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GC-MS and GC-IR Analyses of the Methoxy-1-n-pentyl-3-(1-naphthoyl)-indoles: Regioisomeric Designer Cannabinoids

NCJ Number
254070
Journal
Journal of Chromatographic Science Volume: 56 Issue: 9 Dated: 2018 Pages: 779-788
Author(s)
Amber Thaxton-Weissenfluh; Tarek S. Belal; Jack DeRuiter; Forrest Smith; Younis Abiedalla; Logan Neel; Karim M. Abdel-Hay
Date Published
2018
Length
10 pages
Annotation

This article reports on a project that involved the GC-MS and GC-IR analyses of the methoxy-1-n-pentyl-3-(1-naphthoyl)-indoles, which represent indole ring-substituted analogs of the synthetic cannabinoid JEH-018.

Abstract

The electron ionization mass spectra showed equivalent regioisomeric major fragments resulting from cleavage of the groups attached to the central indole nucleus. The characteristic (M-17)+ fragment ion at m/z 354 resulting from the loss of OH group is significant in the mass spectra of all four compounds. Fragmentation of the naphthoyl and/or pentyl groups yields the cations at m/z 314, 300, 244 and 216. The vapor-phase infrared spectra provide some characteristic absorption bands to identify the individual isomers. Gas chromatographic separations on a capillary column containing a film of trifluoropropylmethyl polysiloxane (Rtx-200) provided excellent resolution of these compounds, their precursor indoles and intermediate pentylindoles. The elution order appears related to the degree of crowding of indole ring substituents. (publisher abstract modified)