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NCJ Number: 250892 Find in a Library
Title: GC-MS Differentiation of the Six Regioisomeric Dimethoxybenzoyl-1-Pentylindoles: Isomeric Cannabinoid Substances
Journal: Science & Justice  Volume:55  Issue:5  Dated:September 2015  Pages:291-298
Author(s): K. M. Abdel-Hay; J. De Ruiter; F. Smith; Tarek S. Belal; C. Randall Clark
Date Published: June 2015
Page Count: 8
Sponsoring Agency: National Institute of Justice (NIJ)
Washington, DC 20531
Grant Number: 2012-DN-BX-K026
Document: HTML
Type: Report (Grant Sponsored); Report (Study/Research); Report (Summary); Report (Technical Assistance); Report (Technical); Research (Applied/Empirical)
Format: Article; Document (Online)
Language: English
Country: United States of America
Annotation: The regioisomeric 1-n-pentyl-3-(methoxybenzoyl)indoles and the 1-n-pentyl-3-(methylbenzoyl)indoles represent potential designer modifications in the synthetic cannabinoid drug category. These six compounds were prepared by a two-step synthetic method. The analytical properties and methods of regioisomeric differentiation were developed in this study.
Abstract: The molecular ion represents the base peak in the EI mass spectra for most of the compounds in this group. The meta- and para-isomers in each series display fragment ions at equivalent masses with some differences in relative abundance of these ions. The ortho-substituted isomers for both the methoxybenzoyl and methylbenzoyl series show a unique fragment ion occurring at M-17. Deuterium labeling for the methoxy group in the ortho-methoxybenzoyl isomer (ortho-OCD3) confirmed the ortho-substituent as the source of the hydrogen in OH (M-17) elimination. The two sets of regioisomers were well resolved by capillary gas chromatography and the elution order reflected increasing molecular linearity. In both sets of compounds the ortho-isomer eluted first and the para-isomer showed the highest retention time. The HPLC separation showed the ortho-isomer eluting first and the meta-isomer eluting last in both sets of regioisomers. (Publisher abstract modified)
Main Term(s): Forensic sciences
Index Term(s): Designer drugs; Drug analysis; Marijuana; National Institute of Justice (NIJ); NIJ grant-related documents
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