Etorphine

Etorphine
Clinical data
AHFS/Drugs.comInternational Drug Names
ATCvet code
Legal status
Legal status
  • AU: S9 (Prohibited substance)
  • BR: Class F1 (Prohibited narcotics)
  • CA: Schedule I
  • DE: Anlage III (Special prescription form required)
  • UK: Class A
  • US: Schedule I and Schedule II
  • UN: Narcotic Schedules I and IV
  • EU: List I (Netherlands)
Identifiers
IUPAC name
  • (5α,6β,14β,18R)-18-[(2R)-2-Hydroxy-2-pentanyl]-6-methoxy-17-methyl-7,8-didehydro-18,19-dihydro-4,5-epoxy-6,14-ethenomorphinan-3-ol
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.035.017
Chemical and physical data
FormulaC25H33NO4
Molar mass411.542 g·mol−1
3D model (JSmol)
SMILES
  • C[C@](CCC)(O)[C@H]1C[C@]23C=C[C@]1(OC)[C@@H]4Oc5c(O)ccc6C[C@H]2N(C)CC[C@]43c65
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 Y
  • Key:CAHCBJPUTCKATP-FAWZKKEFSA-N Y
 NY (what is this?)  (verify)

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.