@article{ref1,
title="Compounds identified in an illicit generic Xanax tablet are the result of a failed synthesis of alprazolam",
journal="Journal of forensic sciences",
year="2023",
author="Kizzire, Koby L. and Langlois, Emily and Brown, Savannah",
volume="ePub",
number="ePub",
pages="ePub-ePub",
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.<p /> <p>Language: en</p>",
language="en",
issn="0022-1198",
doi="10.1111/1556-4029.15315",
url="http://dx.doi.org/10.1111/1556-4029.15315"
}