Created: May 14, 2021
Modified: May 14, 2021
Modified: May 14, 2021
substituted tryptamines
This page is from my personal notes, and has not been specifically reviewed for public consumption. It might be incomplete, wrong, outdated, or stupid. Caveat lector.- Substituted tryptamines - PsychonautWiki
- Tryptamine consists of an indole moeity plus a two-carbon (ethyl) chain with an amine group.
- We can distinguish between ring-substituted and ring-unsubstituted tryptamines. In ring-unsubstituted or 'base' tryptamines, the only substitutions are on the chain.
- One of the simplest (ring-unsubstituted) tryptamines is di-methyl-tryptamine, also known as DMT. It just replaces the NH2 with N-CH3-CH3, adding two methyl groups.
- Further substituting an OH, on the benzene ring at the 4 position, produces psylocin, or 4-HO-DMT. Replacing the OH with O-acetyl, where acetyl means (C=O)-CH3, gives psilacetin, or 4-AcO-DMT. Similarly, replacing the OH group with a phosphate group gives psilocybin.
- Another simple substitution is to 'just make it an amino acid' by attaching a -COOH group as a sibling of the amine group, yielding tryptophan.
- One of the simplest ring substitutions---attaching an OH at the 5 position on the benzene ring---gives serotonin, or 5-hydroxy-tryptamine, or 5HT. Also attaching a COOH group to make it an amino acid gives 5-hydroxy-tryptophan, or 5HTP.