Tryptamine

DescriptionTryptamine is a monoamine alkaloid that can be synthesized by decarboxylation of the amino acid tryptophan. Notably, tryptamine can be found in fungi, plants, Amphibia, animals, and microbes. Tryptamine has an indole ring structure and a fused double ring that is composed of a benzene ring and a pyrrole ring, linked to an amino group by 2-carbon side chain. The indole ring is the vital nucleus of many complex natural products that have significance in drug discovery as well as some synthetic and non-synthetic drugs that are based on tryptamine skeleton. The chemical’s distinct structure is an approximation to the neurotransmitter serotonin as well-known drugs and hallucinogens. Tryptamine’s significance as psychedelic drugs, neuromodulator, and neurotransmitter is well understood due to its presence in mammalian brain in small amounts.

DescriptionTryptamine 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.

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

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

PreparationTryptamine, 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.

DefinitionChEBI: 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.