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{{drugbox |
{{Drugbox
| image = |
| Verifiedfields = changed
| IUPAC_name = 6,14-endoetheno – 7 a (1-(R)-hydroxy-1 methylbutyl)-tetrahydro-nororipavine  
| verifiedrevid = 464368152
| IUPAC_name = 6,14-endoetheno – 7 a (1-(R)-hydroxy-1 methylbutyl)-tetrahydro-nororipavine
| image = Etorphine Wiki Str.png
| image2 = Etorphine3DanJ.gif
 
<!--Clinical data-->
| tradename = 
| Drugs.com = {{drugs.com|international|etorphine}}
| legal_AU = S9
| legal_US = [[Controlled Substances Act|Schedule I and II]]
| legal_status = List 1 ([[Netherlands]])
| legal_UN = N I IV
 
<!--Identifiers-->
| CAS_number_Ref = {{cascite|changed|??}}
| CAS_number = 14521-96-1
| CAS_number = 14521-96-1
| legal status =  
| ATCvet = yes
| legal_status = List 1[[NL]] Schedule I/II(see text)[[US]]
| ATC_prefix = N02
| C = 25 | H = 33 | N = 1 | O = 4
| ATC_suffix = AE90
| PubChem = 644209
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| 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 = {{ebicite|changed|EBI}}
| ChEMBL = 287413
 
<!--Chemical data-->
| C=25 | H=33 | N=1 | O=4  
| molecular_weight = 411.53 g/mol
| molecular_weight = 411.53 g/mol
| smiles = O[C@](C)(CCC)[C@H]6C[C@]53\C=C/[C@]6(OC)[C@@H]4Oc1c2c(ccc1O)C[C@H]5N(CC[C@@]234)C
| InChI = 1/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
| InChIKey = CAHCBJPUTCKATP-FAWZKKEFBM
| 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
}}
}}


{{SI}}
'''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 | author = 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 = J. Am. Chem. Soc. | volume = 89 | issue = 13 | pages = 3281–92 |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 in "poppy straw" and in 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 | chapterurl = http://opioids.com/narcotic-drugs/chapter-3.html | title = Narcotic Drugs | author = Aggrawal A | year = 1995 | publisher = National Book Trust | location = New Delhi | pages = xvi+161 | isbn = 81-237-1383-5 }}</ref> It was later reproduced in 1963 by a research group at [[MacFarlan Smith]] in [[Gorgie]], [[Edinburgh]], led by Professor Kenneth Bentley.<ref>{{cite journal | author = 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 also be produced from [[thebaine]].{{citation needed|date=April 2013}}
 
== 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]] (M5050), also known as 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 as well as Etorphine. The human antidote is generally [[naloxone]], not diprenorphine, and is always prepared prior to the preparation of etorphine to be immediately administered following accidental human exposure to etorphine.
 
One of its main advantages is its speed of operation and, more importantly, the speed with which [[diprenorphine]] reverses the 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 capture of large mammals such as rhinoceroses and elephant; under these circumstances both rapid onset and rapid recovery are very important characteristics. 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 Rhino.<ref name="url_Zoo_Pharm">{{cite web | url = http://wildpharm.com/etorphine-hydrochloride-1mgml.html | title = Etorphine HCl | author = | authorlink = | coauthors = | date = | work = Veterinary medicine for wildlife: immobilisation medicine for animals zoo animals | publisher = Zoo Pharm }}</ref>


== Pharmacology ==
Etorphine is an agonist at [[mu opioid receptor|μ]], [[delta opioid receptor|δ]], and [[kappa opioid receptor|κ]] [[opioid receptors]]. It also has a weak affinity for the ORL1 [[nociceptin]]/[[orphanin FQ]] receptor.<ref name="pmid10688973">{{cite journal | author = Hawkinson JE, Acosta-Burruel M, Espitia SA | title = Opioid activity profiles indicate similarities between the nociceptin/orphanin FQ and opioid receptors | journal = Eur. J. Pharmacol. | volume = 389 | issue = 2-3 | pages = 107–14 |date=February 2000 | pmid = 10688973 | doi = 10.1016/S0014-2999(99)00904-8 }}</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.


==Overview==
In the [[Netherlands]], Etorphine is a list I drug of the [[Opium Law]]. It is used only for veterinary purposes in zoos to immobilize large animals.
'''Etorphine''' ('''Immobilon'''® or '''M99''') is a semi-synthetic [[opioid]] possessing an [[analgesic]] potency approximately 1000-3000 times that of [[morphine]] depending on the test. It was invented in 1963 by a research group at McFarlan-Smith and Co. in Edinburgh, led by Professor Kenneth Bentley.<ref>Bentley KW, Hardy DG. "New potent analgesics in the morphine series." ''Proceedings of the Chemical Society''. 1963;220.</ref><ref>Bentley KW, Hardy DG. "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 of the American Chemical Society''. 1967 Jun 21;89(13):3281-92. PMID 6042764</ref> It can be produced from [[thebaine]]. It is most often used to immobilize elephants and other large mammals. Etorphine is only available legally for [[veterinary medicine|veterinary]] use and is strictly governed by law. [[Diprenorphine]] (M5050) is an opioid receptor antagonist that can be administered in proportion to the amount of etorphine used (1.3 times) to reverse its effects.


'''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.
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.  For both, the 2013 annual aggregate manufacturing quota for both was zero so presumably veterinary supplies of the hydrochloride are imported from Germany and/or the UK.


A close relative, [[dihydroetorphine]] has been used as opiate painkiller for human usage in China. It is claimed to be less addictive than traditional opioids but this has yet to be confirmed.
In the UK, under the Misuse of Drugs Act 1971, Etorphine is controlled as a Class A substance.
==Pharmacology==
Etorphine is an agonist at <math>\mu</math>, <math>\delta</math>, and <math>\kappa</math> [[opioid receptors]]. It also has a weak affinity for the ORL1 [[nociceptin]]/[[orphanin FQ]] receptor.<ref>Hawkinson JE, Acosta-Burruel M, Espitia SA. "Opioid activity profiles indicate similarities between the nociceptin/orphanin FQ and opioid receptors." ''European Journal of Pharmacology''. 2000 Feb 18;389(2-3):107-14. PMID 10688973</ref>


==Legal status==
==Synthesis==
In Hong Kong, Etorphine is regulated under Schedule 1 of Hong Kong's Chapter 134 ''Dangerous Drugs Ordinance''. It can only be used legally by health professionals and for university research purporses. The substance can be given by pharmacists under a prescription. Anyone who supplies the substance without prescription can be fined $10000(HKD). The penalty for trafficking or manufacturing the substance is a $5,000,000 (Hong Kong dollar) 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.
[[File:Etorphine synthesis.png|thumb|700px|center|Etorphine synthesis:<ref>{{Cite doi|10.1021/jm00297a041}}</ref>]]


In the Netherlands, Etorphine is a list I drug of the Opium Law. It is only used for veterinary purposes in zoo's to inmobilise large animals.
== In Popular Culture ==
In the Showtime television series ''[[Dexter (TV series)|Dexter]]'' the lead character of the same name uses Etorphine to immobilize his victims.


In the US, Etorphine is listed as a Schedule I drug, although Etorphine [[hydrochloride]] is classified as Schedule II.
In the TV show "Lewis", Season 7, Episode 1, Etorphine is used by an assassin to kill two persons.


==In popular culture==
== See also ==
Etorphine is the drug which the main character in the books and TV-series about the serial killer and blood spatter specialist ''Dexter'' uses to immobilize his victims. In one episode of the TV-series it is shown that the character uses a fake doctor's name to obtain the controlled substance.
* [[Dihydroetorphine]] – a close analog of etorphine that has been used as an opioid painkiller for human usage in China


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


==External links==
== External links ==
* [http://opioids.com/etorphine/immobilon.html Opioids.com] page on etorphine
* [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]
* [http://www.chm.bris.ac.uk/motm/etorphine/etorphinec.htm Etorphine: Molecule of the Month]


{{Opioids}}
{{Opioidergics}}
 
[[de:Etorphin]]
[[sv:Etorfin]]


[[Category:Semisynthetic opioids]]
[[Category:Semisynthetic opioids]]
[[Category:Mu-opioid agonists]]
[[Category:Mu-opioid agonists]]
[[Category:Opioids]]
[[Category:Morphinans]]
[[Category:Drugs]]
[[Category:Phenols]]
 
[[Category:Alcohols]]
{{WH}}
[[Category:Ethers]]
{{WS}}
[[Category:Nociceptin receptor agonists]]

Latest revision as of 20:17, 6 April 2015

Etorphine
Clinical data
AHFS/Drugs.comInternational Drug Names
ATCvet code
Legal status
Legal status
Identifiers
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
E number{{#property:P628}}
ECHA InfoCard{{#property:P2566}}Lua error in Module:EditAtWikidata at line 36: attempt to index field 'wikibase' (a nil value).
Chemical and physical data
FormulaC25H33NO4
Molar mass411.53 g/mol
3D model (JSmol)
 ☒N☑Y (what is this?)  (verify)

Etorphine (M99) is a semi-synthetic opioid possessing an analgesic potency approximately 1,000–3,000 times that of morphine.[1] It was first prepared in 1960 from oripavine, which does not generally occur in opium poppy extract but rather in "poppy straw" and in the related plants Papaver orientale and Papaver bracteatum.[2] It was later reproduced in 1963 by a research group at MacFarlan Smith in Gorgie, Edinburgh, led by Professor Kenneth Bentley.[3] It can also be produced from thebaine.[citation needed]

Veterinary use

Etorphine is available legally only for veterinary use and is strictly governed by law. It is often used to immobilize elephants and other large mammals. Diprenorphine (M5050), also known as 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 as well as Etorphine. The human antidote is generally naloxone, not diprenorphine, and is always prepared prior to the preparation of etorphine to be immediately administered following accidental human exposure to etorphine.

One of its main advantages is its speed of operation and, more importantly, the speed with which diprenorphine reverses the 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 capture of large mammals such as rhinoceroses and elephant; under these circumstances both rapid onset and rapid recovery are very important characteristics. 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 mg dose is enough to immobilize an African elephant and a 2–4 mg dose is enough to immobilize a Black Rhino.[4]

Pharmacology

Etorphine is an agonist at μ, δ, and κ opioid receptors. It also has a weak affinity for the ORL1 nociceptin/orphanin FQ receptor.[5]

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 (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.

In the Netherlands, Etorphine is a list I drug of the Opium Law. It is used only for veterinary purposes in zoos to immobilize large animals.

In the US, Etorphine is listed as a Schedule I drug with an ACSCN of 9056, although its hydrochloride salt is classified as Schedule II with an ACSCN of 9059. For both, the 2013 annual aggregate manufacturing quota for both was zero so presumably veterinary supplies of the hydrochloride are imported from Germany and/or the UK.

In the UK, under the Misuse of Drugs Act 1971, Etorphine is controlled as a Class A substance.

Synthesis

File:Etorphine synthesis.png
Etorphine synthesis:[6]

In Popular Culture

In the Showtime television series Dexter the lead character of the same name uses Etorphine to immobilize his victims.

In the TV show "Lewis", Season 7, Episode 1, Etorphine is used by an assassin to kill two persons.

See also

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

References

  1. ↑ Bentley KW, Hardy DG (June 1967). "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". J. Am. Chem. Soc. 89 (13): 3281–92. doi:10.1021/ja00989a032. PMID 6042764.
  2. ↑ Aggrawal A (1995). "Chapter 3 Opium: the king of narcotics". Narcotic Drugs. New Delhi: National Book Trust. pp. xvi+161. ISBN 81-237-1383-5.
  3. ↑ Bentley KW, Hardy DG (1963). "New potent analgesics in the morphine series". Proceedings of the Chemical Society. 220: 189–228. doi:10.1039/PS9630000189.
  4. ↑ "Etorphine HCl". Veterinary medicine for wildlife: immobilisation medicine for animals zoo animals. Zoo Pharm.
  5. ↑ Hawkinson JE, Acosta-Burruel M, Espitia SA (February 2000). "Opioid activity profiles indicate similarities between the nociceptin/orphanin FQ and opioid receptors". Eur. J. Pharmacol. 389 (2–3): 107–14. doi:10.1016/S0014-2999(99)00904-8. PMID 10688973.
  6. ↑ Template:Cite doi

External links

Retrieved from "https://www.wikidoc.org/index.php?title=Etorphine&oldid=1083599"