Tryptamine

Description

Tryptamine is an indole alkaloid and intermediate in the biosynthesis of serotonin and the phytohormone melatonin in plants. It increases the levels of the terpenoid indole alkaloids ajmalicine, strictosidine, and catharanthine in cultures of C. roseus. Tryptamine is also a product of tryptophan metabolism in mammals. Tryptamine derivatives have been synthetically produced as hallucinogenic drugs of abuse that act on the serotonergic system.

Chemical properties

Tryptamine is a biogenic imine derived from the decarboxylation of tryptophan. It is a white to orange crystalline Powder, melting point 118°C (decomposition at 145-146°C). Soluble in ethanol and acetone, almost insoluble in ether, benzene, chloroform and water.

The Uses of Tryptamine

Tryptamine is a monoamine alkaloid found in plants. Tryptamine is commonly used in the preparation of biologically active compounds such as neurotransmitters and psychedelics.

What are the applications of Application

Tryptamine is a vasoactive, biogenic amine compound which may function as a neuromodulator

Definition

ChEBI: Tryptamine is an aminoalkylindole consisting of indole having a 2-aminoethyl group at the 3-position. It has a role as a human metabolite, a plant metabolite and a mouse metabolite. It is an aminoalkylindole, an indole alkaloid, an aralkylamino compound and a member of tryptamines. It is a conjugate base of a tryptaminium.

Preparation

Tryptamine, a monoamine alkaloid containing an indole ring structure is derived by the decarboxylation of amino acid tryptophan.

The synthesis of tryptamines is typically conducted following a classic route starting with a Mannich reaction of an indole heterocycle, followed by quaternization of the amine, nucleophilic substitution with highly toxic cyanide and final reduction.

General Description

Tryptamines which are usually found in plants, fungi, animals, etc. are categorized under the monoamine alkaloids class of compounds.

Biochem/physiol Actions

Vasoactive; may have a neuromodulator function; biogenic amine formed from the decarboxylation of tryptophan by L-aromatic amino acid decarboxylase.

Purification Methods

Crystallise tryptamine from *benzene, Et2O (m 114o) or pet ether (m 118o). It has UV: 222n 276, 282 and 291nm (EtOH) and max 226, 275, 281 and 290nm (HCl). [Beilstein 22 II 346, 22 III/IV 4319, 22/10 V 45.]