6020-87-7

Creatine monohydrate or creatine. The chemical name for creatine covered under this investigation is N-(aminoiminomethyl)-N-methylglycine monohydrate. The Chemical Abstracts Service(CAS) registry numbers for this product are 57-00-1 and 6020-87-7.Pure creatine is a white, tasteless,odorless powder, that is a naturally occurring metabolite found in muscle tissue.
Creatine monohydrate is an amino acid produced in the human body that plays a role in replenishing the energy supply to muscle cells.Creatine is usually produced to a purity of 99.5 percent or higher.Until recently, the primary use for creatine was as a laboratory reagent, demand for which was relatively limited.In the early 1990's, however, weight trainersand other athletes began using creatine in the belief that it stimulates muscle growth and reduces muscle fatigue.

Creatine (creatine monohydrate) is a colorless, crystalline substance used in muscle tissue for the production of phosphocreatine, an important factor in the formation of adenosine triphosphate (ATP), the source of energy for muscle contraction and many other functions in the body.

Creatine is a natural compound made from the amino acids l-arginine, glycine, and methionine.Creatine monohydrate is a creatine with one molecule of water connected to it. Our bodies can produce creatine, however they also can take in and store creatine found in diverse meals like meat, eggs, and fish.

Creatine monohydrate supplementation is promoted as an ergogenic aid, which refers to a product purported to enhance energy production,utilization, control, and efficiency (Mujika and Padilla,1997).Creatine is purported to increase power, strength, and muscle mass and to decrease performance time (Demant et al.,1999).
Involved with rapid ATP production primarily in skeletal muscle tissue via the action of creatine kinase(s).

Creatine monohydrate can be synthesized in the laboratory (and commercially), starting from cyanamide and sarcosine (N-methylglycine).

Creatine is a nitrogenous organic acid that occurs naturally in vertebrates and helps to supply energy to all cells in the body, primarily muscle by playing a key role in muscle energy metabolism. It is produced in the liver, pancreas, and kidneys and can also be derived from food and dietary supplements. Creatine provides the energy needed for muscle contraction and substantially improves performance in high-intensity exercise because it improves anaerobic capacity and protein synthesis. Therapeutically, it has been used to treat some types of muscular dystrophy, ocular atrophy, and some types of sclerosis. Creatine (a dietary supplement) is demanded by many athletes and is neither regulated by the Food and Drug Administration (FDA) nor prohibited by the International Olympic Committee (IOC).

Creatine has many benefits for health and performance. The most common is creatine monohydrate, a dietary supplement that improve strength, increase lean muscle mass, and help the muscles recover more quickly during exercise. It can also inhibit the generation of muscle fatigue factors, reduce fatigue and tension, restore physical fitness, accelerate protein synthesis in the human body, make muscles stronger, enhance muscle elasticity, reduce cholesterol, blood lipids, and blood sugar levels, improve middle-aged and elderly Muscular dystrophy, and delay aging.

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.

Early research proposed that the osmotic effect of creatine supplementation serves as a cellular stressor (osmosensing) that acts as an anabolic stimulus for protein synthesis signal pathways. Other reports indicated that creatine directly affects muscle protein synthesis via modulations of components in the mammalian target of rapamycin (mTOR) pathway. Creatine may also directly affect the myogenic process (formation of muscle tissue), by altering secretions of myokines, such as myostatin and insulin-like growth factor-1, and expressions of myogenic regulatory factors, resulting in enhanced satellite cells mitotic activities and differentiation into myofiber. Overall, there is still no clear understanding of the mechanisms of action regarding how creatine affects muscle mass/growth, but current evidence suggests it may exert its effects through multiple approaches, with converging impacts on protein synthesis and myogenesis.

Weight gain
Muscle cramps
Muscle strains and pulls
Stomach upset
Diarrhea
Dizziness
High blood pressure Liver dysfunction
Kidney damage

1. 196 g (2.2 moles) of N-methylglycine (sarcosine) was dissolved in 360 g of water and heated to 80 °C to form a homogeneous solution. 2. the above hot solution was rapidly added to a pre-prepared aqueous solution of S-(carboxymethyl)isothiourea, and the rate of addition was controlled to ensure that the temperature of the reaction system was maintained below 60°C. 3. continuously stirring the reaction mixture at 60 °C for 3 hours to ensure that the reaction proceeds adequately. 4. Upon completion of the reaction, the heating was stopped and the reaction system was transferred to an ice water bath and cooled to 0-5 °C to promote crystallization. 5. The white crystalline product was collected by filtration, the filter cake was washed with a small amount of anhydrous ethanol to remove impurities, and dried to give 238 g of creatine monohydrate (white crystals, melting point 294 °C) in 80% yield. 6. The filtrate was extracted with 300 ml of chloroform in four times and all the chloroform extracts were combined. 7. The chloroform was recovered by distillation at atmospheric pressure and the residue was distilled under vacuum at 0.098 MPa under reduced pressure. 8. The fractions at 104-106 °C were collected to give 156 g of mercaptoacetic acid in 85% yield.

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.]

[1] Patent: CN105777594, 2016, A. Location in patent: Paragraph 0025; 0026