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Gas Chromatography-Mass Spectrometry (GC-MS) and Gas Chromatography-Infrared (GC-IR) Analyses of the Chloro-1-n-pentyl-3-(1-naphthoyl)-Indoles: Regioisomeric Cannabinoids

NCJ Number
Applied Spectroscopy Volume: 73 Issue: 4 Dated: 2019 Pages: 433-443
Date Published
11 pages

This article describes the analytical differentiation of the indole ring regioisomeric chloro-1-n-pentyl-3-(1-naphthoyl)-indoles.


The regioisomeric chloroindole precursor compounds, N-n-pentyl chloroindole synthetic intermediates, and the target chloro-substituted naphthoylindoles showed the equivalent gas chromatographic elution order based on the position of chlorine substitution on the indole ring. The regioisomeric chloro-1-n-pentyl-3-(1-naphthoyl)-indoles yield electron ionization mass spectra having equivalent major fragments resulting from cleavage of the groups attached to the central indole nucleus. Fragment ions occur at m/z 127 and 155 for the naphthyl and naphthoyl cations common to all indoles having the naphthoyl group substituted at the indole-3 position. Fragments resulting from the loss of the naphthoyl and/or n-pentyl groups from the molecular radical cation yield the cations at m/z 318, 304, 248, and 178. The characteristic (M-17)+ fragment ion at m/z 358 resulting from the loss of OH radical is significant in the mass spectra of all these compounds with 1-naphthoyl groups substituted at the indole-3 position. The vapor phase infrared spectra provide a number of characteristic absorption bands to identify the individual isomers. (publisher abstract modified)

Date Published: January 1, 2019