[1-(4-hydroxybutyl)indol-3-yl]-naphthalen-1-ylmethanone

Description

JWH 073 is a mildly selective agonist of the central cannabinoid (CB₁) receptor derived from the aminoalkylindole WIN 55,212-2. The K_i values for binding CB₁ and the peripheral cannabinoid (CB₂) receptor are 8.9 and 38 nM, respectively for a CB₁:CB₂ ratio of 0.23.¹ JWH 073 is one of several synthetic CBs which have been included in smoking mixtures. JWH 073 N-(4-hydroxybutyl) metabolite is expected to be a major urinary metabolite of JWH 073, characterized by monohydroxylation of the N-alkyl chain, based on the metabolism of the closely-related JWH 015 and JWH 018.^2,3 In urine samples, this metabolite of JWH 018 is almost completely glucuronidated.³

Uses

JWH-073 (Indole-d5) 4-Hydroxybutyl is labelled JWH-073 4-Hydroxybutyl (J211275), a urinary metabolite of JWH-073 (B693550) which acts as a partial agonist at both the CB1 and CB2 cannabinoid receptors.

Definition

ChEBI: JWH 073 N-(4-hydroxybutyl) metabolite is an indolecarboxamide.

References

1. Aung, M.M., Griffin, G., Huffman, J.W., et al. Influence of the N-1 alkyl chain length of cannabimimetic indoles upon CB₁ and CB₂ receptor binding Drug Alcohol Depend. 60(2),133-140(2000).
2. Zhang, Q., Ma, P., Cole, R.B., et al. Identification of in vitro metabolites of JWH-015, an aminoalkylindole agonist for the peripheral cannabinoid receptor (CB₂) by HPLC-MS/MS Anal. Bioanal. Chem. 386(5),1345-1355(2006).
3. Sobolevsky, T., Prasolov, I., and Rodchenkov, G. Detection of JWH-018 metabolites in smoking mixture post-administration urine Forensic Sci. Int. 200(1-3),141-147(2010).

Raw materials

Preparation Products