| Size | Price | Stock | Qty |
|---|---|---|---|
| 1mg |
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| Other Sizes |
| Targets |
Ki: 500 nM (Nicotinic receptor) and 11000 nM (Muscarinic receptor)[1]
Lupanine shows binding affinity for the nicotinic receptor with a Ki value of 500 nM. This interaction with nicotinic receptors is consistent with its ganglioplegic activity. It may also interact with specific drugs used for treatment of the CNS and for analgesic activity. |
|---|---|
| ln Vitro |
With a 500 nM Ki, lupanine binds to nicotinic receptors with affinity. With a Ki value of 11000 nM, lupanine exhibits extremely low affinity for muscarinic receptors [1]. Lupanine (0-100 μM) has EC50 and DC50 values of 10.7 μM and 28.2 μM, respectively, making it a mild agonist and desensitizer of SH-SY5Y cells [2].
In vitro, Lupanine shows binding affinity for the nicotinic receptor with a Ki value of 500 nM. Its activity is typically assessed in receptor binding studies using radiolabeled ligands. As a quinolizidine alkaloid, it is used in biological studies with seeds of lupin genotypes of different origins. It has a weak sedative effect on the central nervous system. |
| ln Vivo |
More specifically, lupanine (100–300 mg/kg IP; 175-700 mg/kg PO) is much less hazardous when administered as a single injection to male EOPS Swiss mice (20–22 g) and Hartley guinea pigs (400–500 g). In dogs and cats, lupanine (1–7.5 mg/kg; IV) is superior to sparteine in treating secondary reflex hypertension brought on by carotid artery blockage and hypotension brought on by stimulation of the pulmonary and stomach nerves [1]. When dogs receiving atropine are given an injection of acetylcholine (500 pg/kg IV), nicotinic hypertension is caused [1]. Lupanine has an inhibiting influence on this process.
In vivo, Lupanine has a weak sedative effect on the central nervous system. It has ganglioplegic activity. It may interact with specific drugs used for treatment of the CNS and for analgesic activity. However, comprehensive in vivo efficacy data from published literature are limited. The compound is primarily used as a research tool. |
| Enzyme Assay |
For non-cell-based receptor binding assays, Lupanine can be evaluated using membrane preparations from cells expressing nicotinic receptors. Radioligand binding displacement experiments are performed using a suitable radiolabeled ligand such as [3H]-epibatidine or [125I]-α-bungarotoxin. Membrane homogenates are incubated with increasing concentrations of the test compound and a fixed concentration of the radioligand. Bound radioligand is separated from free by rapid filtration through glass fiber filters. Non-specific binding is determined in the presence of excess unlabeled nicotine. Ki values are calculated from displacement curves using nonlinear regression analysis.
|
| Cell Assay |
For in vitro cellular assays, cells expressing nicotinic receptors are cultured in appropriate media. For functional assays, the compound's ability to modulate receptor activity can be assessed. However, Lupanine is primarily used in receptor binding studies rather than functional cell-based assays. Its activity is typically characterized using radioligand binding displacement experiments.
|
| Animal Protocol |
For in vivo animal studies, Lupanine can be administered to rodents to study its sedative and ganglioplegic effects. In models of CNS activity, its effects on behavior and motor function are assessed. In models of analgesia, its effects on pain responses are evaluated. Dosing regimens vary depending on the specific model and desired exposure levels.
|
| ADME/Pharmacokinetics |
Lupanine has a molecular weight of 248.36 and a molecular formula of C15H24N2O. It has a purity of 98.04%. The compound is a natural quinolizidine alkaloid. It should be stored according to the manufacturer's recommendations. It is for research use only and is not intended for human consumption.
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| Toxicity/Toxicokinetics |
The toxicity profile of Lupanine has not been extensively reported. As a natural alkaloid with ganglioplegic activity, potential adverse effects may include modulation of nicotinic receptor function. The compound is for research use only and is not intended for human consumption. Standard safety precautions should be observed when handling the compound.
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| References |
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| Additional Infomation |
Lupanine is a δ-lactam derived from the oxidation of spatine at the 2-position. It is the main alkaloid in the seeds of the tall lupin (Lupinus exaltatus), Mexican lupin (L. mexicanus), and round-flowered lupin (L. rotundiflorus), and is one of the most important tetracyclic quinolone alkaloids. It is a quinolone alkaloid, a tertiary amine, and a δ-lactam. It is the conjugate base of Lupanine (1+). It is derived from the hydride of spatine. Lupanine has also been reported in Ormosia emarginata, Thermopsis lanceolata, and several other organisms with relevant data. See also: Inflorescence (partial) of Cytisus scoparius.
Lupanine (D-Lupanine, CAS 550-90-3) is a natural ketonic derivative of Sparteine with ganglioplegic activity. It shows binding affinity for the nicotinic receptor with a Ki value of 500 nM. It has a weak sedative effect on the central nervous system and is used in biological studies with quinolizidine alkaloids. It is available for research purposes only. |
| Molecular Formula |
C15H24N2O
|
|---|---|
| Molecular Weight |
248.36
|
| Exact Mass |
412.406
|
| CAS # |
550-90-3
|
| Related CAS # |
Lupanine hydrochloride;1025-39-4
|
| PubChem CID |
91471
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| Appearance |
Colorless to light yellow liquid
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| Density |
0.9±0.1 g/cm3
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| Boiling Point |
457.4±12.0 °C at 760 mmHg
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| Melting Point |
40-44°
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| Flash Point |
221.8±13.1 °C
|
| Vapour Pressure |
0.0±0.5 mmHg at 25°C
|
| Index of Refraction |
1.498
|
| Source |
Originated from plants: Leguminosae Lupinus albus Linn.
|
| LogP |
13.33
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| Hydrogen Bond Donor Count |
0
|
| Hydrogen Bond Acceptor Count |
2
|
| Rotatable Bond Count |
0
|
| Heavy Atom Count |
18
|
| Complexity |
356
|
| Defined Atom Stereocenter Count |
4
|
| SMILES |
O=C1CCC[C@@]2([H])N1C[C@@]3([H])[C@@](CCCC4)([H])N4C[C@]2([H])C3
|
| InChi Key |
JYIJIIVLEOETIQ-XDQVBPFNSA-N
|
| InChi Code |
InChI=1S/C15H24N2O/c18-15-6-3-5-14-11-8-12(10-17(14)15)13-4-1-2-7-16(13)9-11/h11-14H,1-10H2/t11-,12-,13-,14+/m0/s1
|
| Chemical Name |
(1S,2R,9S,10S)-7,15-diazatetracyclo[7.7.1.02,7.010,15]heptadecan-6-one
|
| 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)
|
| Solubility (In Vitro) |
DMSO: ≥ 50 mg/mL (~201.3 mM)
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|---|---|
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 1.25 mg/mL (5.03 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween-80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), Clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of DMSO stock solution (12.5 mg/mL) to 400 μL of PEG300 and mix well; then add 50 μL of Tween-80 and mix well; finally add 450 μL of physiological saline and adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 1.25 mg/mL (5.03 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), Clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of DMSO stock solution (12.5 mg/mL) to 900 μL of 20% SBE-β-CD saline and mix well. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. Solubility in Formulation 3: 1.25 mg/mL (5.03 mM) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), Suspended solution; with ultrasonication. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of DMSO stock solution (12.5 mg/mL) to 900 μL of corn oil and mix well. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 4.0264 mL | 20.1321 mL | 40.2641 mL | |
| 5 mM | 0.8053 mL | 4.0264 mL | 8.0528 mL | |
| 10 mM | 0.4026 mL | 2.0132 mL | 4.0264 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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