14-Phenylpropoxymetopon

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.[1] PPOM is a highly potent analgesic drug several thousand times stronger than morphine, with an even higher in vivo potency than etorphine.[2] 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.[3]

14-Phenylpropoxymetopon
Clinical data
Other names14-Phenylpropoxymetopon, PPOM
Identifiers
IUPAC name
  • 3-Hydroxy-14-(3-phenylpropoxy)-5-methyl-7,8-dihydro-4,5α-epoxy-17-methylmorphinan-6-one
PubChem CID
ChemSpider
Chemical and physical data
FormulaC27H31NO4
Molar mass433.548 g·mol−1
3D model (JSmol)
SMILES
  • C[C@]12C(=O)CC[C@@]3([C@]14CCN([C@@H]3CC5=C4C(=C(C=C5)O)O2)C)OCCCC6=CC=CC=C6
InChI
  • InChI=1S/C27H31NO4/c1-25-22(30)12-13-27(31-16-6-9-18-7-4-3-5-8-18)21-17-19-10-11-20(29)24(32-25)23(19)26(25,27)14-15-28(21)2/h3-5,7-8,10-11,21,29H,6,9,12-17H2,1-2H3/t21-,25+,26+,27-/m1/s1 Y
  • Key:YLXOHYYZBORDAJ-NVSKSXHLSA-N Y
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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 most potent of fentanyl analogues and so would most likely cause pronounced tachyphylaxis following repeated dosing.

See also

References
  1. Spetea M, Schmidhammer H (September 2021). "Recent Chemical and Pharmacological Developments on 14-Oxygenated-N-methylmorphinan-6-ones". Molecules (Basel, Switzerland). 26 (18): 5677. doi:10.3390/molecules26185677. PMC 8464912. PMID 34577147.
  2. Schütz J, Spetea M, Koch M, Aceto MD, Harris LS, Coop A, Schmidhammer H (September 2003). "Synthesis and biological evaluation of 14-alkoxymorphinans. 20. 14-phenylpropoxymetopon: an extremely powerful analgesic". Journal of Medicinal Chemistry. 46 (19): 4182–7. doi:10.1021/jm030878b. PMID 12954070.
  3. Greiner E, Spetea M, Krassnig R, Schüllner F, Aceto M, Harris LS, et al. (April 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 Medicinal Chemistry. 46 (9): 1758–63. doi:10.1021/jm021118o. PMID 12699394.
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