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Phenylethanolamine information


Phenylethanolamine
Ball-and-stick model of the phenylethanolamine molecule
Names
IUPAC name
2-Amino-1-phenylethanol
Identifiers
CAS Number
  • 7568-93-6 checkY
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:16343 checkY
ChEMBL
  • ChEMBL19216 checkY
ChemSpider
  • 975 checkY
ECHA InfoCard 100.028.609 Edit this at Wikidata
KEGG
  • C02735 checkY
PubChem CID
  • 1000
UNII
  • 2P4Y56479O checkY
CompTox Dashboard (EPA)
  • DTXSID10864094 Edit this at Wikidata
InChI
  • 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
SMILES
  • OC(c1ccccc1)CN
Properties
Chemical formula
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
Solubility in water
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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Infobox references

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.

and 28 Related for: Phenylethanolamine information

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Phenylethanolamine

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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...

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Catecholamine

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groups, an intermediate ethyl chain, and a terminal amine group. Phenylethanolamines such as norepinephrine have a hydroxyl group on the ethyl chain.[citation...

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Monoamine neurotransmitter

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Phenethylamine (PEA) N-Methylphenethylamine (endogenous amphetamine isomer) Phenylethanolamine m-Tyramine p-Tyramine 3-Methoxytyramine N-Methyltyramine m-Octopamine...

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Adrenaline

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adrenaline secretion as the activity of the synthesizing enzyme, phenylethanolamine-N-methyltransferase, depends on the high concentration of cortisol...

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Halostachine

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β-hydroxy-phenethylamine (a phenylethanolamine) related to its better-known "parent" biogenic amine, phenylethanolamine, to the adrenergic drug synephrine...

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Etilefrine

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an antihypotensive. It is a sympathomimetic amine of the 3-hydroxy-phenylethanolamine series used in treating orthostatic hypotension of neurological, cardiovascular...

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Dopamine

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cofactors. Norepinephrine is converted into epinephrine by the enzyme phenylethanolamine N-methyltransferase with S-adenosyl-L-methionine as the cofactor....

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Midodrine

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1016/B978-0-12-818655-8.00041-X. ISBN 978-0-12-818656-5. DE 2506110, Zoelss G, "Phenylethanolamine derivs prepn. - by reducing azides, useful as hypertensives", issued...

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Fluconazole

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Fluconazole is an antifungal medication used for a number of fungal infections. This includes candidiasis, blastomycosis, coccidioidomycosis, cryptococcosis...

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Tyramine

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and salts of isomers where they exist, means that meta-tyramine and phenylethanolamine, a substance found in every living human body, and other common, non-hallucinogenic...

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Biogenic amine

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Phenethylamine (PEA) N-Methylphenethylamine (endogenous amphetamine isomer) Phenylethanolamine m-Tyramine p-Tyramine 3-Methoxytyramine N-Methyltyramine m-Octopamine...

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Norfenefrine

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AA, Robertson HA (December 1977). "m-Octopamine, p-octopamine and phenylethanolamine in rat brain: a sensitive, specific assay and the effects of some...

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Terbutaline

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 503–507. Archived from the original on 2010-11-04. GB 1199630, "Phenylethanolamine Derivatives Effective in the Treatment of Bronchospastic Conditions"...

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List of adrenergic drugs

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Fusaric acid Nepicastat Phenopicolinic acid Tropolone PNMTTooltip Phenylethanolamine N-methyltransferase Substrates→Products: Norepinephrine (noradrenaline)→Epinephrine...

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Tobacco

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Ketoconazole

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Ketoconazole, sold under the brand name Nizoral among others, is an antiandrogen, antifungal, and antiglucocorticoid medication used to treat a number...

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Adrenal gland

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cytosol, noradrenaline is converted to epinephrine by the enzyme phenylethanolamine N-methyltransferase (PNMT) and stored in granules. Glucocorticoids...

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Norepinephrine

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Norepinephrine itself can further be converted into epinephrine by the enzyme phenylethanolamine N-methyltransferase with S-adenosyl-L-methionine as cofactor. In mammals...

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Ephedrine

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Ephedrine is a central nervous system (CNS) stimulant that is often used to prevent low blood pressure during anesthesia. It has also been used for asthma...

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Salbutamol

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Salbutamol, also known as albuterol and sold under the brand name Ventolin among others, is a medication that opens up the medium and large airways in...

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Phenylephrine

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Phenylephrine is a medication used as a decongestant for uncomplicated nasal congestion, used to dilate the pupil, used to increase blood pressure (given...

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Amphetamine

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turn, N-methylphenethylamine is metabolized from phenethylamine by phenylethanolamine N-methyltransferase, the same enzyme that metabolizes norepinephrine...

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Methylene blue

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Fusaric acid Nepicastat Phenopicolinic acid Tropolone PNMTTooltip Phenylethanolamine N-methyltransferase Substrates→Products: Norepinephrine (noradrenaline)→Epinephrine...

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Adderall

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turn, N-methylphenethylamine is metabolized from phenethylamine by phenylethanolamine N-methyltransferase, the same enzyme that metabolizes norepinephrine...

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NMDA receptor

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E, Simorowski N, Furukawa H (June 2011). "Subunit arrangement and phenylethanolamine binding in GluN1/GluN2B NMDA receptors". Nature. 475 (7355): 249–253...

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Pseudoephedrine

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Pseudoephedrine (PSE) is a sympathomimetic drug of the phenethylamine and amphetamine chemical classes. It may be used as a nasal/sinus decongestant, as...

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Dextroamphetamine

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turn, N-methylphenethylamine is metabolized from phenethylamine by phenylethanolamine N-methyltransferase, the same enzyme that metabolizes norepinephrine...

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Diphenhydramine

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Fusaric acid Nepicastat Phenopicolinic acid Tropolone PNMTTooltip Phenylethanolamine N-methyltransferase Substrates→Products: Norepinephrine (noradrenaline)→Epinephrine...

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