Psilocin analogs. 1. Synthesis of 3‐[2‐(dialkylamino)ethyl] ‐and 3‐[2‐(cycloalkylamino)ethyl] indol‐4‐ols

Abstract

The synthesis of four dialkyl and three eyeloalkyl analogs of psilocin (4, R ‐ CH3), a hallucinogenic principle found in certain fungi, is described. The synthetic route involves four transformations starting with 6,7‐dihydroindol‐4(5H)one: (1).

SAR of psilocybin analogs: Discovery of a selective 5-HT2C agonist

“…functional activity as an agonist at the 5-HT 2C receptor with some selectivity over the 5-HT 2A and 5-HT 2B receptors (about 10-fold each). A shortening in the length of the linker at the 3-position of the indole ring to a methylene group (13) gave an antagonist at the 5-HT 2A and 5-HT 2C receptors, while 14 (N-methyl, methylene linker), 15 (propylene linker), and 16 (amethyl) all showed reduced affinity and selectivity for the 5-HT 2C receptor. Finally, 17 (side chain moved to the 1-position) was also quite inactive in binding at the 5-HT 2C receptor.…”

“…The compounds prepared (3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14)(15)(16)(17) 8 are shown in Figure 2. Known N-methylated derivatives 3 and 4 were synthesized following published procedures.…”

Bis(4-hydroxy-N,N-di-n-propyltryptammonium) fumarate tetrahydrate

“…The synthesis of 4-HO-DPT was first reported by Repke et al in 1977(Repke et al, 1977. The molecular structure of bis(4-hydroxy-N,N-di-n-propyltryptammonium)-data reports fumarate is shown in Fig.…”

Synthesis of 14C‐labeled 4‐hydroxyindole as an intermediate for the preparation of (S)‐2‐[4‐[2‐[3‐(indol‐2‐[14C]‐4‐yloxy)‐2‐hydroxypropylamino]‐2‐methylpropyl]‐phenoxy]pyridine‐5‐carboxamide (LY368842‐[indole‐14C]) glycolate

“…3 We were interested in the preparation of 14 C-labeled 4-hydroxyindole to be used in the synthesis of radiolabeled b 3 adrenergic agonist LY368842, a compound with a potential for the treatment of obesity and diabetes. 4 There are different methods of the synthesis of 4-hydroxyindole presented in literature.…”