CAS No 54910-89-3 , N-methyl-3-phenyl-3-[4-(trifluoromethyl)phenoxy]propan-1-amine

Title: Fluoxetine
CAS Registry Number: 54910-89-3
CAS Name: N-Methyl-g-[4-(trifluoromethyl)phenoxy]benzenepropanamine
Synonyms: (±)-N-methyl-3-phenyl-3-[(a,a,a-trifluoro-p-tolyl)oxy]propylamine; dl-N-methyl-3-(p-trifluoromethylphenoxy)-3-phenylpropylamine
Molecular Formula: C17H18F3NO
Molecular Weight: 309.33
Percent Composition: C 66.01%, H 5.87%, F 18.43%, N 4.53%, O 5.17%
Literature References: Selective serotonin reuptake inhibitor (SSRI). Prepn: B. B. Malloy, K. K. Schmiegel, DE 2500110; eidem, US 4314081 (1975, 1982 both to Lilly). Pharmacology: D. T. Wong et al., Life Sci. 15, 471 (1974). GC determn in plasma: J. F. Nash et al., Clin. Chem. 28, 2100 (1982). Series of articles on clinical pharmacology and therapeutic efficacy in depression: J. Clin. Psychiatry 46, Suppl. 3(2), 2-67 (1985). Toxicity data: P. Stark et al., ibid. 7. Clinical trial in bulimia nervosa: D. J. Goldstein et al., Br. J. Psychiatry 166, 660 (1995); in obsessive-compulsive disorder: J. J. Lopez-Ibor, Jr. et al., Eur. Neuropsychopharmacol. 6, 111 (1996). Veterinary trial in canine aggression: N. H. Dodman et al., J. Am. Vet. Med. Assoc. 209, 1585 (1996). Comprehensive description: D. S. Risley, R. J. Bopp, Anal. Profiles Drug Subs. 19, 193-219 (1990). Review of clinical experience: P. E. Stokes, A. Holtz, Clin. Ther. 19, 1135-1250 (1997); in premenstrual dysphoric disorder: S. Romano et al., Clin. Ther. 21, 615 (1999).
 
Derivative Type: Hydrochloride
CAS Registry Number: 59333-67-4
Manufacturers' Codes: LY-110140
Trademarks: Adofen (Ferrer); Fluctin (Lilly); Fluoxeren (Menarini); Fontex (Lilly); Foxetin (Gador); Lovan (Lilly); Prozac (Lilly); Reneuron (Juste); Sarafem (Lilly)
Molecular Formula: C17H18F3NO.HCl
Molecular Weight: 345.79
Percent Composition: C 59.05%, H 5.54%, F 16.48%, N 4.05%, O 4.63%, Cl 10.25%
Properties: White to off-white crystalline solid. mp 158.4-158.9°. Soly (mg/ml): methanol, ethanol >100; acetone, acetonitrile, chloroform 33-100; dichloromethane 5-10; ethyl acetate 2-2.5; toluene, cyclohexane, hexane 0.5-0.67. Maximum soly in water: 14 mg/ml. uv max (methanol) 227, 264, 268, 275 nm (E1%1cm 372.0, 29.2, 29.3, 21.5). LD50 in mice, rats (mg/kg): 248, 452 orally (Stark).
Melting point: mp 158.4-158.9°
Absorption maximum: uv max (methanol) 227, 264, 268, 275 nm (E1%1cm 372.0, 29.2, 29.3, 21.5)
Toxicity data: LD50 in mice, rats (mg/kg): 248, 452 orally (Stark)
 
Derivative Type: Oxalate
Molecular Formula: C19H18F3NO5
Molecular Weight: 397.35
Percent Composition: C 57.43%, H 4.57%, F 14.34%, N 3.53%, O 20.13%
Properties: Crystals from ethyl acetate-methanol, mp 179-182° (dec).
Melting point: mp 179-182° (dec)
 
Therap-Cat: Antidepressant; antiobessional; antibulimic.
Keywords: Antidepressant; Serotonin Uptake Inhibitor; Antiobsessional.