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{{DISPLAYTITLE:''gamma''-Glutamylmethylamide}}
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{{chembox
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| verifiedrevid = 443832154
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|  Name = ''gamma''-Glutamylmethylamide
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|  ImageFile = GMA_2D_Structure.png
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|  ImageSize = 200px
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|  ImageName = gamma-Glutamylmethylamide
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|  ImageFile1 = GMA3d.png
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|  ImageSize1 = 200px
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|  ImageName1 = gamma-Glutamylmethylamide
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|  IUPACName =<small>(2''S'')-2-amino-5-(methylamino)-5-oxopentanoic acid</small>
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|  OtherNames = ''N''-Methyl-<small>L</small>-glutamine; metheanine
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| Section1 = {{Chembox Identifiers
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|  ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
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| ChemSpiderID = 388957
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| PubChem = 439925
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| KEGG_Ref = {{keggcite|correct|kegg}}
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| KEGG = C03153
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| InChI = 1/C6H12N2O3/c1-8-5(9)3-2-4(7)6(10)11/h4H,2-3,7H2,1H3,(H,8,9)(H,10,11)/t4-/m0/s1
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| InChIKey = ONXPDKGXOOORHB-BYPYZUCNBU
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
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| StdInChI = 1S/C6H12N2O3/c1-8-5(9)3-2-4(7)6(10)11/h4H,2-3,7H2,1H3,(H,8,9)(H,10,11)/t4-/m0/s1
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
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| StdInChIKey = ONXPDKGXOOORHB-BYPYZUCNSA-N
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| CASNo = 3081-62-7
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|  DrugBank_Ref = {{drugbankcite|correct|drugbank}}
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| DrugBank = DB03473
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| ChEBI_Ref = {{ebicite|correct|EBI}}
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| ChEBI = 58200
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| SMILES = O=C(NC)CC[C@H](N)C(=O)O
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}}
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| Section2 = {{Chembox Properties
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|  Formula = C<sub>6</sub>H<sub>12</sub>N<sub>2</sub>O<sub>3</sub>
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|  MolarMass = 160.17 g/mol
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|  Density = 1.211 g/mL
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|  BoilingPtC = 427.5
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  }}
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}}
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'''''gamma''-Glutamylmethylamide''', also known as '''GMA''', '''''N''-methyl-<small>L</small>-glutamine''', and '''metheanine''', is an [[amino acid]] found in [[green tea]],<ref name="Hypotensive-Yokogoshi">{{cite journal | author=Yokogoshi H, Kobayashi M. | title=Hypotensive effect of gamma-glutamylmethylamide in spontaneously hypertensive rats. | journal=Life Sci. | year=1998 | pages=1065–8 | volume=62 | issue=12 | pmid=9519808 | doi=10.1016/S0024-3205(98)00029-0}}</ref> which is structurally related to <small>L</small>-[[theanine]] and <small>L</small>-[[glutamine]].
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'''''gamma''-Glutamylmethylamide''', also known as '''GMA''', '''''N''-methyl-<small>L</small>-glutamine''', and '''metheanine''', is an amino acid found in green tea, which is structurally related to <small>L</small>-[[theanine]] and <small>L</small>-[[glutamine]].
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GMA has been shown to be an effective [[hypotensive]], more so than <small>L</small>-theanine.<ref name="Hypotensive-Yokogoshi" />
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GMA has been shown to be an effective hypotensive, more so than <small>L</small>-theanine.<
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* [[Green tea]]
 
* [[Green tea]]
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== References ==
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{{reflist}}
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{{DEFAULTSORT:Glutamylmethylamide, gamma-}}
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[[Category:Amino acids]]
   
[[Category:Tea]]
 
[[Category:Tea]]
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{{cardiovascular-drug-stub}}
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[[fa:گاما-گلوتامیل‌متیل‌آمید]]
 

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