6549. Nimetazepam

Nomenclature

CAS number: 2011-67-8
1,3-Dihydro-1-methyl-7-nitro-5-phenyl-2H-1,4-benzodiazepin-2-one; 1-methyl-5-phenyl-7-nitro-1,3-dihydro-2H-1,4-benzodiazepin-2-one; 1-methylnitrazepam; S-1530; Erimin (Sumitomo).
C16H13N3O3; mol wt 295.29.
C 65.08%, H 4.44%, N 14.23%, O 16.25%.

Description and references

The desmethyl derivative of nitrazepam, q.v. Prepn: L. H. Sternbach et al., J. Med. Chem. 6, 261 (1963); E. Reeder, L. H. Sternbach, US 3109843; US 3144439; US 3141890; US 3243427 (1963, 1964, 1964, 1966 all to Hoffmann-La Roche); O. Keller et al., US 3121114; US 3203990 (1964, 1965 to Hoffmann-La Roche); Sorrentino, ZA 6706791 (1968 to Dumex), C.A. 70, 57916c (1969); Yamamoto et al., DE 1816046 (1970 to Sumitomo), C.A. 73, 120690d (1970); Inaba et al., Chem. Pharm. Bull. 19, 722 (1971). Pharmacology: S. Sakai et al., Arzneim.-Forsch. 22, 534 (1972).

Chemical structure

Properties

Pale yellow plates from ethanol, mp 156.5-157.5°. uv max (methanol): 259, 308 nm (ε 15800, 9600). LD50 in male, female mice, rats (mg/kg): 910, 750, 1150, 970 orally; 970, 840, 970, 980 i.p.; 1500, 1500, 1000, 1000 s.c. (Sakai).

Note

This is a controlled substance (depressant): 21 CFR, 1308.14.

Therapeutic Category

Sedative, hypnotic.

Keywords

Sedative/Hypnotic; Benzodiazepine Derivatives