ChemSpider 2D Image | chlormezanone | C11H12ClNO3S

chlormezanone

  • Molecular FormulaC11H12ClNO3S
  • Average mass273.736 Da
  • Monoisotopic mass273.022644 Da
  • ChemSpider ID2616

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(±)-Chlormezanone
1,1-Dioxyde de 2-(4-chlorophényl)-3-méthyl-1,3-thiazinan-4-one [French] [ACD/IUPAC Name]
102818-66-6 [RN]
102818-67-7 [RN]
2-(4-Chlorophenyl)-3-methyl-1,3-thiazinan-4-one 1,1-dioxide [ACD/IUPAC Name]
2-(4-Chlorophenyl)-3-methyl-4-metathiazanone 1,1-Dioxide
2-(4-Chlorophenyl)tetrahydro-3-methyl-4H-1,3-thiazin-4-one 1,1-dioxide
2-(4-Chlorphenyl)-3-methyl-1,3-thiazinan-4-on-1,1-dioxid [German] [ACD/IUPAC Name]
2-(p-Chlorophenyl)perhydro-3-methyl-1,3-thiazin-4-one 1,1-Dioxide
201-307-4 [EINECS]
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

D00268 [DBID]
DivK1c_000886 [DBID]
EU-0100383 [DBID]
HSDB 3300 [DBID]
KBio1_000886 [DBID]
KBio2_000894 [DBID]
KBio2_003462 [DBID]
KBio2_006030 [DBID]
KBio3_001948 [DBID]
KBioGR_001734 [DBID]
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  • Experimental Physico-chemical Properties
  • Predicted Physico-chemical Properties
  • Miscellaneous
    • Safety:

      M03BB02 Wikidata Q5102983
    • Target Organs:

      Others TargetMol T0715
    • Chemical Class:

      A 1,3-thiazine that is 1,3-thiazinan-4-one <element>S</element>,<element>S</element>-dioxide in which a hydrogen at position 2 is substituted by a 4-chlorophenyl group and the hydrogen attached to the nitrogen is substituted by methyl. A non-benzodiazepine muscle relaxant, it was used in the management of anxiety and in the treatment of muscle spasms until being discontinued worldwide by its manuf acturer in 1996, due to rare but serious cutaneous reactions. ChEBI CHEBI:3619
    • Drug Status:

      INN, BAN, JAN Microsource [02300062]
    • Compound Source:

      synthetic Microsource [02300062]
    • Bio Activity:

      Anxiolytic and skeletal muscle relaxant that acts at the benzodiazepine site of GABAA receptors. Tocris Bioscience 0456, 456
      Chlormezanone, a non-benzodiazepine that is used in the management of anxiety. MedChem Express http://www.medchemexpress.com/ginkgolide-a.html, HY-B0353
      GABAA and A-rho Receptors Tocris Bioscience 456
      Ion Channels Tocris Bioscience 456
      Ligand-gated Ion Channels Tocris Bioscience 456
      Membrane Transporter/Ion Channel TargetMol T0715
      Others MedChem Express HY-B0353
      Skeletal muscle relaxant Tocris Bioscience 0456, 456
      Translocator protein TargetMol T0715
  • Gas Chromatography
    • Retention Index (Kovats):

      2194 (Program type: Isothermal; Col... (show more) umn class: Standard non-polar; Column length: 2 m; Column type: Packed; Start T: 220 C; CAS no: 80773; Active phase: SE-30; Carrier gas: N2; Substrate: 1% se-30 on Anachrom ABS(80-100mesh); Data type: Kovats RI; Authors: Musumarra, G.; Scarlata, G.; Romano, G.; Cappello, G.; Clementi, S.; Giulietti, G., Qualitative organic analysis. Part 2. Identification of drugs by principal components analysis of standardized TLC data in four eluent systems and of retention indices on SE 30, J. Anal. Toxicol., 11, 1987, 154-163.) NIST Spectra nist ri
    • Retention Index (Normal Alkane):

      2238 (Program type: Ramp; Column cl... (show more) ass: Standard non-polar; Column length: 2 m; Column type: Packed; Start T: 100 C; End T: 300 C; CAS no: 80773; Active phase: SE-30; Carrier gas: Nitrogen; Substrate: Chromosorb G AW DMCS (80-100 mesh); Data type: Normal alkane RI; Authors: MHA, Directorate of ForensicScience., Forensic Toxicology, 9999.) NIST Spectra nist ri
      2150 (Program type: Ramp; Column cl... (show more) ass: Standard non-polar; Column type: Other; CAS no: 80773; Active phase: Methyl Silicone; Data type: Normal alkane RI; Authors: Ardrey, R.E.; Moffat, A.C., Gas-liquid chromatographic retention indices of 1318 substances of toxicological interest on SE-30 or OV-1 stationary phase, J. Chromatogr., 220, 1981, 195-252.) NIST Spectra nist ri
      2165 (Program type: Ramp; Column cl... (show more) ass: Standard non-polar; Column type: Other; CAS no: 80773; Active phase: Methyl Silicone; Data type: Normal alkane RI; Authors: Ardrey, R.E.; Moffat, A.C., Gas-liquid chromatographic retention indices of 1318 substances of toxicological interest on SE-30 or OV-1 stationary phase, J. Chromatogr., 220, 1981, 195-252.) NIST Spectra nist ri

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

Density: 1.4±0.1 g/cm3
Boiling Point: 534.5±50.0 °C at 760 mmHg
Vapour Pressure: 0.0±1.4 mmHg at 25°C
Enthalpy of Vaporization: 81.1±3.0 kJ/mol
Flash Point: 277.1±30.1 °C
Index of Refraction: 1.580
Molar Refractivity: 65.5±0.4 cm3
#H bond acceptors: 4
#H bond donors: 0
#Freely Rotating Bonds: 1
#Rule of 5 Violations: 0
ACD/LogP: 0.86
ACD/LogD (pH 5.5): 0.52
ACD/BCF (pH 5.5): 1.46
ACD/KOC (pH 5.5): 45.72
ACD/LogD (pH 7.4): 0.52
ACD/BCF (pH 7.4): 1.46
ACD/KOC (pH 7.4): 45.72
Polar Surface Area: 63 Å2
Polarizability: 26.0±0.5 10-24cm3
Surface Tension: 49.1±3.0 dyne/cm
Molar Volume: 196.7±3.0 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) =  -0.26

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  421.05  (Adapted Stein & Brown method)
    Melting Pt (deg C):  171.70  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  3.19E-007  (Modified Grain method)
    MP  (exp database):  116.2 deg C
    Subcooled liquid VP: 2.55E-006 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):  2.882e+004
       log Kow used: -0.26 (estimated)
       no-melting pt equation used
     Water Sol (Exper. database match) =  2500 mg/L (25 deg C)
        Exper. Ref:  MERCK INDEX (1996)

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  27965 mg/L
    Wat Sol (Exper. database match) =  2500.00
       Exper. Ref:  MERCK INDEX (1996)

 ECOSAR Class Program (ECOSAR v0.99h):
    Class(es) found:
       Neutral Organics

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   5.64E-011  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  3.987E-012 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  -0.26  (KowWin est)
  Log Kaw used:  -8.637  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  8.377
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.6450
   Biowin2 (Non-Linear Model)     :   0.4495
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.3334  (weeks-months)
   Biowin4 (Primary Survey Model) :   3.4929  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.0936
   Biowin6 (MITI Non-Linear Model):   0.0300
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -0.8023
 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):  0.00034 Pa (2.55E-006 mm Hg)
  Log Koa (Koawin est  ): 8.377
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  0.00882 
       Octanol/air (Koa) model:  5.85E-005 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.242 
       Mackay model           :  0.414 
       Octanol/air (Koa) model:  0.00466 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant = 108.5233 E-12 cm3/molecule-sec
      Half-Life =     0.099 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     1.183 Hrs
   Ozone Reaction:
      No Ozone Reaction Estimation
   Fraction sorbed to airborne particulates (phi): 0.328 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  600
      Log Koc:  2.778 

 Aqueous Base/Acid-Catalyzed Hydrolysis (25 deg C) [HYDROWIN v1.67]:
    Rate constants can NOT be estimated for this structure!

 Bioaccumulation Estimates from Log Kow (BCFWIN v2.17):
   Log BCF from regression-based method = 0.500 (BCF = 3.162)
       log Kow used: -0.26 (estimated)

 Volatilization from Water:
    Henry LC:  5.64E-011 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 1.718E+007  hours   (7.156E+005 days)
    Half-Life from Model Lake : 1.874E+008  hours   (7.807E+006 days)

 Removal In Wastewater Treatment:
    Total removal:               1.85  percent
    Total biodegradation:        0.09  percent
    Total sludge adsorption:     1.76  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       0.000862        2.37         1000       
   Water     46.1            900          1000       
   Soil      53.8            1.8e+003     1000       
   Sediment  0.089           8.1e+003     0          
     Persistence Time: 975 hr




                    

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