ChemSpider 2D Image | zopiclone | C17H17ClN6O3

zopiclone

  • Molecular FormulaC17H17ClN6O3
  • Average mass388.808 Da
  • Monoisotopic mass388.105072 Da
  • ChemSpider ID5533

More details:



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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

(±)-Zopiclone
(±)-Zopiclone
(±)-Zopiclone
1-Piperazinecarboxylic acid, 4-methyl-, 6-(5-chloro-2-pyridinyl)-6,7-dihydro-7-oxo-5H-pyrrolo[3,4-b]pyrazin-5-yl ester [ACD/Index Name]
256-138-9 [EINECS]
27267 R.P.
43200-80-2 [RN]
4-Méthyl-1-pipérazinecarboxylate de 6-(5-chloro-2-pyridinyl)-7-oxo-6,7-dihydro-5H-pyrrolo[3,4-b]pyrazin-5-yle [French] [ACD/IUPAC Name]
6-(5-Chlor-2-pyridinyl)-7-oxo-6,7-dihydro-5H-pyrrolo[3,4-b]pyrazin-5-yl-4-methyl-1-piperazincarboxylat [German] [ACD/IUPAC Name]
6-(5-Chloro-2-pyridinyl)-7-oxo-6,7-dihydro-5H-pyrrolo[3,4-b]pyrazin-5-yl 4-methyl-1-piperazinecarboxylate [ACD/IUPAC Name]
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

BRN 0768704 [DBID]
D01372 [DBID]
EU-0101270 [DBID]
nchembio747-comp16 [DBID]
RP 27267 [DBID]
RP-27267 [DBID]
Z4900_SIGMA [DBID]
  • Experimental Physico-chemical Properties
  • Predicted Physico-chemical Properties
  • Miscellaneous
    • Safety:

      5 Axon Medchem 1197
      GHS07; GHS08 Biosynth W-106239
      H302; H312; H315; H319; H332; H335; H361 Biosynth W-106239
      H303;H313;H317;H333;H334;H335;H373 Axon Medchem 1197
      no pictogram Axon Medchem 1197
      P101;P102;P103;P260;P262;P263;P264;P270;P280;P304;P312;P340 Axon Medchem 1197
      P261; P280; P305+P351+P338 Biosynth W-106239
      Warning Biosynth W-106239
      Warning Axon Medchem 1197
    • Bio Activity:

      A non benzodiazepine BZR agonist, with little difference in affinity for the BZ1 and BZ2 subtypes; however its CNS effects differ from those of other BZR ligands and this may be due to interaction wit h a different subunit. Tocris Bioscience 1094
      A non benzodiazepine BZR agonist, with little difference in affinity for the BZ1 and BZ2 subtypes; however its CNS effects differ from those of other BZR ligands and this may be due to interaction with a different subunit. Tocris Bioscience 1094
      Benzodiazepine agonist Tocris Bioscience 1094
      GABA Receptor MedChem Express HY-B0741
      GABAA and A-rho Receptors Tocris Bioscience 1094
      Ion Channels Tocris Bioscience 1094
      Ligand-gated Ion Channels Tocris Bioscience 1094
      Membrane Tranporter/Ion Channel MedChem Express HY-B0741
      Membrane Tranporter/Ion Channel; Neuronal Signaling; MedChem Express HY-B0741
      Sedative; Zerenex Molecular [ZBioX-0431]
      Zopiclone(RP27267) is a nonbenzodiazepine hypnotic agent used in the treatment of insomnia. MedChem Express
      Zopiclone(RP27267) is a nonbenzodiazepine hypnotic agent used in the treatment of insomnia.; Target: GABA Receptor; Zopiclone is shown to have useful hypnotic properties but residual effects are detectable using EEG and psychological tests both 10 and 13 h after ingestion. MedChem Express HY-B0741
      Zopiclone(RP27267) is a nonbenzodiazepine hypnotic agent used in the treatment of insomnia.;Target: GABA ReceptorZopiclone is shown to have useful hypnotic properties but residual effects are detectable using EEG and psychological tests both 10 and 13 h after ingestion. The 10-mg dose significantly impairs performance the next day; the 5-mg dose is almost devoid of residual psychomotor effects but is only marginally effective in hastening onset of sleep and does not improve sleep quality. The 7.5-mg dose has definite effects on sleep and limited residual effects the next day. No significant side effects were reported [1]. Zopiclone in a dose of 10 mg/kg (p.o.) significantly reduced it (p less than 0.01) in 30 min and the reduced locomotor activity persisted until 180 min. The reducing effect on locomotor activity by zopiclone was similar to that of nitrazepam and more potent than flurazepam. The effects of zopiclone on brain monoamines (MA) were examined. No significant changes in MedChem Express HY-B0741
  • Gas Chromatography
    • Retention Index (Kovats):

      3156 (estimated with error: 89) NIST Spectra mainlib_335207, mainlib_335084, replib_247516
      3051 (Program type: Isothermal; Col... (show more) umn class: Standard non-polar; Column diameter: 0.2 mm; Column length: 12 m; Column type: Capillary; Start T: 250 C; CAS no: 43200802; Active phase: Ultra-1; Carrier gas: N2; Phase thickness: 0.33 um; Data type: Kovats RI; Authors: Ahrens, B.; Schutz, H.; Seno, H.; Weiler, G., Screening, identification and determination of the two new hypnotics zolpidem and zopiclone, Arzneim. Forsch., 44(7), 1994, 799-802.) NIST Spectra nist ri
    • Retention Index (Normal Alkane):

      3084.5 (Program type: Ramp; Column cl... (show more) ass: Semi-standard non-polar; Column diameter: 0.25 mm; Column length: 30 m; Column type: Capillary; Heat rate: 5 K/min; Start T: 70 C; End T: 320 C; End time: 5 min; Start time: 0.5 min; CAS no: 43200802; Active phase: BPX-5; Phase thickness: 0.25 um; Data type: Normal alkane RI; Authors: Song, S.M.; Marriott, P.; Wynne, P., Comprehensive two-dimensional gas chromatography-quadrupole mass spectrometric analysis of drugs, J. Chromatogr. A, 1058, 2004, 223-232.) NIST Spectra nist ri
      3062.6 (Program type: Complex; Column... (show more) class: Semi-standard non-polar; Column diameter: 0.32 mm; Column length: 15 m; Column type: Capillary; Description: 100 0C (0.4 min) ^ 25 0C/min -> 200 0C ^ 10 0C/min -> 290 0C (10 min); CAS no: 43200802; Active phase: HG-5; Carrier gas: He; Phase thickness: 0.25 um; Data type: Normal alkane RI; Authors: Rasanen, I.; Kontinen, I.; Nokua, J.; Ojanpera, I.; Vuori, E., Precise gas chromatography with retention time locking in comprehensive toxicological screening for drugs in blood, J. Chromatogr. B, 788, 2003, 243-250.) NIST Spectra nist ri
      3090.6 (Program type: Complex; Column... (show more) class: Semi-standard non-polar; Column diameter: 0.32 mm; Column length: 15 m; Column type: Capillary; Description: 70 0C (0.7 min) ^ 20 0C/min -> 140 0C ^ 10 0C/min -> 290 0C (9.5 min); CAS no: 43200802; Active phase: DB-5; Carrier gas: He; Phase thickness: 0.25 um; Data type: Normal alkane RI; Authors: Rasanen, I.; Ojanpera, I.; Vartiovaara, J.; Vuori, E.; Sunila, P., The advantage of dual-column approach and retention indices combined with refined reporting in gas chromatographic drug screening, J. Hi. Res. Chromatogr., 19, 1996, 313-321.) NIST Spectra nist ri

Predicted data is generated using the ACD/Labs Percepta Platform - PhysChem Module

Density: 1.5±0.1 g/cm3
Boiling Point: 580.7±50.0 °C at 760 mmHg
Vapour Pressure: 0.0±1.6 mmHg at 25°C
Enthalpy of Vaporization: 86.9±3.0 kJ/mol
Flash Point: 305.0±30.1 °C
Index of Refraction: 1.688
Molar Refractivity: 96.2±0.4 cm3
#H bond acceptors: 9
#H bond donors: 0
#Freely Rotating Bonds: 3
#Rule of 5 Violations: 0
ACD/LogP: -0.33
ACD/LogD (pH 5.5): -0.59
ACD/BCF (pH 5.5): 1.00
ACD/KOC (pH 5.5): 3.13
ACD/LogD (pH 7.4): 0.56
ACD/BCF (pH 7.4): 1.49
ACD/KOC (pH 7.4): 44.02
Polar Surface Area: 92 Å2
Polarizability: 38.2±0.5 10-24cm3
Surface Tension: 86.1±5.0 dyne/cm
Molar Volume: 252.3±5.0 cm3

Predicted data is generated using the US Environmental Protection Agency’s EPISuite™

                        
 Log Octanol-Water Partition Coef (SRC):
    Log Kow (KOWWIN v1.67 estimate) =  1.54

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  533.82  (Adapted Stein & Brown method)
    Melting Pt (deg C):  228.40  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  9.74E-011  (Modified Grain method)
    MP  (exp database):  178 deg C
    Subcooled liquid VP: 3.79E-009 mm Hg (25 deg C, Mod-Grain method)

 Water Solubility Estimate from Log Kow (WSKOW v1.41):
    Water Solubility at 25 deg C (mg/L):  174.7
       log Kow used: 1.54 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  39124 mg/L

 ECOSAR Class Program (ECOSAR v0.99h):
    Class(es) found:
       Aliphatic Amines
       Esters

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   1.15E-019  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  2.852E-013 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  1.54  (KowWin est)
  Log Kaw used:  -17.328  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  18.868
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.3099
   Biowin2 (Non-Linear Model)     :   0.0091
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   1.5634  (recalcitrant)
   Biowin4 (Primary Survey Model) :   3.2138  (weeks       )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :  -0.3629
   Biowin6 (MITI Non-Linear Model):   0.0008
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -1.5715
 Ready Biodegradability Prediction:   NO

Hydrocarbon Biodegradation (BioHCwin v1.01):
    Structure incompatible with current estimation method!

 Sorption to aerosols (25 Dec C)[AEROWIN v1.00]:
  Vapor pressure (liquid/subcooled):  5.05E-007 Pa (3.79E-009 mm Hg)
  Log Koa (Koawin est  ): 18.868
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  5.94 
       Octanol/air (Koa) model:  1.81E+006 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.995 
       Mackay model           :  0.998 
       Octanol/air (Koa) model:  1 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant = 134.1852 E-12 cm3/molecule-sec
      Half-Life =     0.080 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     0.957 Hrs
   Ozone Reaction:
      No Ozone Reaction Estimation
   Fraction sorbed to airborne particulates (phi): 0.997 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  701.1
      Log Koc:  2.846 

 Aqueous Base/Acid-Catalyzed Hydrolysis (25 deg C) [HYDROWIN v1.67]:
  Total Kb for pH > 8 at 25 deg C :  5.381E-015  L/mol-sec
  Kb Half-Life at pH 8: 4.081E+012  years  
  Kb Half-Life at pH 7: 4.081E+013  years  

 Bioaccumulation Estimates from Log Kow (BCFWIN v2.17):
   Log BCF from regression-based method = 0.484 (BCF = 3.046)
       log Kow used: 1.54 (estimated)

 Volatilization from Water:
    Henry LC:  1.15E-019 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 1.004E+016  hours   (4.183E+014 days)
    Half-Life from Model Lake : 1.095E+017  hours   (4.563E+015 days)

 Removal In Wastewater Treatment:
    Total removal:               1.99  percent
    Total biodegradation:        0.09  percent
    Total sludge adsorption:     1.89  percent
    Total to Air:                0.00  percent
      (using 10000 hr Bio P,A,S)

 Level III Fugacity Model:
           Mass Amount    Half-Life    Emissions
            (percent)        (hr)       (kg/hr)
   Air       6.74e-011       1.91         1000       
   Water     36.3            4.32e+003    1000       
   Soil      63.6            8.64e+003    1000       
   Sediment  0.0972          3.89e+004    0          
     Persistence Time: 2.12e+003 hr




                    

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