Structure via PubChem · Public domain (PubChem)
O-desmethyltramadol
Sign in to saveDesmetramadol (), also known as '''O-desmethyltramadol (O-DSMT'''), is an opioid analgesic and the main active metabolite of tramadol. Tramadol is demethylated by the liver enzyme CYP2D6 to desmetramadol in the same way as codeine, and so similarly to the variation in effects seen with codeine, individuals who have a less active form of CYP2D6 will tend to have reduced analgesic effects from tramadol. Because desmetramadol itself does not need to be metabolized to induce an analgesic effect, it can be used in individuals with CYP2D6 inactivating mutations.
In the Vinony graph
Within Vinony's link graph, O-desmethyltramadol is referenced by 2,338 other articles, and connects out to N-methylserotonin, histamine antagonist and Mitragyna speciosa.
It sits within the topics 3-Hydroxyphenyl compounds, 5-HT2C antagonists and Analgesics.
Its subject is documented across 7 Wikipedia language editions.
Chemical data
- Formula
- C15H23NO2
- Molecular weight
- 249.35 g/mol
- IUPAC name
- 3-[2-[(dimethylamino)methyl]-1-hydroxycyclohexyl]phenol
- SMILES
- CN(C)CC1CCCCC1(C2=CC(=CC=C2)O)O
- InChIKey
- UWJUQVWARXYRCG-UHFFFAOYSA-N
- XLogP
- 2.3
- Polar surface area
- 43.7 Ų
- H-bond donors
- 2
- H-bond acceptors
- 3
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Molecule type
- Small molecule
via ChEMBL · EBI
Wikidata facts
- Subclass of
- chemical compound
- Mass
- 249.172878976
Show 3 more facts
- chemical formula
- C₁₅H₂₃NO₂
- canonical SMILES
- CN(C)CC1CCCCC1(C2=CC(=CC=C2)O)O
- Commons category
- Desmethyltramadol
Sources (2)
via Wikidata · CC0
~4 min read
Encyclopedic overview
12 sectionsContents
- Pharmacology
- Pharmacodynamics
- Pharmacokinetics
- Metabolites
- Society and culture
- Recreational use
- Legality
- United States
- United Kingdom
- Germany
- See also
- References
Desmetramadol (), also known as '''O-desmethyltramadol (O-DSMT'), is an opioid analgesic and the main active metabolite of tramadol. Tramadol is demethylated by the liver enzyme CYP2D6 to desmetramadol in the same way as codeine, and so similarly to the variation in effects seen with codeine, individuals who have a less active form of CYP2D6 will tend to have reduced analgesic effects from tramadol. Because desmetramadol itself does not need to be metabolized to induce an analgesic effect, it can be used in individuals with CYP2D6 inactivating mutations.
Desmetramadol is commonly encountered as a designer drug online in powder form or as an ingredient in pressed pills due to being unscheduled in many jurisdictions. Outside of its role as a metabolite, a chemical used in research, and as a recreational drug, desmetramadol has a very limited history of human usage and is not approved for medicinal use in any country as of 2025.
Excerpted from Wikipedia’s “O-desmethyltramadol” article, available under the CC BY-SA 4.0 licence.