14-Phenylpropoxymetopon

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14-Phenylpropoxymetopon
14-phenylpropoxymetopon.svg
Systematic (IUPAC) name
3-Hydroxy-14-(3-phenylpropoxy)-5-methyl-7,8-dihydro-4,5α-epoxy-17-methylmorphinan-6-one
Clinical data
Identifiers
PubChem CID 10238204
ChemSpider 8413692 YesY
Synonyms 14-Phenylpropoxymetopon, PPOM
Chemical data
Formula C27H31NO4
433.54 g/mol
 YesY (what is this?)  (verify)

14-Phenylpropoxymetopon (PPOM) is an opiate analogue that is a derivative of metopon which has been substituted with a γ-phenylpropoxy group at the 14-position. It is a highly potent analgesic drug several thousand times stronger than morphine, with a similar in vivo potency to etorphine.[1] The 14-phenylpropoxy substitution appears to confer potent μ-opioid agonist activity, even when combined with substitutions such as N-cyclopropyl or N-allyl, which normally result in μ-opioid antagonist compounds.[2]

It has never been used in humans, but would be expected to produce effects similar to those of other potent opioid agonists, including strong analgesia, sedation, euphoria, constipation, itching and respiratory depression which could be harmful or fatal. Tolerance and dependence would be expected to develop rapidly based on the potency of the drug, as it is of a similar strength to the potent fentanyl analogues and so would most likely cause pronounced tachyphylaxis following repeated dosing.

See also[edit]

References[edit]

  1. ^ Schütz, J; Spetea, M; Koch, M; Aceto, MD; Harris, LS; Coop, A; Schmidhammer, H (2003). "Synthesis and biological evaluation of 14-alkoxymorphinans. 20. 14-phenylpropoxymetopon: an extremely powerful analgesic". Journal of Medical Chemistry 46 (19): 4182–7. doi:10.1021/jm030878b. PMID 12954070. 
  2. ^ Greiner, E; Spetea, M; Krassnig, R; Schüllner, F; Aceto, M; Harris, LS; Traynor, JR; Woods, JH; Coop, A; Schmidhammer, H (2003). "Synthesis and biological evaluation of 14-alkoxymorphinans. 18. N-substituted 14-phenylpropyloxymorphinan-6-ones with unanticipated agonist properties: extending the scope of common structure-activity relationships". Journal of Medical Chemistry 46 (9): 1758–63. doi:10.1021/jm021118o. PMID 12699394.