化工社化工社 化学情報印刷レポート · 研究参考用
N-メチル-N-アミジノグリシン
クレアチン · 1-メチルグアニジノ酢酸 · N-メチル-N-アミジノグリシン · N-グアニル-N-メチルグリシン · (1-メチルグアニジノ)酢酸 · メチルグリコシアミン · クレアチン無水物 · N-GUANYL-N-METHYLGLYCINE
識別子と物理属性
| CAS No. | 57-00-1 |
|---|---|
| 分子式 | C4H9N3O2 |
| 平均分子量 | 131.13 g/mol |
| 単同位体質量 | 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 |
| 現地名 | N-メチル-N-アミジノグリシン |
化学・物理的性質
| XLogP | -1.2 |
|---|---|
| 極性表面積 | 90.4 |
| 水素結合供与体数 | 3 |
| 水素結合受容体数 | 3 |
| 回転可能結合数 | 3 |
| 重原子数 | 9 |
| 形式電荷 | 0 |
| 複雑度 | 134 |
| 物質分類 | Biological Agents -> Amino Acids and Derivatives |
| 医薬品 | Pharmaceuticals -> Listed in ZINC15 |
| pH | Neutral reaction to litmus |
| 密度 | 1.33 at 25 °C1,33 g/cm3 |
| 溶解度 | 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 °C水（少し、加熱）水に溶ける。 |
| Dietary Ingredients | Creatine |
| Human Drugs | Breast FeedingLactationMilk, HumanAmino AcidsComplementary Therapies |
| 融点 | Decomposes at 303 °C~295 °C (dec.) |
| 蒸気圧 | 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)] |
| 沸点 | 242.43°C (rough estimate) |
| 屈折率 | 1.5700 (estimate) |
| 貯蔵条件 | Keep in dark place,Inert atmosphere,Room temperature |
| 外観・状態 | 個体 |
| pKa（酸解離定数） | 2.63(at 25℃) |
| 色 | ホワイトからオフホワイト |
| Merck | 14,2568 |
| BRN | 907175 |
| 主な用途 | 食品および飲料パーソナルケア医薬品 |
| 化粧品成分の機能 | スキンコンディショニング |
| 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（分配係数） | -1.258 (est) |
| CAS データベース | 57-00-1(CAS DataBase Reference) |
| NISTの化学物質情報 | Glycine, N-(aminoiminomethyl)-N-methyl-(57-00-1) |
| EPAの化学物質情報 | Glycine, N-(aminoiminomethyl)-N-methyl- (57-00-1) |
| CAS Number Unlabeled | 57-00-1 |
化学的特性
White powder
安全性と法規制
| GHS 分類 | 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. |
|---|---|
| 規制情報 | 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 |
| その他の安全情報 | Evaluation - Chemicals that are unlikely to require further regulation to manage risks to environment |
| 有害性の概要 | A skin and strong eye irritant[Alfa Aesar MSDS] |
| Hazard Classes and Categories | Skin Irrit. 2 (27.7%) |
| 処分方法 | 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. |
| 体内負荷 | 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). |
| 環境中動態 | 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). |
| 毒性の概要 | 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). |
| 水環境危害等級（WGK） | 3 |
| TSCA 収載状態 | TSCA listed |
| 毒性 | 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. |
| 税関コード | 29252900 |
| 危険文句（R） | 36/37/38 |
| 化審法 | 新規公示化学物質（2011年3月31日以前届出） |
| 危険表示 | Xi |
| 安全措置（S） | 26-36 |
| 貯蔵分類 | 11 - Combustible Solids |
| 有害物質データ | 57-00-1(Hazardous Substances Data) |
用途
解説
クレアチン，脊椎動物の筋肉中に存在し，筋肉活動の際，クレアチンリン酸とともに重要な役割を果たす．人体には90～120 g，その90％ は筋肉中に存在する．グリシン，アルギニンおよびL-メチオニンから生合成される．結晶性固体．分解点303 ℃．水，エタノールに可溶，エーテルに不溶．アミノ酸に類似した化合物で、アミノ基のかわりにグアニジン基をもっている。化学式は図のようになる。脊椎動物(せきついどうぶつ)の筋肉には多量に含まれる。 ATP（アデノシン三リン酸）によりリン酸化されクレアチンリン酸（エネルギー貯蔵の役目をするフォスファーゲンの一種）となる。生合成は、アルギニンからグアニジン基がグリシンに移転する経路で行われる。分解は、分子内脱水により環状化合物のクレアチニンとなり、直接尿中に排泄(はいせつ)される。血中または尿中のクレアチニンの量は比較的一定で、筋肉の総量に比例している。
天然物の起源
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.
使用
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.
使用用途
クレアチンは、筋肉が収縮する際のエネルギーであるATP (細胞の中に存在し、生命活動で利用されるエネルギーを保存・利用する上で必要な物質) の再合成に利用され、クレアチンリン酸として筋肉に存在しています。 運動時にはATPが分解される際に発生するエネルギーが使用されますが、ATPの量には限界があるため、運動し続けるにはクレアリン酸によるATPの再合成が必要です。クレアチンには運動時などの持久力や筋力を高める効果があるので、主に短時間で激しい運動を繰り返す際に、クレアチンの運動能力を高める効果が有効です。 また、アスリートだけではなく、クレアチンの高齢者の運動能力に及ぼす効果についても研究が進められており、高齢者の筋力維持やリハビリテーションを目的としたクレアチンの活用方法が研究されています。
製法・合成法
純化方法
Likely impurities are creatinine and other guanidino compounds. It crystallises from the minimum volume of boiling H2O as the monohydrate. The hydrate is also obtained by dissolving in H2O and adding Me2CO. Drying under vacuum over P2O5 or drying at 100o gives the anhydrous base. The anhydrous base can be obtained also by dissolving the hydrate in H2O, seeding with the anhydrous base and cooling in ice. A m of 258 -268o(dec) was reported. The picrate crystallises from 17 parts of H2O with m of 218-220o(dec). [King J Chem Soc 2377 1930, Hoffmann et al. J Am Chem Soc 58 1730 1936, Mendel & Hodgkin Acta Cryst 7 443 1954, Greenstein & Winitz The Chemistry of the Amino Acids J. Wiley, Vol 3 p 2750 1961, Beilstein 4 III 1170, 4 IV 2425.]