Enantioseparation of the carboxamide-type synthetic cannabinoids N-(1-amino-3-methyl-1-oxobutan-2-yl)-1-(5-fluoropentyl)-1H-indazole-3-carboxamide and methyl [1-(5-fluoropentyl)-1H-indazole-3-carbonyl]-valinate in illicit herbal products
Enantioseparation of the carboxamide-type synthetic cannabinoids N-(1-amino-3-methyl-1-oxobutan-2-yl)-1-(5-fluoropentyl)-1H-indazole-3-carboxamide and methyl [1-(5-fluoropentyl)-1H-indazole-3-carbonyl]-valinate in illicit herbal products
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DOI：
10.1016/j.chroma.2016.10.049
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发表时间：
2016-11-18
影响因子：
4.1
通讯作者：
Sawabe, Yoshiyuki
中科院分区：
文献类型：
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作者：
Doi, Takahiro;Asada, Akiko;Sawabe, Yoshiyuki
合成大麻素最近被用作大麻的替代品，是最常被滥用的药物之一。 2014 年鉴定，合成大麻素 N-(1-氨基-3-甲基-1-氧代丁烷-2-基)-1-(5-氟戊基1)-1H-吲唑-3-甲酰胺 (5F-AB-PINACA) 和[1-(5-氟戊基1)-1H-吲唑-3-羰基]-缬氨酸甲酯 (5F-AMB) 是由以下物质组成的甲酰胺： 1-(5-氟戊基1)-1H-吲唑-3-羧酸和缬氨酸酰胺/甲酯。由于其组成，这些分子具有源自其氨基酸结构的手性中心的对映体对。以往对5F-AB-PINACA和5F-AMB的鉴定研究没有考虑对映体的存在，也没有关于合成大麻素对映体纯度的报道。我们合成了这两种化合物的对映体，然后使用直链淀粉三(3-氯-4-甲基苯基氨基甲酸酯)组成的手性固定相柱，通过液相色谱-高分辨质谱法分离对映体。在优化条件下，5F-AB-PINACA和5F-AMB的对映体分辨率分别为2.2和2.3。对10个含有5F-AB-PINACA的草药样品和1个含有5F-AMB的草药样品进行分析，结果显示它们均含有(S)-对映体，但仅在2个样品中检测到(R)-对映体，且比例低于20%。 (C) 2016 Elsevier B.V. 保留所有权利。
Synthetic cannabinoids, recently used as alternatives to Cannabis sativa, are among the most frequently abused drugs. Identified in 2014, the synthetic cannabinoids N-(1-amino-3-methyl-l-oxobutan-2-yl)-1-(5-fluoropenty1)-1H-indazole-3-carboxamide (5F-AB-PINACA) and methyl [1-(5-fluoropenty1)-1H-indazole-3-carbonyl]-valinate (5F-AMB) are carboxamides composed of 1-(5-fluoropenty1)-1H-indazole-3-carboxylic acid and valine amide/methyl ester. Because of their composition, these molecules have pairs of enantiomers derived from the chiral center of their amino acid structures. Previous studies on the identification of 5F-AB-PINACA and 5F-AMB did not consider the existence of enantiomers, and there have been no reports on the enantiopurities of synthetic cannabinoids.We synthesized both enantiomers of these compounds and then separated the enantiomers by liquid chromatography-high-resolution mass spectrometry using a column with a chiral stationary phase consisted with amylose tris (3-chloro-4-methylphenylcarbamate). Under the optimized conditions, the enantiomer resolutions were 2.2 and 2.3 for 5F-AB-PINACA and 5F-AMB, respectively. Analysis of 10 herbal samples containing 5F-AB-PINACA and one herbal sample containing 5F-AMB showed that they all contained the (S)-enantiomer, but the (R)-enantiomer was only detected in two samples and at a ratio of less than 20%. (C) 2016 Elsevier B.V. All rights reserved.