ChemSpider 2D Image | Varenicline | C13H13N3

Varenicline

  • Molecular FormulaC13H13N3
  • Average mass211.262 Da
  • Monoisotopic mass211.110947 Da
  • ChemSpider ID4470510

  • defined stereocentres - 2 of 2 defined stereocentres

More details:

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

Varenicline [Wiki]
(1R,12S)-5,8,14-triazatetracyclo[10.3.1.02,11.04,9]hexadeca-2(11),3,5,7,9-pentaene
(1R,12S)-5,8,14-Triazatetracyclo[10.3.1.02,11.04,9]hexadeca-2,4,6,8,10-pentaen [German] [ACD/IUPAC Name]
(1R,12S)-5,8,14-Triazatetracyclo[10.3.1.02,11.04,9]hexadeca-2,4,6,8,10-pentaene [ACD/IUPAC Name]
(1R,12S)-5,8,14-Triazatétracyclo[10.3.1.02,11.04,9]hexadéca-2,4,6,8,10-pentaène [French] [ACD/IUPAC Name]
249296-44-4 [RN]
6,10-Methano-6H-azepino[4,5-g]quinoxaline, 7,8,9,10-tetrahydro-, (6R,10S)- [ACD/Index Name]
Champix [Trade name]
(1R,12S)-5,8,14-triazatetracyclo[10.3.1.02,11.04,9]hexadeca-2(11),3,5,7,9-pentaene
(1R,12S)-5,8,14-triazatetracyclo[10.3.1.02,11.04,9]hexadeca-2(11),3,5,7,9-pentaene
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

8366 [DBID]
W6HS99O8ZO [DBID]
CP 526555 [DBID]
UN 2811 [DBID]
UN2811 [DBID]
UNII:W6HS99O8ZO [DBID]
UNII-W6HS99O8ZO [DBID]
  • Experimental Physico-chemical Properties
  • Miscellaneous

    • Toxicity:

      Organic Compound; Amine; Drug; Nicotinic Agonist; Metabolite; Synthetic Compound Toxin, Toxin-Target Database T3D2577

    • Chemical Class:

      An organic heterotetracyclic compound that acts as a partial agonist for nicotinic cholinergic receptors and is used (in the form of its tartate salt) as an aid to giving up smoking. ChEBI CHEBI:84500

    • Bio Activity:

      Acetylcholine (Nicotinic) Receptors Tocris Bioscience 3754
      Ion Channels Tocris Bioscience 3754
      Ligand-gated Ion Channels Tocris Bioscience 3754
      Orally active, subtype-selective ?4?2 partial agonist Tocris Bioscience 3754
      Orally active, subtype-selective partial agonist at ?4?2 nicotinic receptors (Ki values are 0.06, 240, 322 and 3540 nM for ?4?2, ?3?4, ?7, ?1??? receptors respectively). Reduces nicotine-evoked dopami ne release in vitro and decreases nicotine self-administration in vivo. Tocris Bioscience 3754
      Orally active, subtype-selective partial agonist at ?4?2 nicotinic receptors (Ki values are 0.06, 240, 322 and 3540 nM for ?4?2, ?3?4, ?7, ?1??? receptors respectively). Reduces nicotine-evoked dopamine release in vitro and decreases nicotine self-administration in vivo. Tocris Bioscience 3754

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

Density: 1.2±0.1 g/cm3
Boiling Point: 400.6±40.0 °C at 760 mmHg
Vapour Pressure: 0.0±0.9 mmHg at 25°C
Enthalpy of Vaporization: 65.2±3.0 kJ/mol
Flash Point: 196.1±27.3 °C
Index of Refraction: 1.667
Molar Refractivity: 63.1±0.3 cm3
#H bond acceptors: 3
#H bond donors: 1
#Freely Rotating Bonds: 0
#Rule of 5 Violations: 0
ACD/LogP: 0.74
ACD/LogD (pH 5.5): -1.82
ACD/BCF (pH 5.5): 1.00
ACD/KOC (pH 5.5): 1.00
ACD/LogD (pH 7.4): -0.84
ACD/BCF (pH 7.4): 1.00
ACD/KOC (pH 7.4): 1.00
Polar Surface Area: 38 Å2
Polarizability: 25.0±0.5 10-24cm3
Surface Tension: 57.9±3.0 dyne/cm
Molar Volume: 169.4±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) =  1.03

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  360.55  (Adapted Stein & Brown method)
    Melting Pt (deg C):  143.74  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  4.65E-006  (Modified Grain method)
    Subcooled liquid VP: 7.41E-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):  5.155e+004
       log Kow used: 1.03 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  12091 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   2.68E-011  atm-m3/mole
   Group Method:   9.74E-015  atm-m3/mole
 Henrys LC [VP/WSol estimate using EPI values]:  2.508E-011 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  1.03  (KowWin est)
  Log Kaw used:  -8.960  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  9.990
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.9101
   Biowin2 (Non-Linear Model)     :   0.9066
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.6070  (weeks-months)
   Biowin4 (Primary Survey Model) :   3.4491  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.1894
   Biowin6 (MITI Non-Linear Model):   0.1050
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model):  0.1089
 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):  0.00988 Pa (7.41E-005 mm Hg)
  Log Koa (Koawin est  ): 9.990
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  0.000304 
       Octanol/air (Koa) model:  0.0024 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.0108 
       Mackay model           :  0.0237 
       Octanol/air (Koa) model:  0.161 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant =  37.7392 E-12 cm3/molecule-sec
      Half-Life =     0.283 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     3.401 Hrs
   Ozone Reaction:
      No Ozone Reaction Estimation
   Fraction sorbed to airborne particulates (phi): 0.0173 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  4159
      Log Koc:  3.619 

 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 = 0.092 (BCF = 1.236)
       log Kow used: 1.03 (estimated)

 Volatilization from Water:
    Henry LC:  2.68E-011 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 3.175E+007  hours   (1.323E+006 days)
    Half-Life from Model Lake : 3.464E+008  hours   (1.443E+007 days)

 Removal In Wastewater Treatment:
    Total removal:               1.89  percent
    Total biodegradation:        0.09  percent
    Total sludge adsorption:     1.80  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       0.000349        6.8          1000       
   Water     40.3            900          1000       
   Soil      59.6            1.8e+003     1000       
   Sediment  0.0856          8.1e+003     0          
     Persistence Time: 1.06e+003 hr

Click to predict properties on the Chemicalize site


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