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Merck
CN

M2696

Metyrapone

≥98% (HPLC), glucocorticoid synthesis inhibitor, 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
NACRES:
NA.77
PubChem Substance ID:
329817949
UNSPSC Code:
51111800
EC Number:
200-206-2
MDL number:
MFCD00006397
Beilstein/REAXYS Number:
163023
Assay:
≥98% (HPLC)
Form:
solid
Quality level:
100

Key Documents

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Product Name

Metyrapone, ≥98% (HPLC), solid

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

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
0000525668
0000525668
0000490863
0000490863
0000481451

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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
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
B J Carroll et al.
Acta psychiatrica Scandinavica, 125(6), 478-491 (2012-01-04)
To test three theories of hypercortisolemia in depression-hypothalamic overdrive, impaired glucocorticoid feedback, or autonomous cortisol production. We applied an overnight low-cortisol feedback strategy by administering metyrapone to hypercortisolemic depressed in-patients and control subjects. Under metyrapone, the increases of plasma adrenocorticotropic
Tamara M Rodela et al.
The Journal of experimental biology, 215(Pt 2), 314-323 (2011-12-23)
In their native environment, gulf toadfish excrete equal quantities of ammonia and urea. However, upon exposure to stressful conditions in the laboratory (i.e. crowding, confinement or air exposure), toadfish decrease branchial ammonia excretion and become ureotelic. The objective of this
View All Related Papers

Global Trade Item Number

SKUGTIN
M2696-50MG04061834045953
M2696-10MG04061832867403

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