ContaminantDB: Levonordefrin

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-05-22 05:41:03 UTC

Update Date

2016-11-09 01:15:53 UTC

Accession Number

CHEM018937

Identification

Common Name

Levonordefrin

Class

Small Molecule

Description

A catecholamine in which the 2-aminoethyl group is substituted with a hydroxy group at C-1 and a methyl group at C-2, with configurations 1R,2S. A metabolite of alpha-methyl-L-dopa, it is an alpha2-adrenergic agonist and acts as a topical nasal decongestant and vasoconstrictor, most often used in dentistry.

Contaminant Sources

HMDB Contaminants - Urine
ToxCast & Tox21 Chemicals

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
alpha-(1-Aminoethyl)-3,4-dihydroxybenzyl alcohol	ChEBI
alpha-Methylnorepinephrine	ChEBI
Corbadrina	ChEBI
Corbadrine	ChEBI
Corbadrinum	ChEBI
Isoadrenaline	ChEBI
Methylnoradrenaline	ChEBI
alpha-Methylnoradrenaline	Kegg
Neo-cobefrin	Kegg
a-(1-Aminoethyl)-3,4-dihydroxybenzyl alcohol	Generator
Α-(1-aminoethyl)-3,4-dihydroxybenzyl alcohol	Generator
a-Methylnorepinephrine	Generator
Α-methylnorepinephrine	Generator
a-Methylnoradrenaline	Generator
Α-methylnoradrenaline	Generator
4-(2-Amino-1-hydroxypropyl)-1,2-benzenediol, (r,r)-isomer	HMDB
4-(2-Amino-1-hydroxypropyl)-1,2-benzenediol, (r,s)-isomer	HMDB
Neo cobefrin	HMDB
Nordefrin hydrochloride, (r,s)-(+,-)-isomer	HMDB
Nordefrin tartrate, (r,s), (r,r) isomer	HMDB
3,4 Dihydroxynorephedrine	HMDB
Hydrochloride, nordefrin	HMDB
Nordefrin	HMDB
Nordefrin hydrochloride	HMDB
Nordefrin tartrate, (r,r), (r,r) isomer	HMDB
Nordefrin, (r,s)-isomer	HMDB
alpha Methylnoradrenaline	HMDB
alpha Methylnorepinephrine	HMDB
4-(2-Amino-1-hydroxypropyl)-1,2-benzenediol hydrochloride, (r,r)-(+,-)-isomer	HMDB
4-(2-Amino-1-hydroxypropyl)-1,2-benzenediol tartrate, (r,r), (r,r)-isomer	HMDB
4-(2-Amino-1-hydroxypropyl)-1,2-benzenediol tartrate, (r,s), (r,r)-isomer	HMDB
NeoCobefrin	HMDB
Nordefrin hydrochloride, (r,r)-(+,-)-isomer	HMDB
Nordefrin, (r,r)-isomer	HMDB
3,4-Dihydroxynorephedrine	HMDB
4-(2-Amino-1-hydroxypropyl)-1,2-benzenediol	HMDB
4-(2-Amino-1-hydroxypropyl)-1,2-benzenediol hydrochloride, (r,s)-(+-)-isomer	HMDB
Cobefrine	HMDB
Methylnorepinephrine	HMDB
Norephrine	HMDB
Levonordefrin	ChEBI

Chemical Formula

C₉H₁₃NO₃

Average Molecular Mass

183.204 g/mol

Monoisotopic Mass

183.090 g/mol

CAS Registry Number

829-74-3

IUPAC Name

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

Traditional Name

levonordefrin

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 Key

GEFQWZLICWMTKF-CDUCUWFYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as phenylpropanes. These are organic compounds containing a phenylpropane moiety.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Phenylpropanes

Direct Parent

Phenylpropanes

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 Framework

Aromatic homomonocyclic compounds

External Descriptors

catecholamine (CHEBI:10304 )

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	14.6 g/L	ALOGPS
logP	-0.77	ALOGPS
logP	-0.39	ChemAxon
logS	-1.1	ALOGPS
pKa (Strongest Acidic)	9.63	ChemAxon
pKa (Strongest Basic)	8.96	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	86.71 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	48.87 m³·mol⁻¹	ChemAxon
Polarizability	18.81 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-000f-9700000000-97a66276892b2b9a6d84	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positive	splash10-03di-4493000000-9bd4051e22d9ba138050	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0159-0900000000-bca9b4d25388d07c977f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014j-0900000000-5eda894ad9ec103325cf	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0zfs-5900000000-2e7d4302e50276d6779d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-0900000000-f0b8ebb5e32926cf168e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-01qi-0900000000-affe67c3772699b13b41	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-2900000000-98e0e5a67c5da9331891	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0900000000-fb62819bff82a937e5bc	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00kb-2900000000-ef244b4a084824e097b1	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0uk9-9600000000-8e21565f2276bece257e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-01x0-0900000000-4d329ca34072b59eedd4	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00di-0900000000-f3d6884a1d9a0b402eb9	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0596-9800000000-0a42555edab27c646a52	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum