Oxymorphol

Oxymorphol

Systematic (IUPAC) name
(5α)-17-Methyl-4,5-epoxymorphinan-3,6,14-triol
Pharmacokinetic data
Metabolism	hepatic
Identifiers
CAS Number	54934-75-7
ATC code	N02A (WHO)
PubChem	CID 6712731
ChemSpider	5144767
ChEMBL	CHEMBL1968360
Synonyms	4,5α-Epoxy-17-methylmorphinan-3,6,14-triol
Chemical data
Formula	C17H21NO4
Molar mass	303.35 g/mol
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 Key:AABLHGPVOULICI-ZOFKVTQNSA-N

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.

A derivatve 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