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A143

Sigma-Aldrich

(S)-(−)-Atenolol

powder

Synonym(s):

(−)-4-[2-Hydroxy-3-[(1-methylethyl)amino]propoxy]benzeneacetamide

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About This Item

Linear Formula:
(CH3)2CHNHCH2CH(OH)CH2OC6H4CH2CONH2
CAS Number:
93379-54-5
Molecular Weight:
266.34
MDL number:
MFCD00074918
UNSPSC Code:
12352200
PubChem Substance ID:
24277807
NACRES:
NA.77

form

powder

optical activity

[α]23/D −10.5°, c = 0.5 in H2O(lit.)

color

white to beige

mp

148-152 °C (lit.)

solubility

0.1 M HCl: soluble

SMILES string

CC(C)NC[C@H](O)COc1ccc(CC(N)=O)cc1

InChI

1S/C14H22N2O3/c1-10(2)16-8-12(17)9-19-13-5-3-11(4-6-13)7-14(15)18/h3-6,10,12,16-17H,7-9H2,1-2H3,(H2,15,18)/t12-/m0/s1

InChI key

METKIMKYRPQLGS-LBPRGKRZSA-N

Gene Information

human ... ADRB1(153)

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Application

(S)-(-)-Atenolol may be used as a standard in the preparation of enantiomer for high-performance liquid chromatography-tandem mass spectrometry studies (HPLC-MS/MS). It has also been used in the β blocking molecule for Raman spectroscopy studies.

Biochem/physiol Actions

(S)-(-)-Atenolol is a β1-adrenergic receptor antagonist and an active enantiomer of atenolol.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Certificates of Analysis (COA)

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The influence of molecular structure modifications on vibrational properties of some beta blockers: a combined raman and DFT study
Farca? A, et al.
Journal of Spectroscopy (New York, NY, United States) (2016)
Kevin F Morris et al.
Chemical physics, 457, 133-146 (2015-08-11)
Molecular dynamics simulations and NMR spectroscopy were used to compare the binding of two β-blocker drugs to the chiral molecular micelle poly-(sodium undecyl-(L)-leucine-valine). The molecular micelle is used as a chiral selector in capillary electrophoresis. This study is part of
A A Pearson et al.
The Journal of pharmacology and experimental therapeutics, 250(3), 759-763 (1989-09-01)
Previous studies have demonstrated that propranolol can lower arterial pressure through an action within the central nervous system. The purpose of this study was to determine 1) whether the hydrophilic beta blocking drug atenolol which is devoid of membrane stabilizing
S A Doggrell
Chirality, 5(1), 8-14 (1993-01-01)
The effects of (+/-)-, (+)-, and (-)-atenolol, sotalol, and amosulalol alone on the rat left atria and portal vein and on the respective beta 1- and beta 2-adrenoceptor-mediated responses to isoprenaline have been determined. (+/-)-Atenolol at 10(-6) M had no
Ulisse Garbin et al.
Mediators of inflammation, 2008, 367590-367590 (2008-04-26)
The endothelium plays a key role in the development of atherogenesis and its inflammatory and proliferative status influences the progression of atherosclerosis. The aim of this study is to compare the effects of two beta blockers such as nebivolol and
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Chromatograms

application for HPLC

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