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                            Library & Multimedia
 Spectroscopic Differentiation and Chromatographic Separation of Regioisomeric Indole Aldehydes: Synthetic Cannabinoids Precursors
NCJ Number
              255749
Journal

*Forensic Chemistry* Volume: 12 Dated: March 2019 Pages: 78-90
Author(s)
          Younis Abiedalla;
                        Lewis W. Smith;
                        Karim M Abdel-Hay;
                        Logan Neel;
                        Tarek S Belal;
                        Amber Thaxton-Weissenfluh;
                        Forrest Smith;
                        Jack DeRuiter;
                        C. Randall Clark
Date Published

March 2019
Length
              13 pages
Annotation
              This study compared the analytical properties of 12 indole aldehydes.
Abstract
              The compounds in this study were the six regioisomeric 2-, 3-, 4-, 5-, 6- and 7-formyl indoles and the corresponding six regioisomeric N-n-pentylindole aldehydes. These compounds can serve as precursor chemicals and synthetic intermediates for several synthetic cannabinoid drugs. These two sets (the six regioisomeric indole aldehydes as well as the six regioisomeric pentylindole aldehydes) each have identical elemental compositions and differ in the position of attachment of the aldehyde group on the indole ring. The electron ionization mass spectra for the indole aldehydes were essentially identical. However, the vapor phase infrared spectra showed differences in the absorption frequencies for the Nsingle bondH and carbonyl groups based on intramolecular interactions. The associated Nsingle bondH absorption band occurs as low as 3467cm-1 while the free band is as high as 3517-cm-1. The aldehyde carbonyl band for the indole aldehydes varies from 1713-cm-1 to 1686-cm-1. Substitution of the aldehyde group on the pyrrole ring for the N-n-pentylindole aldehydes yields lower carbonyl absorption bands. The EI mass spectra for the pentylindole aldehydes are identical with little information for differentiation among these six regioisomeric compounds. The six compounds were separated on a capillary column using gas chromatography and the elution order appears to be related to the steric crowding of the indole ring substituents. (publisher abstract modified)
      
  
          Additional Details
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.
    
  
  
Date Published: March 1, 2019
    
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