N-Desmethyltamoxifen

Modify Date: 2024-01-31 18:51:47

N-Desmethyltamoxifen Structure
N-Desmethyltamoxifen structure
Common Name N-Desmethyltamoxifen
CAS Number 31750-48-8 Molecular Weight 357.48800
Density 1.047 g/cm3 Boiling Point 485.8ºC at 760 mmHg
Molecular Formula C25H27NO Melting Point N/A
MSDS N/A Flash Point 213.2ºC

 Use of N-Desmethyltamoxifen


N-Desmethyltamoxifen is the major metabolite of tamoxifen in humans. N-Desmethyltamoxifen, a poor antiestrogen, is a ten-fold more potent protein kinase C (PKC) inhibitor than Tamoxifen. N-Desmethyltamoxifen is also a potent regulator of ceramide metabolism in human AML cells, limiting ceramide glycosylation, hydrolysis, and sphingosine phosphorylation[1][2][3].

 Names

Name n-desmethyltamoxifen, hydrochloride
Synonym More Synonyms

 N-Desmethyltamoxifen Biological Activity

Description N-Desmethyltamoxifen is the major metabolite of tamoxifen in humans. N-Desmethyltamoxifen, a poor antiestrogen, is a ten-fold more potent protein kinase C (PKC) inhibitor than Tamoxifen. N-Desmethyltamoxifen is also a potent regulator of ceramide metabolism in human AML cells, limiting ceramide glycosylation, hydrolysis, and sphingosine phosphorylation[1][2][3].
Related Catalog
Target

PKC

In Vitro N-desmethyltamoxifen (20-500 ng/ml; 48 hours) has a profound inhibitory effect upon all seven glioma lines (T98G, U87, U138, U373, ALW, AUK, CAS cells)[1]. N-desmethyltamoxifen (1.5-10 μM; 114 hours) inhibits growth of MCF 7 human mammary carcinoma cells[2]. N-desmethyltamoxifen, resulting from the CYP3A4/5-mediated catalysis of tamoxifen, is the major primary quantitative metabolite of tamoxifen[3]. Cell Viability Assay[2] Cell Line: MCF 7 human mammary carcinoma cells Concentration: 1.5, 2.5, 5, 7.5, 10 μM Incubation Time: 114 hours Result: Inhibits growth of MCF 7 human mammary carcinoma cells
References

[1]. Vertosick FT Jr, et al. A comparison of the relative chemosensitivity of human gliomas to tamoxifen and n-desmethyltamoxifen in vitro. J Neurooncol. 1994;19(2):97-103.

[2]. Morad SA, et al. Modification of sphingolipid metabolism by tamoxifen and N-desmethyltamoxifen in acute myelogenous leukemia--Impact on enzyme activity and response to cytotoxics. Biochim Biophys Acta. 2015 Jul;1851(7):919-28.

[3]. Reddel RR,et al. N-desmethyltamoxifen inhibits growth of MCF 7 human mammary carcinoma cells in vitro. Eur J Cancer Clin Oncol. 1983 Aug;19(8):1179-81.

[4]. Seong Hwan Kim,et al. Use of Antidepressants in Patients with Breast Cancer Taking Tamoxifen. J Breast Cancer. 2010 Dec;13(4):325-336.

 Chemical & Physical Properties

Density 1.047 g/cm3
Boiling Point 485.8ºC at 760 mmHg
Molecular Formula C25H27NO
Molecular Weight 357.48800
Flash Point 213.2ºC
Exact Mass 357.20900
PSA 21.26000
LogP 6.04480

 Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
KR6712700
CHEMICAL NAME :
Ethylamine, 2-(p-(1,2-diphenyl-1-butenyl)phenoxy)-N-methyl-, (Z)-
CAS REGISTRY NUMBER :
31750-48-8
LAST UPDATED :
198910
DATA ITEMS CITED :
1
MOLECULAR FORMULA :
C25-H27-N-O
MOLECULAR WEIGHT :
357.53

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
50 ug/kg
SEX/DURATION :
female 4 day(s) after conception
TOXIC EFFECTS :
Reproductive - Fertility - pre-implantation mortality (e.g. reduction in number of implants per female; total number of implants per corpora lutea)
REFERENCE :
CTRRDO Cancer Treatment Reports. (Washington, DC) V.60-71, 1976-87. For publisher information, see JNCIEQ. Volume(issue)/page/year: 64,741,1980

 Safety Information

Hazard Codes Xn

 Synonyms

desmethyl Tamoxifen
N-Desmethyl-psilocybin
N-demethyltamoxifen
N-desmethyl-tamoxifen
Baeocystin
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