ChemSpider 2D Image | Cinchocaine | C20H29N3O2

Cinchocaine

  • Molecular FormulaC20H29N3O2
  • Average mass343.463 Da
  • Monoisotopic mass343.225983 Da
  • ChemSpider ID2917

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

Nupercaine
108
201-632-1 [EINECS]
2-Butoxy-N-[2-(diethylamino)ethyl]-4-chinolincarboxamid [German] [ACD/IUPAC Name]
2-Butoxy-N-[2-(diethylamino)ethyl]-4-chinolincarboximidsäure [German] [ACD/IUPAC Name]
2-Butoxy-N-[2-(diéthylamino)éthyl]-4-quinoléinecarboxamide [French] [ACD/IUPAC Name]
2-Butoxy-N-[2-(diethylamino)ethyl]-4-quinolinecarboxamide [ACD/IUPAC Name]
2-Butoxy-N-[2-(diethylamino)ethyl]-4-quinolinecarboximidic acid [ACD/IUPAC Name]
2-Butoxy-N-[2-(diethylamino)ethyl]quinoline-4-carboxamide
4-Quinolinecarboxamide, 2-butoxy-N-(2-(diethylamino)ethyl)-
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

BAS 00401270 [DBID]
BRN 0275489 [DBID]
BRN 1914064 [DBID]
C07879 [DBID]
C14214 [DBID]
Caswell No. 292 [DBID]
CCRIS 2676 [DBID]
D00733 [DBID]
D0513_SIAL [DBID]
DivK1c_000332 [DBID]
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  • Experimental Physico-chemical Properties
  • Miscellaneous
    • Safety:

      C05AD04 Wikidata Q417603
      D04AB02 Wikidata Q417603
      Danger Biosynth Q-100863
      GHS05; GHS07 Biosynth Q-100863
      H302; H318 Biosynth Q-100863
      N01BB06 Wikidata Q417603
      P280; P305+P351+P338 Biosynth Q-100863
      S01HA06 Wikidata Q417603
      S02DA04 Wikidata Q417603
    • Target Organs:

      Calmodulin inhibitor;Sodium Channel inhibitor;ChE inhibitor TargetMol T0364
    • Chemical Class:

      A monocarboxylic acid amide that is the 2-(diethylamino)ethyl amide of 2-butoxyquinoline-4-carboxylic acid. One of the most potent and toxic of the long-acting local anesthetics, its parenteral use wa s restricted to spinal anesthesia. It is now generally only used (usually as the hydrochloride) in creams and ointments and in suppositories for temporary relief of pain and itching associated with sk in and anorectal conditions. ChEBI CHEBI:247956
    • Bio Activity:

      Calmodulin;Sodium channel;ChE TargetMol T0364
      Dibucaine is a local anesthetic of the amide type now generally used for surface anesthesia. MedChem Express
      Dibucaine is a local anesthetic of the amide type now generally used for surface anesthesia.; Target: Sodium Channel; Dibucaine is an amide local anesthetic. MedChem Express HY-B0552
      Dibucaine is a local anesthetic of the amide type now generally used for surface anesthesia.;Target: Sodium ChannelDibucaine is an amide local anesthetic. Dibucaine reduced the degradation of BSA-gold complex in the reservosomes, which was not caused either by an inhibition of the whole proteolytic activity of the parasite or by a reduction on the expression levels of cruzipain [1].Dibucaine, a quaternary ammonium compound, inhibited SChE to a minimum within 2 min in a reversible manner. The inhibition was very potent. It had an IC(50) of 5.3 microM with BuTch or 3.8 microM with AcTch. The inhibition was competitive with respect to BuTch with a K(i) of 1.3 microM and a linear-mixed type (competitive/noncompetitive) with respect to AcTch with inhibition constants, K(i) and K(I) of 0.66 and 2.5 microM, respectively. Dibucaine possesses a butoxy side chain that is similar to the butryl group of BuTch and longer by an ethylene group from AcTch [2]. MedChem Express HY-B0552
      Membrane Tranporter/Ion Channel MedChem Express HY-B0552
      Membrane Tranporter/Ion Channel; MedChem Express HY-B0552
      Membrane Transporter/Ion Channel TargetMol T0364
      Sodium Channel MedChem Express HY-B0552
  • Gas Chromatography
    • Retention Index (Kovats):

      2872 (estimated with error: 89) NIST Spectra mainlib_191249, replib_247832, replib_379585, replib_250627
      2740 (Program type: Isothermal; Col... (show more) umn class: Standard non-polar; Column length: 6 ft; Column type: Packed; CAS no: 85790; 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):

      2701 (Program type: Ramp; Column cl... (show more) ass: Standard non-polar; Column type: Other; CAS no: 85790; 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
      2714.2 (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: 85790; 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
      2707.3 (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: 85790; 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
      2700.8 (Program type: Ramp; Column cl... (show more) ass: Semi-standard non-polar; Column diameter: 0.32 mm; Column length: 12.5 m; Column type: Capillary; Heat rate: 10 K/min; Start T: 110 C; End T: 290 C; End time: 6.5 min; Start time: 1 min; CAS no: 85790; Active phase: Ultra-2; Phase thickness: 0.5 um; Data type: Normal alkane RI; Authors: Watts, V.W.; Simonick, T.F., A retention index library for commonly encountered drugs and metabolites using tri-n-alkylamines as reference compounds, nitrogen-phosphorus detectors, and dual capillary chromatography, J. Anal. Toxicol., 11, 1987, 210-214.) NIST Spectra nist ri
    • Retention Index (Linear):

      2706 (Program type: Ramp; Column cl... (show more) ass: Standard non-polar; Column diameter: 0.75 mm; Column length: 30 m; Column type: Capillary; Heat rate: 10 K/min; Start T: 160 C; End T: 280 C; End time: 12 min; CAS no: 85790; Active phase: SPB-1; Carrier gas: He; Phase thickness: 1.0 um; Data type: Linear RI; Authors: Christ, D.W.; Noomano, P.; Rosas, M.; Rhone, D., Retention indices by wide-bore capillary gas chromatography with nitrogen-phosphorus detection, J. Anal. Toxicol., 12, 1988, 84-88.) NIST Spectra nist ri
      2677 (Program type: Ramp; Column cl... (show more) ass: Standard non-polar; Column diameter: 0.53 mm; Column length: 12 m; Column type: Capillary; Heat rate: 6 K/min; Start T: 120 C; End T: 250 C; CAS no: 85790; Active phase: CBP-1; Carrier gas: N2; Data type: Linear RI; Authors: Oyama, N.; Sano, T.; Syoyama, M.; Maeda, K., Studies on systematic analysis of poisonous compounds in forensic chemistry. II. Application of capillary column gas chromatography to substance identification by means of retention indices, Eisei Kagaku, 33(5), 1987, 342-348.) NIST Spectra nist ri
      2693 (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: 85790; 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: 85790; 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
      2690 (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: 85790; 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: 496.3±40.0 °C at 760 mmHg
Vapour Pressure: 0.0±1.3 mmHg at 25°C
Enthalpy of Vaporization: 76.4±3.0 kJ/mol
Flash Point: 254.0±27.3 °C
Index of Refraction: 1.558
Molar Refractivity: 103.3±0.3 cm3
#H bond acceptors: 5
#H bond donors: 1
#Freely Rotating Bonds: 10
#Rule of 5 Violations: 0
ACD/LogP: 3.87
ACD/LogD (pH 5.5): 0.64
ACD/BCF (pH 5.5): 1.00
ACD/KOC (pH 5.5): 2.21
ACD/LogD (pH 7.4): 1.76
ACD/BCF (pH 7.4): 4.47
ACD/KOC (pH 7.4): 29.24
Polar Surface Area: 54 Å2
Polarizability: 40.9±0.5 10-24cm3
Surface Tension: 42.7±3.0 dyne/cm
Molar Volume: 320.4±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) =  4.04
    Log Kow (Exper. database match) =  4.40
       Exper. Ref:  Hansch,C et al. (1995)

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  510.04  (Adapted Stein & Brown method)
    Melting Pt (deg C):  217.29  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  1.36E-010  (Modified Grain method)
    Subcooled liquid VP: 1.53E-008 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):  1.185
       log Kow used: 4.40 (expkow database)
       no-melting pt equation used
     Water Sol (Exper. database match) =  42 mg/L (21 deg C)
        Exper. Ref:  BEILSTEIN

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  448.68 mg/L
    Wat Sol (Exper. database match) =  42.00
       Exper. Ref:  BEILSTEIN

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   9.10E-016  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  5.187E-011 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  4.40  (exp database)
  Log Kaw used:  -13.429  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  17.829
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.8293
   Biowin2 (Non-Linear Model)     :   0.9365
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.3714  (weeks-months)
   Biowin4 (Primary Survey Model) :   3.6158  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.3156
   Biowin6 (MITI Non-Linear Model):   0.0866
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -1.4803
 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):  2.04E-006 Pa (1.53E-008 mm Hg)
  Log Koa (Koawin est  ): 17.829
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  1.47 
       Octanol/air (Koa) model:  1.66E+005 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.982 
       Mackay model           :  0.992 
       Octanol/air (Koa) model:  1 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant = 139.1549 E-12 cm3/molecule-sec
      Half-Life =     0.077 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     0.922 Hrs
   Ozone Reaction:
      No Ozone Reaction Estimation
   Fraction sorbed to airborne particulates (phi): 0.987 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  5.818E+004
      Log Koc:  4.765 

 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 = 2.688 (BCF = 487.5)
       log Kow used: 4.40 (expkow database)

 Volatilization from Water:
    Henry LC:  9.1E-016 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 1.192E+012  hours   (4.968E+010 days)
    Half-Life from Model Lake : 1.301E+013  hours   (5.42E+011 days)

 Removal In Wastewater Treatment:
    Total removal:              50.68  percent
    Total biodegradation:        0.48  percent
    Total sludge adsorption:    50.20  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       5.32e-007       1.84         1000       
   Water     10.2            900          1000       
   Soil      83.6            1.8e+003     1000       
   Sediment  6.12            8.1e+003     0          
     Persistence Time: 1.96e+003 hr




                    

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