{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,8,5]],"date-time":"2025-08-05T12:36:32Z","timestamp":1754397392638,"version":"3.40.5"},"reference-count":25,"publisher":"Wiley","issue":"5","license":[{"start":{"date-parts":[[2023,6,16]],"date-time":"2023-06-16T00:00:00Z","timestamp":1686873600000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"content-domain":{"domain":["onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["Journal of Forensic Sciences"],"published-print":{"date-parts":[[2023,9]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>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 <jats:ext-link xmlns:xlink=\"http:\/\/www.w3.org\/1999\/xlink\" xlink:href=\"http:\/\/drugsdata.org\">DrugsData.org<\/jats:ext-link>. The gas chromatography\u2013mass spectrometry (GC\u2013MS) 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\u2010amino\u20105\u2010chlorobenzophenone 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\u2013MS and compared to the tablet submission data. The major compound in this submission, <jats:italic>N<\/jats:italic>\u2010(2\u2010benzoyl\u20104\u2010chlorophenyl)\u20102\u2010chloroacetamide, along with several related byproducts were successfully reproduced indicating that the tablet contents potentially stem from a failure to synthesize alprazolam.<\/jats:p>","DOI":"10.1111\/1556-4029.15315","type":"journal-article","created":{"date-parts":[[2023,6,16]],"date-time":"2023-06-16T11:39:25Z","timestamp":1686915565000},"page":"1825-1834","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":1,"title":["Compounds identified in an illicit generic Xanax tablet are the result of a failed synthesis of alprazolam"],"prefix":"10.1111","volume":"68","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-9256-8984","authenticated-orcid":false,"given":"Koby L.","family":"Kizzire","sequence":"first","affiliation":[{"name":"Department of Forensic Sciences University of New Haven  West Haven Connecticut USA"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Emily","family":"Langlois","sequence":"additional","affiliation":[{"name":"Department of Forensic Sciences University of New Haven  West Haven Connecticut USA"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Savannah","family":"Brown","sequence":"additional","affiliation":[{"name":"Department of Forensic Sciences University of New Haven  West Haven Connecticut USA"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"311","published-online":{"date-parts":[[2023,6,16]]},"reference":[{"key":"e_1_2_8_2_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.neuropharm.2018.01.036"},{"key":"e_1_2_8_3_1","doi-asserted-by":"publisher","DOI":"10.3390\/toxics9020025"},{"key":"e_1_2_8_4_1","doi-asserted-by":"publisher","DOI":"10.1001\/jama.2020.22106"},{"key":"e_1_2_8_5_1","doi-asserted-by":"publisher","DOI":"10.1111\/j.1360\u20100443.1994.tb03743.x"},{"key":"e_1_2_8_6_1","unstructured":"U.S. Food and Drug Administration.FDA Drug Safety Communication: FDA requiring boxed warning updated to improve safe use of benzodiazepine drug class. 09\u201023\u20102020. [cited 2023 May 23]. Available from:https:\/\/www.fda.gov\/drugs\/drug\u2010safety\u2010and\u2010availability\/fda\u2010requiring\u2010boxed\u2010warning\u2010updated\u2010improve\u2010safe\u2010use\u2010benzodiazepine\u2010drug\u2010class"},{"key":"e_1_2_8_7_1","doi-asserted-by":"publisher","DOI":"10.1001\/jama.2021.4513"},{"key":"e_1_2_8_8_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.forsciint.2021.110819"},{"key":"e_1_2_8_9_1","unstructured":"National Institute on Drug Abuse.Trends & statistics: overdose death rates. [cited 2023 May 23]. Available from:https:\/\/www.drugabuse.gov\/drug\u2010topics\/trends\u2010statistics\/overdose\u2010death\u2010rates"},{"key":"e_1_2_8_10_1","doi-asserted-by":"publisher","DOI":"10.3390\/pharmacy6020043"},{"key":"e_1_2_8_11_1","doi-asserted-by":"publisher","DOI":"10.18356\/d5354eb9-en"},{"key":"e_1_2_8_12_1","doi-asserted-by":"publisher","DOI":"10.1002\/wfs2.1393"},{"volume-title":"World drug report 2021","year":"2021","author":"United Nations Office on Drugs and Crime","key":"e_1_2_8_13_1"},{"key":"e_1_2_8_14_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.drugalcdep.2020.108300"},{"key":"e_1_2_8_15_1","unstructured":"DrugsData.org by Erowid Center.Fake Xanax (G3722) sold as Xanax (generic) ID: 8355. [cited 2023 May 23]. Available from:https:\/\/www.drugsdata.org\/view.php?id=8355"},{"key":"e_1_2_8_16_1","doi-asserted-by":"publisher","DOI":"10.1007\/s00044\u2010016\u20101585\u2010z"},{"key":"e_1_2_8_17_1","first-page":"63","volume-title":"Advances in heterocyclic chemistry","author":"Hemming K","year":"2017"},{"key":"e_1_2_8_18_1","doi-asserted-by":"publisher","DOI":"10.1039\/D0RA09198G"},{"key":"e_1_2_8_19_1","doi-asserted-by":"publisher","DOI":"10.3390\/molecules25040999"},{"key":"e_1_2_8_20_1","unstructured":"WallaceWE.NIST chemistry webbook SRD 69. Benzophenone 2\u2010amino\u20105\u2010chloro. [cited 2023 May 23]. 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