A summary of the most common chemical descriptors (InChI Key and SMILES codes) for (R)-Metyrapol are summarized together with 3D and 2D structures and relevant physico-chemical properties.

What is the (R)-Metyrapol?

The molecule (R)-Metyrapol presents a molecular formula of C14H16N2O and its IUPAC name is (1R)-2-methyl-1,2-dipyridin-3-ylpropan-1-ol.

R-metyrapone (brand name Metopirone) is a molecule used as a diagnostic tool in the study of adrenal function and as a treatment for Cushing's syndrome. It is a potent inhibitor of 11β-hydroxylase, an enzyme required for the biosynthesis of cortisol. By inhibiting 11β-hydroxylase, R-metyrapone reduces cortisol synthesis and can be used to assess the feedback inhibition of cortisol on adrenocorticotropic hormone (ACTH) release. In Cushing's syndrome, R-metyrapone can be used as a temporary measure to control cortisol excess while other treatments are initiated..

R-metyrapone was first synthesized in 1955 and was introduced for clinical use in 1963. It exists as a generic medication and is not marketed under any brand name..

The most common side effects of R-metyrapone are gastrointestinal in nature and include nausea, vomiting, and diarrhea. Other reported side effects include headache, dizziness, and rash. R-metyrapone is generally well tolerated and side effects are typically mild and resolve with continued treatment..

R-metyrapone is contraindicated in pregnancy as it can cross the placenta and inhibit cortisol synthesis in the fetus. It is also contraindicated in people with hypersensitivity to the drug..

R-metyrapone is a prescription medication and should be used only as directed by a physician..

3D structure

Cartesian coordinates

Geometry of (R)-Metyrapol in x, y and z coordinates (Å units) to copy/paste elsewhere. Generated with Open Babel software.

2D drawing


(R)-Metyrapol DDFNHFXLQJLFSX-ZDUSSCGKSA-N chemical compound 2D structure molecule svg


Molecule descriptors

IUPAC name(1R)-2-methyl-1,2-dipyridin-3-ylpropan-1-ol
InChI codeInChI=1S/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/t13-/m0/s1

Other names (synonyms)

IUPAC nomenclature provides a standardized method for naming chemical compounds. Although this system is widely used in chemistry, many chemical compounds have also other names commonly used in different contexts. These synonyms can come from a variety of sources and are used for a variety of purposes.

One common source of synonyms for chemical compounds is the common or trivial names, assigned on the basis of appearance, properties, or origin of the molecule.

Another source of synonyms are historical or obsolete names employed in the past, however replaced nowadays by more modern or standardized names.

In addition to common and historical names, chemical compounds may also have synonyms that are specific to a particular field or industry.

  • (R)-Metyrapol

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC5138217

Physico-Chemical properties

IUPAC name(1R)-2-methyl-1,2-dipyridin-3-ylpropan-1-ol
Molecular formulaC14H16N2O
Molecular weight228.29
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity66.95
Topological polar surface area46.0

LogP and topological polar surface area (TPSA) values were estimated using Open Babel software.

The n-octanol/water partition coeficient (Kow) data is applied in toxicology and drug research. Kow values are used, to guess the environmental fate of persistent organic pollutants. High partition coefficients values, tend to accumulate in the fatty tissue of organisms. Molecules with a log(Kow) (or LogP) greater than 5 are considered to bioaccumulate.

TPSA values are the sum of the surface area over all polar atoms or molecules, mainly oxygen and nitrogen, also including hydrogen atoms.

In medicinal chemistry, TPSA is used to assess the ability of a drug to permeabilise cells.

For molecules to penetrate the blood-brain barrier (and act on receptors in the central nervous system), TPSA values below 90 Å2 are required. Thus, molecules with a polar surface area greater than 140 Å2 tend to be poorly permeable to cell membranes.