|Systematic (IUPAC) name|
|6,14-endoetheno – 7 a (1-(R)-hydroxy-1 methylbutyl)-tetrahydro-nororipavine|
|Legal status||Prohibited (S9) (AU) Narcotic Schedules I and IV (UN) List 1 (Netherlands)
Schedule I/II (see text) (United States)
|Mol. mass||411.53 g/mol|
|(what is this?)|
Etorphine (M99) is a semi-synthetic opioid possessing an analgesic potency approximately 1,000–3,000 times that of morphine. 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. It was later reproduced in 1963 by a research group at MacFarlan Smith in Gorgie, Edinburgh, led by Professor Kenneth Bentley. It can also be produced from thebaine.
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. 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 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 a Black Rhino.
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 UK, under the Misuse of Drugs Act 1971, Etorphine is controlled as a Class A substance.
Society and culture
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, Quinn and Huck have a meeting where Quinn picks Huck's brain. He tells her the name of the spy drug is M99. In the episode Everything's Coming Up Mellie, one character describes this M99 as a harmless tranquilizer when used against humans.
In Lewis, Episode 'Down Among the Fearful' Reuben Beatty is murdered by M99, Etorphine.
In Dexter, serial killer Dexter Morgan knocks out his victims using a syringe of M99 (etorphine) in almost every episode throughout the show. He illegally obtains the drug using the pseudonym Dr. Patrick Bateman, DVM.
In The Office, season 9 episode 19, Dwight uses three etorphine darts to render Stanley unconscious.
In The Vampire Diaries, season 5 episode 6, Katherine injects Dr. Wes Maxfield with a substance to make him unconscious. When asked what she used to inject him with she answers by saying she doesn't know although the bottle says avoid contact with eyes and do not ingest. Dr. Maxfield, whilst regaining his consciousness, overhears Katherine and replies by saying it's Etorphine.
- dihydroetorphine – a close analog of etorphine that has been used as an opioid painkiller for human usage in China
- 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.
- 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.
- Bentley KW, Hardy DG (1963). "New potent analgesics in the morphine series". Proceedings of the Chemical Society 220: 189–228. doi:10.1039/PS9630000189.
- "Etorphine HCl". Veterinary medicine for wildlife: immobilisation medicine for animals zoo animals. Zoo Pharm.
- 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.