O-Desmethyltramadol
| 160px | |
| Systematic (IUPAC) name | |
|---|---|
|
3-[2-(1-Amino-1-methylethyl)-1-hydroxycyclohexyl]phenol | |
| Clinical data | |
| Routes of administration | Orally Converted Metabolite, Oral, Insufflation, Rectal, IV |
| Legal status | |
| Legal status |
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| Pharmacokinetic data | |
| Biological half-life | ~ 9 h |
| Identifiers | |
| CAS Number | 73986-53-5 |
| PubChem | CID 130829 |
| Chemical data | |
| Formula | C15H23NO2 |
| Molar mass | 249.349 g/mol[[Script error: No such module "String".]] |
| Script error: No such module "collapsible list". | |
O-Desmethyltramadol is an opioid analgesic and the main active metabolite of tramadol.[1]
(+)-O-Desmethyltramadol is the most important metabolite of tramadol produced in the liver after tramadol is consumed. This metabolite is considerably more potent as a μ opioid agonist than the parent compound,[2].
Tramadol is demethylated by the liver enzyme CYP2D6[3] 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 metabolisers") will tend to get reduced analgesic effects from tramadol.
The two enantiomers of O-desmethyltramadol show quite distinct pharmacological profiles;[4] both (+) and (-)-O-desmethyltramadol are inactive as serotonin reuptake inhibitors,[5] but (-)-O-desmethyltramadol retains activity as a noradrenaline reuptake inhibitor[6] and so the mix of both the parent compound and metabolites produced contributes significantly to the complex pharmacological profile of tramadol.
References
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<references />, or <references group="..." />- ↑ Sevcik, J; Nieber, K; Driessen, B; Illes, P (1993). "Effects of the central analgesic tramadol and its main metabolite, O-desmethyltramadol, on rat locus coeruleus neurones". British journal of pharmacology. 110 (1): 169–76. PMC 2175982 Freely accessible. PMID 8220877.
- ↑ Dayer, P; Desmeules, J; Collart, L (1997). "Pharmacology of tramadol". Drugs. 53 Suppl 2: 18–24. PMID 9190321.
- ↑ Borlak, J; Hermann, R; Erb, K; Thum, T (2003). "A rapid and simple CYP2D6 genotyping assay--case study with the analgetic tramadol". Metabolism: clinical and experimental. 52 (11): 1439–43. doi:10.1016/S0026-0495(03)00256-7. PMID 14624403.
- ↑ Garrido, MJ; Valle, M; Campanero, MA; Calvo, R; Trocóniz, IF (2000). "Modeling of the in vivo antinociceptive interaction between an opioid agonist, (+)-O-desmethyltramadol, and a monoamine reuptake inhibitor, (-)-O-desmethyltramadol, in rats". The Journal of pharmacology and experimental therapeutics. 295 (1): 352–9. PMID 10992001.
- ↑ Bamigbade, TA; Davidson, C; Langford, RM; Stamford, JA (1997). "Actions of tramadol, its enantiomers and principal metabolite, O-desmethyltramadol, on serotonin (5-HT) efflux and uptake in the rat dorsal raphe nucleus". British journal of anaesthesia. 79 (3): 352–6. PMID 9389855.
- ↑ Driessen, B; Reimann, W; Giertz, H (1993). "Effects of the central analgesic tramadol on the uptake and release of noradrenaline and dopamine in vitro". British journal of pharmacology. 108 (3): 806–11. PMC 1908052 Freely accessible. PMID 8467366.
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