Substituted isotryptamine

Substituted isotryptamines, or simply isotryptamines, also known as 2-(1-indolyl)ethylamines, are a group of indoles closely related to the tryptamines but with the ethylamine side chain located at the 1 position of the indole ring system rather than at the 3 position as in tryptamines. Hence, they are positional isomers of tryptamines.

Isotryptamine, the parent compound of the substituted isotryptamines and the simplest isotryptamine.

A variety of isotryptamines have been studied and described, including serotonergic psychedelics and psychoplastogens like 6-MeO-isoDMT;^[1][2] non-hallucinogenic psychoplastogens like isoDMT, 5-MeO-isoDMT, and zalsupindole (DLX-001; AAZ-A-154);^[3][4][5][6] serotonin 5-HT_2C receptor agonists like (S)-5,6-difluoro-isoAMT, Ro60-0175 ((S)-5-fluoro-6-chloro-isoAMT), and PNU-181731;^{[7][8][9][10][11]} serotonin 5-HT₆ receptor modulators;^[12][13][14] and dual monoamine releasing agents and serotonin receptor agonists like isoAMT (PAL-569).^[15][16][17]

JRT is the isotryptamine analogue of LSD and may be considered a cyclized isotryptamine.^[18][19]

Chemical structures of selected isotryptamines

• 
  Isotryptamine
• 
  isoDMT
• 
  6-MeO-isoDMT
• 
  5-MeO-isoDMT
• 
  isoAMT
• 
  Zalsupindole
• 
  Ro60-0175
• 
  PNU-181731
• 
  JRT