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M5391

(±)-Metoprolol (+)-tartrate salt

≥98% (titration), β1-adrenoceptor antagonist, 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
NACRES:
NA.77
PubChem Substance ID:
24278556
UNSPSC Code:
12352200
EC Number:
260-148-9
MDL number:
MFCD00056257
Assay:
≥98% (titration)
Form:
powder
Quality level:
200

Key Documents

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Product Name

(±)-Metoprolol (+)-tartrate salt, ≥98% (titration), powder

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

signalword

Warning

Hazard Classifications

Aquatic Chronic 2 - Repr. 2

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
BCCP4580
BCCM7734
BCCL6869
BCBQ6262
BCBQ6262V

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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
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)
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)
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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DISCOVER Bioactive Small Molecules for Neuroscience

Global Trade Item Number

SKUGTIN
M5391-10G04061834059875
M5391-1G04061834059882
M5391-5G04061834059899

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