Thebaine
| Thebaine | |
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6,7,8,14-tetradehydro-4,5a-epoxy- |
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Other names
Paramorphine |
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| Identifiers | |
| CAS number | 115-37-7  |
| PubChem | 5324289 |
| ChemSpider | 4481822 , 4479543 |
| UNII | 2P9MKG8GX7 |
| KEGG | C06173  |
| MeSH | Thebaine |
| ChEBI | CHEBI:9519 |
| ChEMBL | CHEMBL403893 |
| Jmol-3D images | Image 1 |
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| Properties | |
| Molecular formula | C19H21NO3 |
| Molar mass | 311.37 g mol−1 |
| Pharmacology | |
| Metabolism | O-demethylation [1] |
| Legal status | |
 (verify) (what is:  / ?)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, its name coming from the Greek Θῆβαι, Thēbai, an ancient city in Upper Egypt. A minor constituent of opium, thebaine is chemically similar to both morphine and codeine, but has stimulatory rather than depressant effects. At high doses, it causes convulsions similar to strychnine poisoning. The "unnatural" enantiomer (+)-thebaine does show analgesic effects apparently mediated through opioid receptors, unlike the inactive natural enantiomer (-)-thebaine.[3] Thebaine is not used therapeutically, but as the main alkaloid extracted from Papaver bracteatum (Iranian Poppy), it can be converted industrially into a variety of compounds including oxycodone, oxymorphone, nalbuphine, naloxone, naltrexone, buprenorphine and etorphine.
Thebaine 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.
This alkaloid is biosynthetically related to salutaridine, oripavine, morphine and reticuline.[4]
See also [edit]
References [edit]
- ^ 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
- ^ Novak et al. "Morphine Synthesis and Biosynthesis—An Update" Current Organic Chemistry (2000) 4, 343-362. http://brocku.ca/mathematics-science/departments-and-centres/chemistry/faculty/Hudlicky/CurrOrgChem-2000-4-343.pdf
