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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:50 UTC
Update Date2022-03-07 02:51:41 UTC
HMDB IDHMDB0014647
Secondary Accession Numbers
  • HMDB14647
Metabolite Identification
Common NameLevallorphan
DescriptionLevallorphan, also known as lorfan or naloxiphan, 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. Levallorphan is a drug which is used for the complete or partial reversal of narcotic depression, including respiratory depression, induced by opioids. In humans, levallorphan is involved in the levallorphan action pathway. Levallorphan is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review very few articles have been published on Levallorphan.
Structure
Data?1582753203
Synonyms
ValueSource
LorfanHMDB
NaloxiphanHMDB
Chemical FormulaC19H25NO
Average Molecular Weight283.4079
Monoisotopic Molecular Weight283.193614427
IUPAC Name(1R,9R,10R)-17-(prop-2-en-1-yl)-17-azatetracyclo[7.5.3.0¹,¹⁰.0²,⁷]heptadeca-2(7),3,5-trien-4-ol
Traditional Namelevallorphan
CAS Registry Number152-02-3
SMILES
[H][C@@]12CCCC[C@@]11CCN(CC=C)[C@@H]2CC2=C1C=C(O)C=C2
InChI Identifier
InChI=1S/C19H25NO/c1-2-10-20-11-9-19-8-4-3-5-16(19)18(20)12-14-6-7-15(21)13-17(14)19/h2,6-7,13,16,18,21H,1,3-5,8-12H2/t16-,18+,19+/m0/s1
InChI KeyOZYUPQUCAUTOBP-QXAKKESOSA-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
  • Benzazocine
  • Tetralin
  • 1-hydroxy-2-unsubstituted benzenoid
  • Aralkylamine
  • Piperidine
  • Benzenoid
  • Tertiary aliphatic amine
  • Tertiary amine
  • Organoheterocyclic compound
  • Azacycle
  • Organopnictogen compound
  • Amine
  • Organic oxygen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Process
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point181 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.025 g/LNot Available
LogP3.9Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.025 g/LALOGPS
logP3.91ALOGPS
logP3.76ChemAxon
logS-4ALOGPS
pKa (Strongest Acidic)10.36ChemAxon
pKa (Strongest Basic)9.41ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area23.47 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity87.24 m³·mol⁻¹ChemAxon
Polarizability32.68 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+165.85931661259
DarkChem[M-H]-162.68631661259
DeepCCS[M-2H]-204.56530932474
DeepCCS[M+Na]+179.87130932474
AllCCS[M+H]+171.332859911
AllCCS[M+H-H2O]+168.032859911
AllCCS[M+NH4]+174.332859911
AllCCS[M+Na]+175.232859911
AllCCS[M-H]-175.932859911
AllCCS[M+Na-2H]-175.832859911
AllCCS[M+HCOO]-175.732859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Levallorphan[H][C@@]12CCCC[C@@]11CCN(CC=C)[C@@H]2CC2=C1C=C(O)C=C23642.8Standard polar33892256
Levallorphan[H][C@@]12CCCC[C@@]11CCN(CC=C)[C@@H]2CC2=C1C=C(O)C=C22401.4Standard non polar33892256
Levallorphan[H][C@@]12CCCC[C@@]11CCN(CC=C)[C@@H]2CC2=C1C=C(O)C=C22385.7Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Levallorphan,1TMS,isomer #1C=CCN1CC[C@]23CCCC[C@H]2[C@H]1CC1=CC=C(O[Si](C)(C)C)C=C132318.4Semi standard non polar33892256
Levallorphan,1TBDMS,isomer #1C=CCN1CC[C@]23CCCC[C@H]2[C@H]1CC1=CC=C(O[Si](C)(C)C(C)(C)C)C=C132592.9Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Levallorphan GC-MS (Non-derivatized) - 70eV, Positivesplash10-052f-2090000000-e1bfcb97bfa8788020442017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Levallorphan GC-MS (1 TMS) - 70eV, Positivesplash10-01tc-3049000000-4352cd28b7455258b0012017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Levallorphan GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Levallorphan 10V, Positive-QTOFsplash10-001i-0090000000-c886e11a52629d3b6ace2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Levallorphan 20V, Positive-QTOFsplash10-000x-5090000000-a50bd8ddd987c3505bed2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Levallorphan 40V, Positive-QTOFsplash10-0006-9020000000-78f892a0fe089e1dc6752016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Levallorphan 10V, Negative-QTOFsplash10-001i-0090000000-d24e2a1bbf1c331446e32016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Levallorphan 20V, Negative-QTOFsplash10-001l-0090000000-f90e6f45cb42029ac3f62016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Levallorphan 40V, Negative-QTOFsplash10-0006-1290000000-a9303de3f0f8a329e2f62016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Levallorphan 10V, Negative-QTOFsplash10-001i-0090000000-de4c3229168dbf0710892021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Levallorphan 20V, Negative-QTOFsplash10-001l-0090000000-6bded21078e814eff1992021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Levallorphan 40V, Negative-QTOFsplash10-001i-0290000000-d27c8821f73ae54df17f2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Levallorphan 10V, Positive-QTOFsplash10-001i-0090000000-3c4b9ea0fce2ba47ecaf2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Levallorphan 20V, Positive-QTOFsplash10-001i-0090000000-5b62cdc6cd2bda1045b62021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Levallorphan 40V, Positive-QTOFsplash10-01ow-1960000000-890603e347ff7eb26f472021-09-22Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00504 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00504 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00504
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID10481920
KEGG Compound IDC07069
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkLevallorphan
METLIN IDNot Available
PubChem Compound5359371
PDB IDNot Available
ChEBI ID804148
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
Inhibits neurotransmitter release by reducing calcium ion currents and increasing potassium ion conductance. Receptor for beta-endorphin
Gene Name:
OPRM1
Uniprot ID:
P35372
Molecular weight:
44778.9
References
  1. Picker MJ, Benyas S, Horwitz JA, Thompson K, Mathewson C, Smith MA: Discriminative stimulus effects of butorphanol: influence of training dose on the substitution patterns produced by Mu, Kappa and Delta opioid agonists. J Pharmacol Exp Ther. 1996 Dec;279(3):1130-41. [PubMed:8968334 ]
  2. Traynor JR, Nahorski SR: Modulation by mu-opioid agonists of guanosine-5'-O-(3-[35S]thio)triphosphate binding to membranes from human neuroblastoma SH-SY5Y cells. Mol Pharmacol. 1995 Apr;47(4):848-54. [PubMed:7723747 ]
  3. Selley DE, Sim LJ, Xiao R, Liu Q, Childers SR: mu-Opioid receptor-stimulated guanosine-5'-O-(gamma-thio)-triphosphate binding in rat thalamus and cultured cell lines: signal transduction mechanisms underlying agonist efficacy. Mol Pharmacol. 1997 Jan;51(1):87-96. [PubMed:9016350 ]
  4. Emmerson PJ, Clark MJ, Mansour A, Akil H, Woods JH, Medzihradsky F: Characterization of opioid agonist efficacy in a C6 glioma cell line expressing the mu opioid receptor. J Pharmacol Exp Ther. 1996 Sep;278(3):1121-7. [PubMed:8819494 ]
  5. Morgan D, Picker MJ: The mu opioid irreversible antagonist beta-funaltrexamine differentiates the discriminative stimulus effects of opioids with high and low efficacy at the mu opioid receptor. Psychopharmacology (Berl). 1998 Nov;140(1):20-8. [PubMed:9862398 ]