This Is AuburnElectronic Theses and Dissertations

GC-MS Studies on a Series of 1-pentylacylindoles: Regioisomeric Compounds Related to the Synthetic Cannabinoids.




Alsegiani, Amsha

Type of Degree

Master's Thesis




This thesis is primarily focused on analytical approaches to differentiate twenty isomeric compounds related to designer drugs of the1-pentyl-acylindoles class. The compounds investigated represent a series of synthetic cannabinoids substances associated mainly with naphthoylindole and benzoylindole structures. These compounds represent potential designer modification of banned drugs. Electron-ionization gas chromatography-mass spectrometry (EIGC-MS) was used as the initial method to differentiate and separate the target compounds. Chapter one is a literature review of synthetic cannabinoids history, general pharmacology, metabolism and elimination, in addition to a brief review on the general analytical methods used on synthetic cannabinoids. The project rationale and statement of research objectives are also included. Chapter two compares the analytical properties of the first banned naphthoylindole compound in clandestine samples 1-n-pentyl-3-(1-naphthoyl)indole, JWH-018, with three possible regioisomers, 1-n-pentyl-3-(2-naphthoyl) indole, 1-(1-naphthoyl)-3-n- pentylindole and 1-(2-naphthoyl)-3-n-pentylindole. Chapter three compares the six regioisomers of 1-n-pentyl-3- (dimethoxybenzoyl)-indoles. Chapter four compares JWH-018 with eleven possible regioisomeric 1-n-pentyl-naphthoylindoles.