ChemSpider 2D Image | naloxone | C19H21NO4

naloxone

  • Molecular FormulaC19H21NO4
  • Average mass327.374 Da
  • Monoisotopic mass327.147064 Da
  • ChemSpider ID4447644
  • defined stereocentres - 4 of 4 defined stereocentres


More details:






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

(-)-N-Allyl-14-hydroxynordihydromorphinone
(-)-Naloxone
(5a)-4,5-Epoxy-3,14-dihydroxy-17-(2-propenyl)morphinan-6-one
(5α)-17-Allyl-3,14-dihydroxy-4,5-epoxymorphinan-6-on [German] [ACD/IUPAC Name]
(5α)-17-Allyl-3,14-dihydroxy-4,5-epoxymorphinan-6-one [ACD/IUPAC Name]
(5α)-17-Allyl-3,14-dihydroxy-4,5-époxymorphinane-6-one [French] [ACD/IUPAC Name]
(5α)-3,14-dihydroxy-17-(prop-2-en-1-yl)-4,5-epoxymorphinan-6-one
(5α)-3,14-dihydroxy-17-prop-2-en-1-yl-4,5-epoxymorphinan-6-one
(5α)-4,5-Epoxy-3,14-dihydroxy-17-(2-propenyl)morphinan-6-one
12-Allyl-7,7a,8,9-tetrahydro-3,7a-dihydroxy-4aH-8,9c-iminoethanophenanthro[4,5-bcd]furan-5(6H)-one
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

BRN 1089071 [DBID]
C07252 [DBID]
HSDB 3279 [DBID]
NSC 70413 [DBID]
NSC70413 [DBID]
Prestwick0_000111 [DBID]
Prestwick1_000111 [DBID]
SPBio_002061 [DBID]
  • Experimental Physico-chemical Properties
  • Miscellaneous
    • Safety:

      V03AB15 Wikidata Q282902
    • Chemical Class:

      A synthetic morphinane alkaloid that is morphinone in which the enone double bond has been reduced to a single bond, the hydrogen at position 14 has been replaced by a hydroxy group, and the methyl gr oup attached to the nitrogen has been replaced by an allyl group. A specific opioid antagonist, it is used (commonly as its hydrochloride salt) to reverse the effects of opioids, both following their use of opioids during surgery and in cases of known or suspected opioid overdose. ChEBI CHEBI:7459

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

Density: 1.4±0.1 g/cm3
Boiling Point: 532.8±50.0 °C at 760 mmHg
Vapour Pressure: 0.0±1.5 mmHg at 25°C
Enthalpy of Vaporization: 85.1±3.0 kJ/mol
Flash Point: 276.1±30.1 °C
Index of Refraction: 1.691
Molar Refractivity: 87.3±0.4 cm3
#H bond acceptors: 5
#H bond donors: 2
#Freely Rotating Bonds: 2
#Rule of 5 Violations: 0
ACD/LogP: 1.45
ACD/LogD (pH 5.5): 0.19
ACD/BCF (pH 5.5): 1.00
ACD/KOC (pH 5.5): 7.35
ACD/LogD (pH 7.4): 1.42
ACD/BCF (pH 7.4): 6.64
ACD/KOC (pH 7.4): 125.39
Polar Surface Area: 70 Å2
Polarizability: 34.6±0.5 10-24cm3
Surface Tension: 72.1±5.0 dyne/cm
Molar Volume: 228.1±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) =  0.95
    Log Kow (Exper. database match) =  2.09
       Exper. Ref:  Hansch,C et al. (1995)

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  462.27  (Adapted Stein & Brown method)
    Melting Pt (deg C):  194.97  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  4.25E-011  (Modified Grain method)
    Subcooled liquid VP: 2.6E-009 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):  1415
       log Kow used: 2.09 (expkow database)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  35128 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   5.38E-019  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  1.294E-014 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  2.09  (exp database)
  Log Kaw used:  -16.658  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  18.748
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.3278
   Biowin2 (Non-Linear Model)     :   0.0175
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   1.6976  (recalcitrant)
   Biowin4 (Primary Survey Model) :   2.8066  (weeks       )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.2983
   Biowin6 (MITI Non-Linear Model):   0.0472
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -1.9488
 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):  3.47E-007 Pa (2.6E-009 mm Hg)
  Log Koa (Koawin est  ): 18.748
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  8.65 
       Octanol/air (Koa) model:  1.37E+006 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.997 
       Mackay model           :  0.999 
       Octanol/air (Koa) model:  1 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant = 297.9092 E-12 cm3/molecule-sec
      Half-Life =     0.036 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =    25.851 Min
   Ozone Reaction:
      OVERALL Ozone Rate Constant =     1.200000 E-17 cm3/molecule-sec
      Half-Life =     0.955 Days (at 7E11 mol/cm3)
      Half-Life =     22.920 Hrs
   Reaction With Nitrate Radicals May Be Important!
   Fraction sorbed to airborne particulates (phi): 0.998 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  931.5
      Log Koc:  2.969 

 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 = 0.909 (BCF = 8.115)
       log Kow used: 2.09 (expkow database)

 Volatilization from Water:
    Henry LC:  5.38E-019 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 1.969E+015  hours   (8.204E+013 days)
    Half-Life from Model Lake : 2.148E+016  hours   (8.95E+014 days)

 Removal In Wastewater Treatment:
    Total removal:               2.34  percent
    Total biodegradation:        0.10  percent
    Total sludge adsorption:     2.24  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       9.95e-010       0.83         1000       
   Water     20.9            4.32e+003    1000       
   Soil      79              8.64e+003    1000       
   Sediment  0.0955          3.89e+004    0          
     Persistence Time: 3.26e+003 hr




                    

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