(±)-JWH 398 N-(4-hydroxypentyl) metabolite-d5

JWH 398 is a synthetic cannabinoid (CB) that activates both central CB₁ and peripheral CB₂ receptors (K_i = 2.3 and 2.8 nM, respectively).¹ It has been reported to be an adulterant of herbal products.^2,3 (±)-JWH 398 N-(4-hydroxypentyl) metabolite is an expected phase I metabolite of JWH 398 , detectable in serum and urine. While similar hydroxylated phase I metabolites of synthetic CBs retain activity, the physiological properties of this compound have yet to be determined.^4,5 This product is intended for research and forensic applications. (±)-JWH 398 N-(4-hydroxypentyl) metabolite-d₅ contains five deuterium atoms at the 2, 4, 5, 6, and 7 positions. It is intended for use as an internal standard for the quantification of JWH 398 N-(4-hydroxypentyl) metabolite by GC- or LC-mass spectrometry.

1.Huffman, J.W.Cannabimimetic indoles, pyrroles, and indenes: Structure-activity relationships and receptor interactionsThe cannabinoid receptors49-95(2009) 2.Kikura-Hanajiri, R., Uchiyama, N., and Goda, Y.Survey of current trends in the abuse of psychotropic substances and plants in JapanLeg. Med. (Tokyo)13(3)109-115(2011) 3.Dresen, S., FerreirÓs, N., PÜtz, M., et al.Monitoring of herbal mixtures potentially containing synthetic cannabinoids as psychoactive compoundsJournal of Mass Spectrometry45(10)1186-1194(2010) 4.Brents, L.K., Reichard, E.E., Zimmerman, M., et al.Phase I hydroxylated metabolites of the K2 synthetic cannabinoid JWH-018 retain in vitro and in vivo cannabinoid 1 receptor affinity and activityPLoS One6(7)1-9(2011) 5.Brents, L.K., Gallus-Zawala, A., Radominska-Pandya, A., et al.Monohydroxylated metabolites of the K2 synthetic cannabinoid JWH-073 retainintermediate to high cannabinoid 1 receptor (CB1R) affinity and exhibit neutralantagonist to partial agonist activityBiochemical Pharmacology83952-961(2012)