71771-90-9

Basic information

• Product Name: R(-)-DENOPAMINE
• Synonyms: (-)-(r)-1-(p-hydroxyphenyl)-2-((3,4-dimethoxyphenethyl)amino)ethanol;alpha-(((2-(3,4-dimethoxyphenyl)ethyl)amino)methyl)-4-hydroxy-benzenemethano;kalgut;(-)-α-(3,4-dimethoxyphenethylaminomethyl)-4-hydroxy-benzyl-alcohol;Benzenemethanol, α-[[[2-(3,4-dimethoxyphenyl)ethyl]amino]methyl]-4-hydroxy-, (R)-;Benzenemethanol, α-[[[2-(3,4-dimethoxyphenyl)ethyl]amino]methyl]-4-hydroxy-, (αR)-;Carguto;TA 064
• CAS NO: 71771-90-9
• Molecular Formula: C₁₈H₂₃NO₄
• Molecular Weight: 317.38
• Mol File: 71771-90-9.mol
• Article Data: 13

Chemical Properties

• Melting Point: 135°C
• Boiling Point: 456.67°C (rough estimate)
• Flash Point: 267.6°C
• Appearance: white/powder
• Density: 1.1949 (rough estimate)
• Vapor Pressure: 1.37E-11mmHg at 25°C
• Refractive Index: 1.5740 (estimate)
• Storage Temp.: 2-8°C
• Solubility: DMSO: 26 mg/mL, soluble
• CAS DataBase Reference: R(-)-DENOPAMINE(CAS DataBase Reference)
• NIST Chemistry Reference: R(-)-DENOPAMINE(71771-90-9)
• EPA Substance Registry System: R(-)-DENOPAMINE(71771-90-9)

Safety Data

• Hazard Codes: Xn
• Statements: 62-63
• Safety Statements: 22-36/37/39-45
• WGK Germany: 3
• RTECS: DA4795470
• Hazardous Substances Data: 71771-90-9(Hazardous Substances Data)

Usage

Description

R(-)-DENOPAMINE, also known as Denopamine, is a potent orally-active cardiotonic agent with selective effects on the beta-adrenergic receptors. It is a chiral molecule, with the R(-) enantiomer being the active form. Denopamine's positive inotropic activity is unique as it is not mediated through the release of catecholamines, which results in a lack of effect on heart rate and myocardial oxygen consumption. This characteristic offers significant advantages in the management of congestive heart failure, making it a valuable pharmaceutical candidate.
Brand Name: Kalgut

Uses

Used in Pharmaceutical Industry:
R(-)-DENOPAMINE is used as a cardiotonic agent for the management of congestive heart failure. Its selective action on beta-adrenergic receptors and unique mechanism of positive inotropic activity, without affecting heart rate and myocardial oxygen consumption, make it a beneficial treatment option for patients with this condition.
Used in Research Applications:
R(-)-DENOPAMINE is used as a β-adrenergic agonist in research settings to study its effects on contractility in isolated lymphatic vessels (LVs). This application aids in understanding the underlying mechanisms of action and potential therapeutic uses in various physiological and pathological conditions related to lymphatic function.

Biochem/physiol Actions

Denopamine is a cardiotonic drug.

InChI:InChI=1/C18H23NO4/c1-22-17-8-3-13(11-18(17)23-2)9-10-19-12-16(21)14-4-6-15(20)7-5-14/h3-8,11,16,19-21H,9-10,12H2,1-2H3/t16-/m0/s1

Upstream product

• 62717-74-2 N-[2-(3,4-dimethoxyphenyl)-ethyl]-2-hydroxy-2-(4-methoxyphenyl)ethylamine 
• 63365-60-6 (R)-1-(p-benzyloxyphenyl)-2-[2-(3,4-dimethoxyphenyl)ethylamino]ethanol 
• 71709-05-2 2-<(benzyloxycarbonyl)(3,4-dimethoxyphenethyl)amino>-1-(4-benzyloxyphenyl)ethanone 
• 153225-90-2 (-)-(α)-<<<2-(3,4-dimethoxyphenyl)ethyl>amino>methyl>-(α)-<(1,1-dimethylethyl)dimethylsilyloxy>-4-(2-propenyloxy)benzenemethane 
• 153225-89-9 (R)-2-<(1,1-dimethylethyl)dimethylsilyloxy>-2-<4-(2-propenyloxy)phenyl>acetonitrile 
• 153225-88-8 2-hydroxy-2-<4-(2-propenyloxy)phenyl>acetonitrile 
• 40663-68-1 4-(2-propenyloxy)benzaldehyde 
• 438528-25-7 (R)-(-)-2-azido-1-(4-tert-butyldimethylsilyloxyphenyl)ethanol 
• 102282-10-0 (R)-2-(4-benzyloxyphenyl)oxirane 
• 131965-54-3 (R)-(+)-2-bromo-1-(4'-benzyloxyphenyl) ethanol 
• 120-20-7 2-(3,4-dimethoxyphenyl)-ethylamine 
• 4254-67-5 2-bromo-1-(4-benzyloxyphenyl)-1-ethanone 
• 459867-22-2 1-[4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-2-nitro-ethanol 
• 459867-19-7 N-{2-[4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-2-hydroxy-ethyl}-2-(3,4-dimethoxy-phenyl)-acetamide 

Downstream Products

• 75241-20-2 RP 333 
• 87081-63-8 4-{2-[2-Hydroxy-2-(4-hydroxy-phenyl)-ethylamino]-ethyl}-2-methoxy-phenol 
• 87092-41-9 5-{2-[2-Hydroxy-2-(4-hydroxy-phenyl)-ethylamino]-ethyl}-2-methoxy-phenol 
• 105199-90-4 2-[2-Hydroxy-2-(4-hydroxy-phenyl)-ethyl]-7-methoxy-1,2,3,4-tetrahydro-isoquinolin-6-ol 
• 105199-91-5 2-[2-Hydroxy-2-(4-hydroxy-phenyl)-ethyl]-7-methoxy-1,2,3,4-tetrahydro-isoquinolin-8-ol 

Relevant articles and documents

Denopamine and preparation method of intermediate of denopamine

The invention discloses denopamine and a preparation method of an intermediate of denopamine, and particularly provides a method for preparing denopamine by Ir/f-amphox catalytic asymmetric hydrogenation. According to the method, steps are simple, operati

Asymmetric hydrogenation of α-primary and secondary amino ketones: Efficient asymmetric syntheses of (-)-arbutamine and (-)-denopamine

Two ss-receptor agonists (-)-denopamine and (-)-arbutamine were prepared in good yields and enantioselectivities by asymmetric hydrogenation of unprotected amino ketones for the first time by using Rh catalysts bearing electron-donating phosphine ligands. A series of α-primary and secondary amino ketones were synthesized and hydrogenated to produce various 1,2-amino alcohols in good yields and with good enantioselectivies. This Rh electron-donating phosphine-catalyzed asymmetric hyderogenation repI resents one of the most promising and convenient approaches towards the asymmetric synthesis of chiral amino alcohols.

Effect of ligand structure on the zinc-catalyzed Henry reaction. Asymmetric syntheses of (-)-denopamine and (-)-arbutamine

(Matrix presented) Syntheses of variously modified ligands for the dinuclear zinc catalysts for the asymmetric aldol and nitroaldol (Henry) reactions are reported. Catalytic enantioselective nitroaldol reactions promoted by these modified ligands led to efficient syntheses of the β-preceptor agonists (-)-denopamine and (-)-arbutamine.