ChemSpider 2D Image | prilocaine | C13H20N2O

prilocaine

  • Molecular FormulaC13H20N2O
  • Average mass220.311 Da
  • Monoisotopic mass220.157562 Da
  • ChemSpider ID4737

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Featured data source



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1641
211-957-0 [EINECS]
721-50-6 [RN]
N-(2-Methylphenyl)-2-(propylamino)propanamid
N-(2-méthylphényl)-2-(propylamino)propanamide
N-(2-Methylphenyl)-N2-propylalaninamid [German] [ACD/IUPAC Name]
N-(2-Methylphenyl)-N2-propylalaninamide [ACD/IUPAC Name]
N-(2-Méthylphényl)-N2-propylalaninamide [French] [ACD/IUPAC Name]
N-(2-methylphenyl)-N2-propylalaninamide
prilocaína [Spanish] [INN]
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

046O35D44R [DBID]
UNII:046O35D44R [DBID]
Astra 1512 [DBID]
Astra 1515 [DBID]
BRN 2108498 [DBID]
C07531 [DBID]
D00553 [DBID]
DivK1c_000846 [DBID]
HSDB 3386 [DBID]
KBio1_000846 [DBID]
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  • Experimental Physico-chemical Properties
  • Miscellaneous
    • Safety:

      N01BB04 Wikidata Q413598
      P261; P262 Biosynth Q-100809
    • Chemical Class:

      An amino acid amide in which <element>N</element>-propyl-<stereo>D</stereo><stereo>L</stereo>-alanine and 2-methylaniline have combined to form the amide bond; used as a local anaesthetic. ChEBI CHEBI:8404
    • Bio Activity:

      Others MedChem Express HY-B0137
      Prilocaine is a local anesthetic of the amino amide type.; Target: Others; Prilocaine is a local anesthetic of the amino amide type first prepared by Claes Tegner and Nils L?fgren. MedChem Express HY-B0137
  • Gas Chromatography
    • Retention Index (Kovats):

      1938 (estimated with error: 83) NIST Spectra mainlib_113845, replib_248005, replib_247229, replib_335318
      1822 (Program type: Isothermal; Col... (show more) umn class: Standard non-polar; Column type: Packed; Start T: 170 C; CAS no: 721506; Active phase: OV-101; Data type: Kovats RI; Authors: Delbeke, F.T.; Debackere, M.; Desmet, N., Detection of some local anaesthetics in horse urine and plasma by gas-liquid chromatography, J. Chromatogr., 206, 1981, 594-599.) NIST Spectra nist ri
      1829 (Program type: Isothermal; Col... (show more) umn class: Standard non-polar; Column type: Packed; Start T: 180 C; CAS no: 721506; Active phase: OV-101; Data type: Kovats RI; Authors: Delbeke, F.T.; Debackere, M.; Desmet, N., Detection of some local anaesthetics in horse urine and plasma by gas-liquid chromatography, J. Chromatogr., 206, 1981, 594-599.) NIST Spectra nist ri
      1800 (Program type: Isothermal; Col... (show more) umn class: Standard non-polar; Column length: 6 ft; Column type: Packed; CAS no: 721506; Active phase: OV-101; Carrier gas: N2; Substrate: Chromosorb W; Data type: Kovats RI; Authors: McLinden, V.J.; Stenhouse, A.M., A chromatography system for drug identification, Forensic Sci. Int., 13, 1979, 71-79.) NIST Spectra nist ri
    • Retention Index (Normal Alkane):

      1825 (Program type: Ramp; Column cl... (show more) ass: Standard non-polar; Column length: 2 m; Column type: Packed; Start T: 100 C; End T: 300 C; CAS no: 721506; Active phase: SE-30; Carrier gas: Nitrogen; Substrate: Chromosorb G AW DMCS (80-100 mesh); Data type: Normal alkane RI; Authors: MHA, Directorate of ForensicScience., Forensic Toxicology, 9999., Program type: Ramp; Column cl... (show more) ass: Standard non-polar; Column type: Other; CAS no: 721506; 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
      1841.2 (Program type: Complex; Column... (show more) class: Semi-standard non-polar; Column diameter: 0.32 mm; Column length: 15 m; Column type: Capillary; Description: 100 0C (0.4 min) ^ 25 0C/min -> 200 0C ^ 10 0C/min -> 290 0C (10 min); CAS no: 721506; Active phase: HG-5; Carrier gas: He; Phase thickness: 0.25 um; Data type: Normal alkane RI; Authors: Rasanen, I.; Kontinen, I.; Nokua, J.; Ojanpera, I.; Vuori, E., Precise gas chromatography with retention time locking in comprehensive toxicological screening for drugs in blood, J. Chromatogr. B, 788, 2003, 243-250.) NIST Spectra nist ri
      1842.5 (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: 721506; 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):

      1811 (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: 8 K/min; Start T: 120 C; End T: 280 C; End time: 5 min; CAS no: 721506; Active phase: DB-1; Carrier gas: He; Phase thickness: 0.25 um; Data type: Linear RI; Authors: Perrigo, B.J.; Ballantyne, D.J.; Peel, H.W., Condierations in developing a data base for drugs on a DBI capillary column, J. Can. Soc. Forensic Sci., 17(2), 1984, 41-49., Program type: Ramp; Column cl... (show more) ass: Standard non-polar; Column diameter: 0.32 mm; Column length: 15 m; Column type: Capillary; Heat rate: 8 K/min; Start T: 120 C; End T: 280 C; End time: 5 min; CAS no: 721506; Active phase: DB-1; Carrier gas: He; Phase thickness: 0.25 um; Data type: Linear RI; Authors: Perrigo, B.J.; Peel, H.W.; Ballantyne, D.J., Use of Dual-Column Fused-Silica Capillary Gas Chromatography in Combination with Detector Response Factors for Analytical Toxicology., J. Chromatogr., 341, 1985, 81-88.) NIST Spectra nist ri
      1800 (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: 721506; 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
      1840 (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: 721506; 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: 1.0±0.1 g/cm3
Boiling Point: 361.6±25.0 °C at 760 mmHg
Vapour Pressure: 0.0±0.8 mmHg at 25°C
Enthalpy of Vaporization: 60.7±3.0 kJ/mol
Flash Point: 134.3±23.3 °C
Index of Refraction: 1.543
Molar Refractivity: 67.4±0.3 cm3
#H bond acceptors: 3
#H bond donors: 2
#Freely Rotating Bonds: 5
#Rule of 5 Violations: 0
ACD/LogP: 1.74
ACD/LogD (pH 5.5): -0.33
ACD/BCF (pH 5.5): 1.00
ACD/KOC (pH 5.5): 1.79
ACD/LogD (pH 7.4): 1.33
ACD/BCF (pH 7.4): 4.76
ACD/KOC (pH 7.4): 80.85
Polar Surface Area: 41 Å2
Polarizability: 26.7±0.5 10-24cm3
Surface Tension: 38.5±3.0 dyne/cm
Molar Volume: 214.0±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) =  1.88
    Log Kow (Exper. database match) =  2.11
       Exper. Ref:  Hansch,C et al. (1995)

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  378.65  (Adapted Stein & Brown method)
    Melting Pt (deg C):  136.63  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  2.13E-005  (Modified Grain method)
    MP  (exp database):  37-38 deg C
    BP  (exp database):  159-162 @ 0.1 mm Hg deg C
    Subcooled liquid VP: 2.73E-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):  541
       log Kow used: 2.11 (expkow database)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  5895.2 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   7.18E-011  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  1.141E-008 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  2.11  (exp database)
  Log Kaw used:  -8.532  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  10.642
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   1.0613
   Biowin2 (Non-Linear Model)     :   0.9861
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.6077  (weeks-months)
   Biowin4 (Primary Survey Model) :   3.7101  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.3399
   Biowin6 (MITI Non-Linear Model):   0.1615
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -0.5810
 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):  0.00364 Pa (2.73E-005 mm Hg)
  Log Koa (Koawin est  ): 10.642
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  0.000824 
       Octanol/air (Koa) model:  0.0108 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.0289 
       Mackay model           :  0.0619 
       Octanol/air (Koa) model:  0.463 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant = 104.4189 E-12 cm3/molecule-sec
      Half-Life =     0.102 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     1.229 Hrs
   Ozone Reaction:
      No Ozone Reaction Estimation
   Fraction sorbed to airborne particulates (phi): 0.0454 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  712.8
      Log Koc:  2.853 

 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 = 0.925 (BCF = 8.408)
       log Kow used: 2.11 (expkow database)

 Volatilization from Water:
    Henry LC:  7.18E-011 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River:  1.21E+007  hours   (5.043E+005 days)
    Half-Life from Model Lake :  1.32E+008  hours   (5.502E+006 days)

 Removal In Wastewater Treatment:
    Total removal:               2.36  percent
    Total biodegradation:        0.10  percent
    Total sludge adsorption:     2.26  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       0.000662        2.46         1000       
   Water     21.2            900          1000       
   Soil      78.7            1.8e+003     1000       
   Sediment  0.0937          8.1e+003     0          
     Persistence Time: 1.47e+003 hr




                    

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