Occupational cases of contact dermatitis caused by
exposure to alprenolol have been reported within the
pharmaceutical industry.
Antiadrenergic
(β-receptor).
ChEBI: A secondary alcohol that is propan-2-ol substituted by a 2-allylphenoxy group at position 1 and an isopropylamino group at position 3. It is a beta-adrenergic antagonist used as a antihypertensive, anti-arrhythmia and a sympatholytic agent.
A solution of 24.6 g of o-allyl-epoxypropoxybenzene dissolved in 250 ml of
absolute ethanol saturated with ammonia was placed in an autoclave and
heated on a steam-bath for 2 hours. The alcohol was then removed by
distillation and the residue was redissolved in a mixture of methanol and
ethylacetate. Hydrogen chloride gas was introduced into the solution. The
hydrochloride salt was then precipitated by the addition of ether to yield 11.4
g of product. Five grams of the amine-hydrochloride thus formed were
dissolved in 50 ml of methanol and 9 ml of acetone. The resulting solution
was cooled to about 0°C. At this temperature 5 g of sodium borohydride were
added over a period of 1 hour. Another 2.2 ml of acetone and 0.8 g of sodium
borohydride were added and the solution was kept at room temperature for 1
hour, after which 150 ml of water were added to the solution. The solution
was then extracted with three 100-ml portions of ether which were combined,
dried over potassium carbonate, and evaporated. The free base was then
recrystallized from petrol ether (boiling range 40-60°C) to yield 2.7 g of
material having a melting point of 57°C.
The corresponding hydrochloride was prepared by dissolving 2 g of the
product, prepared above, in 20 ml of acetone, and adding to the resulting
solution acetone saturated with hydrogen chloride until the pH was reduced to
about 3. The precipitated hydrochloride salt was then recrystallized from
acetone.
Occupational cases of contact dermatitis due to this betablocker
were reported in the pharmaceutical industry
