Benzamidenafil

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, but it is not approved by any regulatory agency for such use.[1] It has been found as an undeclared adulterant in supposedly "natural" health supplements.[1][2] In 2009, the supplement manufacturer Hi-Tech Pharmaceuticals recalled its product Stamina-Rx because it was adulterated with benzamidenafil.[3]

Benzamidenafil

Names
IUPAC name N-[(3,4-Dimethoxyphenyl)methyl]-2-(1-hydroxypropan-2-ylamino)-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
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

References

1. Rica Lewis (Aug 16, 2013). "Stamina Rx Ingredients".
2. "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.
3. "FDA MedWatch – Stamina-Rx Dietary Supplement Products". Vanderbuilt University. Archived from the original on 2016-03-04. Retrieved 2014-09-14.