Imipramine
Structural Formula Vector Image
Title: Imipramine
CAS Registry Number: 50-49-7
CAS Name: 10,11-Dihydro-N,N-dimethyl-5H-dibenz[b,f]azepine-5-propanamine
Additional Names: 5-(3-dimethylaminopropyl)-10,11-dihydro-5H-dibenz[b,f]azepine; N-(g-dimethylaminopropyl)iminodibenzyl; imizin
Manufacturers' Codes: G-22355
Molecular Formula: C19H24N2
Molecular Weight: 280.41
Percent Composition: C 81.38%, H 8.63%, N 9.99%
Literature References: Tricyclic antidepressant. Prepn: Haefliger, Schindler, US 2554736 (1951 to Geigy); eidem, Helv. Chim. Acta 37, 472 (1954). Reviews of pharmacology: Crismon, Psychopharmacol. Bull. 4, 151 pp (Oct. 1967); Glassman, Perel, Arch. Gen. Psychiatry 28, 649 (1973). Toxicity data: A. Tobe et al., Arzneim.-Forsch. 31, 1278 (1981). Comprehensive description: D. N. Kender, R. E. Schiesswohl, Anal. Profiles Drug Subs. 14, 37-75 (1985). Comparative clinical trials in depression: R. S. Lipman et al., Arch. Gen. Psychiatry 43, 68 (1986); in anxiety: R.J. Kahn et al., ibid. 79. Clinical trial for panic disorder: D. H. Barlow et al., J. Am. Med. Assoc. 283, 2529 (2000).
Properties: Free base, bp0.1 160°.
Boiling point: bp0.1 160°
 
Derivative Type: Hydrochloride
CAS Registry Number: 113-52-0
Trademarks: Chrytemin (Fujinaga); Deprinol (Dumex); Feinalmin (Sanko); Imidol (Yoshitomi); Imilanyle (Takata); Imiprin (CP Protea); Janimine (Abbott); Melipramine (EGYT); Presamine (USV); Pryleugan (Temmler); Tofranil (Novartis)
Molecular Formula: C19H24N2.HCl
Molecular Weight: 316.87
Percent Composition: C 72.02%, H 7.95%, N 8.84%, Cl 11.19%
Properties: Crystals from acetone, mp 174-175°. Acquires a yellow to reddish discoloration under the influence of light. Freely sol in water, less sol in alcohol, sparingly sol in acetone. LD50 in mice, rats (mg/kg): 400, 490 orally; 110, 90 i.p. (Tobe).
Melting point: mp 174-175°
Toxicity data: LD50 in mice, rats (mg/kg): 400, 490 orally; 110, 90 i.p. (Tobe)
 
Derivative Type: Pamoate
CAS Registry Number: 10075-24-8
Trademarks: Tofranil-PM (Novartis)
Molecular Formula: (C19H24N2)2.C23H16O6
Molecular Weight: 949.18
Percent Composition: C 77.19%, H 6.80%, N 5.90%, O 10.11%
 
Therap-Cat: Antidepressant.
Keywords: Antidepressant; Tricyclics.

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