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Tryptamines

Tryptamines are compounds which share a common indole ring structure. Along with phenethylamines, they form the two principal classes of psychoactive compounds. Tryptamines have been studied by Alexander Shulgin and are the subject of his book TiHKAL, published in 1997. Their main use is recreative, and most of them are thus illegal to consume, produce ad possess.

Contents




[top]Introduction to Tryptamines

<Begin text introduction here>


[top]Chemical description of Tryptamines

Tryptamines are chemical derivatives of tryptamine. Substituents can be present on the aromatic ring (in blue), especially on the positions 4 and 5, and on the amine (in red).

They are derived from the amino acid tryptophan, which is the biological precursor of tryptamine and serotonin, a neurotransmitter.


[top]Uses of Tryptamines



[top]Effects of Tryptamines



[top]General pharmacology of Tryptamines


The pharmacological action of tryptamines is highly related to their similarity with the neurotransmitter serotonin.


[top]Dangers of Tryptamines



[top]Sources of Tryptamines

[top]Natural sources


Despite being a smaller class than phenethylamines, a greater number of different (and psychoactive) tryptamines can be found in nature, and in a wide variety of species.

[top]Synthesis


Two main synthetic pathways can lead to simple tryptamines:

[top]Extension of the indole ring


A conveniently substituted indole ring can be extended to a tryptamine in three steps. First the indole ring (1) is reacted with oxalyl chloride to form an indoleglyoxyl chloride derivative (2), which is subsequently reacted with the desired amine to an indoleglyoxyl amine derivative (3). The latter compound is then reducted with lithium aluminium hydride to yield the tryptamine (4).

This method was employed by A. Shulgin. It is very versatile provided one can get the starting indole ring, and the substituted amine, which may be hard to acquire.

[top]Fisher synthesis of indoles



[top]Legal Status of Tryptamines



[top]History of Tryptamines



[top]Insights for Tryptamines



[top]More Tryptamines Sections and Information


Tryptamines image Gallery
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[top]The Latest Tryptamines Threads


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Contributors: John_bob, Docta, NeuroChi, Alfa
Created by Alfa, 30-08-2009 at 16:38
Last edited by John_bob, 21-02-2016 at 15:33
0 Comments, 29,380 Views

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