Drotebanol

Drotebanol

Clinical data
Synonyms	Drotebanol, Oxymethebanol
Legal status
Legal status	US: Schedule I
Identifiers
IUPAC name 3,4-dimethoxy-9a-methylmorphinan-6β,14-diol
CAS Number	3176-03-2
PubChem CID	5463863
E number	{{#property:P628}}
ECHA InfoCard	{{#property:P2566}}
Chemical and physical data
Formula	C19H27NO4
Molar mass	333.42 g/mol
3D model (JSmol)	Interactive image
Melting point	165 to 167 °C ( °F)
SMILES CN1CC[C@]23C[C@@H](CC[C@]2([C@H]1CC4=C3C(=C(C=C4)OC)OC)O)O

Editor-In-Chief: C. Michael Gibson, M.S., M.D. [1]

Overview

Drotebanol (Oxymethebanol) is a morphinan derivative that acts as an opioid agonist. It was invented by Sankyo Company in Japan during the 1970s. It is synthesised from thebaine.

Drotebanol has powerful antitussive (cough suppressant) effects, and is around 10x more potent than codeine in producing this effect. It also has analgesic effects several times stronger than codeine, but weaker than morphine. In animal studies it was found to be moderately addictive and produced limited physical dependence, but not as severe as that seen with morphine or pethidine. It was previously marketed for human use under the brand name Metebanyl, although it is now no longer used in medicine.