Chemistry:Cyprazepam

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Short description: Chemical compound
Cyprazepam
Cyprazepam.svg
Cyprazepam3d.png
Clinical data
Routes of
administration
Oral
ATC code
  • none
Legal status
Legal status
  • US: Unscheduled
Pharmacokinetic data
MetabolismHepatic
ExcretionRenal
Identifiers
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEMBL
Chemical and physical data
FormulaC19H18ClN3O
Molar mass339.82 g·mol−1
3D model (JSmol)
 ☒N☑Y (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

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

References

  1. 1.0 1.1 Wuest HM, "2-Cycloalkylamino Derivatives of 1,4-Benzodiazipines", US patent 3138586, issued 23 June 1964, assigned to Warner-Lambert Pharmaceutical Compay; Chem. Abstr., 61: 7,032f (1964).
  2. "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. 22 September 2006. doi:10.1002/ardp.19923250810. ISSN 0365-6233. http://www3.interscience.wiley.com/journal/113348763/abstract. 
  3. Matthews B, Victor S, Nigel, Swindell C, "DHA-pharmaceutical agent conjugates", EP patent 1466628, published 13 October 2004, assigned to American Regent Inc.
  4. "Harmonized Tariff Schedule of the United States (2009) - Supplement 1 - PHARMACEUTICAL APPENDIX TO THE HARMONIZED TARIFF SCHEDULE". USA: United States International Trade Commission. 2009. http://www.usitc.gov/publications/docs/tata/hts/bychapter/0910PHARMAPPX.pdf. 
  5. "The acute oral toxicity, repellency, and hazard potential of 998 chemicals to one or more species of wild and domestic birds". Archives of Environmental Contamination and Toxicology 12 (3): 355–82. May 1983. doi:10.1007/BF01059413. PMID 6882015. Bibcode1983ArECT..12..355S. 
  6. World Health Organization (2006). "The use of stems in the selection of International Nonproprietary Names (INN) for pharmaceutical substances". USA: Ministry of health, Syria. http://www.moh.gov.sy/Pages/DrugAndNutrition/documents/INN%20Stems/RevisedFinalStemBook2006.pdf.  [|permanent dead link|dead link}}]