A neuroactive metabolite of L-tryptophan
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Parent Compound(s)
29600L-Tryptophan
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5-Hydroxyindole

Item No. 36431

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
1H-indol-5-ol
CAS Number
1953-54-4
Synonyms
  • NSC 87503
Molecular Formula
C8H7NO
Formula Weight
133.1
Purity
≥98%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMF: 1 mg/mlDMSO: 2 mg/mlEthanol: 5 mg/ml
SMILES
OC1=CC2=C(NC=C2)C=C1
InChi Code
InChI=1S/C8H7NO/c10-7-1-2-8-6(5-7)3-4-9-8/h1-5,9-10H
InChi Key
LMIQERWZRIFWNZ-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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Certificates of Analysis & Batch Specific Data

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    500 mg

    $32

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    1 g

    $61

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    5 g

    $156

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    10 g

    $279

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    Product Description

    5-Hydroxyindole is a neuroactive metabolite of L-tryptophan (Item No. 29600).1 It is formed from L-tryptophan by gut microbiota expressing tryptophanase (TnaA) via 5-hydroxy-L-tyrptophan (5-HTP; Item No. 20539) and indole intermediates.1,2 5-Hydroxyindole (0.03-30 mM) potentiates transient inward currents induced by acetylcholine (Item No. 23829) in Xenopus oocytes expressing α7 nicotinic acetylcholine receptors (nAChRs).3 It also potentiates ion currents induced by serotonin (5-HT; Item No. 14332) in N1E-115 mouse neuroblastoma cells when used at a concentration of 1 mM.4 5-Hydroxyindole (30 mg/kg) decreases gastrointestinal transit time in rats.2 It induces convulsions in rats when administered at doses ranging from 50 to 100 mg/kg.5 Serum 5-hydroxyindole levels are positively correlated with working memory in patients with schizophrenia.1

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Huang, J., Tong, J., Zhang, P., et al. Effects of neuroactive metabolites of the tryptophan pathway on working memory and cortical thickness in schizophrenia. Transl. Psychiatry 11(1), 198 (2021).

    2. Waclawiková, B., Bullock, A., Schwalbe, M., et al. Gut bacteria-derived 5-hydroxyindole is a potent stimulant of intestinal motility via its action on L-type calcium channels. PLoS Biol. 19(1), e3001070 (2021).

    3. Zwart, R., De Filippi, G., Broad, L.M., et al. 5-Hydroxyindole potentiates human α7 nicotinic receptor-mediated responses and enhances acetylcholine-induced glutamate release in cerebellar slices. Neuropharmacology 43(3), 374-384 (2002).

    4. van Hooft, J.A., van der Haar, E., and Vijverberg, H.P. Allosteric potentiation of the 5-HT3 receptor-mediated ion current in N1E-115 neuroblastoma cells by 5-hydroxyindole and analogues. Neuropharmacology 36(4-5), 649-653 (1997).

    5. Mannaioni, G., Carpenedo, R., and Moroni, F. 5-hydroxyindole causes convulsions and increases transmitter release in the CA1 region of the rat hippocampus. Br. J. Pharmacol. 138(1), 245-253 (2003).