The Identification of the Urinary Metabolites of 3-(4-Methoxybenzoyl)-1-Pentylindole (RCS-4), a Novel Cannabimimetic, by Gas ChromatographyMass Spectrometry
The Identification of the Urinary Metabolites of 3-(4-Methoxybenzoyl)-1-Pentylindole (RCS-4), a Novel Cannabimimetic, by Gas ChromatographyMass Spectrometry
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DOI：
10.1093/jat/bks032
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发表时间：
2012-06-01
影响因子：
2.5
通讯作者：
Simonov, Anton
中科院分区：
文献类型：
--
作者：
Kavanagh, Pierce;Grigoryev, Andrej;Simonov, Anton
3-（4-甲氧基苯甲酰基）-1-戊基吲哚（RCS-4）是一种合成的吲哚衍生大麻模拟物，匈牙利当局于2010年通过预警系统首次向欧洲毒品和毒瘾监测中心报告，后来在爱尔兰的商店测试购买中发现。使用气相色谱-质谱，我们已经确定了一系列的RCS-4代谢物的尿样从个人入院的药物中毒症状。代谢物初步鉴定为以下产物：（i）芳香族单羟基化;（ii）二羟基化;（iii）N-戊基链芳香族羟基化/氧化为酮;（iv）O-脱甲基化;（v）N-戊基链O-脱甲基化/单羟基化;（vi）N-戊基链O-脱甲基化/氧化为酮;（vii）N-戊基链O-脱甲基化/芳香族羟基化/氧化为酮;（viii）N-脱戊基化/芳族单羟基化;和（ix）N和O-脱烷基化。未检出母体化合物。发现O-脱甲基代谢物是鉴定RCS-4摄入的最有用的代谢标志物。
3-(4-Methoxybenzoyl)-1-pentylindole (RCS-4), a synthetic indole-derived cannabimimetic, was first reported to the European Monitoring Centre for Drugs and Drug Addiction via the Early Warning System by Hungarian authorities in 2010 and later identified in head shop test purchases in Ireland. Using gas chromatographymass spectrometry, we have identified a series of RCS-4 metabolites in urine samples from individuals admitted to hospitals with symptoms of drug intoxication. The metabolites were tentatively identified as products of (i) aromatic monohydroxylation; (ii) dihydroxylation; (iii) aromatic hydroxylation/oxidation of the N-pentyl chain to a ketone; (iv) O-demethylation; (v) O-demethylation/monohydroxylation of N-pentyl chain; (vi) O-demethylation/oxidation of the N-pentyl chain to a ketone; (vii) O-demethylation/aromatic hydroxylation/oxidation of the N-pentyl chain to a ketone; (viii) N-depentylation/aromatic monohydroxylation; and (ix) N and O-dealkylation. The parent compound was not detected. The O-demethylated metabolites were found to be the most useful metabolic markers for the identification of RCS-4 ingestion.