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335161-14-3

335161-14-3 Structure

335161-14-3 Structure
IdentificationBack Directory
[Name]

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

335161-14-3
[Synonyms]

JWH-073 4-Hydroxybutyl
JWH073-4-Hydroxybutyl metabolite
[1-(4-hydroxybutyl)indol-3-yl]-naphthalen-1-ylmethanone
[Molecular Formula]

C23H21NO2
[MDL Number]

MFCD18428071
[MOL File]

335161-14-3.mol
[Molecular Weight]

343.42
Chemical PropertiesBack Directory
[solubility ]

DMF: 30 mg/ml; DMF:PBS (pH 7.2) (1:9): 0.1 mg/ml; DMSO: 30 mg/ml; Ethanol: 0.5 mg/ml
[form ]

A crystalline solid
Hazard InformationBack Directory
[Description]

JWH 073 is a mildly selective agonist of the central cannabinoid (CB1) receptor derived from the aminoalkylindole WIN 55,212-2. The Ki 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
[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).
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