Title: Phenserine
CAS Registry Number: 101246-66-6; 159652-53-6 (racemate)
CAS Name: (3aS,8aR)-1,2,3,3a,8,8a-Hexahydro-1,3a,8-trimethylpyrrolo[2,3-b]indol-5-ol phenylcarbamate (ester)
Additional Names: (-)-eseroline phenylcarbamate
Molecular Formula: C20H23N3O2
Molecular Weight: 337.42
Percent Composition: C 71.19%, H 6.87%, N 12.45%, O 9.48%
Literature References: Physostigmine, q.v., analog; acetylcholinesterase inhibitor that reduces b-amyloid precursor protein (b-APP) formation. Prepn: M. Polonovski, Bull. Soc. Chim. Fr. 19, 46 (1916). See also: M. Pomponi et al., EP 154864; M. Brufani et al., US 5306825 (1985, 1994 both to Consig. Naz. Delle Ricerche). Anticholinesterase activity: M. Brzostowska et al., Med. Chem. Res. 2, 238 (1992). Pharmacology: S. Iijima et al., Psychopharmacology 112, 415 (1993). Pharmacokinetics: N. H. Greig et al., Acta Neurol. Scand. Suppl. 176, 74 (2000). Mode of action study for regulating b -APP expression: K. T. Y. Shaw et al., Proc. Natl. Acad. Sci. USA 98, 7605 (2001). Review of total synthesis and biological activity: N. H. Greig et al., Med. Res. Rev. 15, 3-31 (1995); A. Brossi et al., Aust. J. Chem. 49, 171-181 (1996). Review of development and therapeutic potential: U. Thatte, IDrugs 3,1222-1228 (2000).
Properties: mp 150°. [a]D -80° (in ethanol).
Melting point: mp 150°
Optical Rotation: [a]D -80° (in ethanol)
Derivative Type: Tartrate
CAS Registry Number: 156910-61-1
Molecular Formula: C20H23N3O2.C4H6O6
Molecular Weight: 487.50
Percent Composition: C 59.13%, H 6.00%, N 8.62%, O 26.26%
Properties: mp 142-145°. [a]D -58.7° (c = 0.75 in methanol). Highly sol in water.
Melting point: mp 142-145°
Optical Rotation: [a]D -58.7° (c = 0.75 in methanol)
Therap-Cat: In treatment of Alzheimer's disease. Cholinesterase inhibitor.
Keywords: Cholinesterase Inhibitor.

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