Posts Tagged ‘ alpha substitution

Alpha Substituted Tryptamines

The tryptamine backbone provides a building block for a large number of research chemicals. One such class is the alpha-substituted tryptamines. There are two carbons between the amine group (NH2) and the indole ring of tryptamine, referred to as alpha and beta.

Short alkyl chains have successfully been substituted at the alpha position nearest the amine group. These include compounds such as AMT and AET, which are releasing agents of serotonin, norepinephrine, and dopamine resulting in stimulating and euphoric effects. At higher doses their psychedelic character becomes more prominent. Potency decreases as alkyl chain length increases, and alpha-propyltryptamine has not been widely explored.

What about substitution on the beta carbon instead? It doesn’t seem hopeful. Substitution at the alpha carbon acts to protect the compound against enzymatic degradation but the beta position does not have this advantage. Little actual data regarding synthesis or effects are available however, and this remains an unexplored possibility.