2084. Chlordiazepoxide

Nomenclature

CAS number: 58-25-3
7-Chloro-N-methyl-5-phenyl-3H-1,4-benzodiazepin-2-amine 4-oxide; 7-chloro-2-methylamino-5-phenyl-3H-1,4-benzodiazepine 4-oxide; methaminodiazepoxide; clopoxide; Helogaphen (Spitzner); Libritabs (Roche); Multum (Chephasaar); Risolid (Dumex); Silibrin (Silesia); Tropium (DDSA).
C16H14ClN3O; mol wt 299.75.
C 64.11%, H 4.71%, Cl 11.83%, N 14.02%, O 5.34%.

Description and references

Prototype of the benzodiazepine anxiolytics. Prepn: Sternbach, US 2893992 (1959 to Hoffmann-La Roche); Sternbach, Reeder, J. Org. Chem. 26, 1111 (1961). Comprehensive description: A. MacDonald et al., Anal. Profiles Drug Subs. 1, 15-51 (1972). Review of pharmacokinetics: D. J. Greenblatt et al., Clin. Pharmacokinet. 3, 381-394 (1978); of pharmacology and effect on cognitive function: J. B. Murray, Genet. Psychol. Monogr. 109 (2), 167-197 (1984). Clinical trial in alcohol withdrawal: A. K. Burroughs et al., Alcohol Alcohol. 20, 263 (1985).

Chemical structure

Properties

Light yellow plates from ethanol, mp 236-236.5°. pK 4.8.

Derivative

Hydrochloride.

Nomenclature

CAS number: 438-41-5
Ansiacal (Beolet); A-Poxide (Abbott); Balance (Yamanouchi); Benzodiapin (Lisapharma); Cebrum (SIFA); Corax (Empire); Disarim (Bial); Elenium (Polfa); Equibral (Ravizza); Labican (Boniscontro); Lentotran (Farmopatria); Librium (Roche); O.C.M. (Gobbi-Novag); Psichial (Lang); Psicoterina (Francia); Reliberan (Geymonat); Seren Vita (Synthelabo); SK-Lygen (SKB); Viansin (Farmocosmici).
C16H14ClN3O.HCl; mol wt 336.22.
C 57.16%, H 4.50%, Cl 21.09%, N 12.50%, O 4.76%.

Properties

Crystals from methanol, mp 213°. Sol in water.

Note

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

Therapeutic Category

Anxiolytic.

Therapeutic Category (Veterinary)

Tranquilizer.

Keywords

Anxiolytic; Benzodiazepine Derivatives