ChemSpider 2D Image | Cinnamylcocaine | C19H23NO4

Cinnamylcocaine

  • Molecular FormulaC19H23NO4
  • Average mass329.390 Da
  • Monoisotopic mass329.162720 Da
  • ChemSpider ID16735745
  • Double-bond stereo - Double-bond stereo

    defined stereocentres - 1 of 4 defined stereocentres


More details:






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

(2R)-8-Méthyl-3-{[(2E)-3-phényl-2-propenoyl]oxy}-8-azabicyclo[3.2.1]octane-2-carboxylate de méthyle [French] [ACD/IUPAC Name]
[1R-(exo,exo)]-8-Methyl-3-[(1-oxo-3-phenyl-2-propenyl)oxy]-8-azabicyclo[3.2.1]octane-2-carboxylic Acid Methyl Ester
521-67-5 [RN]
8-Azabicyclo[3.2.1]octane-2-carboxylic acid, 8-methyl-3-[[(2E)-1-oxo-3-phenyl-2-propen-1-yl]oxy]-, methyl ester, (2R)- [ACD/Index Name]
Cinnamoylecgonine Methyl Ester
Cinnamoylmethylecgonine
Cinnamylcocaine
Ecgoine Cinnamate Methyl Ester
Methyl (2R)-8-methyl-3-{[(2E)-3-phenyl-2-propenoyl]oxy}-8-azabicyclo[3.2.1]octane-2-carboxylate [ACD/IUPAC Name]
Methyl (2R)-8-methyl-3-{[(2E)-3-phenylprop-2-enoyl]oxy}-8-azabicyclo[3.2.1]octane-2-carboxylate
More...

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

Density: 1.2±0.1 g/cm3
Boiling Point: 437.8±45.0 °C at 760 mmHg
Vapour Pressure: 0.0±1.1 mmHg at 25°C
Enthalpy of Vaporization: 69.4±3.0 kJ/mol
Flash Point: 218.5±28.7 °C
Index of Refraction: 1.573
Molar Refractivity: 90.3±0.4 cm3
#H bond acceptors: 5
#H bond donors: 0
#Freely Rotating Bonds: 6
#Rule of 5 Violations: 0
ACD/LogP: 3.06
ACD/LogD (pH 5.5): -0.01
ACD/BCF (pH 5.5): 1.00
ACD/KOC (pH 5.5): 1.15
ACD/LogD (pH 7.4): 1.49
ACD/BCF (pH 7.4): 3.73
ACD/KOC (pH 7.4): 36.35
Polar Surface Area: 56 Å2
Polarizability: 35.8±0.5 10-24cm3
Surface Tension: 48.4±5.0 dyne/cm
Molar Volume: 273.8±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) =  2.70

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  389.41  (Adapted Stein & Brown method)
    Melting Pt (deg C):  106.48  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  2.39E-006  (Modified Grain method)
    Subcooled liquid VP: 1.5E-005 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):  416.2
       log Kow used: 2.70 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  153.16 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   3.92E-012  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  2.489E-009 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  2.70  (KowWin est)
  Log Kaw used:  -9.795  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  12.495
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.8619
   Biowin2 (Non-Linear Model)     :   0.9977
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.5189  (weeks-months)
   Biowin4 (Primary Survey Model) :   3.5473  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.4981
   Biowin6 (MITI Non-Linear Model):   0.1148
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -0.6625
 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):  0.002 Pa (1.5E-005 mm Hg)
  Log Koa (Koawin est  ): 12.495
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  0.0015 
       Octanol/air (Koa) model:  0.767 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.0514 
       Mackay model           :  0.107 
       Octanol/air (Koa) model:  0.984 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant =  72.8218 E-12 cm3/molecule-sec [Cis-isomer]
      OVERALL OH Rate Constant =  75.4818 E-12 cm3/molecule-sec [Trans-isomer]
      Half-Life =    1.763 Hrs (12-hr day; 1.5E6 OH/cm3) [Cis-isomer]
      Half-Life =    1.700 Hrs (12-hr day; 1.5E6 OH/cm3) [Trans-isomer]
   Ozone Reaction:
      OVERALL Ozone Rate Constant =     1.050000 E-17 cm3/molecule-sec [Cis-]
      OVERALL Ozone Rate Constant =     2.100000 E-17 cm3/molecule-sec [Trans-]
      Half-Life =     1.091 Days (at 7E11 mol/cm3) [Cis-isomer]
      Half-Life =    13.097 Hrs (at 7E11 mol/cm3) [Trans-isomer]
   Fraction sorbed to airborne particulates (phi): 0.0793 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  6296
      Log Koc:  3.799 

 Aqueous Base/Acid-Catalyzed Hydrolysis (25 deg C) [HYDROWIN v1.67]:
  Total Kb for pH > 8 at 25 deg C :  1.230E-003  L/mol-sec
  Kb Half-Life at pH 8:      17.852  years  
  Kb Half-Life at pH 7:     178.515  years  

 Bioaccumulation Estimates from Log Kow (BCFWIN v2.17):
   Log BCF from regression-based method = 1.378 (BCF = 23.86)
       log Kow used: 2.70 (estimated)

 Volatilization from Water:
    Henry LC:  3.92E-012 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 2.711E+008  hours   (1.129E+007 days)
    Half-Life from Model Lake : 2.957E+009  hours   (1.232E+008 days)

 Removal In Wastewater Treatment:
    Total removal:               3.81  percent
    Total biodegradation:        0.11  percent
    Total sludge adsorption:     3.70  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       3.31e-005       3.11         1000       
   Water     14.4            900          1000       
   Soil      85.4            1.8e+003     1000       
   Sediment  0.173           8.1e+003     0          
     Persistence Time: 1.71e+003 hr




                    

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