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Sarcosine
Sarcosine
IUPAC name
Other names Sarcosine
N-Methylglycine
Identifiers
CAS number 107-97-1 Yes check.svgY
EC-number 203-538-6
SMILES
InChI
ChemSpider ID 1057
Properties
Molecular formula C3H7NO2
Molar mass 89.093 g/mol
Melting point

208-212 °C decomp.

 Yes check.svgY (what is this?)  (verify)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Sarcosine, also known as N-methyglycine, is an intermediate and byproduct in glycine synthesis and degradation. Sarcosine is metabolized to glycine by the enzyme sarcosine dehydrogenase, while glycine-N-methyl transferase generates sarcosine from glycine. Sarcosine is a natural amino acid found in muscles and other body tissues. In the laboratory, it may be synthesized from chloroacetic acid and methylamine. Sarcosine is found naturally as an intermediate in the metabolism of choline to glycine. Sarcosine is sweet to the taste and dissolves in water. It is used in manufacturing biodegradable surfactants and toothpastes as well as in other applications.

Sarcosine is ubiquitous in biological materials and is present in such foods as egg yolks, turkey, ham, vegetables, legumes, etc.

Sarcosine is formed from dietary intake of choline and from the metabolism of methionine, and 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, purines and serine. The concentration of sarcosine in blood serum of normal human subjects is 1.59 ± 1.08 millimolar.

Contents

Clinical significance

Sarcosine has no known toxicity, as evidenced by the lack of phenotypic manifestations of sarcosinemia, an inborn error of sarcosine metabolism. Sarcosinemia can result from severe folate deficiency because of the folate requirement for the conversion of sarcosine to glycine.

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Schizophrenia

Recently, sarcosine has been investigated in relation to the mental illness schizophrenia. Early evidence suggests that intake of 2 g/day sarcosine as add-on therapy to certain antipsychotics (not clozapine[1]) in schizophrenia gives significant additional reductions in both positive and negative symptomatology as well as the neurocognitive and general psychopathological symptoms that are common to the illness. Sarcosine had been tolerated well.[2] It is also under investigation for the possible prevention of schizophrenic illness during the prodromal stage of the disease. It acts as a type 1 glycine transporter inhibitor. It increases glycine concentrations in the brain thus causing increased NMDA receptor activation and a reduction in symptoms. As such, it might be an interesting treatment option and a possible new direction in the treatment of the mental illness in the future.

Prostate cancer marker

In a paper published in the journal Nature February 12, 2009, sarcosine was shown to activate benign prostate cancer cells and to indicate the malignancy of prostate cancer cells when measured in urine. Sarcosine was identified as a differential metabolite that was greatly increased during prostate cancer progression to metastasis and could be detected in urine. Sarcosine levels were also increased in invasive prostate cancer cell lines relative to benign prostate epithelial cells.[3] Sarcosine levels seemed to control the invasiveness of the cancer.[4]

History

Sarcosine was first isolated and named by the German chemist Justus von Liebig in 1847, while Jacob Volhard first synthesized it in 1862.

See also

References

  1. ^ Lane H, Huang C, Wu P, Liu Y, Chang Y, Lin P, Chen P, Tsai G (2006). "Glycine transporter I inhibitor, N-methylglycine (sarcosine), added to clozapine for the treatment of schizophrenia". Biol Psychiatry 60 (6): 645–9. doi:10.1016/j.biopsych.2006.04.005. PMID 16780811.  
  2. ^ Tsai G, Lane H, Yang P, Chong M, Lange N (2004). "Glycine transporter I inhibitor, N-methylglycine (sarcosine), added to antipsychotics for the treatment of schizophrenia". Biol Psychiatry 55 (5): 452–6. doi:10.1016/j.biopsych.2003.09.012. PMID 15023571.  
  3. ^ http://sciencenow.sciencemag.org/cgi/content/full/2009/211/1?etoc "A Urine Test for Prostate Cancer?"
  4. ^ http://www.nature.com/nature/journal/v457/n7231/pdf/nature07762.pdf Sreekumar et al, "Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression"

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