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L-5-Hydroxytryptophan-d3 is the deuterium-labeled form of L-5-HTP, which is the immediate precursor of the neurotransmitter serotonin and a reserpine antagonist. The unlabeled compound is used to treat fibromyalgia, myoclonus, migraine, and cerebellar ataxia. As a precursor to serotonin, L-5-HTP targets the serotonergic system, increasing serotonin levels in the brain. Serotonin is a key neurotransmitter involved in mood regulation, sleep-wake cycles, and various other physiological functions. L-5-HTP is also a precursor to melatonin, which regulates circadian rhythms. The deuterated form, L-5-HTP-d3, does not exert pharmacological effects through traditional target binding but serves as a tracer for studying the metabolism and pharmacokinetics of L-5-HTP. The deuterium label allows for the specific detection of the compound in biological samples, enabling researchers to study the absorption, distribution, metabolism, and excretion of L-5-HTP. This makes L-5-HTP-d3 a valuable tool for drug development and for studying the role of serotonin in health and disease.
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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].
In vitro, L-5-Hydroxytryptophan-d3 is used as a tracer to study 5-HTP metabolism and its conversion into serotonin and melatonin. The compound is added to cell culture media or biochemical assay systems, and its metabolism is tracked by mass spectrometry. The deuterium label allows for the specific detection of the compound and its metabolites without interference from endogenous unlabeled compounds. In studies of serotonin biosynthesis, L-5-HTP-d3 is used as a substrate for aromatic L-amino acid decarboxylase (AADC), which converts L-5-HTP to serotonin. The formation of deuterated serotonin is measured by LC-MS/MS. In studies of melatonin synthesis, L-5-HTP-d3 is used to track the conversion of serotonin to melatonin via N-acetylation and O-methylation. The compound is also used as an internal standard for the quantification of L-5-HTP in biological samples. Its high purity (≥98%) and isotopic enrichment ensure accurate and reproducible results in these experiments. The compound is typically dissolved in appropriate solvents (e.g., water, methanol) for use in in vitro assays. |
| ln Vivo |
In vivo, L-5-Hydroxytryptophan-d3 is used as a tracer to study the pharmacokinetics and metabolism of L-5-HTP. Following administration to animals or humans, the compound is detected in biological fluids using mass spectrometry, allowing researchers to study the absorption, distribution, metabolism, and excretion of L-5-HTP. The deuterium label ensures that the administered compound can be distinguished from endogenous L-5-HTP, enabling accurate pharmacokinetic studies. In preclinical studies, L-5-HTP-d3 is administered to rodents via oral gavage or intraperitoneal injection, and blood and tissue samples are collected at various time points. The concentration of deuterated L-5-HTP and its metabolites (serotonin, melatonin) is measured by LC-MS/MS. This allows researchers to quantify the conversion of L-5-HTP to serotonin and melatonin in different tissues, assess the impact of disease states on serotonin metabolism, and evaluate the effects of pharmacological interventions. In clinical research, L-5-HTP-d3 may be used in stable isotope tracer studies to assess serotonin synthesis and turnover in humans. The compound's stability and well-characterized properties make it a reliable tool for in vivo metabolic studies.
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| Enzyme Assay |
In vitro enzyme and receptor binding assays for L-5-Hydroxytryptophan-d3 are not typically performed, as the compound is not a pharmacologically active agent in the traditional sense. Instead, the compound is used as a labeled substrate or internal standard in enzymatic assays. For example, in assays of aromatic L-amino acid decarboxylase (AADC) activity, L-5-HTP-d3 is used as a substrate, and the formation of deuterated serotonin is measured by LC-MS/MS. The enzyme is incubated with L-5-HTP-d3 and appropriate cofactors (e.g., pyridoxal phosphate) in a buffered solution at physiological pH and temperature. The reaction is terminated by the addition of acid or organic solvent, and the reaction products are analyzed by mass spectrometry. In assays of tryptophan hydroxylase, L-5-HTP-d3 can be used as a product standard or internal standard. In receptor binding assays, L-5-HTP-d3 is not typically used because it does not bind directly to receptors. However, it may be used to study the binding of L-5-HTP to transporters such as the large neutral amino acid transporter (LAT1). The compound's high purity and isotopic enrichment ensure accurate and reproducible results in these biochemical assays.
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| Cell Assay |
In vitro cell-based assays for L-5-Hydroxytryptophan-d3 involve adding the labeled compound to cell culture media and studying its uptake and metabolism. Cells that express aromatic L-amino acid decarboxylase (AADC) and tryptophan hydroxylase, such as neuronal cells or enterochromaffin cells, are cultured in appropriate medium. L-5-HTP-d3 is added at various concentrations (typically 1-100 μM) for varying periods (minutes to hours). Following incubation, cells and culture media are collected, and metabolites are extracted using appropriate methods. The extracts are then analyzed by LC-MS/MS to measure the deuterium-labeled L-5-HTP, serotonin, and melatonin. This allows researchers to quantify L-5-HTP uptake, conversion to serotonin and melatonin, and the effects of pharmacological interventions on these processes. Cell viability is routinely monitored to ensure that the labeled compound does not affect cell health. Each experiment includes appropriate controls (unlabeled cells, vehicle controls) and is performed in triplicate to ensure statistical reliability. The compound's high purity and isotopic enrichment ensure accurate and reproducible results in these experiments.
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| Animal Protocol |
In vivo animal experiments with L-5-Hydroxytryptophan-d3 involve administration of the labeled compound to animals followed by collection of biological samples for mass spectrometry analysis. The compound is typically administered via oral gavage, intraperitoneal injection, or intravenous infusion at doses ranging from 1-50 mg/kg. Following administration, blood samples are collected at various time points (typically 0, 0.5, 1, 2, 4, 8, 12, 24 hours) to measure the appearance and disappearance of labeled L-5-HTP in the circulation. At the end of the experiment, animals are euthanized, and tissues (brain, liver, kidney, gut) are collected for analysis. Metabolites are extracted from plasma and tissues, and the deuterium enrichment of L-5-HTP, serotonin, and melatonin is measured by LC-MS/MS. This allows researchers to quantify L-5-HTP metabolism in different organs and tissues, assess the impact of disease states on serotonin and melatonin synthesis, and evaluate the effects of pharmacological interventions. All animal procedures are conducted in accordance with institutional animal care and use committee guidelines, with appropriate sample sizes (typically n=4-6 per group) to ensure statistical power. The compound is formulated for administration using appropriate vehicles such as saline or water, in which it is soluble.
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| ADME/Pharmacokinetics |
The pharmacokinetic properties of L-5-Hydroxytryptophan-d3 are studied using the isotope label to track the absorption, distribution, metabolism, and excretion of L-5-HTP. Following oral or intravenous administration, the compound is rapidly absorbed and distributed to tissues, including the brain. The deuterium label allows for the specific detection of administered L-5-HTP in biological samples without interference from endogenous unlabeled L-5-HTP. Pharmacokinetic parameters such as half-life, volume of distribution, clearance, and bioavailability can be calculated from the concentration-time profiles of labeled L-5-HTP in plasma and tissues. L-5-HTP is well-absorbed and crosses the blood-brain barrier, where it is converted to serotonin. The compound is metabolized by aromatic L-amino acid decarboxylase (AADC) to serotonin, which is further metabolized to melatonin and other metabolites. The labeled compound enables precise tracking of these metabolic processes. The pharmacokinetics of L-5-HTP-d3 are expected to be similar to those of unlabeled L-5-HTP, with rapid absorption and elimination. The compound's high purity and isotopic enrichment ensure accurate pharmacokinetic measurements.
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| Toxicity/Toxicokinetics |
The toxicological profile of L-5-Hydroxytryptophan-d3 is consistent with that of unlabeled L-5-HTP, a naturally occurring amino acid and dietary supplement. L-5-HTP is generally well-tolerated when used as a dietary supplement, although it can cause gastrointestinal side effects at high doses. The deuterium label is a stable isotope that does not impart any additional toxicity to the compound. The compound is supplied as a high-purity research chemical for laboratory use only and is not intended for human consumption. Standard safety precautions should be observed when handling the compound, including the use of appropriate personal protective equipment. The compound should be stored in a cool, dry place, away from light and moisture. As with all chemicals, ingestion, inhalation, and skin contact should be avoided. The compound's safety profile is supported by the extensive use of L-5-HTP as a dietary supplement and the use of stable isotope-labeled compounds in research. There are no known adverse effects associated with the use of L-5-HTP-d3 at the concentrations typically used in research applications.
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| References |
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| Additional Infomation |
L-5-Hydroxytryptophan-d3 is a valuable research tool for studying serotonin and melatonin metabolism, neurotransmitter research, and drug development. It is used as a tracer to study 5-HTP metabolism and its conversion into serotonin and melatonin. L-5-HTP is a naturally occurring amino acid and a dietary supplement used as an antidepressant. It is the immediate precursor of the neurotransmitter serotonin and a reserpine antagonist. L-5-HTP is used to treat fibromyalgia, myoclonus, migraine, and cerebellar ataxia. The deuterated form, L-5-Hydroxytryptophan-d3, has the molecular formula C₁₁H₉D₃N₂O₃ and a molecular weight of 223.24 g/mol. The compound incorporates three deuterium atoms at the 4,6,7 positions of the indole ring. It is not a drug and is not approved for any clinical indication. It is strictly for research use only. Its high purity (≥98%) and isotopic enrichment ensure accurate and reproducible results in analytical applications. L-5-HTP-d3 is an essential tool for studying neurotransmitter metabolism, neurological disorders, and the role of serotonin in health and disease.
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| Molecular Formula |
C11H12N2O3
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| Molecular Weight |
223.243067741394
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| Exact Mass |
223.103
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| CAS # |
1276197-29-5
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| Related CAS # |
L-5-Hydroxytryptophan;4350-09-8;L-5-Hydroxytryptophan-d4;1246818-91-6
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| PubChem CID |
162642040
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| Appearance |
Gray to dark gray solid powder
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| LogP |
-1.2
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| Hydrogen Bond Donor Count |
4
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| Hydrogen Bond Acceptor Count |
4
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| Rotatable Bond Count |
3
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| Heavy Atom Count |
16
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| Complexity |
272
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| Defined Atom Stereocenter Count |
1
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| SMILES |
C(O)(=O)[C@H](CC1C2C(=C([2H])C([2H])=C(O)C=2[2H])NC=1)N
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| InChi Key |
LDCYZAJDBXYCGN-BSWQNAMISA-N
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| InChi Code |
InChI=1S/C11H12N2O3/c12-9(11(15)16)3-6-5-13-10-2-1-7(14)4-8(6)10/h1-2,4-5,9,13-14H,3,12H2,(H,15,16)/t9-/m0/s1/i1D,2D,4D
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| Chemical Name |
(2S)-2-amino-3-(4,6,7-trideuterio-5-hydroxy-1H-indol-3-yl)propanoic acid
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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 | 4.4795 mL | 22.3974 mL | 44.7948 mL | |
| 5 mM | 0.8959 mL | 4.4795 mL | 8.9590 mL | |
| 10 mM | 0.4479 mL | 2.2397 mL | 4.4795 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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