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Indole-3-carbaldehyde (I3A), also known as indole-3-aldehyde and 3-formylindole, is a metabolite of dietary L-tryptophan which is synthesized by human gastrointestinal bacteria, particularly species of the Lactobacillus genus.
The process begins by producing 7-chloroindole-3-acetamide by treating 7-chloroindole with a series of reagents, shown farther down. This molecule is then glycosylated and reacted with methyl 7-chloroindole-3-glyoxylate to produce an intermediate that goes on to stabilize into the final product.
Moreover, 3-hydroxymethyl-beta-carboline blocks the sleep-promoting effect of flurazepam in rodents and – by itself – can decrease sleep in a dose-dependent manner. [16] Another derivative, methyl-β-carboline-3-carboxylate, stimulates learning and memory at low doses but can promote anxiety and convulsions at high doses. [ 15 ]
At very low concentrations, however, it has a flowery smell, [3] and is a constituent of many perfumes. It also occurs in coal tar. It has been identified in cannabis. [4] It is the main volatile compound in stinky tofu. [5] When indole is a substituent on a larger molecule, it is called an indolyl group by systematic nomenclature.
Indole-3-carbinol induces a G1 growth arrest of human reproductive cancer cells. [9] This is potentially relevant to the prevention and treatment of cancer, as the G1 phase of cell growth occurs early in the cell life cycle, and, for most cells, is the major period of cell cycle during its lifespan.
In addition to the light- or H 2 O 2-induced formation of FICZ, a number of other enzymatic pathways have been identified to convert Trp to FICZ via the precursor I3A. [2] [3] Oxidative deamination of Trp by aromatic amino acid aminotransferases (ArAT) or L-amino oxidases (LAAO), one of which is the IL4-inducible enzyme IL4I1, converts Trp to indole-3-pyruvate, which after decarboxylation ...
Some organochlorides are considered safe enough for consumption in foods and medicines. For example, peas and broad beans contain the natural chlorinated plant hormone 4-chloroindole-3-acetic acid (4-Cl-IAA); [16] [17] and the sweetener sucralose (Splenda) is widely used in diet products.
5-(2-Aminopropyl)indole (5-API, 5-IT, PAL-571) [1] is an indole and phenethylamine derivative with empathogenic effects. Its preparation was first reported by Albert Hofmann in 1962. [ 2 ] It is a designer drug that has been openly sold as a recreational drug by online vendors since 2011.