1. Anal Bioanal Chem. 2006 Nov;386(5):1345-55. Epub 2006 Sep 6.
Identification of in vitro metabolites of JWH-015, an aminoalkylindole agonist
for the peripheral cannabinoid receptor (CB2) by HPLC-MS/MS.
Zhang Q, Ma P, Cole RB, Wang G.
Department of Chemistry, Xavier University of Louisiana, New Orleans, LA 70125,
USA.
The in vitro microsomal metabolism of JWH-015, a ligand that exhibits a high
binding affinity at the peripheral cannabinoid receptor CB(2), 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).
PMID: 16955257 [PubMed - indexed for MEDLINE]