4921. Imipramine N-Oxide

Nomenclature

CAS number: 6829-98-7
10,11-Dihydro-N,N-dimethyl-5H-dibenz[b,f]azepine-5-propanamine N-oxide; 5-[3-(dimethylamino)propyl]-10,11-dihydro-5H-dibenz[b,f]azepine N-oxide; N-(γ-dimethylaminopropyl)iminodibenzyl N-oxide; IPNO.
C19H24N2O; mol wt 296.41.
C 76.99%, H 8.16%, N 9.45%, O 5.40%.

Description and references

Identification as a metabolite of imipramine, q.v.: V. Fishman, H. Goldenberg, Proc. Soc. Exp. Biol. Med. 110, 187 (1962). Prepn: FR M2508; H. Dyrsting, J. B. Pedersen, US 3574852 (1964, 1971, both to Dumex). Pharmacology: W. Theobald et al., Med. Pharmacol. Exp. 15, 187 (1966). Metabolism: M. H. Bickel, M. Baggiolini, Biochem. Pharmacol. 15, 1155 (1966); R. Minder et al., Arch. Pharmakol. 268, 334 (1971). GLC determn in biological samples: H. J. Weder, M. H. Bickel, J. Chromatogr. 37, 181 (1968); HPLC determn: E. Koyama et al., Ther. Drug Monit. 15, 224 (1993). Clinical trial: W. Rapp et al., Acta Psychiatr. Scand. 49, 77 (1973). Clinical pharmacokinetics: A. Nagy, T. Hansen, Acta Pharmacol. Toxicol. 42, 58 (1978).

Chemical structure

Properties

White needle-shaped crystals, mp 120-123° (dec). Sol in methanol, ether, acetone and benzene. Strongly hygroscopic.

Derivative

Monohydrate.

Properties

mp 75-79°.

Derivative

Hydrochloride.

Nomenclature

CAS number: 20438-98-6
Imiprex (Dumex).
C19H24N2O.HCl; mol wt 332.87.
C 68.56%, H 7.57%, N 8.42%, O 4.81%, Cl 10.65%.

Properties

Colorless crystalline powder, mp 167-174°; also reported as mp 153-155° (dec). Very bitter taste. An aq. soln is moderately acidic. Sol in 75 parts water, in 12 parts 95% ethanol, 4.5 parts chloroform. Nearly insol in ether. LD50 in rats, mice (mg/kg): 90, 150 i.p. (Dyrsting, Pedersen).

Therapeutic Category

Antidepressant.

Keywords

Antidepressant; Tricyclics