Development of chromatographic methods for thebaine detection and quantification along with some of related alkaloid derivatives

Authors

  • Marija Spasevska Alkaloid AD Skopje – Pharmaceutical, Chemical, Cosmetic & Botanical industry, Aleksandar Makedonski No. 12, Skopje,
  • Jane B Bogdanov Institute of Chemistry, Faculty of Natural Sciences and Mathematics, Ss. Cyril and Methodius University, Arhimedova 5, Skopje,
  • Hristina Babunovska Pharmaceutical Quality Control, Alkaloid AD Skopje – Pharmaceutical, Chemical, Cosmetic & Botanical industry, Aleksandar Makedonski No. 12, Skopje,

DOI:

https://doi.org/10.20450/mjcce.2015.685

Keywords:

thebaine, HPLC, purity, GC-MS, physical properties, spectroscopic properties

Abstract

Thebaine is naturally occurring alkaloid  which is of great importance in the pharmaceutical industry and  up to now there is not a Pharmacopoeial monograph for this compound.  There is a definite need for development of  simple procedures for routine quality assessment  based on physical and spectroscopic properties (melting point, UV-Vis, IR, specific optical rotation) and even more importantly a need for development of chromatographic methods for determination of  purity.The main objective of this work was to develop RP-HPLC-UVD method for quantification of thebaine and also to develop complementary GC-MS method for qualitative analysis. The developed HPLC method utilized RP-C18 monolithic column, gradient elution with trifluoroacetic acid and formic acid in water and in acetonitrile and detection at 285nm. The effects of the relevant chromatographic conditions was investigated and the optimized and validated method was usеd for analysis of  three batches of thebaine.  

A procedure that contained different methods for determination and identification of thebaine, was performed with main focus on the HPLC method suitable for quantitative and qualitative determination.  In parallel, to complete the purity profile,  the three batches of thebaine were analyzed by IR, UV-Vis spectroscopy and specific optical rotation and melting point determination.  The analysis of thebaine can be performed in few steps by simple and reproducible methods like IR spectroscopy, specific optical rotation, melting point and the developed HPLC method, later proved by its validation. The developed HPLC-UV method is suitable for transfer to HPLC-MS method. The GC-MS method is quite suited for identification of thebaine  and of the impurities, but is limited to free bases. Additionally, pseduomorphine  and N-oxide derivatives of the related alkaloids are not suitable for GC-MS analysis.

References

T. Aniszewski, Alkaloids–Secrets of Life: Aklaloid Chemistry, Biological Significance, Applications and Ecological Role, Elsevier, 2007.

L. L. C. Books, L. L. C. General Books, Natural Opium Alkaloids: Morphine, Thebaine, Codeine, Poppy Straw, Papaverine, Opiate, Oripavine, Scoulerine, Reticuline, Protopine, General Books.

M. Hesse, Alkaloids: Nature's Curse or Blessing?, Wiley-VCH, 2002.

M. F. Roberts, M. Wink, Alkaloids: Biochemistry, Ecology, and Medicinal Applications, Springer, 1998.

M. J. O'Neil (ed.), The Merck Index: An encyclopedia of chemicals, drugs, and biologicals. 14th ed., Whitehouse Station, NJ 2006.

A. C. Moffat, M. D. Osselton, B. Widdop,: Clarke’s Analysis of Drugs and Poisons, 3rd ed. Pharmaceutical Press: London, 2004.

V. Gambaro, P. Minghetti, S. Arnoldi, M. Colom-bo, L. Dellacqua, A. Casiraghi, K. Guerrini, F. Fare, G. Roda, Analysis of fluid extracts obtained from Papaver rhoeas petals contaminated with Papaver bracteatum petals, Planta Med., 78(12), 1395–1398 (2012).

M. Omidi, F. Koohzadi, M. Solouki, R. Taghizad Farid, H. Alizadeh, Comparison of morphinan alkaloids during different stages of growth in the medicinal plant opium poppy (Papaver somniferum L.), J. Med Plants, 11(44), 140–148 (2012).

Y. Shoyama, F. Kawachi, H. Tanaka, R. Nakai, T. Shibata, K. Nishi, Genetic and alkaloid analysis of Papaver species and their F1 hybrid by RAPD, HPLC and ELISA, Forensic Sci. Int., 91(3), 207–217 (1998).

I. Stranská, M. Skalický, J. Novák, E. Matyášova, V. Hejnak, Analysis of selected poppy (Papaver somniferum L.) cultivars: Pharmaceutically important alkaloids, Industrial Crops and Products, 41(0), 120–126 (2012).

Z. Szucs, B. Szabady, M. Szatrndry, G. Cirnpan, S. Nyiredy, High-throughput analytical strategy with combined planar and column liquid chromatography for improvement of the poppy (Papaver somniferum L.) with a high alkaloid content, Chromatographia, 56, 49–54 (2002).

K. Yoshimatsu, F. Kiuchi, K. Shimomura, Y. Makino, A rapid and reliable solid-phase extraction method for high-performance liquid chromatographic analysis of opium alkaloids from Papaver plants, Chem. Pharm. Bull., 53(11), 1446–1450 (2005).

D. Lavie, J. Rotman, A. Levy, D. Palevitch, A rapid quantitative method for the determination of thebaine in Papaver bracteatum, Phytochemistry, 18(12), 2011–2013 (1979).

J. W. Costin, S. W. Lewis, S. D. Purcell, L. R. Waddell, P. S. Francis, N. W. Barnett, Rapid de-termination of Papaver somniferum alkaloids in process streams using monolithic column high-performance liquid chromatography with chemiluminescence detection, Anal. Chim. Acta, 597(1), 19–23 (2007).

P. S. Francis, J. L. Adcock, J. W. Costin, S. D. Purcell, F. M. Pfeffer, N. W. Barnett, Chemiluminescence detection of opium poppy (Papaver somniferum) alkaloids, J. Pharm. Bio-med. Anal., 48(3), 508–518 (2008).

A. A. Ensafi, F. Hasanpour, T. Khayamian, A. Mokhtari, M. Taei, Simultaneous chemiluminescence determination of thebaine and noscapine using support vector machine regression, Spectrochim. Acta, Part A, 75(2), 867–871 (2010).

N. W. Barnett, B. J. Hindson, S. W. Lewis, S. D. Purcell, Determination of codeine, 6-methoxy-codeine and thebaine using capillary electrophoresis with tris(2,2'-bipyridyl)ruthenium(II) chemiluminescence detection, Anal. Commun., 35(10), 321–324 (1998).

B. J. Hindson, P. S. Francis, S. D. Purcell, N. W. Barnett, Determination of opiate alkaloids in process liquors using capillary electrophoresis, J. Pharm. Biomed. Anal., 43(3), 1164–1168 (2007).

M. Baranska, H. Schulz, A. C. Geoffrey, Chapter 4: Determination of Alkaloids through Infrared and Raman Spectroscopy, In: The Alkaloids: Chemistry and Biology. Academic Press, pp 217–255 2009.

A. Agnihotri, S. C. Tewari, P. Khatod, S. Banerjee, M. Balasubramanian, Determination of thebaine in crude thebaine samples by infrared and ultraviolet spectrophotometric methods, Analyst, 109, 1413–1416 (1984).

G. W. Caldwell, A. D. Gauthier, J. E. Mills, Configurational analysis of thebaine, codeine and 14beta-hydroxycodeinone N-oxides, Magn. Reson. Chem., 34(7), 505–511 (1996).

O. F. Ellingsen, K. E. Malterud, J. K. Wold, Stud-ies on thebaine, III Oxidative colorimetric analysis of thebaine, Arch. Pharm., 318(4), 380–382 (1985).

S. M. Han, N. Purdie, Simultaneous determination of opiates by circular dichroism, Anal. Chem., 58(1), 113–116 (1986).

K. Ikonomovski, Colorimetric determination of thebaine in Papaver bracteatum, J. Pharm. Sci., 70(1), 102–103 (1981).

D. K. Kuila, S. C. Lahiri, Search for suitable mo-bile phase in TLC analysis of different drugs of forensic interest and their gas liquid chromatographic experiment, J. Indian Chem. Soc., 84(1), 69–73 (2007).

J. Pothier, N. Galand, Automated multiple devel-opment thin-layer chromatography for separation of opiate alkaloids and derivatives, J. Chromatogr., 1080(2), 186–191 (2005).

Y. Shoyama, T. Fukada, H. Murakami, Production of monoclonal antibodies and ELISA for thebaine and codeine, Cytotechnology, 19(1), 55–61 (1995).

N. W. Turner, M. Cauchi, E. V. Piletska, C. Pres-ton, S. A. Piletsky, Rapid qualitative and quantitative analysis of opiates in extract of poppy head via FTIR and chemometrics: Towards in-field sensors, Biosensors Bioelectron., 24 (11), 3322–3328 (2009).

G. E. Baiulescu, S. D. Popescu, Determination of codeine, dionin and thebaine by differential pulse polarography, Anal. Lett., 19(5–6), 587–596 (1986).

B. Rezaei, S. Damiri, Development of a voltammetric procedure for assay of thebaine at a multi-walled carbon nanotubes electrode: Quantification and electrochemical studies, J. Solid State Electrochem., 14(6), 1079–1088 (2010).

A. Alnajjar, A. M. Idris, M. Multzenberg, B. McCord, Development of a capillary electrophoresis method for the screening of human urine for multiple drugs of abuse, J. Chromatogr. B, 856(1–2), 62–67 (2007).

G. Cassella, A. H. B. Wu, B. R. Shaw, D. W. Hill, The analysis of thebaine in urine for the detection of poppy seed consumption, J. Anal. Toxicol., 21(5), 376–383 (1997).

R. Kikura-Hanajiri, N. Kaniwa, M. Ishibashi, Y. Makino, S. Kojima, Liquid chromatographic-atmospheric pressure chemical ionization mass spectrometric analysis of opiates and metabolites in rat urine after inhalation of opium, J. Chromatogr. B, 789(1), 139–150 (2003).

M. Shamsipur Mojtaba, N. Fattahi, Extraction and determination of opium alkaloids in urine samples using dispersive liquid-liquid microextraction followed by high-performance liquid chromatography, J. Chromatogr. B, 879(28), 2978–2983 (2011).

Y. R. Zhang, C. Liang, Q. Y. Jin, Analysis of 39 drugs in urine by HPLC after solid-phase extrac-tion, Chin J Forensic Med, 20(1), 14–16 (2005).

B. M. El-Haj, A. M. Al-Amri, H. S. Ali, I. Ahmed, GC–MS detection and characterization of thebaine as a urinary marker of opium use, Forensic Toxicology, 25(2), 62–68 (2007).

B. M. El-Haj, H. S. Ali, N. M. Hamoudi, Oripavine as a new marker of opiate product use, Forensic Toxicology, 29(2), 152–158 (2011).

R. J. Lewis, R. D. Johnson, R. A. Hattrup, Simul-taneous analysis of thebaine, 6-MAM and six abused opiates in postmortem fluids and tissues using Zymark® automated solid-phase extraction and gas chromatography-mass spectrometry, J. Chromatogr. B, 822(1–2), 137–145 (2005).

C. Meadway, S. George, R. Braithwaite, Opiate concentrations following the ingestion of poppy seed products – Evidence for 'the poppy seed defence', Forensic Sci. Int., 96(1), 29–38 (1998).

C. B. Bural, G. N. Demirer, O. Kantoglu, F. B. Dilek, Treatment of opium alkaloid containing wastewater in sequencing batch reactor (SBR)-Effect of gamma irradiation, RaPC, 79(4), 519–526 (2010).

K. Scheidl, F. Wurst, T. Prey, E. Bancher, Quantitative determination of thebaine in Papaver bracteatum. I. Chromatographic separation and in situ evaluation of HPTLC-plates, Fresen Z Anal Chem, 308(5), 428–430 (1981).

G. Sariyar, A. Mat, H. F. Senol, The quantitative determination of thebaine and narcotine by HPLC in some Turkish Papaver species, Acta Pharmaceutica Turcica, 39(2), 73–75 (1997).

S. Seidi, Y. Yamini, A. Heydari, M. Moradi, A. Esrafili, M. Rezazadeh, Determination of thebaine in water samples, biological fluids, poppy capsule, and narcotic drugs, using electromembrane extraction followed by high-performance liquid chromatography analysis, Anal. Chim. Acta, 701(2), 181–188 (2011).

M. P. Gomez-Serranillos, E. Carretero, A. Villar, A new HPLC method for the analysis of alkaloids in poppy straw, Fitoterapia, 66(2), 156–158 (1995).

P. Gomez-Serranillos, E. Carretero, A. Villar, A study of phenanthrenic poppy straw alkaloids by reversed-phase HPLC, Acta Technologiae et Legis Medicamenti, 6(3), 337–342 (1995).

L. Krenn, S. Glantschnig, U. Sorgner, Determina-tion of the live major opium alkaloids by reversed-phase high-performance liquid chromatography on a base-deactivated stationary phase, Chromatographia, 47(1–2), 21-24 (1998).

M. Chiarotti, N. Fucci, M. I. Arufe Martinez, Analysis of illicit heroin origin impurities, derived from thebaine, by gas chromatography, Revista de Toxicologia, 6(3), 369–376 (1989).

L. Iliev, L. Toteva, Determination of morphine, codeine and thebaine in some poppy varieties by gas chromatography, Farmatsiya, 31(4), 13–22 (1981).

O. F. Ellingsen, J. K. Wold, B. S. Paulsen, Quantitative determination of thebaine in Papaver bracteatum Lindl. by an improved gas chromatographic procedure, Norvegica Pharm Acta, 45(3), 93–101 (1983).

B. D. Paul, C. Dreka, E. S. Knight, M. L. Smith, Gas chromatographic/mass spectrometric detection of narcotine, papaverine, and thebaine in seeds of Papaver somniferum, Planta Med., 62(6), 544–547 (1996).

T. Cecchi, Ion-Pair Chromatograpy and Related Techniques, CRC Press, Boca Raton, FL, 2009.

R. Grob, E. Barry, Modern Practice of Gas Chromatography, 4th ed., Wiley-Interscience, 2004.

M. Maturová, D. Pavlásková, F. Santavý, Isolierung der Alkaloide aus einigen Arten der Gattung Papaver, Planta Med., 14(1), 22–41 (1966).

Downloads

Published

2015-11-12

How to Cite

Spasevska, M., Bogdanov, J. B., & Babunovska, H. (2015). Development of chromatographic methods for thebaine detection and quantification along with some of related alkaloid derivatives. Macedonian Journal of Chemistry and Chemical Engineering, 34(2), 231–243. https://doi.org/10.20450/mjcce.2015.685

Issue

Section

Analytical Chemistry