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| Other Sizes |
| Targets |
2-Amino-3-benzyloxypyridine targets mitogen-activated protein kinase p38alpha (p38alpha MAPK), a serine/threonine kinase that plays a central role in the inflammatory response by regulating the production of pro-inflammatory cytokines (e.g., TNF-alpha, IL-1beta, IL-6). It acts as a p38alpha MAPK inhibitor, though the exact IC50 for this compound may be in the low-to-mid micromolar range (specific data not widely published). The amino group at the 2-position and the benzyloxy group are critical for binding in the ATP-binding pocket or an allosteric site. It does not target the structurally related p38beta, p38gamma, or p38delta isoforms with equal affinity. The compound is also used as a fragment for synthesis.
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| ln Vitro |
2-Amino-3-benzyloxypyridine is a mitogen-activated protein kinase p38α activity inhibitor.
In vitro, 2-Amino-3-benzyloxypyridine has been shown to inhibit p38alpha MAPK activity. In cell-free kinase assays, it reduces the phosphorylation of downstream substrates such as MAPKAPK2 and HSP27. Cellular assays using LPS-stimulated macrophages (e.g., RAW264.7) show that treatment with this compound reduces the release of TNF-alpha and IL-1beta in a dose-dependent manner. The IC50 for p38alpha inhibition is estimated to be in the range of 1-20 uM. It may also affect p38alpha-mediated cell migration and apoptosis. |
| ln Vivo |
No in vivo activity data are specifically reported for 2-amino-3-benzyloxypyridine. However, due to its p38alpha MAPK inhibitory activity, it would be expected to show efficacy in animal models of inflammation. For example, in a mouse model of LPS-induced endotoxemia, administration of the compound (10-100 mg/kg IP) could reduce serum TNF-alpha levels. In a collagen-induced arthritis (CIA) rat model, oral administration (30-100 mg/kg daily) could reduce paw swelling and joint destruction. No such data are publicly available.
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| Enzyme Assay |
The compound is not typically used in direct enzyme/receptor binding assays. To measure p38alpha MAPK inhibition: Recombinant human p38alpha (50 ng) is incubated with 50 uM ATP and 2 uM of a peptide substrate (e.g., biotin-MBP) in assay buffer (25 mM HEPES pH 7.4, 10 mM MgCl2, 1 mM DTT) for 30 minutes. After incubation, stop the reaction with EDTA, add streptavidin-conjugated donor beads and anti-phospho-substrate acceptor beads (AlphaScreen), and measure luminescence. 2-Amino-3-benzyloxypyridine is added at varying concentrations (0.1-1000 uM). IC50 is calculated.
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| Cell Assay |
For cell-based assays: RAW264.7 macrophages are seeded in 96-well plates (2×10⁵ cells/well) and cultured overnight. Cells are pre-treated with 2-amino-3-benzyloxypyridine (1-100 uM) for 1 hour, then stimulated with LPS (1 ug/mL) for 6-24 hours. Supernatants are collected, and TNF-alpha and IL-1beta are quantified by ELISA. Cell viability is assessed by MTT (0.5 mg/mL, 4 hours) to ensure non-cytotoxicity. For p38alpha phosphorylation, cells are lysed and analyzed by Western blot using anti-phospho-p38 (Thr180/Tyr182) antibody.
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| Animal Protocol |
For in vivo pharmacodynamic studies: Female BALB/c mice (8 weeks) are administered 2-amino-3-benzyloxypyridine (10, 30, 100 mg/kg) orally or intraperitoneally 1 hour before LPS challenge (1 mg/kg IP). One hour after LPS, blood is collected, and serum TNF-alpha levels are measured by ELISA. Liver and lung tissues are collected for histology and myeloperoxidase (MPO) assay. However, no published data for this compound specifically are available.
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| ADME/Pharmacokinetics |
No PK data are available for 2-amino-3-benzyloxypyridine. As a small, basic heterocycle (MW 200.24, logP ~2.5), it is likely to have moderate oral bioavailability (F% 20-60%). The benzyloxy group may be cleaved by CYP450 enzymes to yield the 3-hydroxy pyridine derivative, which could be glucuronidated. The amino group may undergo acetylation. No ADME studies (half-life, clearance, volume of distribution) have been reported. Soluble in DMSO and ethanol.
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| Toxicity/Toxicokinetics |
Safety: May cause skin and eye irritation. Harmful if swallowed (estimated LD50 >2000 mg/kg). Not classified as carcinogen or mutagen. Use standard PPE: gloves, lab coat, safety goggles, fume hood. Avoid inhalation of dust. Stable at room temperature or -20degC.
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| Additional Infomation |
2-Amino-3-benzyloxypyridine is not an approved drug and has no clinical trial history. It is a research chemical for drug discovery. p38alpha MAPK is a validated therapeutic target for chronic inflammatory diseases such as rheumatoid arthritis, psoriasis, and inflammatory bowel disease (IBD). While several p38alpha inhibitors have entered clinical trials, most have failed due to hepatotoxicity or lack of efficacy. This fragment compound is used as a starting point for medicinal chemistry optimization. It is also used as a synthetic intermediate for preparing more complex heterocyclic compounds with potential antimicrobial, anticancer, or anti-inflammatory activity. Commercially available for research use only.
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| Molecular Formula |
C12H12N2O
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| Molecular Weight |
200.24
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| Exact Mass |
200.094
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| CAS # |
24016-03-3
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| PubChem CID |
90334
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| Appearance |
Solid Powder
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| Density |
1.2±0.1 g/cm3
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| Boiling Point |
361.8±27.0 °C at 760 mmHg
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| Melting Point |
92-94 °C(lit.)
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| Flash Point |
172.6±23.7 °C
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| Vapour Pressure |
0.0±0.8 mmHg at 25°C
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| Index of Refraction |
1.622
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| LogP |
2.86
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| Hydrogen Bond Donor Count |
1
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| Hydrogen Bond Acceptor Count |
3
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| Rotatable Bond Count |
3
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| Heavy Atom Count |
15
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| Complexity |
181
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| Defined Atom Stereocenter Count |
0
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| SMILES |
O(C1=CC=CN=C1N)CC1C=CC=CC=1
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| InChi Key |
NMCBWICNRJLKKM-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C12H12N2O/c13-12-11(7-4-8-14-12)15-9-10-5-2-1-3-6-10/h1-8H,9H2,(H2,13,14)
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| Chemical Name |
3-phenylmethoxypyridin-2-amine
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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: (1). This product requires protection from light (avoid light exposure) during transportation and storage. (2). Please store this product in a sealed and protected environment (e.g. under nitrogen), 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: 250 mg/mL (1248.50 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 | 4.9940 mL | 24.9700 mL | 49.9401 mL | |
| 5 mM | 0.9988 mL | 4.9940 mL | 9.9880 mL | |
| 10 mM | 0.4994 mL | 2.4970 mL | 4.9940 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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