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Synthesis of S (+) and R (‐)‐3‐(2‐aminopropyl)indole from ethyl‐ D ‐ and L ‐tryptophanate
Author(s) -
Repke David B.,
Ferguson Wilfred J.
Publication year - 1976
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570130417
Subject(s) - chemistry , indole test , enantiomer , psychotomimetic , reagent , stereospecificity , hydrochloride , stereochemistry , medicinal chemistry , organic chemistry , catalysis , biochemistry , nmda receptor , receptor
A stereospecific requirement for hallucinogenesis applies to certain molecules containing an asymmetric center. Thus, only the R ‐isomers of substituted phenylisopropylamines and lysergic acid diethylamide are psychotomimetic. The enantiomers of a minor hallucinogen, S (+)‐ and R (‐)‐3‐(2‐aminopropyl)indole (α‐methyltryptamine) ( 6a and 6b ) were synthesized via a 5‐step manipulation from D ‐ and L ‐tryptophan ethyl ester hydrochloride, respectively. Optical purity of these two isomers was determined by pmr spectroscopy of their complexes with a europium chiral shift reagent using the indole C 2 H signal.