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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2022-09-09 19:40:33 UTC
Update Date2022-09-22 18:34:39 UTC
HMDB IDHMDB0341203
Secondary Accession NumbersNone
Metabolite Identification
Common Name(-)-Deoxyephedrine
DescriptionLevmetamfetamine belongs to the class of organic compounds known as amphetamines and derivatives. These are organic compounds containing or derived from 1-phenylpropan-2-amine. This has caused users to test positive for amphetamines. Levmetamfetamine is a drug which is used over-the-counter for nasal congestion. Levmetamfetamine is a very strong basic compound (based on its pKa). The study did not test the oral administration of levomethamphetamine. Currently there are no studies demonstrating "drug liking" scores of oral levomethamphetamine that are similar to racemic methamphetamine or dextromethamphetamine in either recreational users or medicinal users. Levomethamphetamine is a sympathomimetic vasoconstrictor which is the active ingredient in some over-the-counter (OTC) nasal decongestant inhalers in the United States. Among its physiological effects are the vasoconstriction that makes it useful for nasal decongestion. Selegiline itself has neuroprotective and neuro-rescuing effects, but concern over the resulting levomethamphetamine's neurotoxicity led to development of alternative MAOB inhibitors such as rasagiline, that do not produce toxic metabolites. Levomethamphetamine can register on urine drug screens as either methamphetamine, amphetamine, or both, depending on the subject's metabolism and dosage. Levomethamphetamine is the active metabolite of the antiparkinson's drug selegiline. Levomethamphetamine crosses the blood-brain-barrier and acts as a TAAR1 agonist, functioning as a selective norepinephrine releasing agent (with few or no effects on the release of dopamine), so it affects the central nervous system, although its effects are qualitatively distinct relative to those of dextromethamphetamine.
Structure
Thumb
Synonyms
ValueSource
L-DESOXYEPHEDRINEChEMBL
Chemical FormulaC10H15N
Average Molecular Weight149.237
Monoisotopic Molecular Weight149.120449487
IUPAC Namemethyl[(2R)-1-phenylpropan-2-yl]amine
Traditional Name(-)-methamphetamine
CAS Registry NumberNot Available
SMILES
CN[C@H](C)CC1=CC=CC=C1
InChI Identifier
InChI=1S/C10H15N/c1-9(11-2)8-10-6-4-3-5-7-10/h3-7,9,11H,8H2,1-2H3/t9-/m1/s1
InChI KeyMYWUZJCMWCOHBA-SECBINFHSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as amphetamines and derivatives. These are organic compounds containing or derived from 1-phenylpropan-2-amine.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassPhenethylamines
Direct ParentAmphetamines and derivatives
Alternative Parents
Substituents
  • Amphetamine or derivatives
  • Phenylpropane
  • Aralkylamine
  • Secondary amine
  • Secondary aliphatic amine
  • Organic nitrogen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Amine
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Not AvailableNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
logP2.23ALOGPS
logP2.24ChemAxon
logS-2.2ALOGPS
pKa (Strongest Basic)10.21ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area12.03 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity48.48 m³·mol⁻¹ChemAxon
Polarizability18.09 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Kovats Retention Indices

Not Available
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - (-)-Deoxyephedrine CI-B (Non-derivatized)splash10-0udi-0900000000-8d39b849b8598c565a332017-09-12HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (-)-Deoxyephedrine GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a59-9200000000-ad675002f4bc5b9ffdee2017-08-28Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (-)-Deoxyephedrine 10V, Positive-QTOFsplash10-0udi-0900000000-6ca41b91a4dd107137f52017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (-)-Deoxyephedrine 20V, Positive-QTOFsplash10-0uxr-3900000000-7fa23fc8e2e96d14abcc2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (-)-Deoxyephedrine 40V, Positive-QTOFsplash10-0006-9300000000-104f35aae3c1bcbc78872017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (-)-Deoxyephedrine 10V, Negative-QTOFsplash10-0002-0900000000-503d557b64d8fcd09a362017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (-)-Deoxyephedrine 20V, Negative-QTOFsplash10-0002-1900000000-d34387a31168c299ab032017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (-)-Deoxyephedrine 40V, Negative-QTOFsplash10-0ku6-9400000000-3a9b55d0b53a10725f672017-07-26Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedCancer patients undergoing total body irradiation details
UrineDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedCancer patients undergoing total body irradiation details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB09571
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkLevomethamphetamine
METLIN IDNot Available
PubChem Compound36604
PDB IDNot Available
ChEBI IDNot Available
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 References
  1. Simon-Manso Y, Marupaka R, Yan X, Liang Y, Telu KH, Mirokhin Y, Stein SE: Mass Spectrometry Fingerprints of Small-Molecule Metabolites in Biofluids: Building a Spectral Library of Recurrent Spectra for Urine Analysis. Anal Chem. 2019 Sep 17;91(18):12021-12029. doi: 10.1021/acs.analchem.9b02977. Epub 2019 Aug 30. [PubMed:31424920 ]