| Size | Price | Stock | Qty |
|---|---|---|---|
| 50mg |
|
| Targets |
Not applicable as a drug. 5-Hydroxytryptophol is an endogenous metabolite of serotonin (5-HT). It does not have a defined therapeutic target with IC50 or Ki values. Its formation is catalyzed by alcohol dehydrogenase (ADH, EC 1.1.1.1), which reduces the intermediate 5-hydroxyindoleacetaldehyde (5-HIAL) to 5-HTOL. This pathway is favored under conditions of elevated NADH/NAD+ ratio, such as during ethanol metabolism [1].
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|---|---|
| ln Vitro |
Enzymatic Formation: In vitro studies using rat tissue homogenates demonstrated that the presence of ethanol leads to increased formation of 5-HTOL. Tissues such as kidney, lung, and the gastrointestinal tract, in addition to the liver, were shown to contribute to this elevated production during ethanol oxidation [1].
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| ln Vivo |
Response to Ethanol Ingestion: In humans, intake of ethanol causes a dramatic, dose-dependent increase in the urinary excretion of 5-HTOL. This elevation persists for 5-15 hours after ethanol has been completely eliminated from the blood, providing a detection window for recent alcohol consumption of approximately 24 hours. An intake of more than 0.1 g/kg (approximately >7-10 g) of ethanol is typically required to produce a measurable elevation in a urine sample collected the following morning [1].
Correlation with Symptoms: In a study with healthy social drinkers, a dose-dependent association was observed between urinary 5-HTOL levels and self-reported hangover symptoms (headache and nausea) the morning after evening alcohol intake (50 or 80 g ethanol over 2 hours) [1]. Effect of Disulfiram: Treatment with disulfiram (Antabuse), an aldehyde dehydrogenase (ALDH) inhibitor, leads to a sustained elevation in the baseline urinary 5-HTOL/5-HIAA ratio due to the inhibition of 5-HIAA formation and a consequent shift towards 5-HTOL production [1]. Species Distribution: The urinary excretion pattern of 5-HTOL relative to 5-HIAA varies considerably across species. Among the species studied, monkey, ferret, hamster, and rabbit showed a baseline ratio most similar to that of humans [1]. |
| Enzyme Assay |
Alcohol Dehydrogenase (ADH) Activity Assay: The role of human alcohol dehydrogenases (ADH) in the metabolism of serotonin was investigated. It was found that class I ADH is the main enzyme responsible for the reduction of 5-hydroxyindoleacetaldehyde (5-HIAL) to 5-HTOL. The enzyme's activity in this reductive direction is approximately 30 times higher than its activity in the oxidation of 5-HTOL back to 5-HIAL. The reaction is highly dependent on the concentration of the cofactor NADH [1].
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| Animal Protocol |
Tissue Distribution Study in Rats:** Male Sprague-Dawley rats were administered ethanol. At various time points, tissues including liver, kidney, lung, and gastrointestinal tract were collected, and homogenates were prepared. The formation of 5-HTOL in these homogenates was measured to identify the peripheral organs contributing to its increased production during ethanol oxidation [1].
Tissue Distribution Study in Rats: Male Sprague-Dawley rats were administered ethanol. At various time points, tissues including liver, kidney, lung, and gastrointestinal tract were collected, and homogenates were prepared. The formation of 5-HTOL in these homogenates was measured to identify the peripheral organs contributing to its increased production during ethanol oxidation [1]. |
| ADME/Pharmacokinetics |
Metabolism and Excretion: 5-Hydroxytryptophol is an endogenous metabolite of serotonin. It is formed primarily in peripheral organs (intestine, kidney, liver, lung) via the reduction of 5-hydroxyindoleacetaldehyde (5-HIAL) by alcohol dehydrogenase (ADH). Under normal physiological conditions, it is a minor metabolite compared to 5-hydroxyindoleacetic acid (5-HIAA). 5-HTOL is almost entirely (>96%) conjugated in the body before urinary excretion, primarily with glucuronic acid (about 80% as 5-HTOL glucuronide) and to a lesser extent with sulfuric acid. Only a small fraction (about 4%) is excreted as the free (unconjugated) form [1].
Pharmacokinetics in Humans: Following ethanol intake, the urinary excretion of total 5-HTOL increases dramatically. The elevated levels peak several hours after ethanol consumption and decline with an apparent half-life longer than that of ethanol, taking 5-15 hours to return to baseline after ethanol has been eliminated. The response is dose-dependent and highly reproducible [1]. |
| Toxicity/Toxicokinetics |
The literature mentions that administration of tryptophols, including 5-HTOL, to laboratory animals induces sleep. It has also been suggested that 5-HTOL might be involved in provoking adverse physiological symptoms (e.g., diarrhea, headache, fatigue) when a dietary load of serotonin is combined with alcohol ingestion. Additionally, 5-HTOL has been shown to elicit contractions in isolated cerebral arteries by activating serotonergic receptors [1].
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| References | |
| Additional Infomation |
5-Hydroxytryptophanol is an indole compound. It has been reported that 5-hydroxytryptophanol has been detected in the erect mouse-eared bat (Hyrtios erectus), and relevant data are available. 5-Hydroxyindole-3-ethanol.
5-Hydroxytryptophol (5-HTOL) is an endogenous minor metabolite of serotonin. Its primary significance in this paper is as a highly sensitive and specific clinical biomarker for detecting recent alcohol consumption. The measurement of the urinary 5-HTOL/5-HIAA ratio is used to compensate for urine dilution and dietary serotonin intake. A molar ratio above 15 nmol/μmol (or 0.015) is indicative of alcohol intake within the past 24 hours. This biomarker has numerous clinical and forensic applications, including monitoring alcohol relapse in outpatient treatment programs (e.g., for methadone patients), objective evaluation of treatment efforts, detecting high-risk patients in elective surgery, monitoring disulfiram therapy, and distinguishing ingested ethanol from post-sampling microbial artefactual formation in forensic toxicology cases [1]. |
| Molecular Formula |
C10H11NO2
|
|---|---|
| Molecular Weight |
177.2
|
| Exact Mass |
177.078
|
| CAS # |
154-02-9
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| PubChem CID |
9061
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| Appearance |
Yellow to brown solid powder
|
| Density |
1.4±0.1 g/cm3
|
| Boiling Point |
435.2±30.0 °C at 760 mmHg
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| Flash Point |
217.0±24.6 °C
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| Vapour Pressure |
0.0±1.1 mmHg at 25°C
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| Index of Refraction |
1.718
|
| LogP |
0.11
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| Hydrogen Bond Donor Count |
3
|
| Hydrogen Bond Acceptor Count |
2
|
| Rotatable Bond Count |
2
|
| Heavy Atom Count |
13
|
| Complexity |
174
|
| Defined Atom Stereocenter Count |
0
|
| InChi Key |
KQROHCSYOGBQGJ-UHFFFAOYSA-N
|
| InChi Code |
InChI=1S/C10H11NO2/c12-4-3-7-6-11-10-2-1-8(13)5-9(7)10/h1-2,5-6,11-13H,3-4H2
|
| Chemical Name |
3-(2-hydroxyethyl)-1H-indol-5-ol
|
| Synonyms |
Stichoposide Holotoxins Stichoposide A
|
| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month Note: (1). This product requires protection from light (avoid light exposure) during transportation and storage. (2). Please store this product in a sealed and protected environment (e.g. under nitrogen), avoid exposure to moisture. |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
DMSO : ~125 mg/mL (~705.42 mM)
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|---|---|
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.08 mg/mL (11.74 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 20.8 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: ≥ 2.08 mg/mL (11.74 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 20.8 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. View More
Solubility in Formulation 3: ≥ 2.08 mg/mL (11.74 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 5.6433 mL | 28.2167 mL | 56.4334 mL | |
| 5 mM | 1.1287 mL | 5.6433 mL | 11.2867 mL | |
| 10 mM | 0.5643 mL | 2.8217 mL | 5.6433 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.
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