Desmethyltramadol
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| Synonyms | O-Desmethyltramadol; O-DSMT; Omnitram |
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| Metabolism | CYP3A4 and CYP2B6 |
| Biological half-life | 6-8 hours |
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| Formula | C15H23NO2 |
| Molar mass | 249.349 g/mol |
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Desmetramadol (INN), 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 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 ("poor metabolizers") will tend to get reduced analgesic effects from tramadol. This also results in a ceiling effect (dependent on CYP2D6 availability) which limits tramadol's range of therapeutic benefits to the treatment of moderate pain.
Desmetramadol is considerably more potent as a μ-opioid agonist compared to tramadol. It also shows comparatively far lower affinity for the δ- and κ-opioid receptors.
The two enantiomers of desmetramadol show quite distinct pharmacological profiles; both (+) and (−)-desmetramadol are inactive as serotonin reuptake inhibitors, but (−)-desmetramadol retains activity as a norepinephrine reuptake inhibitor, and so the mix of both the parent compound and metabolites contributes significantly to the complex pharmacological profile of tramadol. While the multiple receptor targets can be beneficial in the treatment of pain (especially complex pain syndromes such as neuropathic pain), it increases the potential for drug interactions compared to other opioids, and may also contribute to side effects.
Desmetramadol is also an antagonist of the serotonin 5-HT2C receptor, at pharmacologically relevant concentrations.
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