| Size | Price | Stock | Qty |
|---|---|---|---|
| 5mg |
|
||
| 10mg |
|
||
| 50mg |
|
||
| 100mg | |||
| Other Sizes |
| Targets |
Levetimide targets sigma receptors, particularly sigma-1 and sigma-2 receptors, which are non-opioid, non-phencyclidine binding sites that are involved in various physiological functions, including modulation of neurotransmitter release, neuroprotection, and cell proliferation. Levetimide is a potent inhibitor of [³H](+)pentazocine binding, with a Ki of 2.2 nM. However, unlike its enantiomer dexetimide, which shows stereoselectivity for sigma receptors, Levetimide inhibits [³H]DTG binding (another sigma receptor ligand) without stereoselectivity, with a Ki value of 103 nM. This suggests that Levetimide binds to sigma receptors but does not distinguish between different stereoisomers of sigma receptor ligands. Levetimide is also a muscarinic acetylcholine receptor antagonist, but it is the less active enantiomer compared to dexetimide.
|
|---|---|
| ln Vitro |
Levetimide is not stereoselective (Ki value 103 nM), however it significantly inhibits [3H]DTG binding [1].
In vitro, Levetimide potently inhibits [³H](+)pentazocine binding to sigma receptors with a Ki of 2.2 nM. This binding is stereoselective, as the compound's enantiomer dexetimide has different potency at sigma receptors. However, Levetimide inhibits [³H]DTG binding without stereoselectivity, with a Ki of 103 nM, indicating that it interacts with sigma receptors but does not show stereospecificity for this ligand. The compound's activity at muscarinic receptors is limited, as it is the less active enantiomer compared to dexetimide. Levetimide is used as a negative control or as a tool to study the stereoselectivity of sigma receptor binding. |
| ln Vivo |
In vivo, Levetimide has not been extensively studied as a therapeutic agent due to its lack of significant pharmacological activity. Its primary use is as a research tool to study the stereoselectivity of ligand-receptor interactions and to characterize the binding properties of sigma receptors. The compound's in vivo pharmacokinetics and pharmacological effects are not well-documented in the available literature.
|
| Enzyme Assay |
The non-cellular assay for Levetimide involves competitive radioligand binding to sigma receptors. Membrane preparations from tissues or cells expressing sigma receptors (such as rat brain homogenates or cells transfected with sigma receptor genes) are incubated with a fixed concentration of a radiolabeled sigma receptor ligand (such as [³H](+)pentazocine or [³H]DTG) and varying concentrations of Levetimide. After incubation, bound and free radioligand are separated by filtration, and radioactivity is measured by liquid scintillation counting. The inhibition of radioligand binding by Levetimide is calculated, and the Ki is determined from competition curves. The stereoselectivity of Levetimide's binding is assessed by comparing its potency to that of its enantiomer dexetimide in similar assays.
|
| Cell Assay |
The cellular assay for Levetimide involves testing its effects on sigma receptor-mediated signaling in cultured cells. Cells expressing sigma receptors (such as neuronal or cancer cell lines) are treated with Levetimide, and its effects on cell proliferation, calcium signaling, or other sigma receptor-mediated responses are measured. However, specific protocols for Levetimide in cellular assays are not well-documented, as the compound is primarily used as a binding tool rather than as a functional modulator.
|
| Animal Protocol |
In vivo animal studies for Levetimide have not been extensively reported. As a research tool, it may be used in behavioral studies to assess the role of sigma receptors in various physiological and pathological processes, but its lack of significant activity limits its utility in vivo.
|
| ADME/Pharmacokinetics |
Levetimide has a molecular weight of 362.46 g/mol and a molecular formula of C₂₃H₂₆N₂O₂. The compound is a solid that is soluble in organic solvents. It should be stored in a cool, dry place, protected from light. Its pharmacokinetic properties have not been extensively characterized.
|
| Toxicity/Toxicokinetics |
Levetimide is generally considered to have low toxicity, as it is the less active enantiomer of dexetimide. However, comprehensive toxicology data are lacking. The compound should be handled with appropriate laboratory safety precautions.
|
| References | |
| Additional Infomation |
Levetimide is the R-enantiomer of dexetimide and is considered to be the inactive enantiomer of the muscarinic acetylcholine receptor antagonist. It is a potent inhibitor of [³H](+)pentazocine binding to sigma receptors with a Ki of 2.2 nM, but it does not show stereoselectivity for sigma receptor binding. Levetimide is primarily used as a research tool for studying the stereoselectivity of sigma receptor binding and for characterizing the binding properties of sigma receptor ligands. Its lack of significant pharmacological activity makes it a useful negative control in studies of sigma receptor pharmacology.
|
| Molecular Formula |
C23H26N2O2
|
|---|---|
| Molecular Weight |
362.47
|
| Exact Mass |
362.199
|
| CAS # |
21888-99-3
|
| Related CAS # |
Dexetimide;21888-98-2
|
| PubChem CID |
30844
|
| Appearance |
White to off-white solid powder
|
| Density |
1.178g/cm3
|
| Boiling Point |
543.9ºC at 760mmHg
|
| Flash Point |
282.7ºC
|
| LogP |
3.487
|
| Hydrogen Bond Donor Count |
1
|
| Hydrogen Bond Acceptor Count |
3
|
| Rotatable Bond Count |
4
|
| Heavy Atom Count |
27
|
| Complexity |
529
|
| Defined Atom Stereocenter Count |
1
|
| SMILES |
C1CN(CCC1[C@]2(CCC(=O)NC2=O)C3=CC=CC=C3)CC4=CC=CC=C4
|
| InChi Key |
LQQIVYSCPWCSSD-QHCPKHFHSA-N
|
| InChi Code |
InChI=1S/C23H26N2O2/c26-21-11-14-23(22(27)24-21,19-9-5-2-6-10-19)20-12-15-25(16-13-20)17-18-7-3-1-4-8-18/h1-10,20H,11-17H2,(H,24,26,27)/t23-/m0/s1
|
| Chemical Name |
(3R)-3-(1-benzylpiperidin-4-yl)-3-phenylpiperidine-2,6-dione
|
| Synonyms |
laevo-Benzetimide; l-Benzetimide; Levetimide
|
| 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)
|
| Solubility (In Vitro) |
DMSO : ≥ 100 mg/mL (~275.89 mM)
|
|---|---|
| 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 | 2.7588 mL | 13.7942 mL | 27.5885 mL | |
| 5 mM | 0.5518 mL | 2.7588 mL | 5.5177 mL | |
| 10 mM | 0.2759 mL | 1.3794 mL | 2.7588 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.
Products are for research use only; We do not sell to patients
Copyright 2020 InvivoChem LLC | All Rights Reserved
