PLANNED MAINTENANCE

There will be scheduled maintenance work beginning on Wednesday 26th February 2020 from 11:00 AM through to 12.00 PM (GMT).

During this time, you may not be able to log into ChemSpider. We apologise for any inconvenience this might cause and thank you for your patience.


ChemSpider 2D Image | Paroxetine | C19H20FNO3

Paroxetine

  • Molecular FormulaC19H20FNO3
  • Average mass329.365 Da
  • Monoisotopic mass329.142731 Da
  • ChemSpider ID39888
  • defined stereocentres - 2 of 2 defined stereocentres


More details:



Featured data source



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

(-)-Paroxetine
(-)-trans-4-(p-Fluorophenyl)-3-[[3,4-(methylenedioxy)phenoxy]methyl]piperidine
(3S,4R)-3-[(1,3-Benzodioxol-5-yloxy)methyl]-4-(4-fluorophenyl)piperidine [ACD/IUPAC Name]
(3S,4R)-3-[(1,3-Benzodioxol-5-yloxy)méthyl]-4-(4-fluorophényl)pipéridine [French] [ACD/IUPAC Name]
(3S,4R)-3-[(1,3-Benzodioxol-5-yloxy)methyl]-4-(4-fluorphenyl)piperidin [German] [ACD/IUPAC Name]
(3S-trans)-3-[(1,3-Benzodioxol-5-yl-oxy)methyl]-4-(4-fluorophenyl)piperidine
4327
61869-08-7 [RN]
aropax
BRL 29060A
More...

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

41VRH5220H [DBID]
CHEBI:7936 [DBID]
GF 74 [DBID]
BRL 29060 [DBID]
BRL-29060 [DBID]
C07415 [DBID]
D02362 [DBID]
DivK1c_006884 [DBID]
FG 7051 [DBID]
FG-7051 [DBID]
More...
  • Experimental Physico-chemical Properties
  • Miscellaneous
    • Toxicity:

      Organic Compound; Amine; Organofluoride; Ether; Drug; Food Toxin; Antidepressant; Selective Serotonin Reuptake Inhibitor; Serotonin Uptake Inhibitor; Antidepressant, Second-Generation; Metabolite; Synthetic Compound; Antidepressive Agent Toxin, Toxin-Target Database T3D2868
    • Safety:

      N06AB05 Wikidata Q408471
    • Chemical Class:

      A benzodioxole that consists of piperidine bearing 1,3-benzodioxol-5-yloxy)methyl and 4-fluorophenyl substituents at positions 3 and 4 respectively; the (3<stereo>S</stereo>,4<stereo>R</stereo>)-diast ereomer. Highly potent and selective 5-HT uptake inhibitor that binds with high affinity to the serotonin transporter (Ki = 0.05 nM). Ki values are 1.1, 350 and 1100 nM for inhibition of [3H]-5-HT, [3 H]-l-NA and [3H]-DA uptake respectively. Displays minimal affinity for <greek>alpha</greek>1-, <greek>alpha</greek>2- or <greek>beta</greek>-adrenoceptors, 5-HT<smallsub>2A</smallsub>, 5-HT<smallsub>1 A</smallsub>, D<smallsub>2</smallsub> or H<smallsub>1</smallsub> receptors at concentrations below 1000 nM, however displays weak affinity for muscarinic ACh receptors (Ki = 42 nM). Antidepressant and anxiolytic in vivo. ChEBI CHEBI:7936
      A benzodioxole that consists of piperidine bearing 1,3-benzodioxol-5-yloxy)methyl and 4-fluorophenyl substituents at positions 3 and 4 respectively; the (3S,4R)-diast; ereomer. Highly potent and selec tive 5-HT uptake inhibitor that binds with high affinity to the serotonin transporter (Ki = 0.05 nM). Ki values are 1.1, 350 and 1100 nM for inhibition of [3H]-5-HT, [3H]-l-NA and [3H]-DA uptake respe ctively. Displays minimal affinity for alpha1-, alpha2- or beta-adrenoceptors, 5-HT2A, 5-HT1; A, D2 or H1 receptors at concentrations below 1000 nM, however displays weak affinity for muscarinic ACh r eceptors (Ki = 42 nM). Antidepressant and; anxiolytic in vivo. ChEBI https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:7936
    • Therapeutical Effect:

      Serotonin Uptake Inhibitors Sean Ekins

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

Density: 1.2±0.1 g/cm3
Boiling Point: 451.7±45.0 °C at 760 mmHg
Vapour Pressure: 0.0±1.1 mmHg at 25°C
Enthalpy of Vaporization: 71.1±3.0 kJ/mol
Flash Point: 227.0±28.7 °C
Index of Refraction: 1.561
Molar Refractivity: 87.9±0.3 cm3
#H bond acceptors: 4
#H bond donors: 1
#Freely Rotating Bonds: 4
#Rule of 5 Violations: 0
ACD/LogP: 3.89
ACD/LogD (pH 5.5): 0.61
ACD/BCF (pH 5.5): 1.00
ACD/KOC (pH 5.5): 2.05
ACD/LogD (pH 7.4): 1.46
ACD/BCF (pH 7.4): 2.20
ACD/KOC (pH 7.4): 14.31
Polar Surface Area: 40 Å2
Polarizability: 34.9±0.5 10-24cm3
Surface Tension: 45.5±3.0 dyne/cm
Molar Volume: 271.5±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) =  2.57

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  423.77  (Adapted Stein & Brown method)
    Melting Pt (deg C):  172.51  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  6.49E-008  (Modified Grain method)
    Subcooled liquid VP: 2.18E-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):  537.1
       log Kow used: 2.57 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  3938.3 mg/L

 ECOSAR Class Program (ECOSAR v0.99h):
    Class(es) found:
       Aliphatic Amines
       Vinyl/Allyl Ethers

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   1.91E-009  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  5.237E-011 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  2.57  (KowWin est)
  Log Kaw used:  -7.107  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  9.677
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :  -1.0528
   Biowin2 (Non-Linear Model)     :   0.0000
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   1.9879  (months      )
   Biowin4 (Primary Survey Model) :   3.3315  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :  -0.0302
   Biowin6 (MITI Non-Linear Model):   0.0001
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -0.8566
 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):  0.000291 Pa (2.18E-006 mm Hg)
  Log Koa (Koawin est  ): 9.677
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  0.0103 
       Octanol/air (Koa) model:  0.00117 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.272 
       Mackay model           :  0.452 
       Octanol/air (Koa) model:  0.0854 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant = 423.8937 E-12 cm3/molecule-sec
      Half-Life =     0.025 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =    18.168 Min
   Ozone Reaction:
      OVERALL Ozone Rate Constant =     8.425000 E-17 cm3/molecule-sec
      Half-Life =     0.136 Days (at 7E11 mol/cm3)
      Half-Life =      3.265 Hrs
   Fraction sorbed to airborne particulates (phi): 0.362 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  432
      Log Koc:  2.635 

 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 = 1.278 (BCF = 18.97)
       log Kow used: 2.57 (estimated)

 Volatilization from Water:
    Henry LC:  1.91E-009 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 5.563E+005  hours   (2.318E+004 days)
    Half-Life from Model Lake : 6.069E+006  hours   (2.529E+005 days)

 Removal In Wastewater Treatment:
    Total removal:               3.31  percent
    Total biodegradation:        0.10  percent
    Total sludge adsorption:     3.21  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       0.00836         0.511        1000       
   Water     16.7            1.44e+003    1000       
   Soil      83.2            2.88e+003    1000       
   Sediment  0.164           1.3e+004     0          
     Persistence Time: 1.78e+003 hr




                    

Click to predict properties on the Chemicalize site






Advertisement