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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:52 UTC
Update Date2017-10-23 19:06:35 UTC
HMDB IDHMDB0015652
Secondary Accession Numbers
  • HMDB15652
Metabolite Identification
Common NameLevonordefrin
DescriptionLevonordefrin is only found in individuals that have used or taken this drug. It acts as a topical nasal decongestant and vasoconstrictor, most often used in dentistry.It is designed to mimic the molecular shape of adrenaline. It binds to alpha-adrenergic receptors in the nasal mucosa. Here it can, therefore, cause vasoconstriction
Structure
Thumb
Synonyms
ValueSource
alpha-MethylnoradrenalineKegg
CorbadrineKegg
neo-CobefrinKegg
a-MethylnoradrenalineGenerator
α-methylnoradrenalineGenerator
4-(2-amino-1-Hydroxypropyl)-1,2-benzenediol, (r*,r*)-isomerMeSH
4-(2-amino-1-Hydroxypropyl)-1,2-benzenediol, (r*,s*)-isomerMeSH
neo CobefrinMeSH
Nordefrin hydrochloride, (r*,s*)-(+,-)-isomerMeSH
Nordefrin tartrate, (r*,s*), (r*,r*) isomerMeSH
3,4 DihydroxynorephedrineMeSH
Hydrochloride, nordefrinMeSH
NordefrinMeSH
Nordefrin hydrochlorideMeSH
Nordefrin tartrate, (r*,r*), (r*,r*) isomerMeSH
Nordefrin, (r*,s*)-isomerMeSH
alpha MethylnoradrenalineMeSH
alpha MethylnorepinephrineMeSH
4-(2-amino-1-Hydroxypropyl)-1,2-benzenediol hydrochloride, (r*,r*)-(+,-)-isomerMeSH
4-(2-amino-1-Hydroxypropyl)-1,2-benzenediol tartrate, (r*,r*), (r*,r*)-isomerMeSH
4-(2-amino-1-Hydroxypropyl)-1,2-benzenediol tartrate, (r*,s*), (r*,r*)-isomerMeSH
NeoCobefrinMeSH
Nordefrin hydrochloride, (r*,r*)-(+,-)-isomerMeSH
Nordefrin, (r*,r*)-isomerMeSH
3,4-DihydroxynorephedrineMeSH
4-(2-amino-1-Hydroxypropyl)-1,2-benzenediolMeSH
4-(2-amino-1-Hydroxypropyl)-1,2-benzenediol hydrochloride, (r*,s*)-(+-)-isomerMeSH
CobefrineMeSH
MethylnorepinephrineMeSH
NorephrineMeSH
alpha-MethylnorepinephrineMeSH
Chemical FormulaC9H13NO3
Average Molecular Weight183.2044
Monoisotopic Molecular Weight183.089543287
IUPAC Name4-[(1R,2S)-2-amino-1-hydroxypropyl]benzene-1,2-diol
Traditional Namelevonordefrin
CAS Registry Number829-74-3
SMILES
C[C@H](N)[C@H](O)C1=CC(O)=C(O)C=C1
InChI Identifier
InChI=1S/C9H13NO3/c1-5(10)9(13)6-2-3-7(11)8(12)4-6/h2-5,9,11-13H,10H2,1H3/t5-,9-/m0/s1
InChI KeyGEFQWZLICWMTKF-CDUCUWFYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as phenylpropanes. These are organic compounds containing a phenylpropane moiety.
KingdomChemical entities
Super ClassOrganic compounds
ClassBenzenoids
Sub ClassBenzene and substituted derivatives
Direct ParentPhenylpropanes
Alternative Parents
Substituents
  • Phenylpropane
  • Catechol
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Aralkylamine
  • 1,2-aminoalcohol
  • Secondary alcohol
  • Organic nitrogen compound
  • Aromatic alcohol
  • Primary amine
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Organic oxygen compound
  • Amine
  • Alcohol
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

Role

Industrial application:

  Pharmaceutical industry:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility14.6 g/LALOGPS
logP-0.77ALOGPS
logP-0.39ChemAxon
logS-1.1ALOGPS
pKa (Strongest Acidic)9.63ChemAxon
pKa (Strongest Basic)8.96ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area86.71 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity48.87 m³·mol⁻¹ChemAxon
Polarizability18.81 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000f-9700000000-97a66276892b2b9a6d84View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-03di-4493000000-9bd4051e22d9ba138050View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0159-0900000000-bca9b4d25388d07c977fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014j-0900000000-5eda894ad9ec103325cfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0zfs-5900000000-2e7d4302e50276d6779dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0900000000-f0b8ebb5e32926cf168eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01qi-0900000000-affe67c3772699b13b41View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-2900000000-98e0e5a67c5da9331891View in MoNA
Biological Properties
Cellular Locations
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
No entries found
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB06707 details
UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB06707 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB06707
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID144416
KEGG Compound IDC11768
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkLevonordefrin
METLIN IDNot Available
PubChem Compound164739
PDB IDNot Available
ChEBI ID128939
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:
This alpha-adrenergic receptor mediates its action by association with G proteins that activate a phosphatidylinositol- calcium second messenger system. Its effect is mediated by G(q) and G(11) proteins
Gene Name:
ADRA1A
Uniprot ID:
P35348
Molecular weight:
51486.0
References
  1. Jastak JT, Yagiela JA: Vasoconstrictors and local anesthesia: a review and rationale for use. J Am Dent Assoc. 1983 Oct;107(4):623-30. [PubMed:6355236 ]
  2. Hersh EV, Giannakopoulos H: Beta-adrenergic blocking agents and dental vasoconstrictors. Dent Clin North Am. 2010 Oct;54(4):687-96. doi: 10.1016/j.cden.2010.06.009. [PubMed:20831932 ]
  3. Yang HT, Endoh M: (+/-)-tamsulosin, an alpha 1A-adrenoceptor antagonist, inhibits the positive inotropic effect but not the accumulation of inositol phosphates in rabbit heart. Eur J Pharmacol. 1996 Oct 3;312(3):281-91. [PubMed:8894610 ]
  4. Haenisch B, Walstab J, Herberhold S, Bootz F, Tschaikin M, Ramseger R, Bonisch H: Alpha-adrenoceptor agonistic activity of oxymetazoline and xylometazoline. Fundam Clin Pharmacol. 2010 Dec;24(6):729-39. doi: 10.1111/j.1472-8206.2009.00805.x. [PubMed:20030735 ]

Transporters

General function:
Involved in neurotransmitter:sodium symporter activity
Specific function:
Amine transporter. Terminates the action of noradrenaline by its high affinity sodium-dependent reuptake into presynaptic terminals.
Gene Name:
SLC6A2
Uniprot ID:
P23975
Molecular weight:
69331.42
References
  1. Habecker BA, Willison BD, Shi X, Woodward WR: Chronic depolarization stimulates norepinephrine transporter expression via catecholamines. J Neurochem. 2006 May;97(4):1044-51. Epub 2006 Mar 29. [PubMed:16573647 ]
  2. Bonisch H, Bruss M: The norepinephrine transporter in physiology and disease. Handb Exp Pharmacol. 2006;(175):485-524. [PubMed:16722247 ]
  3. Mandela P, Ordway GA: KCl stimulation increases norepinephrine transporter function in PC12 cells. J Neurochem. 2006 Sep;98(5):1521-30. Epub 2006 Jul 31. [PubMed:16879714 ]
  4. Gutman DA, Owens MJ: Serotonin and norepinephrine transporter binding profile of SSRIs. Essent Psychopharmacol. 2006;7(1):35-41. [PubMed:16989291 ]
  5. Ksiazek P, Buraczynska K, Buraczynska M: Norepinephrine transporter gene (NET) polymorphism in patients with type 2 diabetes. Kidney Blood Press Res. 2006;29(6):338-43. Epub 2006 Nov 23. [PubMed:17124432 ]