This compound has two centers of optical activity. In the metoprolol, both optical isomers (dextrorotatory and levorotatory) are present. In the tartrate portion, only one optically active isomer is present, the (+) form
M5391
(±)-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:
Molecular Weight:
684.81
EC Number:
MDL number:
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.77
Pricing and availability is not currently available.
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Quality Level
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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Related Categories
General description
Application
(±)-Metoprolol (+)-tartrate salt has been used:
- to modulate the immunological parameters in various studies[3][4][5]
- to study its effects onCa2+-calmodulin-dependent protein kinase II (CaMKII) activity in human and experimental heart failure (HF)[6]
- to examine the contribution of the adrenergic receptors to the production of norepinephrine (NE)-mediated O2-[7]
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.
Signal Word
Warning
Hazard Statements
Precautionary Statements
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
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Customers Also Viewed
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
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)
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)
Metoprolol
Koch-Weser J
The New England Journal of Medicine, 301(13), 698-703 (1979)
Tyramine's modulation of immune resistance functions in Litopenaeus vannamei and its signal pathway
Kuo HW, et al.
Developmental and Comparative Immunology (2019)
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Chromatograms
application for HPLCapplication for HPLCapplication for HPLCapplication for HPLCShow More-
What is the optical activity of Product M5391, (±)-Metoprolol (+)-tartrate salt?
1 answer-
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What is the solubility of Product M5391, (±)-Metoprolol (+)-tartrate salt?
1 answer-
The product is soluble in water (>1 g/mL), methanol (> 500 mg/mL), chloroform (496 mg/mL), acetone (1.1 mg/mL), acetonitrile (0.89 mg/mL), and hexane (0.001 mg/mL). This information can be found at in the following reference: The chemicals encyclopedia published by the Royal Society of Chemistry, 12th ed., Entry# 6235.
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What are the recommended storage conditions for Product M5391, (±)-Metoprolol (+)-tartrate salt?
1 answer-
This product can be stored at room temperature. It should be stored in a tightly closed light-resistant container.
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Has Product M5391, (±)-Metoprolol (+)-tartrate salt, been tested in Cell Culture?
1 answer-
This product has not been tested for use in Cell Culture applications.
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What is the Department of Transportation shipping information for this product?
1 answer-
Transportation information can be found in Section 14 of the product's (M)SDS.To access the shipping information for this material, use the link on the product detail page for the product.
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What is the ratio of metoprolol to tartrate in Product M5391, (±)-Metoprolol (+)-tartrate salt?
1 answer-
According to the molecular formula (C15H25NO3)2 · C4H6O6, there are two metroprolol molecules to one tartrate.
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