(+)-O-Desmethylvenlafaxine

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

What is the (+)-O-Desmethylvenlafaxine?

The molecule (+)-O-Desmethylvenlafaxine presents a molecular formula of C16H25NO2 and its IUPAC name is 4-[(1S)-2-(dimethylamino)-1-(1-hydroxycyclohexyl)ethyl]phenol.

Venlafaxine is an antidepressant of the serotonin-norepinephrine reuptake inhibitor (SNRI) class. This means it increases the concentrations of the neurotransmitters serotonin and norepinephrine in the body and the brain. Venlafaxine is used to treat major depressive disorder, anxiety disorders, and panic disorder..

The (+)-O-Desmethylvenlafaxine molecule is the active metabolite of venlafaxine. It is responsible for the majority of the antidepressant and anti-anxiety effects of venlafaxine. It has a half-life of approximately 4-6 hours, which is longer than the half-life of venlafaxine itself (4 hours). This means that the effects of (+)-O-Desmethylvenlafaxine can last longer than the effects of venlafaxine..

(+)-O-Desmethylvenlafaxine is a potent serotonin-norepinephrine reuptake inhibitor (SNRI). It increases the concentrations of the neurotransmitters serotonin and norepinephrine in the body and the brain. This leads to antidepressant and anti-anxiety effects. (+)-O-Desmethylvenlafaxine is also a potent dopamine reuptake inhibitor. This means it increases the concentration of dopamine in the brain. This leads to mood-elevating and anti-addictive effects..

The (+)-O-Desmethylvenlafaxine molecule is the active metabolite of venlafaxine. It is responsible for the majority of the antidepressant and anti-anxiety effects of venlafaxine. It has a half-life of approximately 4-6 hours, which is longer than the half-life of venlafaxine itself (4 hours). This means that the effects of (+)-O-Desmethylvenlafaxine can last longer than the effects of venlafaxine..

3D structure

Cartesian coordinates

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

2D drawing

 

(+)-O-Desmethylvenlafaxine KYYIDSXMWOZKMP-OAHLLOKOSA-N chemical compound 2D structure molecule svg
(+)-O-Desmethylvenlafaxine

 

Molecule descriptors

 
IUPAC name4-[(1S)-2-(dimethylamino)-1-(1-hydroxycyclohexyl)ethyl]phenol
InChI codeInChI=1S/C16H25NO2/c1-17(2)12-15(13-6-8-14(18)9-7-13)16(19)10-4-3-5-11-16/h6-9,15,18-19H,3-5,10-12H2,1-2H3/t15-/m1/s1
InChI KeyKYYIDSXMWOZKMP-OAHLLOKOSA-N
SMILESCN(C)C[C@H](c1ccc(O)cc1)C1(O)CCCCC1

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.

  • (+)-Desvenlafaxine
  • (+)-O-Desmethylvenlafaxine
  • (S)-(+)-O-Desmethyl Venlafaxine
  • (S)-(+)-O-Desmethylvenlafaxine
  • (S)-4-(2-(dimethylamino)-1-(1-hydroxycyclohexyl)ethyl)phenol
  • (S)-O-Desmethyl Venlafaxine
  • 142761-12-4
  • 189BFR45S0
  • 4-[(1S)-2-(DIMETHYLAMINO)-1-(1-HYDROXYCYCLOHEXYL)ETHYL]PHENOL
  • CS-0131893
  • Desvenlafaxine, S-(+)-O-
  • HY-B0602D
  • J-007694
  • O-Desmethylvenlafaxine, (+)-
  • Phenol, 4-((1S)-2-(dimethylamino)-1-(1-hydroxycyclohexyl)ethyl)-
  • Phenol, 4-(2-(dimethylamino)-1-(1-hydroxycyclohexyl)ethyl)-, (S)-
  • Phenol, 4-[(1S)-2-(dimethylamino)-1-(1-hydroxycyclohexyl)ethyl]-
  • Q27251986
  • S-(+)-O-DESMETHYLVENLAFAXINE
  • S-(+)-O-Desmethyl Venlafaxine

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC9342
  • UNII-189BFR45S0
  • AKOS030241085
  • SCHEMBL34863

Physico-Chemical properties

IUPAC name4-[(1S)-2-(dimethylamino)-1-(1-hydroxycyclohexyl)ethyl]phenol
Molecular formulaC16H25NO2
Molecular weight263.375
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity78.68
LogP2.7
Topological polar surface area43.7

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.