Synthetic cannabinoid receptor agonists: Analytical profiles and development of QMPSB, QMMSB, QMPCB, 2F-QMPSB, QMiPSB, and SGT-233

Abstract

A diverse assortment of molecules designed to explore the cannabinoid receptor system and considered new psychoactive substances (NPS) have become known as synthetic cannabinoid receptor agonists (SCRAs). One group of SCRAs that has received little attention involves those exhibiting sulfamoyl benzoate, sulfamoyl benzamide, and N-benzoylpiperidine based structures. In this study, quinolin-8-yl 4-methyl-3-(piperidine-1-sulfonyl)benzoate (QMPSB), quinolin-8-yl 4-methyl-3-(morpholine-4-sulfonyl)benzoate (QMMSB), quinolin-8-yl 4-methyl-3-(piperidine-1-carbonyl)benzoate (QMPCB, SGT-11), quinolin-8-yl 3-(4,4-difluoropiperidine-1-sulfonyl)-4-methylbenzoate (2F-QMPSB, QMDFPSB, SGT-13), quinolin-8-yl 4-methyl-3-[(propan-2-yl)sulfamoyl]benzoate (QMiPSB, SGT-46), and 3-(4,4-difluoropiperidine-1-sulfonyl)-4-methyl-N-(2-phenylpropan-2-yl)benzamide (SGT-233) were extensively characterized (including data on impurities). The analytical profiles may be useful to researchers and scientists who deal with the emergence of NPS during forensic and clinical investigations. The detection of QMPSB was first published in 2016 but it is worth noting that Stargate International, a company originally formed to develop harm reduction solutions, were involved in the investigation and development of these six compounds for potential release between 2011 and early 2014. Whilst information on the prevalence of use of these particular compounds at the present time is limited, one of the key outcomes of the research performed by Stargate International reviewed here was to set the stage for the quinolin-8-yl ester head group that ultimately led to hybridization with an N-alkyl-1H-indole core to give SGT-21 and SGT-32, which became later known as PB-22 (QMPSB/JWH-018 hybrid) and BB-22, respectively, thus, opening the door to a range of SCRAs carrying the quinolin-8-yl head group from about 2012 onwards.