{{Short description|Chemical compound}} {{cs1 config|name-list-style=vanc}} {{Drugbox | verifiedrevid = 447992302 | IUPAC_name = ethyl 1-[2-(oxolan-2-ylmethoxy)ethyl]-4-phenylpiperidine-4-carboxylate | image = Furethidine.svg | image_class = skin-invert-image | width = 160
<!--Clinical data--> | tradename = | pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X --> | pregnancy_US = <!-- A / B / C / D / X --> | pregnancy_category = | legal_AU = S9 | legal_BR = A1 | legal_BR_comment = <ref>{{Cite web |author=Anvisa |author-link=Brazilian Health Regulatory Agency |date=2023-03-31 |title=RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial |trans-title=Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control|url=https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-784-de-31-de-marco-de-2023-474904992 |url-status=live |archive-url=https://web.archive.org/web/20230803143925/https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-784-de-31-de-marco-de-2023-474904992 |archive-date=2023-08-03 |access-date=2023-08-16 |publisher=Diário Oficial da União |language=pt-BR |publication-date=2023-04-04}}</ref> | legal_CA = Schedule I | legal_UK = Class A | legal_US = Schedule I | legal_DE = Anlage I
<!--Pharmacokinetic data--> | bioavailability = | protein_bound = | metabolism = | elimination_half-life = | excretion =
<!--Identifiers--> | CAS_number = 2385-81-1 | ATC_prefix = none | ATC_suffix = | ChEMBL = 2105078 | PubChem = 61306 | DrugBank_Ref = {{drugbankcite|correct|drugbank}} | DrugBank = DB01464 | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID = 55245 | UNII_Ref = {{fdacite|correct|FDA}} | UNII = 6U9XA4JOD4 | KEGG_Ref = {{keggcite|correct|kegg}} | KEGG = D12682
<!--Chemical data--> | C=21 | H=31 | N=1 | O=4 | smiles = O=C(OCC)C3(c1ccccc1)CCN(CCOCC2OCCC2)CC3 | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI = 1S/C21H31NO4/c1-2-25-20(23)21(18-7-4-3-5-8-18)10-12-22(13-11-21)14-16-24-17-19-9-6-15-26-19/h3-5,7-8,19H,2,6,9-17H2,1H3 | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = NNCOZXNZFLUYGG-UHFFFAOYSA-N | synonyms = <small>ethyl 4-phenyl-1-(2-tetrahydrofurfuryloxyethyl)piperidine-4-carboxylate</small> }}
'''Furethidine'''<ref>{{cite patent | country = GB | number = 797448 | title = Novel piperidine compounds and their production | inventor = Frearson PM, Stern ES | assign1 = J F Macfarlan & Co Ltd | pubdate = 2 July 1958 }}</ref><ref>Frearson Peter Marshall; Stern Edward Severin, {{Cite patent|DE|1256219}} (1967 to Glaxo Lab Ltd).</ref><ref>{{cite journal | vauthors=((Frearson, P. M.)), ((Hardy, D. G.)), ((Stern, E. S.)) | journal=Journal of the Chemical Society (Resumed) | title=426. Some new analogues of pethidine. Part IV. Substituents at the 1-position incorporating cyclic ether groups | pages=2103 | date= 1960 | issn=0368-1769 | doi=10.1039/jr9600002103}}</ref> is a 4-phenylpiperidine derivative that is related to the clinically used opioid analgesic drug pethidine (meperidine),<ref>{{cite book | vauthors = Maul C, Buschmann H, Sundermann B | chapter = Opioids: 3.3 Synthetic Opioids. | title = Analgesics | date = 2005 | pages = 159–169 | publisher = Wiley-VCH | isbn = 978-3-527-30403-5 }}</ref> but with around 25x higher potency.<ref>Casy AF, Parfitt RY. Opioid analgesics, chemistry and receptors. 1986, Plenum Press, New York. pp 234-235. {{ISBN|0-306-42130-5}}</ref> According to another source, Furethidine is 500/30 = 16.7 x the potency of pethidine (table VII).<ref>Blair, A. M. J. N.; Stephenson, R. P. (1960). "ANALGESIC ACTION OF ETHYL 4-PHENYLPIPERIDINE-4-CARBOXYLATES WITH OXYGENATED 1-SUBSTITUENTS". British Journal of Pharmacology and Chemotherapy. 15 (2): 247–253. doi:10.1111/j.1476-5381.1960.tb01239.x.</ref><ref>Lister, R. E. (1960). "PHARMACOLOGICAL ACTIONS OF TWO NEW PETHIDINE ANALOGUES". British Journal of Pharmacology and Chemotherapy. 15 (2): 254–259. doi:10.1111/j.1476-5381.1960.tb01240.x. </ref>
Furethidine is not currently used in medicine and is a Class A/Schedule I drug which is controlled under UN drug conventions. It has similar effects to other opioid derivatives, such as analgesia, sedation, nausea and respiratory depression.<ref name="pmid13689779">{{cite journal | vauthors = Cahal DA, Dare JG, Keith D | title = A sequential trial of analgesics in labour | journal = The Journal of Obstetrics and Gynaecology of the British Commonwealth | volume = 68 | pages = 88–93 | date = February 1961 | pmid = 13689779 | doi = 10.1111/j.1471-0528.1961.tb02689.x | s2cid = 27397119 }}</ref> In the United States it is a Schedule I Narcotic controlled substance with the ACSCN of 9626.<ref>{{cite web | title = Controlled Substances - Alphabetical Order | date = 2020 | url = https://www.deadiversion.usdoj.gov/schedules/orangebook/c_cs_alpha.pdf | page = 9 | work = Diversion Control Division | publisher = Drug Enforcement Agency, U.S. Department of Justice }}</ref>
==References== {{Reflist|2}}
== External links == * [https://web.archive.org/web/20050120023230/http://www.unodc.org/unodc/en/bulletin/bulletin_1961-01-01_4_page004.html UNODC Bulletin on Narcotics 1961]
{{Opioidergics}}
Category:Synthetic opioids Category:Tetrahydrofurans Category:4-Phenylpiperidines Category:Carboxylate esters Category:Ethyl esters Category:Mu-opioid receptor agonists
{{analgesic-stub}}