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Synthesis of JHW-250 4-hydroxypentyl Metabolite

Authors: Martha Liu, Kenan Yaser, Dillon Edwards and Uma Sreenivasan
Presented at 43rd National Organic Symposium Jun 23-27 at University of Washington, Seattle


JWH-250 (1-pentyl-3-(2-methoxyphenylacetyl)indole)is one compound in a family of cannabimimeticindolesthat shows a high-affinity for both the central cannabinoid(CB1) and the peripheral cannabinoid(CB2) receptors.1JWH-250 was discovered by Dr. John W. Huffman who created JWH-250 and a number of other compounds to research the structure and function of the endocannabinoidsystem of mammals.

In recent times, these indolecannabimimetics, commonly known as “spice,” have been sold as “legal highs” as a substitute for marijuana and are now coming under regulatory control. The indolecannabimimeticsare metabolized to a variety of hydroxylatedand carboxylatedderivatives.

Identification and quantitation of these drugs in forensic and clinical samples has clinical and societal ramifications and can impact forensic investigations and patient treatment decisions. Certified reference standards are required in order to accurately identify and quantitate these cannabimimeticdrugs and their metabolites.

The aim of this work was to synthesize & optimize the processes for JWH-250 4-hydroxypentyl metabolite through a four step synthetic scheme. Analysis and characterization of JWH-250 4-hydroxypentyl metabolite were accomplished via HPLC, Mass Spectra, and 1H-NMR.

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