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N-Amidinosarkosin
N-GUANYL-N-METHYLGLYCINE · MONOHYDRATE CREATINE · Creatin · Kreatin · N-Methyl-N-amidinoglycine · cretine · Creatine HMB · CreatineAnhydrous
Identifikatoren & physikalische Daten
| CAS No. | 57-00-1 |
|---|---|
| Summenformel | C4H9N3O2 |
| Durchschnittliche Molmasse | 131,13 g/mol |
| Monoisotopische Masse | 131,06947653 g/mol |
| SMILES | CN(CC(=O)O)C(=N)N |
| InChIKey | CVSVTCORWBXHQV-UHFFFAOYSA-N |
| PubChem CID | 586 |
| ChEMBL | CHEMBL283800 |
| ChEBI | CHEBI:16919 |
| EC No. | 200-306-6 |
| DTXSID | DTXSID1040451 |
| Lokaler Name | N-Amidinosarkosin |
Chemische & physikalische Eigenschaften
| XLogP | -1,2 |
|---|---|
| Polarare Oberfläche (TPSA) | 90,4 |
| H-Brücken-Donoren | 3 |
| H-Brücken-Akzeptoren | 3 |
| Frei drehbare Bindungen | 3 |
| Schwere Atome | 9 |
| Formalladung | 0 |
| Komplexität | 134 |
| Stoffklassen | Biological Agents -> Amino Acids and Derivatives |
| Arzneimittel | Pharmaceuticals -> Listed in ZINC15 |
| pH | Neutral reaction to litmus |
| Dichte | 1.33 at 25 °C1,33 g/cm3 |
| Löslichkeit | Slightly soluble in water, insoluble in etherSlightly soluble in ether and ethanolIn water, 1.33X10+4 mg/L at 18 °C13.3 mg/mL at 18 °CWater (Slightly, Heated)Soluble in water. |
| Dietary Ingredients | Creatine |
| Human Drugs | Breast FeedingLactationMilk, HumanAmino AcidsComplementary Therapies |
| Schmelzpunkt | Decomposes at 303 °C~295 °C (dec.) |
| Dampfdruck | 0.00079 [mmHg] |
| Physical Description | Solid[Merck Index] White powder[Alfa Aesar MSDS] |
| Dissociation Constants | pKa1 = 3.8 (carboxylic acid)pKa2 = 12.7 (amine)pKb = 11.02 at 20 °C |
| Collision Cross Section | 126.0 Ų [M+H]+ [CCS Type: DTBuffer gas: N2Ionization: ESI+Dataset: TOXCASTSource Identifier: DTXSID1040451]126 Ų [M+H]+ [CCS Type: DTMethod: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]125.9 Ų [M+H]+ [CCS Type: DTMethod: single field calibrated with Agilent tune mix (Agilent)] |
| Siedepunkt | 242.43°C (rough estimate) |
| Brechungsindex | 1.5700 (estimate) |
| Lagerbedingungen | Keep in dark place,Inert atmosphere,Room temperature |
| Aggregatzustand | Solid |
| pKa (Säurekonstante) | 2.63(at 25℃) |
| Farbe | White to Off-White |
| Merck | 14,2568 |
| BRN | 907175 |
| Hauptanwendungen | 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 (Verteilungskoeffizient) | -1.258 (est) |
| CAS Datenbank | 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 | 57-00-1 |
Sicherheit & Vorschriften
| GHS-Einstufung | This chemical does not meet GHS hazard criteria for 72.3% (149 of 206) of all reports.WarningH315 (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. |
|---|---|
| Regulatorische Informationen | Chemical: Glycine, N-(aminoiminomethyl)-N-methyl-Status: Active Update: 11-10-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/12796Glycine, N-(aminoiminomethyl)-N-methyl-: Does not have an individual approval but may be used under an appropriate group standardCreatine: Does not have an individual approval but may be used under an appropriate group standard |
| Weitere Sicherheitsinformationen | Evaluation - Chemicals that are unlikely to require further regulation to manage risks to environment |
| Gefahrenübersicht | A skin and strong eye irritant[Alfa Aesar MSDS] |
| Hazard Classes and Categories | Skin Irrit. 2 (27.7%) |
| Entsorgungsverfahren | 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 qualitypotential migration in soil or watereffects on animal, aquatic, and plant lifeand conformance with environmental and public health regulations. |
| Körperbelastung | 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). |
| Umweltverhalten | 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). |
| Toxizitätsübersicht | 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 | 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 Sources | 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). |
| Artificial Pollution Sources | 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). |
| Environmental Biodegradation | 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 Classification | No indication of carcinogenicity to humans (not listed by IARC). |
| Environmental Bioconcentration | 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 | 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 | 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). |
| Wassergefährdungsklasse (WGK) | 3 |
| TSCA-Inventar-Status | TSCA listed |
| Zollcode | 29252900 |
| R-Sätze (R) | 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. |
| Gefahrensymbole | Xi |
| Sicherheitshinweise (S) | 26-36 |
| Lagerklasse | 11 - Combustible Solids |
| Gefahrstoffdaten | 57-00-1(Hazardous Substances Data) |
Anwendungen & Verwendung
Occurrence
Creatine 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.
Verwenden
Creatine 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.