14-Methoxydihydromorphinone

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14-Methoxydihydromorphinone
14-methoxydihydromorphinone.svg
Names
IUPAC name
3-Hydroxy-14-methoxy-17-methyl-4,5α-epoxymorphinan-6-one
Systematic IUPAC name
(4R,4aS,7aR,12bS)-9-Hydroxy-4a-methoxy-3-methyl-2,3,4,4a,5,6-hexahydro-1H-4,12-methano[1]benzofuro[3,2-e]isoquinolin-7(7aH)-one
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
PubChem CID
  • InChI=1S/C18H21NO4/c1-19-8-7-17-14-10-3-4-11(20)15(14)23-16(17)12(21)5-6-18(17,22-2)13(19)9-10/h3-4,13,16,20H,5-9H2,1-2H3/t13-,16+,17+,18-/m1/s1
    Key: FCIDDJPMOSRHJG-XFKAJCMBSA-N
  • CO[C@]12CCC(=O)[C@@H]3OC4=C5C(C[C@H]1N(C)CC[C@@]235)=CC=C4O
Properties
C18H21NO4
Molar mass 315.369 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

14-Methoxydihydromorphinone is a semi-synthetic opioid related to 14-methoxymetopon (14-MM), an opioid with a Ki of 0.15 nM, and 14-O-methyloxymorphone (14-OMO) with a Ki of 0.10 nM. By contrast, oxymorphone has a Ki of 0.97 nM and morphine one of 6.55 nM (all at mu receptors). This suggests that both 14-OMO and 14-MM have a higher mu/kappa selectivity than oxymorphone. [1] [2]

See also

References

  1. ↑ Spetea, M; Bohotin, CR; Asim, MF; Stübegger, K; Schmidhammer, H (2010). "In vitro and in vivo pharmacological profile of the 5-benzyl analogue of 14-methoxymetopon, a novel mu opioid analgesic with reduced propensity to alter motor function". Eur J Pharm Sci. 41 (1): 125–135. doi:10.1016/j.ejps.2010.05.018. PMC   2954314 . PMID   20600882.
  2. ↑ Schmidhammer, H; Spetea, M (2011). Synthesis of 14-alkoxymorphinan derivatives and their pharmacological actions. Topics in Current Chemistry. Vol. 299. pp. 63–91. Bibcode:2011chop.book...63S. doi:10.1007/128_2010_77. ISBN   978-3-642-18106-1. PMID   21630508.


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