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                            Library & Multimedia
 Mass Spectral Studies on 1-n-pentyl-3-(1-naphthoyl)indole (JWH-018),  Three Deuterium-labeled Analogues and the Inverse Isomer 1-naphthoyl-3-n-pentylindole
NCJ Number
              249446
Journal

*Rapid Communications in Mass Spectrometry* Volume: 29 Issue: 9 Dated: May 2015 Pages: 871-877
Author(s)
          Amber  Thaxton;
                        Tarek S. Belal;
                        Forrest  Smith;
                        Jack  DeRuiter;
                        Karim M. Abdel-Hay;
                        C. Randall  Clark
Date Published

May 2015
Length
              7 pages
Annotation
              This study compared the electron ionization mass spectrometric (EI-MS) fragmentation of the 1-n-pentyl-3-(1-naphthoyl)indole to its inverse isomer 1-naphthoyl-3-n-pentylindole.
Abstract
              These two substances are directly available from indole using identical precursor reagents and similar reaction conditions. Stable isotope deuterium labeling of the three major regions of the JWH-018 molecule allows confirmation of the structures of the major fragment ions. The spectra for the 1-n-pentyl-3-(1-naphthoyl)-d5-indole, 1-n-pentyl-3-(1-d7-naphthoyl)indole and 1-d11-n-pentyl-3-(1-naphthoyl)indole provide significant assistance in elucidating the structures for the major fragment ions in JWH-018. The study found that 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 fragment ion [M-17]+ at m/z 324 for JWH-018 was formed by the elimination of a hydroxyl radical and the spectra of the three deuterium-labeled derivatives indicated the loss of hydrogen from the naphthalene ring. Further structural analogues suggest the hydrogen comes from the 8-position of the naphthalene ring. The three deuterium-labeled analogues provide significant assistance in confirming the structures for the major fragment ions in the mass spectrum of the traditional synthetic cannabinoid compound, 1-n-pentyl-3-(1-naphthoyl)indole, JWH-018. The 1-naphthoyl-3-n-pentylindole inverse regioisomer can be easily differentiated from the traditional synthetic cannabinoid compound. (Publisher abstract modified)
      
  
          Additional Details
Grant Number(s)
        2012-DN-BX-K026


  
  
        
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        NIJ-Sponsored


  
  
        
  Publication Type
        Research (Applied/Empirical)
                                Report (Study/Research)
                                Report (Grant Sponsored)


  
  
        
  Award
        Forensic Chemistry of Substituted 1-Alkyl-3-Acylindoles: Isomeric Synthetic Cannabinoids.
    
  
  
Date Published: May 1, 2015
    
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