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^N
3D model (Jmol)	Interactive image
ChEBI	CHEBI:78759^N
ChEMBL	ChEMBL447685^Y
ChemSpider	4942657^Y
IUPHAR/BPS	2454
PubChem	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^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
SMILES CCCCCCCCCCCCC/C=C/[C@@H]([C@@H](CO)N(C)C)O
Properties
Chemical formula	C₂₀H₄₁NO₂
Molar mass	327.55 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

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. doi:10.1038/nchembio.767.

Lysophospholipid signaling modulators

Receptor
(ligands)

LPA	Agonists: 1-Oleoyl-LPA 1-Palmitoyl-LPA GRI-977143 LPA OMPT Antagonists: H2L-5186303 H2L-5765834 Ki-16425 TC-LPA5 4 VPC-32183

S1P	Agonists: Amiselimod Cenerimod Ceralifimod CS-2100 CYM-5442 CYM-5520 CYM 5541 CYM-50260 CYM-50308 Dihydro-S1P (sphinganine 1-phosphate) Fingolimod Fingolimod phosphate KRP-203 Phyto-S1P Ponesimod RP-001 RP-002 RPC-1063 SEW-2871 Siponimod S1P SPC TC-G 1006 TC-SP 14 W-061 XAX-162 Antagonists: CS-0777 CYM-50358 JTE-013 TY-52156 VPC-23019 W-146

Enzyme
(inhibitors)

SPT	Myriocin

Ceramidase	Ceranib 1 OEA

SphK	N,N-DMS Safingol SKI II

Others

Precursors: LPA: LPC; S1P: Palmitoyl-CoA
Serine
3-Ketosphinganine (dehydrosphingosine)
Dihydrosphingosine (sphinganine)
Dihydroceramide
Ceramide
Sphingosine

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