ChemSpider 2D Image | Amisulpride | C17H27N3O4S

Amisulpride

  • Molecular FormulaC17H27N3O4S
  • Average mass369.479 Da
  • Monoisotopic mass369.172241 Da
  • ChemSpider ID2074

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275-831-7 [EINECS]
4960
4-Amino-N-[(1-ethyl-2-pyrrolidinyl)methyl]-5-(ethylsulfonyl)-2-methoxybenzamid [German] [ACD/IUPAC Name]
4-Amino-N-[(1-ethyl-2-pyrrolidinyl)methyl]-5-(ethylsulfonyl)-2-methoxybenzamide [ACD/IUPAC Name]
4-Amino-N-[(1-éthyl-2-pyrrolidinyl)méthyl]-5-(éthylsulfonyl)-2-méthoxybenzamide [French] [ACD/IUPAC Name]
4-Amino-N-[(1-ethyl-2-pyrrolidinyl)methyl]-5-(ethylsulfonyl)-o-anisamide
4-amino-N-[(1-ethylpyrrolidin-2-yl)methyl]-5-(ethylsulfonyl)-2-methoxybenzamide
71675-85-9 [RN]
8110R61I4U
amisulprida
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

CHEBI:64045 [DBID]
A2729_SIGMA [DBID]
DAN 2163 [DBID]
  • Experimental Physico-chemical Properties
  • Miscellaneous
    • Safety:

      5 Axon Medchem 1381
      GHS07 Biosynth W-104511
      H302 Biosynth W-104511
      H302 LKT Labs [A5234]
      H303;H313;H317;H333;H334;H335;H373 Axon Medchem 1381
      N05AL05 Wikidata Q418785
      no pictogram Axon Medchem 1381
      P101;P102;P103;P260;P262;P263;P264;P270;P280;P304;P312;P340 Axon Medchem 1381
      R22 LKT Labs [A5234]
      Warning Biosynth W-104511
      Warning Axon Medchem 1381
      Xn Abblis Chemicals AB1009624
      Xn LKT Labs [A5234]
    • Target Organs:

      Dopamine Receptor antagonist;5-HT receptor antagonist TargetMol T0811
    • Chemical Class:

      A member of the class of benzamides resulting from the formal condensation of the carboxy group of 4-amino-5-(ethylsulfonyl)-2-methoxybenzoic acid with the primary amino group of 2-(aminomethyl)-1-eth ylpyrrolidine. It is a potent, selective dopamine D<smallsub>2</smallsub> and D<smallsub>3</smallsub> receptor antagonist. It is an atypical antipsychotic/antischizophrenic agent with limited extrapyr imidal side effects. ChEBI CHEBI:64045
    • Bio Activity:

      7-TM Receptors Tocris Bioscience 2132
      Amisulpride(DAN 2163) is an antipsychotic drug, which is a selective dopamine antagonist (Ki=2.8 nM D2 receptor; Ki=3.2 nM D3 receptor). MedChem Express
      Amisulpride(DAN 2163) is an antipsychotic drug, which is a selective dopamine antagonist (Ki=2.8 nM D2 receptor; Ki=3.2 nM D3 receptor).; Target: D2/D3 receptor; Amisulpride is an atypical antipsychotic used to treat psychosis in schizophrenia and episodes of mania in bipolar disorder. MedChem Express HY-14545
      Amisulpride(DAN 2163) is an antipsychotic drug, which is a selective dopamine antagonist (Ki=2.8 nM D2 receptor; Ki=3.2 nM D3 receptor).;Target: D2/D3 receptorAmisulpride is an atypical antipsychotic used to treat psychosis in schizophrenia and episodes of mania in bipolar disorder. In small doses it is also used to treat depression. Amisulpride functions primarily as a D2 and D3 receptor antagonist. It has high affinity for these receptors with dissociation constants of 2.8 nM and 3.2 nM, respectively [1]. At low doses (< or = 10 mg/kg) amisulpride preferentially blocks presynaptic dopamine autoreceptors that control dopamine synthesis and release in the rat, whereas at higher doses (40-80 mg/kg) postsynaptic dopamine D2 receptor occupancy and antagonism is apparent. In contrast, haloperidol is active in all of these paradigms within the same dose range. Amisulpridepreferentially inhibits in vivo binding of the D2/D3 antagonist [3H]raclopride to the limbic system (ID50 = 17 mg/k MedChem Express HY-14545
      Antiemetic and spasmolytic agent; Zerenex Molecular [ZBioX-0107]
      Dopamine Receptor MedChem Express HY-14545
      Dopamine receptor;5-HT receptor TargetMol T0811
      Dopamine Receptors Tocris Bioscience 2132
      GPCR/G protein MedChem Express HY-14545
      GPCR/G protein; Neuronal Signaling; MedChem Express HY-14545
      Neuroscience TargetMol T0811
      Non-selective Dopamine Tocris Bioscience 2132
      Potent, selective dopamine D2 and D3 receptor antagonist. Ki values are 2.8 and 3.2 nM respectively for human D2 and D3 and > 1000 nM for human D1, D4 and D5 receptors. Shows selectivity for presynapt ic dopamine autoreceptors at low doses and blocks postsynaptic D2/D3 receptors at higher doses. Preferentially interacts with limbic D2-like receptors in vivo. Atypical antipsychotic/antischizophrenic agent with limited extrapyrimidal side effects and a profile distinct from that of haloperidol and remoxipride. Tocris Bioscience 2132
      Potent, selective dopamine D2 and D3 receptor antagonist. Ki values are 2.8 and 3.2 nM respectively for human D2 and D3 and > 1000 nM for human D1, D4 and D5 receptors. Shows selectivity for presynaptic dopamine autoreceptors at low doses and blocks postsynaptic D2/D3 receptors at higher doses. Preferentially interacts with limbic D2-like receptors in vivo. Atypical antipsychotic/antischizophrenic agent with limited extrapyrimidal side effects and a profile distinct from that of haloperidol and remoxipride. Tocris Bioscience 2132
      Selective D2/D3 receptor antagonist; atypical antipsychotic agent Tocris Bioscience 2132

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

Density: 1.2±0.1 g/cm3
Boiling Point: 558.9±50.0 °C at 760 mmHg
Vapour Pressure: 0.0±1.5 mmHg at 25°C
Enthalpy of Vaporization: 84.1±3.0 kJ/mol
Flash Point: 291.8±30.1 °C
Index of Refraction: 1.546
Molar Refractivity: 97.4±0.4 cm3
#H bond acceptors: 7
#H bond donors: 3
#Freely Rotating Bonds: 7
#Rule of 5 Violations: 0
ACD/LogP: 1.60
ACD/LogD (pH 5.5): -1.63
ACD/BCF (pH 5.5): 1.00
ACD/KOC (pH 5.5): 1.00
ACD/LogD (pH 7.4): -0.43
ACD/BCF (pH 7.4): 1.00
ACD/KOC (pH 7.4): 2.07
Polar Surface Area: 110 Å2
Polarizability: 38.6±0.5 10-24cm3
Surface Tension: 45.0±3.0 dyne/cm
Molar Volume: 307.7±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) =  1.11
    Log Kow (Exper. database match) =  1.10
       Exper. Ref:  Mannhold,R et al. (1990)

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  564.86  (Adapted Stein & Brown method)
    Melting Pt (deg C):  242.90  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  5.93E-011  (Modified Grain method)
    MP  (exp database):  126-127 deg C
    Subcooled liquid VP: 6.03E-010 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):  542.5
       log Kow used: 1.10 (expkow database)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  1.2537e+005 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   2.12E-020  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  5.314E-014 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  1.10  (exp database)
  Log Kaw used:  -18.062  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  19.162
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.4747
   Biowin2 (Non-Linear Model)     :   0.1934
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   1.8806  (months      )
   Biowin4 (Primary Survey Model) :   3.2008  (weeks       )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :  -0.0702
   Biowin6 (MITI Non-Linear Model):   0.0029
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -1.5786
 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):  8.04E-008 Pa (6.03E-010 mm Hg)
  Log Koa (Koawin est  ): 19.162
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  37.3 
       Octanol/air (Koa) model:  3.56E+006 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.999 
       Mackay model           :  1 
       Octanol/air (Koa) model:  1 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant = 319.4615 E-12 cm3/molecule-sec
      Half-Life =     0.033 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =    24.107 Min
   Ozone Reaction:
      No Ozone Reaction Estimation
   Fraction sorbed to airborne particulates (phi): 0.999 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  637.3
      Log Koc:  2.804 

 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 = 0.147 (BCF = 1.403)
       log Kow used: 1.10 (expkow database)

 Volatilization from Water:
    Henry LC:  2.12E-020 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 5.309E+016  hours   (2.212E+015 days)
    Half-Life from Model Lake : 5.791E+017  hours   (2.413E+016 days)

 Removal In Wastewater Treatment:
    Total removal:               1.90  percent
    Total biodegradation:        0.09  percent
    Total sludge adsorption:     1.80  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       2.36e-011       0.804        1000       
   Water     41.9            1.44e+003    1000       
   Soil      58              2.88e+003    1000       
   Sediment  0.0918          1.3e+004     0          
     Persistence Time: 1.32e+003 hr




                    

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