1-Phenylethylamine

changed 477188998 1-Phenylethylamine 1-phenylethylamine.svg skin-invert-image 150px Chemical structure of 1-Phenylethylamine 1-Phenylethan-1-amine 1-Phenylethylamine α-Phenylethylamine α-Methylbenzylamine 1-PEA α-PEA 618-36-0 (R/S) 3886-69-9 (R)-(+) 2627-86-3 (S)-(−) correct CAS correct CAS correct CAS correct FDA HZ9DM6B2MT (R/S) correct FDA V022ZK8GZ5 (R)-(+) correct FDA 05780F90V3 (S)-(−) 7408 (R/S) 643189 (R)-(+) 75818 (S)-(−) CC(C1=CC=CC=C1)N (R/S) C[C@H](C1=CC=CC=C1)N (R)-(+) C[C@@H](C1=CC=CC=C1)N (S)-(−) 1S/C8H11N/c1-7(9)8-5-3-2-4-6-8/h2-7H,9H2,1H3 RQEUFEKYXDPUSK-UHFFFAOYSA-N (R/S) 1S/C8H11N/c1-7(9)8-5-3-2-4-6-8/h2-7H,9H2,1H3/t7-/m1/s1 RQEUFEKYXDPUSK-SSDOTTSWSA-N (R)-(+) 1S/C8H11N/c1-7(9)8-5-3-2-4-6-8/h2-7H,9H2,1H3/t7-/m0/s1 RQEUFEKYXDPUSK-ZETCQYMHSA-N (S)-(−) correct chemspider correct EBI 670 7130 correct kegg C02455 correct EBI 278059 correct chemspider 1S/C8H11N/c1-7(9)8-5-3-2-4-6-8/h2-7H,9H2,1H3 correct chemspider RQEUFEKYXDPUSK-UHFFFAOYSA-N 8 11 1 0.94 g/mL −65 °CNovember 2015 187 Corrosive (R)-(+)- (CAS [3886-69-9])(S)-(−)- (CAS [2627-86-3]) 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: α-Phenylethylamine John C. Robinson, Jr. and H. R. Snyder 23 68 1943 10.15227/orgsyn.023.0068 C6H5C(O)CH3 + NH3 + H2 -> C6H5CH(NH2)CH3 + H2O The Leuckart reaction, using ammonium formate, is another method for this transformation. Mann F. G. Saunders B. C. Practical Organic Chemistry, 4th Ed. 1960 Longman London 9780582444072 223–224 https://www.scribd.com/doc/46973684/Practical-Organic-Chemistry-Frederick-George-Mann l-malic acid, a versatile resolving agent in its own right, is used to resolve 1-Phenylethylamine. The dextrorotatory enantiomer crystallizes with the malate, leaving the levorotatory form in solution.10.15227/orgsyn.017.0080 free d- and l-α-Phenylethylamine Organic Syntheses 1937 17 80 A. W. Ingersoll 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). Nakagawasai O, Arai Y, Satoh SE, Satoh N, Neda M, Hozumi M, Oka R, Hiraga H, Tadano T Monoamine oxidase and head-twitch response in mice. Mechanisms of alpha-methylated substrate derivatives Neurotoxicology 25 1–2 223–232 January 2004 14697897 10.1016/S0161-813X(03)00101-3 2004NeuTx..25..223N Arai Y, Toyoshima Y, Kinemuchi H 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 June 1986 10.1254/jjp.41.191 free See also 2-Phenylethylamine References Category:Benzylamines Category:Phenethylamines