Creatine

Creatine
Skeletal formula of creatine
Ball and stick model of creatine
Names
Systematic IUPAC name
2-[Carbamimidoyl(methyl)amino]acetic acid
Other names
N-Carbamimidoyl-N-methylglycine; Methylguanidoacetic acid
Identifiers
3D model (JSmol)
3DMetB00084
907175
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard100.000.278
EC Number200-306-6
240513
KEGG
MeSHCreatine
RTECS numberMB7706000
UNII
Properties
C4H9N3O2
Molar mass131.14 g·mol−1
AppearanceWhite crystals
OdorOdourless
Melting point 255 °C (491 °F; 528 K)
13.3 g L−1 (at 18 °C)
log P−1.258
Acidity (pKa)3.429
Basicity (pKb)10.568
Isoelectric point8.47
Thermochemistry
171.1 J K−1 mol−1 (at 23.2 °C)
189.5 J K−1 mol−1
−538.06–−536.30 kJ mol−1
−2.3239–−2.3223 MJ mol−1
Pharmacology
WHO)
Pharmacokinetics:
3 hours
Hazards
GHS pictogramsThe exclamation-mark pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS)
GHS signal wordWARNING
H315, H319, H335
P261, P305+351+338
Related compounds
Related alkanoic acids
Related compounds
Dimethylacetamide
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
No verify (what is YesYNo ?)
Infobox references

Creatine (n/ or n/[1][2]) is a nitrogenous organic acid that occurs naturally in vertebrates. Its main role is to facilitate recycling of adenosine triphosphate (ATP), the energy currency of the cell, primarily in muscle and brain tissue. This is achieved by recycling adenosine diphosphate (ADP) to ATP via donation of phosphate groups. Creatine also acts as a pH buffer in tissues.[3]

Creatine synthesis primarily occurs in the liver and kidneys.[3][4] On average, it is produced endogenously at an estimated rate of about 8.3 mmol or 1 gram per day in young adults.[4][5] Creatine is also obtained through the diet at a rate of about 1 gram per day from an omnivorous diet.[4][6] Most of the human body's total creatine and phosphocreatine stores are found in skeletal muscle, while the remainder is distributed in the blood, brain, and other tissues.[5][6]

Creatine was identified in 1832 when Michel Eugène Chevreul isolated it from the basified water-extract of skeletal muscle. He later named the crystallized precipitate after the Greek word for meat, κρέας (kreas). In solution, creatine is in equilibrium with creatinine.[7] Creatine is a derivative of the guanidinium cation.

Biosynthesis

Creatine is not an essential nutrient[8] as it is naturally produced in the human body from the amino acids glycine and arginine. In the first step of the biosynthesis these two amino acids are combined by the enzyme EC:2.1.4.1) to form guanidinoacetate, which is then methylated by EC:2.1.1.2), using S-adenosyl methionine as the methyl donor. Creatine itself can be phosphorylated by creatine kinase to form phosphocreatine, which is used as an energy buffer in skeletal muscles and the brain.

CreatineSynthesis(en).png

Synthesis primarily takes place in the kidney and liver, with creatine then being transported to the muscles via the blood. The majority of the human body's total creatine and phosphocreatine stores is located in skeletal muscle, while the remainder is distributed in the blood, brain, and other tissues.[5][6][9] Typically, creatine is produced endogenously at an estimated rate of about 8.3 mmol or 1 gram per day in young adults.[4][5] Creatine is also obtained through the diet at a rate of about 1 gram per day from an omnivorous diet.[5][6] Some small studies suggest that total muscle creatine is significantly lower in vegetarians than non-vegetarians, as expected since vegetables are not a primary source of creatine. However, subjects happened to show the same levels after using supplements.[10]

Genetic deficiencies in the creatine biosynthetic pathway lead to various severe neurological defects.[11] Clinically, there are three distinct disorders of creatine metabolism. Deficiencies in the two synthesis enzymes can cause L-arginine:glycine amidinotransferase deficiency and guanidinoacetate methyltransferase deficiency. Both biosynthetic defects are inherited in an autosomal recessive manner. A third defect, creatine transporter defect, is caused by mutations in SLC6A8 and inherited in a X-linked manner. This condition is related to the transport of creatine into the brain.[12]

Other Languages
العربية: كرياتين
беларуская: Крэацін
български: Креатин
català: Creatina
čeština: Kreatin
dansk: Kreatin
Deutsch: Kreatin
eesti: Kreatiin
Ελληνικά: Κρεατίνη
español: Creatina
Esperanto: Kreatino
français: Créatine
galego: Creatina
한국어: 크레아틴
Հայերեն: Կրեատին
hrvatski: Kreatin
Bahasa Indonesia: Kreatina
italiano: Creatina
עברית: קראטין
latviešu: Kreatīns
lietuvių: Kreatinas
magyar: Kreatin
македонски: Креатин
Nederlands: Creatine
日本語: クレアチン
norsk: Kreatin
polski: Kreatyna
português: Creatina
русский: Креатин
Simple English: Creatine
slovenčina: Kreatín
српски / srpski: Kreatin
srpskohrvatski / српскохрватски: Kreatin
suomi: Kreatiini
svenska: Kreatin
Türkçe: Kreatin
українська: Креатин
中文: 肌酸