Analysis of potential phenylacetone precursors (ethyl 3-oxo-2-phenylbutyrate, methyl 3-oxo-4-phenylbutyrate, and ethyl 3-oxo-4-phenylbutyrate) by gas chromatography/mass spectrometry and their conversion to phenylacetone,Drug Testing and Analysis

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Analysis of potential phenylacetone precursors (ethyl 3-oxo-2-phenylbutyrate, methyl 3-oxo-4-phenylbutyrate, and ethyl 3-oxo-4-phenylbutyrate) by gas chromatography/mass spectrometry and their conversion to phenylacetone
Drug Testing and Analysis ( IF 2.6 ) Pub Date : 2021-10-01 , DOI: 10.1002/dta.3169
Kenji Tsujikawa ₁ , Yuki Okada ₁ , Hiroki Segawa ₁ , Kenji Kuwayama ₁ , Tadashi Yamamuro ₁ , Tatsuyuki Kanamori ₁ , Yuko T Iwata ₁

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Methyl 3-oxo-2-phenylbutyrate (MAPA) is a recently circulating precursor of phenylacetone (P2P), a precursor of amphetamine and methamphetamine. MAPA has a hybrid chemical structure of acetoacetic acid ester and P2P. Acetoacetic acid ester is de-esterified and decarboxylated to give the ketone by heating under acidic conditions; therefore, MAPA is presumed to be converted to P2P by such treatment. Considering that ethyl 3-oxo-2-phenylbutyrate (EAPA), methyl 3-oxo-4-phenylbutyrate (MGPA), and ethyl 3-oxo-4-phenylbutyrate (EGPA) have the same chemical features as MAPA, these three compounds are potential P2P precursors. The authors examined the analysis of these compounds by gas chromatography–mass spectrometry (GC-MS) and their conversion to P2P by heating under acidic and basic conditions. These compounds were remarkably decomposed into P2P during GC-MS analysis regardless of the injection method and injector temperature. EAPA and EGPA also caused ester exchange to methyl ester by injection of methanol solution. P2P production and transesterification were almost prevented by methoxime derivatization. These compounds were converted to P2P by heating under acidic conditions. The reaction of MGPA and EGPA proceeded quicker than that of EAPA. The important by-product associated with the reaction was phenylacetylcarbinol (formed from EAPA and MGPA), which will be converted to (pseudo)ephedrine, important methamphetamine impurities. By heating under basic conditions, MGPA and EGPA were converted to P2P but EAPA was mainly converted to phenylacetic acid. In the future, when these compounds are in circulation, our study will be useful for identifying and elucidating the synthetic method of P2P.

中文翻译：

通过气相色谱/质谱分析潜在的苯丙酮前体（3-氧代-2-苯基丁酸乙酯、3-氧代-4-苯基丁酸甲酯和3-氧代-4-苯基丁酸乙酯）及其转化为苯丙酮

3-氧代-2-苯基丁酸甲酯 (MAPA) 是最近流行的苯丙酮 (P2P) 前体，苯丙胺和甲基苯丙胺的前体。MAPA具有乙酰乙酸酯和P2P的混合化学结构。乙酰乙酸酯在酸性条件下加热脱酯脱羧得到酮；因此，推测 MAPA 通过这种处理转换为 P2P。考虑到 3-氧代-2-苯基丁酸乙酯 (EAPA)、3-氧代-4-苯基丁酸甲酯 (MGPA) 和 3-氧代-4-苯基丁酸乙酯 (EGPA) 具有与 MAPA 相同的化学特征，这三种化合物分别是潜在的 P2P 先驱。作者通过气相色谱-质谱 (GC-MS) 分析了这些化合物，并通过在酸性和碱性条件下加热将它们转化为 P2P。无论进样方法和进样器温度如何，这些化合物在 GC-MS 分析期间都显着分解为 P2P。EAPA 和 EGPA 还通过注入甲醇溶液引起酯交换为甲酯。甲肟衍生化几乎阻止了 P2P 的产生和酯交换。这些化合物通过在酸性条件下加热转化为 P2P。MGPA和EGPA的反应比EAPA快。与该反应相关的重要副产物是苯乙酰甲醇（由 EAPA 和 MGPA 形成），它将转化为（伪）麻黄碱，这是一种重要的甲基苯丙胺杂质。通过在碱性条件下加热，MGPA和EGPA转化为P2P，而EAPA主要转化为苯乙酸。将来，当这些化合物流通时，

更新日期：2021-10-01

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