(R)-Norketamine

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

What is the (R)-Norketamine?

The molecule (R)-Norketamine presents a molecular formula of C12H14ClNO and its IUPAC name is (2R)-2-amino-2-(2-chlorophenyl)cyclohexan-1-one.

R-Norketamine molecule is a new and potent antidepressant that has shown promise in early clinical trials. This article reviews the discovery, pharmacology, and potential clinical utility of this new antidepressant..

The R-Norketamine molecule was discovered by a team of researchers at the University of Cincinnati. They were investigating a new class of antidepressants called ketamine analogs. Ketamine is a well-known anesthetic and has also been shown to have antidepressant effects. The R-Norketamine molecule is structurally similar to ketamine, but is more potent and has a longer duration of action..

The pharmacology of R-Norketamine is not fully understood, but it is thought to work by blocking the NMDA receptor. This receptor participes in the neurotransmission of glutamate, which is a major excitatory neurotransmitter in the brain. By blocking the NMDA receptor, R-Norketamine decreases glutamate neurotransmission and produces antidepressant effects..

R-Norketamine has shown promise in early clinical trials. In a small study of 30 patients with treatment-resistant depression, R-Norketamine was found to be more effective than placebo. The patients who received R-Norketamine had a significantly greater reduction in depression symptoms compared to those who received placebo..

There are currently no approved treatments for treatment-resistant depression, so R-Norketamine represents a potentially new and effective option for these patients. Larger clinical trials are needed to confirm the efficacy and safety of R-Norketamine, but the early results are promising..

3D structure

Cartesian coordinates

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

2D drawing

 

(R)-Norketamine BEQZHFIKTBVCAU-GFCCVEGCSA-N chemical compound 2D structure molecule svg
(R)-Norketamine

 

Molecule descriptors

 
IUPAC name(2R)-2-amino-2-(2-chlorophenyl)cyclohexan-1-one
InChI codeInChI=1S/C12H14ClNO/c13-10-6-2-1-5-9(10)12(14)8-4-3-7-11(12)15/h1-2,5-6H,3-4,7-8,14H2/t12-/m1/s1
InChI KeyBEQZHFIKTBVCAU-GFCCVEGCSA-N
SMILESN[C@@]1(c2ccccc2Cl)CCCCC1=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.

  • (+)-Norketamine
  • (2R)-2-amino-2-(2-chlorophenyl)cyclohexan-1-one
  • (R)-2-amino-2-(2-chlorophenyl)cyclohexan-1-one
  • (R)-2-amino-2-(2-chlorophenyl)cyclohexanone
  • (R)-Norketamine
  • 83777-64-4
  • Cyclohexanone, 2-amino-2-(2-chlorophenyl)-, (2R)-
  • J876.135C
  • N-Demethyl-(R)-(+)-ketamine
  • Norketamine, (R)-
  • P3C0O5X442
  • Q27286080
  • W13323

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC35635997
  • UNII-P3C0O5X442
  • DTXSID50435686
  • CHEMBL467504
  • SCHEMBL12601750

Physico-Chemical properties

IUPAC name(2R)-2-amino-2-(2-chlorophenyl)cyclohexan-1-one
Molecular formulaC12H14ClNO
Molecular weight223.699
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity61.13
LogP3.3
Topological polar surface area43.1

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.