N-Acetyl tryptamine

After serotonin is produced within the pineal gland, it is converted to 5-hydroxy-N-acetyltryptamine by N-acetyl transferase. 5-Hydroxy-N-acetyl-tryptamine is then methylated by O-methyl transferase. SAM is the methylating agent. With this information, draw the synthetic pathway of melatonin. 

Figure 15 shows the various ring closures of III as an assumed intermediate in the reaction of I with II. Structure IV was expected according to Spande et al. [15], where 3-methyl-indole reacted with 2-hydroxy-5-nitrobenzyl bromide, whereas reaction products of type V were formed when tryptophan [16], tryptophan ethyl ester [17] and N-acetyl-tryptamine [15] were allowed to react with 2-hydroxy-5-nitrobenzyl... 

Casnati and coworkers (69, 70) found that y, y-dimethylallyl bromide reacts with N-acetyl-tryptamine similarly to the Koshland s reagent. Two compounds were isolated and their structure (125) and (126) were determined (70). 

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