14-Methoxymetopon

14-Methoxymetopon
Systematic (IUPAC) name
3-Hydroxy-14-methoxy-5,17-dimethyl-7,8-dihydro-4,5α-epoxy-morphinan-6-one
Clinical data
Identifiers
131575-03-6 
PubChem CID 5486940
ChemSpider 4589140 Yes
ChEMBL CHEMBL326684 Yes
Synonyms 14-Methoxymetopon
Chemical data
Formula C19H23NO4
329.39 g/mol
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14-Methoxymetopon is an opiate analogue developed by a team led by Professor Helmut Schmidhammer at the University of Insbruck in the mid 1990s.[1] It is a derivative of metopon in which a methoxy group has been inserted at the 14-position. It is a highly potent analgesic drug that is around 500x stronger than morphine when administered systemically; however, when given spinally or supraspinally, it exhibits analgesic activity up to a million fold greater than morphine.[2] It binds strongly to the μ-opioid receptor and activates it to a greater extent than most similar opioid drugs.[3] This produces an unusual pharmacological profile, and although 14-methoxymetopon acts as a potent μ-opioid full agonist in regards to some effects such as analgesia, a ceiling effect is seen on other effects such as constipation and respiratory depression which is believed to involve interaction with the κ-opioid receptor[4]

References

  1. ↑ US Patent 5886001 - Agonist compounds
  2. ↑ King, MA; Su, W; Nielan, CL; Chang, AH; Schütz, J; Schmidhammer, H; Pasternak, GW (2003). "14-Methoxymetopon, a very potent mu-opioid receptor-selective analgesic with an unusual pharmacological profile". European Journal of Pharmacology 459 (2–3): 203–9. doi:10.1016/S0014-2999(02)02821-2. PMID 12524147.
  3. ↑ Mahurter, L; Garceau, C; Marino, J; Schmidhammer, H; Tóth, G; Pasternak, GW (2006). "Separation of binding affinity and intrinsic activity of the potent mu-opioid 14-methoxymetopon". The Journal of Pharmacology and Experimental Therapeutics 319 (1): 247–53. doi:10.1124/jpet.106.105395. PMID 16801454.
  4. ↑ Freye, E; Schmidhammer, H; Latasch, L (2000). "14-methoxymetopon, a potent opioid, induces no respiratory depression, less sedation, and less bradycardia than sufentanil in the dog". Anesthesia and Analgesia 90 (6): 1359–64. doi:10.1097/00000539-200006000-00018. PMID 10825321.