Molecular structure of 5-Hydroxyindole, CAS Number: 1953-54-4
5-Hydroxyindole (CAS 1953-54-4)
Alternate Names:
1H-indol-5-ol
Application:
5-Hydroxyindole is a reactant for preparation of anthranilic acids
CAS Number:
1953-54-4
Molecular Weight:
133.15
Molecular Formula:
C8H7NO
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
* Refer to Certificate of Analysis for lot specific data.
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SDS & Certificate of Analysis
5-Hydroxyindole functions as a precursor in the biosynthesis of serotonin. At the molecular level, 5-Hydroxyindole interacts with the enzyme tryptophan hydroxylase to catalyze the hydroxylation of tryptophan, leading to the formation of 5-hydroxytryptophan, which is further metabolized to serotonin. 5-Hydroxyindole′s mechanism of action involves its participation in the initial step of serotonin synthesis, contributing to the modulation of various physiological processes.
5-Hydroxyindole (CAS 1953-54-4) References
- 5-Hydroxyindole potentiates human alpha 7 nicotinic receptor-mediated responses and enhances acetylcholine-induced glutamate release in cerebellar slices. | Zwart, R., et al. 2002. Neuropharmacology. 43: 374-84. PMID: 12243767
- 5-hydroxyindole causes convulsions and increases transmitter release in the CA1 region of the rat hippocampus. | Mannaioni, G., et al. 2003. Br J Pharmacol. 138: 245-53. PMID: 12522096
- Effect of 5-hydroxyindole on ethanol potentiation of 5-hydroxytryptamine (5-HT)3 receptor-activated ion current in NCB-20 neuroblastoma cells. | Yang, HS., et al. 2003. Neurosci Lett. 338: 72-6. PMID: 12565143
- Modulation of the function of presynaptic alpha7 and non-alpha7 nicotinic receptors by the tryptophan metabolites, 5-hydroxyindole and kynurenate in mouse brain. | Grilli, M., et al. 2006. Br J Pharmacol. 149: 724-32. PMID: 17016503
- The L293 residue in transmembrane domain 2 of the 5-HT3A receptor is a molecular determinant of allosteric modulation by 5-hydroxyindole. | Hu, XQ. and Lovinger, DM. 2008. Neuropharmacology. 54: 1153-65. PMID: 18436267
- The anti-apoptotic action of 5-hydroxyindole: protection of mitochondrial integrity. | Bae, SJ., et al. 2010. Biol Pharm Bull. 33: 550-5. PMID: 20410584
- Emitting state of 5-hydroxyindole, 5-hydroxytryptophan, and 5-hydroxytryptophan incorporated in proteins. | Petrović, DM., et al. 2013. J Phys Chem B. 117: 10792-7. PMID: 24020960
- Auto-inhibition at a ligand-gated ion channel: a cross-talk between orthosteric and allosteric sites. | Hu, XQ. 2015. Br J Pharmacol. 172: 93-105. PMID: 25176133
- Colony analysis and deep learning uncover 5-hydroxyindole as an inhibitor of gliding motility and iridescence in Cellulophaga lytica. | Chapelais-Baron, M., et al. 2018. Microbiology (Reading). 164: 308-321. PMID: 29458680
- Microhydration of protonated 5-hydroxyindole revealed by infrared spectroscopy. | Klyne, J. and Dopfer, O. 2019. Phys Chem Chem Phys. 21: 2706-2718. PMID: 30663737
- Potential binding modes of the gut bacterial metabolite, 5-hydroxyindole, to the intestinal L-type calcium channels and its impact on the microbiota in rats. | Waclawiková, B., et al. 2023. Gut Microbes. 15: 2154544. PMID: 36511640
- 5-Hydroxyindole slows desensitization of the 5-HT3 receptor-mediated ion current in N1E-115 neuroblastoma cells. | Kooyman, AR., et al. 1993. Br J Pharmacol. 108: 287-9. PMID: 7680589
- Competitive and non-competitive effects of 5-hydroxyindole on 5-HT3 receptors in N1E-115 neuroblastoma cells. | Kooyman, AR., et al. 1994. Br J Pharmacol. 112: 541-6. PMID: 8075873
Inhibitor of:
Tyrosinase.Ordering Information
| Product Name | Catalog # | UNIT | Price | Qty | FAVORITES | |
5-Hydroxyindole, 1 g | sc-254834 | 1 g | $57.00 | |||
5-Hydroxyindole, 5 g | sc-254834A | 5 g | $130.00 |