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Regioselective Friedel-Crafts Type Acylation of Indoles: An Improvement on the Synthesis of Cannabimimetic Indole Metabolites

Authors: Lindsey Hess, Uma Sreenivasan, Kenan Yaser
Presented at American Chemical Society (ACS), Dallas, TX, March 16-20, 2014

Indole cannabimimetics, commonly referred to as "Spice," are psychoactive designer drugs created to mimic the effects of cannabis. While the chemical structures of these compounds do not resemble that of Δ9-tetrahydrocannabinol (THC), the active component of cannabis, they show high binding affinities for the CB1 and CB2 cannabinoid receptors. In the early 2000s, Dr. John Huffman identified different structural subclasses of these cannabinoids that possessed very high binding affinities for the cannabinoid receptors through extensive structure-activity relationship studies. In particular, he discovered that naphthoylindoles (JWH-018 1, JWH-122 2 and JWH-210 3) and phenylacetylindoles (JWH-250 4) are highly active in the endocannabinoid system of mammals.1,2,3
Illegal use and abuse of these synthetic cannabinoids has created a need for certified reference standards to identify and quantify these drugs in clinical and forensic samples. Additionally, due to their fast metabolism in vivo4, the preparation of the major metabolites and their stable-isotope labeled internal standards is of high priority. To this end, a regioselective, highly efficient synthesis of 4-hydroxypentyl or 5-hydroxypentyl metabolites of JWH-018, JWH-210, JWH-250 and JWH-122 has been completed for the development of analytical reference and internal standards.
1. Bioorg. Med. Chem., 2005, 13, 89
2. Bioorg. Med. Chem. Lett., 2005, 15, 4110
3. Bioorg. Med. Chem., 2012, 20, 2067
4. Front. Behav. Neurosci., 2011, 5, 60
5. Org. Lett., 2001, 3, 1005-1007

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