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P7340

(±)-threo-1-Phenyl-2-decanoylamino-3-morpholino-1-propanol hydrochloride

Name: (±)-<I>threo</I>-1-Phenyl-2-decanoylamino-3-morpholino-1-propanol hydrochloride
Brand: SIGMA

Synonym(s):

(±)-threo-PDMP hydrochloride, PDMP hydrochloride

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About This Item

Empirical Formula (Hill Notation):

C₂₃H₃₈N₂O₃·HCl

CAS Number:

80938-69-8

Molecular Weight:

427.02

MDL number:

MFCD00236490

UNSPSC Code:

12352200

PubChem Substance ID:

24278649

NACRES:

NA.77

biological source

synthetic (organic)

Quality Level

100

Assay

≥98% (TLC)

form

powder

solubility

water: 50 mg/mL, clear, colorless

storage temp.

−20°C

SMILES string

Cl.CCCCCCCCCC(=O)N[C@H](CN1CCOCC1)[C@H](O)c2ccccc2

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-;/m1./s1

InChI key

HVJHJOYQTSEKPK-BLDCTAJRSA-N

Related Categories

Exclusive Savings

Biochem/physiol Actions

Glucosylceramide synthase inhibitor; blocks formation of glucosylceramide from ceramide.

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Radin, et al.

Journal of Lipid Research, 26, 183-213 (1993)

Effects of D-threo-PDMP, an inhibitor of glucosylceramide synthetase, on expression of cell surface glycolipid antigen and binding to adhesive proteins by B16 melanoma cells.

J Inokuchi et al.

Journal of cellular physiology, 141(3), 573-583 (1989-12-01)

Incubating B16 melanoma cells with an inhibitor of glucosylceramide (GlcCer) synthetase, D-threo-1-phenyl-2-decanoylamino-3-morpholino-1-propanol (D-threo-PDMP), led to a considerable decrease in the levels of GlcCer and lactosylceramide (LacCer). The content of ganglioside GM3 was little affected, but the ability to bind a

Endogenous β-glucocerebrosidase activity in Abca12⁻/⁻epidermis elevates ceramide levels after topical lipid application but does not restore barrier function.

Jorge F Haller et al.

Journal of lipid research, 55(3), 493-503 (2013-12-03)

ABCA12 mutations disrupt the skin barrier and cause harlequin ichthyosis. We previously showed Abca12(-/-) skin has increased glucosylceramide (GlcCer) and correspondingly lower amounts of ceramide (Cer). To examine why loss of ABCA12 leads to accumulation of GlcCer, de novo sphingolipid

Inhibition of glycosphingolipid synthesis by threo-1-phenyl-2-decanoylamino-3-morpholino-1-propanol (PDMP) and the modulation of IL-1beta-stimulated expression of inducible nitric oxide synthase in rat aortic smooth muscle cells.

A A Weber et al.

British journal of pharmacology, 123(5), 906-910 (1998-04-16)

1. The composition of glycosphingolipids is altered in atherosclerotic tissue. In order to study the possible modulation of interleukin-1beta (IL-1beta)-induced expression of inducible nitric oxide synthase (iNOS) by endogenously synthesized glycosphingolipids, we investigated rat aortic vascular smooth muscle cells (VSMC)

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