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

林立川(Li-Chan Lin)

指導教授 ： 林震煌

國立臺灣師範大學/理學院/化學系/碩士(2002年)

摘要

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。

關鍵字

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

並列摘要

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.

並列關鍵字

2C-T-2 ； MDMA ； GC/MS

參考文獻

1. Ensslin, H.K.; Kovar, K-A.; Maurer, H.H., Toxicological detection of the designer drug 3,4-methylenedioxyethylamphetamine (MDE, “Eve”) and its metabolites in urine by gas chromatography-mass spectrometry and fluorescence polarization immunoassay. J. Chromatogr. B 683 (1996) 189

2. Maurer H.H.; Bickeboeller-Friedrich, J.; Kraemer, T.; Peters, F.T., oxicokinetics and analytical toxicology of amphetamine-derived designer drugs (‘Ecstasy’). Toxicol. Letters 112-113 (2000) 133

3. Sadeghipour, F.; Veuthey, J. -L., Sensitive and selective determination of methylenedioxylated amphetamines by high-performance liquid chromatography with fluorimetric detection J. Chromatogr. A 787 (1997) 137

6. Robert Mathias. Ecstasy damages brain and impairs memory in human. NIDA Dotes, 1999, 14(4): 10－11.

7. Zicker P. Annual survey finds increasing teen use of Ecstasy, Steroids. NIDA Notes, 2001, 16(2): 6－7.