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M2696

Sigma-Aldrich

Metyrapone

≥98% (HPLC), solid

Synonym(s):

2-Methyl-1,2-di-3-pyridyl-1-propanone, Metyrapone, Su-4885

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About This Item

Empirical Formula (Hill Notation):
C14H14N2O
CAS Number:
54-36-4
Molecular Weight:
226.27
Beilstein/REAXYS Number:
163023
EC Number:
200-206-2
MDL number:
MFCD00006397
UNSPSC Code:
51111800
PubChem Substance ID:
329817949
NACRES:
NA.77

sterility

non-sterile

Quality Level

100

assay

≥98% (HPLC)

form

solid

technique(s)

toxicology assay: suitable

mp

52-55 °C (lit.)

solubility

H2O: <2 mg/mL
DMSO: >20 mg/mL

originator

Novartis

shipped in

ambient

storage temp.

room temp

SMILES string

CC(C)(c1cccnc1)C(=O)c2cccnc2

InChI

1S/C14H14N2O/c1-14(2,12-6-4-8-16-10-12)13(17)11-5-3-7-15-9-11/h3-10H,1-2H3

InChI key

FJLBFSROUSIWMA-UHFFFAOYSA-N

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Biochem/physiol Actions

Metyrapone is a glucocorticoid synthesis inhibitor; a standard in assessing adrenal gland function especially in response to stress, as well as pituitary gland function. In addition to acting as a glucocorticoid synthesis inhibitor, Metyrapone also inhibits cytochrome P450-mediated prostaglandin ω/ω-1 hydroxylase activity and impairs learning and memory. Data shows results in activation of the sleep EEG and a robust decrease in quantitative delta sleep.

Features and Benefits

This compound was developed by Novartis. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

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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Metyrapone United States Pharmacopeia (USP) Reference Standard

USP

1443001

Metyrapone

Irit Akirav et al.
Learning & memory (Cold Spring Harbor, N.Y.), 11(2), 188-195 (2004-04-01)
Emotionally charged experiences alter memory storage via the activation of hormonal systems. Previously, we have shown that compared with rats trained for a massed spatial learning task in the water maze in warm water (25 degrees C), animals that were
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Psychosocial stressors can cause physical inactivity, cardiac damage, and hypotension-induced death in the mdx mouse model of Duchenne muscular dystrophy (DMD). Because repeated exposure to mild stress can lead to habituation in wild-type mice, we investigated the response of mdx
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Frontiers in immunology, 13, 864858-864858 (2022-07-06)
Diabetic patients have larger infarcts, worse neurological deficits, and higher mortality rate after an ischemic stroke. Evidence shows that in diabetes, the hypothalamic-pituitary-adrenal (HPA) axis was dysregulated and levels of cortisol increased. Based on the role of the HPA axis
Therese Koal et al.
The Journal of steroid biochemistry and molecular biology, 129(3-5), 129-138 (2012-01-03)
In order to overcome many limitations of immunoassays, high performance liquid chromatography-tandem mass spectrometry (HPLC-MS/MS) has the potential to find its place in the clinical laboratory medicine for quantification of steroid hormones. A prerequisite for the application of a new
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The Journal of clinical investigation, 130(11), 6093-6108 (2020-08-12)
Recent genome-wide association studies (GWAS) identified DUSP8, encoding a dual-specificity phosphatase targeting mitogen-activated protein kinases, as a type 2 diabetes (T2D) risk gene. Here, we reveal that Dusp8 is a gatekeeper in the hypothalamic control of glucose homeostasis in mice
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