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| Other Sizes |
| Targets |
The mechanism of action of 4-ethynylaniline derivatives has been explored in various contexts. 4′-Ethynyl nucleoside analogs, derived from this compound, are potent inhibitors of multidrug-resistant HIV strains, functioning as nucleoside reverse transcriptase inhibitors that block HIV replication by interfering with viral reverse transcriptase. The compound itself is a metabolite of erlotinib, which acts on the epidermal growth factor receptor (EGFR), inhibiting EGFR-associated kinase activity. It does not have intrinsic biological activity but serves as a precursor for bioactive molecules.
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| ln Vitro |
In vitro, 4-ethynylaniline derivatives have demonstrated significant activity as antiviral agents. A series of 4′-ethynyl nucleoside analogs have been synthesized and found to be active against a spectrum of HIV strains, including drug-resistant variants, with low effective concentrations and high selectivity indices. The electrochemical oxidation of 4-ethynylaniline has been studied, revealing that its oxidation products can be hydrolyzed to synthesize diazine compounds with potential antibiotic activity. The parent compound is primarily used as a synthetic intermediate.
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| ln Vivo |
In vivo data for 4-ethynylaniline itself are limited as it is a chemical intermediate and metabolite rather than a drug candidate. Its derivatives, such as 4′-ethynyl nucleoside analogs, may be evaluated in animal models for antiviral efficacy. As a metabolite of erlotinib, it may be detected in plasma following erlotinib administration, but it does not contribute significantly to the therapeutic effects of the parent drug. The compound is primarily used in research for organic synthesis.
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| Enzyme Assay |
Cell-free enzyme assays using 4-ethynylaniline derivatives typically involve testing nucleoside analogs for inhibition of HIV reverse transcriptase. Assays are performed in buffer systems (e.g., Tris-HCl, pH 7.4, containing Mg²⁺ and dNTPs) with purified enzyme and radiolabeled substrates. Inhibitory potency (IC50) is determined by measuring the incorporation of radioactive nucleotides into DNA. The compound's ethynyl group may also be used in Click chemistry-based binding studies to label or detect target proteins in cell-free systems.
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| Cell Assay |
For cell-based studies, 4-ethynylaniline derivatives such as 4′-ethynyl nucleoside analogs are tested in HIV-infected cell cultures (e.g., MT-4 cells or peripheral blood mononuclear cells). Cells are cultured in RPMI-1640 with 10% FBS and treated with varying concentrations of the test compound for 3–7 days. Antiviral activity is assessed by measuring viral replication (p24 antigen ELISA or RT activity) and cell viability (MTT assay). Selectivity indices are calculated from IC50 and CC50 values. Vehicle controls and positive controls (e.g., AZT) are included.
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| Animal Protocol |
In vivo studies with 4-ethynylaniline derivatives may involve administration to rodents via oral gavage or intravenous injection for pharmacokinetic and efficacy evaluations. For antiviral studies, infected animals are treated with the test compound, and viral load is monitored. Blood samples are collected for pharmacokinetic analysis (Cmax, AUC, half-life). Tissue distribution and metabolite identification may also be performed. All procedures follow institutional animal care and use committee guidelines.
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| ADME/Pharmacokinetics |
4-Ethynylaniline is a synthetic chemical intermediate and is not subject to comprehensive pharmacokinetic evaluation as a drug. Its physicochemical properties include a molecular weight of 117.15 g/mol and solubility in organic solvents. As a metabolite of erlotinib, it may be detected in plasma following erlotinib administration. The compound's terminal alkyne and amine groups make it a versatile building block for Click chemistry and pharmaceutical synthesis. It is stable under normal storage conditions and is available in high purity (≥98%).
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| Toxicity/Toxicokinetics |
The toxicological profile of 4-ethynylaniline as a pure chemical reagent has not been extensively characterized. As an aromatic amine, it may pose health hazards, including skin and eye irritation, and potential sensitization. Standard laboratory safety precautions should be observed, including the use of personal protective equipment (gloves, goggles, lab coat) and adequate ventilation. Ingestion or inhalation should be avoided. Appropriate first-aid measures should be in place, and spills should be cleaned up promptly.
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| Additional Infomation |
4-Ethynylaniline is a substituted aniline.
4-Ethynylaniline is not a drug but an important pharmaceutical intermediate and chemical building block. It is a metabolite of erlotinib, an EGFR tyrosine kinase inhibitor used in cancer therapy. The compound is widely used in the synthesis of 4′-ethynyl nucleoside analogs with potent anti-HIV activity. Its terminal alkyne group enables Click chemistry applications for bioconjugation and drug discovery. It is also used as an impurity reference standard for erlotinib. It is not approved for clinical use. |
| Molecular Formula |
C8H7N
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|---|---|
| Molecular Weight |
117.15
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| Exact Mass |
117.057
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| CAS # |
14235-81-5
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| PubChem CID |
3760025
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| Appearance |
Yellow to orange solid powder
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| Density |
1.1±0.1 g/cm3
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| Boiling Point |
223.7±23.0 °C at 760 mmHg
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| Melting Point |
98-102 °C (dec.)(lit.)
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| Flash Point |
98.3±17.9 °C
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| Vapour Pressure |
0.1±0.4 mmHg at 25°C
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| Index of Refraction |
1.590
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| LogP |
1.12
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| Hydrogen Bond Donor Count |
1
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| Hydrogen Bond Acceptor Count |
1
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| Rotatable Bond Count |
1
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| Heavy Atom Count |
9
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| Complexity |
123
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| Defined Atom Stereocenter Count |
0
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| SMILES |
C#CC1=CC=C(C=C1)N
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| InChi Key |
JXYITCJMBRETQX-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C8H7N/c1-2-7-3-5-8(9)6-4-7/h1,3-6H,9H2
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| Chemical Name |
4-ethynylaniline
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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: This product requires protection from light (avoid light exposure) during transportation and storage. |
| 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 (853.61 mM)
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (21.34 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 25.0 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: ≥ 2.5 mg/mL (21.34 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 25.0 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: ≥ 2.5 mg/mL (21.34 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 | 8.5361 mL | 42.6803 mL | 85.3606 mL | |
| 5 mM | 1.7072 mL | 8.5361 mL | 17.0721 mL | |
| 10 mM | 0.8536 mL | 4.2680 mL | 8.5361 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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