Benzylmorphine

Identification

Name
Benzylmorphine
Accession Number
DB01573
Type
Small Molecule
Groups
Experimental, Illicit
Description
Not Available
Structure
Thumb
Synonyms
Not Available
External IDs
IDS-NB-002
Categories
Not Available
UNII
83C78V3OL9
CAS number
14297-87-1
Weight
Average: 375.4602
Monoisotopic: 375.183443671
Chemical Formula
C24H25NO3
InChI Key
RDJGWRFTDZZXSM-RNWLQCGYSA-N
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
IUPAC Name
(1S,5R,13R,14S,17R)-10-(benzyloxy)-4-methyl-12-oxa-4-azapentacyclo[9.6.1.0¹,¹³.0⁵,¹⁷.0⁷,¹⁸]octadeca-7(18),8,10,15-tetraen-14-ol
SMILES
[H][C@@]12OC3=C(OCC4=CC=CC=C4)C=CC4=C3[C@@]11CCN(C)[C@]([H])(C4)[C@]1([H])C=C[C@@H]2O

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
Not Available
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

Synthesis Reference

Bao-Shan Huang, Yansong Lu, Ben-Yi Ji, Aris P Christodoulou, "Preparation of naltrexone from codeine and 3-benzylmorphine." U.S. Patent US6013796, issued March, 1990.

US6013796
General References
Not Available
External Links
PubChem Compound
5362507
PubChem Substance
46504682
ChemSpider
4515062
Wikipedia
Benzylmorphine

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)132 °CPhysProp
water solubility400 mg/LMERCK INDEX (1996)
Predicted Properties
PropertyValueSource
Water Solubility0.0456 mg/mLALOGPS
logP2.71ALOGPS
logP3.07ChemAxon
logS-3.9ALOGPS
pKa (Strongest Acidic)13.78ChemAxon
pKa (Strongest Basic)9.19ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area41.93 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity109.22 m3·mol-1ChemAxon
Polarizability41.37 Å3ChemAxon
Number of Rings6ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9907
Blood Brain Barrier+0.998
Caco-2 permeable+0.8227
P-glycoprotein substrateSubstrate0.8828
P-glycoprotein inhibitor IInhibitor0.5984
P-glycoprotein inhibitor IIInhibitor0.5852
Renal organic cation transporterInhibitor0.7525
CYP450 2C9 substrateNon-substrate0.7405
CYP450 2D6 substrateSubstrate0.8919
CYP450 3A4 substrateSubstrate0.7127
CYP450 1A2 substrateNon-inhibitor0.7559
CYP450 2C9 inhibitorNon-inhibitor0.9054
CYP450 2D6 inhibitorInhibitor0.6622
CYP450 2C19 inhibitorNon-inhibitor0.8224
CYP450 3A4 inhibitorNon-inhibitor0.8889
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.7001
Ames testNon AMES toxic0.8284
CarcinogenicityNon-carcinogens0.9604
BiodegradationNot ready biodegradable0.9962
Rat acute toxicity2.6612 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.6913
hERG inhibition (predictor II)Non-inhibitor0.7378
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as morphinans. These are polycyclic compounds with a four-ring skeleton with three condensed six-member rings forming a partially hydrogenated phenanthrene moiety, one of which is aromatic while the two others are alicyclic.
Kingdom
Organic compounds
Super Class
Alkaloids and derivatives
Class
Morphinans
Sub Class
Not Available
Direct Parent
Morphinans
Alternative Parents
Phenanthrenes and derivatives / Tetralins / Coumarans / Aralkylamines / Alkyl aryl ethers / Piperidines / Benzene and substituted derivatives / Trialkylamines / Secondary alcohols / Oxacyclic compounds
show 3 more
Substituents
Morphinan / Phenanthrene / Tetralin / Coumaran / Alkyl aryl ether / Aralkylamine / Monocyclic benzene moiety / Piperidine / Benzenoid / Secondary alcohol
show 15 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available

Drug created on July 31, 2007 07:10 / Updated on November 02, 2018 05:03