Chemistry:14-Hydroxymorphine
From HandWiki
14-Hydroxymorphine is a semi-synthetic opioid, chemical compound closely related to alkaloid morphine, characterized by an additional hydroxyl group at the 14th position.
It is a potential precursor or metabolite of other potent opioids,[1] such as oxymorphone (which is 14-hydroxydihydromorphinone). Its chemical structure includes the basic morphine skeleton with additional complexity at the 14th carbon atom, It is primarily of interest in chemical and pharmacological research as an intermediate in the synthesis of more potent semi-synthetic opioids.[2][3][4]
14-hydroxymorphine acts primarily as a μ-opioid receptor (MOR) agonist. It also exhibits some activity at other opioid receptors, but its primary action is at the MOR.[4]
References
- ↑ Liras, P.; Kasparian, S. S.; Umbreit, W. W. (October 1975). "Enzymatic transformation of morphine by hydroxysteroid dehydrogenase from Pseudomonas testosteroni". Applied Microbiology 30 (4): 650–656. doi:10.1128/am.30.4.650-656.1975. ISSN 0003-6919. PMID 172013.
- ↑ Ben Haddou, Tanila; Béni, Szabolcs; Hosztafi, Sándor; Malfacini, Davide; Calo, Girolamo; Schmidhammer, Helmut; Spetea, Mariana (2014). "Pharmacological investigations of N-substituent variation in morphine and oxymorphone: opioid receptor binding, signaling and antinociceptive activity". PLOS ONE 9 (6). doi:10.1371/journal.pone.0099231. ISSN 1932-6203. PMID 24919067. Bibcode: 2014PLoSO...999231B.
- ↑ Dumitrascuta, Maria; Bermudez, Marcel; Ben Haddou, Tanila; Guerrieri, Elena; Schläfer, Lea; Ritsch, Andreas; Hosztafi, Sandor; Lantero, Aquilino et al. (2020-03-27). "N-Phenethyl Substitution in 14-Methoxy-N-methylmorphinan-6-ones Turns Selective µ Opioid Receptor Ligands into Dual µ/δ Opioid Receptor Agonists" (in en). Scientific Reports 10 (1): 5653. doi:10.1038/s41598-020-62530-w. ISSN 2045-2322. PMID 32221355. Bibcode: 2020NatSR..10.5653D.
- ↑ 4.0 4.1 Malik, Alaa; Hosztafi, Sándor; Vincze, Anna; Marton, András; Kraszni, Márta; Balogh, György T.; Noszál, Béla; Mazák, Károly (2025). "Characterization of Opioid Agonist Morphine Derivatives with Emphasis on Medicinal Chemistry" (in en). ChemMedChem 20 (4). doi:10.1002/cmdc.202400654. ISSN 1860-7187. PMID 39479891.
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