Sertraline
Structural Formula Vector Image
Title: Sertraline
CAS Registry Number: 79617-96-2
CAS Name: (1S,4S)-4-(3,4-Dichlorophenyl)-1,2,3,4-tetrahydro-N-methyl-1-naphthalenamine
Molecular Formula: C17H17Cl2N
Molecular Weight: 306.23
Percent Composition: C 66.68%, H 5.60%, Cl 23.15%, N 4.57%
Literature References: Selective serotonin reuptake inhibitor (SSRI). Prepn: W. M. Welch et al., EP 30081; eidem, US 4536518 (1981, 1985 both to Pfizer); and stereospecific activity: W. M. Welch et al., J. Med. Chem. 27, 1508 (1984). GC determn in plasma: H. G. Fouda et al., J. Chromatogr. 417, 197 (1987). Comprehensive description: B. M. Johnson, P.-T. L. Chang, Anal. Profiles Drug Subs. Excip. 24, 443-486 (1996). Review of pharmacology and clinical efficacy in depression and obsessive-compulsive disorder: D. Murdoch, D. McTavish, Drugs 44, 604-624 (1992). Clinical trial in posttraumatic stress disorder: K. Brady et al., J. Am. Med. Assoc. 283, 1837 (2000).
 
Derivative Type: Hydrochloride
CAS Registry Number: 79559-97-0
Manufacturers' Codes: CP-51974-1
Trademarks: Lustral (Pfizer); Zoloft (Pfizer)
Molecular Formula: C17H17Cl2N.HCl
Molecular Weight: 342.69
Percent Composition: C 59.58%, H 5.29%, Cl 31.04%, N 4.09%
Properties: Crystals, mp 243-245°. [a]D23 +37.9° (c = 2 in methanol). Soly room temp. (mg/ml): water 3.8; 0.1N HCl 0.51; 0.1N NaOH 0.002; ethanol 15.7; isopropyl alcohol 4.3; chloroform 110; acetone 1.1; N,N-dimethylformamide 88; dimethylsulfoxide 147; ethyl acetate 0.20; acetonitrile 0.85; methanolic 0.1N HCl 47; chloroform/methanol (1:1) 134. pKa (water): 9.48 ± 0.04. pKa (methanol:water, 40:60 v/v): 8.6. pKa (ethanol:water, 1:1 v/v): 8.5. d 1.37.
Melting point: mp 243-245°
pKa: pKa (water): 9.48 ± 0.04; pKa (methanol:water, 40:60 v/v): 8.6; pKa (ethanol:water, 1:1 v/v): 8.5
Optical Rotation: [a]D23 +37.9° (c = 2 in methanol)
Density: d 1.37
 
Therap-Cat: Antidepressant; antiobsessional.
Keywords: Antidepressant; Bicyclics; Antiobsessional; Serotonin Uptake Inhibitor.

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