ChemSpider 2D Image | metoclopramide | C14H22ClN3O2

metoclopramide

  • Molecular FormulaC14H22ClN3O2
  • Average mass299.796 Da
  • Monoisotopic mass299.140045 Da
  • ChemSpider ID4024

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

1740
206-662-9 [EINECS]
364-62-5 [RN]
4-Amino-5-chlor-N-[2-(diethylamino)ethyl]-2-methoxybenzamid [German] [ACD/IUPAC Name]
4-Amino-5-chlor-N-[2-(diethylamino)ethyl]-2-methoxybenzolcarboximidsäure [German] [ACD/IUPAC Name]
4-Amino-5-chloro-N-[2-(diethylamino)ethyl]-2-methoxybenzamide [ACD/IUPAC Name]
4-Amino-5-chloro-N-[2-(diéthylamino)éthyl]-2-méthoxybenzamide [French] [ACD/IUPAC Name]
4-Amino-5-chloro-N-[2-(diethylamino)ethyl]-2-methoxybenzenecarboximidic acid [ACD/IUPAC Name]
Acide 4-amino-5-chloro-N-[2-(diéthylamino)éthyl]-2-méthoxybenzènecarboximidique [French] [ACD/IUPAC Name]
Benzamide, 4-amino-5-chloro-N-(2-(diethylamino)ethyl)-2-methoxy-
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

BRN 1884366 [DBID]
C07868 [DBID]
D00726 [DBID]
DEL 1267 [DBID]
DivK1c_000069 [DBID]
KBio1_000069 [DBID]
KBio2_002118 [DBID]
KBio2_004686 [DBID]
KBio2_007254 [DBID]
KBio3_001527 [DBID]
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  • Experimental Physico-chemical Properties
  • Miscellaneous
    • Safety:

      A03FA01 Wikidata Q421095
    • Chemical Class:

      A member of the class of benzamides resulting from the formal condensation of 4-amino-5-chloro-2-methoxybenzoic acid with the primary amino group of <element>N</element>,<element>N</element>-diethyle thane-1,2-diamine. ChEBI CHEBI:107736
    • Drug Status:

      approved BIONET-Key Organics KS-5055
    • Bio Activity:

      Dopamine Receptor MedChem Express HY-17382
      GPCR/G protein MedChem Express HY-17382
      GPCR/G protein; Neuronal Signaling; MedChem Express HY-17382
      Metoclopramide is a dopamine D2 antagonist that is used as an antiemetic. MedChem Express
      Metoclopramide is a dopamine D2 antagonist that is used as an antiemetic.; IC50 Value:; Target: D2 Receptor; Metoclopramide is a dopamine receptor antagonist which has been used for treatment of a variety of gastrointestinal symptoms over the last thirty years. MedChem Express HY-17382
      Metoclopramide is a dopamine D2 antagonist that is used as an antiemetic.;IC50 Value:;Target: D2 ReceptorMetoclopramide is a dopamine receptor antagonist which has been used for treatment of a variety of gastrointestinal symptoms over the last thirty years. In various countries, metoclopramide is the antiemetic drug of choice in pregnant women. Findings provide reassurance regarding the safety of metoclopramide for the fetus when the drug is given to women to relieve nausea and vomiting during pregnancy. Evidence also supports its use for gastroparesis (poor stomach emptying) and gastroesophageal reflux disease. It appears to bind to dopamine D2 receptors where it is a receptor antagonist, and is also a mixed 5-HT3 receptor antagonist/ 5-HT4 receptor agonist. MedChem Express HY-17382
  • Gas Chromatography
    • Retention Index (Kovats):

      2520 (estimated with error: 89) NIST Spectra mainlib_160689, replib_246767, replib_379664, replib_194482, replib_246775, replib_248027
      2650 (Program type: Isothermal; Col... (show more) umn class: Standard non-polar; Column length: 2 m; Column type: Packed; Start T: 260 C; CAS no: 364625; 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
      2624 (Program type: Isothermal; Col... (show more) umn class: Standard non-polar; Column diameter: 0.20 mm; Column length: 25 m; Column type: Capillary; Start T: 250 C; CAS no: 364625; Active phase: SPB-1; Carrier gas: He; Data type: Kovats RI; Authors: Lora-Tamayo, C.; Rams, M.A.; Chacon, J.M.R., Gas Chromatographic Data for 187 Nitrogen- or Phosphorus-Containing Drugs and Metabolites of Toxicological Interest Analysed on Methyl Silicone Capillary Columns, J. Chromatogr., 374, 1986, 73-85.) NIST Spectra nist ri
    • Retention Index (Normal Alkane):

      2617.6 (Program type: Ramp; Column cl... (show more) ass: Standard non-polar; Column diameter: 0.32 mm; Column length: 12 m; Column type: Capillary; Heat rate: 10 K/min; Start T: 40 C; End T: 290 C; Start time: 1 min; CAS no: 364625; Active phase: SE-30; Carrier gas: He; Phase thickness: 0.25 um; Data type: Normal alkane RI; Authors: Neill, G.P.; Davies, N.W.; McLean, S., Automated screening procedure using gas chromatography-mass spectrometry for identification of drugs after their extraction from biological samples, J. Chromatogr., 565, 1991, 207-224.) NIST Spectra nist ri
      2630 (Program type: Ramp; Column cl... (show more) ass: Standard non-polar; Column type: Other; CAS no: 364625; 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
      2611.6 (Program type: Ramp; Column cl... (show more) ass: Semi-standard non-polar; Column diameter: 0.25 mm; Column length: 30 m; Column type: Capillary; Heat rate: 5 K/min; Start T: 70 C; End T: 320 C; End time: 5 min; Start time: 0.5 min; CAS no: 364625; Active phase: BPX-5; Phase thickness: 0.25 um; Data type: Normal alkane RI; Authors: Song, S.M.; Marriott, P.; Wynne, P., Comprehensive two-dimensional gas chromatography-quadrupole mass spectrometric analysis of drugs, J. Chromatogr. A, 1058, 2004, 223-232.) NIST Spectra nist ri
      2648.5 (Program type: Complex; Column... (show more) class: Semi-standard non-polar; Column diameter: 0.32 mm; Column length: 15 m; Column type: Capillary; Description: 100 0C (0.4 min) ^ 25 0C/min -> 200 0C ^ 10 0C/min -> 290 0C (10 min); CAS no: 364625; 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
      2626.7 (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: 364625; 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):

      2602 (Program type: Complex; Column... (show more) class: Standard non-polar; Column diameter: 0.22 mm; Column length: 12 m; Column type: Capillary; Description: 120C=>8C/min=>270C=>25C/min=>300C; CAS no: 364625; Active phase: BP-1; Carrier gas: He; Phase thickness: 0.25 um; Data type: Linear RI; Authors: Stowell, A.; Wilson, L.W., A simple approach to the interlaboratory transfer of drug retention indices determined by temperature programmed capillary gas chromatography, J. Forensic Sci., 32(5), 1987, 1214-1220.) NIST Spectra nist ri
      2630 (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: 364625; 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: 1.2±0.1 g/cm3
Boiling Point: 418.7±45.0 °C at 760 mmHg
Vapour Pressure: 0.0±1.0 mmHg at 25°C
Enthalpy of Vaporization: 67.2±3.0 kJ/mol
Flash Point: 207.0±28.7 °C
Index of Refraction: 1.554
Molar Refractivity: 82.6±0.3 cm3
#H bond acceptors: 5
#H bond donors: 3
#Freely Rotating Bonds: 7
#Rule of 5 Violations: 0
ACD/LogP: 2.22
ACD/LogD (pH 5.5): -0.60
ACD/BCF (pH 5.5): 1.00
ACD/KOC (pH 5.5): 1.00
ACD/LogD (pH 7.4): 0.55
ACD/BCF (pH 7.4): 1.00
ACD/KOC (pH 7.4): 6.74
Polar Surface Area: 68 Å2
Polarizability: 32.7±0.5 10-24cm3
Surface Tension: 43.8±3.0 dyne/cm
Molar Volume: 257.8±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) =  1.69
    Log Kow (Exper. database match) =  2.62
       Exper. Ref:  Hansch,C et al. (1995)

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  460.16  (Adapted Stein & Brown method)
    Melting Pt (deg C):  193.99  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  1.58E-008  (Modified Grain method)
    MP  (exp database):  147.25 deg C
    Subcooled liquid VP: 2.75E-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):  71.25
       log Kow used: 2.62 (expkow database)
       no-melting pt equation used
     Water Sol (Exper. database match) =  200 mg/L (25 deg C)
        Exper. Ref:  MERCK (1989)

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  11832 mg/L
    Wat Sol (Exper. database match) =  200.00
       Exper. Ref:  MERCK (1989)

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   8.74E-017  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  8.748E-011 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  2.62  (exp database)
  Log Kaw used:  -14.447  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  17.067
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.3254
   Biowin2 (Non-Linear Model)     :   0.0791
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   1.8280  (months      )
   Biowin4 (Primary Survey Model) :   3.1360  (weeks       )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.1211
   Biowin6 (MITI Non-Linear Model):   0.0149
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -1.6343
 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):  3.67E-005 Pa (2.75E-007 mm Hg)
  Log Koa (Koawin est  ): 17.067
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  0.0818 
       Octanol/air (Koa) model:  2.86E+004 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.747 
       Mackay model           :  0.867 
       Octanol/air (Koa) model:  1 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant = 305.4308 E-12 cm3/molecule-sec
      Half-Life =     0.035 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =    25.214 Min
   Ozone Reaction:
      No Ozone Reaction Estimation
   Fraction sorbed to airborne particulates (phi): 0.807 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  373.7
      Log Koc:  2.573 

 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 = 1.317 (BCF = 20.77)
       log Kow used: 2.62 (expkow database)

 Volatilization from Water:
    Henry LC:  8.74E-017 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River:  1.16E+013  hours   (4.833E+011 days)
    Half-Life from Model Lake : 1.265E+014  hours   (5.272E+012 days)

 Removal In Wastewater Treatment:
    Total removal:               3.49  percent
    Total biodegradation:        0.11  percent
    Total sludge adsorption:     3.38  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       1.07e-009       0.84         1000       
   Water     13.4            1.44e+003    1000       
   Soil      86.5            2.88e+003    1000       
   Sediment  0.145           1.3e+004     0          
     Persistence Time: 2.46e+003 hr




                    

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