Metanephrine (CHEM021680)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 18:09:51 UTC
Update Date2016-11-09 01:17:20 UTC
Accession NumberCHEM021680
Identification
Common NameMetanephrine
ClassSmall Molecule
DescriptionMetanephrine, also known as metanephrine, belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety. Metanephrine is possibly soluble (in water) and a very strong basic compound (based on its pKa). Metanephrine participates in a number of enzymatic reactions, within cattle. In particular, Metanephrine can be converted into 3-methoxy-4-hydroxyphenylglycolaldehyde; which is mediated by the enzyme amine oxidase [flavin-containing] a. In addition, Metanephrine and pyrocatechol can be biosynthesized from epinephrine and guaiacol; which is mediated by the enzyme catechol O-methyltransferase. In cattle, metanephrine is involved in the metabolic pathway called the tyrosine metabolism pathway.
Contaminant Sources
  • FooDB Chemicals
  • HMDB Contaminants - Urine
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(+/-)-metanephrineHMDB
3-Methoxy-adrenalineHMDB
3-MethoxyadrenalineHMDB
3-O-Methyl-adrenalineHMDB
3-O-MethylepinephrineHMDB
4-Hydroxy-3-methoxy-N-methylphenethanolamineHMDB
DL-3-O-MethyladrenalineHMDB
DL-MetanephrineHMDB
m-O-MethyladrenalineHMDB
MetadrenalineHMDB
Chemical FormulaC10H15NO3
Average Molecular Mass197.231 g/mol
Monoisotopic Mass197.105 g/mol
CAS Registry Number5001-33-2
IUPAC Name4-[1-hydroxy-2-(methylamino)ethyl]-2-methoxyphenol
Traditional Name(+/-)-metanephrine
SMILESCNCC(O)C1=CC(OC)=C(O)C=C1
InChI IdentifierInChI=1S/C10H15NO3/c1-11-6-9(13)7-3-4-8(12)10(5-7)14-2/h3-5,9,11-13H,6H2,1-2H3
InChI KeyJWJCTZKFYGDABJ-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenols
Sub ClassMethoxyphenols
Direct ParentMethoxyphenols
Alternative Parents
Substituents
  • Methoxyphenol
  • Phenoxy compound
  • Anisole
  • Phenol ether
  • Methoxybenzene
  • Alkyl aryl ether
  • 1-hydroxy-2-unsubstituted benzenoid
  • Aralkylamine
  • Monocyclic benzene moiety
  • Secondary alcohol
  • 1,2-aminoalcohol
  • Secondary amine
  • Ether
  • Secondary aliphatic amine
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Organopnictogen compound
  • Organic oxygen compound
  • Amine
  • Organic nitrogen compound
  • Alcohol
  • Aromatic alcohol
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility13 g/LALOGPS
logP-0.27ALOGPS
logP-0.00068ChemAxon
logS-1.2ALOGPS
pKa (Strongest Acidic)10.05ChemAxon
pKa (Strongest Basic)9.25ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area61.72 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity53.71 m³·mol⁻¹ChemAxon
Polarizability21.13 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-014i-0910000000-a886bef599ae583766b9Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-014i-0910000000-a886bef599ae583766b9Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9300000000-99e319cf43defe7cc611Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0g6r-9553000000-f11ff40fb7a8af16bb25Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001j-0900000000-4c31604c1b2a54419f92Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001j-0900000000-12556e41dd73a4575162Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f6w-4900000000-403de00b0b43ed22918fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0900000000-3d29615883725ba8e07cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0032-1900000000-1ccaa0d8ce9764cdfe35Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0pic-4900000000-051892c7895245a3de0cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001j-0900000000-545ae65ccf6b1aaf8f43Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001a-1900000000-ad33b1d4593df03f60e1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-5900000000-61cd5865cf7abd2bba67Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0900000000-33b506e73b8f2abe6bdbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000b-0900000000-361e5b74103dd493ac47Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4m-6900000000-49bdcf483f24e0b4ffd4Spectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0004063
FooDB IDFDB023296
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG ID46078
BioCyc IDNot Available
METLIN ID65
PDB IDNot Available
Wikipedia LinkMetanephrine
Chemspider ID19844
ChEBI ID144365
PubChem Compound ID21100
Kegg Compound IDC05588
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. van Dam PS, van Gils A, Canninga-van Dijk MR, de Koning EJ, Hofland LJ, de Herder WW: Sequential ACTH and catecholamine secretion in a phaeochromocytoma. Eur J Endocrinol. 2002 Aug;147(2):201-6.
2. Schmidt J, Mohr VD, Metzger P, Zirngibl H: Posttraumatic hypertension secondary to adrenal hemorrhage mimicking pheochromocytoma: case report. J Trauma. 1999 May;46(5):973-5.
3. Artal R, Platt LD, Kammula RK, Strassner HT, Gratacos J, Golde SH: Sympathoadrenal activity in infants of diabetic mothers. Am J Obstet Gynecol. 1982 Feb 15;142(4):436-9.
4. Uchikura K, Horikawa R, Tanimura T, Kabasawa Y: Determination of catecholamines by radioenzymatic assay using ion-pair liquid chromatography. J Chromatogr. 1981 Apr 10;223(1):41-50.
5. Artal R, Hobel CJ, Lam R, Oddie TH, Fisher DA: Free metanephrine in human amniotic fluid as an index of fetal sympathetic nervous system maturation. Am J Obstet Gynecol. 1979 Feb 15;133(4):452-4.
6. Kitamura T, Alroy J, Gatmaitan Z, Inoue M, Mikami T, Jansen P, Arias IM: Defective biliary excretion of epinephrine metabolites in mutant (TR-) rats: relation to the pathogenesis of black liver in the Dubin-Johnson syndrome and Corriedale sheep with an analogous excretory defect. Hepatology. 1992 Jun;15(6):1154-9.
7. Eisenhofer G, Keiser H, Friberg P, Mezey E, Huynh TT, Hiremagalur B, Ellingson T, Duddempudi S, Eijsbouts A, Lenders JW: Plasma metanephrines are markers of pheochromocytoma produced by catechol-O-methyltransferase within tumors. J Clin Endocrinol Metab. 1998 Jun;83(6):2175-85.
8. Higa S, Suzuki T, Sakoda S, Kishimoto S, Takaba Y, Nakajima A, Markey SP: Disturbed function of the pineal gland in familial amyloid polyneuropathy. J Neural Transm. 1987;69(1-2):97-103.
9. Beck O, Faull KF: Extractive acylation and mass spectrometric assay of 3-methoxytyramine, normetanephrine, and metanephrine in cerebrospinal fluid. Anal Biochem. 1985 Sep;149(2):492-500.
10. Goldstein DS, Eisenhofer G, Kopin IJ: Sources and significance of plasma levels of catechols and their metabolites in humans. J Pharmacol Exp Ther. 2003 Jun;305(3):800-11. Epub 2003 Mar 20.
11. Pagliari R, Cottet-Emard JM, Peyrin L: Determination of free and conjugated normetanephrine and metanephrine in human plasma by high-performance liquid chromatography with electrochemical detection. J Chromatogr. 1991 Jan 18;563(1):23-36.
12. Kaplan NM, Kramer NJ, Holland OB, Sheps SG, Gomez-Sanchez C: Single-voided urine metanephrine assays in screening for pheochromocytoma. Arch Intern Med. 1977 Feb;137(2):190-3.
13. Taylor RL, Singh RJ: Validation of liquid chromatography-tandem mass spectrometry method for analysis of urinary conjugated metanephrine and normetanephrine for screening of pheochromocytoma. Clin Chem. 2002 Mar;48(3):533-9.
14. Eisenhofer G, Kopin IJ, Goldstein DS: Catecholamine metabolism: a contemporary view with implications for physiology and medicine. Pharmacol Rev. 2004 Sep;56(3):331-49.