nalorphine (CHEM042808)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-06-03 10:16:35 UTC
Update Date2016-11-09 01:22:48 UTC
Accession NumberCHEM042808
Identification
Common Namenalorphine
ClassSmall Molecule
DescriptionNalorphine is a mixed opioid agonist–antagonist. It acts at two opioid receptors—at the mu receptor it has antagonistic effects, and at the kappa receptors it exerts high-efficacy agonistic characteristics. It is used to reverse opioid overdose and (starting in the 1950s) in a challenge test to determine opioid dependence.
Contaminant Sources
  • STOFF IDENT Compounds
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
Nalorphine serbKegg
Hydrobromide, nalorphineMeSH
LethidroneMeSH
Nalorphine hydrochlorideMeSH
Nalorphine, L-tartrate (1:1)MeSH
Nalorphine hydrobromideMeSH
Nalorphine, (14 alpha)-isomerMeSH
AllylnormorphineMeSH
Hydrochloride, nalorphineMeSH
NalorphineMeSH
Chemical FormulaC19H21NO3
Average Molecular Mass311.381 g/mol
Monoisotopic Mass311.152 g/mol
CAS Registry Number62-67-9
IUPAC Name(1S,5R,13R,14S,17R)-4-(prop-2-en-1-yl)-12-oxa-4-azapentacyclo[9.6.1.0¹,¹³.0⁵,¹⁷.0⁷,¹⁸]octadeca-7(18),8,10,15-tetraene-10,14-diol
Traditional Namenalorphine
SMILES[H][C@@]12OC3=C(O)C=CC4=C3[C@@]11CCN(CC=C)[C@]([H])(C4)[C@]1([H])C=C[C@@H]2O
InChI IdentifierInChI=1S/C19H21NO3/c1-2-8-20-9-7-19-12-4-6-15(22)18(19)23-17-14(21)5-3-11(16(17)19)10-13(12)20/h2-6,12-13,15,18,21-22H,1,7-10H2/t12-,13+,15-,18-,19-/m0/s1
InChI KeyUIQMVEYFGZJHCZ-SSTWWWIQSA-N
Chemical Taxonomy
Description 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.
KingdomOrganic compounds
Super ClassAlkaloids and derivatives
ClassMorphinans
Sub ClassNot Available
Direct ParentMorphinans
Alternative Parents
Substituents
  • Morphinan
  • Phenanthrene
  • Tetralin
  • Coumaran
  • Alkyl aryl ether
  • 1-hydroxy-2-unsubstituted benzenoid
  • Aralkylamine
  • Piperidine
  • Benzenoid
  • Secondary alcohol
  • Tertiary amine
  • Tertiary aliphatic amine
  • Ether
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Organopnictogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Alcohol
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility1.36 g/LALOGPS
logP1.55ALOGPS
logP1.68ChemAxon
logS-2.4ALOGPS
pKa (Strongest Acidic)10.2ChemAxon
pKa (Strongest Basic)8.81ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area52.93 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity89.29 m³·mol⁻¹ChemAxon
Polarizability33.03 ųChemAxon
Number of Rings5ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-7090000000-c2f0177beb4226c08a1fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-1029000000-dcf68d57f8c07010942bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01ox-8095000000-694fe016c76374d4bab9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9040000000-87fbee9035fb3eab689dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0019000000-203e02d1e840c2051995Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03k9-1097000000-54d01b6a2f8ee1eea2b8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0hb9-1090000000-7cc26c4b1800ebaded64Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB11490
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNalorphine
Chemspider IDNot Available
ChEBI IDNot Available
PubChem Compound ID5284595
Kegg Compound IDC11787
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available