M2696

Sigma-Aldrich

Metyrapone

≥98% (HPLC), solid

Synonym(s):
Su-4885, 2-Methyl-1,2-di-3-pyridyl-1-propanone, Metyrapone
Empirical Formula (Hill Notation):
C14H14N2O
CAS Number:
Molecular Weight:
226.27
Beilstein/REAXYS Number:
163023
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.77

Quality Level

sterility

non-sterile

assay

≥98% (HPLC)

form

solid

application(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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Packaging

10, 50 mg in glass bottle

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.

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Target Organs

Respiratory system

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

RIDADR

NONH for all modes of transport

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificate of Analysis
Certificate of Origin
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...
Raúl Pastor et al.
The Journal of pharmacology and experimental therapeutics, 341(2), 455-463 (2012-02-16)
Neuroadaptations underlying sensitization to drugs of abuse seem to influence compulsive drug pursuit and relapse associated with addiction. Our previous data support a role for the corticotropin-releasing factor (CRF) type-1 receptor (CRF₁) in ethanol (EtOH)-induced psychomotor sensitization. CRF₁ is endogenously...
Elena Valassi et al.
Clinical endocrinology, 77(5), 735-742 (2012-04-27)
To evaluate the outcome of preoperative therapy with ketoconazole (KTZ) and/or metyrapone (MTP) in previously untreated patients with Cushing's syndrome (CS). Sixty-two patients with CS (85% ACTH dependent), treated with steroidogenesis inhibitors prior to surgery between 1983 and 2010, were...
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...
Thomas C Neylan et al.
Annals of the New York Academy of Sciences, 1071, 203-215 (2006-08-08)
Studies that have conducted quantitative analysis of the sleep electroencephalogram (EEG) have demonstrated decreased delta sleep in PTSD. Elevations in both hypothalamic (neurohormonal) and extrahypothalamic (neurotransmitter) corticotropin releasing factor (CRF) release is associated with decreased delta sleep activity. We present...

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