Drotebanol

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Drotebanol
Drotebanol.svg
Systematic (IUPAC) name
3,4-Dimethoxy-9a-methylmorphinan-6β,14-diol
Clinical data
AHFS/Drugs.com International Drug Names
Legal status Controlled (S8) (AU) Schedule I (US)
Identifiers
CAS number 3176-03-2 N
ATC code None
PubChem CID 5463863
ChemSpider 16736125 YesY
UNII 7RS2Q8MCK8 YesY
KEGG D01496 YesY
Synonyms Drotebanol, Oxymethebanol
Chemical data
Formula C19H27NO4 
Mol. mass 333.42 g/mol
Physical data
Melt. point 165–167 °C (329–333 °F)
 N (what is this?)  (verify)

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.

It is currently a Schedule I Narcotic controlled substance in the United States with a DEA ACSCN of 9335 and an annual aggregate manufacturing quota of zero.

References[edit]

  1. ^ Kobayashi, S; Hasegawa, K; Mori, M; Takagi, H (1970). "Pharmacological studies on a new specifically potent antitussive agent, 14-hydroxydihydro-6 beta-thebainol-4-methylether (oxymethebanol)". Arzneimittel-Forschung 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.