Dimenoxadol: Difference between revisions

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{{Short description|Opioid analgesic drug}}
{{Drugbox
{{Drugbox
| Verifiedfields = changed
| Watchedfields = changed
| Watchedfields = changed
| verifiedrevid = 399907132
| verifiedrevid = 447990763
| IUPAC_name = 2-dimethylaminoethyl 2-ethoxy-2,2-di(phenyl)acetate
| IUPAC_name = 2-(dimethylamino)ethyl 2-ethoxy-2,2-diphenylacetate
| image = Dimenoxadol.svg
| image = Dimenoxadol.svg
| width = 180
| width = 180
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| pregnancy_US = <!-- A / B / C / D / X -->
| pregnancy_US = <!-- A / B / C / D / X -->
| pregnancy_category =
| pregnancy_category =
| legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 -->
| legal_AU = S9
| legal_CA =
| 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 =
| legal_UK =
| legal_US = Schedule I
| legal_US = Schedule I
| legal_status =
| legal_DE = Anlage I
| legal_UN = P I
| routes_of_administration =
| routes_of_administration =


<!--Pharmacokinetic data-->
<!--Pharmacokinetic data-->
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| protein_bound =
| protein_bound =
| elimination_half-life =
| elimination_half-life =
| excretion =
| excretion =


<!--Identifiers-->
<!--Identifiers-->
| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 509-78-4
| CAS_number = 509-78-4
| ATC_prefix = none
| ATC_prefix = none
| ATC_suffix =
| ATC_suffix =
| PubChem = 17036
| PubChem = 17036
| DrugBank_Ref = {{drugbankcite|changed|drugbank}}
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = DB01461
| DrugBank = DB01461
| ChEMBL = 2104309
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 16137
| ChemSpiderID = 16137
| UNII_Ref = {{fdacite|changed|FDA}}
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 4D65PBX0VK
| UNII = 4D65PBX0VK
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D12672


<!--Chemical data-->
<!--Chemical data-->
| C=20 | H=25 | N=1 | O=3
| C=20 | H=25 | N=1 | O=3
| smiles = CCOC(C1=CC=CC=C1)(C2=CC=CC=C2)C(=O)OCCN(C)C
| molecular_weight = 327.42 g/mol
| smiles = Cl.CCOC(C(=O)OCCN(C)C)(c1ccccc1)c1ccccc1
| InChI = 1/C20H25NO3/c1-4-24-20(17-11-7-5-8-12-17,18-13-9-6-10-14-18)19(22)23-16-15-21(2)3/h5-14H,4,15-16H2,1-3H3
| InChIKey = RHUWRJWFHUKVED-UHFFFAOYAH
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C20H25NO3/c1-4-24-20(17-11-7-5-8-12-17,18-13-9-6-10-14-18)19(22)23-16-15-21(2)3/h5-14H,4,15-16H2,1-3H3
| StdInChI = 1S/C20H25NO3/c1-4-24-20(17-11-7-5-8-12-17,18-13-9-6-10-14-18)19(22)23-16-15-21(2)3/h5-14H,4,15-16H2,1-3H3
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}}
}}


'''Dimenoxadol''' ('''Estocin''') is an [[opioid]] [[analgesic]] which is a diphenylacetic acid derivative, related to other drugs such as [[dextropropoxyphene]].
'''Dimenoxadol''' ([[International Nonproprietary Name|INN]]) (brand name '''Estocin''' (in [[Russia]])), or '''dimenoxadole''' ([[British Approved Name|BAN]]), is an [[opioid]] [[analgesic]] which is a [[benzilic acid]] derivative, closely related to [[benactyzine]] (an [[anticholinergic]]). Further, the structure is similar to [[methadone]] and related compounds like [[dextropropoxyphene]].


It was invented in Germany in the 1950s<ref>Boehringer, A et al, A new and improved analgesic and process for its production, GB patent 716700</ref>, and produces similar effects to other opioids, including [[analgesia]], [[sedation]], [[dizziness]] and [[nausea]].<ref>Gorbatova EN. The pharmacology of estocin, a new analgesic. (Russian). ''Stomatologiia (Moskow)''. 1967 Mar-Apr;46(2):22-5.</ref><ref>Kingisepp GIa, Kurvits KhKh, Nurmand LB. Pharmacology of dimethylaminoethyl ester of diphenylethoxyacetic acid hydrochloride--estocin. (Russian) ''Farmakologiia i Toksikologiia''. 1969 Nov-Dec;32(6):710-2.</ref>
It was invented in Germany in the 1950s,<ref>{{cite patent | country = GB | number = 716700 | title = A new and improved analgesic and process for its production | inventor = Boehringer A, et al. | pubdate = 10/13/1954}}</ref> and produces similar effects to other opioids, including [[analgesia]], [[sedation]], [[dizziness]] and [[nausea]].<ref>{{cite journal | vauthors = Gorbatova EN | title = [The pharmacology of estocin, an new analgesic] | journal = Stomatologiia | volume = 46 | issue = 2 | pages = 22–5 | year = 1967 | pmid = 5232927 }}</ref><ref>{{cite journal | vauthors = Kingisepp GI, Kurvits K, Nurmand LB | title = [Pharmacology of dimethylaminoethyl ester of diphenylethoxyacetic acid hydrochloride--estocin] | journal = Farmakologiia I Toksikologiia | volume = 32 | issue = 6 | pages = 710–2 | year = 1969 | pmid = 5381602 }}</ref><ref>{{cite journal | vauthors = Liberman SS | title = [Analgesic action of estocin (dimethylaminoethyl ester hydrochloride of alpha, alpha-diphenylethoxyacetic acid)] | journal = Farmakologiia I Toksikologiia | volume = 31 | issue = 6 | pages = 668–71 | year = 1968 | pmid = 5729519 }}</ref>


In the United States it is a Schedule I Narcotic controlled substance with an ACSCN of 9617 and a 2013 annual aggregate manufacturing quota of zero.


== References ==
{{Reflist}}


{{Analgesics}}
{{Opioidergics}}


[[Category:Analgesics]]

== References ==
<references/>

[[Category:Synthetic opioids]]
[[Category:Synthetic opioids]]
[[Category:Ethers]]
[[Category:Ethers]]
[[Category:Carboxylate esters]]
[[Category:Carboxylate esters]]
[[Category:Mu-opioid agonists]]
[[Category:Mu-opioid receptor agonists]]
[[Category:Dimethylamino compounds]]



{{analgesic-stub}}
{{analgesic-stub}}

[[sv:Dimenoxadol]]