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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:51 UTC
Update Date2021-09-14 15:19:50 UTC
HMDB IDHMDB0014992
Secondary Accession Numbers
  • HMDB14992
Metabolite Identification
Common NameLevorphanol
DescriptionLevorphanol, also known as levo dromoran or dea no. 9220, 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. It is the "left-handed" (levorotatory) stereoisomer of racemorphan, that is the racemic mixture of the two stereoisomers with differing pharmacology. Levorphanol is a drug which is used for the management of moderate to severe pain or as a preoperative medication where an opioid analgesic is appropriate. Levorphanol shows a high rate of psychotomimetic side effects such as hallucinations and delirium, which have been attributed to its binding to and activation of the KOR. Levorphanol is the INN, BAN, and DCF. Levorphanol is a very strong basic compound (based on its pKa). In humans, levorphanol is involved in levorphanol action pathway. The duration of action is generally long compared to other comparable analgesics and varies from 4 hours to as much as 15 hours. Levorphanol is listed under the Single Convention On Narcotic Drugs 1961 and is regulated like morphine in most countries. The drug has been in medical use in the United States since 1953. Levorphanol is a potentially toxic compound.
Structure
Data?1582753245
Synonyms
ValueSource
Dea no. 9220HMDB
Dea no. 9733HMDB
LevorfanoloHMDB
LevorphanHMDB
LevorphanalHMDB
Levorphanol DL-formHMDB
MethorphinanHMDB
RacemethorphanumHMDB
3 Hydroxy N methylmorphinanHMDB
L DromoranHMDB
Levo dromoranHMDB
Tartrate, levorphanolHMDB
3-Hydroxy-N-methylmorphinanHMDB
ICN brand OF levorphanol tartrateHMDB
L-DromoranHMDB
Levorphanol tartrateHMDB
Levo-dromoranHMDB
LevoDromoranHMDB
Chemical FormulaC17H23NO
Average Molecular Weight257.3706
Monoisotopic Molecular Weight257.177964363
IUPAC Name(1R,9R,10R)-17-methyl-17-azatetracyclo[7.5.3.0¹,¹⁰.0²,⁷]heptadeca-2(7),3,5-trien-4-ol
Traditional Namelevorphanol
CAS Registry Number77-07-6
SMILES
[H][C@@]12CCCC[C@@]11CCN(C)[C@@H]2CC2=C1C=C(O)C=C2
InChI Identifier
InChI=1S/C17H23NO/c1-18-9-8-17-7-3-2-4-14(17)16(18)10-12-5-6-13(19)11-15(12)17/h5-6,11,14,16,19H,2-4,7-10H2,1H3/t14-,16+,17+/m0/s1
InChI KeyJAQUASYNZVUNQP-USXIJHARSA-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
Disposition

Biological location

Source

Route of exposure

Process

Naturally occurring process

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point198 - 199 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.17 g/LNot Available
LogP3.3Not Available
Experimental Spectral Properties

Experimental Collision Cross Sections

PredictorAdduct TypeData SourceCCS Value (Å2)Reference
DeepCCS[M+H]+CBM161.730932474
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.17 g/LALOGPS
logP10(3.29) g/LALOGPS
logP10(2.9) g/LChemAxon
logS10(-3.2) g/LALOGPS
pKa (Strongest Acidic)10.46ChemAxon
pKa (Strongest Basic)9.66ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area23.47 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity78.08 m³·mol⁻¹ChemAxon
Polarizability29.84 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+159.03231661259
DarkChem[M-H]-158.3431661259

Predicted Kovats Retention Indices

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Levorphanol,1TMS,#1CN1CC[C@]23CCCC[C@H]2[C@H]1CC1=CC=C(O[Si](C)(C)C)C=C132204.7Semi standard non polarhttps://arxiv.org/abs/1905.12712
Levorphanol,1TBDMS,#1CN1CC[C@]23CCCC[C@H]2[C@H]1CC1=CC=C(O[Si](C)(C)C(C)(C)C)C=C132498.3Semi standard non polarhttps://arxiv.org/abs/1905.12712
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Levorphanol GC-MS (Non-derivatized) - 70eV, Positivesplash10-00ou-0190000000-14189f3c821f5d9240bf2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Levorphanol GC-MS (1 TMS) - 70eV, Positivesplash10-0hbi-2096000000-da9354b628843987f1422017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Levorphanol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Levorphanol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-0a4i-5930000000-4593c62f1e2a0579a2482014-09-20Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Levorphanol 10V, Positive-QTOFsplash10-0a4i-0090000000-6ba0fc98a8d249fe2da02016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Levorphanol 20V, Positive-QTOFsplash10-0a4i-0090000000-d3e64fd4fd1d790a54bb2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Levorphanol 40V, Positive-QTOFsplash10-0596-6790000000-7a77fc910d8d984d10122016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Levorphanol 10V, Negative-QTOFsplash10-0a4i-0090000000-503f808754310f6363732016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Levorphanol 20V, Negative-QTOFsplash10-0a4i-0090000000-bce69f729c40b2f3bed92016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Levorphanol 40V, Negative-QTOFsplash10-002g-1290000000-97ee80b268d9fa4de6792016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Levorphanol 10V, Positive-QTOFsplash10-0a4i-0090000000-07569ae87a2b34cbffc02021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Levorphanol 20V, Positive-QTOFsplash10-0a4i-0090000000-02552f8621a9e610534e2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Levorphanol 40V, Positive-QTOFsplash10-03di-2960000000-72882cb61c3a77dadafb2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Levorphanol 10V, Negative-QTOFsplash10-0a4i-0090000000-4d2203d29a4418e5d7732021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Levorphanol 20V, Negative-QTOFsplash10-0a4i-0090000000-4d2203d29a4418e5d7732021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Levorphanol 40V, Negative-QTOFsplash10-0f6t-0490000000-d5048ebe52cdbfced4642021-10-11Wishart 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 DB00854 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00854 details
Abnormal Concentrations
Not Available
Predicted Concentrations
BiospecimenValueOriginal ageOriginal sexOriginal conditionComments
Blood0.000 uMAdult (>18 years old)BothNormalPredicted based on drug qualities
Blood0.000 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00854
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID16736212
KEGG Compound IDC08014
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkLevorphanol
METLIN IDNot Available
PubChem Compound5359272
PDB IDNot Available
ChEBI ID119572
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. Highly stereoselective. receptor for enkephalins
Gene Name:
OPRD1
Uniprot ID:
P41143
Molecular weight:
40412.3
References
  1. Prommer E: Levorphanol: the forgotten opioid. Support Care Cancer. 2007 Mar;15(3):259-64. Epub 2006 Oct 13. [PubMed:17039381 ]
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. Allen RM, Granger AL, Dykstra LA: The competitive N-methyl-D-aspartate receptor antagonist (-)-6-phosphonomethyl-deca-hydroisoquinoline-3-carboxylic acid (LY235959) potentiates the antinociceptive effects of opioids that vary in efficacy at the mu-opioid receptor. J Pharmacol Exp Ther. 2003 Nov;307(2):785-92. Epub 2003 Sep 15. [PubMed:12975489 ]
  2. Prommer E: Levorphanol: the forgotten opioid. Support Care Cancer. 2007 Mar;15(3):259-64. Epub 2006 Oct 13. [PubMed:17039381 ]
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 dynorphins. May play a role in arousal and regulation of autonomic and neuroendocrine functions
Gene Name:
OPRK1
Uniprot ID:
P41145
Molecular weight:
42644.7
References
  1. Prommer E: Levorphanol: the forgotten opioid. Support Care Cancer. 2007 Mar;15(3):259-64. Epub 2006 Oct 13. [PubMed:17039381 ]