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      Analysis of 25 C NBOMe in Seized Blotters by HPTLC and GC–MS

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          Abstract

          Use of unauthorized synthetic drugs is a serious, forensic, regulatory and public health issue. In this scenario, consumption of drug-impregnated blotters is very frequent. For decades, blotters have been generally impregnated with the potent hallucinogen known as lysergic acid diethylamide (LSD); however, since 2013 blotter stamps with N-2 methoxybenzyl -substituted phenylethylamine hallucinogen designated as “NBOMes” have been seized in Chile. To address this issue with readily accessible laboratory equipment, we have developed and validated a new HPTLC method for the identification and quantitation of 25-C-NBOMe in seized blotters and its confirmation by GC–MS. The proposed method was validated according to SWGTOX recommendations and is suitable for routine analysis of seized blotters containing 25-C-NBOMe. With the validated method, we analyzed 15 real samples, in all cases finding 25-C-NBOMe in a wide dosage range (701.0–1943.5 µg per blotter). In this situation, we can assume that NBOMes are replacing LSD as the main hallucinogenic drug consumed in blotters in Chile.

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          Scientific Working Group for Forensic Toxicology (SWGTOX) standard practices for method validation in forensic toxicology.

          (2013)
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            Molecular interaction of serotonin 5-HT2A receptor residues Phe339(6.51) and Phe340(6.52) with superpotent N-benzyl phenethylamine agonists.

            Michael Braden, Jason Parrish, John C. Naylor … (2006)
            Experiments were conducted to examine the molecular basis for the high affinity and potency of a new class of 5-HT(2A) receptor agonists, N-benzyl phenethylamines. Competition binding assays at several serotonin receptors confirmed that an N-arylmethyl substitution was necessary for affinity increases up to 300-fold over simple N-alkyl homologs, as well as enhanced selectivity for 5-HT(2A) versus 5-HT(2C) and 5-HT(1A) receptors. PI hydrolysis functional assays confirmed that these N-benzyl phenethylamines are potent and highly efficacious agonists at the rat 5-HT(2A) receptor. Virtual docking of these compounds into a human 5-HT(2A) receptor homology model indicated that the N-benzyl moiety might be interacting with Phe339((6.51)), whereas the phenethylamine portion was likely to be interacting with Phe340((6.52)). Experiments in h5-HT(2A) receptors with Phe339((6.51))L and Phe340((6.52))L mutations seem to support this hypothesis. Dramatic detrimental effects on affinity, potency, and intrinsic activity were observed with the Phe339((6.51))L mutation for all N-benzyl analogs, whereas most N-unsubstituted phenethylamines and traditional agonists were only weakly affected, if at all. Consistent with other published studies, the Phe340((6.52))L mutation detrimentally affected affinity, potency, and intrinsic activity of nearly all compounds tested, although a strong change in intrinsic activity was not seen with most N-aryl analogs. These data further validate the topology of our h5-HT(2A) receptor homology model. It is noteworthy that this study is the first to identify a hitherto unrecognized role for residue 6.51 in agonist activation of a serotonin G protein-coupled receptor (GPCR), whereas most previous reports have suggested a varied and sometimes contradictory role in homologous GPCRs.
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              Synthesis and structure-activity relationships of N-benzyl phenethylamines as 5-HT2A/2C agonists.

              Martin Hansen, Karina Phonekeo, James S Paine … (2014)
              N-Benzyl substitution of 5-HT2A receptor agonists of the phenethylamine structural class of psychedelics (such as 4-bromo-2,5-dimethoxyphenethylamine, often referred to as 2C-B) confer a significant increase in binding affinity as well as functional activity of the receptor. We have prepared a series of 48 compounds with structural variations in both the phenethylamine and N-benzyl part of the molecule to determine the effects on receptor binding affinity and functional activity at 5-HT2A and 5-HT2C receptors. The compounds generally had high affinity for the 5-HT2A receptor with 8b having the highest affinity at 0.29 nM but with several other compounds also exhibiting subnanomolar binding affinities. The functional activity of the compounds was distributed over a wider range with 1b being the most potent at 0.074 nM. Most of the compounds exhibited low to moderate selectivity (1- to 40-fold) for the 5-HT2A receptor in the binding assays, although one compound 6b showed an impressive 100-fold selectivity for the 5-HT2A receptor. In the functional assay, selectivity was generally higher with 1b being more than 400-fold selective for the 5-HT2A receptor.
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                Author and article information

                Journal
                Journal ID (nlm-ta): J Chromatogr Sci
                Journal ID (iso-abbrev): J Chromatogr Sci
                Journal ID (publisher-id): chromsci
                Journal ID (hwp): chromsci
                Title: Journal of Chromatographic Science
                Publisher: Oxford University Press
                ISSN (Print): 0021-9665
                ISSN (Electronic): 1945-239X
                Publication date (Print): August 2016
                Publication date (Electronic): 12 July 2016
                Publication date PMC-release: 12 July 2016
                Volume: 54
                Issue: 7
                Pages: 1153-1158
                Affiliations
                [1 ]Drug Analysis Section, Public Health Institute of Chile , Santiago, Chile
                [2 ]Faculty of Chemical and Pharmaceutical Sciences, University of Chile , Santiago, Chile
                [3 ]Department of Chemistry, Faculty of Sciences, University of Chile , Santiago, Chile
                Author notes
                [* ]Author to whom correspondence should be addressed. Email: bduffau@ 123456gmail.com ; bduffau@ 123456ispch.cl
                Article
                Publisher ID: bmw095
                DOI: 10.1093/chromsci/bmw095
                PMC ID: 4941995
                PubMed ID: 27406128
                SO-VID: 57711ec0-bc88-4cd2-8bd0-0b67b892d976
                Copyright © © The Author 2016. Published by Oxford University Press.
                License:

                This is an Open Access article distributed under the terms of the Creative Commons Attribution Non-Commercial License ( http://creativecommons.org/licenses/by-nc/4.0/), which permits non-commercial re-use, distribution, and reproduction in any medium, provided the original work is properly cited. For commercial re-use, please contact journals.permissions@oup.com

                History
                Date received : 26 June 2015
                Date revision received : 3 May 2016
                Categories
                Subject: Special Issue: Thin layer chromatography

                Data availability:

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