ChemSpider 2D Image | Pergolide | C19H26N2S

Pergolide

  • Molecular FormulaC19H26N2S
  • Average mass314.488 Da
  • Monoisotopic mass314.181671 Da
  • ChemSpider ID43503
  • defined stereocentres - 3 of 3 defined stereocentres


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

(6aR,9R,10aR)-9-(Methylthiomethyl)-7-propyl-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoline
(6aR,9R,10aR)-9-[(Methylsulfanyl)methyl]-7-propyl-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]chinolin
(6aR,9R,10aR)-9-[(méthylsulfanyl)méthyl]-7-propyl-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoléine [French]
(6aR,9R,10aR)-9-[(methylsulfanyl)methyl]-7-propyl-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoline
(8b)-8-[(Methylthio)methyl]-6-propylergoline
(8β)-8-[(Methylsulfanyl)methyl]-6-propylergolin [German] [ACD/IUPAC Name]
(8β)-8-[(Methylsulfanyl)methyl]-6-propylergoline [ACD/IUPAC Name]
(8β)-8-[(Méthylsulfanyl)méthyl]-6-propylergoline [French] [ACD/IUPAC Name]
(8β)-8-[(methylthio)methyl]-6-propylergoline
24MJ822NZ9
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

4651 [DBID]
CHEBI:63617 [DBID]
C07425 [DBID]
DivK1c_000442 [DBID]
KBio1_000442 [DBID]
KBio2_002127 [DBID]
KBio2_004695 [DBID]
KBio2_007263 [DBID]
KBio3_002656 [DBID]
KBioGR_001409 [DBID]
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  • Experimental Physico-chemical Properties
  • Miscellaneous
    • Toxicity:

      Organic Compound; Amine; Ether; Drug; Central Nervous System Agent; Antiparkinson Agent; Antidyskinetic; Dopamine Agonist; Neuroprotective Agent; Metabolite; Synthetic Compound Toxin, Toxin-Target Database T3D3011
    • Safety:

      N04BC02 Wikidata Q415752
    • Chemical Class:

      A diamine that is ergoline in which the <stereo>beta</stereo>-hydrogen at position 8 is replaced by a (methylthio)methyl group and the hydrogen attached to the piperidine nitrogen (position 6) is repl aced by a propyl group. A dopamine D<smallsub>2</smallsub> receptor agonist which also has D<smallsub>1</smallsub> and D<smallsub>2</smallsub> agonist properties, it is used as the mesylate salt in th e management of Parkinson's disease, although it was withdrawn from the U.S. and Canadian markets in 2007 due to an increased risk of cardiac valve dysfunction. ChEBI CHEBI:63617
      A diamine that is ergoline in which the beta-hydrogen at position 8 is replaced by a (methylthio)methyl group and the hydrogen attached to the piperidine nitrogen (position 6) is repl; aced by a propy l group. A dopamine D2 receptor agonist which also has D1 and D2 agonist properties, it is used as the mesylate salt in th; e management of Parkinson's disease, although it was withdrawn from the U.S. and Canadian markets in 2007 due to an increased risk of cardiac valve dysfunction. ChEBI https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:63617
      A diamine that is ergoline in which the beta-hydrogen at position 8 is replaced by a (methylthio)methyl group and the hydrogen attached to the piperidine nitrogen (position 6) is replaced by a propyl group. A dopamine D2 receptor agonist which also has D1 and D2 agonist properties, it is used as the mesylate salt in the management of Parkinson's disease, although it was withdrawn from the U.S. and Canadian markets in 2007 due to an increased risk of cardiac valve dysfunction. ChEBI CHEBI:63617

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

Density: 1.1±0.1 g/cm3
Boiling Point: 491.3±35.0 °C at 760 mmHg
Vapour Pressure: 0.0±1.2 mmHg at 25°C
Enthalpy of Vaporization: 75.8±3.0 kJ/mol
Flash Point: 250.9±25.9 °C
Index of Refraction: 1.614
Molar Refractivity: 97.4±0.3 cm3
#H bond acceptors: 2
#H bond donors: 1
#Freely Rotating Bonds: 4
#Rule of 5 Violations: 0
ACD/LogP: 4.49
ACD/LogD (pH 5.5): 1.74
ACD/BCF (pH 5.5): 2.49
ACD/KOC (pH 5.5): 10.11
ACD/LogD (pH 7.4): 3.22
ACD/BCF (pH 7.4): 75.40
ACD/KOC (pH 7.4): 306.36
Polar Surface Area: 44 Å2
Polarizability: 38.6±0.5 10-24cm3
Surface Tension: 44.6±3.0 dyne/cm
Molar Volume: 279.6±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) =  4.02

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  445.39  (Adapted Stein & Brown method)
    Melting Pt (deg C):  181.97  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  7.43E-009  (Modified Grain method)
    MP  (exp database):  207.5 deg C
    Subcooled liquid VP: 6.39E-007 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):  2.93
       log Kow used: 4.02 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  0.63598 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   6.07E-012  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  1.049E-009 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  4.02  (KowWin est)
  Log Kaw used:  -9.605  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  13.625
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.5019
   Biowin2 (Non-Linear Model)     :   0.0741
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.0997  (months      )
   Biowin4 (Primary Survey Model) :   2.9689  (weeks       )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :  -0.1275
   Biowin6 (MITI Non-Linear Model):   0.0053
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -1.0659
 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):  8.52E-005 Pa (6.39E-007 mm Hg)
  Log Koa (Koawin est  ): 13.625
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  0.0352 
       Octanol/air (Koa) model:  10.4 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.56 
       Mackay model           :  0.738 
       Octanol/air (Koa) model:  0.999 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant = 336.8085 E-12 cm3/molecule-sec
      Half-Life =     0.032 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =    22.865 Min
   Ozone Reaction:
      No Ozone Reaction Estimation
   Reaction With Nitrate Radicals May Be Important!
   Fraction sorbed to airborne particulates (phi): 0.649 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  1.001E+006
      Log Koc:  6.000 

 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 = 2.397 (BCF = 249.7)
       log Kow used: 4.02 (estimated)

 Volatilization from Water:
    Henry LC:  6.07E-012 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 1.711E+008  hours   (7.127E+006 days)
    Half-Life from Model Lake : 1.866E+009  hours   (7.775E+007 days)

 Removal In Wastewater Treatment:
    Total removal:              30.99  percent
    Total biodegradation:        0.33  percent
    Total sludge adsorption:    30.66  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       0.000123        0.762        1000       
   Water     8.49            1.44e+003    1000       
   Soil      88.8            2.88e+003    1000       
   Sediment  2.67            1.3e+004     0          
     Persistence Time: 2.92e+003 hr




                    

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