| Size | Price | Stock | Qty |
|---|---|---|---|
| 500mg |
|
||
| Other Sizes |
| Targets |
Microbial Metabolite
5-Hydroxyindole does not have a single specific pharmacological target. Instead, it is studied for its ability to inhibit ferroptosis, a form of regulated cell death driven by lipid peroxidation. The compound functions as a radical-trapping antioxidant (RTA). Structure-activity relationship studies indicate that while 5-HI inhibits ferroptosis, other isomers like 3-hydroxyindole are more potent. Its targets are the lipid peroxyl radicals responsible for membrane oxidative damage. |
|---|---|
| ln Vitro |
In vitro, 5-Hydroxyindole (5-HI) exhibits protective activity against oxidative stress-induced cell death. In studies using HT-22 mouse hippocampal neurons and N27 rat dopaminergic neurons, 5-HI was shown to inhibit ferroptosis induced by erastin, RSL3, and FINO2. Cytotoxicity was measured via calcein AM, MTT, and LDH release assays. 5-HI was found to be less effective than 3-hydroxyindole but still significantly reduced lipid peroxidation, as measured by the ABTS radical-trapping assay.
|
| ln Vivo |
In vivo activity studies for 5-Hydroxyindole itself are less common than for its derivatives (serotonin or melatonin). However, based on cell culture models showing inhibition of neuronal ferroptosis, 5-HI is hypothesized to provide neuroprotection in animal models of neurodegenerative diseases such as Parkinson's or Alzheimer's. It acts as a radical-trapping antioxidant to prevent the accumulation of phospholipid peroxides, which are key drivers of ferroptosis in brain tissue. Animal studies typically use rodent models of oxidative stress.
|
| Enzyme Assay |
For non-cell assays, the radical-trapping antioxidant activity of 5-Hydroxyindole is measured using the ABTS (2,2'-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid)) decolorization assay. A solution of ABTS is reacted with potassium persulfate to generate the ABTS radical cation. 5-HI is added at various concentrations, and the decrease in absorbance at 734 nm is monitored over time. The Trolox equivalent antioxidant capacity (TEAC) is calculated. This assay directly measures the ability of 5-HI to scavenge free radicals independently of cellular machinery.
|
| Cell Assay |
Standard protocols for assessing ferroptosis inhibition involve seeding HT-22 cells in 96-well plates (10,000 cells/well) in DMEM supplemented with 10% FBS. After 24 hours, cells are pre-treated with 5-Hydroxyindole (e.g., 10-100 uM) for 1 hour, followed by co-treatment with ferroptosis inducers (erastin 1 uM, RSL3 0.1 uM, or FINO2 5 uM) for 24 hours. Cell viability is measured using Calcein-AM staining (live cells) or LDH release assay (cytotoxicity). Intracellular glutathione levels are measured using monochlorobimane fluorescence.
|
| Animal Protocol |
In vivo animal protocols typically use C57BL/6 mice. To study neuroprotection, 5-Hydroxyindole is administered via intraperitoneal (IP) injection (e.g., 10-30 mg/kg) daily for 7-14 days. Ferroptosis is induced by stereotaxic injection of erastin or RSL3 into the hippocampus or by using genetic models. Behavioral tests (Morris water maze for memory, rotarod for motor function) are performed. Brains are harvested post-mortem for analysis of lipid peroxidation markers (malondialdehyde, 4-HNE) and histology.
|
| ADME/Pharmacokinetics |
Pharmacokinetic properties of 5-Hydroxyindole are extrapolated from its analogs. It is likely rapidly absorbed and distributed due to its small, lipophilic structure. It can cross the blood-brain barrier (BBB) given that serotonin metabolites are found in the CNS. The compound is a substrate for monoamine oxidase (MAO) and aldehyde dehydrogenase, leading to the production of 5-hydroxyindoleacetic acid (5-HIAA), the major urinary metabolite. Plasma half-life in rodents is expected to be short (30-60 minutes).
|
| Toxicity/Toxicokinetics |
Toxicology data for 5-Hydroxyindole is not extensive for pharmaceutical use. Based on its structural similarity to indoles, it is likely an irritant to skin, eyes, and respiratory tract. There is no evidence of mutagenicity in standard Ames tests for simple hydroxyindoles. High doses may cause central nervous system depression. Standard handling precautions (gloves, lab coat) are required. It is not a controlled substance.
|
| References | |
| Additional Infomation |
5-Hydroxyindole belongs to the hydroxyindole class of compounds, specifically 1H-indole, where the hydrogen at the 5-position is replaced by a hydroxyl group. It is a human metabolite. Reports have indicated that 5-hydroxyindole is present in Ligusticum striatum, Solanum lycopersicum, and Ligusticum chuanxiong, and relevant data are available for reference.
5-Hydroxyindole is not a drug; it is a biochemical research tool. It has no FDA approval or ongoing clinical trials for therapeutic use. Its primary research applications are in the study of ferroptosis and neuroprotection. The compound is significant as a precursor and metabolite in the serotonin pathway. In diagnostic medicine, 5-HIAA (the acetic acid derivative) is a well-established urinary biomarker for carcinoid tumors, but 5-Hydroxyindole itself is not used clinically. |
| Molecular Formula |
C8H7NO
|
|---|---|
| Molecular Weight |
133.15
|
| Exact Mass |
133.052
|
| CAS # |
1953-54-4
|
| PubChem CID |
16054
|
| Appearance |
Off-white to pink solid
|
| Density |
1.3±0.1 g/cm3
|
| Boiling Point |
343.2±15.0 °C at 760 mmHg
|
| Melting Point |
105-110ºC
|
| Flash Point |
161.4±20.4 °C
|
| Vapour Pressure |
0.0±0.8 mmHg at 25°C
|
| Index of Refraction |
1.739
|
| LogP |
0.97
|
| Hydrogen Bond Donor Count |
2
|
| Hydrogen Bond Acceptor Count |
1
|
| Rotatable Bond Count |
0
|
| Heavy Atom Count |
10
|
| Complexity |
126
|
| Defined Atom Stereocenter Count |
0
|
| SMILES |
O([H])C1C([H])=C([H])C2C([H])=C([H])N([H])C=2C=1[H]
|
| InChi Key |
LMIQERWZRIFWNZ-UHFFFAOYSA-N
|
| InChi Code |
InChI=1S/C8H7NO/c10-7-1-2-8-6(5-7)3-4-9-8/h1-5,9-10H
|
| Chemical Name |
1H-indol-5-ol
|
| HS Tariff Code |
2934.99.9001
|
| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
|
| Solubility (In Vitro) |
DMSO :~50 mg/mL (~375.52 mM)
|
|---|---|
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (18.78 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.5 mg/mL (18.78 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 7.5103 mL | 37.5516 mL | 75.1033 mL | |
| 5 mM | 1.5021 mL | 7.5103 mL | 15.0207 mL | |
| 10 mM | 0.7510 mL | 3.7552 mL | 7.5103 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
Products are for research use only; We do not sell to patients
Copyright 2020 InvivoChem LLC | All Rights Reserved
