6715. Nortriptyline

Nomenclature

CAS number: 72-69-5
3-(10,11-Dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene)-N-methyl-1-propanamine; 10,11-dihydro-N-methyl-5H-dibenzo[a,d]cycloheptene-Δ5,γ-propylamine; 5-(α-methylaminopropylidene)dibenzo[a,d]cyclohepta[1,4]diene; 3-(10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene)-N-methylpropylamine; 10,11-dihydro-5-(3-methylaminopropylidene)-5H-dibenzo[a,d][1,4]cycloheptene; desitriptilina; desmethylamitriptyline.
C19H21N; mol wt 263.38.
C 86.64%, H 8.04%, N 5.32%.

Description and references

Tricyclic antidepressant. Prepn: Hoffsommer et al., J. Org. Chem. 27, 4134 (1962); NL 6408512; E. I. Engelhardt, US 3922305 (1965, 1975 both to Merck & Co.). Alternative process: N. L. Wendler, US 3442949 (1969 to Merck & Co.). GC determn in plasma: J. E. Burch, J. Chromatogr. 308, 165 (1984). Determn in plasma or serum by radioimmunoassay: J. F. Sayegh, Neurochem. Res. 11, 193 (1986). HPLC determn in serum: O. V. Olesen et al., J. Chromatogr. B 746, 233 (2000). Pharmacokinetics: E. H. Rubin et al., J. Clin. Psychiatry 46, 418 (1985). Clinical pharmacogenetics: E. E. Kvist et al., Clin. Pharmacokinet. 40, 869 (2001). Clinical trial in post-stroke depression: J. R. Lipsey et al., Lancet 1, 297 (1984); in treatment-resistant depression: A. A. Nierenberg et al., J. Clin. Psychiatry 64, 35 (2003). Anticholinergic effect and clinical efficacy in urinary dysfunction: I. Nissenkorn et al., Eur. Urol. 12, 109 (1986). Comprehensive description: J. L. Hale, Anal. Profiles Drug Subs. 1, 233-247 (1972).

Chemical structure

Derivative

Hydrochloride.

Nomenclature

CAS number: 894-71-3
Acetexa (Lilly); Allegron (Lilly); Aventyl (Lilly); Noritren (Lundbeck); Nortrilen (Lundbeck); Pamelor (Mallinckrodt); Sensaval (Lundbeck); Vividyl (Lilly).
C19H21N.HCl; mol wt 299.84.
C 76.11%, H 7.40%, N 4.67%, Cl 11.82%.

Properties

Crystals from ether + ethanol, mp 213-215°. Sol in ethanol, water, chloroform. Practically insol in ether, acetone, benzene. uv max (methanol): 240 nm (ε 13900).

Therapeutic Category

Antidepressant.

Therapeutic Category (Veterinary)

In treatment of canine behavioral disorders.

Keywords

Antidepressant; Tricyclics