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
CAS Number	119567-63-4 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:78759 ;
ChEMBL	ChEMBL447685 ;
ChemSpider	4942657 ;
IUPHAR/BPS	2454;
PubChem CID	6438166;
	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).
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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

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.

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[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: 232–234. doi:10.1038/nchembio.767. PMC 3567618. PMID 22267119.