14-Phenylpropoxymetopon

Chemical compound changed 477209024 3-Hydroxy-14-(3-phenylpropoxy)-5-methyl-7,8-dihydro-4,5α-epoxy-17-methylmorphinan-6-one 14-phenylpropoxymetopon.svg skin-invert-image 220 10238204 correct drugbank correct chemspider 8413692 1672083 27 31 1 4 C[C@]12C(=O)CC[C@@]3([C@]14CCN([C@@H]3CC5=C4C(=C(C=C5)O)O2)C)OCCCC6=CC=CC=C6 correct chemspider 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 correct chemspider YLXOHYYZBORDAJ-NVSKSXHLSA-N 14-Phenylpropoxymetopon, PPOM 14-Phenylpropoxymetopon (PPOM) is an opioid analogue that is a derivative of metopon which has been substituted with a γ-phenylpropoxy group at the 14-position. Spetea M, Schmidhammer H Recent Chemical and Pharmacological Developments on 14-Oxygenated-N-methylmorphinan-6-ones Molecules (Basel, Switzerland) 26 18 September 2021 5677 34577147 10.3390/molecules26185677 8464912 free PPOM is a highly potent analgesic drug several thousand times stronger than morphine, with an even higher in vivo potency than 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 46 19 4182–7 September 2003 12954070 10.1021/jm030878b 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 6 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 April 2003 12699394 10.1021/jm021118o 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 14-Cinnamoyloxycodeinone 7-PET N-Phenethylnormorphine N-Phenethyl-14-ethoxymetopon Phenomorphan RAM-378 Ro4-1539 References Category:4,5-Epoxymorphinans Category:Hydroxyarenes Category:Ethers Category:Ketones Category:Mu-opioid receptor agonists Category:Semisynthetic opioids