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Chemical Properties

White to Orange Crystalline Powder

Uses

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

Definition

ChEBI: An aminoalkylindole consisting of indole having a 2-aminoethyl group at the 3-position.

Definition

tryptamine: A naturally occurringalkaloid, C₁₀H₁₂N₂, having an indolering system with a –CH2–CH2–NH2side chain in the 3-position of thenitrogen-containing ring. Derivativesof tryptamines have hallucinogeniceffects. An example in psilocybin.

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.]

References

[1] ANA MARGARIDA ARAúJO. The hallucinogenic world of tryptamines: an updated review[J]. Archives of Toxicology, 2015, 89 8: 1151-1173. DOI: 10.1007/s00204-015-1513-x
[2] ARNAO M B. Phytomelatonin: Discovery, Content, and Role in Plants[C]. 2014: 0. DOI: 10.1155/2014/815769
[3] JIBIAO FAN. Melatonin: A Multifunctional Factor in Plants.[J]. International Journal of Molecular Sciences, 2018, 19 5. DOI: 10.3390/ijms19051528
[4] LORENA ALMAGRO  Maria A P  Francisco Fernández Pérez. Indole alkaloids from Catharanthus roseus: bioproduction and their effect on human health.[J]. Molecules, 2015, 20 2: 2973-3000. DOI: 10.3390/molecules20022973
[5] LAURA CRISTINA BERUMEN. Serotonin receptors in hippocampus.[J]. The Scientific World Journal, 2012: 823493. DOI: 10.1100/2012/823493

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Questions And Answer

• Description

  Tryptamine 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. ;

• Applications

  Analogs of tryptamine that are typically produced by its synthetic modification play a significant role in individuals due to the introduction of functionalities that are biologically active in its nucleus that may cause changes in the mental and physical status of the human brain.
  Substitutions on the indole ring at nitrogen and C-2 of its side chain produce numerous neuroactive compounds ranging from anti-migraine drugs to toxic substances, such as rizatriptan, sumatriptan, and zolmitriptan. A small amount of tryptamine is required due to its fatalities and intoxication for several reasons. ;

• Plants Containing Tryptamine

  In plants, tryptamine in small amounts acts as a promising phase to the plant hormone indole-3-acetic acid in one biosynthetic pathway. N, N-dimethyltryptamine (DMT) is a tryptamine derivative that is an active constituent for the hallucinogenic effect of brew known as the “vine of the souls.” Indigenous Amazonian tribes have traditionally used the drink for therapeutic purposes for effective treatment of some physical maladies and abuse disorders. Magic mushrooms are the most common fungi that contain tryptamine derivatives. ;

• Pharmacology

  Serotonin (5-hydroxytryptamine, 5-HT), which is a natural derivative of tryptamine is a significant signaling hormone that helps in the modulation and regulation of numerous processes within the central nervous system, for instance, cognition, sleep, temperature regulation, memory, and behavior. The mammalian brain contains small traces of tryptamine, which generally act as a modulator or neurotransmitter by releasing serotonin agents. It is also an enhancer of serotonergic activity. Only one minute is required for tryptamine to produce psychotropic phenomena when used recreationally. It has been associated with fatalities and intoxications for multiple reasons including low toxic concentrations. ;

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