| Identification | Back Directory | [Name]
5-Nonyloxytryptamine oxalate | [CAS]
157798-13-5 | [Synonyms]
Nonyloxytryptamine
JORSCLBFSAAOFR-UHFFFAOYSA-N
Nonyloxytryptamine oxalate >=98% (HPLC)
5 Nonyloxytryptamine oxalate,5Nonyloxytryptamine oxalate | [Molecular Formula]
C21H32N2O5 | [MOL File]
157798-13-5.mol | [Molecular Weight]
392.5 |
| Chemical Properties | Back Directory | [storage temp. ]
room temp | [solubility ]
DMSO: soluble2mg/mL, clear (warmed) | [form ]
powder | [color ]
white to yellow to light brown | [InChI]
1S/C19H30N2O.CH4/c1-2-3-4-5-6-7-8-13-22-17-9-10-19-18(14-17)16(11-12-20)15-21-19;/h9-10,14-15,21H,2-8,11-13,20H2,1H3;1H4 | [InChIKey]
LXACPZFRJZIDDI-UHFFFAOYSA-N | [SMILES]
CCCCCCCCCOC1=CC=C(NC=C2CCN)C2=C1.C |
| Hazard Information | Back Directory | [Description]
Nonyloxytryptamine is a potent agonist of the serotonin (5-HT) receptor 5-HT1Dβ with an EC50 value of 68 nM for adenylate cyclase activity in CHOKM6 cells transfected with the human 5-HT1Dβ receptor. It is selective for 5-HT1Dβ over 5-HT1A for its adenylate cyclase activity, with an EC50 greater than 1 μM for 5-HT1A. It binds to 5-HT1Dβ, 5-HT1A, 5-HT1B, 5-HT2A, and 5-HT2C receptors in vitro (Kis = 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. | [Uses]
5-Nonyloxytryptamine Oxalate is a selective 5-HT1B agonist. | [Definition]
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+). | [Biochem/physiol Actions]
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. | [References]
[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 |
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