Synthesis and evaluation of a novel series of N,N-dimethylisotryptamines.
A novel series of N,N-dimethylisotryptamine (isoDMT) derivatives, i.e., derivatives of 1-[2-(dimethylamino)ethyl]indole, was prepared and found to be isosteric with their corresponding N,N-dimethyltryptamine (DMT) counterparts with respect to serotonin receptor (rat fundus) affinity. Whereas the isoDMT derivatives possessed a greater affinity than did their corresponding DMT derivatives, they were relatively ineffective in displacing [3H]-5-HT binding from rat brain (cortex) homogenates. In a drug discrimination paradigm, using rats as subjects, 6-OMe-isoDMT produced effects similar to those of 5-OMe-DMT. Attempts to antagonize the discriminative stimulus effects of the hallucinogen 1-(2,5-dimethoxy-4-methylphenyl)-2-aminopropane (DOM) using two of the isoDMT derivatives proved unsuccessful.
D000818:Animals; D001681:Biological Assay; D001921:Brain / Q000378:metabolism; D002462:Cell Membrane / Q000378:metabolism; D004193:Discrimination Learning / Q000187:drug effects; D007202:Indicators and Reagents; D004130:N,N-Dimethyltryptamine / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000494:pharmacology; D051381:Rats; D011985:Receptors, Serotonin / Q000187:drug effects / Q000378:metabolism; D012702:Serotonin Antagonists / Q000138:chemical synthesis*; D013329:Structure-Activity Relationship; D014363:Tryptamines / Q000138:chemical synthesis*
D007202:Indicators and Reagents; D011985:Receptors, Serotonin; D012702:Serotonin Antagonists; D014363:Tryptamines; D004130:N,N-Dimethyltryptamine