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Citation |
Kizzire KL, Langlois E, Brown S. J. Forensic Sci. 2023; ePub(ePub): ePub. |
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Copyright |
(Copyright © 2023, American Society for Testing and Materials, Publisher John Wiley and Sons) |
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DOI |
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PMID |
37326301 |
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Abstract |
Unintended compounds produced by inexperienced clandestine chemists may present a challenge in laboratories tasked with their identification. In March 2020, an anonymously submitted tablet purchased as a generic form of Xanax was analyzed by Erowid's DrugsData.org. The gas chromatography-mass spectrometry (GC-MS) results publicly released online indicated several unidentified compounds due to a lack of database references at that time. Elucidation by our group indicated the presence of several structurally related compounds that were linked to a failed synthesis of alprazolam. For this case study, a published procedure for the synthesis of alprazolam starting with the chloroacetylation of 2-amino-5-chlorobenzophenone was identified as a potential source of this failure. The procedure was reproduced to identify pitfalls of the methodology and examine its possible link to the illicit tablet. Reaction outcomes were analyzed via GC-MS and compared to the tablet submission data. The major compound in this submission, N-(2-benzoyl-4-chlorophenyl)-2-chloroacetamide, along with several related byproducts were successfully reproduced indicating that the tablet contents potentially stem from a failure to synthesize alprazolam. Language: en |
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Keywords |
benzodiazepines; alprazolam; byproducts; clandestine synthesis; forensic drug analysis; illicit tablets; Xanax |