Sarcosine, also known as ''N''-methylglycine, or monomethylglycine, is a

amino acid Amino acids are organic compounds that contain both amino and carboxylic acid functional groups. Although over 500 amino acids exist in nature, by far the most important are the 22 α-amino acids incorporated into proteins. Only these 22 a ...

with the formula CH₃N(H)CH₂CO₂H. It exists at neutral pH as the

zwitterion In chemistry, a zwitterion ( ; ), also called an inner salt or dipolar ion, is a molecule that contains an equal number of positively and negatively charged functional groups. : (1,2- dipolar compounds, such as ylides, are sometimes excluded from ...

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 Biodegradation is the breakdown of organic matter by microorganisms, such as bacteria and fungi. It is generally assumed to be a natural process, which differentiates it from composting. Composting is a human-driven process in which biodegrada ...

surfactants Surfactants are chemical compounds that decrease the surface tension or interfacial tension between two liquids, a liquid and a gas, or a liquid and a solid. The word ''surfactant'' is a blend of "surface-active agent", coined in 1950. As t ...

and toothpastes as well as in other applications. It is also a reagent in

organic synthesis Organic synthesis is a branch of chemical synthesis concerned with the construction of organic compounds. Organic compounds are molecules consisting of combinations of covalently-linked hydrogen, carbon, oxygen, and nitrogen atoms. Within the gen ...

. Sarcosine is sweet to the taste.

Biochemistry

Sarcosine is an intermediate and byproduct in

glycine Glycine (symbol Gly or G; ) is an amino acid that has a single hydrogen atom as its side chain. It is the simplest stable amino acid. Glycine is one of the proteinogenic amino acids. It is encoded by all the codons starting with GG (G ...

synthesis and degradation. Sarcosine is metabolized to glycine by the enzyme sarcosine dehydrogenase, while glycine-''N''-methyl transferase 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

chloroacetic acid Chloroacetic acid, industrially known as monochloroacetic acid (MCA), is the organochlorine compound with the formula . This carboxylic acid is a useful building block in organic synthesis. It is a colorless solid. Related compounds are dichlo ...

and

methylamine Methylamine, also known as methanamine, is an organic compound with a formula of . This colorless gas is a derivative of ammonia, but with one hydrogen atom being replaced by a methyl group. It is the simplest primary amine. Methylamine is sold ...

. Sarcosine is an intermediate in the metabolism of

choline Choline is a cation with the chemical formula . Choline forms various Salt (chemistry), salts, such as choline chloride and choline bitartrate. An essential nutrient for animals, it is a structural component of phospholipids and cell membrane ...

. Sarcosine, like the related compounds dimethylglycine (DMG) and

trimethylglycine Trimethylglycine is an amino acid derivative with the formula . A colorless, water-soluble solid, it occurs in plants. Trimethylglycine is a zwitterion: the molecule contains both a quaternary ammonium cation, quaternary ammonium group and a carb ...

(betaine, TMG), is formed via the metabolism of nutrients such as

and

methionine Methionine (symbol Met or M) () is an essential amino acid in humans. As the precursor of other non-essential amino acids such as cysteine and taurine, versatile compounds such as SAM-e, and the important antioxidant glutathione, methionine play ...

, 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 Glutathione (GSH, ) is an organic compound with the chemical formula . It is an antioxidant in plants, animals, fungi, and some bacteria and archaea. Glutathione is capable of preventing damage to important cellular components caused by sources ...

creatine Creatine ( or ) is an organic compound with the nominal formula . It exists in various tautomers in solutions (among which are neutral form and various zwitterionic forms). Creatine is found in vertebrates, where it facilitates recycling of ...

purine Purine is a heterocyclic aromatic organic compound that consists of two rings (pyrimidine and imidazole) fused together. It is water-soluble. Purine also gives its name to the wider class of molecules, purines, which include substituted puri ...

s and

serine Serine (symbol Ser or S) is an α-amino acid that is used in the biosynthesis of proteins. It contains an α- amino group (which is in the protonated − form under biological conditions), a carboxyl group (which is in the deprotonated − ...

. The concentration of sarcosine in blood serum of normal human subjects is 1.4 ± 0.6 micromolar.

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.

Schizophrenia

Early evidence suggests sarcosine is an effective and well-tolerated

adjuvant In pharmacology, an adjuvant is a drug or other substance, or a combination of substances, that is used to increase the efficacy or potency of certain drugs. Specifically, the term can refer to: * Adjuvant therapy in cancer management * Anal ...

to many

antipsychotics Antipsychotics, previously known as neuroleptics and major tranquilizers, are a class of psychotropic medication primarily used to manage psychosis (including delusions, hallucinations, paranoia or disordered thought), principally in schizo ...

except clozapine for the treatment of

schizophrenia Schizophrenia () is a mental disorder characterized variously by hallucinations (typically, Auditory hallucination#Schizophrenia, hearing voices), delusions, thought disorder, disorganized thinking and behavior, and Reduced affect display, f ...

, showing significant reductions in both positive and negative symptoms.

Prostate cancer

Sarcosine has also been debated as a biomarker for prostate cancer cells. 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.

History

Sarcosine was first isolated and named by the German chemist

Justus von Liebig Justus ''Freiherr'' von Liebig (12 May 1803 – 18 April 1873) was a Germans, German scientist who made major contributions to the theory, practice, and pedagogy of chemistry, as well as to agricultural and biology, biological chemistry; he is ...

in 1847.

Jacob Volhard Jacob Volhard (4 June 1834 – 14 January 1910) was the German chemist who discovered, together with his student Hugo Erdmann, the Volhard–Erdmann cyclization reaction. He was also responsible for the improvement of the Hell–Volhard–Zel ...

first synthesized it in 1862 while working in the lab of

Hermann Kolbe Adolph Wilhelm Hermann Kolbe (27 September 1818 – 25 November 1884) was a German chemist and academic, and a major contributor to the birth of modern organic chemistry. He was a professor at Marburg and Leipzig. Kolbe was the first to apply t ...

. 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 monochloroacetic acid, Volhard proved that sarcosine was ''N''-methylglycine.

References

{{Use dmy dates, date=April 2017 Alpha-Amino acids Glycine reuptake inhibitors Glycine receptor agonists