14-Phenylpropoxymetopon

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IUPAC_name = 3-hydroxy-14-(3-phenylpropoxy)-5-methyl-7,8-dihydro-4,5α-epoxy-17-methylmorphinan-6-one

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synonyms = 14-Phenylpropoxymetopon, PPOM
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PubChem = 10238204
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C = 27 | H = 31 | N = 1 | O = 4
molecular_weight = 433.54 g/mol
smiles = C [C@] 12C(=O)CC [C@@] 3( [C@] 14CCN( [C@@H] 3CC5=C4C(=C(C=C5)O)O2)C)OCCCC6=CC=CC=C6
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14-Phenylpropoxymetopon (PPOM) is an opiate analogue that is an 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. [Schütz J, Spetea M, Koch M, Aceto MD, Harris LS, Coop A, Schmidhammer H. Synthesis and biological evaluation of 14-alkoxymorphinans. 20. 14-phenylpropoxymetopon: an extremely powerful analgesic. "Journal of Medicinal Chemistry". 2003 Sep 11;46(19):4182-7. PMID 12954070] 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. [Greiner E, Spetea M, Krassnig R, Schüllner F, Aceto M, Harris LS, Traynor JR, Woods JH, Coop A, Schmidhammer H. 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". 2003 Apr 24;46(9):1758-63. PMID 12699394]

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.

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