1-Naphthyl and 4-indolyl arylalkylamines as selective monoamine reuptake inhibitors.
A series of enantiomerically pure 1-naphthyl and 4-indolyl arylalkylamines were prepared and evaluated for their binding affinities to the monoamine transporters. The two series of enantiomers displayed considerable differences in binding selectivity between the monoamine transporters, leading to the design of (S)-4-(3,4-dichlorophenyl)-4-(1H-indol-4-yl)-N-methylbutan-1-amine as a potent inhibitor for the dopamine and serotonin transporters.
Manning
James R
JR
Department of Chemistry, University at Buffalo, The State University of New York, Buffalo, NY 14260-3000, USA.
Sexton
Tammy
T
Childers
Steven R
SR
Davies
Huw M L
HM
D000588:Amines; D000818:Animals; D018687:Antidepressive Agents, Second-Generation; D015306:Biogenic Monoamines / Q000378:metabolism*; D018492:Dopamine Antagonists / Q000138:chemical synthesis; D018765:Dopamine Uptake Inhibitors / Q000138:chemical synthesis; D015195:Drug Design; D006801:Humans; D014179:Neurotransmitter Uptake Inhibitors / Q000138:chemical synthesis* / Q000494:pharmacology*; D011485:Protein Binding; D012702:Serotonin Antagonists / Q000138:chemical synthesis; D017367:Selective Serotonin Reuptake Inhibitors / Q000138:chemical synthesis; D013237:Stereoisomerism
D000588:Amines; D018687:Antidepressive Agents, Second-Generation; D015306:Biogenic Monoamines; D018492:Dopamine Antagonists; D018765:Dopamine Uptake Inhibitors; D014179:Neurotransmitter Uptake Inhibitors; D012702:Serotonin Antagonists; D017367:Selective Serotonin Reuptake Inhibitors