N,N-Dimethylsphingosine

N,N-Dimethylsphingosine (also known as DMS) is an inhibitor of sphingosine kinase.[1][2]

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
  • 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 Y
    Key: YRXOQXUDKDCXME-QWKHPXNBSA-N Y
  • 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).
N verify (what is YN ?)
Infobox references

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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