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A143

(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
NACRES:
NA.77
PubChem Substance ID:
24277807
UNSPSC Code:
12352200
MDL number:
MFCD00074918
Form:
powder
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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)

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.

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Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
0000407124
0000361566
0000407124
0000361566
0000173888

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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)
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
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
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