Acetorphine

Acetorphine
Clinical data
ATC code
  • none
Legal status
Legal status
Identifiers
  • 4,5α-epoxy-7α-(1-hydroxy-1-methylbutyl)-6-methoxy-17-methyl-6,14-endo-ethenomorphinan-3-yl acetate
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
CompTox Dashboard (EPA)
ECHA InfoCard100.291.523 Edit this at Wikidata
Chemical and physical data
FormulaC27H35NO5
Molar mass453.579 g·mol−1
3D model (JSmol)
  • C[C@@](O)(CCC)[C@H]6C[C@]43/C=C/[C@]6(OC)[C@@H]1Oc5c2c(C[C@H]4N(C)CC[C@@]123)ccc5OC(C)=O
  • InChI=1S/C27H35NO5/c1-6-9-24(3,30)19-15-25-10-11-27(19,31-5)23-26(25)12-13-28(4)20(25)14-17-7-8-18(32-16(2)29)22(33-23)21(17)26/h7-8,10-11,19-20,23,30H,6,9,12-15H2,1-5H3/t19-,20-,23-,24-,25-,26+,27-/m1/s1 checkY
  • Key:LFYBMMHFJIAKFE-PMEKXCSPSA-N checkY
 ☒NcheckY (what is this?)  (verify)

Acetorphine is a potent opioid analgesic, up to 8700 times stronger than morphine by weight.[1] It is a derivative of the more well-known opioid etorphine, which is used as a very potent veterinary painkiller and anesthetic medication, primarily for the sedation of large animals such as elephants, giraffes and rhinos.

Acetorphine was developed in 1966 by the Reckitt research group that developed etorphine. Acetorphine was developed for the same purpose as etorphine itself, namely as a strong tranquilizer for use in immobilizing large animals in veterinary medicine. Despite showing some advantages over etorphine, for instance producing less toxic side effects in giraffes,[2] acetorphine was never widely adopted for veterinary use, and etorphine (along with other tranquilizers such as carfentanil and azaperone) remains the drug of choice in this application.

  1. ^ 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". Journal of the American Chemical Society. 89 (13): 3281–92. doi:10.1021/ja00989a032. PMID 6042764.
  2. ^ "The case of etorphine and acetorphine". Bulletin on Narcotics. 1968 (2). UNODC: 51–52. 1968.