Thebaine
From Wikipedia, the free encyclopedia
| Thebaine | |
|---|---|
 |
|
| IUPAC name |
6,7,8,14-tetradehydro-4,5a-epoxy-
3,6-dimethoxy-17-methylmorphinan |
| Other names | Paramorphine |
| Identifiers | |
| CAS number | 115-37-7  |
| PubChem | 5321926 |
| KEGG | C06173 |
| MeSH | Thebaine |
| ChEBI | 9519 |
| SMILES |
CN1CCC23C4C(=CC=C2C1CC5 =C3C(=C(C=C5)OC)O4)OC
|
| ChemSpider ID | 4479543 |
| Properties | |
| Molecular formula | C19H21NO3 |
| Molar mass | 311.37 g mol−1 |
| Pharmacology | |
| Metabolism | O-demethylation [1] |
| Legal status | |
| (what is this?) (verify) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) |
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| Infobox references | |
Thebaine (paramorphine) is an opiate alkaloid. A minor constituent of opium, thebaine is chemically similar to both morphine and codeine, but has stimulatory rather than depressant effects, causing strychnine-like convulsions at higher doses.[3] Thebaine is not used therapeutically, but can be converted industrially into a variety of compounds including oxycodone, oxymorphone, nalbuphine, naloxone, naltrexone, buprenorphine and etorphine.
It is controlled under international law, is listed as a Class A drug under the Misuse of Drugs Act 1971 in the United Kingdom and is controlled as a Schedule II of the Controlled Substances Act in the United States of America.
[edit] References
- ^ Mikus G, Somogyi AA, Bochner F, Eichelbaum M. "Thebaine O-demethylation to oripavine: genetic differences between two rat strains." Xenobiotica. 1991 Nov; 21(11):1501-9. PMID 1763524
- ^ WHO Advisory Group. "The dependence potential of thebaine." Bulletin on Narcotics. 1980; 32(1):45–54. Accessed October 5, 2007. PMID 6778542
- ^ Aceto MD, Harris LS, Abood ME, Rice KC. "Stereoselective mu- and delta-opioid receptor-related antinociception and binding with (+)-thebaine." European Journal of Pharmacology. 1999 Jan 22;365(2-3):143-7. PMID 9988096
