N,N-Dimethylsphingosine

N,N-Dimethylsphingosine
Names
IUPAC name
(E,2R,3S)-2-(Dimethylamino)-octadec-4-ene-1,3-diol
Other names
DMS, N,N-DMS
Identifiers
119567-63-4 N
3D model (Jmol) Interactive image
ChEBI CHEBI:78759 N
ChEMBL ChEMBL447685 YesY
ChemSpider 4942657 YesY
2454
PubChem 6438166
Properties
C20H41NO2
Molar mass 327.55 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

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. Yatomi Y, Ruan F, Megidish T, Toyokuni T, Hakomori S, Igarashi Y (January 1996). "N,N-dimethylsphingosine inhibition of sphingosine kinase and sphingosine 1-phosphate activity in human platelets". Biochemistry. 35 (2): 626–33. doi:10.1021/bi9515533. PMID 8555236.
  2. Edsall LC, Van Brocklyn JR, Cuvillier O, Kleuser B, Spiegel S (September 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 (37): 12892–8. doi:10.1021/bi980744d. PMID 9737868.
  3. Patti GJ, Yanes O, Shriver LP, Courade JP, Tautenhahn R, Manchester M, Siuzdak G (2012). "Metabolomics implicates altered sphingolipids in chronic pain of neuropathic origin". Nature Chemical Biology. doi:10.1038/nchembio.767.
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