2821. Dapoxetine

Nomenclature

CAS number: 119356-77-3
(αS)-N,N-Dimethyl-α-[2-(1-naphthalenyloxy)ethyl]benzenemethanamine; (+)-N,N-dimethyl-1-phenyl-3-(1-naphthalenyloxy)propanamine; LY-210448.
C21H23NO; mol wt 305.41.
C 82.59%, H 7.59%, N 4.59%, O 5.24%.

Description and references

Selective serotonin reuptake inhibitor (SSRI). Prepn: D. W. Robertson et al., EP 288188; eidem, US 5135947 (1988, 1992 both to Lilly). Chiral synthesis: W. J. Wheeler, D. D. O'Bannon, J. Labelled Compd. Radiopharm. 31, 305 (1992). HPLC determn in plasma: C. L. Hamilton, J. D. Cornpropst, J. Chromatogr. 612, 253 (1993). Clinical pharmacokinetics: N. B. Modi et al., J. Clin. Pharmacol. 46, 301 (2006). Clinical trial: J. L. Pryor et al., Lancet 368, 929 (2006). Review of pharmacology and clinical experience: B. Feret, Formulary 40, 227-230 (2005).

Chemical structure

Derivative

Hydrochloride.

Nomenclature

CAS number: 129938-20-1
C21H23NO.HCl; mol wt 341.87.
C 73.78%, H 7.08%, N 4.10%, O 4.68%, Cl 10.37%.

Properties

White crystalline solid from hydrochloric acid and ethyl acetate. [α]D +135.78° (c = 2.18 in methanol).

Therapeutic Category

In treatment of premature ejaculation.

Keywords

Serotonin Uptake Inhibitor