Characterization of an Unknown Cannabinomimetic Compound in an Herbal "Incense" Sample by Gas Chromatography–High Resolution Time-of-Flight Mass Spectrometry
The Application Notebook
Synthetic cannabis products have garnered a great deal of media attention recently. Countless products are being sold at smoke shops, convenience stores, and online sites.
Synthetic cannabis products have garnered a great deal of media attention recently. Countless products are being sold at smoke shops, convenience stores, and online sites. These products are labeled "not for human consumption," but have been reported to have effects similar to cannabis when smoked. These reports have prompted testing in crime laboratories across the country. Some of the products tested have been confirmed to contain synthetic cannabinoids. The identification of these compounds by GC–MS can be challenging, as most of them are not present in commercially available mass spectral libraries. A particular product that received a great deal of media attention in the midwestern United States during 2010 was "Mr. Smiley." This product was reported to contain natural substances such as Mullein and Damiana leaf. It was also reported that when smoked, this product exhibited a "THC-like" high. Shortly before this product was pulled from store shelves, some was purchased for analysis to determine which compounds may be present.
Figure 1: GCâHRT TIC and extracted ion chromatogram for the analyte identified as 1-pentyl-3-(1-naphthoyl)indole or JWH-018. Notice a mass accuracy of 0.2 ppm was achieved.
The sample was initially analyzed by GC–TOFMS, but the most abundant analyte detected was not present in the commercially available NIST mass spectral database.
This application note shows the use of LECO's Pegasus GC–HRT high resolution time-of-flight mass spectrometer to provide an elemental composition based on accurate mass data, which ultimately lead to identification of the unknown compound.
Sample
A 1-gram sample of "Mr. Smiley" was weighed into a 20-mL vial. A 10-mL aliquot of ethyl acetate was added and the sample was sonicated for 10 min.
Experimental
The "Mr. Smiley" extract was analyzed on a LECO Pegasus GC–HRT system using the conditions shown below.
GC: Agilent 7890
Injection: 1 μL, split 50:1 at 275 °C
Column: Rtx-5, 10 m x 0.18 mm x 0.2 μm
Carrier gas: helium at 1.0 mL/min
Oven: 60 °C to 330 °C @ 50 °C/min, hold 10 min
Transfer Line: 300 °C
MS: LECO Pegasus GC–HRT
Acquisition Delay: 120 s
Saved mass range: 40–550 m/z
Flight Path: High Resolution (R = 25,000 FWHM)
Acquisition rate: 20 spectra/s
Source temperature: 250 °C
Results
The accurate mass data provided by the Pegasus GC-HRT was consistent with the formula C24H23NO. A literature search lead to identification of this formula as 1-pentyl-3-(1-naphthoyl)indole, or JWH-018, one of the most common synthetic cannabinoids used in "herbal incense" products.
Conclusions
This application shows how the high resolving power and mass accuracy of the Pegasus GC–HRT facilitate identification of substances absent from commercially available mass spectral libraries. This ability will be required as new abused substances are continually developed.
LECO Corporation
3000 Lakeview Avenue, St. Joseph, MI 49085
tel. (269) 985-5496, fax (269) 982-8977
Website: www.leco.com
New Study Uses MSPE with GC–MS to Analyze PFCAs in Water
January 20th 2025Scientists from the China University of Sciences combined magnetic solid-phase extraction (MSPE) with gas chromatography–mass spectrometry (GC–MS) to analyze perfluoro carboxylic acids (PFCAs) in different water environments.
The Next Frontier for Mass Spectrometry: Maximizing Ion Utilization
January 20th 2025In this podcast, Daniel DeBord, CTO of MOBILion Systems, describes a new high resolution mass spectrometry approach that promises to increase speed and sensitivity in omics applications. MOBILion recently introduced the PAMAF mode of operation, which stands for parallel accumulation with mobility aligned fragmentation. It substantially increases the fraction of ion used for mass spectrometry analysis by replacing the functionality of the quadrupole with high resolution ion mobility. Listen to learn more about this exciting new development.
A Guide To Finding the Ideal Syringe and Needle
January 20th 2025Hamilton has produced a series of reference guides to assist science professionals in finding the best-suited products and configurations for their applications. The Syringe and Needle Reference Guide provides detailed information on Hamilton Company’s full portfolio of syringes and needles. Everything from cleaning and preventative maintenance to individual part numbers are available for review. It also includes selection charts to help you choose between syringe terminations like cemented needles and luer tips.
The Complexity of Oligonucleotide Separations
January 9th 2025Peter Pellegrinelli, Applications Specialist at Advanced Materials Technology (AMT) explains the complexity of oligonucleotide separations due to the unique chemical properties of these molecules. Issues such as varying length, sequence complexity, and hydrophilic-hydrophobic characteristics make efficient separations difficult. Separation scientists are addressing these challenges by modifying mobile phase compositions, using varying ion-pairing reagents, and exploring alternative separation modes like HILIC and ion-exchange chromatography. Due to these complexities, AMT has introduced the HALO® OLIGO column, which offers high-resolution, fast separations through its innovative Fused-Core® technology and high pH stability. Alongside explaining the new column, Peter looks to the future of these separations and what is next to come.
Oasis or Sand Dune? Isolation of Psychedelic Compounds
January 20th 2025Magic mushrooms, once taboo, have recently experienced a renaissance. This new awakening is partially due to new findings that indicate the effects of psilocybin, and its dephosphorylated cousin psilocin may produce long lasting results for patients who might be struggling with anxiety, depression, alcohol and drug abuse, and post-traumatic stress disorder. Hamilton Company has developed a methodology for the isolation and identification of 5 common psychedelic compounds used in the potential treatment of disease. The PRP-1 HPLC column resin remains stable in the harsh alkaline conditions ideal for better separations.
