3419. Donepezil
Nomenclature
CAS number: 120014-06-4
2,3-Dihydro-5,6-dimethoxy-2-[[1-(phenylmethyl)-4-piperidinyl]methyl]-1H-inden-1-one; 5,6-dimethoxy-2-[[1-(phenylmethyl)-4-piperidinyl]methyl]-2,3-dihydro-1H-inden-1-one; 1-benzyl-4-[(5,6-dimethoxy-1-indanon-2-yl)methyl]piperidine. C24H29NO3; mol wt 379.49.
C 75.96%, H 7.70%, N 3.69%, O 12.65%.
Description and references
Reversible acetylcholinesterase inhibitor. Prepn: H. Sugimoto et al., EP 296560, eidem, US 4895841 (1988, 1990 both to Eisai). Synthesis: Y. Iimura et al., J. Labelled Compd. Radiopharm. 27, 835 (1989). HPLC determn of enantiomers in plasma: J. Haginaka, C. Seyama, J. Chromatogr. B 577, 95 (1992). Clinical pharmacokinetics: A. Ohnishi et al., J. Clin. Pharmacol. 33, 1086 (1993). Clinical trials in Alzheimer's disease: R. C. Mohs et al., Neurology 57, 481 (2001); B. Winblad et al., ibid. 489. Review of pharmacology and clinical experience in cognitive disorders: G. C. Román, S. J. Rogers, Expert Opin. Pharmacother. 5, 161-180 (2004).
Derivative
Hydrochloride.Nomenclature
CAS number: 120011-70-3
E-2020; Aricept (Eisai). C24H29NO3.HCl; mol wt 415.95.
C 69.30%, H 7.27%, N 3.37%, O 11.54%, Cl 8.52%.
Properties
White crystalline powder. Crystals from methanol/IPE, mp 211-212° (dec). Freely sol in chloroform; sol in water, glacial acetic acid; slightly sol in ethanol, acetonitrile. Practically insol in ethyl acetate, n-hexane.Therapeutic Category
Nootropic.
Keywords
Nootropic