13071-11-9

Basic information

• Product Name: (R)-(+)-PROPRANOLOL
• Synonyms: R-PROPANOLOL;R-(+)-PROPANOLOL HCL;(R)-(+)-PROPANOLOL HYDROCHLORIDE;(R)-(+)-PROPRANOLOL;R-PROPRANOLOL;(R)-(+)-PROPRANOLOL HYDROCHLORIDE;(R)-PROPRANOLOL HYDROCHLORIDE;(R)-(+)-1-[(1-METHYLETHYL)AMINO]-3-(1-NAPHTHALENYLOXY)-2-PROPANOL HYDROCHLORIDE
• CAS NO: 13071-11-9
• Molecular Formula: C₁₆H₂₁NO₂*ClH
• Molecular Weight: 295.81
• EINECS: 235-961-7
• Product Categories: Amines;Aromatics;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 13071-11-9.mol

Chemical Properties

• Melting Point: 196-198 °C(lit.)
• Boiling Point: 434.9 °C at 760 mmHg
• Flash Point: 216.8 °C
• Appearance: /
• Vapor Pressure: 2.48E-08mmHg at 25°C
• Storage Temp.: 2-8°C
• Solubility: ethanol: 10 mg/mL
• BRN: 5780490
• CAS DataBase Reference: (R)-(+)-PROPRANOLOL(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-(+)-PROPRANOLOL(13071-11-9)
• EPA Substance Registry System: (R)-(+)-PROPRANOLOL(13071-11-9)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• Safety Statements: 22-24/25
• WGK Germany: 3
• Hazardous Substances Data: 13071-11-9(Hazardous Substances Data)

Usage

Uses

1. Pharmaceutical Industry:
(R)-(+)-Propranolol is used as a β-adrenergic blocker for various medical applications, including:
a. Antihypertensive: It helps in the treatment of high blood pressure by blocking the effects of adrenaline on the heart and blood vessels.
b. Antianginal: It is used to prevent chest pain (angina) by reducing the workload on the heart and decreasing oxygen demand.
c. Antiarrhythmic (Class II): It is utilized to regulate abnormal heart rhythms by blocking the effects of adrenaline on the heart.
2. Research Applications:
(R)-(+)-Propranolol is also used in research settings to study the effects of β-adrenergic receptor antagonists on various physiological processes and to understand the differences between the active and less active enantiomers of propranolol.

Biochem/physiol Actions

Less active enantiomer of propranolol.

Mechanism of action

Pronolol hydrochloride is a non-selective beta-receptor blocker that blocks beta receptors in the myocardium and has antagonistic effects on beta1 and beta2 receptors. Slow down the heart rate, inhibit cardiac contractility and conduction, reduce circulating blood volume, and reduce myocardial oxygen consumption.

Purification Methods

The hydrochloride is recrystallised from n-PrOH or Me2CO. It is soluble in H2O and EtOH but is insoluble in Et2O, *C6H6 or EtOAc. The racemate has m 163-164o, and the free base recrystallises from cyclohexane with m 96o. [Howe & Shanks Nature 210 1336 1966.] The S-isomer (below) is the physiologically active isomer.

InChI:InChI=1/C16H21NO2.ClH/c1-12(2)17-10-14(18)11-19-16-9-5-7-13-6-3-4-8-15(13)16;/h3-9,12,14,17-18H,10-11H2,1-2H3;1H/t14-;/m0./s1

Upstream product

• 318-98-9 Inderal 
• 108433-49-4 1-chloro-2-acetoxy-3-(1-naphthyloxy)propane 
• 20133-93-1 1-chloro-3-(1-naphthoxy)-2-propanol 
• 90-15-3 α-naphthol 
• 2461-42-9 3-(1-naphthyloxy)-1,2-epoxypropane 
• 75-31-0 isopropylamine 
• 132005-35-7 (S)-(+)-1-chloro-3-(1-naphthyloxy)-2-propanol 

Downstream Products

• 91796-22-4 (+)-5-Hydroxypropranolol 
• 393828-92-7 (R)-N-desisopropylpropranolol 
• 227176-55-8 (R)-2-Phenyl-butyric acid (R)-1-(isopropylamino-methyl)-2-(naphthalen-1-yloxy)-ethyl ester 
• 227176-57-0 (S)-2-Phenyl-butyric acid (R)-1-(isopropylamino-methyl)-2-(naphthalen-1-yloxy)-ethyl ester 

Relevant articles and documents

Covalent Organic Frameworks with Chirality Enriched by Biomolecules for Efficient Chiral Separation

The separation of racemic compounds is important in many fields, such as pharmacology and biology. Taking advantage of the intrinsically strong chiral environment and specific interactions featured by biomolecules, here we contribute a general strategy is developed to enrich chirality into covalent organic frameworks (COFs) by covalently immobilizing a series of biomolecules (amino acids, peptides, enzymes) into achiral COFs. Inheriting the strong chirality and specific interactions from the immobilized biomolecules, the afforded biomolecules?COFs serve as versatile and highly efficient chiral stationary phases towards various racemates in both normal and reverse phase of high-performance liquid chromatography (HPLC). The different interactions between enzyme secondary structure and racemates were revealed by surface-enhanced Raman scattering studies, accounting for the observed chiral separation capacity of enzymes?COFs.

Establishment and Evaluation of the Novel Tetramethylammonium-L-Hydroxyproline Chiral Ionic Liquid Synergistic System Based on Clindamycin Phosphate for Enantioseparation by Capillary Electrophoresis

Much attention has been paid to chiral ionic liquids (ILs) in analytical chemistry, especially its application in capillary electrophoresis (CE) enantioseparation. However, the investigation of chiral ionic liquids synergistic systems based on antibiotic chiral selectors has been reported in only one article. In this work, a novel chiral ionic liquid, tetramethylammonium-L-hydroxyproline (TMA-L-Hyp), was applied for the first time in CE chiral separation to evaluate its potential synergistic effect with clindamycin phosphate (CP) as the chiral selector. As observed, significantly improved separation was obtained in this TMA-L-Hyp/CP synergistic system compared to TMA-L-Hyp or a CP single system. Several primary factors that might influence the separation were investigated, including CP concentration, TMA-L-Hyp concentration, buffer pH, types and concentrations of organic modifier, applied voltage, and capillary temperature. The best results were obtained with a 40 mM borax buffer (pH 7.6) containing 30 mM TMA-L-Hyp, 80 mM CP, and 20% (v/v) methanol, while the applied voltage and temperature were set at 20 kV and 20°C, respectively. Chirality 27:598-604, 2015.

Ultrafast chiral separations for high throughput enantiopurity analysis

Recent developments in fast chromatographic enantioseparations now make high throughput analysis of enantiopurity on the order of a few seconds achievable. Nevertheless, routine chromatographic determinations of enantiopurity to support stereochemical investigations in pharmaceutical research and development, synthetic chemistry and bioanalysis are still typically performed on the 5-20 min timescale, with many practitioners believing that sub-minute enantioseparations are not representative of the molecules encountered in day to day research. In this study we develop ultrafast chromatographic enantioseparations for a variety of pharmaceutically-related drugs and intermediates, showing that sub-minute resolutions are now possible in the vast majority of cases by both supercritical fluid chromatography (SFC) and reversed phase liquid chromatography (RP-LC). Examples are provided illustrating how such methods can be routinely developed and used for ultrafast high throughput analysis to support enantioselective synthesis investigations.

Uridine, thymidine and inosine used as chiral stationary phases in HPLC

In this paper, we present the first enantioseparations research using thymidine, uridine and inosine as chiral stationary phase bonded to silica gel via 3-(triethoxysilyl)propyl isocyanate in HPLC. Thymidine and uridine chiral stationary phases possess enantioseparation selectivity for alcohols, amines, ketones and carboxylic acids to some degree in normal-phase and reversed-phase mode. This work indicates that nucleoside or deoxynucleoside can be useful for the separation of enantiomers in the liquid phase as a new kind of chiral stationary phase.

Combined use of ionic liquid and hydroxypropyl-β-cyclodextrin for the enantioseparation of ten drugs by capillary electrophoresis

In the present study, hydroxypropyl-β-cyclodextrin and an ionic liquid (1-ethyl-3-methylimidazolium-l-lactate) were used as additives in capillary electrophoresis for the enantioseparation of 10 analytes, including ofloxacin, propranolol hydrochloride, dioxopromethazine hydrochloride, isoprenaline hydrochloride, chlorpheniramine maleate, liarozole, tropicamide, amlodipine benzenesulfonate, brompheniramine maleate, and homatropine methylbromide. The effects of ionic liquid concentrations, salt effect, cations, and anions of ionic liquids on enantioseparation were investigated and the results proved that there was a synergistic effect between hydroxypropyl-β-cyclodextrin and the ionic liquid, and the cationic part of the ionic liquid played an important role in the increased resolution. With the developed dual system, all the enantiomers of 10 analytes were well separated in resolutions of 5.35, 1.76, 1.85, 2.48, 2.88, 1.43, 5.45, 4.35, 2.76, and 2.98, respectively. In addition, the proposed method was applied to the determination of the enantiomeric purity of S-ofloxacin after validation of the method in terms of selectivity, repeatability, linearity range, accuracy, precision, limit of detection (LOD), and limit of quality (LOQ). Chirality 25:409-414, 2013.

Aminoalcohols, III: Preparation of Enantiomerically Pure Pharmacologically Active N-Substituted β-Aminoalcohols

A synthesis of N-substituted β-aminoalcohols is described starting from enantiomerically pure O-MBF- or O-MBE-protected β-aminoalcohols which can be prepared via LiAlH4 reduction of O-protected cyanohydrines. - Keywords: 1,2-Amino-alcohols, enantiomerically pure; N-Alkylation; Clorprenaline; Propranolol; Midodrine