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M2696

Sigma-Aldrich

Metyrapone

≥98% (HPLC), solid

Synonyma:

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

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About This Item

Empirický vzorec (Hillův zápis):
C14H14N2O
Číslo CAS:
54-36-4
Molekulová hmotnost:
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

Osvědčení o analýze (COA)

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Sigma-Aldrich

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Sigma-Aldrich

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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
Angus Lindsay et al.
FASEB journal : official publication of the Federation of American Societies for Experimental Biology, 35(4), e21489-e21489 (2021-03-19)
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
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
Sonja C Schriever et al.
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
Xavier Belda et al.
Hormones and behavior, 62(4), 515-524 (2012-09-19)
A single exposure to some severe stressors causes sensitization of the hypothalamic-pituitary-adrenal (HPA) response to novel stressors. However, the putative factors involved in stress-induced sensitization are not known. In the present work we studied in adult male rats the possible
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