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Drotebanol
Systematic (IUPAC) name
3,4-dimethoxy- 9a-methylmorphinan- 6β,14-diol
Identifiers
CAS number 3176-03-2
ATC code none
PubChem 5463863
Chemical data
Formula C 19H27NO4  
Mol. mass 333.42 g/mol
SMILES eMolecules & PubChem
Synonyms Drotebanol, Oxymethebanol
Physical data
Melt. point 165–167 °C (329–333 °F)
Pharmacokinetic data
Bioavailability  ?
Metabolism  ?
Half life  ?
Excretion  ?
Therapeutic considerations
Pregnancy cat.  ?
Legal status Schedule I (US)
Routes  ?

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.[1] 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.[2] It was previously marketed for human use under the brand name Metebanyl, although it is now no longer used in medicine.

References

  1. ^ Kobayashi S, Hasegawa K, Mori M, Takagi H. Pharmacological studies on a new specifically potent antitussive agent, 14-hydroxydihydro-6 beta-thebainol-4-methylether (oxymethebanol). Arzneimittelforschung. 1970 Jan;20(1):43-6. PMID 5467447
  2. ^ Yanagita T, Miyasato K, Oinuma N, Kiyohara H. Dependence potential of drotebanol, codeine and thebaine tested in rhesus monkeys. UNODC Bulletin on Narcotics. 1977 Issue 1.
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