Compounds identified in an illicit generic Xanax tablet are the result of a failed synthesis of alprazolam.

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.