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]
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.
^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. PMC8464912. PMID 34577147.
^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.
^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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phenylpropoxymetopon, ppom, opiate, analogue, that, derivative, metopon, which, been, substituted, with, phenylpropoxy, group, position, ppom, highly, potent, analgesic, drug, several, thousand, times, stronger, than, morphine, with, even, higher, vivo, potenc. 14 Phenylpropoxymetopon PPOM is an opiate analogue that is a derivative of metopon which has been substituted with a g 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 m opioid agonist activity even when combined with substitutions such as N cyclopropyl or N allyl which normally result in m opioid antagonist compounds 3 14 PhenylpropoxymetoponClinical dataOther names14 Phenylpropoxymetopon PPOMIdentifiersIUPAC name 3 Hydroxy 14 3 phenylpropoxy 5 methyl 7 8 dihydro 4 5a epoxy 17 methylmorphinan 6 onePubChem CID10238204ChemSpider8413692 YChemical and physical dataFormulaC 27H 31N O 4Molar mass433 548 g mol 13D model JSmol Interactive imageSMILES C C 12C O CC C 3 C 14CCN C H 3CC5 C4C C C C5 O O2 C OCCCC6 CC CC C6InChI 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 YKey YLXOHYYZBORDAJ NVSKSXHLSA N Y verify 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 Edit14 Cinnamoyloxycodeinone 7 PET N Phenethylnormorphine N Phenethyl 14 ethoxymetopon Phenomorphan RAM 378 Ro4 1539References Edit 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 Schutz 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 Greiner E Spetea M Krassnig R Schullner 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 This analgesic related article is a stub You can help Wikipedia by expanding it vte Retrieved from https en wikipedia org w index php title 14 Phenylpropoxymetopon amp oldid 1090192926, wikipedia, wiki, book, books, library,
