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. 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]

14-Phenylpropoxymetopon

Clinical data
Other names	14-Phenylpropoxymetopon, PPOM
Identifiers
IUPAC name 3-Hydroxy-14-(3-phenylpropoxy)-5-methyl-7,8-dihydro-4,5α-epoxy-17-methylmorphinan-6-one
PubChem CID	10238204
ChemSpider	8413692 Y
Chemical and physical data
Formula	C27H31NO4
Molar mass	433.54 g/mol g·mol−1
3D model (JSmol)	Interactive image
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 potent fentanyl analogues and so would most likely cause pronounced tachyphylaxis following repeated dosing.