Galanthaminone

Base Information

• Chemical Name: Galanthaminone
• CAS No.: 1668-86-6
• Molecular Formula: C₁₇H₁₉NO₃
• Molecular Weight: 285.343
• 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: 1668-86-6.mol

Synonyms:galanthaminone

Chemical Property of Galanthaminone

Chemical Property:

• Vapor Pressure: 1.59E-06mmHg at 25°C
• Melting Point: 198-199 °C(Solv: ethyl acetate (141-78-6))
• 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: 1.99640
• 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:

98% ^*data from raw suppliers

(+/-)-NARWEDINE 95.00% ^*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
• Uses: Narwedine is the biogenetic precursor of galanthamine, has been studied as a respiratory stimulator. It increases the amplitude and decreases the frequency of cardiac contractions and would therefore be of value in reducing blood loss during surgery. It also inhibits the action of narcotics and hypnotics, and increases the analgesic effect of morphine as well as the pharmacological effects of caffeine, carbazole, arecoline, and nicotine.

Technology Process of Galanthaminone

There total 71 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: 88.0%

C18H23BN2O4 → (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)

Guidance literature:

C₁₈H₂₃BN₂O₄; With methanesulfonic acid; In 1,4-dioxane; water; at 80 ℃; for 4h; Inert atmosphere;

With sodium hydrogencarbonate; In 1,4-dioxane; water; at 20 ℃; pH=8.5; Inert atmosphere;

DOI:10.1021/ja9085534

Reference yield: 83.0%

2-hydroxy-3-methoxy-11-formyl-4α,5,9,10,11,12-hexahydro-6H-benzofuro[3α,3,2-ef][2]benzazepine-6-(1,2)-ethylenediol ketal → (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)

Guidance literature:

2-hydroxy-3-methoxy-11-formyl-4α,5,9,10,11,12-hexahydro-6H-benzofuro[3α,3,2-ef][2]benzazepine-6-(1,2)-ethylenediol ketal; With lithium aluminium tetrahydride;

With hydrogenchloride;

DOI:10.1002/1521-3773(20010817)40:16<3060::AID-ANIE3060>3.0.CO;2-#

Reference yield: 80.0%

4α,5,9,10,11,12-hexahydro-1-bromo-3-methoxy-11-formyl-6H-benzofuro[3a,3,2-ef][2]benzazepine-6-(1,2-propanediol) ketal → (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)

Guidance literature:

4α,5,9,10,11,12-hexahydro-1-bromo-3-methoxy-11-formyl-6H-benzofuro[3a,3,2-ef][2]benzazepine-6-(1,2-propanediol) ketal; With lithium aluminium tetrahydride; hydrogen; In tetrahydrofuran; at 60 - 65 ℃; for 3h; Inert atmosphere; Large scale;

With sodium hydroxide; for 0.25h; Large scale;

With hydrogenchloride; In water; at 60 ℃; for 0.333333h; pH=< 1; Large scale;

DOI:10.1021/op990019q

upstream raw materials:

4'-O-methyl-N-methylnorbelladine

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

formaldehyd

N-(3,5-dibenzyloxy-4-methoxy)benzyl-N-(4-hydroxyphenyl)ethylamine

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.