Morphinone

Morphinone is an opioid that is the intermediate when morphine is being converted to hydromorphone (trade name Dilaudid).[1]

Morphinone
Structural formula
Space-filling model
Names
IUPAC name
(5α)-3-Hydroxy-17-methyl-7,8-didehydro-4,5-epoxy-morphinan-6-one
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.006.714
KEGG
UNII
  • InChI=1S/C17H17NO3/c1-18-7-6-17-10-3-5-13(20)16(17)21-15-12(19)4-2-9(14(15)17)8-11(10)18/h2-5,10-11,16,19H,6-8H2,1H3/t10-,11+,16-,17-/m0/s1 checkY
    Key: PFBSOANQDDTNGJ-YNHQPCIGSA-N checkY
  • InChI=1/C17H17NO3/c1-18-7-6-17-10-3-5-13(20)16(17)21-15-12(19)4-2-9(14(15)17)8-11(10)18/h2-5,10-11,16,19H,6-8H2,1H3/t10-,11+,16-,17-/m0/s1
    Key: PFBSOANQDDTNGJ-YNHQPCIGBO
  • O=C1\C=C/[C@H]5[C@@H]4N(CC[C@@]52c3c(O[C@@H]12)c(O)ccc3C4)C
Properties
C17H17NO3
Molar mass 283.327 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Chemical structure

Morphinone can be described as the ketone of morphine.

Morphinone itself is an active opioid, though its potency is closer to codeine than morphine. It is, however, an important precursor and would fall under the purview of the Controlled Substances Act within the United States. Its legal status in other countries varies.

References
  1. Hung-Wen (Ben) Liu and Tadhg P. Begley, ed. (2020). Comprehensive Natural Products III. ISBN 978-0-08-102691-5.
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