ChemSpider 2D Image | Nicergoline | C24H26BrN3O3

Nicergoline

  • Molecular FormulaC24H26BrN3O3
  • Average mass484.385 Da
  • Monoisotopic mass483.115753 Da
  • ChemSpider ID31373
  • defined stereocentres - 3 of 3 defined stereocentres


More details:



Featured data source



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

(8b)-10-Methoxy-1,6-dimethylergoline-8-methanol 5-Bromo-3-pyridinecarboxylate (Ester)
[(8β)-10-Methoxy-1,6-dimethylergolin-8-yl]methyl 5-bromonicotinate [ACD/IUPAC Name]
[(8β)-10-methoxy-1,6-dimethylergolin-8-yl]methyl 5-bromopyridine-3-carboxylate
[(8β)-10-Methoxy-1,6-dimethylergolin-8-yl]methyl-5-bromnicotinat [German] [ACD/IUPAC Name]
10-Methoxy-1,6-dimethylergoline-8β-methanol 5-bromonicotinate ester
1-Methyllumilysergol 8-(5-Bromonicotinate) 10-Methyl Ether
248-694-6 [EINECS]
27848-84-6 [RN]
3088
3-Pyridinecarboxylic acid, 5-bromo-, [(8β)-10-methoxy-1,6-dimethylergolin-8-yl]methyl ester [ACD/Index Name]
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

BRN 4828393 [DBID]
D01290 [DBID]
DivK1c_000124 [DBID]
FI 6714 [DBID]
KBio1_000124 [DBID]
KBio2_001850 [DBID]
KBio2_004418 [DBID]
KBio2_006986 [DBID]
KBio3_002787 [DBID]
KBioGR_000800 [DBID]
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  • Experimental Physico-chemical Properties
  • Miscellaneous
    • Safety:

      C04AE02 Wikidata Q2623398
    • Compound Source:

      synthetic Microsource [01501133]
    • Bio Activity:

      Adrenergic Receptor MedChem Express HY-B0702
      Cerebroprotective props; Zerenex Molecular [ZBioX-0062]
      GPCR/G protein MedChem Express HY-B0702
      GPCR/G protein; MedChem Express HY-B0702
      Nicergoline is an ergot derivative used to treat senile dementia and other disorders with vascular origins. MedChem Express
      Nicergoline is an ergot derivative used to treat senile dementia and other disorders with vascular origins.; Target: Alpha-1A adrenergic receptor; Nicergoline acts by inhibiting the postsynaptic alpha(1)-adrenoceptors on vascular smooth muscle. MedChem Express HY-B0702
      Nicergoline is an ergot derivative used to treat senile dementia and other disorders with vascular origins.;Target: Alpha-1A adrenergic receptorNicergoline acts by inhibiting the postsynaptic alpha(1)-adrenoceptors on vascular smooth muscle. This inhibits the vasoconstrictor effect of circulating and locally released catecholamines (epinephrine and norepinephrine), resulting in peripheral vasodilation. Nicergoline displaced [3H]-prazosin bound to rat forebrain membranes pretreated with chloroethylclonidine (pKi = 9.9 +/- 0.2) at concentrations 60-fold lower than in rat liver membranes (pKi = 8.1 +/- 0.2). Finally, of the nicergoline metabolites studied, lumilysergol acted as a modest alpha 1 antagonist (bromonicotinic acid was devoid of alpha 1 antagonist activity). In conclusion, nicergoline is a potent and selective alpha 1A-adrenoceptor subtype antagonist, an alpha 1-adrenoceptor subtype which is mainly represented in resistance arteries [1]. MedChem Express HY-B0702

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

Density: 1.5±0.1 g/cm3
Boiling Point: 594.4±50.0 °C at 760 mmHg
Vapour Pressure: 0.0±1.7 mmHg at 25°C
Enthalpy of Vaporization: 88.6±3.0 kJ/mol
Flash Point: 313.3±30.1 °C
Index of Refraction: 1.670
Molar Refractivity: 122.5±0.5 cm3
#H bond acceptors: 6
#H bond donors: 0
#Freely Rotating Bonds: 5
#Rule of 5 Violations: 0
ACD/LogP: 4.34
ACD/LogD (pH 5.5): 3.62
ACD/BCF (pH 5.5): 204.71
ACD/KOC (pH 5.5): 878.51
ACD/LogD (pH 7.4): 4.48
ACD/BCF (pH 7.4): 1455.55
ACD/KOC (pH 7.4): 6246.36
Polar Surface Area: 57 Å2
Polarizability: 48.6±0.5 10-24cm3
Surface Tension: 50.6±7.0 dyne/cm
Molar Volume: 328.0±7.0 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) =  3.62

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  543.33  (Adapted Stein & Brown method)
    Melting Pt (deg C):  232.84  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  1.25E-011  (Modified Grain method)
    Subcooled liquid VP: 2.16E-009 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):  0.5797
       log Kow used: 3.62 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  31.422 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 :   1.98E-017  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  1.374E-011 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  3.62  (KowWin est)
  Log Kaw used:  -15.092  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  18.712
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :  -0.2557
   Biowin2 (Non-Linear Model)     :   0.0000
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   1.3683  (recalcitrant)
   Biowin4 (Primary Survey Model) :   2.6859  (weeks-months)
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :  -0.1508
   Biowin6 (MITI Non-Linear Model):   0.0008
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -1.1810
 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):  2.88E-007 Pa (2.16E-009 mm Hg)
  Log Koa (Koawin est  ): 18.712
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  10.4 
       Octanol/air (Koa) model:  1.26E+006 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.997 
       Mackay model           :  0.999 
       Octanol/air (Koa) model:  1 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant = 367.2558 E-12 cm3/molecule-sec
      Half-Life =     0.029 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =    20.969 Min
   Ozone Reaction:
      No Ozone Reaction Estimation
   Fraction sorbed to airborne particulates (phi): 0.998 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  4.104E+005
      Log Koc:  5.613 

 Aqueous Base/Acid-Catalyzed Hydrolysis (25 deg C) [HYDROWIN v1.67]:
  Total Kb for pH > 8 at 25 deg C :  2.058E-002  L/mol-sec
  Kb Half-Life at pH 8:       1.067  years  
  Kb Half-Life at pH 7:      10.671  years  

 Bioaccumulation Estimates from Log Kow (BCFWIN v2.17):
   Log BCF from regression-based method = 2.086 (BCF = 121.8)
       log Kow used: 3.62 (estimated)

 Volatilization from Water:
    Henry LC:  1.98E-017 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 6.508E+013  hours   (2.712E+012 days)
    Half-Life from Model Lake :   7.1E+014  hours   (2.958E+013 days)

 Removal In Wastewater Treatment:
    Total removal:              16.06  percent
    Total biodegradation:        0.21  percent
    Total sludge adsorption:    15.85  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       2.21e-008       0.699        1000       
   Water     4.56            4.32e+003    1000       
   Soil      94.7            8.64e+003    1000       
   Sediment  0.694           3.89e+004    0          
     Persistence Time: 7.74e+003 hr




                    

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