41303-74-6

Basic information

• Product Name: N-DESMETHYLGALANTHAMINE
• Synonyms: N-DESMETHYLGALANTHAMINE;Norgalanthamine;(-)-N-Demethylgalanthamine;(8aS,10R,12aS)-1,2,3,4,8a,9-Hexahydro-7-methoxy-10H-benzofuro[3a,3,2-ef][2]benzazepin-10-ol;N-Norgalanthamine;Norgalantamine;(4aS,6R,8aS)-4a,5,9,10,11,12-Hexahydro-3-Methoxy-6H-benzofuro[3a,3,2-ef][2]benzazepin-6-ol;NorgalanthaMine-d3 HBr
• CAS NO: 41303-74-6
• Molecular Formula: C₁₆H₁₉NO₃
• Molecular Weight: 273.33
• Product Categories: Various Metabolites and Impurities;Intermediates & Fine Chemicals;Metabolites & Impurities;Pharmaceuticals;Chiral Reagents;Heterocycles;Inhibitors
• Mol File: 41303-74-6.mol
• Article Data: 11

Chemical Properties

• Melting Point: 142-145°C
• Boiling Point: 457.923°C at 760 mmHg
• Flash Point: 230.744°C
• Appearance: /
• Density: 1.309g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.642
• Storage Temp.: -20°C Freezer
• CAS DataBase Reference: N-DESMETHYLGALANTHAMINE(CAS DataBase Reference)
• NIST Chemistry Reference: N-DESMETHYLGALANTHAMINE(41303-74-6)
• EPA Substance Registry System: N-DESMETHYLGALANTHAMINE(41303-74-6)

Safety Data

• Hazardous Substances Data: 41303-74-6(Hazardous Substances Data)

Usage

Chemical Properties

Off-White Solid

Uses

A metabolite of Galanthamine, a selective acetylcholinesterase inhibitor

InChI:InChI=1/C16H19NO3/c1-19-12-3-2-10-9-17-7-6-16-5-4-11(18)8-13(16)20-15(12)14(10)16/h2-5,11,13,17-18H,6-9H2,1H3/t11-,13-,16-/m0/s1

Upstream product

• 24093-81-0 methyl 3,5-dihydroxy-4-methoxybenzoate 
• 13326-69-7 methyl 3,5-bis(benzyloxy)-4-methoxybenzoate 
• 213984-51-1 C₃₃H₃₀F₃NO₄Si 
• 213984-39-5 N-(2,2-Diphenyl-6-trimethylsilanyl-benzo[1,3]dioxol-5-ylmethyl)-2,2,2-trifluoro-N-[2-(4-hydroxy-phenyl)-ethyl]-acetamide 
• 213984-59-9 2,2-Diphenyl-6-trimethylsilanyl-benzo[1,3]dioxole-5-carbaldehyde 
• 213984-66-8 (2,2-Diphenyl-6-trimethylsilanyl-benzo[1,3]dioxol-5-yl)-methanol 
• 65638-94-0 2,2-diphenylbenzo(1,3-dioxole)-5-carboxylic acid methyl ester 
• 213984-05-5 (6-bromo-2,2-diphenylbenzo[1,3]dioxol-5-yl)methanol 
• 70006-59-6 2,2-Diphenyl-1,3-benzodioxol-5-methanol 
• 2150-43-8 3,4-dihydroxybenzoic acid methyl ester 
• 99-50-3 3,4-Dihydroxybenzoic acid 
• 357-70-0 Galantamine 
• 1953-04-4 Galantamine hydrobromide 
• 722499-72-1 (2S,5R)-5-benzyl-2-(3,5-dibenzyloxy-4-methoxyphenyl)-3-[2-(4-hydroxyphenyl)ethyl]-1-(2,2,2-trifluoroacetyl)imidazolidin-4-one 

Downstream Products

• 913380-51-5 10-N-demethyl-10-N-(2-(4-(piperidin-1-ylmethyl)phenoxy)ethan-1-yl)galanthamine 
• 913380-52-6 10-N-demethyl-10-N-(3-(4-(piperidin-1-ylmethyl)phenoxy)propan-1-yl)galanthamine 
• 913380-53-7 10-N-demethyl-10-N-(4-(4-(piperidin-1-ylmethyl)phenoxy)butan-1-yl)galanthamine 
• 913380-54-8 10-N-demethyl-10-N-(5-(4-(piperidin-1-ylmethyl)phenoxy)pentan-1-yl)galanthamine 
• 913380-55-9 10-N-demethyl-10-N-(6-(4-(piperidin-1-ylmethyl)phenoxy)hexan-1-yl)galanthamine 
• 913380-56-0 10-N-demethyl-10-N-(8-(4-(piperidin-1-ylmethyl)phenoxy)octan-1-yl)galanthamine 
• 913380-57-1 10-N-demethyl-10-N-(9-(4-(piperidin-1-ylmethyl)phenoxy)nonan-1-yl)galanthamine 
• 913380-58-2 10-N-demethyl-10-N-(10-(4-(piperidin-1-ylmethyl)phenoxy)decan-1-yl)galanthamine 
• 913380-59-3 10-N-demethyl-10-N-(12-(4-(piperidin-1-ylmethyl)phenoxy)dodecan-1-yl)galanthamine 
• 913380-61-7 10-N-demethyl-10-N-(6-(4-((diethylamino)methyl)phenoxy)hexan-1-yl)galanthamine 
• 913380-62-8 10-N-demethyl-10-N-(4-(4-(morpholino-methyl)phenoxy)butan-1-yl)galanthamine 
• 913380-63-9 10-N-demethyl-10-N-(6-(4-(morpholino-methyl)phenoxy)hexan-1-yl)galanthamine 
• 913380-64-0 10-N-demethyl-10-N-(4-(3-(1-morpholinoethyl)phenoxy)butan-1-yl)galanthamine 
• 913380-65-1 10-N-demethyl-10-N-(6-(3-(1-morpholinoethyl)phenoxy)hexan-1-yl)galanthamine 

Relevant articles and documents

Galantamine derivatives as acetylcholinesterase inhibitors: Docking, design, synthesis, and inhibitory activity

Galantamine (GAL) is a well-known acetylcholinesterase (AChE) inhibitor, and it is widely used for treatment of Alzheimer’s disease. GAL fits well in the catalytic site of AChE, but it is too short to block the peripheral anionic site (PAS) of the enzyme,

Synthesis and evaluation of (-)- and (+)-[11C]galanthamine as PET tracers for cerebral acetylcholinesterase imaging

Improved radiopharmaceuticals for imaging cerebral acetylcholinesterase (AChE) are needed for the diagnosis of Alzheimer's disease (AD). Thus, 11C-labeled (-)-galanthamine and its enantiomers were synthesized as novel agents for imaging the localization and activity of AChE by positron emission tomography (PET). C-11 was incorporated into (-)- and (+)-[ 11C]galanthamine by N-methylation of norgalanthamines with [ 11C]methyl triflate. Simple accumulation of 11C in the brain was measured in an in vivo biodistribution study using mice, whilst donepezil was used as a blocking agent in analogous in vivo blocking studies. In vitro autoradiography of rat brain tissue was performed to investigate the distribution of (-)-[11C]galanthamine, and confirmed the results of PET studies in mice. The radiochemical yields of N-methylation of (-)- and (+)-norgalanthamines were 13.7% and 14.4%, respectively. The highest level of accumulation of 11C in the brains of mice was observed at 10 min after administration (2.1% ID/g). Intravenous pretreatment with donepezil resulted in a 30% decrease in accumulation of (-)-[11C]galanthamine in the striatum; however, levels in the cerebellum were unchanged. In contrast, use of (+)-[11C]galanthamine led to accumulation of radioactivity in the striatum equal to that in the cerebellum, and these levels were unaffected by pretreatment with donepezil. In in vitro autoradiography of regional radioactive signals of brain sections showed that pretreatment with either (-)-galanthamine or donepezil blocked the binding of (-)-[11C] galanthamine to the striatum, while sagittal PET imaging revealed accumulation of (-)-[11C]galanthamine in the brain. These results indicate that (-)-[11C]galanthamine showed specific binding to AChE, whereas (+)-[11C]-galanthamine accumulated in brain tissue by non-specific binding. Thus, optically pure (-)-[11C]galanthamine could be a useful PET tracer for imaging cerebral AChE.

Galanthamine derivatives, methods for their obtaining and use

This invention relates to new compounds that are galanthamine derivatives, to the methods of their obtaining and their use for prophylaxis and/or treatment of neurodegenerative diseases, senile dementia and Alzheimer's disease including. The new galanthamine derivatives obtained according to the invention combine two effects: inhibition of acetylcholinesterase and butyrylcholinesterase activity due to the galanthamine molecule and inhibition of γ-secretase activity characteristic to the peptide fragment.