Morphinone

Morphinone
Names
IUPAC name
(5α)-3-Hydroxy-17-methyl-7,8-didehydro-4,5-epoxy-morphinan-6-one
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.006.714
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PubChem CID
UNII
InChI
  • 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
SMILES
  • O=C1\C=C/[C@H]5[C@@H]4N(CC[C@@]52c3c(O[C@@H]12)c(O)ccc3C4)C
Properties
Chemical formula
 C17H17NO3
Molar mass 283.32 g/mol
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

Morphinone is itself not a very potent opioid but it is the intermediate when morphine is being converted to hydromorphone (trade name Dilaudid) which is 4-6 times as potent as morphine.

Chemical structure

Morphinone can be described as the ketone of morphine.

Morphinone itself is an active opioid although 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


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