Syntheses of Serotonin, N-Methylserotonin, Bufotenine, and Melatonin, and the First Total Synthesis of N-(Indol-3-yl)methyl-N-methyl-5-methoxytryptamine from Tryptamine through a Common Intermediate, 1-Hydroxytryptamine

Simple syntheses of serotonin (la), N-methylserotonin (lb), bufotenine (lc), and melatonin (2), and the first total synthesis of N-(indol-3-y1)methyl-N-methyl-5-methoxytryptamine (3) from tryptamine (4a) are reported through acid catalyzed nucleophilic substitution reaction of 1-hydroxytryptamines.Tryptamine alkaloids such as serotonin (la, Scheme l)? N-methylserotonin (lb)?bufotenine (lc) ?arb