Orthofluorofentanyl - Misplaced Pages

Opioid analgesic

Pharmaceutical compound

Orthofluorofentanyl
Legal status


Legal status	BR: Class F1 (Prohibited narcotics) CA: Schedule I DE: Anlage II (Authorized trade only, not prescriptible) UK: Class A US: Schedule I
Identifiers
IUPAC name N-(2-Fluorophenyl)-N--propanamide
CAS Number	910616-29-4
PubChem CID	101454647
ChemSpider	59009033
UNII	Y1S8D8G19A
KEGG	C22766
CompTox Dashboard (EPA)	DTXSID601036775
Chemical and physical data
Formula	C₂₂H₂₇FN₂O
Molar mass	354.469 g·mol
3D model (JSmol)	Interactive image
SMILES CCC(=O)N(C1CCN(CC1)CCC2=CC=CC=C2)C3=CC=CC=C3F
InChI 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, Orthofluorofentanyl did not appear on the illicit market until August 2016.

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. 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.

Legal status

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

References

Valter K, Arrizabalaga P. Designer Drugs Directory. Elsevier, 1998. pp 148-149, 159. ISBN 0-444-20525-X
Europol 2016 Annual Report on the implementation of Council Decision 2005/387/JHA
Mounteney J, Giraudon I, Denissov G, Griffiths P (July 2015). "Fentanyls: Are we missing the signs? Highly potent and on the rise in Europe". The International Journal on Drug Policy. 26 (7): 626–631. doi:10.1016/j.drugpo.2015.04.003. PMID 25976511.
Armenian P, Vo KT, Barr-Walker J, Lynch KL (May 2018). "Fentanyl, fentanyl analogs and novel synthetic opioids: A comprehensive review". Neuropharmacology. 134 (Pt A): 121–132. doi:10.1016/j.neuropharm.2017.10.016. PMID 29042317. S2CID 21404877.
Drug Enforcement Administration Do (October 2017). "Schedules of Controlled Substances: Temporary Placement of ortho-Fluorofentanyl, Tetrahydrofuranyl Fentanyl, and Methoxyacetyl Fentanyl Into Schedule I. Temporary amendment; temporary scheduling order". Federal Register. 82 (206): 49504–49508. PMID 29091366.