| Revision as of 19:54, 16 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,081 edits Saving copy of the {{drugbox}} taken from revid 456976226 of page Acetorphine for the Chem/Drugbox validation project (updated: 'CAS_number'). |
Latest revision as of 14:59, 21 December 2024 edit Galactic-Radiance (talk | contribs)Extended confirmed users6,153 edits +drugbank |
| Line 1: |
Line 1: |
|
|
{{Short description|Opioid analgesic and anesthetic veterinary drug}} |
|
{{ambox | text = This page contains a copy of the infobox ({{tl|drugbox}}) taken from revid of page ] with values updated to verified values.}} |
|
|
{{Drugbox |
|
{{Drugbox |
|
|
| Verifiedfields = changed |
|
| verifiedrevid = 454116051 |
|
| verifiedrevid = 477239629 |
|
| IUPAC_name = 4,5α-epoxy-7α-(1-hydroxy-1-methylbutyl)-6-methoxy -17-methyl-6,14-endo-ethenomorphinan-3-yl acetate |
|
| IUPAC_name = 4,5α-epoxy-7α-(1-hydroxy-1-methylbutyl)-6-methoxy-17-methyl-6,14-endo-ethenomorphinan-3-yl acetate |
|
| image = Acetorphine.png |
|
| image = Acetorphine structure.svg |
|
|
|
|
|
| width = 220px |
|
|
| image2 = Acetorphine 3D BS.png |
|
|
| width2 = 220px |
|
<!--Clinical data--> |
|
<!--Clinical data--> |
|
| tradename = |
|
| tradename = |
|
| legal_status = |
|
| legal_AU = S9 |
|
|
| legal_BR = F1 |
|
|
| legal_CA = Schedule I |
|
| legal_US = Schedule I |
|
| legal_US = Schedule I |
|
|
| legal_UK = Class A |
|
|
| legal_UN = N I IV |
|
|
| legal_DE = Anlage I |
|
<!--Identifiers--> |
|
<!--Identifiers--> |
|
| CAS_number_Ref = {{cascite|correct|??}} |
|
| CAS_number_Ref = {{cascite|changed|??}} |
|
| CAS_number = <!-- blanked - oldvalue: 25333-77-1 --> |
|
| CAS_number = 25333-77-1 |
|
| ATC_prefix = none |
|
| ATC_prefix = none |
|
| PubChem = 62795 |
|
| PubChem = 62795 |
|
|
| KEGG = D12700 |
|
|
| DrugBank_Ref = |
|
|
| DrugBank = DB01469 |
|
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
|
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
|
| ChemSpiderID = 16736130 |
|
| ChemSpiderID = 16736130 |
| Line 21: |
Line 32: |
|
<!--Chemical data--> |
|
<!--Chemical data--> |
|
| C=27 | H=35 | N=1 | O=5 |
|
| C=27 | H=35 | N=1 | O=5 |
|
| molecular_weight = 453.57 g/mol |
|
|
| smiles = C(O)(CCC)6C43/C=C/6(OC)1Oc5c2c(C4N(C)CC123)ccc5OC(C)=O |
|
| smiles = C(O)(CCC)6C43/C=C/6(OC)1Oc5c2c(C4N(C)CC123)ccc5OC(C)=O |
|
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
|
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
| Line 28: |
Line 38: |
|
| StdInChIKey = LFYBMMHFJIAKFE-PMEKXCSPSA-N |
|
| StdInChIKey = LFYBMMHFJIAKFE-PMEKXCSPSA-N |
|
}} |
|
}} |
|
|
|
|
|
'''Acetorphine''' is a potent ] ], up to 8700 times stronger than ] by weight.<ref>{{cite journal | vauthors = Bentley KW, Hardy DG | title = Novel analgesics and molecular rearrangements in the morphine-thebaine group. 3. Alcohols of the 6,14-endo-ethenotetrahydrooripavine series and derived analogs of N-allylnormorphine and -norcodeine | journal = Journal of the American Chemical Society | volume = 89 | issue = 13 | pages = 3281–92 | date = June 1967 | pmid = 6042764 | doi = 10.1021/ja00989a032 }}</ref> It is a ] of the more well-known opioid ], which is used as a very potent ] painkiller and ] medication, primarily for the sedation of large animals such as elephants, giraffes and rhinos. |
|
|
|
|
|
Acetorphine was developed in 1966 by the ] research group that developed etorphine. Acetorphine was developed for the same purpose as etorphine itself, namely as a strong tranquilizer for use in immobilizing large animals in veterinary medicine. Despite showing some advantages over etorphine, for instance producing less toxic side effects in giraffes,<ref>{{ cite journal | publisher = ] | journal = Bulletin on Narcotics | year = 1968 | volume = 1968 | issue = 2 | title = The case of etorphine and acetorphine | pages = 51–52 | url = http://www.unodc.org/unodc/en/data-and-analysis/bulletin/bulletin_1968-01-01_2_page009.html }}</ref> acetorphine was never widely adopted for veterinary use, and etorphine (along with other tranquilizers such as ] and ]) remains the drug of choice in this application. |
|
|
|
|
|
==Legal Status== |
|
|
===Australia=== |
|
|
|
|
|
Acetorphine is a schedule 9 substance in Australia under the ] (February 2017).<ref name="Poisons Standard">{{cite web | title = Poisons Standard | date = October 2015 | url = https://www.comlaw.gov.au/Details/F2015L01534 | publisher = Australian Government | work = Federal Register of Legislation }}</ref> A schedule 9 drug is outlined in the ] as "Substances which may be abused or misused, the manufacture, possession, sale or use of which should be prohibited by law except when required for medical or scientific research, or for analytical, teaching or training purposes with approval of the CEO."<ref>{{cite web | title = Poisons Act | date = 1964 | publisher = Western Australia | url = http://www.slp.wa.gov.au/pco/prod/FileStore.nsf/Documents/MRDocument:26063P/$FILE/Poisons%20Act%201964%20-%20%5B09-f0-04%5D.pdf?OpenElement | archive-url = https://web.archive.org/web/20151222191725/http://www.slp.wa.gov.au/pco/prod/FileStore.nsf/Documents/MRDocument%3A26063P/%24FILE/Poisons%20Act%201964%20-%20%5B09-f0-04%5D.pdf?OpenElement | archive-date = 2015-12-22 }}</ref> |
|
|
|
|
|
Under the ] 6.0 g is the amount required determining a court of trial, 2.0 g is considered intent to sell and supply.<ref>{{cite web | title = Misuse of Drugs Act | date = 1981 | publisher = Western Australia | url = http://www.slp.wa.gov.au/pco/prod/FileStore.nsf/Documents/MRDocument:28280P/$FILE/Misuse%20Of%20Drugs%20Act%201981%20-%20%5B06-e0-00%5D.pdf?OpenElement | archive-url = https://web.archive.org/web/20151222180141/http://www.slp.wa.gov.au/pco/prod/FileStore.nsf/Documents/MRDocument%3A28280P/%24FILE/Misuse%20Of%20Drugs%20Act%201981%20-%20%5B06-e0-00%5D.pdf?OpenElement | archive-date=2015-12-22}}</ref> |
|
|
|
|
|
===Germany=== |
|
|
|
|
|
Acetorphine is illegal in Germany (]). |
|
|
|
|
|
=== Romania === |
|
|
Acetorphine is prohibited in Romania.<ref>{{Cite web |title=LEGE 143 26/07/2000 - Portal Legislativ |url=https://legislatie.just.ro/Public/DetaliiDocument/23629 |access-date=2024-08-29 |website=legislatie.just.ro}}</ref> |
|
|
|
|
|
=== United Kingdom === |
|
|
Acetorphine is considered a ] drug by the ] since 1971, making its unlawful possession and distribution illegal. Class A drugs are deemed to be the most dangerous. |
|
|
|
|
|
===United States=== |
|
|
|
|
|
Acetorphine is a Schedule I controlled substance in the United States. Its DEA Administrative Controlled Substances Control Number is 9319 and the one salt in use, acetorphine hydrochloride, has a freebase conversion ratio of 0.93. |
|
|
|
|
|
===Italy=== |
|
|
|
|
|
In Italy acetorphine is illegal, as are the parent compounds ] and ].<ref>{{Cite web |last=Salute |first=Ministero della |title=Tabelle delle sostanze stupefacenti e psicotrope |url=https://www.salute.gov.it/portale/medicinaliStupefacenti/dettaglioContenutiMedicinaliStupefacenti.jsp?lingua=italiano&id=3729&area=sostanzeStupefacenti&menu=vuoto&tab=1 |access-date=2022-04-09 |website=www.salute.gov.it |language=IT}}</ref> |
|
|
|
|
|
== See also == |
|
|
* ] |
|
|
|
|
|
== References == |
|
|
{{Reflist|2}} |
|
|
|
|
|
== External links == |
|
|
* |
|
|
* |
|
|
|
|
|
{{Opioidergics}} |
|
|
|
|
|
] |
|
|
] |
|
|
] |
|
|
] |
|
|
] |
|
|
] |
|
|
|
|
|
|
|
|
{{analgesic-stub}} |