Nortilidine

Quality 0.50 · 2 views · Updated 2 months ago

Chemical compound

title: "Nortilidine" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["opioids", "dopamine-reuptake-inhibitors", "nmda-receptor-antagonists", "cyclohexenes"] description: "Chemical compound" topic_path: "general/opioids" source: "https://en.wikipedia.org/wiki/Nortilidine" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0

::summary Chemical compound ::

| IUPAC_name = ethyl (1R,2S)-2-(methylamino)-1-phenylcyclohex-3-ene-1-carboxylate | image = Nortilidine.svg | image_class = skin-invert-image | width = | alt = | image2 = | width2 = | drug_name = | caption = | tradename = | licence_EU = | licence_US = | DailyMedID = | pregnancy_AU = | pregnancy_US = | pregnancy_category = | legal_AU = | legal_CA = | legal_UK = | legal_US = | legal_status = | dependency_liability = | routes_of_administration = | bioavailability = | protein_bound = | metabolism = | elimination_half-life = | excretion = | CAS_number = 38677-94-0 | CAS_supplemental = | ATCvet = | ATC_prefix = | ATC_suffix = | ATC_supplemental = | PubChem = 162321 | PubChemSubstance = | IUPHAR_ligand = | DrugBank = | ChemSpiderID = 142535 | ChEBI_Ref = | ChEBI = 77839 | ChEMBL = 1614654 | UNII = 7145G6817J | synonyms = | C=16 | H=21 | N=1 | O=2 | SMILES = CCOC(=O)[C@]1(CCC=C[C@@H]1NC)C2=CC=CC=C2 | StdInChI = 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 | StdInChIKey = PDJZPNKVLDWEKI-GOEBONIOSA-N | density = | melting_point = | melting_high = | melting_notes = | boiling_point = | boiling_notes = | solubility = | specific_rotation = | sec_combustion =

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

Use

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

References

References

  1. "Process for Substituted Cyclohexenes its Products".
  2. (November 2002). "Sequential first-pass metabolism of nortilidine: the active metabolite of the synthetic opioid drug tilidine". Journal of Clinical Pharmacology.
  3. (February 2015). "Novel psychoactive substances of interest for psychiatry". World Psychiatry.
  4. "Cycloaromatic compounds, analgesic Properties thereof and Method of use thereof as analgesic".
  5. Personal Communication with Derek P. Reynolds
  6. (10 August 2020). "EU Early Warning System Situation Report. Situation report 2". European Monitoring Centre for Drugs and Drug Addiction (EMCDDA).
  7. (2020). "Identifying New/Emerging Psychoactive Substances at the Time of COVID-19; A Web-Based Approach". Frontiers in Psychiatry.

::callout[type=info title="Wikipedia Source"] This article was imported from Wikipedia and is available under the Creative Commons Attribution-ShareAlike 4.0 License. Content has been adapted to SurfDoc format. Original contributors can be found on the article history page. ::

opioidsdopamine-reuptake-inhibitorsnmda-receptor-antagonistscyclohexenes