Author Topic: Novel tryptophan to DMT  (Read 3889 times)

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Novel tryptophan to DMT
« on: January 28, 2002, 03:38:00 PM »
producing DMT

this is kind of sketchy but anyone with enough knowledge to think about using these reactions will be able to fill in the blanks a bit like a chemical aptitude test 

Route 1

Alpha bromo indole propionic acid
Tryptophan is treated with NaNO2 and HBr, to make (probably through a cyclic intermediate involving the neighboring carboxyl group) alpha bromo indole propionic acid (not the iupac name) This reaction is used in a synthesis of thienamycin (where the amino acid is l-threonine rather than tryptophan.)

NN dimethyl tryptophan
Alpha bromo indole propionic acid is treated with an excess of dimethylamine solution. simple nucleophilic substitution creates NN dimethyl tryptophan in the form of the nndimethy ammonium salt. this salt is then trated with acid to precipitate NN dimethytryptophan 

NN Dimethyltryptamine

NN dimethyl tryptophan is then decarboxylated by reflux  without a catalyst in a high boiling point solvent leading to DMT. The standard decarboxylation catalysts-ketones do not work with this as the nn-dimethylamine moety cannot form the imine. As this decarboxylation can be difficult an alternative route is detailed below 

route 2

Tryptyl bromide
alpha bromo indole propionic acid is heated in an inert solvent resulting in indole ethyl bromide (tryptyl bromide). Because of the electron withdrawing effects of the alpha halogen the halocarboxylic acid readily decarboxylates.

NN Dimethyl tryptamine

the resulting tryptyl bromide is then treated with aqueous dimthylamine to yield DMT as the hydrobromide salt. this is then trated with base to liberate the freebase