Codeine-N-oxide

Identification

Name
Codeine-N-oxide
Accession Number
DB01568
Type
Small Molecule
Groups
Experimental, Illicit
Description
Not Available
Structure
Thumb
Synonyms
Not Available
Categories
Not Available
UNII
Z32OFX7V17
CAS number
3688-65-1
Weight
Average: 315.3636
Monoisotopic: 315.147058165
Chemical Formula
C18H21NO4
InChI Key
BDLSDHWCOJPHIE-KFUGMXNISA-N
InChI
InChI=1S/C18H21NO4/c1-19(21)8-7-18-11-4-5-13(20)17(18)23-16-14(22-2)6-3-10(15(16)18)9-12(11)19/h3-6,11-13,17,20H,7-9H2,1-2H3/t11-,12+,13-,17-,18-,19-/m0/s1
IUPAC Name
(1S,4S,5R,13R,14S,17R)-14-hydroxy-10-methoxy-4-methyl-12-oxa-4-azapentacyclo[9.6.1.0¹,¹³.0⁵,¹⁷.0⁷,¹⁸]octadeca-7(18),8,10,15-tetraen-4-ium-4-olate
SMILES
[H][C@@]12OC3=C(OC)C=CC4=C3[C@@]11CC[N@+](C)([O-])[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

General References
Not Available
External Links
PubChem Compound
5359929
PubChem Substance
46504794
ChemSpider
4514400
Wikipedia
Codeine-N-oxide

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)231.5 °CPhysProp
Predicted Properties
PropertyValueSource
Water Solubility0.138 mg/mLALOGPS
logP-0.48ALOGPS
logP0.22ChemAxon
logS-3.4ALOGPS
pKa (Strongest Acidic)13.78ChemAxon
pKa (Strongest Basic)2.75ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area65.57 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity86.65 m3·mol-1ChemAxon
Polarizability32.51 Å3ChemAxon
Number of Rings5ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.6433
Blood Brain Barrier+0.9939
Caco-2 permeable+0.6034
P-glycoprotein substrateSubstrate0.8477
P-glycoprotein inhibitor INon-inhibitor0.7436
P-glycoprotein inhibitor IINon-inhibitor0.9656
Renal organic cation transporterNon-inhibitor0.5157
CYP450 2C9 substrateNon-substrate0.8192
CYP450 2D6 substrateNon-substrate0.5
CYP450 3A4 substrateSubstrate0.7774
CYP450 1A2 substrateNon-inhibitor0.8243
CYP450 2C9 inhibitorNon-inhibitor0.8429
CYP450 2D6 inhibitorNon-inhibitor0.7587
CYP450 2C19 inhibitorNon-inhibitor0.7613
CYP450 3A4 inhibitorNon-inhibitor0.8591
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9033
Ames testNon AMES toxic0.7812
CarcinogenicityNon-carcinogens0.8989
BiodegradationNot ready biodegradable0.8248
Rat acute toxicity2.4831 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.7675
hERG inhibition (predictor II)Non-inhibitor0.8397
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 GC-MS Spectrum - GC-MSPredicted GC-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 / Anisoles / Alkyl aryl ethers / Piperidines / Trialkyl amine oxides / Secondary alcohols / Trisubstituted amine oxides and derivatives / Oxacyclic compounds
show 5 more
Substituents
Morphinan / Phenanthrene / Tetralin / Coumaran / Anisole / Alkyl aryl ether / Piperidine / Benzenoid / Trialkyl amine oxide / Secondary alcohol
show 16 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