(-)-Glutethimide

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

What is the (-)-Glutethimide?

The molecule (-)-Glutethimide presents a molecular formula of C13H15NO2 and its IUPAC name is (3S)-3-ethyl-3-phenylpiperidine-2,6-dione.

Glutethimide is a sedative and hypnotic medication. It was first synthesized in 1869, but was not widely used until the 1950s. It is typically used to treat insomnia and is sometimes used to treat anxiety and seizures. It is a Schedule II Controlled Substance in the United States..

Glutethimide is a central nervous system (CNS) depressant. It works by binding to the GABA receptors in the brain and increasing the activity of the neurotransmitter GABA. This results in a decrease in neuronal activity and leads to sedation and sleep..

Glutethimide is absorbed quickly from the gastrointestinal tract and reaches peak levels in the blood within 1-2 hours. The half-life of the drug is 8-12 hours..

Common side effects of glutethimide include drowsiness, dizziness, and confusion. More serious side effects include slowed breathing, low blood pressure, and coma..

Glutethimide should not be used in people with a history of drug abuse or addiction, as it is highly addictive. It should also be used with caution in people with liver or kidney disease, as it can accumulate in these organs and cause toxicity..

3D structure

Cartesian coordinates

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

2D drawing

 

(-)-Glutethimide JMBQKKAJIKAWKF-ZDUSSCGKSA-N chemical compound 2D structure molecule svg
(-)-Glutethimide

 

Molecule descriptors

 
IUPAC name(3S)-3-ethyl-3-phenylpiperidine-2,6-dione
InChI codeInChI=1S/C13H15NO2/c1-2-13(10-6-4-3-5-7-10)9-8-11(15)14-12(13)16/h3-7H,2,8-9H2,1H3,(H,14,15,16)/t13-/m0/s1
InChI KeyJMBQKKAJIKAWKF-ZDUSSCGKSA-N
SMILESCC[C@@]1(c2ccccc2)CCC(=O)NC1=O

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.

  • (-)-.ALPHA.-PHENYL-.ALPHA.-ETHYLGLUTARIMIDE
  • (-)-Glutethimide
  • (-)-alpha-Phenyl-alpha-ethylglutarimide
  • (3S)-3-ethyl-3-phenyl-piperidine-2,6-dione
  • (3S)-3-ethyl-3-phenylpiperidine-2,6-dione
  • (S)-glutethimide
  • 17575-59-6
  • 2,6-Piperidinedione, 3-ethyl-3-phenyl-, (3S)-
  • 2,6-Piperidinedione, 3-ethyl-3-phenyl-, (S)-
  • A839005
  • BIDD:PXR0118
  • Glutarimide, 2-ethyl-2-phenyl-, (-)-
  • Glutethimide, (S)-
  • IN5W64L102
  • Q27280806

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC1530796
  • UNII-IN5W64L102
  • SCHEMBL113709

Physico-Chemical properties

IUPAC name(3S)-3-ethyl-3-phenylpiperidine-2,6-dione
Molecular formulaC13H15NO2
Molecular weight217.264
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity65.14
LogP2.1
Topological polar surface area46.2

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.