Indole amines

Apply indole derivatives dissolved in sodium bo- [105] rate buffer solution (c = 0 2 mol/1, pH 9 0) — ethanol (1 -I-1) Dip TLC plate in fluorescamine solution to just above starting zone (15 s) Then dry at room temperature and develop In case of indole amines followed by spraying with 40% perchloric acid... 

One of the most common methods for introducing asymmetry into a Pictet-Spengler condensation reaction is to append a non-racemic auxiliary onto the indole amine or... 

Possibly there is a subclass of 5-HT receptors that would be preferentially activated by tryptamine if its endogenous concentrations were ever adequate. Indeed the term tryptamine receptor as first used by Gaddum to describe the effects of all indole amines may be one to which we should return. 

This enzyme [EC 1.13.11.42], also referred to as indole-amine-pyrrole 2,3-dioxygenase, catalyzes the reaction of tryptophan with dioxygen to form A-formylkynurenine. Heme participates as a cofactor. Many substituted and unsubstituted indoleamines, including melatonin, act as... 

Brady suggested from the experiments with copper chelators190 that indole-amine 2,3-dioxygenase is a copper-containing hemoprotein. On the other hand, Hirata et al. found negligible amounts of copper in their highly purified and active preparation of the enzyme191. ... 

A solution containing 1 mg of a free base in 1 ml of ethyl acetate was shaken with 0.5 ml of carbon disulphide for 30 min. Under reduced pressure the solution was evaporated to dryness and the residue dissolved in 1 ml of ethyl acetate. Aliquots of 1 pi were taken for analysis. For phenolic and indolic amines 100-pg aliquots of isothiocyanate derivatives are subjected to reaction with a mixture of BSTFA and TMCS (99 1) at 90°C for 15 min. 

Lately, Willis and coworkers [97,98] have developed a cascade N-annu-lation route to 1-functionalized indoles. Amine, aniline, amide, carbamate, and sulfonamide functional groups can efficiently be introduced as coupling partners if 2-(2-bromo-phenyl)-cyclohex-l-enyl triflate 112 is reacted in the presence of [Pd2dba3] and dpephos or xantphos as ligands to give a variety of tetrahydrocarbazoles 113 in moderate to excellent yields (Scheme 41). 

Imidazole alkaloids, 263 Indole alkaloids, 257-263 dehydrobufotenine, 262 dimeric, 261 indole amines, 261-262 pseudophrynamines, 257-261 trypargine, 262-263 Indole amines, 261-262 Indolizidines... 

Noting the structural resemblance of serotonin to the hallucinogenic indoles dimethyl tryptamine (DMT) and bufotenin, researchers proposed that psychotic symptoms were caused by these or similar compounds generated in schizophrenics by the abnormal transmethylation of endogenous indoleamines (21). Unfortunately, studies were unable to confirm increases in methylated indole amines in the plasma or CSF of schizophrenic patients versus controls (22). The transmethylation hypothesis is also questioned by the recognition that LSD-induced psychosis differs significant ways from the signs and symptoms of schizophrenia (23). 

Deguchi, T. and Barchas, J., Induction of hepatic tyrosine aminotransferase by indole amines, /. Biol. Chem., 246[23], 7217, 1971. 

As mentioned earlier, there are at least 50 putative transmitters that could potentially play a role in synaptic transmission or in neurochemical processes. These include acetylcholine, the aromatic monoamines (catecholamines and indole amines), a variety of primary and polyamines, certain amino acids, certain purine nucleosides and nucleotides, and a large number of peptides. The biosynthesis and regulation of the turnover of these putative transmitters will be discussed in another section of this article. However, it is worth noting here that the synthesis of these sundry transmitters is complex and variable, and in most cases the biologic control of the synthesis and degradation of these compounds is poorly understood at best. 

The primary alcohol in 133 was protected as the benzoyl ester 134 before removal of the aldehyde-protecting group in order to prevent hemiacetal formation between the Cn-OH and the C2i-aldehyde functions. The indole amine in 134 was tosylated under basic conditions, accompanied by some epimerization occurring at C-20, to produce the epimeric mixture 136. The aldehyde function in 136 was converted to a silyl enol ether, and then a hydroxy group was introduced at the C-20 position by treatment with... 

Thin-Layer and Gas-Liquid Chromatographic Methods for the Identification and Estimation of Indole-amines in Urine Samples Biochem. Med. 5(4) 304-310 (1971) ... 

Contrary to plants, higher animals can not synthesize compounds with benzenoid rings from aliphatic precursors, the very few exceptions include estrone and related phenolic steroids (Singleton, 1981). Plants are the source of nearly all the phenols found in animals. Even the phenols that are essential for animals (such as the catechol amines and phenolic indole amines involved in nerve action and associated effects), the vitamin E tocopherols, the vitamin K napthoquinones or menadiones, the ubiquinone benzoquinones, thyroxine, the tyrosine of proteins, and the tyrosine-DOPA derivatives involved in melanin pigment formation, are all drawn either directly or indirectly from plants or are modified from an essential plant precursor, usually phenylalanine (Singleton and Kratzer, 1969). 

Substrate Catalyst 7/cat. Conv. % Indole %° Amine % Other products... 

Psilocin/psilocyn An indole amine/tiyptamine found in mushrooms Psilocybe mexicana. 

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