Fragmentation Pathways of Trifluoroacetyl Derivatives of Methamphetamine, Amphetamine, and Methylenedioxyphenylalkylamine Designer Drugs by Gas Chromatography/Mass Spectrometry
Fragmentation Pathways of Trifluoroacetyl Derivatives of Methamphetamine, Amphetamine, and Methylenedioxyphenylalkylamine Designer Drugs by Gas Chromatography/Mass Spectrometry
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DOI：
10.1155/2011/318148
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发表时间：
2011-01-01
期刊：
影响因子：
--
通讯作者：
Sato, Keizo
中科院分区：
文献类型：
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作者：
Kumazawa, Takeshi;Hara, Kenji;Sato, Keizo
甲基苯丙胺（MA）、安非他明（AM）和亚甲基二氧苯烷基胺设计药物，如3,4-亚甲基二氧苯丙胺（MDMA）、3,4-亚甲基二氧苯丙胺（MDEA）、n -甲基-1-（3,4-亚甲基二氧苯基）2-丁胺素（MBDB）、3,4-亚甲基二氧苯丙胺（MDA）和3,4-（亚甲基二氧苯基）-2-丁胺素（BDB），被广泛滥用为迷幻药。本文用三氟乙酸（TFA）酸酐衍生了这些化合物，并在正模式下使用电子电离气相色谱/质谱分析。所有化合物的TFA衍生物的气相色谱分离使用Equity-5熔融石英毛细管柱与聚（5%二苯基-95%二甲基硅氧烷）固定相成功分离。MA、AM、MDMA、MDEA、MBDB、MDA和BDB的基峰或显著峰分别出现在m/z 154、140、154、168、168、135和135处。这是由于酰胺氮的a-裂解，分裂成TFA亚胺和苄基或亚甲基二氧苄基阳离子。MA和AM的m/z 118， MDMA、MDEA和MDA的m/z 162， MBDB和BDB的m/z 176是通过氢重排裂解苯基丙烷或亚甲基二氧丙烷烃自由基阳离子而产生的。本文对所有化合物的TFA衍生物的断裂途径进行了总结和说明。
Methamphetamine (MA), amphetamine (AM), and the methylenedioxyphenylalkylamine designer drugs, such as 3,4-methylene-dioxymethamphetamine (MDMA), 3,4-methylenedioxyethylamphetamine (MDEA), N-methyl-1-(3,4-methylenedioxyphenyl)2- butanamine (MBDB), 3,4-methylenedioxyamphetamine (MDA), and 3,4-(methylenedioxyphenyl)-2-butanamine (BDB), are widely abused as psychedelics. In this paper, these compounds were derivatized with trifluoroacetic (TFA) anhydride and analyzed by gas chromatography/mass spectrometry using electron ionization in positive mode. Gas chromatographic separation for TFA derivatives of all compounds was successfully resolved using an Equity-5 fused silica capillary column with a poly (5% diphenyl-95% dimethylsiloxane) stationary phase. Base peaks or prominent peaks of MA, AM, MDMA, MDEA, MBDB, MDA, and BDB appeared at m/z 154, 140, 154, 168, 168, 135, and 135, respectively. These occurred due to a-cleavage from the amide nitrogen, splitting into the TFA imine species and benzyl or methylenedioxybenzyl cations. Further prominent fragment ions at m/z 118 for MA and AM, m/z 162 for MDMA, MDEA, and MDA, and m/z 176 for MBDB and BDB were produced by cleavage of the phenylpropane or methylenedioxypropane hydrocarbon radical cation via a hydrogen rearrangement. These fragmentation pathways for the TFA derivatives of all the compounds are summarized and illustrated in this paper.