Physicochemical Properties
| Molecular Formula | C30H28FN3O2 |
| Molecular Weight | 481.56 |
| Exact Mass | 481.216 |
| CAS # | 2769156-00-3 |
| PubChem CID | 165413027 |
| Appearance | Light yellow to yellow solid powder |
| LogP | 5.7 |
| Hydrogen Bond Donor Count | 0 |
| Hydrogen Bond Acceptor Count | 6 |
| Rotatable Bond Count | 7 |
| Heavy Atom Count | 36 |
| Complexity | 744 |
| Defined Atom Stereocenter Count | 0 |
| SMILES | O=C1C2=CC=CC=C2C2N=CC=C3C=C(C=C1C=23)OCCCCN1CCN(C2C=CC=CC=2F)CC1 |
| InChi Key | GWRCLKVKZRBZJA-UHFFFAOYSA-N |
| InChi Code | InChI=1S/C30H28FN3O2/c31-26-9-3-4-10-27(26)34-16-14-33(15-17-34)13-5-6-18-36-22-19-21-11-12-32-29-23-7-1-2-8-24(23)30(35)25(20-22)28(21)29/h1-4,7-12,19-20H,5-6,13-18H2 |
| Chemical Name | 11-[4-[4-(2-fluorophenyl)piperazin-1-yl]butoxy]-16-azatetracyclo[7.7.1.02,7.013,17]heptadeca-1(16),2,4,6,9(17),10,12,14-octaen-8-one |
| HS Tariff Code | 2934.99.9001 |
| 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) |
Biological Activity
| Targets | MAO-A 0.004 ± 0. μM (IC50) 5-HT2A Receptor 0.014 μM (IC50) MAO-B 1.05 ± 0.0 μM (IC50) |
| ln Vitro | Compound I14, MAO-A/5-HT2AR-IN-1, has a noteworthy neurocytoprotective impact on the CORT-induced cell depression model at concentrations of 0–4 μM over a 24-hour period [1]. The active cavity of 5-HT2AR and MAO-A can be occupied by MAO-A/5-HT2AR-IN -1 through the use of numerous hydrogen bonding forces and π–π stacking interaction[1]. With regard to L02 cells (IC50 > 100 μM), SH-SY5Y (IC50 > 10 μM), and PC12 (IC50 > 10 μM), MAO-A/5-HT2AR-IN-1 shows minimal proliferation inhibitory actions, suggesting a good safety profile[1]. |
| ln Vivo | MAO-A/5-HT2AR-IN-1 (compound I14) at 10 and 20 mg/kg, dramatically improves mice's depressive-like behavior[1]. For seven days, MAO-A/5-HT2AR-IN-1 (0–1 μM) enhances the depression-like behavior and zebrafish locomotion[1]. The expression of 5-HT2AR in mouse brain tissue can be decreased and hippocampus neuronal cell injury can be repaired by MAO-A/5-HT2AR-IN-1[1]. A good clearance rate of 345.69 mL/min/kg has been reported for MAO-A/5-HT2AR-IN-1 in rats (2 mg/kg (iv) 10 mg/kg (ig); once)[1]. |
| Cell Assay |
Cell Types: PC12 cells Tested Concentrations: 4.0, 2.0, 1.0, and 0.5 μM (and 500 μM CORT) Incubation Duration: 24 h Experimental Results: demonstrated a significant protective effect on PC12 cells injury at different concentrations compared with the model group, where the best protective effect was observed at 0.5 μM . |
| Animal Protocol |
Animal/Disease Models: ICR male mice (8−10 weeks old, weight 18-20 g)[1] Doses: 10 mg/kg, 20 mg/kg Route of Administration: For 2 weeks Experimental Results: Dramatically improved depression-like behavior in mice, with the low dose group (10 mg/kg) being more potent than with the positive drug (Flu, 20 mg/kg). Had no relevant toxic effects on the liver, kidney, lung, and spleen of mice during the treatment period. Animal/Disease Models: Zebrafish (AB strain, Reserpine-induced zebrafish depression model)[1] Doses: 0.1, 0.5, 1 μM Route of Administration: Given 24 h after reserpine, for 7 days. Experimental Results: demonstrated that zebrafish in the I14 administered group moved Dramatically more distance, faster, and spent Dramatically more time in the upper part compared to the model group. Animal/Disease Models: SD (Sprague-Dawley) rats (male)[1] Doses: 2 mg/kg (iv) 10 mg/kg (ig) Route of Administration: IV, IG; once (pharmacokinetic/PK Analysis) Experimental Results: pharmacokinetic/PK Parameters of MAO-A/5-HT2AR-IN-1 in male SD (Sprague-Dawley) rats[1]. parameter 2 mg/kg (iv) 10 mg /kg (ig) Tm |
| References |
[1]. Development of MAO-A and 5-HT2AR Dual Inhibitors with Improved Antidepressant Activity. J Med Chem. 2022 Oct 13;65(19):13385-13400. |
Solubility Data
| 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 |
| 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 (e.g. IP/IV/IM/SC) Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline) *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). 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)] *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. Injection Formulation 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (i.e. 500 μL 2-Hydroxypropyl-β-cyclodextrin → 500 μL Saline) Injection Formulation 6: DMSO : PEG300 : castor oil : Saline = 5 : 10 : 20 : 65 (i.e. 50 μL DMSO → 100 μLPEG300 → 200 μL castor oil → 650 μL Saline) Injection Formulation 7: Ethanol : Cremophor : Saline = 10： 10 : 80 (i.e. 100 μL Ethanol → 100 μL Cremophor → 800 μL Saline) Injection Formulation 8: Dissolve in Cremophor/Ethanol (50 : 50), then diluted by Saline Injection Formulation 9: EtOH : Corn oil = 10 : 90 (i.e. 100 μL EtOH → 900 μL Corn oil) Injection Formulation 10: EtOH : PEG300：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH → 400 μLPEG300 → 50 μL Tween 80 → 450 μL 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). Oral Formulation 3: Dissolved in PEG400 Oral Formulation 4: Suspend in 0.2% Carboxymethyl cellulose Oral Formulation 5: Dissolve in 0.25% Tween 80 and 0.5% Carboxymethyl cellulose Oral Formulation 6: Mixing with food powders Note: Please be aware that the above formulations are for reference only. InvivoChem strongly recommends customers to read literature methods/protocols carefully before determining which formulation you should use for in vivo studies, as different compounds have different solubility properties and have to be formulated differently. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 2.0766 mL | 10.3829 mL | 20.7658 mL | |
| 5 mM | 0.4153 mL | 2.0766 mL | 4.1532 mL | |
| 10 mM | 0.2077 mL | 1.0383 mL | 2.0766 mL |