In recent years, there has been a rise in the use of New Psychoactive Substances (NPS) that mimic the effects of controlled drugs and licensed medicines, which have become a significant public health concern globally. Synthetic cannabinoids, a rapidly expanding category of NPS, with much higher potency and binding affinity to the cannabinoid receptors than ∆9-tetrahydrocannabinol (THC), have led to serious psychiatric complications and other adverse effects. This project aims to synthesize and analyze four potential metabolites of a synthetic cannabinoid, ADB-5´Br-BUTINACA, to determine if the synthesized metabolites correspond to those produced in human hepatocytes. The metabolites were synthesized by alkylation, amide coupling, and hydrolysis/TFA treatment and analyzed using high-performance liquid chromatography-mass spectrometry (HPLC-MS) and nuclear magnetic resonance (NMR). The reaction strategy combined all three steps into a single process, making it significantly easier to carry out and not requiring much expertise. The results suggest that the synthetic approach used in this project was successful in generating the desired potential metabolites, with overall yields varying from 27.5 % to 57.6 % and high purities ranging from 95.6 % to 99.3 %. However, the overall yields were lower than expected due to product loss during the transfer of the solution mixture, the possibility of side reactions, and incomplete conversion. Further optimization of reaction conditions may be necessary to improve the yield of the synthesized metabolites.
| Identifer | oai:union.ndltd.org:UPSALLA1/oai:DiVA.org:liu-195692 |
| Date | January 2023 |
| Creators | Malekshahineia, Alaa |
| Publisher | Linköpings universitet, Kemi |
| Source Sets | DiVA Archive at Upsalla University |
| Language | English |
| Detected Language | English |
| Type | Student thesis, info:eu-repo/semantics/bachelorThesis, text |
| Format | application/pdf |
| Rights | info:eu-repo/semantics/openAccess |
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