Creatine
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Creatine
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CAS No:
57-00-1
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Formula:
C4H9N3O2
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Chemical Name:
Creatine
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Synonyms:
Glycine,N-(aminoiminomethyl)-N-methyl-;Creatine;N-(Aminoiminomethyl)-N-methylglycine;N-Methyl-N-guanylglycine;Methylguanidoacetic acid;Phosphagen;NSC 8752;Cosmocair C 100;Tego Cosmo C 100;Neotine;Kre-Alkalyn;[N-(Amidino)-N-methylamino]acetic acid;2-(1-Methylguanidino)acetic acid;(N-Methyl-guanidino)-acetic acid;2-[(C-Azaniumylcarbonimidoyl)-methylamino]acetate;2-(N-Methylcarbamimidamido)acetic acid;2087491-49-2
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CAS No:
Description
Creatine, an endogenous amino acid derivative, plays an important role in cellular energy, especially in muscle and brain.
Solid
Creatine is a glycine derivative having methyl and amidino groups attached to the nitrogen. It has a role as a neuroprotective agent, a nutraceutical, a human metabolite, a mouse metabolite and a geroprotector. It is a member of guanidines and a glycine derivative. It is a conjugate acid of a creatinate. It is a tautomer of a creatine zwitterion.|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.|Creatine is an endogenous amino acid derivative produced by vertebrate animals and occurring primarily in muscle cells. Creatine is important for energy storage; it 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.|An amino acid that occurs in vertebrate tissues and in urine. In muscle tissue, creatine generally occurs as phosphocreatine. Creatine is excreted as CREATININE in the urine.
Creatine Basic Attributes
131.13
131.13
907175
200-306-6
MU72812GK0
8752
DTXSID1040451
C37937
2925290090
Characteristics
90.4
-1.2
Solid
1.33 at 25 deg C
303 °C (decomp)
118.1±27.9 °C
1.552
soluble in water.
Store at RT.
7.9X10-4 mm Hg at 25 deg C (est)
Neutral reaction to litmus
Henry's Law constant = 1.7X10-14 atm-cu m/mole at 25 °C (est)
pKa1 = 3.8 (carboxylic acid); pKa2 = 12.7 (amine)|pKb = 11.02 at 20 °C
125.9 Ų [M+H]+ [CCS Type: DT, Method: single field calibrated with Agilent tune mix (Agilent)]|126 Ų [M+H]+ [CCS Type: DT, Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]|126 Ų [M+H]+
Crystals heat of fusion = -537.2, Molar heat capacity = 140.9 J/mole-K|Prisms from water at 100 °C /monohydrate/|1 g is soluble in 75 mL of water /monohydrate/|Hydroxyl radical reaction rate constant = 9.5X10-11 cu cm/molec-sec at 25 °C (est)
Safety Information
NONH for all modes of transport
3
36/37/38
26-36
Xi
P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501
H315
SRP: 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 its 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.
|Warning|H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]|P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, and P501|Aggregated GHS information provided by 101 companies from 12 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Toxicity
Creatine is produced by the liver, pancreas, and kidney for the use of transferring phosphate from adenosine triphosphate (ATP). Creatine is predominantly found in skeletal and cardiac muscle(1).
Creatine's production and use as a diagnostic for myocardial disfunction(1) and as a performance enhancing supplement(2) may result in its release to the environment through various waste streams(SRC).
TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 24(SRC), determined from a water solubility of 1.33X10+4 mg/L(2) and a regression-derived equation(3), indicates that creatine is expected to have very high mobility in soil(SRC). The pKa values for the amino and carboxylic acid moieties of creatine are estimated to be 12.7 and 3.8(4), respectively, indicating that this compound will primarily exist as a zwitter ion and zwitter ions do not volatilize from moist soil surfaces. Creatine is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 7.9X10-4 mm Hg(SRC), determined from a fragment constant method(5). Creatine has been reported to be degraded by activated sludge(6).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 24(SRC), determined from a water solubility of 1.33X10+4 mg/L(2) and a regression-derived equation(3), indicates that creatine is not expected to adsorb to suspended solids and sediment(SRC). The pKa values for the amino and carboxylic acid moieties of creatine are estimated to be 12.7 and 3.8, respectively(4), indicating that this compound will primarily exist as a zwitter ion and zwitter ions do not volatilize from water surfaces. According to a classification scheme(5), an estimated BCF of 3(SRC), determined from its water solubility(2) and a regression-derived equation(3), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Creatine has been shown to be degraded by activated sludge(7).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), creatine, which has an estimated vapor pressure of 7.9X10-4 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), will exist solely in the vapor phase in the atmosphere. Vapor-phase creatine is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 4 hours(SRC), calculated from its rate constant of 9.5x10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Creatine does not absorb light at wavelengths >290 nm(4) and therefore is not expected to be susceptible to direct photolysis by sunlight(SRC).
The rate constant for the vapor-phase reaction of creatine with photochemically-produced hydroxyl radicals has been estimated as 9.5X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 4 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). Creatine is not expected to undergo hydrolysis in the environment due to the lack of hydrolyzable functional groups(2). Creatine does not absorb at wavelengths >290 nm(3) and therefore is not expected to be susceptible to direct photolysis by sunlight(SRC).
An estimated BCF of 3 was calculated for creatine(SRC), using water solubility of 1.33X10+4 mg/L(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is low.
The Koc of creatine is estimated as 24(SRC), using a water solubility of 1.33X10+4 mg/L(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that creatine is expected to have very high mobility in soil.
The pKa values of the amino and carboxy moieties of creatine are 12.7 and 3.8(1), respectively, indicating that this compound will primarily exist as a zwitter ion and ions do not volatilize from water or moist soil surfaces. Creatine is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 7.9X10-4 mm Hg(SRC), determined from a fragment constant method(2).
Occupational exposure to creatine may occur through dermal contact with this compound at workplaces where creatine is produced or used. Increased exposure to creatine among the general population may be limited to those administered the drug, a nutritional supplement. Intentional human exposure may have occurred from creatine use as a possible performance enhancement drug in athletes(1).
The mean creatine level in the urine of 50 patients with muscular dystrophy was 3.56 mmol/L which is much higher than that of the controls 0.24 mmol/L(1). The mean level of creatine in the blood of patients with uremia was 0.1 mmol/L which is over twice that of the controls blood level of 0.04 mmol/L(1).
Drug Information
For nutritional supplementation, also for treating dietary shortage or imbalance.
Creatine, as well as a creatine analogue called cyclocreatine, inhibit growth of a broad range of solid tumors in rat models of cancer; these tumors express high levels of CK. Although the mechanism for tumor inhibition is unknown...
Phosphocreatine inhibits enzymes in the glycolitic pathway, including glyceraldehydes-3-phosphate dehydrogenase, phosphofructokinase and pyruvate kinase.|Safety data are lacking and are urgently needed, especially for long-term use of creatine and for use among the pediatric population (including adolescence) and among those in poor health. There are some reports that long-term use of creatine may be nephrotoxic. This needs further investigation before long-term creatine supplementation can be recommended under any circumstance.|Creatine is contraindicated in those with renal failure and renal disorders such as nephritic syndrome.|Anecdotal reports of adverse events to FDA have included rash, dyspnea, vomiting, diarrhea, nervousness, anxiety, migraine, fatigue, polymyositis, myopathy,seizures and atrial fibrillation.|There are reports of elevated serum creatinine, a metabolite of creatine and a marker of kidney function, in some who take creatine and have normal renal function. This /effect on renal function tests/ is reversible upon discontinuation of creatine.
Creatine is a essential, non-proteinaceous amino acid derivative found in all animals. It is synthesized in the kidney, liver, and pancreas from L-arginine, glycine and L-methionine. Following its 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.
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. CK-MM is the skeletal muscle isoform; CK-BB, the brain isoform, and CK-MB, the isoform found in cardiac muscle. 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.
Within muscle and nerve cells, about 60 to 67% of the creatine entering the cells gets converted to phosphocreatine via the enzyme creatine kinase. About 2% of creatine is converted to creatinine, and both creatine and creatinine are excreted by the kidneys.
3 hours
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 it back to ATP (adenosine triphosphate), an important cellular energy source for short term ATP needs prior to oxidative phosphorylation.|Supplemental creatine may have an energy-generating action during anaerobic exercise and may also have neuroprotective and cardioprotective actions.|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. CK is a key enzyme in involved in cellular energy homeostasis. It reversibly catalyzes the transfer of the high-energy phosphate bond in PCr to adenosine diphosphate (ADP) to form adenosine triphosphate (ATP), and it 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.
Creatine
Creatine Use and Manufacturing
Monosubstituted and N,N-disubstituted compounds, including guanidinocarboxylic acids (eg, creatine), are produced industrially by the reaction of cyanamide with the corresponding amines or aminocarboxylic acids.
Biochemical research, health products, etc.
Glycine, N-(aminoiminomethyl)-N-methyl-: ACTIVE|The literature suggests that some pharmaceutically active compounds originating from human and veterinary therapy are not eliminated completely in municipal sewage treatment plants and are therefore discharged into receiving waters(1). Wastewater treatment processes often were not designed to remove them from the effluent(2). Selected organic waste compounds may be degrading to new and more persistent compounds that may be released instead of or in addition to the parent compound(2).|Commercially isolated from meat extracts
Creatine test system. (a) Identification. A creatine test system is a device intended to measure creatine (a substance synthesized in the liver and pancreas and found in biological fluids) in plasma, serum, and urine. Measurements of creatine are used in the diagnosis and treatment of muscle diseases and endocrine disorders including hyperthyroidism.|Creatine phosphokinase/creatine kinase or isoenzymes test system. (a) Identification. A creatine phosphokinase/creatine kinase or isoenzymes test system is a device intended to measure the activity of the enzyme creatine phosphokinase or its isoenzymes (a group of enzymes with similar biological activity) in plasma and serum. Measurements of creatine phosphokinase and its isoenzymes are used in the diagnosis and treatment of myocardial infarction and muscle diseases such as progressive, Duchenne-type muscular dystrophy.|HPLC determination in cardiac muscle.|1H nuclear magnetic resonance ( NMR) urine analysis as an effective tool to detect creatine supplementation. The detection limit is 10 umol/L (1.31 mg/L).
Computed Properties
Molecular Weight:131.13
XLogP3:-1.2
Hydrogen Bond Donor Count:3
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:3
Exact Mass:131.069476538
Monoisotopic Mass:131.069476538
Topological Polar Surface Area:90.4
Heavy Atom Count:9
Complexity:134
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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