Oxymorphol
Iupac name(5α)-17-Methyl-4,5-epoxymorphinan-3,6,14-triol
Metabolismhepatic
Cas number54934-75-7
Atc prefixN02
Atc suffixA
Pubchem6712731
Chemspiderid5144767
Unii67P6D5Q6YK
Chembl1968360
C17
H21
N1
O4
SmilesCN1CC[C@]23c4c5ccc(c4O[C@H]2C(CC[C@]3([C@H]1C5)O)O)O
Stdinchi1S/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
StdinchikeyAABLHGPVOULICI-ZOFKVTQNSA-N
Synonyms4,5α-Epoxy-17-methylmorphinan-3,6,14-triol

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

  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.