CAS 10476-53-6

(±)-4-Hydroxypropranolol

Description:

(±)-4-Hydroxypropranolol is a beta-blocker that is primarily used in the treatment of cardiovascular conditions such as hypertension and anxiety. It is a racemic mixture, meaning it contains equal parts of two enantiomers, which can exhibit different pharmacological effects. The compound features a hydroxyl group (-OH) at the 4-position of the propranolol structure, enhancing its solubility and bioavailability. Its mechanism of action involves blocking beta-adrenergic receptors, which leads to a decrease in heart rate and blood pressure. The substance is known for its ability to cross the blood-brain barrier, which contributes to its efficacy in treating anxiety-related disorders. In terms of physical properties, (±)-4-Hydroxypropranolol is typically a white to off-white crystalline powder, and it is soluble in water and organic solvents. Safety and efficacy profiles are well-documented, but like all medications, it may have side effects and contraindications that should be considered in clinical use.

Formula: C₁₆H₂₁NO₃

InChI: InChI=1S/C16H21NO3/c1-11(2)17-9-12(18)10-20-16-8-7-15(19)13-5-3-4-6-14(13)16/h3-8,11-12,17-19H,9-10H2,1-2H3

InChI key: InChIKey=CWEPACWBWIOYID-UHFFFAOYSA-N

SMILES: O(CC(CNC(C)C)O)C=1C2=C(C(O)=CC1)C=CC=C2

Synonyms:

• (+/-)-1-Hydroxypropranolol,HCl
• (+/-)-1-Hydroxypropranolol,hydrochloride
• (±)-4-Hydroxypropranolol
• 1-Naphthalenol, 4-[2-hydroxy-3-[(1-methylethyl)amino]propoxy]-
• 2-Propanol, 1-[(4-hydroxy-1-naphthyl)oxy]-3-(isopropylamino)-
• 4-[2-Hydroxy-3-(Propan-2-Ylamino)Propoxy]Naphthalen-1-Ol
• 4-[2-Hydroxy-3-[(1-methylethyl)amino]propoxy]-1-naphthalenol
• 4-[2-Hydroxy-3-[(1-methylethyl)amino]propoxy]-1-naphthalenol Hydrochloride
• 4-{2-Hydroxy-3-[(1-Methylethyl)Amino]Propoxy}Naphthalen-1-Ol Hydrochloride
• Recemic 4-hydroxypropranolol

(R)-4-Hydroxy Propranolol Hydrobromide

Controlled Product

CAS: 10476-53-6

Applications The main metabolite of (R)-Propranolol.
References Shwed, J., et al.: Xenobiotica, 22, 973 (1992), Fujita, K., et al.: Biol. Pharm. Bull., 22, 446 (1999), Walle, U., et al.: Drug Metab. Dispos., 30, 564 (2002),

Formula: C₁₆H₂₁NO₃·HBr

Color and Shape: Neat

Molecular weight: 356.25

Ref: TR-H952530