1-Phenylethylamine

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.

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
CAS Number	618-36-0 (R/S) Y 3886-69-9 (R)-(+) Y 2627-86-3 (S)-(−) Y
3D model (JSmol)	(R/S): Interactive image (R)-(+): Interactive image (S)-(−): Interactive image
ChEBI	CHEBI:670 Y
ChEMBL	ChEMBL278059 Y
ChemSpider	7130 Y
ECHA InfoCard	100.009.588
KEGG	C02455 Y
PubChem CID	7408 (R/S) 643189 (R)-(+) 75818 (S)-(−)
UNII	HZ9DM6B2MT (R/S) Y V022ZK8GZ5 (R)-(+) Y 05780F90V3 (S)-(−) Y
CompTox Dashboard (EPA)	DTXSID40862301
InChI InChI=1S/C8H11N/c1-7(9)8-5-3-2-4-6-8/h2-7H,9H2,1H3 Y Key: RQEUFEKYXDPUSK-UHFFFAOYSA-N Y (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
SMILES (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
Chemical formula	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). Y verify (what is YN ?) Infobox references

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 monoamine oxidase inhibitor (MAOI), as well as an inhibitor of semicarbazide-sensitive amine oxidase (SSAO).^[4][5]

See also

• 2-Phenylethylamine