Drotebanol

Drotebanol

Systematic (IUPAC) name
3,4-dimethoxy- 9a-methylmorphinan- 6β,14-diol
Clinical data
AHFS/Drugs.com	International Drug Names
Pregnancy cat.	?
Legal status	Schedule I (US)
Identifiers
CAS number	3176-03-2 N
ATC code	None
PubChem	CID 5463863
ChemSpider	16736125 Y
UNII	7RS2Q8MCK8 Y
KEGG	D01496 Y
Synonyms	Drotebanol, Oxymethebanol
Chemical data
Formula	C19H27NO4
Mol. mass	333.42 g/mol
SMILES	eMolecules & PubChem
InChI InChI=1S/C19H27NO4/c1-20-9-8-18-11-13(21)6-7-19(18,22)15(20)10-12-4-5-14(23-2)17(24-3)16(12)18/h4-5,13,15,21-22H,6-11H2,1-3H3/t13-,15-,18-,19-/m1/s1 Y Key:LCAHPIFLPICNRW-SVYNMNNPSA-N Y
Physical data
Melt. point	165–167 °C (329–333 °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

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.