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D2571

Sigma-Aldrich

DPPE hydrochloride

≥98% (HPLC)

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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
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.

WGK

nwg

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Information

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Histidine decarboxylase and intracellular histamine in melanoma cells and in a T cell line.
A Falus et al.
Inflammation research : official journal of the European Histamine Research Society ... [et al.], 46 Suppl 1, S51-S52 (1997-03-01)
Jianhua Liu et al.
Breast cancer research and treatment, 100(3), 263-271 (2006-07-11)
DPPE (tesmilifene) plus doxorubicin (DOX) demonstrated a significant improvement in survival versus DOX in a phase III clinical trial in advanced breast cancer. However, DPPE is associated with unusual toxicity in the form of hallucinations, nausea and vomiting which were
Mark Vincent
Medical hypotheses, 66(4), 715-731 (2006-01-18)
Tesmilifene is a novel potentiator of chemotherapy which, when added to doxorubicin, achieved an unexpected and very large survival advantage over doxorubicin alone in a randomized trial in advanced breast cancer. This trial was unusual in that the early endpoints
L Németh et al.
European journal of pediatric surgery : official journal of Austrian Association of Pediatric Surgery ... [et al] = Zeitschrift fur Kinderchirurgie, 8(4), 216-219 (1998-10-23)
Resuscitation in pediatric emergency and some neurological interventions may result in ischemia reperfusion-induced cerebral injuries. Histamine is one of the well established mediators of cerebral swelling and H1- and H2-receptor antagonists could prevent the development of ischemic brain edema. In
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
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