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Cyprazepam

From Wikipedia, the free encyclopedia
Chemical compound

Pharmaceutical compound
Cyprazepam
Clinical data
Routes of
administration		Oral
ATC code
  • none
Legal status
Legal status
Pharmacokinetic data
MetabolismHepatic
ExcretionRenal
Identifiers
  • 10-chloro-N-(cyclopropylmethyl)-3-hydroxy-2-phenyl-3,6-diazabicyclo[5.4.0]undeca-1,6,8,10-tetraen-5-imine
CAS Number
PubChemCID
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard(EPA)
Chemical and physical data
FormulaC19H18ClN3O
Molar mass339.82 g·mol−1
3D model (JSmol)
  • ClC1=CC2=C(N/C(C[N+]([O-])=C2C3=CC=CC=C3)=N/CC4CC4)C=C1
  • 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) checkY
  • Key:UKFDTMNJMKWWNK-UHFFFAOYSA-N checkY
 ☒NcheckY (what is this?)  (verify)

Cyprazepam[1] is a drug which is asedative-hypnoticbenzodiazepine derivative.[2][3][4][5] It has anxiolytic properties,[6] and presumably also hashypnotic,skeletal muscle relaxant,anticonvulsant andamnestic properties.

Synthesis

[edit]

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

Cyprazepam synthesis:[1]

For example, heatingdemoxepam with N-cyclopropylmethylamine leads toamidine formation, the minor tranquilizer cyprazepam.

See also

[edit]

References

[edit]
  1. ^abUS 3138586, Wuest HM, "2-Cycloalkylamino Derivatives of 1,4-Benzodiazipines", issued 23 June 1964, assigned to Warner-Lambert Pharmaceutical Company ; Chem. Abstr., 61: 7,032f (1964).
  2. ^Oelschläger H, Martienssen D, Belal F (22 September 2006)."Ring Contraction of 1,4-Benzodiazepines to 3,4-Dihydroquinazolines During Macro Scale Reduction (Example 5: Cyprazepam)".Archiv der Pharmazie.325 (8). Wiley Interscience:503–507.doi:10.1002/ardp.19923250810.ISSN 0365-6233.S2CID 96638676. Archived fromthe original on 5 January 2013.
  3. ^EP 1466628, Matthews B, Victor S, Nigel, Swindell C, "DHA-pharmaceutical agent conjugates", 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"(PDF). USA: United States International Trade Commission. 2009. Archived fromthe original(PDF) on 31 July 2009. Retrieved19 September 2009.
  5. ^Schafer EW, Bowles WA, Hurlbut J (May 1983). "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.Bibcode:1983ArECT..12..355S.doi:10.1007/BF01059413.PMID 6882015.S2CID 32956594.
  6. ^World Health Organization (2006)."The use of stems in the selection of International Nonproprietary Names (INN) for pharmaceutical substances"(PDF). USA: Ministry of health,Syria. Retrieved19 September 2009.[dead link‍]
1,4-Benzodiazepines
1,5-Benzodiazepines
2,3-Benzodiazepines*
Triazolobenzodiazepines
Imidazobenzodiazepines
Oxazolobenzodiazepines
Thienodiazepines
Thienotriazolodiazepines
Thienobenzodiazepines*
Pyridodiazepines
Pyridotriazolodiazepines
Pyrazolodiazepines
Pyrrolodiazepines
Tetrahydroisoquinobenzodiazepines
Pyrrolobenzodiazepines*
Benzodiazepine prodrugs
* atypical activity profile (notGABAA receptor ligands)
Alcohols
Barbiturates
Benzodiazepines
Carbamates
Flavonoids
Imidazoles
Kava constituents
Monoureides
Neuroactive steroids
Nonbenzodiazepines
Phenols
Piperidinediones
Pyrazolopyridines
Quinazolinones
Volatiles/gases
Others/unsorted
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