An enhancer of ganglioside biosynthesis
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(−)-L-threo-PDMP (hydrochloride)

Item No. 10005278

Technical Information
Formal Name
N-[(1S,2S)-2-hydroxy-1-(4-morpholinylmethyl)-2-phenylethyl]-decanamide, monohydrochloride
CAS Number
161491-04-9
Molecular Formula
C23H38N2O3 • HCl
Formula Weight
Purity
≥98%
Formulation
A solid
Ethanol: SolubleMethanol: Soluble
SMILES
CCCCCCCCCC(N[C@H]([C@@H](O)C1=CC=CC=C1)CN2CCOCC2)=O.Cl
InChi Code
InChI=1S/C23H38N2O3.ClH/c1-2-3-4-5-6-7-11-14-22(26)24-21(19-25-15-17-28-18-16-25)23(27)20-12-9-8-10-13-20;/h8-10,12-13,21,23,27H,2-7,11,14-19H2,1H3,(H,24,26);1H/t21-,23-;/m0./s1
InChi Key
HVJHJOYQTSEKPK-IUQUCOCYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    (–)-L-threo-PDMP is a ceramide derivative and one of the four possible stereoisomers of PDMP (Item No. 62595).1 L-threo-PDMP is an enhancer of ganglioside biosynthesis.2 It increases the activity of ganglioside GM3, -GD3, and -GQ1b synthases and the levels of various gangliosides in primary rat cortical neurons, as well as increases the levels of glucosylceramide, lactosylceramide, and ganglioside GM3 in B16 melanoma cells.2,3 L-threo-PDMP increases neurite outgrowth in primary rat neocortical explants when used at a concentration of 15 µM and increases functional synapse formation in primary rat cortical neurons at 20 µM.4,2 It improves retention of a long-term memory learned prior to forebrain ischemia in rats when administered after ischemia at a dose of 40 mg/kg per day.2 [Matreya, LLC. Catalog No. 1749]

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Inokuchi, J.i., and Radin, N.S. Preparation of the active isomer of 1-phenyl-2-decanoylamino-3-morpholino-1-propanol, inhibitor of murine glucocerebroside synthetase. J. Lipid Res. 28(5), 565-571 (1987).

    2. Inokuchi, J.-i., Mizutani, A., Jimbo, M., et alUp-regulation of ganglioside biosynthesis, functional synapse formation, and memory retention by a synthetic ceramide analog (L-PDMP). Biochm. Biophys. Res. Commun. 237(3), 595-600 (1997).

    3. Inokuchi, J.-i. Neurotrophic and neuroprotective actions of an enhancer of ganglioside biosynthesis. Int. Rev. Neurobiol. 85, 319-336 (2009).

    4. Usuki, S., Hamanoue, M., Kohsaka, S., et alInduction of ganglioside biosynthesis and neurite outgrowth of primary cultured neurons by L-threo-1-phenyl-2-decanoylamino-3-morpholino-1-propanol. J. Neurochem. 67(5), 1821-1830 (1996).