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Substance Name: Phenylephrine [INN:BAN]
RN: 59-42-7
UNII: 1WS297W6MV
InChIKey: SONNWYBIRXJNDC-VIFPVBQESA-N

Note

  • An alpha-1 adrenergic agonist used as a mydriatic, nasal decongestant, and cardiotonic agent.

Molecular Formula

  • C9-H13-N-O2

Molecular Weight

  • 167.207
 

Classification Codes

  • Adrenergic Agents
  • Adrenergic Agonists
  • Adrenergic alpha-1 Receptor Agonists
  • Adrenergic alpha-Agonists
  • Autonomic Agents
  • Cardiotonic Agents
  • Cardiovascular Agents
  • Drug / Therapeutic Agent
  • Human Data
  • Mydriatics
  • Nasal Decongestants
  • Neurotransmitter Agents
  • Peripheral Nervous System Agents
  • Protective Agents
  • Reproductive Effect
  • Respiratory System Agents
  • Sympathomimetics
  • Vasoconstrictor Agents

Names and Synonyms

Name of Substance

  • Phenylephrine
  • Phenylephrine [INN:BAN]

MeSH Heading

  • Phenylephrine

Synonyms

  • (-)-m-Hydroxy-alpha-(methylaminomethyl)benzyl alcohol
  • Ah-Chew
  • AI3-02402
  • Benzenemethanol, 3-hydroxy-alpha-((methylamino)methyl)-, (R)-
  • Benzyl alcohol, m-hydroxy-alpha-((methylamino)methyl)-, (-)-
  • CCRIS 8464
  • EC 200-424-8
  • EINECS 200-424-8
  • Fenilefrina
  • Fenilefrina [INN-Spanish]
  • Hemorid
  • HSDB 3383
  • Isophrin
  • l-(3-Hydroxyphenyl)-N-methylethanolamine
  • l-1-(m-Hydroxyphenyl)-2-methylaminoethanol
  • L-alpha-Hydroxy-beta-methylamino-3-hydroxy-L-ethylbenzene
  • l-m-Hydroxy-alpha-((methylamino)methyl)benzyl alcohol
  • m-Methylaminoethanolphenol
  • m-Oxedrine
  • m-Sympathol
  • m-Sympatol
  • m-Synephrine
  • Mesaton
  • Mesatone
  • Mesatonum
  • Metaoxedrin
  • Metaoxedrine
  • Metaoxedrinum
  • Metasympatol
  • Metasynephrine
  • Mezaton
  • Neosynephrine
  • Phenylephrine
  • Phenylephrine, l-
  • Phenylephrinum
  • Phenylephrinum [INN-Latin]
  • R(-)-Phenylephrine
  • UNII-1WS297W6MV
  • Visadron

Systematic Names

  • Benzenemethanol, 3-hydroxy-alpha-((methylamino)methyl)-, (R)- (9CI)
  • Benzyl alcohol, m-hydroxy-alpha-((methylamino)methyl)-, (-)-
  • Phenylephrine

Registry Numbers

CAS Registry Number

  • 59-42-7

FDA UNII

  • 1WS297W6MV

Related Registry Number

  • 61-76-7 (hydrochloride)

System Generated Number

  • 0000059427

Structure Descriptors

InChI

1S/C9H13NO2/c1-10-6-9(12)7-3-2-4-8(11)5-7/h2-5,9-12H,6H2,1H3/t9-/m0/s1

InChIKey

SONNWYBIRXJNDC-VIFPVBQESA-N

Smiles

c1([C@H](CNC)O)cc(ccc1)O

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
infant TDLo ocular 5500ug/kg (5.5mg/kg) VASCULAR: BP ELEVATION NOT CHARACTERIZED IN AUTONOMIC SECTION Anesthesiology. Vol. 36, Pg. 187, 1972.
mouse LD50 intravenous 38mg/kg (38mg/kg) BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)

SKIN AND APPENDAGES (SKIN): HAIR: OTHER

CARDIAC: PULSE RATE INCREASE WITHOUT FALL IN BP		 Acta Pharmacologica et Toxicologica. Vol. 38, Pg. 474, 1976.
mouse LD50 subcutaneous 875mg/kg (875mg/kg)   Farmakologiya i Toksikologiya Vol. 28, Pg. 46, 1965.
mouse LDLo intraperitoneal 60mg/kg (60mg/kg) CARDIAC: OTHER CHANGES Journal of Pharmacology and Experimental Therapeutics. Vol. 160, Pg. 22, 1968.
rat LD50 intraduodenal 65mg/kg (65mg/kg)   Archives Internationales de Pharmacodynamie et de Therapie. Vol. 180, Pg. 155, 1969.
rat LD50 oral 350mg/kg (350mg/kg)   Archives Internationales de Pharmacodynamie et de Therapie. Vol. 180, Pg. 155, 1969.
rat LD50 subcutaneous 28mg/kg (28mg/kg)   Journal of Pharmacology and Experimental Therapeutics. Vol. 85, Pg. 119, 1945.
women TDLo ocular 188ug/kg (0.188mg/kg) VASCULAR: BP ELEVATION NOT CHARACTERIZED IN AUTONOMIC SECTION Anesthesiology. Vol. 36, Pg. 187, 1972.

Physical Properties

Physical Property Value Units Temp (deg C) Source
pKa Dissociation Constant 8.97 (none)   EXP
log P (octanol-water) -0.31 (none)   EXP
Atmospheric OH Rate Constant 1.63E-10 cm3/molecule-sec 25 EST

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