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| Targets |
4-Amino-2-chloropyrimidine is a competitive inhibitor for acetylcholinesterase (AChE) with a Ki value of 0.18 μM and for butyrylcholinesterase (BChE) with a Ki value of 1.324 μM. It also exhibits high inhibitory activity against glutathione S-transferase (GST) enzyme with an IC₅₀ of 0.037 μM and a Ki of 0.047 μM in vitro. The compound fits in the binding pocket of the 4BDS protein. Through cholinesterase inhibition, it leads to acetylcholine accumulation in the synapse, increasing neurotransmitter concentration and the frequency of cell apoptosis.
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| ln Vitro |
In vitro, 4-Amino-2-chloropyrimidine demonstrates potent enzyme inhibitory activity. It acts as a competitive inhibitor for AChE (Ki = 0.18 μM) and BChE (Ki = 1.324 μM), and shows high inhibitory activity against GST with IC₅₀ = 0.037 μM and Ki = 0.047 μM. Molecular docking studies have been performed to understand the binding interactions of this compound on the active site of target enzymes. It has also been shown to be cytotoxic against cancer cells and virus-infected cells. The compound is used as a biochemical reagent in various in vitro assay systems for enzyme inhibition studies and as a sulfonylation reagent in organic synthesis and drug discovery.
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| ln Vivo |
In vivo data for 4-Amino-2-chloropyrimidine as a standalone compound are limited. The compound is primarily a biochemical reagent and synthetic intermediate rather than a directly administered therapeutic agent. Optical properties and pharmacokinetic properties of this substance have been studied using optical spectroscopy, fluorescence spectroscopy, and molecular modeling techniques. Its in vivo relevance is primarily through the pharmaceutical compounds synthesized from it as a building block. The compound's cholinesterase inhibitory activity suggests potential for in vivo studies in models of neurological conditions, but specific animal study data are not documented in the publicly available literature.
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| Enzyme Assay |
For in vitro enzyme binding assays, 4-Amino-2-chloropyrimidine is evaluated using purified AChE, BChE, or GST enzymes. Enzyme activity is measured spectrophotometrically using appropriate substrates. For AChE inhibition, the Ellman's method is employed: acetylthiocholine iodide is used as substrate, and 5,5'-dithiobis-(2-nitrobenzoic acid) (DTNB) is used as the chromogenic agent. Reaction progress is monitored at 412 nm. The compound (0.001-100 μM) is pre-incubated with the enzyme for 5-10 minutes at 25°C before substrate addition. IC₅₀ values are calculated from dose-response curves, and Ki values are determined from Lineweaver-Burk plots. The compound shows Ki = 0.18 μM for AChE and Ki = 1.324 μM for BChE. For GST inhibition, 1-chloro-2,4-dinitrobenzene (CDNB) and glutathione are used as substrates.
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| Cell Assay |
For in vitro cell-based assays, 4-Amino-2-chloropyrimidine can be evaluated for cytotoxicity against cancer cell lines such as HeLa, MCF-7, or HepG2. Cells are seeded in 96-well plates and treated with the compound at concentrations ranging from 0.1-100 μM for 24-72 hours. Cell viability is assessed using MTT or CCK-8 assays: MTT (3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide) is added to each well, incubated for 4 hours, formazan crystals are dissolved in DMSO, and absorbance is measured at 570 nm. The compound has shown cytotoxic effects against cancer cells. It can also be evaluated in virus-infected cell models to assess antiviral activity.
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| Animal Protocol |
In vivo animal studies for 4-Amino-2-chloropyrimidine are not well-documented. As a biochemical reagent and synthetic intermediate, the compound is not typically administered directly to animals for pharmacological evaluation. However, for compounds synthesized from this pyrimidine building block, standard in vivo protocols would involve administration to rodents (mice or rats) via oral gavage, intravenous injection, or intraperitoneal injection at doses determined from in vitro potency data. Pharmacokinetic sampling would be conducted at multiple time points post-administration for plasma concentration analysis. Specific protocols for this compound are not available in the public literature.
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| ADME/Pharmacokinetics |
Pharmacokinetic data for 4-Amino-2-chloropyrimidine are limited. The compound has a calculated logP of 1.29, indicating moderate lipophilicity suitable for passive membrane permeability. The molecular weight of 129.55 g/mol is well within the favorable range for oral absorption. The compound has a polar surface area (PSA) of 51.8 Ų, suggesting moderate intestinal absorption potential. Optical spectroscopy and fluorescence spectroscopy have been used to study the compound's optical and pharmacokinetic properties. However, empirical pharmacokinetic parameters such as half-life, clearance, volume of distribution, and oral bioavailability are not documented for this compound in the publicly available literature.
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| Toxicity/Toxicokinetics |
Toxicological data for 4-Amino-2-chloropyrimidine are not extensively documented. The compound is classified as a research chemical and should be handled with appropriate laboratory safety precautions. As a chlorinated pyrimidine derivative, it may pose risks of skin and eye irritation. Specific LD₅₀ values, acute toxicity classifications, and chronic toxicity data are not available in the public literature. The compound is intended for research use only and not for human therapeutic applications. Standard safety practices include the use of personal protective equipment (gloves, safety goggles, lab coat), working in a fume hood, and avoiding inhalation and skin contact.
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| Additional Infomation |
2-Chloro-4-aminopyrimidine is a microtubule polymerization inhibitor.
4-Amino-2-chloropyrimidine (CAS 7461-50-9) is primarily a research-grade biochemical reagent and synthetic intermediate, not an FDA-approved pharmaceutical drug. Its mechanism of action involves competitive inhibition of AChE (Ki = 0.18 μM), BChE (Ki = 1.324 μM), and GST (IC₅₀ = 0.037 μM). The compound has been shown to be cytotoxic against cancer cells and virus-infected cells. Molecular docking analysis has been performed to understand binding interactions on enzyme active sites. No clinical trials or approved therapeutic indications exist for this compound. It is used as a building block in pharmaceutical synthesis and as a sulfonylation reagent in organic chemistry and drug discovery. The compound is available with high purity (99.77%) for research applications only and is not intended for human diagnostic or therapeutic use. |
| Molecular Formula |
C4H4CLN3
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| Molecular Weight |
129.55
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| Exact Mass |
129.009
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| CAS # |
7461-50-9
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| PubChem CID |
345752
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| Appearance |
White to yellow solid powder
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| Density |
1.4±0.1 g/cm3
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| Boiling Point |
338.8±15.0 °C at 760 mmHg
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| Melting Point |
197-205 °C
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| Flash Point |
158.7±20.4 °C
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| Vapour Pressure |
0.0±0.7 mmHg at 25°C
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| Index of Refraction |
1.618
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| LogP |
0.44
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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 |
0
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| Heavy Atom Count |
8
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| Complexity |
77.7
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| Defined Atom Stereocenter Count |
0
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| SMILES |
C1=CN=C(N=C1N)Cl
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| InChi Key |
LPBDZVNGCNTELM-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C4H4ClN3/c5-4-7-2-1-3(6)8-4/h1-2H,(H2,6,7,8)
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| Chemical Name |
2-chloropyrimidin-4-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 |
| 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 | 7.7190 mL | 38.5951 mL | 77.1903 mL | |
| 5 mM | 1.5438 mL | 7.7190 mL | 15.4381 mL | |
| 10 mM | 0.7719 mL | 3.8595 mL | 7.7190 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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