N,N-Dimethylsphingosine

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
CAS Number	122314-67-4 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:78759 ;
ChEMBL	ChEMBL447685 ;
ChemSpider	4942657 ;
IUPHAR/BPS	2454;
PubChem CID	6438166;
UNII	L9QRA71834 ;
	InChI 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 Key: YRXOQXUDKDCXME-QWKHPXNBSA-N ; 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;
	SMILES CCCCCCCCCCCCC/C=C/[C@@H]([C@@H](CO)N(C)C)O;
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). verify (what is ?) Infobox references

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

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

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 (3): 232–234. doi:10.1038/nchembio.767. PMC 3567618. PMID 22267119.

[pmid8555236-1] 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.

[pmid9737868-2] 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.

[Patti_2012-3] 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 (3): 232–234. doi:10.1038/nchembio.767. PMC 3567618. PMID 22267119.