Chemistry:Furanylfentanyl

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Short description: Opioid analgesic
Furanylfentanyl
Furanylfentanyl.svg
Furanylfentanyl 3D BS.png
Clinical data
ATC code
  • none
Legal status
Legal status
Identifiers
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
Chemical and physical data
FormulaC24H26N2O2
Molar mass374.484 g·mol−1
3D model (JSmol)

Furanylfentanyl (Fu-F) is an opioid analgesic that is an analog of fentanyl[1] and has been sold as a designer drug.[2][3] It has an ED50 value of 0.02 mg/kg in mice.[4] This makes it approximately one fifth as potent as fentanyl.[5]

Side effects

Side effects of fentanyl analogs are similar to those of fentanyl itself, which include itching, nausea and potentially serious respiratory depression, which can be life-threatening. Fentanyl analogs have killed hundreds of people throughout Europe and the former Soviet republics since the most recent resurgence in use began in Estonia in the early 2000s, and novel derivatives continue to appear.[6]

Life-threatening adverse reactions caused by furanylfentanyl use have been observed in Sweden[7] and Canada.[8] At least seven deaths in Cook County, Illinois, have been linked to furanylfentanyl in 2016, with additional deaths in suburban Chicago in 2017.[9][10][11]

Detection in biological fluids

Furanylfentanyl may be measured in blood or urine to monitor for use, confirm a diagnosis of poisoning, or assist in a medicolegal death investigation. Commercially available immunoassays are often used as initial screening tests, but chromatographic techniques are generally used for confirmation and quantitation. Blood furanylfentanyl concentrations are expected to be in a range of 1-45 μg/L in victims of fatal overdosage.[12][13][14]

Legal status

Furanylfentanyl is illegal in Sweden as of January 2016.[15]

The United States Drug Enforcement Administration (DEA) proposed a temporary placement of furanylfentanyl into Schedule I of the Controlled Substances Act on 27 September 2016.[16] On November 29, 2016, the DEA issued its final rule, making furanylfentanyl Schedule I.[17][18]

See also

References

  1. ↑ "New 4-(heteroanilido)piperidines, structurally related to the pure opioid agonist fentanyl, with agonist and/or antagonist properties". Journal of Medicinal Chemistry 32 (3): 663–671. March 1989. doi:10.1021/jm00123a028. PMID 2563773. 
  2. ↑ "Detection and confirmation of the ring-opened carboxylic acid metabolite of a new synthetic opioid furanylfentanyl". Forensic Toxicology 39: 114–122. August 2020. doi:10.1007/s11419-020-00546-7. ISSN 1860-8973. 
  3. ↑ "In vitro and in vivo pharmaco-dynamic study of the novel fentanyl derivatives: Acrylfentanyl, Ocfentanyl and Furanylfentanyl". Neuropharmacology 209: 109020. May 2022. doi:10.1016/j.neuropharm.2022.109020. PMID 35247453. 
  4. ↑ "Patent US4584303 - N-aryl-N-(4-piperidinyl)amides and pharmaceutical compositions and method employing such compounds". The Boc Group, Inc. 9 April 1984. https://patents.google.com/patent/US4584303. 
  5. ↑ "Analgesic effect and pharmacological mechanism of fentanyl and butorphanol in a rat model of incisional pain". Journal of Clinical Anesthesia 28: 67–73. February 2016. doi:10.1016/j.jclinane.2015.08.010. PMID 26440441. 
  6. ↑ "Fentanyls: Are we missing the signs? Highly potent and on the rise in Europe". The International Journal on Drug Policy 26 (7): 626–631. July 2015. doi:10.1016/j.drugpo.2015.04.003. PMID 25976511. 
  7. ↑ "Intoxications involving the fentanyl analogs acetylfentanyl, 4-methoxybutyrfentanyl and furanylfentanyl: results from the Swedish STRIDA project". Clinical Toxicology 54 (4): 324–332. 20 April 2016. doi:10.3109/15563650.2016.1139715. PMID 26850293. 
  8. ↑ "Notes from the Field: Furanyl-Fentanyl Overdose Events Caused by Smoking Contaminated Crack Cocaine - British Columbia, Canada, July 15-18, 2016". MMWR. Morbidity and Mortality Weekly Report 65 (37): 1015–1016. September 2016. doi:10.15585/mmwr.mm6537a6. PMID 27657853. 
  9. ↑ "Medical Examiner Reports Deaths from Powerful Opioids on the Rise". Cook County Government. 18 April 2016. http://www.cookcountyil.gov/2016/04/18/medical-examiner-reports-deaths-from-powerful-opioids-on-the-rise/. 
  10. ↑ "Analysis of Novel Synthetic Opioids U-47700, U-50488 and Furanyl Fentanyl by LC-MS/MS in Postmortem Casework". Journal of Analytical Toxicology 40 (9): 709–717. November 2016. doi:10.1093/jat/bkw086. PMID 27590036. 
  11. ↑ "New form of synthetic heroin showing up in Chicago-area deaths" (in en-US). McHenry County. http://www.chicagotribune.com/suburbs/mchenry-county/news/ct-heroin-fentanyl-deaths-mchenry-met-20170203-story.html. 
  12. ↑ Baselt, R. (2017) Disposition of Toxic Drugs and Chemicals in Man, 11th edition, Biomedical Publications, Foster City, CA, p. 2315.
  13. ↑ "Analysis of Novel Synthetic Opioids U-47700, U-50488 and Furanyl Fentanyl by LC-MS/MS in Postmortem Casework". Journal of Analytical Toxicology 40 (9): 709–717. November 2016. doi:10.1093/jat/bkw086. PMID 27590036. 
  14. ↑ "Furanylfentanyl in whole blood measured by GC–MS/MS after QuEChERS extraction in a fatal case". Forensic Toxicology 38 (2): 496–504. January 2020. doi:10.1007/s11419-019-00515-9. ISSN 1860-8973. 
  15. ↑ "31 nya ämnen kan klassas som narkotika eller hälsofarlig vara" (in sv). Folkhälsomyndigheten. 17 November 2015. https://www.folkhalsomyndigheten.se/nyheter-och-press/nyhetsarkiv/2015/november/31-nya-amnen-kan-klassas-som-narkotika-eller-halsofarlig-vara/. 
  16. ↑ Drug Enforcement Administration (DEA) (27 September 2016). "Proposed Rule: Schedules of Controlled Substances: Temporary Placement of Furanyl Fentanyl Into Schedule I". Federal Register. https://www.federalregister.gov/documents/2016/09/27/2016-23183/schedules-of-controlled-substances-temporary-placement-of-furanyl-fentanyl-into-schedule-i. 
  17. ↑ "2016 - Final Order: Temporary Placement of Furanyl Fentanyl Into Schedule I". https://www.deadiversion.usdoj.gov/fed_regs/rules/2016/fr1129.htm. 
  18. ↑ "Furanyl Fentanyl Joins U-47,700 As The Second Illicit Opioid Banned By DEA In November". https://www.forbes.com/sites/davidkroll/2016/11/30/furanyl-fentanyl-joins-u-47700-as-the-second-illicit-opioid-dea-banned-in-november/#310b1bb42dba. 



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