Wikipedia:WikiProject Chemicals/Chembox validation/VerifiedDataSandbox and Sarcosine: Difference between pages

{{cs1 config|name-list-style=vanc}}

| Watchedfields = changed

| verifiedrevid = 464387230

| ImageFile = Sarcosine.svg

| 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_Ref = {{fdacite|correct|FDA}}

| EINECS = 203-538-6

| KEGG_Ref = {{keggcite|correct|kegg}}

| MeSHName = Sarcosine

| ChEBI = 15611

| ChEBI_Ref = {{ebicite|correct|EBI}}

| ChEMBL_Ref = {{ebicite|correct|EBI}}

| Beilstein = 1699442

| Gmelin = 2018

| 3DMet = B01190

| SMILES = CNCC(O)=O

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| 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⁻¹ (at 20 °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⁻¹

| DeltaHc = −1667.84–−1667.54 kJ mol⁻¹

| HeatCapacity = 128.9 J K⁻¹ mol⁻¹

}}

|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 a [[amino acid]] with the formula CH₃N(H)CH₂CO₂H. It exists at neutral pH as the [[zwitterion]] CH₃N⁺(H)₂CH₂CO₂⁻, 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 CH₃N⁺(H)₂CH₂CO₂H and CH₃N(H)CH₂CO₂⁻. 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''-methyl transferase]] 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 via the [[Strecker amino acid synthesis]].

==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> 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>

==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}}

{{-}}

{{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]]