Tenuate,Merrell National ,US,1959
Controlled substance (stimulant). Anorexic.
ChEBI: The hydrochloride salt of diethylpropion. A central stimulant and indirect-acting sympathomimetic, it is an appetite depressant and is used as an anoretic in the short term management of obesity.
1,145 g of α-bromopropiophenone and 850 g of diethylamine are combined
under stirring and heated on a water bath to boiling. The precipitate is filtered
off under suction and washed with benzol. The filtrate is shaken up with
aqueous hydrogen chloride, the aqueous solution made alkaline and etherified.
The solution freed of the ether is fractionated. The boiling point (6 mm) is
140°C and the yield 800 g. The base is dissolved in acetic ester and
precipitated with isopropanolic hydrogen chloride. After suction filtration and
washing with ether the yield is found to be 750 g (80%)and the melting point
168°C.
Because it has two large (relative to H or methyl) N-alkylsubstituents, diethylpropion hydrochloride, 1-phenyl-2-diethylaminopropan-1-one hydrochloride (Tenuate, Tepanil),has fewer sympathomimetic, cardiovascular, and CNSstimulatoryeffects than amphetamine. It is reportedly ananorexiant agent that can be used for the treatment of obesityin patients with hypertension and cardiovascular disease.According to the generalization long used for thisgroup of drugs, increasing N-alkyl size reduces central 1effects and increases β effects, even though the effects arelikely mediated principally by indirect NE release.
