A novel metabolite of 3,4-methylenedioxyamphetamine (MDA): formation of 3-methyl-6,7-methylenedioxy-1,2,3,4-tetrahydroisoquinoline and its pharmacological effect.
H Nakagawa, Y Makino, Y Yoshida, S Ohta, M Hirobe
Biological and Pharmaceutical Bulletin June 1993 DOI: 10.1248/bpb.16.579 (opens in new tab)
Study at a glance
AI-extracted from the abstract| Characteristics | Animal study Peer reviewed |
|---|---|
| Population | Rats |
| Interventions | 3 4-methylenedioxyamphetamine (MDA) 3-methyl-6 7-methylenedioxy-1 2 4-tetrahydroisoquinoline (3Me6 7MDTIQ) |
| Measures | open-field test (ambulation score, rearing score) |
| Key points | MDA is metabolized to 3Me6,7MDTIQ in rat brain and urine, with significantly higher levels after (R)-MDA than (S)-MDA, suggesting stereoselective metabolism. Administered 3Me6,7MDTIQ produced behavioral effects distinct from MDA, significantly lowering ambulation and moderately lowering rearing in an open-field test. |
Abstract
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.