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Methyl Guanidine Acetic acid is a chemical compound structurally related to guanidinoacetic acid (GAA, also called glycocyamine), in which one of the hydrogen atoms attached to the guanidine functional group has been replaced by a methyl group (-CH₃).
Methyl Guanidine Acetic acid alters the chemical properties of the molecule, including its solubility, reactivity, and biological activity, while retaining the basic backbone of an acetic acid derivative bound to a guanidine-like functional group.
Methyl Guanidine Acetic acid can be classified as an N-methyl derivative of guanidinoacetic acid, meaning that the methyl group is covalently bonded to the nitrogen atom of the guanidine moiety, which can influence the electron distribution in the molecule and its interactions in biological or chemical systems.
CAS Number: 352-97-6
Molecular Formula: C3H7N3O2
Molecular Weight: 117.11
EINECS Nummber: 206-529-5
Synonyms: Glycocyamine, guanidinoacetic acid, 352-97-6, Guanidineacetic acid, Guanidoacetic acid, N-amidinoglycine, Betacyamine, Guanyl glycine, Betasyamine, guanidinoacetate, Guanidylacetic acid, GLYCINE, N-AMIDINO-, Guanidine, (carboxymethyl)-, glycine, N-(aminoiminomethyl)-, amidinoglycine, Acetic acid, ((aminoiminomethyl)amino)-, 2-(diaminomethylideneamino)acetic acid, 2-carbamimidamidoacetic acid, N-(aminoiminomethyl)-glycine, GO52O1A04E, CHEBI:16344, NSC1901, NSC-1901, NSC-26360, NSC-227847, 2-((AMINO(IMINO)METHYL)AMINO)ACETIC ACID, Acetic acid, [(aminoiminomethyl)amino]-, 2-[[Amino(imino)methyl]amino]acetic acid, CHEBI:131444, 206-529-5, 2-(diaminomethylideneazaniumyl)acetate, 2-Guanidinoacetic acid, Glykocyamin, N-[AMINO(IMINO)METHYL]GLYCINE, N-(Aminoiminomethyl)glycine, N-Guanylglycine, MFCD00004278, N-carbamimidoylglycine, GUANIDINO ACETATE, N-(carbamimidoyl)glycine, NSC 1901, (carbamimidamido)acetic acid, .alpha.-Guanidinoacetic acid, CHEMBL281593, n-amidino-glycine, NMG, EINECS 206-529-5, UNII-GO52O1A04E, Glucocyamine, Guanidoacetate, Guanidylacetate, Guanidineacetate, AI3-17119, a-Guanidinoacetate, b-Guanidinoacetate, beta-Guanidinoacetate, guanidine acetic acid, alpha-Guanidinoacetate, a-Guanidinoacetic acid, b-Guanidinoacetic acid, beta-Guanidinoacetic acid, GUANIDOACETIC_ACID, (carboxymethyl)-Guanidine, alpha-Guanidinoacetic acid, GLYCOCYAMINE [MI], bmse000384, Guanidineacetic acid, 99%, 2-(amidinoamino)acetic acid, SCHEMBL33970, SCHEMBL33971, 2-carbamimidamido-acetic acid, GLYCOCYAMINE [WHO-DD], Glycine, N-amidino- (8CI), GTPL5325, orb1303032, SCHEMBL11866140, SCHEMBL30542331, (Diaminomethylenamino)-essigsaure, DTXSID50861885, MSK8334, [(aminoiminomethyl)amino]-Acetate, HMS3604I10, GAA, Glycocyamine, Guanidinoacetate, NSC26360, AC2229, BDBM50021601, NSC227847, s6340, SBB028198, STL164350, [(aminoiminomethyl)amino]-Acetic acid, 2-[[Amino(imino)methyl]amino]acetate, AKOS005363765, DB02751, FG23711, HY-W021448, 2-[(diaminomethylidene)amino]acetic acid, ([Amino(imino)methyl]amino)acetic acid #, AS-10760, SY015122, DB-069193, CS-0040590, G0167, NS00009387, EN300-49151, C00581, Q2740979, Z586248684, N-(Aminoiminomethyl)-glycine, 2-[[Amino(imino)methyl]amino]acetic acid, NSC 26360, 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
Methyl Guanidine Acetic 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 it is then transformed into creatine by methylation.
Methyl Guanidine Acetic acid is used as a supplement and as a feed additive in poultry farming.
However, the metabolism of creatine from glycocyamine 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.
Methyl Guanidine Acetic acid plays a role in the metabolism of the amino acids serine, threonine, and proline.
Methyl Guanidine Acetic acid is a chemical compound closely related to guanidinoacetic acid (GAA, also called glycocyamine), in which one of the hydrogen atoms of the guanidine group is replaced by a methyl group (-CH₃).
This slight structural modification gives it distinct chemical and biological properties compared to standard guanidinoacetic acid.
Chemically, itMethyl Guanidine Acetic acidcan be described as an N-methyl derivative of guanidinoacetic acid, meaning the guanidine functional group is methylated, while the acetic acid part remains unchanged.
Like glycocyamine, Methyl Guanidine Acetic acid contains a guanidino group (-C(=NH)-NH₂) attached to an acetic acid backbone, but the methylation can affect its reactivity, solubility, and biological activity.
From a biochemical perspective, methyl guanidine acetic acid is particularly interesting because it is closely connected to creatine metabolism, a pathway that is essential in energy storage and transfer in muscle and nerve tissues.
In the body, guanidinoacetic acid serves as a precursor to creatine, which is synthesized primarily in the liver and then transported to tissues with high energy demands, such as skeletal muscle and the brain.
The methylated form, while less common in natural biological systems, can be used in research studies to investigate how modifications of the guanidine group affect the synthesis of creatine and related metabolites, providing insight into enzyme specificity, methylation reactions, and metabolic regulation.
Methyl Guanidine Acetic Acid (MGAA) is a derivative of guanidinoacetic acid (GAA, also called glycocyamine) in which one of the hydrogen atoms of the guanidine functional group has been replaced by a methyl (-CH₃) group, resulting in a subtle yet significant alteration of the molecule’s chemical properties, including its electron density distribution, hydrogen bonding potential, and steric configuration, all of which can affect its reactivity in both chemical and biological systems.
Unlike guanidinoacetic acid, which naturally participates in the body’s creatine biosynthesis pathway, MGAA is primarily of synthetic and research interest, although its structural similarity to GAA allows it to interact with some of the same metabolic enzymes, potentially influencing methylation reactions and energy metabolism studies.
In industrial or laboratory applications, methyl guanidine acetic acid may be employed as a synthetic intermediate in the preparation of more complex organic or biochemical compounds.
Its chemical structure allows it to participate in reactions typical for guanidine derivatives, such as condensation reactions, salt formation, and methylation-dependent transformations, making it a useful building block in the synthesis of pharmaceuticals, amino acid analogues, or biochemical probes.
Additionally, Methyl Guanidine Acetic acid may be studied as a model compound to understand the effects of methylation on guanidine-containing molecules, which is relevant for drug design, metabolic studies, and enzyme kinetics experiments.
From a biochemical perspective, methyl guanidine acetic acid provides a valuable tool for investigating the effects of chemical modifications on guanidine-containing metabolites, especially in studies that aim to understand creatine synthesis, methyl group transfer, and enzyme specificity.
Because GAA is converted in the liver into creatine by methylation using S-adenosylmethionine (SAM) as the methyl donor, Methyl Guanidine Acetic acid serves as a model compound to explore how N-methylation affects enzyme activity, substrate recognition, and product formation, offering insights into the kinetics and regulation of metabolic pathways that are critical in energy-intensive tissues like skeletal muscle, cardiac muscle, and the brain.
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: 3.6 g/L (15 ºC),
Merck: 14,4495,
BRN: 1759179,
InChIKey: BPMFZUMJYQTVII-UHFFFAOYSA-N.
Methyl Guanidine Acetic acid is a chemically modified form of guanidinoacetic acid with a methylated guanidine group, giving it distinct chemical and biological properties.
Methyl Guanidine Acetic acid is used primarily in biochemical research, metabolic studies, and as a synthetic intermediate in organic and pharmaceutical chemistry, while requiring careful handling due to its potential irritant properties and biochemical activity.
Its study provides valuable insight into creatine biosynthesis, methylation effects on guanidine compounds, and structure-activity relationships in both chemical and biological systems.
Methyl Guanidine Acetic 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, glycocyamine is methylated to creatine with S-adenosyl methionine by the enzyme guanidinoacetate N-methyltransferase (GAMT).
The creatine is released into the bloodstream.
Industrially produced gMethyl Guanidine Acetic 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 Methyl Guanidine Acetic acid in acidic aqueous solution is significantly higher than that of creatine, which cyclizes to creatinine under acid catalysis.
Methyl Guanidine Acetic acid is a nutritional feed additive approved by the European Commission for chickens for fattening, weaned piglets and pigs for fattening.
Methyl Guanidine Acetic 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 Methyl Guanidine Acetic acid 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.
Regarding safety, methyl guanidine acetic acid should be treated with caution like other guanidine derivatives.
Methyl Guanidine Acetic acid may act as a skin, eye, or respiratory irritant upon direct contact or inhalation of dust or aerosols.
Its biological effects depend on the dose and exposure route, and while it is generally less toxic than organotin or heavy-metal compounds, high concentrations could still lead to toxicity or metabolic disturbances if accidentally ingested, inhaled, or absorbed through the skin.
In laboratory settings, standard safety precautions—such as the use of gloves, protective eyewear, and proper ventilation—are recommended when handling MGAA to minimize exposure and ensure safe storage and disposal.
In industrial and laboratory applications, methyl guanidine acetic acid is often employed as a synthetic intermediate for pharmaceutical and biochemical compounds, where its guanidine moiety can undergo reactions typical of guanidine derivatives, such as condensation with carbonyl compounds, salt formation with acids, and participation in methylation reactions.
Its use as a building block allows chemists to produce a wide range of guanidine-containing molecules, amino acid analogues, and potential drug candidates, particularly in the study of compounds that influence energy metabolism, neurochemistry, and muscle physiology.
In addition, Methyl Guanidine Acetic acid can be utilized as a reference or standard in analytical chemistry, where researchers study its behavior under different conditions to calibrate assays or to compare the properties of other guanidine derivatives.
From a safety standpoint, methyl guanidine acetic acid is considered moderately hazardous and should be handled with appropriate laboratory safety protocols.
Methyl Guanidine Acetic acid may act as a skin, eye, and respiratory irritant, and prolonged or high-dose exposure could potentially interfere with normal cellular processes, particularly due to its structural similarity to biologically active guanidine compounds.
While it is not highly toxic compared to heavy metals or organotin compounds, improper handling, ingestion, or inhalation could result in localized toxicity, metabolic disruption, or mild systemic effects.
Therefore, MGAA is typically handled in laboratories using gloves, eye protection, fume hoods, and well-ventilated areas, and waste containing Methyl Guanidine Acetic acid must be disposed of according to chemical safety regulations to prevent environmental contamination.
Uses:
Methyl Guanidine Acetic acid is an important marker for renal failure, in kidney transplantation, and for the renal metabolic activity.
A series of studies showed that a combination of betaine and glycocyamine 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.
While less common in commercial use than GAA, Methyl Guanidine Acetic acid is sometimes explored in nutritional and therapeutic research, particularly as a chemical analogue for studying creatine supplementation, energy metabolism, or the effects of methylation on bioavailability and metabolic pathways.
Although it is primarily a research compound, understanding how Methyl Guanidine Acetic acid behaves in metabolic systems can provide insights into the design of modified creatine precursors, performance-enhancing supplements, or treatments for conditions involving impaired creatine metabolism, such as certain muscular or neurological disorders.
Methyl guanidine acetic acid is also used as a synthetic intermediate in organic and medicinal chemistry, where its guanidine moiety and methylated nitrogen provide reactive sites for chemical transformations such as condensation, amidation, salt formation, or further derivatization.
Chemists can employ MGAA to produce guanidine-containing pharmaceuticals, amino acid analogues, and potential drug candidates, particularly in studies where structural analogues of naturally occurring metabolites are needed to probe enzyme specificity or pharmacological activity.
Its unique combination of an acetic acid backbone with a methylated guanidine group makes it a versatile building block for developing compounds that modulate energy metabolism, muscle function, or neurological pathways.
Methyl Guanidine Acetic acid may be used in biochemical research to study creatine metabolism, since guanidinoacetic acid is a direct precursor of creatine in the body.
The methylated derivative can serve as a model compound or intermediate in organic synthesis for pharmaceuticals or biochemical studies.
In theory, it could have applications in metabolic studies or as a dietary supplement precursor, though the natural compound (GAA) is more common for such uses.
One of the primary uses of methyl guanidine acetic acid is in biochemical and physiological research focused on creatine metabolism, because it is a chemically modified analogue of guanidinoacetic acid, which is the natural precursor to creatine in the liver.
Scientists use Methyl Guanidine Acetic acid in experiments to investigate how methylation of the guanidine group affects enzyme activity, substrate recognition, and the overall kinetics of creatine biosynthesis, allowing a deeper understanding of energy metabolism in tissues such as skeletal muscle, cardiac muscle, and the brain.
By comparing MGAA with natural GAA, researchers can elucidate the role of structural modifications in biological pathways and the efficiency of methyl group transfer reactions, which is critical for understanding metabolic diseases, muscle disorders, or neurological conditions where creatine levels are altered.
In addition to its direct synthetic applications, Methyl Guanidine Acetic acid is widely used as a model compound for investigating the effect of chemical modifications on enzymes that process guanidine-containing substrates, such as guanidinoacetate N-methyltransferase, which normally converts GAA to creatine.
By introducing a methyl group, researchers can observe how small structural changes influence enzyme binding, reaction rates, and metabolic flux, providing insights that are relevant for the design of enzyme inhibitors, metabolic modulators, or dietary supplements targeting creatine pathways.
This makes Methyl Guanidine Acetic acid a valuable tool in both basic biochemical research and applied pharmaceutical studies.
Methyl Guanidine Acetic acid can also serve as a reference standard in analytical chemistry, where its predictable chemical properties and similarity to guanidinoacetic acid make it useful for calibrating assays, validating detection methods, or comparing the properties of other guanidine derivatives.
Laboratories studying amino acids, methylated metabolites, or creatine precursors often use Methyl Guanidine Acetic acid to ensure accuracy in quantitative and qualitative analyses, such as chromatography or mass spectrometry, and to help identify or quantify related compounds in biological samples or synthetic reaction mixtures.
Safety Profile:
Methyl guanidine acetic acid, like other guanidine derivatives, may act as a moderate irritant to the skin, eyes, and respiratory tract, meaning that direct contact with the solid compound or exposure to its dust or aerosols can lead to redness, itching, burning sensations, and temporary discomfort, and inhalation of airborne particles may cause coughing, sore throat, or mild respiratory irritation, particularly in individuals with sensitive mucous membranes or pre-existing respiratory conditions.
Although Methyl Guanidine Acetic acid is generally less acutely toxic than heavy metals or organotin compounds, its structural similarity to guanidinoacetic acid means that high doses or prolonged exposure could potentially disrupt metabolic processes, interfere with enzyme function, or cause mild systemic effects, especially in laboratory or experimental settings where concentrated forms are used.
Care must be taken to avoid accidental ingestion or excessive inhalation, as it may affect kidney or liver metabolism in animal studies, and its effects on humans at high concentrations are not fully characterized.
