TITLE

Identification of in vitro metabolites of JWH-015, an aminoalkylindole agonist for the peripheral cannabinoid receptor (CB2) by HPLC-MS/MS

AUTHOR(S)
Zhang, Qiang; Ma, Peng; Cole, Richard B.; Wang, Guangdi
PUB. DATE
December 2006
SOURCE
Analytical & Bioanalytical Chemistry;Dec2006, Vol. 386 Issue 5, p1345
SOURCE TYPE
Academic Journal
DOC. TYPE
Article
ABSTRACT
The in vitro microsomal metabolism of JWH-015, a ligand that exhibits a high binding affinity at the peripheral cannabinoid receptor CB2, has been studied. A total of 22 metabolites were identified and structurally characterized. The metabolites are products of: 1) monohydroxylation on the naphthalene ring ( m/ z 344, M20 and M21), indole ring ( m/ z 344, M17 and M18), or the N-alkyl group ( m/ z 344, M14); 2) arene oxidation leading to dihydrodiols ( m/ z 362, M12 and M15); 3) dihydroxylation on the naphthalene ring ( m/ z 360, M7) or indole ring ( m/ z 360, M13), resulting from a combination of monohydroxylations on both the naphthalene and indole rings ( m/ z 360, M16), or a combination of monohydroxylations on the naphthalene ring and on the N-propyl group ( m/ z 360, M9); 4) trihydroxylation ( m/ z 378, M1, M3, M4, M6, and M10); 5) N-dealkylation ( m/ z 286, M19); 6) N-dealkylation and monohydroxylation on the naphthalene ring ( m/ z 302, M11); 7) N-dealkylation and dihydrodiol formation from arene oxidation ( m/ z 320, M2 and M5); 8) dehydrogenation after monohydroxylation on the N-alkyl group ( m/ z 326, M22); 9) dehydrogenation and monohydroxylation on the indole ring ( m/ z 342, M8).
ACCESSION #
22897016

 

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