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| Targets |
As a stable isotope-labeled amino acid, 2-Amino-3-mercaptopropanoic acid-d2 is not intended for use as a therapeutic agent and therefore does not have a pharmacological target. Its utility is derived from its chemical identity as an analog of cysteine. Cysteine is a proteinogenic amino acid with a thiol side chain that plays crucial roles in protein structure, enzyme catalysis, and redox homeostasis as a precursor to the antioxidant glutathione. In analytical chemistry, the labeled version (d2) behaves identically to the unlabeled counterpart during sample preparation and chromatography, but is differentiated by mass spectrometry, allowing it to serve as a quantitative reference or tracer.
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| ln Vitro |
Stable heavy isotopes of hydrogen, carbon, and other elements have been incorporated into drug molecules, largely as tracers for quantitation during the drug development process. Studies involving the human use of drugs labeled with deuterium suggest that these compounds may offer some advantages when compared with their nondeuterated counterparts. Deuteration has gained attention because of its potential to affect the pharmacokinetic and metabolic profiles of drugs. Deutetrabenazine is the first deuterated drug to receive Food and Drug Administration approval. This deuterated form of the drug tetrabenazine is indicated for the treatment of chorea associated with Huntington's disease as well as tardive dyskinesia. Ongoing clinical trials suggest that a number of other deuterated compounds are being evaluated for the treatment of human diseases and not merely as research tools.
2-Amino-3-mercaptopropanoic acid-d2 possesses the same chemical reactivity as natural cysteine but is not evaluated for classic drug-like bioactivity. It can participate in all biochemical reactions involving cysteine, such as disulfide bond formation and conjugation reactions. In an analytical context, the compound is used to validate the performance of LC-MS/MS assays. For example, it is added to calibration standards and quality control samples to correct for matrix effects, ion suppression, and recovery variability during sample preparation. It can also act as a tracer in metabolic studies, allowing researchers to follow the fate of cysteine through the transsulfuration or glutathione biosynthesis pathways by detecting the deuterium-labeled metabolites. |
| ln Vivo |
Deuterated compounds may, in some cases, offer advantages over nondeuterated forms, often through alterations in clearance. Deuteration may also redirect metabolic pathways in directions that reduce toxicities. The approval of additional deuterated compounds may soon follow. Clinicians will need to be familiar with the dosing, efficacy, potential side effects, and unique metabolic profiles of these new entities.
As a labeled internal standard, 2-Amino-3-mercaptopropanoic acid-d2 is not used for in vivo efficacy studies. However, the unlabeled parent compound, cysteine, is crucial in numerous physiological processes. It is a precursor to the antioxidant glutathione, which protects cells from oxidative damage. Cysteine also plays a role in the metabolism of methionine and taurine. While the labeled version is not administered as a therapeutic, it could be used as a metabolic tracer in animal models of disease. For instance, a deuterated cysteine tracer could be infused into a rodent model of liver disease, and blood samples could be analyzed to measure the turnover rate of glutathione, providing insights into the pathophysiology of the disease. |
| Enzyme Assay |
2-Amino-3-mercaptopropanoic acid-d2 is not designed for use in traditional enzyme or receptor binding assays. However, it is an essential tool for the analytical support of such assays. For an in vitro binding assay that requires measurement of cysteine or glutathione levels as an endpoint, the labeled compound can be used as an internal standard. The protocol involves adding a known, fixed amount of the deuterated standard (e.g., 2-Amino-3-mercaptopropanoic acid-d2) to the biological sample after the assay has been terminated. The sample is then processed and analyzed by LC-MS/MS. The ratio of the signal from the endogenous unlabeled analyte to the exogenous labeled standard is used to calculate the absolute concentration of the analyte via a calibration curve.
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| Cell Assay |
The labeled standard is not used as a treatment in cell-based assays. Instead, it is employed for the quantification of cysteine metabolism in cellular models. For a cell study investigating oxidative stress, cells (e.g., HepG2 hepatocytes) are treated with a test compound. After incubation, the cells are lysed, and a fixed amount of 2-Amino-3-mercaptopropanoic acid-d2 is spiked into the lysate as an internal standard. The lysate is then derivatized (if necessary) and analyzed by LC-MS/MS. The mass spectrometer monitors the transitions for unlabeled cysteine and the deuterated standard. This allows for highly accurate quantification of the intracellular cysteine or glutathione concentrations in the treated cells versus the control cells, providing a precise readout of the test compound's effect on redox balance.
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| Animal Protocol |
2-Amino-3-mercaptopropanoic acid-d2 is not used in animal procedures as a test article. It is added during the sample processing stage of an animal study. For a toxicology study in which plasma cysteine levels are a biomarker, blood collected from the animal is spiked with a known amount of the deuterated internal standard. The sample is then deproteinized, and the supernatant is analyzed by LC-MS/MS. The use of the isotopic internal standard corrects for any losses of analyte during the multi-step sample preparation process. This provides the highest degree of accuracy and precision for determining the concentration of the endogenous biomarker, enabling researchers to draw reliable conclusions about the compound‘s effect on the animal. This is a standard practice in regulated bioanalysis.
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| ADME/Pharmacokinetics |
As a labeled standard, 2-Amino-3-mercaptopropanoic acid-d2 does not require separate pharmacokinetic characterization. If it were administered in vivo, its ADME properties would be identical to those of unlabeled cysteine. Cysteine is a naturally occurring amino acid that is absorbed from the gut via amino acid transporters. It is rapidly metabolized, primarily through pathways leading to glutathione, taurine, and inorganic sulfate. Its plasma half-life is short. It can be synthesized endogenously from methionine via the transsulfuration pathway. Cysteine levels are tightly regulated, and excess is efficiently excreted in urine. The deuterium label is stable and does not alter these processes.
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| Toxicity/Toxicokinetics |
The toxicity of 2-Amino-3-mercaptopropanoic acid-d2 is analogous to that of cysteine itself, which is Generally Recognized as Safe (GRAS) at normal physiological concentrations. However, the compound is an amino acid and is not considered a hazardous material for standard laboratory handling. At supraphysiological doses, cysteine can be nephrotoxic, particularly in animal models of metabolic disease. The deuterated version is supplied as a high-purity powder. Standard safety precautions for handling fine chemicals apply, including the use of gloves, a lab coat, and eye protection. It should be stored at -20degC in a sealed container, protected from moisture and light, to maintain its stability and prevent oxidation of the thiol group.
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| References | |
| Additional Infomation |
The compound has CAS number 124051-54-3. It is also known as DL-Cysteine (3,3-D2) and 3,3-dideutero-DL-cysteine. Its molecular formula is C3H5D2NO2S, and its molecular weight is approximately 123.17 g/mol. It appears as a white to off-white powder with a melting point of about 225degC (decomposes). It should be stored as a powder at -20degC under an inert atmosphere to prevent oxidation. It is soluble in water with the aid of a small amount of hydrochloric acid to help dissolve it. It is intended for research use only.
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| Molecular Formula |
C3H5D2NO2S
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| Molecular Weight |
123.17
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| Exact Mass |
123.032
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| CAS # |
124051-54-3
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| Related CAS # |
2-Amino-3-mercaptopropanoic acid
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| PubChem CID |
12219650
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| Appearance |
Typically exists as solids at room temperature
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| Hydrogen Bond Donor Count |
3
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| Rotatable Bond Count |
2
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| Heavy Atom Count |
7
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| Complexity |
75.3
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| Defined Atom Stereocenter Count |
0
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| SMILES |
[2H]C([2H])(C(C(=O)O)N)S
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| InChi Key |
XUJNEKJLAYXESH-DICFDUPASA-N
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| InChi Code |
InChI=1S/C3H7NO2S/c4-2(1-7)3(5)6/h2,7H,1,4H2,(H,5,6)/i1D2
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| Chemical Name |
2-amino-3,3-dideuterio-3-sulfanylpropanoic 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 | 8.1189 mL | 40.5943 mL | 81.1886 mL | |
| 5 mM | 1.6238 mL | 8.1189 mL | 16.2377 mL | |
| 10 mM | 0.8119 mL | 4.0594 mL | 8.1189 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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