1533. Butriptyline

Nomenclature

CAS number: 35941-65-2
10,11-Dihydro-N,N,β-trimethyl-5H-dibenzo[a,d]cycloheptene-5-propanamine; 5-(3-dimethylamino-2-methylpropyl)-10,11-dihydro-5H-dibenzo[a,d]cycloheptene; 5-(2-methyl-3-dimethylaminopropyl)dibenzo[a,d][1,4]cycloheptadiene; butriptylene.
C21H27N; mol wt 293.45.
C 85.95%, H 9.27%, N 4.77%.

Description and references

Prepn: Winthrop, Davis, BE 613750 (1962 to Ayerst, McKenna & Harrison), C.A. 57, 15036c (1962); eidem, J. Org. Chem. 27, 230 (1962); Villani, US 3409640 (1968 to Schering). Review of pharmacology and clinical data: see J. Med. 2, 249-343 (1971). Metabolic studies: Cameron et al., Arzneim.-Forsch. 24, 93 (1974). Toxicity: Voith, Herr, Arch. Int. Pharmacodyn. Ther. 182, 318 (1969).

Chemical structure

Properties

Oil, bp1 180-185°.

Derivative

Hydrochloride.

Nomenclature

CAS number: 5585-73-9
AY-62014; Evadene (Ayerst); Evadyne (Ayerst).
C21H27N.HCl; mol wt 329.91.
C 76.45%, H 8.55%, N 4.25%, Cl 10.75%.

Properties

Crystals from isopropyl alcohol-ether, mp 188-190° (dec). uv max (methanol): 273, 270, 266 nm (ε 460, 441, 552). Freely sol in water; moderately sol in aliphatic alc, chloroform. Insol in ether, paraffinic hydrocarbons. LD50 in mice (mg/kg): 120 i.p.; 345 orally (Voith, Herr).

Therapeutic Category

Antidepressant.

Keywords

Antidepressant; Tricyclics