ContaminantDB: Metaraminol bitartrate

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

Record Information

Version

1.0

Creation Date

2016-05-22 05:13:36 UTC

Update Date

2026-04-06 13:46:38 UTC

Accession Number

CHEM018413

Identification

Common Name

Metaraminol bitartrate

Class

Small Molecule

Description

Metaraminol (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 Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Metaraminol bitartric acid	Generator
m-Hydroxyphenylpropanolamine	MeSH
Tartrate, metaraminol	MeSH
Metaraminol bitartrate (1:1)	MeSH
Araminol	MeSH
m-Hydroxynorephedrine	MeSH
m Hydroxynorephedrine	MeSH
Bitartrate, metaraminol	MeSH
Isophenylephrine	MeSH
Metaraminol tartrate	MeSH
Aramine	MeSH
Metaradrin	MeSH
Hydroxyphenylpropanolamine	MeSH
m Hydroxyphenylpropanolamine	MeSH
Metaraminol	MeSH
Meta hydroxynorephedrine	MeSH
Meta-hydroxynorephedrine	MeSH
Merck sharp and dohme brand OF metaraminol bitartrate	MeSH
Metaraminol bitartrate	MeSH
Merck brand OF metaraminol bitartrate	MeSH
(2R,3S)-2,3-Dihydroxybutanedioate
3-[(1R,2S)-2-amino-1-hydroxypropyl]phenol

Chemical Formula

C₁₃H₁₉NO₈

Average Molecular Mass

317.294 g/mol

Monoisotopic Mass

317.111 g/mol

CAS Registry Number

33402-03-8

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 Identifier

InChI=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 Key

VENXSELNXQXCNT-OHAABKCISA-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
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 Framework

Not Available

External Descriptors

Not Available

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	12.8 g/L	ALOGPS
logP	-0.59	ALOGPS
logP	-0.045	ChemAxon
logS	-1.1	ALOGPS
pKa (Strongest Acidic)	9.03	ChemAxon
pKa (Strongest Basic)	9.68	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	66.48 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	46.89 m³·mol⁻¹	ChemAxon
Polarizability	17.86 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 LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0009000000-54b9ac33e9f28066b93d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014i-0009000000-54b9ac33e9f28066b93d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-014i-0009000000-54b9ac33e9f28066b93d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0009000000-0a783200fe93b58fd87c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014i-0009000000-0a783200fe93b58fd87c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-014i-0009000000-0a783200fe93b58fd87c	Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

Not Available

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

Not Available

Uses/Sources

Not Available

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

Not Available

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Metaraminol

Chemspider ID

Not Available

ChEBI ID

Not Available

PubChem Compound ID

60196269

Kegg Compound ID

Not Available

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

Not Available

Metaraminol bitartrate (CHEM018413)

Structure for CHEM018413: Metaraminol bitartrate