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860496O

Avanti

Dimethyl Sphingosine (d18:1)

N,N-dimethyl-D-erythro-sphingosine, neat oil

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Synonym(s):
(2R,3S,E)-2-(dimethylamino)octadec-4-ene-1,3-diol, N,N-DMS, D-erythro-N,N-dimethylsphingosine
Empirical Formula (Hill Notation):
C20H41NO2
CAS Number:
119567-63-4
Molecular Weight:
327.55
UNSPSC Code:
12352211
NACRES:
NA.25

form

liquid

packaging

pkg of 1 × 5 mg (860496O-5mg)

manufacturer/tradename

Avanti Polar Lipids 860496O

lipid type

sphingolipids

shipped in

dry ice

storage temp.

−20°C

SMILES string

OC[C@@](N(C)C)([H])[C@]([H])(O)/C=C/CCCCCCCCCCCCC

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+/m0/s1

InChI key

YRXOQXUDKDCXME-YIVRLKKSSA-N

General description

Dimethyl Sphingosine (d18:1), also called as N,N-Dimethyl-d-erythro-sphingosine (DMS), is a natural sphingolipid metabolite. It is found in various tissues.

Application

Dimethyl Sphingosine (d18:1) may be used:
  • to investigate D-erythro-N,N-dimethylsphingosine (DMS)-induced cell death in U937 cells to understand its molecular mechanism
  • to study its effects on intracellular Ca2+ concentration, pH and glutamate uptake in human 1321N1 astrocytes
  • in substrate specificity studies of sphingosine methyltransferase activity in rat kidney homogenate

Dimethyl sphingosine (d18:1) has been used as an inhibitor of sphingosine kinase.

Biochem/physiol Actions

D-erythro-N,N-dimethylsphingosine (DMS) prevents the activity of sphingosine kinase and protein kinase C. It modulates cellular activities. DMS exhibits anti-cancer and apoptotic properties. It is involved in the augmentation of epidermal growth factor receptor (EGFR) and inhibition of src kinase. DMS functions as a potential therapeutic for Chagas disease cardiomyopathy through its anti-parasitic and immunomodulatory properties.
D-erythro-N,N-dimethylsphingosine (DMS) has an ability to inhibit the activity of sphingosine kinase. It also helps to study the role of sphingosine 1-phosphate (SPP) as an intracellular second messenger. DMS exhibits anti-parasitic and immunomodulatory activities. It acts as a potential therapeutic for chronic Chagas disease cardiomyopathy.

Packaging

5 mL Clear Glass Sealed Ampule (860496O-5mg)

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Therapeutic effects of sphingosine kinase inhibitor N, N-dimethylsphingosine (DMS) in experimental chronic Chagas disease cardiomyopathy
Vasconcelos JF, et al.
Scientific reports, 7(1), 6171-6171 (2017)
High-throughput screening assay for sphingosine kinase inhibitors in whole blood using RapidFire mass spectrometry
Highkin MK, et al.
Journal of Biomolecular Screening, 16(2), 272-277 (2011)
N-(4-Hydroxyphenyl) retinamide increases dihydroceramide and synergizes with dimethylsphingosine to enhance cancer cell killing
Wang H, et al.
Molecular Cancer Therapeutics, 7(9), 2967-2976 (2008)
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
Edsall L, et al.
Biochemistry, 37(37), 12892-12898 (1998)
Hyo-Lim Kim et al.
Prostaglandins & other lipid mediators, 86(1-4), 68-72 (2008-05-10)
Previously, we studied N,N-dimethyl-D-erythro-sphingosine (DMS)-induced cell death and signaling in U937 human monocytes; we found that DMS-induced sphingosine kinase- and PKC-independent apoptosis. In the present study, we studied apoptotic responses by three N-methyl derivatives of sphingosine: N-monomethyl-D-erythro-sphingosine (MMS), N,N,N-trimethyl-D-erythro-sphingosine (TMS)
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