8125. Reboxetine

Nomenclature

CAS number: 98769-81-4
(2R)-rel-2-[(R)-(2-Ethoxyphenoxy)phenylmethyl]morpholine; (±)-(2R*)-2-[(αR*)-α-(o-ethoxyphenoxy)benzyl]morpholine.
C19H23NO3; mol wt 313.39.
C 72.82%, H 7.40%, N 4.47%, O 15.32%.

Description and references

Selective noradrenaline reuptake inhibitor. Prepn: P. Melloni et al., DE 2901032; eidem, US 4229449 (1979, 1980 both to Farmitalia Carlo Erba); eidem et al., Eur. J. Med. Chem. - Chim. Ther. 19, 235 (1984). Configuration: P. Melloni et al., Tetrahedron 41, 1393 (1985). HPLC determn of enantiomers in plasma: E. Frigerio et al., J. Chromatogr. A 660, 351 (1994). Metabolism: G. Cocchiara et al., Eur. J. Drug Metab. Pharmacokinet. 16, 231 (1991). Stereoselective kinetics: M. S. Benedetti et al., Chirality 7, 285 (1995). Clinical pharmacokinetics: C. Pellizzoni et al., Biopharm. Drug Dispos. 17, 623 (1996). Clinical trial in depression and social phobia: S. A. Montgomery, J. Psychopharmacol. 11, Suppl., S9 (1997); A. Dubini et al., ibid. S17.

Chemical structure

Properties

mp 170-171°.

Derivative

Methanesulfonate.

Nomenclature

CAS number: 98769-82-5
Reboxetine mesylate; FCE-20124; Edronax (Pharmacia & Upjohn); Prolift (Pfizer); Vestra (Pharmacia & Upjohn).
C19H23NO3.CH3SO3H; mol wt 409.50.
C 58.66%, H 6.65%, N 3.42%, O 23.44%, S 7.83%.

Properties

mp 145-146°.

Therapeutic Category

Antidepressant.

Keywords

Antidepressant