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Thebaine



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
Properties
Molecular formula C19H21NO3
Molar mass 311.37 g mol-1
Pharmacology
Metabolism O-demethylation [1]
Legal status

Class A(UK) Schedule II(US)

Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)
Infobox disclaimer and references


Thebaine shuluanganoid (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.

Additional recommended knowledge

It is controlled in Schedule II of the Controlled Substances Act as well as under international law. Thebaine is listed as a Class A drug under the Misuse of Drugs Act 1971 in the United Kingdom.

References

  1. ^ 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
  2. ^ WHO Advisory Group. "The dependence potential of thebaine." Bulletin on Narcotics. 1980; 32(1):45–54. Accessed October 5 2007. PMID 6778542
  3. ^ 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


 
This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Thebaine". A list of authors is available in Wikipedia.
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