| Revision as of 13:41, 6 December 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 455665664 of page Sarcosine for the Chem/Drugbox validation project (updated: ''). |
Latest revision as of 17:27, 1 August 2024 edit Citation bot (talk | contribs)Bots5,434,155 edits Alter: date, pmc. Add: authors 1-1. Removed parameters. Some additions/deletions were parameter name changes. | Use this bot. Report bugs. | Suggested by Bsoyka | Category:CS1 maint: PMC format | #UCB_Category 6/6 |
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{{cs1 config|name-list-style=vanc}} |
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{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}} |
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{{chembox |
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{{chembox |
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| Watchedfields = changed |
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| verifiedrevid = 412542760 |
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| verifiedrevid = 464387230 |
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| Name = Sarcosine |
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| ImageFile = Sarcosine.svg |
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| ImageFile_Ref = {{chemboximage|correct|??}} |
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| ImageFile_Ref = {{chemboximage|correct|??}} |
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| ImageSize = 150 |
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| ImageFile = Sarcosine.png |
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| ImageName = Skeletal formula of sarcosine |
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| ImageSize = 120px |
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| IUPACName = ''N''-Methylglycine |
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| ImageName = Sarcosine |
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| IUPACName = 2-(Methylamino)acetic acid |
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| SystematicName = (Methylamino)acetic acid |
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|Section1={{Chembox Identifiers |
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| OtherNames = Sarcosine<br/>''N''-Methylglycine |
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| CASNo = 107-97-1 |
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| Section1 = {{Chembox Identifiers |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| PubChem = 1088 |
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| ChemSpiderID = 1057 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| UNII = Z711V88R5F |
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| UNII = Z711V88R5F |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| EINECS = 203-538-6 |
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| KEGG = C00213 |
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| KEGG = C00213 |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| InChI = 1/C3H7NO2/c1-4-2-3(5)6/h4H,2H2,1H3,(H,5,6) |
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| MeSHName = Sarcosine |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| ChEBI = 15611 |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| ChEMBL = 304383 |
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| ChEMBL = 304383 |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| Beilstein = 1699442 |
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| Gmelin = 2018 |
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| 3DMet = B01190 |
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| SMILES = CNCC(O)=O |
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| StdInChI = 1S/C3H7NO2/c1-4-2-3(5)6/h4H,2H2,1H3,(H,5,6) |
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| StdInChI = 1S/C3H7NO2/c1-4-2-3(5)6/h4H,2H2,1H3,(H,5,6) |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = FSYKKLYZXJSNPZ-UHFFFAOYSA-N |
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| StdInChIKey = FSYKKLYZXJSNPZ-UHFFFAOYSA-N |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| CASNo = 107-97-1 |
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}} |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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|Section2={{Chembox Properties |
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| EC-number = 203-538-6 |
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| C=3 | H=7 | N=1 | O=2 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| Appearance = White solid |
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| ChemSpiderID = 1057 |
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| Odor = Odourless |
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| ChEBI_Ref = {{ebicite|changed|EBI}} |
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| Solubility = 89.09 g L<sup>−1</sup> (at 20 °C) |
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| ChEBI = 15611 |
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| SMILES = O=C(O)CNC |
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| Density = 1.093 g/mL |
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| MeltingPtC = 208 to 212 |
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| MeltingPt_notes = experimental |
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| BoilingPtC = |
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| BoilingPt_notes = |
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| LogP = 0.599 |
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| pKa = 2.36 |
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| pKb = 11.64 |
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| LambdaMax = 260 nm |
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| Absorbance = 0.05 |
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}} |
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|Section3={{Chembox Thermochemistry |
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| DeltaHf = −513.50–−512.98 kJ mol<sup>−1</sup> |
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| DeltaHc = −1667.84–−1667.54 kJ mol<sup>−1</sup> |
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| HeatCapacity = 128.9 J K<sup>−1</sup> mol<sup>−1</sup> |
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}} |
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|Section4={{Chembox Related |
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| OtherFunction_label = alkanoic acids |
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| OtherFunction = {{unbulleted list|]|]|]|]|]|]}} |
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| OtherCompounds = ] |
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}} |
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}} |
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| Section2 = {{Chembox Properties |
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| Formula = C<sub>3</sub>H<sub>7</sub>NO<sub>2</sub> |
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| MolarMass = 89.093 g/mol |
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| MeltingPt = 208-212 °C decomp. |
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| pKa=2.23 (carboxyl), 10.01 (amino)<ref>Dawson, R.M.C., et al., ''Data for Biochemical Research'', Oxford, Clarendon Press, 1959.</ref> |
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}} |
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}} |
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}} |
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'''Sarcosine''', also known as '''''N''-methylglycine''', or '''monomethylglycine''', is a ] 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 ] 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. |
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Sarcosine is ubiquitous in biological materials. It is used in manufacturing ] ] and toothpastes as well as in other applications. It is also a reagent in ].<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> |
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Sarcosine is sweet to the taste.{{citation needed|date=February 2022}} |
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==Biochemistry== |
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Sarcosine is an intermediate and byproduct in ] synthesis and degradation. Sarcosine is metabolized to glycine by the enzyme ], while ] generates sarcosine from glycine. Sarcosine is an ] derivative that is naturally found in muscles and other body tissues. In the laboratory, it may be synthesized from ] and ]. Sarcosine is an intermediate in the metabolism of ] to ].<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> |
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Sarcosine, like the related compounds ] (DMG) and ] (betaine, TMG), is formed via the metabolism of nutrients such as ] and ], which both contain ] 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 ], ], ]s and ]. 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> |
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==Industrial synthesis== |
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Sarcosine can be produced industrially via the ]. |
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==Surfactants== |
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A variety of surfactants are produced from sarcosine, for instance ].<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> |
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==Schizophrenia== |
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Early evidence suggests sarcosine is an effective and well-tolerated ] to many ] except clozapine for the treatment of ], 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> |
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==Prostate cancer== |
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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> More recent 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> |
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==History== |
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Sarcosine was first isolated and named by the German chemist ] in 1847. |
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] first synthesized it in 1862 while working in the lab of ]. Prior to the synthesis of sarcosine, it had long been known to be a hydrolysis product of ], a compound found in meat extract. Under this assumption, by preparing the compound with ] and ], 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> |
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== See also == |
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* ] |
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* ] |
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* ] |
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*] |
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== References == |
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{{Reflist|32em}} |
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{{-}} |
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{{Neurotransmitters}} |
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{{Glycine receptor modulators}} |
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{{Ionotropic glutamate receptor modulators}} |
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{{Authority control}} |
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{{Use dmy dates|date=April 2017}} |
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] |
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] |
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] |