160. Adinazolam

Nomenclature

CAS number: 37115-32-5
8-Chloro-N,N-dimethyl-6-phenyl-4H-[1,2,4]triazolo[4,3-a][1,4]benzodiazepine-1-methanamine; 8-chloro-1-[(dimethylamino)methyl]-6-phenyl-4H-s-triazolo[4,3-a][1,4]benzodiazepine; U-41123.
C19H18ClN5; mol wt 351.83.
C 64.86%, H 5.16%, Cl 10.08%, N 19.91%.

Description and references

Triazolobenzodiazepine; dimethylamino derivative of alprazolam, q.v. Prepn: H. Allgeier, A. Gagneux, DE 2201210; GB 1393256 (1972, 1975 both to Ciba-Geigy); J. B. Hester, Jr., US 4250094 (1984 to Upjohn); idem, J. Heterocycl. Chem. 17, 575 (1980). Chromatographic determn in human plasma: G. W. Peng, J. Pharm. Sci. 73, 1173 (1984). Pharmacological profile: R. A. Lahti et al., Neuropharmacology 22, 1277 (1983). Biological activity and metabolism: V. H. Sethy et al., J. Pharm. Pharmacol. 36, 546 (1984). Preliminary clinical study in severe depression: R. E. Pyke et al., Psychopharmacol. Bull. 19, 96 (1983).

Chemical structure

Properties

Crystals from ethyl acetate, mp 171-172.5° (US 4250094). Also reported as mp 165-166° (DE 2201210).

Derivative

Methanesulfonate.

Nomenclature

CAS number: 57938-82-6
Adinazolam mesylate; Deracyn (Upjohn).
C19H18ClN5.CH3SO3H; mol wt 447.94.
C 53.63%, H 4.95%, Cl 7.91%, N 15.63%, S 7.16%, O 10.72%.

Properties

Crystals from methanol-ether, mp 230-244°.

Therapeutic Category

Antidepressant.

Keywords

Antidepressant; Tricyclics