Synthesis and Characterization of N,N-Diallyltryptamines

4-AcO-DALT (3) and 4-OH-DALT (4), sold as the fumarate salt, were from Scientific Supplies (London, UK). 5-MeO-2-Me-DALT HCl (8) and 5-EtO-DALT HCl (9) were available from previous studies.^{[39 (link),42 (link)]}The synthesis of N,N-diallyltryptamines (DALTs) reported in this study adopted the well-established procedure of Speeter and Anthony.^{[66 ]} As summarized in the Supporting Information, the substituted indole starting material (a) was acylated to give the acid chloride intermediate (b) followed by amination with N,N-diallylamine to the yield glyoxalylamide (c). The reduction with lithium aluminum hydride provided the DALT analogs. The reduction of the corresponding glyoxalylamide (c) (0.3 mmol) was carried out under microwave-accelerated conditions as described in detail by the authors previously.^{[35 ,39 (link),42 (link)]} High accuracy electrospray ionization mass spectra of the protonated molecules and their key product ions are summarized in Table 3. All ¹H and ¹³C NMR data for intermediates (c) and DALTs (1) – (17) are presented as Supporting Information.