Selegiline
Title: Selegiline
CAS Registry Number: 14611-51-9
CAS Name: (aR)-N,a-Dimethyl-N-2-propynylbenzeneethanamine
Additional Names: L-(-)-N,a-dimethyl-N-2-propynylphenethylamine; (-)-deprenil; L-deprenyl
Molecular Formula: C13H17N
Molecular Weight: 187.28
Percent Composition: C 83.37%, H 9.15%, N 7.48%
Literature References: Monoamine oxidase-B inhibitor related structurally to pargyline, q.v. Prepn of racemate: FR M 2635 (1964 to Chinoin), C.A. 63, 2927e (1965); of (-)-form: NL 6605956 (1966 to Chinoin), C.A. 67, 21611y (1967); J. S. Fowler, J. Org. Chem. 42, 2637 (1977). See also: Z. Ecsery et al., US 4564706 (1986 to Chinoin). Effects of racemate on CNS: J. Knoll et al., Arch. Int. Pharmacodyn. 155, 154 (1965). Comparative pharmacology of isomers: K. Magyar et al., Acta Physiol. Acad. Sci. Hung. 32, 377 (1967). Preliminary study in Alzheimer's disease: L. S. Schneider et al., Am. J. Psychiatry 150, 321 (1993). Review of pharmacology: E. H. Heinonen, R. Lammintausta, Acta Neurol. Scand. 84, Suppl 136, 44-59 (1991); of efficacy in Parkinson's disease: D. W. Robin, Am. J. Med. Sci. 302, 392-395 (1991). Symposium: Mov. Disord. 8, Suppl. 1, S1-S44 (1993). Review of veterinary use in canine cognitive dysfunction: W. W. Ruehl, B. L. Hart in Psychopharmacology of Animal Behavior Disorders, N. H. Dodman, L. Shuster, Eds. (Blackwell Sci., Malden, Mass., 1998) pp 283-304.
Properties: Oil, bp0.8 92-93°. nD20 1.5180. [a]D20 -11.2°.
Boiling point: bp0.8 92-93°
Optical Rotation: [a]D20 -11.2°
Index of refraction: nD20 1.5180
 
Derivative Type: Hydrochloride
CAS Registry Number: 14611-52-0
Trademarks: Anipryl (Deprenyl); Antiparkin (Viatris); Amindan (Desitin); Carbex (Endo); Déprényl (Orion); Egibren (Chiesi); Eldepryl (Somerset); Jumex (Chiesi); Movergan (Orion); Otrasel (Cephalon); Plurimen (Viatris); Seledat (Master); Selegam (Hexal); Selepark (Betapharm); Selgimed (Hennig); Xilopar (Cephalon); Zelapar (Valeant)
Molecular Formula: C13H17N.HCl
Molecular Weight: 223.74
Percent Composition: C 69.79%, H 8.11%, N 6.26%, Cl 15.85%
Properties: Crystals, mp 141-142°. [a]D25 -10.8° (c = 6.48 in water). Freely sol in water, chloroform, methanol. LD50 in rats (mg/kg): 81 i.v., 280 s.c. (Magyar).
Melting point: mp 141-142°
Optical Rotation: [a]D25 -10.8° (c = 6.48 in water)
Toxicity data: LD50 in rats (mg/kg): 81 i.v., 280 s.c. (Magyar)
 
Derivative Type: (±)-Form
CAS Registry Number: 2323-36-6
Additional Names: Deprenyl; phenylisopropyl-N-methylpropinylamine
Properties: Oil, bp5 103-110°. nD20 1.5224.
Boiling point: bp5 103-110°
Index of refraction: nD20 1.5224
 
Derivative Type: (±)-Form hydrochloride
Manufacturers' Codes: E-250
Properties: LD50 in rats (mg/kg): 63 i.v., 126 s.c., 385 orally (Knoll).
Toxicity data: LD50 in rats (mg/kg): 63 i.v., 126 s.c., 385 orally (Knoll)
 
Therap-Cat: Antiparkinsonian.
Therap-Cat-Vet: In treatment of canine cognitive dysfunction syndrome.
Keywords: Antiparkinsonian; Monoamine Oxidase Inhibitor.

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