Drotebanol

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Drotebanol
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Systematic (IUPAC) name
3,4-dimethoxy- 9a-methylmorphinan- 6β,14-diol
Legal status
Legal status
Identifiers
CAS Number 3176-03-2
ATC code none
PubChem CID 5463863
Synonyms Drotebanol, Oxymethebanol
Chemical data
Formula C19H27NO4
Molar mass 333.42 g/mol[[Script error: No such module "String".]]
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Physical data
Melting point 165 to 167 °C (329 to 333 °F)
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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

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  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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