17159-42-1

Basic information

• Product Name: metyrapol
• Synonyms: metyrapol;2-Methyl-1,2-bis(3-pyridinyl)-1-propanol;2-Methyl-1,2-bis(3-pyridyl)-1-propanol;Metrapol;Reduced metyrapone;SU-5236;Metyrapol (racemic mixture);2-methyl-1,2-dipyridin-3-ylpropan-1-ol
• CAS NO: 17159-42-1
• Molecular Formula: C14H16N2O
• Molecular Weight: 228.293
• Mol File: 17159-42-1.mol

Chemical Properties

• Boiling Point: 373.2°C at 760 mmHg
• Flash Point: 179.5°C
• Appearance: /
• Density: 1.132g/cm³
• Vapor Pressure: 3.13E-06mmHg at 25°C
• Refractive Index: 1.577
• CAS DataBase Reference: metyrapol(CAS DataBase Reference)
• NIST Chemistry Reference: metyrapol(17159-42-1)
• EPA Substance Registry System: metyrapol(17159-42-1)

Safety Data

• Hazardous Substances Data: 17159-42-1(Hazardous Substances Data)

Usage

InChI:InChI=1/C14H16N2O/c1-14(2,12-6-4-8-16-10-12)13(17)11-5-3-7-15-9-11/h3-10,13,17H,1-2H3

Upstream product

• 54-36-4 metyrapone 

Related news

Regular paperDetermination of metyrapone and the enantiomers of its chiral metabolite metyrapol (cas 17159-42-1) in human plasma and urine using coupled achiral-chiral liquid chromatography08/15/2019

A coupled achiral-chiral liquid chromatographic assay has been developed to determine the concentrations of metyrapone and the enantiomers of its chiral metabolite metyrapol in plasma and urine. The chromatographic system consisted of a silica precolumn (75 × 4.6 mm I.D.) coupled in-line to a 2...detailed

Assay of metyrapone, metyrapol (cas 17159-42-1) and the isomeric mono-N-oxides of metyrapone in biological fluids by high-performance liquid chromatography08/14/2019

A sensitive high-performance liquid chromatographic (HPLC) method for the analysis of metyrapone [2-methyl-1,2-di-(3-pyridyl)-1-propanone], its reduced metabolite metyrapol and metyrapone mono-N-oxide metabolites in biological fluids is reported. These components were extracted into dichlorometh...detailed

Relevant articles and documents

In situ 1H NMR study of cytochrome P450 inhibition by metyrapol in mycobacterium aurum MO1

In situ 1H NMR was used to monitor incubations of Mycobacterium aurum MO1 with thiomorpholine or morpholine in the presence of metyrapone, a specific inhibitor of P450. Unexpected signals were detected and assigned to metyrapol, the reduction product of metyrapone. The inhibitory effects of racemic metyrapol and of its (-)-enantiomer were compared to that of metyrapone. They are similar.

Stereoselective reductive metabolism of metyrapone and inhibitory activity of metyrapone metabolites, metyrapol enantiomers, on steroid 11β- hydroxylase in the rat

Pharmacokinetics of metyrapone and metyrapol enantiomers was studied in the rat to determine the stereoselective reductive metabolism of metyrapone. The HPLC method using a chiral column was developed for the stereoselective analysis of metyrapol enantiomers in rat plasma. The AUC ratio of (-)- and (+)-metyrapol appeared in rat plasma after i.v. administration of metyrapone was about 3:1. The interconversion of (-)- or (+)-metyrapol to its antipode was negligible, and the reverse reaction from metyrapol to metyrapone was insignificant. There were similar kinetic parameters of (-)-metyrapol to those of (+)-metyrapol after i.v. administration of racemic metyrapol. These results indicate metyrapone displays product-stereoselective reductive metabolism in the rat. The inhibition of steroid 11β-hydroxylase by metyrapone, racemic metyrapol, (-)-metyrapol or (+)-metyrapol was analyzed in rat adrenal homogenates. Metyrapol was equally as potent as metyrapone in the inhibition of steroid 11β-hydroxylase and each enantiomer of metyrapol showed similar inhibitory activity on the rat adrenal steroid 11β- hydroxylase. These results indicate there is an insignificant difference in the inhibitory effects on steroid 11β-hydroxylase of metyrapol enantiomers, and that the inhibitory effects of metyrapol may be involved in the pharmacological activity of metyrapone in vivo.

Reduction of drug ketones by dihydrodiol dehydrogenases, carbonyl reductase and aldehyde reductase of human liver

In this study, we compared the enzymatic reduction of 10 drugs with a ketone group by homogeneous carbonyl reductase, aldehyde reductase and three dihydrodiol dehydrogenases of human liver cytosol. At least one and in some cases all of the three dihydrodi