1-Phenylethylamine

Chemical compound From Wikipedia, the free encyclopedia

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.

Quick facts Names, Identifiers ...
1-Phenylethylamine
Chemical structure of 1-Phenylethylamine
Chemical structure of 1-Phenylethylamine
Names
Preferred IUPAC name
1-Phenylethan-1-amine
Other names
  • 1-Phenylethylamine
  • α-Phenylethylamine
  • α-Methylbenzylamine
  • 1-PEA
  • α-PEA
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.009.588 Edit this at Wikidata
KEGG
UNII
  • InChI=1S/C8H11N/c1-7(9)8-5-3-2-4-6-8/h2-7H,9H2,1H3 checkY
    Key: RQEUFEKYXDPUSK-UHFFFAOYSA-N checkY
  • (R/S): InChI=1S/C8H11N/c1-7(9)8-5-3-2-4-6-8/h2-7H,9H2,1H3
    Key: RQEUFEKYXDPUSK-UHFFFAOYSA-N
  • (R)-(+): InChI=1S/C8H11N/c1-7(9)8-5-3-2-4-6-8/h2-7H,9H2,1H3/t7-/m1/s1
    Key: RQEUFEKYXDPUSK-SSDOTTSWSA-N
  • (S)-(−): InChI=1S/C8H11N/c1-7(9)8-5-3-2-4-6-8/h2-7H,9H2,1H3/t7-/m0/s1
    Key: RQEUFEKYXDPUSK-ZETCQYMHSA-N
  • (R/S): CC(C1=CC=CC=C1)N
  • (R)-(+): C[C@H](C1=CC=CC=C1)N
  • (S)-(−): C[C@@H](C1=CC=CC=C1)N
Properties
C8H11N
Molar mass 121.183 g·mol−1
Density 0.94 g/mL
Melting point −65 °C[citation needed]
Boiling point 187 °C (369 °F; 460 K)
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 Corrosive
Related compounds
Related stereoisomers
 (R)-(+)- (CAS [3886-69-9])
(S)-(−)- (CAS [2627-86-3])
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Preparation and optical resolution

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

C6H5C(O)CH3 + NH3 + H2 → C6H5CH(NH2)CH3 + H2O

The Leuckart reaction, using ammonium formate, is another method for this transformation.[2]

l-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.[3]

Pharmacology

Similarly to benzylamine and analogues like pargyline, 1-phenylethylamine has been found to act as a very weak monoamine oxidase inhibitor (MAOI), as well as an inhibitor of semicarbazide-sensitive amine oxidase (SSAO).[4][5]

See also

References

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