N,N-Dimethylsphingosine
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Preferred IUPAC name (2R,3S,4E)-2-(Dimethylamino)octadec-4-ene-1,3-diol | |
Other names DMS, N,N-DMS | |
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Properties | |
Chemical formula | 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 |
Chemical compound
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
- ^ 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.
- ^ 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.
- ^ 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.
- v
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Lysophospholipid signaling modulators
(ligands)
LPARTooltip Lysophosphatidic acid receptor |
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S1PRTooltip Sphingosine-1-phosphate receptor |
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(inhibitors)
SPTTooltip Serine C-palmitoyltransferase | |
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Ceramidase |
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SphKTooltip Sphingosine kinase |
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- Precursors: LPA: LPC; S1P: Palmitoyl-CoA
- Serine
- 3-Ketosphinganine (dehydrosphingosine)
- Dihydrosphingosine (sphinganine)
- Dihydroceramide
- Ceramide
- Sphingosine
See also: Receptor/signaling modulators