| Identification | Back Directory | [Name]
PSYCHOSINE | [CAS]
2238-90-6 | [Synonyms]
PSYCHOSIN
PSYCHOSINE
PSYCHOSINE(RG)
LYSO-CEREBROSIDE
PSYCHOSINE USP/EP/BP
Galactosylsphingosine
O-Galactosylsphingosine
Psychosine (free amine)
Sphingosine galactoside
LYSO-CERAMIDEGALACTOSIDE
1-β-d-galactosylsphingosine
D-GALACTOSYL-B1-1' SPHINGOSN
1-B-D-GALACTOSYLSPHINOGOSINE
Galactosylsphingosine (d18:1)
1-BETA-D-GALACTOSYLSPHINGOSINE
D-GALACTOSYL-B1-1' SPHINGOSINE
SPHINGOSINE, 1-BETA-D-GALACTOSYL
Psychosine (Galactosylsphingosine)
1-O-β-D-Galactopyranosylsphingosine
SPHINGOSYL-BETA-D-GALACTOPYRANOSIDE
Galactosyl(beta) Sphingosine (d18:1)
PEONIDIN-3-O-GALACTOSIDE CHLORIDE(RG)
b-D-Galactosylsphingosine - Synthetic
D-galactosyl-1-1'-D-erythro-sphingosine
D-galactosyl-β1-1'-D-erythro-sphingosine
D-GALACTOSYL-B1-1'-D-ERYTHRO-SPHINGOSINE
Psychosine Quantitative Mass Spec Standard
(2S,3R,4E)-1-(β-D-Galactopyranosyloxy)-2-amino-4-octadecene-3-ol
[(2S,3R,4E)-2-Amino-3-hydroxy-4-octadecenyl]β-D-galactopyranoside
β-D-Galactopyranoside, (2S,3R,4E)-2-amino-3-hydroxy-4-octadecen-1-yl
(2R,3R,4S,5S,6R)-2-[(E,2S,3R)-2-amino-3-hydroxy-octadec-4-enoxy]-6-(hydroxymethyl)oxane-3,4,5-triol | [Molecular Formula]
C24H47NO7 | [MDL Number]
MFCD07374280 | [MOL File]
2238-90-6.mol | [Molecular Weight]
461.63 |
| Chemical Properties | Back Directory | [Melting point ]
190 °C (decomp) | [Boiling point ]
664.3±55.0 °C(Predicted) | [density ]
1.14±0.1 g/cm3(Predicted) | [storage temp. ]
-20°C | [solubility ]
Chloroform/Methanol/DI water (5:1:0.1): soluble; Ethanol: soluble | [form ]
lyophilized powder | [pka]
11.74±0.45(Predicted) |
| Hazard Information | Back Directory | [Description]
Galactosylsphingosine is a bioactive sphingolipid. It potentiates LPS-induced production of inflammatory cytokines, decreases the mitochondrial membrane potential, and induces cell death in mouse astrocytes, effects that can be reversed by the sphingosine-1-phosphate receptor agonist FTY720 phosphate . Galactosylsphingosine (0.1 and 1 μM) induces demyelination of mouse cerebellar slices. It inhibits PDGF-induced translocation of PKC to the cell surface and induces apoptosis in MO3.13 oligodendrocytes. Galactosylsphingosine (10 and 15 μM) inhibits gene transcription mediated by peroxisome proliferator-activated receptor α (PPARα) in reporter assays using C6 glial cells. Levels of galactosylsphingosine are increased in postmortem brain from patients with Krabbe disease, a lysosomal storage disorder characterized by a β-galactosylceramidase deficiency.[Matreya, LLC. Catalog No. 1305] | [Uses]
Psychosine is a cationic lysosphingolipid that displays neuroprotective effects against quisqualate. | [Definition]
ChEBI: A glycosylsphingoid consisting of sphingosine having a beta-D-galactosyl residue attached at the 1-position. | [General Description]
Galactosyl(β) Sphingosine (d18:1) is a substrate for the enzyme endoglycoceramidase I (EGCase I). It has sphingosine backbone with galactose attached to it and is a brain glycospingolipid. | [Biochem/physiol Actions]
Galatosylsphingosine or psychosine is a cytotoxic lipid which accumulates in oligodendrocytes due to dysfunctional lysosomal enzyme galactosylceramidase and is implicated in globoid cell leukodystrophy. Psychosine accumulation induces demyelination, astrocyte dysfunction and pro-inflammatory cytokine release in Krabbe disease. | [Enzyme inhibitor]
This cationic brain lysosphingolipid (FWfree-base = 461.64 g/mol; CAS 2238- 90-6), also known as 1-O-b-D-galactosylsphingosine, inhibits metabotropic a1-adrenergic receptor signaling-induced phospholipase C activation in rat brain astrocytes. Psychosine also exerts protective effects against quisqualate, suggesting it may be useful in prophylaxis of neurodegenerative disorders arising from over-stimulation of hippocampal Group 1 metabolotropic glutamate receptor, or mGluR. Psychosine is the product of the reaction catalyzed by sphingosine b-galactosyltransferase and is the substrate for psychosine sulfotransferase and galactosylceramidase. Target(s): cerebroside-sulfatase, or arylsulfatase A; cytochrome c oxidase; cytokinesis; electron transport; galactosylgalactosylglucosylceramidase; glucocerebrosidase, lysosome; b-glucosidase; phosphorylase kinase; protein kinase C (11- 14); protein-tyrosine sulfotransferase; and sphingomyelinase. |
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Sigma-Aldrich
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Alfa Chemistry
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Energy Chemical
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