Cyprazepam

Cyprazepam

Clinical data
Pregnancy category	?
Routes of administration	Oral
ATC code	none
Legal status
Legal status	Schedule IV(US)
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
PubChem (CID)	27452
ChemSpider	16736916
UNII	933N61G4SL
KEGG	D03631
ChEMBL	CHEMBL2104165
Chemical and physical data
Formula	C19H18ClN3O
Molar mass	339.819 g/mol
3D model (Jmol)	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) Key:UKFDTMNJMKWWNK-UHFFFAOYSA-N
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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.

Synthesis

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

Cyprazepam synthesis:^[7]

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

See also

• Benzodiazepine

References

1. US Patent 3138586
2. Herbert Oelschläger; Doris Martienssen; F. Belal (22 September 2006). "Ring Contraction of 1,4-Benzodiazepines to 3,4-Dihydroquinazolines During Macro Scale Reduction (Example 5: Cyprazepam)". Archiv der Pharmazie. Wiley Interscience. 325 (8): 503–507. doi:10.1002/ardp.19923250810. ISSN 0365-6233.
3. Bradley Matthews; Shashoua Victor; Webb Nigel; Swindell Charles (13 October 2004). "DHA-pharmaceutical agent conjugates - European Patent Application EP1466628". Patents online. Retrieved 19 September 2009.
4. "Harmonized Tariff Schedule of the United States (2009) - Supplement 1 - PHARMACEUTICAL APPENDIX TO THE HARMONIZED TARIFF SCHEDULE" (PDF). USA: United States International Trade Commission. 2009. Archived from the original (PDF) on 31 July 2009. Retrieved 19 September 2009.
5. E. W. Schafer; W. A. Bowles, Jr; J. Hurlbut (1983). "The Acute Oral Toxicity, Repellency, and Hazard Potential of 998 Chemicals to One or More Species of Wild and Domestic Birds" (PDF). Arch. Environ. Contam. Toxicol. USA. 12 (3): 355–382. doi:10.1007/BF01059413. PMID 6882015. Retrieved 19 September 2009.
6. World Health Organisation (2006). "The use of stems in the selection of International Nonproprietary Names (INN) for pharmaceutical substances" (PDF). USA: Ministry of health, Syria. Retrieved 19 September 2009.
7. H. M. Wuest, U.S. Patent 3,138,586 (1964); Chem. Abstr. , 61: 7,032f (1964).