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 15687-07-7 Y 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 (what is this?)
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.
For example, heating demoxepam with N-cyclopropylmethylamine leads to amidine formation, the minor tranquilizer cyprazepam.
See also [ ]
References [ ]
^ US 3138586
^ 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 . Wiley Interscience. 325 (8): 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
^ "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. 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 ]
^ US 3138586 , Wuest HM, published 1964 ; Chem. Abstr., 61: 7,032f (1964).
Benzodiazepines
1,4-Benzodiazepines 1,5-Benzodiazepines 2,3-Benzodiazepines* Triazolobenzodiazepines Imidazobenzodiazepines
Bretazenil
Climazolam
EVT-201
FG-8205
Flumazenil
GL-II-73
Imidazenil
123 I-Iomazenil
L-655,708
Loprazolam
Midazolam
PWZ-029
Remimazolam
Ro15-4513
Ro48-6791
Ro48-8684
Ro4938581
Sarmazenil
SH-053-R-CH3-2′F
Oxazolobenzodiazepines Thienodiazepines Thienotriazolodiazepines Thienobenzodiazepines *Pyridodiazepines Pyridotriazolodiazepines Pyrazolodiazepines Pyrrolodiazepines Tetrahydroisoquinobenzodiazepines Pyrrolobenzodiazepines *Benzodiazepine prodrugs * atypical activity profile (not GABAA receptor ligands)
GABA A receptor positive modulatorsAlcohols
Butanol
Chloralodol
Chlorobutanol (cloretone)
Ethanol (alcohol) (alcoholic drink )
Ethchlorvynol
Isobutanol
Isopropanol
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Petrichloral
Propanol
tert -Butanol (2M2P)
tert -Pentanol (2M2B)
Tribromoethanol
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Trifluoroethanol
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Org 25,435
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(e.g., sulfonmethane (sulfonal) , tetronal , trional )
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Unsorted benzodiazepine site positive modulators: α-Pinene
See also: Receptor/signaling modulators • GABA receptor modulators • GABA metabolism/transport modulators