Orthofluorofentanyl

Orthofluorofentanyl
Legal status
Legal status	CA: Schedule I; DE: Anlage II (Authorized trade only, not prescriptible); UK: Class A; US: Schedule I;
Identifiers
	IUPAC name N-(2-Fluorophenyl)-N-[1-(2-phenylethyl)-4-piperidinyl]-propanamide;
CAS Number	910616-29-4;
PubChem CID	101454647;
ChemSpider	59009033;
UNII	Y1S8D8G19A;
CompTox Dashboard (EPA)	DTXSID601036775 ;
Chemical and physical data
Formula	C22H27FN2O
Molar mass	354.469 g·mol−1
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,^[1] Orthofluorofentanyl did not appear on the illicit market until August 2016.^[2]

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.^[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

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

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
^ 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.
^ Armenian P, Vo KT, Barr-Walker J, Lynch KL (2017). "Fentanyl, fentanyl analogs and novel synthetic opioids: A comprehensive review" (PDF). Neuropharmacology. doi:10.1016/j.neuropharm.2017.10.016. PMID 29042317.
^ 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.

[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.

[pmid29042317-4] Armenian P, Vo KT, Barr-Walker J, Lynch KL (2017). "Fentanyl, fentanyl analogs and novel synthetic opioids: A comprehensive review" (PDF). Neuropharmacology. doi:10.1016/j.neuropharm.2017.10.016. PMID 29042317.

[pmid29091366-5] 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.

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Side effects

Legal status

See also

References