CREATINE

N-amidinosarcosine = 2-(1-Methylguanidino)acetic acid

CAS Number: 57-00-1
Molecular Weight: 131.13
Beilstein: 907175
EC Number: 200-306-6
MDL number: MFCD00004282
Molecular Formula: C4H9N3O2
PubChem Substance ID: 24892273

Creatine is an organic compound with the nominal formula (H2N)(HN)CN(CH3)CH2CO2H. 
N-amidinosarcosine exists in various modifications (tautomers) in solution. 
Creatine is found in vertebrates where it facilitates recycling of adenosine triphosphate (ATP), primarily in muscle and brain tissue. 
Recycling is achieved by converting adenosine diphosphate (ADP) back to ATP via donation of phosphate groups. 
Creatine also acts as a buffer.
An amino acid derivative that occurs in vertebrate tissues and in urine. 
In muscle tissue, creatine generally occurs as phosphocreatine. 
Creatine is excreted as creatinine in the urine.

Definition
Creatine is a substance that is found naturally in muscle cells. 
Creatine helps your muscles produce energy during heavy lifting or high-intensity exercise.
Creatine is an amino acid that occurs naturally in the human body, where Creatine is made in the liver, pancreas, and kidneys and stored mainly in muscle tissue. 
Creatine is also found in sources of protein such as meat and fish. 
The average daily human intake of creatine from nutritional sources is about one gram per day.
Creatine is an endogenous amino acid derivative produced by vertebrate animals and occurring primarily in muscle cells. 
Creatine is important for energy storage; Creatine is phosphorylated to creatine phosphate, which serves as a phosphate donor in the conversion of ADP to ATP and supplies energy necessary for muscle contraction. 
Dietary supplementation with creatine may improve muscle wasting associated with cancer and other chronic diseases.

What is Creatine?
Creatine is an amino acid, with the chemical name methyl guanidine-acetic acid, that can be converted into the phosphocreatine.  
Phosphocreatine is storage mechanism muscle cells use to regenerate the cells primary source of energy adenosine triphosphate (ATP).  
Phosphocreatine has the ability to react with adenosine diphosphate (ADP), a byproduct of muscle contraction, and convert ADP to ATP for immediate energy.

Application
Creatine (Cr) and phosphocreatine (PCr) are involved with rapid ATP production primarily in skeletal muscle tissue via the action of creatine kinase(s). 
Creatine may be used as a supplement to study its uptake mechanism and metabolism of action.

Biochem/physiol Actions
Creatine is a nitrogenous compound that acts as a high-energy reservoir for the rapid regeneration of ATP. 
Approximately 95% of creatine is found in skeletal muscle, primarily as phosphocreatine. 
Creatine can be acquired through dietary consumption or formed from L-arginine, glycine, and L-methionine in a multi-step reaction that occurs in the kidneys and liver. 
Creatine is then transported to muscle tissue. 
Creatine supplementation is used for the enhancement of sports performance, primarily by increasing muscle mass. 
Creatine is also being investigated as a treatment of neuromuscular diseases, where Creatine may aid in neuroprotection and by improving the cellular bioenergetic state.

Food and cooking
When creatine is mixed with protein and sugar at high temperatures (above 148 ℃), the resulting reaction produces carcinogenic heterocyclic amines (HCAs).
Such a reaction happens when grilling or pan-frying meat.Creatine content (as a percentage of crude protein) can be used as an indicator of meat quality.

Metabolic role
Creatine is a naturally occurring non-protein compound of which the primary metabolic role is to combine creatine with a phosphoryl group to generate phosphocreatine, which is used to regenerate ATP or adenosine triphosphate. 
Most of the human body's total creatine and phosphocreatine stores are found in skeletal muscle, while the remainder is distributed in the blood, brain, testes, and other tissues.

Biosynthesis
Creatine synthesis primarily occurs in the liver and kidneys.
On average, N-amidinosarcosine is produced endogenously at an estimated rate of about 8.3 mmol or 1 gram per day in young adults.
Creatine is not an essential nutrient. 
N-amidinosarcosine is an amino acid derivative, naturally produced in the human body from the amino acids glycine and arginine, with an additional requirement for methionine to catalyze the transformation of guanidinoacetate to creatine

Pharmacology    
Creatine is a essential, non-proteinaceous amino acid derivative found in all animals. 
2-(1-Methylguanidino)acetic acid is synthesized in the kidney, liver, and pancreas from L-arginine, glycine and L-methionine. 
Following 2-(1-Methylguanidino)acetic acid'S biosynthesis, creatine is transported to the skeletal muscle, heart, brain and other tissues. 
Most of the creatine is metabolized in these tissues to phosphocreatine (creatine phosphate). 
Phosphocreatine is a major energy storage form in the body. 
Supplemental creatine may have an energy-generating action during anaerobic exercise and may also have neuroprotective and cardioprotective actions.

Mechanism of action
In the muscles, a fraction of the total creatine binds to phosphate - forming creatine phosphate. 
The reaction is catalysed by creatine kinase, and the result is phosphocreatine (PCr). 
Phosphocreatine binds with adenosine diphosphate to convert back to ATP (adenosine triphosphate), an important cellular energy source for short term ATP needs prior to oxidative phosphorylation.
Creatine, creatine kinase and phosphocreatine make up an intricate cellular enegy buffering and transport system connecting sites of energy production in the mitochondria with sites of energy consumption. 
Creatine kinase is a key enzyme in involved in cellular energy homeostasis. 
Creatine kinase reversibly catalyzes the transfer of the high-energy phosphate bond in PCr to adenosine diphosphate (ADP) to form adenosine triphosphate (ATP).
Creatine kinase catalyzes the transfer of the high-energy phosphate bond in ATP to creatine to form PCr. 
During periods of intense exercise and skeletal muscle contraction, bioenergetic metabolism switches from one in which oxidative phosphorylation is the major pathway of ATP production to one in which so-called anaerobic glycolysis becomes dominant.

Bionecessity    
Creatine is a non-protein amino acid found in animals, in much lesser amounts, plants. 
Creatine is synthesized in the kidney, liver and pancreas from the amino acids L-arginine, glycine and L methionine. 
Following 2-(1-Methylguanidino)acetic acid's biosynthesis, creatine is transported to the skeletal muscle, heart, brain and other tissues. 
Most of the creatine in these tissues is metabolized to phosphocreatine (creatine phosphate). 
Phosphocreatine is a major energy storage form in the body.

Absorption, Distribution and Excretion    
In muscle and nerve, most of the creatine is phosphorylated to phosphocreatine (pCr) in a reaction that is catalyzed by the enezyme creatine kinase (CK), there are three isoforms of (isoenzymes) of CK. 
Most of the PCr in the body is in skeletal muscle.
Creatine is absorbed from the small intestines and enters the portal circulation and is transported to the liver. 
The ingested creatine, and the creatine made in the liver, is then transported into the systemic circulation and distributed into various tissues of the body, including muscle and nerves, by crossing the cell membrane via a specific creatine-transported system against a 200:1 gradient.

Biological Half-Life: 3 hours

Disposal Methods    
The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. 
Recycle any unused portion of the material for 2-(1-Methylguanidino)acetic acid's approved use or return it to the manufacturer or supplier. 
Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.

First-aid measures
Eye Contact: Rinse immediately with plenty of water, also under the eyelids, for at least 15 minutes. 
Get medical attention. S
kin Contact: Wash off immediately with plenty of water for at least 15 minutes. 
Get medical attention immediately if symptoms occur.
Inhalation: Remove to fresh air. 
Get medical attention immediately if symptoms occur.
Ingestion: Clean mouth with water and drink afterwards plenty of water. 
Get medical attention if symptoms occur.

Stability and reactivity
Stability: Stable under normal conditions. 
Conditions to : Avoid Incompatible products.
Incompatible Materials: Strong oxidizing agents
Engineering Measures: None under normal use conditions. 

Personal Protective Equipment
Eye/face Protection :Wear appropriate protective eyeglasses or chemical safety goggles.
Skin and body protection: Wear appropriate protective gloves and clothing to prevent skin exposure. 
Respiratory Protection: No protective equipment is needed under normal use conditions. 
Hygiene Measures: Handle in accordance with good industrial hygiene and safety practice.

Alternative Names
creatine
57-00-1
Creatin
Kreatin
N-amidinosarcosine
Krebiozon
2-(1-Methylguanidino)acetic acid
N-methyl-N-guanylglycine
Glycine, N-(aminoiminomethyl)-N-methyl-
methylglycocyamine
Creatine, hydrate
(alpha-Methylguanido)acetic acid
Pyrolysate
N-carbamimidoyl-N-methylglycine
Methylguanidoacetic acid
2-(1-methylcarbamimidamido)acetic acid
Creatine (8CI)
alpha-Methylguanidino acetic acid
2-[carbamimidoyl(methyl)amino]acetic acid
Creatine, anhydrous