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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-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
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.

4-Fluorofentanyl was sold briefly on the US black market in the early 1980s, 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. 4-Fluorofentanyl is made by the same synthetic route as fentanyl, but by substituting para-fluoroaniline for aniline in the synthesis.

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.

In 2020, the Drug Enforcement Agency warned about the increasing prevalence of parafluorofentanyl in Arizona.

See also

• 3-Methylbutyrfentanyl
• 3-Methylfentanyl
• 4-Fluorobutyrfentanyl
• 4-Fluoroisobutyrfentanyl
• α-Methylfentanyl
• Acetylfentanyl
• Butyrfentanyl
• Furanylfentanyl
• Orthofluorofentanyl
• List of fentanyl analogues

References

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.

• Drugs not assigned an ATC code
• Synthetic opioids
• Piperidines
• 4-Fluorophenyl compounds
• Propionamides
• Anilides
• Mu-opioid receptor agonists
• Designer drugs
• Fentanyl