Tryptamine Tryptophan

Tryptamine, tryptophan and their derivatives are widely used in the synthesis of indolo[3,2,l-naphthyridine derivatives. Thus, refluxing tryptamine 35 with 2-formylbenzoic acid 36 in alcohol followed by the addition of concentrated hydrochloric acid afforded hexahydrobenzo[/z]indolo[3,2,l-[Pg.194]

The decarboxylation of amino acids (name in brackets) leads to the biogenic amines phenyl-ethylamine (phenylalanine), tyramine (tyrosine), tryptamine (tryptophan), histamine (histidine), putrescine (ornithine) and cadaverine (lysine). The content of these compounds in some types of cheese is presented in Table 10.34. These values can fluctuate greatly depending on the degree of ripening. On average, 350-500 pmol per person per day are consumed. Apart from cheese. 

Tryptamine Tryptophan Serotonine, melatonine Locan tissue animal and plant hormones (catecholamines), effect on blood pressure, intestinal peristalsis, mental functions... 

The appearance of the 2-(indol-3yl)ethylamine (tryptamine) unit in both tryptophan-derived natural products and in synthetic materials having potential pharmacological activity has generated a great deal of interest in the synthesis of such compounds. Several procedures which involve either direct 3-alkylation or tandem 3-functionalization/modification have been developed. Similarly, methodology applicable to preparation of tryptophan analogues has been widely explored. 

Chapter 13, Introduction of the Tryptamine and Tryptophan Side-Chains. 125... 

Amines, Amino acids, peptides, e g tryptophan, tryptamine, peptides with terminal tryptophan groups... 

The reactions of tryptophan and of tryptamine derivatives with formaldehyde require special comment. Whereas tryptamine and its 5- and 7-methoxy and i id-A-methyl and -ethyl derivatives react... 

The second line of circumstantial evidence quoted in support of this hypothesis is the ready formation of l,2,3,4-tetrahydro-/3-carboline derivatives under pseudo-physiological conditions of temperature, pH, and concentration. Tryptamine and aldehydes, trypt-amine and a-keto acids, and tryptophan and aldehydes condense at room temperature in a Pictet-Spengler type intramolecular Mannich reaction in the pH range 5.2-8.0 (cf. Section III, A, 1, a). It was argued that experiments of this type serve as models for biochemical reactions and may be used in evidence. 

Whatever the detailed biogenetic steps, there is almost general agreement that j3-earboline derivatives originate in living systems from tryptophan or tryptamine. 

The biogenetie origin of jS-earboline systems with extended rings has been repeatedly diseussed. Almost invariably tryptophan or tryptamine is assumed to give rise to the major portion of the j8-earboline nueleus. Attention in these discussions was focused on the elaboration of the non-carboline portion of these molecules. Discussion of these... 

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