120013-56-1

Basic information

• Product Name: 6-O-DESMETHYL DONEPEZIL
• Synonyms: 6-O-DESMETHYL DONEPEZIL;1-Benzyl-4-[(6-hydroxy-5-methoxy-1-oxo-indan-2-yl)methylpiperidine;2,3-Dihydro-6-hydroxy-5-Methoxy-2-[[1-(phenylMethyl)-4-piperidinyl]Methyl]-1H-inden-1-one;2-((1-benzylpiperidin-4-yl)methyl)-6-hydroxy-5-methoxy-2,3-dihydro-1H-inden-1-one
• CAS NO: 120013-56-1
• Molecular Formula: C₂₃H₂₇NO₃
• Molecular Weight: 365.47
• Product Categories: Intermediates & Fine Chemicals;Metabolites & Impurities;Pharmaceuticals;Heterocycles;Heterocycles, Metabolites & Impurities, Pharmaceuticals, Intermediates & Fine Chemicals
• Mol File: 120013-56-1.mol

Chemical Properties

• Melting Point: 57-59°C
• Boiling Point: 545.3±50.0 °C(Predicted)
• Appearance: /
• Density: 1.190±0.06 g/cm3(Predicted)
• Storage Temp.: -20°C Freezer
• Solubility: Chloroform (Slightly), Dichloromethane, Methanol (Slightly)
• PKA: 9.46±0.40(Predicted)
• Stability: Temperature Sensitive
• CAS DataBase Reference: 6-O-DESMETHYL DONEPEZIL(CAS DataBase Reference)
• NIST Chemistry Reference: 6-O-DESMETHYL DONEPEZIL(120013-56-1)
• EPA Substance Registry System: 6-O-DESMETHYL DONEPEZIL(120013-56-1)

Safety Data

• Hazardous Substances Data: 120013-56-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
6-O-DESMETHYL DONEPEZIL is used as a therapeutic agent for the treatment of cognitive impairment and neurodegenerative diseases. As a metabolite of Donepezil, an inhibitor of acetylcholinesterase, it helps enhance cognitive function by increasing the levels of acetylcholine in the brain, which is essential for memory and learning.
Used in Research and Development:
6-O-DESMETHYL DONEPEZIL is used as a research compound for studying the mechanisms of acetylcholinesterase inhibition and its effects on cognitive function. This application aids in the development of new drugs and therapies for the treatment of Alzheimer's disease and other related conditions.
Used in Quality Control and Standardization:
6-O-DESMETHYL DONEPEZIL is used as a reference material for quality control and standardization in the pharmaceutical industry. Its chemical properties and well-defined structure make it an ideal candidate for ensuring the consistency, purity, and potency of Donepezil and its related products.

Upstream product

• 1135-24-6 3-(4-hydroxy-3-methoxyphenyl)acrylic acid 
• 1135-24-6 (E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid 
• 90843-62-2 6-hydroxy-5-methoxyindan-1-one 
• 1135-23-5 3-(4-hydroxy-3-methoxyphenyl)propionic acid 
• 120014-06-4 donepezil 

Downstream Products

• 1033718-50-1 tert-butyl 2-(2-((1-benzylpiperidin-4-yl)methyl)-6-methoxy-3-oxo-2,3-dihydro-1H-inden-5-yloxy)acetate 

Relevant articles and documents

Combining chalcones with donepezil to inhibit both cholinesterases and aβ fibril assembly

The fact that the number of people with Alzheimer's disease is increasing, combined with the limited availability of drugs for its treatment, emphasize the need for the development of novel effective therapeutics for treating this brain disorder. Herein, we focus on generating 12 chalcone-donepezil hybrids, with the goal of simultaneously targeting amyloid-β (Aβ) peptides as well as cholinesterases (i.e., acetylcholinesterase (AChE) and butyrylcholinesterase (BChE)). We present the design, synthesis, and biochemical evaluation of these two series of novel 1,3-chalcone-donepezil (15a-15f) or 1,4-chalcone-donepezil (16a-16f) hybrids. We evaluate the relationship between their structures and their ability to inhibit AChE/BChE activity as well as their ability to bind Aβ peptides. We show that several of these novel chalcone-donepezil hybrids can successfully inhibit AChE/BChE as well as the assembly of N-biotinylated Aβ(1-42) oligomers. We also demonstrate that the Aβ binding site of these hybrids differs from that of Pittsburgh Compound B (PIB).

Multifunctional donepezil analogues as cholinesterase and BACE1 inhibitors

A series of 22 donepezil analogues were synthesized through alkylation/benzylation and compared to donepezil and its 6-O-desmethyl adduct. All the compounds were found to be potent inhibitors of both acetylcholinesterase (AChE) and butyrylcholinesterase (BChE), two enzymes responsible for the hydrolysis of the neurotransmitter acetylcholine in Alzheimer’s disease patient brains. Many of them displayed lower inhibitory concentrations of EeAChE (IC50 = 0.016 ± 0.001 μM to 0.23 ± 0.03 μM) and EfBChE (IC50 = 0.11 ± 0.01 μM to 1.3 ± 0.2 μM) than donepezil. One of the better compounds was tested against HsAChE and was found to be even more active than donepezil and inhibited HsAChE better than EeAChE. The analogues with the aromatic substituents were generally more potent than the ones with aliphatic substituents. Five of the analogues also inhibited the action of β-secretase (BACE1) enzyme.