Orthofluorofentanyl

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Orthofluorofentanyl
Orthofluorofentanyl Structure.svg
O-fluorofentanyl.png
Legal status
Legal status
Identifiers
  • N-(2-Fluorophenyl)-N-[1-(2-phenylethyl)-4-piperidinyl]-propanamide
CAS Number
PubChem CID
ChemSpider
UNII
Chemical and physical data
FormulaC22H27FN2O
Molar mass354.469 g·mol−1
3D model (JSmol)
  • CCC(=O)N(C1CCN(CC1)CCC2=CC=CC=C2)C3=CC=CC=C3F
  • InChI=1S/C22H27FN2O/c1-2-22(26)25(21-11-7-6-10-20(21)23)19-13-16-24(17-14-19)15-12-18-8-4-3-5-9-18/h3-11,19H,2,12-17H2,1H3
  • Key:BKUWDIVZCJNXRA-UHFFFAOYSA-N

Orthofluorofentanyl (o-fluorofentanyl, 2-fluorofentanyl) is an opioid analgesic that is an analog of fentanyl and has been sold online as a designer drug. While the structural isomer p-fluorofentanyl was one of the first illicit fentanyl analogues identified in 1981,[1] Orthofluorofentanyl did not appear on the illicit market until August 2016.[2]

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.[3] A new wave of fentanyl analogues and associated deaths began in around 2014 in the US, and have continued to grow in prevalence; especially since 2016 these drugs have been responsible for hundreds of overdose deaths every week.[4]

Legal status[edit]

Orthofluorofentanyl was placed into Schedule I in the US in October 2017, in order to avoid an imminent hazard to public safety.[5]

See also[edit]

References[edit]

  1. ^ Valter K, Arrizabalaga P. Designer Drugs Directory. Elsevier, 1998. pp 148-149, 159. ISBN 0-444-20525-X
  2. ^ Europol 2016 Annual Report on the implementation of Council Decision 2005/387/JHA
  3. ^ Jane Mounteney; Isabelle Giraudon; Gleb Denissov; Paul Griffiths (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.
  4. ^ Armenian P, Vo KT, Barr-Walker J, Lynch KL (2017). "Fentanyl, fentanyl analogs and novel synthetic opioids: A comprehensive review" (PDF). Neuropharmacology. 134 (Pt A): 121–132. doi:10.1016/j.neuropharm.2017.10.016. PMID 29042317. S2CID 21404877.
  5. ^ Drug Enforcement Administration, Department of Justice (2017). "Schedules of Controlled Substances: Temporary Placement of ortho-Fluorofentanyl, Tetrahydrofuranyl Fentanyl, and Methoxyacetyl Fentanyl Into Schedule I. Temporary amendment; temporary scheduling order". Fed Regist. 82 (206): 49504–8. PMID 29091366.