ChemSpider 2D Image | diacetylmorphine | C21H23NO5

diacetylmorphine

  • Molecular FormulaC21H23NO5
  • Average mass369.411 Da
  • Monoisotopic mass369.157623 Da
  • ChemSpider ID4575379

  • defined stereocentres - 5 of 5 defined stereocentres

More details:

Featured data source
The Merck Index Online

Validated by Experts, Validated by Users, Non-Validated, Removed by Users

diacetylmorphine [Wiki]
(5α,6α)-17-Methyl-7,8-didehydro-4,5-epoxymorphinan-3,6-diyl diacetate [ACD/IUPAC Name]
(5α,6α)-17-Methyl-7,8-didehydro-4,5-epoxymorphinan-3,6-diyl-diacetat [German] [ACD/IUPAC Name]
209-217-7 [EINECS]
561-27-3 [RN]
7,8-Dihydro-4,5a-epoxy-17-methylmorphinan-3,6a-diol Diacetate
Diacétate de (5α,6α)-17-méthyl-7,8-didéhydro-4,5-époxymorphinane-3,6-diyle [French] [ACD/IUPAC Name]
MFCD00468072 [MDL number]
Morphinan-3,6-diol, 7,8-didehydro-4,5-epoxy-17-methyl-, diacetate (ester), (5α,6α)- [ACD/Index Name]
(1S,5R,13R,14S,17R)-10-(acetyloxy)-4-methyl-12-oxa-4-azapentacyclo[9.6.1.01,13.05,17.07,18]octadeca-7(18),8,10,15-tetraen-14-yl acetate
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

70D95007SX [DBID]
QC8050000 [DBID]
C06534 [DBID]
CHEBI:27808 [DBID]
DEA No. 9200 [DBID]
H159_SIGMA [DBID]
HSDB 6473 [DBID]
UNII-70D95007SX [DBID]
  • Experimental Physico-chemical Properties
  • Miscellaneous

    • Toxicity:

      Organic Compound; Amine; Ether; Ester; Drug; Analgesic, Opioid; Narcotic; Synthetic Compound Toxin, Toxin-Target Database T3D4562

    • Safety:

      N07BC06 Wikidata Q60168

    • Chemical Class:

      A morphinane alkaloid that is morphine bearing two acetyl substituents on the O-3 and O-6 positions. As with other opioids, heroin is used as both an analgesic and a recreational drug. Frequent and re gular administration is associated with tolerance and physical dependence, which may develop into addiction. Its use includes treatment for acute pain, such as in severe physical trauma, myocardial in farction, post-surgical pain, and chronic pain, including end-stage cancer and other terminal illnesses. ChEBI CHEBI:27808, https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:27808

Predicted data is generated using the ACD/Labs Percepta Platform - PhysChem Module, version: 14.00

Density: 1.4±0.1 g/cm3
Boiling Point: 492.9±45.0 °C at 760 mmHg
Vapour Pressure: 0.0±1.3 mmHg at 25°C
Enthalpy of Vaporization: 76.0±3.0 kJ/mol
Flash Point: 251.9±28.7 °C
Index of Refraction: 1.629
Molar Refractivity: 97.2±0.4 cm3
#H bond acceptors: 6
#H bond donors: 0
#Freely Rotating Bonds: 4
#Rule of 5 Violations: 0
ACD/LogP: 1.52
ACD/LogD (pH 5.5): -0.47
ACD/BCF (pH 5.5): 1.00
ACD/KOC (pH 5.5): 1.13
ACD/LogD (pH 7.4): 1.24
ACD/BCF (pH 7.4): 3.62
ACD/KOC (pH 7.4): 57.34
Polar Surface Area: 65 Å2
Polarizability: 38.5±0.5 10-24cm3
Surface Tension: 57.9±5.0 dyne/cm
Molar Volume: 273.7±5.0 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) =  1.80
    Log Kow (Exper. database match) =  1.58
       Exper. Ref:  Avdeef,A et al. (1996)

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  424.35  (Adapted Stein & Brown method)
    Melting Pt (deg C):  159.85  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  6.2E-008  (Modified Grain method)
    MP  (exp database):  173 deg C
    BP  (exp database):  272-274 @ 12 mm Hg deg C
    VP  (exp database):  7.59E-10 mm Hg at 25 deg C
    Subcooled liquid VP: 2.21E-008 mm Hg (25 deg C, exp database VP )

 Water Solubility Estimate from Log Kow (WSKOW v1.41):
    Water Solubility at 25 deg C (mg/L):  2152
       log Kow used: 1.58 (expkow database)
       no-melting pt equation used
     Water Sol (Exper. database match) =  600 mg/L (25 deg C)
        Exper. Ref:  SEIDELL,A (1941)

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  8.3565 mg/L
    Wat Sol (Exper. database match) =  600.00
       Exper. Ref:  SEIDELL,A (1941)

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   1.00E-012  atm-m3/mole
   Group Method:   Incomplete
   Exper Database: 6.15E-13  atm-m3/mole
 Henrys LC [VP/WSol estimate using EPI values]:  1.400E-011 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  1.58  (exp database)
  Log Kaw used:  -10.600  (exp database)
      Log Koa (KOAWIN v1.10 estimate):  12.180
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.7174
   Biowin2 (Non-Linear Model)     :   0.9918
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.0633  (months      )
   Biowin4 (Primary Survey Model) :   3.3398  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.5422
   Biowin6 (MITI Non-Linear Model):   0.1017
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -0.8319
 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):  2.95E-006 Pa (2.21E-008 mm Hg)
  Log Koa (Koawin est  ): 12.180
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  1.02 
       Octanol/air (Koa) model:  0.372 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.974 
       Mackay model           :  0.988 
       Octanol/air (Koa) model:  0.967 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant = 229.5868 E-12 cm3/molecule-sec
      Half-Life =     0.047 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     0.559 Hrs
   Ozone Reaction:
      OVERALL Ozone Rate Constant =    20.000000 E-17 cm3/molecule-sec
      Half-Life =     0.057 Days (at 7E11 mol/cm3)
      Half-Life =      1.375 Hrs
   Fraction sorbed to airborne particulates (phi): 0.981 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  7182
      Log Koc:  3.856 

 Aqueous Base/Acid-Catalyzed Hydrolysis (25 deg C) [HYDROWIN v1.67]:
  Total Kb for pH > 8 at 25 deg C :  6.741E-001  L/mol-sec
  Kb Half-Life at pH 8:      11.900  days   
  Kb Half-Life at pH 7:     118.997  days   

 Bioaccumulation Estimates from Log Kow (BCFWIN v2.17):
   Log BCF from regression-based method = 0.517 (BCF = 3.285)
       log Kow used: 1.58 (expkow database)

 Volatilization from Water:
    Henry LC:  6.15E-013 atm-m3/mole  (Henry experimental database)
    Half-Life from Model River:  1.83E+009  hours   (7.624E+007 days)
    Half-Life from Model Lake : 1.996E+010  hours   (8.317E+008 days)

 Removal In Wastewater Treatment:
    Total removal:               2.00  percent
    Total biodegradation:        0.09  percent
    Total sludge adsorption:     1.91  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       9.09e-006       0.617        1000       
   Water     32.8            1.44e+003    1000       
   Soil      67.1            2.88e+003    1000       
   Sediment  0.0885          1.3e+004     0          
     Persistence Time: 1.54e+003 hr

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