects. The synthesis involved a variety of chemicals, including p-hydroxyphenylpropionic acid, benzyl chloride, thionyl chloride, and various other reagents and solvents, which were used to perform esterification, benzylation, saponification, formylation, bromination, and reduction reactions, among others. These chemicals served to construct the complex molecular structures of the analogs, with the ultimate goal of understanding how changes in the molecular structure affect the reactivity and potential therapeutic applications of these compounds.