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Record Information
Version3.6
Creation Date2012-09-06 15:16:50 UTC
Update Date2016-02-11 01:29:49 UTC
HMDB IDHMDB14748
Secondary Accession NumbersNone
Metabolite Identification
Common NameMetaraminol
DescriptionMetaraminol is only found in individuals that have used or taken this drug. It is an adrenergic agonist that acts predominantly at alpha adrenergic receptors and also stimulates the release of norepinephrine. It has been used primarily as a vasoconstrictor in the treatment of hypotension. [PubChem]Metaraminol acts through peripheral vasoconstriction by acting as a pure alpha-1 adrenergic receptor agonist, consequently increasing systemic blood pressure (both systolic & diastolic). Its effect is thought to be associated with the inhibition of adenyl cyclase which leads to an inhibition of the production of cAMP. Another effect of Metaraminol is that it releases norepinephrine from its storage sites indirectly.
Structure
Thumb
Synonyms
ValueSource
(-)-erythro-MetaraminolChEBI
1-(m-Hydroxyphenyl)-2-amino-1-propanolChEBI
1-MetaraminolChEBI
2-amino-1-(m-Hydroxyphenyl)-1-propanolChEBI
3-HydroxyphenylisopropanolamineChEBI
alpha-(1-Aminoethyl)-3-hydroxybenzenemethanolChEBI
alpha-(m-Hydroxyphenyl)-beta-aminopropanolChEBI
HydroxynorephedrineChEBI
L-MetaraminolChEBI
m-Hydroxy norephedrineChEBI
m-HydroxyphenylpropanolamineChEBI
m-HydroxypropadrineChEBI
MetaraminolumChEBI
a-(1-Aminoethyl)-3-hydroxybenzenemethanolGenerator
α-(1-aminoethyl)-3-hydroxybenzenemethanolGenerator
a-(m-Hydroxyphenyl)-b-aminopropanolGenerator
α-(m-hydroxyphenyl)-β-aminopropanolGenerator
Metaraminol bitartrateHMDB
Chemical FormulaC9H13NO2
Average Molecular Weight167.205
Monoisotopic Molecular Weight167.094628665
IUPAC Name3-[(1R,2S)-2-amino-1-hydroxypropyl]phenol
Traditional Namemetaraminol
CAS Registry Number54-49-9
SMILES
C[C@H](N)[C@H](O)C1=CC(O)=CC=C1
InChI Identifier
InChI=1S/C9H13NO2/c1-6(10)9(12)7-3-2-4-8(11)5-7/h2-6,9,11-12H,10H2,1H3/t6-,9-/m0/s1
InChI KeyInChIKey=WXFIGDLSSYIKKV-RCOVLWMOSA-N
Chemical Taxonomy
DescriptionThis compound 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
  • Aralkylamine
  • Phenol
  • Secondary alcohol
  • 1,2-aminoalcohol
  • Hydrocarbon derivative
  • Aromatic alcohol
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Amine
  • Alcohol
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Drug
Biofunction
  • Adrenergic Agents
  • Adrenergic alpha-Agonists
  • Sympathomimetics
  • Vasoconstrictor Agents
Application
  • Pharmaceutical
Cellular locations
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point107.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility1.28e+01 g/LNot Available
LogP0.6Not Available
Predicted Properties
PropertyValueSource
Water Solubility12.8 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity46.89 m3·mol-1ChemAxon
Polarizability17.84 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00610
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00610
  • Not Applicable
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00610
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID5695
KEGG Compound IDC07146
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkMetaraminol
NuGOwiki LinkHMDB14748
Metagene LinkHMDB14748
METLIN IDNot Available
PubChem Compound5906
PDB IDNot Available
ChEBI ID6794
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Koga S, Shiraishi K, Saito Y: Post-traumatic priapism treated with metaraminol bitartrate: case report. J Trauma. 1990 Dec;30(12):1591-3. [2258979 ]
  2. Block T, Sturm W, Ernst G, Staehler G, Schmiedt E: [Metaraminol in therapy of various forms of priapism]. Urologe A. 1988 Jul;27(4):225-9. [3140463 ]
  3. McDonald M, Santucci RA: Successful management of stuttering priapism using home self-injections of the alpha-agonist metaraminol. Int Braz J Urol. 2004 Mar-Apr;30(2):121-2. [15703094 ]

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. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [17016423 ]
  3. Tatsuta M, Iishi H, Baba M, Yano H, Sakai N, Uehara H, Hirasawa R, Nakaizumi A: Alpha1-adrenoceptor stimulation enhances experimental gastric carcinogenesis induced by N-methyl-N'-nitro-N-nitrosoguanidine in Wistar rats. Int J Cancer. 1998 Jul 29;77(3):467-9. [9663612 ]