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

Description

N-DESMETHYLGALANTHAMINE, a metabolite of Galanthamine, is an off-white solid with significant biological properties. It functions as a selective acetylcholinesterase inhibitor, which makes it a promising candidate for various pharmaceutical applications.

Uses

Used in Pharmaceutical Industry:
N-DESMETHYLGALANTHAMINE is used as a therapeutic agent for the treatment of neurodegenerative diseases, particularly Alzheimer's disease. Its selective acetylcholinesterase inhibitory activity helps improve cognitive function and memory by increasing the levels of acetylcholine in the brain.
Used in Research and Development:
N-DESMETHYLGALANTHAMINE is used as a research compound for studying the mechanisms of neurodegenerative diseases and the development of novel therapeutic strategies. Its chemical properties and biological activities make it a valuable tool in the design and synthesis of new drugs targeting acetylcholinesterase.
Used in Drug Delivery Systems:
N-DESMETHYLGALANTHAMINE can be employed in the development of innovative drug delivery systems to enhance its bioavailability, stability, and targeted delivery to the brain. This may involve the use of nanoparticles, liposomes, or other advanced drug delivery technologies to improve the efficacy and safety of N-DESMETHYLGALANTHAMINE-based treatments.

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

• 596828-90-9 galanthamine N-oxide 
• 134332-50-6 galanthamine N-oxide 
• 271769-63-2 C₁₆H₁₇NO₃ 
• 27229-56-7 [3,5-bis(benzyloxy)-4-methoxyphenyl]methanol 
• 99-24-1 methyl galloate 
• 13326-72-2 3,5-bis(benzyloxy)-4-methoxybenzaldehyde 
• 24093-81-0 methyl 3,5-dihydroxy-4-methoxybenzoate 
• 13326-69-7 methyl 3,5-bis(benzyloxy)-4-methoxybenzoate 
• 722499-81-2 C₂₇H₂₅F₃N₂O₅ 
• 722499-75-4 C₂₇H₂₃F₃N₂O₅ 
• 722499-71-0 (2S,5R)-5-benzyl-2-(3,5-dibenzyloxy-4-methoxyphenyl)-3-[2-(4-hydroxyphenyl)ethyl]imidazolidin-4-one 
• 722499-74-3 C₂₇H₂₃F₃N₂O₆ 
• 722499-80-1 C₂₈H₂₂F₆N₂O₈S 
• 722499-73-2 C₄₁H₃₅F₃N₂O₆ 

Downstream Products

• 357-70-0 Galantamine 
• 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 

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.

Design, synthesis and evaluation of galanthamine derivatives as acetylcholinesterase inhibitors

A new series of galanthamine derivatives have been designed, synthesized and evaluated as acetylcholinesterase inhibitors. All of the new compounds prepared showed high AChE inhibitory activities, with compound 3e that has an N-hexyl-benzyl piperidine substituent on the nitrogen atom reaching the best inhibitory activity for AChE (IC50 = 5.62 nM). The docking study performed with AutoDock demonstrated that 3e was nicely accommodated by AChE.