Synthesis and structure of 4-hydroxy-N-isopropyltryptamine (4-HO-NiPT) and its precursors
U. Laban, Marilyn Naeem, A.r. Chadeayne, James A. Golen, David R. Manke
Acta Crystallographica Section E Crystallographic Communications March 10, 2023 DOI: 10.1107/s2056989023002098 via OpenAlex
Summary
The compound 4-hydroxy-N-isopropyltryptamine (4-HO-NiPT) was synthesized in three steps from 4-benzyloxyindole. The synthesis involved treatment with oxalyl chloride and isopropylamine, reduction, and hydrogenation. Crystal structures of the final compound and all three synthetic precursors are reported.
Study at a glance
| Characteristics | Chemical synthesis and structural characterization Peer reviewed |
|---|---|
| Keywords | Oxalyl chloride Acetamide Crystal structure Isopropylamine Indole test |
| Citations | 2 |
| Key finding | The synthesis and crystal structures of 4-hydroxy-N-isopropyltryptamine and its synthetic precursors are presented. |
Abstract
The title compound, 4-hydroxy- N -isopropyltryptamine ( 4 ) or 4-HO-NiPT (systematic name: 3-{2-[(propan-2-yl)amino]ethyl}-1 H -indol-4-ol), C 13 H 18 N 2 O, was synthesized in three steps from 4-benzyloxyindole ( 1 ) (systematic name: 4-phenoxy-1 H -indole), C 15 H 13 NO. ( 1 ) was treated with oxalyl chloride and isopropylamine to produce N -isopropyl-4-benzyloxy-3-indoleglyoxylamide ( 2 ) {systematic name: 2-[4-(benzyloxy)-1 H -indol-3-yl]-2-oxo- N -(propan-2-yl)acetamide}, C 20 H 20 N 2 O 3 . ( 2 ) was reduced to generate 4-benzyloxy- N -isopropyltryptamine (3) or 4-HO-NiPT, which was characterized as its chloride salt 4-benzyloxy- N -isopropyltryptammonium chloride ( 3a ) (systematic name: {2-[4-(benzyloxy)-1 H -indol-3-yl]ethyl}(propan-2-yl)azanium chloride), C 20 H 25 N 2 O·Cl. Finally the benzyl group of (3) was removed via hydrogenation to generate 4-HO-NiPT. The crystal structures of the title compound and all three synthetic precursors are presented.