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| Targets |
As a stable isotope-labeled compound, Homovanillic acid-d5 does not exert pharmacological effects through traditional target binding. Instead, its "target" is the analytical method in which it is used as a reference standard. The compound is designed to have identical chemical properties to unlabeled homovanillic acid but with a distinct mass due to the presence of five deuterium atoms. This allows it to co-elute with unlabeled homovanillic acid in chromatographic separation while being distinguishable by mass spectrometry. Homovanillic acid itself is a dopamine metabolite that is used as a biomarker for dopamine turnover and neuroendocrine tumors. It has been associated with aromatic amino acid decarboxylase deficiency, celiac disease, growth hormone deficiency, and sepiapterin reductase deficiency. The d5-labeled version of homovanillic acid enables researchers to accurately quantify homovanillic acid levels in biological samples, providing a tool for studying catecholamine metabolism and neurochemical pathways.
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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, Homovanillic acid-d5 is used as an internal standard for the quantification of homovanillic acid in biological samples by LC-MS/MS. The compound is added to samples at known concentrations prior to sample preparation to correct for matrix effects, extraction efficiency, and instrument variability. The deuterium labeling ensures that the compound can be distinguished from endogenous homovanillic acid in mass spectrometry-based assays, allowing for accurate quantification even in complex biological matrices. The compound is typically dissolved in appropriate solvents (e.g., methanol, DMSO) to prepare stock and working solutions for analytical applications. In method development and validation studies, Homovanillic acid-d5 is used to assess the accuracy, precision, and robustness of analytical methods for homovanillic acid quantification. The compound's chemical properties are identical to those of unlabeled homovanillic acid, ensuring that it behaves identically during sample preparation and chromatographic separation. |
| ln Vivo |
In vivo, Homovanillic acid-d5 enables precise tracking of homovanillic acid metabolism in complex biological systems. Following administration to animals or humans, the compound can be detected in biological fluids using mass spectrometry, allowing researchers to study the metabolism and excretion of homovanillic acid. The deuterium label ensures that the administered compound can be distinguished from endogenous homovanillic acid, enabling accurate pharmacokinetic and metabolic studies. Homovanillic acid is a dopamine metabolite that is used as a biomarker for dopamine turnover and neuroendocrine tumors. The d5-labeled version of homovanillic acid can be used to study the kinetics of homovanillic acid formation and excretion, as well as the factors that influence its levels in the body. In clinical research, Homovanillic acid-d5 may be used in stable isotope tracer studies to assess dopamine metabolism and neuroendocrine function.
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| Enzyme Assay |
In vitro enzyme assays for Homovanillic acid-d5 are not typically performed, as the compound is primarily used as an analytical standard. However, the compound can be used in enzymatic assays to study the activity of enzymes involved in dopamine metabolism, such as monoamine oxidase (MAO) and catechol-O-methyltransferase (COMT). In these assays, the enzyme is incubated with dopamine or other substrates, and the formation of homovanillic acid is measured. Homovanillic acid-d5 can be used as an internal standard to quantify the formation of homovanillic acid in these assays. The compound's chemical properties are identical to those of unlabeled homovanillic acid, ensuring that it behaves identically in biochemical assays. Typical assay conditions include incubation at 25-37°C in appropriate buffer systems, with reaction products measured by mass spectrometry.
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| Cell Assay |
In vitro cell-based experiments with Homovanillic acid-d5 involve adding the labeled compound to cell culture media and studying its uptake and metabolism. Cells are cultured in standard growth media, and Homovanillic acid-d5 is added at various concentrations for varying periods. 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 homovanillic acid and its metabolites. This allows researchers to quantify homovanillic acid uptake, metabolism, and excretion in cell models. In studies of dopamine metabolism, Homovanillic acid-d5 can be used to assess the activity of MAO and COMT in cell culture systems. 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.
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| Animal Protocol |
In vivo animal experiments with Homovanillic acid-d5 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 1-100 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 homovanillic acid in the circulation. Urine samples are also collected to study the excretion of homovanillic acid and its metabolites. At the end of the experiment, animals are euthanized, and tissues (liver, kidney, brain) are collected for analysis. Metabolites are extracted from plasma, urine, and tissues, and the deuterium enrichment of homovanillic acid and its metabolites is measured by LC-MS/MS. This allows researchers to quantify homovanillic acid metabolism in different organs and tissues, assess the impact of disease states on homovanillic acid homeostasis, 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 DMSO, in which it is soluble.
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| ADME/Pharmacokinetics |
The pharmacokinetic properties of Homovanillic acid-d5 are studied using the isotope label to track the absorption, distribution, metabolism, and excretion of homovanillic acid. Following oral or intravenous administration, the compound is rapidly absorbed and distributed to tissues. The deuterium label allows for the specific detection of administered homovanillic acid in biological samples without interference from endogenous unlabeled homovanillic acid. Pharmacokinetic parameters such as half-life, volume of distribution, clearance, and bioavailability can be calculated from the concentration-time profiles of labeled homovanillic acid in plasma and urine. Homovanillic acid is a dopamine metabolite that is used as a biomarker for dopamine turnover. The labeled compound enables precise tracking of these metabolic processes. The pharmacokinetics of Homovanillic acid-d5 are expected to be similar to those of unlabeled homovanillic acid, with rapid distribution and elimination.
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| Toxicity/Toxicokinetics |
The toxicological profile of Homovanillic acid-d5 is consistent with that of unlabeled homovanillic acid, a dopamine metabolite that is naturally present in the body. Homovanillic acid is a normal component of urine and is generally considered non-toxic at physiological concentrations. 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.
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| References | |
| Additional Infomation |
Homovanillic acid-d5 is a valuable research tool for analytical chemistry, neurochemical research, and pharmacokinetics. It is the deuterated form of homovanillic acid, a dopamine metabolite. Homovanillic acid-d5 has the molecular formula C₉H₅D₅O₄ and a molecular weight of 187.20 g/mol. Homovanillic acid is a dopamine metabolite that has been associated with aromatic amino acid decarboxylase deficiency, celiac disease, growth hormone deficiency, and sepiapterin reductase deficiency. The compound is a labeled metabolite of dihydroxyphenylacetic acid and a neuroendocrine tumor marker. It is crucial for studies involving catecholamine metabolism, neurochemical pathway analysis, and pharmacokinetics. The compound is not a drug and is not approved for any clinical indication. It is strictly for research use only. Its role as a stable isotope-labeled internal standard makes it an essential tool for quantitative analysis of homovanillic acid in a variety of biological matrices.
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| Molecular Formula |
C9H5D5O4
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| Molecular Weight |
187.20
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| Exact Mass |
187.089
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| CAS # |
53587-32-9
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| Related CAS # |
Homovanillic acid;306-08-1
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| PubChem CID |
12347943
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| Appearance |
White to off-white solid powder
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| LogP |
1.027
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| Hydrogen Bond Donor Count |
2
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| Hydrogen Bond Acceptor Count |
4
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| Rotatable Bond Count |
3
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| Heavy Atom Count |
13
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| Complexity |
181
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| Defined Atom Stereocenter Count |
0
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| SMILES |
[2H]C1=C(C(=C(C(=C1C([2H])([2H])C(=O)O)[2H])OC)O)[2H]
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| InChi Key |
QRMZSPFSDQBLIX-DVHRWRHBSA-N
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| InChi Code |
InChI=1S/C9H10O4/c1-13-8-4-6(5-9(11)12)2-3-7(8)10/h2-4,10H,5H2,1H3,(H,11,12)/i2D,3D,4D,5D2
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| Chemical Name |
2,2-dideuterio-2-(2,3,6-trideuterio-4-hydroxy-5-methoxyphenyl)acetic 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 Note: Please store this product in a sealed and protected environment (e.g. under nitrogen), avoid exposure to moisture and light. |
| 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: 250 mg/mL (1335.47 mM)
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.08 mg/mL (11.11 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 (11.11 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 (11.11 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 | 5.3419 mL | 26.7094 mL | 53.4188 mL | |
| 5 mM | 1.0684 mL | 5.3419 mL | 10.6838 mL | |
| 10 mM | 0.5342 mL | 2.6709 mL | 5.3419 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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