Recent Studies in the Field of Indole Compounds

An analytical perspective on favoured synthetic routes to the psychoactive tryptamines

“…Complete reduction was then achieved in boiling dioxane [12]. This observation is rather interesting since these ␤-hydroxy derivatives are normally known to be synthesised by the reduction of N-1-substituted amides [13,14], which is attributed to the substituted indole nitrogen not facilitating elimination of the ␤-hydroxy group.…”

“…When N-1-ethyl-␤-OH-DMT 8 was exposed to aqueous HCl, Heinzelman and Szmuszkovicz reported that the coloured, dimeric acid transformation product showed increased hypotensive activity in hypertensive rats, when compared to the monomer [13]. Based on UV and IR data the structure of this dimer, formed by self-condensation, was speculated to be 9 but attempts to characterise this compound unambiguously failed ( Fig.…”

“…The presence of ␤-hydroxylated byproducts can contribute to the formation of dimeric compounds [13]. This is attributed to the instability of these compounds in the presence of aqueous acids where deep red solutions can also be observed.…”

“…Based on UV and IR data the structure of this dimer, formed by self-condensation, was speculated to be 9 but attempts to characterise this compound unambiguously failed ( Fig. 2B) [13].…”

“…Interestingly, some ␤-hydroxylated tryptamines have been found to have significant pharmacological effects, such as hypotension [13][14][15]. The presence of ␤-hydroxylated byproducts can contribute to the formation of dimeric compounds [13].…”