Identification of N,N-bis(1-pentylindol-3-yl-carboxy)naphthylamine (BiPICANA) found in an herbal blend product in the Tokyo metropolitan area and its cannabimimetic effects evaluated by in vitro [35S]GTPγS binding assays
Identification of N,N-bis(1-pentylindol-3-yl-carboxy)naphthylamine (BiPICANA) found in an herbal blend product in the Tokyo metropolitan area and its cannabimimetic effects evaluated by in vitro [35S]GTPγS binding assays
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DOI：
10.1007/s11419-014-0253-6
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发表时间：
2015-01-01
影响因子：
2.2
通讯作者：
Nakae, Dai
中科院分区：
文献类型：
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作者：
Nakajima, Jun'ichi;Takahashi, Misako;Nakae, Dai
2013年6月，我们在东京都市区对未受管制的精神药物进行了仔细调查，在一种草药产品中发现了一种新的化合物。它被鉴定为NNEI（MN-24）的类似物，不同之处在于其分子具有另一个N-戊基吲哚-羰基：N，N-双（1-戊基吲哚-3-基-羧基）萘胺（BiPICANA，化合物2）。化合物2通过硅胶和十八烷基键合型硅胶（C18，ODS）柱纯化，并通过液相色谱-质谱、精确质谱、核磁共振光谱和X射线晶体学确认。以前没有报道过化合物2的药理学信息;我们对化合物2与大麻素受体结合能力的实验表明，它对CB 1和CB 2受体具有亲和力（EC 50分别为3.80和8.77 x 10（-7）M）。这是第一份在可疑草药产品中鉴定化合物2并证明其与大麻素受体结合亲和力的报告。本报告还介绍了AM-1220和AM-2233的氮杂环庚烷异构体（化合物3和4）的结合亲和力，这些异构体也存在于日本的商业产品中。
During our careful survey of unregulated psychotropic drugs in June 2013 in the Tokyo metropolitan area, we found a new compound in a herbal product. It was identified as an analog of NNEI (MN-24) and differed in that its molecule possessed another N-pentyl indole-carbonyl group: N, N-bis(1-pentylindol-3-yl-carboxy)naphtylamine (BiPICANA, compound 2). Compound 2 was purified by silica and octadecyl group bonded type silica gel (C18, ODS) columns and confirmed by liquid chromatography-mass spectrometry, accurate mass spectrometry, nuclear magnetic resonance spectroscopy, and X-ray crystallography. No pharmacological information on compound 2 has been reported previously; our experiments on the binding ability of compound 2 to cannabinoid receptors revealed that it has affinities for CB1 and CB2 receptors (EC50 = 3.80 and 8.77 x 10(-7) M, respectively). This is the first report identifying compound 2 in a dubious herbal product and demonstrating its binding affinities to cannabinoid receptors. Binding affinities of azepane isomers (compounds 3 and 4) of AM-1220 and AM-2233, also found in commercial products in Japan, are also presented in this report.