Acrylfentanyl

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Acrylfentanyl
Acrylfentanyl.svg
Clinical data
ATC code
  • None
Legal status
Legal status
Identifiers
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
Chemical and physical data
Formula C22H26N2O
Molar mass 334.46 g·mol−1
3D model (JSmol)

Acrylfentanyl (also known as acryloylfentanyl or Egyptenyl) 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] In animal studies the IC50 or 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.[5][6][7][8]

Side effects[edit]

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.[9]

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.[10] However, acute intoxications with acrylfentanyl on mice[11] 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.[12][13]

Legal status[edit]

Acrylfentanyl is a Schedule I controlled substance in the United States.[14] As of 16 August 2016, it is illegal in Sweden.[15]

See also[edit]

References[edit]

  1. ^ "Acrylfentanyl (hydrochloride)". Cayman Chemical. 
  2. ^ Ujváry, István; Jorge, Rita; Christie, Rachel; Le Ruez, Thomas; Danielson, Helgi Valur; Kronstrand, Robert; Elliott, Simon; Gallegos, Ana; Sedefov, Roumen; Evans-Brown, Michael (July 2017). "Acryloylfentanyl, a recently emerged new psychoactive substance: a comprehensive review". Forensic Toxicology. 35 (2): 232–243. doi:10.1007/s11419-017-0367-8. 
  3. ^ Breindahl, Torben; Kimergård, Andreas; Andreasen, Mette Findal; Pedersen, Daniel Sejer (August 2016). "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. doi:10.1002/dta.2046. ISSN 1942-7611. PMID 27476446. 
  4. ^ Helander, Anders; Bäckberg, Matilda (2016). "New Psychoactive Substances (NPS) – the Hydra monster of recreational drugs". Clinical Toxicology: 1–3. doi:10.1080/15563650.2016.1217003. ISSN 1556-3650. PMID 27549399. 
  5. ^ Maryanoff, Bruce E.; Simon, Eric J.; Gioannini, Theresa; Gorissen, H. (August 1982). "Potential affinity labels for the opiate receptor based on fentanyl and related compounds". Journal of Medicinal Chemistry. 25 (8): 913–919. doi:10.1021/jm00350a006. PMID 6288945. 
  6. ^ Dong, Ning; Lu, Wen-cong; Chen, Nian-yi; Zhu, You-cheng; Chen, Kai-xian (January 2005). "Using support vector classification for SAR of fentanyl derivatives". Acta Pharmacologica Sinica. 26 (1): 107–112. doi:10.1111/j.1745-7254.2005.00014.x. ISSN 1745-7254. PMID 15659122. 
  7. ^ Essawi, M. Y. (April 1999). "Fentanyl analogues with a modified propanamido group as potential affinity labels: synthesis and in vivo activity". Die Pharmazie. 54 (4): 307–308. ISSN 0031-7144. PMID 10234745. 
  8. ^ Zhu, Y. Q.; Ge, G. L.; Fang, S. N.; Zhu, Y. C.; Dai, Q. Y.; Tan, Z. Y.; Huang, Z. M.; Chen, X. J. (March 1981). "强效镇痛剂研究——Ⅰ.芬太尼类衍生物的合成及其镇痛作用 (Studies on potent analgesics. I. Synthesis and analgesic activity of derivatives of fentanyl)". Yao Xue Xue Bao = Acta Pharmaceutica Sinica (in Chinese). 16 (3): 199–210. ISSN 0513-4870. PMID 6264735. 
  9. ^ Mounteney, Jane; Giraudon, Isabelle; Denissov, Gleb; Griffiths, Paul (July 2015). "Fentanyls: Are we missing the signs? Highly potent and on the rise in Europe". International Journal of Drug Policy. 26 (7): 626–631. doi:10.1016/j.drugpo.2015.04.003. PMID 25976511. 
  10. ^ url=http://www.phdmc.org/news-releases-coat/133-community-overdose-action-team-issues-alert-2-feb-17
  11. ^ Maryanoff, Bruce E.; Simon, Eric J.; Gioannini, Theresa; Gorissen, H. (August 1982). "Potential affinity labels for the opiate receptor based on fentanyl and related compounds". Journal of Medicinal Chemistry. 25 (8): 913–919. doi:10.1021/jm00350a006. PMID 6288945. 
  12. ^ "Akrylfentanyl narkotikaklassas" (in Swedish). Rättsmedicinalverket. 9 August 2016. 
  13. ^ "Farligt stof i omløb - mistanken rettes mod acryl fentanyl" (in Danish). mynewsdesk. 6 September 2016. 
  14. ^ "Controlled Substances by DEA Drug Code Number" (PDF). Drug Enforcement Agency. 
  15. ^ "31 nya ämnen kan klassas som narkotika eller hälsofarlig vara" (in Swedish). Folkhälsomyndigheten. 21 June 2016.