Acrylfentanyl Explained

Acrylfentanyl (also known as acryloylfentanyl) is a highly potent opioid analgesic that is an analog of fentanyl and has been sold online as a designer drug.[1] [2] [3] [4] [5] In animal studies the IC50 (the half maximal inhibitory concentration for acrylfentanyl to displace naloxone) is 1.4 nM, being slightly more potent than fentanyl itself (1.6 nM) as well as having a longer duration of action.[6] [7] [8] [9]

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.[10]

As acrylamide derivatives are often used in drug discovery to make covalent inhibitors which will bind irreversibly to its target, acrylfentanyl is claimed to be naloxone resistant.[11] However, acute intoxications with acrylfentanyl on mice[12] threatened by naloxone (2 mg/kg) have shown that acrylfentanyl could be displaced from the opioid receptor.

Acrylfentanyl has been linked to 20 deaths in Sweden as well as two deaths in Denmark in summer 2016.[13] [14]

Legal status

Acrylfentanyl is a Schedule I controlled substance in the United States.[15] As of 16 August 2016, it is an illegal medicine in Sweden.[16]

See also

Notes and References

  1. Web site: Acrylfentanyl (hydrochloride) . Cayman Chemical.
  2. Ujváry I, Jorge R, Christie R, Le Ruez T, Danielsson HV, Kronstrand R, Elliott S, Gallegos A, Sedefov R, Evans-Brown M . 30184205 . Acryloylfentanyl, a recently emerged new psychoactive substance: a comprehensive review . Forensic Toxicology . July 2017 . 232–243 . 35 . 2 . 10.1007/s11419-017-0367-8 .
  3. Breindahl T, Kimergård A, Andreasen MF, Pedersen DS . Identification of a new psychoactive substance in seized material: the synthetic opioid N-phenyl-N-[1-(2-phenethyl)piperidin-4-yl]prop-2-enamide (Acrylfentanyl) . Drug Testing and Analysis . 9 . 3 . 415–422 . March 2017 . 27476446 . 5396312 . 10.1002/dta.2046 .
  4. Helander A, Bäckberg M . New Psychoactive Substances (NPS) - the Hydra monster of recreational drugs . Clinical Toxicology . 55 . 1 . 1–3 . January 2017 . 27549399 . 10.1080/15563650.2016.1217003 . 35645218 .
  5. Bilel S, Azevedo Neto J, Arfè R, Tirri M, Gaudio RM, Fantinati A, Bernardi T, Boccuto F, Marchetti B, Corli G, Serpelloni G, De-Giorgio F, Malfacini D, Trapella C, Calo' G, Marti M . 6 . In vitro and in vivo pharmaco-dynamic study of the novel fentanyl derivatives: Acrylfentanyl, Ocfentanyl and Furanylfentanyl . Neuropharmacology . 209 . 109020 . May 2022 . 35247453 . 10.1016/j.neuropharm.2022.109020 . 247172069 . free . 11392/2497907 . free .
  6. Maryanoff BE, Simon EJ, Gioannini T, Gorissen H . Potential affinity labels for the opiate receptor based on fentanyl and related compounds . Journal of Medicinal Chemistry . 25 . 8 . 913–919 . August 1982 . 6288945 . 10.1021/jm00350a006 .
  7. Dong N, Lu WC, Chen NY, Zhu YC, Chen KX . Using support vector classification for SAR of fentanyl derivatives . Acta Pharmacologica Sinica . 26 . 1 . 107–112 . January 2005 . 15659122 . 10.1111/j.1745-7254.2005.00014.x . free .
  8. Essawi MY . Fentanyl analogues with a modified propanamido group as potential affinity labels: synthesis and in vivo activity . Die Pharmazie . 54 . 4 . 307–308 . April 1999 . 10234745 .
  9. Zhu YQ, Ge GL, Fang SN, Zhu YC, Dai QY, Tan ZY, Huang ZM, Chen XJ . 6 . [Studies on potent analgesics. I. Synthesis and analgesic activity of derivatives of fentanyl (author's transl)] ]. zh . Yao Xue Xue Bao = Acta Pharmaceutica Sinica . 16 . 3 . 199–210 . March 1981 . 6264735 .
  10. Mounteney J, Giraudon I, Denissov G, Griffiths P . 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 . 25976511 . 10.1016/j.drugpo.2015.04.003 .
  11. Web site: PHDMC - Community Overdose Action Team Issues Alert. www.phdmc.org. 1 February 2017.
  12. Maryanoff BE, Simon EJ, Gioannini T, Gorissen H . Potential affinity labels for the opiate receptor based on fentanyl and related compounds . Journal of Medicinal Chemistry . 25 . 8 . 913–919 . August 1982 . 6288945 . 10.1021/jm00350a006 .
  13. Web site: Akrylfentanyl narkotikaklassas . Acrylfentanyl is classified as a drug . Rättsmedicinalverket . Forensic Medicine Agency . 9 August 2016 . sv.
  14. Web site: Farligt stof i omløb - mistanken rettes mod acryl fentanyl . Dangerous substance in circulation - suspicion is directed at Acrylfentanyl . mynewsdesk. 6 September 2016. da. 6 September 2016. https://web.archive.org/web/20160909213606/http://www.mynewsdesk.com/dk/nordjyllands-politi/pressreleases/farligt-stof-i-omloeb-mistanken-rettes-mod-acryl-fentanyl-1547605. 9 September 2016. dead.
  15. Web site: Controlled Substances by DEA Drug Code Number . Drug Enforcement Administration.
  16. Web site: 31 nya ämnen kan klassas som narkotika eller hälsofarlig vara . 31 new substances can be classified as narcotic drugs or hazardous substances . Folkhälsomyndigheten . The Public Health Authority . sv . 21 June 2016.

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