iPedia Free Information Center

Information about Sarcosine

Sarcosine
IUPAC name2-(Methylamino)acetic acid
Other namesSarcosine
N-Methylglycine
Identifiers
CAS number107-97-1
SMILESCNCC(O)=O
Properties
Molecular formulaC3H7NO2
Molar mass89.09 g/mol
Melting point 208-212 °C (decomp.)
Boiling point decomp.
Except where noted otherwise, data are given for
materials in their standard state
(at 25 C, 100 kPa)


Sarcosine is the N-methyl derivative of glycine. It 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 reported to be 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 reported to be 1.59 ± 1.08 micromoles per liter.

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.

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, general psychiatric and depressive 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.

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

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. 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. PMID 15023571. 
IUPAC nomenclature is a system of naming chemical compounds and of describing the science of chemistry in general. It is developed and kept up to date under the auspices of the International Union of Pure and Applied Chemistry (IUPAC).
..... Click the link for more information.
CAS registry numbers are unique numerical identifiers for chemical compounds, polymers, biological sequences, mixtures and alloys. They are also referred to as CAS numbers, CAS RNs or CAS #s.
..... Click the link for more information.
smiles

File extension: .smi
Type of format: chemical file format

The simplified molecular input line entry specification or SMILES
..... Click the link for more information.
A chemical formula is a concise way of expressing information about the atoms that constitute a particular chemical compound. A chemical formula is also a short way of showing how a chemical reaction occurs.
..... Click the link for more information.
Molar mass, symbol M,[1] is the mass of one mole of a substance (chemical element or chemical compound).[2] It is a physical property which is characteristic of each pure substance.
..... Click the link for more information.
The melting point of a crystalline solid is the temperature range at which it changes state from solid to liquid. Although the phrase would suggest a specific temperature and is commonly and incorrectly used as such in most textbooks and literature, most crystalline compounds
..... Click the link for more information.
boiling point of a liquid is the temperature at which the vapor pressure of the liquid equals the environmental pressure surrounding the liquid.[1][2][3][4]
..... Click the link for more information.
standard state of a material is its state at 1 bar (100 kilopascals exactly). This pressure was changed from 1 atm (101.325 kilopascals) by IUPAC in 1990.[1] The standard state of a material can be defined at any given temperature, most commonly 25 degrees Celsius,
..... Click the link for more information.
In chemistry, a methyl group is a hydrophobic alkyl functional group derived from methane (CH4). It has the formula -CH3 and is very often abbreviated as -Me in the structure of a molecule. This hydrocarbon unit can be found in many organic compounds.
..... Click the link for more information.
For the plant, see .


Glycine (abbreviated as Gly or G)[1] is the organic compound with the formula HO2CCH2NH2.
..... Click the link for more information.
amino acid is a molecule that contains both amine and carboxyl functional groups. In biochemistry, this term refers to alpha-amino acids with the general formula H2NCHRCOOH, where R is an organic substituent.
..... Click the link for more information.
Chloroacetic acid is the chemical compound with the formula ClCH2CO2H. This carboxylic acid is a useful building block in organic synthesis. Like other chloroacetic acids and related halocarbons, it is a potentially dangerous alkylating agent.
..... Click the link for more information.
Methylamine is the chemical compound with a formula of CH3NH2. It is a derivative of ammonia, wherein one H atom is replaced by a methyl group. It is the simplest primary amine.
..... Click the link for more information.
Choline is an organic compound, classified as an essential nutrient[1][2][3] and usually grouped within the Vitamin B complex. This natural amine is found in the lipids that make up cell membranes and in the neurotransmitter acetylcholine.
..... Click the link for more information.
Methionine (abbreviated as Met or M)[1] is an α-amino acid with the chemical formula HO2CCH(NH2)CH2CH2SCH3. This essential amino acid is classified as nonpolar.
..... Click the link for more information.
Glutathione (GSH) is a tripeptide. It contains an unusual peptide linkage between the amine group of cysteine and the carboxyl group of the glutamate side chain. Glutathione, an antioxidant, protects cells from toxins such as free radicals.
..... Click the link for more information.
Creatine is nitrogenous organic acid which naturally occurs in vertebrates and helps to supply energy to muscle and nerve cells. Creatine was identified in 1832 when Michel Eugène Chevreul discovered it as a component of skeletal muscle which he later named creatine after the Greek
..... Click the link for more information.
Purine (1) is a heterocyclic aromatic organic compound, consisting of a pyrimidine ring fused to an imidazole ring. Purines make up one of the two groups of nitrogenous bases. Pyrimidines make up the other group.
..... Click the link for more information.
Serine (abbreviated as Ser or S)[1] is an organic compound with the formula HO2CCH(NH2)CH2OH. It is one of the 20 naturally occurring proteinogenic amino acids. Its codons are UCU, UCC, UCA, UCG, AGU and AGC.
..... Click the link for more information.
Sarcosinemia
Classification & external resources

Sarcosine
ICD-10 E 72.5
ICD-9 270.8

OMIM 268900
DiseasesDB 29841

Sarcosinemia is characterized by an increased concentration of sarcosine in blood plasma and urine.
..... Click the link for more information.
MeSH D005494 Signs of folic acid deficiency are often subtle.

Presentation

Diarrhea, loss of appetite, and weight loss can occur. Additional signs are weakness, sore tongue, headaches, heart palpitations, irritability, and behavioral disorders.
..... Click the link for more information.
Folic acid and folate (the anion form) are forms of the water-soluble Vitamin B9. These occur naturally in food and can also be taken as supplements. Folate gets its name from the Latin word folium ("leaf").
..... Click the link for more information.
Schizophrenia
Classification & external resources

Eugen Bleuler (1857–1939) coined the term "Schizophrenia" in 1908
ICD-10 F 20.
ICD-9 295

OMIM 181500
DiseasesDB 11890
MedlinePlus 000928
eMedicine med/2072   emerg/520


..... Click the link for more information.
The term antipsychotic is applied to a group of drugs used to treat psychosis. Common conditions with which antipsychotics might be used include schizophrenia, mania and delusional disorder.
..... Click the link for more information.
The term symptom (from the Greek σύμπτωμα meaning 'chance', 'mishap' or 'casualty', itself derived from συμπιπτω
..... Click the link for more information.
In medicine, a prodrome is an early symptom indicating the development of a disease, or indicating that a disease attack is imminent. For example fever, malaise, headache and anorexia (lack of desire to eat) are part of the prodrome for the mumps.
..... Click the link for more information.
For the plant, see .


Glycine (abbreviated as Gly or G)[1] is the organic compound with the formula HO2CCH2NH2.
..... Click the link for more information.
In animals, the brain or encephalon (Greek for "in the skull"), is the control center of the central nervous system, responsible for behavior. The brain is located in the head, protected by the skull and close to the primary sensory apparatus of vision, hearing,
..... Click the link for more information.
NMDA receptor (NMDAR) is an ionotropic receptor for glutamate (NMDA (N-methyl d-aspartate) is a name of its selective specific agonist). Activation of NMDA receptors results in the opening of an ion channel that is nonselective to cations.
..... Click the link for more information.
Justus von Liebig

Justus von Liebig-chemist
Born 12 May 1803(1803--)
Darmstadt, Grand Duchy of Hesse
..... Click the link for more information.


This article is copied from an article on Wikipedia.org - the free encyclopedia created and edited by online user community. The text was not checked or edited by anyone on our staff. Although the vast majority of the wikipedia encyclopedia articles provide accurate and timely information please do not assume the accuracy of any particular article. This article is distributed under the terms of GNU Free Documentation License.
Herod_Archelaus


page counter