Drotebanol

Title: Drotebanol
CAS Registry Number: 3176-03-2
CAS Name: (6b)-3,4-Dimethoxy-17-methylmorphinan-6,14-diol
Additional Names: 6b,14-dihydroxy-3,4-dimethoxy-N-methylmorphinan; 14-hydroxydihydro-6b-thebainol 4-methyl ether; dihydro-14-hydroxy-4-O-methyl-6b-thebainol; dihydro-14-hydroxy-6b-thebainol 4-methyl ether; oxymethebanol
Trademarks: Metebanyl (Sankyo)
Molecular Formula: C19H27NO4
Molecular Weight: 333.42
Percent Composition: C 68.44%, H 8.16%, N 4.20%, O 19.19%
Literature References: Prepn from thebaine: JP 64 26726 (1964 to Sankyo), C.A. 62, 11869b (1965). Metabolism: H. Shindo et al., Yakugaku Zasshi 90, 36 (1970), C.A. 72, 88520q (1970). Pharmacology: S. Kobayashi et al., Arzneim.-Forsch. 20, 43 (1970). Dependence potential in rhesus monkeys: T. Yanagita et al., Bull. Narc. 29, 33 (1977).
Properties: Minute crystals, very slightly hygroscopic, slightly bitter taste. mp 165.5-166.5°. Slightly sol in water. Freely sol in ethanol, chloroform. Sol in acetone, benzene, toluene. Very slightly sol in ether. LD50 in mice (mg/kg): 1300 orally, 1150 s.c., 91 i.v. (Kobayashi).
Melting point: mp 165.5-166.5°
Toxicity data: LD50 in mice (mg/kg): 1300 orally, 1150 s.c., 91 i.v. (Kobayashi)
NOTE: This is a controlled substance (opium derivative): 21 CFR, 1308.11.
Therap-Cat: Antitussive.
Keywords: Antitussive.
Droxicam Droxidopa DSPA DTAF D-Tagatose

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.