(-)-Sparteine

CAS# 90-39-1

(-)-Sparteine

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Chemical structure

(-)-Sparteine

3D structure

Chemical Properties of (-)-Sparteine

Cas No. 90-39-1 SDF Download SDF
PubChem ID 644020 Appearance Powder
Formula C15H26N2 M.Wt 234.3
Type of Compound Alkaloids Storage Desiccate at -20°C
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Chemical Name (1S,2R,9S,10S)-7,15-diazatetracyclo[7.7.1.02,7.010,15]heptadecane
SMILES C1CCN2CC3CC(C2C1)CN4C3CCCC4
Standard InChIKey SLRCCWJSBJZJBV-ZQDZILKHSA-N
Standard InChI InChI=1S/C15H26N2/c1-3-7-16-11-13-9-12(14(16)5-1)10-17-8-4-2-6-15(13)17/h12-15H,1-11H2/t12-,13-,14-,15+/m0/s1
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Source of (-)-Sparteine

The herbs of Parochetus communis

Biological Activity of (-)-Sparteine

DescriptionSparteine is a strong inhibitor of mephenytoin p-hydroxylation.

(-)-Sparteine Dilution Calculator

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(-)-Sparteine Molarity Calculator

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Preparing Stock Solutions of (-)-Sparteine

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 4.268 mL 21.3402 mL 42.6803 mL 85.3606 mL 106.7008 mL
5 mM 0.8536 mL 4.268 mL 8.5361 mL 17.0721 mL 21.3402 mL
10 mM 0.4268 mL 2.134 mL 4.268 mL 8.5361 mL 10.6701 mL
50 mM 0.0854 mL 0.4268 mL 0.8536 mL 1.7072 mL 2.134 mL
100 mM 0.0427 mL 0.2134 mL 0.4268 mL 0.8536 mL 1.067 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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References on (-)-Sparteine

Tri-Allelic Haplotypes Determine and Differentiate Functionally Normal Allele CYP2D6*2 and Impaired Allele CYP2D6*41.[Pubmed:33043448]

Clin Pharmacol Ther. 2020 Oct 12.

CYP2D6 metabolizes 20-25% of all clinically used drugs and its complex genetic polymorphism is a major determinant of drug safety and efficacy. We investigated the basis for the functional difference between the two common alleles *2 (g.2851C>T + g.4181G>C, normal function) and *41 (additional intronic g.2989G>A, reduced function). A recently reported far-distant enhancer polymorphism rs5758550A/G linked to *2 has been suggested to play a decisive role. Genotyping of two white cohorts confirmed strong linkage of rs5758550G to *2, whereas no influence was found on metabolic ratio of sparteine or hepatic expression. Genomic plasmid constructs carrying individual variants or combinations thereof were expressed in COS1 and Huh7 cells. Both g.2851C>T(R296C) and g.2989G>A reduced enzyme activity and protein levels similarly by ~ 50-65% compared to reference (*1), whereas the double variant had only ~ 20% activity. Although the unexpected loss of function caused by g.2851C>T was compensated by g.4181G>C (mimicking the EM-phenotype of *2), the additional loss of function due to intronic g.2989G>A in the triple variant was not compensated (mimicking the IM-phenotype of *41). We also confirmed increased erroneous splicing in carriers of g.2989G>A but not of g.2851C>T as a likely explanation for the impaired function of *41. In conclusion, our data demonstrate g.2989G>A as causal variant of impaired allele CYP2D6*41 whereas triple-haplotypes have to be considered to explain the functional difference between *2 and *41. These data are important for genotyping strategies and clinical implementation of CYP2D6 pharmacogenetics.

Insight into the Bonding and Aggregation of Alkyllithiums by Experimental Charge Density Studies and Energy Decomposition Analyses.[Pubmed:32811141]

J Am Chem Soc. 2020 Sep 16;142(37):15897-15906.

In this Article, the organolithiums [((-)-Sparteine)Li(t)Bu] (1), [(ABCO)Li(t)Bu]2 (2), and [(ABCO)2(Li(i)Pr)4] (3) are investigated by means of experimental and theoretical charge density determination to elucidate the nature of the Li-C and Li-N bonds. Furthermore, the valence shell charge concentrations (VSCCs) in the nonbonding region of the deprotonated Calpha-atom will provide some insight on the localization of the carbanionic lone pair. Analysis of the electron density (rho(rBCP)), Laplacian (nabla(2)rho(rBCP)), and the energy decomposition (EDA) confirmed that the Li-C/N bond exhibits astonishingly similar characteristics, to reveal an increasingly polar contact with decreasing aggregate size. This explains former observations on the incorporation of halide salts in organolithium reagents. Furthermore, it could be shown that the bonding properties of the (i)Pr group are similar to those of the (t)Bu substituent. The accuracy of fit to all previously determined properties in organolithiums is remarkable.

Induction of CD4(+)CD25(+) Regulatory T Cells from In Vitro Grown Human Mononuclear Cells by Sparteine Sulfate and Harpagoside.[Pubmed:32781652]

Biology (Basel). 2020 Aug 6;9(8). pii: biology9080211.

Regulatory T cells (Tregs) are key players in the regulation of inflammatory responses. In this study, two natural molecules, namely, sparteine sulfate (SS) and harpagoside (Harp), were investigated for their ability to induce Tregs in human peripheral blood mononuclear cells (PBMCs). PBMCs were isolated from healthy volunteers and grown in the presence or absence of ConA, with TGF-beta, SS or Harp. Expression of the mRNA of FoxP3, TGF-beta, IL-10 and GAPDH was assessed via q-PCR. The expression of Treg markers including CD4, CD25, CD127 and FoxP3 was measured via flow cytometry. The secretion of IL-10 and TGF-beta by cultured cells was assessed by ELISA. Furthermore, the suppressive role of SS and Harp on PBMCs in vitro was tested via allogeneic mixed lymphocyte reaction (MLR). Data obtained show that both compounds increased the expression of FoxP3, TGF-beta and IL-10 mRNA in resting PBMCs but to a lesser extent in activated cells. Moreover, they significantly increased the percent of CD4(+)CD25(+)FoxP3(+)CD127(-) Tregs in activated and naive PBMCs. Functionally, both compounds caused a significant reduction in the stimulation index in allogeneic MLR. Together, our data demonstrate for the first time that SS and Harp can induce human Tregs in vitro and therefore have great potential as anti-inflammatory agents.

The anticonvulsant effect of sparteine on pentylenetetrazole-induced seizures in rats: a behavioral, electroencephalographic, morphological and molecular study.[Pubmed:32729055]

J Mol Histol. 2020 Oct;51(5):503-518.

Abnormal synchronous activity in neurons generates epileptic seizures. Antiepileptic drugs (AEDs) are effective in 70% of patients, but this percentage is drastically lower in developing countries. Sparteine is a quinolizidine alkaloid synthesized from most Lupine species and has a probable anticonvulsive effect. For this reason, the objective of the present work was to study the anticonvulsant effect of sparteine using a dose-effect curve and to determine its effectiveness against seizures using behavioral, electroencephalographic, morphological and molecular data. Wistar rats were grouped into control [saline solution (0.9%), pentylenetetrazole (90 mg/kg), and sparteine (13, 20 and 30 mg/kg), intraperitoneal (i.p.)] and experimental (sparteine + pentylenetetrazole) groups. The rats were implanted with surface electrodes to register electrical activity, and convulsive behavior was evaluated according to Velisek's scale. The rats were perfused to obtain brain slices for cresyl violet staining and cellular density quantification as well as for immunohistochemistry for NeuN and GFAP. Other animals were used to determine the hippocampal mRNA expression of the M2 and M4 acetylcholine receptors by qPCR. Sparteine exhibited a better anticonvulsant effect at a dose of 30 mg/kg (i.p.) than at the other doses used. This anticonvulsant effect was characterized by a decrease in the severity of convulsive behavior, 100% survival, an inhibitory effect on epileptiform activity 75 min after pentylenetetrazole administration, and the conservation of the cellular layers of CA1, CA3 and the dentate gyrus (DG); however, astrogliosis was observed after 30 mg/kg sparteine treatment. In addition, sparteine treatment increased the mRNA expression of the M4 receptor three hours after administration. According to our findings, the effective dose of sparteine as an anticonvulsant agent by i.p. injection is 30 mg/kg. The astrogliosis that was observed after sparteine administration may be a compensatory mechanism to diminish excitability and maintain neuronal homeostasis, possibly through redistributing potassium and glutamate. The increase in the mRNA expression of the M4 receptor may suggest the participation of the M4 receptor in the anticonvulsive effect of sparteine, as the activation of this receptor may inhibit acetylcholine release and facilitate the subsequent release of GABA. However, the precise mechanisms by which sparteine produces these effects are not known, and therefore, further experiments are necessary.

Resolution of Vaulted Biaryl Ligands via Borate Esters of Quinine and Quinidine.[Pubmed:32687706]

J Org Chem. 2020 Aug 21;85(16):10432-10450.

Given the sudden and unexplained rise in the cost of (+)- and (-)-Sparteine, an alternative method for the resolution of vaulted biaryls has been developed. This method involves the reaction of a racemic vaulted biaryl ligand with one equivalent of BH3.SMe2 and one equivalent of either quinine or quinidine. A precipitate then forms from the resulting mixture of diastereomeric borates as a result of differential solubilities. Hydrolysis of the precipitate then liberates the (S)-ligand in the case of quinine and the (R)-ligand in the case of quinidine, both with >99% ee. This method has been applied to 16 different vaulted biaryl ligands, including 10 whose preparation is described here for the first time. In addition, proof of principle has been demonstrated for the dynamic thermodynamic resolution of the vaulted biaryl ligands with this method in combination with a nonchiral copper(II) complex that can racemize the ligand.

Scientific opinion on the risks for animal and human health related to the presence of quinolizidine alkaloids in feed and food, in particular in lupins and lupin-derived products.[Pubmed:32626161]

EFSA J. 2019 Nov 5;17(11):e05860.

The European Commission asked EFSA for a scientific opinion on the risks for animal and human health related to the presence of quinolizidine alkaloids (QAs) in feed and food. This risk assessment is limited to QAs occurring in Lupinus species/varieties relevant for animal and human consumption in Europe (i.e. Lupinus albus L., Lupinus angustifolius L., Lupinus luteus L. and Lupinus mutabilis Sweet). Information on the toxicity of QAs in animals and humans is limited. Following acute exposure to sparteine (reference compound), anticholinergic effects and changes in cardiac electric conductivity are considered to be critical for human hazard characterisation. The CONTAM Panel used a margin of exposure (MOE) approach identifying a lowest single oral effective dose of 0.16 mg sparteine/kg body weight as reference point to characterise the risk following acute exposure. No reference point could be identified to characterise the risk of chronic exposure. Because of similar modes of action for QAs, the CONTAM Panel used a group approach assuming dose additivity. For food, the highest mean concentration of Total QAs (TotQAs) (i.e. the 6 most abundant QAs) was found in lupin seed samples classified as 'Lupins (dry) and similar-'. Due to the limited data on occurrence and consumption, dietary exposure was calculated for some specific scenarios and no full human health risk characterisation was possible. The calculated margin of exposures (MOEs) may indicate a risk for some consumers. For example, when lupin seeds are consumed without a debittering step, or as debittered lupin seeds high in QA content and when 'lupin-based meat imitates' are consumed. For horses, companion and farm animals, other than salmonids, the available database on adverse effects was too limited to identify no-observed-adverse-effect levels and/or lowest-observed-adverse-effect levels and no risk characterisation was possible. For salmonids, the CONTAM Panel considers the risk for adverse effects to be low.

Synthesis and Applications of the C2-Symmetrical Diamine 2,7-Diazabicyclo[4.4.1]undecane.[Pubmed:32353240]

J Org Chem. 2020 Jun 5;85(11):7424-7432.

Chiral diamines are particularly useful as ligands for asymmetric catalysis. In an effort to expand the library of such diamines, the synthesis and resolution of the C2-symmetric diamine 2,7-diazabicyclo[4.4.1]undecane [(-)-1] are reported. Diamine (-)-1 has been prepared in multigram quantities from the known bicyclic diketone 7 in four steps without the need for chromatographic purification. Derivatives of (-)-1, i.e., the bis-methylated diamine (+)-5 and two diastereomeric tricyclic analogs, were evaluated as potential sparteine surrogates. The solid-state structure of the (+)-5-methyllithium complex was obtained. High levels of asymmetric induction were observed while using (+)-5 as a ligand in palladium-mediated asymmetric allylations.

Improved Synthesis and Isolation of Bedaquiline.[Pubmed:32118176]

ACS Omega. 2020 Feb 17;5(7):3607-3611.

Bedaquiline (BDQ) is the most critical pharmaceutical in the world for treating multidrug-resistant Mycobacterium tuberculosis. Despite it being highly effective, BDQ asymmetric synthesis remains a challenge. Herein, the influence of chiral bases, namely, bis(1-phenylethyl)amine, bisoxazoline, and sparteine on the diastereoselective lithiation reaction to obtain BDQ was investigated. The highest diastereoselective ratio (dr) emerged as 90:10 from the (+)-bis[(R)-1-phenylethyl] lithium amide. This is a significant improvement from the 50:50 dr achieved from the commercial synthesis. Thereafter, the desired (90:10 RS, SR) diastereomeric mixture was easily isolated via a gravity column and subjected to chiral supercritical fluid chromatography (SFC) to access the desired enantiomer (1R, 2S)-BDQ. The advantages of this procedure are enhanced diastereoselection as well as a greener, faster way to achieve excellent enantioseparation (up to 1.0 g scale).

Profile and Content of Residual Alkaloids in Ten Ecotypes of Lupinus mutabilis Sweet after Aqueous Debittering Process.[Pubmed:32009208]

Plant Foods Hum Nutr. 2020 Jun;75(2):184-191.

The evaluation of the level of alkaloids in edible Lupinus species is crucial from a food safety point of view. Debittering of lupin seeds has a long history; however, the control of the level of alkaloids after processing the seeds is typically only evaluated by changes in the bitter taste. The aim of this study was to evaluate the profile and residual levels of quinolizidine alkaloids (QA) in (Lupinus mutabilis Sweet) after aqueous debittering process. Samples from 10 ecotypes from different areas of Peru were analyzed before and after the process. Based on results obtained by gas chromatography and mass spectrometry, from eight alkaloids identified before the debittering process, only small amounts of lupanine (avg. 0.0012 g/100 g DM) and sparteine (avg. 0.0014 g/100 g DM) remained in the seeds after the debittering process, and no other alkaloids were identified. The aqueous debittering process reduced the content of alkaloids to levels far below the maximal level allowed by international regulations (

Regiodivergent enantioselective C-H functionalization of Boc-1,3-oxazinanes and application to the synthesis of beta(2) and beta(3)-amino acids.[Pubmed:31620675]

Nat Catal. 2019 Oct;2(10):882-888.

beta(2)- and beta(3)-Amino acids are important chiral building blocks for the design of new pharmaceuticals and peptidomimetics. Here we report a straightforward regio- and enantiodivergent access to these compounds using a one-pot reaction composed of sparteine-mediated enantioselective lithiation of a Boc-1,3-oxazinane, transmetallation to zinc and direct or migratory Negishi coupling with an organic electrophile. The regioselectivity of the Negishi coupling was highly ligand-controlled and switchable to obtain the C4- or the C5-functionalized product exclusively. High enantioselectivities were achieved on a broad range of examples, and a catalytic version in chiral diamine was developed using the (+)-sparteine surrogate. Selected C4- and C5-functionalized Boc-1,3-oxazinanes were subsequently converted to highly enantio-enriched beta(2)- and beta(3)-amino acids with the (R) or (S) configuration, depending on the sparteine enantiomer employed in the lithiation step.

Lupin (Lupinus spp.) seeds exert anthelmintic activity associated with their alkaloid content.[Pubmed:31227784]

Sci Rep. 2019 Jun 21;9(1):9070.

The growing range of drug resistant parasitic nematode populations threatens the sustainability of ruminant farming worldwide. In this context, nutraceuticals, animal feed that provides necessary dietary requirements while ensuring parasite control, could contribute to increase farming sustainability in developed and low resource settings. In this study, we evaluated the anthelmintic potential of lupin seed extracts against the major ruminant trichostrongylids, Haemonchus contortus and Teladorsagia circumcincta. In vitro observations showed that seed extracts from commercially available lupin varieties could significantly but moderately inhibit larval migration. This anthelmintic effect was mediated by the seed alkaloid content and was potent against both fully susceptible and multidrug resistant H. contortus isolates as well as a susceptible T. circumcincta isolate. Analytical chemistry revealed a set of four lupanine and sparteine-derivatives with anthelmintic activity, and electrophysiology assays on recombinant nematode acetylcholine receptors suggested an antagonistic mode of action for lupin alkaloids. An in vivo trial in H. contortus infected lupin-fed ewes and goats failed to demonstrate any direct anthelmintic effect of crude lupin seeds but infected lupin-fed goats suffered significantly less parasite-mediated blood losses. Altogether, our findings suggest that the anthelmintic potential of lupin remains limited. However, the potent alkaloids identified could lead to the development of novel drugs or may be used in combination with current anthelmintics to improve their efficacy.

Phytochemical Information and Biological Activities of Quinolizidine Alkaloids in Sophora: A Comprehensive Review.[Pubmed:31215388]

Curr Drug Targets. 2019;20(15):1572-1586.

Quinolizidine alkaloids, a main form of alkaloids found in the genus Sophora, have been shown to have many pharmacological effects. This review aims to summarize the photochemical reports and biological activities of quinolizidine alkaloids in Sophora. The collected information suggested that a total of 99 quinolizidine alkaloids were isolated and detected from different parts of Sophora plants, represented by lupinine-type, cytisine-type, sparteine-type, and matrine-type. However, quality control needs to be monitored because it could provide basic information for the reasonable and efficient use of quinolizidine alkaloids as medicines and raw materials. The nonmedicinal parts may be promising to be used as a source of quinolizidine alkaloid raw materials and to reduce the waste of resources and environmental pollution. In addition, the diversity of chemical compounds based on the alkaloid scaffold to make a biological compound library needs to be extended, which may reduce toxicity and find new bioactivities of quinolizidine alkaloids. The bioactivities most reported are in the fields of antitumor activity along with the effects on the cardiovascular system. However, those studies rely on theoretical research, and novel drugs based on quinolizidine alkaloids are expected.

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