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Donepezil Hydrochloride

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Donepezil Hydrochloride Basic information
Donepezil Hydrochloride Chemical Properties
  • Melting point:220-222°C
  • storage temp. -20°C Freezer
  • form powder
  • color white to off-white
  • Merck 14,3419
  • InChIKeyXWAIAVWHZJNZQQ-UHFFFAOYSA-N
  • CAS DataBase Reference120011-70-3(CAS DataBase Reference)
Safety Information
  • Hazard Codes Xi
  • Risk Statements 36/37/38
  • Safety Statements 26-36
  • RIDADR UN 2811
  • WGK Germany 1
  • RTECS NK8927885
  • HazardClass 6.1
  • PackingGroup II
Donepezil Hydrochloride Usage And Synthesis
  • DescriptionAricept was launched in Canada, Germany, the UK and the US for treatment of mild to moderate Alzheimer’s disease and dementia. It was prepared in three steps beginning with the condensation of 5,6-dimethoxy-1-indanone with 1-benzylpiperidine- 4-carboxaldehyde. Aricept is a reversible, non-competitive inhibitor of acetylcholinesterase. It is 570-1250 times more selective for acetylcholinesterase than for butylcholinesterase. It has a greater affinity for brain over peripheral acetylcholinesterase with no inhibition in cardiac and smooth muscle, but with slight effects in striated muscle. Aricept inhibited all three isozymes (type A, G2 and G4) of acetylcholinesterase thereby delaying the decline of cholinergics found in the AD brain and slowing the loss of cognitive abilities. It has a 60-70 hr half-life, readily penetrates the CNS, and is 100% bioavailable through the gut with no hepatotoxicity.
  • Chemical PropertiesDonepezil hydrochloride is known chemically as (±)-2, 3-dihydro-5, 6-dimethoxy-2-[[1-(phenylmethyl)-4-piperidinyl]methyl]-1H-inden-1-one hydrochloride[1]. Donepezil hydrochloride is commonly referred to in the pharmacological literature as E2020. It has an empirical formula of C24H29NO3HCl and a molecular weight of 415.96. Donepezil hydrochloride is a white crystalline powder and is freely soluble in chloroform, soluble in water and in glacial acetic acid, slightly soluble in ethanol and in acetonitrile, and practically insoluble in ethyl acetate and in n-hexane.
  • OriginatorEisai (Japan)
  • UsesA nootropic. An inhibitor of acetylcholinesterase
  • UsesA labelled nootropic. An inhibitor of acetylcholinesterase.
  • UsesAntialzheimer
  • UsesLabeled Donepezil, intended for use as an internal standard for the quantification of Donepezilby GC- or LC-mass spectrometry.
  • DefinitionChEBI: Donepezil hydrochloride is a centrally acting reversible acetyl cholinesterase inhibitor. Its main therapeutic use is in the treatment of Alzheimer's disease where it is used to increase cortical acetylcholine.
  • Manufacturing ProcessThis reaction was conducted in an argon atmosphere. 2.05 ml of diisopropylamine was added to 10 ml of anhydrous THF, followed by addition of 9.12 ml of a 1.6 M solution of n-butyl lithium in hexane at 0°C. The mixture was stirred at 0°C for 10 min and then cooled to -78°C, and a solution of 2.55 g of 5,6-dimethoxy-1-indanone in 30 ml of anhydrous THF and 2.31 ml of hexamethyl-phosphoric amide were added thereto. The mixture was stirred at -78°C for 15 min, and a solution of 2.70 g of 1-benzyl- 4-piperidinecarboaldehyde in 30 ml of anhydrous THF was added thereto. The temperature of the mixture was gradually raised to room temperature, followed by stirring for 2 hr. An aqueous 1% ammonium chloride solution was added thereto, and the organic phase was separated. The water phase was extracted with ethyl acetate, and the organic phases were combined with each other. The combined organic phase was washed with a saturated saline solution, dried over magnesium sulfate, and concentrated in vacuo. The resulting residue was purified by making use of a silica gel column (methylene chloride:methanol=500:1-100:1). The eluate was concentrated in vacuo, and the residue was dissolved in methylene chloride. A 10% solution of hydrochloric acid in ethyl acetate was added to the resulting solution, followed by concentration in vacuo to obtain a crystal, which was recrystallized from methanol/IPE to obtain 3.40 g (yield: 62%) 1-benzyl-4-[(5,6-dimethoxy-1- indanon)-2-ylidenyl]methylpiperidine HCl; melting point 237°-238°C.
    4 g of 1-benzyl-4-[(5,6-dimethoxy-1-indanon)-2-ylidenyl]methylpiperidine was dissolved in 16 ml of THF, followed by addition of 0.04 g of 10% palladiumcarbon. The mixture was hydrogenated at room temperature under atmospheric pressure for 6 hr. The catalyst was filtered off, and the filtrate was concentrated in vacuo. The residue was purified by making use of a silica gel column (methylene chloride:methanol=50:1). The eluate was concentrated in vacuo, and the residue was dissolved in methylene chloride. A 10% solution of hydrochloric acid in ethyl acetate was added to the resulting solution, followed by concentration in vacuo to obtain a crystal, which was recrystallized from methanol/IPE to obtain 0.36 g (yield: 82%) of the 1-benzyl-4-[(5,6-dimethoxy-1-indanon)-2-yl-methylpiperidine]-hydrochloride (donepezil HCl) having the melting point: 211°C-212°C (dec.).
    Later it was described the synthesis of the donepezil HCl from 5,6-dimethoxy- 2-(pyridin-4-yl)methylene-indan-1-one by the reaction with H2 over platinum dioxide at room temperature in acetic acid-methanol mixture to give 4-[(5,6- dimethoxy-1-indanon)-2-yl]methylpiperidine. The last one yielded donepesyl HCl by refluxing with benzyl bromide and triethylamine for 4 hours with the following addition of methanolic HCl (10%).
  • brand nameAricept (Eisai Medical Research).
  • Therapeutic FunctionAnti-Alzheimer's disease
  • PharmacologyDonepezil hydrochloride is a second-generation highly selective acetylcholinesterase inhibitor developed by the Japanese company Eisai Pharmaceutical Company. It was first marketed in the United States in 1997 for the treatment of Alzheimer's disease. Donepezil is the second drug approved by the FDA for the treatment of Alzheimer's disease. It is a highly selective, long-acting, reversible acetylcholinesterase inhibitor with a piperidine group. Compared with tacrine, donepezil hydrochloride is more selective for neuronal acetylcholinease, has better pharmacodynamics, pharmacokinetics and safety indicators, and is well tolerated. It is an alternative drug to tacrine.
    Donepezil hydrochloride is a cholinesterase inhibitor. After taking it, patients mainly increase the content of acetylcholine in the synapses that are directly involved in nerve transmission by inhibiting the activity of acetylcholine lipase. Donepezil hydrochloride can Effectively improve patients 'brain function and improve patients' cognitive ability. Currently, donepezil hydrochloride is a commonly used drug in the treatment of mild to moderate senile dementia. Donepezil hydrochloride tablets are suitable for the treatment of memory degeneration of dementia caused by various reasons. Donepezil hydrochloride has the effect of nourishing brain neurons, repairing damaged brain nerves, and can rapidly improve patients' cognitive function and memory.
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