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).[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.

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
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

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
  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. 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.
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