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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2013/10/23 18:43:24」(JST)

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Etorphine 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]}

Etorphine is often used to immobilize elephants and other large mammals. Etorphine is available legally only for veterinary use and is strictly governed by law. 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.

One of its main advantages in general veterinary work is its speed of operation and, more importantly, the speed with which diprenorphine reverses the effects. For example, operations on valuable animals such as racehorses, using alternative anaesthetics risks the animal injuring itself as the anesthetic wears off. The rapid action of etorphine and diprenorphine means the animal can be back on its feet within a relatively short time and aware of its surroundings more quickly, thus reducing any tendency to panic and move around rapidly while still partially under the influence of the anesthetic. For this reason, its use is popular with many vets.

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 5-15mg dose is enough to immobilize an african elephant and a 2-4mg dose is enough to immobilize an Black Rhino.^[4]

A close relative, dihydroetorphine, has been used as an opioid painkiller for human usage in China. It is claimed to be less addictive than traditional opioids but this has yet to be confirmed.

Pharmacology[edit]

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[edit]

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, although Etorphine hydrochloride is classified as Schedule II.

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

In media[edit]

It was used on the Blue Bloods television series by a fanatical mother and son serial killer team who prey on prostitutes in the episode "Lonely Hearts Club".

In the Defiance episode of Scandal (TV series), Quinn and Huck have a meeting where Quinn picks Huck's brain. He tells her the name of the spy drug is M99.

In Lewis (TV series), Episode 'Down Among the Fearful' Reuben Beatty is murdered by M99, Etorphine.

In "Dexter (TV series)", Dexter knocks out his victims using a syringe of M99 in numerous episodes throughout the show.

In The Office (U.S. TV Series), season 9 episode 19, Dwight uses three etorphine darts to render Stanley unconscious.

References[edit]

^ Bentley, KW; Hardy, DG (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". Journal of the American Chemical Society 89 (13): 3281–92. doi:10.1021/ja00989a032. PMID 6042764.
^ Opium: the king of narcotics
^ Bentley KW, Hardy DG. "New potent analgesics in the morphine series." Proceedings of the Chemical Society. 1963;220.
^ http://wildpharm.com/etorphine-hydrochloride-1mgml.html
^ 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

External links[edit]

Opioids.com page on etorphine
Etorphine: Molecule of the Month

English Journal

Chemical immobilization of free-ranging fallow deer (Dama dama): effect of needle length on induction time.

Bergvall UA1, Kjellander P, Ahlqvist P, Johansson Ö, Sköld K, Arnemo JM.
Journal of wildlife diseases.J Wildl Dis.2015 Apr;51(2):484-7. doi: 10.7589/2013-11-290. Epub 2015 Jan 14.
We evaluated impact of the needle length, sex, and body condition on chemical immobilization induction time in 50 (29 males and 21 females) free-ranging fallow deer (Dama dama) in Sweden, 2006-11. Induction time is probably the single most important factor when immobilizing free-ranging wildlife wit
PMID 25588014

Accelerated induction of etorphine immobilization in blue wildebeest (Connochaetes taurinus) through the addition of hyaluronidase.

Dittberner MJ1, Venter L, Naidoo V.
Veterinary anaesthesia and analgesia.Vet Anaesth Analg.2015 Mar;42(2):173-7. doi: 10.1111/vaa.12188. Epub 2014 Jun 25.
OBJECTIVE: To study the effects of the addition of hyaluronidase (HA) to an etorphine/azaperone drug combination on induction times of immobilization.STUDY DESIGN: Experimental part-randomized 'blinded' cross-over study.ANIMALS: Eight wild managed blue wildebeest (Connochaetes taurinus).METHODS: Ani
PMID 24962404

Hypoxia following etorphine administration in goats (Capra hircus) results more from pulmonary hypertension than from hypoventilation.

Meyer LC1,2, Hetem RS3, Mitchell D4, Fuller A5,6.
BMC veterinary research.BMC Vet Res.2015 Feb 3;11(1):18. doi: 10.1186/s12917-015-0337-5.
BACKGROUND: Etorphine, a potent opioid agonist, causes pulmonary hypertension and respiratory depression. Whether etorphine-induced pulmonary hypertension negatively influences pulmonary gas exchange and exacerbates the effects of ventilator depression and the resultant hypoxemia is unknown. To dete
PMID 25644810

Japanese Journal

オピエートのフロンティア電子密度の統計解析

水上善博
滋賀大学教育学部紀要. 3, 自然科学 54, 35-39, 2004
… occupied molecular orbitals of 25 opiates are calculated by semi-empirical AM1 molecular orbital calculations.Calculated opiates are morphine, oxymorphone, levorphanol, nalorphine, naloxone, levallorphan, heroin, codeine, etorphine, dihydromorphine, normorphine, pentazocine, apomorphine, buprenorphine, butorpahnol, dihydrocodeine, oxycodone, thebaine, bremazocine, cyclazocine, ketocyclazocine, naloxazone, naltrexazone, oxymorphazone.25 molecules have common molecular skeleton that includes 10 atoms(one nitrogen atom, one oxygen atom and 8 carbon …
NAID 110001183530

Evidence for the Existence of the β-Endorphin-Sensitive "ε-Opioid Receptor" in the Brain: The Mechanisms of ε-Mediated Antinociception

NARITA Minoru,TSENG Leon F.
The Japanese journal of pharmacology 76(3), 233-253, 1998-03
… The functional ε-opioid receptors in the brain are stimulated by bremazocine and etorphine as well as β-endorphin, but not by selective μ-, δ- or κ-opioid receptor agonists. …
NAID 10008191728

Etorphine inhibits cell growth and induces apoptosis in SK-N-SH cells: involvement of pertussis toxin-sensitive G proteins

YIN De-Ling,REN Xiu-Hai,ZHENG Zhen-Lin,PU Lu,JIANG Li-Zhen,MA Lan,PEI Gang
Neuroscience research : the official journal of the Japan Neuroscience Society 29(2), 121-127, 1997-10
NAID 10005827935

Related Pictures

★リンクテーブル★

リンク元

「オピオイド」

Etorphine
Systematic (IUPAC) name
	6,14-endoetheno – 7 a (1-(R)-hydroxy-1 methylbutyl)-tetrahydro-nororipavine
Clinical data
AHFS/Drugs.com	International Drug Names
Pregnancy cat.	?
Legal status	Prohibited (S9) (AU) Narcotic Schedules I and IV (UN) List 1 (Netherlands); Schedule I/II (see text) (United States)
Identifiers
CAS number	14521-96-1
ATCvet code	QN02AE90
PubChem	CID 644209
DrugBank	DB01497
ChemSpider	559231
UNII	42M2Y6NU9O
KEGG	D07937
ChEMBL	CHEMBL287413
Chemical data
Formula	C25H33NO4
Mol. mass	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 InChI=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 ; Key:CAHCBJPUTCKATP-FAWZKKEFSA-N ;
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　　[★]

英: opioid
同: 類麻薬
関: オピオイド受容体

オピオイド受容体に結合するモルフィン様物質のことを指す。

内因性のオピオイドペプチドが発見され、これらは内因性オピオイドペプチドと呼ばれるようになった。

作用

縮瞳

モルフィンと多くのμ,κアゴニストは瞳孔の縮小を引き起こす。これは瞳孔を支配する副交感神経の興奮による。μアゴニストを中毒量投与すると縮瞳し、pinpoints pupupilsはpathognomonicである。(GOO.559)

オピオイドとオピオイド類似物質の作用

GOO.552

Drugs	RECEPTOR TYPES
Drugs	μ受容体	δ受容体	κ受容体
morphine	＋＋＋		＋
methadone	＋＋＋
etorphine	＋＋＋	＋＋＋	＋＋＋
levorphanol	＋＋＋
fentanyl	＋＋＋
sufentanil	＋＋＋	＋	＋
DAMGO	＋＋＋
butorphanol	P		＋＋＋
buprenorphine	P		ーー
naloxone	ーーー	ー	ーー
naltrexone	ーーー	ー	ーーー
CTOP	ーーー
diprenorphine	ーーー	ーー	ーーー
β-funaltrexamine	ーーー	ー	＋＋
naloxonazine	ーーー	ー	ー
nalorphine	ーーー		＋
pentazocine	P		＋＋
nalbuphine	ーー		＋＋
naloxone benzoylhydrazone	ーーー	ー	ー
bremazocine	＋＋＋	＋＋	＋＋＋
ethylketocyclazocine	P	＋	＋＋＋
U50,488			＋＋＋
U69,593			＋＋＋
spiradoline	＋		＋＋＋
nor-Binaltorphimine	ー	ー	ーーー
naltrindole	ー	ーーー	ー
DPDPE		＋＋
[[［[D-Ala2,Glu4］deltorphin]]		＋＋

DSLET	＋	＋＋
endogenous Peptides
met-enkephalin	＋＋	＋＋＋
leu-enkephalin	＋＋	＋＋＋
β-endorphin	＋＋＋	＋＋＋
dynorphin A	＋＋		＋＋＋
dynorphin B	＋	＋	＋＋＋
α-neoendorphin	＋	＋	＋＋＋

＋アゴニスト　ーアンタゴニスト　P partial agonist

各鎮痛薬のオピオイド受容体への作用

　　　　　　　　　μ受容体　κ受容体

レミフェンタニル　＋＋＋　　ー

フェンタニル　　　＋＋＋　　－

モルヒネ　　　　　＋＋＋　　＋

ペチジン　　　　　＋＋　　　＋

トラマドール　　　＋　　　　－

ペンタゾシン　　　ー　　　　＋＋

ブプレノルフィン　Ｐ　　　　ー

ナロキソン　　　　ー　　　　－

[1] Bentley, KW; Hardy, DG (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". Journal of the American Chemical Society 89 (13): 3281–92. doi:10.1021/ja00989a032. PMID 6042764.

[2] Opium: the king of narcotics

[3] Bentley KW, Hardy DG. "New potent analgesics in the morphine series." Proceedings of the Chemical Society. 1963;220.

[4] ttp://wildpharm.com/etorphine-hydrochloride-1mgml.html

[5] 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

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案内

案内

etorphine