Wikipedia:WikiProject Chemicals/Chembox validation/VerifiedDataSandbox and Etorphine: Difference between pages

{{Short description|Semi-synthetic opioid}}

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 464368152

| IUPAC_name = (5α,6β,14β,18R)-18-[(2''R'')-2-Hydroxy-2-pentanyl]-6-methoxy-17-methyl-7,8-didehydro-18,19-dihydro-4,5-epoxy-6,14-ethenomorphinan-3-ol

| image = Etorphine.svg

| width = 150

| image2 = Etorphine-3D.png

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<!--Clinical data-->| tradename =

| Drugs.com = {{drugs.com|international|etorphine}}

| legal_AU = S9

| legal_BR = F1

| legal_CA = Schedule I

| legal_DE = Anlage III

| legal_EU = [[Opium_Law#List_I_drugs|List I]]

| legal_EU_comment = ([[Netherlands]])

| legal_UK = Class A

| legal_US = Schedule I

| legal_US_comment = and [[Controlled Substances Act|Schedule II]]

| legal_UN = N I IV

<!--Identifiers-->| CAS_number_Ref = {{cascite|changed|??}}

| CAS_number = 14521-96-1

| ATCvet = yes

| ATC_prefix = N02

| ATC_suffix = AE90

| PubChem = 644209

| DrugBank_Ref = {{drugbankcite|correct|drugbank}}

| IUPHAR_ligand = 1625

| DrugBank = DB01497

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 559231

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 42M2Y6NU9O

| KEGG_Ref = {{keggcite|correct|kegg}}

| KEGG = D07937

| ChEBI_Ref = {{ebicite|changed|EBI}}

| ChEBI = 4912

| ChEMBL_Ref =

| ChEMBL = 140050

| C = 25

| H = 33

| N = 1

| O = 4

| smiles = C[C@](CCC)(O)[C@H]1C[C@]23C=C[C@]1(OC)[C@@H]4Oc5c(O)ccc6C[C@H]2N(C)CC[C@]43c65

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 1S/C25H33NO4/c1-5-8-22(2,28)17-14-23-9-10-25(17,29-4)21-24(23)11-12-26(3)18(23)13-15-6-7-16(27)20(30-21)19(15)24/h6-7,9-10,17-18,21,27-28H,5,8,11-14H2,1-4H3/t17-,18-,21-,22-,23-,24+,25-/m1/s1

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = CAHCBJPUTCKATP-FAWZKKEFSA-N

'''Etorphine''' ('''M99''') is a semi-synthetic [[opioid]] possessing an [[analgesic]] potency approximately 1,000–3,000 times that of [[morphine]].<ref name="pmid6042764">{{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 = 3281–3292 | date = June 1967 | pmid = 6042764 | doi = 10.1021/ja00989a032 }}</ref> It was first prepared in 1960 from [[oripavine]], which does not generally occur in [[opium poppy]] extract but rather the related plants ''[[oriental poppy|Papaver orientale]]'' and ''[[Papaver bracteatum]]''.<ref name="urlOpium: the king of narcotics">{{cite book | chapter = Chapter 3 Opium: the king of narcotics | chapter-url = http://opioids.com/narcotic-drugs/chapter-3.html | title = Narcotic Drugs | vauthors = Aggrawal A | year = 1995 | publisher = National Book Trust | location = New Delhi | pages = xvi+161 | isbn = 81-237-1383-5 }}</ref> It was reproduced in 1963 by a research group at [[MacFarlan Smith]] in [[Gorgie]], [[Edinburgh]], led by Kenneth Bentley.<ref>{{cite journal |vauthors=Bentley KW, Hardy DG | title = New potent analgesics in the morphine series | journal = Proceedings of the Chemical Society | year = 1963 | volume = 220 | pages = 189–228 | doi = 10.1039/PS9630000189 }}</ref> It can be produced from [[thebaine]].<ref>{{Cite journal | vauthors = Huang XR, Srimurugan S, Lee GH, Chen C |date=February 2011 |title=A Facile Synthesis and Structural Verification of Etorphine and Dihydroetorphine from Codeine |journal=Journal of the Chinese Chemical Society |volume=58 |issue=1 |pages=101–107 |doi=10.1002/jccs.201190048 |issn=0009-4536|doi-access=free }}</ref>

== Veterinary use ==

Etorphine is available legally only for [[veterinary medicine|veterinary]] use and is strictly governed by law. It is often used to immobilize [[elephant]]s and other large mammals. [[Diprenorphine]] (Revivon) is an opioid receptor antagonist that can be administered in proportion to the amount of etorphine used (1.3 times) to reverse its effects. Veterinary-strength etorphine is fatal to humans. For this reason the package as supplied to vets always includes the human antidote along with the etorphine.

The human antidote is generally [[naloxone]], not diprenorphine, and is always prepared before the preparation of etorphine to be immediately administered following accidental human exposure to etorphine. The {{LD50}} in humans is 3&nbsp;μg which led to the requirement that the medicine include an equal dose of an antidote, [[diprenorphine]] or [[naloxone]].

One of its main advantages is its speed of operation, and more importantly, the speed that [[diprenorphine]] reverses its effects. The high incidence of side effects, including severe cardiopulmonary depression, has caused etorphine to fall into disfavor in general veterinary practice. However, its high potency, combined with the rapid action of both etorphine and its antagonist, diprenorphine, means that it has found a place for use in the capture of large mammals such as rhinoceroses and elephants, where rapid onset and rapid recovery are both very important. The high potency of etorphine means that sufficient etorphine can be administered to large wild mammals by projectile syringe (dart).

'''Large Animal Immobilon''' is a combination of etorphine plus [[acepromazine]] maleate. An etorphine antidote '''Large Animal Revivon''' contains mainly diprenorphine for animals and a human-specific [[naloxone]]-based antidote, which should be prepared prior to the etorphine. A 5–15&nbsp;mg dose is enough to immobilize an [[African elephant]] and a 2–4&nbsp;mg dose is enough to immobilize a [[black rhinoceros]].<ref name="url_Zoo_Pharm">{{cite web | url = http://wildpharm.com/etorphine-hydrochloride-1mgml.html | title = Etorphine HCl | work = Veterinary medicine for wildlife: immobilisation medicine for animals zoo animals | publisher = Zoo Pharm | access-date = 2013-10-11 | archive-date = 2016-09-08 | archive-url = https://web.archive.org/web/20160908005713/http://wildpharm.com/etorphine-hydrochloride-1mgml.html | url-status = dead }}</ref>

== Pharmacology ==

Etorphine is a potent, non-selective [[full agonist]] of the [[μ-opioid receptor|μ-]], [[delta opioid receptor|δ-]], and [[kappa opioid receptor|κ-opioid receptor]]s.<ref name="Pasternak2013">{{cite book| vauthors = Pasternak G |title=The Opiate Receptors|url=https://books.google.com/books?id=vhfyBwAAQBAJ&pg=PA444|date=17 April 2013|publisher=Springer Science & Business Media|isbn=978-1-60761-990-1|pages=444–}}</ref><ref name="GharagozlouHashemi2006">{{cite journal | vauthors = Gharagozlou P, Hashemi E, DeLorey TM, Clark JD, Lameh J | title = Pharmacological profiles of opioid ligands at kappa opioid receptors | journal = BMC Pharmacology | volume = 6 | issue = 1 | pages = 3 | date = January 2006 | pmid = 16433932 | pmc = 1403760 | doi = 10.1186/1471-2210-6-3 | doi-access = free }}</ref> It has a weak [[affinity (pharmacology)|affinity]] for the [[nociceptin receptor]].<ref name="pmid10688973">{{cite journal | vauthors = Hawkinson JE, Acosta-Burruel M, Espitia SA | title = Opioid activity profiles indicate similarities between the nociceptin/orphanin FQ and opioid receptors | journal = European Journal of Pharmacology | volume = 389 | issue = 2–3 | pages = 107–114 | date = February 2000 | pmid = 10688973 | doi = 10.1016/S0014-2999(99)00904-8 }}</ref> Etorphine has an LD₅₀ of 3&nbsp;μg in humans.<ref>{{cite book | title = Veterinary Pharmacology and Therapeutics | page = 32 | veditors = Riviere JE, Papich MG | isbn = 978-0-8138-2061-3| date = 2009-03-17 | vauthors = Riviere JE, Papich MG | publisher = John Wiley & Sons }}</ref>

== Legal status ==

In [[Hong Kong]], etorphine is regulated under Schedule 1 of Hong Kong's Chapter 134 ''Dangerous Drugs Ordinance''. It can be used legally only by health professionals and for university research purposes. The substance can be given by pharmacists under a prescription. Anyone who supplies the substance without prescription can be fined $10,000 ([[Hong Kong dollar|HKD]]). The penalty for trafficking or manufacturing the substance is a $5,000,000 (HKD) fine and life imprisonment. Possession of the substance for consumption without license from the Department of Health is illegal with a $1,000,000 (HKD) fine and/or 7 years of jail time.<ref>{{Cite web |title=Hong Kong e-Legislation |url=https://www.elegislation.gov.hk/checkconfig/checkClientConfig.jsp?applicationId=RA001 |access-date=2022-03-30 |website=www.elegislation.gov.hk}}</ref>

In the [[Netherlands]], etorphine is a Schedule I drug of the [[Opium Law]]. It is used only for veterinary purposes in zoos to immobilize large animals.<ref>{{Cite web | work = Ministerie van Binnenlandse Zaken en Koninkrijksrelaties|title=Opiumwet |url=https://wetten.overheid.nl/BWBR0001941/2021-10-28#BijlageI |access-date=2022-03-30 |language=nl}}</ref>

In the US, etorphine is listed as a [[Controlled Substances Act#Schedule I controlled substances|Schedule I]] drug with an ACSCN of 9056, although its [[hydrochloride]] [[Salt (chemistry)|salt]] is classified as [[Controlled Substances Act#Schedule II controlled substances|Schedule II]] with an ACSCN of 9059.<ref>{{Cite web | title = Etorphine | work = PubChem | id = CID 26721 |url=https://pubchem.ncbi.nlm.nih.gov/compound/26721 |access-date=2022-03-30 | publisher = U.S. National Library of Medicine |language=en}}</ref>

In the UK, under the [[Misuse of Drugs Act 1971]], etorphine is controlled as a Class A substance.<ref>{{Cite web |title=List of most commonly encountered drugs currently controlled under the misuse of drugs legislation |url=https://www.gov.uk/government/publications/controlled-drugs-list--2/list-of-most-commonly-encountered-drugs-currently-controlled-under-the-misuse-of-drugs-legislation |access-date=2022-03-30 |website=GOV.UK |language=en}}</ref>

In Italy '''Etorphine''' is illegal, as are the parent compounds [[Dihydroetorphine]] and [[Acetorphine]]. (Datas from 2022)<ref>{{Cite web | work = Ministero della Salute |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 |language=IT}}</ref>

== See also ==

* [[6,14-Endoethenotetrahydrooripavine]] - the central nucleus of all [[Bentley compounds|Bentley compound]] opioids under which class etorphine falls

* [[Dihydroetorphine]] – a close analog of etorphine that has been used as an opioid painkiller for human usage in China

* [[Thienorphine]]

* [[Equianalgesic|Opioid potency comparison]]

== References ==

{{Reflist|30em}}

== External links ==

* [http://opioids.com/etorphine/immobilon.html Opioids.com] page on etorphine

* [http://www.chm.bris.ac.uk/motm/etorphine/etorphinec.htm Etorphine: Molecule of the Month]

{{Opioidergics}}

[[Category:Analgesics]]

[[Category:Delta-opioid receptor agonists]]

[[Category:4,5-Epoxymorphinans]]

[[Category:Ethers]]

[[Category:Semisynthetic opioids]]

[[Category:Kappa-opioid receptor agonists]]

[[Category:Mu-opioid receptor agonists]]

[[Category:Nociceptin receptor agonists]]

[[Category:Phenols]]

[[Category:Tertiary alcohols]]