N,O-Didesmethyltramadol

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N,O-Didesmethyltramadol
Identifiers

IUPAC name 3-[1-hydroxy-2-(methylaminomethyl)cyclohexyl]phenol
CAS Number	138853-73-3
PubChem CID	9816106
ChemSpider	7991856
UNII	F6F6QC876T
ChEBI	CHEBI:173687
CompTox Dashboard (EPA)	DTXSID90932422
Chemical and physical data
Formula	C₁₄H₂₁NO₂
Molar mass	235.327 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES CNCC1CCCCC1(C2=CC(=CC=C2)O)O
InChI InChI=1S/C14H21NO2/c1-15-10-12-5-2-3-8-14(12,17)11-6-4-7-13(16)9-11/h4,6-7,9,12,15-17H,2-3,5,8,10H2,1H3/t12-,14+/m1/s1 Key:CJXNQQLTDXASSR-OCCSQVGLSA-N

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.

References

^ Gillen C, Haurand M, Kobelt DJ, Wnendt S (August 2000). "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. doi:10.1007/s002100000266. PMID 10961373.
^ Leppert W (2011). "CYP2D6 in the metabolism of opioids for mild to moderate pain". Pharmacology. 87 (5–6): 274–285. doi:10.1159/000326085. PMID 21494059.
^ DePriest AZ, Puet BL, Holt AC, Roberts A, Cone EJ (July 2015). "Metabolism and Disposition of Prescription Opioids: A Review". Forensic Science Review. 27 (2): 115–145. PMID 26227254.
^ Barbosa J, Faria J, Queirós O, Moreira R, Carvalho F, Dinis-Oliveira RJ (November 2016). "Comparative metabolism of tramadol and tapentadol: a toxicological perspective". Drug Metabolism Reviews. 48 (4): 577–592. doi:10.1080/03602532.2016.1229788. PMID 27580162.
^ "Controlled Drugs and Substances Act (S.C. 1996, c. 19)". Justice Laws Website. Government of Canada. 24 November 2023.