Acrylfentanyl

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Acrylfentanyl
Clinical data
ATC code
  • None
Legal status
Legal status
Identifiers
  • N-Phenyl-N-[1-(2-phenylethyl)piperidin-4-yl]prop-2-enamide
JSmol)
  • C=CC(=O)N(c2ccccc2)C1CCN(CC1)CCc3ccccc3

  • HCl: C=CC(=O)N(c2ccccc2)C1CCN(CC1)CCc3ccccc3.Cl
  • InChI=1S/C22H26N2O/c1-2-22(25)24(20-11-7-4-8-12-20)21-14-17-23(18-15-21)16-13-19-9-5-3-6-10-19/h2-12,21H,1,13-18H2
  • Key:RFQNLMWUIJJEQF-UHFFFAOYSA-N

  • HCl: InChI=1S/C22H26N2O.ClH/c1-2-22(25)24(20-11-7-4-8-12-20)21-14-17-23(18-15-21)16-13-19-9-5-3-6-10-19;/h2-12,21H,1,13-18H2;1H
  • Key:YUHNRLIKLNYPDD-UHFFFAOYSA-N

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

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

References

  1. ^ "Acrylfentanyl (hydrochloride)". Cayman Chemical.
  2. S2CID 30184205
    .
  3. PMID 27476446
    .
  4. S2CID 35645218
    .
  5. S2CID 247172069
    .
  6. PMID 6288945
    .
  7. PMID 15659122
    .
  8. PMID 10234745
    .
  9. PMID 6264735
    .
  10. PMID 25976511
    .
  11. ^ "PHDMC - Community Overdose Action Team Issues Alert". www.phdmc.org. 1 February 2017.
  12. PMID 6288945
    .
  13. ^ "Akrylfentanyl narkotikaklassas" [Acrylfentanyl is classified as a drug]. Rättsmedicinalverket [Forensic Medicine Agency] (in Swedish). 9 August 2016.
  14. ^ "Farligt stof i omløb - mistanken rettes mod acryl fentanyl" [Dangerous substance in circulation - suspicion is directed at Acrylfentanyl] (in Danish). mynewsdesk. 6 September 2016. Archived from the original on 9 September 2016. Retrieved 6 September 2016.
  15. ^ "Controlled Substances by DEA Drug Code Number" (PDF). Drug Enforcement Administration.
  16. ^ "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] (in Swedish). 21 June 2016.
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