18690-56-7

Usage

Chemical class

Tryptamine

Structure

Structurally related to the neurotransmitter serotonin

Function

Potent monoamine oxidase inhibitor and serotonin releasing agent

Therapeutic applications

Investigation for potential use in the treatment of depression and anxiety

Psychoactive properties

Known for its psychedelic effects

Legal status

Controlled substance in some countries due to potential for abuse.

Upstream product

• 95202-45-2 1-benzyl-2-methyl 1H-indole-3-carboxyaldehyde 
• 614-31-3 N-benzyl-N-phenylhydrazine 
• 14267-92-6 1-chloro-4-pentyne 
• 60011-57-6 1-benzyl-2-methyl-3-cyanomethylindole 

Relevant academic research and scientific papers

Efficient one-pot synthesis of tryptamines and tryptamine homologues by amination of chloroalkynes

A new method was developed for the one-pot synthesis of substituted 3-(2-aminoethyl)- and 3-(3-aminopropyl)indoles from commercially available aryl hydrazines and chloroalkylalkynes. Various tryptamine derivatives were prepared directly in good yield with excellent regioselectivity. The method involves a new domino reaction sequence consisting of a titanium-catalyzed amination of the chloroalkylalkyne, [3+3]-rearrangement of the resulting aryl hydrazone, and nucleophilic substitution of the chloride by ammonia.

A CONVENIENT SYNTHESIS OF TRYPTAMINES

Reaction of tosylmethyl isocyanide with substituted formyl indoles gave the nitrile with one more carbon atom.Hydrogenation of this nitrile afforded the corresponding tryptamine.