14-Hydroxymorphine

Last updated
14-Hydroxymorphine
14-Hydroxymorphine.svg
14-Hydroxymorphine molecule ball.png
Names
IUPAC name
17-Methyl-7,8-didehydro-4,5α-epoxymorphinan-3,6α,14-triol
Systematic IUPAC name
(4R,4aS,7S,7aR,12bS)-3-Methyl-2,3,4,4a,7,7a-hexahydro-1H-4,12-methano[1]benzofuro[3,2-e]isoquinoline-4a,7,9-triol
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
PubChem CID
UNII
  • InChI=1S/C17H19NO4/c1-18-7-6-16-13-9-2-3-10(19)14(13)22-15(16)11(20)4-5-17(16,21)12(18)8-9/h2-5,11-12,15,19-21H,6-8H2,1H3/t11-,12+,15-,16-,17+/m0/s1 Yes check.svgY
    Key: WYMBHLXUDPDGQJ-BRJGLHKUSA-N Yes check.svgY
  • InChI=1S/C17H19NO4/c1-18-7-6-16-13-9-2-3-10(19)14(13)22-15(16)11(20)4-5-17(16,21)12(18)8-9/h2-5,11-12,15,19-21H,6-8H2,1H3/t11-,12+,15-,16-,17+/m0/s1
    Key: 1S/C17H19NO4/c1-18-7-6-16-13-9-2-3-10(19)14(13)22-15(16)11(20)4-5-17(16,21)12(18)8-9/h2-5,11-12,15,19-21H,6-8H2,1H3/t11-,12+,15-,16-,17+/m0/s1
  • CN1CC[C@]23[C@@H]4[C@H](C=C[C@]2([C@H]1CC5=C3C(=C(C=C5)O)O4)O)O
Properties
C17H19NO3
Molar mass 301.34 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

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

  1. ↑ 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. PMC   187243 . PMID   172013.
  2. ↑ 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) e99231. Bibcode:2014PLoSO...999231B. doi: 10.1371/journal.pone.0099231 . ISSN   1932-6203. PMC   4053365 . PMID   24919067.
  3. ↑ Dumitrascuta, Maria; Bermudez, Marcel; Ben Haddou, Tanila; Guerrieri, Elena; Schläfer, Lea; Ritsch, Andreas; Hosztafi, Sandor; Lantero, Aquilino; Kreutz, Christoph; Massotte, Dominique; Schmidhammer, Helmut; Wolber, Gerhard; Spetea, Mariana (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". Scientific Reports. 10 (1): 5653. Bibcode:2020NatSR..10.5653D. doi:10.1038/s41598-020-62530-w. ISSN   2045-2322. PMC   7101422 . PMID   32221355.
  4. 1 2 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". ChemMedChem. 20 (4) e202400654. doi:10.1002/cmdc.202400654. ISSN   1860-7187. PMC   11831872 . PMID   39479891.
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