Thebaine

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Thebaine
Thebaine skeletal.svg
Thebaine.gif
Names
IUPAC names
6,7,8,14-tetradehydro-4,5a-epoxy-
3,6-dimethoxy-17-methylmorphinan
Other names
Paramorphine
Identifiers
115-37-7 YesY
ChEBI CHEBI:9519 YesY
ChEMBL ChEMBL403893 YesY
ChemSpider 4481822 YesY
4479543 YesY
Jmol interactive 3D Image
KEGG C06173 N
MeSH Thebaine
PubChem 5324289
UNII 2P9MKG8GX7 YesY
Properties
C19H21NO3
Molar mass 311.37 g/mol
Pharmacology
Legal status
Low [2]
Pharmacokinetics:
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. Butorphanol can also be derived from thebaine and is scheduled separately from butorphanol derived by other processes[4]. More distant chemical and structural thebaine derivatives include emetics, stimulants, and both pure and mixed opioid agonists as well as antagonists, partial agonists, and inverse agonists. The derivative tetrahydrothebaine is an intermediate in the synthesis of many semi-synthetic opioids including dihydromorphine.[5]

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.[6] 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.[7]

In 2012 146,000 kilograms of thebaine were produced.[8] 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.[9]

See also[edit]

References[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. ^ http://www.deadiversion.usdoj.gov/schedules/orangebook/a_sched_alpha.pdf
  5. ^ Inside Narcotics, pp 345-353
  6. ^ "Controlled Drugs and Substances Act". Justice Laws Website. Government of Canada. 2012-11-06. Retrieved 2014-01-12. 
  7. ^ 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. 
  8. ^ Narcotic Drugs 2014 (pdf). INTERNATIONAL NARCOTICS CONTROL BOARD. 2015. p. 21. ISBN 9789210481571. 
  9. ^ "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.