| Size | Price | Stock | Qty |
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| 500mg |
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| 1g |
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| 2g |
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| Other Sizes |
Purity: ≥98%
| Targets |
Pseudopelletierine targets acetylcholine esterase (AChE) as an inhibitor. By inhibiting AChE, it prevents the breakdown of acetylcholine, leading to increased cholinergic signaling. The compound also inhibits mitochondrial membrane potential, which may contribute to its anti-cancer effects. It triggers a stimulant reflex similar to strychnine and has been shown to be effective against tapeworms, ringworms, and nematodes. Pseudopelletierine's interaction with cholinergic pathways and its effects on cellular energy metabolism make it a valuable tool for studying neurological and inflammatory conditions.
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| ln Vitro |
In vitro, pseudopelletierine has been shown to inhibit cancer cell viability and exhibit inhibitory effects on inflammatory diseases. It inhibits mitochondrial membrane potential, which may contribute to its anti-cancer effects. Simple bark-extracts containing pseudopelletierine have been shown to be effective in vitro against intestinal bacteria such as Salmonella typhi, Vibrio cholerae, herpes simplex virus, HIV, and tumors. Nematicidal activity assays have shown differences in activity between isopelletierine and pseudopelletierine. Pseudopelletierine derivatives have been synthesized to mimic the anti-inflammatory activity of curcumin while improving its bioavailability.
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| ln Vivo |
In vivo, pseudopelletierine triggers a stimulant reflex similar to strychnine and is effective against tapeworms, ringworms, and nematodes. It has been shown to be effective in treating inflammatory diseases. The compound has been used in traditional medicine for its anthelmintic properties. For in vivo formulation, pseudopelletierine free base can be prepared in a solution of 10% DMSO + 40% PEG300 + 5% Tween 80 + 45% saline. However, detailed in vivo efficacy data in modern pharmacological models are limited, and the compound is primarily used in research settings.
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| Enzyme Assay |
In vitro enzyme/receptor binding assays for pseudopelletierine typically involve measuring its inhibition of acetylcholinesterase (AChE) activity. The assay uses a colorimetric method based on Ellman's reaction, where AChE is incubated with varying concentrations of pseudopelletierine and the substrate acetylthiocholine. The hydrolysis of acetylthiocholine produces thiocholine, which reacts with 5,5′-dithiobis-(2-nitrobenzoic acid) (DTNB) to produce a yellow color measured at 412 nm. The IC₅₀ value for AChE inhibition is calculated from the dose-response curve. This assay confirms the compound's mechanism as an AChE inhibitor.
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| Cell Assay |
In vitro cell-based assays for pseudopelletierine evaluate its effects on cancer cell viability and inflammatory responses. Cancer cells (e.g., HEK293, various carcinoma lines) are cultured in appropriate media and treated with serial dilutions of pseudopelletierine for 24-72 hours. Cell viability is assessed using MTT or CellTiter-Glo assays. Mitochondrial membrane potential is measured using fluorescent dyes such as JC-1. Inflammatory responses are evaluated by measuring cytokine production in immune cells stimulated with lipopolysaccharide (LPS). The compound's effects on cell proliferation, apoptosis, and inflammatory markers are quantified to determine its bioactivity.
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| Animal Protocol |
In vivo animal experiments for pseudopelletierine are limited in modern pharmacological literature. However, the compound has been studied in the context of traditional medicine for its anthelmintic properties. For potential in vivo studies, pseudopelletierine can be administered orally or via intraperitoneal injection in animal models of parasitic infection or inflammation. The compound can be formulated in 10% DMSO + 40% PEG300 + 5% Tween 80 + 45% saline. Pharmacodynamic endpoints would include assessment of parasite burden, inflammatory markers, and survival. However, comprehensive modern in vivo studies are lacking.
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| ADME/Pharmacokinetics |
Pharmacokinetic (PK) data for pseudopelletierine are limited. The compound has a molecular weight of 153.22 g/mol and is a volatile, strong base. One gram dissolves in about 2.5 ml water and 10 ml ether; it is freely soluble in alcohol and chloroform, sparingly soluble in petroleum ether. The hydrochloride salt form provides aqueous solubility not achievable with the free base. The free base has limited aqueous solubility and oxidative sensitivity. Pseudopelletierine is sparingly soluble in methanol, which influences its bioavailability. Comprehensive ADME studies are needed.
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| Toxicity/Toxicokinetics |
The toxicity profile of pseudopelletierine has been characterized in basic toxicological studies. The acute subcutaneous LDLo in mice is 200 mg/kg, and in guinea pigs it is 230 mg/kg. The compound causes skin irritation (Category 2), serious eye irritation (Category 2), and specific target organ toxicity - single exposure (Category 3). Under fire conditions, it may decompose and emit toxic fumes. The compound should be handled with appropriate personal protective equipment, including gloves and eye protection. For research use only, not for human therapeutic use.
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| References |
: Vallejo-López M, Écija P, Vogt N, Demaison J, Lesarri A, Basterretxea FJ, Cocinero EJ. N-Methyl Inversion and Accurate Equilibrium Structures in Alkaloids: Pseudopelletierine. Chemistry. 2017 Nov 21;23(65):16491-16496. doi: 10.1002/chem.201702232. Epub 2017 Oct 9. PubMed PMID: 28759141.
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| Additional Infomation |
It has been reported that pomegranates contain 9-methyl-9-azabicyclo[3.3.1]nonane-3-one, and there is relevant data.
Pseudopelletierine (NSC 116056, Granatan-3-one, Granatonine) is a naturally occurring tropane alkaloid and the main alkaloid derived from the root-bark of Punica granatum. It is an acetylcholine esterase inhibitor that has been shown to be effective in treating inflammatory diseases. The synthesis of pseudopelletierine is based on a modification of the classic Ugi 4-component reaction and was achieved through asymmetric synthesis. The crystal structure of pseudopelletierine was determined by X-ray diffraction and found to have a monoclinic form with space group P2/c. Pseudopelletierine has been shown to inhibit cancer cell viability and mitochondrial membrane potential. It is primarily a research tool and has not progressed to clinical trials. |
| Molecular Formula |
C9H15NO
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| Molecular Weight |
153.2215
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| Exact Mass |
153.115
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| CAS # |
552-70-5
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| Related CAS # |
552-70-5;6164-62-1 (HCl);6164-64-3 (sulfate hydrate);6164-61-0 (hydrate);
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| PubChem CID |
11096
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| Appearance |
Typically exists as solid at room temperature
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| Density |
1.0±0.1 g/cm3
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| Boiling Point |
246.7±15.0 °C at 760 mmHg
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| Melting Point |
63-65°C
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| Flash Point |
95.9±10.0 °C
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| Vapour Pressure |
0.0±0.5 mmHg at 25°C
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| Index of Refraction |
1.497
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| LogP |
0.63
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| Hydrogen Bond Donor Count |
0
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| Hydrogen Bond Acceptor Count |
2
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| Rotatable Bond Count |
0
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| Heavy Atom Count |
11
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| Complexity |
162
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| Defined Atom Stereocenter Count |
0
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| SMILES |
O=C1C([H])([H])C2([H])C([H])([H])C([H])([H])C([H])([H])C([H])(C1([H])[H])N2C([H])([H])[H]
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| InChi Key |
RHWSKVCZXBAWLZ-OCAPTIKFSA-N
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| InChi Code |
InChI=1S/C9H15NO/c1-10-7-3-2-4-8(10)6-9(11)5-7/h7-8H,2-6H2,1H3/t7-,8+
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| Chemical Name |
9-Methyl-9-azabicyclo[3.3.1]nonan-3-one
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| Synonyms |
Pseudopelletierine Granatan-3-one Granatonine NSC 116056
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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 |
| 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 | 6.5266 mL | 32.6328 mL | 65.2656 mL | |
| 5 mM | 1.3053 mL | 6.5266 mL | 13.0531 mL | |
| 10 mM | 0.6527 mL | 3.2633 mL | 6.5266 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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