thebaine: Definition from Answers.com

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`
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)
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

^ 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 (N02A)

Opium
derivatives

Whole Opium
Preparations

B & O Supprettes • Black Drop • Compote/Kompot/Polish Heroin • Diacodium Diascordium • Dover's powder • Granulated Opium • Laudanum • Mithridate • Nepenthe • Opium • Paregoric • Poppy Straw Concentrate(PSC) aka Concentrate of Poppy Straw • Poppy tea • Powdered Opium • Smoking Opium • Theriac

Natural Opiates

Narcotic Opium Alkaloids & Precursors see also: Components of Opium	Calcium Morphenate • Codeine • Dihydroneopine • Dihydronepenthone • Dihydrothebaine • Meconic Acid • Morphine • Narceine • Narcotine/Noscapine • Neopine • Nepenthone • Oripavine • Protopine • Pseudomorphine • Thebaine

Alkaloid Salts Mixtures	Pantopon • Papaveretum (Omnopon) • Tetrapon

Semi-Synthetics

Morphine-Codeine Group	Codeine • Codeine methylbromide • Codeine Barbiturate Salts • Codeine Salicylate • Heterocodeine • Isocodeine • Isomorphine • Morphine • Myrophine • Nalodeine • Normorphine • Morpholinylethylmorphine (Pholcodine) • Transisocodeine

Codeine Analogues	Benzylmorphine • Ethylmorphine (Dionine) (Codethyline, Dionine, &c.) • Propylmorphine

Dihydrocodeine Series	Acetyldihydrocodeine • Dihydrocodeine • Dihydroisocodeine • 7,8-dihydroisocodeine • Diacetyldihydrocodeine • Dihydrocodeine • Dihydroisocodeine • Nicocodeine • Nicodicodeine • Thebacetyl

Hydrocodone-Oxycodone Series (Codeineones)	1-carbethoxy-14-hydroxydihydrocodeinone • 1-carboxy-14-hydroxydihydrocodeinone • 7,8-dihydrocodeineone • Bromoisopropyldihydrocodeinone • Codeinone • Acetyldihydrocodeinone (Dihydrocodeinone enol acetate) • Hydrocodone • Monodihydrocodeineone • Noroxycodone • Propropyldihydrocodeinone • Oxycodone • Thebacon

Morphones (Morphinone Group)	14-Ethoxymetopon • 14-Methoxymetopon • 14-O-Methyloxymorphone • 14-Phenylpropoxymetopon • 14-phenylpropoxy-5-methyl-hydromorphone • 14ß-Hydroxymorphone • 7-Spiroindanyloxymorphone • 8,14-Dihydroxydihydromorphinone • Acetylmorphone • Bromoisopropropyldihydromorphinone • Codorphone • Hydromorphinone (Monohydromorphinone) • Hydromorphone • Isopropropyldihydrocodeinone • Isopropropyldihydromorphinone • Methyldihydromorphinone • Metopon • Morphinone • N-Phenethyl-14-ethoxymetopon • Oxymorphone • Pentamorphone • Semorphone •

Morphinols & Morphols incl. Dihydroneopine Group	14-Hydroxydihydrocodeine • 14-Hydroxymorphine • 14-Hydroxydihydroisocodeine • 14-hydroxydihydrocodeine (Oxycodeine [sic]) • 14ß-Hydroxyisomorphine • 14ß-Hydroxymorphine 6-Hydrocodol • 6 beta-Oxymorphol • Alphahydrocodol/α-hydrocodol (Dihydroneopine) • Hydrocodol (Dihydroneopine) • Hydromorphinol • Hydromorphol • Morphinol • Morphol • N-demethyl14-hydroxydihydrocodeine • Oxymorphinol • Oxymorphol

Morphides	α-chlorocodide (Alphachlorocodide/Chlorocodide) • α-chloromorphide • Bromocodide • Bromomorphide(8-Bromomorphide, 3-Bromomorphide) • Chlorocodide • Chloromorphide • Codide • Fluorocodide(8-Fluorocodide) • Fluormorphide • Iodocodide • Iodomorphide (8-Iodomorphide) • Morphide

Misc. Substituted Morphine Derivatives	2-(p-Nitrophenyl)-4-isopropylmorphine 2,4-Dinitrophenylmorphine N-Phenethylnormorphine

Dihydromorphine Group	6-Acetyldihydromorphine • 6-Monoacetyldihydromorphine • 6-Monoacetyldihydrocodeine • 6-Methyldihydromorphine • Acetyldihydromorphine • Dihydroisomorphine • Dihydromorphine • Ethyldihydromorphine • Ethyldihydromorphinone • Hydroxycodeine • Methyldihydromorphine (Dihydroheterocodeine)

Bentley Compounds (Etorphine Group)	6,14-Endoethenotetrahydrooripavine • BU-48 • Acetorphine • Alletorphine • Butorphine • Dihydroetorphine • Etorphine • Cyprenorphine • Diprenorphine (M5050) • N-cyclopropylmethyl-noretorphine

Desomorphine-Codoxime Group	6-Methylenedihydrodesoxymorphine • Azidomorphine • Codoxime • Desocodeine • Dihydrodesoxycodeine/Desocodeine • Dihydrodesoxymorphine (Desomorphine) • Methyldesorphine

Heroin-MAM-Nicomorphine Group (3- and/or 6- esters)	3-Monoacetylmorphine • 6-Monoacetylmorphine • 6-Mononicotinoylmorphine • Acetylcodeine • Acetylpropionylmorphine(Monoacetylpropionylmorphine) • α-diacetylmorphine • Diacetylcodeine • Diacetyldihydrocodeine • Diacetyldihydromorphine (Dihydroheroin) • Diacetylheterocodeine • Diacetylisocodeine • Diacetylisomorphine • Diacetyl-N-cyanomorphine • Diacetylpropionylmorphine • Dibenzylmorphine • Dibutanoylmorphine • Dipropanoylmorphine • Disalicyloylmorphine • Heroin-7,8-Oxide • Heroin (Diacetylmorphine) • Monoacetylmorphine • Nicocodeine • Nicodicodeine • Nicodimorphine (Nicodihydromorphine) • Nicomorphine •

Nitrogen Morphine Derivatives	1-Nitrocodeine 14-hydroxydihydrocodeineN-oxide • 2-Nitromorphine • Codeine-N-Oxide • Heroin-N-Oxide • Hydromorphone-N-Oxide • Morphine-N-Oxide Oxycodone N-oxide

Halogenated Morphine Derivatives	1-Bromocodeine • 1-Bromodihydrocodeine • 1-Bromodihydrocodeinone • 1-Bromodihydromorphine • 1-Bromodihydromorphinone • 1-Bromoheroin • 1-Chlorocodeine • 1-Chlorodihydrocodeine • 1-Chlorodihydrocodeinone • 1-Chlorodihydromorphine • 1-Chlorodihydromorphinone • 1-Chloroheroin • 1-Fluorocodeine • 1-Fluorodihydrocodeine • 1-Fluorodihydrocodeinone • 1-Fluorodihydromorphine • 1-Fluorodihydromorphinone • 1-Fluoroheroin • 1-Iodocodeine • 1-Iododihydrocodeine • 1-Iododihydrocodeinone • 1-Iododihydromorphine • 1-Iododihydromorphinone • 1-Iodoheroin • 14-Chlorocodeine • 14-Fluorodihydromorphinone • 2-Chloromorphine • 6ß-Chlorocodeine

Morphazones	Acetylmorphazone • Hydromorphazone • Morphazone • Oxymorphazone

Other Morphine Derivatives	7-PET • 6ß-Thiomorphine • Acetomorphine • Apocodeine • Apomorphine • Chlornaltrexamine • Cyclocodeine • Cyclomorphine • Dicodeine Dimorphine N-N-Propylapomorphine • Pentacodeine • Pentamorphine • Pseudomorphine • Pseudocodeine • Tetracodeine • Tetramorphine • Tricodeine • Trimorphine

Derivatives of Thebaine	1-Bromothebaine • 1-Iodothebaine • 1-Fluorothebaine • 2'-Chlorothebaine • 2'-Methylthebaine • 7-Chlorothebaine • Tetrahydrothebaine

Derivatives of Oripavine	Nepenthone • Thevinone •

Derivatives of Other Opium Alkaloids	α-Dihydroneopine • Dihydroneopine

Active Opiate
Metabolites

Codeine-N-Oxide (Genocodeine) • Hydromorphone-N-Oxide • Heroin-7,8-Oxide • Morphine-3-glucuronide • Morphine-6-glucuronide • Monoacetylmorphine • Morphine-N-Oxide (Genomorphine) • Naltrexol • Norcodeine • Normorphine

Morphinans

Morphinan Series	4-chlorophenylpyridomorphinan • Cyclorphan • Dextro-3-hydroxy-N-allylmorphinan • Dimemorfan • Levargorphan • Levallorphan • Levorphanol • Levorphan • Levophenacylmorphan • Levomethorphan • Norlevorphanol • N-Methylmorphinan • Oxilorphan • Phenomorphan • Methorphan / Racemethorphan • Racemorphan • Ro4-1539 • Stephodeline • Xorphanol

Buprenorphine Group	Buprenorphine • 18,19-Dehydrobuprenorphine (HS-599) • Norbuprenorphine • Thienorphine

Others	1-Nitroaknadinine • 14-episinomenine • 5,6-Dihydronorsalutaridine • 6-Ketonalbuphine • Aknadinine • Butorphanol • Cephakicine • Cephasamine • Cyprodime • Drotebanol • Fenfangjine G • Nalbuphine • Sinococuline • Sinomenine (Cocculine) • Tannagine

Benzomorphans

5,9-DEHB • Allylnormetazocine • Anazocine • Bremazocine • Cogazocine • Cyclazocine • Dezocine • Eptazocine • Etazocine • Ethylketocyclazocine • Fluorophen • Ketazocine • Metazocine • Pentazocine • Phenazocine • Quadazocine • Thiazocine • Tonazocine • Volazocine • Zenazocine

4-Phenylpiperidines

Pethidines (Meperidines)	Allylnorpethidine • Anileridine • Benzethidine • Carperidine • Difenoxin • Diphenoxylate • Etoxeridine (Carbetidine) • Furethidine • Hydroxypethidine (Bemidone) • Hydroxymethoxypethidine • Morpheridine • Oxpheneridine (Carbamethidine) • Meperidine-N-Oxide • Pethidine (Meperidine) • Pethidine Intermediate A • Pethidine Intermediate B (Norpethidine) • Pethidine Intermediate C (Pethidinic Acid) • Pheneridine • Phenoperidine • Piminodine • Properidine (Ipropethidine) • Sameridine

Prodines	Allylprodine • Isopromedol • Meprodine (α-meprodine / β-meprodine) • MPPP (Desmethylprodine) • PEPAP • Prodine (α-prodine / β-prodine) • Prosidol • Trimeperidine (Promedol)

Ketobemidones	Acetoxyketobemidone • Droxypropine • Ketobemidone • Methylketobemidone • Propylketobemidone

Others	Alvimopan • Loperamide • Phenadone • Picenadol • tecodine

Open Chain
Opioids

Amidones	Dextromethadone • Dextroisomethadone • Dipipanone • Hexalgon (Norpipanone) • Isomethadone • Levoisomethadone • Levomethadone • Methadone • Methadone intermediate • Normethadone • Norpipanone • Phenadoxone (Heptazone) • Pipidone

Methadols	Dimepheptanol (Racemethadol) • Levacetylmethadol • Levomethadyl acetate (Acetylmethadol) • Noracetylmethadol

Moramides	Dextromoramide • Levomoramide • Moramide intermediate • Racemoramide

Thiambutenes	Diethylthiambutene (Themalon) • Dimethylthiambutene • Ethylmethylthiambutene • Piperidylthiambutene • Pyrrolidinylthiambutene • Thiambutene • Tipepidine

Phenalkoxams	Dextropropoxyphene (Propoxyphene) • Dimenoxadol • Dioxaphetyl Butyrate • Levopropoxyphene • Norpropoxyphene

Ampromides	Diampromide • Phenampromide • Propiram

Tilidine Group	Bisnortilidine • Nortilidine • Prodilidine • Tilidine •

Others	IC-26 • Isoaminile • Lefetamine • R-4066

Anilidopiperidines

3-Allylfentanyl • 3-Methylfentanyl • 3-Methylthiofentanyl • Alfentanil • α-methylacetylfentanyl • α-methylfentanyl • α-methylthiofentanyl • Benzylfentanyl • β-hydroxyfentanyl • β-hydroxythiofentanyl • β-methylfentanyl • Brifentanil • Carfentanil • Fentanyl • Lofentanil • Mirfentanil • Ocfentanil • Ohmefentanyl • Parafluorofentanyl • Phenaridine • Remifentanil • Sufentanil • Thalamonial • Thenylfentanyl • Thiofentanyl • Trefentanil

Oripavine-derived
Synthetics

6,14-Endoethenotetrahydrooripavine • 7-PET • Acetorphine • Alletorphine • BU-48 • Buprenorphine • Butorphine • Cyprenorphine • Dihydroetorphine • Diprenorphine (M5050) • Etorphine • 18,19-Dehydrobuprenorphine (HS-599) • N-cyclopropylmethyl-noretorphine • Nepenthone • Norbuprenorphine • Thevinone • Thienorphine

Phenazepines

Ethoheptazine • Meptazinol • Metheptazine • Metethoheptazine • Proheptazine

Pirinitramides

Bezitramide • Piritramide

Benzimidazoles

Clonitazene • Etonitazene • Nitazene

Indoles

18-MC • 7-Acetoxymitragynine • 7-Hydroxymitragynine • Akuammidine • Akuammine • Eseroline • Hodgkinsine • Ibogaine • Mitragynine • Noribogaine • Pericine • ψ-Akuammigine

Diphenylmethylpiperazines

BW373U86 • DPI-221 • DPI-287 • DPI-3290 • SNC-80

Opioid peptides
see also: The Opioid Peptides

Casomorphin • DADLE • DALDA • DAMGO • Dermenkephalin • Dermorphin • Deltorphin • DPDPE • Dynorphin • Endomorphin • Endorphin • Enkephalin • Gliadorphin • Morphiceptin • Nociceptin • Octreotide • Opiorphin • Rubiscolin • TRIMU 5

Tramadol Group

O-Desmethyltramadol • Tapentadol • Tramadol •

Others

Estocine • Azaprocin • BDPC • Befiradol • BRL-52537 • C-8813 • Ciramadol • Enadoline • Faxeladol • Herkinorin • J-113,397 • JTC-801 • Methopholine • NNC 63-0532 • Phenadone • Profadol • Ro64-6198 • Salvinorin A • SB-612,111 • SC-17599 • RWJ-394,674 • TAN-67 • Tecodine • Tifluadom • Viminol • W-18 • Zipeprol

Opioid Antagonists
&
Inverse-Agonists

5'-Guanidinonaltrindole • β-Funaltrexamine • 6β-Naltrexol • Alvimopan • Amiphenazole • Binaltorphimine • Chlornaltrexamine • Clocinnamox • Cyclazocine • Cyprodime • Diprenorphine (M5050) • Fedotozine • JDTic • Levallorphan • Methocinnamox • Methylnaltrexone • Nalfurafine • Nalmefene • Nalmexone • Naloxazone • Naloxonazine • Naloxone • Naloxone benzoylhydrazone • Nalorphine • Naltrexone • Naltriben • Naltrindole • Norbinaltorphimine • Oxilorphan • S-allyl-3-hydroxy-17-thioniamorphinan (SAHTM)

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