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. 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 names	4,5α-Epoxy-17-methylmorphinan-3,6,14-triol
ATC code	N02A (WHO)
Pharmacokinetic data
Metabolism	hepatic
Identifiers
IUPAC name (5α)-17-Methyl-4,5-epoxymorphinan-3,6,14-triol
CAS Number	54934-75-7
PubChem CID	6712731
ChemSpider	5144767
UNII	67P6D5Q6YK
ChEMBL	ChEMBL1968360^Y
Chemical and physical data
Formula	C17H21NO4
Molar mass	303.358 g·mol^−1
3D model (JSmol)	Interactive image
SMILES CN1CC[C@]23c4c5ccc(c4O[C@H]2C(CC[C@]3([C@H]1C5)O)O)O
InChI 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^Y Key:AABLHGPVOULICI-ZOFKVTQNSA-N^Y

A derivative of oxymorphol, 8-hydroxy-6-α-oxymorphol, was discovered in the first decade of this century and the subject of a patent application by Endo for an analgesic and antitussive.[2]

References

1. α-Oxymorphol as "Hydromorphinol"
2. http://www.faqs.org/patents/app/20090018154