Acetorphine

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
Clinical data
ATC code
  • none
Legal status
Legal status
  • AU: S9 (Prohibited substance)
  • CA: Schedule I
  • DE: Anlage I (Authorized scientific use only)
  • UK: Class A
  • US: Schedule I
  • UN: Narcotic Schedules I and IV
Identifiers
IUPAC name
  • 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
CompTox Dashboard (EPA)
ECHA InfoCard100.291.523
Chemical and physical data
FormulaC27H35NO5
Molar mass453.579 g·mol−1
3D model (JSmol)
SMILES
  • 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
  • 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 Y
  • Key:LFYBMMHFJIAKFE-PMEKXCSPSA-N Y
 NY (what is this?)  (verify)

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.

Australia

Acetorphine is a schedule 9 substance in Australia under the Poisons Standard (February 2017).[3] A schedule 9 drug is outlined in the Poisons Act 1964 as "Substances which may be abused or misused, the manufacture, possession, sale or use of which should be prohibited by law except when required for medical or scientific research, or for analytical, teaching or training purposes with approval of the CEO."[4]

Under the Misuse of Drugs Act 1981 6.0g is the amount required determining a court of trial, 2.0g is considered intent to sell and supply.[5]

Germany

Acetorphine is illegal in Germany (Anlage I)

United Kingdom

Acetorphine is considered a Class A drug by the UK Misuse of Drugs Act since 1971, making its unlawful possession and distribution illegal. Class A drugs are deemed to be the most dangerous.

United States

Acetorphine is a Schedule I controlled substance in the United States. Its DEA Administrative Controlled Substances Control Number is 9319 and the one salt in use, acetorphine hydrochloride, has a freebase conversion ratio of 0.93.

Italy

In Italy Acetorphine is illegal, as are the parent compounds Etorphine and Dihydroetorphine. (Data from 2022)[6]

See also

References
  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. UNODC. 1968 (2): 51–52. 1968.
  3. "Poisons Standard". Federal Register of Legislation. Australian Government. October 2015.
  4. "Poisons Act" (PDF). Western Australia. 1964. Archived from the original (PDF) on 2015-12-22.
  5. "Misuse of Drugs Act" (PDF). Western Australia. 1981. Archived from the original (PDF) on 2015-12-22.
  6. Salute, Ministero della. "Tabelle delle sostanze stupefacenti e psicotrope". www.salute.gov.it (in Italian). Retrieved 2022-04-09.


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