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Alprenolol

CAS No.
13655-52-2
Chemical Name:
Alprenolol
Synonyms
Alpheprol;Alprenolol;ALLPRENOLOL;dl-Alprenolol;(RS)-Alprenolol;Alprenolol USP/EP/BP;(-)-Alprenolol hydrate D-tartrate;3-(o-Allylphenoxy)-1-isopropylamino-2-propanol;1-Isopropylamino-3-(2-allyl)phenoxypropan-2-ol;1-(2-Allylphenoxy)-3-(isopropylamino)-2-propanol
CBNumber:
CB7874989
Molecular Formula:
C15H23NO2
Molecular Weight:
249.35
MDL Number:
MFCD00242735
MOL File:
13655-52-2.mol
MSDS File:
SDS
Last updated:2023-05-21 10:59:17

Alprenolol Properties

Melting point 57.5°C
Boiling point 392.45°C (rough estimate)
Density 1.0065 (rough estimate)
refractive index 1.5250 (estimate)
storage temp. Store at -20°C
solubility DMF: 20 mg/ml; DMSO: 15 mg/ml; Ethanol: 5 mg/ml; PBS (pH 7.2): 1 mg/ml
form A crystalline solid
pka pKa 9.63 (Uncertain)
Water Solubility 366.9mg/L(22.5 ºC)
FDA UNII 877K5MQ27W
NIST Chemistry Reference 2-Propanol, 1-[(1-methylethyl)amino]-3-[2-(2-propenyl)phenoxy]-(13655-52-2)
ATC code C07AA01

SAFETY

Risk and Safety Statements

Hazard Codes  T
Risk Statements  23/24/25-43
Safety Statements  36/37/39-45
RIDADR  3249
HazardClass  6.1(b)
PackingGroup  III
Toxicity mammal (species unspecified),LD50,intraperitoneal,102mg/kg (102mg/kg),Pharmaceutical Chemistry Journal Vol. 8, Pg. 137, 1974.

Alprenolol price More Price(16)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Cayman Chemical 25338 Alprenolol ≥98% 13655-52-2 25mg $57 2024-03-01 Buy
Cayman Chemical 25338 Alprenolol ≥98% 13655-52-2 50mg $85 2024-03-01 Buy
Cayman Chemical 25338 Alprenolol ≥98% 13655-52-2 100mg $133 2024-03-01 Buy
Biosynth Carbosynth FA166898 Alprenolol 13655-52-2 25mg $150 2021-12-16 Buy
AK Scientific 0249CA Alprenolol 13655-52-2 50mg $202 2021-12-16 Buy
Product number Packaging Price Buy
25338 25mg $57 Buy
25338 50mg $85 Buy
25338 100mg $133 Buy
FA166898 25mg $150 Buy
0249CA 50mg $202 Buy

Alprenolol Chemical Properties,Uses,Production

Description

Occupational cases of contact dermatitis caused by exposure to alprenolol have been reported within the pharmaceutical industry.

Originator

Aptol,Globopharm,Switz.

Uses

Antiadrenergic (β-receptor).

Definition

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.

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

Contact allergens

Occupational cases of contact dermatitis due to this betablocker were reported in the pharmaceutical industry

Alprenolol Preparation Products And Raw materials

Raw materials

Preparation Products

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Alprenolol 1-Isopropylamino-3-(2-allyl)phenoxypropan-2-ol 2-Propanol, 1-[(1-methylethyl)amino]-3-[2-(2-propenyl)phenoxy]- Alpheprol dl-Alprenolol ALLPRENOLOL (-)-Alprenolol hydrate D-tartrate 1-(2-Allylphenoxy)-3-(isopropylamino)-2-propanol 1-(Isopropylamino)-3-[2-(2-propenyl)phenoxy]-2-propanol 3-(o-Allylphenoxy)-1-isopropylamino-2-propanol [S,(-)]-3-[2-(2-Propenyl)phenoxy]-1-isopropylamino-2-propanol (R)-3-[2-(2-Propenyl)phenoxy]-1-isopropylamino-2-propanol [R,(+)]-3-[2-(2-Propenyl)phenoxy]-1-isopropylamino-2-propanol 1-(Isopropylamino)-3-(2-allylphenoxy)-2-propanol {2-hydroxy-3-[2-(prop-2-en-1-yl)phenoxy]propyl}(propan-2-yl)amine (RS)-Alprenolol 2-Propanol, 1-[(1-methylethyl)amino]-3-[2-(2-propen-1-yl)phenoxy]- Alprenolol USP/EP/BP anti-arrhythmic,5-hydroxytryptamine Receptor,anti-hypertensive,Inhibitor,Alprenolol,inhibit,Serotonin Receptor,anti-anginal,5-HT Receptor,β-adrenoceptor,5-HT1B,5-HT1A 13655-52-2 C15H23NO2C4H6O6