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Phase I Hydroxylated Metabolites of the K2 Synthetic Cannabinoid JWH-018 Retain In Vitro and In Vivo Cannabinoid 1 Receptor Affinity and Activity

Figure 1

Structures of JWH-018 and six JWH-018 hydroxylated products.

A. JWH-018 [(1-pentyl-1H-indol-3-yl)-1-naphthalenyl-methanone] B. M1 [(4-hydroxy-1-pentyl-1H-indol-3-yl)(naphthalen-1-yl)methanone] C. M2 [(5-hydroxy-1-pentyl-1H-indol-3-yl)(naphthalen-1-yl)methanone] D. M3 [(6-hydroxy-1-pentyl-1H-indol-3-yl)(naphthalen-1-yl)methanone] E. M4 [(7-hydroxy-1-pentyl-1H-indol-3-yl)naphthalen-1-yl)methanone] F. M5 [(1-(5-hydroxypentyl)-1H-indol-3-yl)(naphthalen-1-yl)methanone] G. M6 [5-(3-(1-naphthoyl)-1H-indol-1-yl)pentanoic acid].

Figure 1

doi: https://doi.org/10.1371/journal.pone.0021917.g001