5-Hydroxyindole

• Description:

  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].

• 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.

• Shipping Conditions:

  Room Temperature

• Storage Conditions:

  -20°C, 3 years; 4°C, 2 years (Powder)

• Scientific Category:

  Natural Products

• Clinical Information:

  No Development Reported

• Isoform:

  L-type calcium channel; Microbial Metabolite

• CAS Number:

  [1953-54-4]