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M5391

Sigma-Aldrich

(±)-Metoprolol (+)-tartrate salt

≥98% (titration), powder

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

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

新产品

Certificates of Analysis (COA)

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  1. Which document(s) contains shelf-life or expiration date information for a given product?

    If available for a given product, the recommended re-test date or the expiration date can be found on the Certificate of Analysis.

  2. How do I get lot-specific information or a Certificate of Analysis?

    The lot specific COA document can be found by entering the lot number above under the "Documents" section.

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  4. What is the Department of Transportation shipping information for this product?

    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. 

  5. What is the solubility of Product M5391, (±)-Metoprolol (+)-tartrate salt?

    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.

  6. Has Product M5391, (±)-Metoprolol (+)-tartrate salt, been tested in Cell Culture?

    This product has not been tested for use in Cell Culture applications.

  7. What are the recommended storage conditions for Product M5391, (±)-Metoprolol (+)-tartrate salt?

    This product can be stored at room temperature. It should be stored in a tightly closed light-resistant container.

  8. What is the optical activity of Product M5391, (±)-Metoprolol (+)-tartrate salt?

    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

  9. What is the ratio of metoprolol to tartrate in Product M5391, (±)-Metoprolol (+)-tartrate salt?

    According to the molecular formula (C15H25NO3)2 · C4H6O6, there are two metroprolol molecules to one tartrate.

  10. My question is not addressed here, how can I contact Technical Service for assistance?

    Ask a Scientist here.

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
Current Cardiovascular Drugs (2005)
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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