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研究生： 林立川
Li-Chan Lin
論文名稱： 氣相層析質譜法對亞甲雙氧甲基安非他命類毒品之旋光性與2,5-二甲氧基-4-乙硫基苯乙胺(2C-T-2)之分析研究
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： 2003
畢業學年度： 91
語文別： 中文
中文關鍵詞： 2,5-二甲氧基-4-乙硫基苯乙胺 、亞甲雙氧甲基安非他命 、氣相層析質譜法
英文關鍵詞： 2C-T-2, MDMA, GC/MS
論文種類： 學術論文
相關次數： 點閱：316  下載：0 
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    • 中文摘要
    3,4-methylenedioxyamphetamine（3,4-MDA）、3,4-methylenedioxy-
    methamphetamine（3,4-MDMA）會因為立體中心的而會有不同的神經毒性。故本研究以S-(－)-N-(trifluoroacetyl)prolyl chloride（S-TPC）試劑衍生上具立體中心的3,4-MDA、3,4-MDMA，並利用氣相層析質譜儀來證明成功分離3,4-MDA、3,4-MDMA的R、S form，另外將衍生物層析分離、水解得到單一立體中心的產物。
    本研究對新興苯乙胺類濫用藥物2-(4-ethylsulfanyl)-2,5-dimeth-
    oxyphenylethylamine （2C-T-2）所做的定性分析與代謝成分分析。在定性分析中訂出70eV的EI質譜（m/z：241，212，197，183，153）。代謝成分分析上是將20mg/kg的量注射大白鼠，蒐集24hr的尿液進行分析研究。所蒐集的尿液在經過加酸加熱水解和乙醚的萃取濃縮之後，利用氣相層析質譜儀加上模擬類似藥物2C-B的代謝途徑找到2-(4-ethylsulfanyl-2,5-dimethoxy-phenyl)-ethanol、1-acetoamino-2-
    (2-hydroxy-4-ethylsulfanyl-5-methoxyphenyl)-ethane以及1-aceto-
    amino-2-(2-methoxy-4-ethylsulfanyl-5-hydroxyphenyl)-ethane的代謝物，並且以選擇離子（SIM）的方式確認之。

    Abstract
    For 3,4-methylenedioxyamphetamine (3,4-MDA)、3,4-methylenedi-
    oxymethamphetamine (3,4-MDMA), different stereoisomers cause different neurotoxicity. In this study, we describe a simple method for R- and S-isomer by reaction of S-(－)-N-(trifluoroacetyl)prolyl chloride (S-TPC). Using gas chromatography / mass spectrometry separated derivatives of 3,4-MDA and 3,4-MDMA successfully. Furthermore, we could separate and hydrolyze the derivatives, then we could gain the single form of 3,4-MDA and 3,4-MDMA.
    A simple and specific method based on gas-chromatography-selected
    ion monitoring mass spectrometry (GC-SIM-MS) for the analysis of in vivo metabolism of 2,5-dimethoxy-4-ethylthiophenethylamine (2C-T-2) in rats is described. Three male rats were administered 20 mg/kg of 2C-T-2 by intra-peritoneal injection, and 24h urine fractions were collected before and after administration for analysis. After hydrolysis of the urine samples, the metabolites were extracted by liquid-liquid extraction and analyzed by a quadruple mass spectrometer in the selected ion monitoring mode. The findings show that three metabolites of 2-(4-ethylsulfanyl-2,5-dimethoxyphenyl)-ethanol (MW: 242), 1-acetoamino-2-(2-hydroxy-4-ethylsulfanyl-5-methoxyphenyl)-ethane (MW: 269) and 1-acetoamino-2-(2-methoxy-4-ethylsulfanyl-5-
    hydroxyphenyl)-ethane (MW: 269) are present and the metabolic pathway for 2C-T-2 in the rat is proposed.

    目錄 中文摘要….………………………………………………………….i 英文摘要…………………………………………………………… ii 目錄..………………………………………………………………..iii 圖目錄………………………………………………………………vi 表目錄………………………………………………………………ix 第一章、緒論……………………………………………………………1 1-1 分析物簡介………………………………………………………….1 1-1-1 MDMA系列毒品…………………………………………….1 1-1-2 2C-T-2………………………………………………………...5 1-2 研究目的…………………………………………………………….9 1-2-1 MDA與MDMA的鏡相異構物分離……………………….9 1-2-2新興毒品2C-T-2的性質與代謝……..…………………….11 第二章、各類濫用藥物特性以及質譜分析……………………………13 2-1 濫用藥物種類……………………………………………………...13 2-1-1中樞神經抑制劑…………………………………………….13 2-1-2中樞神經興奮劑…………………………………………….15 2-1-3 幻覺劑……………………………………………………...16 2-2濫用藥物的檢測方法以及質譜儀的分析…………………...16 2-2-1揮發性的興奮劑與麻醉止痛劑的鑑定法………………….17 2-2-2非揮發性的興奮劑與麻醉止痛劑的鑑定法………………18 第三章、儀器、藥品與實驗方法………………………………………20 3-1 儀器………………………………………………………………...20 3-1-1 氣相層析質譜法…………………………………………...20 3-1-2 氣相層析儀………………………………………………...21 3-1-3 界面…………………………….…………………………..26 3-1-4 質譜儀……………………………………………………...27 3-1-5 資料處理…………………………………………………...31 3-1-7 質譜儀校正…………………………………….…………..32 3-1-8 氣相層析質譜儀個裝置之廠牌、型號、規格……………34 3-1-9 其他儀器、器材之廠牌、型號、規格……………………35 3-2 藥品………………………………………………………………...36 3-3 MDA與MDMA鏡相異構物之分離……………………………...38 3-3-1 S-TPC之合成……………………………………………….38 3-3-2 S-TPC與MDA、MDMA的衍生反應…………………….39 3-3-3 管柱層析以及水解條件…………………………………...40 3-3-4 GC-MS的最佳化…………………………………………...41 3-3-5 氣相層析條件……….……………………………………..41 3-4 2C-T-2的性質以及代謝物的分析…………………………………42 3-4-1 2C-T-2的氣相層析條件…………………..……………….42 3-4-2 老鼠的代謝實驗…………………………………………...42 3-4-3 尿液的水解與萃取………………………………………...43 3-4-4 2C-T-2代謝物的氣相層析條件……………………………47 第四章、結果討論……………………………………………………...48 4-1 MDA、MDMA鏡相異構物的分離………………………………48 4-1-1 利用GC-MS分離衍生物情形以及質譜解析……………..48 4-1-2 衍生物經管柱層析後以GC-MS確認分離情形…………..52 4-1-3 單一立體中心產物與毛細管電泳結合…………………….55 4-2 對新興濫用藥物2C-T-2性質與代謝物成分分析……………….57 4-2-1 2C-T-2藥品的氣相層析質譜圖……………………………..57 4-2-2 2C-T-2代謝物路徑推測……………………………………..60 4-2-3 老鼠尿液中2C-T-2殘餘藥量測試…………………………63 4-2-4 老鼠尿液中代謝物鑑定…………………………………….65 4-2-5 老鼠尿液中代謝物的質譜解析…………………………….70 4-2-6 酸性條件與鹼性條件萃取比較…………………………….74 4-2-7 其他老鼠實驗……………………………………………….76 第五章、結論…………………………………………………………..80 參考資料………………………………………………………………..81 發表論文………………………………………………………………..88

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