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| Targets |
5-Hydroxytryptophol (non-deuterated) is a metabolite of serotonin; it does not have a specific drug target but is used as a biomarker. The parent compound, serotonin (5-HT), targets 5-HT receptors (a family of G protein-coupled receptors and ligand-gated ion channels). 5-Hydroxytryptophol is formed from serotonin via the intermediate 5-hydroxyindoleacetaldehyde by the action of alcohol dehydrogenase (ADH) or aldehyde reductase. The levels of 5-hydroxytryptophol reflect serotonin turnover and alcohol metabolism. The deuterated version (5-Hydroxytryptophol-d4) is used as an internal standard for quantification, not for activity studies.
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| ln Vitro |
Drug compounds have included stable heavy isotopes of carbon, hydrogen, and other elements, mostly as quantitative tracers while the drugs were being developed. Because deuteration may have an effect on a drug's pharmacokinetics and metabolic properties, it is a cause for concern [1].
5-Hydroxytryptophol-d4 is not used for in vitro activity studies; it serves exclusively as an analytical internal standard. The non-deuterated parent compound, 5-hydroxytryptophol, is used in cell culture studies of serotonin metabolism. When cells that metabolize serotonin (e.g., neuronal cells, platelets, or enterochromaffin cells) are treated with serotonin (1-100 uM), 5-hydroxytryptophol can be detected in culture medium. The compound can also be produced in vitro by incubating serotonin with MAO and alcohol dehydrogenase. Its formation is used as a marker of serotonin turnover. The deuterated version is not used in these activity assays; its sole purpose is analytical quantification. |
| ln Vivo |
In vivo, 5-hydroxytryptophol (non-deuterated) is a naturally occurring metabolite of serotonin that is excreted in human urine. Its levels in urine and blood increase significantly after acute alcohol ingestion, making it a sensitive and specific marker for recent alcohol consumption. The ratio of 5-hydroxytryptophol to 5-hydroxyindoleacetic acid (5-HIAA, the major serotonin metabolite) is used as a biomarker for alcohol consumption, as alcohol shifts serotonin metabolism from the oxidative pathway (to 5-HIAA) toward the reductive pathway (to 5-hydroxytryptophol). The deuterated version (5-Hydroxytryptophol-d4) is not used for in vivo efficacy studies; it is used as an internal standard to quantify 5-hydroxytryptophol levels in biological samples.
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| Enzyme Assay |
For non-cellular assays (analytical quantification), 5-Hydroxytryptophol-d4 is prepared as a stock solution in methanol or acetonitrile (1 mg/mL). For LC-MS/MS analysis, a calibration curve for 5-hydroxytryptophol is prepared in human urine or plasma (0.1-1000 ng/mL) with a fixed concentration of 5-Hydroxytryptophol-d4 (e.g., 10-50 ng/mL). Sample preparation: 500 uL urine or plasma + 50 uL internal standard + 1 mL ethyl acetate for liquid-liquid extraction. After vortexing and centrifugation, the organic layer is evaporated to dryness, reconstituted in 100 uL mobile phase (0.1% formic acid in water and acetonitrile, 90:10, v/v), and injected onto a C18 column (2.1×100 mm, 1.8 um). MRM transitions: 5-hydroxytryptophol 178→160, 5-Hydroxytryptophol-d4 182→164.
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| Cell Assay |
For cell-based assays, neuronal cell lines (e.g., SH-SY5Y, PC12 cells) or serotonin-producing cells (e.g., RBL-2H3 basophilic leukemia cells) are seeded in 6-well plates (1×10⁶ cells/well) in DMEM with 10% FBS. For serotonin metabolism studies, cells are treated with serotonin (1-100 uM) for 1-24 hours. Cell culture medium is collected, and 5-hydroxytryptophol levels are measured by LC-MS/MS using 5-Hydroxytryptophol-d4 as internal standard. For studies of alcohol effects, cells are co-treated with ethanol (10-100 mM) to increase conversion of serotonin to 5-hydroxytryptophol relative to 5-HIAA. Cell viability is assessed by MTT assay. Cell lysates can also be analyzed for the ratio of 5-hydroxytryptophol to 5-HIAA.
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| Animal Protocol |
For in vivo animal experiments, rodent models are used to study alcohol-induced changes in serotonin metabolism. Rats or mice are administered ethanol (1-4 g/kg, intraperitoneally or orally by gavage). Urine samples are collected at multiple time points (0-24 hours) in metabolic cages. Blood samples are collected from the tail vein or by cardiac puncture. 5-Hydroxytryptophol and 5-HIAA levels are measured by LC-MS/MS using 5-Hydroxytryptophol-d4 as internal standard. The 5-hydroxytryptophol to 5-HIAA ratio is calculated and used as a biomarker of acute alcohol consumption. In some studies, deuterated 5-hydroxytryptophol can be administered intravenously as a tracer for pharmacokinetic studies.
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| ADME/Pharmacokinetics |
5-Hydroxytryptophol-d4 has a molecular weight of 181.22. The compound is a solid with a light brown to brown appearance. It is soluble in DMSO, methanol, and ethanol. The deuterium labeling (four deuterium atoms) provides a mass shift of +4 Da, enabling clear differentiation from endogenous non-deuterated 5-hydroxytryptophol in mass spectrometry. The compound should be stored as a powder at -20degC for up to 3 years. In solution, it is stable at -80degC for up to 6 months and at -20degC for up to 1 month. Protect from light during storage as indole derivatives can be light-sensitive.
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| Toxicity/Toxicokinetics |
5-Hydroxytryptophol-d4 is a stable isotope-labeled compound with minimal toxicity at analytical concentrations (ng-ug per sample). The non-deuterated parent compound, 5-hydroxytryptophol, is an endogenous serotonin metabolite present in human urine at low concentrations. It is generally non-toxic at physiological levels. No toxicity studies have been reported for the deuterated version. Standard laboratory safety precautions for handling organic compounds should be followed. The compound is non-radioactive and safe for use in research laboratories.
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| References | |
| Additional Infomation |
5-Hydroxytryptophol-d4 is an analytical standard and research tool, not an approved drug. No clinical trials have been conducted with the deuterated version for therapeutic purposes. The non-deuterated parent compound, 5-hydroxytryptophol, is used as a clinical biomarker for acute alcohol consumption, particularly in forensic toxicology and alcohol abstinence monitoring, as well as in studies of alcoholism and relapse prevention. It is also used in neuropharmacology research to study serotonin metabolism, monoamine oxidase activity, and sleep regulation. The deuterated version is used as an internal standard for quantitative LC-MS/MS analysis of 5-hydroxytryptophol in clinical and research settings. It is not intended for human therapeutic use.
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| Molecular Formula |
C10H7D4NO2
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| Molecular Weight |
181.22
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| Exact Mass |
177.079
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| CAS # |
66640-87-7
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| Related CAS # |
5-Hydroxytryptophol;154-02-9
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| PubChem CID |
71749399
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| Appearance |
Light brown to brown solid powder
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| LogP |
1.408
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| Hydrogen Bond Donor Count |
3
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| Hydrogen Bond Acceptor Count |
2
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| Rotatable Bond Count |
2
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| Heavy Atom Count |
13
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| Complexity |
174
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| Defined Atom Stereocenter Count |
0
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| SMILES |
[2H]C([2H])(C1=CNC2=C1C=C(C=C2)O)C([2H])([2H])O
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| InChi Key |
KQROHCSYOGBQGJ-KHORGVISSA-N
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| 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/i3D2,4D2
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| Chemical Name |
3-(1,1,2,2-tetradeuterio-2-hydroxyethyl)-1H-indol-5-ol
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| 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 |
| 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) |
May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples
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| Solubility (In Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.
Injection Formulations
Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)(e.g. IP/IV/IM/SC) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). View More
Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). View More
Oral Formulation 3: Dissolved in PEG400 (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 5.5182 mL | 27.5908 mL | 55.1815 mL | |
| 5 mM | 1.1036 mL | 5.5182 mL | 11.0363 mL | |
| 10 mM | 0.5518 mL | 2.7591 mL | 5.5182 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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