ALPRENOLOL HYDROCHLORIDE Property

Melting point:

107-109°

storage temp. 

2-8°C

solubility 

H₂O: 50 mg/mL

form 

powder

color 

off-white

Water Solubility 

Soluble in water (100mM)

Stability:

Hygroscopic

InChIKey

RRCPAXJDDNWJBI-UHFFFAOYSA-N

CAS DataBase Reference

13707-88-5

Safety

Hazard Codes 

Xn

Risk Statements 

22

RIDADR 

3249

WGK Germany 

3

RTECS 

UA5425000

HazardClass 

6.1(b)

PackingGroup 

III

Toxicity

LD50 in mice, rats, rabbits (mg/kg): 278.0, 597.0, 337.3 orally (Marmo)

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

ALPRENOLOL HYDROCHLORIDE Chemical Properties,Usage,Production

Chemical Properties

White or almost white, crystalline powder or colourless crystals.

Originator

Aptol,Globopharm,Switz.

Uses

Alprenlol Hydrochloride acts as a β-adrenergic blocking agent against arrhythmia.

Uses

aldose reductase inhibitor

Manufacturing Process

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.

Therapeutic Function

Beta-adrenergic blocker

Biological Activity

β -adrenoceptor ( β 2 > β 1 > β 3 ) and 5-HT 1A receptor antagonist.

storage

room temperature (desiccate)