Structure-activity relationships for hallucinogenic N,N-dialkyltryptamines: photoelectron spectra and serotonin receptor affinities of methylthio and methylenedioxy derivatives.
Serotonin receptor affinity and photelectron spectral data were obtained on a number of substituted N,N-dimethyltryptamines. Evidence is presented that electron-donating substituents in the 5-position lead to enhanced behavioral disruption activity and serotonin receptor affinity as compared to unsubstituted N,N-dimethyltryptamine and analogues substituted in the 4- or 6-position. Some correlation was found between ionization potentials and behavioral activity, which may have implications concerning the mechanism of receptor binding.
D000818:Animals; D055598:Chemical Phenomena; D002627:Chemistry, Physical; D004583:Electrons; D005260:Female; D006213:Hallucinogens / Q000138:chemical synthesis*; D066298:In Vitro Techniques; D008297:Male; D004130:N,N-Dimethyltryptamine / Q000494:pharmacology; D051381:Rats; D011919:Rats, Inbred Strains; D011985:Receptors, Serotonin / Q000187:drug effects*; D013057:Spectrum Analysis / Q000379:methods; D013329:Structure-Activity Relationship; D014363:Tryptamines / Q000138:chemical synthesis* / Q000494:pharmacology
D006213:Hallucinogens; D011985:Receptors, Serotonin; D014363:Tryptamines; D004130:N,N-Dimethyltryptamine