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 Y
PubChem	5321926
KEGG	C06173
MeSH	Thebaine
ChEBI	9519
SMILES	CN1CCC23C4C(=CC=C2C1CC5 =C3C(=C(C=C5)OC)O4)OC
ChemSpider ID	4479543
Properties
Molecular formula	C19H21NO3
Molar mass	311.37 g mol−1
Pharmacology
Metabolism	O-demethylation [1]
Legal status	Class A(UK) Schedule II(US)
Y (what is this?)  (verify) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Thebaine (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.

It 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.

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