{{Short description|Chemical compound}} {{Drugbox | verifiedrevid = 447830929 | IUPAC_name = Ethyl 4-(3-hydroxyphenyl)-1-methyl-piperidine-4-carboxylate | image = hydroxypethidine.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 = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / 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 | routes_of_administration =
<!--Pharmacokinetic data--> | bioavailability = | protein_bound = | metabolism = | elimination_half-life = | excretion =
<!--Identifiers--> | CAS_number = 468-56-4 | CAS_number_Ref = {{Cascite|correct|CAS}} | ATC_prefix = none | ATC_suffix = | PubChem = 61120 | ChEMBL = 1182665 | DrugBank_Ref = {{drugbankcite|correct|drugbank}} | DrugBank = | ChEBI = 135085 | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID = 55068 | UNII_Ref = {{fdacite|correct|FDA}} | UNII = W1J43H2B3K | KEGG_Ref = {{keggcite|correct|kegg}} | KEGG = D12681
<!--Chemical data--> | C=15 | H=21 | N=1 | O=3 | smiles = O=C(OCC)C2(c1cccc(O)c1)CCN(C)CC2 | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI = 1S/C15H21NO3/c1-3-19-14(18)15(7-9-16(2)10-8-15)12-5-4-6-13(17)11-12/h4-6,11,17H,3,7-10H2,1-2H3 | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = WTJBNMUWRKPFRS-UHFFFAOYSA-N }}
'''Hydroxypethidine''' ('''Bemidone''') is an opioid analgesic that is an analogue of the more commonly used pethidine (meperidine). Hydroxypethidine is slightly more potent than meperidine as an analgesic, 1.5x meperidine in potency,<ref name="pmid5319798">{{cite journal | vauthors = Beckett AH, Casy AF | title = Analgesics and their antagonists: biochemical aspects and structure-activity relationships | journal = Progress in Medicinal Chemistry | volume = 4 | issue = | pages = 171–218 | date = February 1965 | pmid = 5319798 | doi = 10.1016/s0079-6468(08)70169-3 | isbn = 9780444533234 | url = }}</ref> and it also has NMDA antagonist properties like its close relative ketobemidone.<ref>{{cite journal | vauthors = Harris I | title = The addiction liability of some analogues of meperidine. | journal = Journal of Pharmacology and Experimental Therapeutics | date = 1949 | volume = 97 | issue = 2 | pages = 182–190 | doi = 10.1016/S0022-3565(25)03685-7 | url = https://jpet.aspetjournals.org/content/97/2/182 | url-access = subscription }}</ref>
Hydroxypethidine has similar effects to other opioids, and produces analgesia, sedation and euphoria. Side effects can include itching, nausea and potentially serious respiratory depression which can be life-threatening.
Hydroxypethidine is under international control under the Single Convention on Narcotic Drugs 1961 and therefore controlled like morphine in most countries; in the United States it is a Schedule I Narcotic controlled substance with an ACSCN of 9627 and a 2014 annual aggregate manufacturing quota of 2 grams. The salt in use is the hydrochloride, with a free base conversion ratio of 0.878. <ref>{{cite web | title = Conversion Factors for Controlled Substances | url = http://www.deadiversion.usdoj.gov/quotas/conv_factor/index.html | work = Diversion Control Division | publisher = Drug Enforcement Administration, U.S. Department of Justice | access-date = 2016-02-27 | archive-date = 2016-03-02 | archive-url = https://web.archive.org/web/20160302162948/http://deadiversion.usdoj.gov/quotas/conv_factor/index.html | url-status = dead }}</ref>
==See also== * 4-Fluoromeperidine
== References == {{Reflist|1}}
{{Opioidergics}}
Category:Synthetic opioids Category:4-Phenylpiperidines Category:3-Hydroxyphenyl compounds Category:Carboxylate esters Category:Mu-opioid receptor agonists Category:NMDA receptor antagonists