4199-10-4

Basic information

• Product Name: (S)-(-)-PROPRANOLOL HYDROCHLORIDE
• Synonyms: (S)-(-)-1-[(1-METHYLETHYL)AMINO]-3-(1-NAPHTHALENYLOXY)-2-PROPANOL HYDROCHLORIDE;(S)-1-ISOPROPYLAMINO-3-(1-NAPHTHYLOXY)-2-PROPANOL HYDROCHLORIDE;S-(-)-PROPANOLOL HCL;S(-)-PROPRANOLOL HCL;(S)-(-)-PROPRANOLOL HYDROCHLORIDE;(S)-PROPRANOLOL HYDROCHLORIDE;2S-(-)-PROPANOLOL HYDROCHLORIDE;(S)-[2-hydroxy-3-(naphthyloxy)propyl]isopropylammonium chloride
• CAS NO: 4199-10-4
• Molecular Formula: C₁₆H₂₁NO₂*ClH
• Molecular Weight: 295.8
• EINECS: 224-096-0
• Product Categories: Adrenoceptor;Amines;Aromatics;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 4199-10-4.mol
• Article Data: 19

Chemical Properties

• Melting Point: 193-195 °C(lit.)
• Boiling Point: 434.9 °C at 760 mmHg
• Flash Point: 216.8 °C
• Appearance: /powder
• Storage Temp.: 2-8°C
• Solubility: ethanol: 10 mg/mL
• BRN: 3574966
• CAS DataBase Reference: (S)-(-)-PROPRANOLOL HYDROCHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-(-)-PROPRANOLOL HYDROCHLORIDE(4199-10-4)
• EPA Substance Registry System: (S)-(-)-PROPRANOLOL HYDROCHLORIDE(4199-10-4)

Safety Data

• Hazard Codes: Xn
• Statements: 20/21/22
• Safety Statements: 36
• WGK Germany: 3
• Hazardous Substances Data: 4199-10-4(Hazardous Substances Data)

Usage

Description

(S)-(-)-Propranolol is the active enantiomer of propranolol, a β-adrenergic receptor antagonist with log Kd values of -8.16, -9.08, and -6.93 for β1, β2, and β3, respectively. It is also a non-specific serotonin receptor antagonist. Propanolol was one of the first β-adrenergic receptor blockers to be widely used in clinical practice for the treatment of hypertension, angina pectoris, and cardiac ischemia.

Chemical Properties

(S)-(-)-1-(Isopropylamino)-3-(1-naphthyloxy)-2-propanol hydrochloride

Uses

Different sources of media describe the Uses of 4199-10-4 differently. You can refer to the following data:
1. active enantiomer, 5-HT1 receptor antagonist
2. The S-enantiomer of Propranolol (P831800). β?Adrenergic blocker. Antihypertensive; antianginal; antiarrhythmic (class II).
3. Antihypertensor;Beta-adrenergic blocking agent

Biological Activity

More active enantiomer of the β -adrenoceptor antagonist propranolol ((RS)-1-[(1-Methylethyl)amino]-3-(1-naphthalenyloxy)-2-propanol hydrochloride ).

Biochem/physiol Actions

(S)-(?)-Propranolol hydrochloride is biologically active enantiomer. It acts as β1 receptor antagonist in thalamocortical neurons. (S)-(?)-Propranolol hydrochloride elicits its inhibitory function on the β1 adrenoceptor in trigeminovascular pain pathway and serves as a preventive medicine in migraine.

Purification Methods

The (+)-salt is the active isomer which blocks isoprenaline tachycardia and is a -adrenergic blocker. [Leclerc et al. Trends Pharmacol Sci 2 18 1981, Howe & Shanks Nature 210 1336 1966.]

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

• 90-15-3 α-naphthol 
• 36141-41-0 S-(-)-1-chloro-3-isopropylamino-2-propanol hydrochloride 
• 16204-21-0 N-isopropyl-3-(naphthyloxy)-2-oxo-1-propylamine hydrochloride 
• 61249-00-1 (S)-(1-naphthyl) glycidyl ether 
• 75-31-0 isopropylamine 
• 56715-28-7 (R)-1-(1-naphthyloxy)-2,3-epoxypropane 
• 108508-19-6 (R)-(-)-1-chloro-2-acetoxy-3-(1-naphthyloxy)propane 
• 67-64-1 acetone 
• 227176-56-9 (R)-2-Phenyl-butyric acid (S)-1-(isopropylamino-methyl)-2-(naphthalen-1-yloxy)-ethyl ester 
• 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 
• 115314-14-2 (2s)-(+)-glycidyl 3-nitrobenzenesulfonate 
• 213130-05-3 (2RS,4R)-4-(1-naphthyloxy)methyl-2-oxo-1,3,2-dioxathiolane 
• 56715-19-6 (S)-3-(1-naphthyloxy)-1,2-propanediol 

Downstream Products

• 227176-57-0 (S)-2-Phenyl-butyric acid (R)-1-(isopropylamino-methyl)-2-(naphthalen-1-yloxy)-ethyl ester 
• 227176-56-9 (R)-2-Phenyl-butyric acid (S)-1-(isopropylamino-methyl)-2-(naphthalen-1-yloxy)-ethyl ester 
• 227176-55-8 (R)-2-Phenyl-butyric acid (R)-1-(isopropylamino-methyl)-2-(naphthalen-1-yloxy)-ethyl ester 
• 91796-22-4 (+)-5-Hydroxypropranolol 
• 393828-92-7 (R)-N-desisopropylpropranolol 
• 81907-79-1 (-)-5-Hydroxypropranolol 
• 393828-91-6 (S)-N-desisopropylpropranolol 

Relevant articles and documents

Catalytic Asymmetric Nitroaldol Reaction: An Efficient Synthesis of (S) Propranolol Using the Lanthanum Binaphthol Complex

(S) Propranolol, a more potent optical isomer of the widely used β-blocker, was conveniently synthesized in a highly enantioselective manner by the lanthanum-(R)-(+)-binaphthol complex catalyzed asymmetric nitroaldol reaction.

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.