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Substance Name: Metaraminol [INN:BAN]
RN: 54-49-9
UNII: 818U2PZ2EH
InChIKey: WXFIGDLSSYIKKV-RCOVLWMOSA-N

Note

  • A sympathomimetic agent that acts predominantly at alpha-1 adrenergic receptors. It has been used primarily as a vasoconstrictor in the treatment of HYPOTENSION.

Molecular Formula

  • C9-H13-N-O2

Molecular Weight

  • 167.2067
 

Classification Codes

  • Adrenergic Agents
  • Adrenergic Agonists
  • Adrenergic alpha-1 Receptor Agonists
  • Adrenergic alpha-Agonists
  • Autonomic Agents
  • Cardiovascular Agents
  • Drug / Therapeutic Agent
  • Neurotransmitter Agents
  • Peripheral Nervous System Agents
  • Sympathomimetics
  • Vasoconstrictor Agents
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Names and Synonyms

Name of Substance

  • Metaraminol
  • Metaraminol [INN:BAN]

MeSH Heading

  • Metaraminol

Synonyms

  • (-)-Erythro-metaraminol
  • 1-(m-Hydroxyphenyl)-2-amino-1-propanol
  • 1-alpha-(1-Aminoethyl)-m-hydroxybenzyl alcohol
  • 1-Metaraminol
  • 2-Amino-1-(m-hydroxyphenyl)-1-propanol
  • 3-Hydroxyphenylisopropanolamine
  • alpha-(1-Aminoethyl)-3-hydroxybenzenemethanol
  • alpha-(1-Aminoethyl)-m-hydroxybenzyl alcohol
  • alpha-(m-Hydroxyphenyl)-beta-aminopropanol
  • Benzenemethanol, alpha-(1-aminoethyl)-3-hydroxy-, (R-(R*,S*))-
  • Benzyl alcohol, alpha-(1-aminoethyl)-m-hydroxy-, (-)-
  • CCRIS 8465
  • HSDB 2716
  • Hydroxynorephedrine
  • Icoral B
  • l-Metaraminol
  • m-Hydroxy norephedrine
  • m-Hydroxy-alpha-(1-aminoethyl)-benzyl alcohol
  • m-Hydroxynorephedrine
  • m-Hydroxyphenylpropanolamine
  • m-Hydroxypropadrine
  • Metaradrine
  • Metaraminol
  • Metaraminolum
  • Metaraminolum [INN-Latin]
  • Metaraminolum [Latin]
  • Pressonex
  • Pressorol
  • UNII-818U2PZ2EH

Systematic Names

  • Benzenemethanol, alpha-(1-aminoethyl)-3-hydroxy-, (R-(R*,S*))-
  • Benzyl alcohol, alpha-(1-aminoethyl)-m-hydroxy-, (-)-

Registry Numbers

CAS Registry Number

  • 54-49-9

FDA UNII

  • 818U2PZ2EH

Related Registry Number

  • 33402-03-8 (bitartrate (1:1) (salt))

System Generated Number

  • 0000054499

Structure Descriptors

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

InChIKey

WXFIGDLSSYIKKV-RCOVLWMOSA-N

Smiles

C[C@H](N)[C@H](O)c1cccc(O)c1

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intravenous 51mg/kg (51mg/kg)   "Drug Dosages in Laboratory Animals - A Handbook," Rev. ed., Barnes, C.D., and L.G. Eltherington, Berkeley, Univ. of California Press, 1973Vol. -, Pg. 155, 1973.
mouse LD50 oral 99mg/kg (99mg/kg)   "Drug Dosages in Laboratory Animals - A Handbook," Rev. ed., Barnes, C.D., and L.G. Eltherington, Berkeley, Univ. of California Press, 1973Vol. -, Pg. 155, 1973.
mouse LD50 subcutaneous 92mg/kg (92mg/kg)   "Drug Dosages in Laboratory Animals - A Handbook," Rev. ed., Barnes, C.D., and L.G. Eltherington, Berkeley, Univ. of California Press, 1973Vol. -, Pg. 155, 1973.
rat LD50 intraperitoneal 41mg/kg (41mg/kg)   "Drug Dosages in Laboratory Animals - A Handbook," Rev. ed., Barnes, C.D., and L.G. Eltherington, Berkeley, Univ. of California Press, 1973Vol. -, Pg. 155, 1973.
rat LD50 oral 240mg/kg (240mg/kg)   "Drug Dosages in Laboratory Animals - A Handbook," Rev. ed., Barnes, C.D., and L.G. Eltherington, Berkeley, Univ. of California Press, 1973Vol. -, Pg. 155, 1973.
rat LD50 subcutaneous 117mg/kg (117mg/kg)   "Drug Dosages in Laboratory Animals - A Handbook," Rev. ed., Barnes, C.D., and L.G. Eltherington, Berkeley, Univ. of California Press, 1973Vol. -, Pg. 155, 1973.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 107.5 deg C   EXP
Boiling Point 218 deg C   EXP
pKa Dissociation Constant 8.79 (none)   EXP
log P (octanol-water) -0.27 (none)   EXP
Water Solubility 1.00E+06 mg/L 25 EST
Vapor Pressure 1.67E-05 mm Hg 25 EST
Henry's Law Constant 4.10E-15 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 1.31E-10 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.