Characterization of hallucinogenic phenethylamines using high-resolution mass spectrometry for non-targeted screening purposes

Pasin, D; Cawley, A; Bidny, S; Fu, S

Characterization of hallucinogenic phenethylamines using high-resolution mass spectrometry for non-targeted screening purposes

Pasin, D

Cawley, A

Bidny, S Fu, S

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Publication Type:: Journal Article
Citation:: Drug Testing and Analysis, 2017, 9 (10), pp. 1620 - 1629
Issue Date:: 2017-10-01

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Field	Value	Language
dc.contributor.author	Pasin, D https://orcid.org/0000-0002-5037-7290	en_US
dc.contributor.author	Cawley, A https://orcid.org/0000-0002-3442-8617	en_US
dc.contributor.author	Bidny, S	en_US
dc.contributor.author	Fu, S https://orcid.org/0000-0002-6238-3612	en_US
dc.date.available	2017-01-23	en_US
dc.date.issued	2017-10-01	en_US
dc.identifier.citation	Drug Testing and Analysis, 2017, 9 (10), pp. 1620 - 1629	en_US
dc.identifier.issn	1942-7603	en_US
dc.identifier.uri	http://hdl.handle.net/10453/123716
dc.description.abstract	Copyright © 2017 John Wiley & Sons, Ltd. Hallucinogenic phenethylamines such as 2,5-dimethoxyphenethylamines (2C–X) and their N-(2-methoxybenzyl) derivatives (25X–NBOMe) have seen an increase in novel analogues in recent years. These rapidly changing analogues make it difficult for laboratories to rely on traditional targeted screening methods to detect unknown new psychoactive substances (NPS). In this study, twelve 2C–X, six 2,5-dimethoxyamphetamines (DOX), and fourteen 25X–NBOMe derivatives, including two deuterated derivatives (2C–B-d6 and 25I–NBOMe-d9), were analyzed using ultra-performance liquid chromatography coupled with quadrupole time-of-flight mass spectrometry (UPLC-QTOF-MS). Collision-induced dissociation (CID) experiments were performed using collision energies set at 10, 20, and 40 eV. For 2C–X and DOX derivatives, common losses were observed including neutral and radical losses such as NH3 (17.0265 Da), •CH6N (32.0500 Da), C2H7N (45.0578 Da) and C2H9N (47.0735 Da). 2C–X derivatives displayed common product ions at m/z 164.0837 ([C10H12O2]+•), 149.0603 ([C9H9O2]+), and 134.0732 ([C9H10O]+•) while DOX derivatives had common product ions at m/z 178.0994 ([C11H14O2]+•), 163.0754 ([C10H11O2]+), 147.0804 ([C10H11O]+), and 135.0810 ([C9H11O]+). 25X–NBOMe had characteristic product ions at m/z 121.0654 ([C8H9O]+) and 91.0548 ([C7H7]+) with minor common losses corresponding to 2-methylanisole (C8H10O, 122.0732 Da), 2-methoxybenzylamine (C8H11NO, 137.0847 Da), and •C9H14NO (152.1074 Da). Novel analogues of the selected classes can be detected by applying neutral loss filters (NLFs) and extracting the common product ions. Copyright © 2017 John Wiley & Sons, Ltd.	en_US
dc.relation.ispartof	Drug Testing and Analysis	en_US
dc.relation.isbasedon	10.1002/dta.2171	en_US
dc.subject.classification	Analytical Chemistry	en_US
dc.subject.mesh	Dimethoxyphenylethylamine	en_US
dc.subject.mesh	Hallucinogens	en_US
dc.subject.mesh	Designer Drugs	en_US
dc.subject.mesh	Chromatography, High Pressure Liquid	en_US
dc.subject.mesh	Mass Spectrometry	en_US
dc.title	Characterization of hallucinogenic phenethylamines using high-resolution mass spectrometry for non-targeted screening purposes	en_US
dc.type	Journal Article
utslib.citation.volume	10	en_US
utslib.citation.volume	9	en_US
utslib.for	0301 Analytical Chemistry	en_US
utslib.for	1115 Pharmacology and Pharmaceutical Sciences	en_US
utslib.for	0601 Biochemistry and Cell Biology	en_US
pubs.embargo.period	Not known	en_US
pubs.organisational-group	/University of Technology Sydney
pubs.organisational-group	/University of Technology Sydney/Faculty of Science
pubs.organisational-group	/University of Technology Sydney/Faculty of Science/School of Mathematical and Physical Sciences
pubs.organisational-group	/University of Technology Sydney/Strength - CCET - Centre for Clean Energy Technology
pubs.organisational-group	/University of Technology Sydney/Strength - CFS - Centre for Forensic Science
utslib.copyright.status	open_access
pubs.issue	10	en_US
pubs.publication-status	Published	en_US
pubs.volume	9	en_US

Abstract:

Copyright © 2017 John Wiley & Sons, Ltd. Hallucinogenic phenethylamines such as 2,5-dimethoxyphenethylamines (2C–X) and their N-(2-methoxybenzyl) derivatives (25X–NBOMe) have seen an increase in novel analogues in recent years. These rapidly changing analogues make it difficult for laboratories to rely on traditional targeted screening methods to detect unknown new psychoactive substances (NPS). In this study, twelve 2C–X, six 2,5-dimethoxyamphetamines (DOX), and fourteen 25X–NBOMe derivatives, including two deuterated derivatives (2C–B-d6 and 25I–NBOMe-d9), were analyzed using ultra-performance liquid chromatography coupled with quadrupole time-of-flight mass spectrometry (UPLC-QTOF-MS). Collision-induced dissociation (CID) experiments were performed using collision energies set at 10, 20, and 40 eV. For 2C–X and DOX derivatives, common losses were observed including neutral and radical losses such as NH3 (17.0265 Da), •CH6N (32.0500 Da), C2H7N (45.0578 Da) and C2H9N (47.0735 Da). 2C–X derivatives displayed common product ions at m/z 164.0837 ([C10H12O2]+•), 149.0603 ([C9H9O2]+), and 134.0732 ([C9H10O]+•) while DOX derivatives had common product ions at m/z 178.0994 ([C11H14O2]+•), 163.0754 ([C10H11O2]+), 147.0804 ([C10H11O]+), and 135.0810 ([C9H11O]+). 25X–NBOMe had characteristic product ions at m/z 121.0654 ([C8H9O]+) and 91.0548 ([C7H7]+) with minor common losses corresponding to 2-methylanisole (C8H10O, 122.0732 Da), 2-methoxybenzylamine (C8H11NO, 137.0847 Da), and •C9H14NO (152.1074 Da). Novel analogues of the selected classes can be detected by applying neutral loss filters (NLFs) and extracting the common product ions. Copyright © 2017 John Wiley & Sons, Ltd.

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http://hdl.handle.net/10453/123716