2-(1-methylcarbamimidamido)acetic acid

• ChemBase ID: 34
• Molecular Formular: C4H9N3O2
• Molecular Mass: 131.13316
• Monoisotopic Mass: 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

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-(1-methylcarbamimidamido)acetic acid
• IUPAC Traditional name: creatine
• Brand Name: Cosmocair C 100; Creatin; Kreatin; Krebiozon; Phosphagen; Pyrolysate
• Synonyms: 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; N-胺肉胺酸; α-甲胍乙酸; 肌酸; 无水肌酸

Database IDs

• CAS Number: 57-00-1
• EC Number: 200-306-6
• MDL Number: MFCD00004282
• Beilstein Number: 907175
• Merck Index: 142568
• PubChem SID: 160963497; 46504868; 24857517; 24892273
• PubChem CID: 586
• CHEBI ID: 16919
• ATC CODE: C01EB06
• CHEMBL: 283800
• Chemspider ID: 566
• DrugBank ID: DB00148
• Gmelin ID: 240513
• KEGG ID: C00300
• MeSH Name: Creatine
• Unique Ingredient Identifier: MU72812GK0
• Wikipedia Title: Creatine

CALCULATED PROPERTIES

JChem

• Acid pKa: 3.501029
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): -2.8677905
• LogD (pH = 7.4): -2.8642461
• Log P: -2.864224
• Molar Refractivity: 42.0127 cm^3
• Polarizability: 11.747328 Å^3
• Polar Surface Area: 90.41 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -1.59
• LOG S: -1.5
• Solubility (Water): 4.11e+00 g/l

PROPERTIES

Physical Property

• Solubility: 13.3 g L^-1 (at 18 °C) in water; 13.3 mg/mL at 18 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)]
• Apperance: White crystals
• Melting Point: ~295 °C (dec.); 255°C; ca 290°C dec.
• Density: 1.33
• Partition Coefficient: -1.258
• Hydrophobicity(logP): -0.2
• pKa: 3.429
• pKb: 10.568
• Isoelectric Point: 8.47
• Odor: Odourless
• Heat Capacity: 171.1 J K^-1 mol^-1 (at 23.2 °C)
• Std enthalpy of combustion: -2.3239–-2.3223 MJ mol^-1
• Std enthalpy of formation: -538.06–-536.30 kJ mol^-1
• Std molar entropy: 189.5 J K^-1 mol^-1

Safety Information

• RTECS: MB7706000
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38; r36/37/38
• Safety Statements: 26-36; 26-37; s26, s36
• TSCA Listed: 是
• GHS Pictograms: GHS exclamation mark; GHS07
• GHS Signal Word: WARNING; Warning
• GHS Hazard statements: 315, 319, 335; H315-H319-H335
• GHS Precautionary statements: 261, 305+351+338; P261-P305 + P351 + P338; P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Pharmacology Properties

• Half Life: 3 hours

Product Information

• Purity: ≥99.0% (NT); 95+%; 98%
• Grade: anhydrous
• Impurities: ≤0.5% water
• Linear Formula: H2NC(=NH)N(CH3)CH2CO2H
• Classification: Genuine Natural Compounds

DETAILS

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

Packaging
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.

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