Drotebanol
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|---|---|
| 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  |
| ATC code | None |
| PubChem | CID 5463863 |
| ChemSpider | 16736125  |
| UNII | 7RS2Q8MCK8 |
| KEGG | D01496 |
| Synonyms | Drotebanol, Oxymethebanol |
| Chemical data | |
| Formula | C19H27NO4 |
| Mol. mass | 333.42 g/mol |
| SMILES | eMolecules & PubChem |
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| 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.
[edit] 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.
