ChemSpider 2D Image | Pizotifen | C19H21NS

Pizotifen

  • Molecular FormulaC19H21NS
  • Average mass295.442 Da
  • Monoisotopic mass295.139465 Da
  • ChemSpider ID25497

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0BY8440V3N
15574-96-6 [RN]
239-632-9 [EINECS]
2693
4-(1-Methyl-4-piperidylidene)-9,10-dihydro-4H-benzo[4,5]cyclohepta[1,2-b]thiophene
4-(9,10-Dihydro-4H-benzo[4,5]cyclohepta[1,2-b]thien-4-ylidene)-1-methylpiperidine
4-(9,10-Dihydro-4H-benzo[4,5]cyclohepta[1,2-b]thiophen-4-yliden)-1-methylpiperidin [German] [ACD/IUPAC Name]
4-(9,10-Dihydro-4H-benzo[4,5]cyclohepta[1,2-b]thiophen-4-ylidene)-1-methylpiperidine [ACD/IUPAC Name]
4-(9,10-Dihydro-4H-benzo[4,5]cyclohepta[1,2-b]thiophén-4-ylidène)-1-méthylpipéridine [French] [ACD/IUPAC Name]
Piperidine, 4-(9,10-dihydro-4H-benzo(4,5)cyclohepta(1,2-b)thien-4-ylidene)-1-methyl-
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

BC 105 [DBID]
BRN 0753534 [DBID]
NSC291564 [DBID]
  • Experimental Physico-chemical Properties
  • Miscellaneous
    • Safety:

      GHS07; GHS08 Biosynth W-108016
      H302; H361 Biosynth W-108016
      P281 Biosynth W-108016
      Warning Biosynth W-108016
    • Target Organs:

      5-HT Receptor antagonist TargetMol T1442
    • Chemical Class:

      A benzocycloheptathiophene that is 9,10-dihydro-4<element>H</element>-benzo[4,5]cyclohepta[1,2-<ital>b</ital>]thiophene 4-ylidene)-1-methylpiperidine which is joined from the 4 position to the 4 posit ion of an <element>N</element>-methylpiperidine moiety by a double bond. It is a sedating antihistamine, with strong serotonin antagonist and weak antimuscarinic activity. It is generally used as the malate salt for the treatment of migraine and the prevention of headache attacks during cluster periods. ChEBI CHEBI:50212
    • Bio Activity:

      5-HT Receptor MedChem Express HY-B0115
      5-HT Receptor TargetMol T1442
      GPCR/G protein MedChem Express HY-B0115
      GPCR/G protein; Neuronal Signaling; MedChem Express HY-B0115
      Neuroscience TargetMol T1442
      Pizotifen(Pizotyline) is a highly selective 5-HT receptor blocking agent, which is a benzocycloheptane based drug. MedChem Express
      Pizotifen(Pizotyline) is a highly selective 5-HT receptor blocking agent, which is a benzocycloheptane based drug.; Target: 5-HT receptor; Pizotifen, is a benzocycloheptane based drug used as a medicine, primarily as a preventative to reduce the frequency of recurrent migraine headaches [1]. MedChem Express HY-B0115
      Pizotifen(Pizotyline) is a highly selective 5-HT receptor blocking agent, which is a benzocycloheptane based drug.;Target: 5-HT receptorPizotifen, is a benzocycloheptane based drug used as a medicine, primarily as a preventative to reduce the frequency of recurrent migraine headaches [1]. Pizotifen proved to be a highly selective 5-HT receptor blocking agent both in vivo (on saphenous veins) and in vitro (on saphenous veins and basilar arteries) from dogs and humans [2].;Three groups of pregnant mice were treated daily with oral doses (0.24, 0.6 and 1.2 mg/kg) of pipethiadene and pizotifen from day 4 to day 16 of gestation. The following parameters were investigated: reproductive health of the dams, external, skeletal and visceral malformations of fetuses and frequencies of micronuclei and chromosome aberrations in bone marrow cells of dams. Oral administration of Pipethiadene or Pizotifen produced no teratogenic effects. However, the significant reduction of fetal weight after al MedChem Express HY-B0115
  • Gas Chromatography
    • Retention Index (Kovats):

      2484 (estimated with error: 89) NIST Spectra mainlib_246719, replib_123421, replib_247178
      2367 (Program type: Isothermal; Col... (show more) umn class: Standard non-polar; Column length: 2 m; Column type: Packed; Start T: 240 C; CAS no: 15574966; 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
      2412 (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: 15574966; 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):

      2358.3 (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: 15574966; 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
      2375 (Program type: Ramp; Column cl... (show more) ass: Standard non-polar; Column type: Capillary; CAS no: 15574966; Active phase: Polydimethyl siloxanes; Data type: Normal alkane RI; Authors: Schutz, H.; Wollrab A., The significance of the retention index in toxicologic analysis II, Pharmazie in unzerer Zeit, 17(4), 1988, 97-101., Program type: Ramp; Column cl... (show more) ass: Standard non-polar; Column type: Other; CAS no: 15574966; 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

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

Density: 1.2±0.1 g/cm3
Boiling Point: 436.7±45.0 °C at 760 mmHg
Vapour Pressure: 0.0±1.0 mmHg at 25°C
Enthalpy of Vaporization: 69.3±3.0 kJ/mol
Flash Point: 217.9±28.7 °C
Index of Refraction: 1.631
Molar Refractivity: 90.4±0.3 cm3
#H bond acceptors: 1
#H bond donors: 0
#Freely Rotating Bonds: 0
#Rule of 5 Violations: 1
ACD/LogP: 6.13
ACD/LogD (pH 5.5): 2.01
ACD/BCF (pH 5.5): 3.85
ACD/KOC (pH 5.5): 13.12
ACD/LogD (pH 7.4): 3.34
ACD/BCF (pH 7.4): 81.88
ACD/KOC (pH 7.4): 278.63
Polar Surface Area: 31 Å2
Polarizability: 35.8±0.5 10-24cm3
Surface Tension: 47.7±3.0 dyne/cm
Molar Volume: 253.7±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) =  5.20

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  407.75  (Adapted Stein & Brown method)
    Melting Pt (deg C):  163.65  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  2.02E-007  (Modified Grain method)
    Subcooled liquid VP: 5.38E-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):  0.3712
       log Kow used: 5.20 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  5.9504 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   2.57E-008  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  2.116E-007 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  5.20  (KowWin est)
  Log Kaw used:  -5.979  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  11.179
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.5110
   Biowin2 (Non-Linear Model)     :   0.0949
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.1418  (months      )
   Biowin4 (Primary Survey Model) :   2.9964  (weeks       )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :  -0.2344
   Biowin6 (MITI Non-Linear Model):   0.0045
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -1.6146
 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):  0.000717 Pa (5.38E-006 mm Hg)
  Log Koa (Koawin est  ): 11.179
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  0.00418 
       Octanol/air (Koa) model:  0.0371 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.131 
       Mackay model           :  0.251 
       Octanol/air (Koa) model:  0.748 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant = 218.6990 E-12 cm3/molecule-sec
      Half-Life =     0.049 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     0.587 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): 0.191 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  5.516E+005
      Log Koc:  5.742 

 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 = 3.307 (BCF = 2027)
       log Kow used: 5.20 (estimated)

 Volatilization from Water:
    Henry LC:  2.57E-008 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 3.916E+004  hours   (1632 days)
    Half-Life from Model Lake : 4.273E+005  hours   (1.781E+004 days)

 Removal In Wastewater Treatment:
    Total removal:              83.11  percent
    Total biodegradation:        0.71  percent
    Total sludge adsorption:    82.40  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       0.000499        0.0253       1000       
   Water     7.53            1.44e+003    1000       
   Soil      57.2            2.88e+003    1000       
   Sediment  35.3            1.3e+004     0          
     Persistence Time: 2.43e+003 hr




                    

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