Structure via PubChem · Public domain (PubChem)
(−)-etorphine
Sign in to saveAlso known as (-)-etorphine, (αR,5α,7α)-4,5-epoxy-3-hydroxy-6-methoxy-α,17-dimethyl-α-propyl-6,14-ethenomorphinan-7-methanol
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 the related plants Papaver orientale and Papaver bracteatum. It was reproduced in 1963 by a research group at MacFarlan Smith in Edinburgh, led by Kenneth Bentley. It can be produced from thebaine.
Chemical data
- Formula
- C25H33NO4
- Molecular weight
- 411.5 g/mol
- IUPAC name
- (1R,2S,6R,14R,15R,19R)-19-[(2R)-2-hydroxypentan-2-yl]-15-methoxy-5-methyl-13-oxa-5-azahexacyclo[13.2.2.12,8.01,6.02,14.012,20]icosa-8(20),9,11,16-tetraen-11-ol
- SMILES
- CCC[C@](C)([C@H]1C[C@@]23C=C[C@@]1([C@H]4[C@@]25CCN([C@@H]3CC6=C5C(=C(C=C6)O)O4)C)OC)O
- InChIKey
- CAHCBJPUTCKATP-FAWZKKEFSA-N
- XLogP
- 3.1
- Polar surface area
- 62.2 Ų
- H-bond donors
- 2
- H-bond acceptors
- 5
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Phase 2
- Molecule type
- Small molecule
via ChEMBL · EBI
Research
1,138 papers- Effects of Butorphanol on Respiration in White Rhinoceros (Ceratotherium simum) Immobilized with Etorphine-Azaperone.Journal of wildlife diseases · 2024
- Etorphine poisoning.South African medical journal = Suid-Afrikaanse tydskrif vir geneeskunde · 2003
- Effect of Azaperone on Induction Times in Etorphine-Immobilized White Rhinoceros (Ceratotherium simum).Journal of wildlife diseases · 2022
- Immobilon: curiously strong.Lancet (London, England) · 1977
- Immobilization of white-tailed deer by etorphine and xylazine and its antagonism by nalmefene and yohimbine.Journal of wildlife diseases · 1987
via PubMed
Wikidata facts
- Mass
- 411.240958536
Show 5 more facts
- chemical formula
- C₂₅H₃₃NO₄
- canonical SMILES
- CCCC(C)(C1CC23C=CC1(C4C25CCN(C3CC6=C5C(=C(C=C6)O)O4)C)OC)O
- subject has role
- narcotic
- Commons category
- Etorphine
- isomeric SMILES
- O(C)[C@@]12[C@]3([C@@]45[C@@]([C@@H](CC6=C4C(O3)=C(O)C=C6)N(C)CC5)(C[C@@]1([C@](CCC)(C)O)[H])C=C2)[H]
via Wikidata · CC0
~5 min read
Encyclopedic overview
7 sectionsContents
- Veterinary use
- Pharmacology
- Legal status
- In popular culture
- See also
- References
- External links
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 the related plants Papaver orientale and Papaver bracteatum. It was reproduced in 1963 by a research group at MacFarlan Smith in Edinburgh, led by Kenneth Bentley. It can be produced from thebaine.
== Veterinary use == Etorphine is available legally only for veterinary use and is strictly governed by law. It is often used to immobilise elephants 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.
Excerpted from Wikipedia’s “(−)-etorphine” article, available under the CC BY-SA 4.0 licence.