487. Amitriptyline

Nomenclature

CAS number: 50-48-6
3-(10,11-Dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene)-N,N-dimethyl-1-propanamine; 10,11-dihydro-N,N-dimethyl-5H-dibenzo[a,d]cycloheptene-Δ5,γ-propylamine; 5-(γ-dimethylaminopropylidene)-5H-dibenzo[a,d]-10,11-dihydrocycloheptene; 10,11-dihydro-5-(γ-dimethylaminopropylidene)-5H-dibenzo[a,d]cycloheptene; 5-(3-dimethylaminopropylidene)dibenzo[a,d][1,4]cycloheptadiene.
C20H23N; mol wt 277.40.
C 86.59%, H 8.36%, N 5.05%.

Description and references

Prepn: Hoffsommer et al., J. Org. Chem. 27, 4134 (1962); 28, 1751 (1963); J. Med. Chem. 8, 555 (1965); Engelhardt et al., BE 584061 (1960 to Merck & Co.); GB 858187; GB 858188 (both 1961 to Hoffmann-La Roche); Tristram, Tull, US 3205264 (1965 to Merck & Co.). HPLC determn in plasma: A. Zarghi et al., Boll. Chim. Farm. 140, 458 (2001). Toxicity data: A. Tobe et al., Arzneim.-Forsch. 31, 1278 (1981). Comprehensive description: K. W. Blessel et al., Anal. Profiles Drug Subs. 3, 127-148 (1974). Review of pharmacology and use in chronic pain: H. M. Bryson, M. I. Wilde, Drugs Aging 8, 459-476 (1996).

Chemical structure

Derivative

Hydrochloride.

Nomenclature

CAS number: 549-18-8
Ro-4-1575; Adepril (Teofarma); Amineurin (Hexal); Domical (Berk); Elavil (AstraZeneca); Endep (Roche); Euplit (Desitin); Laroxyl (Roche); Lentizol (Lundbeck); Miketorin (Schering); Redomex (Lundbeck); Saroten (Bayer); Sarotex (Lundbeck); Triptizol (SIT); Tryptanol (Merck & Co.); Tryptizol (Merck & Co.).
C20H23N.HCl; mol wt 313.86.
C 76.54%, H 7.71%, N 4.46%, Cl 11.30%.

Properties

Minute crystals, mp 196-197°. Freely sol in water, chloroform, alc. uv max (methanol): 240 nm (ε 13800). pKa 9.4. LD50 in mice, rats (mg/kg): 350, 380 orally; 65, 75 i.p. (Tobe).

Therapeutic Category

Antidepressant.

Keywords

Antidepressant; Tricyclics