Chemistry:N,N-Dimethylsphingosine

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N,N-Dimethylsphingosine
Dimethylsphingosine.svg
Names
Preferred IUPAC name
(2R,3S,4E)-2-(Dimethylamino)octadec-4-ene-1,3-diol
Other names
DMS, N,N-DMS
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
UNII
Properties
C20H41NO2
Molar mass 327.553 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references
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N,N-Dimethylsphingosine (also known as DMS) is an inhibitor of sphingosine kinase.[1][2]

In rats with neuropathic pain, the natural metabolite DMS is unregulated in the dorsal horn. Furthermore, DMS induces mechanical hypersensitivity when injected into rats.[3]

References

  1. "N,N-dimethylsphingosine inhibition of sphingosine kinase and sphingosine 1-phosphate activity in human platelets". Biochemistry 35 (2): 626–33. January 1996. doi:10.1021/bi9515533. PMID 8555236. 
  2. "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 (37): 12892–8. September 1998. doi:10.1021/bi980744d. PMID 9737868. 
  3. "Metabolomics implicates altered sphingolipids in chronic pain of neuropathic origin". Nature Chemical Biology 8: 232–234. 2012. doi:10.1038/nchembio.767. PMID 22267119.