Demoxepam

Demoxepam[1] is a drug which is a benzodiazepine derivative. It is a metabolite of chlordiazepoxide and has anticonvulsant properties[2][3] and presumably other characteristic benzodiazepine properties.

Demoxepam
Pharmacokinetic data
Elimination half-life35–40 hours
Identifiers
IUPAC name
  • 7-Chloro-1,3-dihydro-5-phenyl-2H-1,4-benzodiazepin-2-one-4-oxide
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.012.287
Chemical and physical data
FormulaC15H11ClN2O2
Molar mass286.713 g·mol−1
3D model (JSmol)
SMILES
  • ClC1=CC2=C(NC(C[N+]([O-])=C2C3=CC=CC=C3)=O)C=C1
InChI
  • InChI=1S/C15H11ClN2O2/c16-11-6-7-13-12(8-11)15(10-4-2-1-3-5-10)18(20)9-14(19)17-13/h1-8H,9H2,(H,17,19) Y
  • Key:GGRWZBVSUZZMKS-UHFFFAOYSA-N Y
 NY (what is this?)  (verify)

Synthesis

Demoxepam is also an intermediate in the synthesis of oxazepam; it is also used in one of the syntheses of medazepam. It can be considered directly analogous/synonoymous with the synthesis of chlordiazepoxide, with the exception that instead of methylamine, hydroxide ion is the choice of base; here acid is not used for the cyclodehydration step though.

Demoxepam synthesis: Reeder Earl, Sternbach Leo Henryk, U.S. Patent 3,136,815 (1959 to Hoffmann La Roche).

See also

References
  1. US Patent 3136815
  2. "nortetrazepam". psychotropics.dk. 2003. Retrieved 7 December 2009.
  3. "LIST OF INTERNATIONAL NON-PROPRIETARY NAMES (INNS), PROVIDED FOR PHARMACEUTICAL SUBSTANCES BY THE WORLD HEALTH ORGANIZATION, WHICH ARE FREE OF DUTY" (PDF). Official Journal of the European Communities. eur-lex.europa.eu. 23 October 2001. Retrieved 7 December 2009.
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