thebaine: Definition from Answers.com

Wikipedia: 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	311.36 g mol^-1
Pharmacology
Metabolism	O-demethylation via CYP450 2D6^[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 (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 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

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

Opioids
Opiate derivatives	6-methyldihydromorphine • Acetyldihydrocodeine • Acetyldihydrocodeinone • Acetylmorphone • Benzylmorphine • β-4-morpholinylethylmorphine • Codeine • Codeine-N-Oxide • Codeinone • Desomorphine • Diacetyldihydromorphine • Dihydrocodeine • Dihydrocodeinone enol acetate • Dihydrohydroxycodeinone • Dihydrodesoxymorphine • Dihydroheroin • Dihydroisocodeine • Dihydromorphine • Dipropanoylmorphine • Ethylmorphine • Heroin (Diamorphine) • Heterocodeine • Hydrocodone • Hydromorphinol • Hydromorphone • Laudanum • Methyldesorphine • Methyldihydromorphine • Metopon • Monoacetylmorphine • Morphine-N-Oxide • Morphine • Morphinone • Morphine-6-glucuronide • Myorphine • Nalbuphine • Nalmefene • Nalorphine • Naloxone • Naltrexone • Nicocodeine • Nicodicodeine • Nicomorphine • Norcodeine • Normorphine • Omnopon • Opium • Oripavine • Oxycodone • Oxymorphone • Pantopon • Papaveretum • Paregoric • Pholcodeine • Pseudomorphine • Tetrapon • Thebacon • Thebaine
Morphinans	Butorphanol • Cyclorphan • Dextro-3-hydroxy-N-allylmorphinan • Dextorphan • Levallorphan • Levorphanol • Levorphan • Levophenacylmorphan • Levomethorphan • Norlevorphanol • Phenomorphan • Racemethorphan
Benzomorphans	Cyclazocine • Dezocine • Ethylketocyclazocine • Ketazocine • Metazocine • Pentazocine • Phenazocine
4-Phenylpiperidines	Anileridine • Carbetidine • Carperidine • Difenoxin • Diphenoxylate • Etoxeridine • Furethidine • Ipropethidine • Loperamide • Morpheridine • MPPP • Oxpheneridine • PEPAP • Pethidine (Meperidine) • Pethidine Intermediate A • Pethidine Intermediate B • Pethidine Intermediate C • Pheneridine • Phenoperidine • Piminodine • Properidine • Sameridine • Trimeperidine
Prodines	α-prodine • Allylprodine • β-prodine • β-meprodine • Prodine •
Bemidones	Bemidone • Hydroxypethidine • Ketobemidone •
Anilidopiperidines	3-methylfentanyl • 3-methylthiofentanyl • Alfentanil • α-methylacetylfentanyl • α-methylfentanyl • α-methylthiofentanyl • β-hydroxyfentanyl • β-hydroxythiofentanyl • Bezitramide • Brifentanil • Carfentanil • Fentanyl • Lofentanil • Ohmefentanyl • Parafluorofentanyl • Remifentanil • Sufentanil • Thiofentanyl • Trefentanil
Open chain opioids	β-acetylmethadol • Dextromethadone • Dextromoramide • Dextropropoxyphene • Diethylthiambutene • Dimethylthiambutene • Dipipanone • Ethylmethylthiambutene • Isomethadone • Lefetamine • Levo-α-acetylmethadol • Levomethadone • Levomoramide • Levopropoxyphene • Methadone • Methadone Intermediate • Moramide Intermediate • Noracymethadol • Norpipanone • Phenadoxone • Propoxyphene • Racemoramide
Oripavine derivatives	Acetorphine • Buprenorphine • Cyprenorphine • Dihydroetorphine • Diprenorphine • Etorphine
Phenalkoxams	Dextropropoxyphene • Dimenoxadol • Dioxaphetyl Butyrate •
Ampromides	Diampromide • Phenampromide • Propiram •
Others	Ciramadol • Clonitazene • Codomine • Dimepheptanol • Drotebanol • Ethoheptazine • Etonitazene • Faxeladol • Heptazone • Meptazinol • Metheptazine • Narcotine • O-Desmethyltramadol • Picenadol • Piritramide • Proheptazine • Racemorphan • Semorphone • Tapentadol • Tilidine • Tramadol • Zipeprol

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