A novel metabolite of 3,4-methylenedioxyamphetamine (MDA): formation of 3-methyl-6,7-methylenedioxy-1,2,3,4-tetrahydroisoquinoline and its pharmacological effect.
In 3,4-methylenedioxyamphetamine (MDA)-treated rat brain and urine, 3-methyl-6,7-methylenedioxy-1,2,3,4-tetrahydroisoquinoline (3Me6,7MDTIQ) was detected as a new metabolite. The content of 3Me6,7MDTIQ in (R)-MDA-treated rat was significantly higher than that in (S)-MDA-treated brain and urine. This result suggests that this metabolism of MDA contains stereoselective pathways. The pharmacological effects of 3Me6,7MDTIQ on behavior differed from those of MDA. The ambulation score of 3Me6,7MDTIQ was significantly decreased compared to the control, and the rearing score of 3Me6,7MDTIQ was moderately decreased compared to the control in an open-field test.
Nakagawa
H
H
Faculty of Pharmaceutical Sciences, University of Tokyo, Japan.
Makino
Y
Y
Yoshida
Y
Y
Ohta
S
S
Hirobe
M
M
D015104:3,4-Methylenedioxyamphetamine / Q000378:metabolism*; D000818:Animals; D001522:Behavior, Animal / Q000187:drug effects; D001921:Brain / Q000378:metabolism; D003500:Cyclization; D008401:Gas Chromatography-Mass Spectrometry; D007546:Isoquinolines / Q000378:metabolism* / Q000494:pharmacology / Q000652:urine; D008297:Male; D051379:Mice; D008815:Mice, Inbred Strains; D009043:Motor Activity / Q000187:drug effects; D051381:Rats; D017208:Rats, Wistar; D013237:Stereoisomerism
D007546:Isoquinolines; C082997:3-methyl-6,7-methylenedioxy-1,2,3,4-tetrahydroisquinoline; D015104:3,4-Methylenedioxyamphetamine