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D7815

R(−)-Denopamine

Name: R(−)-Denopamine
Brand: SIGMA

≥98% (HPLC), powder

Synonym(s):

(−)-α-(3,4-Dimethoxyphenethylaminomethyl)-4-hydroxybenzylalcohol

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About This Item

Empirical Formula (Hill Notation):

C₁₈H₂₃NO₄

CAS Number:

71771-90-9

Molecular Weight:

317.38

MDL number:

MFCD00867122

UNSPSC Code:

12352116

PubChem Substance ID:

24278687

NACRES:

NA.77

Quality Level

100

Assay

≥98% (HPLC)

form

powder

color

white

solubility

DMSO: 10 mg/mL, clear
H₂O: insoluble

storage temp.

2-8°C

SMILES string

COc1ccc(CCNC[C@H](O)c2ccc(O)cc2)cc1OC

InChI

1S/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

InChI key

VHSBBVZJABQOSG-INIZCTEOSA-N

Gene Information

human ... ADRB1(153)

Application

R(-)-Denopamine has been used as an β-adrenergic agonist to study its effects on contractility in isolated lymphatic vessels (LVs).

Biochem/physiol Actions

Denopamine is a cardiotonic drug.

β₁-adrenoceptor agonist.

Features and Benefits

This compound is featured on the β-Adrenoceptors page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Caution

Light sensitive.

Pictograms

GHS08

Signal Word

Warning

Hazard Statements

H361

Precautionary Statements

P281

Hazard Classifications

Repr. 2

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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[A one-month combined use of selective adrenergic beta 1- and alpha 1-agonists for postprandial hypotension in patients with autonomic failure].

M Hirayama et al.

Rinsho shinkeigaku = Clinical neurology, 40(8), 787-790 (2001-02-24)

In 1993, we reported the pathophysiology of postprandial hypotension (PPH) in patients with sympathetic dysfunction: a fall of BP resulted from both excess systemic vasodilation and lack of compensatory increase of cardiac output and vascular resistance in the leg arteries.

Asymmetric hydrogenation of alpha-primary and secondary amino ketones: efficient asymmetric syntheses of (-)-arbutamine and (-)-denopamine.

Gao Shang et al.

Chemistry (Weinheim an der Bergstrasse, Germany), 13(27), 7780-7784 (2007-06-27)

Two beta-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 alpha-primary and secondary amino ketones

The role of β-adrenergic receptors in the cardioprotective effects of beta-preconditioning (βPC).

Ruduwaan Salie et al.

Cardiovascular drugs and therapy, 25(1), 31-46 (2011-01-13)

To determine the mechanism whereby transient stimulation of the β-adrenergic receptor subtypes (β-AR) elicit cardioprotection against subsequent ischaemia. Isolated rat hearts were subjected to 35 min regional ischaemia (RI) and reperfusion and infarct size (IS) determined. Hearts were preconditioned with

Prolongation of the life span of cardiomyopathic hamster by the adrenergic beta 1-selective partial agonist denopamine.

H Kurosawa et al.

Japanese journal of pharmacology, 72(4), 325-333 (1996-12-01)

Influence of cardiotonic agents on the prognosis of heart failure depends on the individual therapeutic agents, and favorable and unfavorable effects of these agents have been reported in clinical trials. We studied the effect of the cardiotonic agent denopamine on

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

Barry M Trost et al.

Organic letters, 4(16), 2621-2623 (2002-08-03)

[reaction: see text] 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 beta-receptor agonists

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