Nortilidine

Nortilidine[1] is the major active metabolite of tilidine. It is formed from tilidine by demethylation in the liver. The racemate has opioid analgesic effects roughly equivalent in potency to that of morphine[2] but virtually all of the opioid activity resides in the (1S,2R) isomer.[3] The (1R,2S) isomer has NMDA antagonist activity. The drug also acts as a dopamine reuptake inhibitor.[4] The reversed-ester of nortilidine is also known[5] which has almost identical properties to nortilidine.[6]

Nortilidine
Identifiers
CAS Number
PubChem CID
ChemSpider
UNII
ChEBI
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC16H21NO2
Molar mass259.3434 g/mol g·mol−1
3D model (JSmol)

See also
  • O-Desmethyltramadol, another opioid metabolite with additional (non-opioid) mechanisms of analgesia

References
  1. US Patent 3792080 - Process for Substituted Cyclohexenes its Products
  2. J Clin Pharmacol. 2002 Nov ;42 (11):1257-61 - Sequential first-pass metabolism of nortilidine: the active metabolite of the synthetic opioid drug tilidine
  3. Opiates: George R. Lenz page 439, Table 9-30 (78)
  4. Schifano, Fabrizio; Orsolini, Laura; Duccio Papanti, G.; Corkery, John M. (2015). "Novel psychoactive substances of interest for psychiatry". World Psychiatry. 14 (1): 15–26. doi:10.1002/wps.20174. ISSN 1723-8617. PMC 4329884.
  5. US Patent 4291059 - Cycloaromatic compounds, analgesic Properties thereof and Method of use thereof as analgesic
  6. Personal Communication with Derek P. Reynolds


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