O-Desmethyltramadol

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

What is the O-Desmethyltramadol?

The molecule O-Desmethyltramadol presents a molecular formula of C15H23NO2 and its IUPAC name is 3-[(1R,2R)-2-[(dimethylamino)methyl]-1-hydroxycyclohexyl]phenol.

O-Desmethyltramadol is a potent and selective mu-opioid receptor agonist with a Ki of 3.4 nM and an EC50 of 7.8 nM. O-Desmethyltramadol has approximately 10-fold higher affinity for the mu-opioid receptor than tramadol and is a more potent analgesic than tramadol. O-Desmethyltramadol is metabolized to M1 by CYP2D6 and to M2 by CYP3A4. The elimination half-life of O-desmethyltramadol is 6.5 hours..

O-Desmethyltramadol (O-DTM, Brand name: Numorphan) is a synthetic opioid analgesic drug and is the active metabolite of tramadol. O-DTM is around 10 times more potent than tramadol. O-DTM is a mu-opioid receptor agonist with a Ki of 3.4 nM and an EC50 of 7.8 nM. The elimination half-life of O-desmethyltramadol is 6.5 hours..

O-DTM is used for the treatment of moderate to severe pain. It exists in oral, intramuscular, and rectal formulations. The oral bioavailability of O-DTM is approximately 70%. The peak plasma concentration is reached in 1-2 hours..

O-DTM is metabolized to M1 by CYP2D6 and to M2 by CYP3A4. The major metabolites of O-DTM are M1 and M2. M1 is an active metabolite with mu-opioid receptor agonist activity. M2 is a inactive metabolite..

The most common side effects of O-DTM are constipation, nausea, vomiting, dizziness, and headache..

O-DTM is a Schedule II controlled substance in the United States..

3D structure

Cartesian coordinates

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

2D drawing

 

O-Desmethyltramadol UWJUQVWARXYRCG-HIFRSBDPSA-N chemical compound 2D structure molecule svg
O-Desmethyltramadol

 

Molecule descriptors

 
IUPAC name3-[(1R,2R)-2-[(dimethylamino)methyl]-1-hydroxycyclohexyl]phenol
InChI codeInChI=1S/C15H23NO2/c1-16(2)11-13-6-3-4-9-15(13,18)12-7-5-8-14(17)10-12/h5,7-8,10,13,17-18H,3-4,6,9,11H2,1-2H3/t13-,15+/m1/s1
InChI KeyUWJUQVWARXYRCG-HIFRSBDPSA-N
SMILESCN(C)C[C@H]1CCCC[C@]1(O)c1cccc(O)c1

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.

  • (+)-O-Demethyltramadol
  • (+)-O-Desmethyltramadol
  • (RR,SS)-3-(2-((DIMETHYLAMINO)METHYL)-1-HYDROXYCYCLOHEXYL)PHENOL
  • 144830-14-8
  • 2WA8F50C3F
  • 3-((1R,2R)-2-((dimethylamino)methyl)-1-hydroxycyclohexyl)phenol
  • 3-[(1R,2R)-2-[(DIMETHYLAMINO)METHYL]-1-HYDROXYCYCLOHEXYL]PHENOL
  • 3-[(1R,2R)-2-[(dimethylamino)methyl]-1-hydroxy-cyclohexyl]phenol
  • 3-{(1R,2R)-2-[(dimethylamino)methyl]-1-hydroxycyclohexyl}phenol
  • 80456-81-1
  • 80456-81-1 (free base)
  • 9W28LW2ET5
  • BDBM50176258
  • BDBM50176263
  • Desmetramadol
  • Desmetramadol, R,R-(+)-
  • Desmetramadol, cis-(+)-
  • Mono-O-demethyltramadol
  • NCGC00165941-01
  • O-DESMETHYL TRAMADOL
  • O-DSMT
  • O-Desmethyltramadol
  • PHENOL, 3-((1R,2R)-2-((DIMETHYLAMINO)METHYL)-1-HYDROXYCYCLOHEXYL)-, REL-
  • Phenol, 3-((1R,2R)-2-((dimethylamino)methyl)-1-hydroxycyclohexyl)-
  • Phenol, 3-(2-((dimethylamino)methyl)-1-hydroxycyclohexyl)-, (1R-cis)-
  • Phenol, 3-(2-((dimethylamino)methyl)-1-hydroxycyclohexyl)-, cis-(+/-)-
  • Q63395330
  • RAC-3-((1R,2R)-2-((DIMETHYLAMINO)METHYL)-1-HYDROXYCYCLOHEXYL)PHENOLC
  • rel-3-((1R,2R)-2-((dimethylamino)methyl)-1-hydroxycyclohexyl)phenol
  • tramadol M1 metabolite

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC2509756
  • UNII-2WA8F50C3F
  • UNII-9W28LW2ET5
  • AKOS030241093
  • DTXSID401044548
  • DTXSID901313651
  • CHEMBL1400
  • CHEMBL201556
  • CHEBI:165221
  • SCHEMBL2517055

Physico-Chemical properties

IUPAC name3-[(1R,2R)-2-[(dimethylamino)methyl]-1-hydroxycyclohexyl]phenol
Molecular formulaC15H23NO2
Molecular weight249.349
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity73.71
LogP2.3
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.