|Related Categories||Bioactive Small Molecules, Cell Biology, Cell Signaling and Neuroscience, Neurobiology, Neuroscience,|
|drug control||USDEA Schedule II; Home Office Schedule 2; stupéfiant; kontrollierte Droge in Deutschland; regulated under CDSA - not available from Sigma-Aldrich Canada|
|solubility||alcohol: soluble1 in 10 of alcohol|
|benzene: soluble1 in 18 in benzene|
|chloroform: soluble50 mg/ml, clear, yellow|
|diethyl ether: soluble1 in 135 of ether|
The (-)-isomer of thebaine is the naturally-occurring constituent of opium that is a precursor of morphine. It has poor antinociceptive activity and induces convulsions. It binds to μ and δ opioid receptors in vitro.
Thebaine dissolves in chloroform at 50 mg/ml to yield a clear, yellow solution. It soluble in alcohol, ether, and benzene at 1:10, 1: 135, and 1:18 parts respectively. However, thebaine does not dissolve in water.
Thebaine has been used for the synthesis of neopinone/codeinone ring systems1. Thebaine has also been used as a 1 mg/ml standard in methanol for urine thebaine analysis in individuals who had consumed poppy seeds2.
Certificate of Analysis
Certificate of Origin
|Precautionary statements||P260-P280-P284-P301 + P310-P302 + P350-P310|
|Personal Protective Equipment||Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges|
|Hazard Codes (Europe)||T+|
|Risk Statements (Europe)||26/27/28|
|Safety Statements (Europe)||22-36/37/39-45|
|RIDADR||UN 1544 6.1/PG 2|
1. Morphine support studies. 2. Formation of the neopinone/codeinone ring system via intramolecular 1, 6-addition of an amino moiety to a dienyl ketone. Toth, J. E., and Fuchs, P. L. J. Org. Chem. 51(13), 2594-2596, (1986)
Determination of thebaine in water samples, biological fluids, poppy capsule, and narcotic drugs, using electromembrane extraction followed by high-performance liquid chromatography analysis. Seidi S, Yamini Y, Heydari A, et al. Anal. Chim. Acta 701(2), 181-8, (2011)
Optimized ultrasound-assisted extraction procedure for the analysis of opium alkaloids in papaver plants by cyclodextrin-modified capillary electrophoresis. Fakhari AR, Nojavan S, Ebrahimi SN, et al. J. Sep. Sci. 33(14), 2153-9, (2010)
Simultaneous chemiluminescence determination of thebaine and noscapine using support vector machine regression. Ensafi AA, Hasanpour F, Khayamian T, et al. Spectrochim. Acta. A. Mol. Biomol. Spectrosc. 75(2), 867-71, (2010)
Regiospecific and stereoselective syntheses of (+/-) morphine, codeine, and thebaine via a highly stereocontrolled intramolecular 4 + 2 cycloaddition leading to a phenanthrofuran system. Stork G, Yamashita A, Adams J, et al. J. Am. Chem. Soc. 131(32), 11402-6, (2009)
Investigation of abiogenic stress-induced alterations in the level of secondary metabolites in poppy plants (Papaver somniferum L.). Szabó B, Lakatos A, Koszegi T, et al. Acta Biol. Hung. 59(4), 425-38, (2008)
Separation and determination of five major opium alkaloids with mixed mode of hydrophilic/cation-exchange monolith by pressurized capillary electrochromatography. Lin X, Wang J, Li L, et al. J. Sep. Sci. 30(17), 3011-7, (2007)
Cinnamoyl derivatives of 7alpha-aminomethyl-6,14-endo-ethanotetrahydrothebaine and 7alpha-aminomethyl-6,14-endo-ethanotetrahydrooripavine and related opioid ligands. Rennison D, Neal AP, Cami-Kobeci G, et al. J. Med. Chem. 50(21), 5176-82, (2007)
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