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N-Amidinosarkosin

Creatine

HCID 586
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Grundinformationen

CAS
57-00-1
Standard-SMILES
CN(CC(=O)O)C(=N)N
InChIKey
CVSVTCORWBXHQV-UHFFFAOYSA-N
Summenformel
C4H9N3O2
Durchschnittliche Molmasse
131,13 g/mol
Monoisotopische Masse
131,06947654

Überblick

Creatine is a glycine derivative having methyl and amidino groups attached to the nitrogen. It has a role as a geroprotector, a nutraceutical, a neuroprotective agent, a mouse metabolite and a human metabolite. It is a glycine derivative and a member of guanidines. It is a conjugate acid of a creatinate. It is a tautomer of a creatine zwitterion.

Namen und Bezeichner

Bevorzugter Name
Creatine
IUPAC
2-[carbamimidoyl(methyl)amino]acetic acid
Lokaler Name
N-Amidinosarkosin
Englischer Name
Creatine
Summenformel
C4H9N3O2
Molmasse
131.13

Namen und Synonyme

creatine57-00-1CreatinN-amidinosarcosineKreatinKrebiozonmethylglycocyamineN-methyl-N-guanylglycineGlycine, N-(aminoiminomethyl)-N-methyl-Pyrolysate(alpha-Methylguanido)acetic acidN-carbamimidoyl-N-methylglycine
Weitere Namen anzeigen
N-GUANYL-N-METHYLGLYCINEMONOHYDRATE CREATINEN-Methyl-N-amidinoglycinecretineCreatine HMBCreatineAnhydrousNutrition Creatinecreatine zwitterion
Cosmocair C 100KreatinumNeotine2-(1-methylcarbamimidamido)acetic acidN-(aminoiminomethyl)-N-methylglycinealpha-Methylguanidino acetic acid2-[carbamimidoyl(methyl)amino]acetic acidNSC-8752

Datenbank-Bezeichner

CAS
57-00-1、6020-87-7
PubChem CID
586
DTXSID
DTXSID1040451
ChEMBL
CHEMBL283800
ChEBI
CHEBI:16919
UNII
MU72812GK0
EC Number
200-306-6
Nikkaji
J9.321A

Eigenschaften

Berechnete StruktureigenschaftenWird ergänzt

XLogP
-1,2
Polarare Oberfläche (TPSA)
90,4 Ų
H-Brücken-Donoren
3
H-Brücken-Akzeptoren
3
Frei drehbare Bindungen
3
Schwere Atome
9
Formalladung
0
Komplexität
134

Experimentelle und physikochemische Eigenschaften

Chemical ClassesBiological Agents -> Amino Acids and Derivatives
DrugsPharmaceuticals -> Listed in ZINC15
pHNeutral reaction to litmus
Density1.33 at 25 °C
Solubility · 4 Einträge

Slightly soluble in water, insoluble in ether

Slightly soluble in ether and ethanol

In water, 1.33X10+4 mg/L at 18 °C

13.3 mg/mL at 18 °C

Dietary IngredientsCreatine
Human DrugsBreast Feeding; Lactation; Milk, Human; Amino Acids; Complementary Therapies
Melting Point · 2 Einträge

Decomposes at 303 °C

303 °C

Vapor Pressure0.00079 [mmHg]
Physical Description · 2 Einträge

Solid; [Merck Index] White powder; [Alfa Aesar MSDS]

Solid

Dissociation Constants · 2 Einträge

pKa1 = 3.8 (carboxylic acid); pKa2 = 12.7 (amine)

pKb = 11.02 at 20 °C

Collision Cross Section · 4 Einträge

126.0 Ų [M+H]+ [CCS Type: DT; Buffer gas: N2; Ionization: ESI+; Dataset: TOXCAST; Source Identifier: DTXSID1040451]

126 Ų [M+H]+ [CCS Type: DT; Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]

125.9 Ų [M+H]+ [CCS Type: DT; Method: single field calibrated with Agilent tune mix (Agilent)]

126 Ų [M+H]+

Physikochemische Eigenschaften

Schmelzpunkt
295 °C · ~295 °C (dec.)
Siedepunkt
242.43 °C · 242.43°C (rough estimate)
Dichte
1 · 1,33 g/cm3
Brechungsindex
1.57 · 1.5700 (estimate)
storage temp.
Keep in dark place,Inert atmosphere,Room temperature
Löslichkeit
Water (Slightly, Heated)
Aggregatzustand
Solid
pka
2.63 · 2.63(at 25℃)
Farbe
White to Off-White
Wasserlöslichkeit
Soluble in water.
Merck
14 · 14,2568
BRN
907175 · 907175
Major Application
food and beveragespersonal carepharmaceutical
Kosmetik-Inhaltsstoffe Funktionen
SKIN CONDITIONING
InChI
1S/C4H9N3O2/c1-7(4(5)6)2-3(8)9/h2H2,1H3,(H3,5,6)(H,8,9)
InChIKey
CVSVTCORWBXHQV-UHFFFAOYSA-N
SMILES
CN(CC(O)=O)C(N)=N
LogP
-1.258 · -1.258 (est)
CAS Datenbank
57 · 57-00-1(CAS DataBase Reference)
NIST chemische Informationen
Glycine, N-(aminoiminomethyl)-N-methyl-(57-00-1)
EPA chemische Informationen
Glycine, N-(aminoiminomethyl)-N-methyl- (57-00-1)
CAS Number Unlabeled
57 · 57-00-1

Sicherheit und Regulatorisches

Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.

GHS-Klassifizierung

GHS Classification · 5 Einträge

This chemical does not meet GHS hazard criteria for 72.3% (149 of 206) of all reports.

Warning

H315 (27.7%): Causes skin irritation [Warning Skin corrosion/irritation]

P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 206 reports by companies from 13 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Gefahrenhinweise

Regulatory Information · 4 Einträge

Chemical: Glycine, N-(aminoiminomethyl)-N-methyl-

REACH registered substance: N-amidinosarcosine (EC: 200-306-6)

Glycine, N-(aminoiminomethyl)-N-methyl-: Does not have an individual approval but may be used under an appropriate group standard

Creatine: Does not have an individual approval but may be used under an appropriate group standard

Other Safety InformationEvaluation - Chemicals that are unlikely to require further regulation to manage risks to environment
Hazards SummaryA skin and strong eye irritant; [Alfa Aesar MSDS]
Hazard Classes and CategoriesSkin Irrit. 2 (27.7%)

Sicherheit und Schutzausrüstung

Disposal Methods · 1 Eintrag

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.

Toxikologische Informationen

Body Burden · 1 Eintrag

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).

Environmental Fate · 3 Einträge

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).

Sicherheitsdaten

wgk
3
tsca
TSCA listed
hs_code
29252900
risk_code
36/37/38
Toxizität
A compound that is phosphorylated to phosphocreatine, which represents a store of high-energy phosphoryl groups in muscle that can be transferred to ADP, yielding ATP for muscle contraction. The enzyme involved in phosphate transfer between them is creatine phosphokinase that catalyzes the reaction Phosphocreatine+ADP→ATP+creatine An increase in serum creatine phosphokinase may be indicative of damage to non-hepatic tissue but not to the liver.
hazard_code
Xi
safety_code
26-36
Speicherklasse
11 - Combustible Solids
Giftige Stoffe Daten
57-00-1(Hazardous Substances Data)

Chemie und Industrie

Pharmakologische Informationen

Bionecessity · 1 Eintrag

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 its 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.

Pharmacodynamics · 1 Eintrag

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.

Mechanism of Action · 3 Einträge

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.

Biological Half-Life3 hours
Metabolism/Metabolites · 2 Einträge

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.

Half Life: 3 hours

Absorption, Distribution and Excretion · 2 Einträge

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.

Tissue LocationsAdipose Tissue
Cellular LocationsCytoplasm
Metabolite Pathways3-Phosphoglycerate dehydrogenase deficiency

Verwendung und Herstellung

Uses · 3 Einträge

An amino acid found mainly in skeletal and cardiac muscle; Involved in the transfer of high energy phosphate in muscle cells; [Merck Index] Used in the diagnosis of myocardial dysfunction and as a dietary supplement to enhance athletic performance; [HSDB]

Used in diagnosis of myocardial disfunction; dietary supplement for exercise performance

For nutritional supplementation, also for treating dietary shortage or imbalance

Methods of ManufacturingMonosubstituted 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.
Household ProductsInformation on 3 consumer products that contain Creatine in the following categories is provided:
General Manufacturing Information · 3 Einträge

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

Anwendungen

OccurrenceCreatine is an amino acid that occurs naturally in dairy products, seafood, and beef. It is manufactured by the body in the liver, kidney, and pancreas.

VerwendenCreatine is used for gyrate atrophy, McArdle's disease, muscular dystrophy, amyotrophic lateral sclerosis, and rheumatoid arthritis. It is used in congestive heart disease to improve exercise tolerance and to enhance athletic performance.

Vor- und nachgelagerte Produkte

Nachgelagerte Produkte

Polyinosinic acid-polycytidylic acidcorrosion inhibitor HS-132-Imino-1-methylimidazolidin-4-on2-[5H-CHROMENO[4,3-D]PYRIMIDIN-2-YL(METHYL)AMINO]ACETIC ACID

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Toxicity Summary · 1 Eintrag

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.

Soil Adsorption/Mobility · 1 Eintrag

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.

Natural Pollution SourcesCreatine 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).
Artificial Pollution SourcesCreatine'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).
Environmental Biodegradation · 2 Einträge

AEROBIC: Creatine has been reported to be aerobically degraded by activated sludge(1).

ANAEROBIC: Creatine, at a concn of 500 umol/10 ml, was fermented into methane by methanogenic enrichment cultures from Leine River mud (lake Kolksee, Germany) and black pond mud, containing Methanosarcina barkeri(1). Creatine was fermented into methane with an efficiency of 1.59 moles of methane/mole of creatine(1). Creatine did not support growth of a pure culture of M. barkeri(1).

Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).
Environmental Bioconcentration · 1 Eintrag

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.

Volatilization from Water/Soil · 1 Eintrag

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).

Non-Human Toxicity Excerpts/LABORATORY ANIMALS: Chronic Exposure or Carcinogenicity/ Chronic creatine supplementation in rats down-regulates creatine transporter protein expression. ... Leading to lower amounts entering cell at any given time.
Environmental Abiotic Degradation · 1 Eintrag

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).