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] The (1R,2S) isomer has NMDA antagonist activity. The drug also acts as a dopamine reuptake inhibitor.[3] The reversed-ester of nortilidine is also known, as is the corresponding analogue with the cyclohexene ring replaced by cyclopentane,[4] which have almost identical properties to nortilidine.[5]

Nortilidine
Identifiers
IUPAC name
  • ethyl (1R,2S)-2-(methylamino)-1-phenylcyclohex-3-ene-1-carboxylate
CAS Number
PubChem CID
ChemSpider
UNII
ChEBI
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC16H21NO2
Molar mass259.349 g·mol−1
3D model (JSmol)
SMILES
  • CCOC(=O)[C@]1(CCC=C[C@@H]1NC)C2=CC=CC=C2
InChI
  • InChI=1S/C16H21NO2/c1-3-19-15(18)16(13-9-5-4-6-10-13)12-8-7-11-14(16)17-2/h4-7,9-11,14,17H,3,8,12H2,1-2H3/t14-,16+/m0/s1
  • Key:PDJZPNKVLDWEKI-GOEBONIOSA-N

Use

Nortilidine has been sold as a designer drug, first being identified in Poland in May 2020.[6][7]

See also
  • Desmetramadol, another opioid metabolite with additional (non-opioid) mechanisms of analgesia, which has also been sold as a designer drug
  • Tapentadol

References
  1. US 3792080, "Process for Substituted Cyclohexenes its Products"
  2. Hajda JP, Jähnchen E, Oie S, Trenk D (November 2002). "Sequential first-pass metabolism of nortilidine: the active metabolite of the synthetic opioid drug tilidine". Journal of Clinical Pharmacology. 42 (11): 1257–61. doi:10.1177/009127002762491352. PMID 12412825. S2CID 12390653.
  3. Schifano F, Orsolini L, Duccio Papanti G, Corkery JM (February 2015). "Novel psychoactive substances of interest for psychiatry". World Psychiatry. 14 (1): 15–26. doi:10.1002/wps.20174. PMC 4329884. PMID 25655145.
  4. US 4291059, "Cycloaromatic compounds, analgesic Properties thereof and Method of use thereof as analgesic"
  5. Personal Communication with Derek P. Reynolds
  6. "EU Early Warning System Situation Report. Situation report 2". European Monitoring Centre for Drugs and Drug Addiction (EMCDDA). 10 August 2020. {{cite web}}: Missing or empty |url= (help)
  7. Catalani V, Arillotta D, Corkery JM, Guirguis A, Vento A, Schifano F (2020). "Identifying New/Emerging Psychoactive Substances at the Time of COVID-19; A Web-Based Approach". Frontiers in Psychiatry. 11: 632405. doi:10.3389/fpsyt.2020.632405. PMC 7900492. PMID 33633599.


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