Levonordefrin

Common Name

Levonordefrin Description

Levonordefrin 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 molecliar shape of adrenaline. It binds to alpha-adrenergic receptors in the nasal mucosa. Here it can, therefore, cause vasoconstriction Structure

Synonyms

Value Source 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 Formlia

C₉H₁₃NO₃ Average Molecliar Weight

183.2044 Monoisotopic Molecliar Weight

183.089543287 IUPAC Name

4-[(1R,2S)-2-amino-1-hydroxypropyl]benzene-1,2-diol Traditional Name

levonordefrin CAS Registry Number

829-74-3 SMILES

InChI Identifier

InChI Key

GEFQWZLICWMTKF-CDUCUWFYSA-N Chemical Taxonomy Description

This compound belongs to the class of chemical entities known as phenylpropanes. These are organic compounds containing a phenylpropane moiety. Kingdom

Chemical entities Super Class

Organic compounds Class

Benzenoids Sub Class

Benzene and substituted derivatives Direct Parent

Phenylpropanes Alternative Parents

Catechols

Aralkylamines

1-hydroxy-4-unsubstituted benzenoids

1-hydroxy-2-unsubstituted benzenoids

Secondary alcohols

1,2-aminoalcohols

Organopnictogen compounds

Monoalkylamines

Hydrocarbon derivatives

Aromatic alcohols

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

Molecliar Framework

Aromatic homomonocyclic compounds External Descriptors

catecholamine (CHEBI:10304 )

Ontology Status

Expected but not Quantified Origin

Drug

Biofunction

Nasal Decongestants

Vasoconstrictor Agents

Application

Pharmaceutical

Cellliar locations

Membrane

Physical Properties State

Solid Experimental Properties

Property Value Reference Melting PointNot AvailableNot Available Boiling PointNot AvailableNot Available Water SolubilityNot AvailableNot Available LogPNot AvailableNot Available

Predicted Properties

Property Value Source Water Solubility14.6 mg/mLALOGPS 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 Rlie of FiveYesChemAxon Ghose FilterYesChemAxon Vebers RlieYesChemAxon MDDR-like RlieYesChemAxon

Spectra Spectra

Spectrum Type Description Splash Key Predicted LC-MS/MS

Predicted LC-MS/MS Spectrum – 10V, PositiveNot Available Predicted LC-MS/MS

Predicted LC-MS/MS Spectrum – 20V, PositiveNot Available Predicted LC-MS/MS

Predicted LC-MS/MS Spectrum – 40V, PositiveNot Available Predicted LC-MS/MS

Predicted LC-MS/MS Spectrum – 10V, NegativeNot Available Predicted LC-MS/MS

Predicted LC-MS/MS Spectrum – 20V, NegativeNot Available Predicted LC-MS/MS

Predicted LC-MS/MS Spectrum – 40V, NegativeNot Available

Biological Properties Cellliar Locations

Membrane

Biofluid Locations

Blood

Urine

Tissue Location

Not Available Pathways

Not Available Normal Concentrations

Biofluid Status Value Age Sex Condition Reference Details BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB06707

21059682

details UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB06707

21059682

details

Abnormal Concentrations

Not Available Associated Disorders and Diseases Disease References

None Associated OMIM IDs

None External Links DrugBank ID

DB06707 DrugBank Metabolite ID

Not Available Phenol Explorer Compound ID

Not Available Phenol Explorer Metabolite ID

Not Available FoodDB ID

Not Available KNApSAcK ID

Not Available Chemspider ID

144416 KEGG Compound ID

C11768 BioCyc ID

Not Available BiGG ID

Not Available Wikipedia Link

Levonordefrin NuGOwiki Link

HMDB15652 Metagene Link

HMDB15652 METLIN ID

Not Available PubChem Compound

164739 PDB ID

Not Available ChEBI ID

128939

Product: Bufexamac

References Synthesis Reference Not Available Material Safety Data Sheet (MSDS) Not Available General References Not 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 ]

PMID: 12948856

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Reverse transcriptase

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