N , N -dimethylglycine

Structural formula
General
Surname	N , N -dimethylglycine
other names	Dimethylaminoacetic acid; DMG;
Molecular formula	C 4 H 9 NO 2
Brief description	white odorless solid
External identifiers / databases
EC number	214-267-8
ECHA InfoCard	100.012.971
PubChem	673
ChemSpider	653
DrugBank	DB02083
Wikidata	Q4369
properties
Molar mass	103.12 g mol −1
Physical state	firmly
Melting point	178-182 ° C ; 189–194 ° C (hydrochloride);
solubility	soluble in water
safety instructions
GHS labeling of hazardous substances Caution
H and P phrases	H: 302
	P: 264-270-301 + 312-280
Toxicological data	> 650 mg kg −1 ( LD 50 , rat , oral )
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

N , N -Dimethylglycine is a chemical compound from the group of carboxylic acids and glycine derivatives .

Occurrence

N , N -dimethylglycine occurs naturally in all plants and animals. It is only produced in very small quantities in humans. It is not a vitamin and there are no known deficiency symptoms. The compound is formed in the multistage biosynthesis of glycine from choline as an intermediate product through the transamination of betaine with betaine homocysteine methylase and is converted to sarcosine by dimethylglycine oxidase with elimination of formaldehyde .

Extraction and presentation

N , N -Dimethylglycin can be prepared by alkylation of glycine by Clarke-Eschweiler reaction- are prepared. In this reaction, glycine is treated with aqueous formaldehyde in formic acid , both of which serve as both a solvent and reducing agent . Hydrochloric acid is then added to give the hydrochloride . The free amino acid can be obtained by neutralization with silver (I) oxide .

{\ displaystyle \ mathrm {H_ {2} NCH_ {2} COOH + 2 \ CH_ {2} O + 2 \ HCOOH \ longrightarrow}}

{\ displaystyle \ mathrm {(CH_ {3}) _ {2} NCH_ {2} COOH + 2 \ CO_ {2} +2 \ H_ {2} O}}

properties

N , N -dimethylglycine is a flammable white odorless solid that is soluble in water.

use

N , N -dimethylglycine is a natural N -methylated glycine that is used in comparative analyzes with other N -methylated glycines such as sarcosine and betaine . It is used in the development of glycine-based ionic liquids and emulsifiers and can also be used as a biomarker of protein breakdown in COPD patients.

It is advertised as a means of lowering elevated homocysteine levels (cardiovascular diseases), as a radical scavenger and an immunomodulator. In athletes and sports animals (e.g. horses), endurance performance is to be increased and tiredness reduced. Older, non-double-blind studies showed some positive effects on the constancy of the blood sugar level and on reduced lactate levels during exercise. Recent studies have not been able to confirm this effect. It is listed in the doping rules as an ineffective e-supplement (substances with which neither a short-term nor long-term positive influence on performance is likely).

Its sodium salt, sodium N , N -dimethylglycinate, is approved as a feed additive for broilers.

safety instructions

With nitrosating agents (e.g. nitrites , nitrous acid , nitrous gases) it can lead to the formation of carcinogenic nitrosamines .

Individual evidence

↑ ^a ^b ^c ^d ^e ^f ^g Entry on N, N-dimethylglycine in the GESTIS substance database of the IFA , accessed on January 8, 2020(JavaScript required) .

↑ ^a ^b ^c Data sheet N, N-Dimethylglycine, ≥99% from Sigma-Aldrich , accessed on August 14, 2015 ( PDF ).

↑ Data sheet N, N-Dimethylglycine hydrochloride from Sigma-Aldrich , accessed on August 14, 2015 ( PDF ).

↑ Uli P. Burgerstein, Michael B. Zimmermann, Hugo Schurgast: Burgerstein's Handbook of Nutrients Prevention and healing through a balanced diet . Georg Thieme Verlag, 2007, ISBN 978-3-8304-2194-8 , p. 268 ( limited preview in Google Book search).

^ Peter C. Heinrich, Matthias Müller, Lutz Graeve: Löffler / Petrides Biochemistry and Pathobiochemistry . Springer-Verlag, 2014, ISBN 978-3-642-17972-3 , pp. 342 ( limited preview in Google Book search).

↑ Harold A. Harper, David W. Martin, Peter A. Mayes, Victor W. Rodwell: Medical Biochemistry . Springer-Verlag, 2013, ISBN 978-3-662-22150-1 , p. 310 ( limited preview in Google Book search).

^ HT Clarke, HB Gillespie, SZ Weisshaus: The Action of Formaldehyde on Amines and Amino Acids. In: Journal of the American Chemical Society. 55, 1933, p. 4571, doi : 10.1021 / ja01338a041 .

↑ Holly M Greene, SJ Wickler, RE Bray, MJ Burrill, C. London: The effect of N, N-dimethylglycine on athletic performance at altitude in horses and mules. Equine medicine 01/1996; 12 (4): 499-501.

↑ Antidoping Switzerland: Dimethylglycine ( Memento from April 19, 2016 in the Internet Archive ), accessed on August 15, 2015.

↑ Rüdiger Nickel, Theo Rous: The Anti-Doping Handbook Documents, Rules, Materials 2008. Vol. 2 . Meyer & Meyer Verlag, 2008, ISBN 978-3-89899-391-3 , p. 200 ( limited preview in Google Book Search).

↑ Regulation (EU) No. 371/2011 (PDF) for the approval of dimethylglycine sodium salt as a feed additive for broiler chickens (approval holder: Taminco NV).

[GESTIS-1] ↑ ^a ^b ^c ^d ^e ^f ^g Entry on N, N-dimethylglycine in the GESTIS substance database of the IFA , accessed on January 8, 2020(JavaScript required) .

[Sigma-2] Data sheet N, N-Dimethylglycine, ≥99% from Sigma-Aldrich , accessed on August 14, 2015 ( PDF ).

[Sigma_HCL-3] Data sheet N, N-Dimethylglycine hydrochloride from Sigma-Aldrich , accessed on August 14, 2015 ( PDF ).

[Uli_P._Burgerstein,_Michael_B._Zimmermann,_Hugo_Schurgast-4] Uli P. Burgerstein, Michael B. Zimmermann, Hugo Schurgast: Burgerstein's Handbook of Nutrients Prevention and healing through a balanced diet . Georg Thieme Verlag, 2007, ISBN 978-3-8304-2194-8 , p. 268 ( limited preview in Google Book search).

[Peter_C._Heinrich,_Matthias_Müller,_Lutz_Graeve-5] Peter C. Heinrich, Matthias Müller, Lutz Graeve: Löffler / Petrides Biochemistry and Pathobiochemistry . Springer-Verlag, 2014, ISBN 978-3-642-17972-3 , pp. 342 ( limited preview in Google Book search).

[Harold_A._Harper,_David_W._Martin,_Peter_A._Mayes,_Victor_W._Rodwell-6] Harold A. Harper, David W. Martin, Peter A. Mayes, Victor W. Rodwell: Medical Biochemistry . Springer-Verlag, 2013, ISBN 978-3-662-22150-1 , p. 310 ( limited preview in Google Book search).

[DOI10.1021/ja01338a041-7] HT Clarke, HB Gillespie, SZ Weisshaus: The Action of Formaldehyde on Amines and Amino Acids. In: Journal of the American Chemical Society. 55, 1933, p. 4571, doi : 10.1021 / ja01338a041 .

[Holly-8] Holly M Greene, SJ Wickler, RE Bray, MJ Burrill, C. London: The effect of N, N-dimethylglycine on athletic performance at altitude in horses and mules. Equine medicine 01/1996; 12 (4): 499-501.

[Antidoping_Schweiz-9] Antidoping Switzerland: Dimethylglycine ( Memento from April 19, 2016 in the Internet Archive ), accessed on August 15, 2015.

[Rüdiger_Nickel,_Theo_Rous-10] Rüdiger Nickel, Theo Rous: The Anti-Doping Handbook Documents, Rules, Materials 2008. Vol. 2 . Meyer & Meyer Verlag, 2008, ISBN 978-3-89899-391-3 , p. 200 ( limited preview in Google Book Search).