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Thebaine skeletal.svg
IUPAC names
Other names
115-37-7 YesY
ChEMBL ChEMBL403893 YesY
ChemSpider 4481822 YesY
4479543 YesY
Jmol interactive 3D Image
KEGG C06173 N
MeSH Thebaine
PubChem 5324289
Molar mass 311.37 g/mol
Legal status
Low [2]
O-demethylation [1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YesYN ?)
Infobox references

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.[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, is controlled as an analog of a Schedule II drug per the Analog Act in the United States of America, and is controlled with its derivatives and salts, as a Schedule I substance of the Controlled Drugs and Substances Act in Canada.[4] The 2013 US Drug Enforcement Administration (DEA) aggregate manufacturing quota for thebaine (ACSCN 9333) was unchanged from the previous year at 145 metric tons.

This alkaloid is biosynthetically related to salutaridine, oripavine, morphine and reticuline.[5]

In 2012 146,000 kilograms of thebaine were produced.[6]

See also[edit]


  1. ^ 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. 
  2. ^ WHO Advisory Group (1980). "The dependence potential of thebaine". Bulletin on Narcotics 32 (1): 45–54. PMID 6778542. 
  3. ^ 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. 
  4. ^ "Controlled Drugs and Substances Act". Justice Laws Website. Government of Canada. 2012-11-06. Retrieved 2014-01-12. 
  5. ^ 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. 
  6. ^ Narcotic Drugs 2014 (pdf). INTERNATIONAL NARCOTICS CONTROL BOARD. 2015. p. 21. ISBN 9789210481571.