α-Methylmelatonin, also known as α-methyl-5-methoxy-N-acetyltryptamine, is a synthetic tryptamine derivative and analogue of the monoamine neurotransmitter melatonin. It is a metabolite of α-methyltryptophan, α-methyl-5-hydroxytryptophan, and α-methylserotonin that can be formed in small amounts via aralkylamine N-acetyltransferase (AANAT). α-Methyltryptophan and α-methyl-5-hydroxytryptophan are prodrugs of α-methylserotonin that have serotonergic actions and have been suggested for potential therapeutic use. However, while formation of α-methylmelatonin can occur from these compounds, α-alkylated tryptamines show 95% reduced suitability as substrates for AANAT compared to non-α-alkylated tryptamines in vitro and no α-methylmelatonin could be detected with administration of α-methyltryptophan in vivo in animals. α-Methyl-N-acetylserotonin is an intermediate is the formation of α-methylmelatonin from α-methylserotonin.
See also Substituted tryptamine
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