Concise Synthesis of Potential 4-Hydroxy-5-fluoropentyl Side-Chain Metabolites of Four Synthetic Cannabinoids

Autor:	Huiling Liu, Xiongyu Wu, Erik Vestling, Jakob Wallgren, Johan Dahlén, Peter Konradsson, Anders Rexander
Rok vydání:	2020
Předmět:	Drug Cannabinoid receptor Metabolite media_common.quotation_subject Organic Chemistry Hydroxylation chemistry.chemical_compound chemistry Biochemistry Synthetic cannabinoids medicine Side chain Drug intoxication Reference standards media_common medicine.drug
Zdroj:	Synlett. 31:517-520
ISSN:	1437-2096 0936-5214
DOI:	10.1055/s-0039-1691571
Popis:	Synthetic cannabinoids are a group of compounds that act on the CB1 receptor and are used illicitly as substitutes for cannabis. Given the rapid and extensive metabolism of synthetic cannabinoids, urinary biomarkers are essential if proof of drug intake is to be obtained in forensic laboratories. To identify good biomarker candidates, the metabolism of synthetic cannabinoids must be studied and reference standards need to be acquired. Studies on the metabolism of synthetic cannabinoids containing a terminally fluorinated pentyl side chain have shown that hydroxylation can occur at the four position of the side chain. This makes the 4-hydroxy-5-fluoropentyl side-chain metabolite a good urinary biomarker for proving intake of the corresponding parent drug, as this compound cannot be formed from its nonfluorinated analogue. Here, a concise synthetic route to the 4-hydroxy-5-fluoropentyl side-chain metabolites of the synthetic cannabinoids STS-135, MAM-2201, AM-2201, and XLR-11 is reported.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::d84cc8b8cc10c85f18cb19c16812f029 https://doi.org/10.1055/s-0039-1691571 Zobrazit plný text záznamu