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                            Funding & Awards
 Forensic Chemistry of Substituted 1-Alkyl-3-Acylindoles: Isomeric Synthetic Cannabinoids.
Award Information
Awardee
              Auburn University
Award #
              2012-DN-BX-K026
Funding Category
              Competitive
Location
                    Auburn University, AL
Awardee County
              Lee
Congressional District
              3
Status
              Closed
Funding First Awarded
              2012
Total funding (to date)
              $865,784
Original Solicitation
              NIJ FY 12 Basic Scientific Research to Support Forensic Science for Criminal Justice Purposes
Description of original award (Fiscal Year 2012, $865,784)
The continued manufacture, distribution, importation and abuse of the synthetic cannabinoids have resulted in the recent placement of many of these compounds into Federal Schedule 1 control. These compounds have no recognized therapeutic use and pose an imminent hazard to the public safety. The synthesis of these compounds, especially the JWH compounds, is relatively straightforward and can allow for clandestine production and further designer drug development. There are a number of commercially available precursor materials to produce the substituted indoles and legal control of all these substances is not possible. Indole is readily available from many commercial suppliers and, if controlled, indole can be synthesized from other commercial precursors in essentially a one-step process. Thus, as legal controls intensify, it is likely that the clandestine production of JWH-type compounds will increase, as well as the production of new designer drug derivatives as observed over the past several decades with the amphetamine, MDMA, piperazine and bath salt classes of controlled substances. The substituted indoles represent a relatively new chemical category of drugs of abuse. Forensic chemists do not have significant experience in this area of drug/organic chemistry. It is critical that an extensive forensic chemical study for a complete series of isomeric indoles of the JWH style be made available to the forensic chemistry community. The first question to be addressed in this project concerns the uniqueness of the 1,3-indole ring substitution pattern: Are the spectral data obtained from the 1-alkyl-3-acylindoles unique to only the 1,3-indole ring substitution pattern? The precursor chemicals are available to prepare the acyl group substituted indole for every indole ring position (ie seven isomers for mono-acyl indole). While the 1-alkyl-3-acylindoles are the most likely candidates for the clandestine market, it is important for the forensic chemist to know that the analytical data generated eliminates the other isomeric indole ring substitution patterns of the equivalent substituent. Designer drug development among the indole cannabinoid compounds is another key issue of forensic importance. As regulatory controls tighten with respect to available indole cannabinoids, designer derivative exploration and synthesis is expected to grow more intense. This designer exploration will likely parallel that observed in the phenylalkylamine series of drugs and involve methoxy, dimethoxy, bromo-dimethoxy, methylenedioxy, trifluoromethyl, chloro, and methyl substituents, as well as regiosiomers of these substitution patterns. These aromatic ring substituents are known to enhance CNS hallucinogenic or entactogenic activity in the phenethylamines, bath salt and piperazine drugs of abuse. Many of these aromatic ring substituted precursor materials are commercially available and can be readily incorporated into the structural framework of the JWH-style indole cannabinoid compounds. It could be argued that isomer differentiation is not necessary in forensic science based on the U. S. Controlled Substance Analog Act. The law should make all these isomers controlled substances. However the forensic chemist is faced with the same basic dilemma: The compound must be specifically identified in order to know if it is an analog of a controlled substance. A proactive investigation of the forensic analytical chemistry of these future designer substances is an objective of this project. The resulting analytical data and methods represent important advancements in forensic drug chemistry. The relationship between drug/isomer structure and analytical properties such as mass spectral fragmentation will be evaluated by the synthesis of labeled (isotopic and homologous labels) synthetic cannabinoid compounds. ca/ncf



  
Grant-Funded Publications
        
                      GC-MS and GC-IR analysis of regioisomeric cannabinoids related to 1-(5-fluoropentyl)-3-(1-naphthoyl)-indole
                  Spectroscopic Differentiation and Chromatographic Separation of Regioisomeric Indole Aldehydes: Synthetic Cannabinoids Precursors
                  Spectroscopic Differentiation and Regioisomeric Indole Aldehydes: Synthetic Cannabinoids Precursors
                  Forensic Chemistry of Substituted 1-Alkyl-3-Acylindoles: Isomeric Synthetic Cannabinoids
                  GC-MS and GC-IR analysis of regioisomeric cannabinoids related to 1-(5-fluoropentyl)-3-(1-naphthoyl)-indole
                  Analytical Studies on the 2-naphthoyl substituted-l-n-pentylindoles Regioisomeric Synthetic Cannabinoids
                  Differentiation of Methylated Indole Ring Regioisomers of JWH-007: GC-MS and GC-IR Studies
                  Correlation of Vapor Phase Infrared Spectra and Regioisomeric Structure in Synthetic cannabinoids
                  GC-MS and GC-IR Analyses of the Methoxy-1-n-pentyl-3-(1-naphthoyl)-indoles: Regioisomeric Designer Cannabinoids
                  GC-MS Analysis of the Regioisomeric Methoxy- and Methyl-Benzoyl-1-Pentylindoles: Isomeric Synthetic Cannabinoids
                  Analytical Differentiation of 1-Alkyl-3-acylindoles and 1-Acyl-3-alkylindoles: Isomeric Synthetic Cannabinoids
                  GC-MS Differentiation of the Six Regioisomeric Dimethoxybenzoyl-1-Pentylindoles: Isomeric Cannabinoid Substances
                  GC-MS Studies on the Six Naphthoyl-Substituted 1-N-Pentyl-Indoles: JWH-018 and Five Regioisomeric Equivalents
                  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
                  GC-MS and FTIR Evaluation of the Six Benzoyl-substituted-1-pentylindoles: Isomeric Synthetic Cannabinoids

  
Date Created: August 22, 2012
    
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                  Nanoparticle-Decorated Micropillars As Integrated Raman Spectroscopy and Mass Spectrometry Substrates for Quantitative and High-Throughput Toxicology Drug Analysis
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