:1-Phenylethylamine
{{chembox
|Watchedfields = changed
|verifiedrevid = 477188998
|Name = 1-Phenylethylamine
|ImageFile = 1-phenethylamine.png
|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 = {{cascite|correct|CAS}}
|CASNo1_Ref = {{cascite|correct|CAS}}
|CASNo2_Ref = {{cascite|correct|CAS}}
|UNII_Ref = {{fdacite|correct|FDA}}
|UNII = HZ9DM6B2MT
|UNII_Comment = (R/S)
|UNII1_Ref = {{fdacite|correct|FDA}}
|UNII1 = V022ZK8GZ5
|UNII1_Comment = (R)-(+)
|UNII2_Ref = {{fdacite|correct|FDA}}
|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 = C[C@H](C1=CC=CC=C1)N
|SMILES1_Comment = (R)-(+)
|SMILES2 = C[C@@H](C1=CC=CC=C1)N
|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 = {{chemspidercite|correct|chemspider}}
|ChEBI_Ref = {{ebicite|correct|EBI}}
|ChEBI = 670
|ChemSpiderID = 7130
|KEGG_Ref = {{keggcite|correct|kegg}}
|KEGG = C02455
|ChEMBL_Ref = {{ebicite|correct|EBI}}
|ChEMBL = 278059
|StdInChI_Ref = {{stdinchicite|correct|chemspider}}
|StdInChI = 1S/C8H11N/c1-7(9)8-5-3-2-4-6-8/h2-7H,9H2,1H3
|StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
|StdInChIKey = RQEUFEKYXDPUSK-UHFFFAOYSA-N
}}
|Section2 = {{Chembox Properties
|C=8|H=11|N=1
|Density = 0.94 g/mL
|MeltingPt = -65 C{{citation needed|date=November 2015}}
|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:{{OrgSynth | title = α-Phenylethylamine | author = John C. Robinson, Jr. and H. R. Snyder | volume = 23 | pages = 68 | year = 1943 | doi = 10.15227/orgsyn.023.0068}}
:{{chem2|C6H5C(O)CH3 + NH3 + H2 -> C6H5CH(NH2)CH3 + H2O}}
The Leuckart reaction, using ammonium formate, is another method for this transformation.{{cite book|last1= Mann |first1= F. G. |last2= Saunders |first2= B. C.|title=Practical Organic Chemistry, 4th Ed.|year=1960|publisher=Longman|location=London|isbn=9780582444072|pages=223–224|url=https://www.scribd.com/doc/46973684/Practical-Organic-Chemistry-Frederick-George-Mann}}
{{sc|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.{{cite journal |doi=10.15227/orgsyn.017.0080|title=d- and l-α-Phenylethylamine|journal=Organic Syntheses|year=1937|volume=17|page=80|author=A. W. Ingersoll}}
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).{{cite journal | vauthors = Nakagawasai O, Arai Y, Satoh SE, Satoh N, Neda M, Hozumi M, Oka R, Hiraga H, Tadano T | title = Monoamine oxidase and head-twitch response in mice. Mechanisms of alpha-methylated substrate derivatives | journal = Neurotoxicology | volume = 25 | issue = 1–2 | pages = 223–232 | date = January 2004 | pmid = 14697897 | doi = 10.1016/S0161-813X(03)00101-3 | bibcode = 2004NeuTx..25..223N | url = }}{{cite journal | vauthors = Arai Y, Toyoshima Y, Kinemuchi H | title = 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 | journal = Jpn J Pharmacol | volume = 41 | issue = 2 | pages = 191–197 | date = June 1986 | pmid = | doi = 10.1254/jjp.41.191 | url = | doi-access = free }}