Sarcosine

Structural formula
General
Surname	Sarcosine
other names	Sarcosine N -methylglycine Methylaminoacetic acid SARCOSINE ( INCI )
Molecular formula	C 3 H 7 NO 2
Brief description	colorless, crystalline solid
External identifiers / databases
CAS number 107-97-1 EC number 203-538-6 ECHA InfoCard 100.003.217 PubChem 1088 ChemSpider 1057 DrugBank DB12519 Wikidata Q414157
properties
Molar mass	89.09 g mol −1
Physical state	firmly
Melting point	208 ° C
boiling point	Decomposition: 212 ° C
solubility	very good in water (1480 g l −1 at 20 ° C)
safety instructions
GHS labeling of hazardous substances no GHS pictograms H and P phrases H: no H-phrases P: no P-phrases
Thermodynamic properties
ΔH f 0	−513.3 kJ / mol
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Sarcosine (abbr .: Sar) is a non-proteinogenic amino acid . It is of glycine derived, an intermediate level of amino acid metabolism and a peptide component of the antibiotic actinomycin , the immunosuppressant cyclosporin and the angiotensin II - receptors - antagonists Saralasin . It is also found in muscles and other body tissues. Sarcosine also serves as a precursor for the preparation of certain surfactants (u. A. Acylsarcosines, z. B. lauroyl sarcosine and oleoyl sarcosine ), and is used in the printing of azo dyes .

Intramolecular rearrangement can result in alanine from sarcosine and glycine through demethylation .

history

Sarcosine was first isolated from the creatine of the meat broth by Justus von Liebig ( Greek σάρξ , sarx = meat), which is where the name comes from.

Medical relevance

While human urine usually does not contain sarcosine, it can be found in the urine of patients with prostate cancer . As a biomarker , it can therefore be used to diagnose prostate cancer. A distinction can be made between benign prostatic hyperplasia (benign enlargement of the prostate ) and metastatic and non-metastatic prostate cancer.

In addition, sarcosine at doses of 2 g per day in combination with other neuroleptics , with the exception of clozapine , reduced the typical symptoms of schizophrenia .

See also

• Betaine
• Sarkosyl

Individual evidence

1. ↑ Entry on SARCOSINE in the CosIng database of the EU Commission, accessed on March 4, 2020.
2. ↑ ^{a b c d} Entry on sarcosine in the GESTIS substance database of the IFA , accessed on June 6, 2018(JavaScript required) .
3. ↑ Data sheet Sarcosine at Acros, accessed on June 6, 2018.
4. ↑ David R. Lide (Ed.): CRC Handbook of Chemistry and Physics . 90th edition. (Internet version: 2010), CRC Press / Taylor and Francis, Boca Raton, FL, Standard Thermodynamic Properties of Chemical Substances, pp. 5-24.
5. ^ K. Lindner: Tenside, textile auxiliaries, washing raw materials. Volumes I-III, Wissenschaftliche Verlagsgesellschaft, Stuttgart 1964–1971.
6. ^ A. Sreekumar, LM Poisson et al .: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. In: Nature. Volume 457, Number 7231, February 2009, pp. 910-914. doi: 10.1038 / nature07762 . PMID 19212411 . PMC 2724746 (free full text).
7. ↑ H. Lane, C. Huang, P. Wu, Y. Liu, Y. Chang, P. Lin, P. Chen, G. Tsai: Glycine transporter I inhibitor, N-methylglycine (sarcosine), added to clozapine for the treatment of schizophrenia . In: Biological Psychiatry . tape 60 , no. 6 , 2006, p. 645-649 , doi : 10.1016 / j.biopsych.2006.04.005 , PMID 16780811 .
8. ↑ G. Tsai, H. Lane, P. Yang, M. Chong, N. Lange: Glycine transporter I inhibitor, N-methylglycine (sarcosine), added to antipsychotics for the treatment of schizophrenia . In: Biological Psychiatry . tape 55 , no. 5 , 2004, p. 452-456 , doi : 10.1016 / j.biopsych.2003.09.012 , PMID 15023571 .