157798-13-5

Nonyloxytryptamine is a potent agonist of the serotonin (5-HT) receptor 5-HT_1Dβ with an EC₅₀ value of 68 nM for adenylate cyclase activity in CHOKM6 cells transfected with the human 5-HT_1Dβ receptor. It is selective for 5-HT_1Dβ over 5-HT_1A for its adenylate cyclase activity, with an EC₅₀ greater than 1 μM for 5-HT_1A. It binds to 5-HT_1Dβ, 5-HT_1A, 5-HT_1B, 5-HT_2A, and 5-HT_2C receptors in vitro (K_is = 1.2-315 nM). Nonyloxytryptamine also inhibits reovirus-mediated cell death in a dose-dependent manner but has no effect on reovirus attachment or internalization.

5-Nonyloxytryptamine Oxalate is a selective 5-HT1B agonist.

ChEBI: 5-nonyloxytryptamine oxalate is an oxalate salt obtained by reaction of 5-nonyloxytryptamine with one equivalent of oxalic acid. 5-HT1B selective agonist, several times more potent than sumatriptan and inactive as a 5-HT1A agonist (Ki at 5-HT1B = 1 nM, selectivity over 5-HT1A > 300-fold). It has a role as a serotonergic agonist. It contains a 5-nonyloxytryptaminium(1+).

Nonyloxytryptamine (5-nonyloxytryptamine) is a potent and selective 5-HT1B receptor agonist. Nonyloxytryptamine is a polysialic acid (PSA) mimick that triggers PSA-mediated functions. Nonyloxytryptamine enhances neurite outgrowth of cultured primary neurons, protects neurons from oxidative stress, enhanced Schwann cell proliferation, reduces migration of astrocytes and enhances myelination in vitro.

[1] RICHARD A. GLENNON. 5-(Nonyloxy)tryptamine: A Novel High-Affinity 5-HT1D.beta. Serotonin Receptor Agonist[J]. Journal of Medicinal Chemistry, 1994, 37 18: 2828-2830. DOI: 10.1021/jm00044a001
[2] BERNARDO A MAINOU. Serotonin Receptor Agonist 5-Nonyloxytryptamine Alters the Kinetics of Reovirus Cell Entry.[J]. Journal of Virology, 2015: 8701-8712. DOI: 10.1128/jvi.00739-15