hydroxypethidine
{{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
| tradename =
| pregnancy_AU =
| pregnancy_US =
| pregnancy_category =
| legal_AU =
| 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 =
| legal_US = Schedule I
| legal_DE = Anlage I
| routes_of_administration =
| bioavailability =
| protein_bound =
| metabolism =
| elimination_half-life =
| excretion =
| 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
| 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,{{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 = }} and it also has NMDA antagonist properties like its close relative ketobemidone.{{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 }}
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. {{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 }}