14-Methoxymetopon

14-Methoxymetopon

14-Methoxymetopon
chemical structure
Systematic (IUPAC) name
3-Hydroxy-14-methoxy-5,17-dimethyl-7,8-dihydro-4,5α-epoxy-morphinan-6-one
Identifiers
CAS Registry Number  N
PubChem CID:
ChemSpider  YesY
ChEMBL  YesY
Synonyms 14-Methoxymetopon
Chemical data
Formula C19H23NO4
Molecular mass 329.39 g/mol
 N   

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
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