An active metabolite of tamoxifen
Related Products
Parent Compound(s)
13258Tamoxifen 11629Tamoxifen (citrate)
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N-Desmethyltamoxifen (hydrochloride)

Item No. 40673

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
2-[4-[(1Z)-1,2-diphenyl-1-buten-1-yl]phenoxy]-N-methyl-ethanamine
CAS Number
15917-65-4
Molecular Formula
C25H27NO • HCl
Formula Weight
394.0
Purity
≥95%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMSO: Sparingly soluble: 1-10 mg/mLEthanol: Slightly soluble: 0.1-1mg/mLPBS (pH 7.2): Slightly soluble: 0.1-1mg/mL
SMILES
CC/C(C1=CC=CC=C1)=C(C2=CC=CC=C2)/C3=CC=C(C=C3)OCCNC.Cl
InChi Code
InChI=1S/C25H27NO.ClH/c1-3-24(20-10-6-4-7-11-20)25(21-12-8-5-9-13-21)22-14-16-23(17-15-22)27-19-18-26-2;/h4-17,26H,3,18-19H2,1-2H3;1H/b25-24-;
InChi Key
GMLHJWZEYLTNJW-BJFQDICYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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Certificates of Analysis & Batch Specific Data

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    5 mg

    $153

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    10 mg

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    25 mg

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    50 mg

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    Product Description

    N-Desmethyltamoxifen is an active metabolite of the estrogen receptor antagonist tamoxifen (Item Nos. 13258 | 11629).1 It is formed from tamoxifen by the cytochrome P450 (CYP) isoforms CYP2D6, CYP2C19, CYP3A5, or CYP3A4. N-Desmethyltamoxifen is an inhibitor of PKC (IC50 = 8 µM for the rat enzyme).2 It decreases iron (III) chloride and ascorbate-induced increases in thiobarbituric acid reactive substances (TBARS) in rat liver microsomes (IC50 = 17.5 µM).3 N-Desmethyltamoxifen induces relaxation in isolated and washed rat aortic rings (pD2 = 9), an effect that can be blocked with the selective estrogen receptor degrader ICI 182780 (fulvestrant; Item No. 10011269).4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Desta, Z., Ward, B.A., Soukhova, N.V., et al. Comprehensive evaluation of tamoxifen sequential biotransformation by the human cytochrome P450 system in vitro: Prominent roles for CYP3A and CYP2D6. J. Pharmacol. Exp. Ther. 310(3), 1062-1075 (2004).

    2. O'Brian, C.A., Liskamp, R.M., Solomon, D.H., et al. Triphenylethylenes: A new class of protein kinase C inhibitors. J. Natl. Cancer Inst. 76(6), 1243-1246 (1986).

    3. Wiseman, H., Laughton, M.J., Arnstein, H.R., et al. The antioxidant action of tamoxifen and its metabolites. Inhibition of lipid peroxidation. FEBS Lett. 263(2), 192-194 (1990).

    4. Montenegro, M.F., Ceron, C.S., Salgado, M.C.O., et al. Tamoxifen and its metabolites cause acute vasorelaxation of aortic rings by inducing vasodilator prostanoid synthesis. J. Cardiovasc. Pharmacol. 58(6), 647-653 (2011).