Article · Wikipedia archive · Last revised Jun 5, 2026

Oxymorphol

Oxymorphol is oxymorphone which has been hydrogenated at the 6-position and consists of a mixture of 4,5α-epoxy-17-methylmorphinan-3,6β,14-triol and 4,5α-epoxy-17-methylmorphinan-3,6α,14-triol (hydromorphinol). It is produced by the human body as an active metabolite of oxymorphone and some bacteria as an intermediate in turning morphine into hydromorphone. It can also be manufactured and is the subject of patents by drug companies looking for new semi-synthetic analgesics and cough suppressants.

Last revised
Jun 5, 2026
Read time
≈ 1 min
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187 w
Citations
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Source
Wikipedia ↗
Oxymorphol
Clinical data
Other names4,5α-Epoxy-17-methylmorphinan-3,6,14-triol
ATC code
Pharmacokinetic data
Metabolismhepatic
Identifiers
  • (5α)-17-Methyl-4,5-epoxymorphinan-3,6,14-triol
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC17H21NO4
Molar mass303.358 g·mol−1
3D model (JSmol)
  • CN1CC[C@]23c4c5ccc(c4O[C@H]2C(CC[C@]3([C@H]1C5)O)O)O
  • InChI=1S/C17H21NO4/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/h2-3,11-12,15,19-21H,4-8H2,1H3/t11?,12-,15+,16+,17-/m1/s1 checkY
  • Key:AABLHGPVOULICI-ZOFKVTQNSA-N checkY

Oxymorphol is oxymorphone which has been hydrogenated at the 6-position and consists of a mixture of 4,5α-epoxy-17-methylmorphinan-3,6β,14-triol and 4,5α-epoxy-17-methylmorphinan-3,6α,14-triol (hydromorphinol).1 It is produced by the human body as an active metabolite of oxymorphone and some bacteria as an intermediate in turning morphine into hydromorphone.2 It can also be manufactured and is the subject of patents by drug companies looking for new semi-synthetic analgesics and cough suppressants.

A derivative of oxymorphol, 8-hydroxy-6-α-oxymorphol, was discovered in the first decade of the 21st century and the subject of a patent application by Endo Pharmaceuticals for an analgesic and antitussive.3

References

References

  1. "α-Oxymorphol as "Hydromorphinol"".
  2. Cone EJ, Darwin WD, Buchwald WF, Gorodetzky CW (1983). "Oxymorphone metabolism and urinary excretion in human, rat, guinea pig, rabbit, and dog". Drug Metabolism and Disposition: The Biological Fate of Chemicals. 11 (5): 446–50. doi:10.1016/S0090-9556(25)08048-1. PMID 6194952.
  3. "OPIOID AND METHODS OF MAKING AND USING THE SAME - Patent application". www.faqs.org. Archived from the original on 2014-05-02.