ChemSpider 2D Image | dextilidine | C17H23NO2

dextilidine

  • Molecular FormulaC17H23NO2
  • Average mass273.370 Da
  • Monoisotopic mass273.172882 Da
  • ChemSpider ID27988
  • defined stereocentres - 2 of 2 defined stereocentres


More details:






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

dextilidine [INN]
(+)-(1S,2R)-ethyl-2-dimethylamino-1-phenyl-3-cyclohexen-1-carboxylate
(1S,2R)-2-(Diméthylamino)-1-phényl-3-cyclohexène-1-carboxylate d'éthyle [French] [ACD/IUPAC Name]
243-774-7 [EINECS]
2510
251-048-6 [EINECS]
257-522-9 [EINECS]
2728MV084C
32447-90-8 [RN]
3474
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

DEA No. 9750 [DBID]
  • Miscellaneous
    • Chemical Class:

      An ethyl 2-(dimethylamino)-1-phenylcyclohex-3-ene-1-carboxylate that has <stereo>S</stereo> configuration at the carbon bearing the phenyl group and <stereo>R</stereo> configuration at the carbon bear ing the dimethylamino group. The opioid analgesic tilidine is the racemate comprising equimolar amounts of dextilidine and its enantiomer, <ital>ent</ital>-dextilidine. A prodrug, tilidine is converte d by the liver to the active analgesic, nortilidine; virtually all of the opioid activity resides in the (1<stereo>S</stereo>,2<stereo>R</stereo>) isomer (i.e. the isomer derived from dextilidine). ChEBI CHEBI:77822

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

Density: 1.1±0.1 g/cm3
Boiling Point: 354.2±42.0 °C at 760 mmHg
Vapour Pressure: 0.0±0.8 mmHg at 25°C
Enthalpy of Vaporization: 59.9±3.0 kJ/mol
Flash Point: 114.0±18.8 °C
Index of Refraction: 1.548
Molar Refractivity: 81.3±0.4 cm3
#H bond acceptors: 3
#H bond donors: 0
#Freely Rotating Bonds: 5
#Rule of 5 Violations: 0
ACD/LogP: 3.00
ACD/LogD (pH 5.5): 0.34
ACD/BCF (pH 5.5): 1.00
ACD/KOC (pH 5.5): 2.39
ACD/LogD (pH 7.4): 2.03
ACD/BCF (pH 7.4): 12.32
ACD/KOC (pH 7.4): 115.76
Polar Surface Area: 30 Å2
Polarizability: 32.2±0.5 10-24cm3
Surface Tension: 41.4±5.0 dyne/cm
Molar Volume: 255.7±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) =  3.72

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  348.79  (Adapted Stein & Brown method)
    Melting Pt (deg C):  105.73  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  2.29E-005  (Modified Grain method)
    BP  (exp database):  95.75 @ 0.01 mm Hg deg C
    Subcooled liquid VP: 0.000141 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):  118.1
       log Kow used: 3.72 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  102.14 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 :   1.49E-008  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  6.975E-008 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  3.72  (KowWin est)
  Log Kaw used:  -6.215  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  9.935
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.5305
   Biowin2 (Non-Linear Model)     :   0.7425
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.2903  (weeks-months)
   Biowin4 (Primary Survey Model) :   3.2457  (weeks       )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.3814
   Biowin6 (MITI Non-Linear Model):   0.1333
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -1.2205
 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):  0.0188 Pa (0.000141 mm Hg)
  Log Koa (Koawin est  ): 9.935
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  0.00016 
       Octanol/air (Koa) model:  0.00211 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.00573 
       Mackay model           :  0.0126 
       Octanol/air (Koa) model:  0.145 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant = 155.6406 E-12 cm3/molecule-sec
      Half-Life =     0.069 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     0.825 Hrs
   Ozone Reaction:
      OVERALL Ozone Rate Constant =    20.000000 E-17 cm3/molecule-sec
      Half-Life =     0.057 Days (at 7E11 mol/cm3)
      Half-Life =      1.375 Hrs
   Fraction sorbed to airborne particulates (phi): 0.00917 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  1.147E+004
      Log Koc:  4.060 

 Aqueous Base/Acid-Catalyzed Hydrolysis (25 deg C) [HYDROWIN v1.67]:
  Total Kb for pH > 8 at 25 deg C :  2.680E-004  L/mol-sec
  Kb Half-Life at pH 8:      81.939  years  
  Kb Half-Life at pH 7:     819.392  years  

 Bioaccumulation Estimates from Log Kow (BCFWIN v2.17):
   Log BCF from regression-based method = 2.166 (BCF = 146.4)
       log Kow used: 3.72 (estimated)

 Volatilization from Water:
    Henry LC:  1.49E-008 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 6.497E+004  hours   (2707 days)
    Half-Life from Model Lake : 7.089E+005  hours   (2.954E+004 days)

 Removal In Wastewater Treatment:
    Total removal:              19.08  percent
    Total biodegradation:        0.23  percent
    Total sludge adsorption:    18.85  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       0.0255          0.75         1000       
   Water     16.2            900          1000       
   Soil      81.8            1.8e+003     1000       
   Sediment  1.98            8.1e+003     0          
     Persistence Time: 1.19e+003 hr




                    

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