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,[1] but it is not approved by any regulatory agency for such use. It 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]

Benzamidenafil
Names
Preferred IUPAC name
N-[(3,4-Dimethoxyphenyl)methyl]-2-[(1-hydroxypropan-2-yl)amino]-5-nitrobenzamide
Other names
Xanthoanthrafil
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
MeSH C442640
PubChem CID
UNII
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. 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.
  2. Miranda Hitti. "Stamina-Rx Supplements Recalled". WebMD. Retrieved 2022-08-17.


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