Structure via PubChem · Public domain (PubChem)
drotebanol
Sign in to saveDrotebanol (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.
Chemical data
- Formula
- C19H27NO4
- Molecular weight
- 333.4 g/mol
- IUPAC name
- (1R,9R,10S,13R)-3,4-dimethoxy-17-methyl-17-azatetracyclo[7.5.3.01,10.02,7]heptadeca-2(7),3,5-triene-10,13-diol
- SMILES
- CN1CC[C@]23C[C@@H](CC[C@]2([C@H]1CC4=C3C(=C(C=C4)OC)OC)O)O
- InChIKey
- LCAHPIFLPICNRW-SVYNMNNPSA-N
- XLogP
- 1.6
- Polar surface area
- 62.2 Ų
- H-bond donors
- 2
- H-bond acceptors
- 5
- Formal charge
- 0
via PubChem
Research
2 papers- Dependence potential of drotebanol, codeine and thebaine tested in rhesus monkeys.Bulletin on narcotics · 1977
- Effect of the centrally acting antitussives on ascites tumor cells.Japanese journal of pharmacology · 1983
via PubMed
Wikidata facts
- Subclass of
- chemical compound
- Mass
- 333.194
Show 5 more facts
- subject has role
- narcotic
- chemical formula
- C₁₉H₂₇NO₄
- canonical SMILES
- CN1CCC23CC(CCC2(C1CC4=C3C(=C(C=C4)OC)OC)O)O
- isomeric SMILES
- CN1CC[C@]23C[C@@H](CC[C@]2([C@H]1CC4=C3C(=C(C=C4)OC)OC)O)O
- has characteristic
- bitterness
Sources (2)
via Wikidata · CC0
~1 min read
Encyclopedic overview
1 sectionsContents
- References
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.
Excerpted from Wikipedia’s “drotebanol” article, available under the CC BY-SA 4.0 licence.