2387. Clomipramine

Nomenclature

CAS number: 303-49-1
3-Chloro-10,11-dihydro-N,N-dimethyl-5H-dibenz[b,f]azepine-5-propanamine; 3-chloro-5-[3-(dimethylamino)propyl]-10,11-dihydro-5H-dibenz[b,f]azepine; 5-(γ-dimethylaminopropyl)-3-chloroiminodibenzyl; chlorimipramine; G-34586.
C19H23ClN2; mol wt 314.85.
C 72.48%, H 7.36%, Cl 11.26%, N 8.90%.

Description and references

Serotonin reuptake inhibitor. Prepn: P. N. Craig et al., J. Org. Chem. 26, 135 (1961); W. Schindler, H. Dietrich, CH 371799; eidem, US 3467650 (1963, 1969 both to Geigy). Crystal and molecular structure of the hydrochloride: M. L. Post, A. S. Horn, Acta Crystallogr. 33B, 2590 (1977). HPLC determn in serum: H. Weigmann et al., J. Chromatogr. B 710, 227 (1998). Veterinary trial in canine compulsive disorder: C. J. Hewson et al., J. Am. Vet. Med. Assoc. 213, 1760 (1998); in canine separation anxiety: S. Petit et al., Rev. Med. Vet. 150, 133 (1999). Review of pharmacology and clinical experience in obsessive-compulsive disorder and depression: M. D. Peters et al., Clin. Pharm. 9, 165-178 (1990).

Chemical structure

Properties

bp0.3 160-170°.

Derivative

Hydrochloride.

Nomenclature

CAS number: 17321-77-6
Anafranil (Novartis); Clomicalm (Novartis).
C19H23ClN2.HCl; mol wt 351.31.
C 64.96%, H 6.89%, Cl 20.18%, N 7.97%.

Properties

Crystals from acetone-ether/methanol-ether, mp 189-190° (Craig); also reported as crystals from acetone, mp 191.5-192° (Schindler, Dietrich). Freely sol in water, methanol, methylene chloride. Practically insol in ethyl ether, hexane.

Therapeutic Category

Antidepressant; antiobsessional agent.

Therapeutic Category (Veterinary)

In treatment of canine separation anxiety.

Keywords

Antidepressant; Tricyclics ; Antiobsessional