| Size | Price | Stock | Qty |
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| 1mg |
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| Other Sizes |
| Targets |
The primary known target of (S)-(-)-O-Demethylbuchenavianine is acetylcholinesterase (AChE), the enzyme responsible for hydrolyzing the neurotransmitter acetylcholine in the synaptic cleft. By inhibiting AChE, it may increase acetylcholine levels and enhance cholinergic neurotransmission. It may also have activity at butyrylcholinesterase (BChE). Other potential targets are not well characterized. The compound may also interact with other neurotransmitter systems, but data are lacking. No receptor binding studies have been published.
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| ln Vitro |
In vitro, (S)-(-)-O-Demethylbuchenavianine has been reported to show inhibitory activity against acetylcholinesterase (AChE). However, specific IC50 values are not publicly available. Based on the structure, it is likely a moderate AChE inhibitor, similar to other acridine alkaloids. It may also have weak antioxidant or anti-inflammatory activity. No specific cytotoxicity or antibacterial data are available. The compound is not a standard tool in most pharmacological assays. Any reported activity is limited to natural product screening studies.
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| ln Vivo |
There are no reported in vivo studies for (S)-(-)-O-Demethylbuchenavianine. As a natural product alkaloid, it may have been tested in early-stage animal models for cognitive enhancement (due to AChE inhibition), but no published data are available. It is not used as a therapeutic agent and has no known in vivo efficacy. The compound is a research chemical and has not been evaluated in standard animal models of disease. Any in vivo activity is speculative based on its structure-activity relationship with other acridine-based AChE inhibitors (e.g., tacrine).
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| Enzyme Assay |
A cell‑free acetylcholinesterase inhibition assay can be performed using the Ellman method. Prepare a reaction mixture containing 0.1 M phosphate buffer (pH 8.0), 0.5 mM DTNB (5,5'-dithiobis-(2-nitrobenzoic acid)), and 0.5 mM acetylthiocholine iodide. Add (S)-(-)-O-Demethylbuchenavianine at varying concentrations (0.1-100 microM) and 0.1 U/mL AChE (electric eel). Incubate at 25degC for 10-30 min. Measure absorbance at 412 nm. Compare to control (no inhibitor) and calculate percent inhibition. IC50 can be determined by fitting a dose-response curve. For comparative purposes, tacrine (a known AChE inhibitor) can be used as a positive control. The assay is performed in 96-well plates for high-throughput screening.
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| Cell Assay |
For cell-based assays, culture SH-SY5Y human neuroblastoma cells (which express AChE) in 96-well plates. Treat cells with (S)-(-)-O-Demethylbuchenavianine at concentrations of 0.1-100 microM for 24-48 hours. Measure cell viability by MTT assay to assess cytotoxicity. For AChE activity in cells, after treatment, wash cells, lyse in 0.1% Triton X-100, and use the lysate (20-50 microg protein) in the Ellman assay as described in the cell‑free protocol. A decrease in AChE activity in lysates indicates cellular target engagement. For functional assays, measure acetylcholine levels in culture medium by HPLC-ECD or by using a choline/acetylcholine assay kit. No specific receptor activation assays have been reported.
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| Animal Protocol |
No standard in vivo animal protocols are available for (S)-(-)-O-Demethylbuchenavianine. A hypothetical protocol for assessing cognitive enhancement could be performed using a scopolamine-induced amnesia model in mice. Administer scopolamine (1 mg/kg IP) to induce memory impairment. (S)-(-)-O-Demethylbuchenavianine (e.g., 1-30 mg/kg IP or PO) would be given 30 min before behavioral testing. Assess memory using the Morris water maze, passive avoidance test, or Y-maze. Improvements in memory retention would suggest AChE inhibition. However, no such studies have been published. This protocol is speculative and provided as a template only. The compound has not been validated in any animal model.
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| ADME/Pharmacokinetics |
No pharmacokinetic data are available for (S)-(-)-O-Demethylbuchenavianine. As an acridine alkaloid, it is likely to have moderate lipophilicity and may be orally bioavailable. It may cross the blood-brain barrier due to its structural similarity to known CNS-active acridines. Metabolism may involve phase I (oxidation, demethylation) and phase II (conjugation) pathways. Half-life, clearance, and volume of distribution are unknown. For research purposes, the compound is stored as a powder at -20degC, protected from light and moisture. Solubility in DMSO and other organic solvents is expected but not well characterized.
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| Toxicity/Toxicokinetics |
Safety and toxicity data for (S)-(-)-O-Demethylbuchenavianine are not available. As an acridine derivative, it may be cytotoxic at high concentrations. Some acridine alkaloids are known to intercalate DNA and may have mutagenic potential. Standard laboratory safety precautions (gloves, lab coat, safety glasses, fume hood) should be used when handling this compound. Avoid inhalation and skin contact. It is not intended for human or veterinary use. No data on LD50, skin/eye irritation, or carcinogenicity are available.
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| References | |
| Additional Infomation |
This compound is a research-grade natural product, not an approved drug. It is used for natural product chemistry research, structure-activity relationship studies of acetylcholinesterase inhibitors, and as a potential lead compound for Alzheimer's disease research. No clinical trials are registered. It may also be used as a reference standard for phytochemical analysis of plant extracts. The compound is typically available in small quantities (milligrams) for research use. Molecular formula: C20H18N2O2, molecular weight: 318.37 g/mol. Purity: typically >95% by HPLC. For research use only. Not for diagnostic or therapeutic use.
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| Molecular Formula |
C21H21NO4
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|---|---|
| Molecular Weight |
351.40
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| Exact Mass |
351.147
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| CAS # |
91147-18-1
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| PubChem CID |
57342532
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| Appearance |
Solid powder
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| LogP |
3.965
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| Hydrogen Bond Donor Count |
2
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| Hydrogen Bond Acceptor Count |
5
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| Rotatable Bond Count |
2
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| Heavy Atom Count |
26
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| Complexity |
556
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| Defined Atom Stereocenter Count |
1
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| SMILES |
N1(C)C2=C(N(C)C(=O)N(CCCN3C(=O)C4=C(N(C)C3=O)N=CN4C)C2=O)N=C1
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| InChi Key |
BBZGOLNDVQZCIH-AWEZNQCLSA-N
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| InChi Code |
InChI=1S/C21H21NO4/c1-22-10-6-5-9-14(22)19-15(23)11-16(24)20-17(25)12-18(26-21(19)20)13-7-3-2-4-8-13/h2-4,7-8,11-12,14,23-24H,5-6,9-10H2,1H3/t14-/m0/s1
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| Chemical Name |
5,7-dihydroxy-8-[(2S)-1-methylpiperidin-2-yl]-2-phenylchromen-4-one
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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) |
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 | 2.8458 mL | 14.2288 mL | 28.4576 mL | |
| 5 mM | 0.5692 mL | 2.8458 mL | 5.6915 mL | |
| 10 mM | 0.2846 mL | 1.4229 mL | 2.8458 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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