PSYCHOSINE Chemical Properties

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)

Safety Information

Hazard Codes 

Xn

Risk Statements 

20/21/22

Safety Statements 

36

WGK Germany 

3

PSYCHOSINE Usage And Synthesis

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.

PSYCHOSINE(2238-90-6)Related Product Information

• PSYCHOSINE
• PSYCHOSINE
• N-ACETYL-PSYCHOSINE, C2-CEREBROSIDE,N-ACETYL-PSYCHOSINE
• D-ERYTHRO-SPHINGOSINE
• N-STEAROYL-D35-PSYCHOSINE
• N-Pentadecanoyl-psychosine?
• N-STEAROYL-PSYCHOSINE
• BODIPY(R) FL C12-GALACTOCEREBROSIDE
• GALACTOSYL CERAMIDE, [GALACTOSE-6-3H]
• PSYCHOSINE, [GALACTOSE-6-3H]
• psychosine-3'-sulfate ester
• Psychosine from bovine brain
• 2,3,4,6-TETRA-O-ACETYL-BETA-D-GALACTOPYRANOSY(1-4)-2,3,6-TRI-O-ACETYL-BETA-D-GLUCOPYRANOSYL CERAMIDE
• TNPAL-GALACTOCEREBROSIDE
• C6 NBD GALACTOSYL CERAMIDE
• C24:0-SULFATIDE
• N-STEAROYL-D35-PSYCHOSINE, PERDEUTERATED
• PSYCHOSINE, N-ACETYL