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

Abstract

This 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-AB-CHMFUPPYCA) and both isomers were synthesized using two specific routes which supported the correct identification of the 'research chemical' as 3,5-AB-CHMFUPPYCA. 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-http://mc.manuscriptcentral.com/dta Drug Testing and Analysis

Identification and analytical characterization of six synthetic cannabinoids NNL‐3, 5F–NPB‐22‐7N, 5F–AKB‐48‐7N, 5F–EDMB‐PINACA, EMB‐FUBINACA, and EG‐018

“…The difference between the protonated molecule of 5 and MMB-FUBINACA (C 21 H 23 FN 3 O 3 + ) [28,29] was an additional CH 2 [28] The 13 C NMR spectrum of 5 was similar to that of MMB-FUBINACA, [28] except for the O-ethyl moiety (positions 1″' to 2″') as shown in Table 6. The difference between the protonated molecule of 5 and MMB-FUBINACA (C 21 H 23 FN 3 O 3 + ) [28,29] was an additional CH 2 [28] The 13 C NMR spectrum of 5 was similar to that of MMB-FUBINACA, [28] except for the O-ethyl moiety (positions 1″' to 2″') as shown in Table 6.…”

“…The doublet carbon atoms at position 3″ to 5″ and the spin-spin coupling constants ( 1 J C-F = 160.6 Hz, 2 J C-F = 19.2 Hz, 3 J C-F = 5.4 Hz), which were characteristic for 13 C-19 F interactions, [23] proved the C-5″ position fluoro substituted pentyl moiety. [17] Because the NMR spectra showed an AA'BB' splitting patterns in phenyl group (position 4 0 to 7 0 ), we hypothesized that the remaining C 6 H 4 N 3 O unit was a benzo[d] [1,2,3]triazol group. [17] Because the NMR spectra showed an AA'BB' splitting patterns in phenyl group (position 4 0 to 7 0 ), we hypothesized that the remaining C 6 H 4 N 3 O unit was a benzo[d] [1,2,3]triazol group.…”

“…[1][2][3][4][5][6] The NPS market continues to be characterized by the large number of new substances being reported. [1][2][3][4][5][6] The NPS market continues to be characterized by the large number of new substances being reported.…”

“…[5] Synthetic cannabinoids act on the same brain receptors CB 1 and/or CB 2 as tetrahydrocannabinol (THC), one of the main active compounds found in natural cannabis. After the first detection of one indazole 7N positional isomer compound NNL-1, [17] three more indazole 7N positional isomer compounds of NNL-3 (1), 5F-NPB-22-7N (2), and 5F-AKB-48-7N (3) were identified this time. [6,18] SC use has repeatedly been reported to produce serious adverse health effects, including but not limited to excited delirium, acute kidney injury, seizures, psychosis, hallucinations, cardiotoxic effects, coma, and death.…”

“…The CB 1 receptor is responsible for the typical physiological and particularly the psychotropic effects of cannabis, whereas the CB 2 receptor may mediate immune modulatory effects. Interestingly, NNL-3 showed a new type of 1H-benzo[d] [1,2,3]triazole moiety connected to the carboxylate group. [19][20][21] Several powdered materials seized by police authorities were submitted to our laboratory for structure identification.…”