研究生: |
陳雯雄 Wen-Xiong Chen |
---|---|
論文名稱: |
液相層析質譜法對色胺類衍生物之分析研究 Analysis of tryptamines by Liquid-Chromatography/Mass Spectrometry |
指導教授: |
林震煌
Lin, Cheng-Huang |
學位類別: |
碩士 Master |
系所名稱: |
化學系 Department of Chemistry |
論文出版年: | 2008 |
畢業學年度: | 96 |
語文別: | 中文 |
中文關鍵詞: | 液相層析質譜儀 、阿達瑪轉換 、色胺類濫用藥物 |
論文種類: | 學術論文 |
相關次數: | 點閱:227 下載:0 |
分享至: |
查詢本校圖書館目錄 查詢臺灣博碩士論文知識加值系統 勘誤回報 |
本研究以LC-ESI/MS (liquid chromatography-electrospray ionization/mass spectrometry,液相層析電噴灑質譜儀)分析色胺類濫用藥物,歸納出色胺類濫用藥物的特徵譜峰。在ESI游離模式下,一級胺類(α-methyltryptamine, AMT;5-methoxy-α-methyltryptamine, 5-MeO-AMT)與三級胺類(N,N-dimethyltryptamine, DMT; N,N-diethyltryptamine, DET; N,N-dipropyltryptamine, DPT; N,N-dibutyltryptamine, DBT; N,N-diisopropyltryptamine, DIPT; 5-methoxy-N,N-dimethyltryptamine, 5-MeO-DMT; 5-methoxy-N,N-di-isopropyltryptamine, 5-MeO-DIPT)藥物,可觀察到兩種特殊斷裂途徑。此兩種斷裂途徑分別為α-斷裂(α-cleavage)和β-斷裂(β-cleavage),可做為刑事鑑定的特徵峰。此外,為了改善色胺類的偵測靈敏度,本研究引用阿達瑪轉換(Hadamard Transform)技術來提高訊號/雜訊的比值。實驗中使用了一個高效能液相層析(High Performance Liquid Chromatography, HPLC)幫浦與一個高壓精密注射泵來完成進樣的工作。將阿達瑪序列由電腦經RS232介面傳輸到注射泵,使樣品溶液與HPLC流析溶劑,可按照阿達瑪序列的方式,流入Tee connector再進入分離管柱。分析物經管柱分離以後,以ESI的方式,可在SIM (selected ion monitoring)或SRM (selected reaction monitoring)的模式下讀取數據。以DMT為測試樣品,在阿達瑪序列n = 1023 時,訊號/雜訊的比值可提高約一個數量級。
Characteristic mass fragmentation of 9 tryptamine standards, including a-methyltryptamine, 5-methoxy-a-methyltryptamine, N,N-dimethyltryptamine, N,N-diethyltryptamine, N,N-dipropyltryptamine, N,N-dibutyltryptamine, N,N-diisopropyltryptamine, 5-methoxy-N,N-dimethyltryptamine and 5-methoxy-N,N-diisopropyltryptamine, were investigated and compared by means of LC-ESI/MS (liquid chromatography-electrospray ionization/mass spectrometry). As a result, the protonated molecular ion ([M+H]+) and two types of fragments produced from the α-cleavage and β-cleavage processes, were found to be characteristic and useful in the rapid screening and confirmation of tryptamine derivatives. Furthermore, in order to improve signal-to-noise (S/N) ratio, Hadamard transform (HT) technique was applied. Novel sample injection device was developed to achieve multiple sample injections, where a syringe pump and Tee connector were employed. The injection device permitted precise successive injections, resulting in clearly modulated chromatograms encoded by Hadamard matrices. After inverse Hadamard transformation of the encoded chromatogram, the S/N ratios of the signals were substantially improved compared with those expected from theoretical values.
[1] Yergey, A. L.; Edmonds, C. G.; Lewis I. A. S.; Vestal, M. L. Liquid Chromatography/Mass Spectrometry Techniques and Applications. New York: Plenum Press,1990
[2] Brown, M. A. Ed. Liquid Chromatography/Mass Spectrometry Applications in Agricultural, Pharmaceutical, and Environmental Chemistry. Washington, DC: American Chemical Society,1990
[3] Covey, T. R.; Lee, E. D.; Bruins, A. P.; Henion, J. D. Anal. Chem. 1986, 58, 1451A
[4] Vestal, M. L. Science. 1984, 226, 275
[5] Vestal, M. L. Spectra. 1983, 9, 1
[6] (a) Yamashita, M.; Fenn, J. B. J. Phys. Chem. 1984, 88, 4451;(b) Yamashita, M.; Fenn, J. B. J. Phys. Chem. 1984, 88, 4671
[7] Meng, C. K.; Mann, M.; Fenn, J. B. Phys. D-Atoms, Molecules and Clusters 1988, 10, 361-368
[8] Marshall, A. G.; Verdun, F. R. Fourier Transforms in NMR, Optical, and Mass Spectrometry. New York: Elsevier,1990
[9] Marshall, A. G. Fourier, Hadamard, and Hilbert Transforms in Chemistry. New York: Plenum Press,1982
[10] Griffiths, P. R. Science. 1983, 222, 297
[11] Perkins, W. D. J. Chem. Educ. 1986, 63, A5, A296
[12] Glasser, L. J. Chem. Educ. 1987, 64, A228, A260, A306
[13] Griffiths, P. R. Ed. Transform Techniques. New York: Pleunum Press,1978
[14] Treado, P. J.; Morris, M. D. Anal. Chem. 1989, 61, 723A
[15] Harwit, M. O.; Sloane, N. J. A. HADAMARD TRANSFORM OPTICS. New York: Academic Press,1979
[16] Kaljurand, M.; Küllok, E. Chromatographia, 1978, 11, 328-330
[17] Brayan, J. G.; Malcolme-Lawes, D. J.; Mew, C. D.; Xie, S. J. Autom. Chem. 1995, 17, 77-82
[18] Kaneta, T.; Yamaguchi, Y.; Imasaka, T. Anal. Chem. 1999, 71, 5444-5446
[19] Kaneta, T.; Kosai, K.; Imasaka, T. Anal. Chem. 2002, 74,2257-2260
[20] Hata, K.; Kichise, Y.; Kanata, T.; Imasaka, T. Anal. Chem. 2003, 75,1765-1768
[21] Hata, K.; Kaneta, T.; Imasaka, T. Anal. Chem. 2004, 76,4421-4425
[22] Hata, K.; Kaneta, T.; Imasaka, T. Electrophoresis 2007,28,328-334
[23] DeVerse, R. A.; Hammaker, R. M.; Fateley, W. G. Viob. Spectro. 1999, 19,177-186
[24] Fateley, W. G.; Hammaker, R. M.; Paukstelis, J. V. Applied. Specto. 1993, 47, 1464-1470
[25] Ashida, J.;Kupce, E.; Amoureux, J. P. J. Magne. Resonan. 2006, 178,129-135
[26] Lescop, E.; Rasia, R.; Brutscher, B. J. Am. Soc. 2008, 130, 5014
[27] Burnley, B. T.; Kalverda, A. P.; Paisey, S. J. J. Bio. NMR. 2007, 39, 239-245
[28] Szumlas, A.W.; Ray, S. J.; Hieftje, G. M. Anal. Chem. 2006, 78, 4474-4481
[29] Clowers, B. H.; Belov, M. E.; Prior, D. C.; William, F. D.; Ibrahim, D.; Smith, R. D. Anal. Chem. 2008, 80, 2464-2473
[30] Clowers, B. H.; Siems,W. F.; Hill H. H.; Massick, S. M. Anal. Chem. 2006, 78, 44-51
[31] Nicolos, D. E. J. Pharm. Sci. 1981, 70, 839
[32] Spoerke, D. G.; Hall, A. H. Emerg. Med. Clin. North Am. 1990, 8, 579
[33] Kikura-Hanajiri, R.; Hayashi, M.; Saisho, K.; Goda, Y. J. Chromatogra. B. 2005, 825, 29-37
[34] Barker, S. A.; Monti, J. A.; Christian, S. T. Int. Rev. Neurobio. 1981, 22, 83-110
[35] A. Shulgin, A. Shulgin, THINKAL (Tryptamines I Have Known and Loved): The continuation, Transform Press, Berkeley, 1997
[36] McKenna, D. J.; Tower, G. H. N. J. Psychoactive Drugs. 1984, 16, 347
[37] Smith, R. L.; Canton, H.; Barrett, R. J.; Sanders-Bush, E. Pharmar. Biochem. and Behavi. 1998, 61, 323-330
[38] Jeremy, B.; Jonathan, O. Head Magzine 1977, 11,56-61
[39] Fumiko, N.; Ryouichi N.; Kanako, S. H. K. Europ. J. Phar. 2007, 559, 132-137
[40] Takahashi, M.; Nagashima, M.; Suzuki, J.; Seto, T.; Yasuda, I.; Yoshida, T. J. Heal. Sci. 2008, 54, 89-96
[41] Skoog, A.; Holler, F.; Nieman, A. Principles of Instrumental Analysis, fifth ed. BROOKS/COLE 1997
[42] Snyder, L. R.; Kirkland, J. J. Introduction to Modern Liquid Chromatography.Wiley,New York 1974
[43] Lovins, R. E.; Ellis, S. R.; Tolbert, G. D.; McKinney, C. R. Anal Chem. 1973, 45,1553
[44] Scott, R. P. W.; Scott, C. G.; Munroe, M.; Hess, J. J. Chromatogr. 1974, 99,395
[45] McFadden, W. H.; Schwartz, H. L.; Evans, S. J. Chromatogr. 1976, 122, 389
[46] Jones, P. R.; Yang, S. K. Anal. Chem. 1975, 47,1000
[47] Talroze, V. L.; Karpov, G. V.; Gorodetskii, I. G. J. Phys. Chem. 1968, 42,1658
[48] Blackey, C. R.; McAdams, M. J.; Vestal, M. L. J. Chromatogr. 1978, 158,261
[49] Vestal, M. L. Mass Spectrom Rev. 1983, 2,447
[50] Taylor, G. I., Proc. R Soc. London A 1964, A280,383
[51] Rayleigh, Lord Philos. Mag. 1882, 14,184
[52] Rayleigh, Lord The Theory of sound; Dover: New York,1945
[53] Doyle, A.; Moltett, D. R.; Vonnegut, B. J. Colloid Sci. 1964, 19,136
[54] Dole, M.; Mack, L. L.; Hines, R. L.; Mobley,R. C.; Ferguson, L. D.; Alice, M. B. J. Chem. Phys. 1968, 49,2240
[55] Iribarne, J. V.; Thomson, B. A. J. Chem. Phys. 1976, 64,2287
[56] Thomson, B. A.; Iribarne, J. V. J. Chem. Phys. 1979, 71,4451
[57] Fenn, J. B. J. Am. Soc. Mass Spetrom. 1993, 4,524
[58] VERONIKA R. MEYER Practical High-Performance Liquid Chromatography. Wiley,New York,1999