Nortilidine

Nortilidine
Identifiers
  • 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)
  • CCOC(=O)[C@]1(CCC=C[C@@H]1NC)C2=CC=CC=C2
  • 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

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]

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.