Quick Search
Methylguanidoacetic acid is a metabolite of glycine in which the amino group has been converted into a guanidine by guanylation (transfer of a guanidine group from arginine).
In vertebrate organism Methylguanidoacetic acid is then transformed into creatine by methylation.
Methylguanidoacetic acid is used as a supplement and as a feed additive in poultry farming.
CAS: 352-97-6
MF: C3H7N3O2
MW: 117.11
EINECS: 206-529-5
Synonyms
N-Amidinoglycin;(Aminoiminomethyl)aminoacetic acid;GLYCOCYAMINE(GUANIDINOACETIC ACID)(P);Guanidineacetic acid,N-Amidinoglycine, N-Guanylglycine, Glycocyamine;Guanidineacetic acid 99%;Guanidineacetic acid,glucocyamine,Glycocyamine;BetacyaMine;NSC 1901
However, the metabolism of creatine from Methylguanidoacetic acid in the liver causes a depletion of methyl groups.
This causes homocysteine levels to rise, which has been shown to produce cardiovascular and skeletal problems.
Methylguanidoacetic acid plays a role in the metabolism of the amino acids serine, threonine, and proline.
The N-amidino derivative of glycine.
Methylguanidoacetic acid is a metabolite of creatine and is formed by reaction with the amino acid arginine.
Methylguanidoacetic acid is also synthesized from guanidinoacetate, which is derived from the oxidation of arginine.
Methylguanidoacetic acid can be found in human serum and eye disorders such as glaucoma.
The analytical method for Methylguanidoacetic acid involves the conversion of guanidine to guanidinoacetic acid using nitrous acid, followed by gas chromatographic separation of the products.
The concentration of Methylguanidoacetic acid in human serum has been shown to have an inverse relationship with body mass index (BMI).
This means that people with a higher BMI have lower levels of Methylguanidoacetic acids in their blood than those who are thinner.
Methylguanidoacetic acid has also been shown to increase energy metabolism and inhibit glycolysis in humans.
Methylguanidoacetic acid is a metabolic intermediate product of glycine in the human body, it is the direct precursor of creatine biosynthesis.
Methylguanidoacetic acid can promote insulin secretion and affect insulin metabolism; it can also be used as an anti-diabetic compound to improve symptoms of hyperglycemia.
Methylguanidoacetic acid, also known as glycocyamine, is an organic compound with the chemical formula C3H7N5O2.
Methylguanidoacetic acid is characterized by the presence of a guanidine group and an acetic acid moiety, making it a derivative of both amino acids and guanidine.
Methylguanidoacetic acid is a naturally occurring intermediate in the biosynthesis of creatine, which is crucial for energy metabolism in muscle tissues.
Methylguanidoacetic acid is typically a white crystalline solid that is soluble in water, reflecting its polar nature due to the presence of amino and carboxylic acid functional groups.
Methylguanidoacetic acid has been studied for its potential benefits in enhancing athletic performance and cognitive function, as it serves as a precursor to creatine.
Additionally, Methylguanidoacetic acid may have implications in various biochemical pathways and is of interest in research related to metabolic disorders.
Safety data indicates that Methylguanidoacetic acid should be handled with care, as with many chemical substances, to avoid potential health risks.
Methylguanidoacetic acid Chemical Properties
Melting point: 300 °C(lit.)
Boiling point: 218.88°C (rough estimate)
Density: 1.4020 (rough estimate)
Refractive index: 1.4900 (estimate)
Storage temp.: Keep in dark place,Inert atmosphere,Room temperature
Solubility: 6 M NaOH : 50 mg/mL, clear, colorless
pka: 2.82(at 25℃)
Form: Solid
Color: White to Off-White
Water Solubility: 3.6g/L(15 ºC)
Merck: 14,4495
BRN: 1759179
InChIKey: BPMFZUMJYQTVII-UHFFFAOYSA-N
CAS DataBase Reference: 352-97-6(CAS DataBase Reference)
EPA Substance Registry System: Glycocyamine (352-97-6)
Production
Biochemical synthesis
Methylguanidoacetic acid is formed in the mammalian organism primarily in the kidneys by transferring the guanidine group of L-arginine by the enzyme L-Arg:Gly-amidinotransferase (AGAT) to the amino acid glycine.
From L-arginine, ornithine is thus produced, which is metabolized in the urea cycle by carbamoylation to citrulline.
In a further step, Methylguanidoacetic acid is methylated to creatine with S-adenosyl methionine by the enzyme guanidinoacetate N-methyltransferase (GAMT).
The creatine is released into the bloodstream.
Properties
Industrially produced Methylguanidoacetic acid is sold as a white (to yellowish) fine powder, which is granulated for improve handling, metering and uptake with starch into aggregates with a mean diameter of 200-400 microns.
The granulate provides a long-term stability of glycocyamine.
The shelf Life of Methylguanidoacetic acid in acidic aqueous solution is significantly higher than that of creatine, which cyclizes to creatinine under acid catalysis.
Uses
As a supplement
A series of studies showed that a combination of betaine and Methylguanidoacetic acid improves the symptoms of patients with chronic illness, including heart disease, without toxicity.
Betaine can provide a methyl group to glycocyamine, via methionine, for the formation of creatine.
In overall, such treatment led to less fatigue, greater strength and endurance, and an improved sense of well-being.
The patients with cardiac decompensation (arteriosclerosis or rheumatic disease) and congestive heart failure had improved cardiac function.
The patients gained weight (improved nitrogen balance) and saw lessened symptoms of arthritis and asthma and increased libido, and those people suffering from hypertension experienced transient reduced blood pressure.
Also the studies shows the increase of glucose tolerance in both diabetic subjects and subjects without diabetes.
Methylguanidoacetic acid is an important marker for renal failure, in kidney transplantation, and for the renal metabolic activity.
As a feed additive
Methylguanidoacetic acid is a nutritional feed additive approved by the European Commission for chickens for fattening, weaned piglets and pigs for fattening.
Methylguanidoacetic acid is supposed to lead with a "vegetarian diet" (meaning without feeding of animal protein) to higher feed conversion, higher weight gain and improved muscle increase already at a low dosage (600 g/to feed).
Possible benefits of glycocyamine supplementation can not yet be conclusively assessed, neither in other breeding, fattening and domestic animals nor for high-performance athletes, analogous to the glycocyamine metabolite creatine.
The simultaneous intake of methyl providing substances such as betaine appears advisable because of the risk of homocysteine formation with glycocyamine alone.
