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| Targets |
Levophacetoperan targets the dopamine and norepinephrine transporters (DAT and NET) in the central nervous system. By binding to these transporters, the compound inhibits the reuptake of dopamine and norepinephrine from the synaptic cleft, increasing the concentrations of these neurotransmitters in the synapse. This results in enhanced dopaminergic and noradrenergic signaling, which is associated with increased alertness, improved mood, and appetite suppression. The compound's mechanism of action is similar to that of other psychostimulants, such as methylphenidate and amphetamine, but its potency and selectivity may differ due to its distinct stereochemistry and ester configuration. In vitro, Levophacetoperan competitively inhibits dopamine uptake in the striatum and cortex of rats, as well as norepinephrine uptake in the hypothalamus and brainstem.
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| ln Vitro |
In vitro, levophaacetoperane competitively inhibits dopamine uptake in the striatum and cortex of rats, as well as norepinephrine uptake in the hypothalamus and brain. A psychostimulant is levophaacetoperane [1]. Levopaphen has been utilized as an anorectic and antidepressant. The reverse ester of methylphenidate is called levaphene.
In vitro, Levophacetoperan competitively inhibits dopamine uptake in rat striatal and cortical synaptosomes, as well as norepinephrine uptake in hypothalamic and brainstem synaptosomes. The compound's inhibitory activity is concentration-dependent, and its potency for dopamine and norepinephrine transporters has been characterized in radioligand binding and uptake assays. In addition to its effects on monoamine transporters, Levophacetoperan may have other pharmacological activities, including effects on serotonin transporters or receptors, although these are less well-characterized. The compound's in vitro activity is consistent with its psychostimulant and antidepressant effects observed in vivo. |
| ln Vivo |
In vivo, Levophacetoperan has been used as an antidepressant and anorectic agent. The compound's psychostimulant effects are associated with increased locomotor activity and reduced food intake in animal models. In dogs, Levophacetoperan has been shown to reverse apnea after a single intravenous injection, indicating its potential as a respiratory stimulant. The compound's effects on mood and appetite are consistent with its mechanism of action as a dopamine and norepinephrine reuptake inhibitor. However, its clinical use has been limited, and it is primarily a research compound.
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| Enzyme Assay |
The non-cellular assay for Levophacetoperan involves measuring its binding affinity for dopamine and norepinephrine transporters using radioligand binding assays. Membrane preparations from rat striatum (for DAT) or rat cerebral cortex (for NET) are incubated with a radiolabeled transporter ligand (such as [³H]-WIN 35,428 for DAT or [³H]-nisoxetine for NET) and varying concentrations of Levophacetoperan. After incubation, bound and free radioligand are separated by filtration, and radioactivity is measured by liquid scintillation counting. The inhibition of radioligand binding by Levophacetoperan is calculated, and the IC50 or Ki is determined from competition curves. The selectivity of the compound for DAT over NET is assessed by comparing its potency in these two assays.
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| Cell Assay |
The cellular assay for Levophacetoperan involves measuring its inhibition of dopamine or norepinephrine uptake in cultured cells or synaptosomes. Cells expressing the human dopamine transporter or norepinephrine transporter (or rat synaptosomes prepared from brain regions) are incubated with a radiolabeled substrate (such as [³H]-dopamine or [³H]-norepinephrine) in the presence of varying concentrations of Levophacetoperan. The uptake of the radiolabeled substrate is measured after a defined incubation period, and the inhibition by Levophacetoperan is calculated. The IC50 for uptake inhibition is determined from concentration-response curves. The compound's effects on cell viability are assessed to ensure that the observed inhibition of uptake is not due to non-specific cytotoxicity.
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| Animal Protocol |
The in vivo animal studies for Levophacetoperan typically use rodent models to assess its psychostimulant, antidepressant, and anorectic effects. In the open field test, rodents are treated with Levophacetoperan, and locomotor activity is measured to assess stimulant effects. In the forced swim test or tail suspension test, the compound's antidepressant-like effects are assessed by measuring the reduction in immobility time. In food intake studies, the compound's anorectic effects are assessed by measuring food consumption over a defined period. In apnea reversal studies, dogs are anesthetized and apnea is induced, and the reversal of apnea by intravenous administration of Levophacetoperan is assessed by monitoring respiratory parameters.
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| ADME/Pharmacokinetics |
Levophacetoperan HCl has a molecular weight of 269.77 g/mol and a molecular formula of C₁₄H₂₀ClNO₂. The compound is soluble in water and organic solvents. It should be stored in a cool, dry place, protected from light and moisture. Its pharmacokinetic properties, including absorption, distribution, metabolism, and excretion, have been characterized in preclinical studies.
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| Toxicity/Toxicokinetics |
Levophacetoperan HCl is generally well-tolerated in preclinical studies at therapeutically relevant doses. However, as a psychostimulant, it may cause dose-dependent side effects such as increased heart rate, elevated blood pressure, insomnia, and anorexia. The compound's safety profile is consistent with that of other psychostimulants, such as methylphenidate and amphetamine. Comprehensive toxicology data are limited, and the compound is not widely used clinically.
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| References |
[1]. Ramirez A, et al. [Effects of levophacetoperane, pemoline, fenozolone, and centrophenoxine on catecholamines and serotonin uptake in various parts of the rat brain]. C R Acad Sci Hebd Seances Acad Sci D. 1978 Jul 3;187(1):53-6.
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| Additional Infomation |
Levophacetoperan HCl (Lidepran®) is a centrally acting sympathomimetic agent that has been used as an antidepressant and anorectic. It is the reverse ester of methylphenidate and acts as a dopamine and norepinephrine reuptake inhibitor. The compound has been studied for its potential in the treatment of depression, as an appetite suppressant, and as a respiratory stimulant. Although its clinical use has been limited, Levophacetoperan remains a subject of research for its pharmacological properties and as a tool for studying monoamine transporter function.
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| Molecular Formula |
C14H19NO2.HCL
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| Molecular Weight |
269.7671
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| Exact Mass |
269.118
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| CAS # |
23257-56-9
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| Related CAS # |
Levophacetoperane;24558-01-8
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| PubChem CID |
76957863
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| Appearance |
White to off-white solid powder
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| Density |
1.07g/cm3
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| Boiling Point |
325.1ºC at 760mmHg
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| Flash Point |
150.4ºC
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| LogP |
3.563
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| Hydrogen Bond Donor Count |
2
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| Hydrogen Bond Acceptor Count |
3
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| Rotatable Bond Count |
4
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| Heavy Atom Count |
18
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| Complexity |
249
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| Defined Atom Stereocenter Count |
2
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| SMILES |
[H][C@]1(NCCCC1)[C@H](OC(C)=O)C2=CC=CC=C2.[H]Cl
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| InChi Key |
LDPSCUMJCVDWCB-DTPOWOMPSA-N
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| InChi Code |
InChI=1S/C14H19NO2.ClH/c1-11(16)17-14(12-7-3-2-4-8-12)13-9-5-6-10-15-13;/h2-4,7-8,13-15H,5-6,9-10H2,1H3;1H/t13-,14-;/m1./s1
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| Chemical Name |
[(R)-phenyl-[(2R)-piperidin-2-yl]methyl] acetate;hydrochloride
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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: Please store this product in a sealed and protected environment, avoid exposure to moisture. |
| 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) |
DMSO : ~16.67 mg/mL (~61.79 mM)
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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 | 3.7069 mL | 18.5343 mL | 37.0686 mL | |
| 5 mM | 0.7414 mL | 3.7069 mL | 7.4137 mL | |
| 10 mM | 0.3707 mL | 1.8534 mL | 3.7069 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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