# Hydroxypethidine

> Mediated Wiki article. Canonical URL: https://mediated.wiki/source/Hydroxypethidine
> Markdown URL: https://mediated.wiki/source/Hydroxypethidine.md
> Source: https://en.wikipedia.org/wiki/Hydroxypethidine
> Source revision: 1308513480
> License: Creative Commons Attribution-ShareAlike 4.0 International (https://creativecommons.org/licenses/by-sa/4.0/)

{{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](/source/Di%C3%A1rio_Oficial_da_Uni%C3%A3o) |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](/source/opioid) [analgesic](/source/analgesic) that is an [analogue](/source/analog_(chemistry)) of the more commonly used [pethidine](/source/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](/source/NMDA_antagonist) properties like its close relative [ketobemidone](/source/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](/source/itching), [nausea](/source/nausea) and potentially serious [respiratory depression](/source/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](/source/4-Fluoropethidine)

== 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

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Adapted from the Wikipedia article [Hydroxypethidine](https://en.wikipedia.org/wiki/Hydroxypethidine) by Wikipedia contributors ([contributor history](https://en.wikipedia.org/wiki/Hydroxypethidine?action=history)). Available under [Creative Commons Attribution-ShareAlike 4.0 International](https://creativecommons.org/licenses/by-sa/4.0/). Changes may have been made.