2-(1-methylcarbamimidamido)acetic acid

• ChemBase编号: 34
• 分子式: C4H9N3O2
• 平均质量: 131.13316
• 单一同位素质量: 131.06947654
• SMILES: OC(=O)CN(C)C(=N)N
• Canonical SMILES: OC(=O)CN(C(=N)N)C
• InChI: InChI=1S/C4H9N3O2/c1-7(4(5)6)2-3(8)9/h2H2,1H3,(H3,5,6)(H,8,9)
• InChIKey: CVSVTCORWBXHQV-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 2-(1-methylcarbamimidamido)acetic acid
• IUPAC传统名: creatine
• 商标名: Cosmocair C 100; Creatin; Kreatin; Krebiozon; Phosphagen; Pyrolysate
• 别名: N-胺肉胺酸; α-甲胍乙酸; 肌酸; 无水肌酸; 2-(1-methylguanidino)acetic acid; 2-(Methylguanidino)ethanoic acid; Creatine; Creatine, anhydrous; (alpha-Methylguanido)acetic acid; Creatine, hydrate; N-Methyl-N-guanylglycine; N-Amidinosarcosine; Methylguanidoacetic acid; Creatine (8CI); Creatine; (α-Methylguanido)acetic acid

登记号

• CAS号: 57-00-1
• EC号: 200-306-6
• MDL号: MFCD00004282
• Beilstein号: 907175
• 默克索引号: 142568
• PubChem SID: 160963497; 46504868; 24857517; 24892273
• PubChem CID: 586
• CHEBI ID: 16919
• ATC码: C01EB06
• CHEMBL: 283800
• Chemspider ID: 566
• DrugBank ID: DB00148
• Gmelin ID: 240513
• KEGG ID: C00300
• 医学主题词(MeSH): Creatine
• 美国药典/FDA物质标识码: MU72812GK0
• 维基百科标题: Creatine

理论计算性质

JChem

• Acid pKa: 3.501029
• 质子受体: 5
• 质子供体: 3
• LogD (pH = 5.5): -2.8677905
• LogD (pH = 7.4): -2.8642461
• Log P: -2.864224
• 摩尔折射率: 42.0127 cm^3
• 极化性: 11.747328 Å^3
• 极化表面积: 90.41 Å^2
• 可自由旋转的化学键: 2
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: -1.59
• LOG S: -1.5
• 溶解度: 4.11e+00 g/l

分子性质

理化性质

• 溶解度: 13.3 g L^-1 (at 18 °C) in water; 13.3 mg/mL at 18 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)]
• 外观: White crystals
• 熔点: ~295 °C (dec.); 255°C; ca 290°C dec.
• 密度: 1.33
• 分配系数: -1.258
• 疏水性(logP): -0.2
• pKa: 3.429
• pKb: 10.568
• 等电点: 8.47
• 气味: Odourless
• 热容: 171.1 J K^-1 mol^-1 (at 23.2 °C)
• 标准摩尔燃烧焓 (ΔcH^o298): -2.3239–-2.3223 MJ mol^-1
• 标准摩尔生成焓 (ΔfH^o298): -538.06–-536.30 kJ mol^-1
• 标准摩尔熵 (S^o298): 189.5 J K^-1 mol^-1

安全信息

• RTECS编号: MB7706000
• 欧盟危险性物质标志: 刺激性(Irritant) (Xi)
• 德国WGK号: 3
• 危险公开号: 36/37/38; r36/37/38
• 安全公开号: 26-36; 26-37; s26, s36
• TSCA收录: 是
• GHS危险品标识: GHS exclamation mark; GHS07
• GHS警示词: WARNING; Warning
• GHS危险声明: 315, 319, 335; H315-H319-H335
• GHS警示性声明: 261, 305+351+338; P261-P305 + P351 + P338; P261-P305+P351+P338-P302+P352-P321-P405-P501A
• 个人保护装置: dust mask type N95 (US), Eyeshields, Gloves

药理学性质

• 半衰期: 3 hours

产品相关信息

• 纯度: ≥99.0% (NT); 95+%; 98%
• 级别: anhydrous
• 杂质: ≤0.5% water
• 线性分子式: H2NC(=NH)N(CH3)CH2CO2H
• 分类: Genuine Natural Compounds

详细说明

DrugBank - DB00148

• Drug Groups: approved; nutraceutical
• Description: 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. [PubChem]
• Indication: For nutritional supplementation, also for treating dietary shortage or imbalance
• Pharmacology: Creatine is a essential, non-proteinaceous amino acid found in all animals and, in some plants. Creatine 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.
• Affected Organisms: Humans and other mammals
• Half Life: 3 hours
• References: Burke DG, Chilibeck PD, Parise G, Tarnopolsky MA, Candow DG: Effect of alpha-lipoic acid combined with creatine monohydrate on human skeletal muscle creatine and phosphagen concentration. Int J Sport Nutr Exerc Metab. 2003 Sep;13(3):294-302. [Pubmed] ; Dangott B, Schultz E, Mozdziak PE: Dietary creatine monohydrate supplementation increases satellite cell mitotic activity during compensatory hypertrophy. Int J Sports Med. 2000 Jan;21(1):13-6. [Pubmed] ; Hespel P, Op't Eijnde B, Van Leemputte M, Urso B, Greenhaff PL, Labarque V, Dymarkowski S, Van Hecke P, Richter EA: Oral creatine supplementation facilitates the rehabilitation of disuse atrophy and alters the expression of muscle myogenic factors in humans. J Physiol. 2001 Oct 15;536(Pt 2):625-33. [Pubmed] ; Hultman E, Soderlund K, Timmons JA, Cederblad G, Greenhaff PL: Muscle creatine loading in men. J Appl Physiol. 1996 Jul;81(1):232-7. [Pubmed] ; Juhn M: Popular sports supplements and ergogenic aids. Sports Med. 2003;33(12):921-39. [Pubmed]
• External Links: Wikipedia; PDRhealth; Drugs.com

Sigma Aldrich - C0780

包装
10 mg in autosmp vl
50, 100, 500 g in poly bottle
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 it may aid in neuroprotection and by improving the cellular bioenergetic state.

Sigma Aldrich - 291196

包装
5 g in glass bottle
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 it may aid in neuroprotection and by improving the cellular bioenergetic state.

Sigma Aldrich - 27890

Other Notes
Identification of creatine as a cofactor of thiamine-diphosphate kinase1
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 it may aid in neuroprotection and by improving the cellular bioenergetic state.

参考文献

• Burke DG, Chilibeck PD, Parise G, Tarnopolsky MA, Candow DG: Effect of alpha-lipoic acid combined with creatine monohydrate on human skeletal muscle creatine and phosphagen concentration. Int J Sport Nutr Exerc Metab. 2003 Sep;13(3):294-302. Pubmed
• Dangott B, Schultz E, Mozdziak PE: Dietary creatine monohydrate supplementation increases satellite cell mitotic activity during compensatory hypertrophy. Int J Sports Med. 2000 Jan;21(1):13-6. Pubmed
• Hespel P, Op't Eijnde B, Van Leemputte M, Urso B, Greenhaff PL, Labarque V, Dymarkowski S, Van Hecke P, Richter EA: Oral creatine supplementation facilitates the rehabilitation of disuse atrophy and alters the expression of muscle myogenic factors in humans. J Physiol. 2001 Oct 15;536(Pt 2):625-33. Pubmed
• Hultman E, Soderlund K, Timmons JA, Cederblad G, Greenhaff PL: Muscle creatine loading in men. J Appl Physiol. 1996 Jul;81(1):232-7. Pubmed
• Juhn M: Popular sports supplements and ergogenic aids. Sports Med. 2003;33(12):921-39. Pubmed