ChemSpider 2D Image | azatadine | C20H22N2

azatadine

  • Molecular FormulaC20H22N2
  • Average mass290.402 Da
  • Monoisotopic mass290.178314 Da
  • ChemSpider ID18709

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11-(1-Methyl-4-piperidinyliden)-6,11-dihydro-5H-benzo[5,6]cyclohepta[1,2-b]pyridin [German] [ACD/IUPAC Name]
11-(1-Methyl-4-piperidinylidene)-6,11-dihydro-5H-benzo[5,6]cyclohepta[1,2-b]pyridine [ACD/IUPAC Name]
11-(1-Méthyl-4-pipéridinylidène)-6,11-dihydro-5H-benzo[5,6]cyclohepta[1,2-b]pyridine [French] [ACD/IUPAC Name]
11-(1-Methylpiperidin-4-ylidene)-6,11-dihydro-5H-benzo[5,6]cyclohepta[1,2-b]pyridine
223-615-8 [EINECS]
2327
3964-81-6 [RN]
4-Aza-5-(N-methyl-4-piperidinylidene)-10,11-dihydro-5H-dibenzo[a,d]cycloheptene
5H-Benzo[5,6]cyclohepta[1,2-b]pyridine, 6,11-dihydro-11-(1-methyl-4-piperidinylidene)- [ACD/Index Name]
6,11-Dihydro-11-(1-methyl-4-piperidinylidene)-5H-benzo[5,6]cyclohepta[1,2-b]pyridine
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

94Z39NID6C [DBID]
Sch 10649 [DBID]
C07774 [DBID]
UNII:94Z39NID6C [DBID]
UNII-94Z39NID6C [DBID]
  • Experimental Physico-chemical Properties
  • Miscellaneous
    • Safety:

      R06AX09 Wikidata Q599160
    • Chemical Class:

      A benzo[5,6]cyclohepta[1,2-<ital>b</ital>]pyridine having a 1-methylpiperidin-4-ylidene group at the 11-position. ChEBI CHEBI:2946
    • Bio Activity:

      Azatadine is an histamine and cholinergic inhibitor with IC50 of 6.5 nM and 10 nM, respectively. MedChem Express
      Azatadine is an histamine and cholinergic inhibitor with IC50 of 6.5 nM and 10 nM, respectively.; Target: Histamine Receptor; Azatadine, a new antihistamine, was evaluated for its efficacy in 20 patients with chronic allergic rhinitis. MedChem Express HY-B0170
      Azatadine is an histamine and cholinergic inhibitor with IC50 of 6.5 nM and 10 nM, respectively.;Target: Histamine ReceptorAzatadine, a new antihistamine, was evaluated for its efficacy in 20 patients with chronic allergic rhinitis. Eighty percent of patients had symptomatic relief with a twice daily dosage of 2 mg. Sedation was volunteered as a side effect by six of the patients and was admitted by two further patients after specific questioning. A choice reaction time test gave slowing of motor function in these sedated patients. Four of the previously sedated patients experienced good symptomatic control with minimal sedation when the azatadine dose was reduced to 1 mg twice daily; slowing of motor function was not observed at this, the normal recommended dose.Azatadine delays the onset of dyspnea-induced by aerosolized histamine, acetylcholine and serotonin in the conscious guinea-pig with PD50 of 0.01 mg/kg, 0.739 mg/kg and 0.86 mg/kg. Azatadine protects conscious guinea-pig MedChem Express HY-B0170
      GPCR/G protein MedChem Express HY-B0170
      GPCR/G protein; Immunology/Inflammation; MedChem Express HY-B0170
      Histamine Receptor MedChem Express HY-B0170
  • Gas Chromatography
    • Retention Index (Kovats):

      2501 (estimated with error: 83) NIST Spectra mainlib_248317, replib_119057, replib_121370, replib_247184, replib_247206, replib_379425
      2375 (Program type: Ramp; Column cl... (show more) ass: Standard non-polar; Column diameter: 0.20 mm; Column length: 12 m; Column type: Capillary; Heat rate: 30 K/min; Start T: 100 C; End T: 310 C; End time: 5 min; Start time: 3 min; CAS no: 3964816; Active phase: Methyl Silicone; Carrier gas: He; Phase thickness: 0.33 um; Data type: Kovats RI; Authors: Maurer, H.; Pfleger, K., Identification and Differentiation of Alkylamine Antihistamines and Their Metabolites in Urine by Computerized Gas Chromatography-Mass Spectrometry, J. Chromatogr., 430, 1988, 31-41.) NIST Spectra nist ri
    • Retention Index (Normal Alkane):

      2372.8 (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: 3964816; 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
      2415 (Program type: Ramp; Column cl... (show more) ass: Standard non-polar; Column type: Other; CAS no: 3964816; 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
      2382 (Program type: Ramp; Column cl... (show more) ass: Standard non-polar; Column length: 2 m; Column type: Packed; Heat rate: 10 K/min; Start T: 220 C; End T: 270 C; CAS no: 3964816; Active phase: OV-101; Substrate: Chromosorb (100-120 mesh); Data type: Normal alkane RI; Authors: Cailleux, A.; Turcant, A.; Premel-Cabic, A.; Allain, P., Identification and Quantitation of Neutral and Basic Drugs in Blood By Gas Chromatography and Mass Spectrometry, J. Chromatogr. Sci., 19, 1981, 163-176.) NIST Spectra nist ri
      2405.7 (Program type: Ramp; Column cl... (show more) ass: Semi-standard non-polar; Column diameter: 0.53 mm; Column length: 12 m; Column type: Capillary; Heat rate: .5 K/min; Start T: 100 C; End T: 310 C; End time: 10 min; Start time: 2 min; CAS no: 3964816; Active phase: DB-5; Carrier gas: He; Phase thickness: 1.0 um; Data type: Normal alkane RI; Authors: Drummer, O.H.; Horomidis, S.; Kourtis, S.K.; Syrjanen, M.L.; Tippet, P., Capillary gas chromatographic drug screen for use in forensic toxicology, J. Anal. Toxicol., 18, 1994, 134-138.) NIST Spectra nist ri
    • Retention Index (Linear):

      2368 (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: 3964816; 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

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

Density: 1.1±0.1 g/cm3
Boiling Point: 450.1±45.0 °C at 760 mmHg
Vapour Pressure: 0.0±1.1 mmHg at 25°C
Enthalpy of Vaporization: 70.9±3.0 kJ/mol
Flash Point: 226.0±28.7 °C
Index of Refraction: 1.617
Molar Refractivity: 90.1±0.3 cm3
#H bond acceptors: 2
#H bond donors: 0
#Freely Rotating Bonds: 0
#Rule of 5 Violations: 0
ACD/LogP: 4.97
ACD/LogD (pH 5.5): 1.23
ACD/BCF (pH 5.5): 1.02
ACD/KOC (pH 5.5): 5.26
ACD/LogD (pH 7.4): 2.69
ACD/BCF (pH 7.4): 29.48
ACD/KOC (pH 7.4): 152.29
Polar Surface Area: 16 Å2
Polarizability: 35.7±0.5 10-24cm3
Surface Tension: 48.0±3.0 dyne/cm
Molar Volume: 257.5±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) =  4.20
    Log Kow (Exper. database match) =  3.59
       Exper. Ref:  BioByte (1995)

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  407.47  (Adapted Stein & Brown method)
    Melting Pt (deg C):  164.04  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  2.03E-007  (Modified Grain method)
    Subcooled liquid VP: 5.47E-006 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):  9.483
       log Kow used: 3.59 (expkow database)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  427.61 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   6.20E-011  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  8.180E-009 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  3.59  (exp database)
  Log Kaw used:  -8.596  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  12.186
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.3588
   Biowin2 (Non-Linear Model)     :   0.0214
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   1.9387  (months      )
   Biowin4 (Primary Survey Model) :   2.9849  (weeks       )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :  -0.2447
   Biowin6 (MITI Non-Linear Model):   0.0037
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -1.0689
 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):  0.000729 Pa (5.47E-006 mm Hg)
  Log Koa (Koawin est  ): 12.186
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  0.00411 
       Octanol/air (Koa) model:  0.377 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.129 
       Mackay model           :  0.248 
       Octanol/air (Koa) model:  0.968 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant = 208.6476 E-12 cm3/molecule-sec
      Half-Life =     0.051 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     0.615 Hrs
   Ozone Reaction:
      OVERALL Ozone Rate Constant =  1064.699951 E-17 cm3/molecule-sec
      Half-Life =     0.001 Days (at 7E11 mol/cm3)
      Half-Life =      1.550 Min
   Fraction sorbed to airborne particulates (phi): 0.188 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  1.017E+006
      Log Koc:  6.007 

 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 = 2.064 (BCF = 116)
       log Kow used: 3.59 (expkow database)

 Volatilization from Water:
    Henry LC:  6.2E-011 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 1.609E+007  hours   (6.705E+005 days)
    Half-Life from Model Lake : 1.756E+008  hours   (7.315E+006 days)

 Removal In Wastewater Treatment:
    Total removal:              15.25  percent
    Total biodegradation:        0.20  percent
    Total sludge adsorption:    15.04  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       0.000241        0.0253       1000       
   Water     10.7            1.44e+003    1000       
   Soil      88.1            2.88e+003    1000       
   Sediment  1.16            1.3e+004     0          
     Persistence Time: 2.28e+003 hr




                    

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