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Merck
CN

27890

Creatine

anhydrous, ≥99.0% (NT)

Synonym(s):

(α-Methylguanido)acetic acid, N-Amidinosarcosine

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About This Item

Linear Formula:
H2NC(=NH)N(CH3)CH2CO2H
CAS Number:
Molecular Weight:
131.13
EC Number:
200-306-6
UNSPSC Code:
12352200
PubChem Substance ID:
Beilstein/REAXYS Number:
907175
MDL number:
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assay

≥99.0% (NT)

impurities

≤0.5% water

mp

~295 °C (dec.)

SMILES string

CN(CC(O)=O)C(N)=N

InChI

1S/C4H9N3O2/c1-7(4(5)6)2-3(8)9/h2H2,1H3,(H3,5,6)(H,8,9)

InChI key

CVSVTCORWBXHQV-UHFFFAOYSA-N

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Biochem/physiol Actions

Creatine is a nitrogenous compound that acts as a high-energy reservoir for the rapid regeneration of ATP.
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.

Other Notes

Identification of creatine as a cofactor of thiamine-diphosphate kinase

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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Subrata Patra et al.
Amino acids, 42(6), 2319-2330 (2011-07-20)
The creatine/creatine kinase (CK) system plays a key role in cellular energy buffering and transport. In vertebrates, CK has four isoforms expressed in a tissue-specific manner. In the process of creatine biosynthesis several other important metabolites are formed. The anticancer
H Shikata et al.
FEBS letters, 201(1), 101-104 (1986-05-26)
Thiamin-diphosphate (TDP) kinase which catalyzes thiamin triphosphate formation from TDP requires a low-molecular-mass cofactor in addition to ATP and Mg2+. The cofactor was isolated in a crystalline form from pig skeletal muscle and identified as creatine by proton NMR, mass
Philippe Généreux et al.
Journal of the American College of Cardiology, 65(6), 533-543 (2015-02-14)
Bifurcation lesions are frequent among patients with symptomatic coronary disease treated by percutaneous coronary intervention. Current evidence recommends a conservative (provisional) approach when treating the side branch (SB). The TRYTON (Prospective, Single Blind, Randomized Controlled Study to Evaluate the Safety
Theo Wallimann et al.
Amino acids, 40(5), 1271-1296 (2011-03-31)
The pleiotropic effects of creatine (Cr) are based mostly on the functions of the enzyme creatine kinase (CK) and its high-energy product phosphocreatine (PCr). Multidisciplinary studies have established molecular, cellular, organ and somatic functions of the CK/PCr system, in particular
Dan Atar et al.
European heart journal, 36(2), 112-119 (2014-09-03)
The MITOCARE study evaluated the efficacy and safety of TRO40303 for the reduction of reperfusion injury in patients undergoing revascularization for ST-elevation myocardial infarction (STEMI). Patients presenting with STEMI within 6 h of the onset of pain randomly received TRO40303

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