Synthesis and characterization of barbarin, a possible source of unexplained aminorex identifications in forensic science.,Drug Testing and Analysis

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Synthesis and characterization of barbarin, a possible source of unexplained aminorex identifications in forensic science.
Drug Testing and Analysis ( IF 2.6 ) Pub Date : 2020-06-22 , DOI: 10.1002/dta.2883
Jacob Machin ₁ , Taylor Childers ₁ , Sucheta Kudrimoti ₁ , Rod Eisenberg ₂ , Clara Fenger ₃ , Petra Hartmann ₄ , George Maylin ₅ , Theodore Shults ₆ , Thomas Tobin ₁

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Aminorex is a US DEA Schedule 1 controlled substance occasionally detected in racing horses. A number of aminorex identifications in sport horses were thought to have been caused by exposure to plant sources of aminorex. Glucobarbarin, found in plants of the Brassicaceae family, has been suggested as a potential proximate chemical source by being metabolized in the plant or the horse to aminorex. In Brassicaceae, glucobarbarin is hydrolyzed by myrosinase to yield barbarin, which serves as an insect repellant and/or attractant and is structurally related to aminorex. The synthesis, purification, and characterization of barbarin is now reported for use as a reference standard in aminorex related research concerning equine urinary identifications of aminorex and also for possible use in equine administration experiments. Synthesis of barbarin was performed via ring closure between phenylethanolamine and carbon disulfide in tetrahydrofuran with the catalyst pyridine under reflux. The reaction yielded a white crystalline substance that was purified and chemically characterized as barbarin for use as a Certified Reference Standard or for studies related to equine aminorex identification.

中文翻译：

barbarin 的合成和表征，这是法医科学中无法解释的氨基雷克斯鉴定的可能来源。

Aminorex 是一种美国 DEA 附表 1 受控物质，偶尔会在赛马中检测到。运动马中的许多aminorex 鉴定被认为是由于暴露于植物来源的aminorex 引起的。Glucobarbarin 存在于十字花科植物中，通过在植物或马中代谢为氨基瑞克斯，已被认为是潜在的邻近化学来源。在十字花科中，glucobarbarin 被黑芥子酶水解产生 barbarin，其用作驱虫剂和/或引诱剂，并且在结构上与aminorex 相关。现在有报道称，barbarin 的合成、纯化和表征可用作aminorex 相关研究的参考标准，这些研究涉及aminorex 的马尿鉴定，也可能用于马给药实验。Barbarin 的合成是通过苯基乙醇胺和二硫化碳在四氢呋喃中与催化剂吡啶在回流下闭环进行的。该反应产生了一种白色结晶物质，该物质被纯化并在化学上鉴定为 barbarin，用作认证参考标准或用于与马氨基雷克斯鉴定相关的研究。

更新日期：2020-06-22

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