: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 }}

See also

References

{{Reflist}}

{{DEFAULTSORT:Phenethylamine, 1-}}

Category:Benzylamines

Category:Phenethylamines