title: Identification of pyrolysis products of the new psychoactive substance 2-amino-1-(4-bromo-2,5-dimethoxyphenyl)ethanone hydrochloride (bk-2C-B) and its iodo analogue bk-2C-I.
abstract: 2-Amino-1-(4-bromo-2,5-dimethoxyphenyl)ethanone hydrochloride (bk-2C-B) has recently emerged as a new psychoactive substance (NPS). It is most commonly consumed orally, although there are indications that it might also be ingested by inhalation or 'smoking'. Information about the stability of bk-2C-B when exposed to heat is unavailable and the potential for pyrolytic degradation and formation of unknown substances available for inhalation prompted an investigation using a simulated 'meth pipe' scenario. Twelve products following pyrolysis of bk-2C-B were detected and verified by organic synthesis of the corresponding standards. In addition, 2-amino-1-(4-iodo-2,5-dimethoxyphenyl)ethanone hydrochloride (bk-2C-I) was characterized for the first time and subjected to pyrolysis as well. Similar products were formed, which indicated that the replacement of the bromo with the iodo substituent did not affect the pyrolysis pattern under the conditions used. Two additional products were detected in the bk-2C-I pyrolates, namely 1-(2,5-dimethoxyphenyl)-ethanone and 1-iodo-4-ethenyl-5-methoxyphenol. The potential ingestion of pyrolysis products with unknown toxicity adds an element of concern. Copyright © 2017 John Wiley & Sons, Ltd.
authors.affiliation: Department of Justice Sciences, University of Alabama at Birmingham, 1201 University Boulevard, Birmingham, AL, 35294, USA.
authors.forename: Kelly B
authors.initials: KB
authors.lastname: Texter
authors.affiliation: Department of Justice Sciences, University of Alabama at Birmingham, 1201 University Boulevard, Birmingham, AL, 35294, USA.
authors.forename: Rachel
authors.initials: R
authors.lastname: Waymach
authors.affiliation: Department of Pharmacology and Therapeutics, School of Medicine, Trinity Centre for Health Sciences, St James's Hospital, Dublin 8, Ireland.
authors.forename: Pierce V
authors.initials: PV
authors.lastname: Kavanagh
authors.affiliation: School of Chemistry, Trinity College Dublin, University of Dublin College Green, Dublin 2, D02 EV57, Ireland.
authors.forename: John E
authors.initials: JE
authors.lastname: O'Brien
authors.affiliation: School of Pharmacy and Pharmaceutical Sciences, Trinity College Dublin, The University of Dublin, College Green, Dublin 2, D02 EV57.
authors.forename: Brian
authors.initials: B
authors.lastname: Talbot
authors.affiliation: School of Pharmacy and Biomolecular Sciences, Liverpool John Moores University, Byrom Street, Liverpool, L3 3AF, UK.
authors.forename: Simon D
authors.identifier: http://orcid.org/0000-0001-8632-5372
authors.initials: SD
authors.lastname: Brandt
authors.affiliation: Department of Justice Sciences, University of Alabama at Birmingham, 1201 University Boulevard, Birmingham, AL, 35294, USA.
authors.forename: Elizabeth A
authors.identifier: http://orcid.org/0000-0001-8711-4833
authors.initials: EA
authors.lastname: Gardner
mesh_terms: D000098:Acetophenones / Q000032:analysis* / Q000737:chemistry*; D008401:Gas Chromatography-Mass Spectrometry / Q000379:methods* / Q000592:standards; D011619:Psychotropic Drugs / Q000032:analysis* / Q000737:chemistry*; D000077319:Pyrolysis
chemical_list: D000098:Acetophenones; D011619:Psychotropic Drugs; C000605764:2-amino-1-(4-bromo-2,5-dimethoxyphenyl)ethan-1-one
keywords: forensic chemistry; new psychoactive substances; phenethylamines; profiling; pyrolysis