Benzamidenafil

Benzamidenafil
Names
	Preferred IUPAC name N-[(3,4-Dimethoxyphenyl)methyl]-2-[(1-hydroxypropan-2-yl)amino]-5-nitrobenzamide
	Other names Xanthoanthrafil
Identifiers
CAS Number	1020251-53-9;
3D model (JSmol)	Interactive image;
ChemSpider	8286399;
MeSH	C442640
PubChem CID	10110873;
UNII	B6ZMZ878RF;
CompTox Dashboard (EPA)	DTXSID501031839 ;
	InChI InChI=1S/C19H23N3O6/c1-12(11-23)21-16-6-5-14(22(25)26)9-15(16)19(24)20-10-13-4-7-17(27-2)18(8-13)28-3/h4-9,12,21,23H,10-11H2,1-3H3,(H,20,24) Key: ZISFCTXLAXIEMV-UHFFFAOYSA-N; InChI=1/C19H23N3O6/c1-12(11-23)21-16-6-5-14(22(25)26)9-15(16)19(24)20-10-13-4-7-17(27-2)18(8-13)28-3/h4-9,12,21,23H,10-11H2,1-3H3,(H,20,24) Key: ZISFCTXLAXIEMV-UHFFFAOYAW;
	SMILES COC1=C(OC)C=C(CNC(=O)C2=CC(=CC=C2NC(C)CO)[N+]([O-])=O)C=C1;
Properties
Chemical formula	C19H23N3O6
Molar mass	389.408 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Benzamidenafil or xanthoanthrafil is a synthetic drug that acts as a PDE5 inhibitor. It has the same mechanism of action as pharmaceutical drugs used to treat erectile dysfunction,^[1] but it is not approved by any regulatory agency for such use.

The drug has been found as an undeclared adulterant in supposedly "natural" health supplements.^[1] In 2009, the supplement manufacturer Hi-Tech Pharmaceuticals recalled its product Stamina-Rx because it was adulterated with benzamidenafil.^[2]

References

^ ^a ^b Zou, Peng; Hou, Peiling; Oh, Sharon Sze-Yin; Ge, Xiaowei; Bloodworth, Bosco Chen; Low, Min-Yong; Koh, Hwee-Ling (2008). "Identification of benzamidenafil, a new class of phosphodiesterase-5 inhibitor, as an adulterant in a dietary supplement". Journal of Pharmaceutical and Biomedical Analysis. 47 (2): 255–259. doi:10.1016/j.jpba.2008.01.004. PMID 18280079.
^ Miranda Hitti. "Stamina-Rx Supplements Recalled". WebMD. Retrieved 2022-08-17.