8428. Selegiline

Nomenclature

CAS number: 14611-51-9
(αR)-N,α-Dimethyl-N-2-propyn-1-ylbenzeneethanamine; l-(-)-N,α-dimethyl-N-2-propynylphenethylamine; l-N-(2-phenylisopropyl)-N-methylprop-2-ynylamine; (-)-deprenil; l-deprenyl; Emsam (Somerset).
C13H17N; mol wt 187.28.
C 83.37%, H 9.15%, N 7.48%.

Description and references

Monoamine oxidase-B inhibitor related structurally to pargyline, q.v. Prepn of racemate: FR 1368136; GB 1031425 (1964, 1966 both to Chinoin); of (-)-form: NL 6605956; GB 1153578 (1966, 1969 both to Chinoin); J. S. Fowler, J. Org. Chem. 42, 2637 (1977) DOI PubMed. Pharmacology and toxicology of racemate: J. Knoll et al., Arch. Int. Pharmacodyn. 155, 154 (1965) PubMed; of isomers: K. Magyar et al., Acta Physiol. Acad. Sci. Hung. 32, 377 (1967) PubMed. Review of pharmacology: E. H. Heinonen, R. Lammintausta, Acta Neurol. Scand. Suppl. 136, 44-59 (1991) PubMed; of efficacy in Parkinson's disease: D. W. Robin, Am. J. Med. Sci. 302, 392-395 (1991) DOI PubMed; K. L. Poston, C. Waters, Expert Opin. Pharmacother. 8, 2615-2624 (2007) DOI PubMed. 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. Review of transdermal selegiline in major depressive disorder: D. S. Robinson, J. D. Amsterdam, J. Affect. Disord. 105, 15-23 (2008) DOI PubMed.

Chemical structure

Properties

Oil, bp0.8 92-93°. nD20 1.5180.

Derivative

Hydrochloride.

Nomenclature

CAS number: 14611-52-0
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).
C13H17N.HCl; mol wt 223.74.
C 69.79%, H 8.11%, N 6.26%, Cl 15.85%.

Properties

Crystals, mp 141-142°. [α]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).

Derivative

(±)-Form.

Nomenclature

CAS number: 2323-36-6
Deprenyl; phenylisopropyl-N-methylpropinylamine.

Properties

Oil, bp5 104-110°. nD20 1.5229.

Derivative

(±)-Form hydrochloride.

Nomenclature

CAS number: 2079-54-1
E-250.

Properties

Crystals from ethanol + ether, mp 131-131.5°. LD50 in rats (mg/kg): 63 i.v., 126 s.c., 385 orally (Knoll).

Therapeutic Category

Antiparkinsonian; antidepressent.

Therapeutic Category (Veterinary)

In treatment of canine cognitive dysfunction syndrome.

Keywords

Antiparkinsonian; Monoamine Oxidase Inhibitor; Antidepressant