1-Phenylethylamine

Quality 0.50 · 1 view · Updated 2 months ago

title: "1-Phenylethylamine" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["benzylamines", "phenethylamines"] topic_path: "general/benzylamines" source: "https://en.wikipedia.org/wiki/1-Phenylethylamine" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0

|Watchedfields = changed |verifiedrevid = 477188998 |Name = 1-Phenylethylamine |ImageFile = 1-phenethylamine.png | ImageClass = skin-invert-image |ImageSize = 150px |ImageName = Chemical structure of 1-Phenylethylamine |PIN = 1-Phenylethan-1-amine |OtherNames = {{Unbulleted list | 1-Phenylethylamine | α-Phenylethylamine | α-Methylbenzylamine | 1-PEA | α-PEA |Section1 = {{Chembox Identifiers |CASNo = 618-36-0 |CASNo_Comment = (R/S) |CASNo1 = 3886-69-9 |CASNo1_Comment = (R)-(+) |CASNo2 = 2627-86-3 |CASNo2_Comment = (S)-(−) |CASNo_Ref = |CASNo1_Ref = |CASNo2_Ref = |UNII_Ref = |UNII = HZ9DM6B2MT |UNII_Comment = (R/S) |UNII1_Ref = |UNII1 = V022ZK8GZ5 |UNII1_Comment = (R)-(+) |UNII2_Ref = |UNII2 = 05780F90V3 |UNII2_Comment = (S)-(−) |PubChem = 7408 |PubChem_Comment = (R/S) |PubChem1 = 643189 |PubChem1_Comment = (R)-(+) |PubChem2 = 75818 |PubChem2_Comment = (S)-(−) |SMILES = CC(C1=CC=CC=C1)N |SMILES_Comment = (R/S) |SMILES1 = CC@HN |SMILES1_Comment = (R)-(+) |SMILES2 = CC@@HN |SMILES2_Comment = (S)-(−) |InChI = 1S/C8H11N/c1-7(9)8-5-3-2-4-6-8/h2-7H,9H2,1H3 |InChIKey = RQEUFEKYXDPUSK-UHFFFAOYSA-N |InChI_Comment = (R/S) |InChI1 = 1S/C8H11N/c1-7(9)8-5-3-2-4-6-8/h2-7H,9H2,1H3/t7-/m1/s1 |InChIKey1 = RQEUFEKYXDPUSK-SSDOTTSWSA-N |InChI1_Comment = (R)-(+) |InChI2 = 1S/C8H11N/c1-7(9)8-5-3-2-4-6-8/h2-7H,9H2,1H3/t7-/m0/s1 |InChIKey2 = RQEUFEKYXDPUSK-ZETCQYMHSA-N |InChI2_Comment = (S)-(−) |ChemSpiderID_Ref = |ChEBI_Ref = |ChEBI = 670 |ChemSpiderID = 7130 |KEGG_Ref = |KEGG = C02455 |ChEMBL_Ref = |ChEMBL = 278059 |StdInChI_Ref = |StdInChI = 1S/C8H11N/c1-7(9)8-5-3-2-4-6-8/h2-7H,9H2,1H3 |StdInChIKey_Ref = |StdInChIKey = RQEUFEKYXDPUSK-UHFFFAOYSA-N |Section2 = {{Chembox Properties |C=8|H=11|N=1 |Density = 0.94 g/mL |MeltingPt = −65 °C |BoilingPtC = 187 |Section3 = {{Chembox Hazards |MainHazards = Corrosive |Section9 = {{Chembox Related |OtherFunction = (R)-(+)- (CAS [3886-69-9]) (S)-(−)- (CAS [2627-86-3]) |OtherFunction_label = stereoisomers

1-Phenylethylamine (1-PEA or α-PEA), also known as α-methylbenzylamine, is the organic compound with the formula C6H5CH(NH2)CH3. This primary amine is a colorless liquid is often used in chiral resolutions. Like benzylamine, it is relatively basic and forms stable ammonium salts and imines.

Preparation and optical resolution

1-Phenylethylamine may be prepared by the reductive amination of acetophenone:

: The Leuckart reaction, using ammonium formate, is another method for this transformation.

-malic acid is used to resolve 1-Phenylethylamine, a versatile resolving agent in its own right. The dextrorotatory enantiomer crystallizes with the malate, leaving the levorotatory form in solution.

Pharmacology

Similarly to benzylamine and analogues like pargyline, 1-phenylethylamine has been found to act as a monoamine oxidase inhibitor (MAOI), as well as an inhibitor of semicarbazide-sensitive amine oxidase (SSAO).

References

References

  1. John C. Robinson, Jr. and H. R. Snyder. (1943). "α-Phenylethylamine".
  2. (1960). "Practical Organic Chemistry, 4th Ed.". Longman.
  3. A. W. Ingersoll. (1937). "d- and l-α-Phenylethylamine". Organic Syntheses.
  4. (January 2004). "Monoamine oxidase and head-twitch response in mice. Mechanisms of alpha-methylated substrate derivatives". Neurotoxicology.
  5. (June 1986). "Studies of monoamine oxidase and semicarbazide-sensitive amine oxidase. II. Inhibition by alpha-methylated substrate-analogue monoamines, alpha-methyltryptamine, alpha-methylbenzylamine and two enantiomers of alpha-methylbenzylamine". Jpn J Pharmacol.

::callout[type=info title="Wikipedia Source"] This article was imported from Wikipedia and is available under the Creative Commons Attribution-ShareAlike 4.0 License. Content has been adapted to SurfDoc format. Original contributors can be found on the article history page. ::

benzylaminesphenethylamines