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dc.contributor.authorMorris, Noreen
dc.contributor.authorMcLaughlin, Gavin
dc.contributor.authorKavanagh, Pierce V.
dc.contributor.authorPower, John D.
dc.contributor.authorTwamley, Brendan
dc.contributor.authorO'Brien, John
dc.contributor.authorTalbot, Brian
dc.contributor.authorDowling, Geraldine
dc.contributor.authorBrandt, Simon D.
dc.identifier.citationMorris, N., McLaughlin, G., Kavanagh, Pierce V., Power, J.D.,Twamley, B., O'Brien, Talbot, B., Dowling, G., Brandt, S. D. (2016). The synthesis and characterization of the ‘research chemical’ N-(1- amino-3-methyl-1-oxobutan-2-yl)-1-(cyclohexylmethyl)-3-(4-fluorophenyl) -1H-pyrazole-5-carboxamide (3,5-AB-CHMFUPPYCA) and differentiation from its 5,3-regioisomer. Drug Testing and Analysis. 8 (9), 920-929en_US
dc.identifier.otherFaculty of Science & Health - Life and Physical - Articlesen_US
dc.description.abstractThis study presents the identification of N-(1-amino-3-methyl-1-oxobutan-2-yl)-1- (cyclohexylmethyl)-3-(4-fluorophenyl)-1H-pyrazole-5-carboxamide that was termed 3,5-AB-CHMFUPPYCA. This compound was obtained from a UK-based Internet vendor, who erroneously advertised this ‘research chemical’ as AZ-037 and which would have been associated with (S)-N-(1-amino-3-methyl-1-oxobutan-2-yl)-1-(5- fluoropentyl)-5-(4-fluorophenyl)-1H-pyrazole-3-carboxamide. The presence of the pyrazole core indicates a bioisosteric replacement of an indazole ring that is frequently associated with synthetic cannabinoids of the “PINACA”, “FUBINACA” and “CHMINACA” series. The pyrazole ring system present in 3,5-AB-CHMFUPPYCA gives rise to the regioisomer N-(1-amino-3-methyl-1-oxobutan-2-yl)-1- (cyclohexylmethyl)-5-(4-fluorophenyl)-1H-pyrazole-3-carboxamide (named 5,3-ABCHMFUPPYCA) and both isomers were synthesized using two specific routes which supported the correct identification of the ‘research chemical’ as 3,5-ABCHMFUPPYCA. Both isomers could be conveniently differentiated. Interestingly, a route specific chlorine-containing by-product also was observed during the synthesis of 3,5-AB-CHMFUPPYCA and identified as N-(1-amino-3-methyl-1-oxobutan-2-yl)-4- chloro-1-(cyclohexylmethyl)-3-(4-fluorophenyl)-1H-pyrazole-5-carboxamide. An extensive analytical characterization included chromatographic, spectroscopic, mass spectrometric platforms as well as crystal structure analysis. The syntheses and analytical characterizations of both AB-CHMFUPPYCA isomers are reported for the first time and it serves as a reminder that the possibility of mislabeling of ‘research chemicals’ cannot be excluded. The pharmacological activities of both ABCHMFUPPYCA isomers remain to be exploreden_US
dc.relation.ispartofDrug Testing and Analysisen_US
dc.rightsAttribution-NonCommercial-NoDerivs 3.0 Ireland*
dc.subjectPsychoactive substancesen_US
dc.titleThe synthesis and characterization of the ‘research chemical’ N-(1- amino-3-methyl-1-oxobutan-2-yl)-1-(cyclohexylmethyl)-3-(4-fluorophenyl) -1H-pyrazole-5-carboxamide (3,5-AB-CHMFUPPYCA) and differentiation from its 5,3-regioisomer.en_US
dc.rights.accessOpen Accessen_US
dc.subject.departmentFaculty of Science and Healthen_US

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