From Wikipedia, the free encyclopedia
Chemical compound
Cyprazepam
Routes of administration Oral
ATC code
Legal status
Metabolism
Hepatic
Excretion
Renal
10-chloro-N -(cyclopropylmethyl)-3-hydroxy-2-phenyl-3,6-diazabicyclo[5.4.0]undeca-1,6,8,10-tetraen-5-imine
CAS Number
PubChem
CID
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (
EPA )
Formula C 19 H 18 Cl N 3 O
Molar mass 339.82 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)
Y Key:UKFDTMNJMKWWNK-UHFFFAOYSA-N
Y
N Y
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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:
[1]
For example, heating
demoxepam with N-cyclopropylmethylamine leads to
amidine formation, the minor tranquilizer cyprazepam.
See also
References
^
a
b
US 3138586 , Wuest HM, "2-Cycloalkylamino Derivatives of 1,4-Benzodiazipines", issued 23 June 1964, assigned to Warner-Lambert Pharmaceutical Compay ; Chem. Abstr., 61: 7,032f (1964).
^ 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 from
the original on 5 January 2013.
^
EP 1466628 , Matthews B, Victor S, Nigel, Swindell C, "DHA-pharmaceutical agent conjugates", published 13 October 2004, assigned to American Regent Inc.
^
"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 .
^ 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 .
^ 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 . Retrieved 19 September 2009 . [
dead link ]
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