GC-MS Differentiation of the Six Regioisomeric Dimethoxybenzoyl-1-Pentylindoles: Isomeric Cannabinoid Substances

• NCJ Number: 250892
• 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: September 2015
• Length: 8 pages
• Grant Number(s): 2012-DN-BX-K026
• Agencies: NIJ-Sponsored
• Publication Type: Research (Applied/Empirical); Report (Technical); Report (Technical Assistance); Report (Summary); Report (Study/Research); Report (Grant Sponsored)
• Award: Forensic Chemistry of Substituted 1-Alkyl-3-Acylindoles: Isomeric Synthetic Cannabinoids.

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)