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Synthesis of emerging cathinones and validation of a SPE GC–MS method for their simultaneous quantification in blood

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dc.contributor.authorJúlio, Sara
dc.contributor.authorFerro, Raquel A.
dc.contributor.authorSantos, Susana
dc.contributor.authorAlexandre, Andrea
dc.contributor.authorCaldeira, Maria João
dc.contributor.authorFranco, João
dc.contributor.authorBarroso, Mário
dc.contributor.authorGaspar, Helena
dc.date.accessioned2023-08-24T11:20:55Z
dc.date.available2023-08-24T11:20:55Z
dc.date.issued2023
dc.descriptionThis work was supported by the Portuguese Foundation for Science and Technology (FCT) through Strategic Projects UIDP/04046/2020 and UIDB/04046/2020 to BioISI—BioSystems and Integrative Sciences Institute; UID/04292/2020 to MARE—Marine and Environmental Sciences Centre; CQE—UIDB/00100/2020, UIDP/00100/2020, and IMS—LA/P/0056/2020, to Centro de Química Estrutural, Institute of Molecular Sciences; Portuguese Mass Spectrometry Network (LISBOA-01-0145FEDER-022125) and National NMR Network (PTNMR), partially supported by Infrastructure Project N° 022161 (co-financed by FEDER through COMPETE 2020, POCI and PORL and FCT through PIDDAC).pt_PT
dc.description.abstractOver the past 15 years, synthetic cathinones have emerged as an important class of new psychoactive substances (NPS) worldwide. The proliferation of these psychostimulants and their sought-after effects among recreational drug users pose a serious threat to public health and enormous challenges to forensic laboratories. For forensic institutions, it is essential to be one step ahead of covert laboratories, foreseeing the structural changes possible to introduce in the core skeleton of cathinones while maintaining their stimulating activity. In this manner, it is feasible to equip themselves with standards of possible new cathinones and validated analytical methods for their qualitative and quantitative detection. Therefore, the aim of the work herein described was to synthesize emerging cathinones based on the evolving patterns in the illicit drug market, and to develop an analytical method for their accurate determination in forensic situations. Five so far unreported cathinones [4′-methyl-N-dimethylbuphedrone (4-MDMB), 4′-methyl-N-ethylbuphedrone (4-MNEB), 4′-methyl-N-dimethylpentedrone (4-MDMP), 4′-methyl-N-dimethylhexedrone (4-MDMH), and 4′-methyl-N-diethylbuphedrone (4-MDEB)] and a sixth one, 4′-methyl-N-ethylpentedrone, already reported to EMCDDA and also known as 4-MEAP, were synthesized and fully characterized by nuclear magnetic resonance (NMR) spectroscopy and mass spectrometry (MS). An analytical method for the simultaneous quantification of these cathinones in blood, using solid phase extraction (SPE) combined with gas chromatography-mass spectrometry (GC–MS) was developed and validated. The results prove that this methodology is selective, linear, precise, and accurate. For all target cathinones, the extraction efficiency was higher than 73%, linearity was observed in the range of 10 (lower limit of quantification, LLOQ) to 800 ng/mL, with coefficients of determination higher than 0.99, and the limits of detection (LODs) were 5 ng/mL for all target cathinones. The stability of these cathinones in blood matrices is dependent on the storage conditions; 4-MNEB is the most stable compound and 4-MDMH is the least stable compound. The low limits obtained allow the detection of the compounds in situations where they are involved, even if present at low concentrations.pt_PT
dc.description.versioninfo:eu-repo/semantics/publishedVersionpt_PT
dc.identifier.citationJúlio S, Ferro RA, Santos S, Alexandre A, Caldeira MJ, Franco J, Barroso M, Gaspar H. Synthesis of emerging cathinones and validation of a SPE GC-MS method for their simultaneous quantification in blood. Anal Bioanal Chem. 2023 Feb;415(4):571-589. doi: 10.1007/s00216-022-04440-6. Epub 2022 Dec 9. PMID: 36494605.pt_PT
dc.identifier.doi10.1007/s00216-022-04440-6pt_PT
dc.identifier.issn1618-2642
dc.identifier.issn1618-2650
dc.identifier.urihttp://hdl.handle.net/10400.8/8733
dc.language.isoengpt_PT
dc.peerreviewedyespt_PT
dc.publisherSpringerpt_PT
dc.relationBiosystems and Integrative Sciences Institute
dc.relationBiosystems and Integrative Sciences Institute
dc.relationCentro de Química Estrutural
dc.relationCentro de Química Estrutural
dc.relation.publisherversionhttps://pubmed.ncbi.nlm.nih.gov/36494605/pt_PT
dc.rights.urihttp://creativecommons.org/licenses/by/4.0/pt_PT
dc.subjectNPSpt_PT
dc.subjectSynthetic cathinonespt_PT
dc.subjectNMRpt_PT
dc.subjectBloodpt_PT
dc.subjectGC–MSpt_PT
dc.titleSynthesis of emerging cathinones and validation of a SPE GC–MS method for their simultaneous quantification in bloodpt_PT
dc.typejournal article
dspace.entity.typePublication
oaire.awardTitleBiosystems and Integrative Sciences Institute
oaire.awardTitleBiosystems and Integrative Sciences Institute
oaire.awardTitleCentro de Química Estrutural
oaire.awardTitleCentro de Química Estrutural
oaire.awardURIinfo:eu-repo/grantAgreement/FCT/6817 - DCRRNI ID/UIDP%2F04046%2F2020/PT
oaire.awardURIinfo:eu-repo/grantAgreement/FCT/6817 - DCRRNI ID/UIDB%2F04046%2F2020/PT
oaire.awardURIinfo:eu-repo/grantAgreement/FCT/6817 - DCRRNI ID/UIDB%2F00100%2F2020/PT
oaire.awardURIinfo:eu-repo/grantAgreement/FCT/6817 - DCRRNI ID/UIDP%2F00100%2F2020/PT
oaire.citation.endPage589pt_PT
oaire.citation.issue4pt_PT
oaire.citation.startPage571pt_PT
oaire.citation.titleAnalytical and Bioanalytical Chemistrypt_PT
oaire.citation.volume415pt_PT
oaire.fundingStream6817 - DCRRNI ID
oaire.fundingStream6817 - DCRRNI ID
oaire.fundingStream6817 - DCRRNI ID
oaire.fundingStream6817 - DCRRNI ID
person.familyNameFerro
person.familyNameBarroso
person.familyNameGuerreiro Galla Gaspar
person.givenNameRaquel A.
person.givenNameMário
person.givenNameHelena Margarida
person.identifierE-6798-2012
person.identifier.ciencia-id3F1C-52DF-3B49
person.identifier.ciencia-id5110-F476-ECCC
person.identifier.ciencia-id761C-044C-995B
person.identifier.orcid0000-0002-2300-0711
person.identifier.orcid0000-0001-8848-2734
person.identifier.orcid0000-0002-1613-7023
person.identifier.scopus-author-id7003891380
project.funder.identifierhttp://doi.org/10.13039/501100001871
project.funder.identifierhttp://doi.org/10.13039/501100001871
project.funder.identifierhttp://doi.org/10.13039/501100001871
project.funder.identifierhttp://doi.org/10.13039/501100001871
project.funder.nameFundação para a Ciência e a Tecnologia
project.funder.nameFundação para a Ciência e a Tecnologia
project.funder.nameFundação para a Ciência e a Tecnologia
project.funder.nameFundação para a Ciência e a Tecnologia
rcaap.rightsclosedAccesspt_PT
rcaap.typearticlept_PT
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