title: Test purchase, identification and synthesis of 2-amino-1-(4-bromo-2, 5-dimethoxyphenyl)ethan-1-one (bk-2C-B).
abstract: 2-Amino-1-(4-bromo-2,5-dimethoxyphenyl)ethan-1-one (bk-2C-B) has been recently offered for purchase by a variety of Internet retailers. This substance may be considered a cathinone analogue of the phenethylamine 2-(4-bromo-2,5-dimethoxyphenyl)ethan-1-amine (2C-B) which suggests that it may have psychoactive effects in humans. A test purchase of bk-2C-B was carried out and its identity was confirmed by a range of analytical techniques including nuclear magnetic resonance spectroscopy, gas and liquid chromatography, and high-resolution mass spectrometry. Confirmation was also obtained from the synthesis of bk-2C-B based on the implementation of the Delépine reaction in which the α-brominated intermediate was reacted with hexamethylenetetramine to afford the primary amine. Analysis of underivatized bk-2C-B by gas chromatography-mass spectrometry (GC-MS) showed that there was potential for artificial formation of 1-(4-bromo-2,5-dimethoxyphenyl)ethanone and a pyrazine dimer, these substances were not detected when employing liquid chromatographic analysis. Ion chromatography and X-ray crystallography analysis confirmed that the purchased bk-2C-B consisted of a hydrochloride and hydrobromide salt mixture, which indicated that it might have been prepared by the hexamethylenetetramine route followed by hydrochloric acid hydrolysis of the quaternary ammonium salt. X-ray crystallography also revealed that the purchased (mixed HCl/HBr salt) and synthesized bk-2C-B (HCl salt) exists as polymorphs.
authors: Department of Pharmacology and Therapeutics, School of Medicine, Trinity Centre for Health Sciences, St James Hospital, Dublin 8, Ireland.|Forensic Science Laboratory, Garda HQ, Dublin 8, Ireland.
authors: John D
authors: JD
authors: Power
authors: Department of Pharmacology and Therapeutics, School of Medicine, Trinity Centre for Health Sciences, St James Hospital, Dublin 8, Ireland.
authors: Pierce
authors: P
authors: Kavanagh
authors: School of Chemistry, Trinity College, Dublin 2, Ireland.
authors: John
authors: J
authors: O'Brien
authors: Department of Pharmacology and Therapeutics, School of Medicine, Trinity Centre for Health Sciences, St James Hospital, Dublin 8, Ireland.
authors: Michael
authors: M
authors: Barry
authors: Department of Pharmacology and Therapeutics, School of Medicine, Trinity Centre for Health Sciences, St James Hospital, Dublin 8, Ireland.|School of Chemistry, Trinity College, Dublin 2, Ireland.
authors: Brendan
authors: B
authors: Twamley
authors: School of Pharmacy and Pharmaceutical Sciences, Trinity College, Dublin 2, Ireland.
authors: Brian
authors: B
authors: Talbot
authors: The State Laboratory, Backweston Lab Complex, Celbridge, Co, Kildare, Ireland.
authors: Geraldine
authors: G
authors: Dowling
authors: School of Pharmacy and Biomolecular Sciences, Liverpool John Moores University, Byrom Street, L3 3AF, Liverpool, UK.
authors: Simon D
authors: SD
authors: Brandt
mesh_terms: D000098:Acetophenones / Q000032:analysis* / Q000138:chemical synthesis*; D002853:Chromatography, Liquid; D018360:Crystallography, X-Ray; D015198:Designer Drugs / Q000032:analysis* / Q000138:chemical synthesis; D004118:Dimethoxyphenylethylamine / Q000031:analogs & derivatives* / Q000032:analysis; D008401:Gas Chromatography-Mass Spectrometry; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D021241:Spectrometry, Mass, Electrospray Ionization; D015813:Substance Abuse Detection / Q000379:methods*
chemical_list: D000098:Acetophenones; D015198:Designer Drugs; D004118:Dimethoxyphenylethylamine; C079321:2-(4-bromo-2,5-dimethoxyphenyl)ethylamine; C000605764:2-amino-1-(4-bromo-2,5-dimethoxyphenyl)ethan-1-one
keywords: 2C-B; beta keto-phenethylamines; bk-2C-B; cathinones; forensic; new psychoactive substances; synthesis