1499. Bupropion

Nomenclature

CAS number: 34911-55-2
1-(3-Chlorophenyl)-2-[(1,1-dimethylethyl)amino]-1-propanone; (±)-2-(tert-butylamino)-3′-chloropropiophenone; m-chloro-α-(tert-butylamino)propiophenone; amfebutamone.
C13H18ClNO; mol wt 239.74.
C 65.13%, H 7.57%, Cl 14.79%, N 5.84%, O 6.67%.

Description and references

Unicyclic aminoketone with noradrenergic and dopaminergic activity. Prepn: N. B. Mehta, D. A. Yeowell, DE 2059618 (1971 to Wellcome Found.); N. B. Mehta, US 3819706 (1974 to Burroughs Wellcome). Pharmacology: F. Soroko et al., J. Pharm. Pharmacol. 29, 767 (1977). Preclinical toxicology: W. E. Tucker, J. Clin. Psychiatry 44, 60-62 (1983). Pharmacokinetics in smokers: P.-H. Hsyu et al., J. Clin. Pharmacol. 37, 737 (1997). Clinical trial in attention deficit disorder with hyperactivity: C. K. Conners et al., J. Am. Acad. Child Adolesc. Psychiatry 34, 1314 (1996); in smoking cessation: D. E. Jorenby et al., N. Engl. J. Med. 340, 685 (1999). Review of pharmacology and clinical efficacy in depression: S. G. Bryant et al., Clin. Pharm. 2, 525-537 (1983); of mechanism of action studies: J. A. Ascher et al., J. Clin. Psychiatry 56, 395-401 (1995); of clinical use in smoking cessation: R. West, Expert Opin. Pharmacother. 4, 533-540 (2003).

Chemical structure

Properties

Pale yellow oil, bp.005 52°. Sol in methanol, ethanol, acetone, ether, benzene. Very hygroscopic and susceptible to decompn.

Derivative

Hydrochloride.

Nomenclature

CAS number: 31677-93-7
Budeprion (Teva); Wellbutrin (GSK); Zyban (GSK).
C13H18ClNO.HCl; mol wt 276.20.
C 56.53%, H 6.93%, Cl 25.67%, N 5.07%, O 5.79%.

Properties

Crystals from isopropanol and abs ethanol, mp 233-234°. Bitter, anesthetizing taste. Soly (mg/ml): water 312; alcohol 193; 0.1N HCl 333. pKa: 7.9. LD50 in mice, rats (mg/kg): 230, 210 i.p.; 575, 600 orally (Soroko).

Therapeutic Category

Antidepressant; aid in smoking cessation.

Keywords

Antidepressant