# Oxpheneridine

> Mediated Wiki article. Canonical URL: https://mediated.wiki/source/Oxpheneridine
> Markdown URL: https://mediated.wiki/source/Oxpheneridine.md
> Source: https://en.wikipedia.org/wiki/Oxpheneridine
> Source revision: 1337350722
> License: Creative Commons Attribution-ShareAlike 4.0 International (https://creativecommons.org/licenses/by-sa/4.0/)

{{Short description|Chemical compound}}
{{Drugbox
| verifiedrevid = 447992561
| IUPAC_name = ethyl 1-(2-hydroxy-2-phenylethyl)-4-phenylpiperidine-4-carboxylate
| image = Oxpheneridine.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_CA = <!-- Schedule I -->
| legal_UK =  
| legal_US =  
| legal_status =

<!--Pharmacokinetic data-->
| bioavailability =  
| protein_bound =  
| metabolism =  
| elimination_half-life =  
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<!--Identifiers-->
| CAS_number = 546-32-7
| ATC_prefix = none
| ATC_suffix =  
| PubChem = 56863
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank =  
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 51270
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 5OO7RKH9WL

<!--Chemical data-->
| C=22 | H=27 | N=1 | O=3 
| smiles = O=C(OCC)C3(c1ccccc1)CCN(CC(O)c2ccccc2)CC3
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C22H27NO3/c1-2-26-21(25)22(19-11-7-4-8-12-19)13-15-23(16-14-22)17-20(24)18-9-5-3-6-10-18/h3-12,20,24H,2,13-17H2,1H3
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = DBDXZFAMJLGFGD-UHFFFAOYSA-N
| synonyms =  
}}

'''Oxpheneridine'''<ref>CS Patent 109234</ref> is a 4-[phenyl](/source/phenyl)[piperidine](/source/piperidine) derivative that is related to the [opioid](/source/opioid) [analgesic](/source/analgesic) drug [pethidine](/source/pethidine) (meperidine).

Oxpheneridine is not currently used in medicine. Presumably it has similar effects to other opioid derivatives, such as [analgesia](/source/analgesia), [sedation](/source/sedation), [nausea](/source/nausea) and [respiratory depression](/source/respiratory_depression).

Unlike most opioid derivatives, oxpheneridine is not specifically listed as an illegal drug. In the [UNODC](/source/UNODC) narcotics report of 1958, they state that it was not possible to administer oxpheneridine in high doses as it is poorly soluble and highly irritating, and at the low doses administered it did not produce addiction in animals. This appears to be the only time oxpheneridine has been investigated, and so its pharmacological properties have not been well established.

Oxpheneridine would probably be regarded as a [controlled substance analogue](/source/Federal_Analog_Act) of pethidine on the grounds of its related chemical structure in some jurisdictions such as the United States, Australia and New Zealand.

In Canada, Oxpheneridine is specifically excluded from the illegal drugs list on the Controlled Drugs and Substances Act schedules, presumably on the basis of the lack of addictive potential found by the UNODC. 

==Synthesis==
Alkylation of [normeperidine](/source/normeperidine) [77-17-8] with [styrene oxide](/source/styrene_oxide) completes the synthesis.<ref>{{cite journal |author=Perrine, T. D. |author2=Eddy, N. B. | journal=The Journal of Organic Chemistry | title=The Preparation and Analgesic Activity of 4-Carbethoxy-4-phenyl-1-(2-phenylethyl)piperidine and Related Compounds | volume=21 | issue=1 | pages=125–126 | date= January 1956 | doi=10.1021/jo01107a028}}</ref><ref>{{cite journal |author=Protiva, M. |author2=Jílek, J. O. |author3=Pomykáček, J. |author4=Jirkovský, J. |author5=Vejdělek, Z. J. | journal=Collection of Czechoslovak Chemical Communications | title=Synthetische Analgetica V. Synthetische Versuche auf Basis von 4-Phenyl-4-carbäthoxypiperidin (Norpethidin) | volume=28 | issue=10 | pages=2627–2636 | date= 1963 | doi=10.1135/cccc19632627}}</ref>

== See also ==
* [Opioid](/source/Opioid)
* [Meperidine](/source/Meperidine)
* [Pheneridine](/source/Pheneridine)
* [Fentanyl](/source/Fentanyl)
* [Carbamethidine](/source/Carbamethidine)

== References ==
{{Reflist|2}}
*[http://www.unodc.org/unodc/en/bulletin/bulletin_1958-01-01_1_page009.html UNODC Bulletin on Narcotics 1958]
*[http://www.canlii.org/ca/as/1996/c19/part3321.html Canadian Controlled Drug Schedules]

{{Opioidergics}}

Category:Synthetic opioids
Category:4-Phenylpiperidines
Category:Secondary alcohols
Category:Phenylethanolamines
Category:Mu-opioid receptor agonists

{{analgesic-stub}}

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