Compound: metaraminol
SMILES: Oc1cc(ccc1)[C@@H](O)[C@@H](N)C
InChIKey: WXFIGDLSSYIKKV-RCOVLWMOSA-N
Synonyms: metaraminol, L-Metaraminol, Metaradrine, Hydroxynorephedrine, m-Hydroxypropadrine, 1-Metaraminol, Pressorol, m-Hydroxy norephedrine, (-)-Erythro-metaraminol, Icoral B, m-Hydroxyphenylpropanolamine, 54-49-9, Metaraminolum, 3-[(1R,2S)-2-amino-1-hydroxypropyl]phenol, 3-Hydroxyphenylisopropanolamine, 1-(m-Hydroxyphenyl)-2-amino-1-propanol, 2-Amino-1-(m-hydroxyphenyl)-1-propanol, alpha-(m-Hydroxyphenyl)-beta-aminopropanol, alpha-(1-Aminoethyl)-m-hydroxybenzyl alcohol, m-Hydroxy-alpha-(1-aminoethyl)-benzyl alcohol, 1-alpha-(1-Aminoethyl)-m-hydroxybenzyl alcohol, 818U2PZ2EH, Benzenemethanol, alpha-(1-aminoethyl)-3-hydroxy-, (R-(R*,S*))-, CHEBI:6794, DTXSID8023268, 3-((1R,2S)-2-amino-1-hydroxypropyl)phenol, Metaradrin, Isophenylephrine, metaraminolo, m Hydroxynorephedrine, meta Hydroxynorephedrine, Hydroxyphenylpropanolamine, RefChem:811236, m Hydroxyphenylpropanolamine, DTXCID703268, C01CA09, Metaraminolum [Latin], Pressonex, Metaraminolum [INN-Latin], Metaraminol (INN), METARAMINOL [INN], Metaraminol [INN:BAN], HSDB 2716, UNII-818U2PZ2EH, CCRIS 8465, 54-49-9 (free), Benzyl alcohol, alpha-(1-aminoethyl)-m-hydroxy-, (-)-, (1R,2S)-Metaraminol, METARAMINOL [MI], (-)-erythro-Methraminol, METARAMINOL [HSDB], METARAMINOL [VANDF], METARAMINOL [WHO-DD], SCHEMBL136778, GTPL7229, orb1710731, CHEMBL1201319, NIOSH/DN4340000, SCHEMBL29379078, EBC-26120, T0279L, AKOS006277341, DB00610, NCGC00178024-01, NCGC00178024-02, SBI-0206715.P001, DN43400000, NS00005483, C07146, D08192, EN300-7455644, Q409981, BRD-K96253961-046-03-1, BRD-K96253961-046-04-9, BRD-K96253961-046-05-6, alpha-(1-Aminoethyl)-m-hydroxybenzyl alcohol, (-)-erythro-, Benzyl alcohol, alpha-(1-aminoethyl)-m-hydroxy-, (-)-erythro-
Theoretical properties:
molecular_formula: C9H13NO2
molecular_weight: 167.20 g/mol
exact_mass: 167.094628657 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 3
hydrogen_bond_acceptor_count: 3
rotatable_bond_count: 2
heavy_atom_count: 12
topological_polar_surface_area: 66.5 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
Descriptions:
pubchem: Metaraminol is a member of the class of phenylethanolamines that is 2-amino-1-phenylethanol substituted by a methyl group at position 2 and a phenolic hydroxy group at position 1. A sympathomimetic agent , it is used in the treatment of hypotension. It has a role as a sympathomimetic agent, an alpha-adrenergic agonist and a vasoconstrictor agent.
chebi: A member of the class of phenylethanolamines that is 2-amino-1-phenylethanol substituted by a methyl group at position 2 and a phenolic hydroxy group at position 1. A  sympathomimetic agent , it is used in the treatment of hypotension.
chembl: METARAMINOL is a small molecule listed in the ChEMBL database and has reached clinical trial phase 4.0.
wikipedia: Metaraminol, also known as metaradrine and sold under the brand name Aramine among others,  is a sympathomimetic medication which is used in the prevention and treatment of hypotension (low blood pressure), particularly as a complication of anesthesia. It is given by intramuscular or intravenous administration.
Side effects of metaraminol include reflex bradycardia among others. Metaraminol is a norepinephrine releasing agent and at high doses a α1-adrenergic receptor agonist with some β-adrenergic effect. It is a substituted amphetamine and is closely related to phenylpropanolamine, ephedrine, and oxilofrine.
Metaraminol was approved for medical use in the United States in September 1954.