Thebaine

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Thebaine
Image:Thebaine.png
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^[1]. 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

Template:Aromatic-stub

v • d • e Opioids (N02A)
Opiate derivatives	Whole Opium Preparations Dover's Powder • Granulated Opium • Laudanum • Mithridate • Opium • Paregoric • Poppy Straw Concentrate • Poppy tea • Powdered Opium • Raw Opium • Smoking Opium Natural Opiates Codeine • Morphine • Narceine • Noscapine • Omnopon • Oripavine • Pantopon • Papaveretum • Pseudomorphine • Tetrapon • Thebaine Semisynthetics 2,4-Dinitrophenylmorphine • 14-Hydroxyazidomorphine • 14-Ethoxymetopon • 14-Methoxymetopon • 14-Phenylpropoxymetopon • 6-Ketonalbuphine • 6-Methyldihydromorphine • 6-Methylenedihydrodesoxymorphine • 6-Methylene-14-hydroxydihydrodesoxymorphine • 8,14-Dihydroxydihydromorphinone • Acetylcodeine • Acetyldihydrocodeine • Acetylmorphone • Azidocodeine • Azidomorphine • Benzylmorphine • Chloromorphide • Clocinnamox • Codeine • Codeinone • Codorphone • Codoxime • Desocodeine • Desomorphine • Diacetyldihydromorphine • Dihydrocodeine • Dihydrocodeinone enol acetate • Dihydrohydroxycodeinone • Dihydrodesoxymorphine • Dihydroheroin • Dihydroheterocodeine • Dihydroisocodeine • Dihydromorphine • Dibutanoylmorphine • Dipropanoylmorphine • Ethyldihydromorphinone • Ethyldihydromorphine • Ethylmorphine • Heroin (Diamorphine) • Heroin-7,8-Oxide • Heterocodeine • Hydrocodone • Hydromorphinol • Hydromorphone • Isocodeine • Methyldesorphine • Methyldihydromorphine • Methylnaltrexone • Metopon • Morphinone • Myrophine • N-Phenethyl-14-ethoxymetopon • Nalbuphine • Nalfurafine • Nalmefene • Nalodeine • Nalorphine • Naloxone • Naltrexone • Naltrindole • Nicocodeine • Nicodicodeine • Nicomorphine • Oxycodone • Oxymorphone • Pholcodine • Semorphone • Thebacon Opiate metabolites Codeine-N-Oxide • Morphine-3-glucuronide • Morphine-6-glucuronide • Monoacetylmorphine • Morphine-N-Oxide • Naltrexol • Norcodeine • Normorphine
Morphinans	Aknadinine • Butorphanol • Cyclorphan • Cyprodime • Dextro-3-hydroxy-N-allylmorphinan • Dextromethorphan • Dextrorphan • Dimemorfan • Drotebanol • Levargorphan • Levallorphan • Levorphanol • Levorphan • Levophenacylmorphan • Levomethorphan • Norlevorphanol • Oxilorphan • Phenomorphan • Racemethorphan • Racemorphan • Salutaridine (Sinoacutine) • Sinococuline • Sinomenine (Cocculine)
Benzomorphans	5,9-DEHB • Anazocine • Bremazocine • Cogazocine • Cyclazocine • Dezocine • Eptazocine • Etazocine • Ethylketocyclazocine • Fluorophen • Ketazocine • Metazocine • Pentazocine • Phenazocine • Quadazocine • Thiazocine
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 • α-meprodine • α-prodine • β-meprodine • β-prodine • Isopromedol • Meprodine • MPPP • PEPAP • Prodine • Prosidol • Trimeperidine (Promedol) Ketobemidones Acetoxyketobemidone • Droxypropine • Ketobemidone • Methylketobemidone • Propylketobemidone Others Alvimopan • Loperamide • Picenadol
Open Chain Opioids	Amidones Dextromethadone • Dipipanone • Hexalgon • Isomethadone • Levomethadone • Methadone • Methadone intermediate • Normethadone • Norpipanone • Phenadoxone (Heptazone) • Pipidone Methadols Acetylmethadol • α-methadol • α-acetylmethadol • β-methadol • β-acetylmethadol • Dimepheptanol (Racemethadol) • Levo-α-acetylmethadol • Noracymethadol Moramides Dextromoramide • Levomoramide • Moramide intermediate • Racemoramide Thiambutenes Thiambutene • Diethylthiambutene • Dimethylthiambutene • Ethylmethylthiambutene • Tipepidine Phenalkoxams Dextropropoxyphene • Dimenoxadol • Dioxaphetyl Butyrate • Levopropoxyphene • Propoxyphene Ampromides Diampromide • Phenampromide • Propiram Others IC-26 • 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 • Ohmefentanyl • Parafluorofentanyl • Phenaridine • Remifentanil • Sufentanil • Thenylfentanyl • Thiofentanyl • Trefentanil
Oripavine derivatives	7-PET • Acetorphine • Alletorphine • BU-48 • Buprenorphine • Cyprenorphine • Dihydroetorphine • Diprenorphine • Etorphine • N-cyclopropylmethyl-noretorphine • Nepenthone • Norbuprenorphine • Thevinone
Phenazepines	Ethoheptazine • Meptazinol • Metheptazine • Metethoheptazine • Proheptazine
Pirinitramides	Bezitramide • Piritramide
Benzimidazoles	Clonitazene • Etonitazene
Indoles	7-Acetoxymitragynine • 7-Hydroxymitragynine • Akuammidine • Akuammine • Eseroline • Ibogaine • Mitragynine • ψ-Akuammigine
Diphenylmethylpiperazines	BW373U86 • DPI-221 • DPI-287 • DPI-3290 • SNC-80
Opioid Peptides	Casomorphin • DADLE • DALDA • DAMGO • Dermenkephalin • Dermorphin • Deltorphin • DPDPE • Dynorphin • Endomorphin • Endorphin • Enkephalin • TRIMU 5
Others	4-(p-Bromophenyl)-4-(dimethylamino)-1-phenethylcyclohexanol • C-8813 • Ciramadol • Enadoline • Faxeladol • Herkinorin • JTC-801 • Methopholine • NNC 63-0532 • Noscapine/Narcotine • O-Desmethyltramadol • Salvinorin A • RWJ-394,674 • Tapentadol • Tifluadom • Tilidine • Tramadol • Viminol • W-18 • Zipeprol
Narcotic Antagonists	5'-Guanidinonaltrindole • β-Funaltrexamine • Binaltorphimine • Cyclazocine • Cyclohexyl-alpha-phenethylallylamine • Diprenorphine • M5050 • Levallorphan • Nalmefene • Naloxazone • Naloxonazine • Naloxone • Nalorphine • Naltrexone • Naltrindole • Norbinaltorphimine • Oxilorphan

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Acknowledgement and Attribution Regarding Sources of Content

Some of the initial content on this page may be incorporated in part from copyleft sources in the public domain including wikis such as Wikipedia and AskDrWiki. Drug information for patients came from the The National Library of Medicine. Infectious disease information may have come from the Centers for Disease Control (CDC). Differential Diagnoses are drawn from clinicians as well as an amalgamation of 3 sources: 1.The Disease Database; 2. Kahan, Scott, Smith, Ellen G. In A Page: Signs and Symptoms. Malden, Massachusetts: Blackwell Publishing, 2004:3; 3. Sailer, Christian, Wasner, Susanne. Differential Diagnosis Pocket. Hermosa Beach, CA: Borm Bruckmeir Publishing LLC, 2002:7 .