furethidine

{{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

| tradename =

| pregnancy_AU =

| pregnancy_US =

| pregnancy_category =

| legal_AU = S9

| legal_BR = A1

| legal_BR_comment = {{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}}

| legal_CA = Schedule I

| legal_UK = Class A

| legal_US = Schedule I

| legal_DE = Anlage I

| bioavailability =

| protein_bound =

| metabolism =

| elimination_half-life =

| excretion =

| 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

| 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 = ethyl 4-phenyl-1-(2-tetrahydrofurfuryloxyethyl)piperidine-4-carboxylate

}}

Furethidine{{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 }}Frearson Peter Marshall; Stern Edward Severin, {{Cite patent|DE|1256219}} (1967 to Glaxo Lab Ltd).{{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}} is a 4-phenylpiperidine derivative that is related to the clinically used opioid analgesic drug pethidine (meperidine),{{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 }} but with around 25x higher potency.Casy AF, Parfitt RY. Opioid analgesics, chemistry and receptors. 1986, Plenum Press, New York. pp 234-235. {{ISBN|0-306-42130-5}} According to another source, Furethidine is 500/30 = 16.7 x the potency of pethidine (table VII).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.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.

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.{{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 }} In the United States it is a Schedule I Narcotic controlled substance with the ACSCN of 9626.{{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 }}