Editing Creatine (section)

{{Short description|Chemical compound}}
{{distinguish|creatinine|keratin}}
{{pp-pc}}
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{{Use dmy dates|date=January 2018}}

{{chembox
| Verifiedfields = changed
| Watchedfields  = changed
| verifiedrevid  = 464366517
| ImageFile      = CreatineStructure.png
| ImageFile_Ref  = {{chemboximage|correct|??}}
| ImageClass     = skin-invert
| ImageCaption   = Skeletal formula of neutral form of creatine
| ImageName      = Skeletal formula of neutral form of creatine
| ImageFile1     = CreatineZwitter.png
| ImageFile1_Ref = {{chemboximage|correct|??}}
| ImageClass1    = skin-invert
| ImageCaption1  = Skeletal formula of one of the [[zwitterionic]] forms of creatine
| ImageName1     = Skeletal formula of one of [[zwitterionic]] forms of creatine
| ImageFile2     = File:Creatine zwitterion ball.png
| ImageFile2_Ref = {{chemboximage|correct|??}}
| ImageCaption2  = Ball and stick model of one zwitterionic form of creatine
| ImageSize2     = 160
| ImageName2     = Ball and stick model of creatine
| SystematicName = 2-[Carbamimidoyl(methyl)amino]acetic acid
| OtherNames     = ''N''-Carbamimidoyl-''N''-methylglycine; Methylguanidoacetic acid; ''N''-amidinosarcosine
| Section1       = {{Chembox Identifiers
| CASNo = 57-00-1
| CASNo_Ref = {{cascite|correct|CAS}}
| PubChem = 586
| ChemSpiderID = 566
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| UNII = MU72812GK0
| UNII_Ref = {{fdacite|correct|FDA}}
| EINECS = 200-306-6
| DrugBank = DB00148
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| KEGG = C00300
| KEGG_Ref = {{keggcite|correct|kegg}}
| MeSHName = Creatine
| ChEBI = 16919
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 283800
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| RTECS = MB7706000
| Beilstein = 907175
| Gmelin = 240513
| 3DMet = B00084
| SMILES = CN(CC(=O)O)C(=N)N
| StdInChI = 1S/C4H9N3O2/c1-7(4(5)6)2-3(8)9/h2H2,1H3,(H3,5,6)(H,8,9)
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = CVSVTCORWBXHQV-UHFFFAOYSA-N
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
}}
| Section2       = {{Chembox Properties
| C=4 | H=9 | N=3 | O=2
| Appearance = White crystals
| Odor = Odourless
| MeltingPtC = 255
| Solubility = 13.3 g L<sup>−1</sup> (at 18 °C)
| LogP = −1.258
| pKa = 3.429
| pKb = 10.568
| IsoelectricPt = 8.47
| Density = 1.33 g/cm<sup>3</sup>
| VaporPressure = 0.001 mmHg 
}}
| Section5       = {{Chembox Thermochemistry
| DeltaHf = −538.06–−536.30 kJ mol<sup>−1</sup>
| DeltaHc = −2.3239–−2.3223 MJ mol<sup>−1</sup>
| Entropy = 189.5 J K<sup>−1</sup> mol<sup>−1</sup>
| HeatCapacity = 171.1 J K<sup>−1</sup> mol<sup>−1</sup> (at 23.2 °C)
}}
| Section6       = {{Chembox Pharmacology
| ATCCode_prefix = C01
| ATCCode_suffix = EB06
| HalfLife = 3 hours
}}
| Section7       = {{Chembox Hazards
| GHSPictograms = {{gHS exclamation mark}}
| GHSSignalWord = '''WARNING'''
| HPhrases = {{h-phrases|315|319|335}}
| PPhrases = {{p-phrases|261|305+351+338}}
| NFPA-H = 1
| NFPA-F = 1
| NFPA-R = 0
| AutoignitionPt = > 400 °C
| FlashPtC = 118.1
| LD50 = > 2000 mg/kg (dermal, rat)
| ExternalSDS = [https://www.chemicalbook.com/msds/Creatine.htm ChemicalBook]
}}
| Section8       = {{Chembox Related
| OtherFunction_label = alkanoic acids
| OtherFunction = {{unbulleted list|[[Sarcosine]]|[[Dimethylglycine]]|[[Glycocyamine]]|[[n-Methyl-D-aspartic acid|''N''-Methyl-D-aspartic acid]]|[[beta-Methylamino-L-alanine|''beta''-Methylamino-L-alanine]]|[[Guanidinopropionic acid]]}}
| OtherCompounds = [[Dimethylacetamide]]
}}
}}

'''Creatine''' ({{IPAc-en|ˈ|k|r|iː|ə|t|iː|n}} or {{IPAc-en|ˈ|k|r|iː|ə|t|ɪ|n}})<ref>{{cite book|title=Essentials of Creatine in Sports and Health | veditors = Stout JR, Antonio J, Kalman E |year=2008|publisher=Humana|isbn=978-1-59745-573-2}}</ref> is an [[organic compound]] with the nominal formula {{chem2|(H2N)(HN)CN(CH3)CH2CO2H}}. It exists in various [[tautomer]]s in solutions (among which are neutral form and various [[zwitterionic]] forms). Creatine is found in [[vertebrate]]s, where it facilitates recycling of [[adenosine triphosphate]] (ATP), primarily in [[muscle]] and [[brain]] tissue. Recycling is achieved by converting [[adenosine diphosphate]] (ADP) back to ATP via donation of [[phosphate group]]s. Creatine also acts as a [[Buffer solution|buffer]].<ref name="pmid26202197">{{cite journal | vauthors = Barcelos RP, Stefanello ST, Mauriz JL, Gonzalez-Gallego J, Soares FA | title = Creatine and the Liver: Metabolism and Possible Interactions | journal = Mini Reviews in Medicinal Chemistry | volume = 16 | issue = 1 | pages = 12–8 | year = 2016 | pmid = 26202197 | doi = 10.2174/1389557515666150722102613 | quote = The process of creatine synthesis occurs in two steps, catalyzed by L-arginine:glycine amidinotransferase (AGAT) and guanidinoacetate N-methyltransferase (GAMT), which take place mainly in kidney and liver, respectively. This molecule plays an important energy/pH buffer function in tissues, and to guarantee the maintenance of its total body pool, the lost creatine must be replaced from diet or de novo synthesis. }}</ref>