title: Analytical differentiation of 1-alkyl-3-acylindoles and 1-acyl-3-alkylindoles: isomeric synthetic cannabinoids.
abstract: The 1-alkyl-3-acylindoles and the inverse regioisomeric 1-acyl-3-alkylindoles can be prepared directly from a common set of precursor materials and using similar synthetic strategies. The EI mass spectra for these isomers show a number of unique ions which allow for the differentiation of the 1-alkyl-3-acylindole compounds from the inverse regioisomeric 1-acyl-3-alkylindoles. The base peak at m/z 214 in the 1-n-pentyl-3-benzoylindole represents the M-77 cation fragment resulting from the loss of the phenyl group, and this ion is not observed in the inverse isomer. The 1-benzoyl-3-n-pentylindole inverse regioisomer shows a base peak at m/z 105 for the benzoyl cation. Thus, these two base peaks are the result of fragmentation initiated at the carbonyl-oxygen for both isomers. The 1-pentyl-3-benzoylindole is characterized by the strong intensity carbonyl band at 1703 cm(-1), while the amide carbonyl appears as a strong band of equal intensity at 1681 cm(-1) in the 1-benzoyl-3-pentyl regioisomer.
authors.affiliation: Department of Drug Discovery and Development Harrison, School of Pharmacy, Auburn University , Auburn, AL 36849, United States.
authors.forename: Jack
authors.initials: J
authors.lastname: DeRuiter
authors.forename: Forrest T
authors.initials: FT
authors.lastname: Smith
authors.forename: Karim
authors.initials: K
authors.lastname: Abdel-Hay
authors.forename: C Randall
authors.initials: CR
authors.lastname: Clark
mesh_terms: D002186:Cannabinoids / Q000032:analysis* / Q000737:chemistry*; D008401:Gas Chromatography-Mass Spectrometry; D007211:Indoles / Q000737:chemistry*; D007536:Isomerism; D021241:Spectrometry, Mass, Electrospray Ionization; D017550:Spectroscopy, Fourier Transform Infrared; D013329:Structure-Activity Relationship
chemical_list: D002186:Cannabinoids; D007211:Indoles