N,O-Didesmethyltramadol Explained
N,O-Didesmethyltramadol (tramadol metabolite M5) is an opioid derivative which is one of two active metabolites of the opioid analgesic medication tramadol. It is many times less potent than the other active metabolite O-Desmethyltramadol but is still more potent as a mu opioid receptor agonist than tramadol itself, unlike the other metabolites N-desmethyltramadol, N,N-didesmethyltramadol, and N,N,O-tridesmethyltramadol which are entirely without opioid activity.[1] [2] [3] [4] As with tramadol and O-desmethyltramadol it is found as a mixture of the (1S,2S)- and (1R,2R)-enantiomers, although the separate enantiomers of N,O-didesmethyltramadol have not been studied individually. It is specifically listed as a Schedule I drug in Canada,[5] presumably due to concerns it may be subject to abuse as a designer drug in a similar manner to other opioid active metabolites such as O-desmethyltramadol and nortilidine.
See also
Notes and References
- Gillen C, Haurand M, Kobelt DJ, Wnendt S . Affinity, potency and efficacy of tramadol and its metabolites at the cloned human mu-opioid receptor . Naunyn-Schmiedeberg's Archives of Pharmacology . 362 . 2 . 116–121 . August 2000 . 10.1007/s002100000266 . 10961373 .
- Leppert W . CYP2D6 in the metabolism of opioids for mild to moderate pain . Pharmacology . 2011 . 87 . 5–6 . 274–285 . 10.1159/000326085 . 21494059 .
- DePriest AZ, Puet BL, Holt AC, Roberts A, Cone EJ . Metabolism and Disposition of Prescription Opioids: A Review . Forensic Science Review . 27 . 2 . 115–145 . July 2015 . 26227254 .
- Barbosa J, Faria J, Queirós O, Moreira R, Carvalho F, Dinis-Oliveira RJ . Comparative metabolism of tramadol and tapentadol: a toxicological perspective . Drug Metabolism Reviews . 48 . 4 . 577–592 . November 2016 . 27580162 . 10.1080/03602532.2016.1229788 .
- Web site: Controlled Drugs and Substances Act (S.C. 1996, c. 19) . Justice Laws Website . 24 November 2023 . Government of Canada .
