5-Hydroxyindole

5-Hydroxyindole is an orally active hydroxylated indole and tryptophan metabolite. 5-Hydroxyindole activates α7 nicotinic acetylcholine receptors and acts on intestinal L-type calcium channels. 5-Hydroxyindole slows down the desensitization of 5-HT3 receptor-mediated ion currents in cells. 5-Hydroxyindole causes convulsions and loss of consciousness. 5-Hydroxyindole is used in the study of neuroblastoma, schizophrenia, and diseases related to intestinal motility disorders[1][2][3][4][5][6][7].

Product Specifications

CAS Number

[1953-54-4]

UNSPSC

12352005

Hazard Statement

H302, H315, H319, H335

Target

Calcium Channel; Endogenous Metabolite; nAChR

Type

Natural Products

Related Pathways

Membrane Transporter/Ion Channel; Metabolic Enzyme/Protease; Neuronal Signaling

Field of Research

Cancer; Endocrinology; Neurological Disease

Assay Protocol

https://www.medchemexpress.com/5-hydroxyindole.html

Purity

99.94

Solubility

DMSO : 50 mg/mL (ultrasonic)

Smiles

OC1=CC2=C(C=C1)NC=C2

Molecular Formula

C8H7NO

Molecular Weight

133.15

Precautions

H302, H315, H319, H335

References & Citations

[1]Kooyman AR, et, al. 5-Hydroxyindole slows desensitization of the 5-HT3 receptor-mediated ion current in N1E-115 neuroblastoma cells. Br J Pharmacol. 1993 Feb;108 (2) :287-9.|[2]LaPorte M, et, al. 5-Hydroxyindoles by intramolecular alkynol-furan diels-alder cycloaddition. J Org Chem. 2013 Jan 4;78 (1) :167-74.|[3]Huang J, et al. Effects of neuroactive metabolites of the tryptophan pathway on working memory and cortical thickness in schizophrenia. Transl Psychiatry. 2021 Apr 1;11 (1) :198.|[4]Zwart R, et al. 5-Hydroxyindole potentiates human alpha 7 nicotinic receptor-mediated responses and enhances acetylcholine-induced glutamate release in cerebellar slices. Neuropharmacology. 2002 Sep;43 (3) :374-84.|[5]Van Hooft J A, et al. Allosteric potentiation of the 5-HT3 receptor-mediated ion current in N1E-115 neuroblastoma cells by 5-hydroxyindole and analogues. Neuropharmacology, 1997, 36 (4-5) : 649-653.|[6]Mannaioni G, et al. 5-hydroxyindole causes convulsions and increases transmitter release in the CA1 region of the rat hippocampus. Br J Pharmacol. 2003 Jan;138 (1) :245-53.|[7]Waclawiková B, et al. Gut bacteria-derived 5-hydroxyindole is a potent stimulant of intestinal motility via its action on L-type calcium channels. PLoS Biol. 2021 Jan 22;19 (1) :e3001070.