ChemSpider 2D Image | cyproheptadine | C21H21N

cyproheptadine

  • Molecular FormulaC21H21N
  • Average mass287.398 Da
  • Monoisotopic mass287.167389 Da
  • ChemSpider ID2810

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129-03-3 [RN]
1-Methyl 1-(5H-dibenzo[a,d]cycloheptenylidene)piperidine
1-Methyl-4-(5-dibenzo[a,e]cycloheptatrienylidene)piperidine
204-928-9 [EINECS]
2YHB6175DO
4-(5H-Dibenzo[a,d][7]annulen-5-yliden)-1-methylpiperidin [German] [ACD/IUPAC Name]
4-(5H-Dibenzo[a,d][7]annulen-5-ylidene)-1-methylpiperidine [ACD/IUPAC Name]
4-(5H-Dibenzo[a,d][7]annulén-5-ylidène)-1-méthylpipéridine [French] [ACD/IUPAC Name]
4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-methylpiperidine
4-Dibenzo[a,d]cyclohepten-5-ylidene-1-methyl-piperidine
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

AIDS001635 [DBID]
AIDS-001635 [DBID]
BRN 1685976 [DBID]
C06935 [DBID]
CCRIS 5232 [DBID]
HSDB 3048 [DBID]
Lopac-C-6022 [DBID]
MK 141 [DBID]
NCGC00015252-01 [DBID]
NCGC00015252-02 [DBID]
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  • Experimental Physico-chemical Properties
  • Miscellaneous
    • Safety:

      R06AX02 Wikidata Q417884
    • Chemical Class:

      The product resulting from the formal oxidative coupling of position 5 of 5<element>H</element>-dibenzo[<ital>a</ital>,<ital>d</ital>]cycloheptene with position 4 of 1-methylpiperidine resulting in th e formation of a double bond between the two fragments. It is a sedating antihistamine with antimuscarinic and calcium-channel blocking actions. It is used (particularly as the hydrochloride sesquihyd rate) for the relief of allergic conditions including rhinitis, conjunctivitis due to inhalant allergens and foods, urticaria and angioedema, and in pruritic skin disorders. Unlike other antihistamine s, it is also a seratonin receptor antagonist, making it useful in conditions such as vascular headache and anorexia. ChEBI CHEBI:4046
    • Bio Activity:

      Antihistaminic and antiserotonergic agent Zerenex Molecular [ZBioX-0643]
  • Gas Chromatography
    • Retention Index (Kovats):

      2489 (estimated with error: 83) NIST Spectra mainlib_250706, replib_246696, replib_248054, replib_312947, replib_379484
      2340 (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: 129033; 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
      2356 (Program type: Isothermal; Col... (show more) umn class: Standard non-polar; Column length: 2 m; Column type: Packed; Start T: 240 C; CAS no: 129033; 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
      2400 (Program type: Isothermal; Col... (show more) umn class: Standard non-polar; Column length: 6 ft; Column type: Packed; CAS no: 129033; 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):

      2348.4 (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: 129033; 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
      2360.4 (Program type: Ramp; Column cl... (show more) ass: Standard non-polar; Column diameter: 0.26 mm; Column length: 30 m; Column type: Capillary; Heat rate: 8 K/min; Start T: 120 C; End T: 280 C; End time: 22 min; Start time: 1 min; CAS no: 129033; Active phase: DB-1; Carrier gas: He; Phase thickness: 0.25 um; Data type: Normal alkane RI; Authors: Manca, D.; Ferron, L.; Weber, J-P., A System for Toxicological Screening by Capillary Gas Chromatography with Use of Drug Retention Index Based on Nitrogen-Containing Reference Compounds, Clin. Chem., 35(4), 1989, 601-607.) NIST Spectra nist ri
      2366 (Program type: Ramp; Column cl... (show more) ass: Standard non-polar; Column type: Capillary; CAS no: 129033; 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: 129033; 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
      2355 (Program type: Ramp; Column cl... (show more) ass: Standard non-polar; Column length: 2 m; Column type: Packed; Heat rate: 5 K/min; Start T: 150 C; End T: 300 C; CAS no: 129033; Active phase: OV-1; Substrate: Gas Chrom P; Data type: Normal alkane RI; Authors: Marozzi, E.; Gambaro, V.; Saligari, E.; Mariani, R.; Lodi, F., Use of the retention index in gas chromatographic studies of drugs, J. Anal. Toxicol., 6, 1982, 185-192.) NIST Spectra nist ri
      2360 (Program type: Ramp; Column cl... (show more) ass: Standard non-polar; Column length: 2 m; Column type: Packed; Heat rate: 5 K/min; Start T: 150 C; End T: 300 C; CAS no: 129033; Active phase: SE-30; Substrate: Gas Chrom P; Data type: Normal alkane RI; Authors: Marozzi, E.; Gambaro, V.; Saligari, E.; Mariani, R.; Lodi, F., Use of the retention index in gas chromatographic studies of drugs, J. Anal. Toxicol., 6, 1982, 185-192.) 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: 129033; 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
      2357.6 (Program type: Ramp; Column cl... (show more) ass: Semi-standard non-polar; Column diameter: 0.53 mm; Column length: 15 m; Column type: Capillary; Heat rate: 15 K/min; Start T: 90 C; End T: 320 C; CAS no: 129033; Active phase: DB-5; Carrier gas: He; Phase thickness: 1.5 um; Data type: Normal alkane RI; Authors: Takeda, A.; Tanaka, H.; Shinohara, T.; Ohtake, I., Systematic analysis of acid, neutral and basic drugs in horse plasma by combination of solid-phase extraction, non-aqueous partitioning and gas chromatography-mass spectrometry, J. Chromatogr. B, 758, 2001, 235-248.) NIST Spectra nist ri
    • Retention Index (Linear):

      2333 (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: 129033; 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
      2355 (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: 129033; 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: 440.1±45.0 °C at 760 mmHg
Vapour Pressure: 0.0±1.1 mmHg at 25°C
Enthalpy of Vaporization: 69.7±3.0 kJ/mol
Flash Point: 194.5±25.6 °C
Index of Refraction: 1.630
Molar Refractivity: 91.6±0.3 cm3
#H bond acceptors: 1
#H bond donors: 0
#Freely Rotating Bonds: 0
#Rule of 5 Violations: 1
ACD/LogP: 6.41
ACD/LogD (pH 5.5): 2.11
ACD/BCF (pH 5.5): 4.70
ACD/KOC (pH 5.5): 15.39
ACD/LogD (pH 7.4): 3.51
ACD/BCF (pH 7.4): 115.65
ACD/KOC (pH 7.4): 378.98
Polar Surface Area: 3 Å2
Polarizability: 36.3±0.5 10-24cm3
Surface Tension: 45.7±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) =  5.17
    Log Kow (Exper. database match) =  4.69
       Exper. Ref:  Sangster (1993)

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  403.56  (Adapted Stein & Brown method)
    Melting Pt (deg C):  150.31  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  9.29E-007  (Modified Grain method)
    MP  (exp database):  112.8 deg C
    Subcooled liquid VP: 6.81E-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):  1.135
       log Kow used: 4.69 (expkow database)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  1.9843 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   9.20E-009  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  3.095E-007 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  4.69  (exp database)
  Log Kaw used:  -6.425  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  11.115
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.4055
   Biowin2 (Non-Linear Model)     :   0.0357
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.3092  (weeks-months)
   Biowin4 (Primary Survey Model) :   3.1451  (weeks       )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :  -0.0703
   Biowin6 (MITI Non-Linear Model):   0.0097
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -1.7089
 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):  0.000908 Pa (6.81E-006 mm Hg)
  Log Koa (Koawin est  ): 11.115
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  0.0033 
       Octanol/air (Koa) model:  0.032 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.107 
       Mackay model           :  0.209 
       Octanol/air (Koa) model:  0.719 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant = 260.7774 E-12 cm3/molecule-sec
      Half-Life =     0.041 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =    29.531 Min
   Ozone Reaction:
      OVERALL Ozone Rate Constant =  1089.899902 E-17 cm3/molecule-sec
      Half-Life =     0.001 Days (at 7E11 mol/cm3)
      Half-Life =      1.514 Min
   Fraction sorbed to airborne particulates (phi): 0.158 (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 = 2.911 (BCF = 815.3)
       log Kow used: 4.69 (expkow database)

 Volatilization from Water:
    Henry LC:  9.2E-009 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 1.079E+005  hours   (4495 days)
    Half-Life from Model Lake : 1.177E+006  hours   (4.905E+004 days)

 Removal In Wastewater Treatment:
    Total removal:              65.52  percent
    Total biodegradation:        0.59  percent
    Total sludge adsorption:    64.93  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       0.000936        0.0246       1000       
   Water     14.1            900          1000       
   Soil      69.6            1.8e+003     1000       
   Sediment  16.3            8.1e+003     0          
     Persistence Time: 1.25e+003 hr




                    

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