Etorphine

Structural formula
General
Non-proprietary name	Etorphine
other names	(5 R , 6 R , 7 R , 9 R , 13 S , 14 R ) -7 - [( R ) -2-hydroxypentan-2-yl] 6-methoxy-17-methyl-4,5-epoxy-6 , 14-ethenomorphinan-3-ol
Molecular formula	C 25 H 33 NO 4
External identifiers / databases
EC number	238-535-9
ECHA InfoCard	100.035.017
PubChem	26721
ChemSpider	24895
DrugBank	DB01497
Wikidata	Q416827
Drug information
ATC code	Q N02AE90
Drug class	analgesic
Mechanism of action	Opioid
properties
Molar mass	411.53 g · mol -1
safety instructions
	Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
H and P phrases	H: 300-330-361
	P: ?
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Etorphine (M99) is a semi-synthetic relative of morphine with an exceptionally high analgesic potency , about 1000 to 3000 times that of morphine. It is used to immobilize large wild animals such as elephants and other large mammals. Etorphine is approved for veterinary use only. A close relative, the even more effective dihydroetorphine , which can be produced by hydrogenation of the double bond , is initially only used in China as a pain reliever in human medicine.

Etorphine was first synthesized in 1963 by Bentley and Hardy and can be obtained from the starting substance thebaine .

Diprenorphine (M5050) is a potent opioid receptor antagonist and can be used to neutralize the effects of etorphine (factor 1: 1.3). A preparation variant especially for large animals ( Large Animal Immobilon ) also contains azepromazine maleate, the associated antagonist Large Animal Revivon mainly consists of diprenorphine.

When immobilizing large wild animals, a second person should be available who is familiar with the substance used and possible countermeasures (here: antidote naloxone ) in the event that the vet accidentally injects himself with etorphine while handling the injection syringe; even a small amount could be fatal due to rapid onset of respiratory depression .

Etorphine is not a safe narcotic in practical use . Some wild animals only survive in 90% of the use cases, which forces a very sensitive dosage; on the other hand, underdosing is life-threatening for those treating.

Legal status in Germany

Etorphine is a marketable and prescription narcotic drug in the Federal Republic of Germany due to its listing in Appendix 3 BtMG. Handling without permission or prescription is generally punishable. Further information can be found in the main article Narcotics Law in Germany .

Media presence

In the television series Dexter , M99 is used by protagonist and serial killer Dexter Morgan to stun his victims with an injection. The sedative works within a few seconds and enables him to immobilize his victims for several hours. Both in the television series The Vampire Diaries , Ethorphin is used in season 5, episode 6, as well as in various episodes in the television series Scandal . Ethorphine is also used for several murders in the television series Lewis - Der Oxford Krimi , episode "Voices from Beyond". In Jacques Berndorf's novel Eifel-Filz, an M99 margarine mixture is painted on two crossbow arrows in order to subsequently kill two people. M99 is also used in Blue Bloods in season 2, episode 7 to stun and then strangle a person.

Trade names

Novartis : M99 (ZA), Wildlife Pharmaceuticals: Captivon (ZA)
Fixed combination with acepromazine : Novartis: Large Animal Immobilon (UK)

Individual evidence

↑ Template: CL Inventory / not harmonized There is not yet a harmonized classification for this substance . A labeling of Etorphine in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), which was retrieved on February 7, 2020, is reproduced from a self-classification by the distributor .
↑ ^a ^b Eberhard Schröder, Clemens Rufer, Ralph Schmiechen, Arzneimittelchemie I, Georg Thieme Verlag 1976, ISBN 3-13-520601-7 .
↑ Michael Kock, David Meltzer, Richard Burroughs: Chemical and Physical Restraint of Wild Animals: A Training and Field Manual for African Species. IWCS, 2006. ISBN 0-62035811-4 , ISBN 978-0-62035811-8 . P. 90 (PDF) .
^ GN Volans, BA Whittle: Letter: Accidental injection of Immobilon. In: British medical journal. Volume 2, Number 6033, August 1976, pp. 472-473, PMID 953617 . PMC 1687589 (free full text).

[1] Template: CL Inventory / not harmonized There is not yet a harmonized classification for this substance . A labeling of Etorphine in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), which was retrieved on February 7, 2020, is reproduced from a self-classification by the distributor .

[SRS-2] Eberhard Schröder, Clemens Rufer, Ralph Schmiechen, Arzneimittelchemie I, Georg Thieme Verlag 1976, ISBN 3-13-520601-7 .

[3] Michael Kock, David Meltzer, Richard Burroughs: Chemical and Physical Restraint of Wild Animals: A Training and Field Manual for African Species. IWCS, 2006. ISBN 0-62035811-4 , ISBN 978-0-62035811-8 . P. 90 (PDF) .

[PMID953617-4] GN Volans, BA Whittle: Letter: Accidental injection of Immobilon. In: British medical journal. Volume 2, Number 6033, August 1976, pp. 472-473, PMID 953617 . PMC 1687589 (free full text).