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β-Aminoarteether (SM934 free base)

Cat No.:V75168 Purity: ≥98%
β-Aminoarteether (SM934 free base) is an orally bioactive Artemisinin analogue.
β-Aminoarteether (SM934 free base)
β-Aminoarteether (SM934 free base) Chemical Structure CAS No.: 133162-24-0
Product category: NLR
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
1mg
Other Sizes

Other Forms of β-Aminoarteether (SM934 free base):

  • β-Aminoarteether maleate
Official Supplier of:
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Top Publications Citing lnvivochem Products
Product Description
β-Aminoarteether (SM934 free base) is an orally bioactive Artemisinin analogue. Beta-Aminoarteether may be utilized in the study of inflammatory and autoimmune diseases, such as lupus disease.
β-Aminoarteether (SM934 free base) is an orally active artemisinin derivative. With a CAS number of 133162-24-0, a molecular formula of C17H29NO5, and a molecular weight of 327.42, this compound can be used for inflammation and autoimmune disease research, such as lupus diseases. β-Aminoarteether is an artemisinin derivative in which the lactone of (+)-artemisinin has been converted into the corresponding lactol 2-aminoethyl ether.
Biological Activity I Assay Protocols (From Reference)
Targets
Inflammatory pathways and autoimmune disease mechanisms. β-Aminoarteether (SM934 free base) is an orally active artemisinin derivative that can be used for inflammation and autoimmune disease research, such as lupus diseases. Artemisinin derivatives are known to have immunomodulatory effects, including the modulation of cytokine production and the inhibition of immune cell activation.
ln Vitro
After 24 hours of IFN-γ stimulation, β-Aminoarteether (SM934; 10 µM) administration directly increases IL-10 production and decreases IL-12/23p40 production in primary peritoneal macrophages[1]. whilst having no effect on Treg differentiation, decreased Th1 and Th17 polarization[1].
In vitro, β-Aminoarteether is an artemisinin derivative with oral activity. Artemisinin derivatives are known to have immunomodulatory effects, including the modulation of cytokine production and the inhibition of immune cell activation. The compound's activity in autoimmune disease models suggests that it may modulate inflammatory pathways and reduce autoantibody production.
ln Vivo
β-Aminoarteether (SM934; 1-10 mg/kg; oral administration; daily; for 3 months) therapy boosts the survival rate of NZB/W F1 mice and considerably delays the advancement of glomerulonephritis. Macrophages from NZB/W F1 mice produce more IL-10 when treated with β-aminoarteether[1].
In vivo, β-Aminoarteether can be used for inflammation and autoimmune disease research, such as lupus diseases. The compound is orally active, making it suitable for oral administration in animal models. In lupus models, artemisinin derivatives have been shown to reduce disease severity, decrease autoantibody levels, and ameliorate organ damage.
Enzyme Assay
The in vitro enzyme/receptor binding (cell-free) assay for β-Aminoarteether is not a typical enzyme inhibition assay, as the compound's mechanism of action is primarily immunomodulatory rather than enzyme inhibition. The compound's activity is typically assessed in cell-based assays measuring cytokine production, immune cell activation, or autoantibody production.
Cell Assay
In vitro cellular assays for β-Aminoarteether are performed using immune cells such as macrophages, T cells, or B cells. Cells are treated with varying concentrations of the compound, and inflammatory cytokine production (e.g., TNF-α, IL-6, IL-1β) is measured by ELISA. T cell proliferation and activation are assessed by flow cytometry. In autoimmune disease models, the compound's ability to inhibit autoantibody production by B cells can also be evaluated.
Animal Protocol
Animal/Disease Models: Female NZB/W F1 mice (Six and half months old)[1]
Doses: 1 mg/kg, 3 mg/kg, and 10 mg/kg
Route of Administration: Oral administration; daliy; for 3 months
Experimental Results: Dramatically delayed the progression of glomerulonephritis and increased the survival rate of NZB/W F1 mice.
In vivo animal experiments for β-Aminoarteether are conducted in rodent models of autoimmune diseases, such as lupus-prone MRL/lpr mice or NZB/W F1 mice. The compound is administered orally at various dose levels. Pharmacodynamic endpoints include the measurement of autoantibody levels (anti-dsDNA antibodies), assessment of proteinuria and kidney function, histopathological evaluation of kidney and other organ damage, and measurement of inflammatory cytokine levels in serum or tissues.
ADME/Pharmacokinetics
β-Aminoarteether (SM934 free base) is an orally active artemisinin derivative, suggesting good oral bioavailability. As a small molecule with a molecular weight of 327.42 g/mol and a molecular formula of C17H29NO5, the compound is expected to have favorable absorption and distribution properties. However, detailed pharmacokinetic parameters such as half-life, Cmax, AUC, and clearance have not been extensively reported.
Toxicity/Toxicokinetics
Toxicology data for β-Aminoarteether are limited. The compound is an artemisinin derivative, and artemisinin-based compounds have been extensively used as antimalarial drugs with established safety profiles. However, the specific safety profile of β-Aminoarteether has not been extensively reported. The compound is used for research purposes only and is not approved for human use.
References

[1]. SM934 treated lupus-prone NZB × NZW F1 mice by enhancing macrophage interleukin-10 production and suppressing pathogenic T cell development. PLoS One. 2012;7(2):e32424.

[2]. The artemisinin analog SM934 alleviates dry eye disease in rodent models by regulating TLR4/NF-κB/NLRP3 signaling. Acta Pharmacol Sin. 2021;42(4):593-603.

Additional Infomation
β-Aminoartemisinin is a derivative of artemisinin in which the (+)-artemisinin lactone is converted into the corresponding 2-aminoethyl ether lactone (the new stereocenter is in the β(S) configuration). It is an artemisinin derivative and also a primary amino compound.
β-Aminoarteether (CAS: 133162-24-0) has a molecular formula of C17H29NO5 and a molecular weight of 327.42. It is also known as SM934 free base. β-Aminoarteether is an orally active artemisinin derivative used for inflammation and autoimmune disease research, such as lupus diseases. The compound is not approved for human use and is intended for research purposes only.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C17H29NO5
Molecular Weight
327.42
Exact Mass
327.204
CAS #
133162-24-0
Related CAS #
β-Aminoarteether maleate; 133162-25-1
PubChem CID
10019350
Appearance
Light yellow to yellow oil
LogP
2.1
Hydrogen Bond Donor Count
1
Hydrogen Bond Acceptor Count
6
Rotatable Bond Count
3
Heavy Atom Count
23
Complexity
462
Defined Atom Stereocenter Count
8
SMILES
C[C@@H]1CC[C@H]2[C@H]([C@H](O[C@H]3[C@@]24[C@H]1CC[C@](O3)(OO4)C)OCCN)C
InChi Key
HPGHCIXRRLNXRN-XQLAAWPRSA-N
InChi Code
InChI=1S/C17H29NO5/c1-10-4-5-13-11(2)14(19-9-8-18)20-15-17(13)12(10)6-7-16(3,21-15)22-23-17/h10-15H,4-9,18H2,1-3H3/t10-,11-,12+,13+,14+,15-,16-,17-/m1/s1
Chemical Name
2-[[(1R,4S,5R,8S,9R,10S,12R,13R)-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.04,13.08,13]hexadecan-10-yl]oxy]ethanamine
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 Data
Solubility (In Vitro)
DMSO: ~50 mg/mL (~152.7 mM; with ultrasonication and warming by heating to 60°C)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.5 mg/mL (7.64 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 (25.0 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: ≥ 2.5 mg/mL (7.64 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (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 (25.0 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 3.0542 mL 15.2709 mL 30.5418 mL
5 mM 0.6108 mL 3.0542 mL 6.1084 mL
10 mM 0.3054 mL 1.5271 mL 3.0542 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.

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Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
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Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
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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.
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