Structural Formula Vector Image
Title: Diazepam
CAS Registry Number: 439-14-5
CAS Name: 7-Chloro-1,3-dihydro-1-methyl-5-phenyl-2H-1,4-benzodiazepin-2-one
Additional Names: 7-chloro-1-methyl-5-phenyl-3H-1,4-benzodiazepin-2(1H)-one; methyl diazepinone; diacepin
Manufacturers' Codes: LA-III; Ro-5-2807; Wy-3467; NSC-77518
Trademarks: Apaurin (Krka); Bialzepam (Bial); Calmpose (Ranbaxy); Ceregulart (Kaken); Dialar (Novartis); Diastat (Xcel); Diazemuls (Alpharma); Eurosan (Mepha); Faustan (Temmler); Gewacalm (Nycomed); Lamra (Merckle); Noan (Teofarma); Novazam (Gš¢rier); Paceum (Orion); Paxate (BMS); Relanium (Polfa); Seduxen (Gedeon Richter); Servizepam (Novartis); Stesolid (Alpharma); Unisedil (Merck KGaA); Valiquid (Roche); Valium (Roche); Vival (Alpharma)
Molecular Formula: C16H13ClN2O
Molecular Weight: 284.74
Percent Composition: C 67.49%, H 4.60%, Cl 12.45%, N 9.84%, O 5.62%
Literature References: Prepn: L. H. Sternbach, E. Reeder, J. Org. Chem. 26, 4936 (1961); E. Reeder, L. H. Sternbach, US 3371085 (1968 to Hoffmann-La Roche). Purification: G. Chase, US 3102116 (1963 to Hoffmann-La Roche). Synthesis: M. Gates, J. Org. Chem. 45, 1675 (1980); M. Ishikura et al., ibid. 47, 2456 (1982). Binding study in rat brain: R. F. Squires, C. Braestrup, Nature 266, 732 (1977). Comprehensive description: A. MacDonald et al., Anal. Profiles Drug Subs. 1, 79-99 (1972). Review of clinical pharmacokinetics: M. Mandelli et al., Clin. Pharmacokinet. 3, 72-91 (1978); and metabolism: L. Bertilsson et al., Pharmacol. Ther. 45, 85-91 (1990). Review of clinical experience and dependency potential in anxiety: J. B. Murray, J. Psychol. 124, 655-674 (1990); of use in seizure treatment: J. M. Pellock, Drug Saf. 27, 383-392 (2004).
Properties: Colorless to light yellow crystalline compound. Prisms from ethanol, mp 131.5-134.5°. pKa 3.4. Sol in chloroform, DMF, benzene, acetone, alc. Practically insol in water.
Melting point: mp 131.5-134.5°
pKa: pKa 3.4
NOTE: This is a controlled substance (depressant): 21 CFR, 1308.14.
Therap-Cat: Anxiolytic; muscle relaxant (skeletal); anticonvulsant.
Keywords: Anxiolytic; Benzodiazepine Derivatives; Muscle Relaxant (Skeletal); Anticonvulsant.

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