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M5391

Sigma-Aldrich

(±)-Metoprolol (+)-tartrate salt

≥98% (titration), powder

Synonym(s):

(±)1-(Isopropylamino)-3-[p-(β-methoxyethyl)phenoxy]-2-propanol (+)-tartrate salt, Lopressor

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About This Item

Linear Formula:
(C15H25NO3)2 · C4H6O6
CAS Number:
56392-17-7
Molecular Weight:
684.81
EC Number:
260-148-9
MDL number:
MFCD00056257
UNSPSC Code:
12352200
PubChem Substance ID:
24278556
NACRES:
NA.77

Quality Level

200

Assay

≥98% (titration)

form

powder

color

white to off-white

solubility

H2O: 50 mg/mL

originator

Novartis

SMILES string

O[C@H]([C@@H](O)C(O)=O)C(O)=O.COCCc1ccc(OCC(O)CNC(C)C)cc1.COCCc2ccc(OCC(O)CNC(C)C)cc2

InChI

1S/2C15H25NO3.C4H6O6/c2*1-12(2)16-10-14(17)11-19-15-6-4-13(5-7-15)8-9-18-3;5-1(3(7)8)2(6)4(9)10/h2*4-7,12,14,16-17H,8-11H2,1-3H3;1-2,5-6H,(H,7,8)(H,9,10)/t;;1-,2-/m..1/s1

InChI key

YGULWPYYGQCFMP-CEAXSRTFSA-N

Gene Information

human ... ADRB1(153)

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General description

Metoprolol has antihypertensive and anti-ischemic properties. It is used to treat arrhythmias.

Application

(±)-Metoprolol (+)-tartrate salt has been used:
  • to modulate the immunological parameters in various studies
  • to study its effects onCa2+-calmodulin-dependent protein kinase II (CaMKII) activity in human and experimental heart failure (HF)
  • to examine the contribution of the adrenergic receptors to the production of norepinephrine (NE)-mediated O2-

Biochem/physiol Actions

β1-adrenoceptor antagonist.

Features and Benefits

This compound is a featured product for Neuroscience research. Click here to discover more featured Neuroscience products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.
This compound was developed by Novartis. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

Other Notes

Shelf-life of the powder is at least 4 years.

Pictograms

Health hazardEnvironment
GHS08,GHS09

Signal Word

Warning

Hazard Statements

H361d,H411

Hazard Classifications

Aquatic Chronic 2 - 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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The acute modulation of norepinephrine on immune responses and genes expressions via adrenergic receptors in the giant freshwater prawn, Macrobrachium rosenbergii
Chang CC, et al.
Fish & Shellfish Immunology, 46(2), 459-467 (2015)
Metoprolol
Koch-Weser J
The New England Journal of Medicine, 301(13), 698-703 (1979)
CaMKII Activity Persists During Chronic beta-Adrenoceptor Blockade in Experimental and Human Heart Failure
Dewenter M, et al.
Circulation. Heart Failure, 10(5), e003840-e003840 (2017)
L Brynne et al.
The Journal of pharmacology and experimental therapeutics, 286(3), 1152-1158 (1998-09-11)
The concentration-effect relationship of l-propranolol and dl-metoprolol were investigated in spontaneous hypertensive rats using reduction in exercise-induced tachycardia as a pharmacodynamic endpoint. The influence of protein binding on the effect relationship was also assessed. The rats were assigned to treatment
Octopamine enhances the immune responses of freshwater giant prawn, Macrobrachium rosenbergii, via octopamine receptors
Kuo HW and Cheng W
Developmental and Comparative Immunology, 81, 19-32 (2018)
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