1-Phenylethylamine

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

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:^[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]

References

^ John C. Robinson, Jr. and H. R. Snyder (1943). "α-Phenylethylamine". Organic Syntheses. 23: 68. doi:10.15227/orgsyn.023.0068.
^ Mann, F. G.; Saunders, B. C. (1960). Practical Organic Chemistry, 4th Ed. London: Longman. pp. 223–224. ISBN 9780582444072.
^ A. W. Ingersoll (1937). "d- and l-α-Phenylethylamine". Organic Syntheses. 17: 80. doi:10.15227/orgsyn.017.0080.
^ Nakagawasai O, Arai Y, Satoh SE, Satoh N, Neda M, Hozumi M, Oka R, Hiraga H, Tadano T (January 2004). "Monoamine oxidase and head-twitch response in mice. Mechanisms of alpha-methylated substrate derivatives". Neurotoxicology. 25 (1–2): 223–232. Bibcode:2004NeuTx..25..223N. doi:10.1016/S0161-813X(03)00101-3. PMID 14697897.
^ Arai Y, Toyoshima Y, Kinemuchi H (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. 41 (2): 191–197. doi:10.1254/jjp.41.191.

[1] John C. Robinson, Jr. and H. R. Snyder (1943). "α-Phenylethylamine". Organic Syntheses. 23: 68. doi:10.15227/orgsyn.023.0068.

[2] Mann, F. G.; Saunders, B. C. (1960). Practical Organic Chemistry, 4th Ed. London: Longman. pp. 223–224. ISBN 9780582444072.

[3] A. W. Ingersoll (1937). "d- and l-α-Phenylethylamine". Organic Syntheses. 17: 80. doi:10.15227/orgsyn.017.0080.

[NakagawasaiAraiSatoh2004-4] Nakagawasai O, Arai Y, Satoh SE, Satoh N, Neda M, Hozumi M, Oka R, Hiraga H, Tadano T (January 2004). "Monoamine oxidase and head-twitch response in mice. Mechanisms of alpha-methylated substrate derivatives". Neurotoxicology. 25 (1–2): 223–232. Bibcode:2004NeuTx..25..223N. doi:10.1016/S0161-813X(03)00101-3. PMID 14697897.

[AraiToyoshimaKinemuchi1986-5] Arai Y, Toyoshima Y, Kinemuchi H (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. 41 (2): 191–197. doi:10.1254/jjp.41.191.

[1]

[2]

[3]

[4]

[5]

Preparation and optical resolution

Pharmacology

See also

References