Description
Sarcosine(cas:107-97-1) is the N-methyl derivative of glycine. It can be metabolized to the glycine through sarcosine dehydrogenase. It can be naturally found in many body tissues including muscles. In the laboratory, sarcosine could be synthesized through the reaction between chloroacetic acid and methylamine. Sarcosine is a potential interesting direction for the treatment of mental illness such as schizophrenia, possibly being related to its effect of increasing the glycine content in the brain, which increased the NMDA receptor activity. Sarcosine is also effective in the treatment of depression. Recent study has shown that sarcosine might be an important bio-marker for prostate cancer.
Chemical Properties
Sarcosine, also known as N-methylglycine, is ubiquitous in biological materials and is present in such foods as egg yolks, turkey, ham, vegetables, legumes, etc. It reduced the production of sebum and imperfections linked to hyperseborrhea, thereby refining skin texture. Sarcosine matifies skin perfecting treatments and treatments for oily skin.
Sarcosine is a natural amino acid found in muscles and other body tissues. It is found naturally as an intermediate in the metabolism of choline to glycine. Sarcosine is a white and deliquescence crystalline power. It is sweet to the taste and dissolves in water. It is used in manufacturing biodegradable surfactants and toothpastes as well as in other applications.
Biological Functions
Sarcosine reduces dihydrotestosterone (DHT) by inhibiting the enzyme 5 alphareductase. Sebum production is stimulated by androgens. 5 alpha-reductase metabolises testosterone in the skin into its more potent form dihydrotestosterone (DHT) that is responsible for the overproduction of sebum. As a result, sarcosine reduces shine, tightens and reduces pore size, evens tone and complexion.
Uses
sarcosine is an intermediate in the production glycine from dietary consumption of choline. It is used in making toothpastes and biodegradable surfactants. Sarcosine can be found in foods such as vegetables, ham, egg yolks, turkey and legumes. The normal concentrations of sarcosine in human serum and in human urine are 1.4 µM and 1.6 µM respectively.
Sarcosine has been observed to improve treatment of the mental illness known as schizophrenia: 2 g per day consumption of sarcosine (in addition to antipsychotic drug therapy) results in significant additional reductions not only both positive and negative symptoms, but also general psychopathological and neurocognitive symptoms. Sarcosine is thought to work by increasing glycine concentrations in the brain which causes increased NMDA receptor activation. Interestingly, consumption of sarcosine also reduced depressive symptoms in patients with schizophrenia. A clinical study showed sarcosine to be significantly more effective in treating major depression than the established antidepressant drug Citalopram.
Preparation
Sarcosine is prepared by boiling creatine with an aqueous solution of 10 times its weight of barium hydroxide until all odour of ammonia has disappeared. The creatine is decomposed into sarcosine and urea, the latter product being further split up into ammonia and carbonic acid.The excess of barium hydroxide is removed by a current of carbon dioxide, the liquid boiled, filtered, and evaporated to a syrup, from which the sarcosine is deposited in foliated crystals on standing. Sarcosine also results from the action of acids or alkalies on caffeine and theobromine (Vol.VI); and w. Paulmann (Arch. Pharm., 232, 601) recommends the hydrolysis of caffeine as the best method for the preparation of sarcosine, the yield being 60% of the theoretical.
References
https://en.wikipedia.org/wiki/Sarcosine
https://pubchem.ncbi.nlm.nih.gov/compound/sarcosine#section=Top
Chemical Properties
White crystalline powder
Uses
Has been found in starfish and sea urchins. It is used as intermediate in the synthesis of antienzyme agents for toothpaste. Found to be a marker for prostate cancer bioagression.
Uses
sarcosine is a naturally occurring amino acid that is used in cosmetic formulations as a skin conditioner. There are some studies indicating that it is effective for oily skin. Its chemical name is n-methyl glycine.
Uses
Sarcosine can improve people's intelligence, especially for exams such as the students need to temporarily increase the effectiveness of intelligence is more obvious. sarcosine can increase muscle strength and anaerobic explosiveness.To prevent damage caused by the brain injury. Sarcosine can effectively improve athletic performance,power, and shorten muscle recovery time.
Uses
Sarcosine is an important component for the production of the amino acid glycine and a byproduct of glycine breakdown. In the body, it is produced by converting dietary choline to glycine or breaking down methionine into glycine. It can also be synthesized in the laboratory with chloroacetic acid and methylamine. Sarcosine has a unique mild sweetness. Since a derivative of creatine helps prevent tooth decay and causes foam, it acts as an ingredient in toothpaste. Sarcosine can also be used as a drug, and research over the past 20 years has revealed its role in treating mental health disorders such as schizophrenia and depression.
Definition
ChEBI: Sarcosine is a N-alkylglycine that is the N-methyl derivative of glycine. It is an intermediate in the metabolic pathway of glycine. It has a role as a glycine transporter 1 inhibitor, a glycine receptor agonist, a human metabolite, an Escherichia coli metabolite and a mouse metabolite. It is a N-alkylglycine, a N-methyl-amino acid and a member of N-methylglycines. It is a conjugate base of a sarcosinium. It is a conjugate acid of a sarcosinate. It is a tautomer of a sarcosine zwitterion.
General Description
Deliquescent crystals or powder. Has a sweetish taste.
Air & Water Reactions
Deliquescent. Water soluble.
Reactivity Profile
Sarcosine is an amide. Amides/imides react with azo and diazo compounds to generate toxic gases. Flammable gases are formed by the reaction of organic amides/imides with strong reducing agents. Amides are very weak bases (weaker than water). Imides are less basic yet and in fact react with strong bases to form salts. That is, they can react as acids. Mixing amides with dehydrating agents such as P2O5 or SOCl2 generates the corresponding nitrile. The combustion of these compounds generates mixed oxides of nitrogen (NOx). Sarcosine is incompatible with acids. .
Fire Hazard
Flash point data for Sarcosine are not available. Sarcosine is probably combustible.
Biological Activity
Endogenous inhibitor of GlyT1 that displays antipsychotic activity. Potentiates the action of glycine on the NMDA glycine binding site.
Side effects
Sarcosine, a dietary supplement, is generally considered harmless with minimal side-effects. However, some individuals report experiencing euphoria and hyperactivity after consuming it. Men taking sarcosine may have an increased risk for prostate cancer, while others may experience sleeplessness, irritability, and headaches.
Sarcosine: The Super Nutrient That May Reverse Schizophrenia Symptoms
Purification Methods
Crystallise sarcosine from absolute EtOH, 95% EtOH or H2O. It sublimes at 180-185o/0.3mm with 99.1% recovery [Gross & Gradsky J Am Chem Soc 77 1678 1955]. [Cocker & Harris J Chem Soc 1291 1940, Cocker & Lapworth J Chem Soc 1897 1931, Greenstein & Winitz The Chemistry of the Amino Acids J. Wiley, Vol 3 p 2750 1961, Beilstein 4 III 1121, 4 IV 2363.]
