14133-90-5

Basic information

• Product Name: 4-HYDROXY PROPRANOLOL HCL
• Synonyms: 4-HYDROXY PROPRANOLOL HCL;4-HYDROXYPROPRANOLOL HYDROCHLORIDE;(R)-4-Hydroxy Propranolol Hydrochloride;4-[(2R)-2-Hydroxy-3-[(1-methylethyl)amino]propoxy]-1-naphthalenol Hydrochloride;(S)-4-Hydroxy Propranolol Hydrochloride;4-[(2S)-2-Hydroxy-3-[(1-methylethyl)amino]propoxy]-1-naphthalenol Hydrochloride;rac-4-Hydroxy Propranolol Hydrochloride;(±)-4-Hydroxypropranolol-d7 HCl
• CAS NO: 14133-90-5
• Molecular Formula: C16H22ClNO3
• Molecular Weight: 311.8
• Product Categories: Intermediates & Fine Chemicals;Metabolites & Impurities;Pharmaceuticals;Metabolites & Impurities, Pharmaceuticals, Intermediates & Fine Chemicals
• Mol File: 14133-90-5.mol
• Article Data: 2

Chemical Properties

• Melting Point: 156-158°C
• Boiling Point: 487.5°Cat760mmHg
• Flash Point: 248.6°C
• Appearance: /
• Density: 1.168g/cm³
• Storage Temp.: 2-8°C
• Solubility: DMSO (Slightly), Methanol (Slightly)
• Stability: Hygroscopic
• CAS DataBase Reference: 4-HYDROXY PROPRANOLOL HCL(CAS DataBase Reference)
• NIST Chemistry Reference: 4-HYDROXY PROPRANOLOL HCL(14133-90-5)
• EPA Substance Registry System: 4-HYDROXY PROPRANOLOL HCL(14133-90-5)

Safety Data

• Hazardous Substances Data: 14133-90-5(Hazardous Substances Data)

Usage

Description

4-HYDROXY PROPRANOLOL HCL, also known as 4-hydroxypropranolol hydrochloride, is a metabolite of propranolol, a non-selective beta-blocker used in the treatment of various cardiovascular conditions. It is an off-white solid and is derived from the metabolism of both (R)and (S)-enantiomers of propranolol. The presence of 4-hydroxypropranolol HCL in the body indicates the extent of propranolol metabolism and can be used to assess the effectiveness of the drug in patients.

Uses

Used in Pharmaceutical Industry:
4-HYDROXY PROPRANOLOL HCL is used as a metabolite for assessing the pharmacokinetics and pharmacodynamics of propranolol in patients. It helps in understanding the drug's metabolism, distribution, and elimination, which can be crucial for optimizing dosage and treatment regimens.
Used in Cardiovascular Research:
4-HYDROXY PROPRANOLOL HCL is used as a research compound for studying the effects of propranolol on cardiovascular conditions. It can provide insights into the drug's mechanism of action, potential side effects, and its interaction with other medications.
Used in Drug Metabolism Studies:
4-HYDROXY PROPRANOLOL HCL is used as a biomarker for evaluating the metabolic pathways of propranolol. This information can be valuable for understanding individual variations in drug response and for developing personalized treatment strategies.
Used in Quality Control:
4-HYDROXY PROPRANOLOL HCL is used as a reference compound in the quality control of propranolol formulations. It helps ensure the purity, potency, and consistency of the drug, which is essential for maintaining its therapeutic effectiveness and safety.

Biological Activity

(±)-4-hydroxy propranolol, an active metabolite of propranolol, blocks β1- and β2-adrenergic receptors (β1-ars, β2-ars). also, (±)-4-hydroxy propranolol has antioxidant properties at micromolar concentrations. β1- and β2-ars, expressed in cardiac myocytes, mediate an increase in contractility by gs-dependent coupling to adenylyl cyclase.

in vitro

compared to the control, (±)-4-hydroxy propranolol potently blocked the lipid peroxidation in a concentration-dependent fashion in endothelial cells. when pretreated with (±)-4-hydroxy propranolol at 0.067 to 6.7 μm, the degrees of protection were increased against the glutathione loss in the endothelial cells. additionally, (±)-4-hydroxy propranolol effectively preserved the loss of cell survival because of the radical stress [1].

in vivo

rats were injected intravenously with (±)-4-hydroxy propranolol into the femoral vein at 0.1 ml/100 g. (±)-4-hydroxy propranolol induced an increase in heart rate in a dose-dependent manner in rats depleted of catecholamines, which suggested that (±)-4-hydroxy propranolol had intrinsic sympathomimetic activity. the response of (±)-4-hydroxy propranolol was inhibited when rats were pretreated with 0.5 mg/kg propranolol [2].

IC 50

1.1 μm: inhibits lipid peroxidation in endothelial cells.

references

[1]. mak, i. potent antioxidant properties of 4-hydroxyl-propranolol. journal of pharmacology and experimental therapeutics. 2003; 308(1): 85-90. [2]. fitzgerald, j., & o'donnell, s. pharmacology of 4-hydroxypropranolol, a metabolite of propranolol. british journal of pharmacology. 1971; 43(1): 222-235.

Upstream product

• 107396-85-0 1-(4-Isopropoxy-naphthalen-1-yloxy)-3-isopropylamino-propan-2-ol 

Relevant articles and documents

Synthesis of enantiomeric 4-hydroxypropranolols from 1,4-dihydroxynaphthalene

Both (R)- and (S)-enantiomers of 4-hydroxypropranolol were effectively prepared from 1,4-dihydroxynaphthalene in eight steps. The overall yields were around 30%.