ChemSpider 2D Image | Rivastigmine | C14H22N2O2

Rivastigmine

  • Molecular FormulaC14H22N2O2
  • Average mass250.337 Da
  • Monoisotopic mass250.168121 Da
  • ChemSpider ID70377

  • defined stereocentres - 1 of 1 defined stereocentres

More details:

Featured data source
The Merck Index Online

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

(S)-3-(1-(dimethylamino)ethyl)phenyl ethyl(methyl)carbamate
(S)-N-ethyl-3-[(1-dimethylamino)ethyl]-N-methylphenylcarbamate
123441-03-2 [RN]
3-((1S)-1-(Dimethylamino)ethyl)phenyl ethylmethylcarbamate
3-[(1S)-1-(Dimethylamino)ethyl]phenyl ethyl(methyl)carbamate [ACD/IUPAC Name]
3-[(1S)-1-(Dimethylamino)ethyl]phenyl-ethyl(methyl)carbamat [German] [ACD/IUPAC Name]
415973-05-6 [RN]
carbamic acid, ethyl(methyl)-, 3-[(1S)-1-(dimethylamino)ethyl]phenyl ester
Carbamic acid, N-ethyl-N-methyl-, 3-[(1S)-1-(dimethylamino)ethyl]phenyl ester [ACD/Index Name]
Éthyl(méthyl)carbamate de 3-[(1S)-1-(diméthylamino)éthyl]phényle [French] [ACD/IUPAC Name]
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

7562 [DBID]
C11766 [DBID]
D03822 [DBID]
ENA-713 [DBID]
  • Experimental Physico-chemical Properties
  • Miscellaneous

    • Safety:

      N06DA03 Wikidata Q411887

    • Target Organs:

      AChE inhibitor TargetMol T0229

    • Chemical Class:

      A carbamate ester obtained by formal condensation of the carboxy group of ethyl(methyl)carbamic acid with the phenolic OH group of 3-[(1<stereo>S</stereo>)-1-(dimethylamino)ethyl]phenol. A reversible cholinesterase inhibitor. ChEBI CHEBI:8874
      A carbamate ester obtained by formal condensation of the carboxy group of ethyl(methyl)carbamic acid with the phenolic OH group of 3-[(1S)-1-(dimethylamino)ethyl]phenol. A reversible ; cholinesterase inhibitor. ChEBI https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:8874
      A carbamate ester obtained by formal condensation of the carboxy group of ethyl(methyl)carbamic acid with the phenolic OH group of 3-[(1S)-1-(dimethylamino)ethyl]phenol. A reversible cholinesterase in hibitor. ChEBI CHEBI:8874

    • Bio Activity:

      AChE MedChem Express HY-17368
      AChE TargetMol T0229
      Neuronal Signaling MedChem Express HY-17368
      Neuronal Signaling; MedChem Express HY-17368
      Neuroscience TargetMol T0229
      Rivastigmine, an cholinesterase inhibitor(IC50= 5.5 uM), inhibits both butyrylcholinesterase and acetylcholinesterase MedChem Express
      Rivastigmine, an cholinesterase inhibitor(IC50= 5.5 uM), inhibits both butyrylcholinesterase and acetylcholinesterase; IC50 value: 5.5 uM; Target: AChE; Rivastigmine is a parasympathomimetic or cholinergic agent for the treatment of mild to moderate dementia of the Alzheimer's type and dementia due to Parkinson's disease. MedChem Express HY-17368
      Rivastigmine, an cholinesterase inhibitor(IC50= 5.5 uM), inhibits both butyrylcholinesterase and acetylcholinesterase;IC50 value: 5.5 uM;Target: AChERivastigmine is a parasympathomimetic or cholinergic agent for the treatment of mild to moderate dementia of the Alzheimer's type and dementia due to Parkinson's disease. The drug can be administered orally or via a transdermal patch; the latter form reduces the prevalence of side effects, which typically include nausea and vomiting. The drug is eliminated through the urine, and appears to have relatively few drug-drug interactions. Rivastigmine, a cholinesterase inhibitor, inhibits both butyrylcholinesterase and acetylcholinesterase. It is thought to work by inhibiting these cholinesterase enzymes, which would otherwise break down the brain chemical acetylcholine. MedChem Express HY-17368

Predicted data is generated using the ACD/Labs Percepta Platform - PhysChem Module, version: 14.00

Density: 1.0±0.1 g/cm3
Boiling Point: 316.2±34.0 °C at 760 mmHg
Vapour Pressure: 0.0±0.7 mmHg at 25°C
Enthalpy of Vaporization: 55.8±3.0 kJ/mol
Flash Point: 145.0±25.7 °C
Index of Refraction: 1.518
Molar Refractivity: 73.1±0.3 cm3
#H bond acceptors: 4
#H bond donors: 0
#Freely Rotating Bonds: 5
#Rule of 5 Violations: 0
ACD/LogP: 2.14
ACD/LogD (pH 5.5): -0.50
ACD/BCF (pH 5.5): 1.00
ACD/KOC (pH 5.5): 1.00
ACD/LogD (pH 7.4): 1.09
ACD/BCF (pH 7.4): 2.03
ACD/KOC (pH 7.4): 26.20
Polar Surface Area: 33 Å2
Polarizability: 29.0±0.5 10-24cm3
Surface Tension: 36.9±3.0 dyne/cm
Molar Volume: 241.2±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) =  2.24

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  319.09  (Adapted Stein & Brown method)
    Melting Pt (deg C):  89.12  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  0.00017  (Modified Grain method)
    Subcooled liquid VP: 0.000704 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):  2908
       log Kow used: 2.24 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  2513.4 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 :   6.80E-011  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  1.926E-008 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  2.24  (KowWin est)
  Log Kaw used:  -8.556  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  10.796
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.5026
   Biowin2 (Non-Linear Model)     :   0.1468
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.3444  (weeks-months)
   Biowin4 (Primary Survey Model) :   3.3922  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :  -0.0864
   Biowin6 (MITI Non-Linear Model):   0.0208
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -0.9593
 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):  0.0939 Pa (0.000704 mm Hg)
  Log Koa (Koawin est  ): 10.796
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  3.2E-005 
       Octanol/air (Koa) model:  0.0153 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.00115 
       Mackay model           :  0.00255 
       Octanol/air (Koa) model:  0.551 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant = 102.4021 E-12 cm3/molecule-sec
      Half-Life =     0.104 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     1.253 Hrs
   Ozone Reaction:
      No Ozone Reaction Estimation
   Fraction sorbed to airborne particulates (phi): 0.00185 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  312
      Log Koc:  2.494 

 Aqueous Base/Acid-Catalyzed Hydrolysis (25 deg C) [HYDROWIN v1.67]:
  Total Kb for pH > 8 at 25 deg C :  1.716E-005  L/mol-sec
  Kb Half-Life at pH 8:    1279.653  years  
  Kb Half-Life at pH 7: 1.280E+004  years  

 Bioaccumulation Estimates from Log Kow (BCFWIN v2.17):
   Log BCF from regression-based method = 1.028 (BCF = 10.66)
       log Kow used: 2.24 (estimated)

 Volatilization from Water:
    Henry LC:  6.8E-011 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 1.362E+007  hours   (5.676E+005 days)
    Half-Life from Model Lake : 1.486E+008  hours   (6.192E+006 days)

 Removal In Wastewater Treatment:
    Total removal:               2.54  percent
    Total biodegradation:        0.10  percent
    Total sludge adsorption:     2.44  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       0.000601        2.51         1000       
   Water     19.2            900          1000       
   Soil      80.7            1.8e+003     1000       
   Sediment  0.102           8.1e+003     0          
     Persistence Time: 1.53e+003 hr

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