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PSYCHOSINE

Product Name
PSYCHOSINE
CAS No.
2238-90-6
Chemical Name
PSYCHOSINE
Synonyms
PSYCHOSIN;PSYCHOSINE;PSYCHOSINE(RG);LYSO-CEREBROSIDE;PSYCHOSINE USP/EP/BP;Galactosylsphingosine;O-Galactosylsphingosine;Psychosine (free amine);Sphingosine galactoside;LYSO-CERAMIDEGALACTOSIDE
CBNumber
CB4245038
Molecular Formula
C24H47NO7
Formula Weight
461.63
MOL File
2238-90-6.mol
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PSYCHOSINE Property

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)
color 
White to off-white
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Safety

Hazard Codes 
Xn
Risk Statements 
20/21/22
Safety Statements 
36
WGK Germany 
3
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Danger
Hazard statements

H225Highly Flammable liquid and vapour

H370Causes damage to organs

Precautionary statements

P210Keep away from heat/sparks/open flames/hot surfaces. — No smoking.

P260Do not breathe dust/fume/gas/mist/vapours/spray.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P370+P378In case of fire: Use … for extinction.

P403+P233Store in a well-ventilated place. Keep container tightly closed.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
P9256
Product name
Psychosine from bovine brain
Purity
lyophilized powder, ≥98% (TLC)
Packaging
1mg
Price
$114
Updated
2025/07/31
Sigma-Aldrich
Product number
P9256
Product name
Psychosine from bovine brain
Purity
lyophilized powder, ≥98% (TLC)
Packaging
10mg
Price
$520
Updated
2025/07/31
Cayman Chemical
Product number
20338
Product name
Galactosylsphingosine (d18:1)
Purity
≥95%
Packaging
1mg
Price
$63
Updated
2024/03/01
Cayman Chemical
Product number
20338
Product name
Galactosylsphingosine (d18:1)
Purity
≥95%
Packaging
5mg
Price
$230
Updated
2024/03/01
Cayman Chemical
Product number
20338
Product name
Galactosylsphingosine (d18:1)
Purity
≥95%
Packaging
10mg
Price
$335
Updated
2024/03/01
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PSYCHOSINE Chemical Properties,Usage,Production

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.

References

[1] CATHERINE O’SULLIVAN  Kumlesh K D. Galactosylsphingosine (psychosine)-induced demyelination is attenuated by sphingosine 1-phosphate signalling.[J]. Journal of cell science, 2015, 128 21: 3878-3887. DOI: 10.1242/jcs.169342
[2] JACQUELINE A HAWKINS-SALSBURY. Psychosine, the cytotoxic sphingolipid that accumulates in globoid cell leukodystrophy, alters membrane architecture.[J]. Journal of Lipid Research, 2013, 54 12: 3303-3311. DOI: 10.1194/jlr.m039610
[3] YUSUF A. HANNUN  Robert M B. Lysosphingolipids Inhibit Protein Kinase C: Implications for the Sphingolipidoses[J]. Science, 1987, 235 4789. DOI: 10.1126/science.3101176
[4] EHTISHAMUL HAQ . Dysfunction of peroxisomes in twitcher mice brain: A possible mechanism of psychosine-induced disease[J]. Biochemical and biophysical research communications, 2006, 343 1: Pages 229-238. DOI: 10.1016/j.bbrc.2006.02.131

PSYCHOSINE Preparation Products And Raw materials

Raw materials

Preparation Products

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2238-90-6, PSYCHOSINERelated Search:

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

  • SPHINGOSYL-BETA-D-GALACTOPYRANOSIDE
  • SPHINGOSINE, 1-BETA-D-GALACTOSYL
  • PSYCHOSIN
  • b-D-Galactosylsphingosine - Synthetic
  • PSYCHOSINE
  • 1-BETA-D-GALACTOSYLSPHINGOSINE
  • 1-B-D-GALACTOSYLSPHINOGOSINE
  • LYSO-CERAMIDEGALACTOSIDE
  • LYSO-CEREBROSIDE
  • D-GALACTOSYL-B1-1'-D-ERYTHRO-SPHINGOSINE
  • D-GALACTOSYL-B1-1' SPHINGOSINE
  • D-GALACTOSYL-B1-1' SPHINGOSN
  • 1-β-d-galactosylsphingosine
  • (2R,3R,4S,5S,6R)-2-[(E,2S,3R)-2-amino-3-hydroxy-octadec-4-enoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
  • Galactosylsphingosine
  • PSYCHOSINE(RG)
  • (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
  • 1-O-β-D-Galactopyranosylsphingosine
  • O-Galactosylsphingosine
  • PEONIDIN-3-O-GALACTOSIDE CHLORIDE(RG)
  • D-galactosyl-1-1'-D-erythro-sphingosine
  • Galactosylsphingosine (d18:1)
  • Psychosine (Galactosylsphingosine)
  • β-D-Galactopyranoside, (2S,3R,4E)-2-amino-3-hydroxy-4-octadecen-1-yl
  • Galactosyl(beta) Sphingosine (d18:1)
  • Psychosine Quantitative Mass Spec Standard
  • PSYCHOSINE USP/EP/BP
  • D-galactosyl-β1-1'-D-erythro-sphingosine
  • Psychosine (free amine)
  • Sphingosine galactoside
  • Galactosylsphingosine (d18:1) (synthetic)
  • Galactosyl(β) Sphingosine (d18:1)
  • 2238-90-6
  • C24H47NO7
  • BioChemical
  • Metabolomics
  • Metabolic Libraries
  • Lipid Library
  • Miscellaneous Natural Products
  • disease marker