Α-Methylmelatonin

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α-Methylmelatonin is a synthetic compound related to the sleep hormone melatonin. It’s a tryptamine derivative that can be formed in small amounts in the body from related molecules such as α-methyltryptophan, α-methyl-5-hydroxytryptophan, and α-methylserotonin, through the enzyme aralkylamine N-acetyltransferase (AANAT). These related compounds are prodrugs that can lead to α-methylserotonin with serotonin-like activity. However, when tryptophan derivatives are α-alkylated, they become poor substrates for AANAT—about 95% less effective—so α-methylmelatonin is not detected in vivo after administering α-methyltryptophan in animals. An intermediate in the formation pathway is α-methyl-N-acetylserotonin.