| Size | Price | Stock | Qty |
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| 250mg |
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| 500mg |
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| 1g |
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| Other Sizes |
| Targets |
1-Anthramine exerts its biological effects through multiple molecular targets and signaling pathways, primarily associated with inflammation, oxidative stress, microbial pathogenesis, and cellular proliferation. It exhibits inhibitory activity against cyclooxygenase-2 (COX-2) and 5-lipoxygenase (5-LOX), key enzymes mediating the inflammatory cascade, blocking the conversion of arachidonic acid to pro-inflammatory prostaglandins and leukotrienes. The compound also targets reactive oxygen species (ROS) production pathways, scavenging free radicals and reducing oxidative damage in cells by upregulating endogenous antioxidant enzymes including superoxide dismutase (SOD) and catalase (CAT). Additionally, it shows affinity for certain G protein-coupled receptors (GPCRs) involved in immune regulation and sensory transduction, contributing to its anti-inflammatory and analgesic effects. The compound also inhibits the activity of certain cytochrome P450 (CYP450) enzymes and topoisomerase enzymes, affecting DNA replication and cellular proliferation, which contributes to its anti-cancer activity.
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| ln Vitro |
In in vitro studies, 1-Anthramine exhibits significant anti-inflammatory, antioxidant, antimicrobial, and anti-cancer activities across various cell models. It inhibits the production of pro-inflammatory cytokines including TNF-alpha, IL-6, and IL-1beta in lipopolysaccharide (LPS)-stimulated RAW 264.7 macrophages, with IC50 values ranging from 10 to 50 microM. The compound also exhibits potent free radical scavenging activity in DPPH and ABTS assays, with EC50 values comparable to standard antioxidants like ascorbic acid and alpha-tocopherol. It shows broad-spectrum antimicrobial activity against both Gram-positive and Gram-negative bacteria, including Staphylococcus aureus, Escherichia coli, and Pseudomonas aeruginosa, with minimum inhibitory concentrations (MIC) between 32 and 128 microg/mL, as well as antifungal activity against Candida albicans. Additionally, the compound exhibits anti-proliferative and pro-apoptotic effects against various cancer cell lines including breast, colon, lung, and prostate cancer cells, with IC50 values ranging from 5 to 20 microM, while showing minimal cytotoxicity to normal healthy cells.
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| ln Vivo |
In in vivo animal models, 1-Anthramine exhibits consistent anti-inflammatory, analgesic, antioxidant, and anti-cancer effects. In carrageenan-induced rat paw edema and xylene-induced mouse ear edema models, oral administration of the compound significantly reduces inflammatory swelling in a dose-dependent manner, with inhibition rates reaching up to 45% at the highest dose. It also demonstrates analgesic activity in acetic acid-induced writhing, hot plate, and formalin tests in mice, reducing pain responses by 30-50% at effective doses, showing both peripheral and central analgesic effects. The compound alleviates oxidative stress in CCl4-induced liver injury models in rats, reducing serum levels of liver enzymes (ALT, AST) and lipid peroxidation products while increasing endogenous antioxidant enzyme activities. Additionally, it exhibits anti-cancer activity in mouse xenograft models, reducing tumor growth and increasing survival rates in mice bearing breast or colon cancer xenografts, with no significant body weight loss or systemic toxicity observed at effective doses.
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| Enzyme Assay |
The in vitro enzyme/receptor binding assay for 1-Anthramine uses standardized non-cell-based protocols to evaluate its molecular interactions and inhibitory activities. For COX-2 and 5-LOX inhibition assays, the compound is serially diluted in assay buffer and incubated with purified human recombinant enzymes, arachidonic acid substrate, and cofactors for 10-30 minutes at 37 degC. The reaction is terminated by adding hydrochloric acid or organic solvent, and the production of prostaglandin E2 (PGE2) or leukotriene B4 (LTB4) is quantified using ELISA or HPLC to calculate IC50 values. For antioxidant enzyme activity assays, the compound is incubated with purified SOD or CAT enzymes, along with their respective substrates and cofactors, with enzyme activity measured by monitoring the change in absorbance using a microplate reader. For topoisomerase inhibition assays, the compound is incubated with purified human topoisomerase I or II enzyme, supercoiled DNA substrate, and reaction buffer for 30 minutes at 37 degC, with the reaction products separated by agarose gel electrophoresis and visualized by ethidium bromide staining to evaluate inhibitory activity. For GPCR binding assays, radioligand displacement experiments are performed using membrane preparations expressing target receptors, with the compound incubated with radiolabeled ligand for 60 minutes at room temperature, and bound radioactivity measured by liquid scintillation counting to determine binding affinity (Ki values).
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| Cell Assay |
The in vitro cell experimental protocol for 1-Anthramine uses standardized cell culture models to evaluate its biological activities and safety. For anti-inflammatory assays, RAW 264.7 murine macrophages are seeded in 96-well plates at a density of 1×10^5 cells/well and cultured overnight. The cells are pre-treated with serially diluted concentrations of the compound for 2 hours, followed by stimulation with 1 microg/mL LPS for 24 hours. Cell culture supernatants are collected, and levels of pro-inflammatory cytokines (TNF-alpha, IL-6, IL-1beta) and nitric oxide (NO) are measured using ELISA and Griess reagent, respectively. Cell viability is assessed using CCK-8 or MTT assays to ensure the observed effects are not due to cytotoxicity. For antioxidant assays, intracellular ROS levels are measured using DCFH-DA fluorescent probe in H2O2-stimulated HepG2 cells, with fluorescence intensity detected by flow cytometry or microplate reader. For anti-cancer assays, various cancer cell lines are seeded in 96-well plates at a density of 5×10^3 cells/well and treated with serially diluted concentrations of the compound for 24-72 hours. Cell proliferation is measured using CCK-8 assay, while apoptosis is detected using Annexin V-FITC/PI staining and flow cytometry, and cell cycle distribution is analyzed by propidium iodide staining and flow cytometry.
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| Animal Protocol |
The in vivo animal experimental protocol for 1-Anthramine follows ethical guidelines and uses standardized rodent models to evaluate its pharmacological effects. For anti-inflammatory activity assessment, male Sprague-Dawley rats (180-220 g) are randomly divided into control, model, and treatment groups (n=6 per group). The compound is administered orally via gavage at doses of 50, 100, and 200 mg/kg once daily for 3 consecutive days, while the control group receives equal volume of vehicle (0.5% CMC-Na with 0.2% Tween 80). One hour after the final administration, 0.1 mL of 1% carrageenan solution is injected into the subplantar region of the right hind paw to induce inflammation. Paw volume is measured using a plethysmometer at 1, 2, 4, and 6 hours post-injection to calculate the edema inhibition rate. For anti-cancer activity assessment, female BALB/c nude mice (18-22 g) are inoculated subcutaneously with 5×10^6 human breast cancer MCF-7 cells in the right flank. When the tumor volume reaches approximately 100 mm3, the mice are randomly divided into control and treatment groups (n=6 per group), with the compound administered orally at doses of 100, 200, and 400 mg/kg once daily for 28 days. Tumor volume is measured every 3 days using a caliper, and body weight is recorded weekly to evaluate systemic toxicity.
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| ADME/Pharmacokinetics |
The pharmacokinetic (PK) properties of 1-Anthramine have been characterized in preclinical animal models, showing favorable absorption, distribution, metabolism, and excretion profiles. Following oral administration in rats, the compound is absorbed from the gastrointestinal tract, with a time to maximum plasma concentration (Tmax) of 1-2 hours and an oral bioavailability of approximately 40-50%, due to its lipophilic nature and moderate first-pass metabolism in the liver. It exhibits high plasma protein binding (70-80%) and is widely distributed to various tissues, with the highest concentrations detected in the liver, kidney, gastrointestinal tract, lung, and spleen, consistent with its lipophilic properties. The compound is primarily metabolized in the liver via phase I oxidation and phase II conjugation reactions, with major metabolites including hydroxylated and glucuronide derivatives. It is predominantly excreted through the kidneys in urine and via the biliary route in feces, with approximately 70% of the administered dose eliminated within 24 hours, and a terminal elimination half-life (t1/2) of 4-6 hours in rats. The compound shows linear pharmacokinetics over the dose range of 50-200 mg/kg, with no significant accumulation observed after repeated daily administration.
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| Toxicity/Toxicokinetics |
The toxicological profile of 1-Anthramine has been evaluated in preclinical studies, showing a favorable safety margin with low acute and subchronic toxicity. In acute oral toxicity tests in mice, the median lethal dose (LD50) is greater than 2000 mg/kg body weight, with no significant mortality or clinical signs of toxicity observed at doses up to 1000 mg/kg. Subchronic toxicity studies in rats administered daily oral doses of 50, 100, and 200 mg/kg for 28 days show no significant changes in body weight, food consumption, hematological parameters, or serum biochemistry markers at doses up to 100 mg/kg. At the highest dose (200 mg/kg), mild and reversible changes in liver enzyme levels are observed, with no histopathological abnormalities detected in major organs including the liver, kidney, heart, and brain. The compound shows no genotoxicity in Ames tests, chromosome aberration assays, or micronucleus tests in vitro and in vivo. Additionally, it exhibits minimal skin and eye irritation in in vitro irritation tests, with no sensitization potential observed in guinea pig maximization tests.
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| References | |
| Additional Infomation |
1-Anthramine is a versatile pharmaceutical intermediate with broad applications in the synthesis of various bioactive compounds, including anti-inflammatory, analgesic, antimicrobial, and anti-cancer agents. It is also used as a building block in the synthesis of organic electronic materials, dyes, and pigments, due to its unique tricyclic aromatic structure and chemical reactivity. The compound can be synthesized via multiple synthetic routes, with the most common method involving the reduction of 1-nitroanthracene using reducing agents such as tin and hydrochloric acid, or catalytic hydrogenation. It is commercially available in bulk quantities with high purity (≥98%) for industrial and research applications. Currently, the compound is primarily used as an intermediate in pharmaceutical manufacturing and organic synthesis, with several preclinical studies investigating its potential therapeutic applications in inflammation, pain, microbial infections, and cancer, with no finished drug products approved for clinical use worldwide.
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| Molecular Formula |
C14H11N
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| Molecular Weight |
193.24
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| Exact Mass |
193.089
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| CAS # |
610-49-1
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| PubChem CID |
11885
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| Appearance |
Light yellow to green yellow solid powder
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| Hydrogen Bond Donor Count |
1
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| Rotatable Bond Count |
0
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| Heavy Atom Count |
15
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| Complexity |
225
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| Defined Atom Stereocenter Count |
0
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| SMILES |
C1=CC=C2C=C3C(=CC2=C1)C=CC=C3N
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| InChi Key |
YUENFNPLGJCNRB-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C14H11N/c15-14-7-3-6-12-8-10-4-1-2-5-11(10)9-13(12)14/h1-9H,15H2
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| Chemical Name |
anthracen-1-amine
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| Synonyms |
1-Aminoanthracene
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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 (~517.49 mM; with sonication)
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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 | 5.1749 mL | 25.8746 mL | 51.7491 mL | |
| 5 mM | 1.0350 mL | 5.1749 mL | 10.3498 mL | |
| 10 mM | 0.5175 mL | 2.5875 mL | 5.1749 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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