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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.
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 is the subject of on-going biomedical research into its possible anticarcinogenic, [4] antioxidant, and anti-atherogenic effects. [5] Research on indole-3-carbinol has been conducted primarily using laboratory animals and cultured cells. [6] Limited and inconclusive human studies have been reported.
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 ]
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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.
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 ...
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