Metaraminol bitartrate (CHEM018413)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 05:13:36 UTC
Update Date2016-11-09 01:15:47 UTC
Accession NumberCHEM018413
Identification
Common NameMetaraminol bitartrate
ClassSmall Molecule
DescriptionMetaraminol (INN; trade names Aramine, Metaramin, and Pressonex), also known as metaradrine, a stereoisomer of meta-hydroxynorephedrine (3,β-dihydroxyamphetamine), is a potent sympathomimetic amine used in the prevention and treatment of hypotension, particularly as a complication of anesthesia. It is an α1-adrenergic receptor agonist with some β effect.Metaraminol is also used in the treatment of priapism. Although not approved for this use, it appears to be effective.
Contaminant Sources
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
Metaraminol bitartric acidGenerator
m-HydroxyphenylpropanolamineMeSH
Tartrate, metaraminolMeSH
Metaraminol bitartrate (1:1)MeSH
AraminolMeSH
m-HydroxynorephedrineMeSH
m HydroxynorephedrineMeSH
Bitartrate, metaraminolMeSH
IsophenylephrineMeSH
Metaraminol tartrateMeSH
AramineMeSH
MetaradrinMeSH
HydroxyphenylpropanolamineMeSH
m HydroxyphenylpropanolamineMeSH
MetaraminolMeSH
Meta hydroxynorephedrineMeSH
Meta-hydroxynorephedrineMeSH
Merck sharp and dohme brand OF metaraminol bitartrateMeSH
Metaraminol bitartrateMeSH
Merck brand OF metaraminol bitartrateMeSH
(2R,3S)-2,3-Dihydroxybutanedioate
3-[(1R,2S)-2-amino-1-hydroxypropyl]phenol
Chemical FormulaC13H19NO8
Average Molecular Mass317.294 g/mol
Monoisotopic Mass317.111 g/mol
CAS Registry Number33402-03-8
IUPAC Name(2R,3S)-2,3-dihydroxybutanedioic acid; 3-[(1R,2S)-2-amino-1-hydroxypropyl]phenol
Traditional Name(-)-tartaric acid; metaraminol
SMILES[H][C@](O)(C(O)=O)[C@]([H])(O)C(O)=O.[H][C@@](C)(N)[C@]([H])(O)C1=CC(O)=CC=C1
InChI IdentifierInChI=1S/C9H13NO2.C4H6O6/c1-6(10)9(12)7-3-2-4-8(11)5-7;5-1(3(7)8)2(6)4(9)10/h2-6,9,11-12H,10H2,1H3;1-2,5-6H,(H,7,8)(H,9,10)/t6-,9-;1-,2+/m0./s1
InChI KeyVENXSELNXQXCNT-OHAABKCISA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as phenylpropanes. These are organic compounds containing a phenylpropane moiety.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassPhenylpropanes
Direct ParentPhenylpropanes
Alternative Parents
Substituents
  • Phenylpropane
  • Beta-hydroxy acid
  • Phenol
  • Short-chain hydroxy acid
  • Sugar acid
  • Aralkylamine
  • 1-hydroxy-2-unsubstituted benzenoid
  • 1-hydroxy-4-unsubstituted benzenoid
  • Fatty acid
  • Alpha-hydroxy acid
  • Dicarboxylic acid or derivatives
  • Hydroxy acid
  • Monosaccharide
  • 1,2-aminoalcohol
  • Secondary alcohol
  • Carboxylic acid derivative
  • Carboxylic acid
  • Carbonyl group
  • Organonitrogen compound
  • Organooxygen compound
  • Primary aliphatic amine
  • Alcohol
  • Organic nitrogen compound
  • Primary amine
  • Amine
  • Aromatic alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkNot Available
External DescriptorsNot Available
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 Solubility12.8 g/LALOGPS
logP-0.59ALOGPS
logP-0.045ChemAxon
logS-1.1ALOGPS
pKa (Strongest Acidic)9.03ChemAxon
pKa (Strongest Basic)9.68ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area66.48 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity46.89 m³·mol⁻¹ChemAxon
Polarizability17.86 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0009000000-54b9ac33e9f28066b93dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-0009000000-54b9ac33e9f28066b93dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-0009000000-54b9ac33e9f28066b93dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0009000000-0a783200fe93b58fd87cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0009000000-0a783200fe93b58fd87cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-0009000000-0a783200fe93b58fd87cSpectrum
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 IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkMetaraminol
Chemspider IDNot Available
ChEBI IDNot Available
PubChem Compound ID60196269
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available