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2821. Dapoxetine Nomenclature CAS number: 119356-77-3 (¦ÁS)-N,N-Dimethyl-¦Á-[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). Synthesis: W. J. Wheeler, D. D. O'Bannon, J. Labelled Compd. Radiopharm. 31, 305 (1992) DOI; S. Kang, H.-K. Lee, J. Org. Chem. 75, 237 (2010) DOI PubMed. HPLC determn in plasma: C. L. Hamilton, J. D. Cornpropst, J. Chromatogr. 612, 253 (1993) DOI PubMed. Clinical pharmacokinetics: N. B. Modi et al., J. Clin. Pharmacol. 46, 301 (2006) DOI PubMed. Clinical trial: J. L. Pryor et al., Lancet 368, 929 (2006) DOI PubMed; C. G. McMahon et al., J. Sex. Med. 8, 524 (2011) DOI PubMed. Review of pharmacology and clinical experience: B. Feret, Formulary 40, 227-230 (2005); A. M. Feige et al., Clin. Pharmacol. Ther. 89, 125 (2011) DOI PubMed. Chemical structure Properties Colorless oil. [¦Á]D28 + 63.2¡ã (c=0.3 in chloroform). Derivative Hydrochloride. Nomenclature CAS number: 129938-20-1 Priligy (Janssen-Cilag). 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. [¦Á]D +135.78¡ã (c = 2.18 in methanol). Therapeutic Category In treatment of premature ejaculation. Keywords Serotonin Uptake Inhibitor |

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