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-life	35–40 hours
Identifiers
IUPAC name 7-Chloro-1,3-dihydro-5-phenyl-2H-1,4-benzodiazepin-2-one-4-oxide
CAS Number	963-39-3^N
PubChem CID	13756
ChemSpider	10441314^Y
UNII	8X1XP5M0SB
KEGG	D02600^Y
ChEMBL	ChEMBL1597677^N
CompTox Dashboard (EPA)	DTXSID4046155
ECHA InfoCard	100.012.287
Chemical and physical data
Formula	C15H11ClN2O2
Molar mass	286.713 g·mol^−1
3D model (JSmol)	Interactive image
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

• Benzodiazepine
• Chlordiazepoxide

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.