InChI=1/C24H25NO3/c1-25-12-11-24-17-8-9-19(26)23(24)28-22-20(27-14-15-5-3-2-4-6-15)10-7-16(21(22)24)13-18(17)25/h2-10,17-19,23,26H,11-14H2,1H3/t17-,18+,19-,23-,24-/m0/s1

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Search term: RDJGWRFTDZZXSM-RNWLQCGYBX
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Inherent Properties, Identifiers and References

ChemSpider ID:	4515062
Empirical Formula:	C₂₄H₂₅NO₃
Molecular Weight:	375.4602
Nominal Mass:	375 Da
Average Mass:	375.4602 Da
Monoisotopic Mass:	375.183444 Da

Systematic Name:

SMILES:

O[C@H]2\C=C/[C@H]6[C@@H]5N(CC[C@@]61c4c(O[C@H]12)c(OCc3ccccc3)ccc4C5)C

InChI:

InChI=1/C24H25NO3/c1-25-12-11-24-17-8-9-19(26)23(24)28-22-20(27-14-15-5-3-2-4-6-15)10-7-16(21(22)24)13-18(17)25/h2-10,17-19,23,26H,11-14H2,1H3/t17-,18+,19-,23-,24-/m0/s1

InChIKey:

RDJGWRFTDZZXSM-RNWLQCGYBX

Std. InChI:

InChI=1S/C24H25NO3/c1-25-12-11-24-17-8-9-19(26)23(24)28-22-20(27-14-15-5-3-2-4-6-15)10-7-16(21(22)24)13-18(17)25/h2-10,17-19,23,26H,11-14H2,1H3/t17-,18+,19-,23-,24-/m0/s1

Std. InChIKey:

RDJGWRFTDZZXSM-RNWLQCGYSA-N

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Wikipedia Article(s)

Benzylmorphine (Peronine) is a semi-synthetic opiate narcotic introduced to the international market in 1896 and that of the United States very shortly thereafter. It is much like codeine, containing a benzyl group attached to the morphine molecule just as the methyl group creates codeine and the ethyl group creates ethylmorphine or dionine (used as a generic name for that drug just as peronine is for benzylmorphine). It is about 90 per cent as strong as codeine by weight. Benzylmorphine is used in much the same way as codeine and ethylmorphine, primarily as a moderate strength analgesic, for eye surgery as a 1 to 2 per cent solution, and as a cough suppressant. It was available in the United States prior to 1914 and was still used until the 1960s, but fell into disuse once alternative opiate derivatives became preferred by doctors (i.e. hydrocodone as an analgesic and pholcodeine as a cough suppressant) Benzylmorphine is now a Schedule I Controlled Substance in the USA and is regulated internationally under UN drug conventions. Benzylmorphine is an active metabolite of the opioid analgesic myrophine, formed in the liver. It has a metabolic fate similar to that of codeine. Benzylmorphine is used as the hydrochloride (free base conversion ratio 0.91) and methylsulphonate(0.80) and has a US DEA Administrative Controlled Substance Control Number of 9052. Read more... or Edit at Wikipedia...

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Names and Synonyms

Validated by Experts, Validated by Users, Non-Validated, Removed by Users, Redirected by Users, Redirect Approved by Experts

(5a,6a)-3-(Benzyloxy)-17-methyl-7,8-didehydro-4,5-epoxymorphinan-6-ol

(5alpha,6alpha)-3-(Benzyloxy)-17-methyl-7,8-didehydro-4,5-epoxymorphinan-6-ol

14297-87-1 [RN]

238-230-0 [EINECS/ELINCS]

630-86-4 [RN]

Morphinan-6-ol, 7,8-didehydro-4,5-epoxy-17-methyl-3-(phenylmethoxy)-, (5.alpha.,6.alpha.)-

morphinan-6-ol, 7,8-didehydro-4,5-epoxy-17-methyl-3-(phenylmethoxy)-, (5alpha,6alpha)-

Peronine

3-Benzyloxy-4,5alpha-epoxy-17-methyl-7-morphinen-6alpha-ol

3-O-benzylmorphine

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Database ID(s)

Validated by Experts, Validated by Users, Non-Validated, Removed by Users, Redirected by Users, Redirect Approved by Experts

ACD/Labs Predicted Properties

ACD/LogP:	2.85	# of Rule of 5 Violations:	0
ACD/LogD (pH 5.5):		ACD/LogD (pH 7.4):
ACD/BCF (pH 5.5):		ACD/BCF (pH 7.4):
ACD/KOC (pH 5.5):		ACD/KOC (pH 7.4):
#H bond acceptors:	4	#H bond donors:	1
#Freely Rotating Bonds:	4	Polar Surface Area:	30.93 Å²
Index of Refraction:	1.689	Molar Refractivity:	107.57 cm³
Molar Volume:	281.5 cm³	Polarizability:	42.64 10^-24cm³
Surface Tension:	63.5 dyne/cm	Density:	1.33 g/cm³
Flash Point:	287.9 °C	Enthalpy of Vaporization:	87.66 kJ/mol
Boiling Point:	552.5 °C at 760 mmHg	Vapour Pressure:	4.85E-13 mmHg at 25°C

EPI Summary

            
 Log Octanol-Water Partition Coef (SRC):
    Log Kow (KOWWIN v1.67 estimate) =  2.98

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  489.87  (Adapted Stein & Brown method)
    Melting Pt (deg C):  207.87  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  3.22E-011  (Modified Grain method)
    MP  (exp database):  132 deg C
    Subcooled liquid VP: 3.8E-010 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):  124.9
       log Kow used: 2.98 (estimated)
       no-melting pt equation used
     Water Sol (Exper. database match) =  400 mg/L ( deg C)
        Exper. Ref:  MERCK INDEX (1996)

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  0.69886 mg/L
    Wat Sol (Exper. database match) =  400.00
       Exper. Ref:  MERCK INDEX (1996)

 ECOSAR Class Program (ECOSAR v0.99h):
    Class(es) found:
       Aliphatic Amines
       Vinyl/Allyl Alcohols

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   6.12E-015  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  1.274E-013 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  2.98  (KowWin est)
  Log Kaw used:  -12.602  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  15.582
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.7849
   Biowin2 (Non-Linear Model)     :   0.8483
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   1.8934  (months      )
   Biowin4 (Primary Survey Model) :   3.0846  (weeks       )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.1776
   Biowin6 (MITI Non-Linear Model):   0.0112
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -0.9720
 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):  5.07E-008 Pa (3.8E-010 mm Hg)
  Log Koa (Koawin est  ): 15.582
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  59.2 
       Octanol/air (Koa) model:  938 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  1 
       Mackay model           :  1 
       Octanol/air (Koa) model:  1 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant = 253.0838 E-12 cm3/molecule-sec
      Half-Life =     0.042 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     0.507 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): 1 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  5.248E+004
      Log Koc:  4.720 

 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 = 1.598 (BCF = 39.63)
       log Kow used: 2.98 (estimated)

 Volatilization from Water:
    Henry LC:  6.12E-015 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 1.854E+011  hours   (7.724E+009 days)
    Half-Life from Model Lake : 2.022E+012  hours   (8.426E+010 days)

 Removal In Wastewater Treatment:
    Total removal:               5.52  percent
    Total biodegradation:        0.12  percent
    Total sludge adsorption:     5.40  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       1.36e-005       0.584        1000       
   Water     10.8            1.44e+003    1000       
   Soil      88.9            2.88e+003    1000       
   Sediment  0.258           1.3e+004     0          
     Persistence Time: 2.67e+003 hr

SimBioSys LASSO

Descriptors: 0, 0, 0, 0, 0, 0, 0, 5, 0, 0, 1, 2, 5, 7, 10, 2, 12, 0, 0, 0, 2, 0, 0, 0

Category	Target	PDB Code	LASSO Score
Other Enzymes	AChE, acetylcholinesterase	1eve	0.04
Nuclear Hormone Receptors	PPARg, peroxisome proliferator activated receptor	1fm9	0.03
Other Enzymes	HIVRT, HIV reverse transcriptase	1rt1	0.02
Kinases	SRC, tyrosine kinase SRC	2src	0.01
Other Enzymes	HMGR, hydroxymethylglutaryl-CoA reductase	1hw8	0.01
Serine Proteases	Thrombin	1ba8	0.01
Other Enzymes	HIVPR, HIV protease	1hpx	0.01
Metalloenzymes	PDE5, phosphodiesterase 5	1xp0	0.01
Kinases	PDGFrb, platelet derived growth factor receptor kinase	N/A	0.01
Nuclear Hormone Receptors	MR, mineralocorticoid receptor	2aa2	0.01
Nuclear Hormone Receptors	PR, progesterone receptor	1sr7	0.01
Kinases	HSP90, human heat shock protein 90	1uy6	0.01
Other Enzymes	PARP, poly(ADP-ribose) polymerase	1efy	0.01
Nuclear Hormone Receptors	GR, glucocorticoid receptor	1m2z	0.00
Other Enzymes	PNP, purine nucleoside phosphorylase	1b8o	0.00
Other Enzymes	AmpC, AmpC beta-lactamase	1xgj	0.00
Folate Enzymes	GART, glycinamide ribonucleotide transformylase	1c2t	0.00
Nuclear Hormone Receptors	ER, estrogen receptor; agonist	1l2i	0.00
Nuclear Hormone Receptors	ER, estrogen receptor; antagonist	3ert	0.00
Folate Enzymes	DHFR, dihydrofolate reductase	3dfr	0.00
Metalloenzymes	ACE, angiotensin-converting enzyme	1o86	0.00
Kinases	VEGFr2, vascular endothelial growth factor receptor	1vr2	0.00
Other Enzymes	GPB, glycogen phosphorylase	1a8i	0.00
Serine Proteases	Trypsin	1bju	0.00
Other Enzymes	InhA, enoyl ACP reductase	1p44	0.00
Other Enzymes	SAHH, S-adenosyl-homocysteine hydrolase	1a7a	0.00
Kinases	FGFr1, fibroblast growth factor receptor kinase	1agw	0.00
Kinases	TK, thymidine kinase	1kim	0.00
Other Enzymes	ALR2, aldose reductase	1ah3	0.00
Other Enzymes	NA, neuraminidase	1a4g	0.00
Nuclear Hormone Receptors	RXRa, retinoic X receptor R	1mvc	0.00
Metalloenzymes	ADA, adenosine deaminase	1stw	0.00
Kinases	P38 MAP, P38 mitogen activated protein	1kv2	0.00
Nuclear Hormone Receptors	AR, androgen receptor	1xq2	0.00
Other Enzymes	COX-2, cyclooxygenase-2	1cx2	0.00
Kinases	CDK2, cyclindependent kinase 2	1ckp	0.00
Metalloenzymes	COMT, catechol O-methyltransferase	1h1d	0.00
Other Enzymes	COX-1, cyclooxygenase-1	1p4g	0.00
Serine Proteases	FXa, factor Xa	1f0r	0.00
Kinases	EGFr, epidermal growth factor receptor	1m17	0.00