N-Desmethyltamoxifen

N-Desmethyltamoxifen
Clinical data
Other names	ICI-55,548; Nortamoxifen; NDMTAM
Drug class	Selective estrogen receptor modulator
Identifiers
	IUPAC name 2-[4-[(Z)-1,2-Diphenylbut-1-enyl]phenoxy]-N-methylethanamine;
CAS Number	31750-48-8;
PubChem CID	6378383;
ChemSpider	2297759;
UNII	OOJ759O35C;
KEGG	C16546;
ChEBI	CHEBI:80554;
CompTox Dashboard (EPA)	DTXSID501315924 ;
ECHA InfoCard	100.170.899
Chemical and physical data
Formula	C25H27NO
Molar mass	357.497 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CC/C(=C(\C1=CC=CC=C1)/C2=CC=C(C=C2)OCCNC)/C3=CC=CC=C3;
	InChI InChI=1S/C25H27NO/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/b25-24-; Key:NYDCDZSEEAUOHN-IZHYLOQSSA-N;

N-Desmethyltamoxifen (developmental code name ICI-55,548) is a major metabolite of tamoxifen, a selective estrogen receptor modulator (SERM).^[1]^[2] N-Desmethyltamoxifen is further metabolized into endoxifen (4-hydroxy-N-desmethyltamoxifen), which is thought to be the major active form of tamoxifen in the body.^[1]^[2]^[3] In one study, N-desmethyltamoxifen had an affinity for the estrogen receptor of 2.4% relative to estradiol.^[4] For comparison, tamoxifen, endoxifen, and afimoxifene (4-hydroxytamoxifen) had relative binding affinities of 2.8%, 181%, and 181%, respectively.^[4]