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THEBAINE

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 Structure
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
form powder
pka6.05(at 15℃)
Water Solubility <10mg/L(room temperature)
EPA Substance Registry SystemMorphinan, 6,7,8,14-tetradehydro-4,5-epoxy-3,6-dimethoxy-17-methyl-,(5.alpha.)- (115-37-7)
Safety Information
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
MSDS Information
ProviderLanguage
SigmaAldrich English
THEBAINE Usage And Synthesis
DescriptionThe naturally occurring opiate alkaloid thebaine is present in high concentrations in poppy straw; lower concentrations of the co deine alkaloid are present.
Chemical PropertiesTan Solid
UsesControllled substance (opiate).
UsesThebaine 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.
UsesThebaine 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.
HazardToxic by ingestion, may induce addiction.
Health HazardAlthough 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 allergensThe 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 MethodsCrystallise 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.
ReferencesPelletier, 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)
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