Metaraminol (CED0006932)

Record Information

Version

1.0

Creation Date

2016-05-25 18:21:33 UTC

Update Date

2026-05-14 16:43:57 UTC

Accession Number

CHEM022144

Identification

Common Name

Metaraminol

Class

Small Molecule

Description

Metaraminol is an organic compound with the chemical formula C9H13NO2 and an average molecular weight of 167.21 g/mol. Metaraminol belongs to the phenylpropanes, a subclass of benzene and substituted derivatives within the organic compounds. It is identified as a benzenoid superclass member. The compound is recorded as being found in or released from six distinct sources. These include healthcare, pharmaceuticals, and veterinary products, specifically as cardiac stimulants excluding cardiac glycosides. Other recorded sources are food, food processing and cookware, including food preservation and the treatment of hops; household cleaning and consumer products, such as bleaching agents and tobacco smoke filters; and antennas within electrical and electronic equipment. Exposure to the compound occurs via intramuscular and intravenous routes. Regarding its biological activity, metaraminol has two recorded protein targets. It acts as an agonist of the Alpha-1A adrenergic receptor (ADRA1A) and the D(2) dopamine receptor (DRD2).

Contaminant Type

Not Available

Chemical Structure

MOL SDF 3D SDF PDB SMILES InChI View 3D Structure

Synonyms

Value	Source
(-)-Erythro-metaraminol	ChEBI
1-(m-Hydroxyphenyl)-2-amino-1-propanol	ChEBI
1-Metaraminol	ChEBI
2-Amino-1-(m-hydroxyphenyl)-1-propanol	ChEBI
3-Hydroxyphenylisopropanolamine	ChEBI
alpha-(1-Aminoethyl)-3-hydroxybenzenemethanol	ChEBI
alpha-(m-Hydroxyphenyl)-beta-aminopropanol	ChEBI
Hydroxynorephedrine	ChEBI
L-Metaraminol	ChEBI
m-Hydroxy norephedrine	ChEBI
m-Hydroxyphenylpropanolamine	ChEBI
m-Hydroxypropadrine	ChEBI
Metaraminolum	ChEBI
a-(1-Aminoethyl)-3-hydroxybenzenemethanol	Generator
Α-(1-aminoethyl)-3-hydroxybenzenemethanol	Generator
a-(m-Hydroxyphenyl)-b-aminopropanol	Generator
Α-(m-hydroxyphenyl)-β-aminopropanol	Generator
Metaraminol bitartrate	HMDB
Araminol	HMDB
Bitartrate, metaraminol	HMDB
Merck sharp and dohme brand OF metaraminol bitartrate	HMDB
Metaradrin	HMDB
Metaraminol tartrate	HMDB
m-Hydroxynorephedrine	HMDB
Isophenylephrine	HMDB
Meta hydroxynorephedrine	HMDB
Meta-hydroxynorephedrine	HMDB
Aramine	HMDB
Merck brand OF metaraminol bitartrate	HMDB
Tartrate, metaraminol	HMDB
m Hydroxynorephedrine	HMDB
Metaraminol bitartrate (1:1)	HMDB
Hydroxyphenylpropanolamine	HMDB
m Hydroxyphenylpropanolamine	HMDB

Chemical Formula

C₉H₁₃NO₂

Average Molecular Mass

167.205 g/mol

Monoisotopic Mass

167.095 g/mol

CAS Registry Number

54-49-9

IUPAC Name

3-[(1R,2S)-2-amino-1-hydroxypropyl]phenol

Traditional Name

metaraminol

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 Key

WXFIGDLSSYIKKV-RCOVLWMOSA-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
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Aralkylamine
1,2-aminoalcohol
Secondary alcohol
Organic nitrogen compound
Aromatic alcohol
Hydrocarbon derivative
Primary amine
Organopnictogen compound
Organic oxygen compound
Organooxygen compound
Organonitrogen compound
Primary aliphatic amine
Amine
Alcohol
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

phenylethanolamines (CHEBI:6794 )

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Organoleptic Effects

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	2	ChemAxon
Refractivity	46.89 m³·mol⁻¹	ChemAxon
Polarizability	17.84 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	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	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum	splash10-006x-9500000000-19e4ba301696c4b31705	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	splash10-00kb-2920000000-b05bd4da1530670783f5	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0uxr-0900000000-54fdef7fb806e9618517	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0udi-1900000000-53aa60f30061472008e2	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0a4i-3900000000-03da43641cb5f6da239a	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-056r-9700000000-bb18dd53ad6ac9a58e4f	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-004i-9300000000-3d3ebdc9e7c553d5122c	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0uxr-0900000000-cb591339823fe58da583	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0ue9-0900000000-72d52af9c83300b1cf21	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-001i-5900000000-bf0b8aab46d5d2c3aab6	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-014i-0900000000-0ed81878c7665d2668c8	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00r2-0900000000-432f771c7524342b7012	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-006x-8900000000-01eebcaa27ee21836f1e	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0udi-0900000000-7cfdf32533cde65b37fb	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-001i-0900000000-e5f86599f7aaea978c90	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0pvi-9600000000-1f433b6e4686c25920c0	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0002-0900000000-78917da9a8c1cc2ba5dc	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-05fu-2900000000-edfa5053e3bba3a40bfa	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0006-9300000000-8cb77e21838a1ccce636	Not Available	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, D₂O, predicted)	Not Available	Not Available	View Spectrum
1D NMR	¹H NMR Spectrum (1D, D₂O, predicted)	Not Available	Not Available	View Spectrum

Toxicity Profile

Mechanism of Toxicity

Not Available

Carcinogenicity (IARC Classification)

Not Available

Minimum Risk Level

Not Available

Symptoms

Not Available

Treatment

Not Available

Toxicity Values

Toxicity Value	Unit	Value Range	Organism	Dose Descriptor	Route of Exposure	Predicted or Experimental	Reference
274.0	Log mg/kg	[150:490]	Rat	LD50	oral	predicted	Not Available

Health Effects

Health Effect	Relationship	Direction	Reference

Exposure Sources

Source ID	Source	Sector	Reference
233	Brushes	Personal care & cosmetics	Not Available
286	Cardiac stimulants excl. cardiac glycosides	Healthcare, pharmaceuticals & veterinary products	Not Available
506	Antennas	Electrical & Electronic Equipment	Not Available
545	Food Preservation	Food, food processing & cookware	Not Available
553	Treatment Of Hops	Food, food processing & cookware	Not Available
555	Bleaching Agents	Household cleaning & consumer products	Not Available
569	Tobacco Smoke Filters	Household cleaning & consumer products	Not Available
610	Aftersun Products	Personal care & cosmetics	Not Available
611	Anti Perspirants Or Body Deoderants	Personal care & cosmetics	Not Available
615	Eye Makeup Products	Personal care & cosmetics	Not Available
617	Lip Care Products	Personal care & cosmetics	Not Available
618	Lip Makeup Products	Personal care & cosmetics	Not Available
632	Apparel	Textiles, leather & furnishings	Not Available
642	Footwear	Textiles, leather & furnishings	Not Available
650	Purses Luggage Hand Bags	Textiles, leather & furnishings	Not Available
653	Sewing	Textiles, leather & furnishings	Not Available

Pathways

2 pathways

Metaraminol Drug Metabolism Action Pathway

Metaraminol Predicted Metabolism Pathway

Targets

Structure	Protein	UniProt ID	Organism	Relationship	Details
Click to view 3D structure	Kynureninase	P70712	Rattus norvegicus	Predicted (SEA)	0.0778492
Click to view 3D structure	Kynureninase	Q16719	Humans	Predicted (SEA)	0.622794
Click to view 3D structure	Alpha-2A adrenergic receptor	P08913	Humans	Predicted (SEA)	218.912
Click to view 3D structure	5-hydroxytryptamine receptor 7	P34969	Humans	Predicted (SEA)	290.611
Click to view 3D structure	Alpha-2C adrenergic receptor	P18825	Humans	Predicted (SEA)	174.071
Click to view 3D structure	Cytochrome P450 3A4	P08684	Humans	Predicted (SEA)	947.114
Click to view 3D structure	Cytochrome P450 2D6	P10635	Humans	Predicted (SEA)	673.707
Click to view 3D structure	Carbonic anhydrase 2	P00918	Humans	Predicted (SEA)	318.014
Click to view 3D structure	Alpha-1A adrenergic receptor	P35348	Humans	Predicted (SEA)	272.005
Click to view 3D structure	17-beta-hydroxysteroid dehydrogenase type 2	P37059	Humans	Predicted (SEA)	19.7737
Click to view 3D structure	17-beta-hydroxysteroid dehydrogenase type 1	P14061	Humans	Predicted (SEA)	19.7737
Click to view 3D structure	5-hydroxytryptamine receptor 2C	P28335	Humans	Predicted (SEA)	523.302
Click to view 3D structure	5-hydroxytryptamine receptor 2B	P41595	Humans	Predicted (SEA)	409.098
Click to view 3D structure	Carbonic anhydrase 12	O43570	Humans	Predicted (SEA)	243.512
Click to view 3D structure	Cytochrome P450 2C9	P11712	Humans	Predicted (SEA)	1087.71
Click to view 3D structure	Sodium-dependent noradrenaline transporter	P23975	Humans	Predicted (SEA)	301.899
Click to view 3D structure	Trace amine-associated receptor 1	Q96RJ0	Humans	Predicted (SEA)	36.5891
Click to view 3D structure	Alpha-1A adrenergic receptor	P43140	Rattus norvegicus	Predicted (SEA)	210.193
Click to view 3D structure	Carbonic anhydrase 5A, mitochondrial	P35218	Humans	Predicted (SEA)	162.705
Click to view 3D structure	Sodium-dependent serotonin transporter	P31645	Humans	Predicted (SEA)	500.103
Click to view 3D structure	5-hydroxytryptamine receptor 2A	P28223	Humans	Predicted (SEA)	816.405
Click to view 3D structure	Cytochrome P450 2C19	P33261	Humans	Predicted (SEA)	788.068
Click to view 3D structure	5-hydroxytryptamine receptor 2C	P08909	Rat	Predicted (SEA)	260.094
Click to view 3D structure	5-hydroxytryptamine receptor 2A	P14842	Rattus norvegicus	Predicted (SEA)	421.398
Click to view 3D structure	5-hydroxytryptamine receptor 2B	P30994	Rattus norvegicus	Predicted (SEA)	34.7208