Parafluorofentanyl

Parafluorofentanyl
Clinical data
Other names	4-Fluorofentanyl; Para-fluorofentanyl; pFF
ATC code	none;
Legal status
Legal status	BR: Class F1 (Prohibited narcotics); CA: Schedule I; DE: Anlage I (Authorized scientific use only); UK: Class A; US: Schedule I;
Identifiers
	IUPAC name N-(4-fluorophenyl)-N-[1-(2-phenylethyl)piperidin-4-yl]propanamide;
CAS Number	90736-23-5 ;
PubChem CID	62300;
ChemSpider	56096 ;
UNII	I45R05QM0Z;
KEGG	C22769;
ChEBI	CHEBI:61074 ;
CompTox Dashboard (EPA)	DTXSID0048929 ;
Chemical and physical data
Formula	C22H27FN2O
Molar mass	354.469 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES Fc1ccc(cc1)N(C(=O)CC)C3CCN(CCc2ccccc2)CC3;
	InChI InChI=1S/C22H27FN2O/c1-2-22(26)25(20-10-8-19(23)9-11-20)21-13-16-24(17-14-21)15-12-18-6-4-3-5-7-18/h3-11,21H,2,12-17H2,1H3 ; Key:KXUBAVLIJFTASZ-UHFFFAOYSA-N ;
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Parafluorofentanyl (4-fluorofentanyl, pFF) is an opioid analgesic analogue of fentanyl developed by Janssen Pharmaceuticals in the 1960s.^[1]

4-Fluorofentanyl was sold briefly on the US black market in the early 1980s,^{[citation needed]} before the introduction of the Federal Analog Act which for the first time attempted to control entire families of drugs based on their structural similarity rather than scheduling each drug individually as they appeared.^[2] 4-Fluorofentanyl is made by the same synthetic route as fentanyl, but by substituting para-fluoroaniline for aniline in the synthesis.^[3]

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 thousands 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.^[4]

In 2020, the Drug Enforcement Agency warned about the increasing prevalence of parafluorofentanyl in Arizona.^[5]^[6]

References

^ US patent 3164600
^ Henderson GL (March 1988). "Designer drugs: past history and future prospects". Journal of Forensic Sciences. 33 (2): 569–75. doi:10.1520/JFS11976J. PMID 3286815.
^ Ulens C, Van Boven M, Daenens P, Tytgat J (September 2000). "Interaction of p-fluorofentanyl on cloned human opioid receptors and exploration of the role of Trp-318 and His-319 in mu-opioid receptor selectivity" (PDF). The Journal of Pharmacology and Experimental Therapeutics. 294 (3): 1024–33. PMID 10945855.
^ 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): 626–31. doi:10.1016/j.drugpo.2015.04.003. PMID 25976511.
^ "DEA warns of newly encountered fentanyl-like drug in Arizona". KNXV. December 28, 2020.
^ "DEA in Arizona warns of 'extremely dangerous' form of fentanyl". KTAR.com. December 29, 2020.

[1] US patent 3164600

[2] Henderson GL (March 1988). "Designer drugs: past history and future prospects". Journal of Forensic Sciences. 33 (2): 569–75. doi:10.1520/JFS11976J. PMID 3286815.

[3] Ulens C, Van Boven M, Daenens P, Tytgat J (September 2000). "Interaction of p-fluorofentanyl on cloned human opioid receptors and exploration of the role of Trp-318 and His-319 in mu-opioid receptor selectivity" (PDF). The Journal of Pharmacology and Experimental Therapeutics. 294 (3): 1024–33. PMID 10945855.

[4] 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): 626–31. doi:10.1016/j.drugpo.2015.04.003. PMID 25976511.

[5] "DEA warns of newly encountered fentanyl-like drug in Arizona". KNXV. December 28, 2020.

[6] "DEA in Arizona warns of 'extremely dangerous' form of fentanyl". KTAR.com. December 29, 2020.

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See also

References