Drotebanol

Drotebanol
Clinical data
Other names	Drotebanol, Oxymethebanol
AHFS/Drugs.com	International Drug Names
ATC code	none;
Legal status
Legal status	AU: S8 (Controlled drug); CA: Schedule I; DE: Anlage I (Authorized scientific use only); US: Schedule I;
Identifiers
	IUPAC name 3,4-Dimethoxy-9a-methylmorphinan-6β,14-diol;
CAS Number	3176-03-2 ;
PubChem CID	5463863;
ChemSpider	16736125 ;
UNII	7RS2Q8MCK8;
KEGG	D01496 ;
ChEMBL	ChEMBL2104603 ;
CompTox Dashboard (EPA)	DTXSID301017908 ;
Chemical and physical data
Formula	C19H27NO4
Molar mass	333.42 g/mol g·mol−1
3D model (JSmol)	Interactive image;
Melting point	165 to 167 °C (329 to 333 °F)
	SMILES CN1CC[C@]23C[C@@H](CC[C@]2([C@H]1CC4=C3C(=C(C=C4)OC)OC)O)O;
	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 ; Key:LCAHPIFLPICNRW-SVYNMNNPSA-N ;
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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.

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

^ 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.
^ 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.

[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.

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