Imipramine N-Oxide
Structural Formula Vector Image
Title: Imipramine N-Oxide
CAS Registry Number: 6829-98-7
CAS Name: 10,11-Dihydro-N,N-dimethyl-5H-dibenz[b,f]azepine-5-propanamine N-oxide
Additional Names: 5-[3-(dimethylamino)propyl]-10,11-dihydro-5H-dibenz[b,f]azepine N-oxide; N-(g-dimethylaminopropyl)iminodibenzyl N-oxide; IPNO
Molecular Formula: C19H24N2O
Molecular Weight: 296.41
Percent Composition: C 76.99%, H 8.16%, N 9.45%, O 5.40%
Literature 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).
Properties: White needle-shaped crystals, mp 120-123° (dec). Sol in methanol, ether, acetone and benzene. Strongly hygroscopic.
Melting point: mp 120-123° (dec)
Derivative Type: Monohydrate
Properties: mp 75-79°.
Melting point: mp 75-79°
Derivative Type: Hydrochloride
CAS Registry Number: 20438-98-6
Trademarks: Imiprex (Dumex)
Molecular Formula: C19H24N2O.HCl
Molecular Weight: 332.87
Percent Composition: 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).
Melting point: mp 167-174°; mp 153-155° (dec)
Toxicity data: LD50 in rats, mice (mg/kg): 90, 150 i.p. (Dyrsting, Pedersen)
Therap-Cat: Antidepressant.
Keywords: Antidepressant; Tricyclics.

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