174689-39-5

Basic information

• Product Name: 1-(2-ETHYLPHENOXY)-3-[[(1S)-1,2,3,4-TETRAHYDRO-1-NAPHTHALENYL]AMINO]-(2S)-2-PROPANOL HYDROCHLORIDE
• Synonyms: 1-(2-ETHYLPHENOXY)-3-[[(1S)-1,2,3,4-TETRAHYDRO-1-NAPHTHALENYL]AMINO]-(2S)-2-PROPANOL HYDROCHLORIDE;SR 59230A HYDROCHLORIDE;SR59230AHCl;3-(2-Ethylphenoxy)-1-[[(1S)-1,2,3,4-tetrahydronaphth-1-yl]amino]-(2S)-2-propanol oxalate salt;SR 59230A
• CAS NO: 174689-39-5
• Molecular Formula: C21H27NO2.C2H2O4
• Molecular Weight: 415.48
• Product Categories: Adrenoceptor
• Mol File: 174689-39-5.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 542.6°Cat760mmHg
• Flash Point: 281.9°C
• Appearance: white/
• Density: g/cm³
• Vapor Pressure: 1.27E-11mmHg at 25°C
• Storage Temp.: Store at RT
• Solubility: DMSO: >10mg/mL
• CAS DataBase Reference: 1-(2-ETHYLPHENOXY)-3-[[(1S)-1,2,3,4-TETRAHYDRO-1-NAPHTHALENYL]AMINO]-(2S)-2-PROPANOL HYDROCHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(2-ETHYLPHENOXY)-3-[[(1S)-1,2,3,4-TETRAHYDRO-1-NAPHTHALENYL]AMINO]-(2S)-2-PROPANOL HYDROCHLORIDE(174689-39-5)
• EPA Substance Registry System: 1-(2-ETHYLPHENOXY)-3-[[(1S)-1,2,3,4-TETRAHYDRO-1-NAPHTHALENYL]AMINO]-(2S)-2-PROPANOL HYDROCHLORIDE(174689-39-5)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• Hazardous Substances Data: 174689-39-5(Hazardous Substances Data)

Usage

Uses

SR 59230A was used in the identification of β-adrenoceptors in rat aorta.3 It was tested as a potential therapeutic agent in improving cardiac function in rat model of heart failure.4

Hazard

A poison.

Biological Activity

Potent and selective β 3 adrenoceptor antagonist (IC 50 values are 40, 408 and 648 nM for β 3 , β 1 and β 2 receptors respectively). Orally active in vivo . Also available as part of the β -Adrenoceptor Antagonist Tocriset? .

Biochem/physiol Actions

SR 59230A is a β3-adrenoceptor antagonist. It has high affinity for the β3 adrenoceptors occurring in human gut that affect the function of human colonic circular smooth muscle.1 It is reported that SR 59230A inhibits the Kir2.1-2.3 cardiac potassium channels.2

InChI:InChI=1/C21H27NO2.C2H2O4/c1-2-16-8-4-6-13-21(16)24-15-18(23)14-22-20-12-7-10-17-9-3-5-11-19(17)20;3-1(4)2(5)6/h3-6,8-9,11,13,18,20,22-23H,2,7,10,12,14-15H2,1H3;(H,3,4)(H,5,6)/t18-,20-;/m0./s1

Upstream product

• 1092799-92-2 (S)-3-(2'-ethylphenoxy)-propane-1,2-diol 
• 90-00-6 o-Hydroxyethylbenzene 
• 144-62-7 oxalic acid 
• 1430052-95-1 1-(2′-ethylphenoxy)-2,3-epoxy-propane 
• 23357-46-2 (R)-1,2,3,4-Tetrahydro-1-naphthylamine 
• 7149-82-8 rac-3-(2-ethylphenoxy)propane-1,2-diol 
• 1092799-94-4 (R)-3-(2'-ethylphenoxy)-propane-1,2-diol 
• 1616790-43-2 1-(2′-ethylphenoxy)-2,3-epoxy-propane 
• 23357-52-0 (S)-1,2,3,4-tetrahydronapht-1-yl-amine 

Relevant articles and documents

Synthesis of all of the stereoisomers of β3-adrenoceptor antagonist SR 59230 based on the spontaneous resolution of 3-(2-ethylphenoxy)propane-1,2-diol

Racemic 3-(2-ethylphenoxy)propane-1,2-diol 2 has been effectively resolved into (S)- and (R)-enantiomers by a preferential crystallization procedure. Non-racemic diols 2, obtained via a Mitsunobu reaction, have been converted into the non-racemic 1,2-epox