ChemSpider 2D Image | LFW48MY844 | C19H21ClN2O2S

LFW48MY844

  • Molecular FormulaC19H21ClN2O2S
  • Average mass376.900 Da
  • Monoisotopic mass376.101227 Da
  • ChemSpider ID2015280

More details:






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

138977-28-3 [RN]
2H-2-Benzazepine-2-carbothioamide, N-[2-(4-chlorophenyl)ethyl]-1,3,4,5-tetrahydro-7,8-dihydroxy- [ACD/Index Name]
Capsazepine
LFW48MY844
N-[2-(4-Chlorophenyl)ethyl]-1,3,4,5-tetrahydro-7,8-dihydroxy-2H-2-benzazepine-2-carbothioamide
N-[2-(4-Chlorophenyl)ethyl]-7,8-dihydroxy-1,3,4,5-tetrahydro-2H-2-benzazepine-2-carbothioamide [ACD/IUPAC Name]
N-[2-(4-Chlorophényl)éthyl]-7,8-dihydroxy-1,3,4,5-tétrahydro-2H-2-benzazépine-2-carbothioamide [French] [ACD/IUPAC Name]
N-[2-(4-Chlorphenyl)ethyl]-7,8-dihydroxy-1,3,4,5-tetrahydro-2H-2-benzazepin-2-carbothioamid [German] [ACD/IUPAC Name]
[138977-28-3]
N-[2-(4-Chlorophenyl)ethyl]-1,3,4,5-tetrahydro-7,8-dihydroxy-2H-2-benzazepine-2-carbothioamide
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

Bio1_000394 [DBID]
Bio1_000883 [DBID]
Bio1_001372 [DBID]
Bio2_000270 [DBID]
Bio2_000750 [DBID]
C191_SIGMA [DBID]
EU-0100373 [DBID]
KBio2_000270 [DBID]
KBio2_002838 [DBID]
KBio2_005406 [DBID]
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  • Experimental Physico-chemical Properties
  • Miscellaneous
    • Chemical Class:

      A benzazepine that is 2,3,4,5-tetrahydro-1<element>H</element>-2-benzazepine which is substituted by hydroxy groups at positions 7 and 8 and on the nitrogen atom by a 2-(<ital>p</ital>-chlorophenyl)et hylaminothiocarbonyl group. A synthetic analogue of capsaicin, it was the first reported capsaicin receptor antagonist. ChEBI CHEBI:70773
    • Bio Activity:

      Capsazepine is a synthetic analogue of the sensory neurone excitotoxin, capsaicin; potent TRPV1 receptor antagonist with IC50 of 562 nM. MedChem Express http://www.medchemexpress.com/Hoechst-33258-analog.html, HY-15640
      Capsazepine is a synthetic analogue of the sensory neurone excitotoxin, capsaicin; potent TRPV1 receptor antagonist with IC50 of 562 nM. ;IC50 Value: 562 nM (Rat TRPV1) [1]Capsazepine blocks the painful sensation of heat caused by capsaicin which activates the TRPV1 ion channel.;In vitro: Capsazepine potentiated the effect of TRAIL, as shown by its effect on intracellular esterase activity; activation of caspase-8,-9, and -3; and colony-formation assay. Capsazepine induced death receptors (DRs) DR5 and DR4, but not decoy receptors, at the transcriptional level and in a non-cell-type-specific manner [2]. Capsazepine (10 microM) reversibly reduced or abolished the current response to capsaicin (500 nM) of voltage-clamped dorsal root ganglion (DRG) neurones from rats [3].;In vivo: Capsazepine (1-100 microM, 45 min preincubation) inhibited the evoked CGRP-LI release. Capsaicin-induced release was significantly inhibited by 77, 92 and 96% with 10, 30 and 100 microM capsazepine, respec MedChem Express HY-15640
      Ion Channels Tocris Bioscience 464
      Membrane Tranporter/Ion Channel MedChem Express HY-15640
      Membrane Tranporter/Ion Channel; MedChem Express HY-15640
      Selective vanilloid receptor antagonist (Ki = 3.2 ?M). Inhibits carrageenan inflammation-induced hyperalgesic responses in the rat. Also activates amiloride-sensitive epithelial Na+ channel ENaC?. Als o available as part of the Vanilloid TRPV1 Receptor Tocriset™. Tocris Bioscience 0464
      Selective vanilloid receptor antagonist (Ki = 3.2 ?M). Inhibits carrageenan inflammation-induced hyperalgesic responses in the rat. Also activates amiloride-sensitive epithelial Na+ channel ENaC?. Also available as part of the Vanilloid TRPV1 Receptor Tocriset?. Tocris Bioscience 464
      Selective vanilloid receptor antagonist (Ki = 3.2 muM). Inhibits carrageenan inflammation-induced hyperalgesic responses in the rat. Also activates amiloride-sensitive epithelial Na+ channel ENaCdelta. Also available as part of the Vanilloid TRPV1 Receptor Tocriset?. Tocris Bioscience 464
      Transient Receptor Potential Channels Tocris Bioscience 464
      TRP Channel MedChem Express HY-15640
      TRPV Tocris Bioscience 464
      Vanilloid receptor antagonist; also activator of ENaC? Tocris Bioscience 0464, 464
      Vanilloid receptor antagonist; also activator of ENaCdelta Tocris Bioscience 464

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

Density: 1.4±0.1 g/cm3
Boiling Point: 581.1±60.0 °C at 760 mmHg
Vapour Pressure: 0.0±1.7 mmHg at 25°C
Enthalpy of Vaporization: 90.1±3.0 kJ/mol
Flash Point: 305.3±32.9 °C
Index of Refraction: 1.672
Molar Refractivity: 104.4±0.3 cm3
#H bond acceptors: 4
#H bond donors: 3
#Freely Rotating Bonds: 5
#Rule of 5 Violations: 0
ACD/LogP: 3.50
ACD/LogD (pH 5.5): 3.71
ACD/BCF (pH 5.5): 388.26
ACD/KOC (pH 5.5): 2482.42
ACD/LogD (pH 7.4): 3.70
ACD/BCF (pH 7.4): 384.29
ACD/KOC (pH 7.4): 2457.03
Polar Surface Area: 88 Å2
Polarizability: 41.4±0.5 10-24cm3
Surface Tension: 66.1±3.0 dyne/cm
Molar Volume: 279.0±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) =  4.35

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  522.23  (Adapted Stein & Brown method)
    Melting Pt (deg C):  222.98  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  9.77E-013  (Modified Grain method)
    Subcooled liquid VP: 1.28E-010 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):  31.75
       log Kow used: 4.35 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  1.4814 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   7.49E-017  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  1.526E-014 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  4.35  (KowWin est)
  Log Kaw used:  -14.514  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  18.864
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.9368
   Biowin2 (Non-Linear Model)     :   0.7865
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.0685  (months      )
   Biowin4 (Primary Survey Model) :   3.2864  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :  -0.1768
   Biowin6 (MITI Non-Linear Model):   0.0042
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -1.0101
 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):  1.71E-008 Pa (1.28E-010 mm Hg)
  Log Koa (Koawin est  ): 18.864
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  176 
       Octanol/air (Koa) model:  1.79E+006 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  1 
       Mackay model           :  1 
       Octanol/air (Koa) model:  1 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant = 234.1737 E-12 cm3/molecule-sec
      Half-Life =     0.046 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     0.548 Hrs
   Ozone Reaction:
      No Ozone Reaction Estimation
   Reaction With Nitrate Radicals May Be Important!
   Fraction sorbed to airborne particulates (phi): 1 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  3.503E+005
      Log Koc:  5.544 

 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 = 2.649 (BCF = 445.9)
       log Kow used: 4.35 (estimated)

 Volatilization from Water:
    Henry LC:  7.49E-017 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 1.518E+013  hours   (6.323E+011 days)
    Half-Life from Model Lake : 1.656E+014  hours   (6.898E+012 days)

 Removal In Wastewater Treatment:
    Total removal:              47.97  percent
    Total biodegradation:        0.46  percent
    Total sludge adsorption:    47.51  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       3.42e-006       1.1          1000       
   Water     7.97            1.44e+003    1000       
   Soil      86.5            2.88e+003    1000       
   Sediment  5.54            1.3e+004     0          
     Persistence Time: 3.03e+003 hr




                    

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