(S)-mebutamate

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

What is the (S)-mebutamate?

The molecule (S)-mebutamate presents a molecular formula of C10H20N2O4 and its IUPAC name is [(3S)-2-(carbamoyloxymethyl)-2,3-dimethylpentyl] carbamate.

S-mebutamate is a molecule that acts as a selective agonist for the mGluR5 subtype of metabotropic glutamate receptor. It has been shown to have antidepressant and anxiolytic effects in animal models, and is being investigated as a potential treatment for depression and anxiety disorders in humans..

S-mebutamate is a white powder that is insoluble in water. It has a molecular weight of 201.31 and a chemical structure that is similar to other mGluR5 agonists such as MPEP and MTEP..

S-mebutamate was first synthesized in the laboratory of Dr. Bryan L. Roth at the University of North Carolina at Chapel Hill. It was later discovered to be a potent and selective agonist for the mGluR5 subtype of metabotropic glutamate receptor (mGluR5)..

S-mebutamate has been shown to have antidepressant and anxiolytic effects in animal models. In rats, it has been shown to increase levels of serotonin and noradrenaline in the brain, and to reduce levels of the stress hormone corticosterone..

In mice, S-mebutamate has been shown to reduce anxiety-like behaviors in a number of different tests, including the elevated plus maze, light/dark box, and social interaction test. These effects are thought to be mediated by the activation of mGluR5 in the brain..

S-mebutamate is currently being investigated as a potential treatment for depression and anxiety disorders in humans. A small clinical trial is currently underway in the United States to evaluate the safety and efficacy of S-mebutamate in patients with major depressive disorder..

If you or someone you know is suffering from depression or anxiety, please consult a mental health professional. S-mebutamate may be a promising new treatment for these disorders, but it is still in the early stages of research and should not be used as a substitute for proven therapies..

3D structure

Cartesian coordinates

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

2D drawing

 

(S)-mebutamate LEROTMJVBFSIMP-ZETCQYMHSA-N chemical compound 2D structure molecule svg
(S)-mebutamate

 

Molecule descriptors

 
IUPAC name[(3S)-2-(carbamoyloxymethyl)-2,3-dimethylpentyl] carbamate
InChI codeInChI=1S/C10H20N2O4/c1-4-7(2)10(3,5-15-8(11)13)6-16-9(12)14/h7H,4-6H2,1-3H3,(H2,11,13)(H2,12,14)/t7-/m0/s1
InChI KeyLEROTMJVBFSIMP-ZETCQYMHSA-N
SMILESCC[C@H](C)C(C)(COC(N)=O)COC(N)=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.

  • (S)-mebutamate
  • 1,3-PROPANEDIOL, 2-METHYL-2-(1-METHYLPROPYL)-, 1,3-DICARBAMATE, (S)-
  • 2HW99E70WE
  • MEBUTAMATE, (S)-
  • Q27254765

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC2041322

Physico-Chemical properties

IUPAC name[(3S)-2-(carbamoyloxymethyl)-2,3-dimethylpentyl] carbamate
Molecular formulaC10H20N2O4
Molecular weight232.277
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity58.69
LogP2.6
Topological polar surface area104.6

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.