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Bevantolol is a cardioselective β-adrenergic blocker. Bevantolol is used as an antianginal, antihypertensive, antiarrhythmic.

ChEBI: The hydrochloride salt of bevantolol.

Vantol (Parke-Davis).

Moderately toxic by ingestion.

Bevantolol hydrochloride is a cardioselective (β₁) adrenergic blocker, devoid of intrinsic sympathomimetic and local anesthetic activities. As with other agents of this category, it is useful in the treatment of hypertension and angina.

Warner-Lambert (USA)

To a solution of 50 g (1.25 mol) of NaOH in 1200 ml H2O was added 108 g (1 mol) of m-cresol freshly distilled and at 15°C in one lot 117ml (1.5 mol) of epichlorohydrin. The emulsion was stirred at room temperature for 16 hours in a creased flask. The product was taken up in 1000 ml of toluene and washed with 500 ml water. Distillation yielded 135.7 g=82% of 3-(m-tolyloxy)-1,2- epoxypropane, b.p. 61°C at 0.05 mm.
Preparation of bevantolol hydrochloride:
To a suitable reactor under a nitrogen blanket is added 13.7 kg of β-(3,4- dimethoxyphenyl)ethylamine. The amine is cooled to 5°C and 12.5 kg of 3- (m-tolyloxy)-1,2-epoxypropane is added maintaining the temperature between 5-10°C. After 10 hours, the mixture is seeded with bevantolol free base; seeding is repeated approximately every 2 hours until it is evident that crystallization has started. After stirring for 48 hours at 10°C, 26 L of hexane is added. The temperature is raised to 25°C and stirring is continued for 48 hours. The slurry is filtered and the collected solid is dried under vacuum. The product is dissolved in 60 L of isopropyl alcohol and the solution is filtered. The reactor and filter are rinsed with 186 L of isopropyl alcohol and 2.7 kg of anhydrous hydrogen chloride is added to the combined filtrate. The batch is heated to reflux for 2 hours. The temperature is adjusted to 65°C and the solution is seeded with bevantolol hydrochloride crystals. The mixture is held at this temperature with stirring until a heavy sand-like slurry is present. The mixture is allowed to cool to ambient temperature without stirring or artificial cooling. It is then cooled to 20°C. The slurry is centrifuged and the product rinsed with isopropyl alcohol until the filtrate is colorless. After being vacuum dried at 50-55°C the product is milled if necessary; yield of bevantolol hydrochloride 22.7 kg (78.6%); melting point 137-138°C.

Antiarrhythmic, Beta-adrenergic blocker

A poison by intraperitoneal andintravenous route. Moderately toxic by ingestion. Whenheated to decomposition it emits toxic vapors of NOx,HCl, and Cl-.

Store at -20°C