76792-97-7

Basic information

• Product Name: (R)-4-Hydroxy Propranolol
• Synonyms: (+)-Hydroxypropranolo;(R)-4-Hydroxy Propranolol;4-[(2R)-2-Hydroxy-3-[(1-methylethyl)amino]propoxy]-1-naphthalenol;(+)-Hydroxypropranolol;(R)-1-(Isopropylamino)-3-[(4-hydroxynaphthalen-1-yl)oxy]-2-propanol
• CAS NO: 76792-97-7
• Molecular Formula: C₁₆H₂₁NO₃
• Molecular Weight: 275.34
• Product Categories: Various Metabolites and Impurities
• Mol File: 76792-97-7.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 487.526 °C at 760 mmHg
• Flash Point: 248.647 °C
• Appearance: /
• Density: 1.168
• CAS DataBase Reference: (R)-4-Hydroxy Propranolol(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-4-Hydroxy Propranolol(76792-97-7)
• EPA Substance Registry System: (R)-4-Hydroxy Propranolol(76792-97-7)

Safety Data

• Hazardous Substances Data: 76792-97-7(Hazardous Substances Data)

Usage

Description

(R)-4-Hydroxy Propranolol is a chemical compound and an active metabolite of the drug propranolol, which is used to treat high blood pressure, chest pain, and other conditions. It is formed in the liver through the process of oxidation and exhibits beta-adrenergic blocking activity, affecting the functioning of the sympathetic nervous system by blocking the action of adrenaline. Its chemical structure consists of a hydroxy group and a chiral center, existing in different enantiomeric forms. (R)-4-Hydroxy Propranolol has been studied for its potential role in the treatment of various cardiovascular and neurological disorders and is also used as a reference standard in research and clinical settings.

Uses

Used in Pharmaceutical Industry:
(R)-4-Hydroxy Propranolol is used as an active metabolite of propranolol for the treatment of high blood pressure and chest pain. Its beta-adrenergic blocking activity helps in managing these conditions effectively.
Used in Research and Clinical Settings:
(R)-4-Hydroxy Propranolol is used as a reference standard in research and clinical settings to study its potential role in the treatment of various cardiovascular and neurological disorders. Its unique chemical structure and chiral center make it a valuable compound for scientific investigations.
Used in Cardiovascular Applications:
(R)-4-Hydroxy Propranolol is used as a beta-blocker for the treatment of cardiovascular disorders, such as high blood pressure and chest pain. Its ability to block the action of adrenaline helps in reducing the heart rate and blood pressure, providing relief from these conditions.
Used in Neurological Applications:
(R)-4-Hydroxy Propranolol is used in the study and potential treatment of neurological disorders. Its beta-adrenergic blocking activity may have beneficial effects on certain neurological conditions, and ongoing research aims to explore these possibilities further.

Upstream product

• 525-66-6 propranolol 
• 84-85-5 4-methoxynaphth-1-ol 
• 90-15-3 α-naphthol 
• 2461-42-9 3-(1-naphthyloxy)-1,2-epoxypropane 
• 318-98-9 Inderal 
• 18507-09-0 4-Methoxypropranolol 
• 14133-79-0 (+/-)-4-Methoxypropranolol hydrochloride 

Downstream Products

• 130-15-4 [1,4]naphthoquinone 

Relevant articles and documents

Multistage Reactive Transmission-Mode Desorption Electrospray Ionization Mass Spectrometry

Elucidating reaction mechanisms is important for advancing many areas of science such as catalyst development. It is often difficult to probe fast reactions at ambient conditions with high temporal resolution. In addition, systems involving reagents that

Covalent binding of a reactive metabolite derived from propranolol and its active metabolite 4-hydroxypropranolol to hepatic microsomal proteins of the rat

Repeated administration of propranolol (PL) to rats causes the inhibition of cytochrome P450-2D (P450-2D) enzyme. We recently found that 4- hydroxypropranolol (4-OH-PL) was biotransformed to 1,4-naphthoquinone (1,4- NQ) by superoxide (SO) anions in medium containing rat liver microsomes and NADPH and proposed that the binding of the quinone to P450-2D apoproteins might be one of mechanisms for the enzyme inhibition [Narimatsu et al. (1995) Chem. Res. Toxicol. 8, 721-728]. In this study, we have searched for possible sources of SO for the conversion of 4-OH-PL to 1,4-NQ in rat liver microsomes and determined the radioactivity covalently bound to microsomal proteins after incubation of radioactive PL and 4-OH-PL with rat liver microsomes. Elimination of 4-OH-PL from a mixture containing microsomes and NADPH was suppressed by carbon monoxide. Antibodies raised to P450-2B1 and -3A2 partially, and antibody against NADPH-cytochrome P450 reductase (fp2) markedly suppressed the reaction. 1,4-NQ was formed concomitantly with 4-OH- PL elimination by a reconstituted preparation of fp2. Binding studies using naphthalene ring (NR)- and side chain (SC)-radiolabeled PL and 4-OH-PL showed that radioactivity covalently bound to microsomal proteins was much higher from 4-OH-PL than from PL for the NR-labeled compounds, but higher from PL than from 4-OH-PL for the SC-labeled compounds. These results suggest that the 4-OH-PL formed from PL by P450-2D enzyme is converted to 1,4-NQ with loss of the side chain, and the 1,4-NQ accounts for most of the radioactivity covalently bound to microsomal proteins, including the P450-2D enzymes. The SO for conversion of 4-OH-PL to 1,4-NQ is supplied mainly by fp2 with some contribution by P450 enzymes.

Ring-hydroxylated propranolol: Synthesis and β-receptor antagonist and vasodilating activities of the seven isomers

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