American Chemical Society Division of
Abstract
The benzylic ketone analogs of the psychoactive phenylisopropylamine
methamphetamine (MA), MCAT, and of 3,4-methylenedioxymethamphetamine (MDMA),
MDMCAT, were synthesized and compared to the nonketo
compounds for their abilities to inhibit reuptake transporter-mediated [3H]serotonin
accumulation into human platelets. MCAT inhibited [3H]serotonin uptake into platelets with an IC50 of
33.7 ± 9.0 uM while MA exhibited an IC50
of 11.7 ± 1.0 uM; this difference was not
significant. The methylenedioxy-substituted compounds
were about 6-fold more potent (P < 0.05) than the unsubstituted
compounds in this assay; MDMCAT displayed an IC50 of 5.8 ± 0.7 uM and MDMA had an IC50 of 2.1 ± 0.3 uM. The difference in potency between MDMCAT and MDMA was
significant at P < 0.01. These results indicate that beta-keto derivatization of
psychoactive phenylalkylamines does not have a major
impact on the drugs' ablility to inhibit serotonin
uptake and that phenyl ring substitutions can enhance potency.
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