NAV

Benzylmorphine

Identification

Generic Name
Benzylmorphine
DrugBank Accession Number
DB01573
Background

Not Available

Type
Small Molecule
Groups
Experimental, Illicit
Structure
3D
Similar Structures
Weight
Average: 375.4602
Monoisotopic: 375.183443671
Chemical Formula
C24H25NO3
Synonyms
Not Available
External IDs
  • IDS-NB-002
Poor quality drug data slowing you down?
Unlock 38% more drug discovery time and eliminate decision-making doubts with this one-stop guide to quality drug data.
Download eBook
Poor quality drug data slowing you down?
Download eBook

Pharmacology

Indication

Not Available

Reduce drug development failure rates
Build, train, & validate machine-learning models
with evidence-based and structured datasets.
See how
Build, train, & validate predictive machine-learning models with structured datasets.
See how
Contraindications & Blackbox Warnings
Prevent Adverse Drug Events Today
Tap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.
Learn more
Avoid life-threatening adverse drug events with our Clinical API
Learn more
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

Adverse Effects
Improve decision support & research outcomes
With structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!
See the data
Improve decision support & research outcomes with our structured adverse effects data.
See a data sample
Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Not Available
Food Interactions
Not Available

Categories

Drug Categories
Not Available
Chemical TaxonomyProvided by Classyfire
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
Alcohol / Alkyl aryl ether / Amine / Aralkylamine / Aromatic heteropolycyclic compound / Azacycle / Benzenoid / Coumaran / Ether / Hydrocarbon derivative
show 15 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
83C78V3OL9
CAS number
14297-87-1
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[9.6.1.0^{1,13}.0^{5,17}.0^{7,18}]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

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
PubChem Compound
5362507
PubChem Substance
46504682
ChemSpider
4515062
ZINC
ZINC000004214989
Wikipedia
Benzylmorphine

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

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
Polarizability41.38 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/MSsplash10-004i-0009000000-9827d6b512f365448074
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-00di-0109000000-9ba83c0bdc0a2f78e6a0
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-004i-0009000000-6024f8cc2913f58bb8d8
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-00di-0059000000-758daa627bc66cebd2f8
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-00bd-6059000000-058222eb09f838b0092c
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-00di-1139000000-7c4afeb6b8398a39ebfe
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-194.8846355
predicted
DarkChem Lite v0.1.0
[M-H]-186.13835
predicted
DeepCCS 1.0 (2019)
[M+H]+194.8542355
predicted
DarkChem Lite v0.1.0
[M+H]+188.9763
predicted
DeepCCS 1.0 (2019)
[M+Na]+194.4139355
predicted
DarkChem Lite v0.1.0
[M+Na]+196.29295
predicted
DeepCCS 1.0 (2019)

Drug created at July 31, 2007 13:10 / Updated at June 12, 2020 16:51