Analytical Studies on the 2-naphthoyl substituted-l-n-pentylindoles Regioisomeric Synthetic Cannabinoids

• NCJ Number: 253496
• Journal: Journal of Chromatography B-Analytical Technologies in the Biomedical and Life Sciences Volume: 1077-1078 Dated: March 2018 Pages: 77-84
• Author(s): Amber Thaxton-Weissenfluh; Amsha S. Alsegiani; Younis Abiedalla; Jack DeRuiter; Forrest Smith; C. R. Clark
• Date Published: March 2018
• Length: 8 pages
• Grant Number(s): 2012-DN-BX-K026
• Agencies: NIJ-Sponsored
• Publication Type: Research (Applied/Empirical); Report (Study/Research); Report (Grant Sponsored); Program/Project Description
• Award: Forensic Chemistry of Substituted 1-Alkyl-3-Acylindoles: Isomeric Synthetic Cannabinoids.

Annotation

This article reports on analytical studies of the 2-naphthoyl substituted-1-n -pentylindoles with reference to regioisomeric synthetic cannabinoids.

Abstract

The six 1-n-pentyl-2-, 3-, 4-, 5-, 6- and 7-(2-naphthoyl)-indoles each have the same substituents attached to the indole ring, identical elemental composition (C24H23NO) yielding identical nominal and accurate masses. The electron ionization mass spectra of the 2-naphthoyl substituted isomers share equivalent major fragment ions resulting from cleavage of the groups attached to the central indole nucleus with some differences in relative abundances. These six regioisomers were successfully resolved on a Rtx-5 and Rxi-17Sil MS stationary phases and the molecules having both substituent groups on the same side of the indole ring (1,2- and 1,7-substituents) show the least retention. The more linear molecules have higher relative retention properties. A comparison of the GC properties of the 1-naphthoyl- and 2-naphthoyl groups attached at identical positions of the indole ring showed higher GC retention for the 2-naphthoyl substituted isomer in all cases evaluated. The amide inverse isomers (1-naphthoyl-3-n-pentylindoles) were separated from the 1-n-pentyl-3-naphthoyl-indoles on a Rtx-200 stationary phase. The two inverse amide isomers having the 1- and 2-naphthoyl groups substituted at the 1-position of the indole ring elute before either of the N-alkyl-indole isomers having the 1- and 2-naphthoyl groups substituted at the 3-position of the indole ring. The amide inverse isomers yield EI mass spectra easily distinguishing these amides from the ketone isomers having the naphthoyl groups at the indole 3-position. (publisher abstract modified)