N,N-Dimethylsphingosine
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
  • InChI=1S/C20H41NO2/c1-4-5-6-7-8-9-10-11-12-13-14-15-16-17-20(23)19(18-22)21(2)3/h16-17,19-20,22-23H,4-15,18H2,1-3H3/b17-16+/t19-,20+/m1/s1 checkY
    Key: YRXOQXUDKDCXME-QWKHPXNBSA-N checkY
  • InChI=1/C20H41NO2/c1-4-5-6-7-8-9-10-11-12-13-14-15-16-17-20(23)19(18-22)21(2)3/h16-17,19-20,22-23H,4-15,18H2,1-3H3/b17-16+/t19-,20+/m1/s1
    Key: YRXOQXUDKDCXME-QWKHPXNBBF
  • CCCCCCCCCCCCC/C=C/[C@@H]([C@@H](CO)N(C)C)O
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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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. 8: 232–234. doi:10.1038/nchembio.767. PMC 3567618. PMID 22267119.
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