Phenylethanolamine

Phenylethanolamine
Ball-and-stick model of the phenylethanolamine molecule
Names
IUPAC name
2-Amino-1-phenylethanol
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.028.609 Edit this at Wikidata
KEGG
UNII
  • InChI=1S/C8H11NO/c9-6-8(10)7-4-2-1-3-5-7/h1-5,8,10H,6,9H2 checkY
    Key: ULSIYEODSMZIPX-UHFFFAOYSA-N checkY
  • InChI=1/C8H11NO/c9-6-8(10)7-4-2-1-3-5-7/h1-5,8,10H,6,9H2
    Key: ULSIYEODSMZIPX-UHFFFAOYAE
  • OC(c1ccccc1)CN
Properties
C8H11NO
Molar mass 137.18 g/mol
Appearance pale yellow solid
Melting point 56 to 57 °C (133 to 135 °F; 329 to 330 K)
Boiling point 157 to 160 °C (315 to 320 °F; 430 to 433 K) at 17 mmHg
soluble
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Phenylethanolamine (sometimes abbreviated PEOH), or β-hydroxyphenethylamine, is a trace amine with a structure similar to those of other trace phenethylamines as well as the catecholamine neurotransmitters dopamine, norepinephrine, and epinephrine. As an organic compound, phenylethanolamine is a β-hydroxylated phenethylamine that is also structurally related to a number of synthetic drugs in the substituted phenethylamine class. In common with these compounds, phenylethanolamine has strong cardiovascular activity[1] and, under the name Apophedrin, has been used as a drug to produce topical vasoconstriction.[2]

In appearance, phenylethanolamine is a white solid.

Phenylethanolamine is perhaps best known in the field of bioscience as part of the enzyme name "phenylethanolamine N-methyl transferase", referring to an enzyme which is responsible for the conversion of norepinephrine into epinephrine, as well as other related transformations.[3]

  1. ^ W. H. Hartung (1945). "Beta-phenethylamine derivatives." Ind. Eng. Chem. 37 126–136.
  2. ^ The Merck Index, 10th Ed. (1983), p. 1051, Merck & Co., Rahway.
  3. ^ J. Axelrod (1966). "Methylation reactions in the formation and metabolism of catecholamines and other biogenic amines. Pharmacol. Rev. 18 95–113.