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P7340

Sigma-Aldrich

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

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

Biochem/physiol Actions

Glucosylceramide synthase inhibitor; blocks formation of glucosylceramide from ceramide.

Storage Class Code

11 - Combustible Solids

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)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Radin, et al.
Journal of Lipid Research, 26, 183-213 (1993)
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
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
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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