Discipline: Chemistry and Chemical Sciences
Subcategory: Chemistry (not Biochemistry)
Session: 3
Room: Exhibit Hall A
Terrell 'Terry' Shields Jr - University of New Orleans
Co-Author(s): Ryan McKinnie, Tasneam Darweesh, Phoebe Zito, Mark Trudell; Department of Chemistry, University of New Orleans, New Orleans, Louisiana, 70148
A new trend in the use of illicit substances has swept the globe as clandestine chemists are synthesizing new cannabinoid analogues for illegal consumption. These novel synthetic cannabinoids (SCBs) are based off an indazole backbone with varying substituents that bind to the endogenous cellular membrane G protein-coupled CB1 and CB2 receptors. These compounds and their metabolites have remained undetected via established drug testing methods allowing drug dealers elude law enforcement agencies and prosecution by the judicial system. Developed methods for the synthesis of many of these compounds has generated novel samples that have been characterized via HPLC and MS/MS methods to provide retention times and the mass of generated fragments. These data are being used to create an SCB library that provides important information in detection for drug testing and allow governments to codify laws against these novel compounds. Sample preparation for HPLC followed a modified method reported by Uchiyama (2012, 2013)1,2. In brief, stock solutions of 1 mg/mL of SCB compounds in HPLC grade methanol were prepared and diluted to 0.5 mg/mL. Samples solutions were analyzed using an Agilent 1200 HPLC with a diode array detector and sepperated on an Grace C18 colun (100 mm x 2.1 mm ID 1.8 μm). Samples were injected manually using a 10 μL injection loop. The column temperature was set to 40 degrees Celsius with a flow rate of 1.0 mL/min. A gradient profile was used with, 0.1% formic acid in water (A) and 0.1% formic acid in acetonitrile (B). Refer to Uchiyama et al. for further details.1,2 Results Table of selected novel synthetic cannabinoids with compound name, molecular formula, major substituent, molecular weight, M+1 ion, major product ion, and common precursor ions, samples HPLC chromatogram, and absorbance chromatogram, as well as Full ion, Product ion, and Precursor ion MS scans of selected SCs displayed denotes successful characterization from substituent groups. Conclusions The characterization of the novel synthetic cannabinoids was successful. HPLC generated unique retention times for each sample in the utilized gradient method of 0.1% formic acid in water and acetonitrile; MS/MS produced fragmentation patterns consistent with the substituents for each compound and subsequent ion fragments of those substituent ions. Future Work Re-run several samples at lower MS collision energies to fine tune measuring of the adamantyl group SCs; test further SCs; publish findings
Funder Acknowledgement(s): Oscar J. Tolmas Charitable Trust and the Chemical Analysis & Mass Spectrometry (CAMS) Facility at UNO
Faculty Advisor: Ashok Puri, apuri@uno.edu
Role: Reviewed and witnessed synthesis of compounds from Ryan McKinnie, TasneamDarweesh, and Dr. Mark Trudell; assisted in method utilization as presented by Dr. Zitooperated HPLC and MS to gather data 85% of the data collected for the abstract and for publication; photographs and figures created/designed by Terry Shields with assistance from the Chemical Analysis & Mass Spectrometry (CAMS) Facility at UNO.