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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.
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.