View source for Sarcosine

{{cs1 config|name-list-style=vanc}}
{{chembox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 464387230
| ImageFile = Sarcosine.svg
| ImageFile_Ref = {{chemboximage|correct|??}}
| ImageSize = 150
| ImageName = Skeletal formula of sarcosine
| IUPACName = ''N''-Methylglycine
| SystematicName = (Methylamino)acetic acid
|Section1={{Chembox Identifiers
| CASNo = 107-97-1
| CASNo_Ref = {{cascite|correct|CAS}}
| PubChem = 1088
| ChemSpiderID = 1057
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| UNII = Z711V88R5F
| UNII_Ref = {{fdacite|correct|FDA}}
| EINECS = 203-538-6
| KEGG = C00213
| KEGG_Ref = {{keggcite|correct|kegg}}
| MeSHName = Sarcosine
| ChEBI = 15611
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 304383
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| Beilstein = 1699442
| Gmelin = 2018
| 3DMet = B01190
| SMILES = CNCC(O)=O
| StdInChI = 1S/C3H7NO2/c1-4-2-3(5)6/h4H,2H2,1H3,(H,5,6)
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = FSYKKLYZXJSNPZ-UHFFFAOYSA-N
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
}}
|Section2={{Chembox Properties
| C=3 | H=7 | N=1 | O=2 
| Appearance = White solid
| Odor = Odourless
| Solubility = 89.09 g L<sup>−1</sup> (at 20&nbsp;°C)
| Density = 1.093 g/mL
| MeltingPtC  = 208 to 212
| MeltingPt_notes = experimental
| BoilingPtC = 
| BoilingPt_notes = 
| LogP = 0.599
| pKa = 2.36
| pKb = 11.64
| LambdaMax = 260 nm
| Absorbance = 0.05
}}
|Section3={{Chembox Thermochemistry
| DeltaHf = −513.50–−512.98 kJ mol<sup>−1</sup>
| DeltaHc = −1667.84–−1667.54 kJ mol<sup>−1</sup>
| HeatCapacity = 128.9 J K<sup>−1</sup> mol<sup>−1</sup>
}}
|Section4={{Chembox Related
| OtherFunction_label = alkanoic acids
| OtherFunction = {{unbulleted list|[[Dimethylglycine]]|[[Glycocyamine]]|[[Creatine]]|[[n-Methyl-D-aspartic acid|''N''-Methyl-<small>D</small>-aspartic acid]]|[[beta-Methylamino-L-alanine|''beta''-Methylamino-<small>L</small>-alanine]]|[[Guanidinopropionic acid]]}}
| OtherCompounds = [[Dimethylacetamide]]
}}
}}

'''Sarcosine''', also known as '''''N''-methylglycine''', or '''monomethylglycine''', is an [[amino acid]] with the formula CH<sub>3</sub>N(H)CH<sub>2</sub>CO<sub>2</sub>H.  It exists at neutral pH as the [[zwitterion]] CH<sub>3</sub>N<sup>+</sup>(H)<sub>2</sub>CH<sub>2</sub>CO<sub>2</sub><sup>−</sup>, which can be obtained as a white, water-soluble powder.  Like some amino acids, sarcosine converts to a cation at low pH and an anion at high pH, with the respective formulas CH<sub>3</sub>N<sup>+</sup>(H)<sub>2</sub>CH<sub>2</sub>CO<sub>2</sub>H and CH<sub>3</sub>N(H)CH<sub>2</sub>CO<sub>2</sub><sup>−</sup>.  Sarcosine is a close relative of glycine, with a secondary amine in place of the primary amine.

Sarcosine is ubiquitous in biological materials.  It is used in manufacturing [[biodegradable]] [[surfactants]] and toothpastes as well as in other applications. It is also a reagent in [[organic synthesis]].<ref>{{cite book |doi=10.1002/047084289X.rn02457|chapter=N -Methylglycine |title=Encyclopedia of Reagents for Organic Synthesis |year=2022 |last1=Ganesh |first1=Madhu |last2=Rao |first2=Madhuri P. |pages=1–4 |isbn=9780471936237 }}</ref>

Sarcosine is sweet to the taste.{{citation needed|date=February 2022}}

==Biochemistry==
Sarcosine is an intermediate and byproduct in [[glycine]] synthesis and degradation. Sarcosine is metabolized to glycine by the enzyme [[sarcosine dehydrogenase]], while [[Glycine N-methyltransferase|glycine-N-methyltransferase]] generates sarcosine from glycine. Sarcosine is an [[amino acid]] derivative that is naturally found in muscles and other body tissues. In the laboratory, it may be synthesized from [[chloroacetic acid]] and [[methylamine]]. Sarcosine is an intermediate in the metabolism of [[choline]] to [[glycine]].<ref>{{cite journal |doi=10.1016/j.molmet.2019.05.012|title=Formate Metabolism in Health and Disease |year=2020 |last1=Pietzke |first1=Matthias |last2=Meiser |first2=Johannes |last3=Vazquez |first3=Alexei |journal=Molecular Metabolism |volume=33 |pages=23–37 |pmid=31402327 |pmc=7056922 }}</ref> 
 
Sarcosine, like the related compounds [[dimethylglycine]] (DMG) and [[trimethylglycine]] (betaine, TMG), is formed via the metabolism of nutrients such as [[choline]] and [[methionine]], which both contain [[methyl groups]] used in a wide range of biochemical reactions. Sarcosine is rapidly degraded to glycine, which, in addition to its importance as a constituent of protein, plays a significant role in various physiological processes as a prime metabolic source of components of living cells such as [[glutathione]], [[creatine]], [[purine]]s and [[serine]]. The concentration of sarcosine in blood serum of normal human subjects is 1.4 ± 0.6 micromolar.<ref>{{cite journal | vauthors = Allen RH, Stabler SP, Lindenbaum J | title = Serum betaine, N,N-dimethylglycine and N-methylglycine levels in patients with cobalamin and folate deficiency and related inborn errors of metabolism | journal = Metabolism | volume = 42 | issue = 11 | pages = 1448–60 | date = November 1993 | pmid = 7694037 | doi = 10.1016/0026-0495(93)90198-W }}</ref>

==Industrial synthesis==
Sarcosine can be produced industrially from esters of [[chloroacetic acid]].<ref>{{cite book |last1=Koenig |first1=Günter |last2=Lohmar |first2=Elmar |last3=Rupprich |first3=Norbert |title=Ullmann's Encyclopedia of Industrial Chemistry |chapter=Chloroacetic Acids |date=2000 |doi=10.1002/14356007.a06_537 |isbn=3-527-30673-0 }}</ref>

==Surfactants==
A variety of surfactants are produced from sarcosine, for instance [[sodium lauroyl sarcosinate]].<ref>{{cite book |doi=10.1002/14356007.a25_747.pub2|chapter=Surfactants|title=Ullmann's Encyclopedia of Industrial Chemistry|year=2019|last1=Holmberg|first1=Krister|pages=1–56|isbn=9783527306732|s2cid=242339510}}</ref>

==Schizophrenia==
Early evidence suggests sarcosine is an effective and well-tolerated [[Adjuvant therapy|adjuvant]] to many [[antipsychotics]] except clozapine for the treatment of [[schizophrenia]], showing significant reductions in both positive and negative symptoms.<ref>{{cite journal | vauthors = Lane HY, Huang CL, Wu PL, Liu YC, Chang YC, Lin PY, Chen PW, Tsai G | title = Glycine transporter I inhibitor, N-methylglycine (sarcosine), added to clozapine for the treatment of schizophrenia | journal = Biological Psychiatry | volume = 60 | issue = 6 | pages = 645–9 | date = September 2006 | pmid = 16780811 | doi = 10.1016/j.biopsych.2006.04.005 | s2cid = 42741531 }}</ref><ref>{{cite journal | vauthors = Tsai G, Lane HY, Yang P, Chong MY, Lange N | title = Glycine transporter I inhibitor, N-methylglycine (sarcosine), added to antipsychotics for the treatment of schizophrenia | journal = Biological Psychiatry | volume = 55 | issue = 5 | pages = 452–6 | date = March 2004 | pmid = 15023571 | doi = 10.1016/j.biopsych.2003.09.012 | s2cid = 35723786 }}</ref> 

==Prostate cancer==
Sarcosine has also been debated as a biomarker for prostate cancer cells.<ref>{{cite journal | vauthors = Struys EA, Heijboer AC, van Moorselaar J, Jakobs C, Blankenstein MA | title = Serum sarcosine is not a marker for prostate cancer | journal = Annals of Clinical Biochemistry | volume = 47 | issue = Pt 3 | pages = 282 | date = May 2010 | pmid = 20233752 | doi = 10.1258/acb.2010.009270 | doi-access = free }}</ref><ref>{{cite journal | vauthors = Pavlou M, Diamandis EP | title = The search for new prostate cancer biomarkers continues | journal = Clinical Chemistry | volume = 55 | issue = 7 | pages = 1277–9 | date = July 2009 | pmid = 19478024 | doi = 10.1373/clinchem.2009.126870 | doi-access = free }}</ref> Other research has suggested that sarcosine plays an active role in the progression of prostate cancer, as addition of sarcosine to prostate epithelial cells caused the emergence of a new invasive phenotype.<ref>{{Cite journal |last1=Khan |first1=Amjad P |last2=Rajendiran |first2=Thekkelnaycke M |last3=Bushra |first3=Ateeq |last4=Asangani |first4=Irfan A |last5=Athanikar |first5=Jyoti N |last6=Yocum |first6=Anastasia K |last7=Mehra |first7=Rohit |last8=Siddiqui |first8=Javed |last9=Palapattu |first9=Ganesh |last10=Wei |first10=John T |last11=Michailidis |first11=George |last12=Sreekumar |first12=Arun |last13=Chinnaiyan |first13=Arul M |date=May 2013 |title=The Role of Sarcosine Metabolism in Prostate Cancer Progression |url=https://doi.org/10.1593/neo.13314 |journal=Neoplasia |volume=15 |issue=5 |pages=491–IN13 |doi=10.1593/neo.13314 |issn=1476-5586 |pmc=3638352 |pmid=23633921}}</ref>

==History==
Sarcosine was first isolated and named by the German chemist [[Justus von Liebig]] in 1847.

[[Jacob Volhard]] first synthesized it in 1862 while working in the lab of [[Hermann Kolbe]].  Prior to the synthesis of sarcosine, it had long been known to be a hydrolysis product of [[creatine]], a compound found in meat extract.  Under this assumption, by preparing the compound with [[methylamine]] and [[monochloroacetic acid]], Volhard proved that sarcosine was ''N''-methylglycine.<ref>{{cite book |last1=Rocke |first1=Alan J. |year=1993 |chapter=The Theory of Chemical Structure and the Structure of Chemical Theory |chapter-url=http://publishing.cdlib.org/ucpressebooks/view?docId=ft5g500723&chunk.id=d0e7179&toc.depth=1&toc.id=d0e7179&brand=eschol |pages=239–64 |title=The Quiet Revolution: Hermann Kolbe and the Science of Organic Chemistry |location=Berkeley |publisher=University of California |isbn=978-0-520-08110-9}}</ref>

== See also ==
* [[Glycine]]
* [[Dimethylglycine]]
* [[Trimethylglycine]]
*[[Oncometabolism]]

== References ==
{{Reflist|32em}}

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{{Neurotransmitters}}
{{Glycine receptor modulators}}
{{Ionotropic glutamate receptor modulators}}
{{Authority control}}

{{Use dmy dates|date=April 2017}}

[[Category:Alpha-Amino acids]]
[[Category:Glycine reuptake inhibitors]]
[[Category:Glycine receptor agonists]]