oxprenolol
oxprenolol Basic information
- Product Name:
- oxprenolol
- Synonyms:
-
- 1-(2-allyloxyphenoxy)-3-isopropylaminopropan-2-ol
- 2-Propanol, 1-(1-methylethyl)amino-3-2-(2-propenyloxy)phenoxy-
- 1-(Isopropylamino)-2-hydroxy-3-[o-(allyloxy)phenoxy]propane
- 1-[o-(Allyloxy)phenoxy]-3-(isopropylamino)-2-propanol
- 2-Propanol, 1-[(1-methylethyl)amino]-3-[2-(2-propenyloxy)phenoxy]- (9CI)
- 2-Propanol, 1-[o-(allyloxy)phenoxy]-3-(isopropylamino)- (7CI, 8CI)
- Coretal
- dl-Oxprenolol
- CAS:
- 6452-71-7
- MF:
- C15H23NO3
- MW:
- 265.35
- EINECS:
- 2292579
- Mol File:
- 6452-71-7.mol
oxprenolol Chemical Properties
- Melting point:
- 78-80°
- Boiling point:
- 408.57°C (rough estimate)
- Density
- 1.0479 (rough estimate)
- refractive index
- 1.5000 (estimate)
- solubility
- Dichloromethane (Slightly), Methanol (Slightly)
- form
- Solid
- pka
- 13.89±0.20(Predicted)
- color
- White to Off-White
- Stability:
- Stable under recommended storage conditions., Stable Under Recommended Storage C
oxprenolol Usage And Synthesis
Description
Oxprenolol induced contact dermatitis in a worker at a pharmaceutical plant, in the division for drug synthesis. Epichlorhydrin was also used for the production of both propranolol and oxprenolol.
Originator
Trasicor,Ciba Geigy ,Italy,1970
Uses
Oxprenolol is a free base of Oxprenolol Hydrochloride(O870500) which is a β-Adrenergic blocker. Antihypertensive, antianginal, antiarrhythmic.
Uses
Vasodilator(coronary).
Definition
ChEBI: 1-(propan-2-ylamino)-3-(2-prop-2-enoxyphenoxy)-2-propanol is an aromatic ether.
Manufacturing Process
75 grams of pyrocatechol monoallyl ether, 75 grams of epichlorohydrin, 75 grams of potassium carbonate and 400 ml of acetone are stirred and heated at the boil for 12 hours. The potassium carbonate is then filtered off. The solvent is distilled off in a water-jet vacuum. The residual oil is dissolved in ether and agitated with 2 N sodium hydroxide solution. The ether is separated, dried and distilled off. The residue is distilled in a water-jet vacuum. 3-(ortho-allyloxy-phenoxy)-1,2-epoxypropane passes over at 145° to 157°C under 11 mm Hg pressure. A solution of 15 grams of 3-(ortho-allyloxyphenoxy)-1,2-epoxypropane and 15 grams of isopropylamine in 20 ml of ethanol is refluxed for 4 hours. The excess amine and the alcohol are then distilled off under vacuum, to leave 1-isopropylamino-2-hydroxy-3-(orthoallyloxy-phenoxy)-propane which melts at 75° to 80°C after recrystallization from hexane.
brand name
Trasicor (Novartis).
Therapeutic Function
Antiarrhythmic
Contact allergens
The beta-blocker oxprenolol induced contact dermatitis in a worker at a pharmaceutical plant, in a division for drug synthesis. Epichlorhydrin was also used for the production of drugs propranolol and oxprenolol.
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