| Size | Price | Stock | Qty |
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| 1mg |
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| 5mg |
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| 10mg | |||
| Other Sizes |
| Targets |
The primary target of Anisatin is the GABAA receptor. It acts as a non-competitive antagonist (channel blocker), binding to the picrotoxinin (PTX) site located within the chloride ion channel. It also inhibits [3H]diazepam binding enhanced by GABA, indicating a negative allosteric modulation of the benzodiazepine site via channel blockade.
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| ln Vitro |
Without altering the baseline specific binding to rat brain membranes, anisatin blocks [3H]diazepam binding that is increased by either GABA or pentobarbital[1].
In vitro, Anisatin is a potent inhibitor of [3H]EBOB binding to the picrotoxinin site on rat brain GABAA receptors, with an IC50 of 282 nM. This confirms it is a high-affinity ligand for the chloride channel pore. It acts as a potent non-competitive antagonist, blocking the receptor's function and leading to increased neuronal excitability. |
| ln Vivo |
Anisatin has been shown to have an LD50 in mice ranging from 0.76 to 1 mg/kg (po and ip)[1].
Anisatin is a potent convulsant and neurotoxin in vivo. By blocking GABAA receptors, it disrupts inhibitory neurotransmission in the central nervous system, leading to neuronal hyperexcitability and convulsive seizures. Ingestion of seeds containing anisatin leads to severe symptoms including seizures, vomiting, and neurotoxicity, making it a potent tool for seizure research. |
| Enzyme Assay |
The standard non-cellular assay for Anisatin is a [3H]EBOB (ethynylbicycloorthobenzoate) binding assay. Rat brain synaptic membranes are prepared and incubated with 2 nM [3H]EBOB and varying concentrations of Anisatin (e.g., 1 nM to 100 uM). After incubation at 25degC for 90 min, bound and free ligand are separated by filtration to determine the IC50 for displacement.
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| Cell Assay |
N/A. However, its effect on GABAA receptor function can be studied in cultured primary neurons using patch-clamp electrophysiology. Neurons are held at -60 mV, and GABA is puffed onto the cell to evoke an inhibitory postsynaptic current (IPSC). Anisatin is then applied and the reduction in the amplitude of the GABA-evoked current is measured.
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| Animal Protocol |
Anisatin is used as a seizure-inducing agent. A standard in vivo protocol involves administering Anisatin (e.g., 2-10 mg/kg) to Swiss Webster mice via intraperitoneal injection. Immediately after injection, mice are observed for the latency to onset of clonic or tonic-clonic seizures. The time to myoclonic jerks and the percentage of animals seizing are recorded.
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| ADME/Pharmacokinetics |
Anisatin has an absolute oral bioavailability of 22.6% in mouse blood. Following intravenous administration (0.5 mg/kg) and oral administration (1 mg/kg), its pharmacokinetics are characterized using UPLC-MS/MS. As a neurotoxin, it is absorbed and distributed to the brain, where it binds to GABAA receptors to exert its effects.
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| Toxicity/Toxicokinetics |
Toxicity Summary
Anisatin is a GABA system antagonist. It binds non-competitively to the bitter substance binding site of the GABA receptor, prolonging the closure time of the receptor channel and reducing its opening probability. (A345) Anisatin is a potent neurotoxin. Its oral LD50 in mice is extremely low, indicating high acute toxicity. Ingestion of the Japanese star anise plant, which contains anisatin, causes severe poisoning characterized by epileptic seizures, vomiting, and neurotoxicity. It should be handled with extreme caution as a hazardous chemical. |
| References |
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| Additional Infomation |
Anisatin has been reported to be present in star anise (Illicium simonsii), large star anise (Illicium majus), and other organisms with relevant data. Anisatin is a plant toxin found in Japanese star anise (Illicium anisatum). Japanese star anise is used in Japan as incense, known as "shikimi," and also in traditional external remedies. (L1226)
Anisatin is a classic natural product toxin used as a tool to study the pharmacology of the GABAA receptor's picrotoxin site. It is structurally distinct from picrotoxin itself and is isolated from a different plant source, providing a complementary chemical tool for probing the structure-activity relationships (SAR) of the ion channel pore. It is not used clinically. |
| Molecular Formula |
C15H20O8
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|---|---|
| Molecular Weight |
328.31
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| Exact Mass |
328.116
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| CAS # |
5230-87-5
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| PubChem CID |
115121
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| Appearance |
White to off-white solid powder
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| Density |
1.149g/cm3
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| Boiling Point |
251.2ºC at 760 mmHg
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| Melting Point |
227-228ºC
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| Flash Point |
106.7ºC
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| Index of Refraction |
1.486
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| LogP |
-1.9
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| Hydrogen Bond Donor Count |
4
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| Hydrogen Bond Acceptor Count |
8
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| Rotatable Bond Count |
0
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| Heavy Atom Count |
23
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| Complexity |
621
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| Defined Atom Stereocenter Count |
8
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| SMILES |
C[C@@H]1C[C@H]([C@]2([C@@]13C[C@H]([C@]([C@@]24COC4=O)(C)O)OC(=O)[C@@H]3O)O)O
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| InChi Key |
GEVWHIDSUOMVRI-QWNPAUMXSA-N
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| InChi Code |
InChI=1S/C15H20O8/c1-6-3-7(16)15(21)13(6)4-8(23-10(18)9(13)17)12(2,20)14(15)5-22-11(14)19/h6-9,16-17,20-21H,3-5H2,1-2H3/t6-,7-,8-,9+,12+,13+,14+,15-/m1/s1
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| Chemical Name |
(1S,2R,4R,5R,6S,7R,8R,11R)-4,5,7,11-tetrahydroxy-2,7-dimethylspiro[9-oxatricyclo[6.3.1.01,5]dodecane-6,3'-oxetane]-2',10-dione
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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 | 3.0459 mL | 15.2295 mL | 30.4590 mL | |
| 5 mM | 0.6092 mL | 3.0459 mL | 6.0918 mL | |
| 10 mM | 0.3046 mL | 1.5230 mL | 3.0459 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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