ChemSpider 2D Image | Amantadine | C10H17N

Amantadine

  • Molecular FormulaC10H17N
  • Average mass151.249 Da
  • Monoisotopic mass151.136093 Da
  • ChemSpider ID2045

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1-Adamantanamin [German] [ACD/IUPAC Name]
1-Adamantanamine [ACD/IUPAC Name]
1-Adamantanamine [French] [ACD/IUPAC Name]
1-Adamantanamine (8CI)
1-Amantadine
1-aminoadamantan
1-aminoadamantane
1-Aminodiamantane
1-Aminotricyclo[3.3.1.13,7]decane
211-560-2 [EINECS]
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

GP 38026 [DBID]
06649_FLUKA [DBID]
138576_ALDRICH [DBID]
AIDS001627 [DBID]
AIDS-001627 [DBID]
BRN 2204333 [DBID]
C06818 [DBID]
CHEBI:2618 [DBID]
DivK1c_000815 [DBID]
e2 [DBID]
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  • Experimental Physico-chemical Properties
  • Miscellaneous
    • Safety:

      22-36/37/38 Alfa Aesar H30076
      26-36/37 Alfa Aesar H30076
      H302+H312+H332 W&J PharmaChem, Inc. [300033]
      H302-H315-H319-H335 Alfa Aesar H30076
      Harmful/Irritant SynQuest 3230-1-X0, 59340
      IRRITANT Matrix Scientific 101734
      P261-P280-P305+P351+P338-P304+P340-P405-P501a Alfa Aesar H30076
      P302+P352+P304+P312+P503+P351+P338+P403+P235+P280+P260 W&J PharmaChem, Inc. [300033]
      Warning Alfa Aesar H30076
      WARNING: Irritates skin and eyes, harmful if swallowed Alfa Aesar H30076
    • Chemical Class:

      A member of the class of adamantanes that is used as an antiviral and antiparkinson drug. ChEBI CHEBI:2618
    • Bio Activity:

      Antiviral agent; Zerenex Molecular [ZBioX-0675]
  • Gas Chromatography
    • Retention Index (Kovats):

      1098 (estimated with error: 174) NIST Spectra mainlib_232354, replib_234672, replib_238492, replib_250716, replib_379474
      1256 (Program type: Isothermal; Col... (show more) umn class: Standard non-polar; Column length: 2 m; Column type: Packed; Start T: 230 C; CAS no: 768945; Active phase: PMS-1000; Carrier gas: N2; Substrate: Chromaton N-AW-DMCS; Data type: Kovats RI; Authors: Arutyunov, Y.I.; Kudryashov, S.Y.; Onuchak, L.A., Analysis of Mixtures Containing Unknown Components by Gas Chromatography: Determination of Molecular Mass, J. Anal. Chem. USSR (Engl. Transl.), 59(4), 2004, 358-365, In original 403-411.) NIST Spectra nist ri
      1266 (Program type: Isothermal; Col... (show more) umn class: Standard non-polar; Column length: 1 m; Column type: Packed; Start T: 160 C; CAS no: 768945; Active phase: PMS-1000; Carrier gas: N2; Substrate: Chromatron N-AW; Data type: Kovats RI; Authors: Kurbatova, S.V.; Moiseev, I.K.; Kudryashov, S.Yu.; Yashkin, S.N.; Postnikova, I.V., Chromatographic examination of the intermediate products of midantane synthesis, J. Anal. Chem. USSR (Engl. Transl.), 54(1), 1999, 75-77.) NIST Spectra nist ri
      1292 (Program type: Isothermal; Col... (show more) umn class: Standard non-polar; Column length: 1 m; Column type: Packed; Start T: 200 C; CAS no: 768945; Active phase: OV-101; Carrier gas: N2; Substrate: Chromaton N-AW; Data type: Kovats RI; Authors: Kurbatova, S.V.; Yashkin, S.N.; Moiseev, I.K.; Zemtsova, M.N., A study of the cell effect for adamantane derivatives by gas-liquid chromatography, Russ. J. Phys. Chem. (Engl. Transl.), 73(9), 1999, 1486-1489., Program type: Isothermal; Col... (show more) umn class: Standard non-polar; Column length: 1 m; Column type: Packed; Start T: 200 C; CAS no: 768945; Active phase: OV-101; Substrate: Chromaton N-AW; Data type: Kovats RI; Authors: Kurbatova, S.V.; Moiseev, I.K.; Zemtsova, M.N.; Kudryashov, S.Yu., Gas chromatography of aminoadamantanes, J. Anal. Chem. USSR (Engl. Transl.), 53(8), 1998, 732-734.) NIST Spectra nist ri
      1297 (Program type: Isothermal; Col... (show more) umn class: Standard non-polar; Column diameter: 0.25 mm; Column length: 50 m; Column type: Capillary; Start T: 200 C; CAS no: 768945; Active phase: OV-101; Carrier gas: N2; Data type: Kovats RI; Authors: Suslov, I.A.; Rudenko, B.A.; Arzamastsev, A.P., Capillary chromatography of adamantane derivatives, Zh. Anal. Khim., 43, 1988, 328-332.) NIST Spectra nist ri
      1272 (Program type: Isothermal; Col... (show more) umn class: Standard non-polar; Column length: 2 m; Column type: Packed; Start T: 140 C; CAS no: 768945; Active phase: SE-30; Carrier gas: N2; Substrate: 1% se-30 on Anachrom ABS(80-100mesh); Data type: Kovats RI; Authors: Musumarra, G.; Scarlata, G.; Romano, G.; Cappello, G.; Clementi, S.; Giulietti, G., Qualitative organic analysis. Part 2. Identification of drugs by principal components analysis of standardized TLC data in four eluent systems and of retention indices on SE 30, J. Anal. Toxicol., 11, 1987, 154-163.) NIST Spectra nist ri
      1216 (Program type: Isothermal; Col... (show more) umn class: Semi-standard non-polar; Column length: 1 m; Column type: Packed; Start T: 160 C; CAS no: 768945; Active phase: Apiezon L; Carrier gas: N2; Substrate: Chromatron N-AW; Data type: Kovats RI; Authors: Kurbatova, S.V.; Moiseev, I.K.; Kudryashov, S.Yu.; Yashkin, S.N.; Postnikova, I.V., Chromatographic examination of the intermediate products of midantane synthesis, J. Anal. Chem. USSR (Engl. Transl.), 54(1), 1999, 75-77.) NIST Spectra nist ri
      1240 (Program type: Isothermal; Col... (show more) umn class: Semi-standard non-polar; Column length: 1 m; Column type: Packed; Start T: 200 C; CAS no: 768945; Active phase: Apiezon L; Carrier gas: N2; Substrate: Chromaton N-AW; Data type: Kovats RI; Authors: Kurbatova, S.V.; Yashkin, S.N.; Moiseev, I.K.; Zemtsova, M.N., A study of the cell effect for adamantane derivatives by gas-liquid chromatography, Russ. J. Phys. Chem. (Engl. Transl.), 73(9), 1999, 1486-1489., Program type: Isothermal; Col... (show more) umn class: Semi-standard non-polar; Column length: 1 m; Column type: Packed; Start T: 200 C; CAS no: 768945; Active phase: Apiezon L; Substrate: Chromaton N-AW; Data type: Kovats RI; Authors: Kurbatova, S.V.; Moiseev, I.K.; Zemtsova, M.N.; Kudryashov, S.Yu., Gas chromatography of aminoadamantanes, J. Anal. Chem. USSR (Engl. Transl.), 53(8), 1998, 732-734.) NIST Spectra nist ri
      1395 (Program type: Isothermal; Col... (show more) umn class: Standard polar; Column length: 1 m; Column type: Packed; Start T: 160 C; CAS no: 768945; Active phase: Carbowax 20M; Carrier gas: N2; Substrate: Chromatron N-AW; Data type: Kovats RI; Authors: Kurbatova, S.V.; Moiseev, I.K.; Kudryashov, S.Yu.; Yashkin, S.N.; Postnikova, I.V., Chromatographic examination of the intermediate products of midantane synthesis, J. Anal. Chem. USSR (Engl. Transl.), 54(1), 1999, 75-77.) NIST Spectra nist ri
    • Retention Index (Normal Alkane):

      1257 (Program type: Ramp; Column cl... (show more) ass: Standard non-polar; Column type: Other; CAS no: 768945; Active phase: Methyl Silicone; Data type: Normal alkane RI; Authors: Ardrey, R.E.; Moffat, A.C., Gas-liquid chromatographic retention indices of 1318 substances of toxicological interest on SE-30 or OV-1 stationary phase, J. Chromatogr., 220, 1981, 195-252.) NIST Spectra nist ri
      1221.1 (Program type: Complex; Column... (show more) class: Semi-standard non-polar; Column diameter: 0.32 mm; Column length: 15 m; Column type: Capillary; Description: 70 0C (0.7 min) ^ 20 0C/min -> 140 0C ^ 10 0C/min -> 290 0C (9.5 min); CAS no: 768945; Active phase: DB-5; Carrier gas: He; Phase thickness: 0.25 um; Data type: Normal alkane RI; Authors: Rasanen, I.; Ojanpera, I.; Vartiovaara, J.; Vuori, E.; Sunila, P., The advantage of dual-column approach and retention indices combined with refined reporting in gas chromatographic drug screening, J. Hi. Res. Chromatogr., 19, 1996, 313-321.) NIST Spectra nist ri
    • Retention Index (Linear):

      1211 (Program type: Ramp; Column cl... (show more) ass: Standard non-polar; Column diameter: 0.25 mm; Column length: 15 m; Column type: Capillary; Heat rate: 5 K/min; Start T: 100 C; End T: 295 C; CAS no: 768945; Active phase: SE-30; Carrier gas: He; Phase thickness: 0.25 um; Data type: Linear RI; Authors: Anderson, W.H.; Stafford, D.T., Applications of capillary gas chromatography in routine toxicological analyses, J. Hi. Res. Chromatogr. & Chromatogr. Comm., 6, 1983, 247-254.) NIST Spectra nist ri
      1250 (Program type: Ramp; Column cl... (show more) ass: Standard non-polar; Column length: 1.8 m; Column type: Packed; Heat rate: 8 K/min; Start T: 130 C; End T: 290 C; End time: 8 min; Start time: 2 min; CAS no: 768945; Active phase: SE-30; Carrier gas: N2; Substrate: Chromosorb W; Data type: Linear RI; Authors: Perrigo, B.J.; Peel, H.W., The use of retention indices and temperature-programmed gas chromatography in analytical toxicology, J. Chromatogr. Sci., 19, 1981, 219-226.) NIST Spectra nist ri

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

Density: 1.1±0.1 g/cm3
Boiling Point: 225.7±8.0 °C at 760 mmHg
Vapour Pressure: 0.1±0.4 mmHg at 25°C
Enthalpy of Vaporization: 46.2±3.0 kJ/mol
Flash Point: 96.0±9.7 °C
Index of Refraction: 1.558
Molar Refractivity: 45.7±0.3 cm3
#H bond acceptors: 1
#H bond donors: 2
#Freely Rotating Bonds: 0
#Rule of 5 Violations: 0
ACD/LogP: 2.22
ACD/LogD (pH 5.5): -0.56
ACD/BCF (pH 5.5): 1.00
ACD/KOC (pH 5.5): 1.00
ACD/LogD (pH 7.4): -0.37
ACD/BCF (pH 7.4): 1.00
ACD/KOC (pH 7.4): 1.00
Polar Surface Area: 26 Å2
Polarizability: 18.1±0.5 10-24cm3
Surface Tension: 46.8±3.0 dyne/cm
Molar Volume: 141.8±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) =  2.43
    Log Kow (Exper. database match) =  2.44
       Exper. Ref:  Hansch,C et al. (1995)

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  214.19  (Adapted Stein & Brown method)
    Melting Pt (deg C):  35.11  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  0.00398  (Modified Grain method)
    MP  (exp database):  180 deg C
    Subcooled liquid VP: 0.163 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):  6292
       log Kow used: 2.44 (expkow database)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  1764.4 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   8.32E-006  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  1.259E-007 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  2.44  (exp database)
  Log Kaw used:  -3.468  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  5.908
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.6454
   Biowin2 (Non-Linear Model)     :   0.5616
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.6772  (weeks-months)
   Biowin4 (Primary Survey Model) :   3.5194  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.5188
   Biowin6 (MITI Non-Linear Model):   0.3328
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model):  0.0774
 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):  21.7 Pa (0.163 mm Hg)
  Log Koa (Koawin est  ): 5.908
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  1.38E-007 
       Octanol/air (Koa) model:  1.99E-007 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  4.99E-006 
       Mackay model           :  1.1E-005 
       Octanol/air (Koa) model:  1.59E-005 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant =  40.3085 E-12 cm3/molecule-sec
      Half-Life =     0.265 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     3.184 Hrs
   Ozone Reaction:
      No Ozone Reaction Estimation
   Fraction sorbed to airborne particulates (phi): 8.01E-006 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  384.6
      Log Koc:  2.585 

 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 = 1.179 (BCF = 15.09)
       log Kow used: 2.44 (expkow database)

 Volatilization from Water:
    Henry LC:  8.32E-006 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River:       87.8  hours   (3.658 days)
    Half-Life from Model Lake :       1061  hours   (44.21 days)

 Removal In Wastewater Treatment:
    Total removal:               3.39  percent
    Total biodegradation:        0.10  percent
    Total sludge adsorption:     2.83  percent
    Total to Air:                0.46  percent
      (using 10000 hr Bio P,A,S)

 Level III Fugacity Model:
           Mass Amount    Half-Life    Emissions
            (percent)        (hr)       (kg/hr)
   Air       0.347           6.37         1000       
   Water     23.7            900          1000       
   Soil      75.8            1.8e+003     1000       
   Sediment  0.175           8.1e+003     0          
     Persistence Time: 890 hr


 Log Octanol-Water Partition Coef (SRC):
    Log Kow (KOWWIN v1.67 estimate) =  2.43
    Log Kow (Exper. database match) =  2.44
       Exper. Ref:  Hansch,C et al. (1995)

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  214.19  (Adapted Stein & Brown method)
    Melting Pt (deg C):  35.11  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  0.00398  (Modified Grain method)
    MP  (exp database):  180 deg C
    Subcooled liquid VP: 0.163 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):  6292
       log Kow used: 2.44 (expkow database)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  1764.4 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   8.32E-006  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  1.259E-007 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  2.44  (exp database)
  Log Kaw used:  -3.468  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  5.908
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.6454
   Biowin2 (Non-Linear Model)     :   0.5616
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.6772  (weeks-months)
   Biowin4 (Primary Survey Model) :   3.5194  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.5188
   Biowin6 (MITI Non-Linear Model):   0.3328
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model):  0.0774
 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):  21.7 Pa (0.163 mm Hg)
  Log Koa (Koawin est  ): 5.908
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  1.38E-007 
       Octanol/air (Koa) model:  1.99E-007 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  4.99E-006 
       Mackay model           :  1.1E-005 
       Octanol/air (Koa) model:  1.59E-005 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant =  40.3085 E-12 cm3/molecule-sec
      Half-Life =     0.265 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     3.184 Hrs
   Ozone Reaction:
      No Ozone Reaction Estimation
   Fraction sorbed to airborne particulates (phi): 8.01E-006 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  384.6
      Log Koc:  2.585 

 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 = 1.179 (BCF = 15.09)
       log Kow used: 2.44 (expkow database)

 Volatilization from Water:
    Henry LC:  8.32E-006 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River:       87.8  hours   (3.658 days)
    Half-Life from Model Lake :       1061  hours   (44.21 days)

 Removal In Wastewater Treatment:
    Total removal:               3.39  percent
    Total biodegradation:        0.10  percent
    Total sludge adsorption:     2.83  percent
    Total to Air:                0.46  percent
      (using 10000 hr Bio P,A,S)

 Level III Fugacity Model:
           Mass Amount    Half-Life    Emissions
            (percent)        (hr)       (kg/hr)
   Air       0.347           6.37         1000       
   Water     23.7            900          1000       
   Soil      75.8            1.8e+003     1000       
   Sediment  0.175           8.1e+003     0          
     Persistence Time: 890 hr




                    

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