Parafluorofentanyl

Parafluorofentanyl (4-Fluorofentanyl) is an opioid analgesic being an analogue of fentanyl developed by Janssen Pharmaceutica in the 1960s.[1]

Parafluorofentanyl

Clinical data
ATC code	none
Legal status
Legal status	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^Y
PubChem CID	62300
ChemSpider	56096^Y
UNII	I45R05QM0Z
ChEBI	CHEBI:61074^Y
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^Y Key:KXUBAVLIJFTASZ-UHFFFAOYSA-N^Y
^NY (what is this?)  (verify)

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.[2] 4-Fluorofentanyl is made with 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 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.[4]

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.