Tryptamine derivatives, hydroxylation

The procedure has also been applied for the hydroxylation of aromatic amines. Aniline and its /V-alkyl-substimted derivatives show similar behavior under similar conditions to afford the meta-substi tuted aminophenols as the major hydroxylated product.627 Product formation was interpreted by the attack of protonated hydrogen peroxide on the anilinium ion protected by /V-protonation from oxidation or degradation. Indoles, indolines, and tetrahydroquinoline have also been successfully hydroxylated with H202 in HF-SbF5 with the hydroxyl group meta to the nitrogen function.559,628 Hydroxylation of tryptophane and tryptamine derivatives affords pretonine and serotonine derivatives in 42% and 38% yields, respectively.629... 

S Sra, S. Hearst, E- The 6-Hydroxylation of Tryptamine Derivatives A Way of Producing Psychoactive Metabolites ... 

Biosynthesis C. is formed from tryptamine and the monoterpene loganin by way of strictosidine and strictosamide . Numerous naturally occurring and cytotoxic derivatives of C. are known, especially derivatives hydroxylated and methoxylated in the 7-, 9-, 10-, or 11-positions. 

It is really difficult to interpret and match the data obtained through submerged cultural condition with that of fruit bodies grown in wild to ascertain the biosynthesis mechanism. Some observations indicate that surface cultures of Psilocybe semilanceata have a high hydroxylation and phosphorylation capacity, although the ability to methylate tryptamine derivatives is low. These findings are in accordance with the earlier mentioned hypothesis that the fungus may have alternate route to convert 4-hydroxytryptamine to psilocybin. 

Tryptamine and its Al-methyl and A/Al-dimethyl derivatives (Figure 6.70) are widely distributed in plants, as are simple hydroxylated derivatives such as 5-hydroxytryptamine (serotonin). These are formed (Figure 6.70) by a series of decarboxylation, methylation, and hydroxylation reactions, though the sequences of these reactions are found to vary according to final product and/or... 

The one-carbon unit required for the formation of the /8-carboline tricycle is derived from 5-methyltetrahydrofolic acid, a cofactor present in platelets ( ). This finding led to a diagnostic assay which allows for the measurement of the enzyme activity of human platelets in terms of their ability to produce, on addition of tryptamine, TBC 25. This alkaloid, when given to rats, led to two metabolites hydroxylated in the aromatic ring at C-6 and C-7, respectively (59). The formation of these metabolites may proceed via an arene oxide. 

Brimblecombe I find your evidence concerning the psychotherapeutic drugs—the tranquillizers and anti-depressants—rather more convincing than the evidence relating to the psychotomimetic drugs. For example, the evidence for the 6-hydroxylation of tryptamine in vivo is not very strong and we would like to know that the hydroxylated mescaline derivative that you mentioned is a psychotomimetic drug. 

Jepson, J. B., Zaltzman, P. and Udenfriend, S., Microsomal hydroxylation of tryptamine, indoleacetic acid and related compounds, to 6-hydroxy derivates, Biochim, Biophys. Act. 62, 91 (1962). 

Tryptophan-Derived Indole and Indole Monoterpene Alkaloids As for alkaloids derived from tyrosine and phenylalanine, those derived from tryptophan are formed after decarboxylation of the amino acid (into tryptamine) and possible hydroxylation of the aromatic carbocycle (e.g., serotonin) and N-methylation (e.g., psilocin). As previously, tryptamine can also react through Pictet-Spengler reactions to form tetrahydro-p-carbolines, which can be aromatized, for example, into harmine (Scheme 1.8) [16]. 

---