Structure-activity relationships for hallucinogenic N,N-dialkyltryptamines: photoelectron spectra and serotonin receptor affinities of methylthio and methylenedioxy derivatives

Abstract

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.

Nanonization of a chemically synthesized flavone HMDF (3-hydroxy-3′,4′-methylenedioxyflavone) by entrapping within calcium phosphate nanoparticles and exploring its antioxidant role on neural cells in vitro and zebrafish in vivo

“…HMDF has a methylenedioxy group fused at its ring B (figure 1(c)). The 3,4-(methylenedioxy) phenyl ring of HMDF is a rigid planar group that forces the 2p-orbital (with lone pairs of electrons) on oxygen of the methylenedioxy bridge into maximal overlap or conjugation with the p-orbital of the attached aromatic ring B, possibly increasing the electron density in ring B [9,10] and thus causing its high antioxidant activity [5]. Moreover, there are reports that incorporation of substituents, e.g.…”

“…Moreover, there are reports that incorporation of substituents, e.g. methylthio or methylenedioxy, at various positions of N,N-dialkyltryptamines induces significant changes in the neuropharmacological properties of these indolealkylamines [9,10]; since HMDF also has a methylenedioxy group fused at its ring B, this drew our interest in exploring HMDF as a neuroprotective agent against the oxidative stress-induced damages in neural cells. Another reason behind our selection of a flavone for developing a neuroprotective drug is that flavonoids have the ability to cross the blood-brain barrier [11,12].…”