ChemSpider 2D Image | mefloquine | C17H16F6N2O

mefloquine

  • Molecular FormulaC17H16F6N2O
  • Average mass378.312 Da
  • Monoisotopic mass378.116669 Da
  • ChemSpider ID37171

  • defined stereocentres - 2 of 2 defined stereocentres

More details:

Featured data source
The Merck Index Online

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

(-)-(11S,2'R)-erythro-Mefloquine
(+)-Mefloquine
(R*,S*)-(±)-a-2-Piperidinyl-2,8-bis(trifluoromethyl)-4-quinolinemethanol
(S)-[2,8-Bis(trifluormethyl)-4-chinolinyl][(2R)-2-piperidinyl]methanol [German] [ACD/IUPAC Name]
(S)-[2,8-Bis(trifluorométhyl)-4-quinoléinyl][(2R)-2-pipéridinyl]méthanol [French] [ACD/IUPAC Name]
(S)-[2,8-Bis(trifluoromethyl)-4-quinolinyl][(2R)-2-piperidinyl]methanol [ACD/IUPAC Name]
(S)-[2,8-Bis(trifluoromethyl)quinolin-4-yl][(2R)-piperidin-2-yl]methanol
4-Quinolinemethanol, α-[(2R)-2-piperidinyl]-2,8-bis(trifluoromethyl)-, (αS)- [ACD/Index Name]
51742-87-1 [RN]
53230-10-7 [RN]
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

3777 [DBID]
CHEBI:63687 [DBID]
TML814419R [DBID]
UNII:TML814419R [DBID]
AIDS008727 [DBID]
AIDS-008727 [DBID]
HSDB 6853 [DBID]
nchembio.87-comp20 [DBID]
Ro 215998 [DBID]
UNII-TML814419R [DBID]
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  • Miscellaneous

    • Chemical Class:

      An optically active form of [2,8-bis(trifluoromethyl)quinolin-4-yl]-(2-piperidyl)methanol having (<minus/>)-(11<stereo>S</stereo>,2'<stereo>R</stereo>)-<stereo>erythro</stereo>-configuration. An antim alarial agent, used in racemic form, which acts as a blood schizonticide; its mechanism of action is unknown. ChEBI CHEBI:63687

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

Density: 1.4±0.1 g/cm3
Boiling Point: 415.7±40.0 °C at 760 mmHg
Vapour Pressure: 0.0±1.0 mmHg at 25°C
Enthalpy of Vaporization: 70.5±3.0 kJ/mol
Flash Point: 205.2±27.3 °C
Index of Refraction: 1.519
Molar Refractivity: 83.0±0.3 cm3
#H bond acceptors: 3
#H bond donors: 2
#Freely Rotating Bonds: 4
#Rule of 5 Violations: 0
ACD/LogP: 2.87
ACD/LogD (pH 5.5): 0.20
ACD/BCF (pH 5.5): 1.00
ACD/KOC (pH 5.5): 1.33
ACD/LogD (pH 7.4): 1.47
ACD/BCF (pH 7.4): 2.95
ACD/KOC (pH 7.4): 24.42
Polar Surface Area: 45 Å2
Polarizability: 32.9±0.5 10-24cm3
Surface Tension: 36.5±3.0 dyne/cm
Molar Volume: 273.4±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) =  3.85

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  407.47  (Adapted Stein & Brown method)
    Melting Pt (deg C):  168.01  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  3.74E-009  (Modified Grain method)
    Subcooled liquid VP: 1.12E-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):  21.82
       log Kow used: 3.85 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  248.89 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   6.49E-013  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  8.532E-011 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  3.85  (KowWin est)
  Log Kaw used:  -10.576  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  14.426
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :  -0.1608
   Biowin2 (Non-Linear Model)     :   0.0000
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   1.5216  (recalcitrant)
   Biowin4 (Primary Survey Model) :   2.9258  (weeks       )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :  -0.0002
   Biowin6 (MITI Non-Linear Model):   0.0000
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model):  0.3569
 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):  1.49E-005 Pa (1.12E-007 mm Hg)
  Log Koa (Koawin est  ): 14.426
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  0.201 
       Octanol/air (Koa) model:  65.5 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.879 
       Mackay model           :  0.941 
       Octanol/air (Koa) model:  1 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant =  51.3068 E-12 cm3/molecule-sec
      Half-Life =     0.208 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     2.502 Hrs
   Ozone Reaction:
      No Ozone Reaction Estimation
   Fraction sorbed to airborne particulates (phi): 0.91 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  1.918E+005
      Log Koc:  5.283 

 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 = 1.615 (BCF = 41.24)
       log Kow used: 3.85 (estimated)

 Volatilization from Water:
    Henry LC:  6.49E-013 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 1.755E+009  hours   (7.311E+007 days)
    Half-Life from Model Lake : 1.914E+010  hours   (7.976E+008 days)

 Removal In Wastewater Treatment:
    Total removal:              23.72  percent
    Total biodegradation:        0.27  percent
    Total sludge adsorption:    23.45  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       1.14e-005       5            1000       
   Water     4.22            4.32e+003    1000       
   Soil      94.6            8.64e+003    1000       
   Sediment  1.21            3.89e+004    0          
     Persistence Time: 7.98e+003 hr

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