Synthesis of JWH-018 metabolite

by Wright, Patience M.; Durham, Bill; Emerson, Elizabeth Lauren

Beginning in 2004, herbal mixts. with the name "Spice" or "K2" were sold in "headshops" and on the internet. These mixts. contain 1-pentyl-3-(1-naphthoyl)indole, also known as JWH-018. Although JWH-018 and delta-9-tetrahydrocannabinol (Δ9-THC) have different structures, both give cannabis-like effects after consumption. Hallucination, distorted perception, and tachycardia are common effects of usage. Due to this, the Drug Enforcement Agency (DEA) is conducting further studies to det. if these mixts. should be permanently placed on the controlled substances list prohibiting their sale and consumption. For this project, the authors synthesized the JWH-018 metabolite and analyzed the products using gas chromatog.-mass spectroscopy (GC/MS). The metabolite was synthesized to mimic the metabolized product found in K2 users' urine after its consumption. Hydroxylation on the alkyl chain is the most common metabolite found in urine; therefore, the authors choose to synthesize it to act as an anal. std. to compare to urine samples of K2 users. Since the carboxylic acid form is the second most common metabolite found, future studies will work toward continuing the synthesis.