ChemSpider 2D Image | 3,4-Methylenedioxyamphetamine | C10H13NO2

3,4-Methylenedioxyamphetamine

  • Molecular FormulaC10H13NO2
  • Average mass179.216 Da
  • Monoisotopic mass179.094635 Da
  • ChemSpider ID1555

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3,4-Methylenedioxyamphetamine [Wiki]
(±)-3,4-(Methylenedioxy)amphetamine
(R,S)-3,4-Methylenedioxyamphetamine
1-(1,3-Benzodioxol-5-yl)-2-propanamin [German] [ACD/IUPAC Name]
1-(1,3-Benzodioxol-5-yl)-2-propanamine [ACD/IUPAC Name]
1-(1,3-Benzodioxol-5-yl)-2-propanamine [French] [ACD/IUPAC Name]
1-(1,3-benzodioxol-5-yl)propan-2-amine
1-(3,4-Methylenedioxyphenyl)-2-aminopropane
1,3-Benzodioxole-5-ethanamine, α-methyl- [ACD/Index Name]
1,3-Benzodioxole-5-ethanamine, α-methyl- (9CI)
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

EA 1299 [DBID]
AI3-24882 [DBID]
BRN 0150196 [DBID]
DEA No. 7400 [DBID]
DivK1c_000964 [DBID]
EA-1299 [DBID]
KBio1_000964 [DBID]
NINDS_000964 [DBID]
NSC27106 [DBID]
NSC9978 [DBID]
  • Gas Chromatography
    • Retention Index (Kovats):

      1515 (estimated with error: 89) NIST Spectra mainlib_352965, replib_125758, replib_248177, replib_250570, replib_313160, replib_335530
      1495 (Program type: Isothermal; Col... (show more) umn class: Standard non-polar; Column length: 2 m; Column type: Packed; Start T: 150 C; CAS no: 4764174; Active phase: OV-101; Carrier gas: N2; Data type: Kovats RI; Authors: Huber, J.F.K.; Kenndler, E.; Reich, G., Quantitation of the Information Content of Multi-Dimensional Gas Chromatography and Low- Resolution Mass Spectrometry in the Identification of Doping Drugs, J. Chromatogr., 172, 1979, 15-30.) NIST Spectra nist ri
      1484 (Program type: Isothermal; Col... (show more) umn class: Semi-standard non-polar; Column type: Packed; Start T: 160 C; CAS no: 4764174; Active phase: Apiezon L; Data type: Kovats RI; Authors: Huber, J.F.K.; Kenndler, E.; Reich, G., Quantitation of the Information Content of Multi-Dimensional Gas Chromatography and Low- Resolution Mass Spectrometry in the Identification of Doping Drugs, J. Chromatogr., 172, 1979, 15-30.) NIST Spectra nist ri
      1483 (Program type: Isothermal; Col... (show more) umn class: Semi-standard non-polar; Column type: Packed; Start T: 160 C; CAS no: 4764174; Active phase: Apiezon L; Substrate: Chromosorb W; Data type: Kovats RI; Authors: Donike, M.; Stratmann, D., Gas-chromatographische identifizierung von stimulantien der phenylathylaminreihe mit hilfe der retnetions-indices, Z. Anal. Chem., 279(2), 1976, 129-131.) NIST Spectra nist ri
      2204 (Program type: Isothermal; Col... (show more) umn class: Standard polar; Column type: Packed; Start T: 180 C; CAS no: 4764174; Active phase: PEG-20M; Carrier gas: N2; Data type: Kovats RI; Authors: Huber, J.F.K.; Kenndler, E.; Reich, G., Quantitation of the Information Content of Multi-Dimensional Gas Chromatography and Low- Resolution Mass Spectrometry in the Identification of Doping Drugs, J. Chromatogr., 172, 1979, 15-30., Program type: Isothermal; Col... (show more) umn class: Standard polar; Column type: Packed; Start T: 180 C; CAS no: 4764174; Active phase: PEG-20M; Substrate: Chromosorb W; Data type: Kovats RI; Authors: Donike, M.; Stratmann, D., Gas-chromatographische identifizierung von stimulantien der phenylathylaminreihe mit hilfe der retnetions-indices, Z. Anal. Chem., 279(2), 1976, 129-131.) NIST Spectra nist ri
    • Retention Index (Normal Alkane):

      1472 (Program type: Ramp; Column cl... (show more) ass: Standard non-polar; Column length: 2 m; Column type: Packed; Start T: 100 C; End T: 300 C; CAS no: 4764174; Active phase: SE-30; Carrier gas: Nitrogen; Substrate: Chromosorb G AW DMCS (80-100 mesh); Data type: Normal alkane RI; Authors: MHA, Directorate of ForensicScience., Forensic Toxicology, 9999., Program type: Ramp; Column cl... (show more) ass: Standard non-polar; Column type: Other; CAS no: 4764174; 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
      1480 (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: 10 K/min; Start T: 160 C; End T: 300 C; CAS no: 4764174; Active phase: Polymethylsiloxane, (PMS-20000); Carrier gas: He; Phase thickness: 0.33 um; Data type: Normal alkane RI; Authors: Gambaro, V.; Saligari, E.; Froldi, R.; Bianchi, L., Analysis of street drugs by means of HRGC, Bollettino Chimico Farmaceutica, 36(4), 1997, 359-367.) NIST Spectra nist ri
      1464.6 (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: 4764174; 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
      1460 (Program type: Ramp; Column cl... (show more) ass: Standard non-polar; Column length: 6 ft; 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: 4764174; Active phase: SE-30; Carrier gas: N2; Substrate: Chromosorb W AW DMS; Data type: Normal alkane RI; Authors: Peel, H.W.; Perrigo, B., A practical gas chromatographic screening procedure for toxicological analysis, Can.Soc.Forens.Sci.J., 9(2), 1975, 69-74., Program type: Ramp; Column cl... (show more) ass: Standard non-polar; Column length: 6 ft; 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: 4764174; Active phase: SE-30; Carrier gas: Nitrogen; Substrate: Chromosorb W AW DMS (80-100 mesh); Data type: Normal alkane RI; Authors: Peel, H.W.; Perrigo, B., A practical gas chromatographic screening procedure for toxicological analysis, Can. Soc. Forens. Sci. J., 9(2), 1976, 69-74.) NIST Spectra nist ri
      1496.3 (Program type: Ramp; Column cl... (show more) ass: Semi-standard non-polar; Column diameter: 0.32 mm; Column length: 15 m; Column type: Capillary; Heat rate: 15 K/min; Start T: 100 C; End T: 280 C; End time: 5 min; CAS no: 4764174; Active phase: DB-5MS; Carrier gas: He; Phase thickness: 0.25 um; Data type: Normal alkane RI; Authors: Amalfitano, G.; Bessard, J.; Vincent, F.; Eysseric, H.; Bessard, G., Gas chromatographic quantitation of dextropropoxyphene and norpropoxyphene in urine after solid-phase extraction, J. Anal. Toxicol., 20, 1996, 547-554.) NIST Spectra nist ri
      1469.2 (Program type: Ramp; Column cl... (show more) ass: Semi-standard non-polar; Column diameter: 0.2 mm; Column length: 12.5 m; Column type: Capillary; Heat rate: 25 K/min; Start T: 75 C; End T: 320 C; End time: 2 min; CAS no: 4764174; Active phase: Ultra-2; Phase thickness: 0.11 um; Data type: Normal alkane RI; Authors: Hemmersbach, P.; de la Torre, R., Review. Stimulants, narcotics and .beta.-blockers: 25 years of development in analytical techniques for doping control, J. Chromatogr. B, 687, 1996, 221-238.) NIST Spectra nist ri
      1457.4 (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: 30 K/min; Start T: 85 C; End T: 280 C; Start time: 1 min; CAS no: 4764174; Active phase: HP-5MS; Carrier gas: He; Phase thickness: 0.25 um; Data type: Normal alkane RI; Authors: Kronstrand, R., Identification of N-methyl-1-(3,4-methylenedioxy-phenyl)-2-butanamine (MBDB) in urine from drug users, J. Anal. Toxicol., 20, 1996, 512-516.) NIST Spectra nist ri
    • Retention Index (Linear):

      1443 (Program type: Ramp; Column cl... (show more) ass: Standard non-polar; Column diameter: 0.25 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: 4764174; Active phase: DB-1; Carrier gas: He; Phase thickness: 0.25 um; Data type: Linear RI; Authors: Perrigo, B.J.; Ballantyne, D.J.; Peel, H.W., Condierations in developing a data base for drugs on a DBI capillary column, J. Can. Soc. Forensic Sci., 17(2), 1984, 41-49., 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: 4764174; 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
      1434 (Program type: Ramp; Column cl... (show more) ass: Standard non-polar; Column diameter: 0.25 mm; Column length: 15 m; Column type: Capillary; Heat rate: 5 K/min; Start T: 100 C; End T: 295 C; CAS no: 4764174; Active phase: SE-30; Carrier gas: He; Phase thickness: 0.25 um; Data type: Linear RI; Authors: Anderson, W.H.; Stafford, D.T., Applications of capillary gas chromatography in routine toxicological analyses, J. Hi. Res. Chromatogr. & Chromatogr. Comm., 6, 1983, 247-254.) NIST Spectra nist ri
      1470 (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: 4764174; 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
      1508.8 (Program type: Complex; Column... (show more) class: Semi-standard non-polar; Column diameter: 0.25 mm; Column length: 30 m; Column type: Capillary; Description: Multi-step temperature program; T(initial)=60C; T(final)=270C; CAS no: 4764174; Active phase: VF-5MS; Carrier gas: He; Phase thickness: 0.25 um; Data type: Linear RI; Authors: Tret'yakov, K.V., Retention Data. NIST Mass Spectrometry Data Center., 2008.) 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: 281.7±9.0 °C at 760 mmHg
Vapour Pressure: 0.0±0.6 mmHg at 25°C
Enthalpy of Vaporization: 52.1±3.0 kJ/mol
Flash Point: 134.9±26.0 °C
Index of Refraction: 1.564
Molar Refractivity: 50.1±0.3 cm3
#H bond acceptors: 3
#H bond donors: 2
#Freely Rotating Bonds: 2
#Rule of 5 Violations: 0
ACD/LogP: 1.67
ACD/LogD (pH 5.5): -1.45
ACD/BCF (pH 5.5): 1.00
ACD/KOC (pH 5.5): 1.00
ACD/LogD (pH 7.4): -0.80
ACD/BCF (pH 7.4): 1.00
ACD/KOC (pH 7.4): 1.00
Polar Surface Area: 44 Å2
Polarizability: 19.9±0.5 10-24cm3
Surface Tension: 48.1±3.0 dyne/cm
Molar Volume: 154.0±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) =  1.82
    Log Kow (Exper. database match) =  1.64
       Exper. Ref:  Hansch,C & Leo,A (1985)
    Log Kow (Exper. database match) =  1.64
       Exper. Ref:  Sangster (1994)

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  281.85  (Adapted Stein & Brown method)
    Melting Pt (deg C):  75.39  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  0.00169  (Modified Grain method)
    Subcooled liquid VP: 0.00509 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):  2.25e+004
       log Kow used: 1.64 (expkow database)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  593.58 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   1.25E-009  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  1.771E-008 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  1.64  (exp database)
  Log Kaw used:  -7.292  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  8.932
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   1.1345
   Biowin2 (Non-Linear Model)     :   0.9987
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.6365  (weeks-months)
   Biowin4 (Primary Survey Model) :   3.7182  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.5411
   Biowin6 (MITI Non-Linear Model):   0.5261
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model):  0.5959
 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):  0.679 Pa (0.00509 mm Hg)
  Log Koa (Koawin est  ): 8.932
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  4.42E-006 
       Octanol/air (Koa) model:  0.00021 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.00016 
       Mackay model           :  0.000354 
       Octanol/air (Koa) model:  0.0165 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant =  92.9166 E-12 cm3/molecule-sec
      Half-Life =     0.115 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     1.381 Hrs
   Ozone Reaction:
      No Ozone Reaction Estimation
   Fraction sorbed to airborne particulates (phi): 0.000257 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  345.5
      Log Koc:  2.538 

 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 = 0.563 (BCF = 3.654)
       log Kow used: 1.64 (expkow database)

 Volatilization from Water:
    Henry LC:  1.25E-009 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River:  6.27E+005  hours   (2.613E+004 days)
    Half-Life from Model Lake : 6.841E+006  hours   (2.85E+005 days)

 Removal In Wastewater Treatment:
    Total removal:               2.02  percent
    Total biodegradation:        0.09  percent
    Total sludge adsorption:     1.93  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       0.0127          2.76         1000       
   Water     30.7            900          1000       
   Soil      69.2            1.8e+003     1000       
   Sediment  0.0847          8.1e+003     0          
     Persistence Time: 1.19e+003 hr




                    

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