N,N-Dimethylsphingosine

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Cat.No. 4640 - N,N-Dimethylsphingosine | C20H41NO2 | CAS No. 119567-63-4
Description: Sphingosine kinase inhibitor
Chemical Name: (2S,3R,4E)-2-(Dimethylamino)-4-octadecene-1,3-diol
Purity: ≥98% (HPLC)
Datasheet
Citations
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Literature

Biological Activity

Competitive sphingosine kinase (SphK) inhibitor. Exhibits inhibitory activity in platelets and in cytosolic extracts from U937, Swiss 3T3 and PC12 cells. Selectively inhibits sphingosine phosphorylation; does not inhibit N-acylation, and displays no inhibitory effect on protein kinase C at concentrations that inhibit SphK. Increases the release of IL-1β and MCP-1 in cultured astrocytes; thought to mediate mechanical allodynia via this mechanism.

Technical Data

M. Wt 327.55
Formula C20H41NO2
Storage Store at -20°C
Purity ≥98% (HPLC)
CAS Number 119567-63-4
PubChem ID 5282309
InChI Key YRXOQXUDKDCXME-YIVRLKKSSA-N
Smiles O[C@@H]([C@H](CO)N(C)C)/C=C/CCCCCCCCCCCCC

The technical data provided above is for guidance only. For batch specific data refer to the Certificate of Analysis.

All Tocris products are intended for laboratory research use only.

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 9.83 30

Preparing Stock Solutions

The following data is based on the product molecular weight 327.55. Batch specific molecular weights may vary from batch to batch due to solvent of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 3.05 mL 15.26 mL 30.53 mL
5 mM 0.61 mL 3.05 mL 6.11 mL
10 mM 0.31 mL 1.53 mL 3.05 mL
50 mM 0.06 mL 0.31 mL 0.61 mL

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Product Datasheets

Safety Datasheet

References

References are publications that support the biological activity of the product.

Patti et al (2012) Metabolomics implicates altered sphingolipids in chronic pain of neuropathic origin. Nat.Chem.Biol. 8 232 PMID: 22267119

Edsall et al (1998) N,N-dimethylsphingosine is a potent competitive inhibitor of sphingosine kinase but not of protein kinase C: modulation of cellular levels of sphingosine 1-phosphate and ceramide. Biochemistry 37 12892 PMID: 9737868

Yatomi et al (1996) N,N-dimethylsphingosine inhibition of sphingosine kinase and sphingosine 1-phosphate activity in human platelets. Biochemistry 35 626 PMID: 8555236


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Citations for N,N-Dimethylsphingosine

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