{{Short description|Opioid analgesic}}{{Drugbox | Verifiedfields = changed | verifiedrevid = 451463728 | IUPAC_name = ''N''-(4-fluorophenyl)-''N''-[1-(2-phenylethyl)piperidin-4-yl]propanamide | image = Parafluorofentanyl.svg | image_class = skin-invert-image | width = 220px | image2 = P-fluorofentanyl.png | image_class2 = bg-transparent | width2 = 220px
<!--Clinical data--> | tradename = | pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X --> | pregnancy_US = <!-- A / B / C / D / X --> | pregnancy_category = | legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 --> | legal_BR = F1 | legal_CA = Schedule I | legal_UK = Class A | legal_US = Schedule I | legal_DE = Anlage I | routes_of_administration =
<!--Pharmacokinetic data--> | bioavailability = | protein_bound = | metabolism = | elimination_half-life = | excretion =
<!--Identifiers--> | CAS_number_Ref = {{cascite|correct|??}} | CAS_number = 90736-23-5 | ATC_prefix = none | ATC_suffix = | PubChem = 62300 | KEGG = C22769 | DrugBank_Ref = {{drugbankcite|correct|drugbank}} | DrugBank = | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID = 56096 | ChEBI_Ref = {{ebicite|correct|EBI}} | ChEBI = 61074 | UNII_Ref = {{fdacite|changed|FDA}} | UNII = I45R05QM0Z
<!--Chemical data--> | C=22 | H=27 | F=1 | N=2 | O=1 | smiles = Fc1ccc(cc1)N(C(=O)CC)C3CCN(CCc2ccccc2)CC3 | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI = 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 | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = KXUBAVLIJFTASZ-UHFFFAOYSA-N | synonyms = 4-Fluorofentanyl; ''para''-Fluorofentanyl; pFF }}
'''Parafluorofentanyl''' ('''4-fluorofentanyl''', '''''para''-fluorofentanyl''', '''pFF''') is an opioid analgesic analogue of fentanyl developed by Janssen Pharmaceuticals in the 1960s.<ref>{{ cite patent | country = US | status = patent | number = 3164600 }}</ref>
Parafluorofentanyl was sold briefly on the US black market in the early 1980s,{{citation needed|date=September 2015}} 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.<ref>{{cite journal | vauthors = Henderson GL | title = Designer drugs: past history and future prospects | journal = Journal of Forensic Sciences | volume = 33 | issue = 2 | pages = 569–75 | date = March 1988 | doi = 10.1520/JFS11976J | pmid = 3286815 }}</ref> Parafluorofentanyl is made by the same synthetic route as fentanyl, but by substituting ''para''-fluoroaniline for aniline in the synthesis.<ref>{{cite journal | vauthors = Ulens C, Van Boven M, Daenens P, Tytgat J | title = Interaction of <em>p</em>-fluorofentanyl on cloned human opioid receptors and exploration of the role of Trp-318 and His-319 in μ-opioid receptor selectivity | journal = The Journal of Pharmacology and Experimental Therapeutics | volume = 294 | issue = 3 | pages = 1024–33 | date = September 2000 | doi = 10.1016/S0022-3565(24)39167-0 | pmid = 10945855 | url = http://jpet.aspetjournals.org/content/294/3/1024.full.pdf }}</ref>
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.<ref>{{cite journal | vauthors = Mounteney J, Giraudon I, Denissov G, Griffiths P | title = Fentanyls: Are we missing the signs? Highly potent and on the rise in Europe | journal = The International Journal on Drug Policy | volume = 26 | issue = 7 | pages = 626–31 | date = July 2015 | pmid = 25976511 | doi = 10.1016/j.drugpo.2015.04.003 | url = http://www.ijdp.org/article/S0955-3959%2815%2900097-3/abstract | url-access = subscription }}</ref>
In 2020, the Drug Enforcement Agency warned about the increasing prevalence of parafluorofentanyl in Arizona.<ref>{{Cite web |url=https://www.abc15.com/news/dea-warns-of-newly-encountered-fentanyl-like-drug-in-arizona |title=DEA warns of newly encountered fentanyl-like drug in Arizona |date=December 28, 2020 |website=KNXV}}</ref><ref>{{Cite web |url=https://ktar.com/story/3775298/dea-in-arizona-warns-of-extremely-dangerous-form-of-fentanyl/ |title=DEA in Arizona warns of 'extremely dangerous' form of fentanyl |date=December 29, 2020 |website=KTAR.com}}</ref>
== See also == * 3-Methylbutyrfentanyl * 3-Methylfentanyl * 4-Fluorobutyrfentanyl * 4-Fluoroisobutyrfentanyl * α-Methylfentanyl * Acetylfentanyl * Butyrfentanyl * Furanylfentanyl * Orthofluorofentanyl * List of fentanyl analogues
== References == {{Reflist}}
{{Opioidergics}}
Category:Synthetic opioids Category:Piperidines Category:4-Fluorophenyl compounds Category:Propionamides Category:Anilides Category:Mu-opioid receptor agonists Category:Designer drugs Category:Fentanyl