The substituted indoles represent a relatively new chemical category of drugs of abuse. These substituted indoles can exist in a number of regioisomeric forms. We have prepared several series of regioisomers of the indole ring to establish the analytical uniqueness of the 1,3-indole ring substitution pattern.      While the 1-alkyl-3-acylindoles are the most likely candidates for cannabinoid activity, it is important to know that the analytical data generated eliminates the other indole ring substitution patterns of the equivalent substituent. Our research has evaluated the 1-pentyl indoles having the acyl group substituted at all six of the remaining available indole ring substitution positions. Analytical comparisons will be made for the six benzoyl and the six 1-naphthoyl indole regioisomers. These studies focus on chromatographic, mass spectral and infrared evaluation of these compounds.     The inverse isomers representing the specific reversal of the relative positions of the two common indole substituents found in the synthetic cannabinoids have been prepared and evaluated in this project (1-benzoyl-3-n-pentylindole compared to 1-n-pentyl-3-benzoylindole and 1-naphthoyl-3-n-pentylindole compared to 1-n-pentyl-3-naphthoylindole, JWH-018).     The overall goal of these studies is to provide an analytical framework for the identification of individual substituted indoles to the exclusion of all other possible isomeric and homologous forms of these compounds. The analytical profiling and differentiation of these compounds make use of GC-MS,  IR, and some exact mass GC-TOF-MS studies. In addition, stable isotope labelling experiments with deuterium or carbon-13 provide specific information about fragmentation products in mass spectrometry. The mass spectra of labelled compounds yield mass shifts compared to the unlabelled fragments allowing structure verification.

Forensic chemistry of substituted 1-alkyl-3-acylindoles: Isomeric synthetic cannabinoids

248th National Meeting (2014)

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