N-Acetyltryptamine

N-Acetyltryptamine (N10-Acetyltryptamine) is a mixed agonist-antagonist of the melatonin receptor. N-Acetyltryptamine inhibits acetylserotonin methyltransferase, blocks the conversion of N-acetylserotonin to melatonin, and inhibits neuronal firing activity in suprachiasmatic nucleus neurons. N-Acetyltryptamine is a physiological constituent of mammalian blood. N-Acetyltryptamine is a metabolite of tryptamine in Bacillus cereus^{[1][2][3][4][5]}. In Vitro:N-acetyltryptamine is present in daytime plasma of rats, rhesus macaques, and humans, establishing it as a physiological constituent of mammalian blood^[1].
N-acetyltryptamine (100 μM-10 mM) exhibits concentration-dependent mixed agonist-antagonist effects on Melatonin (HY-B0075)-evoked responses in rat SCN neurones, acting as an antagonist at 100 μM (blocking Melatonin-evoked responses with a smaller reduction in firing) and as an agonist at 1-10 mM (suppressing neuronal discharge)^[2].
N-Acetyltryptamine acts as a noncompetitive inhibitor versus Tryptamine (HY-B2132) and an uncompetitive inhibitor versus Acetyl-CoA (Acetyl coenzyme A) (HY-114293) in the GST-AANAT-catalyzed reaction, supporting an ordered BiBi ternary complex mechanism where N-acetyltryptamine is the first product released^[3].
N-Acetyltryptamine is formed as an artifact during the extraction of Tryptamine with ethyl acetate under mild basic conditions via base-catalyzed aminolysis, as confirmed by TLC, mass spectrometry, and comparison with the authentic synthetic complex^[4].
N-Acetyltryptamine during senescence completely inhibits melatonin synthesis without altering N-acetylserotonin levels in detached Asahi rice leaves^[5].
N-Acetyltryptamine is a genuine metabolite of tryptamine in Bacillus cereus, not an extraction artifact^[4].