Cyprazepam

Cyprazepam^[1] is a drug which is a sedative-hypnotic benzodiazepine derivative.^[2][3][4][5] It has anxiolytic properties,^[6] and presumably also has hypnotic, skeletal muscle relaxant, anticonvulsant and amnestic properties.

Cyprazepam

Clinical data
Routes of administration	Oral
ATC code	none
Legal status
Legal status	US: Unscheduled
Pharmacokinetic data
Metabolism	Hepatic
Excretion	Renal
Identifiers
IUPAC name 10-chloro-N-(cyclopropylmethyl)-3-hydroxy-2-phenyl-3,6-diazabicyclo[5.4.0]undeca-1,6,8,10-tetraen-5-imine
CAS Number	15687-07-7 Y
PubChem CID	27452
ChemSpider	16736916 Y
UNII	933N61G4SL
KEGG	D03631 Y
ChEMBL	ChEMBL2104165 N
CompTox Dashboard (EPA)	DTXSID70897505
Chemical and physical data
Formula	C19H18ClN3O
Molar mass	339.82 g·mol−1
3D model (JSmol)	Interactive image
SMILES ClC1=CC2=C(N/C(C[N+]([O-])=C2C3=CC=CC=C3)=N/CC4CC4)C=C1
InChI InChI=1S/C19H18ClN3O/c20-15-8-9-17-16(10-15)19(14-4-2-1-3-5-14)23(24)12-18(22-17)21-11-13-6-7-13/h1-5,8-10,13H,6-7,11-12H2,(H,21,22) Y Key:UKFDTMNJMKWWNK-UHFFFAOYSA-N Y
NY (what is this?)  (verify)

Synthesis

The lactam moiety in benzodiazepams is active towards nucleophiles and numerous analogues have been made by exploiting this fact.

Cyprazepam synthesis:^[1]

For example, heating demoxepam with N-cyclopropylmethylamine leads to amidine formation, the minor tranquilizer cyprazepam.

See also

• Benzodiazepine