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Saving copy of the {{drugbox}} taken from revid 456616350 of page Drotebanol for the Chem/Drugbox validation project (updated: 'CAS_number').
 
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{{Short description|Chemical compound}}
{{ambox | text = This page contains a copy of the infobox ({{tl|drugbox}}) taken from revid [{{fullurl:Drotebanol|oldid=456616350}} 456616350] of page [[Drotebanol]] with values updated to verified values.}}
{{Drugbox
{{Drugbox
| Verifiedfields = changed
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 411017960
| verifiedrevid = 461091590
| IUPAC_name = 3,4-dimethoxy- 9a-methylmorphinan- 6β,14-diol
| IUPAC_name = 3,4-Dimethoxy-17-methylmorphinan-6β,14-diol
| image = Drotebanol.svg
| image = Drotebanol.svg
| width = 200
| width = 200
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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 = S8
| legal_BR = A1
| legal_CA = <!-- / Schedule I, II, III, IV, V, VI, VII, VIII -->
| 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 = <!-- GSL / P / POM / CD / Class A, B, C -->
| legal_UK = <!-- GSL / P / POM / CD / Class A, B, C -->
| legal_US = Schedule I
| legal_US = Schedule I
| legal_status =
| legal_DE = Anlage I
| legal_status = SE: Förteckning II
| routes_of_administration =
| routes_of_administration =


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<!--Identifiers-->
<!--Identifiers-->
| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number_Ref = {{cascite|changed|??}}
| CAS_number = <!-- blanked - oldvalue: 3176-03-2 -->
| CAS_number = 3176-03-2
| ATC_prefix = none
| ATC_prefix = none
| ATC_suffix =
| ATC_suffix =
| ChEMBL_Ref = {{ebicite|changed|EBI}}
| ChEMBL = 2104603
| PubChem = 5463863
| PubChem = 5463863
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 16736125
| ChemSpiderID = 16736125
| UNII_Ref = {{fdacite|changed|FDA}}
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 7RS2Q8MCK8
| UNII = 7RS2Q8MCK8
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG_Ref = {{keggcite|correct|kegg}}
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<!--Chemical data-->
<!--Chemical data-->
| C=19 | H=27 | N=1 | O=4
| C=19 | H=27 | N=1 | O=4
| molecular_weight = 333.42 g/mol
| smiles = CN1CC[C@]23C[C@@H](CC[C@]2([C@H]1CC4=C3C(=C(C=C4)OC)OC)O)O
| smiles = CN1CC[C@]23C[C@@H](CC[C@]2([C@H]1CC4=C3C(=C(C=C4)OC)OC)O)O
| InChI = 1/C19H27NO4/c1-20-9-8-18-11-13(21)6-7-19(18,22)15(20)10-12-4-5-14(23-2)17(24-3)16(12)18/h4-5,13,15,21-22H,6-11H2,1-3H3/t13-,15-,18-,19-/m1/s1
| InChIKey = LCAHPIFLPICNRW-SVYNMNNPBL
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C19H27NO4/c1-20-9-8-18-11-13(21)6-7-19(18,22)15(20)10-12-4-5-14(23-2)17(24-3)16(12)18/h4-5,13,15,21-22H,6-11H2,1-3H3/t13-,15-,18-,19-/m1/s1
| StdInChI = 1S/C19H27NO4/c1-20-9-8-18-11-13(21)6-7-19(18,22)15(20)10-12-4-5-14(23-2)17(24-3)16(12)18/h4-5,13,15,21-22H,6-11H2,1-3H3/t13-,15-,18-,19-/m1/s1
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| melting_high = 167
| melting_high = 167
}}
}}

'''Drotebanol''' ('''Oxymethebanol''') is a [[morphinan]] derivative that acts as an [[opioid]] agonist. It was invented by [[Daiichi Sankyo Co.|Sankyo Company]] in Japan during the 1970s. It is synthesised from [[thebaine]].

Drotebanol has powerful [[antitussive]] (cough suppressant) effects, and is around 10x more potent than codeine in producing this effect. It also has analgesic effects several times stronger than codeine, but weaker than morphine.<ref>{{cite journal | vauthors = Kobayashi S, Hasegawa K, Mori M, Takagi H | title = Pharmacological studies on a new specifically potent antitussive agent, 14-hydroxydihydro-6 beta-thebainol-4-methylether (oxymethebanol) | journal = Arzneimittel-Forschung | volume = 20 | issue = 1 | pages = 43–46 | date = January 1970 | pmid = 5467447 }}</ref> In animal studies it was found to be moderately addictive and produced limited physical dependence, but not as severe as that seen with morphine or pethidine.<ref name="pmid405065">{{cite journal | vauthors = Yanagita T, Miyasato K, Oinuma N, Yiyohara H | title = Dependence potential of drotebanol, codeine and thebaine tested in rhesus monkeys | journal = Bulletin on Narcotics | volume = 29 | issue = 1 | pages = 33–46 | date = 1977 | pmid = 405065 | url = http://www.unodc.org/unodc/en/data-and-analysis/bulletin/bulletin_1977-01-01_1_page005.html }}</ref> It was previously marketed for human use under the brand name '''Metebanyl''', although it is now no longer used in medicine.

It is currently a Schedule I Narcotic controlled substance in the United States with a DEA ACSCN of 9335 and an annual aggregate manufacturing quota of zero.

== References ==
{{Reflist|2}}

{{Opioidergics}}

[[Category:Diols]]
[[Category:Antitussives]]
[[Category:Morphinans]]
[[Category:Mu-opioid receptor agonists]]
[[Category:Phenol ethers]]
[[Category:Semisynthetic opioids]]
[[Category:Cyclohexanols]]
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