sarcosine

Also known as 2-(methylamino)acetic acid, N-methylglycine, methylglycine

Sarcosine, also known as '''N-methylglycine, or monomethylglycine', is a non-proteinogenic amino acid with the formula CH3N(H)CH2CO2H. It is the N''-methyl derivative of glycine, with a secondary amine in place of the primary amine, and occurs naturally in muscles and other body tissues as an intermediate in the metabolism of choline to glycine. It was first isolated and named by the German chemist Justus von Liebig in 1847.

Chemical data

Formula: C3H7NO2
Molecular weight: 89.09 g/mol
IUPAC name: 2-(methylamino)acetic acid
SMILES: CNCC(=O)O
InChIKey: FSYKKLYZXJSNPZ-UHFFFAOYSA-N
XLogP: -2.8
Polar surface area: 49.3 Å²
H-bond donors: 2
H-bond acceptors: 3
Formal charge: 0

via PubChem

Research

3,617 papers

Sarcosine decreases in sarcopenia and enhances muscle regeneration and adipose thermogenesis by activating anti-inflammatory macrophages.

~8 min read

Article

14 sections

Contents

Chemistry
Industrial synthesis
Surfactants
Biochemistry
Distribution
Pharmacology
Pharmacodynamics
Pharmacokinetics
Research
Schizophrenia
Prostate cancer
History
See also
References

Sarcosine, also known as '''N-methylglycine, or monomethylglycine', is a non-proteinogenic amino acid with the formula CH3N(H)CH2CO2H. It is the N-methyl derivative of glycine, with a secondary amine in place of the primary amine, and occurs naturally in muscles and other body tissues as an intermediate in the metabolism of choline to glycine. It was first isolated and named by the German chemist Justus von Liebig in 1847.

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. It has a mildly sweet taste.