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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:
Molecular Weight:
319.87
MDL number:
UNSPSC Code:
51111800
PubChem Substance ID:
NACRES:
NA.77

$106.00


Available to ship onMay 02, 2025Details


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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 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

11 - Combustible Solids

wgk_germany

nwg

flash_point_f

Not applicable

flash_point_c

Not applicable


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G Veszely et al.
Current medicinal chemistry, 9(14), 1349-1357 (2002-07-23)
Endogenous histamine regulates the haematopoiesis. Histidine decarboxylase inhibitor decreases the histamine level, and its intracellular antagonist decreases the histamine effect. The effect of histidine decarboxylase inhibitor (alpha-fluoromethyl histidine) and the intracellular antagonist of histamine [N'N-diethyl-2-4-(phenylmethyl) phenoxyethan-amine-HCl] was investigated on the
Peter J Ferguson et al.
Cancer letters, 274(2), 279-289 (2008-11-07)
N,N-diethyl-2-[4-(phenylmethyl)phenoxyl]ethanamine (tesmilifene), a tamoxifen derivative with antihistamine activity, greatly enhanced the survival of doxorubicin-treated, advanced stage breast cancer patients in a phase III trial. However, the molecular basis of tesmilifene action is not firmly established. The effects of tesmilifene on
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
M Poirot et al.
Bioorganic & medicinal chemistry, 8(8), 2007-2016 (2000-09-26)
New compounds have been synthesized based on the structure of the anti-tumoral drug tamoxifen and its diphenylmethane derivative, N,N-diethyl-2-[(4-phenyl-methyl)-phenoxy]-ethanamine, HCl (DPPE). These new compounds have no affinity for the estrogen receptor (ER) and bind with various affinity to the anti-estrogen
L J Brandes et al.
Breast cancer research and treatment, 49(1), 61-68 (1998-08-07)
N,N-diethyl-2-[4-(phenylmethyl)phenoxy] ethanamine.HCl (DPPE) is a diphenylmethane analog of tamoxifen that antagonizes the intracellular binding of histamine to growth-regulatory sites, a proportion of which represents P450 enzymes, in microsomes and nuclei. We previously reported increased response rates and decreased myelotoxicity in

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