| IUPAC names
| Other names
|3D model (Jmol)||Interactive image|
|ChemSpider|| 4481822 |
|Molar mass||311.37 g/mol|
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
|(what is ?)|
Thebaine (paramorphine), also known as codeine methyl enol ether, is an opiate alkaloid, its name coming from the Greek Θῆβαι, Thēbai (Thebes), 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 synthetic enantiomer (+)-thebaine does show analgesic effects apparently mediated through opioid receptors, unlike the inactive natural enantiomer (−)-thebaine. 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. Butorphanol can also be derived from thebaine and is scheduled separately from butorphanol derived by other processes.
Thebaine is controlled under international law, is listed as a Class A drug under the Misuse of Drugs Act 1971 in the United Kingdom, is controlled as an analog of a Schedule II drug per the Analog Act in the United States, and is controlled with its derivatives and salts, as a Schedule I substance of the Controlled Drugs and Substances Act in Canada. The 2013 US Drug Enforcement Administration (DEA) aggregate manufacturing quota for thebaine (ACSCN 9333) was unchanged from the previous year at 145 metric tons.
In 2012 146,000 kilograms of thebaine were produced. In 2013, Australia was the main producer of poppy straw rich in thebaine, followed by Spain and then France. Together, those three countries accounted for about 99 per cent of global production of such poppy straw.
- 6,14-Endoethenotetrahydrooripavine - the central nucleus of the 'bentley compound' class of opioids which are derived from thebaine
- WHO Advisory Group (1980). "The dependence potential of thebaine". Bulletin on Narcotics. 32 (1): 45–54. PMID 6778542.
- Mikus, G.; Somogyi, A. A.; Bochner, F.; Eichelbaum, M. (1991). "Thebaine O-demethylation to oripavine: Genetic differences between two rat strains". Xenobiotica. 21 (11): 1501–9. doi:10.3109/00498259109044400. PMID 1763524.
- Aceto, M. D.; Harris, L. S.; Abood, M. E.; Rice, K. C. (1999). "Stereoselective μ- and δ-opioid receptor-related antinociception and binding with (+)-thebaine". European Journal of Pharmacology. 365 (2–3): 143–7. doi:10.1016/S0014-2999(98)00862-0. PMID 9988096.
- "Controlled Drugs and Substances Act". Justice Laws Website. Government of Canada. 2012-11-06. Retrieved 2014-01-12.
- Novak, B.; Hudlicky, T.; Reed, J.; Mulzer, J.; Trauner, D. (2000). "Morphine Synthesis and Biosynthesis-An Update" (PDF). Current Organic Chemistry. 4 (3): 343–62. doi:10.2174/1385272003376292.
- Narcotic Drugs 2014 (pdf). INTERNATIONAL NARCOTICS CONTROL BOARD. 2015. p. 21. ISBN 9789210481571.
- "Narcotic Drugs: Estimated World Requirements for 2015; Statistics for 2013" (PDF). International Narcotics Control Board. United Nations International Narcotics Control Board. 2015. p. 151 ff. Retrieved January 7, 2016.