Xorphanol

Xorphanol

Systematic (IUPAC) name
N-(Cyclobutylmethyl)-8β-methyl-6-methylenemorphinan-3-ol
Identifiers
CAS Number	77287-89-9 Y
ATC code	none
PubChem	CID: 5488631
ChemSpider	20121496 N
UNII	L415991P58 Y
Chemical data
Formula	C23H31NO
Molecular mass	337.498 g/mol
SMILES C[C@H]1CC(=C)C[C@@]23[C@@H]1[C@@H](CC4=C2C=C(C=C4)O)N(CC3)CC5CCC5
InChI InChI=1S/C23H31NO/c1-15-10-16(2)22-21-11-18-6-7-19(25)12-20(18)23(22,13-15)8-9-24(21)14-17-4-3-5-17/h6-7,12,16-17,21-22,25H,1,3-5,8-11,13-14H2,2H3/t16-,21+,22-,23+/m0/s1 N Key:AZJPPZHRNFQRRE-AZIXLERZSA-N N
NY (what is this?)  (verify)

Xorphanol (TR-5379) is an opioid analgesic from the morphinan family of drugs. It is a mixed agonist–antagonist at the μ-opioid receptor and produces potent analgesic effects with little potential for dependence or abuse.

Side effects in animal studies were relatively mild, with only sedation and nausea being prominent, although it also produced convulsions at the highest dose tested. However human trials revealed additional side effects such as headaches and euphoria, and this was the subject of a lawsuit between the drug's inventors and the company to which they had licensed the marketing rights, which claimed that these side effects had not been revealed to them during the license negotiations. This dispute resulted in the drug never being marketed commercially, although it is still used in scientific research.

See also

• 6-Methylenedihydrodesoxymorphine
• Butorphanol
• Nalmefene