| | THEBAINE Basic information |
| Product Name: | THEBAINE | | Synonyms: | PARAMORPHINE;THEBAINE;(-)-thebain;6,7,8,14-tetradehydro-4,5-alpha-epoxy-3,6-dimethoxy-17-methyl-morphina;6,7,8,14-tetradehydro-4,5-epoxy-3,6-dimethoxy-17-methyl-morphina(5-alpha;Morphinan, 6,7,8,14-tetradehydro-4,5alpha-epoxy-3,6-dimethoxy-17-methyl-;Morphinan, 6,7,8,14-tetradehydro-4,5-epoxy-3,6-dimethoxy-17-methyl-, (5alpha)-;Tebain | | CAS: | 115-37-7 | | MF: | C19H21NO3 | | MW: | 311.37 | | EINECS: | 204-084-1 | | Product Categories: | Chiral Reagents;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals | | Mol File: | 115-37-7.mol |  |
| | THEBAINE Chemical Properties |
| Melting point | 183-186°C (dec.) | | alpha | D15 -219° (p = 2 in alc); D23 -230° (p = 5 in chloroform) | | Boiling point | 451.42°C (rough estimate) | | density | 1.3050 | | refractive index | 1.5000 (estimate) | | storage temp. | Controlled Substance, -20°C Freezer | | solubility | H2O: 2.2 mg/mL, slightly soluble | | pka | 6.05(at 15℃) | | form | powder | | Water Solubility | <10mg/L(room temperature) | | EPA Substance Registry System | Morphinan, 6,7,8,14-tetradehydro-4,5-epoxy-3,6-dimethoxy-17-methyl-,(5.alpha.)- (115-37-7) |
| Hazard Codes | T+ | | Risk Statements | 26/27/28 | | Safety Statements | 22-36/37/39-45 | | RIDADR | UN 1544 6.1/PG 2 | | WGK Germany | 3 | | RTECS | QD2975000 | | HazardClass | 6.1(b) | | PackingGroup | III |
| | THEBAINE Usage And Synthesis |
| Description | The naturally occurring opiate alkaloid thebaine is
present in high concentrations in poppy straw; lower
concentrations of the co deine alkaloid are present. | | Description | Thebaine (Item No. 14043) is an analytical reference material categorized as a precursor in the synthesis of morphine (Item Nos. ISO60147 | 15464) and codeine (Item Nos. ISO60140 | 15459). Thebaine is a potential impurity in the illicit synthesis of heroin (Item Nos. ISO60187 | 9001543 | 9003076). Thebaine is regulated as a Schedule II compound in the United States. This product is intended for research and forensic applications. | | Chemical Properties | Tan Solid | | Uses | Thebaine is present in opium at 0.3–1.5%.It is extracted from opium or from latex ofthe plant Papaver bracteatum, in which it ispresent at up to 26%. It is used to producecodeine. | | Uses | Controllled substance (opiate). | | Uses | Thebaine is used in the manufacture of other opiate
pharmaceuticals, such as bupren and morphine, and
caused contact dermatitis in a laboratory worker at an
opiate-manufacturing pharmaceutical company, who
was also sensitive to co deine. | | Definition | ChEBI: Thebaine is a morphinane alkaloid and an organic heteropentacyclic compound. It is a conjugate base of a thebaine(1+). | | Hazard | Toxic by ingestion, may induce addiction. | | Health Hazard | Although thebaine has a morphine- orcodeine-like structure, its pharmacologyaction is somewhat different. It is a convulsantpoison like strychnine, rather thana narcotic. High doses can cause ataxia andconvulsion
LD50 value, intraperitoneal (mice): 42 mg/kg
Thebaine is a habit-forming compound. Itis a controlled substance (opiate) listed underU.S. Code of Federal Regulations (Title 21Part 1308.12, 1985). | | Contact allergens | The naturally occurring opiate alkaloid thebaine is present in concentrated poppy straw, and in small concentrations in codeine alkaloid. It is used in the manufacture of other opiate pharmaceuticals, such as buprenorphine and morphine, and caused contact dermatitis in a laboratory worker at an opiates manufacturing pharmaceutical company, also sensitive to codeine. | | Purification Methods | Crystallise Thebaine from Et2O or EtOH. Sublime it at 170-180o. The hydrochloride decomposes >182o (from MeOH/Et2O). [Beilstein 27 II 177, 27 III/IV 2271.] It is a NARCOTIC. | | References | Pelletier, Thiboumery., Annalen, 16,38 (1835)
Kane., ibid, 19, 9 (1836)
Anderson., ibid, 86, 184 (1853)
Howerd., Ber., 17,527 (1884)
Pschorr, Zeidler., ibid, 27,2961 (1894)
Freund, Michaels, Gobel., ibid, 30, 1357 (1897)
Knorr., ibid, 36, 3074 (1903)
Freund, Holthof., ibid, 37, 2780 (1904)
Pschorr, Pfaff, Herrschmann., ibid, 38, 3163 (1905)
Reichard., Pharm. Zeit., 47,623 (1906)
Hildebrandt., Arch. expo Path. Pharm., 65,54 (1911)
Kruger, Eddy, Sumwalt., Suppl. No. 165, Public Health Reports, Washington
(1943)
Flieschhacker, Pasal, Vieboeck., Monatsh., 99, 300 (1968)
Eppenberger, Warren, Repoport., Helv. Chim. Acta, 51,381 (1968) |
| | THEBAINE Preparation Products And Raw materials |
| Raw materials | CODEINONE-->Morphinan, 6,7,8,14-tetradehydro-4,5-epoxy-3,6-dimethoxy-17-methyl-5-(trimethylsilyl)-, (5β)--->Morphinan, 7,8-didehydro-4,5-epoxy-3,6,6-trimethoxy-17-methyl-, (5α)--->(5alpha)-6,7-didehydro-4,5-epoxy-3,6-dimethoxy-17-methylmorphinan-->HYDROCODONE-->6-O-METHYLCODEINE-->Trimethoxymethane-->CODEINE | | Preparation Products | 17-Northebaine-->HYDROCODONE BITARTRATE RELATED COMPOUND A CII (70 MG) (MORPHINAN-6-ONE, 4-HYDROXY-3-METHOXY-17-METHYL)-->(4aS,7aR)-3,4,6,7,7a,8-Hexahydro-12-hydroxy-11-methoxy-7-methyldibenz[d,f]indol-2(5H)-one-->(5alpha)-6,7,8,14-tetradehydro-4,5-epoxy-6-methoxy-17-methylmorphinan-3-ol-->Naltrexone 3-Methyl Ether-->OXYCODONE HYDROCHLORIDE |
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