Cyprazepam

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Cyprazepam
Cyprazepam.svg
Cyprazepam3d.png
Systematic (IUPAC) name
10-chloro-N-(cyclopropylmethyl)-3-hydroxy-2-phenyl-3,6-diazabicyclo[5.4.0]undeca-1,6,8,10-tetraen-5-imine
Clinical data
Pregnancy
category
  •  ?
Routes of
administration		 Oral
Legal status
Legal status
Pharmacokinetic data
Metabolism Hepatic
Excretion Renal
Identifiers
CAS Number 15687-07-7 YesY
ATC code none
PubChem CID 27452
ChemSpider 16736916 YesY
UNII 933N61G4SL YesY
KEGG D03631 YesY
ChEMBL CHEMBL2104165 N
Chemical data
Formula C19H18ClN3O
Molar mass 339.819 g/mol
3D model (Jmol) Interactive image
 NYesY (what is this?)  (verify)

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[edit]

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[edit]

References[edit]

  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. 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. [dead link]
  7. ^ H. M. Wuest, U.S. Patent 3,138,586 (1964); Chem. Abstr. , 61: 7,032f (1964).


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