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:

99% BY HPLC ^*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
• Uses: It is used for neurological diseases and trauma-induced movement disorders, multiple neuritis, ramitis and so on. Galantamine is approved for the treatment of mild-to-moderate AD.It is a reversible specific inhibitor of AChE,and in addition it modulates central nicotinic receptors toincrease cholinergic neurotransmission. A selective acetylcholinesterase inhibitor. Useful for the treatment of Alzheimer's disease. synthetic fluoroquinolone antibiotic agent
• Description: Galantamine is an Amaryllidaceae alkaloid which is first obtained from the plant of snowdrop (Galanthus nivalis), and nowadays, it’s extracted from the plants of Narcissus and Galanthus species or obtained from chemosynthesis. In many areas in Europe such as Bulgaria, eastern Turkey, and the Caucasus, the plants of Galanthus are native species. But its earliest pharmaceutical applications are seldom known. Plaitakis and Duvoisin hypothesized that “moly” in ancient Homer’s epic might be snowdrops. In Homer’s epic Odyssey, “moly” was used as an antidote by Odysseus against Circe’s poisonous drugs. To be used as an antidote may be the plants of Galanthus’ oldest medicinal records. But there is not much evidence for that. There is little evidence of the traditional application of the plants of Galanthus, and it is certain that until the Second World War, the plants of Galanthus and other genera of Amaryllidaceae were not frequently used in European drugsItalian scholar Iannello studied Pancratium illyricum L., an Amaryllidaceae species endemic to Sardinia, and isolated a new galantamine-type alkaloid in its leaves. This new galantamine-type compound exhibited a pronounced in?vitro AChE inhibitory activity (IC50? =? 3.5±1.1? μM) in comparison with the reference standard galantamine hydrobromide (IC50?=?1.5±0.2?μM)
• Physical properties: Hydrobromide of galantamine can be used as drug although galantamine can’t be used as drugsAppearance: an almost white powder. Solubility: soluble in water; slightly soluble in alcohol; and insoluble in acetone, trichloromethane, and diethyl ether. Melting point: 269–270?°C. Specific optical rotation: ?90 to ?100°.
• Indications: Its formulation includes capsule, tablet, and oral solution. It is used in the symptomatic treatment of mild to moderately severe dementia in Alzheimer’s disease.
• Clinical Use: Before the 1990s, galantamine was mainly used to treat poliomyelitis sequelae, muscle atrophy, postoperative intestinal muscle paralysis, urinary retention, and myasthenia gravis. In the 1990s, it was found that galantamine had improved memory impairment in mice, suggesting that it might be effective for central cholinergic disorders in Alzheimer’s diseaseIn a 3–6?months’ well-designed clinical trial, recipients of galantamine achieved significant improvements in cognitive symptoms compared to placebo recipients. Galantamine also improved activities of daily living in these patients and significantly reduced the requirement for caregiver assistance with activities of daily living. Clinical development of new indications of galanthamine is currently underway, such as smoking cessation and improving cognitive impairment in schizophrenia and mania.
• Drug interactions: Potentially hazardous interactions with other drugs Antibacterials: erythromycin increases concentration of galantamine.

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:

(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

Galantamine hydrobromide

(-)-narwedine

Refernces

• 1、 Kobayashi,Ishikawa,Kihara,et al.. "Isolation of N demethylgalanthamine from the bulbs of Crinum asiaticum L. var. japanicum baker (Amaryllidaceae)". . p. 2553 - 2555. Retrieved 1976.
• 2、 Li, Lei,Yang, Qiao,Wang, Yuan,Jia, Yanxing. "Catalytic Asymmetric Total Synthesis of (-)-Galanthamine and (-)-Lycoramine". . p. 6255 - 6259. Retrieved 2015.
• 3、 Ajavakom, Vachiraporn,Bellingham, Richard K.,Brown, Richard C. D.,Camp, Nicholas P.,Kemp, Stephen C.,McLean, Neville J.,Miller, Iain R.,Moustafa, Gamal A. I.. "Transition-Metal-Mediated Chemo- and Stereoselective Total Synthesis of (?)-Galanthamine". . p. 1325 - 1334. Retrieved 2022/01/27.
• 4、 Venkatesh, Telugu,Mainkar, Prathama S.,Chandrasekhar, Srivari. "Total synthesis of (±)-galanthamine from GABA through regioselective aryne insertion". . p. 2192 - 2198. Retrieved 2019/02/27.