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D2571

Sigma-Aldrich

DPPE hydrochloride

≥98% (HPLC)

Synonym(s):

BMS-217380-01, N,N-Diethyl-2-[4-(phenylmethyl) phenoxy]ethanamine hydrochloride, Tesmilifene hydrochloride, YMB1002, [2-(4-Benzyl-phenoxy)-ethyl]-diethyl-amine hydrochloride

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About This Item

Empirical Formula (Hill Notation):
C19H25NO·HCl
CAS Number:
92981-78-7
Molecular Weight:
319.87
MDL number:
MFCD11114012
UNSPSC Code:
51111800
PubChem Substance ID:
329798745
NACRES:
NA.77

Quality Level

100

Assay

≥98% (HPLC)

form

powder

color

white

solubility

H2O: 16 mg/mL

storage temp.

2-8°C

SMILES string

Cl.CCN(CC)CCOc1ccc(Cc2ccccc2)cc1

InChI

1S/C19H25NO.ClH/c1-3-20(4-2)14-15-21-19-12-10-18(11-13-19)16-17-8-6-5-7-9-17;/h5-13H,3-4,14-16H2,1-2H3;1H

InChI key

TXLHNFOLHRXMAU-UHFFFAOYSA-N

Biochem/physiol Actions

DPPE is a potent, selective ligand of the microsomal anti-estrogen binding site. DPPE is a tamoxifen derivataive that binds with high affinity to the anti-estrogen binding site, but unlike tamoxifen, does not bind to the estrogen receptor. DPPE sensitizes MDR tumor cells to chemotherapy and also inhibits histamine binding at the intracellular histamine site.

Features and Benefits

This compound is featured on the Nuclear Receptors (Steroids) page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Storage Class Code

11 - Combustible Solids

WGK

nwg

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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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Leonard Reyno et al.
Journal of clinical oncology : official journal of the American Society of Clinical Oncology, 22(2), 269-276 (2004-01-15)
N,N-diethyl-2-[4-(phenylmethyl)phenoxy]ethanamine (DPPE; tesmilifene) is a novel agent that augments chemotherapy cytotoxicity in vitro and in vivo. A phase II trial combining DPPE and doxorubicin (DOX) in metastatic breast carcinoma showed increased response over that expected with DOX. We report a
H Hiramatsu et al.
Japanese journal of cancer research : Gann, 88(10), 1003-1008 (1998-01-01)
In 5-day incubation of an estrogen receptor-negative human ovarian cancer cell line (KF) with N,N-diethyl-2-[4-(phenylmethyl)phenoxy]ethanamine-HCl (DPPE), the concentration of DPPE required for 50% inhibition of KF cell proliferation (IC50) was 1.7 microM. The IC50 of DPPE for inhibition of protein
Young H Choi et al.
The Journal of pharmacy and pharmacology, 62(8), 1084-1088 (2010-07-29)
It has been reported that docetaxel is a P-glycoprotein substrate and is metabolized via the cytochrome P450 (CYP) 3A subfamily in rats. Tesmilifene is a substrate of the CYP3A subfamily and is an inhibitor of P-glycoprotein. Thus, the effects of
Kouki Kase et al.
Organic letters, 9(5), 931-934 (2007-01-31)
[reaction: see text] A highly practical, general method for catalytic formation of substituted pyridines from a variety of unactivated nitriles and alpha,omega-diynes is given. The reactions which were catalyzed by 5 mol % of dppe/CoCl2-6H2O in the presence of Zn
K Kudoh et al.
European journal of cancer (Oxford, England : 1990), 33(1), 122-128 (1997-01-01)
This study was designed to the elucidate sensitising effects of the intracellular histamine antagonist, N,N-diethyl-2[4-(phenylmethyl)phenoxy] ethanamine HCl (DPPE) on the antitumour activity of cis-diamminedichloroplatinum (II) (CDDP) using human ovarian cancer cell lines with different sensitivities to CDDP (KF, sensitive) KFra
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