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T2019 Sigma

Thebaine

powder

Synonym: Paramorphine

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Properties

Related Categories Bioactive Small Molecule Alphabetical Index, Bioactive Small Molecules, Cell Biology, Cell Signaling and Neuroscience, Neurobiology,
form   powder
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
  H2O: insoluble

Description

Biochem/physiol Actions

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.

Preparation Note

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.

Physical form

Alkaloid powder

Application

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.

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Safety & Documentation

Safety Information

Symbol 
GHS06  GHS06
Signal word 
Danger
Hazard statements 
Precautionary statements 
Hazard Codes (Europe) 
T+
Risk Statements (Europe) 
Safety Statements (Europe) 
22-36/37/39-45
RIDADR 
UN 1544PSN1 6.1 / PGIII
WGK Germany 
3
RTECS 
QD2975000

Documents

Certificate of Analysis

Certificate of Origin

Protocols & Articles

Peer-Reviewed Papers

References

Set your institution to view full text papers.

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)

2. The analysis of thebaine in urine for the detection of poppy seed consumption. Cassella G, Wu AH, Shaw BR, et al. J. Anal. Toxicol. 21(5), 376-83, (1997)

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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)

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Further investigations into the N-demethylation of oripavine using iron and stainless steel. Kok GB and Scammells PJ Org. Biomol. Chem. 9(4), 1008-11, (2011)

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Consensus 3D model of μ-opioid receptor ligand efficacy based on a quantitative Conformationally Sampled Pharmacophore. Shim J, Coop A, and MacKerell AD J. Phys. Chem. B 115(22), 7487-96, (2011)

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Thebaine in hair as a marker for chronic use of illegal opium poppy substances. Lee S, Park Y, Han E, et al. Forensic Sci. Int. 204(1-3), 115-8, (2011)

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Stereoselective mu- and delta-opioid receptor-related antinociception and binding with (+)-thebaine. Aceto, M.D., et al. Eur. J. Pharmacol. 365, 143, (1999)

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The biosynthesis of papaverine proceeds via (S)-reticuline. Han X, Lamshöft M, Grobe N, et al. Phytochemistry 71(11-12), 1305-12, (2010)

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Designation of oripavine as a basic class of controlled substance. Final rule. Fed. Regist. 72(184), 54208-10, (2007)

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WHO Expert Committee on Drug Dependence. World Health Organ. Tech. Rep. Ser. (942), i, 1-21, 23-4 passim, (2006)

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N-demethylation of N-methyl alkaloids with ferrocene. Kok GB and Scammells PJ Bioorg. Med. Chem. Lett. 20(15), 4499-502, (2010)

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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)

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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)

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Highly selective and potent mu opioid ligands by unexpected substituent on morphine skeleton. Li W, Tao YM, Tang Y, et al. Bioorg. Med. Chem. Lett. 20(1), 418-21, (2010)

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Determination of opiate alkaloids in process liquors using capillary electrophoresis. Hindson BJ, Francis PS, Purcell SD, et al. J. Pharm. Biomed. Anal. 43(3), 1164-8, (2007)

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Recent developments in the chemistry of thebaine and its transformation products as pharmacological targets. Berényi S, Csutorás C, and Sipos A Curr. Med. Chem. 16(25), 3215-42, (2009)

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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)

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Synthesis of buprenorphine from oripavine via N-demethylation of oripavine quaternary salts. Werner L, Machara A, Adams DR, et al. J. Org. Chem. 76(11), 4628-34, (2011)

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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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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)

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One-pot conversion of thebaine to hydrocodone and synthesis of neopinone ketal. Carroll RJ, Leisch H, Rochon L, et al. J. Org. Chem. 74(2), 747-52, (2009)

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Fatality involving the ingestion of phenazepam and poppy seed tea. Bailey K, Richards-Waugh L, Clay D, et al. J. Anal. Toxicol. 34(8), 527-32, (2010)

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Pharmacological mechanisms underlying the antinociceptive and tolerance effects of the 6,14-bridged oripavine compound 030418. Wen Q, Yu G, Li YL, et al. Acta Pharmacol. Sin. 32(10), 1215-24, (2011)

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Analysis of fluid extracts obtained from Papaver rhoeas petals contaminated with Papaver bracteatum petals. Gambaro V, Minghetti P, Arnoldi S, et al. Planta Med. 78(12), 1395-8, (2012)

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Urinary excretion of morphine and biosynthetic precursors in mice. Grobe N, Lamshöft M, Orth RG, et al. Proc. Natl. Acad. Sci. U. S. A. 107(18), 8147-52, (2010)

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Rat CYP2D2, not 2D1, is functionally conserved with human CYP2D6 in endogenous morphine formation. Grobe N, Kutchan TM, and Zenk MH FEBS Lett. 586(13), 1749-53, (2012)

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Exposure of consumers to morphine from poppy seeds in Hungary. Zentai A, Sali J, Szeitzné-Szabó M, et al. Food Addit. Contam. Part A. Chem. Anal. Control. Expo. Risk Assess. 29(3), 403-14, (2012)

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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)

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Merck 14,9276

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