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| Targets |
3-Pyridylacetic acid hydrochloride has been identified as a dipeptidyl peptidase-4 (DPP-4) inhibitor and is classified as an endogenous metabolite. DPP-4 is an enzyme that degrades incretin hormones (GLP-1 and GIP), which are involved in glucose metabolism. The compound also targets pathways related to bone metabolism, as it is an impurity of risedronate. In addition, it may interact with enzymes involved in nicotine metabolism and pyridine derivative processing.
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| ln Vitro |
In vitro, 3-pyridylacetic acid hydrochloride significantly reduces osteoclast formation and activity. Studies have shown that the compound inhibits bone resorption markers in a dose-dependent manner when tested on human osteoclast precursors. It also exhibits activity against DPP-4 (dipeptidyl peptidase-4), suggesting potential applications in diabetes research. As a nicotine metabolite, it is also used in studies of tobacco alkaloid breakdown pathways.
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| ln Vivo |
In vivo, 3-pyridylacetic acid hydrochloride is used to study nicotine metabolism and the pharmacokinetics of tobacco alkaloids. It has been detected as a urinary metabolite in smokers. As a DPP-4 inhibitor, it may have potential for managing glucose metabolism, though no direct in vivo efficacy data for this specific compound are available. It is also an impurity of risedronate and is studied in the context of bisphosphonate drug quality control and analytical testing.
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| Enzyme Assay |
For non-cellular assays (enzyme inhibition), DPP-4 activity is measured using a fluorometric assay. The reaction mixture (50 uL) contains 50 mM Tris-HCl (pH 8.0), 0.1 mg/mL BSA, 10 uM Gly-Pro-AMC (a fluorogenic substrate), and various concentrations of 3-pyridylacetic acid hydrochloride (0-500 uM). The reaction is initiated by adding recombinant human DPP-4 (2 ng/uL) and incubated at 37degC for 30 minutes. The reaction is stopped with 150 uL of 150 mM sodium acetate (pH 4.0). Fluorescence (excitation 360 nm, emission 460 nm) is measured, and IC₅0 is determined.
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| Cell Assay |
For cell-based assays, human osteoclast precursors (e.g., CD14+ monocytes isolated from peripheral blood) are seeded in 96-well plates (1×10⁴ cells/well) in alpha-MEM with 10% FBS, 50 ng/mL M-CSF, and 50 ng/mL RANKL. After 5 days of differentiation into osteoclasts, cells are treated with 3-pyridylacetic acid hydrochloride (0-500 uM) for 48-72 hours. Osteoclast formation is assessed by TRAP (tartrate-resistant acid phosphatase) staining. Bone resorption activity is measured by seeding cells on calcium phosphate-coated plates and quantifying resorbed area after 5-7 days.
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| Animal Protocol |
For in vivo animal experiments, rodent models are used to study bone metabolism and risedronate impurities. Mice (e.g., C57BL/6, 8-10 weeks old) are ovariectomized to induce bone loss. The compound is administered orally or intraperitoneally at doses of 1-50 mg/kg/day for 4-8 weeks. Bone mineral density (BMD) is measured by DEXA or micro-CT. TRAP5b (a serum marker of bone resorption) is measured by ELISA. Alternatively, the compound can be used in pharmacokinetic studies following administration to rats, with blood and urine collected for LC-MS analysis to measure 3-pyridylacetic acid levels.
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| ADME/Pharmacokinetics |
3-Pyridylacetic acid hydrochloride has a molecular weight of 173.6, with high purity (>99% in some preparations). It is soluble in water and organic solvents. As an endogenous metabolite and nicotine breakdown product, it is generally non-toxic at physiological concentrations. In research settings, the compound has low acute toxicity. Standard laboratory safety precautions should be followed. The hydrochloride salt form is stable under normal storage conditions (powder at -20degC, sealed).
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| Toxicity/Toxicokinetics |
3-Pyridylacetic acid hydrochloride has low acute toxicity; no specific LD₅0 has been reported. As an endogenous metabolite, it is considered safe at physiological concentrations. Standard laboratory safety precautions should be followed. No significant adverse effects are expected at typical research doses.
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| References | |
| Additional Infomation |
3-Pyridylacetic acid hydrochloride is a research compound and not an approved drug. It has not undergone clinical trials for therapeutic use. Its primary applications include use as a reference standard for risedronate impurity testing (pharmaceutical quality control), as a chemical intermediate for the synthesis of anti-inflammatory agents and herbicides, and as a research tool in studies of nicotine metabolism and DPP-4 inhibition. It is classified as an endogenous metabolite and is available for research use only. No pharmacological mechanism for therapeutic benefit has been established for this compound alone.
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| Molecular Formula |
C7H8CLNO2
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|---|---|
| Molecular Weight |
173.60
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| Exact Mass |
173.024
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| CAS # |
6419-36-9
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| Related CAS # |
3-Pyridineacetic acid;501-81-5;3-Pyridylacetic acid-d4 hydrochloride;1219802-37-5
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| PubChem CID |
2723724
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| Appearance |
White to off-white solid powder
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| Boiling Point |
301.6ºC at 760 mmHg
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| Melting Point |
161-163 °C(lit.)
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| LogP |
1.51
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| Hydrogen Bond Donor Count |
2
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| Hydrogen Bond Acceptor Count |
3
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| Rotatable Bond Count |
2
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| Heavy Atom Count |
11
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| Complexity |
125
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| Defined Atom Stereocenter Count |
0
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| SMILES |
C1=CC(=CN=C1)CC(=O)O.Cl
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| InChi Key |
XVCCOEWNFXXUEV-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C7H7NO2.ClH/c9-7(10)4-6-2-1-3-8-5-6;/h1-3,5H,4H2,(H,9,10);1H
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| Chemical Name |
2-pyridin-3-ylacetic acid;hydrochloride
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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, 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: 100 mg/mL (576.04 mM)
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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 | 5.7604 mL | 28.8018 mL | 57.6037 mL | |
| 5 mM | 1.1521 mL | 5.7604 mL | 11.5207 mL | |
| 10 mM | 0.5760 mL | 2.8802 mL | 5.7604 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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