(S)-amisulpride

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

What is the (S)-amisulpride?

The molecule (S)-amisulpride presents a molecular formula of C17H27N3O4S and its IUPAC name is 4-amino-N-[[(2S)-1-ethylpyrrolidin-2-yl]methyl]-5-ethylsulfonyl-2-methoxybenzamide.

S-amisulpride is a dopamine antagonist that is used to treat schizophrenia and other mental disorders. It works by blocking the dopamine receptors in the brain. This results in a decrease in the symptoms of schizophrenia, such as hallucinations, delusions, and thought disorder. S-amisulpride exists as a tablet, an oral solution, and an injectable form..

3D structure

Cartesian coordinates

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

2D drawing

 

(S)-amisulpride NTJOBXMMWNYJFB-LBPRGKRZSA-N chemical compound 2D structure molecule svg
(S)-amisulpride

 

Molecule descriptors

 
IUPAC name4-amino-N-[[(2S)-1-ethylpyrrolidin-2-yl]methyl]-5-ethylsulfonyl-2-methoxybenzamide
InChI codeInChI=1S/C17H27N3O4S/c1-4-20-8-6-7-12(20)11-19-17(21)13-9-16(25(22,23)5-2)14(18)10-15(13)24-3/h9-10,12H,4-8,11,18H2,1-3H3,(H,19,21)/t12-/m0/s1
InChI KeyNTJOBXMMWNYJFB-LBPRGKRZSA-N
SMILESCCN1CCC[C@H]1CNC(=O)c1cc(S(=O)(=O)CC)c(N)cc1OC

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.

  • (?)-Amisulpride
  • (S)-(-)-N-(1-ethyl-2-pyrrolidinylmethyl)-2-methoxy-4-amino-5-ethylsulphonylbenzamide
  • (S)-4-Amino-N-((1-ethylpyrrolidin-2-yl)methyl)-5-(ethylsulfonyl)-2-methoxybenzamide
  • (S)-4-Amino-N-[(1-ethyl-2-pyrrolidinyl)methyl]-5-(ethylsulfonyl)-2-methoxybenzamide
  • (S)-amisulpride
  • 4-amino-N-[[(2S)-1-ethylpyrrolidin-2-yl]methyl]-5-ethylsulfonyl-2-methoxybenzamide
  • 71675-92-8
  • Amisulpride, (S)-
  • Benzamide, 4-amino-N-(((2S)-1-ethyl-2-pyrrolidinyl)methyl)-5-(ethylsulfonyl)-2-methoxy-
  • CS-0090362
  • ES3TWM82E8
  • ESAMISULPRIDE
  • EX-A5710
  • HY-126068
  • Q27277333
  • S-(-)-Amisulpride

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC1846088
  • UNII-ES3TWM82E8
  • DTXSID301316207
  • SCHEMBL675545

Physico-Chemical properties

IUPAC name4-amino-N-[[(2S)-1-ethylpyrrolidin-2-yl]methyl]-5-ethylsulfonyl-2-methoxybenzamide
Molecular formulaC17H27N3O4S
Molecular weight369.479
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity101.78
LogP3.3
Topological polar surface area110.1

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.