{{short description|Opioid analgesic}} {{Drugbox | Verifiedfields = changed | verifiedrevid = 464199917 | IUPAC_name = ''N''-[2,5-Dimethyl-1-(2-phenylethyl)piperidin-4-yl]-''N''-phenylpropanamide | image = Phenaridine.svg | image_class = skin-invert-image <!--| imageL = Phenaridine.svg | widthL = 120px-->
<!--| imageR = <div style="position:relative; top:75px; left:0px; {{Transform-rotate|-90|display=block}}">file:Phenaridine 3D BS.png</div>- | widthR = 160px-->
<!--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_CA = | legal_UK = | legal_US = Schedule I<ref>{{cite journal | author = Drug Enforcement Administration | title = Schedules of Controlled Substances:Temporary Placement of Fentanyl-Related Substances in Schedule I. Temporary amendment; temporary scheduling order | journal = Federal Register | volume = 83 | issue = 25 | pages = 5188–92 | date = February 2018 | pmid = 29932611 }}</ref> | legal_status = | routes_of_administration =
<!--Pharmacokinetic data--> | bioavailability = | protein_bound = | metabolism = | elimination_half-life = | excretion =
<!--Identifiers--> | CAS_number_Ref = {{cascite|changed|??}} | CAS_number = 42045-97-6 | ATC_prefix = none | ATC_suffix = | PubChem = 162056 | DrugBank_Ref = {{drugbankcite|correct|drugbank}} | DrugBank = | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID = 142327 | UNII_Ref = {{fdacite|changed|FDA}} | UNII = S07S9928YH
<!--Chemical data--> | C=24 | H=32 | N=2 | O=1 | smiles = O=C(N(c1ccccc1)C3CC(N(CCc2ccccc2)CC3C)C)CC | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI = 1S/C24H32N2O/c1-4-24(27)26(22-13-9-6-10-14-22)23-17-20(3)25(18-19(23)2)16-15-21-11-7-5-8-12-21/h5-14,19-20,23H,4,15-18H2,1-3H3 | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = ODPKHHGQKIYCTJ-UHFFFAOYSA-N | synonyms = }}
'''Phenaridine''' ('''2,5-dimethylfentanyl''') is an opioid analgesic that is an analogue of fentanyl. It was developed in 1972,<ref name=riley>{{cite journal | vauthors = Riley TN, Hale DB, Wilson MC | title = 4-Anilidopiperidine analgesics. I. Synthesis and analgesic activity of certain ring-methylated 1-substituted 4-propananilidopiperidines | journal = Journal of Pharmaceutical Sciences | volume = 62 | issue = 6 | pages = 983–6 | date = June 1973 | pmid = 4712637 | doi = 10.1002/jps.2600620627 | bibcode = 1973JPhmS..62..983R }}</ref> and is used for surgical anasthesia.<ref name="pmid1862963">{{cite journal | vauthors = Osipova NA, Petrova VV, Novikov GA, Dolgopolova TV, Zhukova OI, Mel'nikova ZL, Smolina TA | title = [The new Soviet narcotic analgesic phenaridine as a component of general anesthesia during cancer surgery] | language = ru | journal = Anesteziologiia I Reanimatologiia | issue = 1 | pages = 42–6 | date = 1991 | pmid = 1862963 }}</ref><ref name="pmid1680749">{{cite journal | vauthors = Vlasenko EV, Durgarian LK, Azlivian AS, Sarukhanian KV | title = [The evaluation of the analgesic action of phenaridine when combined with agents used in anesthesiological practice] | language = ru | journal = Farmakologiia i Toksikologiia | volume = 54 | issue = 3 | pages = 17–20 | date = 1991 | pmid = 1680749 }}</ref> Phenaridine has similar effects to fentanyl. It is slightly less potent than fentanyl in rats. 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. Irresponsible use of fentanyl analogues administrated in several times larger doses than recommended, have ended up in a death of 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.<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 }}</ref>
== See also == * 3-Methylfentanyl * 4-Fluorofentanyl * α-Methylfentanyl * Acetylfentanyl * Fentanyl tropane * Furanylfentanyl * List of fentanyl analogues
== References == {{Reflist|2}}
{{Opioidergics}}
Category:Synthetic opioids Category:Piperidines Category:Propionamides Category:Anilides Category:Mu-opioid receptor agonists